Benzhydryl derivatives

Abstract

Benzhydryl derivatives of the formula I, 1

Description

[0001] The invention relates to benzhydryl derivatives of the formula I, 2

[0002] where the index and the variables are as defined below:

[0003] X is oxygen or sulfur;

[0004] R1, R3 are halogen, cyano, nitro, hydroxyl, mercapto, amino,

[0005] C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-alkoxy, C2-C6-alkenyloxy, C2-C6-alkynyloxy, C1-C6-alkylcarbonyloxy, formyloxy, C1-C6-alkylthio, C2-C6-alkenylthio, C2-C6-alkynylthio, C1-C6-alkylamino, di-C1-C6-alkylamino, C1-C6-alkylcarbonyl or formyl, where the carbon atoms in the radicals mentioned may be partially or fully halogenated;

[0006] R2 is halogen, cyano, nitro, hydroxyl, mercapto, amino, C1-C6-alkyl, C1-C6-alkoxy, C1-C6-haloalkyl or C1-C6-haloalkoxy, where the groups R2 may be different if n=2;

[0007] R4 is C1-C6-alkyl, C2-C6-alkenyl or C2-C6-alkynyl, where the carbon atoms in these radicals may be unsubstituted or partially or fully halogenated;

[0008] R5, R6 are hydroxyl, C1-C6-alkyl, C2-C6-alkenyl, C1-C6-haloalkyl, C2-C6-haloalkenyl, C1-C6-alkoxy, C2-C6-alkenyloxy, C1-C6-haloalkoxy, C2-C6-haloalkenyloxy, C3-C8-cycloalkyl, C3-C8-cycloalkyl-C1-C3-alkyl, C3-C8-cycloalkoxy or C3-C8-cycloalkyl-C1-C3-alkoxy;

[0009] n is 0, 1 or 2.

[0010] Additionally, the invention relates to processes for preparing the compounds I, to compositions comprising them and to the use of the compounds I for controlling phytopathogenic fungi.

[0011] In JP 08225474 various benzhydryl alcohols have been described as starting materials for pharmaceutics.

[0012] EP-A 461 079 discloses various benzhydryl alcohols having herbicidal action.

[0013] Benzhydryl alcohols having fungicidal action are already known, for example

[0014] (RS)-2,4′-difluoro-alpha-(1H-1,2,4-triazol-1-ylmethyl)benzhydryl alcohol (flutriafol; EP-A 015 756) or

[0015] (R,S)-2,4′-dichloro-alpha-(pyrimidin-5-yl)benzhydryl alcohol (fenarimol; GB 1 218 623). However, their action is not entirely satisfactory.

[0016] Benzophenones having fungicidal action are known from EP-A 727 141.

[0017] It is an object of the present invention to provide benzhydryl derivatives having a higher efficacy in the control of harmful fungi.

[0018] We have found that this object is achieved by the benzhydryl derivatives of the formula I. Furthermore, we have found processes for preparing the compounds I and compositions comprising them for controlling harmful fungi.

[0019] The compounds of the formula I differ from the benzhydryl alcohols disclosed in JP 08225474 by the substitution pattern on the phenyl rings.

[0020] The compounds of the formula I differ from the herbicidally active benzhydryl alcohols disclosed in EP-A 461 079 by the substituents of the phenyl rings, which substituents are fixed in positions 2, 2, 2′, 2′, 3′, 4 and 4′.

[0021] The compounds of the formula I are secondary alcohols or thiols, whereas the compounds disclosed in EP-A 015 756 and GB 1 218 623 are tertiary alcohols which furthermore differ from compounds of the formula I in the substitution pattern on the phenyl rings.

[0022] The compounds of the formula I differ from the fungicidally active benzophenones disclosed in EP-A 727 141 in that the keto group is replaced by an alcohol or thiol function, and by the substitution patterns on the phenyl rings.

[0023] In the definitions of the symbols given in the formulae above, collective terms were used which, in general, represent the following substituents:

[0024] Halogen: fluorine, chlorine, bromine or iodine, preferably chlorine or bromine;

[0025] Alkyl: saturated, straight-chain or branched hydrocarbon radicals having 1 to 4 or 1 to 6 carbon atoms, for example C1-C6-alkyl, such as methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl, 1,1-dimethylethyl, pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl, hexyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1,1,2-trimethylpropyl, 1,2,2-trimethylpropyl, 1-ethyl-1-methylpropyl and 1-ethyl-2-methylpropyl;

[0026] Haloalkyl: straight-chain or branched alkyl groups having 1 to 6 carbon atoms (as mentioned above), it being possible for some or all of the hydrogen atoms in these groups to be replaced by halogen atoms as mentioned above, for example 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 and pentafluoroethyl;

[0027] Alkoxy: straight-chain or branched alkyl groups having 1 to 6 carbon atoms (as mentioned above), which are attached to the phenyl ring via an oxygen atom (—O—);

[0028] Haloalkoxy: straight-chain or branched haloalkyl groups having 1 to 6 carbon atoms (as mentioned above) which are attached to the phenyl ring via an oxygen atom (—O—);

[0029] Alkylthio: straight-chain or branched alkyl groups having 1 to 6 or 1 to 4 carbon atoms (as mentioned above) which are attached to the phenyl ring via a sulfur atom (—S—);

[0030] Alkylamino: a straight-chain or branched alkyl group having 1 to 6 carbon atoms (as mentioned above) which is attached to the phenyl ring via an amino group (—NH—);

[0031] Dialkylamino: two independent straight-chain or branched alkyl groups having in each case 1 to 6 carbon atoms (as mentioned above) which are attached to the phenyl ring via a nitrogen atom;

[0032] Alkylcarbonyloxy: a straight-chain or branched alkyl group having 1 to 6 carbon atoms (as mentioned above) which is attached to the phenyl ring via a carbonyloxy group (—CO2—);

[0033] Alkenyl: unsaturated, straight-chain or branched hydrocarbon radicals having 2 to 6 carbon atoms and a double bond in any position, for example C2-C6-alkenyl such as ethenyl, 1-propenyl, 2-propenyl, 1-methylethenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl-1-propenyl, 2-methyl-1-propenyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-methyl-1-butenyl, 2-methyl-1-butenyl, 3-methyl-1-butenyl, 1-methyl-2-butenyl, 2-methyl-2-butenyl, 3-methyl-2-butenyl, 1-methyl-3-butenyl, 2-methyl-3-butenyl, 3-methyl-3-butenyl, 1,1-dimethyl-2-propenyl, 1,2-dimethyl-1-propenyl, 1,2-dimethyl-2-propenyl, 1-ethyl-1-propenyl, 1-ethyl-2-propenyl, 1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, 5-hexenyl, 1-methyl-1-pentenyl, 2-methyl-1-pentenyl, 3-methyl-1-pentenyl, 4-methyl-1-pentenyl, 1-methyl-2-pentenyl, 2-methyl-2-pentenyl, 3-methyl-2-pentenyl, 4-methyl-2-pentenyl, 1-methyl-3-pentenyl, 2-methyl-3-pentenyl, 3-methyl-3-pentenyl, 4-methyl-3-pentenyl, 1-methyl-4-pentenyl, 2-methyl-4-pentenyl, 3-methyl-4-pentenyl, 4-methyl-4-pentenyl, 1,1-dimethyl-2-butenyl, 1,1-dimethyl-3-butenyl, 1,2-dimethyl-1-butenyl, 1,2-dimethyl-2-butenyl, 1,2-dimethyl-3-butenyl, 1,3-dimethyl-1-butenyl, 1,3-dimethyl-2-butenyl, 1,3-dimethyl-3-butenyl, 2,2-dimethyl-3-butenyl, 2,3-dimethyl-1-butenyl, 2,3-dimethyl-2-butenyl, 2,3-dimethyl-3-butenyl, 3,3-dimethyl-1-butenyl, 3,3-dimethyl-2-butenyl, 1-ethyl-1-butenyl, 1-ethyl-2-butenyl, 1-ethyl-3-butenyl, 2-ethyl-1-butenyl, 2-ethyl-2-butenyl, 2-ethyl-3-butenyl, 1,1,2-trimethyl-2-propenyl, 1-ethyl-1-methyl-2-propenyl, 1-ethyl-2-methyl-1-propenyl and 1-ethyl-2-methyl-2-propenyl;

[0034] Haloalkenyl: unsaturated, straight-chain or branched hydrocarbon radicals having 2 to 6 carbon atoms and a double bond in any position (as mentioned above), it being possible for some or all of the hydrogen atoms in these groups to be replaced by halogen atoms as mentioned above, in particular by fluorine, chlorine and bromine;

[0035] Alkenyloxy: unsaturated, straight-chain or branched hydrocarbon radicals having 2 to 6 carbon atoms and a double bond in any position which is not adjacent to the heteroatom (as mentioned above), which are attached to the phenyl ring via an oxygen atom (—O—);

[0036] Haloalkenyloxy: unsaturated, straight-chain or branched alkenyloxy groups having 3 to 6 carbon atoms (as mentioned above), it being possible for some or all of the hydrogen atoms in these groups to be replaced by halogen atoms as mentioned above, in particular by fluorine, chlorine and bromine;

[0037] Alkenylthio: unsaturated, straight-chain or branched hydrocarbon radicals having 2 to 6 carbon atoms and a double bond in any position which is not adjacent to the heteroatom (as mentioned above), which are attached to the phenyl ring via a sulfur atom (—S—);

[0038] Alkynyl: straight-chain or branched hydrocarbon groups having 2 to 6 carbon atoms and a triple bond in any position, for example C2-C6-alkynyl such as ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methyl-2-propynyl, 1-pentynyl, 2-pentynyl, 3-pentynyl, 4-pentynyl, 1-methyl-2-butynyl, 1-methyl-3-butynyl, 2-methyl-3-butynyl, 3-methyl-1-butynyl, 1,1-dimethyl-2-propynyl, 1-ethyl-2-propynyl, 1-hexynyl, 2-hexynyl, 3-hexynyl, 4-hexynyl, 5-hexynyl, 1-methyl-2-pentynyl, 1-methyl-3-pentynyl, 1-methyl-4-pentynyl, 2-methyl-3-pentynyl, 2-methyl-4-pentynyl, 3-methyl-1-pentynyl, 3-methyl-4-pentynyl, 4-methyl-1-pentynyl, 4-methyl-2-pentynyl, 1,1-dimethyl-2-butynyl, 1,1-dimethyl-3-butynyl, 1,2-dimethyl-3-butynyl, 2,2-dimethyl-3-butynyl, 3,3-dimethyl-1-butynyl, 1-ethyl-2-butynyl, 1-ethyl-3-butynyl, 2-ethyl-3-butynyl and 1-ethyl-1-methyl-2-propynyl;

[0039] Alkynyloxy: unsaturated, straight-chain or branched hydrocarbon radicals having 3 to 6 carbon atoms and a triple bond in any position which is not adjacent to the heteroatom (as mentioned above), which are attached to the skeleton via an oxygen atom (—O—);

[0040] Alkynylthio: unsaturated, straight-chain or branched hydrocarbon radicals having 3 to 6 carbon atoms and a triple bond in any position which is not adjacent to the heteroatom (as mentioned above), which are attached to the skeleton via a sulfur atom (—S—).

[0041] With respect to the intended use of the benzhydryl compounds of the formula I, the following meanings of the substituents are particularly preferred, in each case on their own or in combination:

[0042] Benzhydryl derivatives of the formula I as claimed in claim 1 where the variables are as defined below:

[0043] X is oxygen or sulfur;

[0044] R1, R3 independently of one another are halogen, hydroxyl, mercapto, amino,

[0045] C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-haloalkyl, C2-C6-haloalkenyl, C2-C6-haloalkynyl, C1-C6-alkoxy, C2-C6-alkenyloxy, C2-C6-alkynyloxy, C1-C6-haloalkoxy, C2-C6-haloalkenyloxy, C2-C6-haloalkynyloxy, C1-C6-alkylcarbonyloxy, C1-C6-haloalkylcarbonyloxy, formyloxy, C1-C6-alkylthio, C2-C6-alkenylthio, C2-C6-alkynylthio, C1-C6-haloalkylthio, C2-C6-haloalkenylthio, C2-C6-haloalkynylthio, C1-C6-alkylamino, di-C1-C6-alkylamino, C1-C6-haloalkylamino, di-C1-C6-haloalkylamino, C1-C6-alkylcarbonyl, C1-C6-haloalkylcarbonyl or formyl;

[0046] R2 is halogen, hydroxyl, C1-C6-alkyl, C1-C6-alkoxy, C1-C6-haloalkyl or C1-C6-haloalkoxy, where the radicals R2 may be different if n=2;

[0047] R4 is C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-haloalkyl, C2-C6-haloalkenyl or C2-C6-haloalkynyl;

[0048] R5, R6 independently of one another are hydroxyl, C1-C6-alkoxy, C2-C6-alkenyloxy, C1-C6-haloalkoxy or C2-C6-haloalkenyloxy;

[0049] n is 0, 1 or 2.

[0050] Particular preference is given to compounds I in which X is oxygen or sulfur;

[0051] R1 and R3 independently of one another are halogen, hydroxyl, mercapto, amino, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy or C1-C6-alkylcarbonyl;

[0052] R2 is halogen, hydroxyl, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy or C1-C6-haloalkoxy, where the radicals R2 may be different if n=2;

[0053] R4 is methyl;

[0054] R5, R6 independently of one another are hydroxyl, C1-C6-alkoxy, C2-C6-alkenyloxy, C1-C6-haloalkoxy or C2-C6-haloalkenyloxy and

[0055] n is 0 or 1.

[0056] Especially preferred are compounds I in which X is oxygen.

[0057] Preference is furthermore given to compounds I in which R1 and R3 independently of one another are halogen, hydroxyl, amino, mercapto, nitro, cyano, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkylcarbonyloxy, C1-C6-haloalkylcarbonyloxy, C1-C6-alkylthio, C1-C6-haloalkylthio, C1-C6-alkylcarbonyl or C1-C6-haloalkylcarbonyl. Here, particular mention may be made of: fluorine, chlorine, bromine or iodine, hydroxyl, mercapto, amino, methyl, ethyl, methoxy, ethoxy, methylcarbonyloxy, ethylcarbonyloxy, methylthio, ethylthio, trifluoromethyl, difluoromethoxy or chlorofluoromethoxy.

[0058] In addition, preference is given to compounds I in which R1 and R3 independently of one another are halogen, hydroxyl, mercapto, amino, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy or C1-C6-haloalkoxy. Here, particular mention may be made of: fluorine, chlorine, bromine or iodine, hydroxyl, mercapto, amino, methyl, ethyl, methoxy, ethoxy, trifluoromethyl, difluoromethoxy or chlorofluoromethoxy.

[0059] Particular preference is furthermore given to compounds I in which R1 and R3 independently of one another are halogen, such as fluorine, chlorine, bromine or iodine, hydroxyl, C1-C6-alkyl, such as methyl or ethyl, C1-C6-alkoxy, such as methoxy or ethoxy, or C1-C6-alkylcarbonyloxy, such as methylcarbonyloxy or ethylcarbonyloxy.

[0060] In addition, particular preference is given to compounds I in which R1 and R3 independently of one another are halogen, such as fluorine, chlorine, bromine or iodine, hydroxyl, C1-C6-alkyl, such as methyl or ethyl, or C1-C6-alkoxy, such as methoxy or ethoxy.

[0061] Very particular preference is given to compounds I in which R1 and R3 independently of one another are halogen, such as chlorine or bromine, or C1-C6-alkyl, such as methyl or ethyl.

[0062] Likewise, very particular preference is given to compounds I in which R1 and R3 independently of one another are hydroxyl, C1-C6-alkoxy, such as methoxy or ethoxy, or C1-C6-alkylcarbonyloxy, such as methylcarbonyloxy or ethylcarbonyloxy.

[0063] In addition, very particular preference is given to compounds I in which R1 and R3 independently of one another are hydroxyl or C1-C6-alkoxy, such as methoxy or ethoxy.

[0064] Moreover, preference is also given to compounds I in which R2 is halogen, hydroxyl, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy or C1-C6-haloalkoxy, where the groups R2 may be different if n=2. Here, particular mention may be made of: fluorine, chlorine, bromine, iodine, methyl, ethyl, trifluoromethyl, difluoromethoxy, chlorofluoromethoxy.

[0065] Especially preferred are also compounds I in which R2 is halogen, hydroxyl or C1-C6-alkoxy, such as methoxy or ethoxy.

[0066] Very particular preference is given to compounds I in which R2 is halogen, in particular bromine or chlorine.

[0067] Moreover, particular preference is given to compounds I in which R4 is C1-C6-alkyl or C1-C6-haloalkyl. Here, particular mention may be made of: methyl, ethyl and trifluoromethyl.

[0068] Especially preferred are compounds I in which R4 is methyl.

[0069] Moreover, particular preference is given to compounds I in which R5 and R6 independently of one another are hydroxyl, C1-C6-alkoxy, C2-C6-alkenyloxy, C1-C6-haloalkoxy or C2-C6-haloalkenyloxy. Here, particular mention may be made of: hydroxyl, methoxy, ethoxy, n-propoxy, isopropoxy, butoxy, pentoxy, hexoxy, propenyloxy, trifluoromethoxy, difluoromethoxy and chlorofluoromethoxy.

[0070] Particular preference is furthermore given to compounds I in which R5 and R6 independently of one another are hydroxyl or C1-C6-alkoxy, such as methoxy, ethoxy, propoxy, butoxy, pentoxy and hexoxy.

[0071] Very particular preference is given to compounds I in which R5 and R6 are methoxy.

[0072] In addition, particular preference is given to compounds I in which n is 0 or 1, very particularly preferably 1.

[0073] Very particular preference is given to compounds I in which R1 and R3 independently of one another are fluorine, chlorine, bromine, iodine, hydroxyl, mercapto, methylthio, amino, methyl, ethyl, trifluoromethyl, methoxy, difluoromethoxy, fluorochloromethoxy, trifluoromethoxy, methylcarbonyloxy or ethylcarbonyloxy, R2 is fluorine, chlorine, bromine, iodine, hydroxyl, methyl, trifluoromethyl, methoxy, ethoxy, difluoromethoxy or chlorofluoromethoxy, R4 is methyl, ethyl or trifluoromethyl, R5 and R6 independently of one another are hydroxyl, methoxy, ethoxy, n-propoxy, isopropoxy or n-butoxy and n is 0 or 1.

[0074] With respect to their use, particular preference is given to the compounds I-A compiled in the tables below. The groups mentioned in the tables for a substituent are furthermore in their own right, independently of the combination in which they are mentioned, a particularly preferred embodiment of the substituent in question.

[0075] Table 1

[0076] Compounds of formula I-A in which n is 0, R4 is methyl and R6 is methoxy and the combination of the radicals R1, R3 and R5 for a compound corresponds in each case to one row of Table A

[0077] Table 2

[0078] Compounds of the formula I-A in which n is 1, R2 is 3-methyl, R4 is methyl and R6 is methoxy and the combination of the radicals R1, R3 and R5 for a compound in each case corresponds to one row of Table A

[0079] Table 3

[0080] Compounds of the formula I-A in which n is 1, R2 is 5-methyl, R4 is methyl and R6 is methoxy and the combination of the radicals R1, R3 and R5 for a compound in each case corresponds to one row of Table A, where R1 is different from R3

[0081] Table 4

[0082] Compounds of the formula I-A in which n is 1, R2 is 3-trifluoromethyl, R4 is methyl and R6 is methoxy and the combination of the radicals R1, R3 and R5 for a compound in each case corresponds to one row of Table A

[0083] Table 5

[0084] Compounds of the formula I-A in which n is 1, R2 is 5-trifluoromethyl, R4 is methyl and R6 is methoxy and the combination of the radicals R1, R3 and R5 for a compound in each case corresponds to one row of Table A, where R1 is different from R3

[0085] Table 6

[0086] Compounds of the formula I-A in which n is 1, R2 is 3-hydroxyl, R4 is methyl and R6 is methoxy and the combination of the radicals R1, R3 and R5 for a compound in each case corresponds to one row of Table A

[0087] Table 7

[0088] Compounds of the formula I-A in which n is 1, R2 is 5-hydroxyl, R4 is methyl and R6 is methoxy and the combination of the radicals R1, R3 and R5 for a compound in each case corresponds to one row of Table A, where R1 is different from R3

[0089] Table 8

[0090] Compounds of the formula I-A in which n is 1, R2 is 3-methoxy, R4 is methyl and R6 is methoxy and the combination of the radicals R1, R3 and R5 for a compound in each case corresponds to one row of Table A

[0091] Table 9

[0092] Compounds of the formula I-A in which n is 1, R2 is 5-methoxy, R4 is methyl and R6 is methoxy and the combination of the radicals R1, R3 and R5 for a compound in each case corresponds to one row of Table A, where R1 is different from R3

[0093] Table 10

[0094] Compounds of the formula I-A in which n is 1, R2 is 3-ethoxy, R4 is methyl and R6 is methoxy and the combination of the radicals R1, R3 and R5 for a compound in each case corresponds to one row of Table A

[0095] Table 11

[0096] Compounds of the formula I-A in which n is 1, R2 is 5-ethoxy, R4 is methyl and R6 is methoxy and the combination of the radicals R1, R3 and R5 for a compound in each case corresponds to one row of Table A, where R1 is different from R3

[0097] Table 12

[0098] Compounds of the formula I-A in which n is 1, R2 is 3-difluoromethoxy, R4 is methyl and R6 is methoxy and the combination of the radicals R1, R3 and R5 for a compound in each case corresponds to one row of Table A

[0099] Table 13

[0100] Compounds of the formula I-A in which n is 1, R2 is 5-difluoromethoxy, R4 is methyl and R6 is methoxy and the combination of the radicals R1, R3 and R5 for a compound in each case corresponds to one row of Table A, where R1 is different from R3

[0101] Table 14

[0102] Compounds of the formula I-A in which n is 1, R2 is 3-chlorofluoromethoxy, R4 is methyl and R6 is methoxy and the combination of the radicals R1, R3 and R5 for a compound in each case corresponds to one row of Table A

[0103] Table 15

[0104] Compounds of the formula I-A in which n is 1, R2 is 5-chlorofluoromethoxy, R4 is methyl and R6 is methoxy and the combination of the radicals R1, R3 and R5 for a compound in each case corresponds to one row of Table A, where R1 is different from R3

[0105] Table 16

[0106] Compounds of the formula I-A in which n is 1, R2 is 3-fluorine, R4 is methyl and R6 is methoxy and the combination of the radicals R1, R3 and R5 for a compound in each case corresponds to one row of Table A

[0107] Table 17

[0108] Compounds of the formula I-A in which n is 1, R2 is 5-fluorine, R4 is methyl and R6 is methoxy and the combination of the radicals R1, R3 and R5 for a compound in each case corresponds to one row of Table A, where R1 is different from R3

[0109] Table 18

[0110] Compounds of the formula I-A in which n is 1, R2 is 3-chlorine, R4 is methyl and R6 is methoxy and the combination of the radicals R1, R3 and R5 for a compound in each case corresponds to one row of Table A

[0111] Table 19

[0112] Compounds of the formula I-A in which n is 1, R2 is 5-chlorine, R4 is methyl and R6 is methoxy and the combination of the radicals R1, R3 and R5 for a compound in each case corresponds to one row of Table A, where R1 is different from R3

[0113] Table 20

[0114] Compounds of the formula I-A in which n is 1, R2 is 3-bromine, R4 is methyl and R6 is methoxy and the combination of the radicals R1, R3 and R5 for a compound in each case corresponds to one row of Table A

[0115] Table 21

[0116] Compounds of the formula I-A in which n is 1, R2 is 5-bromine, R4 is methyl and R6 is methoxy and the combination of the radicals R1, R3 and R5 for a compound in each case corresponds to one row of Table A, where R1 is different from R3

[0117] Table 22

[0118] Compounds of the formula I-A in which n is 1, R2 is 3-iodine, R4 is methyl and R6 is methoxy and the combination of the radicals R1, R3 and R5 for a compound in each case corresponds to one row of Table A

[0119] Table 23

[0120] Compounds of the formula I-A in which n is 1, R2 is 5-iodine, R4 is methyl and R6 is methoxy and the combination of the radicals R1, R3 and R5 for a compound in each case corresponds to one row of Table A, where R1 is different from R3

[0121] Table 24

[0122] Compounds of the formula I-A in which n is 0, R4 is ethyl and R6 is methoxy and the combination of the radicals R1, R3 and R5 for a compound in each case corresponds to one row of Table A

[0123] Table 25

[0124] Compounds of the formula I-A in which n is 1, R2 is 3-methyl, R4 is ethyl and R6 is methoxy and the combination of the radicals R1, R3 and R5 for a compound in each case corresponds to one row of Table A

[0125] Table 26

[0126] Compounds of the formula I-A in which n is 1, R2 is 5-methyl, R4 is ethyl and R6 is methoxy and the combination of the radicals R1, R3 and R5 for a compound in each case corresponds to one row of Table A, where R1 is different from R3

[0127] Table 27

[0128] Compounds of the formula I-A in which n is 1, R2 is 3-trifluoromethyl, R4 is ethyl and R6 is methoxy and the combination of the radicals R1, R3 and R5 for a compound in each case corresponds to one row of Table A

[0129] Table 28

[0130] Compounds of the formula I-A in which n is 1, R2 is 5-trifluoromethyl, R4 is ethyl and R6 is methoxy and the combination of the radicals R1, R3 and R5 for a compound in each case corresponds to one row of Table A, where R1 is different from R3

[0131] Table 29

[0132] Compounds of the formula I-A in which n is 1, R2 is 3-hydroxy, R4 is ethyl and R6 is methoxy and the combination of the radicals R1, R3 and R5 for a compound in each case corresponds to one row of Table A

[0133] Table 30

[0134] Compounds of the formula I-A in which n is 1, R2 is 5-hydroxy, R4 is ethyl and R6 is methoxy and the combination of the radicals R1, R3 and R5 for a compound in each case corresponds to one row of Table A, where R1 is different from R3

[0135] Table 31

[0136] Compounds of the formula I-A in which n is 1, R2 is 3-methoxy, R4 is ethyl and R6 is methoxy and the combination of the radicals R1, R3 and R5 for a compound in each case corresponds to one row of Table A

[0137] Table 32

[0138] Compounds of the formula I-A in which n is 1, R2 is 5-methoxy, R4 is ethyl and R6 is methoxy and the combination of the radicals R1, R3 and R5 for a compound in each case corresponds to one row of Table A, where R1 is different from R3

[0139] Table 33

[0140] Compounds of the formula I-A in which n is 1, R2 is 3-ethoxy, R4 is ethyl and R6 is methoxy and the combination of the radicals R1, R3 and R5 for a compound in each case corresponds to one row of Table A

[0141] Table 34

[0142] Compounds of the formula I-A in which n is 1, R2 is 5-ethoxy, R4 is ethyl and R6 is methoxy and the combination of the radicals R1, R3 and R5 for a compound in each case corresponds to one row of Table A, where R1 is different from R3

[0143] Table 35

[0144] Compounds of the formula I-A in which n is 1, R2 is 3-difluoromethoxy, R4 is ethyl and R6 is methoxy and the combination of the radicals R1, R3 and R5 for a compound in each case corresponds to one row of Table A

[0145] Table 36

[0146] Compounds of the formula I-A in which n is 1, R2 is 5-difluoromethoxy, R4 is ethyl and R6 is methoxy and the combination of the radicals R1, R3 and R5 for a compound in each case corresponds to one row of Table A, where R1 is different from R3

[0147] Table 37

[0148] Compounds of the formula I-A in which n is 1, R2 is 3-chlorofluoromethoxy, R4 is ethyl and R6 is methoxy and the combination of the radicals R1, R3 and R5 for a compound in each case corresponds to one row of Table A

[0149] Table 38

[0150] Compounds of the formula I-A in which n is 1, R2 is 5-chlorofluoromethoxy, R4 is ethyl and R6 is methoxy and the combination of the radicals R1, R3 and R5 for a compound in each case corresponds to one row of Table A, where R1 is different from R3

[0151] Table 39

[0152] Compounds of the formula I-A in which n is 1, R2 is 3-fluorine, R4 is ethyl and R6 is methoxy and the combination of the radicals R1, R3 and R5 for a compound in each case corresponds to one row of Table A

[0153] Table 40

[0154] Compounds of the formula I-A in which n is 1, R2 is 5-fluorine, R4 is ethyl and R6 is methoxy and the combination of the radicals R1, R3 and R5 for a compound in each case corresponds to one row of Table A, where R1 is different from R3

[0155] Table 41

[0156] Compounds of the formula I-A in which n is 1, R2 is 3-chlorine, R4 is ethyl and R6 is methoxy and the combination of the radicals R1, R3 and R5 for a compound in each case corresponds to one row of Table A

[0157] Table 42

[0158] Compounds of the formula I-A in which n is 1, R2 is 5-chlorine, R4 is ethyl and R6 is methoxy and the combination of the radicals R1, R3 and R5 for a compound in each case corresponds to one row of Table A, where R1 is different from R3

[0159] Table 43

[0160] Compounds of the formula I-A in which n is 1, R2 is 3-bromine, R4 is ethyl and R6 is methoxy and the combination of the radicals R1, R3 and R5 for a compound in each case corresponds to one row of Table A

[0161] Table 44

[0162] Compounds of the formula I-A in which n is 1, R2 is 5-bromine, R4 is ethyl and R6 is methoxy and the combination of the radicals R1, R3 and R5 for a compound in each case corresponds to one row of Table A, where R1 is different from R3

[0163] Table 45

[0164] Compounds of the formula I-A in which n is 1, R2 is 3-iodine, R4 is ethyl and R6 is methoxy and the combination of the radicals R1, R3 and R5 for a compound in each case corresponds to one row of Table A

[0165] Table 46

[0166] Compounds of the formula I-A in which n is 1, R2 is 5-iodine, R4 is ethyl and R6 is methoxy and the combination of the radicals R1, R3 and R5 for a compound in each case corresponds to one row of Table A, where R1 is different from R3

[0167] Table 47

[0168] Compounds of the formula I-A in which n is 0, R4 is trifluoromethyl and R6 is methoxy and the combination of the radicals R1, R3 and R5 for a compound in each case corresponds to one row of Table A

[0169] Table 48

[0170] Compounds of the formula I-A in which n is 1, R2 is 3-methyl, R4 is trifluoromethyl and R6 is methoxy and the combination of the radicals R1, R3 and R5 for a compound in each case corresponds to one row of Table A

[0171] Table 49

[0172] Compounds of the formula I-A in which n is 1, R2 is 5-methyl, R4 is trifluoromethyl and R6 is methoxy and the combination of the radicals R1, R3 and R5 for a compound in each case corresponds to one row of Table A, where R1 is different from R3

[0173] Table 50

[0174] Compounds of the formula I-A in which n is 1, R2 is 3-trifluoromethyl, R4 is trifluoromethyl and R6 is methoxy and the combination of the radicals R1, R3 and R5 for a compound in each case corresponds to one row of Table A

[0175] Table 51

[0176] Compounds of the formula I-A in which n is 1, R2 is 5-trifluoromethyl, R4 is trifluoromethyl and R6 is methoxy and the combination of the radicals R1, R3 and R5 for a compound in each case corresponds to one row of Table A, where R1 is different from R3

[0177] Table 52

[0178] Compounds of the formula I-A in which n is 1, R2 is 3-hydroxyl, R4 is trifluoromethyl and R6 is methoxy and the combination of the radicals R1, R3 and R5 for a compound in each case corresponds to one row of Table A

[0179] Table 53

[0180] Compounds of the formula I-A in which n is 1, R2 is 5-hydroxy, R4 is trifluoromethyl and R6 is methoxy and the combination of the radicals R1, R3 and R5 for a compound in each case corresponds to one row of Table A, where R1 is different from R3

[0181] Table 54

[0182] Compounds of the formula I-A in which n is 1, R2 is 3-methoxy, R4 is trifluoromethyl and R6 is methoxy and the combination of the radicals R1, R3 and R5 for a compound in each case corresponds to one row of Table A

[0183] Table 55

[0184] Compounds of the formula I-A in which n is 1, R2 is 5-methoxy, R4 is trifluoromethyl and R6 is methoxy and the combination of the radicals R1, R3 and R5 for a compound in each case corresponds to one row of Table A, where R1 is different from R3

[0185] Table 56

[0186] Compounds of the formula I-A in which n is 1, R2 is 3-ethoxy, R4 is trifluoromethyl and R6 is methoxy and the combination of the radicals R1, R3 and R5 for a compound in each case corresponds to one row of Table A

[0187] Table 57

[0188] Compounds of the formula I-A in which n is 1, R2 is 5-ethoxy, R4 is trifluoromethyl and R6 is methoxy and the combination of the radicals R1, R3 and R5 for a compound in each case corresponds to one row of Table A, where R1 is different from R3

[0189] Table 58

[0190] Compounds of the formula I-A in which n is 1, R2 is 3-difluoromethoxy, R4 is trifluoromethyl and R6 is methoxy and the combination of the radicals R1, R3 and R5 for a compound in each case corresponds to one row of Table A

[0191] Table 59

[0192] Compounds of the formula I-A in which n is 1, R2 is 5-difluoromethoxy, R4 is trifluoromethyl and R6 is methoxy and the combination of the radicals R1, R3 and R5 for a compound in each case corresponds to one row of Table A, where R1 is different from R3

[0193] Table 60

[0194] Compounds of the formula I-A in which n is 1, R2 is 3-chlorofluoromethoxy, R4 is trifluoromethyl and R6 is methoxy and the combination of the radicals R1, R3 and R5 for a compound in each case corresponds to one row of Table A

[0195] Table 61

[0196] Compounds of the formula I-A in which n is 1, R2 is 5-chlorofluoromethoxy, R4 is trifluoromethyl and R6 is methoxy and the combination of the radicals R1, R3 and R5 for a compound in each case corresponds to one row of Table A, where R1 is different from R3

[0197] Table 62

[0198] Compounds of the formula I-A in which n is 1, R2 is 3-fluorine, R4 is trifluoromethyl and R6 is methoxy and the combination of the radicals R1, R3 and R5 for a compound in each case corresponds to one row of Table A

[0199] Table 63

[0200] Compounds of the formula I-A in which n is 1, R2 is 5-fluorine, R4 is trifluoromethyl and R6 is methoxy and the combination of the radicals R1, R3 and R5 for a compound in each case corresponds to one row of Table A, where R1 is different from R3

[0201] Table 64

[0202] Compounds of the formula I-A in which n is 1, R2 is 3-chlorine, R4 is trifluoromethyl and R6 is methoxy and the combination of the radicals R1, R3 and R5 for a compound in each case corresponds to one row of Table A

[0203] Table 65

[0204] Compounds of the formula I-A in which n is 1, R2 is 5-chlorine, R4 is trifluoromethyl and R6 is methoxy and the combination of the radicals R1, R3 and R5 for a compound in each case corresponds to one row of Table A, where R1 is different from R3

[0205] Table 66

[0206] Compounds of the formula I-A in which n is 1, R2 is 3-bromine, R4 is trifluoromethyl and R6 is methoxy and the combination of the radicals R1, R3 and R5 for a compound in each case corresponds to one row of Table A

[0207] Table 67

[0208] Compounds of the formula I-A in which n is 1, R2 is 5-bromine, R4 is trifluoromethyl and R6 is methoxy and the combination of the radicals R1, R3 and R5 for a compound in each case corresponds to one row of Table A, where R1 is different from R3

[0209] Table 68

[0210] Compounds of the formula I-A in which n is 1, R2 is 3-iodine, R4 is trifluoromethyl and R6 is methoxy and the combination of the radicals R1, R3 and R5 for a compound in each case corresponds to one row of Table A

[0211] Table 69

[0212] Compounds of the formula I-A in which n is 1, R2 is 5-iodine, R4 is trifluoromethyl and R6 is methoxy and the combination of the radicals R1, R3 and R5 for a compound in each case corresponds to one row of Table A, where R1 is different from R3

[0213] Table 70

[0214] Compounds of the formula I-A in which n is 0, R4 is methyl and R6 is ethoxy and the combination of the radicals R1, R3 and R5 for a compound in each case corresponds to one row of Table A

[0215] Table 71

[0216] Compounds of the formula I-A in which n is 1, R2 is 3-methyl, R4 is methyl and R6 is ethoxy and the combination of the radicals R1, R3 and R5 for a compound in each case corresponds to one row of Table A

[0217] Table 72

[0218] Compounds of the formula I-A in which n is 1, R2 is 5-methyl, R4 is methyl and R6 is ethoxy and the combination of the radicals R1, R3 and R5 for a compound in each case corresponds to one row of Table A, where R1 is different from R3

[0219] Table 73

[0220] Compounds of the formula I-A in which n is 1, R2 is 3-trifluoromethyl, R4 is methyl and R6 is ethoxy and the combination of the radicals R1, R3 and R5 for a compound in each case corresponds to one row of Table A

[0221] Table 74

[0222] Compounds of the formula I-A in which n is 1, R2 is 5-trifluoromethyl, R4 is methyl and R6 is ethoxy and the combination of the radicals R1, R3 and R5 for a compound in each case corresponds to one row of Table A, where R1 is different from R3

[0223] Table 75

[0224] Compounds of the formula I-A in which n is 1, R2 is 3-hydroxyl, R4 is methyl and R6 is ethoxy and the combination of the radicals R1, R3 and R5 for a compound in each case corresponds to one row of Table A

[0225] Table 76

[0226] Compounds of the formula I-A in which n is 1, R2 is 5-hydroxyl, R4 is methyl and R6 is ethoxy and the combination of the radicals R1, R3 and R5 for a compound in each case corresponds to one row of Table A, where R1 is different from R3

[0227] Table 77

[0228] Compounds of the formula I-A in which n is 1, R2 is 3-methoxy, R4 is methyl and R6 is ethoxy and the combination of the radicals R1, R3 and R5 for a compound in each case corresponds to one row of Table A

[0229] Table 78

[0230] Compounds of the formula I-A in which n is 1, R2 is 5-methoxy, R4 is methyl and R6 is ethoxy and the combination of the radicals R1, R3 and R5 for a compound in each case corresponds to one row of Table A, where R1 is different from R3

[0231] Table 79

[0232] Compounds of the formula I-A in which n is 1, R2 is 3-ethoxy, R4 is methyl and R6 is ethoxy and the combination of the radicals R1, R3 and R5 for a compound in each case corresponds to one row of Table A

[0233] Table 80

[0234] Compounds of the formula I-A in which n is 1, R2 is 5-ethoxy, R4 is methyl and R6 is ethoxy and the combination of the radicals R1, R3 and R5 for a compound in each case corresponds to one row of Table A, where R1 is different from R3

[0235] Table 81

[0236] Compounds of the formula I-A in which n is 1, R2 is 3-difluoromethoxy, R4 is methyl and R6 is ethoxy and the combination of the radicals R1, R3 and R5 for a compound in each case corresponds to one row of Table A

[0237] Table 82

[0238] Compounds of the formula I-A in which n is 1, R2 is 5-difluoromethoxy, R4 is methyl and R6 is ethoxy and the combination of the radicals R1, R3 and R5 for a compound in each case corresponds to one row of Table A, where R1 is different from R3

[0239] Table 83

[0240] Compounds of the formula I-A in which n is 1, R2 is 3-chlorofluoromethoxy, R4 is methyl and R6 is ethoxy and the combination of the radicals R1, R3 and R5 for a compound in each case corresponds to one row of Table A

[0241] Table 84

[0242] Compounds of the formula I-A in which n is 1, R2 is 5-chlorofluoromethoxy, R4 is methyl and R6 is ethoxy and the combination of the radicals R1, R3 and R5 for a compound in each case corresponds to one row of Table A, where R1 is different from R3

[0243] Table 85

[0244] Compounds of the formula I-A in which n is 1, R2 is 3-fluorine, R4 is methyl and R6 is ethoxy and the combination of the radicals R1, R3 and R5 for a compound in each case corresponds to one row of Table A

[0245] Table 86

[0246] Compounds of the formula I-A in which n is 1, R2 is 5-fluorine, R4 is methyl and R6 is ethoxy and the combination of the radicals R1, R3 and R5 for a compound in each case corresponds to one row of Table A, where R1 is different from R3

[0247] Table 87

[0248] Compounds of the formula I-A in which n is 1, R2 is 3-chlorine, R4 is methyl and R6 is ethoxy and the combination of the radicals R1, R3 and R5 for a compound in each case corresponds to one row of Table A

[0249] Table 88

[0250] Compounds of the formula I-A in which n is 1, R2 is 5-chlorine, R4 is methyl and R6 is ethoxy and the combination of the radicals R1, R3 and R5 for a compound in each case corresponds to one row of Table A, where R1 is different from R3

[0251] Table 89

[0252] Compounds of the formula I-A in which n is 1, R2 is 3-bromine, R4 is methyl and R6 is ethoxy and the combination of the radicals R1, R3 and R5 for a compound in each case corresponds to one row of Table A

[0253] Table 90

[0254] Compounds of the formula I-A in which n is 1, R2 is 5-bromine, R4 is methyl and R6 is ethoxy and the combination of the radicals R1, R3 and R5 for a compound in each case corresponds to one row of Table A, where R1 is different from R3

[0255] Table 91

[0256] Compounds of the formula I-A in which n is 1, R2 is 3-iodine, R4 is methyl and R6 is ethoxy and the combination of the radicals R1, R3 and R5 for a compound in each case corresponds to one row of Table A

[0257] Table 92

[0258] Compounds of the formula I-A in which n is 1, R2 is 5-iodine, R4 is methyl and R6 is ethoxy and the combination of the radicals R1, R3 and R5 for a compound in each case corresponds to one row of Table A, where R1 is different from R3

[0259] Table 93

[0260] Compounds of the formula I-A in which n is 0, R4 is ethyl and R6 is ethoxy and the combination of the radicals R1, R3 and R5 for a compound in each case corresponds to one row of Table A

[0261] Table 94

[0262] Compounds of the formula I-A in which n is 1, R2 is 3-methyl, R4 is ethyl and R6 is ethoxy and the combination of the radicals R1, R3 and R5 for a compound in each case corresponds to one row of Table A

[0263] Table 95

[0264] Compounds of the formula I-A in which n is 1, R2 is 5-methyl, R4 is ethyl and R6 is ethoxy and the combination of the radicals R1, R3 and R5 for a compound in each case corresponds to one row of Table A, where R1 is different from R3

[0265] Table 96

[0266] Compounds of the formula I-A in which n is 1, R2 is 3-trifluoromethyl, R4 is ethyl and R6 is ethoxy and the combination of the radicals R1, R3 and R5 for a compound in each case corresponds to one row of Table A

[0267] Table 97

[0268] Compounds of the formula I-A in which n is 1, R2 is 5-trifluoromethoxy, R4 is ethyl and R6 is ethoxy and the combination of the radicals R1, R3 and R5 for a compound in each case corresponds to one row of Table A, where R1 is different from R3

[0269] Table 98

[0270] Compounds of the formula I-A in which n is 1, R2 is 3-hydroxy, R4 is ethyl and R6 is ethoxy and the combination of the radicals R1 , R3 and R5 for a compound in each case corresponds to one row of Table A

[0271] Table 99

[0272] Compounds of the formula I-A in which n is 1, R2 is 5-hydroxy, R4 is ethyl and R6 is ethoxy and the combination of the radicals R1, R3 and R5 for a compound in each case corresponds to one row of Table A, where R1 is different from R3

[0273] Table 100

[0274] Compounds of the formula I-A in which n is 1, R2 is 3-methoxy, R4 is ethyl and R6 is ethoxy and the combination of the radicals R1, R3 and R5 for a compound in each case corresponds to one row of Table A

[0275] Table 101

[0276] Compounds of the formula I-A in which n is 1, R2 is 5-methoxy, R4 is ethyl and R6 is ethoxy and the combination of the radicals R1, R3 and R5 for a compound in each case corresponds to one row of Table A, where R1 is different from R3

[0277] Table 102

[0278] Compounds of the formula I-A in which n is 1, R2 is 3-ethoxy, R4 is ethyl and R6 is ethoxy and the combination of the radicals R1, R3 and R5 for a compound in each case corresponds to one row of Table A

[0279] Table 103

[0280] Compounds of the formula I-A in which n is 1, R2 is 5-ethoxy, R4 is ethyl and R6 is ethoxy and the combination of the radicals R1, R3 and R5 for a compound in each case corresponds to one row of Table A, where R1 is different from R3

[0281] Table 104

[0282] Compounds of the formula I-A in which n is 1, R2 is 3-difluoromethoxy, R4 is ethyl and R6 is ethoxy and the combination of the radicals R1, R3 and R5 for a compound in each case corresponds to one row of Table A

[0283] Table 105

[0284] Compounds of the formula I-A in which n is 1, R2 is 5-difluoromethoxy, R4 is ethyl and R6 is ethoxy and the combination of the radicals R1, R3 and R5 for a compound in each case corresponds to one row of Table A, where R1 is different from R3

[0285] Table 106

[0286] Compounds of the formula I-A in which n is 1, R2 is 3-chlorofluoromethoxy, R4 is ethyl and R6 is ethoxy and the combination of the radicals R1, R3 and R5 for a compound in each case corresponds to one row of Table A

[0287] Table 107

[0288] Compounds of the formula I-A in which n is 1, R2 is 5-chlorofluoromethoxy, R4 is ethyl and R6 is ethoxy and the combination of the radicals R1 , R3 and R5 for a compound in each case corresponds to one row of Table A, where R1 is different from R3

[0289] Table 108

[0290] Compounds of the formula I-A in which n is 1, R2 is 3-fluorine, R4 is ethyl and R6 is ethoxy and the combination of the radicals R1, R3 and R5 for a compound in each case corresponds to one row of Table A

[0291] Table 109

[0292] Compounds of the formula I-A in which n is 1, R2 is 5-fluorine, R4 is ethyl and R6 is ethoxy and the combination of the radicals R1, R3 and R5 for a compound in each case corresponds to one row of 35 Table A, where R1 is different from R3

[0293] Table 110

[0294] Compounds of the formula I-A in which n is 1, R2 is 3-chlorine, R4 is ethyl and R6 is ethoxy and the combination of the radicals R1, R3 and R5 for a compound in each case corresponds to one row of Table A

[0295] Table 111

[0296] Compounds of the formula I-A in which n is 1, R2 is 5-chlorine, R4 is ethyl and R6 is ethoxy and the combination of the radicals R1, R3 and R5 for a compound in each case corresponds to one row of Table A, where R1 is different from R3

[0297] Table 112

[0298] Compounds of the formula I-A in which n is 1, R2 is 3-bromine, R4 is ethyl and R6 is ethoxy and the combination of the radicals R1, R3 and R5 for a compound in each case corresponds to one row of Table A

[0299] Table 113

[0300] Compounds of the formula I-A in which n is 1, R2 is 5-bromine, R4 is ethyl and R6 is ethoxy and the combination of the radicals R1, R3 and R5 for a compound in each case corresponds to one row of Table A, where R1 is different from R3

[0301] Table 114

[0302] Compounds of the formula I-A in which n is 1, R2 is 3-iodine, R4 is ethyl and R6 is ethoxy and the combination of the radicals R1, R3 and R5 for a compound in each case corresponds to one row of Table A

[0303] Table 115

[0304] Compounds of the formula I-A in which n is 1, R2 is 5-iodine, R4 is ethyl and R6 is ethoxy and the combination of the radicals R1, R3 and R5 for a compound in each case corresponds to one row of Table A, where R1 is different from R3

[0305] Table 116

[0306] Compounds of the formula I-A in which n is 0, R4 is trifluoromethyl and R6 is ethoxy and the combination of the radicals R1, R3 and R5 for a compound in each case corresponds to one row of Table A

[0307] Table 117

[0308] Compounds of the formula I-A in which n is 1, R2 is 3-methyl, R4 is trifluoromethyl and R6 is ethoxy and the combination of the radicals R1, R3 and R5 for a compound in each case corresponds to one row of Table A

[0309] Table 118

[0310] Compounds of the formula I-A in which n is 1, R2 is 5-methyl, R4 is trifluoromethyl and R6 is ethoxy and the combination of the radicals R1, R3 and R5 for a compound in each case corresponds to one row of Table A, where R1 is different from R3

[0311] Table 119

[0312] Compounds of the formula I-A in which n is 1, R2 is 3-trifluoromethyl, R4 is trifluoromethyl and R6 is ethoxy and the combination of the radicals R1, R3 and R5 for a compound in each case corresponds to one row of Table A

[0313] Table 120

[0314] Compounds of the formula I-A in which n is 1, R2 is 5-trifluoromethyl, R4 is trifluoromethyl and R6 is ethoxy and the combination of the radicals R1, R3 and R5 for a compound in each case corresponds to one row of Table A, where R1 is different from R3

[0315] Table 121

[0316] Compounds of the formula I-A in which n is 1, R2 is 3-hydroxy, R4 is trifluoromethyl and R6 is ethoxy and the combination of the radicals R1, R3 and R5 for a compound in each case corresponds to one row of Table A

[0317] Table 122

[0318] Compounds of the formula I-A in which n is 1, R2 is 5-hydroxy, R4 is trifluoromethyl and R6 is ethoxy and the combination of the radicals R1 , R3 and R5 for a compound in each case corresponds to one row of Table A, where R1 is different from R3

[0319] Table 123

[0320] Compounds of the formula I-A in which n is 1, R2 is 3-methoxy, R4 is trifluoromethyl and R6 is ethoxy and the combination of the radicals R1, R3 and R5 for a compound in each case corresponds to one row of Table A

[0321] Table 124

[0322] Compounds of the formula I-A in which n is 1, R2 is 5-methoxy, R4 is trifluoromethyl and R6 is ethoxy and the combination of the radicals R1, R3 and R5 for a compound in each case corresponds to one row of Table A, where R1 is different from R3

[0323] Table 125

[0324] Compounds of the formula I-A in which n is 1, R2 is 3-ethoxy, R4 is trifluoromethyl and R6 is ethoxy and the combination of the radicals R1, R3 and R5 for a compound in each case corresponds to one row of Table A

[0325] Table 126

[0326] Compounds of the formula I-A in which n is 1, R2 is 5-ethoxy, R4 is trifluoromethyl and R6 is ethoxy and the combination of the radicals R1, R3 and R5 for a compound in each case corresponds to one row of Table A, where R1 is different from R3

[0327] Table 127

[0328] Compounds of the formula I-A in which n is 1, R2 is 3-difluoromethoxy, R4 is trifluoromethyl and R6 is ethoxy and the combination of the radicals R1, R3 and R5 for a compound in each case corresponds to one row of Table A

[0329] Table 128

[0330] Compounds of the formula I-A in which n is 1, R2 is 5-difluoromethoxy, R4 is trifluoromethyl and R6 is ethoxy and the combination of the radicals R1, R3 and R5 for a compound in each case corresponds to one row of Table A, where R1 is different from R3

[0331] Table 129

[0332] Compounds of the formula I-A in which n is 1, R2 is 3-chlorofluoromethoxy, R4 is trifluoromethyl and R6 is ethoxy and the combination of the radicals R1, R3 and R5 for a compound in each case corresponds to one row of Table A

[0333] Table 130

[0334] Compounds of the formula I-A in which n is 1, R2 is 5-chlorofluoromethoxy, R4 is trifluoromethyl and R6 is ethoxy and the combination of the radicals R1, R3 and R5 for a compound in each case corresponds to one row of Table A, where R1 is different from R3

[0335] Table 131

[0336] Compounds of the formula I-A in which n is 1, R2 is 3-fluorine, R4 is trifluoromethyl and R6 is ethoxy and the combination of the radicals R1, R3 and R5 for a compound in each case corresponds to one row of Table A

[0337] Table 132

[0338] Compounds of the formula I-A in which n is 1, R2 is 5-fluorine, R4 is trifluoromethyl and R6 is ethoxy and the combination of the radicals R1 , R3 and R5 for a compound in each case corresponds to one row of Table A, where R1 is different from R3

[0339] Table 133

[0340] Compounds of the formula I-A in which n is 1, R2 is 3-chlorine, R4 is trifluoromethyl and R6 is ethoxy and the combination of the radicals R1, R3 and R5 for a compound in each case corresponds to one row of Table A

[0341] Table 134

[0342] Compounds of the formula I-A in which n is 1, R2 is 5-chlorine, R4 is trifluoromethyl and R6 is ethoxy and the combination of the radicals R1 , R3 and R5 for a compound in each case corresponds to one row of Table A, where R1 is different from R3

[0343] Table 135

[0344] Compounds of the formula I-A in which n is 1, R2 is 3-bromine, R4 is trifluoromethyl and R6 is ethoxy and the combination of the radicals R1, R3 and R5 for a compound in each case corresponds to one row of Table A

[0345] Table 136

[0346] Compounds of the formula I-A in which n is 1, R2 is 5-bromine, R4 is trifluoromethyl and R6 is ethoxy and the combination of the radicals R1, R3 and R5 for a compound in each case corresponds to one row of Table A, where R1 is different from R3

[0347] Table 137

[0348] Compounds of the formula I-A in which n is 1, R2 is 3-iodine, R4 is trifluoromethyl and R6 is ethoxy and the combination of the radicals R1, R3 and R5 for a compound in each case corresponds to one row of Table A

[0349] Table 138

[0350] Compounds of the formula I-A in which n is 1, R2 is 5-iodine, R4 is trifluoromethyl and R6 is ethoxy and the combination of the radicals R1, R3 and R5 for a compound in each case corresponds to one row of Table A, where R1 is different from R3

TABLE A
3	I-A
No.	R1	R3	R5
A-1	CH3	CH3	OH
A-2	CH2CH3	CH3	OH
A-3	CF3	CH3	OH
A-4	F	CH3	OH
A-5	Cl	CH3	OH
A-6	Br	CH3	OH
A-7	I	CH3	OH
A-8	OH	CH3	OH
A-9	SH	CH3	OH
A-10	SCH3	CH3	OH
A-11	NH2	CH3	OH
A-12	OCH3	CH3	OH
A-13	OCHF2	CH3	OH
A-14	OCHFCl	CH3	OH
A-15	OCF3	CH3	OH
A-16	OC(═O)CH3	CH3	OH
A-17	OC(═O)CH2CH3	CH3	OH
A-18	CH2CH3	CH2CH3	OH
A-19	CF3	CH2CH3	OH
A-20	F	CH2CH3	OH
A-21	Cl	CH2CH3	OH
A-22	Br	CH2CH3	OH
A-23	I	CH2CH3	OH
A-24	OH	CH2CH3	OH
A-25	SH	CH2CH3	OH
A-26	SCH3	CH2CH3	OH
A-27	NH2	CH2CH3	OH
A-28	OCH3	CH2CH3	OH
A-29	OCHF2	CH2CH3	OH
A-30	OCHFCl	CH2CH3	OH
A-31	OCF3	CH2CH3	OH
A-32	OC(═O)CH3	CH2CH3	OH
A-33	OC(═O)CH2CH3	CH2CH3	OH
A-34	CF3	CF3	OH
A-35	F	CF3	OH
A-36	Cl	CF3	OH
A-37	Br	CF3	OH
A-38	I	CF3	OH
A-39	OH	CF3	OH
A-40	SH	CF3	OH
A-41	SCH3	CF3	OH
A-42	NH2	CF3	OH
A-43	OCH3	CF3	OH
A-44	OCHF2	CF3	OH
A-45	OCHFCl	CF3	OH
A-46	OCF3	CF3	OH
A-47	OC(═O)CH3	CF3	OH
A-48	OC(═O)CH2CH3	CF3	OH
A-49	F	F	OH
A-50	Cl	F	OH
A-51	Br	F	OH
A-52	I	F	OH
A-53	OH	F	OH
A-54	SH	F	OH
A-55	SCH3	F	OH
A-56	NH2	F	OH
A-57	OCH3	F	OH
A-58	OCHF2	F	OH
A-59	OCHFCl	F	OH
A-60	OCF3	F	OH
A-61	OC(═O)CH3	F	OH
A-62	OC(═O)CH2CH3	F	OH
A-63	Cl	Cl	OH
A-64	Br	Cl	OH
A-65	I	Cl	OH
A-66	OH	Cl	OH
A-67	SH	Cl	OH
A-68	SCH3	Cl	OH
A-69	NH2	Cl	OH
A-70	OCH3	Cl	OH
A-71	OCHF2	Cl	OH
A-72	OCHFCl	Cl	OH
A-73	OCF3	Cl	OH
A-74	OC(═O)CH3	Cl	OH
A-75	OC(═O)CH2CH3	Cl	OH
A-76	Br	Br	OH
A-77	I	Br	OH
A-78	OH	Br	OH
A-79	SH	Br	OH
A-80	SCH3	Br	OH
A-81	NH2	Br	OH
A-82	OCH3	Br	OH
A-83	OCHF2	Br	OH
A-84	OCHFCl	Br	OH
A-85	OCF3	Br	OH
A-86	OC(═O)CH3	Br	OH
A-87	OC(═O)CH2CH3	Br	OH
A-88	I	I	OH
A-89	OH	I	OH
A-90	SH	I	OH
A-91	SCH3	I	OH
A-92	NH2	I	OH
A-93	OCH3	I	OH
A-94	OCHF2	I	OH
A-95	OCHFCl	I	OH
A-96	OCF3	I	OH
A-97	OC(═O)CH3	I	OH
A-98	OC(═O)CH2CH3	I	OH
A-99	OH	OH	OH
A-100	SH	OH	OH
A-101	SCH3	OH	OH
A-102	NH2	OH	OH
A-103	OCH3	OH	OH
A-104	OCHF2	OH	OH
A-105	OCHFCl	OH	OH
A-106	OCF3	OH	OH
A-107	OC(═O)CH3	OH	OH
A-108	OC(═O)CH2CH3	OH	OH
A-109	SH	SH	OH
A-110	SCH3	SH	OH
A-111	NH2	SH	OH
A-112	OCH3	SH	OH
A-113	OCHF2	SH	OH
A-114	OCHFCl	SH	OH
A-115	OCF3	SH	OH
A-116	OC(═O)CH3	SH	OH
A-117	OC(═O)CH2CH3	SH	OH
A-118	SCH3	SCH3	OH
A-119	NH2	SCH3	OH
A-120	OCH3	SCH3	OH
A-121	OCHF2	SCH3	OH
A-122	OCHFCl	SCH3	OH
A-123	OCF3	SCH3	OH
A-124	OC(═O)CH3	SCH3	OH
A-125	OC(═O)CH2CH3	SCH3	OH
A-126	NH2	NH2	OH
A-127	OCH3	NH2	OH
A-128	OCHF2	NH2	OH
A-129	OCHFCl	NH2	OH
A-130	OCF3	NH2	OH
A-131	OC(═O)CH3	NH2	OH
A-132	OC(═O)CH2CH3	NH2	OH
A-133	OCH3	OCH3	OH
A-134	OCHF2	OCH3	OH
A-135	OCHFCl	OCH3	OH
A-136	OCF3	OCH3	OH
A-137	OC(═O)CH3	OCH3	OH
A-138	OC(═O)CH2CH3	OCH3	OH
A-139	OCHF2	OCHF2	OH
A-140	OCHFCl	OCHF2	OH
A-141	OCF3	OCHF2	OH
A-142	OC(═O)CH3	OCHF2	OH
A-143	OC(═O)CH2CH3	OCHF2	OH
A-144	OCHFCl	OCHFCl	OH
A-145	OCF3	OCHFCl	OH
A-146	OC(═O)CH3	OCHFCl	OH
A-147	OC(═O)CH2CH3	OCHFCl	OH
A-148	OCF3	OCF3	OH
A-149	OC(═O)CH3	OCF3	OH
A-150	OC(═O)CH2CH3	OCF3	OH
A-151	OC(═O)CH3	OC(═O)CH3	OH
A-152	OC(═O)CH2CH3	OC(═O)CH3	OH
A-153	OC(═O)CH2CH3	OC(═O)CH2CH3	OH
A-154	CH3	CH3	OCH3
A-155	CH2CH3	CH3	OCH3
A-156	CF3	CH3	OCH3
A-157	F	CH3	OCH3
A-158	Cl	CH3	OCH3
A-159	Br	CH3	OCH3
A-160	I	CH3	OCH3
A-161	OH	CH3	OCH3
A-162	SH	CH3	OCH3
A-163	SCH3	CH3	OCH3
A-164	NH2	CH3	OCH3
A-165	OCH3	CH3	OCH3
A-166	OCHF2	CH3	OCH3
A-167	OCHFCl	CH3	OCH3
A-168	OCF3	CH3	OCH3
A-169	OC(═O)CH3	CH3	OCH3
A-170	OC(═O)CH2CH3	CH3	OCH3
A-171	CH2CH3	CH2CH3	OCH3
A-172	CF3	CH2CH3	OCH3
A-173	F	CH2CH3	OCH3
A-174	Cl	CH2CH3	OCH3
A-175	Br	CH2CH3	OCH3
A-176	I	CH2CH3	OCH3
A-177	OH	CH2CH3	OCH3
A-178	SH	CH2CH3	OCH3
A-179	SCH3	CH2CH3	OCH3
A-180	NH2	CH2CH3	OCH3
A-181	OCH3	CH2CH3	OCH3
A-182	OCHF2	CH2CH3	OCH3
A-183	OCHFCl	CH2CH3	OCH3
A-184	OCF3	CH2CH3	OCH3
A-185	OC(═O)CH3	CH2CH3	OCH3
A-186	OC(═O)CH2CH3	CH2CH3	OCH3
A-187	CF3	CF3	OCH3
A-188	F	CF3	OCH3
A-189	Cl	CF3	OCH3
A-190	Br	CF3	OCH3
A-191	I	CF3	OCH3
A-192	OH	CF3	OCH3
A-193	SH	CF3	OCH3
A-194	SCH3	CF3	OCH3
A-195	NH2	CF3	OCH3
A-196	OCH3	CF3	OCH3
A-197	OCHF2	CF3	OCH3
A-198	OCHFCl	CF3	OCH3
A-199	OCF3	CF3	OCH3
A-200	OC(═O)CH3	CF3	OCH3
A-201	OC(═O)CH2CH3	CF3	OCH3
A-202	F	F	OCH3
A-203	Cl	F	OCH3
A-204	Br	F	OCH3
A-205	I	F	OCH3
A-206	OH	F	OCH3
A-207	SH	F	OCH3
A-208	SCH3	F	OCH3
A-209	NH2	F	OCH3
A-210	OCH3	F	OCH3
A-211	OCHF2	F	OCH3
A-212	OCHFCl	F	OCH3
A-213	OCF3	F	OCH3
A-214	OC(═O)CH3	F	OCH3
A-215	OC(═O)CH2CH3	F	OCH3
A-216	Cl	Cl	OCH3
A-217	Br	Cl	OCH3
A-218	I	Cl	OCH3
A-219	OH	Cl	OCH3
A-220	SH	Cl	OCH3
A-221	SCH3	Cl	OCH3
A-222	NH2	Cl	OCH3
A-223	OCH3	Cl	OCH3
A-224	OCHF2	Cl	OCH3
A-225	OCHFCl	Cl	OCH3
A-226	OCF3	Cl	OCH3
A-227	OC(═O)CH3	Cl	OCH3
A-228	OC(═O)CH2CH3	Cl	OCH3
A-229	Br	Br	OCH3
A-230	I	Br	OCH3
A-231	OH	Br	OCH3
A-232	SH	Br	OCH3
A-233	SCH3	Br	OCH3
A-234	NH2	Br	OCH3
A-235	OCH3	Br	OCH3
A-236	OCHF2	Br	OCH3
A-237	OCHFCl	Br	OCH3
A-238	OCF3	Br	OCH3
A-239	OC(═O)CH3	Br	OCH3
A-240	OC(═O)CH2CH3	Br	OCH3
A-241	I	I	OCH3
A-242	OH	I	OCH3
A-243	SH	I	OCH3
A-244	SCH3	I	OCH3
A-245	NH2	I	OCH3
A-246	OCH3	I	OCH3
A-247	OCHF2	I	OCH3
A-248	OCHFCl	I	OCH3
A-249	OCF3	I	OCH3
A-250	OC(═O)CH3	I	OCH3
A-251	OC(═O)CH2CH3	I	OCH3
A-252	OH	OH	OCH3
A-253	SH	OH	OCH3
A-254	SCH3	OH	OCH3
A-255	NH2	OH	OCH3
A-256	OCH3	OH	OCH3
A-257	OCHF2	OH	OCH3
A-258	OCHFCl	OH	OCH3
A-259	OCF3	OH	OCH3
A-260	OC(═O)CH3	OH	OCH3
A-261	OC(═O)CH2CH3	OH	OCH3
A-262	SH	SH	OCH3
A-263	SCH3	SH	OCH3
A-264	NH2	SH	OCH3
A-265	OCH3	SH	OCH3
A-266	OCHF2	SH	OCH3
A-267	OCHFCl	SH	OCH3
A-268	OCF3	SH	OCH3
A-269	OC(═O)CH3	SH	OCH3
A-270	OC(═O)CH2CH3	SH	OCH3
A-271	SCH3	SCH3	OCH3
A-272	NH2	SCH3	OCH3
A-273	OCH3	SCH3	OCH3
A-274	OCHF2	SCH3	OCH3
A-275	OCHFCl	SCH3	OCH3
A-276	OCF3	SCH3	OCH3
A-277	OC(═O)CH3	SCH3	OCH3
A-278	OC(═O)CH2CH3	SCH3	OCH3
A-279	NH2	NH2	OCH3
A-280	OCH3	NH2	OCH3
A-281	OCHF2	NH2	OCH3
A-282	OCHFCl	NH2	OCH3
A-283	OCF3	NH2	OCH3
A-284	OC(═O)CH3	NH2	OCH3
A-285	OC(═O)CH2CH3	NH2	OCH3
A-286	OCH3	OCH3	OCH3
A-287	OCHF2	OCH3	OCH3
A-288	OCHFCl	OCH3	OCH3
A-289	OCF3	OCH3	OCH3
A-290	OC(═O)CH3	OCH3	OCH3
A-291	OC(═O)CH2CH3	OCH3	OCH3
A-292	OCHF2	OCHF2	OCH3
A-293	OCHFCl	OCHF2	OCH3
A-294	OCF3	OCHF2	OCH3
A-295	OC(═O)CH3	OCHF2	OCH3
A-296	OC(═O)CH2CH3	OCHF2	OCH3
A-297	OCHFCl	OCHFCl	OCH3
A-298	OCF3	OCHFCl	OCH3
A-299	OC(═O)CH3	OCHFCl	OCH3
A-300	OC(═O)CH2CH3	OCHFCl	OCH3
A-301	OCF3	OCF3	OCH3
A-302	OC(═O)CH3	OCF3	OCH3
A-303	OC(═O)CH2CH3	OCF3	OCH3
A-304	OC(═O)CH3	OC(═O)CH3	OCH3
A-305	OC(═O)CH2CH3	OC(═O)CH3	OCH3
A-306	OC(═O)CH2CH3	OC(═O)CH2CH3	OCH3
A-307	CH3	CH3	OCH2CH3
A-308	CH2CH3	CH3	OCH2CH3
A-309	CF3	CH3	OCH2CH3
A-310	F	CH3	OCH2CH3
A-311	Cl	CH3	OCH2CH3
A-312	Br	CH3	OCH2CH3
A-313	I	CH3	OCH2CH3
A-314	OH	CH3	OCH2CH3
A-315	SH	CH3	OCH2CH3
A-316	SCH3	CH3	OCH2CH3
A-317	NH2	CH3	OCH2CH3
A-318	OCH3	CH3	OCH2CH3
A-319	OCHF2	CH3	OCH2CH3
A-320	OCHFCl	CH3	OCH2CH3
A-321	OCF3	CH3	OCH2CH3
A-322	OC(═O)CH3	CH3	OCH2CH3
A-323	OC(═O)CH2CH3	CH3	OCH2CH3
A-324	CH2CH3	CH2CH3	OCH2CH3
A-325	CF3	CH2CH3	OCH2CH3
A-326	F	CH2CH3	OCH2CH3
A-327	Cl	CH2CH3	OCH2CH3
A-328	Br	CH2CH3	OCH2CH3
A-329	I	CH2CH3	OCH2CH3
A-330	OH	CH2CH3	OCH2CH3
A-331	SH	CH2CH3	OCH2CH3
A-332	SCH3	CH2CH3	OCH2CH3
A-333	NH2	CH2CH3	OCH2CH3
A-334	OCH3	CH2CH3	OCH2CH3
A-335	OCHF2	CH2CH3	OCH2CH3
A-336	OCHFCl	CH2CH3	OCH2CH3
A-337	OCF3	CH2CH3	OCH2CH3
A-338	OC(═O)CH3	CH2CH3	OCH2CH3
A-339	OC(═O)CH2CH3	CH2CH3	OCH2CH3
A-340	CF3	CF3	OCH2CH3
A-341	F	CF3	OCH2CH3
A-342	Cl	CF3	OCH2CH3
A-343	Br	CF3	OCH2CH3
A-344	I	CF3	OCH2CH3
A-345	OH	CF3	OCH2CH3
A-346	SH	CF3	OCH2CH3
A-347	SCH3	CF3	OCH2CH3
A-348	NH2	CF3	OCH2CH3
A-349	OCH3	CF3	OCH2CH3
A-350	OCHF2	CF3	OCH2CH3
A-351	OCHFCl	CF3	OCH2CH3
A-352	OCF3	CF3	OCH2CH3
A-353	OC(═O)CH3	CF3	OCH2CH3
A-354	OC(═O)CH2CH3	CF3	OCH2CH3
A-355	F	F	OCH2CH3
A-356	Cl	F	OCH2CH3
A-357	Br	F	OCH2CH3
A-358	I	F	OCH2CH3
A-359	OH	F	OCH2CH3
A-360	SH	F	OCH2CH3
A-361	SCH3	F	OCH2CH3
A-362	NH2	F	OCH2CH3
A-363	OCH3	F	OCH2CH3
A-364	OCHF2	F	OCH2CH3
A-365	OCHFCl	F	OCH2CH3
A-366	OCF3	F	OCH2CH3
A-367	OC(═O)CH3	F	OCH2CH3
A-368	OC(═O)CH2CH3	F	OCH2CH3
A-369	Cl	Cl	OCH2CH3
A-370	Br	Cl	OCH2CH3
A-37l	I	Cl	OCH2CH3
A-372	OH	Cl	OCH2CH3
A-373	SH	Cl	OCH2CH3
A-374	SCH3	Cl	OCH2CH3
A-375	NH2	Cl	OCH2CH3
A-376	OCH3	Cl	OCH2CH3
A-377	OCHF2	Cl	OCH2CH3
A-378	OCHFCl	Cl	OCH2CH3
A-379	OCF3	Cl	OCH2CH3
A-380	OC(═O)CH3	Cl	OCH2CH3
A-381	OC(═O)CH2CH3	Cl	OCH2CH3
A-382	Br	Br	OCH2CH3
A-383	I	Br	OCH2CH3
A-384	OH	Br	OCH2CH3
A-385	SH	Br	OCH2CH3
A-386	SCH3	Br	OCH2CH3
A-387	NH2	Br	OCH2CH3
A-388	OCH3	Br	OCH2CH3
A-389	OCHF2	Br	OCH2CH3
A-390	OCHFCl	Br	OCH2CH3
A-391	OCF3	Br	OCH2CH3
A-392	OC(═O)CH3	Br	OCH2CH3
A-393	OC(═O)CH2CH3	Br	OCH2CH3
A-394	I	I	OCH2CH3
A-395	OH	I	OCH2CH3
A-396	SH	I	OCH2CH3
A-397	SCH3	I	OCH2CH3
A-398	NH2	I	OCH2CH3
A-399	OCH3	I	OCH2CH3
A-400	OCHF2	I	0CH2CH3
A-401	OCHFCl	I	OCH2CH3
A-402	OCF3	I	OCH2CH3
A-403	OC(═O)CH3	I	OCH2CH3
A-404	OC(═O)CH2CH3	I	OCH2CH3
A-405	OH	OH	OCH2CH3
A-406	SH	OH	OCH2CH3
A-407	SCH3	OH	OCH2CH3
A-408	NH2	OH	OCH2CH3
A-409	OCH3	OH	OCH2CH3
A-410	OCHF2	OH	OCH2CH3
A-411	OCHFCl	OH	OCH2CH3
A-412	OCF3	OH	OCH2CH3
A-413	OC(═O)CH3	OH	OCH2CH3
A-414	OC(═O)CH2CH3	OH	OCH2CH3
A-415	SH	SH	OCH2CH3
A-416	SCH3	SH	OCH2CH3
A-417	NH2	SH	OCH2CH3
A-418	OCH3	SH	OCH2CH3
A-419	OCHF2	SH	OCH2CH3
A-420	OCHFCl	SH	OCH2CH3
A-421	OCF3	SH	OCH2CH3
A-422	OC(═O)CH3	SH	OCH2CH3
A-423	OC(═O)CH2CH3	SH	OCH2CH3
A-424	SCH3	SCH3	OCH2CH3
A-425	NH2	SCH3	OCH2CH3
A-426	OCH3	SCH3	OCH2CH3
A-427	OCHF2	SCH3	OCH2CH3
A-428	OCHFCl	SCH3	OCH2CH3
A-429	OCF3	SCH3	OCH2CH3
A-430	OC(═O)CH3	SCH3	OCH2CH3
A-431	OC(═O)CH2CH3	SCH3	OCH2CH3
A-432	NH2	NH2	OCH2CH3
A-433	OCH3	NH2	OCH2CH3
A-434	OCHF2	NH2	OCH2CH3
A-435	OCHFCl	NH2	OCH2CH3
A-436	OCF3	NH2	OCH2CH3
A-437	OC(═O)CH3	NH2	OCH2CH3
A-438	OC(═O)CH2CH3	NH2	OCH2CH3
A-439	OCH3	OCH3	OCH2CH3
A-440	OCHF2	OCH3	OCH2CH3
A-441	OCHFCl	OCH3	OCH2CH3
A-442	OCF3	OCH3	OCH2CH3
A-443	OC(═O)CH3	OCH3	OCH2CH3
A-444	OC(═O)CH2CH3	OCH3	OCH2CH3
A-445	OCHF2	OCHF2	OCH2CH3
A-446	OCHFCl	OCHF2	OCH2CH3
A-447	OCF3	OCHF2	OCH2CH3
A-448	OC(═O)CH3	OCHF2	OCH2CH3
A-449	OC(═O)CH2CH3	OCHF2	OCH2CH3
A-450	OCHFCl	OCHFCl	OCH2CH3
A-451	OCF3	OCHFCl	OCH2CH3
A-452	OC(═O)CH3	OCHFCl	OCH2CH3
A-453	OC(═O)CH2CH3	OCHFCl	OCH2CH3
A-454	OCF3	OCF3	OCH2CH3
A-455	OC(═O)CH3	OCF3	OCH2CH3
A-456	OC(═O)CH2CH3	OCF3	OCH2CH3
A-457	OC(═O)CH3	OC(═O)CH3	OCH2CH3
A-458	OC(═O) CH2CH3	OC(═O)CH3	OCH2CH3
A-459	OC(═O)CH2CH3	OC(═O)CH2CH3	OCH2CH3
A-460	CH3	CH3	OCH2CH2CH3
A-461	CH2CH3	CH3	OCH2CH2CH3
A-462	CF3	CH3	OCH2CH2CH3
A-463	F	CH3	OCH2CH2CH3
A-464	Cl	CH3	OCH2CH2CH3
A-465	Br	CH3	OCH2CH2CH3
A-466	I	CH3	OCH2CH2CH3
A-467	OH	CH3	OCH2CH2CH3
A-468	SH	CH3	OCH2CH2CH3
A-469	SCH3	CH3	OCH2CH2CH3
A-470	NH2	CH3	OCH2CH2CH3
A-471	OCH3	CH3	OCH2CH2CH3
A-472	OCHF2	CH3	OCH2CH2CH3
A-473	OCHFCl	CH3	OCH2CH2CH3
A-474	OCF3	CH3	OCH2CH2CH3
A-475	OC(═O)CH3	CH3	OCH2CH2CH3
A-476	OC(═O)CH2CH3	CH3	OCH2CH2CH3
A-477	CH2CH3	CH2CH3	OCH2CH2CH3
A-478	CF3	CH2CH3	OCH2CH2CH3
A-479	F	CH2CH3	OCH2CH2CH3
A-480	Cl	CH2CH3	OCH2CH2CH3
A-481	Br	CH2CH3	OCH2CH2CH3
A-482	I	CH2CH3	OCH2CH2CH3
A-483	OH	CH2CH3	OCH2CH2CH3
A-484	SH	CH2CH3	OCH2CH2CH3
A-485	SCH3	CH2CH3	OCH2CH2CH3
A-486	NH2	CH2CH3	OCH2CH2CH3
A-487	OCH3	CH2CH3	OCH2CH2CH3
A-488	OCHF2	CH2CH3	OCH2CH2CH3
A-489	OCHFCl	CH2CH3	OCH2CH2CH3
A-490	OCF3	CH2CH3	OCH2CH2CH3
A-491	OC(═O)CH3	CH2CH3	OCH2CH2CH3
A-492	OC(═O)CH2CH3	CH2CH3	OCH2CH2CH3
A-493	CF3	CF3	OCH2CH2CH3
A-494	F	CF3	OCH2CH2CH3
A-495	Cl	CF3	OCH2CH2CH3
A-496	Br	CF3	OCH2CH2CH3
A-497	I	CF3	OCH2CH2CH3
A-498	OH	CF3	OCH2CH2CH3
A-499	SH	CF3	OCH2CH2CH3
A-500	SCH3	CF3	OCH2CH2CH3
A-501	NH2	CF3	OCH2CH2CH3
A-502	OCH3	CF3	OCH2CH2CH3
A-503	OCHF2	CF3	OCH2CH2CH3
A-504	OCHFCl	CF3	OCH2CH2CH3
A-505	OCF3	CF3	OCH2CH2CH3
A-506	OC(═O)CH3	CF3	OCH2CH2CH3
A-507	OC(═O)CH2CH3	CF3	OCH2CH2CH3
A-508	F	F	OCH2CH2CH3
A-509	Cl	F	OCH2CH2CH3
A-510	Br	F	OCH2CH2CH3
A-511	I	F	OCH2CH2CH3
A-512	OH	F	OCH2CH2CH3
A-513	SH	F	OCH2CH2CH3
A-514	SCH3	F	OCH2CH2CH3
A-515	NH2	F	OCH2CH2CH3
A-516	OCH3	F	OCH2CH2CH3
A-517	OCHF2	F	OCH2CH2CH3
A-518	OCHFCl	F	OCH2CH2CH3
A-519	OCF3	F	OCH2CH2CH3
A-520	OC(═O)CH3	F	OCH2CH2CH3
A-521	OC(═O)CH2CH3	F	OCH2CH2CH3
A-522	Cl	Cl	OCH2CH2CH3
A-523	Br	Cl	OCH2CH2CH3
A-524	I	Cl	OCH2CH2CH3
A-525	OH	Cl	OCH2CH2CH3
A-526	SH	Cl	OCH2CH2CH3
A-527	SCH3	Cl	OCH2CH2CH3
A-528	NH2	Cl	OCH2CH2CH3
A-529	OCH3	Cl	OCH2CH2CH3
A-530	OCHF2	Cl	OCH2CH2CH3
A-531	OCHFCl	Cl	OCH2CH2CH3
A-532	OCF3	Cl	OCH2CH2CH3
A-533	OC(═O)CH3	Cl	OCH2CH2CH3
A-534	OC(═O)CH2CH3	Cl	OCH2CH2CH3
A-535	Br	Br	OCH2CH2CH3
A-536	I	Br	OCH2CH2CH3
A-537	OH	Br	OCH2CH2CH3
A-538	SH	Br	OCH2CH2CH3
A-539	SCH3	Br	OCH2CH2CH3
A-540	NH2	Br	OCH2CH2CH3
A-541	OCH3	Br	OCH2CH2CH3
A-542	OCHF2	Br	OCH2CH2CH3
A-543	OCHFCl	Br	OCH2CH2CH3
A-544	OCF3	Br	OCH2CH2CH3
A-545	OC(═O)CH3	Br	OCH2CH2CH3
A-546	OC(═O)CH2CH3	Br	OCH2CH2CH3
A-547	I	I	OCH2CH2CH3
A-548	OH	I	OCH2CH2CH3
A-549	SH	I	OCH2CH2CH3
A-550	SCH3	I	OCH2CH2CH3
A-551	NH2	I	OCH2CH2CH3
A-552	OCH3	I	OCH2CH2CH3
A-553	OCHF2	I	OCH2CH2CH3
A-554	OCHFCl	I	OCH2CH2CH3
A-555	OCF3	I	OCH2CH2CH3
A-556	OC(═O)CH3	I	OCH2CH2CH3
A-557	OC(═O)CH2CH3	I	OCH2CH2CH3
A-558	OH	OH	OCH2CH2CH2
A-559	SH	OH	OCH2CH2CH3
A-560	SCH3	OH	OCH2CH2CH3
A-561	NH2	OH	OCH2CH2CH3
A-562	OCH3	OH	OCH2CH2CH3
A-563	OCHF2	OH	OCH2CH2CH3
A-564	OCHFCl	OH	OCH2CH2CH3
A-565	OCF3	OH	OCH2CH2CH3
A-566	OC(═O)CH3	OH	OCH2CH2CH3
A-567	OC(═O)CH2CH3	OH	OCH2CH2CH3
A-568	SH	SH	OCH2CH2CH3
A-569	SCH3	SH	OCH2CH2CH3
A-570	NH2	SH	OCH2CH2CH3
A-571	OCH3	SH	OCH2CH2CH3
A-572	OCHF2	SH	OCH2CH2CH3
A-573	OCHFCl	SH	OCH2CH2CH3
A-574	OCF3	SH	OCH2CH2CH3
A-575	OC(═O)CH3	SH	OCH2CH2CH3
A-576	OC(═O)CH2CH3	SH	OCH2CH2CH3
A-577	SCH3	SCH3	OCH2CH2CH3
A-578	NH2	SCH3	OCH2CH2CH3
A-579	OCH3	SCH3	OCH2CH2CH3
A-580	OCHF2	SCH3	OCH2CH2CH3
A-581	OCHFCl	SCH3	OCH2CH2CH3
A-582	OCF3	SCH3	OCH2CH2CH3
A-583	OC(═O)CH3	SCH3	OCH2CH2CH3
A-584	OC(═O)CH2CH3	SCH3	OCH2CH2CH3
A-585	NH2	NH2	OCH2CH2CH3
A-586	OCH3	NH2	OCH2CH2CH3
A-587	OCHF2	NH2	OCH2CH2CH3
A-588	OCHFCl	NH2	OCH2CH2CH3
A-589	OCF3	NH2	OCH2CH2CH3
A-590	OC(═O)CH3	NH2	OCH2CH2CH3
A-591	OC(═O)CH2CH3	NH2	OCH2CH2CH3
A-592	OCH3	OCH3	OCH2CH2CH3
A-593	OCHF2	OCH3	OCH2CH2CH3
A-594	OCHFCl	OCH3	OCH2CH2CH3
A-595	OCF3	OCH3	OCH2CH2CH3
A-596	OC(═O)CH3	OCH3	OCH2CH2CH3
A-597	OC(═O)CH2CH3	OCH3	OCH2CH2CH3
A-598	OCHF2	OCHF2	OCH2CH2CH3
A-599	OCHFCl	OCHF2	OCH2CH2CH3
A-600	OCF3	OCHF2	OCH2CH2CH3
A-601	OC(═O)CH3	OCHF2	OCH2CH2CH3
A-602	OC(═O)CH2CH3	OCHF2	OCH2CH2CH3
A-603	OCHFCl	OCHFCl	OCH2CH2CH3
A-604	OCF3	OCHFCl	OCH2CH2CH3
A-605	OC(═O)CH3	OCHFCl	OCH2CH2CH3
A-606	OC(═O)CH2CH3	OCHFCl	OCH2CH2CH3
A-607	OCF3	OCF3	OCH2CH2CH3
A-608	OC(═O)CH3	OCF3	OCH2CH2CH3
A-609	OC(═O)CH2CH3	OCF3	OCH2CH2CH3
A-610	OC(═O)CH3	OC(═O)CH3	OCH2CH2CH3
A-611	OC(═O)CH2CH3	OC(═O)CH3	OCH2CH2CH3
A-612	OC(═O)CH2CH3	OC(═O)CH2CH3	OCH2CH2CH3
A-613	CH3	CH3	OCH(CH3)2
A-614	CH2CH3	CH3	OCH(CH3)2
A-615	CF3	CH3	OCH(CH3)2
A-616	F	CH3	OCH(CH3)2
A-617	Cl	CH3	OCH(CH3)2
A-618	Br	CH3	OCH(CH3)2
A-619	I	CH3	OCH(CH3)2
A-620	OH	CH3	OCH(CH3)2
A-621	SH	CH3	OCH(CH3)2
A-622	SCH3	CH3	OCH(CH3)2
A-623	NH2	CH3	OCH(CH3)2
A-624	OCH3	CH3	OCH(CH3)2
A-625	OCHF2	CH3	OCH(CH3)2
A-626	OCHFCl	CH3	OCH(CH3)2
A-627	OCF3	CH3	OCH(CH3)2
A-628	OC(═O)CH3	CH3	OCH(CH3)2
A-629	OC(═O)CH2CH3	CH3	OCH(CH3)2
A-630	CH2CH3	CH2CH3	OCH(CH3)2
A-631	CF3	CH2CH3	OCH(CH3)2
A-632	F	CH2CH3	OCH(CH3)2
A-633	Cl	CH2CH3	OCH(CH3)2
A-634	Br	CH2CH3	OCH(CH3)2
A-635	I	CH2CH3	OCH(CH3)2
A-636	OH	CH2CH3	OCH(CH3)2
A-637	SH	CH2CH3	OCH(CH3)2
A-638	SCH3	CH2CH3	OCH(CH3)2
A-639	NH2	CH2CH3	OCH(CH3)2
A-640	OCH3	CH2CH3	OCH(CH3)2
A-641	OCHF2	CH2CH3	OCH(CH3)2
A-642	OCHFCl	CH2CH3	OCH(CH3)2
A-643	OCF3	CH2CH3	OCH(CH3)2
A-644	OC(═O)CH3	CH2CH3	OCH(CH3)2
A-645	OC(═O)CH2CH3	CH2CH3	OCH(CH3)2
A-646	CF3	CF3	OCH(CH3)2
A-647	F	CF3	OCH(CH3)2
A-648	Cl	CF3	OCH(CH3)2
A-649	Br	CF3	OCH(CH3)2
A-650	I	CF3	OCH(CH3)2
A-651	OH	CF3	OCH(CH3)2
A-652	SH	CF3	OCH(CH3)2
A-653	SCH3	CF3	OCH(CH3)2
A-654	NH2	CF3	OCH(CH3)2
A-655	OCH3	CF3	OCH(CH3)2
A-656	OCHF2	CF3	OCH(CH3)2
A-657	OCHFCl	CF3	OCH(CH3)2
A-658	OCF3	CF3	OCH(CH3)2
A-659	OC(═O)CH3	CF3	OCH(CH3)2
A-660	OC(═O)CH2CH3	CF3	OCH(CH3)2
A-661	F	F	OCH(CH3)2
A-662	Cl	F	OCH(CH3)2
A-663	Br	F	OCH(CH3)2
A-664	I	F	OCH(CH3)2
A-665	OH	F	OCH(CH3)2
A-666	SH	F	OCH(CH3)2
A-667	SCH3	F	OCH(CH3)2
A-668	NH2	F	OCH(CH3)2
A-659	OCH3	F	OCH(CH3)2
A-670	OCHF2	F	OCH(CH3)2
A-671	OCHFCl	F	OCH(CH3)2
A-672	OCF3	F	OCH(CH3)2
A-673	OC(═O)CH3	F	OCH(CH3)2
A-674	OC(═O)CH2CH3	F	OCH(CH3)2
A-675	Cl	Cl	OCH(CH3)2
A-676	Br	Cl	OCH(CH3)2
A-677	I	Cl	OCH(CH3)2
A-678	OH	Cl	OCH(CH3)2
A-679	SH	Cl	OCH(CH3)2
A-680	SCH3	Cl	OCH(CH3)2
A-681	NH2	Cl	OCH(CH3)2
A-682	OCH3	Cl	OCH(CH3)2
A-683	OCHF2	Cl	OCH(CH3)2
A-684	OCHFCl	Cl	OCH(CH3)2
A-685	OCF3	Cl	OCH(CH3)2
A-686	OC(═O)CH3	Cl	OCH(CH3)2
A-687	OC(═O)CH2CH3	Cl	OCH(CH3)2
A-688	Br	Br	OCH(CH3)2
A-689	I	Br	OCH(CH3)2
A-690	OH	Br	OCH(CH3)2
A-69l	SH	Br	OCH(CH3)2
A-692	SCH3	Br	OCH(CH3)2
A-693	NH2	Br	OCH(CH3)2
A-694	OCH3	Br	OCH(CH3)2
A-695	OCHF2	Br	OCH(CH3)2
A-696	OCHFCl	Br	OCH(CH3)2
A-697	OCF3	Br	OCH(CH3)2
A-698	OC(═O)CH3	Br	OCH(CH3)2
A-699	OC(═O)CH2CH3	Br	OCH(CH3)2
A-700	I	I	OCH(CH3)2
A-701	OH	I	OCH(CH3)2
A-702	SH	I	OCH(CH3)2
A-703	SCH3	I	OCH(CH3)2
A-704	NH2	I	OCH(CH3)2
A-705	OCH3	I	OCH(CH3)2
A-706	OCHF2	I	OCH(CH3)2
A-707	OCHFCl	I	OCH(CH3)2
A-708	OCF3	I	OCH(CH3)2
A-709	OC(═O)CH3	I	OCH(CH3)2
A-710	OC(═O)CH2CH3	I	OCH(CH3)2
A-711	OH	OH	OCH(CH3)2
A-712	SH	OH	OCH(CH3)2
A-713	SCH3	OH	OCH(CH3)2
A-714	NH2	OH	OCH(CH3)2
A-715	OCH3	OH	OCH(CH3)2
A-716	OCHF2	OH	OCH(CH3)2
A-717	OCHFCl	OH	OCH(CH3)2
A-718	OCF3	OH	OCH(CH3)2
A-719	OC(═O)CH3	OH	OCH(CH3)2
A-720	OC(═O)CH2CH3	OH	OCH(CH3)2
A-721	SH	SH	OCH(CH3)2
A-722	SCH3	SH	OCH(CH3)2
A-723	NH2	SH	OCH(CH3)2
A-724	OCH3	SH	OCH(CH3)2
A-725	OCHF2	SH	OCH(CH3)2
A-726	OCHFCl	SH	OCH(CH3)2
A-727	OCF3	SH	OCH(CH3)2
A-728	OC(═O)CH3	SH	OCH(CH3)2
A-729	OC(═O)CH2CH3	SH	OCH(CH3)2
A-730	SCH3	SCH3	OCH(CH3)2
A-731	NH2	SCH3	OCH(CH3)2
A-732	OCH3	SCH3	OCH(CH3)2
A-733	OCHF2	SCH3	OCH(CH3)2
A-734	OCHFCl	SCH3	OCH(CH3)2
A-735	OCF3	SCH3	OCH(CH3)2
A-736	OC(═O)CH3	SCH3	OCH(CH3)2
A-737	OC(═O)CH2CH3	SCH3	OCH(CH3)2
A-738	NH2	NH2	OCH(CH3)2
A-739	OCH3	NH2	OCH(CH3)2
A-740	OCHF2	NH2	OCH(CH3)2
A-741	OCHFCl	NH2	OCH(CH3)2
A-742	OCF3	NH2	OCH(CH3)2
A-743	OC(═O)CH3	NH2	OCH(CH3)2
A-744	OC(═O)CH2CH3	NH2	OCH(CH3)2
A-745	OCH3	OCH3	OCH(CH3)2
A-746	OCHF2	OCH3	OCH(CH3)2
A-747	OCHFCl	OCH3	OCH(CH3)2
A-748	OCF3	OCH3	OCH(CH3)2
A-749	OC(═O)CH3	OCH3	OCH(CH3)2
A-750	OC(═O)CH2CH3	OCH3	OCH(CH3)2
A-751	OCHF2	OCHF2	OCH(CH3)2
A-752	OCHFCl	OCHF2	OCH(CH3)2
A-753	OCF3	OCHF2	OCH(CH3)2
A-754	OC(═O)CH3	OCHF2	OCH(CH3)2
A-755	OC(═O)CH2CH3	OCHF2	OCH(CH3)2
A-756	OCHFCl	OCHFCl	OCH(CH3)2
A-757	OCF3	OCHFCl	OCH(CH3)2
A-758	OC(═O)CH3	OCHFCl	OCH(CH3)2
A-759	OC(═O)CH2CH3	OCHFCl	OCH(CH3)2
A-760	OCF3	OCF3	OCH(CH3)2
A-761	OC(═O)CH3	OCF3	OCH(CH3)2
A-762	OC(═O)CH2CH3	OCF3	OCH(CH3)2
A-763	OC(═O)CH3	OC(═O)CH3	OCH(CH3)2
A-764	OC(═O)CH2CH3	OC(═O)CH3	OCH(CH3)2
A-765	OC(═O)CH2CH3	OC(═O)CH2CH3	OCH(CH3)2
A-766	CH3	CH3	OCH2CH2CH2CH3
A-767	CH2CH3	CH3	OCH2CH2CH2CH3
A-768	CF3	CH3	OCH2CH2CH2CH3
A-769	F	CH3	OCH2CH2CH2CH3
A-770	Cl	CH3	OCH2CH2CH2CH3
A-771	Br	CH3	OCH2CH2CH2CH3
A-772	I	CH3	OCH2CH2CH2CH3
A-773	OH	CH3	OCH2CH2CH2CH3
A-774	SH	CH3	OCH2CH2CH2CH3
A-775	SCH3	CH3	OCH2CH2CH2CH3
A-776	NH2	CH3	OCH2CH2CH2CH3
A-777	OCH3	CH3	OCH2CH2CH2CH3
A-778	OCHF2	CH3	OCH2CH2CH2CH3
A-779	OCHFCl	CH3	OCH2CH2CH2CH3
A-780	OCF3	CH3	OCH2CH2CH2CH3
A-781	OC(═O)CH3	CH3	OCH2CH2CH2CH3
A-782	OC(═O)CH2CH3	CH3	OCH2CH2CH2CH3
A-783	CH2CH3	CH2CH3	OCH2CH2CH2CH3
A-784	CF3	CH2CH3	OCH2CH2CH2CH3
A-785	F	CH2CH3	OCH2CH2CH2CH3
A-786	Cl	CH2CH3	OCH2CH2CH2CH3
A-787	Br	CH2CH3	OCH2CH2CH2CH3
A-788	I	CH2CH3	OCH2CH2CH2CH3
A-789	OH	CH2CH3	OCH2CH2CH2CH3
A-790	SH	CH2CH3	OCH2CH2CH2CH3
A-791	8CH3	CH2CH3	OCH2CH2CH2CH3
A-792	NH2	CH2CH3	OCH2CH2CH2CH3
A-793	OCH3	CH2CH3	OCH2CH2CH2CH3
A-794	OCHF2	CH2CH3	OCH2CH2CH2CH3
A-795	OCHFCl	CH2CH3	OCH2CH2CH2CH3
A-796	OCF3	CH2CH3	OCH2CH2CH2CH3
A-797	OC(═O)CH3	CH2CH3	OCH2CH2CH2CH3
A-798	OC(═O)CH2CH3	CH2CH3	OCH2CH2CH2CH3
A-799	CF3	CF3	OCH2CH2CH2CH3
A-800	F	CF3	OCH2CH2CH2CH3
A-801	Cl	CF3	OCH2CH2CH2CH3
A-802	Br	CF3	OCH2CH2CH2CH3
A-803	I	CF3	OCH2CH2CH2CH3
A-804	OH	CF3	OCH2CH2CH2CH3
A-805	SH	CF3	OCH2CH2CH2CH3
A-806	SCH3	CF3	OCH2CH2CH2CH3
A-807	NH2	CF3	OCH2CH2CH2CH3
A-808	OCH3	CF3	OCH2CH2CH2CH3
A-809	OCHF2	CF3	OCH2CH2CH2CH3
A-810	OCHFCl	CF3	OCH2CH2CH2CH3
A-811	OCF3	CF3	OCH2CH2CH2CH3
A-812	OC(═O)CH3	CF3	OCH2CH2CH2CH3
A-813	OC(═O)CH2CH3	CF3	OCH2CH2CH2CH3
A-814	F	F	OCH2CH2CH2CH3
A-815	Cl	F	OCH2CH2CH2CH3
A-816	Br	F	OCH2CH2CH2CH3
A-817	I	F	OCH2CH2CH2CH3
A-818	OH	F	OCH2CH2CH2CH3
A-819	SH	F	OCH2CH2CH2CH3
A-820	SCH3	F	OCH2CH2CH2CH3
A-821	NH2	F	OCH2CH2CH2CH3
A-822	OCH3	F	OCH2CH2CH2CH3
A-823	OCHF2	F	OCH2CH2CH2CH3
A-824	OCHFCl	F	OCH2CH2CH2CH3
A-825	OCF3	F	OCH2CH2CH2CH3
A-826	OC(═O)CH3	F	OCH2CH2CH2CH3
A-827	OC(═O)CH2CH3	F	OCH2CH2CH2CH3
A-828	Cl	Cl	OCH2CH2CH2CH3
A-829	Br	Cl	OCH2CH2CH2CH3
A-830	I	Cl	OCH2CH2CH2CH3
A-831	OH	Cl	OCH2CH2CH2CH3
A-832	SH	Cl	OCH2CH2CH2CH3
A-833	SCH3	Cl	OCH2CH2CH2CH3
A-834	NH2	Cl	OCH2CH2CH2CH3
A-835	OCH3	Cl	OCH2CH2CH2CH3
A-836	OCHF2	Cl	OCH2CH2CH2CH3
A-837	OCHFCl	Cl	OCH2CH2CH2CH3
A-838	OCF3	Cl	OCH2CH2CH2CH3
A-839	OC(═O)CH3	Cl	OCH2CH2CH2CH3
A-840	OC(═O)CH2CH3	Cl	OCH2CH2CH2CH3
A-841	Br	Br	OCH2CH2CH2CH3
A-842	I	Br	OCH2CH2CH2CH3
A-843	OH	Br	OCH2CH2CH2CH3
A-844	SH	Br	OCH2CH2CH2CH3
A-845	SCH3	Br	OCH2CH2CH2CH3
A-846	NH2	Br	OCH2CH2CH2CH3
A-847	OCH3	Br	OCH2CH2CH2CH3
A-848	OCHF2	Br	OCH2CH2CH2CH3
A-849	OCHFCl	Br	OCH2CH2CH2CH3
A-850	OCF3	Br	OCH2CH2CH2CH3
A-851	OC(═O)CH3	Br	OCH2CH2CH2CH3
A-852	OC(═O)CH2CH3	Br	OCH2CH2CH2CH3
A-853	I	I	OCH2CH2CH2CH3
A-854	OH	I	OCH2CH2CH2CH3
A-855	SH	I	OCH2CH2CH2CH3
A-856	SCH3	I	OCH2CH2CH2CH3
A-857	NH2	I	OCH2CH2CH2CH3
A-858	OCH3	I	OCH2CH2CH2CH3
A-859	OCHF2	I	OCH2CH2CH2CH3
A-860	OCHFCl	I	OCH2CH2CH2CH3
A-861	OCF3	I	OCH2CH2CH2CH3
A-862	OC(═O)CH3	I	OCH2CH2CH2CH3
A-863	OC(═O)CH2CH3	I	OCH2CH2CH2CH3
A-864	OH	OH	OCH2CH2CH2CH3
A-865	SH	OH	OCH2CH2CH2CH3
A-866	SCH3	OH	OCH2CH2CH2CH3
A-867	NH2	OH	OCH2CH2CH2CH3
A-868	OCH3	OH	OCH2CH2CH2CH3
A-869	OCHF2	OH	OCH2CH2CH2CH3
A-870	OCHFCl	OH	OCH2CH2CH2CH3
A-871	OCF3	OH	OCH2CH2CH2CH3
A-872	OC(═O)CH3	OH	OCH2CH2CH2CH3
A-873	OC(═O)CH2CH3	OH	OCH2CH2CH2CH3
A-874	SH	SH	OCH2CH2CH2CH3
A-875	SCH3	SH	OCH2CH2CH2CH3
A-876	NH2	SH	OCH2CH2CH2CH3
A-877	OCH3	SH	OCH2CH2CH2CH3
A-878	OCHF2	SH	OCH2CH2CH2CH3
A-879	OCHFCl	SH	OCH2CH2CH2CH3
A-880	OCF3	SH	OCH2CH2CH2CH3
A-881	OC(═O)CH3	SH	OCH2CH2CH2CH3
A-882	OC(═O)CH2CH3	SH	OCH2CH2CH2CH3
A-883	SCH3	SCH3	OCH2CH2CH2CH3
A-884	NH2	SCH3	OCH2CH2CH2CH3
A-885	OCH3	SCH3	OCH2CH2CH2CH3
A-886	OCHF2	SCH3	OCH2CH2CH2CH3
A-887	OCHFCl	SCH3	OCH2CH2CH2CH3
A-888	OCF3	SCH3	OCH2CH2CH2CH3
A-889	OC(═O)CH3	SCH3	OCH2CH2CH2CH3
A-890	OC(═O)CH2CH3	SCH3	OCH2CH2CH2CH3
A-891	NH2	NH2	OCH2CH2CH2CH3
A-892	OCH3	NH2	OCH2CH2CH2CH3
A-893	OCHF2	NH2	OCH2CH2CH2CH3
A-894	OCHFCl	NH2	OCH2CH2CH2CH3
A-895	OCF3	NH2	OCH2CH2CH2CH3
A-896	OC(═O)CH3	NH2	OCH2CH2CH2CH3
A-897	OC(═O)CH2CH3	NH2	OCH2CH2CH2CH3
A-898	OCH3	OCH3	OCH2CH2CH2CH3
A-899	OCHF2	OCH3	OCH2CH2CH2CH3
A-900	OCHFCl	OCH3	OCH2CH2CH2CH3
A-901	OCF3	OCH3	OCH2CH2CH2CH3
A-902	OC(═O)CH3	OCH3	OCH2CH2CH2CH3
A-903	OC(═O)CH2CH3	OCH3	OCH2CH2CH2CH3
A-904	OCHF2	OCHF2	OCH2CH2CH2CH3
A-905	OCHFCl	OCHF2	OCH2CH2CH2CH3
A-906	OCF3	OCHF2	OCH2CH2CH2CH3
A-907	OC(═O)CH3	OCHF2	OCH2CH2CH2CH3
A-908	OC(═O)CH2CH3	OCHF2	OCH2CH2CH2CH3
A-909	OCHFCl	OCHFCl	OCH2CH2CH2CH3
A-910	OCF3	OCHFCl	OCH2CH2CH2CH3
A-911	OC(═O)CH3	OCHFCl	OCH2CH2CH2CH3
A-912	OC(═O)CH2CH3	OCHFCl	OCH2CH2CH2CH3
A-913	OCF3	OCF3	OCH2CH2CH2CH3
A-914	OC(═O)CH3	OCF3	OCH2CH2CH2CH3
A-915	OC(═O)CH2CH3	OCF3	OCH2CH2CH2CH3
A-916	OC(═O)CH3	OC(═O)CH3	OCH2CH2CH2CH3
A-917	OC(═O)CH2CH3	OC(═O)CH3	OCH2CH2CH2CH3
A-918	OC(═O)CH2CH3	OC(═O)CH2CH3	OCH2CH2CH2CH3

[0351] The compounds of the formula I can be obtained by different routes. Compounds of the formula I in which X is oxygen are obtained, for example, by reacting aldehydes of the formula II, 4

[0352] where the variables R1, R2, R3 and n are as defined for formula I and may be protected by a protective group Q which is removed after the reaction, with halobenzene derivatives of the formula III, 5

[0353] where the variables R4, R5 and R6 are as defined for formula I and A is halogen, and A is converted, in an intermediate step, into a group B, where B is a suitable metal or a suitable halometal group.

[0354] Suitable groups A are fluorine, chlorine, bromine or iodine, preferably chlorine or bromine.

[0355] Suitable groups B are, for example, Li, Na, MgY (Y=halogen, in particular Br), Sn(R′)2 (R′=CH3, CH2CH3), ZnR′, Cu(CN)ZnI [cf. J. March, Advanced Organic Chemistry, J. Wiley & Sons, New York, 1992, pp. 920-929 and the literature cited therein].

[0356] Preferred groups B are Na and MgY.

[0357] The reaction is carried out by converting the halogen group A into the group B in a manner known per se, followed by in situ reaction of the resulting benzene derivatives with aldehydes of the formula II [cf. J. March, Advanced Organic Chemistry, J. Wiley & Sons, New York, 1992, pp. 920-929 and the literature cited therein].

[0358] If B is Li, Na or MgY, the reaction is carried out, for example, at temperatures of from −20° C. to 150° C., preferably from 20° C. to 100° C., in an inert organic solvent, using at least equimolar amounts of Li, Na or Mg, based on the halobenzene III, and, if B is Li or Na, if appropriate under reaction-accelerating conditions, such as the addition of dibromoethane or iodine, or the use of ultrasound [cf. J. March, Advanced Organic Chemistry, J. Wiley & Sons, New York, 1992, pp. 920-929 and the literature cited therein].

[0359] The protective group Q is introduced into the aldehydes of the formula II by methods known from the literature [cf. T. W. Greene, Protective Groups in Organic Chemistry, J. Wiley & Sons, 1991, pp. 10-142].

[0360] Suitable protective groups for R1, R2, R3=hydroxyl, mercapto or amino are, for example, groups that can be removed under Lewis-acidic conditions, such as alkyl, in particular methyl.

[0361] In a preferred embodiment of the reaction, the variables R1, R2 and R3 are inert under the reaction conditions.

[0362] For preparing compounds I in which R1 and R3 contain carbonyl functionalities, the process described below, which uses the corresponding benzophenones IV as starting materials, is preferred.

[0363] Suitable solvents are aliphatic hydrocarbons, such as pentane, hexane, cyclohexane and petroleum ether, aromatic hydrocarbons, such as toluene, o-, m- and p-xylene, halogenated hydrocarbons, such as methylene chloride, chloroform and chlorobenzene, ethers, such as diethyl ether, diisopropyl ether, tert-butyl methyl ether, dioxane, anisole and tetrahydrofuran, nitrites, such as acetonitrile and propionitrile, preferably ethers, very particularly preferably diethyl ether and tetrahydrofuran.

[0364] It is also possible to use mixtures of the solvents mentioned.

[0365] The starting materials are generally reacted with one another in equimolar amounts. In terms of yield, it may be advantageous to use an excess of compounds of the formula III, based on compounds of the formula II.

[0366] The reaction mixtures are worked up in a customary manner, for example by mixing with water, phase separation and, if required, chromatographic purification of the crude products. Some intermediates and end products are obtained in the form of colorless or slightly brownish, viscous oils, which are purified or freed from volatile components under reduced pressure and at moderately elevated temperature. If the intermediates and end products are obtained as solids, purification can also be carried out by recrystallization or digestion.

[0367] The starting materials of the formula II required for preparing the compounds I can be prepared, for example, by reducing the corresponding benzoic acids or benzoic esters with diisobutylaluminum hydride, described, for example, in EP-A 727 141, or they can be prepared in the manner known per se [cf. J. March, Advanced Organic Chemistry, J. Wiley & Sons, New York, 1992, pp. 501-521, pp 641-758, pp. 982-1161.].

[0368] The starting materials of the formula III required for preparing the compounds I can be prepared by methods known from the literature from gallic acid or its derivatives, or in a manner known per se [cf. J. March, Advanced Organic Chemistry, J. Wiley & Sons, New York, 1992, pp. 501-521, pp. 641-758, pp. 982-1161.]

[0369] Compounds of the formula I in which X is oxygen can also be prepared by reduction of the analogous benzophenone derivatives of the formula IV, 6

[0370] where the variables are as defined for formula I or denote a group which, after the reaction, can be converted into these radicals, using hydrides or by catalytic reduction with H2.

[0371] Suitable hydrides are, preferably, borohydrides and aluminum hydrides, such as NaBH4 or LiAlH4 [cf. M. Hudlicky, Reductions in Organic Chemistry, ACS Monograph 188, American Chemical Society, Washington D.C., 1996, p. 152 ff.; Tetrahedron Lett. 28 (4), pp. 4725-4728 (1987)], or elemental aluminum in ammonia [cf. Chem. Soc. Jpn. 63(1), pp. 290-292 (1990)].

[0372] The reaction is usually carried out at temperatures of from −78° C. to 120° C., preferably from −78° C. to 0° C., in an inert organic solvent.

[0373] Suitable solvents are aliphatic hydrocarbons, such as pentane, hexane, cyclohexane and petroleum ether, aromatic hydrocarbons, such as toluene, o-, m- and p-xylene, halogenated hydrocarbons, such as methylene chloride, chloroform and chlorobenzene, ethers, such as diethyl ether, diisopropyl ether, tert-butyl methyl ether, dioxane, anisole and tetrahydrofuran, preferably ethers, articularly preferably tetrahydrofuran. It is also possible to use mixtures of the solvents mentioned.

[0374] The starting materials are generally reacted with one another in equimolar amounts. In terms of yield, it may be advantageous to employ an excess of reducing agent, based on compounds of the formula IV.

[0375] The reaction mixtures are worked up in a customary manner, for example by mixing with water, phase separation and, if required, chromatographic purification of the crude products. Some intermediates and end products are obtained in the form of colorless or slightly brownish, viscous oils, which are purified or freed from volatile components under reduced pressure and at moderately elevated temperature. If the intermediates and end products are obtained as solids, purification can also be carried out by recrystallization or digestion.

[0376] The reduction can also be carried out in the manner known per se using H2 and catalysts based on transition metals. Suitable transition metals are palladium, platinum, rhodium and ruthenium.

[0377] This reaction is usually carried out at temperatures of from 0° C. to 150° C., preferably from 0° C. to 50° C., in an inert organic solvent [cf. Organotransition Metal Chemistry, Academic Press, New York, 1974, pp. 65-70 and the literature cited therein; JP-A 10273455].

[0378] Suitable solvents are aliphatic hydrocarbons, such as pentane, hexane, cyclohexane and petroleum ether, aromatic hydrocarbons, such as toluene, o-, m- and p-xylene, halogenated hydrocarbons, such as methylene chloride, chloroform and chlorobenzene, ethers, such as diethyl ether, diisopropyl ether, tert-butyl methyl ether, dioxane, anisole and tetrahydrofuran, alcohols, such as methanol, ethanol, n-propanol, isopropanol, n-butanol and tert-butanol, particularly preferably methanol, ethanol or isopropanol. It is also possible to use mixtures of the solvents mentioned.

[0379] In a preferred embodiment of the reduction with H2, chiral catalysts are employed, so that it is possible to obtain the (R) or (S) isomer of the benzhydryl alcohol I in a selective manner [cf. Org. Lett. 2(5), pp. 659-662, (2000)].

[0380] If the variables R1, R2 or R3 are groups which can be reduced under the reaction conditions, such as nitro or formyl, it may be necessary to re-establish these groups after the reaction by selective oxidation. It may also be advantageous to introduce such reducible groups only after the reduction of the benzophenones IV has taken place, by oxidizing appropriate groups (for example introducing a nitro group by oxidation of an amino group or introducing a formyl group by oxidation of a hydroxyl group).

[0381] Compounds I in which R1 is formyl can be obtained, for example, by selective oxidation of corresponding compounds in which R1 is hydroxymethyl, which may be formed in the reduction according to the invention from a formyl group [cf. M. Hudlicky, Oxidations in Organic Chemistry, ACS Monograph 186, American Chemical Society, Washington D.C., 1990, pp. 114-127].

[0382] It may also be advantageous to obtain compounds of the formula I in which R1 is hydroxyl by reducing compounds of the formula IV in which R1 is alkylcarbonyloxy. Here, R1 and the keto group that bridges the phenyl groups are reduced simultaneously.

[0383] For compounds I in which the variables R1, R2 , R3 or R4 are alkenyl or alkynyl, the process described above, which uses halobenzene derivatives III and aldehydes II as starting materials, is preferred.

[0384] The reaction mixtures are worked up in a customary manner, for example by mixing with water, phase separation and, if required, chromatographic purification of the crude products. Some intermediates and end products are obtained in the form of colorless or slightly brownish, viscous oils, which are purified or freed from volatile components under reduced pressure and at moderately elevated temperature. If the intermediates and end products are obtained as solids, purification can also be carried out by recrystallization or digestion.

[0385] The starting materials of the formula IV required for preparing the compounds I are known from the literature (for example from EP-A 727 141), or they can be prepared in accordance with the literature cited.

[0386] If individual compounds I are not accessible by the routes described above, they can be prepared by derivatization of other compounds I. 7

[0387] The benzhydryl thiols Ib can be obtained from the corresponding alcohols Ia under conditions known from the literature. The reaction is usually carried out at temperatures of from 0° C. to 180° C., preferably from 20° C. to 140° C., in an inert organic solvent [cf. Liebigs Ann. Chem., p. 177 (1989)].

[0388] Suitable solvents are aliphatic hydrocarbons, such as pentane, hexane, cyclohexane and petroleum ether, aromatic hydrocarbons, such as toluene, o-, m- and p-xylene, halogenated hydrocarbons, such as methylene chloride, chloroform and chlorobenzene, ethers, such as diethyl ether, diisopropyl ether, tert-butyl methyl ether, dioxane, anisole and tetrahydrofuran, and dimethylene glycol, particularly preferably toluene and dimethylene glycol.

[0389] It is also possible to use mixtures of the solvents mentioned.

[0390] Suitable sulfurizing agents are, for example, phosphorus pentasulfide or Lawesson's reagent.

[0391] The starting materials are generally reacted with one another in equimolar amounts. In terms of yield, it may be advantageous to employ an excess of sulfurizing agent, based on Ia.

[0392] Benzhydryl thiols Ib can also be obtained by reducing the corresponding thioketones V, which can be prepared from the benzophenones IV. 8

[0393] The reduction to give the benzhydryl thiols Ib can be carried out using, for example, borohydrides or aluminum hydrides [cf. Synth. Commun. 23 (9), pp. 1267-1271 (1993); Tetrahedron: Asymmetry 7(12), pp. 3553-3558 (1996); Can. J. Chem. 48, p. 3593, (1970)], or using elemental ytterbium in tetrahydrofuran [cf. Chem. Lett. 3, p. 611 (1994)].

[0394] The conversion of the benzophenones IV into the thioketones V is carried out analogously to the reaction of the benzhydryl alcohols Ia described above.

[0395] The compounds I are suitable as fungicides. They have excellent activity against a broad spectrum of phytopathogenic fungi, in particular from the class of the Ascomycetes, Deuteromycetes, Phycomycetes and Basidiomycetes. Some of them act systemically and can be employed in crop protection as foliar- and soil-acting fungicides.

[0396] They are especially important for controlling a large number of fungi in a variety of crop plants such as wheat, rye, barley, oats, rice, maize, grass, bananas, cotton, soya, coffee, sugar cane, grape vines, fruit species, ornamentals and vegetable species such as cucumbers, beans, tomatoes, potatoes and cucurbits, and also in the seeds of these plants.

[0397] Specifically, they are suitable for controlling the following plant diseases:

[0398] Alternaria species in vegetables and fruit,

[0399] Botrytis cinerea (gray mold) in strawberries, vegetables, ornamentals and grape vines,

[0400] Cercospora arachidicola in groundnuts,

[0401] Erysiphe cichoracearum and Sphaerotheca fuliginea in cucurbits,

[0402] Erysiphe graminis (powdery mildew) in cereals,

[0403] Fusarium and Verticillium species in a variety of plants,

[0404] Helminthosporium species in cereals,

[0405] Mycosphaerella species in bananas and groundnuts,

[0406] Phytophthora infestans in potatoes and tomatoes,

[0407] Plasmopara viticola in grape vines,

[0408] Podosphaera leucotricha in apples,

[0409] Pseudocercosporella herpotrichoides in wheat and barley,

[0410] Pseudoperonospora species in hops and cucumbers,

[0411] Puccinia species in cereals,

[0412] Pyricularia oryzae in rice,

[0413] Rhizoctonia species in cotton, rice and lawns,

[0414] Septoria nodorum in wheat,

[0415] Uncinula necator in grape vines,

[0416] Ustilago species in cereals and sugar cane, and

[0417] Venturia species (scab) in apples and pears.

[0418] The compounds I are also suitable for controlling harmful fungi such as Paecilomyces variotii in the protection of materials (for example wood, paper, paint dispersions, fibers or tissues) and in the protection of stored products.

[0419] The compounds I are employed by treating the fungi or the plants, seeds, materials to be protected against fungal attack or the soil with a fungicidally effective amount of the active compounds. The application may be carried out before or after the infection of the materials, plants or seeds by the fungi.

[0420] The fungicidal compositions generally comprise from 0.1 to 95, preferably from 0.5 to 90, % by weight of active compound.

[0421] For use in crop protection, the application rates are, depending on the kind of effect desired, from 0.01 to 2.0 kg of active compound per ha.

[0422] The treatment of seeds generally requires active compound quantities of from 0.001 to 0.1 g, preferably from 0.01 to 0.05 g, per kilogram of seed.

[0423] For use in the protection of materials or stored products, the active compound application rate depends on the kind of application area and effect desired. Customary application rates in the protection of materials are, for example, from 0.001 g to 2 kg, preferably from 0.005 g to 1 kg, of active compound per cubic meter of treated material.

[0424] The compounds I can be converted into the customary formulations, e.g. solutions, emulsions, suspensions, dusts, powders, pastes and granules. The use form depends on the specific intended use; in any case, it should ensure fine and uniform distribution of the compound according to the invention.

[0425] The formulations are prepared in a known manner, e.g. by extending the active compound with solvents and/or carriers, if desired using emulsifiers and dispersants, it also being possible to use other organic solvents as auxiliary solvents if water is used as the diluent. Suitable auxiliaries for this purpose are essentially: solvents such as aromatics (e.g. xylene), chlorinated aromatics (e.g. chlorobenzenes), paraffins (e.g. mineral oil fractions), alcohols (e.g. methanol, butanol), ketones (e.g. cyclohexanone), amines (e.g. ethanolamine, dimethylformamide) and water; carriers such as ground natural minerals (e.g. kaolins, clays, talc, chalk) and ground synthetic minerals (e.g. finely divided silica, silicates); emulsifiers such as nonionic and anionic emulsifiers (e.g. polyoxyethylene fatty alcohol ethers, alkylsulfonates and arylsulfonates), and dispersants such as lignosulfite waste liquors and methylcellulose.

[0426] Suitable surfactants are the alkali metal, alkaline earth metal and ammonium salts of lignosulfonic acid, naphthalenesulfonic acid, phenolsulfonic acid, dibutylnaphthalenesulfonic acid, alkylarylsulfonates, alkyl sulfates, alkylsulfonates, fatty alcohol sulfates and fatty acids and alkali metal salts and alkaline earth metal salts thereof, salts of sulfated fatty alcohol glycol ethers, condensation products of sulfonated naphthalene and naphthalene derivatives with formaldehyde, condensation products of naphthalene or of naphthalenesulfonic acid with phenol and formaldehyde, polyoxyethylene octylphenol ethers, ethoxylated isooctylphenol, octylphenol, nonylphenol, alkylphenol polyglycol ethers, tributylphenyl polyglycol ethers, alkylaryl polyether alcohols, isotridecyl alcohol, 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.

[0427] Suitable for preparing directly sprayable solutions, emulsions, pastes or oil dispersions are petroleum fractions having medium to high boiling points, such as kerosene or diesel oil, furthermore coal-tar oils and oils of plant or animal origin, aliphatic, cyclic and aromatic hydrocarbons, for example benzene, toluene, xylene, paraffin, tetrahydronaphthalene, alkylated naphthalenes or derivatives thereof, methanol, ethanol, propanol, butanol, chloroform, carbon tetrachloride, cyclohexanol, cyclohexanone, chlorobenzene, isophorone, strongly polar solvents, for example dimethylformamide, dimethyl sulfoxide, N-methylpyrrolidone and water.

[0428] Powders, compositions for broadcasting and dusts can be prepared by mixing or jointly grinding the active substances with a solid carrier.

[0429] Granules, for example coated granules, impregnated granules and homogeneous granules, can be prepared by binding the active compounds to solid carriers. Solid carriers are, for example, mineral earths, such as silica gel, silicas, 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 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.

[0430] The formulations generally 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 from 95% to 100% (according to the NMR spectrum).

[0431] Examples of Formulations are:

[0432] I. 5 parts by weight of a compound according to the invention are thoroughly mixed with 95 parts by weight of finely divided kaolin. This affords a dusting composition comprising 5% by weight of the active compound.

[0433] II. 30 parts by weight of a compound according to the invention are thoroughly mixed with a mixture of 92 parts by weight of pulverulent silica gel and 8 parts by weight of paraffin oil which had been sprayed onto the surface of this silica gel. This affords an active compound preparation having good adhesive properties (active compound content 23% by weight).

[0434] III. 10 parts by weight of a compound according to the invention are dissolved in a mixture comprising 90 parts by weight of xylene, 6 parts by weight of the addition product of 8 to 10 mol of ethylene oxide to 1 mol of oleic acid N-monoethanolamide, 2 parts by weight of the calcium salt of dodecylbenzenesulfonic acid and 2 parts by weight of the addition product of 40 mol of ethylene oxide to 1 mol of castor oil (active compound content 9% by weight).

[0435] IV. 20 parts by weight of a compound according to the invention are dissolved in a mixture comprising 60 parts by weight of cyclohexanone, 30 parts by weight of isobutanol, 5 parts by weight of the addition product of 7 mol of ethylene oxide to 1 mol of isooctylphenol and 5 parts by weight of the addition product of 40 mol of ethylene oxide to 1 mol of castor oil (active compound content 16% by weight).

[0436] V. 80 parts by weight of a compound according to the invention are mixed well with 3 parts by weight of the sodium salt of 45 diisobutylnaphthalene-α-sulfonic acid, 10 parts by weight of the sodium salt of a lignosulfonic acid from a sulfite waste liquor and 7 parts by weight of pulverulent silica gel, and ground in a hammer mill (active compound content 80% by weight).

[0437] VI. 90 parts by weight of a compound according to the invention are mixed with 10 parts by weight of N-methyl-α-pyrrolidone, affording a solution which is suitable for use in the form of very small drops (active compound content 90% by weight).

[0438] VII. 20 parts by weight of a compound according to the invention are dissolved in a mixture comprising 40 parts by weight of cyclohexanone, 30 parts by weight of isobutanol, 20 parts by weight of the addition product of 7 mol of ethylene oxide to 1 mol of isooctylphenol and 10 parts by weight of the addition product of 40 mol of ethylene oxide to 1 mol of castor oil. The solution is poured into 100 000 parts by weight of water and finely dispersed therein, affording an aqueous dispersion comprising 0.02% by weight of active compound.

[0439] VIII. 20 parts by weight of a compound according to the invention are mixed well with 3 parts by weight of the sodium salt of diisobutylnaphthalene-α-sulfonic acid, 17 parts by weight of the sodium salt of a lignosulfonic acid from a sulfite waste liquor and 60 parts by weight of pulverulent silica gel, and ground in a hammer mill. The mixture is finely dispersed in 20 000 parts by weight of water, affording a spray liquor comprising 0.1% by weight of active compound.

[0440] The active compounds can be applied as such, in the form of their formulations or in the application forms prepared therefrom, for example in the form of directly sprayable solutions, powders, suspensions or dispersions, emulsions, oil dispersions, pastes, dusting compositions, compositions for broadcasting, or granules, by spraying, atomizing, dusting, broadcasting or watering. The application forms depend entirely on the intended uses; in any case, they should ensure the finest dispersion possible of the active compounds according to the invention.

[0441] Aqueous use forms can be prepared from emulsion concentrates, pastes or wettable powders (spray powders, oil dispersions) by addition of water. To prepare emulsions, pastes or oil dispersions, the substances can be homogenized in water as such or dissolved in an oil or solvent, by means of wetting agents, tackifiers, dispersants or emulsifiers. However, concentrates comprising active compound, wetting agent, tackifier, dispersant or emulsifier and possibly solvent or oil which are suitable for dilution with water can also be prepared.

[0442] The active compound concentrations in the ready-to-use preparations can be varied over a relatively wide range. In general, they are from 0.0001 to 10%, preferably from 0.01 to 1%.

[0443] It is also possible to use the active compounds with good success in the ultra-low-volume method (ULV), it being possible to apply formulations comprising more than 95% by weight of active compound or even the active compound without additives.

[0444] Oils of various types, herbicides, fungicides, other pesticides and bactericides can be added to the active compounds, if desired even immediately prior to application (tank mix). These agents can be added to the compositions according to the invention in a weight ratio of 1:10 to 10:1.

[0445] The compositions according to the invention in the use form as fungicides may also be present in combination with other active compounds, for example with herbicides, insecticides, growth regulators, fungicides or else with fertilizers. In many cases, a mixture of the compounds I, or of the compositions comprising them, in the use form as fungicides with other fungicides results in a broader fungicidal spectrum of activity.

[0446] The following list of fungicides in combination with which the compounds according to the invention can be used is intended to illustrate the possible combinations, but not to impose any limitation:

[0447] a sulfur, dithiocarbamates and their derivatives, such as iron(III) dimethyldithiocarbamate, zinc dimethyldithio-carbamate, zinc ethylenebisdithiocarbamate, manganese ethylenebisdithiocarbamate, manganese zinc ethylenediamine-bisdithiocarbamate, tetramethylthiuram disulfides, ammonia complex of zinc (N,N-ethylenebisdithiocarbamate), ammonia complex of zinc (N,N′-propylenebisdithiocarbamate), zinc (N,N′-propylenebisdithiocarbamate), N,N′-polypropylenebis-(thiocarbamoyl)disulfide;

[0448] nitro derivatives, such as dinitro-(1-methylheptyl)phenyl crotonate, 2-sec-butyl-4,6-dinitrophenyl-3,3-dimethyl acrylate, 2-sec-butyl-4,6-dinitrophenylisopropyl carbonate, diisopropyl 5-nitroisophthalate;

[0449] heterocyclic substances, such as 2-heptadecyl-2-imidazoline acetate, 2,4-dichloro-6-(o-chloroanilino)-s-triazine, O,O-diethyl phthalimidophosphonothioate, 5-amino-1-[bis(dimethylamino)phosphinyl]-3-phenyl-1,2,4-triazole, 2,3-dicyano-1,4-dithioanthraquinone, 2-thio-1,3-dithiolo-[4,5-b]quinoxaline, methyl 1-(butylcarbamoyl)-2-benzimidazole-carbamate, 2-methoxycarbonylaminobenzimidazole, 2-(furyl-(2))-benzimidazole, 2-(thiazolyl-(4))-benzimidazole, N-(1,1,2,2-tetrachloroethylthio)tetrahydrophthalimide, N-trichloromethylthiotetrahydrophthalimide, N-trichloro-methylthiophthalimide,

[0450] N-dichlorofluoromethylthio-N′,N′-dimethyl-N-phenylsulfuric diamide, 5-ethoxy-3-trichloromethyl-1,2,3-thiadiazole, 2-thiocyanatomethylthiobenzothiazole, 1,4-dichloro-2,5-dimethoxybenzene, 4-(2-chlorophenylhydrazono)-3-methyl-5-isoxazolone, pyridine 2-thio-1-oxide, 8-hydroxyquinoline or its copper salt, 2,3-dihydro-5-carboxanilido-6-methyl-1,4-oxathiine, 2,3-dihydro-5-carboxanilido-6-methyl-1,4-oxathiine 4,4-dioxide, 2-methyl-5,6-dihydro-4H-pyran-3-carboxanilide, 2-methylfuran-3-carboxanilide, 2,5-dimethyl-furan-3-carboxanilide, 2,4,5-trimethylfuran-3-carboxanilide, N-cyclohexyl-2,5-dimethylfuran-3-carboxamide, N-cyclohexyl-N-methoxy-2,5-dimethylfuran-3-carboxamide, 2-methylbenzanilide, 2-iodobenzanilide, N-formyl-N-morpholine 2,2,2-trichloroethyl acetal, piperazine-1,4-diylbis-1-(2,2,2-trichloroethyl)-formamide, 1-(3,4-dichloroanilino)-1-formylamino-2,2,2-tri-chloroethane, 2,6-dimethyl-N-tridecylmorpholine or its salts, 2,6-dimethyl-N-cyclododecylmorpholine or its salts, N-[3-(p-tert-butylphenyl)-2-methylpropyl]-cis-2,6-dimethyl-morpholine, N-[3-(p-tert-butylphenyl)-2-methylpropyl]-piperidine, 1-[2-(2,4-dichlorophenyl)-4-ethyl-1,3-dioxolan-2-ylethyl]-1H-1,2,4-triazole, 1-[2-(2,4-dichlorophenyl)-4-n-propyl-1,3-dioxolan-2-ylethyl]-1H-1,2,4-triazole, N-(n-propyl)-N-(2,4,6-trichlorophenoxyethyl)-N′-imidazolylurea, 1-(4-chlorophenoxy)-3,3-dimethyl-1-(1H-1,2,4-triazol-1-yl)-2-butanone, 1-(4-chlorophenoxy)-3,3-dimethyl-1-(1H-1,2,4-triazol-1-yl)-2-butanol, (2RS, 3RS)-1-[3-(2-chlorophenyl)-2-(4-fluorophenyl)oxiran-2-ylmethyl]-1H-1,2,4-triazole, α- (2-chlorophenyl) -α-(4-chlorophenyl) -5-pyrimidinemethanol, 5-butyl-2-dimethylamino-4-hydroxy-6-methylpyrimidine, bis-(p-chlorophenyl)-3-pyridinemethanol, 1,2-bis(3-ethoxycarbonyl-2-thioureido)benzene, 1,2-bis-(3-methoxycarbonyl-2-thioureido)-benzene,

[0451] strobilurins, such as methyl E-methoxyimino[α-(o-tolyloxy)-o-tolyl]acetate, methyl E-2-{2-[6-(2-cyanophenoxy)-pyrimidin-4-yloxy]phenyl}-3-methoxyacrylate, methyl E-methoxy-imino[α-(2-phenoxyphenyl)lacetamide, methyl E-methoxyimino-[α-(2,5-dimethylphenoxy)-o-tolyl]acetamide, methyl E-2-{2-[(2-trifluoromethylpyrid-6-yl)oxymethyl]phenyl}-3-methoxyacrylate, methyl (E,E)-methoximino-{2-[1-(3-trifluoro-methylphenyl)ethylideneaminooxymethyl]phenyl}acetate, methyl N-(2-{[1-(4-chlorophenyl)-1H-pyrazol-3-yl]oxymethyl}phenyl)-N-methoxycarbamate,

[0452] anilinopyrimidines, such as N-(4,6-dimethylpyrimidin-2-yl)aniline, N-[4-methyl-6-(l-propynyl)pyrimidin-2-yl]aniline, N-[4-methyl-6-cyclopropylpyrimidin-2-yl]aniline, phenylpyrroles, such as 4-(2,2-difluoro-1,3-benzodioxol-4-yl)pyrrole-3-carbonitrile,

[0453] cinnamamides, such as 3-(4-chlorophenyl)-3-(3,4-dimethoxy-phenyl)acryloylmorpholine,

[0454] and a variety of fungicides, such as dodecylguanidine acetate, 3-[3-(3,5-dimethyl-2-oxycyclohexyl)-2-hydroxyethyl]glutarimide, hexachlorobenzene, methyl N-(2,6-dimethylphenyl)-N-(2-furoyl)-DL-alaninate, DL-N-(2,6-dimethylphenyl)-N-(2′-methoxyacetyl)-alanine methyl ester, N-(2,6-dimethylphenyl)-N-chloroacetyl-D,L-2-aminobutyrolactone, DL-N-(2,6-dimethylphenyl)-N-(phenyl-acetyl)alanine methyl ester, 5-methyl-5-vinyl-3-(3,5-dichloro-phenyl)-2,4-dioxo-1,3-oxazolidine, 3-(3,5-dichlorophenyl)-5-methyl-5-methoxymethyl-1,3-oxazolidine-2,4-dione, 3-(3,5-dichlorophenyl)-1-isopropyl carbamoylhydantoin, N-(3,5-dichlorophenyl)-1,2-dimethylcyclopropane-1,2-dicarboximide, 2-cyano-[N-(ethylaminocarbonyl)-2-meth-oximino]acetamide, 1-[2-(2,4-dichlorophenyl)pentyl]-1H-1,2,4-triazole, 2,4-difluoro-α-(1H-1,2,4-triazolyl-1-methyl)-benzhydryl alcohol, N-(3-chloro-2,6-dinitro-4-trifluoromethyl-phenyl)-5-trifluoromethyl-3-chloro-2-aminopyridine, 1-((bis-(4-fluorophenyl)methylsilyl)methyl)-1H-1,2,4-triazole.

Synthesis Examples

[0455] The procedures given in the synthesis examples below were used to obtain further compounds I by appropriate modification of the starting materials. The compounds obtained in this manner are listed in the tables which follow, together with physical data.

EXAMPLE 1

Preparation of 5-bromo-6,6′-dimethyl-2,2′, 3′, 4′-tetramethoxybenz-hydryl alcohol

[0456] 9

[0457] 2.36 g of 2,3,4-trimethoxy-6-methylbromobenzene and 0.32 g of agnesium turnings were initially charged in 5 ml of anhydrous tetrahydrofuran, 0.57 ml of 1,2-dibromoethane was added and the reaction mixture was heated at reflux temperature for about 40 min. After cooling to 30° C., 1.40 g of 5-bromo-2-methoxy-6-methylbenzaldehyde were added dropwise, and the solution was stirred for about two hours. Water/2N hydrochloric acid (1/1) was added, the aqueous phase was extracted with ethyl acetate, the organic phases were washed with water and dried and the solvent was distilled off, and the residue was then purified by column chromatography (mobile phase petroleum ether/ethyl acetate 85/5). 1.5 g of the title compound were isolated as a violet viscous oil.

EXAMPLE 2

Preparation of 2,5-dichloro-6,6′-dimethyl-2′, 3′, 4′-trimethoxy-benzhydryl alcohol

[0458] 10

[0459] Under protective gas conditions, at about −78° C. , 1 ml of a 1-molar solution of LiAlH4 in tetrahydrofuran was added dropwise to a solution of 0.37 g of 2,5-dichloro-6,6′-dimethyl-2′, 3′, 4′-trimethoxybenzophenone in 20 ml of anhydrous tetrahydrofuran, and the mixture was stirred for about 1 hour. At 20-25° C. , sat. NaHCO3 solution was added to the reaction solution, the solution was extracted with ethyl acetate and the organic phase was washed with water and sat. NaCl solution and dried, and the solvent was then distilled off. The residue gave, after purification by column chromatography (mobile phase: ethyl acetate/cyclohexane 1:9), 150 mg of the title compound as a yellow viscous oil.

EXAMPLE 3

Preparation of 5-chloro-2-hydroxy-6,6′-dimethyl-2′, 3′, 4′-trimethoxybenzhydryl alcohol

[0460] 11

[0461] At −20° C. , under an atmosphere of protective gas, 3 mmol of a 1-molar solution of LiAlH4 in tetrahydrofuran (THF) were added dropwise to a solution of 0.86 g of 5-chloro-2-hydroxy-6,6′-dimethyl-2′, 3′, 4′-trimethoxybenzophenone in 10 ml of anhydrous THF. The reaction mixture was warmed to room temperature and then admixed with ice water, acidified with dilute hydrochloric acid and extracted with ethyl acetate. The combined organic phases were washed with sat. NaCl solution, dried and purified by column chromatography (mobile phase: ethyl acetate/cyclohexane 3:7). This gave 0.46 mg of the title compound as a white solid of m.p. 140-142° C.

TABLE I
12
							phys. data
No.	R1	(R2)n	R3	R4	R5	R5	(m.p.[° C.])
I-1	OCH3	5-Br	CH3	CH3	OCH3	OCH3	oil
I-2	Cl	5-Cl	CH3	CH3	OCH3	OCH3	oil
I-3	OH	5-Cl	CH3	CH3	OCH3	OCH3	140-142

Examples of the Activity Against Harmful Fungi

[0462] The fungicidal activity of the compounds of the formula I was demonstrated by the following experiments:

[0463] The active compounds were formulated, separately or together, as a 10% strength emulsion in a mixture of 70% by weight of cyclohexanone, 20% by weight of Nekanil® LN (Lutensol® AP6, wetting agent having emulsifying and dispersing action based on ethoxylated alkylphenols) and 10% by weight of Wettol® EM (nonionic emulsifier based on ethoxylated castor oil) and diluted with water to the desired concentration.

[0464] After conclusion of the tests, in each case the lowest concentration at which the compounds still caused 80-100% inhibition in comparison to untreated controls (activity 45 threshold or minimum concentration) was determined.

Use Example 1—Activity Against Mildew of Wheat

[0465] Leaves of potted wheat seedlings cv. “Kanzler” were sprayed to runoff point with an aqueous preparation of active compound which had been prepared from a stock solution made of 10% of active compound, 63% of cyclohexanone and 27% of emulsifier. 24 hours after the spray coating had dried on, the leaves were dusted with spores of mildew of wheat (Erysiphe graminis forma specialis tritici). The test plants were then placed in a greenhouse at 20-24° C. and 60-90% rel. atmospheric humidity. After 7 days, the extent of the mildew development was determined visually as % infection of the total leaf area.

[0466] In this test, the plants which had been treated with 4 or 16 ppm of the active compounds I-1, I-2 and 1-3 showed an infection of in each case at most 30%, whereas the untreated plants were infected to 90%.

Claims

1. A benzhydryl derivative of the formula I,

2. A compound of the formula I as claimed in claim 1 where X is oxygen.

3. A compound of the formula I as claimed in claim 1 where the variables are as defined below: R1, R3 independently of one another are halogen, hydroxyl, amino, mercapto, nitro, cyano, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkylcarbonyloxy, C1-C6-haloalkylcarbonyloxy, C1-C6-alkylthio, C1-C6-haloalkylthio, C1-C6-alkylcarbonyl or C1-C6-haloalkylcarbonyl.

4. A compound of the formula I as claimed in claim 1 where R2 is halogen, hydroxyl, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy or C1-C6-haloalkoxy.

5. A compound of the formula I as claimed in claim 1 where R4 is C1-C6-alkyl or C1-C6-haloalkyl.

6. A compound of the formula I as claimed in claim 1 where R5, R6 are hydroxyl, C1-C6-alkoxy, C2-C6-alkenyloxy, C1-C6-haloalkoxy or C2-C6-haloalkenyloxy.

7. A compound of the formula I as claimed in claim 1, where the variables are as defined below: R1, R3 are halogen, hydroxyl, amino, mercapto, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy or C1-C6-alkylcarbonyl; R2 is halogen, hydroxyl, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy or C1-C6-haloalkoxy; R4 is methyl; R5, R6 are C1-C6-alkoxy; n is 0 or 1.

8. A process for preparing compounds of the formula I as claimed in claim 1 in which X is oxygen, by reacting aldehydes of the formula II,

9. A process for preparing compounds of the formula I as claimed in claim 1 in which X is oxygen, by reduction of benzophenone derivatives of the formula IV,

10. A composition suitable for controlling phytopathogenic harmful fungi, which comprises a solid or liquid carrier and a compound of the formula I as claimed in claim 1.

11. A method for controlling phytopathogenic fungi, which comprises treating the fungi or the materials, plants, the soil or the seed to be protected against fungal attack with an effective amount of a compound of the formula I as claimed in claim 1.