Substituted pyridine herbicides

Abstract

Compounds of the formula (I) in which the substituents are as defined in claim 1 are suitable for use as herbicides.

Description

[0001] The present invention relates to novel herbicidally active pyridine ketones, to processes for their preparation, to compositions which comprise these compounds, and to their use for controlling weeds, in particular in crops of useful plants, or for inhibiting plant growth.

[0002] Pyridine ketones having herbicidal action are described, for example, in WO 00/15615 and WO/0039094.

[0003] We have now found novel pyridine ketones having herbicidal and growth-inhibiting properties.

[0004] The present invention thus provides compounds of the formula I 1

[0005] in which

[0006] is 0 or 1;

[0007] R1 is a C1-C6alkylene, C3-C6alkenylene or C3-C6alkynylene chain which may be mono- or polysubstituted by halogen or R5, where the unsaturated bonds of the chain are not attached directly to the substituent X1;

[0008] X1 is oxygen, —O(CO)—, —(CO)O—, —O(CO)O—, —N(R6)—O—, —O—NR51—, thio, sulfinyl, sulfonyl, —SO2NR7—, —NR52SO2— or —NR8—;

[0009] R2 is a C1-C8alkyl, C3-C6alkenyl or C3-C6alkynyl group which is mono- or polysubstituted by halogen, hydroxyl, amino, formyl, nitro, cyano, mercapto, carbamoyl, C1-C6alkoxy, C1-C6alkoxycarbonyl, C2-C6alkenyl, C2-C6haloalkenyl, C2-C6alkynyl, C2-C6haloalkynyl C3-C6cycloalkyl, by halogen-substituted C3-C6cycloalkyl, or by C3-C6alkenyloxy, C3-C6alkynyloxy, C1-C6haloalkoxy, C3-C6haloalkenyloxy, cyano-C1-C6alkoxy, C1-C6alkoxy-C1-C6alkoxy, C1-C6alkoxy-C1-C6alkoxy-C1-C6alkoxy, C1-C6alkylthio-C1-C6alkoxy, C1-C6alkyl-sulfinyl-C1-C6alkoxy, C1-C6alkylsulfonyl-C1-C6alkoxy, C1-C6alkoxycarbonyl-C1-C6alkoxy, C1-C6alkoxycarbonyl, C1-C6alkylcarbonyl, C1-C6alkylthio, C1-C6alkylsulfinyl, C1-C6alkylsulfonyl, C1-C6haloalkylthio, C1-C6haloalkylsulfinyl, C1-C6haloalkylsulfonyl, oxiranyl, which for its part may be substituted by C1-C6alkyl, or by (3-oxetanyl)oxy, which for its part may be substituted by C1-C6alkyl, or by benzylthio, benzylsulfinyl, benzylsulfonyl, C1-C6alkylamino, di(C1-C6alkyl)amino, RgS(O)2O, R10N(R11)SO2—, thiocyanato, phenyl, phenoxy, phenylthio, phenylsulfinyl or phenylsulfonyl;

[0010] where the phenyl- or benzyl-containing groups for their part may be substituted by one or more C1-C6alkyl, C1-C6haloalkyl, C1-C6alkoxy, C1-C6haloalkoxy, halogen, cyano, hydroxyl or nitro groups, or

[0011] R2 is phenyl which may be mono- or polysubstituted by C1-C6alkyl, C1-C6haloalkyl, C1-C6alkoxy, C1-C6haloalkoxy, halogen, cyano, hydroxyl or nitro; or

[0012] R2 is C3-C6cycloalkyl, C1-C6alkoxy- or C1-C6alkyl-substituted C3-C6cycloalkyl, 3-oxetanyl or C1-C6alkyl-substituted 3-oxetanyl;

[0013] or, if Q is Q2 or Q3, or is Q1 in which R14 and R22 are a C2-C3alkylene chain, R2 is additionally also a five- to ten-membered monocyclic or fused bicyclic ring system which may be aromatic, saturated or partially saturated and may contain 1 to 4 heteroatoms selected from the group consisting of nitrogen, oxygen and sulfur, where the ring system is attached directly or via a C1-C4alkylene, C2-C4alkenyl-C1-C4alkylene, C2-C4alkynyl-C1-C4alkylene, —N(R12)-C1-C4alkylene, —SO—C1-C4alkylene or —SO2-C1-C4alkylene group to the substituent X1 and where each ring system may not contain more than two oxygen atoms and not more than two sulfur atoms and the ring system for its part may be mono-, di- or trisubstituted by C1-C6alkyl, C1-C6haloalkyl, C2-C6alkenyl, C2-C6haloalkenyl, C2-C6alkynyl, C2-C6haloalkynyl, C1-C6alkoxy, hydroxyl, C1-C6haloalkoxy, C3-C6alkenyloxy, C3-C6alkynyloxy, mercapto, C1-C6alkylthio, C1-C6haloalkylthio, C3-C6alkenylthio, C3-C6haloalkenylthio, C3-C6alkynylthio, C2-C5alkoxyalkylthio, C3-C5acetylalkylthio, C3-C6alkoxycarbonylalkylthio, C2-C4cyanoalkythio, C1-C6alkylsulfinyl, C1-C6haloalkylsulfinyl, C1-C6alkylsulfonyl, C1-C6haloalkylsulfonyl, aminosulfonyl, C1-C2alkylaminosulfonyl, di(C1-C2alkyl)aminosulfonyl, di(C1-C4alkyl)amino, halogen, cyano, nitro, phenyl and benzylthio, where phenyl and benzylthio for their part may be substituted on the phenyl ring by C1-C3alkyl, C1-C3haloalkyl, C1-C3alkoxy, C1-C3haloalkoxy, halogen, cyano or nitro, and where the substituents on the nitrogen in the heterocyclic ring are different from halogen; or

[0014] R2 is hydrogen or unsubstituted C1-C8alkyl if

[0015] a) R1 is substituted by the group R5, or

[0016] b) Q is the group Q2, or

[0017] c) Q is the group Q3 in which X1 is —O(CO)—, —(CO)O—, —N(R6)—O—, —O—NR51—, —SO2NR7—, —NR52SO2— or —NR8—; or

[0018] d) Q is the group Q1 in which X1 is —N(R6)—O—, —O—NR51—, —SO2NR7—, —NR52SO2— or —NR8—, or

[0019] e) Q is the group Q1 in which R14 and R22 in Q1 are a C2-C3alkylene chain and X1 is —O(CO)— or —(CO)O—,

[0020] R3 is C1-C3haloalkyl;

[0021] R4 is hydrogen, halogen, C1-C3alkyl, C1-C3haloalkyl, C1-C3alkoxy, C1-C3alkoxy-C1-C3alkyl or C1-C3alkoxy-C1-C3alkoxy;

[0022] R5 is hydroxyl, C1-C6alkoxy, C3-C6cycloalkyloxy, C1-C6alkoxy-C1-C6alkoxy, C1-C6alkoxy-C1-C6alkoxy-C1-C6alkoxy or C1-C2alkylsulfonyloxy;

[0023] R6, R7, R8, R9, R10, R11, R12, R51, and R52 independently of one another are hydrogen, C1-C6alkyl, C1-C6haloalkyl, C1-C6alkoxycarbonyl, C1-C6alkylcarbonyl, C1-C6alkoxy-C1-C6alkyl, C1-C6alkoxy-C1-C6alkyl substituted by C1-C6alkoxy, benzyl or phenyl, where phenyl and benzyl for their part may be mono- or polysubstituted by C1-C6alkyl, C1-C6haloalkyl, C1-C6alkoxy, C1-C6haloalkoxy, halogen, cyano, hydroxyl or nitro; where R6 and R9 are not simultaneously hydrogen and hydrogen, C1-C6alkoxycarbonyl or C1-C6alkylcarbonyl, respectively;

[0024] Q is Q12

[0025] in which

[0026] A1 is C(R14R15), NR16 or oxygen;

[0027] A2 is C(R17R18), C(O), —C═N—O—R19, oxygen, thio, sulfinyl, sulfonyl, —NR20 or ethylene; with the provisos that A1 is different from oxygen if A2 is oxygen, C(O), thio, sulfinyl, —C═N—O—R19, NR20 or C(R17R18), where R17 and R18 independently of one another are C1-C4alkoxy, C1-C4alkylthio, C1-C4alkylsulfinyl, C1-C4alkylsulfonyl; and A1 is different from NR16 if A2 is thio, sulfinyl or C(R17R18), where R17 and R18 independently of one another are C1-C4alkoxy, C1-C4alkylthio, C1-C4alkylsulfinyl, C1-C4alkylsulfonyl; R14 and R22 independently of one another are hydrogen, C1-C4alkyl, C1-C4haloalkyl, C3-C4alkenyl, C3-C4alkynyl, C1-C4alkylthio, C1-C4alkylsulfinyl, C1-C4alkylsulfonyl, C1-C4alkylsulfonyloxy, C1-C4alkoxy, C1-C4alkoxycarbonyl or C1-C4alkylcarbonyl;

[0028] R15 and R21 independently of one another are hydrogen, C1-C4alkyl, C1-C4haloalkyl, C3-C4alkenyl or C3-C4alkynyl;

[0029] R17 is hydrogen, C1-C4alkyl, C1-C4haloalkyl, C1-C4alkoxy, C1-C4alkylthio, C1-C4alkylsulfinyl or C1-C4alkylsulfonyl;

[0030] R18 is hydrogen, C1-C4alkyl, C1-C4haloalkyl, C3-C4alkenyl, C3-C4alkynyl, C1-C4alkoxy, C1-C4alkylthio, C1-C4alkylsulfinyl, C1-C4alkylsulfonyl or C1-C4dialkoxyalkyl-C1-C4alkyl;

[0031] R20 is C1-C4alkyl, C3-C6cycloalkyl, C3-C4alkenyl, C3-C4alkynyl, C1-C4alkylcarbonyl, C1-C4alkyl-carbonyloxy, di(C1-C4alkyl)aminocarbonyl or benzyl, where the phenyl group may be mono- or polysubstituted by C1-C6alkyl, C1-C6haloalkyl, C1-C6alkoxy, C1-C6haloalkoxy, halogen, cyano, hydroxyl or nitro;

[0032] R19 and R16 independently of one another are hydrogen, C1-C4alkyl, C3-C6cycloalkyl, C3-C4alkenyl, C3-C4alkynyl, benzyl or phenyl, where phenyl and benzyl for their part may be mono- or polysubstituted by C1-C6alkyl, C1-C6haloalkyl, C1-C6alkoxy, C1-C6haloalkoxy, halogen, cyano, hydroxyl or nitro;

[0033] or R14 and R22 together form a C2-C3alkylene chain;

[0034] or R14 and R15 together and/or R17 and R18 together and/or R21 and R22 together form a C2-C4alkylene chain which may be interrupted by oxygen and/or carbonyl and/or sulfur, with the proviso that the oxygen and sulfur atoms are separated by at least one methylene group;

[0035] or R14 and R18 together form a C2-C4alkylene chain; or

[0036] R22 and R18 together form a C2-C4alkylene chain;

[0037] or R18 together with R22 or R14 forms a direct bond;

[0038] or R16 and R18 together form a C2-C4alkylene chain;

[0039] R13 is hydroxyl, O31M+, where M+is an alkali metal cation or ammonium cation, halogen, C1-C12alkylsulfonyloxy, amino, C1-C4alkylthio, C1-C12alkylsulfinyl, C1-C12alkylsulfonyl C1-C12haloalkylthio, C1-C12haloalkylsulfinyl, C1-C12haloalkylsulfonyl, C1-C6alkoxy-C1-C6alkylthio, C1-C6alkoxy-C1-C6alkylsulfinyl, C1-C6alkoxy-C1-C6alkylsulfonyl, C3-C12alkenyl-thio, C3-C12alkenylsulfinyl, C3-C12alkenylsulfonyl, C3-C12alkynylthio, C3-C12alkynylsulfinyl, C3-C12alkynylsulfonyl, C1-C4alkoxycarbonyl-C1-C4alkylthio, C1-C4alkoxycarbonyl-C1-C4alkyl-sulfinyl, C1-C4alkoxycarbonyl-C1-C4alkylsulfonyl, (C1-C4alkoxy)2P(O)O, C1-C4alkyl-(C1-C4alkoxy)P(O)O, H(C1-C4alkoxy)P(O)O, R23R24N, R25R26NNH, R27R28NC(O)O—, R29R30NC(O)NH—, C1-C18alkylcarbonyloxy, C2-C18alkenylcarbonyloxy, C2-C18alkynyl-carbonyloxy, C3-C6cycloalkylcarbonyloxy, C1-C12alkoxycarbonyloxy, C1-C12alkylthio-carbonyloxy, C1-C12alkylthiocarbamoyl, where the alkyl, alkenyl and alkynyl groups may be substituted by halogen, C1-C6alkoxy, C1-C6alkylthio, C1-C6alkylsulfinyl, C1-C6alkylsulfonyl or cyano;

[0040] or R13 is phenoxy, phenylthio, phenylsulfinyl, phenylsulfonyl, phenylsulfonylamino, phenylsulfonyloxy or benzoyloxy, where the phenyl groups for their part may be substituted by one or more halogen, nitro, cyano, C1-C4alkyl, C1-C4haloalkyl, C1-C4alkoxy or C1-C4halo-alkoxy groups;

[0041] or R13 is a group Het1-thio, Het2-sulfinyl, Het3-sulfonyl, Het4—(CO)O or Het5—N(R33); in which Het1, Het2, Het3, Het4 and Het5 independently of one another are a five- to ten-membered monocyclic or fused bicyclic ring system which may be aromatic or partially saturated and may contain 1 to 4 heteroatoms selected from the group consisting of nitrogen, oxygen and sulfur, and where each ring system may not contain more than 2 oxygen atoms and not more than 2 sulfur atoms, and where the ring system itself can be substituted by C1-C6alkyl, C1-C6haloalkyl, C1-C6alkoxy, C1-C6haloalkoxy, C1-C6alkylthio, C1-C6alkylsulfinyl, C1-C6alkyl-sulfonyl, di(C1-C4alkyl)aminosulfonyl, di(C1-C4alkyl)amino, halogen, cyano, nitro or phenyl, and where the substituents on the nitrogen in the heterocyclic ring are different from halogen;

[0042] R23, R24, R25, R26, R27, R28, R29, R30 and R33 independently of one another are C1-C6alkyl;

[0043] or R23 and R24 together or R25 and R26 together or R27 and R28 together or R29 and R30 together are pyrolidino, piperidino, morpholino, thiomorpholino, which may be mono- or polysubstituted by methyl groups; or Q is Q2 3

[0044] in which

[0045] R34 is hydrogen, C1-C4alkyl, C1-C4haloalkyl, C3-C6cycloalkyl, C2-C4alkenyl, C2-C4alkynyl or benzyl, where the phenyl group may be mono- or polysubstituted by C1-C6alkyl, C1-C6halo-alkyl, C1-C6alkoxy, C1-C6haloalkoxy, halogen, cyano, hydroxyl or nitro;

[0046] R35 is hydrogen, C1-C4alkyl, C1-C4haloalkyl, C3-C6cycloalkyl, C3-C4alkenyl, C3-C4alkynyl or benzyl, where the phenyl group may be mono- or polysubstituted by C1-C6alkyl, C1-C6halo-alkyl, C1-C6alkoxy, C1-C6haloalkoxy, halogen, cyano, hydroxyl or nitro;

[0047] R36 is hydroxyl, O−M+, where M+ is an alkali metal cation or ammonium cation, halogen, C1-C12alkylsulfonyloxy, amino, C1-C4alkylthio, C1-C12alkylsulfinyl, C1-C12alkylsulfonyl, C1-C12haloalkylthio, C1-C12haloalkylsulfinyl, C1-C12haloalkylsulfonyl, C1-C6alkoxy-C1-C6alkylthio, C1-C6alkoxy-C1-C6alkylsulfinyl, C1-C6alkoxy-C1-C6alkylsulfonyl, C3-C12alkenyl-thio, C3-C12alkenylsulfinyl, C3-C12alkenylsulfonyl, C3-C12alkynylthio, C3-C12alkynylsulfinyl, C3-C12alkynylsulfonyl, C1-C4alkoxycarbonyl-C1-C4alkylthio, C1-C4alkoxycarbonyl -C1-C4alkyl-sulfinyl, C1-C4alkoxycarbonyl-C1-C4alkylsulfonyl, (C1-C4alkoxy)2P(O)O, C1-C4alkyl-(C1-C4alkoxy)P(O)O, H(C1-C4alkoxy)P(O)O, R37R38N, R39R40NNH, R41R42NC (O)O—, R43R44NC(O)NH—, C1-C18alkylcarbonyloxy, C2-C18alkenylcarbonyloxy, C2-C18alkynyl -carbonyloxy, C3-C6cycloalkylcarbonyloxy, C1-C12alkoxycarbonyloxy, C1-C12alkylthio-carbonyloxy or C1-C12alkylthiocarbamoyl, where the alkyl, alkenyl and alkynyl groups may be substituted by halogen, C1-C6alkoxy, C1-C6alkylthio, C1-C6alkylsulfinyl, C1-C6alkylsulfonyl or cyano; or

[0048] R36 is phenoxy, phenylthio, phenylsulfinyl, phenylsulfonyl, phenylsulfonylamino, phenylsulfonyloxy or benzoyloxy, where the phenyl groups for their part may be mono- or polysubstituted by halogen, nitro, cyano, C1-C4alkyl, C1-C4haloalkyl, C1-C4alkoxy, C1-C4halo-alkoxy,

[0049] or R36 is a group Het7-thio, Het8-sulfinyl, Het9-sulfonyl, Het10—(CO)O or Het11—N(R47); in which Het7, Het8, Het9, Het10 and Het11 independently of one another are a five- to ten-membered monocyclic or fused bicyclic ring system which may be aromatic or partially saturated and may contain 1 to 4 heteroatoms selected from the group consisting of nitrogen, oxygen and sulfur, and where each ring system may not contain more than 2 oxygen atoms and not more than 2 sulfur atoms, and where the ring system for its part may be substituted by C1-C6alkyl, C1-C6haloalkyl, C1-C6alkoxy, C1-C6haloalkoxy, C1-C6alkylthio, C1-C6alkylsulfinyl, C1-C6alkylsulfonyl, di(C1-C4alkyl)aminosulfonyl, di(C1-C4alkyl)amino, halogen, cyano, nitro or phenyl, and where the substituents on the nitrogen in the heterocyclic ring are different from halogen;

[0050] R37, R38, R39, R40, R41, R42, R43, R44 and R47 independently of one another are hydrogen or C1-C6alkyl; or

[0051] R37 and R38 together or R39 and R40 together or R41 and R42 together or R43 and R44 together are pyrolidino, piperidino, morpholino, thiomorpholino, which may be mono- or polysubstituted by methyl groups; or Q is Q34

[0052] in which

[0053] R49 is C1-C4alkyl, C1-C4haloalkyl, C3-C6cycloalkyl or halogen-substituted C3-C6cycloalkyl;

[0054] R50 is C1-C3alkylene which may be substituted by halogen, hydroxyl, C1-C6alkoxy, C2-C6alkenyl, C2-C6alkynyl, C3-C6cycloalkyl, C1-C6alkoxy-C1-C6alkoxy, C1-C6alkoxy,-C1-C6alkoxy-C1-C6alkoxy, (3-oxetanyl)oxy, or by C1-C6alkyl-substituted (3-oxetanyl)oxy, or by benzylthio, benzylsulfinyl, benzylsulfonyl, phenyl, phenoxy, phenylthio, phenylsulfinyl or phenylsulfonyl, where the phenyl- and benzyl-containing groups for their part may be substituted by one or more C1-C6alkyl, C1-C6haloalkyl, C1-C6alkoxy, C1-C6haloalkoxy, halogen, cyano, hydroxyl or nitro groups;

[0055] or R50 is phenyl, where the phenyl-containing group for its part may be substituted by one or more C1-C6alkyl, C1-C16haloalkyl, C1-C6alkoxy, C1-C6haloalkoxy, halogen, cyano, hydroxyl or nitro,

[0056] or R50 is C3-C6cycloalkyl, C1-C6alkoxy- or C1-C6alkyl-substituted C3-C6cycloalkyl, 3-oxetanyl or C1-C6alkyl-substituted 3-oxetanyl; and

[0057] n is 0, 1 or 2; and agronomically acceptable salts/N-oxides/isomers/enantiomers of these compounds.

[0058] The alkyl groups occurring in the definitions of the substituents can be straight-chain or branched and are, for example, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, iso-butyl, tert-butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl and dodecyl and their branched isomers. Alkoxy, alkenyl and alkynyl radicals are derived from the alkyl radicals mentioned. The alkenyl and alkynyl groups can be mono- or polyunsaturated.

[0059] Halogen is generally fluorine, chlorine, bromine or iodine, preferably fluorine and chlorine. This also applies, correspondingly, to halogen in combination with other meanings, such as haloalkyl or halophenyl.

[0060] Haloalkyl groups preferably have a chain length of from 1 to 6 carbon atoms. Haloalkyl is, for example, fluoromethyl, difluoromethyl, trifluoromethyl, chloromethyl, dichloromethyl, trichloromethyl, 2,2,2-trifluoroethyl, 2-fluoroethyl, 2-chloroethyl, pentafluoroethyl, 1,1-difluoro-2,2,2-trichloroethyl, 2,2,3,3-tetrafluoroethyl and 2,2,2-trichloroethyl; preferably trichloro-methyl, difluorochloromethyl, difluoromethyl, trifluoromethyl and dichlorofluoromethyl.

[0061] Suitable haloalkenyl groups are alkenyl groups which are mono- or polysubstituted by halogen, halogen being fluorine, chlorine, bromine and iodine and in particular fluorine and chlorine, for example 2,2-difluoro-1-methylvinyl, 3-fluoropropenyl, 3-chloropropenyl, 3-bromopropenyl, 2,3,3-trifluoropropenyl, 2,3,3-trichloropropenyl and 4,4,4-trifluorobut-2-en-1-yl. Among the C3-C20alkenyl groups which are mono-, di- or trisubstituted by halogen, preference is given to those having a chain length of from 3 to 5 carbon atoms.

[0062] Suitable haloalkynyl groups are, for example, alkynyl groups which are mono- or polysubstituted by halogen, halogen being bromine, iodine and in particular fluorine and chlorine, for example 3-fluoropropynyl, 3-chloropropynyl, 3-bromopropynyl, 3,3,3-trifluoro-propynyl and 4,4,4-trifluorobut-2-yn-1-yl. Among the alkynyl groups which are mono- or polysubstituted by halogen, preference is given to those having a chain length of from 3 to 5 carbon atoms.

[0063] In the context of the present invention, the alkali metal cation M+ (for example in the definition of R13) is preferably the sodium cation or the potassium cation.

[0064] Alkoxy groups preferably have a chain length of from 1 to 6 carbon atoms. Alkoxy is, for example, methoxy, ethoxy, propoxy, i-propoxy, n-butoxy, isobutoxy, sec-butoxy and tert-butoxy and also the isomeric pentyloxy and hexyloxy radicals; preferably methoxy and ethoxy. Alkylcarbonyl is preferably acetyl or propionyl. Alkoxycarbonyl is, for example, methoxycarbonyl, ethoxycarbonyl, propoxycarbonyl, isopropoxycarbonyl, n-butoxycarbonyl, isobutoxycarbonyl, sec-butoxycarbonyl or tert-butoxycarbonyl; preferably methoxycarbonyl or ethoxycarbonyl. Haloalkoxy groups preferably have a chain length of from 1 to 8 carbon atoms. Haloalkoxy is, for example, fluoromethoxy, difluoromethoxy, trifluoromethoxy, 2,2,2-trifluoroethoxy, 1,1,2,2-tetrafluoroethoxy, 2-fluoroethoxy, 2-chloroethoxy, 2,2-difluoroethoxy and 2,2,2-trichloroethoxy; preferably difluoromethoxy, 2-chloroethoxy and trifluoromethoxy. Alkylthio groups preferably have a chain length of from 1 to 8 carbon atoms. Alkylthio is, for example, methylthio, ethylthio, propylthio, isopropylthio, n-butylthio, isobutylthio, sec-butylthio or tert-butylthio, preferably methylthio and ethylthio. Alkylsulfinyl is, for example, methylsulfinyl, ethylsulfinyl, propylsulfinyl, isopropylsulfinyl, n-butylsulfinyl, isobutylsulfinyl, sec-butylsulfinyl, tert-butylsulfinyl; preferably methylsulfinyl and ethylsulfinyl.

[0065] Alkylsulfonyl is, for example, methylsulfonyl, ethylsulfonyl, propylsulfonyl, isopropylsulfonyl, n-butylsulfonyl, isobutylsulfonyl, sec-butylsulfonyl or tert-butylsulfonyl; preferably methylsulfonyl or ethylsulfonyl. Alkoxyalkoxy groups preferably have a chain length of from 1 to 8 carbon atoms. Examples of alkoxyalkoxy groups are: methoxymethoxy, methoxyethoxy, methoxypropoxy, ethoxymethoxy, ethoxyethoxy, propoxymethoxy or butoxybutoxy. Alkylamino is, for example, methylamino, ethylamino, n-propylamino, isopropylamino or the isomeric butylamines. Dialkylamino is, for example, dimethylamino, methylethylamino, diethylamino, n-propylmethylamino, dibutylamino and diisopropylamino. Preference is given to alkylamino groups having a chain length of from 1 to 4 carbon atoms. Alkoxyalkyl groups preferably have a chain length of 1 to 6 carbon atoms. Alkoxyalkyl is, for example, methoxymethyl, methoxyethyl, ethoxymethyl, ethoxyethyl, n-propoxymethyl, n-propoxyethyl, isopropoxymethyl or isopropoxyethyl. Alkylthioalkyl groups preferably have from 1 to 8 carbon atoms. Alkylthioalkyl is, for example, methylthiomethyl, methylthioethyl, ethylthiomethyl, ethylthioethyl, n-propylthiomethyl, n-propylthioethyl, isopropylthiomethyl, isopropylthioethyl, butylthiomethyl, butylthioethyl or butylthiobutyl. The cycloalkyl groups preferably have from 3 to 8 ring carbon atoms, for example cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl and cyclooctyl. Phenyl, also as part of a substituent such as phenoxy, benzyl, benzyloxy, benzoyl, phenylthio, phenylalkyl, phenoxyalkyl, may be substituted. In this case, the substituents can be in ortho, meta and/or para position. The preferred substituent positions are the ortho and para positions to the ring attachment point.

[0066] The compounds of the formula I may occur in different tautomeric forms, for example, if R3 is hydroxyl, in the preferred formulae I′ and I″″ 5

[0067] The invention also embraces the salts which can be formed by compounds of the formula I, preferably with amines, alkali metal and alkaline earth metal bases or quarternary ammonium bases. Suitable salt formers are described, for example, in WO 98/41089.

[0068] The invention also embraces the salts which can be formed by the compounds of the formula I with amines, alkali metal and alkaline earth metal bases or quarternary ammonium bases. Among the alkali metal and alkaline earth metal hydroxides, the hydroxides of lithium, sodium, potassium, magnesium or calcium, in particular those of sodium or potassium, may be emphasized as salt formers.

[0069] Examples of amines suitable for ammonium salt formation are both ammonia and primary, secondary and tertiary C1-C18alkylamines, C1-C4hydroxyalkylamines and C2-C4alkoxy-alkylamines, for example methylamine, ethylamine, n-propylamine, isopropylamine, the four isomeric butylamines, n-amylamine, isoamylamine, hexylamine, heptylamine, octylamine, nonylamine, decylamine, pentadecylamine, hexadecylamine, heptadecylamine, octadecylamine, methylethylamine, methylisopropylamine, methylhexylamine, methylnonyl-amine, methylpentadecylamine, methyloctadecylamine, ethylbutylamine, ethylheptylamine, ethyloctylamine, hexylheptylamine, hexyloctylamine, dimethylamine, diethylamine, di-n-propylamine, diisopropylamine, di-n-butylamine, di-n-amylamine, diisoamylamine, dihexylamine, diheptylamine, dioctylamine, ethanolamine, n-propanolamine, isopropanol-amine, N,N-diethanolamine, N-ethylpropanolamine, N-butylethanolamine, allylamine, n-butenyl-2-amine, n-pentenyl-2-amine, 2,3-dimethylbutenyl-2-amine, dibutenyl-2-amine, n-hexenyl-2-amine, propylenediamine, trimethylamine, triethylamine, tri-n-propylamine, triisopropylamine, tri-n-butylamine, triisobutylamine, tri-sec-butylamine, tri-n-amylamine, methoxyethylamine and ethoxyethylamine; heterocyclic amines, for example pyridine, quinoline, isoquinoline, morpholine, piperidine, pyrrolidine, indoline, quinuclidine and azepine; primary arylamines, for example anilines, methoxyanilines, ethoxyanilines, o,m,p-toluidines, phenylenediamines, benzidines, naphthylamines and o,m,p-chloroanilines; but in particular triethylamine, isopropylamine and diisopropylamine.

[0070] Preferred quarternary ammonium bases which are suitable for salt formation correspond, for example, to the formula [N(RaRbRcRd)]OH, in which Ra, Rb, Rc, and Rd independently of one another are C1-C4alkyl. Other suitable tetraalkylammonium bases with other anions can be obtained, for example, by anion exchange reactions.

[0071] Compounds of formula I, wherein p is 0, are preferred.

[0072] Preferred compounds of the formula I are those in which R1 is —CH2—, —CH2CH2—, —CF2, —CH═CHCH2—, —CH(CH3)— or —C═CCH2—, but particularly preferably —CH2— where in each case the free valences on the left are attached to the pyridine ring.

[0073] Preference is furthermore given to those compounds of the formula I, in which X1 is oxygen, sulfonyl or a group —NR52SO2—, in particular oxygen.

[0074] Of particular interest are compounds of the formula I, in which R2 is —CH2OCH3, —CH2OCH2CH3, —CH2CH2OCH3, —CH2CH2SO2CH3 or —CH2OCH2CH2OCH3, preferably —CH2CH2OCH3, those compounds standing out in which X1 is oxygen and R1 is —CH2—.

[0075] Among this group, preference is given to those compounds in which Q is Q1 and R13 is hydroxyl.

[0076] Emphasis is furthermore given to the compounds of the formula I in which R2 67

[0077] If, in these preferred meanings of R2, no free valency is indicated, as, for example, in the case of 8

[0078] the point of attachment is the carbon atom indicated by “CH”.

[0079] In a further preferred group of compounds of the formula I, R3 is CF3, CF2CF3, CF2Cl, CF2H or CCl3, particularly preferably CF3, where R4 is preferably hydrogen or methyl, particularly preferably hydrogen.

[0080] R6, R7, R8, R9, R10, R11, R12, R51 and R52 independently of one another are in particular hydrogen, C1-C4alkyl, C1-C6alkoxy-C1-C6alkyl or C1-C6alkoxy-C1-C6alkyl which is substituted by C1-C6alkoxy, where in a preferred group of compounds of the formula I additionally Q is Q2 and R1 is methylene.

[0081] Very particularly preferably, Q is Q1 and R13 is hydroxyl or halogen, in particular hydroxyl. Among this group, emphasis is given to those compounds in which

[0082] a) A1 is C(R14R15) or NR16 and A2 is C(R17R18), C(O) or oxygen, or

[0083] b) A1 is C(R14R15) and A2 is C(R17R18) and R14 and R22 together form a C2-C3alkylene chain, preferably an ethylene chain, where R15, R17, R18 and R21, are particularly preferably hydrogen; or

[0084] c) A2 is C(O) or C(R17R18), A1 is C(R14R15) and R14, R15, R17 and R18 independently of one another are hydrogen, methyl, ethyl, methoxycarbonyl or ethoxycarbonyl; or

[0085] d) R14 and R15 or R21 and R22 together form a C2alkylene chain (cyclopropyl ring), A2 is CH2 and R21 and R22 or R14 and R15 independently of one another are hydrogen, C1-C4alkyl, methoxycarbonyl or ethoxycarbonyl; or

[0086] e) A2 is C(R17R18) and A1 is C(R14R15) and R18 and R14 together form a C2-C3alkylene chain.

[0087] In a further outstanding group of compounds of the formula I, Q is Q3, R49 is cyclopropyl and R50—S(O)n is methylthio, ethylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl.

[0088] The compounds of the formula I can be prepared by processes known per se, for example those described in WO 97/46530 or WO 00/15615 or WO/0039094, for example in the case of compounds of the formula I, 9

[0089] in which R1, R2, R3, R4 and X1 are as defined under formula I and Q is a group 10

[0090] by, for example, either

[0091] a) reacting a compound of the formula Ia 11

[0092] in which R1, R2, R3, R4 and X1 are as defined under formula I and Y1 is a leaving group, for example halogen or cyano, in an inert organic solvent in the presence of a base with a compound of the formula II 12

[0093] in which R22, R21, A2 and A1 are as defined under formula I, to give the compounds of the formulae IIIa and IIb 13

[0094] and then isomerizing these for example in the presence of a base and a catalytic amount of dimethylaminopyridine (DMAP) or a source of cyanide, for example acetone cyanohydrin; or

[0095] b) reacting a compound of the formula Ib 14

[0096] in which R1, R2, R3, R4 and X1 are as defined under formula I, with a compound of the formula II 15

[0097] in which R22, R21, A1 and A2 are as defined under formula I, in an inert organic solvent in the presence of a base and a coupling agent to give the compounds of the formula IIIa or IIIb 16

[0098] and then isomerizing these, for example as described under route a).

[0099] Compounds of the formula I, in which Q is a group 17

[0100] are prepared similarly to a known process (for example WO 97/46530), wherein either

[0101] a) a compound of the formula Ia 18

[0102] in which R1, R2, R3, R4 and X1 are as defined under formula I and Y1 is a leaving group, for example halogen or cyano, is reacted with a compound of the formula IIa 19

[0103] in which R34 and R35 are as defined, in an inert organic solvent in the presence of a base to give the compound of the formula IIIc 20

[0104] in which R1, R2, R3, R4, R34, R35 and X1 are as defined under formula I, and this compound is then isomerized, for example in the presence of a base and a catalytic amount of a source of cyanide; or

[0105] b) a compound of the formula Ib 21

[0106] in which R1, R2, R3, R4 and X1 are as defined under formula I, is reacted with a compound of the formula IIa 22

[0107] in which R34 and R35 are as defined above, in an inert organic solvent in the presence of a base and a coupling agent to give the compound of the formula IIIc 23

[0108] and this compound is then isomerized as described under route a).

[0109] The compounds of the formula I, in which Q is a group 24

[0110] in which n is 0 and R50 and R49 are as defined above, are prepared similarly to known processes (for example those described in WO 00/15615, WO/0039094 or WO 97/43270), wherein either

[0111] a) a compound of the formula IV 25

[0112] in which X1, R1, R2, R3, R4 and R49 are as defined above, is converted in the presence of a base, carbon disulfide and an alkylating agent of the formula V

R50—Y2  (V),

[0113] in which R50 is as defined under formula I, and Y2 is a leaving group, for example halogen or sulfonate, into the compound of the formula VI 26

[0114] in which R1, R2, R3, R4, R50, X1 and R49 are as defined above, and this compound is then cyclized with hydroxylamine hydrochloride, if appropriate in a solvent, in the presence of a base, for example sodium acetate, to give the isomeric compounds of the formulae Ic and Id 27

[0115] and these compounds are then oxidized with an oxidizing agent, for example with peracids, for example meta-chloroperbenzoic acid (m-CPBA) or peracetic acid, to give the corresponding sulfoxides (n=1) and sulfones (n=2) of the formulae Ie and If, respectively. Isomers of the formulae Ic and Id (in which n=0) or Ie and If (in which n=1 or 2) can be separated and purified by column chromatography, using a suitable mobile phase.

[0116] The intermediates of the formulae Ia, Ib, IV and VI are novel and were developed specifically for the preparation of the compounds of the formula I. Accordingly, they also form part of the subject-matter of the present invention. Together, the novel intermediates of the formulae Ia, Ib, IV and VI correspond to formula XX 28

[0117] in which

[0118] Q is hydroxyl, halogen, cyano or C1-C6alkoxy, or is a group of the formula 29

[0119] or —CH2(CO)R49; and

[0120] R1, R3, R4, R49, R50, X1 and p are as defined under formula I and R2 is a C1-C8alkyl, C3-C6alkenyl or C3-C6alkynyl group which is mono- or polysubstituted by halogen, hydroxyl, amino, formyl, nitro, cyano, mercapto, carbamoyl, C1-C6alkoxy, C1-C6alkoxycarbonyl, C2-C6alkenyl, C2-C6haloalkenyl, C2-C6alkynyl, C2-C6haloalkynyl, C3-C6cycloalkyl, by halogen-substituted C3-C6cycloalkyl, or by C3-C6alkenyloxy, C3-C6alkynyloxy, C1-C6haloalkoxy, C3-C6haloalkenyloxy, cyano-C1-C6alkoxy, C1-C6alkoxy-C1-C6alkoxy, C1-C6alkoxy-C1-C6alkoxy-C1-C6alkoxy, C1-C6alkylthio-C1-C6alkoxy, C1-C6alkylsulfinyl-C1-C6alkoxy, C1-C6alkylsulfonyl-C1-C6alkoxy, C1-C6alkoxycarbonyl-C1-C6alkoxy, C1-C6alkoxycarbonyl, C1-C6alkylcarbonyl, C1-C6alkylthio, C1-C6alkylsulfinyl, C1-C6alkylsulfonyl, C1-C6haloalkylthio, C1-C6haloalkylsulfinyl, C1-C6-haloalkylsulfonyl, oxiranyl, which for its part may be substituted by C1-C6alkyl, or by (3-oxetanyl)oxy, which for its part may be substituted by C1-C6alkyl, or by benzylthio, benzylsulfinyl, benzylsulfonyl, C1-C6alkylamino, di(C1-C6alkyl)amino, RgS(O)2O, R10N(R11)SO2—, thiocyanato, phenyl, phenoxy, phenylthio, phenylsulfinyl or phenylsulfonyl; where the phenyl- or benzyl-containing groups for their part may be substituted by one or more C1-C6alkyl, C1-C6haloalkyl, C1-C6alkoxy, C1-C6haloalkoxy, halogen, cyano, hydroxyl or nitro groups, or

[0121] R2 is phenyl which may be mono- or polysubstituted by C1-C6alkyl, C1-C6haloalkyl, C1-C6alkoxy, C1-C6haloalkoxy, halogen, cyano, hydroxyl or nitro; or

[0122] R2 is C3-C6cycloalkyl, C1-C6alkoxy- or C1-C6alkyl-substituted C3-C6cycloalkyl, 3-oxetanyl or C1-C6alkyl-substituted 3-oxetanyl; or

[0123] if X1 is —N(R6)—O—, —O—NR51, SO2NR7— or —NR52SO2— and R6, R7, R51 and R52 are as defined under formula I,

[0124] R2 may additionally be hydrogen, unsubstituted C1-C6alkyl, or a five- to ten-membered monocyclic or fused bicyclic ring system which may be aromatic, saturated or partially saturated and may contain 1 to 4 heteroatoms selected from the group consisting of nitrogen, oxygen and sulfur, where the ring system is attached directly or via a C1-C4alkylene, C2-C4alkenyl-C1-C4alkylene, C2-C4alkynyl-C1-C4alkylene, —N(R12)—C1-C4alkylene, —SO—C1-C4alkylene or —SO2—C1-C4alkylene group to the substituent X1, and where each ring system may not contain more than 2 oxygen atoms and not more than two sulfur atoms, and where the ring system for its part may be mono-, di- or trisubstituted by C1-C6alkyl, C1-C6haloalkyl, C2-C6alkenyl, C2-C6haloalkenyl, C2-C6alkynyl, C2-C6haloalkynyl, C1-C6alkoxy, hydroxyl, C1-C6haloalkoxy, C3-C6alkenyloxy, C3-C6alkynyloxy, mercapto, C1-C6alkylthio, C1-C6-haloalkylthio, C3-C6alkenylthio, C3-C6haloalkenylthio, C3-C6alkynylthio, C2-C5alkoxyalkylthio, C3-C5acetylalkylthio, C3-C6alkoxycarbonylalkylthio, C2-C4cyanoalkylthio, C1-C6alkylsulfinyl, C1-C6haloalkylsulfinyl, C1-C6alkylsulfonyl, C1-C6haloalkylsulfonyl, aminosulfonyl, C1-C2alkylaminosulfonyl, di(C1-C2alkyl)aminosulfonyl, di(C1-C4alkyl)amino, halogen, cyano, nitro, phenyl and benzylthio, where phenyl and benzylthio for their part may be substituted on the phenyl ring by C1-C3alkyl, C1-C3haloalkyl, C1-C3alkoxy, C1-C3haloalkoxy, halogen, cyano or nitro, and where the substituents on the nitrogen in the heterocyclic ring are different from halogen.

[0125] The preparation of the compounds of the formula I is illustrated in more detail in reaction schemes 1 and 2 below. 30

[0126] Reaction scheme 1 is preferably used to prepare the compounds of the formula I having the group Q1, in which R13 is hydroxyl, and the compounds of the formula I having the group Q2, in which R36 is hydroxyl. 31

[0127] Compounds of the formula I, in which p is 1, i.e. the corresponding N-oxides of the formula I, can be prepared by reacting a compound of the formula I, in which p is 0, with a suitable oxidizing agent, for example the H2O2/urea adduct in the presence of an acid anhydride, e.g. trifluoroacetic anhydride. Such oxidations are known from the literature, for example from J. Med. Chem., 32 (12), 2561-73, 1989 or WO 00/15615.

[0128] According to reaction scheme 1, route a), the carboxylic acid derivatives of the formula Ia in which Y1 is a leaving group such as halogen, for example iodine, bromine, and in particular chlorine, N-oxyphthalimide or N,O-dimethylhydroxylamino or part of an activated ester, for example 32

[0129] (formed from dicyclohexylcarbodiimide (DCC) and the corresponding carboxylic acid) or 33

[0130] formed from N-ethyl N′-(3-dimethylaminopropyl)carbodiimide (EDC) and the corresponding carboxylic acid) are used as starting materials for preparing the compounds of the formula I in which Q denotes the groups Q1 and Q2 and R13 and R36 are hydroxyl. The starting materials are reacted in an inert organic solvent such as a halogenated hydrocarbon, for example dichloromethane, a nitrile, for example acetonitrile, or an aromatic hydrocarbon, for example toluene, and in the presence of a base such as an alkylamine, for example triethylamine, an aromatic amine, for example pyridine or 4-dimethylaminopyridine (DMAP) with the dione derivatives of the formula II or pyrazoles of the formula IIa, to give the isomeric enol ethers of the formula IIIa, IIIb or IIIc. This esterification can be carried out at temperatures of from 0° C. to 110° C.

[0131] The isomerization of the ester derivatives of the formulae IIIa, IIIb and IIIc to derivatives of the formula I (in which R13 and R36 are hydroxyl) can be carried out, for example, similarly to EP-A-0 353 187, EP-A-0 316 491 or WO 97/46530 in the presence of a base such as an alkylamine, for example triethylamine, a carbonate, for example potassium carbonate, and a catalytic amount of DMAP or a source of cyanide, such as acetone cyanohydrin or potassium cyanide. In particular if a cyanide compound of the formula Ia (Y1=cyano) is used, or in the presence of a catalytic amount of acetone cyanohydrin or potassium cyanide, the two reaction steps can be carried out in situ without isolating the intermediates III.

[0132] According to reaction scheme 1, route b), the desired derivatives of the formula I (in which R13 and R36 are hydroxyl) can be obtained, for example, similarly to E. Haslem, Tetrahedron, 2409-2433, 36, 1980, by esterifying the carboxylic acids of the formula Ib with the dione derivatives of the formula II or pyrazoles of the formula IIa in an inert solvent such as a halogenated hydrocarbon, for example dichloromethane, a nitrile, for example acetonitrile, or an aromatic hydrocarbon, for example toluene, in the presence of a base such as an alkylamine, for example triethylamine, and a coupling agent such as 2-chloro-1-methyl-pyridinium iodide. Depending on the solvent used, this esterification is carried out at temperatures of from 0° C. to 110° C., giving initially, as described under route a), the isomeric ester of the formula IIIa, II Ib or IIIc, which can be isomerized as described under route a), for example in the presence of a base and a catalytic amount of DMAP, or a source of cyanide, for example acetone cyanohydrin, to give the desired derivative of the formula I (R13 and R36=hydroxyl). The activated carboxylic acid derivatives of the formula Ia in reaction scheme 1 (route a), in which Y, is a leaving group such as halogen, for example bromine, iodine or, in particular, chlorine, can be prepared by known standard processes, for example those described in C. Ferri “Reaktionen der organischen Synthese” [Reactions of organic sythesis], Georg Thieme Verlag, Stuttgart, 1978, page 460 ff. Such reactions are generally known and described in the literature in different variations with respect to the leaving group Y1.

[0133] The preparation of the compounds of the formula I, in which Q denotes the group Q3, can be carried out according to reaction scheme 2 by reacting the β-diketone derivative of the formula IV for example similarly to Synthesis 1991, 301; ibid. 1988, 793; or Tetrahedron 32, 3055, 1976, with carbon disulfide in the presence of a base such as a carbonate, for example potassium carbonate, a metal hydride, for example sodium hydride, or potassium fluoride on aluminum, and an alkylating agent of the formula V, in which Y2 is a leaving group such as halogen, for example iodine, bromine and, in particular, chlorine, CH3SO2O— or 34

[0134] This reaction is expediently carried out in a solvent such as an amide, for example N,N-dimethylformamide (DMF), a sulfoxide, for example dimethyl sulfoxide (DMSO), or a nitrile, for example acetonitrile. The ketene thioacetal of the formula VI that is formed is cyclized with the aid of hydroxylamine hydrochloride in the presence of a base such as sodium acetate in a solvent such as an alcohol, for example ethanol, or an ether, for example tetrahydrofuran, to give the isomeric compounds of the formulae Ic and Id (in which n is 0). This cyclization reaction is carried out at temperatures of from 0° C. to 100° C. If appropriate, the compounds of the formulae Ic and Id in which n is 0 can be oxidized similarly to known standard processes as described, for example, in H. O. House, “Modern Synthetic Reactions”, W. A. Benjamin, Inc., Menlo Park, Calif., 1972, pages 334-335 and 353-354, to give the corresponding sulfones and sulfoxides of the formulae Ie and If (n=1 or 2).

[0135] The compounds of the formula IV in reaction scheme 2 can be obtained by standard processes for example from the corresponding compounds of the formula Ia 35

[0136] in which R1, R2, R3, R4, and X1 are as defined above and Y1 is a leaving group, for example halogen, for example by Claisen condensation, or from the compounds of the formula Ia by reaction with a ketocarboxylic acid salt of the formula VII 36

[0137] in which R49 is as defined under formula I and M+ is an alkali metal ion (cf., for example, WO 96/26192).

[0138] Compounds of the formula I, in which R1 is, in particular C1-C2alkyl, can, for example, also be prepared by heating an N-oxide of the formula IX under known reaction conditions in the presence of an acid anhydride (see, for example, Konno, K.; Hashimoto, K.; Shirahama, H.; Matsumoto, T.; Heterocycles 1986, 24, 2169, or WO 00/1 5615) and hydrolyzing the resulting products (Ig) in a protic solvent, for example water or a water/methanol mixture, if appropriate in the presence of a base (for example lithium hydroxide or sodium hydroxide), and then converting the resulting alcohol X in the presence of a base, for example sodium hydride or potassium hydroxide, if appropriate in the presence of a phase-transfer catalyst or a crown ether, and an alkylating agent R2-Y3, in which R2 is as defined under formula I and Y3 is a leaving group, for example halogen or methyl sulfonate, in an aprotic solvent, for example, tetrahydrofuran or dimethylformamide, into the corresponding derivatives of the formula Ih (in which X1 is oxygen). Compounds of the formula I, in which R2 is C1-C6alkoxymethyl or 2-tetrahydropyranyl or 2-tetrahydrofuryl, can be prepared, for example, by treating an alcohol of the formula X with a vinyl ether of the formula VE1, in which R03, R04, and R05 are C1-C6alkyl or R03 together with R05 forms a C2-C3alkylene chain, in the presence of an acidic catalyst, for example para-toluenesulphonic acid, in an inert solvent, for example methylene chloride. Such reactions are generally known in the literature (see, for example, Synthesis, p. 169,1973). The two reaction sequences are demonstrated using the example below: 37

[0139] Compounds of the formula I, in which R1 is, in particular, C1-C2alkyl or C1-C2haloalkyl, can, for example, also be prepared by oxidzing a compound of the formula XI, in which R13 is in particular chlorine, C1-C4alkoxycarbonyloxy or benzoylcarbonyloxy (prepared similarly to WO 00/15615 or WO/0039094), under known halogenation conditions using, for example, N-bromosuccinimide or N-chlorosuccinimide in the presence of light and a free-radical initiator such as benzoyl peroxide to give the 1-bromo or 1-chloro, 1,1-dibromo or 1,1-dichloro compound and then refunctionalizing these compounds into the corresponding derivatives of the formula I, for example by reaction with a nucleophile R2-Z, in which Z is, for example, —SH, —OH, —C(O)OH, —O—N(R51)H, —N(R6)—OH, —SO2N(R52)H or —N(R8)H and R2, R52, R8, R6 and R51 are as defined under formula I, in the presence of a base, for example sodium hydride, potassium hydroxide or potassium carbonate, followed by aqueous work-up. These reaction sequences, too, are demonstrated by the example below. 38

[0140] Compounds of the formula I, in which Q denotes Q1 or Q2 and in which R13 or R36 are different from hydroxyl or halogen, can be prepared by conversion processes generally known from the literature, for example acylations or carbamoylations with appropriate acid chlorides from compounds of the formula I, in which R13 or R36 is hydroxyl, in the presence of a suitable base, or they can be prepared by nucleophilic substitution reactions on chlorides of the formula I, in which R13 and R36 are chlorine, the chlorides likewise being obtainable according to known processes by reaction with a chlorinating agent, such as phosgene, thionyl chloride or oxalyl chloride. The starting materials used are, for example, appropriately substituted amines, or hydroxylamines directly, or alkylsulfonamides, mercaptans, thiophenols, phenols, heterocyclic amines or heterocyclic thiols in the presence of a base, for example 5-ethyl-2-methylpyridine, diisopropylethylamine, triethylamine, sodium bicarbonate, sodium acetate or potassium carbonate.

[0141] Compounds of the formula I, in which R13 and R36 contain thio groups, can be oxidized similarly to known standard processes using, for example, peracids, for example meta-chloroperbenzoic acid (m-CPBA) or peracetic acid, to give the corresponding sulfones and sulfoxides of the formula I. The degree of oxidation at the sulfur atom (SO— or SO2—) can be controlled by the amount of oxidizing agent.

[0142] The resulting derivatives of the formula I, in which R13 and R36 are different from hydroxyl, can likewise occur in different isomeric forms which, if appropriate, can be isolated in pure form. Accordingly, the invention also embraces all of these stereoisomeric forms. Examples of these isomeric forms are the formulae I*, I** and I*** below in which Q denotes the group Q1. 39

[0143] The compounds of the formulae II and IIa are known and can be prepared similarly as described, for example, in WO 92/07837, JP 10265441, DE-A-3818958, EP-A-0 338 992, DE-A-3902818, EP-A-0 278 742, WO 98/29412, JP 02059566, U.S. Pat. No. 5,089,046, GB-A-2205316, WO 00/27821 or EP-A-0 384 736.

[0144] The required intermediates of the formula Ib (or Ik, Il or Im) are synthesized similarly to known processes as described, for example, in WO 00/15615, WO/00139094 or WO 97/46530, or they can be prepared for example, according to generally known conversion methods such as the Stille (see, for example Angew. Chem. 1986, 98(6), 504-19), Heck (see, for example, Angew. Chem. 1994, 106 (23/24), 2473-506), Sonogashira (see, for example, “Comprehensive Organometallic Synthesis”, Pergamon Verlag, Oxford, Vol 3, 1991, page 521 ff.) or Wittig (for example C. Ferri “Reaktionen der organischen Synthese”, Georg Thieme Verlag, Stuttgart, 1978, p. 354 ff.) reactions, starting from halogen derivatives of the formula XIV (preparation as described in WO 00/15615 or WO/0039094) or XVII (preparation similar to EP 522392) (reaction scheme 5): 40

[0145] Intermediates of the formula Ib, in which R1, R2, R3, R4 and X1 are as defined under formula I, can also be prepared by the method according to reaction scheme 6: 41

[0146] Using generally known oxidation methods such as dihydroxylation, Wacker oxidation, epoxidation, hydroboration with subsequent oxidation, starting with vinyl or allyl compounds of the formula XVIII (preparation as described in WO 00/15615 or WO/0039094), intermediates of the formulae Il, In, Iq and Ir are obtained which can be converted by conversion processes known to the person skilled in the art (for example alcohol activation, for example as sulfonate, alkylation, for example using an alkylating agent R2—Y3 or R5-Y3, in which R2 and R5 are as defined under formula I and Y3 is a leaving group, for example halogen), in the presence of a base, or using nucleophile reactions, for example with a nucleophile Z—R2, in which Z and R2 are as defined above, into compounds of the formula I.

[0147] Intermediates of the formula Ib, in which R1 is C1-C2alkyl and R2, R3, R4and X1 are as defined under formula I, can also be prepared by reacting a compound of the formula XIVa, in which R3 and R4 are as defined above under formula I and Y4 is halogen, with a nucleophile R2—Z, in which Z is —SH, —OH, —C(O)OH, —O—N(R51)H, —N(R6)—OH —SO2N(R52)H or —N(R8)H and R2, R52, R8, R6, R51 are as defined above under formula I, in the presence of a base such as sodium hydride or an alkaline earth metal oxide or carbonate in an inert solvent such as dimethylformamide or THF at temperatures between −5 and 160° C., or, to prepare the corresponding sulfinyl or sulfonyl derivatives of the formula Iu, by reacting with an oxidizing agent such as m-chloroperbenzoic acid or sodium periodate, or sodium perborate, with, depending on the degree of oxidation, temperature control known to the person skilled in the art (for example −30° C.−+50° C. for n=1 and −20° C.-+100° C. for n=2 respectively) , in an inert solvent such as dichloromethane, to give compound of the formula Iv. In reaction scheme 7 below, this is illustrated in more detail for the case Z═OH, SH, SO2N(R52)H and N(R8)H: 42

[0148] Intermediates of the formula I, in which Q denotes a group OR02 (R02=C1-C6alkyl), can be converted by hydrolysis using, for example, a base, for example LiOH, in a protic solvent, for example H2O or H2O/methanol mixtures, into products of the formula Ib.

[0149] For preparing all further compounds of the formula I functionalized according to the definitions of R1, R2, R3, R4 and X1, there are a large number of suitable known standard methods, for example alkylation, halogenation, acylation, amidation, oximation, oxidation and reduction, the choice of the preparation methods which are suitable depending on the properties (reactivity) of the substituents in the intermediates.

[0150] The reactions to give compounds of the formula I are advantageously carried out in aprotic inert organic solvents. Such solvents are hydrocarbons such as benzene, toluene, xylene or cyclohexane, chlorinated hydrocarbons such as dichloromethane, trichloromethane, tetrachloromethane or chlorobenzene, ethers such as diethyl ether, ethylene glycol dimethyl ether, diethylene glycol dimethyl ether, tetrahydrofuran or dioxane, nitrites such as acetonitrile or propionitrile, amides such as N,N-dimethylformamide, diethylformamide or N-methylpyrrolidinone. The reaction temperatures are advantageously between −20° C. and +120° C. In general, the reactions are slightly exothermic and, as a rule, they can be carried out at room temperature. To shorten the reaction time, or else to start the reaction, the mixture may be heated briefly to the boiling point of the reaction mixture. The reaction times can also be shortened by adding a few drops of base as reaction catalyst. Suitable bases are, in particular, tertiary amines such as trimethylamine, triethylamine, quinuclidine, 1,4-diazabicyclo[2.2.2]octane, 1,5-diazabicyclo[4.3.0]non-5-ene or 1,5-diazabicyclo-[5.4.0]undec-7-ene. However, inorganic bases such as hydrides, e.g. sodium hydride or calcium hydride, hydroxides, e.g. sodium hydroxide or potassium hydroxide, carbonates such as sodium carbonate and potassium carbonate, or hydrogen carbonates such as potassium hydrogen carbonate and sodium hydrogen carbonate may also be used as bases. The bases can be used as such or else with catalytic amounts of a phase-transfer catalyst, for example a crown ether, in particular 18-crown-6, or a tetraalkylammonium salt.

[0151] The compounds of the formula I can be isolated in the customary manner by concentrating and/or by evaporating the solvent and purified by recrystallization or trituration of the solid residue in solvents in which they are not readily soluble, such as ethers, aromatic hydrocarbons or chlorinated hydrocarbons.

[0152] All application methods which are conventionally used in agriculture, for example pre-emergence application, post-emergence application and seed treatment, as well as various methods and techniques, for example the controlled release of active ingredients, are suitable for the use according to the invention of the compounds of the formula I or of compositions comprising them. To this end, the active ingredient in solution is applied to mineral carriers for granules or to polymerized granules (urea/formaldehyde) and dried. If appropriate, an additional coating can be applied (coated granules), which allows the active ingredient to be released in a controlled manner over a specific period of time.

[0153] The compounds of the formula I can be employed as herbicides as such, i.e. as obtained from synthesis. However, they are preferably processed in the customary manner together with the auxiliaries conventionally used in the art of formulation, for example to give emulsifiable concentrates, directly sprayable or dilutable solutions, dilute emulsions, wettable powders, soluble powders, dusts, granules or microcapsules. Such formulations are described, for example, in WO 97/34485 on pages 9 to 13. The application methods such as spraying, atomizing, dusting, wetting, scattering or pouring, as well as the type of composition, are chosen to suit the intended aims and the prevailing circumstances.

[0154] The formulations, i.e. the compositions, preparations or products which comprise the active ingredient of the formula I or at least one active ingredient of the formula I and, as a rule, one or more solid or liquid formulation auxiliaries, are prepared in the known manner, for example by intimately mixing and/or grinding the active ingredients together with the formulation auxiliaries, for example solvents or solid carriers. Furthermore, surface-active compounds (surfactants) may additionally be used when preparing the formulations. Examples of solvents and solid carriers are indicated for example in WO 97/34485 on page 6.

[0155] Suitable surface-active compounds are, depending on the nature of the active ingredient of the formula I to be formulated, nonionic, cationic and/or anionic surfactants and surfactant mixtures which have good emulsifying, dispersing and wetting properties. Examples of suitable anionic, nonionic and cationic surfactants are enumerated, for example, in WO 97/34485 on pages 7 and 8. The surfactants conventionally used in the art of formulation which are described, inter alia, in “McCutcheon's Detergents and Emulsifiers Annual” MC Publishing Corp., Ridgewood N.J., 1981, Stache, H., “Tensid-Taschenbuch” [“Surfactants Guide”], Carl Hanser Verlag, Munich/Vienna, 1981 and M. and J. Ash, “Encyclopedia of Surfactants”, Vol I-III, Chemical Publishing Co., New York, 1980-81 are furthermore also suitable for preparing the herbicidal compositions according to the invention.

[0156] As a rule, the herbicidal formulations comprise 0.1 to 99% by weight, in particular 0.1 to 95% by weight, of herbicide, 1 to 99.9% by weight, in particular 5 to 99.8% by weight, of a solid or liquid formulation auxiliary and 0 to 25% by weight, in particular 0.1 to 25% by weight, of a surfactant. While concentrated compositions are more preferred as commercially available goods, the end consumer uses, as a rule, dilute compositions. The compositions can also comprise further additives such as stabilizers, for example epoxidized or non-epoxidized vegetable oils (epoxidized coconut oil, rapeseed oil or soya oil), antifoams, e.g. silicone oil, preservatives, viscosity regulators, binders, tackifiers and fertilizers or other active ingredients.

[0157] As a rule, the active ingredients of the formula I are applied to the plant or its environment at rates of 0.001 to 4 kg/ha, in particular 0.005 to 2 kg/ha. The dosage required for the desired action can be determined by experiments. It depends on the type of the action, the developmental stage of the crop plant and of the weed, and on the application (location, timing, method) and can, owing to these parameters, vary within wide limits.

[0158] The compounds of the formula I are distinguished by herbicidal and growth-inhibitory properties which allow them to be employed in crops of useful plants, in particular in cereals, cotton, soya, sugar beet, sugar cane, plantation crops, rapeseed, maize and rice and for the non-selective control of weeds. Crops are also to be understood as including those which have been rendered tolerant to herbicides or classes of herbicides by means of conventional plant-breeding or genetic-engineering methods. The weeds to be controlled may be both mono- and dicotyledonous weeds such as Stellaria, Nasturtium, Agrostis, Digitaria, Avena, Setaria, Sinapis, Lolium, Solanum, Echinochloa, Scirpus, Monochoria, Sagittaria, Bromus, Alopecurus, Sorghum halepense, Rottboellia, Cyperus, Abutilon, Sida, Xanthium, Amaranthus, Chenopodium, lpomoea, Chrysanthemum, Galium, Viola and Veronica.

[0159] The examples which follow illustrate the invention in greater detail without limiting it.

PREPARATION EXAMPLES

Example H1

Preparation of ethyl 2-bromomethyl-6-trifluoromethyinicotinate

[0160] 434.4 g (1.866 mol) of ethyl 2-methyl-6-trifluoromethyinicotinate (preparation similar to Heterocycles 129, 46,1997) and 398.5 g (2.239 mol) of N-bromosuccinimide in 3 500 ml of carbon tetrachloride in the presence of 30.6 g (0.1866 mol) of α,α-azaisobutyronitrile are heated at 75° C., with irradiation from a 150 Watt lamp. After 3 hours, the reaction is terminated, the mixture is cooled to 15° C. and precipitated succinimide is removed by filtration. After evaporation of the solvent, the residue is distilled under reduced pressure. This gives ethyl 2-bromomethyl-6-trifluoromethylnicotinate as an oily product (260.2 g, 44.7% of theory, b.p. 74° C./0.04 mmHg).

Example H2

2-(2-Methoxyethoxymethyl)-6-trifluoromethylnicotinic acid

[0161] At room temperature,177.2 g of ethyl 2-bromomethyl-6-trifluoromethylnicotinate are dissolved in 3 000 ml of toluene and reacted with 398 ml (1.704 mol) of a 21% ethanolic solution of sodium ethoxide. After 8 hours at room temperature, 1500 ml of ethanol and 100 ml of 30% aqueous sodium hydroxide solution are added with vigorous stirring, and the reaction mixture is stirred at this temperature for another 4 hours. The reaction mixture is poured into water and extracted with ethyl acetate, and the aqueous phase is acidified to pH 1. Following extraction with ethyl acetate, drying over sodium sulfate, evaporation under reduced pressure and trituration with hexane, pure 2-(2-methoxyethoxymethyl)-6-trifluoro-methylnicotinic acid is obtained in the form of white crystals of melting point 62-63° C.

Example H3

4-Hydroxy-3-[2-(2-methoxyethoxymethyl)-6-trifluoromethylpyridine-3-carbonyl]-bicyclo[3.2.1]oct-3-en-2-one

[0162] 24.9 g (0.1 mol) of 2-(2-methoxyethoxymethyl)-6-trifluoromethyinicotinic acid are dissolved in 200 ml of methylene chloride and 20 ml of oxalyl chloride, and 0.1 ml of dimethylformamide is then added dropwise. After the strong evolution of gas has ceased, triethylamine (27.9 ml, 0.2 mol), dimethylaminopyridine (1.22 g, 0.01 mol) and 15.2 g (0.11 mol) of bicyclo[3.2.1]octane-2,4-dione are added at a temperature of from 0 to 5° C. After 3 hours at 22° C., the reaction mixture is extracted with 2 N hydrochloric acid. The methylenechloride phase is separated off, washed with water and then extracted with 10% aqueous sodium bicarbonate solution, dried over sodium sulfate and concentrated. This gives 36.9 g (100% of theory) of 4-oxobicyclo[3.2.1]oct-2-en-2-yl 2-(2-methoxyethoxymethyl)-6-trifluoromethyl -nicotininate as an oil, which can be used further without purification.

[0163] 36.9 g (0.1 mol) of 4-oxobicyclo[3.2.1]oct-2-en-2-yl 2-(2-methoxyethoxymethyl)-6-trifluoro-methylnicotinate and 27.9 ml (0.2 mol) of triethylamine are dissolved in 400 ml of acetonitrile. At a temperature of 22° C., 0.92 ml (0.01 mol) of acetone cyanohydrin is added. After 18 hours at 22° C., the reaction mixture is poured into a water/2 N hydrochloric acid mixture and extracted with ethyl acetate. The ethyl acetate phase is washed with water and then with concentrated sodium chloride solution, dried over sodium sulfate and concentrated, and the residue is triturated with hexane. Filtration gives 27.9 g (75.6% of theory) of 4-hydroxyl-3-[2-(2-methoxyethoxymethyl)-6-trifluoromethylpyridine-3-carbonyl]bicyclo[3.2.1]oct-3-en-2-one in the form of white crystals (m.p. 55-56° C.).

Example H4

3-(2-Hydroxy-4-oxobicyclo[3.2.1]oct-2-en-3-carbonyl)-6-trifluoromethylpyridin-2-yl methyl acetate

[0164] 5.0 g (1 mmol) of 4-hydroxy-3-(2-methyl-1-oxy-6-trifluoromethylpyridin-3-carbonyl) -bicyclo[3.2.1]oct-3-en-2-one (preparation as described in WO 00/15615) are dissolved in 100 ml of toluene and, in the presence of 6.9 ml (0.073 mol) of acetic anhydride, heated at reflux temperature for 10 hours. The mixture is then partitioned between water and ethyl acetate and the organic phase is dried over sodium sulfate and concentrated under reduced pressure. The residue that remains is chromatographed on silica gel. The viscous oil obtained by eluting with a mixture of toluene, ethyl alcohol, dioxane, triethylamine and water (100:40:20:20:5 parts by volume) is dissolved in ethyl acetate and washed successively with 10% hydrochloric acid and water. The organic solution is dried over Na2SO4 and concentrated, giving 2.14 g (38%) of pure 3-(2-hydroxy-4-oxobicyclo[3.2.1]oct-2-ene-3-carbonyl)-6-trifluoromethylpyridin-2-ylmethyl acetate in the form of an oil. 1H-NMR (250 MHz, CDCl3): 17.06 (s), 1H; 7.67 (s), 2H; 5.27 (d, J=12.5 Hz), 1H; 5.20 (d, J=12.5 Hz), 1H; 3.18, (t, J=5.0 Hz), 1H; 2.92, (t, J=5.0 Hz), 1H; 2.29-1.98 (m), 4H; 2.00, (s), 3H; 1.81-1.73 ppm (m), 2H.

Example H5

4-Hydroxy-3-(2-oxiranylmethoxymethyl-6-trifluoromethylpyridine-3-carbonyl)-bicyclo[3.2.1]oct-3-en-2-one

[0165] 5 g (0.013 mol) of 3-(2-hydroxy-4-oxobicyclo[3.2.1]oct-2-ene-3-carbonyl)-6-trifluoromethyl-pyridin-2-ylmethyl acetate are dissolved in 60 ml of methanol/water (3:1 mixture), and 1.4 g (0.046 mol) of lithium hydroxide hydrate are added a little at a time at a temperature of 22° C. After 3 hours at 22° C., the reaction mixture is poured into ethyl acetate and 10% hydrochloric acid, and the organic phase is washed three times with water, dried with sodium sulfate and concentrated. This gives 4.1 g of 4-hydroxy-3-(2-hydroxymethyl-6-trifluoromethylpyridine-3-carbonyl)bicyclo[3.2.1]oct-3-en-2-one as an oil which can be reacted further without purification.

[0166] 1.5 g of 4-hydroxy-3-(2-hydroxymethyl-6-trifluoromethylpyridine-3-carbonyl)-bicyclo[3.2.1]oct -3-en-2-one are dissolved in 15 ml of dimethylformamide and, at room temperature, treated with 0.4 g of sodium hydride (80% suspension in oil, 0.013 mol), a little at a time. After 15 minutes at a temperature of 22° C., 3 ml (0.036 mol) of epibromohydrin are added dropwise, and the reaction mixture is stirred at this temperature for another 18 hours. Ethyl acetate is then added, and the mixture is acidified to pH 3 using 10% hydrochloric acid and extracted with ethyl acetate. The organic phase is dried over sodium sulfate and the crude product is purified chromatographically (mobile phase: toluene/ethyl alcohol/dioxane/triethylamine/water 100:40:20:20:5 parts by volume). This gives the title compound (triethylamine salt) in the form of a yellowish resin, which is released similarly to example H4. Trituration with hexane gives 600 mg of pure 4-hydroxy-3-(2-oxiranylmethoxy-methyl-6-trifluoromethylpyridin-3-carbonyl)bicyclo[3.2.1]oct-3-en-2-one of melting point 54-56° C.

Example H6

(5-Hydroxy-1,3-dimethyl-1H-pyrazol-4-yl)-[2-(2-methoxyethoxymethyl)-6-trifluoromethylpridin-3-yl]methanone

[0167] 1.0 g (0.004 mol) of 2-(2-methoxyethoxymethyl)-6-trifluoromethyinicotinic acid is dissolved in 10 ml of oxalyl chloride. Three drops of dimethylformamide are added, and the mixture is stirred at room temperature for 1 hour. The mixture is then concentrated using a rotary evaporator, and the residue (2-(2-methoxyethoxymethyl)-6-trifluoromethyinicotinoyl chloride) is taken up in 10 ml of methylene chloride. At a temperature of 0° C., 0.84 ml (0.006 mol) of triethylamine and 0.45 g (0.004 mol) of 2,5-dimethyl-2,4-dihydropyrazol-3-one are added. After 2 hours at a temperature of 22° C., the solvent is removed using a vacuum rotary evaporator, and the residue that remains is dissolved in 10 ml of acetonitrile and, to rearrange the intermediate (2,5-dimethyl-2H-pyrazol-3-yl 2-(2-methoxyethoxymethyl)-6-trifluoromethylnicotinate), admixed with 0.1 ml of acetone cyanohydrin and 1.13 ml (0.008 mol) of triethylamine. The reaction solution is stirred at room temperature for four hours and then concentrated. The syrup that remains is chromatographed on silica gel. The viscous oil obtained by eluting with a mixture of toluene, ethyl alcohol, dioxane, triethylamine and water (100:40:20:20:5 parts by volume) is dissolved in ethyl acetate and washed successively with 10% hydrochloric acid and water. The organic solution is dried over Na2SO4 and concentrated, giving 0.93 g of (5-hydroxy-1,3-dimethyl-1H-pyrazol-4-yl)-[2-(2-methoxyethoxymethyl)-6-trifluoromethylpyridin-3-yl]methanone in the form of a viscous oil. 1H NMR (300 MHz, CDCl3, δ in ppm): 7.81, (d, J=6 Hz), 1H; 7.74, (d, J=6 Hz), 1H; 4.84, (s), 2H; 2H: 3.71, (s), 3H; 3.59, (t, J=6 Hz) 2H; 3.38, (dd, J 4.0, 3.0 Hz), 1H; 3.26, (s), 3H; 1.82 ppm, (s), 1H.

[0168] Preferred compounds of the formula I and their intermediates are listed in the tables below.

[0169] In the table below, the left-hand valency of the radical R1 is attached to the pyridine ring. If no free valency is indicated in the substituent R2, as, for example, in the case of 43

[0170] ,the point of attachment is at the “CH” carbon atom.

[0171] In the table below, the compounds of the formula I are represented as:

A-Q

[0172] where the formula A

	(A)
44
denotes the following radicals:
Radical	R1	R2	R4	R3	X1	p
A1	CH2	CH3	H	CF3	O	0
A2	CH2	CH2CH3	H	CF3	O	0
A3	CH2	(CH3)2CH	H	CF3	O	0
A4	CH2	PhCH2	H	CF3	O	0
A5	CH2	CH3	H	CF3	S	0
A6	CH2	CH3	H	CF3	SO	0
A7	CH2	CH3	H	CF3	SO2	0
A8	CH2	CH3OCH2	H	CF3	O	0
A9	CH2	CH3CH2OCH2	H	CF3	O	0
A10	CH2	CH3OCH2CH2	H	CF3	O	0
A11	CH2	CH3CH2OCH2CH2	H	CF3	O	0
A12	CH2	CH3OC(CH3)2CH2	H	CF3	O	0
A13	CH2	CH3OCH(CH3)CH2	H	CF3	O	0
A14	CH2	CH3OCH2CH(CH3)	H	CF3	O	0
A15	CH2	CH3OCH2C(CH3)2	H	CF3	O	0
A16	CH2	CH3OCH(CH3)	H	CF3	O	0
A17	CH2	CH3OC(CH3)2	H	CF3	O	0
A18	CH2	HC≡CCH2	H	CF3	O	0
A19	CH2	H2C═CHCH2	H	CF3	O	0
A20	CH2	CH3C≡CCH2	H	CF3	O	0
A21	CH2	45	H	CF3	O	0
A22	CH2	46	H	CF3	O	0
A23	CH2	47	H	CF3	O	0
A24	CH2	48	H	CF3	O	0
A25	CH2	49	H	CF3	O	0
A26	CH2	50	H	CF3	O	0
A27	CH2	51	H	CF3	O	0
A28	CH2	52	H	CF3	O	0
A29	CH2	53	H	CF3	O	0
A30	CH2	54	H	CF3	O	0
A31	CH2	55	H	CF3	O	0
A32	CH2	56	H	CF3	O	0
A33	CH2	57	H	CF3	O	0
A34	CH2	58	H	CF3	O	0
A35	CH2	59	H	CF3	O	0
A36	CH2	60	H	CF3	O	0
A37	CH2	61	H	CF3	O	0
A38	CH2	62	H	CF3	O	0
A39	CH2	63	H	CF3	O	0
A40	CH2	64	H	CF3	O	0
A41	CH2	65	H	CF3	O	0
A42	CH2	66	H	CF3	O	0
A43	CH2	67	H	CF3	O	0
A44	CH2	68	H	CF3	O	0
A45	CH2	69	H	CF3	O	0
A46	CH2	70	H	CF3	O	0
A47	CH2	71	H	CF3	O	0
A48	CH2	72	H	CF3	O	0
A49	CH2	73	H	CF3	O	0
A50	CH2	74	H	CF3	O	0
A51	CH2	75	H	CF3	O	0
A52	CH2	76	H	CF3	O	0
A53	CH2	77	H	CF3	O	0
A54	CH2	78	H	CF3	O	0
A55	CH2	79	H	CF3	O	0
A56	CH2	80	H	CF3	O	0
A57	CH2	81	H	CF3	O	0
A58	CH2	82	H	CF3	O	0
A59	CH2	83	H	CF3	O	0
A60	CH2	84	H	CF3	O	0
A61	CH2	85	H	CF3	O	0
A62	CH2	86	H	CF3	O	0
A63	CH2	87	H	CF3	O	0
A64	CH2	88	H	CF3	O	0
A65	CH2	89	H	CF3	O	0
A66	CH2	90	H	CF3	O	0
A67	CH2	91	H	CF3	O	0
A68	CH2	92	H	CF3	O	0
A69	CH2	93	H	CF3	O	0
A70	CH2	94	H	CF3	O	0
A71	CH2	95	H	CF3	O	0
A72	CH2	96	H	CF3	O	0
A73	CH2	97	H	CF3	O	0
A74	CH2	98	H	CF3	O	0
A75	CH2	99	H	CF3	O	0
A76	CH2	100	H	CF3	O	0
A77	CH2	101	H	CF3	O	0
A78	CH2	102	H	CF3	O	0
A79	CH2	103	H	CF3	O	0
A80	CH2	104	H	CF3	O	0
A81	CH2	105	H	CF3	O	0
A82	CH2	106	H	CF3	O	0
A83	CH2	107	H	CF3	O	0
A84	CH2	108	H	CF3	O	0
A85	CH2	109	H	CF3	O	0
A86	CH2	110	H	CF3	O	0
A87	CH2	111	H	CF3	O	0
A88	CH2	112	H	CF3	O	0
A89	CH2	113	H	CF3	O	0
A90	CH2	114	H	CF3	O	0
A91	CH2CH2	CH3	H	CF3	O	0
A92	CH2CH2	CH3CH2	H	CF3	O	0
A93	CH2CH2	(CH3)2CH	H	CF3	O	0
A94	CH2CH2	PhCH2	H	CF3	O	0
A95	CH2CH2	CH3	H	CF3	S	0
A96	CH2CH2	CH3	H	CF3	SO	0
A97	CH2CH2	CH3	H	CF3	SO2	0
A98	CH2CH2	(CH3)2CHCH2	H	CF3	O
A99	CH2CH2	CH3OCH2	H	CF3	O	0
A100	CH2CH2	CH3CH2OCH2	H	CF3	O	0
A101	CH2CH2	CH3OCH2CH2	H	CF3	O	0
A102	CH2CH2	CH3CH2OCH2CH2	H	CF3	O	0
A103	CH2CH2	CH3OC(CH3)2CH2	H	CF3	O	0
A104	CH2CH2	CH3OCH(CH3)CH2	H	CF3	O	0
A105	CH2CH2	CH3OCH2CH(CH3)	H	CF3	O	0
A106	CH2CH2	CH3OCH2C(CH3)2	H	CF3	O	0
A107	CH2CH2	CH3OCH(CH3)	H	CF3	O	0
A108	CH2CH2	CH3OC(CH3)2	H	CF3	O	0
A109	CH2CH2	HC≡CCH2	H	CF3	O	0
A110	CH2CH2	H2C═CHCH2	H	CF3	O	0
A111	CH2CH2	CH3C≡CCH2	H	CF3	O	0
A112	CH2CH2	115	H	CF3	O	0
A113	CH2CH2	116	H	CF3	O	0
A114	CH2CH2	117	H	CF3	O	0
A115	CH2CH2	118	H	CF3	O	0
A116	CH2CH2	119	H	CF3	O	0
A117	CH2CH2	120	H	CF3	O	0
A118	CH2CH2	121	H	CF3	O	0
A119	CH2CH2	122	H	CF3	O	0
A120	CH2CH2	123	H	CF3	O	0
A121	CH2CH2	124	H	CF3	O	0
A122	CH2CH2	125	H	CF3	O	0
A123	CH2CH2	126	H	CF3	O	0
A124	CH2CH2	127	H	CF3	O	0
A125	CH2CH2	128	H	CF3	O	0
A126	CH2CH2	129	H	CF3	O	0
A127	CH2CH2	130	H	CF3	O	0
A128	CH2CH2	131	H	CF3	O	0
A129	CH2CH2	132	H	CF3	O	0
A130	CH2CH2	133	H	CF3	O	0
A131	CH2CH2	134	H	CF3	O	0
A132	CH2CH2	135	H	CF3	O	0
A133	CH2CH2	136	H	CF3	O	0
A134	CH2CH2	137	H	CF3	O	0
A135	CH2CH2	138	H	CF3	O	0
A136	CH2CH2	139	H	CF3	O	0
A137	CH2CH2	140	H	CF3	O	0
A138	CH2CH2	141	H	CF3	O	0
A139	CH2CH2	142	H	CF3	O	0
A140	CH2CH2	143	H	CF3	O	0
A141	CH2CH2	144	H	CF3	O	0
A142	CH2CH2	145	H	CF3	O	0
A143	CH2CH2	146	H	CF3	O	0
A144	CH2CH2	147	H	CF3	O	0
A145	CH2CH2	148	H	CF3	O	0
A146	CH2CH2	149	H	CF3	O	0
A147	CH2CH2	150	H	CF3	O	0
A148	CH2CH2	151	H	CF3	O	0
A149	CH2CH2	152	H	CF3	O	0
A150	CH2CH2	153	H	CF3	O	0
A151	CH2CH2	154	H	CF3	O	0
A152	CH2CH2	155	H	CF3	O	0
A153	CH2CH2	156	H	CF3	O	0
A154	CH2CH2	157	H	CF3	O	0
A155	CH2CH2	158	H	CF3	O	0
A156	CH2CH2	159	H	CF3	O	0
A157	CH2CH2	160	H	CF3	O	0
A158	CH2CH2	161	H	CF3	O	0
A159	CH2CH2	162	H	CF3	O	0
A160	CH2CH2	163	H	CF3	O	0
A161	CH2CH2	164	H	CF3	O	0
A162	CH2CH2	165	H	CF3	O	0
A163	CH2CH2	166	H	CF3	O	0
A164	CH2CH2	167	H	CF3	O	0
A165	CH2CH2	168	H	CF3	O	0
A166	CH2CH2	169	H	CF3	O	0
A167	CH2CH2	170	H	CF3	O	0
A168	CH2CH2	171	H	CF3	O	0
A169	CH2CH2	172	H	CF3	O	0
A170	CH2CH2	173	H	CF3	O	0
A171	CH2CH2	174	H	CF3	O	0
A172	CH2CH2	175	H	CF3	O	0
A173	CH2CH2	176	H	CF3	O	0
A174	CH2CH2	177	H	CF3	O	0
A175	CH2CH2	178	H	CF3	O	0
A176	CH2CH2	179	H	CF3	O	0
A177	CH2CH2	180	H	CF3	O	0
A178	CH2CH2	181	H	CF3	O	0
A179	CH2CH2	182	H	CF3	O	0
A180	CH2CH2	183	H	CF3	O	0
A181	CH2CH2	184	H	CF3	O	0
A182	CH(OCH3)CH2	CH3	H	CF3	O	0
A183	CH(OCH3)CH2	CH3CH2	H	CF3	O	0
A184	CH(OCH3)CH2	(CH3)2CH	H	CF3	O	0
A185	CH(OCH3)CH2	PhCH2	H	CF3	O	0
A186	CH(OCH3)CH2	CH3	H	CF3	S	0
A187	CH(OCH3)CH2	CH3	H	CF3	SO	0
A188	CH(OCH3)CH2	CH3	H	CF3	SO2	0
A189	CH(OCH3)CH2	CH3CH2CH2	H	CF3	O	0
A190	CH(OCH3)CH2	CH3OCH2	H	CF3	O	0
A191	CH(OCH3)CH2	CH3CH2OCH2	H	CF3	O	0
A192	CH(OCH3)CH2	CH3OCH2CH2	H	CF3	O	0
A193	CH(OCH3)CH2	CH3CH2OCH2CH2	H	CF3	O	0
A194	CH(OCH3)CH2	CH3OC(CH3)2CH2	H	CF3	O	0
A195	CH(OCH3)CH2	CH3OCH(CH3)CH2	H	CF3	O	0
A196	CH(OCH3)CH2	CH3OCH2CH(CH3)	H	CF3	O	0
A197	CH(OCH3)CH2	CH3OCH2C(CH3)2	H	CF3	O	0
A198	CH(OCH3)CH2	CH3OCH(CH3)	H	CF3	O	0
A199	CH(OCH3)CH2	CH3OC(CH3)2	H	CF3	O	0
A200	CH(OCH3)CH2	HC≡CCH2	H	CF3	O	0
A201	CH(OCH3)CH2	H2C═CHCH2	H	CF3	O	0
A202	CH(OCH3)CH2	CH3C≡CCH2	H	CF3	O	0
A203	CH(OCH3)CH2	185	H	CF3	O	0
A204	CH(OCH3)CH2	186	H	CF3	O	0
A205	CH(OCH3)CH2	187	H	CF3	O	0
A206	CH(OCH3)CH2	188	H	CF3	O	0
A207	CH(OCH3)CH2	189	H	CF3	O	0
A208	CH(OCH3)CH2	190	H	CF3	O	0
A209	CH(OCH3)CH2	191	H	CF3	O	0
A210	CH(OCH3)CH2	192	H	CF3	O	0
A211	CH(OCH3)CH2	193	H	CF3	O	0
A212	CH(OCH3)CH2	194	H	CF3	O	0
A213	CH(OCH3)CH2	195	H	CF3	O	0
A214	CH(OCH3)CH2	196	H	CF3	O	0
A215	CH(OCH3)CH2	197	H	CF3	O	0
A216	CH(OCH3)CH2	198	H	CF3	O	0
A217	CH(OCH3)CH2	199	H	CF3	O	0
A218	CH(OCH3)CH2	200	H	CF3	O	0
A219	CH(OCH3)CH2	201	H	CF3	O	0
A220	CH(OCH3)CH2	202	H	CF3	O	0
A221	CH(OCH3)CH2	203	H	CF3	O	0
A222	CH(OCH3)CH2	204	H	CF3	O	0
A223	CH(OCH3)CH2	205	H	CF3	O	0
A224	CH(OCH3)CH2	206	H	CF3	O	0
A225	CH(OCH3)CH2	207	H	CF3	O	0
A226	CH(OCH3)CH2	208	H	CF3	O	0
A227	CH(OCH3)CH2	209	H	CF3	O	0
A228	CH(OCH3)CH2	210	H	CF3	O	0
A229	CH(OCH3)CH2	211	H	CF3	O	0
A230	CH(OCH3)CH2	212	H	CF3	O	0
A231	CH(OCH3)CH2	213	H	CF3	O	0
A232	CH(OCH3)CH2	214	H	CF3	O	0
A233	CH(OCH3)CH2	215	H	CF3	O	0
A234	CH(OCH3)CH2	216	H	CF3	O	0
A235	CH(OCH3)CH2	217	H	CF3	O	0
A236	CH(OCH3)CH2	218	H	CF3	O	0
A237	CH(OCH3)CH2	219	H	CF3	O	0
A238	CH(OCH3)CH2	220	H	CF3	O	0
A239	CH(OCH3)CH2	221	H	CF3	O	0
A240	CH(OCH3)CH2	222	H	CF3	O	0
A241	CH(OCH3)CH2	223	H	CF3	O	0
A242	CH(OCH3)CH2	224	H	CF3	O	0
A243	CH(OCH3)CH2	225	H	CF3	O	0
A244	CH(OCH3)CH2	226	H	CF3	O	0
A245	CH(OCH3)CH2	227	H	CF3	O	0
A246	CH(OCH3)CH2	228	H	CF3	O	0
A247	CH(OCH3)CH2	229	H	CF3	O	0
A248	CH(OCH3)CH2	230	H	CF3	O	0
A249	CH(OCH3)CH2	231	H	CF3	O	0
A250	CH(OCH3)CH2	232	H	CF3	O	0
A251	CH(OCH3)CH2	233	H	CF3	O	0
A252	CH(OCH3)CH2	234	H	CF3	O	0
A253	CH(OCH3)CH2	235	H	CF3	O	0
A254	CH(OCH3)CH2	236	H	CF3	O	0
A255	CH(OCH3)CH2	237	H	CF3	O	0
A256	CH(OCH3)CH2	238	H	CF3	O	0
A257	CH(OCH3)CH2	239	H	CF3	O	0
A258	CH(OCH3)CH2	240	H	CF3	O	0
A259	CH(OCH3)CH2	241	H	CF3	O	0
A260	CH(OCH3)CH2	242	H	CF3	O	0
A261	CH(OCH3)CH2	243	H	CF3	O	0
A262	CH(OCH3)CH2	244	H	CF3	O	0
A263	CH(OCH3)CH2	245	H	CF3	O	0
A264	CH(OCH3)CH2	246	H	CF3	O	0
A265	CH(OCH3)CH2	247	H	CF3	O	0
A266	CH(OCH3)CH2	248	H	CF3	O	0
A267	CH(OCH3)CH2	249	H	CF3	O	0
A268	CH(OCH3)CH2	250	H	CF3	O	0
A269	CH(OCH3)CH2	251	H	CF3	O	0
A270	CH(OCH3)CH2	252	H	CF3	O	0
A271	CH(OCH3)CH2	253	H	CF3	O	0
A272	CH(OCH3)CH2	254	H	CF3	O	0
A273	CH2CH(OCH3)CH2	CH3	H	CF3	O	0
A274	CH2CH(OCH3)CH2	CH3CH2	H	CF3	O	0
A275	CH2CH(OCH3)CH2	(CH3)2CH	H	CF3	O	0
A276	CH2CH(OCH3)CH2	PhCH2	H	CF3	O	0
A277	CH2CH(OCH3)CH2	CH3	H	CF3	S	0
A278	CH2CH(OCH3)CH2	CH3	H	CF3	SO	0
A279	CH2CH(OCH3)CH2	CH3	H	CF3	SO2	0
A280	CH2CH(OCH3)CH2	CH3CH2CH2	H	CF3	O	0
A281	CH2CH(OCH3)CH2	CH3OCH2	H	CF3	O	0
A282	CH2CH(OCH3)CH2	CH3CH2OCH2	H	CF3	O	0
A283	CH2CH(OCH3)CH2	CH3OCH2CH2	H	CF3	O	0
A284	CH2CH(OCH3)CH2	CH3CH2OCH2CH2	H	CF3	O	0
A285	CH2CH(OCH3)CH2	CH3OC(CH3)2CH2	H	CF3	O	0
A286	CH2CH(OCH3)CH2	CH3OCH(CH3)CH2	H	CF3	O	0
A287	CH2CH(OCH3)CH2	CH3OCH2CH(CH3)	H	CF3	O	0
A288	CH2CH(OCH3)CH2	CH3OCH2C(CH3)2	H	CF3	O	0
A289	CH2CH(OCH3)CH2	CH3OCH(CH3)	H	CF3	O	0
A290	CH2CH(OCH3)CH2	CH3OC(CH3)2	H	CF3	O	0
A291	CH2CH(OCH3)CH2	HC≡CCH2	H	CF3	O	0
A292	CH2CH(OCH3)CH2	H2C═CHCH2	H	CF3	O	0
A293	CH2CH(OCH3)CH2	CH3C≡CCH2	H	CF3	O	0
A294	CH2CH(OCH3)CH2	255	H	CF3	O	0
A295	CH2CH(OCH3)CH2	256	H	CF3	O	0
A296	CH2CH(OCH3)CH2	257	H	CF3	O	0
A297	CH2CH(OCH3)CH2	258	H	CF3	O	0
A298	CH2CH(OCH3)CH2	259	H	CF3	O	0
A299	CH2CH(OCH3)CH2	260	H	CF3	O	0
A300	CH2CH(OCH3)CH2	261	H	CF3	O	0
A301	CH2CH(OCH3)CH2	262	H	CF3	O	0
A302	CH2CH(OCH3)CH2	263	H	CF3	O	0
A303	CH2CH(OCH3)CH2	264	H	CF3	O	0
A304	CH2CH(OCH3)CH2	265	H	CF3	O	0
A305	CH2CH(OCH3)CH2	266	H	CF3	O	0
A306	CH2CH(OCH3)CH2	267	H	CF3	O	0
A307	CH2CH(OCH3)CH2	268	H	CF3	O	0
A308	CH2CH(OCH3)CH2	269	H	CF3	O	p
A309	CH2CH(OCH3)CH2	270	H	CF3	O
A310	CH2CH(OCH3)CH2	271	H	CF3	O	0
A311	CH2CH(OCH3)CH2	272	H	CF3	O	0
A312	CH2CH(OCH3)CH2	273	H	CF3	O	0
A313	CH2CH(OCH3)CH2	274	H	CF3	O	0
A314	CH2CH(OCH3)CH2	275	H	CF3	O	0
A315	CH2CH(OCH3)CH2	276	H	CF3	O	0
A316	CH2CH(OCH3)CH2	277	H	CF3	O	0
A317	CH2CH(OCH3)CH2	278	H	CF3	O	0
A318	CH2CH(OCH3)CH2	279	H	CF3	O	0
A319	CH2CH(OCH3)CH2	280	H	CF3	O	0
A320	CH2CH(OCH3)CH2	281	H	CF3	O	0
A321	CH2CH(OCH3)CH2	282	H	CF3	O	0
A322	CH2CH(OCH3)CH2	283	H	CF3	O	0
A323	CH2CH(OCH3)CH2	284	H	CF3	O	0
A324	CH2CH(OCH3)CH2	285	H	CF3	O	0
A325	CH2CH(OCH3)CH2	286	H	CF3	O	0
A326	CH2CH(OCH3)CH2	287	H	CF3	O	0
A327	CH2CH(OCH3)CH2	288	H	CF3	O	0
A328	CH2CH(OCH3)CH2	289	H	CF3	O	0
A329	CH2CH(OCH3)CH2	290	H	CF3	O	0
A330	CH2CH(OCH3)CH2	291	H	CF3	O	0
A331	CH2CH(OCH3)CH2	292	H	CF3	O	0
A332	CH2CH(OCH3)CH2	293	H	CF3	O	0
A333	CH2CH(OCH3)CH2	294	H	CF3	O	0
A334	CH2CH(OCH3)CH2	295	H	CF3	O	0
A335	CH2CH(OCH3)CH2	296	H	CF3	O	0
A336	CH2CH(OCH3)CH2	297	H	CF3	O	0
A337	CH2CH(OCH3)CH2	298	H	CF3	O	0
A338	CH2CH(OCH3)CH2	299	H	CF3	O	0
A339	CH2CH(OCH3)CH2	300	H	CF3	O	0
A340	CH2CH(OCH3)CH2	301	H	CF3	O	0
A341	CH2CH(OCH3)CH2	302	H	CF3	O	0
A342	CH2CH(OCH3)CH2	303	H	CF3	O	0
A343	CH2CH(OCH3)CH2	304	H	CF3	O	0
A344	CH2CH(OCH3)CH2	305	H	CF3	O	0
A345	CH2CH(OCH3)CH2	306	H	CF3	O	0
A346	CH2CH(OCH3)CH2	307	H	CF3	O	0
A347	CH2CH(OCH3)CH2	308	H	CF3	O	0
A348	CH2CH(OCH3)CH2	309	H	CF3	O	0
A349	CH2CH(OCH3)CH2	310	H	CF3	O	0
A350	CH2CH(OCH3)CH2	311	H	CF3	O	0
A351	CH2CH(OCH3)CH2	312	H	CF3	O	0
A352	CH2CH(OCH3)CH2	313	H	CF3	O	0
A353	CH2CH(OCH3)CH2	314	H	CF3	O	0
A354	CH2CH(OCH3)CH2	315	H	CF3	O	0
A355	CH2CH(OCH3)CH2	316	H	CF3	O	0
A356	CH2CH(OCH3)CH2	317	H	CF3	O	0
A357	CH2CH(OCH3)CH2	318	H	CF3	O	0
A358	CH2CH(OCH3)CH2	319	H	CF3	O	0
A359	CH2CH(OCH3)CH2	320	H	CF3	O	0
A360	CH2CH(OCH3)CH2	321	H	CF3	O	0
A361	CH2CH(OCH3)CH2	322	H	CF3	O	0
A362	CH2CH(OCH3)CH2	323	H	CF3	O	0
A363	CH2CH(OCH3)CH2	324	H	CF3	O	0
A364	CH═CHCH2	CH3	H	CF3	O	0
A365	CH═CHCH2	CH3CH2	H	CF3	O	0
A366	CH═CHCH2	(CH3)2CH	H	CF3	O	0
A367	OH═CHCH2	PhCH2	H	CF3	O	0
A368	CH═CHCH2	CH3	H	CF3	S	0
A369	CH═CHCH2	CH3	H	CF3	SO	0
A370	CH═CHCH2	CH3	H	CF3	SO2	0
A371	CH═CHCH2	CH3CH2CH2	H	CF3	O	0
A372	CH═CHCH2	CH3OCH2	H	CF3	O	0
A373	CH═CHCH2	CH3CH2OCH2	H	F3	O	0
A374	CH═CHCH2	CH3OCH2CH2	H	CF3	O	0
A375	CH═CHCH2	CH3CH2OCH2CH2	H	CF3	O	0
A376	CH═CHCH2	CH3OC(CH3)2CH2	H	CF3	O	0
A377	CH═CHCH2	CH3OCH(CH3)CH2	H	CF3	O	0
A378	CH═CHCH2	CH3OCH2CH(CH3)	H	CF3	O	0
A379	CH═CHCH2	CH3OCH2C(CH3)2	H	CF3	O	0
A380	CH═CHCH2	CH3OCH(CH3)	H	CF3	O	0
A381	CH═CHCH2	CH3OC(CH3)2	H	CF3	O	0
A382	CH═CHCH2	HC≡CCH2	H	CF3	O	0
A383	CH═CHCH2	H2C═CHCH2	H	CF3	O	0
A384	CH═CHCH2	CH3C≡CCH2	H	CF3	O	0
A385	CH═CHCH2	325	H	CF3	O	0
A386	CH═CHCH2	326	H	CF3	O	0
A387	CH═CHCH2	327	H	CF3	O	0
A388	CH═CHCH2	328	H	CF3	O	0
A389	CH═CHCH2	329	H	CF3	O	0
A390	CH═CHCH2	330	H	CF3	O	0
A391	CH═CHCH2	331	H	CF3	O	0
A392	CH═CHCH2	332	H	CF3	O	0
A393	CH═CHCH2	333	H	CF3	O	0
A394	CH═CHCH2	334	H	CF3	O	0
A395	CH═CHCH2	335	H	CF3	O	0
A396	CH═CHCH2	336	H	CF3	O	0
A397	CH═CHCH2	337	H	CF3	O	0
A398	CH═CHCH2	338	H	CF3	O	0
A399	CH═CHCH2	339	H	CF3	O	0
A400	CH═CHCH2	340	H	CF3	O	0
A401	CH═CHCH2	341	H	CF3	O	0
A402	CH═CHCH2	342	H	CF3	O	0
A403	CH═CHCH2	343	H	CF3	O	0
A404	CH═CHCH2	344	H	CF3	O	0
A405	CH═CHCH2	345	H	CF3	O	0
A406	CH═CHCH2	346	H	CF3	O	0
A407	CH═CHCH2	347	H	CF3	O	0
A408	CH═CHCH2	348	H	CF3	O	0
A409	CH═CHCH2	349	H	CF3	O	0
A410	CH═CHCH2	350	H	CF3	O	0
A411	CH═CHCH2	351	H	CF3	O	0
A412	CH═CHCH2	352	H	CF3	O	0
A413	CH═CHCH2	353	H	CF3	O	0
A414	CH═CHCH2	354	H	CF3	O	0
A415	CH═CHCH2	355	H	CF3	O	0
A416	CH═CHCH2	356	H	CF3	O	0
A417	CH═CHCH2	357	H	CF3	O	0
A418	CH═CHCH2	358	H	CF3	O	0
A419	CH═CHCH2	359	H	CF3	O	0
A420	CH═CHCH2	360	H	CF3	O	0
A421	CH═CHCH2	361	H	CF3	O	0
A422	CH═CHCH2	362	H	CF3	O	0
A423	CH═CHCH2	363	H	CF3	O	0
A424	CH═CHCH2	364	H	CF3	O	0
A425	CH═CHCH2	365	H	CF3	O	0
A426	CH═CHCH2	366	H	CF3	O	0
A427	CH═CHCH2	367	H	CF3	O	0
A428	CH═CHCH2	368	H	CF3	O	0
A429	CH═CHCH2	369	H	CF3	O	0
A430	CH═CHCH2	370	H	CF3	O	0
A431	CH═CHCH2	371	H	CF3	O	0
A432	CH═CHCH2	372	H	CF3	O	0
A433	CH═CHCH2	373	H	CF3	O	0
A434	CH═CHCH2	374	H	CF3	O	0
A435	CH═CHCH2	375	H	CF3	O	0
A436	CH═CHCH2	376	H	CF3	O	0
A437	CH═CHCH2	377	H	CF3	O	0
A438	CH═CHCH2	378	H	CF3	O	0
A439	CH═CHCH2	379	H	CF3	O	0
A440	CH═CHCH2	380	H	CF3	O	0
A441	CH═CHCH2	381	H	CF3	O	0
A442	CH═CHCH2	382	H	CF3	O	0
A443	CH═CHCH2	383	H	CF3	O	0
A444	CH═CHCH2	384	H	CF3	O	0
A445	CH═CHCH2	385	H	CF3	O	0
A446	CH═CHCH2	386	H	CF3	O	0
A447	CH═CHCH2	387	H	CF3	O	0
A448	CH═CHCH2	388	H	CF3	O	0
A449	CH═CHCH2	389	H	CF3	O	0
A450	CH═CHCH2	390	H	CF3	O	0
A451	CH═CHCH2	391	H	CF3	O	0
A452	CH═CHCH2	392	H	CF3	O	0
A453	CH═CHCH2	393	H	CF3	O	0
A454	CH═CHCH2	394	H	CF3	O	0
A455	C≡CCH2	CH3	H	CF3	O	0
A456	C≡CCH2	CH3CH2	H	CF3	O	0
A457	C≡CCH2	(CH3)2CH	H	CF3	O	0
A458	C≡CCH2	PhCH2	H	CF3	O	0
A459	C≡CCH2	CH3	H	CF3	S	0
A460	C≡CCH2	CH3	H	CF3	SO	0
A461	C≡CCH2	CH3	H	CF3	SO2	0
A462	C≡CCH2	CH3CH2CH2	H	CF3	O	0
A463	C≡CCH2	CH3OCH2	H	CF3	O	0
A464	C≡CCH2	CH3CH2OCH2	H	CF3	O	0
A465	C≡CCH2	CH3OCH2CH2	H	CF3	O	0
A466	C≡CCH2	CH3CH2OCH2CH2	H	CF3	O	0
A467	C≡CCH2	CH3OC(CH3)2CH2	H	CF3	O	0
A468	C≡CCH2	CH3OCH(CH3)CH2	H	CF3	O	0
A469	C≡CCH2	CH3OCH2CH(CH3)	H	CF3	O	0
A470	C≡CCH2	CH3OCH2C(CH3)2	H	CF3	O	0
A471	C≡CCH2	CH3OCH(CH3)	H	CF3	O	0
A472	C≡CCH2	CH3OC(CH3)2	H	CF3	O	0
A473	C≡CCH2	HC≡CCH2	H	CF3	O	0
A474	C≡CCH2	H2C═CHCH2	H	CF3	O	0
A475	C≡CCH2	CH3C≡CCH2	H	CF3	O	0
A476	C≡CCH2	395	H	CF3	O	0
A477	C≡CCH2	396	H	CF3	O	0
A478	C≡CCH2	397	H	CF3	O	0
A479	C≡CCH2	398	H	CF3	O	0
A480	C≡CCH2	399	H	CF3	O	0
A481	C≡CCH2	400	H	CF3	O	0
A482	C≡CCH2	401	H	CF3	O	0
A483	C≡CCH2	402	H	CF3	O	0
A484	C≡CCH2	403	H	CF3	O	0
A485	C≡CCH2	404	H	CF3	O	0
A486	C≡CCH2	405	H	CF3	O	0
A487	C≡CCH2	406	H	CF3	O	0
A488	C≡CCH2	407	H	CF3	O	0
A489	C≡CCH2	408	H	CF3	O	0
A490	C≡CCH2	409	H	CF3	O	0
A491	C≡CCH2	410	H	CF3	O	0
A492	C≡CCH2	411	H	CF3	O	0
A493	C≡CCH2	412	H	CF3	O	0
A494	C≡CCH2	413	H	CF3	O	0
A495	C≡CCH2	414	H	CF3	O	0
A496	C≡CCH2	415	H	CF3	O	0
A497	C≡CCH2	416	H	CF3	O	0
A498	C≡CCH2	417	H	CF3	O	0
A499	C≡CCH2	418	H	CF3	O	0
A500	C≡CCH2	419	H	CF3	O	0
A501	C≡CCH2	420	H	CF3	O	0
A502	C≡CCH2	421	H	CF3	O	0
A503	C≡CCH2	422	H	CF3	O	0
A504	C≡CCH2	423	H	CF3	O	0
A505	C≡CCH2	424	H	CF3	O	0
A506	C≡CCH2	425	H	CF3	O	0
A507	C≡CCH2	426	H	CF3	O	0
A508	C≡CCH2	427	H	CF3	O	0
A509	C≡CCH2	428	H	CF3	O	0
A510	C≡CCH2	429	H	CF3	O	0
A511	C≡CCH2	430	H	CF3	O	0
A512	C≡CCH2	431	H	CF3	O	0
A513	C≡CCH2	432	H	CF3	O	0
A514	C≡CCH2	433	H	CF3	O	0
A515	C≡CCH2	434	H	CF3	O	0
A516	C≡CCH2	435	H	CF3	O	0
A517	C≡CCH2	436	H	CF3	O	0
A518	C≡CCH2	437	H	CF3	O	0
A519	C≡CCH2	438	H	CF3	O	0
A520	C≡CCH2	439	H	CF3	O	0
A521	C≡CCH2	440	H	CF3	O	0
A522	C≡CCH2	441	H	CF3	O	0
A523	C≡CCH2	442	H	CF3	O	0
A524	C≡CCH2	443	H	CF3	O	0
A525	C≡CCH2	444	H	CF3	O	0
A526	C≡CCH2	445	H	CF3	O	0
A527	C≡CCH2	446	H	CF3	O	0
A528	C≡CCH2	447	H	CF3	O	0
A529	C≡CCH2	448	H	CF3	O	0
A530	C≡CCH2	449	H	CF3	O	0
A531	C≡CCH2	450	H	CF3	O	0
A532	C≡CCH2	451	H	CF3	O	0
A533	C≡CCH2	452	H	CF3	O	0
A534	C≡CCH2	453	H	CF3	O	0
A535	C≡CCH2	454	H	CF3	O	0
A536	C≡CCH2	455	H	CF3	O	0
A537	C≡CCH2	456	H	CF3	O	0
A538	C≡CCH2	457	H	CF3	O	0
A539	C≡CCH2	458	H	CF3	O	0
A540	C≡CCH2	459	H	CF3	O	0
A541	C≡CCH2	460	H	CF3	O	0
A542	C≡CCH2	461	H	CF3	O	0
A543	C≡CCH2	462	H	CF3	O	0
A544	C≡CCH2	463	H	CF3	O	0
A545	C≡CCH2	464	H	CF3	O	0
A546	CH2	CH3	H	CF2Cl	O	0
A547	CH2	CH3CH2	H	CF2Cl	O	0
A548	CH2	(CH3)2CH	H	CF2Cl	O	0
A549	CH2	PhCH2	H	CF2Cl	O	0
A550	CH2	CH3	H	CF2Cl	S	0
A551	CH2	CH3	H	CF2Cl	SO	0
A552	CH2	CH3	H	CF2Cl	SO2	0
A553	CH2	CH3CH2CH2	H	CF2Cl	O	0
A554	CH2	CH3OCH2	H	CF2Cl	O	0
A555	CH2	CH3CH2OCH2	H	CF2Cl	O	0
A556	CH2	CH3OCH2CH2	H	CF2Cl	O	0
A557	CH2	CH3CH2OCH2CH2	H	CF2Cl	O	0
A558	CH2	CH3OC(CH3)2CH2	H	CF2Cl	O	0
A559	CH2	CH3OCH(CH3)CH2	H	CF2Cl	O	0
A560	CH2	CH3OCH2CH(CH3)	H	CF2Cl	O	0
A561	CH2	CH3OCH2C(CH3)2	H	CF2Cl	O	0
A562	CH2	CH3OCH(CH3)	H	CF2Cl	O	0
A563	CH2	CH3OC(CH3)2	H	CF2Cl	O	0
A564	CH2	HC≡CCH2	H	CF2Cl	O	0
A565	CH2	H2C═CHCH2	H	CF2Cl	O	0
A566	CH2	CH3C≡CCH2	H	CF2Cl	O	0
A567	CH2	465	H	CF2Cl	O	0
A568	CH2	466	H	CF2Cl	O	0
A569	CH2	467	H	CF2Cl	O	0
A570	CH2	468	H	CF2Cl	O	0
A571	CH2	469	H	CF2Cl	O	0
A572	CH2	470	H	CF2Cl	O	0
A573	CH2	471	H	CF2Cl	O	0
A574	CH2	472	H	CF2Cl	O	0
A575	CH2	473	H	CF2Cl	O	0
A576	CH2	474	H	CF2Cl	O	0
A577	CH2	475	H	CF2Cl	O	0
A578	CH2	476	H	CF2Cl	O	0
A579	CH2	477	H	CF2Cl	O	0
A580	CH2	478	H	CF2Cl	O	0
A581	CH2	479	H	CF2Cl	O	0
A582	CH2	480	H	CF2Cl	O	0
A583	CH2	481	H	CF2Cl	O	0
A584	CH2	482	H	CF2Cl	O	0
A585	CH2	483	H	CF2Cl	O	0
A586	CH2	484	H	CF2Cl	O	0
A587	CH2	485	H	CF2Cl	O	0
A588	CH2	486	H	CF2Cl	O	0
A589	CH2	487	H	CF2Cl	O	0
A590	CH2	488	H	CF2Cl	O	0
A591	CH2	489	H	CF2Cl	O	0
A592	CH2	490	H	CF2Cl	O	0
A593	CH2	491	H	CF2Cl	O	0
A594	CH2	492	H	CF2Cl	O	0
A595	CH2	493	H	CF2Cl	O	0
A596	CH2	494	H	CF2Cl	O	0
A597	CH2	495	H	CF2Cl	O	0
A598	CH2	496	H	CF2Cl	O	0
A599	CH2	497	H	CF2Cl	O	0
A600	CH2	498	H	CF2Cl	O	0
A601	CH2	499	H	CF2Cl	O	0
A602	CH2	500	H	CF2Cl	O	0
A603	CH2	501	H	CF2Cl	O	0
A604	CH2	502	H	CF2Cl	O	0
A605	CH2	503	H	CF2Cl	O	0
A606	CH2	504	H	CF2Cl	O	0
A607	CH2	505	H	CF2Cl	O	0
A608	CH2	506	H	CF2Cl	O	0
A609	CH2	507	H	CF2Cl	O	0
A610	CH2	508	H	CF2Cl	O	0
A611	CH2	509	H	CF2Cl	O	0
A612	CH2	510	H	CF2Cl	O	0
A613	CH2	511	H	CF2Cl	O	0
A614	CH2	512	H	CF2Cl	O	0
A615	CH2	513	H	CF2Cl	O	0
A616	CH2	514	H	CF2Cl	O	0
A617	CH2	515	H	CF2Cl	O	0
A618	CH2	516	H	CF2Cl	O	0
A619	CH2	517	H	CF2Cl	O	0
A620	CH2	518	H	CF2Cl	O	0
A621	CH2	519	H	CF2Cl	O	0
A622	CH2	520	H	CF2Cl	O	0
A623	CH2	521	H	CF2Cl	O	0
A624	CH2	522	H	CF2Cl	O	0
A625	CH2	523	H	CF2Cl	O	0
A626	CH2	524	H	CF2Cl	O	0
A627	CH2	525	H	CF2Cl	O	0
A628	CH2	526	H	CF2Cl	O	0
A629	CH2	527	H	CF2Cl	O	0
A630	CH2	528	H	CF2Cl	O	0
A631	CH2	529	H	CF2Cl	O	0
A632	CH2	530	H	CF2Cl	O	0
A633	CH2	531	H	CF2Cl	O	0
A634	CH2	532	H	CF2Cl	O	0
A635	CH2	533	H	CF2Cl	O	0
A636	CH2	534	H	CF2Cl	O	0
A637	CH2	CH3	H	CHF2	O	0
A638	CH2	CH2CH3	H	CHF2	O	0
A639	CH2	(CH3)2CH	H	CHF2	O	0
A640	CH2	PhCH2	H	CHF2	O	0
A641	CH2	CH3	H	CHF2	S	0
A642	CH2	CH3	H	CHF2	O	0
A643	CH2	CH3	H	CHF2	O	0
A644	CH2	CH3OCH2	H	CHF2	O	0
A645	CH2	CH3CH2OCH2	H	CHF2	O	0
A646	CH2	CH3OCH2CH2	H	CHF2	O	0
A647	CH2	CH3CH2OCH2CH2	H	CHF2	O	0
A648	CH2	CH3OC(CH3)2CH2	H	CHF2	O	0
A649	CH2	CH3OCH(CH3)CH2	H	CHF2	O	0
A650	CH2	CH3OCH2CH(CH3)	H	CHF2	O	0
A651	CH2	CH3OCH2C(CH3)2	H	CHF2	O	0
A652	CH2	CH3OCH(CH3)	H	CHF2	O	0
A653	CH2	CH3OC(CH3)2	H	CHF2	O	0
A654	CH2	HC≡CCH2	H	CHF2	O	0
A655	CH2	H2C═CHCH2	H	CHF2	O	0
A656	CH2	CH3C≡CCH2	H	CHF2	O	0
A657	CH2	535	H	CHF2	O	0
A658	CH2	536	H	CHF2	O	0
A659	CH2	537	H	CHF2	O	0
A660	CH2	538	H	CHF2	O	0
A661	CH2	539	H	CHF2	O	0
A662	CH2	540	H	CHF2	O	0
A663	CH2	541	H	CHF2	O	0
A664	CH2	542	H	CHF2	O	0
A665	CH2	543	H	CHF2	O	0
A666	CH2	544	H	CHF2	O	0
A667	CH2	545	H	CHF2	O	0
A668	CH2	546	H	CHF2	O	0
A669	CH2	547	H	CHF2	O	0
A670	CH2	548	H	CHF2	O	0
A671	CH2	549	H	CHF2	O	0
A672	CH2	550	H	CHF2	O	0
A673	CH2	551	H	CHF2	O	0
A674	CH2	552	H	CHF2	O	0
A675	CH2	553	H	CHF2	O	0
A676	CH2	554	H	CHF2	O	0
A677	CH2	555	H	CHF2	O	0
A678	CH2	556	H	CHF2	O	0
A679	CH2	557	H	CHF2	O	0
A680	CH2	558	H	CHF2	O	0
A681	CH2	559	H	CHF2	O	0
A682	CH2	560	H	CHF2	S	0
A683	CH2	561	H	CHF2	SO	0
A684	CH2	562	H	CHF2	SO2	0
A685	CH2	563	H	CHF2	O	0
A686	CH2	564	H	CHF2	O	0
A687	CH2	565	H	CHF2	O	0
A688	CH2	566	H	CHF2	O	0
A689	CH2	567	H	CHF2	O	0
A690	CH2	568	H	CHF2	O	0
A691	CH2	569	H	CHF2	O	0
A692	CH2	570	H	CHF2	O	0
A693	CH2	571	H	CHF2	O	0
A694	CH2	572	H	CHF2	O	0
A695	CH2	573	H	CHF2	O	0
A696	CH2	574	H	CHF2	O	0
A697	CH2	575	H	CHF2	O	0
A698	CH2	576	H	CHF2	O	0
A699	CH2	577	H	CHF2	O	0
A700	CH2	578	H	CHF2	O	0
A701	CH2	579	H	CHF2	O	0
A702	CH2	580	H	CHF2	O	0
A703	CH2	581	H	CHF2	O	0
A704	CH2	582	H	CHF2	O	0
A705	CH2	583	H	CHF2	O	0
A706	CH2	584	H	CHF2	O	0
A707	CH2	585	H	CHF2	O	0
A708	CH2	586	H	CHF2	O	0
A709	CH2	587	H	CHF2	O	0
A710	CH2	588	H	CHF2	O	0
A711	CH2	589	H	CHF2	O	0
A712	CH2	590	H	CHF2	O	0
A713	CH2	591	H	CHF2	O	0
A714	CH2	592	H	CHF2	O	0
A715	CH2	593	H	CHF2	O	0
A716	CH2	594	H	CHF2	O	0
A717	CH2	595	H	CHF2	O	0
A718	CH2	596	H	CHF2	O	0
A719	CH2	597	H	CHF2	O	0
A720	CH2	598	H	CHF2	O	0
A721	CH2	599	H	CHF2	O	0
A722	CH2	600	H	CHF2	O	0
A723	CH2	601	H	CHF2	O	0
A724	CH2	602	H	CHF2	O	0
A725	CH2	603	H	CHF2	O	0
A726	CH2	604	H	CHF2	O	0
A727	CH2	CH3	H	CF3	O	1
A728	CH2	CH2CH3	H	CF3	O	1
A729	CH2	(CH3)2CH	H	CF3	O	1
A730	CH2	PhCH2	H	CF3	O	1
A731	CH2	CH3	H	CF3	S	1
A732	CH2	CH3	H	CF3	SO	1
A733	CH2	CH3	H	CF3	SO2	1
A734	CH2	CH3OCH2	H	CF3	O	1
A735	CH2	CH3CH2OCH2	H	CF3	O	1
A736	CH2	CH3OCH2CH2	H	CF3	O	1
A737	CH2	CH3CH2OCH2CH2	H	CF3	O	1
A738	CH2	CH3OC(CH3)2CH2	H	CF3	O	1
A739	CH2	CH3OCH(CH3)CH2	H	CF3	O	1
A740	CH2	CH3OCH2CH(CH3)	H	CF3	O	1
A741	CH2	CH3OCH2C(CH3)2	H	CF3	O	1
A742	CH2	CH3OCH(CH3)	H	CF3	O	1
A743	CH2	CH3OC(CH3)2	H	CF3	O	1
A744	CH2	HC≡CCH2	H	CF3	O	1
A745	CH2	H2C═CHCH2	H	CF3	O	1
A746	CH2	CH3C≡CCH2	H	CF3	O	1
A747	CH2	605	H	CF3	O	1
A748	CH2	606	H	CF3	O	1
A749	CH2	607	H	CF3	O	1
A750	CH2	608	H	CF3	O	1
A751	CH2	609	H	CF3	O	1
A752	CH2	610	H	CF3	O	1
A753	CH2	611	H	CF3	O	1
A754	CH2	612	H	CF3	O	1
A755	CH2	613	H	CF3	O	1
A756	CH2	614	H	CF3	O	1
A757	CH2	615	H	CF3	O	1
A758	CH2	616	H	CF3	O	1
A759	CH2	617	H	CF3	O	1
A760	CH2	618	H	CF3	O	1
A761	CH2	619	H	CF3	O	1
A762	CH2	620	H	CF3	O	1
A763	CH2	621	H	CF3	O	1
A764	CH2	622	H	CF3	O	1
A765	CH2	623	H	CF3	O	1
A766	CH2	624	H	CF3	O	1
A767	CH2	625	H	CF3	O	1
A768	CH2	626	H	CF3	O	1
A769	CH2	627	H	CF3	O	1
A770	CH2	628	H	CF3	O	1
A771	CH2	629	H	CF3	O	1
A772	CH2	630	H	CF3	O	1
A773	CH2	631	H	CF3	O	1
A774	CH2	632	H	CF3	O	1
A775	CH2	633	H	CF3	O	1
A776	CH2	634	H	CF3	O	1
A777	CH2	635	H	CF3	O	1
A778	CH2	636	H	CF3	O	1
A779	CH2	637	H	CF3	O	1
A780	CH2	638	H	CF3	O	1
A781	CH2	639	H	CF3	O	1
A782	CH2	640	H	CF3	O	1
A783	CH2	641	H	CF3	O	1
A784	CH2	642	H	CF3	O	1
A785	CH2	643	H	CF3	O	1
A786	CH2	644	H	CF3	O	1
A787	CH2	645	H	CF3	O	1
A788	CH2	646	H	CF3	O	1
A789	CH2	647	H	CF3	O	1
A790	CH2	648	H	CF3	O	1
A791	CH2	649	H	CF3	O	1
A792	CH2	650	H	CF3	O	1
A793	CH2	651	H	CF3	O	1
A794	CH2	652	H	CF3	O	1
A795	CH2	653	H	CF3	O	1
A796	CH2	654	H	CF3	O	1
A797	CH2	655	H	CF3	O	1
A798	CH2	656	H	CF3	O	1
A799	CH2	657	H	CF3	O	1
A800	CH2	658	H	CF3	O	1
A801	CH2	659	H	CF3	O	1
A802	CH2	660	H	CF3	O	1
A803	CH2	661	H	CF3	O	1
A804	CH2	662	H	CF3	O	1
A805	CH2	663	H	CF3	O	1
A806	CH2	664	H	CF3	O	1
A807	CH2	665	H	CF3	O	1
A808	CH2	666	H	CF3	O	1
A809	CH2	667	H	CF3	O	1
A810	CH2	668	H	CF3	O	1
A811	CH2	669	H	CF3	O	1
A812	CH2	670	H	CF3	O	1
A813	CH2	671	H	CF3	O	1
A814	CH2	672	H	CF3	O	1
A815	CH2	673	H	CF3	O	1
A816	CH2	674	H	CF3	O	1
A817	CH2	CH3SCH2CH2	H	CF3	O	0
A818	CH2	CH3SOCH2CH2	H	CF3	O	0
A819	CH2	CH3SO2CH2CH2	H	CF3	O	0
A820	CH2	CH3OCH2CH2	H	CF2Cl	O	1
A821	CH2	CH3OCH2CH2	H	CF2H	O	1
A822	CH2	CH3OCH2CH2	F	CF3	O	0
A823	CH2	CH3OCH2CH2	CH3	CF3	O	0
A824	CH2	CH3OCH2CH2	CH3	CF3	O	1
A825	CH2	CH3OCH2CH2	H	CF3	S	0
A826	CH2	CH3OCH2CH2	H	CF3	SO	0
A827	CH2	CH3OCH2CH2	CH3	CF3	SO2	0
A828	CH2	CH3SO2CH2CH2	CH3	CF3	O	0
A829	CH2	675	H	CF3	S	0
A830	CH2	676	H	CF3	S	0
A831	CH2	677	CH3	CF3	S	0
A832	CH2	678	CH3	CF3	S	0
A833	CH2	CH3C(O)	H	CF3	O	0
A834	CH2	CF3CH2	H	CF3	O	0
A835	CH2	CH3OCH2CH2OCH2CH2	H	CF3	O	0
A836	CH2	HC≡CCH2CH2	H	CF3	O	0
A837	CH2	679	H	CF3	O	0
A838	CH2	CH3CH2C(OCH3)HOCH2CH2	H	CF3	O	0
A839	CH2	(CH3)3CC(O)	H	CF3	O	0
A840	CH2	CH2═CHCH2OCH2CH2	H	CF3	O	0
A841	CH2	CH3CH2CH2OCH2CH2	H	CF3	O	0
A842	CH2	680	H	CF3	O	0
A843	CH2	n-Heptyl-C(O)	H	CF3	O	0
A844	CH2	Phenyl-C(O)	H	CF3	O	0
A845	CH2	CF3CH2OCH2CH2	H	CF3	O	0
A846	CH2	CH3OCH2CH2CH2	H	CF3	O	0
A847	CH2	HOCH2CH2CH2	H	CF3	O	0
A848	CH2	681	H	CF3	O	0
A849	CH2	N≡CCH2CH2	H	CF3	O	0
A850	CH2	ClCH2CH2	H	CF3	O	0
A851	CH2	682	H	CF3	O	0
A852	CH2	683	H	CF3	O	0
A853	CH2	CH3OCH2C(Br)HCH2	H	CF3	O	0
A854	CH2	684	H	CF3	O	0
A855	CH2	685	H	CF3	O	0
A856	CH2	HOCH2CH2	H	CF3	O	0
A857	CH2	686	H	CF3	O	0
A858	CH2	CH3(OCH2CH2)3	H	CF3	O	0
A859	CH2	CH3CH2OC(CH3)HOCH2CH2	H	CF3	O	0
A860	CH2	n-Heptyl-C(O)OCH2CH2	H	CF3	O	0
A861	CH2	CH3C(O)OCH2CH2	H	CF3	O	0
A862	CH2	CH3SO2OCH2CH2	H	CF3	O	0
A863	CH2	687	H	CF3	O	0
A864	CH2	CH3	H	CF3	—NCH3SO2—	0
A865	CH2	HOCH2C(OH)HCH2	H	CF3	O	0
A866	CH2	Phenyl-C(O)OCH2CH2	H	CF3	O	0
A867	CH2	t-Butyl-C(O)OCH2CH2	H	CF3	O	0
A868	CH2	CH3OC(O)CH2	H	CF3	O	0

[0173] In the table below, in the case of rings, the ring attachment points for the substituents A1 and A2 are at the carbon atom which is marked “C”, for example 688

[0174] in the case of open-chain structures, “(CH3)2C” denotes, for example, 689

[0175] In the formula A-Q, Q denotes Q1

690
and Q1 denotes the following radicals B:
Radical	A1	A2	n	R21	R22	R13
B1	CH2	CH2	0	H	H	OH
B2	CH2	CH2	0	CH3	H	OH
B3	CH2	CH2	0	CH3	CH3	OH
B4	(CH3)CH	CH2	0	CH3	CH3	OH
B5	(CH3)2C	CH2	0	CH3	CH3	OH
B6	CH	CH	0	CH3	-	OH
B7	CH2	CH2	0	CH3	CH2═CHCH2	OH
B8	CH2	CH2	0	CH3	HC≡CCH2	OH
B9	CH2	CH2	0	CH3	CH3S	OH
B10	CH2	CH2	0	CH3	CH3SO	OH
B11	CH2	CH2	0	CH3	CH3SO2	OH
B12	CH2	CH2	0	CH3	CH30	OH
B13	CH2	CH2	0	CH3	CH3OC(O)	OH
B14	CH2	CH2	0	CH3	CH3CH2OC(O)	OH
B15	CH2	(CH3)2C	0	H	H	OH
B16	691	CH2	0	H	H	OH
B17	692	CH2	0	H	H	OH
B18	693	CH2	0	CH3	H	OH
B19	694	CH2	0	CH3	CH3	OH
B20	695	CH2	0	H	H	OH
B21	696	CH2	0	CH3	H	OH
B22	697	CH2	0	CH3	CH3	OH
B23	(CH3)2C	O	0	CH3	CH3	OH
B24	CH2	O	0	CH3	CH3	OH
B25	CH3N	O	0	CH3	CH3	OH
B26	698	O	0	CH3	CH3	OH
B27	CH3N	CH2	0	CH3	CH3	OH
B28	CH3N	(CH3)CH	0	H	H	OH
B29	CH3N	(CH3)CH	0	CH3	H	OH
B30	NH	(CH3)C	0	H	-	OH
B31	NH	CH	0	CH3	-	OH
B32	CH3N	(CH3)C	0	H	-	OH
B33	CH3N	CH	0	CH3	-	OH
B34	O	(CH3)2C	0	H	-	OH
B35	O	(CH3)2C	0	CH3	CH3	OH
B36	O	(CH3)2C	0	CH3	H	OH
B37	O	(CH3)C	0	H	-	OH
B38	O	CH	0	CH3	-	OH
B39	(CH3)2C	C═O	0	CH3	CH3	OH
B40	(CH3)2C	(OH)CH	0	CH3	CH3	OH
B41	699	C═O	0	CH3	CH3	OH
B42	700	C═O	0	CH2	CH2	OH
B43	(CH3)2C	701	0	CH3	CH3	OH
B44	(CH3)2C	702	0	CH3	CH3	OH
B45	(CH3)2C	703	0	CH3	CH3	OH
B46	(CH3)2C	704	0	CH3	CH3	OH
B47	(CH3)2C	HON═C	0	CH3	CH3	OH
B48	(CH3)2C	CH3ON═C	0	CH3	CH3	OH
B49	(CH3)2C	BnON═C	0	CH3	CH3	OH
B50	CH	O	1	H	CH2	OH
B51	CH	C═0	1	H	CH2	OH
B52	CH	CH2	1	H	CH2	OH
B53	CH	CH3N	1	H	CH2	OH
B54	CH	CH2CH2	1	H	CH2	OH
B55	CH	C═O	2	H	CH2	OH
B56	CH	CH2	2	H	CH2	OH
B57	CH	CH2	1	H	CH2	Cl
B58	CH	CH2	1	H	CH2	NH2
B59	CH	CH2	1	H	CH2	CH3SO2NH
B60	CH	CH2	1	H	CH2	CH3OCH2CH2S
B61	CH	CH2	1	H	CH2	CH3OCH2CH2SO
B62	CH	CH2	1	H	CH2	CH3OCH2CH2SO2
B63	CH	CH2	1	H	CH2	(CH3)2NC(O)NH
B64	CH	CH2	1	H	CH2	PhC(O)O
B65	CH	CH2	1	H	CH2	CH3OC(O)O
B66	CH	CH2	1	H	CH2	CH3(CH2)7S
B67	CH	CH2	1	H	CH2	CH3(CH2)7SO
B68	CH	CH2	1	H	CH2	CH3(CH2)7SO2
B69	CH	CH2	1	H	CH2	(CH3)2NSO2NH
B70	CH	CH2	1	H	CH2	PhS
B71	CH	CH2	1	H	CH2	PhSO
B72	CH	CH2	1	H	CH2	PhSO2
B73	CH	CH2	1	H	CH2	705
B74	CH	CH2	1	H	CH2	706
B75	(CH3)2C	C═O	0	CH3	CH3	Cl
B76	(CH3)2C	C═O	0	CH3	CH3	NH2
B77	(CH3)2C	C═O	0	CH3	CH3	CH3SO2NH
B78	(CH3)2C	C═O	0	CH3	CH3	CH3OCH2CH2S
B79	(CH3)2C	C═O	0	CH3	CH3	CH3OCH2CH2SO
B80	(CH3)2C	C═O	0	CH3	CH3	CH3OCH2CH2SO2
B81	(CH3)2C	C═O	0	CH3	CH3	(CH3)2NC(O)NH
B82	(CH3)2C	C═O	0	CH3	CH3	PhC(O)O
B83	(CH3)2C	C═O	0	CH3	CH3	CH3OC(O)O
B84	(CH3)2C	C═O	0	CH3	CH3	CH3(CH2)7S
B85	(CH3)2C	C═O	0	CH3	CH3	CH3(CH2)7SO
B86	(CH3)2C	C═O	0	CH3	CH3	CH3(CH2)7SO2
B87	(CH3)2C	C═O	0	CH3	CH3	(CH3)2NSO2NH
B88	(CH3)2C	C═O	0	CH3	CH3	PhS
B89	(CH3)2C	C═O	0	CH3	CH3	PhSO
B90	(CH3)2C	C═O	0	CH3	CH3	PhSO2
B91	(CH3)2C	C═O	0	CH3	CH3	707
B92	(CH3)2C	C═O	0	CH3	CH3	708
B93	(CH3)2C	CH2	0	H	H	Cl
B94	(CH3)2C	CH2	0	H	H	NH2
B96	(CH3)2C	CH2	0	H	H	CH3OCH2CH2S
B97	(CH3)2C	CH2	0	H	H	CH3OCH2CH2SO
B98	(CH3)2C	CH2	0	H	H	CH3OCH2CH2SO2
B99	(CH3)2C	CH2	0	H	H	(CH3)2NC(O)NH
B100	(CH3)2C	CH2	0	H	H	PhC(O)O
B101	(CH3)2C	CH2	0	H	H	CH3OC(O)O
B102	(CH3)2C	CH2	0	H	H	CH3(CH2)7S
B103	(CH3)2C	CH2	0	H	H	CH3(CH2)7SO
B104	(CH3)2C	CH2	0	H	H	CH3(CH2)7SO2
B105	(CH3)2C	CH2	0	H	H	(CH3)2NSO2NH
B106	(CH3)2C	CH2	0	H	H	PhS
B107	(CH3)2C	CH2	0	H	H	PhSO
B108	(CH3)2C	CH2	0	H	H	PhSO2
B109	(CH3)2C	CH2	0	H	H	709
B110	(CH3)2C	CH2	0	H	H	710
B111	CH2	(CH3)CH	0	H	H	OH
B112	CH2	CH2	1	H	CH2	t-Butyl-C(O)O
B113	CH2	CH2	1	H	CH2	t-Heptyl-C(O)O

[0176] or Q in the formula A-Q denotes Q2

711
and Q2 denotes the following radicals C:
Radical	R34	R35	R36
C1	CH3	H	OH
C2	CH3	CH3	OH
C3	H	HC≡CCH2	OH
C4	H	CH3SO2	OH
C5	H	CH3	OH
C6	H	PhCH2	OH
C7	CF3	CH3	OH
C8	712	CH3	OH
C9	CH3OCH2CH2OCH2	CH3	OH
C10	H	CH3	Cl
C11	H	CH3	NH2
C12	H	CH3	CH3SO2NH
C13	H	CH3	CH3OCH2CH2S
C14	H	CH3	CH3OCH2CH2SO
C15	H	CH3	CH3OCH2CH2SO2
C16	H	CH3	(CH3)2NC(O)NH
C17	H	CH3	PhO(O)O
C18	H	CH3	CH3OC(O)O
C19	H	CH3	CH3(CH2)7S
C20	H	CH3	CH3(CH2)7SO
C21	H	CH3	CH3(CH2)7SO2
C22	H	CH3	(CH3)2NSO2NH
C23	H	CH3	PhS
C24	H	CH3	PhSO
C25	H	CH3	PhSO2
C26	H	CH3	713
C27	H	CH3	714
C28	H	CH3	CH3SO2O
C29	H	CH3	p-TolylSO2O

[0177] or Q in the formula A-Q denotes Q3

715
and Q3 denotes the following radicals D (the point of attachment of R49 to
the heterocycle is the “CH” group):
	Radical	R49	R50	n
	D1	716	CH3	0
	D2	717	CH3	1
	D3	718	CH3	2
	D4	719	CF3	0
	D5	720	CF3	1
	D6	721	CF3	2
	D7	722	Ph	0
	D8	723	Ph	1
	D9	724	Ph	2
	D10	725	PhCH2	0
	D11	726	PhCH2	1
	D12	727	PhCH2	2

[0178]

TABLE 1
Intermediates for preparing the compounds of the formula I,
represented as formula
A-Q
in which Q denotes hydroxyl:
OH	OH	OH	OH	OH	OH	OH	OH	OH	OH	OH	OH
—	—	—	—	—	—	—	A8	A9	A10	A11	A12
A13	A14	A15	A16	A17	A18	A19	A20	A21	A22	A23	A24
A25	A26	A27	A28	A29	A30	A31	A32	A33	A34	A35	A36
A37	A38	A39	A40	A41	A42	A43	A44	A45	A46	A47	A48
A49	A50	A51	A52	A53	A54	A55	A56	A57	A58	A59	A60
A61	A62	A63	A64	A65	A66	A67	A68	A69	A70	A71	A72
A73	A74	A75	A76	A77	A78	A79	A80	A81	A82	A83	A84
A85	A86	A87	A88	A89	A90	—	—	—	—	—	—
—	—	A99	A100	A101	A102	A103	A104	A105	A106	A107	A108
A109	A110	A111	A112	A113	A114	A115	A116	A117	A118	A119	A120
A121	A122	A123	A124	A125	A126	A127	A128	A129	A130	A131	A132
A133	A134	A135	A136	A137	A138	A139	A140	A141	A142	A143	A144
A145	A146	A147	A148	A149	A150	A151	A152	A153	A154	A155	A156
A157	A158	A159	A160	A161	A162	A163	A164	A165	A166	A167	A168
A169	A170	A171	A172	A173	A174	A175	A176	A177	A178	A179	A180
A181	A182	A183	A184	A185	A186	A187	A188	A189	A190	A191	A192
A193	A194	A195	A196	A197	A198	A199	A200	A201	A202	A203	A204
A205	A206	A207	A208	A209	A210	A211	A212	A213	A214	A215	A216
A217	A218	A219	A220	A221	A222	A223	A224	A225	A226	A227	A228
A229	A230	A231	A232	A233	A234	A235	A236	A237	A238	A239	A240
A241	A242	A243	A244	A245	A246	A247	A248	A249	A250	A251	A252
A253	A254	A255	A256	A257	A258	A259	A260	A261	A262	A263	A264
A265	A266	A267	A268	A269	A270	A271	A272	A273	A274	A275	A276
A277	A278	A279	A280	A281	A282	A283	A284	A285	A286	A287	A288
A289	A290	A291	A292	A293	A294	A295	A296	A297	A298	A299	A300
A301	A302	A303	A304	A305	A306	A307	A308	A309	A310	A311	A312
A313	A314	A315	A316	A317	A318	A319	A320	A321	A322	A323	A324
A325	A326	A327	A328	A329	A330	A331	A332	A333	A334	A335	A336
A337	A338	A339	A340	A341	A342	A343	A344	A345	A346	A347	A348
A349	A350	A351	A352	A353	A354	A355	A356	A357	A358	A359	A360
A361	A362	A363	A364	A365	A366	A367	A368	A369	A370	A371	A372
A373	A374	A375	A376	A377	A378	A379	A380	A381	A382	A383	A384
A385	A386	A387	A388	A389	A390	A391	A392	A393	A394	A395	A396
A397	A398	A399	A400	A401	A402	A403	A404	A405	A406	A407	A408
A409	A410	A411	A412	A413	A414	A415	A416	A417	A418	A419	A420
A421	A422	A423	A424	A425	A426	A427	A428	A429	A430	A431	A432
A433	A434	A435	A436	A437	A438	A439	A440	A441	A442	A443	A444
A445	A446	A447	A448	A449	A450	A451	A452	A453	A454	A455	A456
A457	A458	A459	A460	A461	A462	A463	A464	A465	A466	A467	A468
A469	A470	A471	A472	A473	A474	A475	A476	A477	A478	A479	A480
A481	A482	A483	A484	A485	A486	A487	A488	A489	A490	A491	A492
A493	A494	A495	A496	A497	A498	A499	A500	A501	A502	A503	A504
A505	A506	A507	A508	A509	A510	A511	A512	A513	A514	A515	A516
A517	A518	A519	A520	A521	A522	A523	A524	A525	A526	A527	A528
A529	A530	A531	A532	A533	A534	A535	A536	A537	A538	A539	A540
A541	A542	A543	A544	A545	—	—	—	—	—	—	—
—	A554	A555	A556	A557	A558	A559	A560	A561	A562	A563	A564
A565	A566	A567	A568	A569	A570	A571	A572	A573	A574	A575	A576
A577	A578	A579	A580	A581	A582	A583	A584	A585	A586	A587	A588
A589	A590	A591	A592	A593	A594	A595	A596	A597	A598	A599	A600
A601	A602	A603	A604	A605	A606	A607	A608	A609	A610	A611	A612
A613	A614	A615	A616	A617	A618	A619	A620	A621	A622	A623	A624
A625	A626	A627	A628	A629	A630	A631	A632	A633	A634	A635	A636
—	—	—	—	—	—	—	A644	A645	A646	A647	A648
A649	A650	A651	A652	A653	A654	A655	A656	A657	A658	A659	A660
A661	A662	A663	A664	A665	A666	A667	A668	A669	A670	A671	A672
A685	A686	A687	A688	A689	A690	A691	A692	A693	A694	A695	A696
A697	A698	A699	A700	A701	A702	A703	A704	A705	A706	A707	A708
A709	A710	A711	A712	A713	A714	A715	A716	A717	A718	A719	A720
A721	A722	A723	A724	A725	A726	—	—	—	—	—	—
A733	A734	A735	A736	A737	A738	A739	A740	A741	A742	A743	A744
A745	A746	A747	A748	A749	A750	A751	A752	A753	A754	A755	A756
A757	A758	A759	A760	A761	A762	A763	A764	A765	A766	A767	A768
A769	A770	A771	A772	A773	A774	A775	A776	A777	A778	A779	A780
A781	A782	A783	A784	A785	A786	A787	A788	A789	A790	A791	A792
A793	A794	A795	A796	A797	A798	A799	A800	A801	A802	A803	A804
A805	A806	A807	A808	A809	A810	A811	A812	A813	A814	A815	A816
A817	A818	A819	A820	A821	A822	A823	A824	A825	A826	A827	A828
A829	A830	A831	A832	—	—	—	—	—	—	—	—

[0179]

TABLE 2
Compounds of the formula I, represented as compounds of the formula
A-Q
in which Q denotes Q1 and Q1 denotes the radical B52:
B52	B52	B52	B52	B52	B52	B52	B52	B52	B52	B52	B52
A1	A2	A3	A4	A5	A6	A7	A8	A9	A10	A11	A12
A13	A14	A15	A16	A17	A18	A19	A20	A21	A22	A23	A24
A25	A26	A27	A28	A29	A30	A31	A32	A33	A34	A35	A36
A37	A38	A39	A40	A41	A42	A43	A44	A45	A46	A47	A48
A49	A50	A51	A52	A53	A54	A55	A56	A57	A58	A59	A60
A61	A62	A63	A64	A65	A66	A67	A68	A69	A70	A71	A72
A73	A74	A75	A76	A77	A78	A79	A80	A81	A82	A83	A84
A85	A86	A87	A88	A89	A90	A91	A92	A93	A94	A95	A96
A97	A98	A99	A100	A101	A102	A103	A104	A105	A106	A107	A108
A109	A110	A111	A112	A113	A114	A115	A116	A117	A118	A119	A120
A121	A122	A123	A124	A125	A126	A127	A128	A129	A130	A131	A132
A133	A134	A135	A136	A137	A138	A139	A140	A141	A142	A143	A144
A145	A146	A147	A148	A149	A150	A151	A152	A153	A154	A155	A156
A157	A158	A159	A160	A161	A162	A163	A164	A165	A166	A167	A168
A169	A170	A171	A172	A173	A174	A175	A176	A177	A178	A179	A180
A181	A182	A183	A184	A185	A186	A187	A188	A189	A190	A191	A192
A193	A194	A195	A196	A197	A198	A199	A200	A201	A202	A203	A204
A205	A206	A207	A208	A209	A210	A211	A212	A213	A214	A215	A216
A217	A218	A219	A220	A221	A222	A223	A224	A225	A226	A227	A228
A229	A230	A231	A232	A233	A234	A235	A236	A237	A238	A239	A240
A241	A242	A243	A244	A245	A246	A247	A248	A249	A250	A251	A252
A253	A254	A255	A256	A257	A258	A259	A260	A261	A262	A263	A264
A265	A266	A267	A268	A269	A270	A271	A272	A273	A274	A275	A276
A277	A278	A279	A280	A281	A282	A283	A284	A285	A286	A287	A288
A289	A290	A291	A292	A293	A294	A295	A296	A297	A298	A299	A300
A301	A302	A303	A304	A305	A306	A307	A308	A309	A310	A311	A312
A313	A314	A315	A316	A317	A318	A319	A320	A321	A322	A323	A324
A325	A326	A327	A328	A329	A330	A331	A332	A333	A334	A335	A336
A337	A338	A339	A340	A341	A342	A343	A344	A345	A346	A347	A348
A349	A350	A351	A352	A353	A354	A355	A356	A357	A358	A359	A360
A361	A362	A363	A364	A365	A366	A367	A368	A369	A370	A371	A372
A373	A374	A375	A376	A377	A378	A379	A380	A381	A382	A383	A384
A385	A386	A387	A388	A389	A390	A391	A392	A393	A394	A395	A396
A397	A398	A399	A400	A401	A402	A403	A404	A405	A406	A407	A408
A409	A410	A411	A412	A413	A414	A415	A416	A417	A418	A419	A420
A421	A422	A423	A424	A425	A426	A427	A428	A429	A430	A431	A432
A433	A434	A435	A436	A437	A438	A439	A440	A441	A442	A443	A444
A445	A446	A447	A448	A449	A450	A451	A452	A453	A454	A455	A456
A457	A458	A459	A460	A461	A462	A463	A464	A465	A466	A467	A468
A469	A470	A471	A472	A473	A474	A475	A476	A477	A478	A479	A480
A481	A482	A483	A484	A485	A486	A487	A488	A489	A490	A491	A492
A493	A494	A495	A496	A497	A498	A499	A500	A501	A502	A503	A504
A505	A506	A507	A508	A509	A510	A511	A512	A513	A514	A515	A516
A517	A518	A519	A520	A521	A522	A523	A524	A525	A526	A527	A528
A529	A530	A531	A532	A533	A534	A535	A536	A537	A538	A539	A540
A541	A542	A543	A544	A545	A546	A547	A548	A549	A550	A551	A552
A553	A554	A555	A556	A557	A558	A559	A560	A561	A562	A563	A564
A565	A566	A567	A568	A569	A570	A571	A572	A573	A574	A575	A576
A577	A578	A579	A580	A581	A582	A583	A584	A585	A586	A587	A588
A589	A590	A591	A592	A593	A594	A595	A596	A597	A598	A599	A600
A601	A602	A603	A604	A605	A606	A607	A608	A609	A610	A611	A612
A613	A614	A615	A616	A617	A618	A619	A620	A621	A622	A623	A624
A625	A626	A627	A628	A629	A630	A631	A632	A633	A634	A635	A636
A637	A638	A639	A640	A641	A642	A643	A644	A645	A646	A647	A648
A649	A650	A651	A652	A653	A654	A655	A656	A657	A658	A659	A660
A661	A662	A663	A664	A665	A666	A667	A668	A669	A670	A671	A672
A673	A674	A675	A676	A677	A678	A679	A680	A681	A682	A683	A684
A685	A686	A687	A688	A689	A690	A691	A692	A693	A694	A695	A696
A697	A698	A699	A700	A701	A702	A703	A704	A705	A706	A707	A708
A709	A710	A711	A712	A713	A714	A715	A716	A717	A718	A719	A720
A721	A722	A723	A724	A725	A726	A727	A728	A729	A730	A731	A732
A733	A734	A735	A736	A737	A738	A739	A740	A741	A742	A743	A744
A745	A746	A747	A748	A749	A750	A751	A752	A753	A754	A755	A756
A757	A758	A759	A760	A761	A762	A763	A764	A765	A766	A767	A768
A769	A770	A771	A772	A773	A774	A775	A776	A777	A778	A779	A780
A781	A782	A783	A784	A785	A786	A787	A788	A789	A790	A791	A792
A793	A794	A795	A796	A797	A798	A799	A800	A801	A802	A803	A804
A805	A806	A807	A808	A809	A810	A811	A812	A813	A814	A815	A816
A817	A818	A819	A820	A821	A822	A823	A824	A825	A826	A827	A828
A829	A830	A831	A832	—	—	—	—	—	—	—	—

[0180]

TABLE 3
Compounds of the formula I, represented as compounds of the formula
A-Q
in which Q denotes Q1 and Q1 denotes the radical B39:
B39	B39	B39	B39	B39	B39	B39	B39	B39	B39	B39	B39
A1	A2	A3	A4	A5	A6	A7	A8	A9	A10	A11	A12
A13	A14	A15	A16	A17	A18	A19	A20	A21	A22	A23	A24
A25	A26	A27	A28	A29	A30	A31	A32	A33	A34	A35	A36
A37	A38	A39	A40	A41	A42	A43	A44	A45	A46	A47	A48
A49	A50	A51	A52	A53	A54	A55	A56	A57	A58	A59	A60
A61	A62	A63	A64	A65	A66	A67	A68	A69	A70	A71	A72
A73	A74	A75	A76	A77	A78	A79	A80	A81	A82	A83	A84
A85	A86	A87	A88	A89	A90	A91	A92	A93	A94	A95	A96
A97	A98	A99	A100	A101	A102	A103	A104	A105	A106	A107	A108
A109	A110	A111	A112	A113	A114	A115	A116	A117	A118	A119	A120
A121	A122	A123	A124	A125	A126	A127	A128	A129	A130	A131	A132
A133	A134	A135	A136	A137	A138	A139	A140	A141	A142	A143	A144
A145	A146	A147	A148	A149	A150	A151	A152	A153	A154	A155	A156
A157	A158	A159	A160	A161	A162	A163	A164	A165	A166	A167	A168
A169	A170	A171	A172	A173	A174	A175	A176	A177	A178	A179	A180
A181	A182	A183	A184	A185	A186	A187	A188	A189	A190	A191	A192
A193	A194	A195	A196	A197	A198	A199	A200	A201	A202	A203	A204
A205	A206	A207	A208	A209	A210	A211	A212	A213	A214	A215	A216
A217	A218	A219	A220	A221	A222	A223	A224	A225	A226	A227	A228
A229	A230	A231	A232	A233	A234	A235	A236	A237	A238	A239	A240
A241	A242	A243	A244	A245	A246	A247	A248	A249	A250	A251	A252
A253	A254	A255	A256	A257	A258	A259	A260	A261	A262	A263	A264
A265	A266	A267	A268	A269	A270	A271	A272	A273	A274	A275	A276
A277	A278	A279	A280	A281	A282	A283	A284	A285	A286	A287	A288
A289	A290	A291	A292	A293	A294	A295	A296	A297	A298	A299	A300
A301	A302	A303	A304	A305	A306	A307	A308	A309	A310	A311	A312
A313	A314	A315	A316	A317	A318	A319	A320	A321	A322	A323	A324
A325	A326	A327	A328	A329	A330	A331	A332	A333	A334	A335	A336
A337	A338	A339	A340	A341	A342	A343	A344	A345	A346	A347	A348
A349	A350	A351	A352	A353	A354	A355	A356	A357	A358	A359	A360
A361	A362	A363	A364	A365	A366	A367	A368	A369	A370	A371	A372
A373	A374	A375	A376	A377	A378	A379	A380	A381	A382	A383	A384
A385	A386	A387	A388	A389	A390	A391	A392	A393	A394	A395	A396
A397	A398	A399	A400	A401	A402	A403	A404	A405	A406	A407	A408
A409	A410	A411	A412	A413	A414	A415	A416	A417	A418	A419	A420
A421	A422	A423	A424	A425	A426	A427	A428	A429	A430	A431	A432
A433	A434	A435	A436	A437	A438	A439	A440	A441	A442	A443	A444
A445	A446	A447	A448	A449	A450	A451	A452	A453	A454	A455	A456
A457	A458	A459	A460	A461	A462	A463	A464	A465	A466	A467	A468
A469	A470	A471	A472	A473	A474	A475	A476	A477	A478	A479	A480
A481	A482	A483	A484	A485	A486	A487	A488	A489	A490	A491	A492
A493	A494	A495	A496	A497	A498	A499	A500	A501	A502	A503	A504
A505	A506	A507	A508	A509	A510	A511	A512	A513	A514	A515	A516
A517	A518	A519	A520	A521	A522	A523	A524	A525	A526	A527	A528
A529	A530	A531	A532	A533	A534	A535	A536	A537	A538	A539	A540
A541	A542	A543	A544	A545	A546	A547	A548	A549	A550	A551	A552
A553	A554	A555	A556	A557	A558	A559	A560	A561	A562	A563	A564
A565	A566	A567	A568	A569	A570	A571	A572	A573	A574	A575	A576
A577	A578	A579	A580	A581	A582	A583	A584	A585	A586	A587	A588
A589	A590	A591	A592	A593	A594	A595	A596	A597	A598	A599	A600
A601	A602	A603	A604	A605	A606	A607	A608	A609	A610	A611	A612
A613	A614	A615	A616	A617	A618	A619	A620	A621	A622	A623	A624
A625	A626	A627	A628	A629	A630	A631	A632	A633	A634	A635	A636
A637	A638	A639	A640	A641	A642	A643	A644	A645	A646	A647	A648
A649	A650	A651	A652	A653	A654	A655	A656	A657	A658	A659	A660
A661	A662	A663	A664	A665	A666	A667	A668	A669	A670	A671	A672
A673	A674	A675	A676	A677	A678	A679	A680	A681	A682	A683	A684
A685	A686	A687	A688	A689	A690	A691	A692	A693	A694	A695	A696
A697	A698	A699	A700	A701	A702	A703	A704	A705	A706	A707	A708
A709	A710	A711	A712	A713	A714	A715	A716	A717	A718	A719	A720
A721	A722	A723	A724	A725	A726	A727	A728	A729	A730	A731	A732
A733	A734	A735	A736	A737	A738	A739	A740	A741	A742	A743	A744
A745	A746	A747	A748	A749	A750	A751	A752	A753	A754	A755	A756
A757	A758	A759	A760	A761	A762	A763	A764	A765	A766	A767	A768
A769	A770	A771	A772	A773	A774	A775	A776	A777	A778	A779	A780
A781	A782	A783	A784	A785	A786	A787	A788	A789	A790	A791	A792
A793	A794	A795	A796	A797	A798	A799	A800	A801	A802	A803	A804
A805	A806	A807	A808	A809	A810	A811	A812	A813	A814	A815	A816
A817	A818	A819	A820	A821	A822	A823	A824	A825	A826	A827	A828
A829	A830	A831	A832	—	—	—	—	—	—	—	—

[0181]

TABLE 4
Compounds of the formula I, represented as compounds of the formula
A-Q
in which Q denotes Q1 and Q1 denotes the radical B3:
B3	B3	B3	B3	B3	B3	B3	B3	B3	B3	B3	B3
—	—	—	—	—	—	—	A8	A9	A10	A11	A12
A13	A14	A15	A16	A17	A18	A19	A20	A21	A22	A23	A24
A25	A26	A27	A28	A29	A30	A31	A32	A33	A34	A35	A36
A37	A38	A39	A40	A41	A42	A43	A44	A45	A46	A47	A48
A49	A50	A51	A52	A53	A54	A55	A56	A57	A58	A59	A60
A61	A62	A63	A64	A65	A66	A67	A68	A69	A70	A71	A72
A73	A74	A75	A76	A77	A78	A79	A80	A81	A82	A83	A84
A85	A86	A87	A88	A89	A90	—	—	—	—	—	—
—	—	A99	A100	A101	A102	A103	A104	A105	A106	A107	A108
A109	A110	A111	A112	A113	A114	A115	A116	A117	A118	A119	A120
A121	A122	A123	A124	A125	A126	A127	A128	A129	A130	A131	A132
A133	A134	A135	A136	A137	A138	A139	A140	A141	A142	A143	A144
A145	A146	A147	A148	A149	A150	A151	A152	A153	A154	A155	A156
A157	A158	A159	A160	A161	A162	A163	A164	A165	A166	A167	A168
A169	A170	A171	A172	A173	A174	A175	A176	A177	A178	A179	A180
A181	A182	A183	A184	A185	A186	A187	A188	A189	A190	A191	A192
A193	A194	A195	A196	A197	A198	A199	A200	A201	A202	A203	A204
A205	A206	A207	A208	A209	A210	A211	A212	A213	A214	A215	A216
A217	A218	A219	A220	A221	A222	A223	A224	A225	A226	A227	A228
A229	A230	A231	A232	A233	A234	A235	A236	A237	A238	A239	A240
A241	A242	A243	A244	A245	A246	A247	A248	A249	A250	A251	A252
A253	A254	A255	A256	A257	A258	A259	A260	A261	A262	A263	A264
A265	A266	A267	A268	A269	A270	A271	A272	A273	A274	A275	A276
A277	A278	A279	A280	A281	A282	A283	A284	A285	A286	A287	A288
A289	A290	A291	A292	A293	A294	A295	A296	A297	A298	A299	A300
A301	A302	A303	A304	A305	A306	A307	A308	A309	A310	A311	A312
A313	A314	A315	A316	A317	A318	A319	A320	A321	A322	A323	A324
A325	A326	A327	A328	A329	A330	A331	A332	A333	A334	A335	A336
A337	A338	A339	A340	A341	A342	A343	A344	A345	A346	A347	A348
A349	A350	A351	A352	A353	A354	A355	A356	A357	A358	A359	A360
A361	A362	A363	A364	A365	A366	A367	A368	A369	A370	A371	A372
A373	A374	A375	A376	A377	A378	A379	A380	A381	A382	A383	A384
A385	A386	A387	A388	A389	A390	A391	A392	A393	A394	A395	A396
A397	A398	A399	A400	A401	A402	A403	A404	A405	A406	A407	A408
A409	A410	A411	A412	A413	A414	A415	A416	A417	A418	A419	A420
A421	A422	A423	A424	A425	A426	A427	A428	A429	A430	A431	A432
A433	A434	A435	A436	A437	A438	A439	A440	A441	A442	A443	A444
A445	A446	A447	A448	A449	A450	A451	A452	A453	A454	A455	A456
A457	A458	A459	A460	A461	A462	A463	A464	A465	A466	A467	A468
A469	A470	A471	A472	A473	A474	A475	A476	A477	A478	A479	A480
A481	A482	A483	A484	A485	A486	A487	A488	A489	A490	A491	A492
A493	A494	A495	A496	A497	A498	A499	A500	A501	A502	A503	A504
A505	A506	A507	A508	A509	A510	A511	A512	A513	A514	A515	A516
A517	A518	A519	A520	A521	A522	A523	A524	A525	A526	A527	A528
A529	A530	A531	A532	A533	A534	A535	A536	A537	A538	A539	A540
A541	A542	A543	A544	A545	—	—	—	—	—	—	—
—	A554	A555	A556	A557	A558	A559	A560	A561	A562	A563	A564
A565	A566	A567	A568	A569	A570	A571	A572	A573	A574	A575	A676
A577	A578	A579	A580	A581	A582	A583	A584	A585	A586	A587	A588
A589	A590	A591	A592	A593	A594	A595	A596	A597	A598	A599	A600
A601	A602	A603	A604	A605	A606	A607	A608	A609	A610	A611	A612
A613	A614	A615	A616	A617	A618	A619	A620	A621	A622	A623	A624
A625	A626	A627	A628	A629	A630	A631	A632	A633	A634	A635	A636
—	—	—	—	—	—	—	A644	A645	A646	A647	A648
A649	A650	A651	A652	A653	A654	A655	A656	A657	A658	A659	A660
A661	A662	A663	A664	A665	A666	A667	A668	A669	A670	A671	A672
A685	A686	A687	A688	A689	A690	A691	A692	A693	A694	A695	A696
A697	A698	A699	A700	A701	A702	A703	A704	A705	A706	A707	A708
A709	A710	A711	A712	A713	A714	A715	A716	A717	A718	A719	A720
A721	A722	A723	A724	A725	A726	—	—	—	—	—	—
A733	A734	A735	A736	A737	A738	A739	A740	A741	A742	A743	A744
A745	A746	A747	A748	A749	A750	A751	A752	A753	A754	A755	A756
A757	A758	A759	A760	A761	A762	A763	A764	A765	A766	A767	A768
A769	A770	A771	A772	A773	A774	A775	A776	A777	A778	A779	A780
A781	A782	A783	A784	A785	A786	A787	A788	A789	A790	A791	A792
A793	A794	A795	A796	A797	A798	A799	A800	A801	A802	A803	A804
A805	A806	A807	A808	A809	A810	A811	A812	A813	A814	A815	A816
A817	A818	A819	A820	A821	A822	A823	A824	A825	A826	A827	A828
A829	A830	A831	A832	—	—	—	—	—	—	—	—

[0182]

TABLE 5
Compounds of the formula I, represented as compounds of the formula
A-Q
in which Q denotes Q2 and Q2 denotes the radical C5:
C5	C5	C5	C5	C5	C5	C5	C5	C5	C5	C5	C5
A1	A2	A3	A4	A5	A6	A7	A8	A9	A10	A11	A12
A13	A14	A15	A16	A17	A18	A19	A20	A21	A22	A23	A24
A25	A26	A27	A28	A29	A30	A31	A32	A33	A34	A35	A36
A37	A38	A39	A40	A41	A42	A43	A44	A45	A46	A47	A48
A49	A50	A51	A52	A53	A54	A55	A56	A57	A58	A59	A60
A61	A62	A63	A64	A65	A66	A67	A68	A69	A70	A71	A72
A73	A74	A75	A76	A77	A78	A79	A80	A81	A82	A83	A84
A85	A86	A87	A88	A89	A90	A91	A92	A93	A94	A95	A96
A97	A98	A99	A100	A101	A102	A103	A104	A105	A106	A107	A108
A109	A110	A111	A112	A113	A114	A115	A116	A117	A118	A119	A120
A121	A122	A123	A124	A125	A126	A127	A128	A129	A130	A131	A132
A133	A134	A135	A136	A137	A138	A139	A140	A141	A142	A143	A144
A145	A146	A147	A148	A149	A150	A151	A152	A153	A154	A155	A156
A157	A158	A159	A160	A161	A162	A163	A164	A165	A166	A167	A168
A169	A170	A171	A172	A173	A174	A175	A176	A177	A178	A179	A180
A181	A182	A183	A184	A185	A186	A187	A188	A189	A190	A191	A192
A193	A194	A195	A196	A197	A198	A199	A200	A201	A202	A203	A204
A205	A206	A207	A208	A209	A210	A211	A212	A213	A214	A215	A216
A217	A218	A219	A220	A221	A222	A223	A224	A225	A226	A227	A228
A229	A230	A231	A232	A233	A234	A235	A236	A237	A238	A239	A240
A241	A242	A243	A244	A245	A246	A247	A248	A249	A250	A251	A252
A253	A254	A255	A256	A257	A258	A259	A260	A261	A262	A263	A264
A265	A266	A267	A268	A269	A270	A271	A272	A273	A274	A275	A276
A277	A278	A279	A280	A281	A282	A283	A284	A285	A286	A287	A288
A289	A290	A291	A292	A293	A294	A295	A296	A297	A298	A299	A300
A301	A302	A303	A304	A305	A306	A307	A308	A309	A310	A311	A312
A313	A314	A315	A316	A317	A318	A319	A320	A321	A322	A323	A324
A325	A326	A327	A328	A329	A330	A331	A332	A333	A334	A335	A336
A337	A338	A339	A340	A341	A342	A343	A344	A345	A346	A347	A348
A349	A350	A351	A352	A353	A354	A355	A356	A357	A358	A359	A360
A361	A362	A363	A364	A365	A366	A367	A368	A369	A370	A371	A372
A373	A374	A375	A376	A377	A378	A379	A380	A381	A382	A383	A384
A385	A386	A387	A388	A389	A390	A391	A392	A393	A394	A395	A396
A397	A398	A399	A400	A401	A402	A403	A404	A405	A406	A407	A408
A409	A410	A411	A412	A413	A414	A415	A416	A417	A418	A419	A420
A421	A422	A423	A424	A425	A426	A427	A428	A429	A430	A431	A432
A433	A434	A435	A436	A437	A438	A439	A440	A441	A442	A443	A444
A445	A446	A447	A448	A449	A450	A451	A452	A453	A454	A455	A456
A457	A458	A459	A460	A461	A462	A463	A464	A465	A466	A467	A468
A469	A470	A471	A472	A473	A474	A475	A476	A477	A478	A479	A480
A481	A482	A483	A484	A485	A486	A487	A488	A489	A490	A491	A492
A493	A494	A495	A496	A497	A498	A499	A500	A501	A502	A503	A504
A505	A506	A507	A508	A509	A510	A511	A512	A513	A514	A515	A516
A517	A518	A519	A520	A521	A522	A523	A524	A525	A526	A527	A528
A529	A530	A531	A532	A533	A534	A535	A536	A537	A538	A539	A540
A541	A542	A543	A544	A545	A546	A547	A548	A549	A550	A551	A552
A553	A554	A555	A556	A557	A558	A559	A560	A561	A562	A563	A564
A565	A566	A567	A568	A569	A570	A571	A572	A573	A574	A575	A576
A577	A578	A579	A580	A581	A582	A583	A584	A585	A586	A587	A588
A589	A590	A591	A592	A593	A594	A595	A596	A597	A598	A599	A600
A601	A602	A603	A604	A605	A606	A607	A608	A609	A610	A611	A612
A613	A614	A615	A616	A617	A618	A619	A620	A621	A622	A623	A624
A625	A626	A627	A628	A629	A630	A631	A632	A633	A634	A635	A636
A637	A638	A639	A640	A641	A642	A643	A644	A645	A646	A647	A648
A649	A650	A651	A652	A653	A654	A655	A656	A657	A658	A659	A660
A661	A662	A663	A664	A665	A666	A667	A668	A669	A670	A671	A672
A673	A674	A675	A676	A677	A678	A679	A680	A681	A682	A683	A684
A685	A686	A687	A688	A689	A690	A691	A692	A693	A694	A695	A696
A697	A698	A699	A700	A701	A702	A703	A704	A705	A706	A707	A708
A709	A710	A711	A712	A713	A714	A715	A716	A717	A718	A719	A720
A721	A722	A723	A724	A725	A726	A727	A728	A729	A730	A731	A732
A733	A734	A735	A736	A737	A738	A739	A740	A741	A742	A743	A744
A745	A746	A747	A748	A749	A750	A751	A752	A753	A754	A755	A756
A757	A758	A759	A760	A761	A762	A763	A764	A765	A766	A767	A768
A769	A770	A771	A772	A773	A774	A775	A776	A777	A778	A779	A780
A781	A782	A783	A784	A785	A786	A787	A788	A789	A790	A791	A792
A793	A794	A795	A796	A797	A798	A799	A800	A801	A802	A803	A804
A805	A806	A807	A808	A809	A810	A811	A812	A813	A814	A815	A816
A817	A818	A819	A820	A821	A822	A823	A824	A825	A826	A827	A828
A829	A830	A831	A832	—	—	—	—	—	—	—	—

[0183]

TABLE 6
Compounds of the formula I, represented as compounds of the formula
A-Q
in which Q denotes Q2 and Q2 denotes the radical C2:
C2	C2	C2	C2	C2	C2	C2	C2	C2	C2	C2	C2
A1	A2	A3	A4	A5	A6	A7	A8	A9	A10	A11	A12
A13	A14	A15	A16	A17	A18	A19	A20	A21	A22	A23	A24
A25	A26	A27	A28	A29	A30	A31	A32	A33	A34	A35	A36
A37	A38	A39	A40	A41	A42	A43	A44	A45	A46	A47	A48
A49	A50	A51	A52	A53	A54	A55	A56	A57	A58	A59	A60
A61	A62	A63	A64	A65	A66	A67	A68	A69	A70	A71	A72
A73	A74	A75	A76	A77	A78	A79	A80	A81	A82	A83	A84
A85	A86	A87	A88	A89	A90	A91	A92	A93	A94	A95	A96
A97	A98	A99	A100	A101	A102	A103	A104	A105	A106	A107	A108
A109	A110	A111	A112	A113	A114	A115	A116	A117	A118	A119	A120
A121	A122	A123	A124	A125	A126	A127	A128	A129	A130	A131	A132
A133	A134	A135	A136	A137	A138	A139	A140	A141	A142	A143	A144
A145	A146	A147	A148	A149	A150	A151	A152	A153	A154	A155	A156
A157	A158	A159	A160	A161	A162	A163	A164	A165	A166	A167	A168
A169	A170	A171	A172	A173	A174	A175	A176	A177	A178	A179	A180
A181	A182	A183	A184	A185	A186	A187	A188	A189	A190	A191	A192
A193	A194	A195	A196	A197	A198	A199	A200	A201	A202	A203	A204
A205	A206	A207	A208	A209	A210	A211	A212	A213	A214	A215	A216
A217	A218	A219	A220	A221	A222	A223	A224	A225	A226	A227	A228
A229	A230	A231	A232	A233	A234	A235	A236	A237	A238	A239	A240
A241	A242	A243	A244	A245	A246	A247	A248	A249	A250	A251	A252
A253	A254	A255	A256	A257	A258	A259	A260	A261	A262	A263	A264
A265	A266	A267	A268	A269	A270	A271	A272	A273	A274	A275	A276
A277	A278	A279	A280	A281	A282	A283	A284	A285	A286	A287	A288
A289	A290	A291	A292	A293	A294	A295	A296	A297	A298	A299	A300
A301	A302	A303	A304	A305	A306	A307	A308	A309	A310	A311	A312
A313	A314	A315	A316	A317	A318	A319	A320	A321	A322	A323	A324
A325	A326	A327	A328	A329	A330	A331	A332	A333	A334	A335	A336
A337	A338	A339	A340	A341	A342	A343	A344	A345	A346	A347	A348
A349	A350	A351	A352	A353	A354	A355	A356	A357	A358	A359	A360
A361	A362	A363	A364	A365	A366	A367	A368	A369	A370	A371	A372
A373	A374	A375	A376	A377	A378	A379	A380	A381	A382	A383	A384
A385	A386	A387	A388	A389	A390	A391	A392	A393	A394	A395	A396
A397	A398	A399	A400	A401	A402	A403	A404	A405	A406	A407	A408
A409	A410	A411	A412	A413	A414	A415	A416	A417	A418	A419	A420
A421	A422	A423	A424	A425	A426	A427	A428	A429	A430	A431	A432
A433	A434	A435	A436	A437	A438	A439	A440	A441	A442	A443	A444
A445	A446	A447	A448	A449	A450	A451	A452	A453	A454	A455	A456
A457	A458	A459	A460	A461	A462	A463	A464	A465	A466	A467	A468
A469	A470	A471	A472	A473	A474	A475	A476	A477	A478	A479	A480
A481	A482	A483	A484	A485	A486	A487	A488	A489	A490	A491	A492
A493	A494	A495	A496	A497	A498	A499	A500	A501	A502	A503	A504
A505	A506	A507	A508	A509	A510	A511	A512	A513	A514	A515	A516
A517	A518	A519	A520	A521	A522	A523	A524	A525	A526	A527	A528
A529	A530	A531	A532	A533	A534	A535	A536	A537	A538	A539	A540
A541	A542	A543	A544	A545	A546	A547	A548	A549	A550	A551	A552
A553	A554	A555	A556	A557	A558	A559	A560	A561	A562	A563	A564
A565	A566	A567	A568	A569	A570	A571	A572	A573	A574	A575	A576
A577	A578	A579	A580	A581	A582	A583	A584	A585	A586	A587	A588
A589	A590	A591	A592	A593	A594	A595	A596	A597	A598	A599	A600
A601	A602	A603	A604	A605	A606	A607	A608	A609	A610	A611	A612
A613	A614	A615	A616	A617	A618	A619	A620	A621	A622	A623	A624
A625	A626	A627	A628	A629	A630	A631	A632	A633	A634	A635	A636
A637	A638	A639	A640	A641	A642	A643	A644	A645	A646	A647	A648
A649	A650	A651	A652	A653	A654	A655	A656	A657	A658	A659	A660
A661	A662	A663	A664	A665	A666	A667	A668	A669	A670	A671	A672
A673	A674	A675	A676	A677	A678	A679	A680	A681	A682	A683	A684
A685	A686	A687	A688	A689	A690	A691	A692	A693	A694	A695	A696
A697	A698	A699	A700	A701	A702	A703	A704	A705	A706	A707	A708
A709	A710	A711	A712	A713	A714	A715	A716	A717	A718	A719	A720
A721	A722	A723	A724	A725	A726	A727	A728	A729	A730	A731	A732
A733	A734	A735	A736	A737	A738	A739	A740	A741	A742	A743	A744
A745	A746	A747	A748	A749	A750	A751	A752	A753	A754	A755	A756
A757	A758	A759	A760	A761	A762	A763	A764	A765	A766	A767	A768
A769	A770	A771	A772	A773	A774	A775	A776	A777	A778	A779	A780
A781	A782	A783	A784	A785	A786	A787	A788	A789	A790	A791	A792
A793	A794	A795	A796	A797	A798	A799	A800	A801	A802	A803	A804
A805	A806	A807	A808	A809	A810	A811	A812	A813	A814	A815	A816
A817	A818	A819	A820	A821	A822	A823	A824	A825	A826	A827	A828
A829	A830	A831	A832	—	—	—	—	—	—	—	—

[0184]

TABLE 7
Compounds of the formula I, represented as compounds of the formula
A-Q
in which Q denotes Q2 and Q2 denotes the radicals D1, D2 or D3:
D1/D2/	D1/D2/	D1/D2/	D1/D2/	D1/D2/	D1/D2/	D1/D2/	D1/D2/	D1/D2/	D1/D2/	D1/D2/	D1/D2/
D3	D3	D3	D3	D3	D3	D3	D3	D3	D3	D3	D3
—	—	—	—	—	—	—	A8	A9	A10	A11	A12
A13	A14	A15	A16	A17	A18	A19	A20	A21	A22	A23	A24
A25	A26	A27	A28	A29	A30	A31	A32	A33	A34	A35	A36
A37	A38	A39	A40	A41	A42	A43	A44	A45	A46	A47	A48
A49	A50	A51	A52	A53	A54	A55	A56	A57	A58	A59	A60
A61	A62	A63	A64	A65	A66	A67	A68	A69	A70	A71	A72
A73	A74	A75	A76	A77	A78	A79	A80	A81	A82	A83	A84
A85	A86	A87	A88	A89	A90	—	—	—	—	—	—
—	—	A99	A100	A101	A102	A103	A104	A105	A106	A107	A108
A109	A110	A111	A112	A113	A114	A115	A116	A117	A118	A119	A120
A121	A122	A123	A124	A125	A126	A127	A128	A129	A130	A131	A132
A133	A134	A135	A136	A137	A138	A139	A140	A141	A142	A143	A144
A145	A146	A147	A148	A149	A150	A151	A152	A153	A154	A155	A156
A157	A158	A159	A160	A161	A162	A163	A164	A165	A166	A167	A168
A169	A170	A171	A172	A173	A174	A175	A176	A177	A178	A179	A180
A181	A182	A183	A184	A185	A186	A187	A188	A189	A190	A191	A192
A193	A194	A195	A196	A197	A198	A199	A200	A201	A202	A203	A204
A205	A206	A207	A208	A209	A210	A211	A212	A213	A214	A215	A216
A217	A218	A219	A220	A221	A222	A223	A224	A225	A226	A227	A228
A229	A230	A231	A232	A233	A234	A235	A236	A237	A238	A239	A240
A241	A242	A243	A244	A245	A246	A247	A248	A249	A250	A251	A252
A253	A254	A255	A256	A257	A258	A259	A260	A261	A262	A263	A264
A265	A266	A267	A268	A269	A270	A271	A272	A273	A274	A275	A276
A277	A278	A279	A280	A281	A282	A283	A284	A285	A286	A287	A288
A289	A290	A291	A292	A293	A294	A295	A296	A297	A298	A299	A300
A301	A302	A303	A304	A305	A306	A307	A308	A309	A310	A311	A312
A313	A314	A315	A316	A317	A318	A319	A320	A321	A322	A323	A324
A325	A326	A327	A328	A329	A330	A331	A332	A333	A334	A335	A336
A337	A338	A339	A340	A341	A342	A343	A344	A345	A346	A347	A348
A349	A350	A351	A352	A353	A354	A355	A356	A357	A358	A359	A360
A361	A362	A363	A364	A365	A366	A367	A368	A369	A370	A371	A372
A373	A374	A375	A376	A377	A378	A379	A380	A381	A382	A383	A384
A385	A386	A387	A388	A389	A390	A391	A392	A393	A394	A395	A396
A397	A398	A399	A400	A401	A402	A403	A404	A405	A406	A407	A408
A409	A410	A411	A412	A413	A414	A415	A416	A417	A418	A419	A420
A421	A422	A423	A424	A425	A426	A427	A428	A429	A430	A431	A432
A433	A434	A435	A436	A437	A438	A439	A440	A441	A442	A443	A444
A445	A446	A447	A448	A449	A450	A451	A452	A453	A454	A455	A456
A457	A458	A459	A460	A461	A462	A463	A464	A465	A466	A467	A468
A469	A470	A471	A472	A473	A474	A475	A476	A477	A478	A479	A480
A481	A482	A483	A484	A485	A486	A487	A488	A489	A490	A491	A492
A493	A494	A495	A496	A497	A498	A499	A500	A501	A502	A503	A504
A505	A506	A507	A508	A509	A510	A511	A512	A513	A514	A515	A516
A517	A518	A519	A520	A521	A522	A523	A524	A525	A526	A527	A528
A529	A530	A531	A532	A533	A534	A535	A536	A537	A538	A539	A540
A541	A542	A543	A544	A545	—	—	—	—	—	—	—
—	A554	A555	A556	A557	A558	A559	A560	A561	A562	A563	A564
A565	A566	A567	A568	A569	A570	A571	A572	A573	A574	A575	A576
A577	A578	A579	A580	A581	A582	A583	A584	A585	A586	A587	A588
A589	A590	A591	A592	A593	A594	A595	A596	A597	A598	A599	A600
A601	A602	A603	A604	A605	A606	A607	A608	A609	A610	A611	A612
A613	A614	A615	A616	A617	A618	A619	A620	A621	A622	A623	A624
A625	A626	A627	A628	A629	A630	A631	A632	A633	A634	A635	A636
—	—	—	—	—	—	—	A644	A645	A646	A647	A648
A649	A650	A651	A652	A653	A654	A655	A656	A657	A658	A659	A660
A661	A662	A663	A664	A665	A666	A667	A668	A669	A670	A671	A672
A685	A686	A687	A688	A689	A690	A691	A692	A693	A694	A695	A696
A697	A698	A699	A700	A701	A702	A703	A704	A705	A706	A707	A708
A709	A710	A711	A712	A713	A714	A715	A716	A717	A718	A719	A720
A721	A722	A723	A724	A725	A726	—	—	—	—	—	—
A733	A734	A735	A736	A737	A738	A739	A740	A741	A742	A743	A744
A745	A746	A747	A748	A749	A750	A751	A752	A753	A754	A755	A756
A757	A758	A759	A760	A761	A762	A763	A764	A765	A766	A767	A768
A769	A770	A771	A772	A773	A774	A775	A776	A777	A778	A779	A780
A781	A782	A783	A784	A785	A786	A787	A788	A789	A790	A791	A792
A793	A794	A795	A796	A797	A798	A799	A800	A801	A802	A803	A804
A805	A806	A807	A808	A809	A810	A811	A812	A813	A814	A815	A816
A817	A818	A819	A820	A821	A822	A823	A824	A825	A826	A827	A828
A829	A830	A831	A832	—	—	—	—	—	—	—	—

[0185]

TABLE 8
Compounds of the formula Ip:
728
in which R1, R2, R3, R4, X1 and p have the same meaning as given for the radical A,
and n is 0,1 or 2:
A	A	A	A	A	A	A	A	A	A	A	A
—	—	—	—	—	—	—	A8	A9	A10	A11	A12
A13	A14	A15	A16	A17	A18	A19	A20	A21	A22	A23	A24
A25	A26	A27	A28	A29	A30	A31	A32	A33	A34	A35	A36
A37	A38	A39	A40	A41	A42	A43	A44	A45	A46	A47	A48
A49	A50	A51	A52	A53	A54	A55	A56	A57	A58	A59	A60
A61	A62	A63	A64	A65	A66	A67	A68	A69	A70	A71	A72
A73	A74	A75	A76	A77	A78	A79	A80	A81	A82	A83	A84
A85	A86	A87	A88	A89	A90	—	—	—	—	—	—
—	—	A99	A100	A101	A102	A103	A104	A105	A106	A107	A108
A109	A110	A111	A112	A113	A114	A115	A116	A117	A118	A119	A120
A121	A122	A123	A124	A125	A126	A127	A128	A129	A130	A131	A132
A133	A134	A135	A136	A137	A138	A139	A140	A141	A142	A143	A144
A145	A146	A147	A148	A149	A150	A151	A152	A153	A154	A155	A156
A157	A158	A159	A160	A161	A162	A163	A164	A165	A166	A167	A168
A169	A170	A171	A172	A173	A174	A175	A176	A177	A178	A179	A180
A181	A182	A183	A184	A185	A186	A187	A188	A189	A190	A191	A192
A193	A194	A195	A196	A197	A198	A199	A200	A201	A202	A203	A204
A205	A206	A207	A208	A209	A210	A211	A212	A213	A214	A215	A216
A217	A218	A219	A220	A221	A222	A223	A224	A225	A226	A227	A228
A229	A230	A231	A232	A233	A234	A235	A236	A237	A238	A239	A240
A241	A242	A243	A244	A245	A246	A247	A248	A249	A250	A251	A252
A253	A254	A255	A256	A257	A258	A259	A260	A261	A262	A263	A264
A265	A266	A267	A268	A269	A270	A271	A272	A273	A274	A275	A276
A277	A278	A279	A280	A281	A282	A283	A284	A285	A256	A287	A288
A289	A290	A291	A292	A293	A294	A295	A296	A297	A298	A299	A300
A301	A302	A303	A304	A305	A306	A307	A308	A309	A310	A311	A312
A313	A314	A315	A316	A317	A318	A319	A320	A321	A322	A323	A324
A325	A326	A327	A328	A329	A330	A331	A332	A333	A334	A335	A336
A337	A338	A339	A340	A341	A342	A343	A344	A345	A346	A347	A348
A349	A350	A351	A352	A353	A354	A355	A356	A357	A358	A359	A360
A361	A362	A363	A364	A365	A366	A367	A368	A369	A370	A371	A372
A373	A374	A375	A376	A377	A378	A379	A380	A381	A382	A383	A384
A385	A386	A387	A388	A389	A390	A391	A392	A393	A394	A395	A396
A397	A398	A399	A400	A401	A402	A403	A404	A405	A406	A407	A408
A409	A410	A411	A412	A413	A414	A415	A416	A417	A418	A419	A420
A421	A422	A423	A424	A425	A426	A427	A428	A429	A430	A431	A432
A433	A434	A435	A436	A437	A438	A439	A440	A441	A442	A443	A444
A445	A446	A447	A448	A449	A450	A451	A452	A453	A454	A455	A456
A457	A458	A459	A460	A461	A462	A463	A464	A465	A466	A467	A468
A469	A470	A471	A472	A473	A474	A475	A476	A477	A478	A479	A480
A481	A482	A483	A484	A485	A486	A487	A488	A489	A490	A491	A492
A493	A494	A495	A496	A497	A498	A499	A500	A501	A502	A503	A504
A505	A506	A507	A508	A509	A510	A511	A512	A513	A514	A515	A516
A517	A518	A519	A520	A521	A522	A523	A524	A525	A526	A527	A528
A529	A530	A531	A532	A533	A534	A535	A536	A537	A538	A539	A540
A541	A542	A543	A544	A545	—	—	—	—	—	—	—
—	A554	A555	A556	A557	A558	A559	A560	A561	A562	A563	A564
A565	A566	A567	A568	A569	A570	A571	A572	A573	A574	A575	A576
A577	A578	A579	A580	A581	A582	A583	A584	A585	A586	A587	A588
A589	A590	A591	A592	A593	A594	A595	A596	A597	A598	A599	A600
A601	A602	A603	A604	A605	A606	A607	A608	A609	A610	A611	A612
A613	A614	A615	A616	A617	A618	A619	A620	A621	A622	A623	A624
A625	A626	A627	A628	A629	A630	A631	A632	A633	A634	A635	A636
—	—	—	—	—	—	—	A644	A645	A646	A647	A648
A649	A650	A651	A652	A653	A654	A655	A656	A657	A658	A659	A660
A661	A662	A663	A664	A665	A666	A667	A668	A669	A670	A671	A672
A685	A686	A687	A688	A689	A690	A691	A692	A693	A694	A695	A696
A697	A698	A699	A700	A701	A702	A703	A704	A705	A706	A707	A708
A709	A710	A711	A712	A713	A714	A715	A716	A717	A718	A719	A720
A721	A722	A723	A724	A725	A726	—	—	—	—	—	—
A733	A734	A735	A736	A737	A738	A739	A740	A741	A742	A743	A744
A745	A746	A747	A748	A749	A750	A751	A752	A753	A754	A755	A756
A757	A758	A759	A760	A761	A762	A763	A764	A765	A766	A767	A768
A769	A770	A771	A772	A773	A774	A775	A776	A777	A778	A779	A780
A781	A782	A783	A784	A785	A786	A787	A788	A789	A790	A791	A792
A793	A794	A795	A796	A797	A798	A799	A800	A801	A802	A803	A804
A805	A806	A807	A808	A809	A810	A811	A812	A813	A814	A815	A816
A817	A818	A819	A820	A821	A822	A823	A824	A825	A826	A827	A828
A829	A830	A831	A832	—	—	—	—	—	—	—	—

[0186]

TABLE 9
Compounds of the formula I, represented as compounds of the formula
A-Q
in which A denotes A10:
A10	A10	A10	A10	A10	A10	A10	A10	A10	A10	A10	A10
B1	B2	—	B4	B5	B6	B7	B8	B9	B10	B11	B12
B13	B14	B15	B16	B17	B18	B19	B20	B21	B22	B23	B24
B25	B26	B27	B28	B29	B30	B31	B32	B33	B34	B35	B36
B37	B38	—	B40	B41	B42	B43	B44	B45	B46	B47	B48
B49	B50	B51	—	B53	B54	B55	B56	B57	B58	B59	B60
B61	B62	B63	B64	B65	B66	B67	B68	B69	B70	B71	B72
B73	B74	B75	B76	B77	B78	B79	B80	B81	B82	B83	B84
B85	B86	B87	B88	B89	B90	B91	B92	B93	B94		B96
B97	B98	B99	B100	B101	B102	B103	B104	B105	B106	B107	B108
B109	B110	—	—	—	—	—	—	—	—	—	—

[0187]

TABLE 10
Compounds of the formula I, represented as compounds of the formula
A-Q
in which A denotes A10:
A10	A10	A10	A10	A10	A10	A10	A10	A10	A10	A10	A10
C1	—	C3	C4	—	C6	C7	C8	C9	C10	C11	C12
C13	C14	C15	C16	C17	C18	C19	C20	C21	C22	C23	C24
C25	C26	C27	—	—	—	—	—	—	—	—	—

[0188]

TABLE 11
Compounds of the formula I, represented as compounds of the formula
A-Q
in which A denotes A10:
A10	A10	A10	A10	A10	A10	A10	A10	A10	A10	A10	A10
—	—	—	D4	D5	D6	D7	D8	D9	D10	D11	D12

[0189]

TABLE 12
Compounds of the formula I, represented as compounds of the formula
A-Q
in which A denotes A556:
A556	A556	A556	A556	A556	A556	A556	A556	A556	A556	A556	A556
B1	B2	—	B4	B5	B6	B7	B8	B9	B10	B11	B12
B13	B14	B15	B16	B17	B18	B19	B20	B21	B22	B23	B24
B25	B26	B27	B28	B29	B30	B31	B32	B33	B34	B35	B36
B37	B38	—	B40	B41	B42	B43	B44	B45	B46	B47	B48
B49	B50	B51	—	B53	B54	B55	B56	B57	B58	B59	B60
B61	B62	B63	B64	B65	B66	B67	B68	B69	B70	B71	B72
B73	B74	B75	B76	B77	B78	B79	B80	B81	B82	B83	B84
B85	B86	B87	B88	B89	B90	B91	B92	B93	B94		B96
B97	B98	B99	B100	B101	B102	B103	B104	B105	B106	B107	B108
B109	B110	—	—	—	—	—	—	—	—	—	—

[0190]

TABLE 13
Compounds of the formula I, represented as compounds of the formula
A-Q
in which A denotes A556:
A556	A556	A556	A556	A556	A556	A556	A556	A556	A556	A556	A556
C1	—	C3	C4	—	C6	C7	C8	C9	C10	C11	C12
C13	C14	C15	C16	C17	C18	C19	C20	C21	C22	C23	C24
C25	C26	C27	—	—	—	—	—	—	—	—	—

[0191]

TABLE 14
Compounds of the formula I, represented as compounds of the formula
A-Q
in which A denotes A556:
A556	A556	A556	A556	A556	A556	A556	A556	A556	A556	A556	A556
—	—	—	D4	D5	D6	D7	D8	D9	D10	D11	D12

[0192]

TABLE 15
Compounds of the formula I, represented as compounds of the formula
A-Q
in which A denotes A646:
A646	A646	A646	A646	A646	A646	A646	A646	A646	A646	A646	A646
B1	B2	—	B4	B5	B6	B7	B8	B9	B10	B11	B12
B13	B14	B15	B16	B17	B18	B19	B20	B21	B22	B23	B24
B25	B26	B27	B28	B29	B30	B31	B32	B33	B34	B35	B36
B37	B38	—	B40	B41	B42	B43	B44	B45	B46	B47	B48
B49	B50	B51	—	B53	B54	B55	B56	B57	B58	B59	B60
B61	B62	B63	B64	B65	B66	B67	B68	B69	B70	B71	B72
B73	B74	B75	B76	B77	B78	B79	B80	B81	B82	B83	B84
B85	B86	B87	B88	B89	B90	B91	B92	B93	B94		B96
B97	B98	B99	B100	B101	B102	B103	B104	B105	B106	B107	B108
B109	B110	—	—	—	—	—	—	—	—	—	—

[0193]

TABLE 16
Compounds of the formula I, represented as compounds of the formula
A-Q
in which A denotes A646:
A646	A646	A646	A646	A646	A646	A646	A646	A646	A646	A646	A646
C1	—	C3	C4	—	C6	C7	C8	C9	C10	C11	C12
C13	C14	C15	C16	C17	C18	C19	C20	C21	C22	C23	C24
C25	C26	C27	—	—	—	—	—	—	—	—	—

[0194]

TABLE 17
Compounds of the formula I, represented as compounds of the formula
A-Q
in which A denotes A646:
A646	A646	A646	A646	A646	A646	A646	A646	A646	A646	A646	A646
—	—	—	D4	D5	D6	D7	D8	D9	D10	D11	D12

[0195]

TABLE 18
Physical data for the compounds of the formula I
given in the tables above: (the melting points are given in ° C.)
	Compound	m.p. (range)	Phys. state
	A1-C2	138-140	crystalline
	A2-C2	138-140	crystalline
	A833-B52 (K+)	145-150	crystalline
	A833-B52 (H4)	—	oil
	A830-B52	—	amorphous/liquid
	A829-B52	—	oil
	A829-B1	—	oil
	A10-B52 (H3)	54-56	crystalline
	A10-B1	71-73	crystalline
	A10-B3	—	viscous
	A10-B14	—	viscous
	A10-B39	99-100	crystalline
	A736-B52	100-102	crystalline
	A10-C2 (H6)	—	viscous
	A57-B52 (H5)	54-56	crystalline
	A18-B52	71-74	crystalline
	A8-B52	95-98	crystalline
	A19-B52	53-55	crystalline
	A1-C5	32-34	crystalline
	A2-C5	32-33	crystalline
	A10-C5	—	resin
	A11-C5	38-39	crystalline
	A11-B52	—	resin
	A834-B52	—	crystalline
	A835-B52	—	viscous
	A854-B52	—	viscous
	A90-B52	—	viscous
	A33-B52	113-115	crystalline
	A556-B52	—	crystalline
	A646-B52	—	viscous
	A868-B52	106-107	crystalline
	A855-B52	—	viscous
	A817-B52	—	viscous
	A819-B52	—	crystalline
	A856-B52	—	solid
	A857-B52	—	viscous
	A63-B52	—	resin
	A20-B52	—	solid
	A858-B52	—	resin
	A836-B52	—	crystalline
	A859-B52	—	viscous
	A818-B52	—	viscous
	A837-B52	—	viscous
	A28-B52	—	viscous
	A28-B52 (Et3NH+)	—	crystalline
	A838-B52	—	viscous
	A839-B52	—	viscous
	A860-B52	—	viscous
	A860-B113	—	viscous
	A861-B52	90-93	crystalline
	A840-B52	—	oil
	A841-B52	41-43	crystalline
	A842-B52	—	viscous
	A843-B52	—	viscous
	A866-B100	96-98	crystalline
	A844-B52	—	viscous
	A866-B112	—	viscous
	A867-B112	—	viscous
	A856-B112	79-81	crystalline
	A20-C5	—	viscous
	A10-C28	—	resin
	A11-C28	—	resin
	A10-B52 (Et3NH+)	—	viscous
	A862-B52	—	viscous
	A24-B52	102-105	crystalline
	A845-B52	40-44	crystalline
	A837-B52	—	viscous
	(Et3NH+)
	A67-B52	68-69	crystalline
	A863-B52	80-80	crystalline
	A10-B17	40-42	crystalline
	A846-B52	—	crystalline
	A847-B52	—	viscous
	A848-B52	—	crystalline
	A56-B52	—	vitreous
	A26-B52	—	vitreous
	A849-B52	—	viscous
	A10-B4	—	viscous
	A865-B52	—	viscous
	A850-B52	63-64	crystalline
	A10-C29	—	resin
	A10-B111	76-78	crystalline
	A3-C5	—	resin
	A834-C5	—	resin
	A851-B52	—	vitreous
	A852-B52	—	viscous
	A10-B25	—	amorphous/liquid
	A853-B52	—	viscous
	A27-B52	—	oil
	A864-C5	149-150	crystalline
	A864-B52	110-112	crystalline
	A834-B39	—	oil
	A-852-OH	—	oil
	A-851-OH	102-103	crystalline
	A-835-OH	—	oil
	A-24-OH	—	solid
	A-858-OH	—	oil
	A-859-OH	—	oil
	A-864-OH	—	solid
	A-851-OH	73-74	crystalline
	A-848-OH	81-82	crystalline
	A-27-OH	—	oil
	A-855-OH	102-104	crystalline
	A-90-OH	111-114	crystalline
	A-124-OH	117-119	crystalline
	A-834-OH	—	crystalline
	A-852-OH	—	oil
	A-851-OH	102-103	crystalline
	A-835-OH	—	oil
	A10-OH	62-63	crystalline
	A830-OH	157-158	crystalline
	A831-OH	188-189	crystalline
	A829-OH	131-134	crystalline
	A832-OH	110-112	crystalline

[0196]

	TABLE 19
	Physical data for the compounds of the formula I given in the tables above: (the
	melting points given in ° C.,):
	In the following formulas, end-standing valences denote methyl groups (in all cases except
	alkyne or alkene groups) or hydrogen (in the case of alkyne or alkene groups), for example
	729	can also drawn as	730
and
	731	can be also drawn as	732
Comp.		m.p. (range)
No.	Corresponding Formula	Phys. state
1.001	733	138-140 crystalline
1.002	734	145-150 crystalline
1.003	735	oil
1.004	736	oil
1.005	737	oil
1.006	738	oil
1.007	739	54-46 crystalline
1.008	740	crystalline
1.009	741	viscous, 1H NMR; 1.82 (s); 3.26 (s); 3.37-3.39 (m); 3.57-3.60(m); 3.71(s); 4.84 (s); 7.74 (d); 7.82 (d)
1.010	742	viscous
1.011	743	viscous
1.012	744	99-100 crystalline
1.013	745	100-102 crystalline
1.014	746	viscous
1.015	747	54-56 crystalline
1.016	748	71-74 crystalline
1.017	749	95-98 crystalline
1.018	750	53-55 crystalline
1.019	751	32-34 crystalline
1.020	752	32-33 crystalline
1.021	753	resin
1.022	754	38-39 crystalline
1.023	755	resin
1.024	756	crystalline
1.025	757	viscous
1.026	758	viscous
1.027	759	viscous
1.028	760	113-115 crystalline
1.029	761	crystalline
1.030	762	viscous
1.031	763	106-107 crystalline
1.032	764	viscous
1.033	765	viscous
1.034	766	crystalline
1.035	767	crystalline
1.036	768	viscous
1.037	769	resin
1.038	770	solid
1.039	771	resin
1.040	772	crystalline
1.041	773	viscous
1.042	774	viscous
1.043	775	viscous
1.044	776	viscous
1.045	777	crystalline
1.046	778	viscous
1.047	779	viscous
1.048	780	viscous
1.049	781	viscous
1.050	782	90-93
1.051	783	oil
1.052	784	41-43
1.053	785	viscous
1.054	786	viscous
1.055	787	96-98
1.056	788	viscous
1.057	789	viscous
1.058	790	viscous
1.059	791	79-81
1.060	792	viscous
1.061	793	viscous
1.062	794	viscous
1.063	795	crystalline
1.064	796	viscous
1.065	797	102-105 crystalline
1.066	798	40-44 crystalline
1.067	799	viscous
1.068	800	68-69 crystalline
1.069	801	78-80 crystalline
1.070	802	40-42
1.071	803	crystalline
1.072	804	viscous
1.073	805	46-47 crystalline
1.074	806	vitreous
1.075	807	vitreous
1.076	808	75-76
1.077	809	viscous
1.078	810	viscous
1.079	811	viscous
1.080	812	63-64 crystalline
1.081	813	resin
1.082	814	76-78 crystalline
1.083	815	resin
1.084	816	resin
1.085	817	vitreous
1.086	818	viscous
1.087	819	oil
1.088	820	viscous
1.089	821	oil
1.090	822	149-150 crystalline
1.091	823	110-112 crystalline
1.092	824	crystalline

BIOLOGICAL EXAMPLES

Example B1

[0197] Herbicidal action before emergence of the plants (pre-emergence action)

[0198] Monocotyledonous and dicotyledonous test plants are sown in standard soil in pots. Immediately after sowing, the test substances are sprayed on at an optimum dosage (500 l of water/ha) as an aqueous suspension (prepared from a wettable powder (example F3, b) according to WO 97/34485) or emulsion (prepared from an emulsion concentrate (example F1, c) according to WO 97/34485). The test plants are then grown under optimum conditions in a greenhouse.

[0199] After a test period of 4 weeks, the test is evaluated using a 9-level scale of ratings (1=complete damage, 9=no effect). Ratings of 1 to 4 (in particular 1 to 3) mean good to very good herbicidal action.

TABLE B1
Pre-emergence action: (“NT” means “not tested”):
Compound	g/ha	Panicum	Digitaria	Echino.	Abutilon	Amaranthus	Chenop.
A10-B1	250	2	2	2	1	1	1
A10-B52, (H3)	250	1	1	1	1	1	1
A830-B52	250	4	9	3	5	4	4
A1-C2	250	6	3	3	4	3	1
A833-B52 (K+)	250	1	2	2	1	2	1
A833-B52, (H4)	250	1	1	1	1	1	1
A10-B1	250	2	2	2	1	1	1
A10-B3	250	1	1	1	1	1	1
A10-B14	250	3	6	3	1	1	1
A10-B39	250	1	1	1	1	1	1
A736-B52	250	1	4	2	1	1	1
A10-C2 (H6)	250	3	3	3	1	2	1
A57-B52 (H5)	250	1	1	1	1	1	1
A18-B52	250	1	1	1	2	2	NT
A8-B52	250	1	1	1	1	1	NT
A19-B52	250	1	1	1	1	2	NT
A1-C5	250	2	2	1	2	2	1
A2-C5	250	1	2	2	1	1	1
A10-C5	250	2	3	1	1	1	1
A11-C5	250	1	2	1	1	1	1
A11-B52	250	1	1	1	1	2	1
A834-B52	250	1	1	1	1	2	1
A835-B52	250	1	2	1	2	1	2
A556-B52	250	1	1	1	1	2	1
A646-B52	250	1	1	1	1	2	1
A819-B52	250	7	9	7	1	2	1
A63-B52	250	2	3	1	5	3	NT
A20-B52	250	1	1	1	3	3	NT
A836-B52	250	1	2	1	5	2	3
A837-B52	250	1	2	2	1	2	NT
A28-B52	250	1	2	2	2	3	NT
A28-B52 (Et3NH+)	250	1	2	2	3	1	NT
A838-B52	250	1	3	2	1	1	1
A839-B52	250	1	3	2	1	1	1
A840-B52	250	1	2	2	2	2	1
A841-B52	250	1	2	1	1	1	1
A842-B52	250	1	6	2	2	2	1
A843-B52	250	1	2	2	1	1	1
A844-B52	250	1	2	2	1	1	1
A20-C5	250	1	2	2	1	1	1
A10-C28	250	1	3	2	1	1	1
A11-C28	250	2	2	1	2	1	1
A10-B52 (Et3NH+)	250	1	1	2	1	1	1
A24-B52	250	1	1	1	1	1	1
A845-B52	250	1	1	1	1	1	1
A837-B52 (Et3NH+)	250	1	1	2	1	1	1
A67-B52	250	1	2	2	3	2	1
A10-B17	250	1	1	1	4	2	1
A846-B52	250	1	1	1	2	1	1
A847-B52	250	1	3	2	4	1	4
A848-B52	250	1	1	1	7	1	1
A56-B52	250	1	2	1	3	1	1
A26-B52	250	1	1	1	1	1	1
A849-B52	250	1	2	2	2	1	1
A10-B4	250	2	3	1	3	1	1
A850-B52	250	1	2	1	1	2	1
A10-C29	250	2	2	1	1	1	NT
A10-B111	250	1	1	1	1	1	NT
A3-C5	250	1	2	2	1	1	NT
A834-C5	250	1	3	1	1	2	NT
A851-B52	250	1	1	1	1	1	1
A852-B52	250	1	1	1	4	1	2
A10-B25	250	1	1	2	1	1	1
A853-B52	250	1	1	2	1	1	2
A27-B52	250	1	2	3	4	1	3

[0200] The same results are obtained when the compounds of the formula I are formulated according to the other examples of WO 97/34485.

Example B2

Post-emergence Herbicidal Action

[0201] Monocotyledonous and dicotyledonous test plants are grown in standard soil in pots. At the 2- to 3-leaf stage of the test plants, the test substances are sprayed at optimum dosage (500 l of water/ha) as an aqueous suspension (prepared from a wettable powder (example F3, b) according to WO 97/34485) or emulsion (prepared from an emulsion concentrate (example F1, c) according to WO 97/34485). The test plants are then grown further under optimum conditions in a greenhouse.

[0202] After a test period of 2 to 3 weeks, the test is evaluated using a 9-level scale of rating (1=complete damage, 9=no effect). Ratings of 1 to 4 (in particular 1 to 3) mean good to very good herbicidal action.

TABLE B2
Post-emergence action:
Compound	g/ha	Panicum	Digitaria	Echino.	Abutilon	Xanth.	Ipopur.	Amaranth	Chenop.
A10-B1	250	2	2	2	2	2	2	2	1
A10-B52, (H3)	250	1	1	2	1	2	2	2	1
A830-B52	250	4	9	3	5	4	5	4	4
A829-B52	250	2	6	4	3	6	4	2	2
A829-B1	250	7	9	7	7	4	6	2	2
A1-C2	250	7	8	4	3	4	3	2	4
A833-B52 (K+)	250	3	3	4	3	2	3	3	3
A833-B52, (H4)	250	3	3	4	3	1	2	2	3
A10-B3	250	1	1	3	1	1	2	1	1
A10-B14	250	2	2	3	2	2	2	2	1
A10-B39	250	1	3	3	1	2	2	1	1
A736-B52	250	1	1	2	1	2	2	1	1
A10-C2 (H6)	250	2	4	3	2	1	3	1	1
A57-B52 (H5)	250	1	1	2	1	2	2	1	1
A18-B52	250	1	1	2	1	2	2	1	1
A8-B52	250	1	1	1	1	2	1	1	1
A19-B52	250	1	1	2	1	2	1	1	1
A1-C5	250	4	2	2	2	4	2	2	1
A2-C5	250	1	2	2	2	2	2	1	1
A10-C5	250	2	2	2	2	2	2	1	1
A11-C5	250	1	2	2	2	2	2	2	1
A11-B52	250	1	1	2	2	2	2	1	1
A834-B52	250	1	1	2	2	2	2	1	1
A835-B52	250	1	1	2	2	3	2	2	1
A854-B52	250	1	2	2	2	2	2	1	1
A90-B52	250	2	2	3	2	3	4	3	1
A33-B52	250	2	2	2	2	3	2	2	1
A556-B52	250	1	2	2	1	2	2	2	1
A646-B52	250	1	2	2	2	2	2	2	1
A855-B52	250	2	2	2	2	2	2	2	1
A817-B52	250	1	2	2	2	2	2	2	1
A819-B52	250	2	3	2	2	2	2	2	1
A856-B52	250	2	2	2	2	2	1	2	1
A857-B52	250	2	2	2	2	2	2	2	1
A63-B52	250	1	2	2	2	2	2	2	2
A20-B52	250	1	2	2	2	2	2	2	1
A858-B52	250	2	2	2	2	2	2	1	2
A836-B52	250	2	2	2	2	3	3	2	1
A859-B52	250	1	2	2	2	2	2	2	1
A818-B52	250	2	2	3	2	2	2	2	1
A837-B52	250	1	2	2	2	2	2	1	1
A28-B52	250	1	2	2	2	3	4	1	1
A28-B52	250	1	2	2	2	3	2	2	1
(Et3NH+)
A838-B52	250	2	2	3	1	2	2	2	1
A839-B52	250	2	2	2	2	2	2	2	1
A860-B52	250	2	1	2	2	2	2	2	1
A861-B52	250	2	3	5	3	2	2	2	1
A840-B52	250	2	3	4	3	3	3	2	1
A841-B52	250	2	4	4	3	3	3	1	1
A842-B52	250	3	3	5	3	3	3	2	1
A843-B52	250	2	3	3	3	3	6	3	1
A844-B52	250	2	3	4	3	3	3	3	1
A856-B112	250	3	3	5	2	3	3	3	1
A20-C5	250	2	3	4	3	3	3	2	1
A10-C28	250	4	4	4	3	3	3	2	1
A11-C28	250	3	4	4	3	3	3	2	1
A10-B52	250	2	2	2	2	2	2	2	1
(Et3NH+)
A862-B52	250	2	2	3	3	2	5	2	1
A24-B52	250	2	2	2	2	2	2	2	1
A845-B52	250	2	2	2	2	2	2	2	1
A837-B52	250	2	2	2	2	2	2	2	1
(Et3NH+)
A67-B52	250	2	2	2	2	2	3	2	1
A863-B52	250	2	2	3	2	2	3	2	1
A10-B17	250	2	1	2	2	2	2	2	1
A846-B52	250	1	2	2	2	2	1	2	2
A847-B52	250	1	2	1	2	2	4	3	1
A848-B52	250	2	2	2	2	2	2	1	1
A56-B52	250	1	2	2	2	2	2	1	1
A26-B52	250	2	2	2	2	2	2	2	1
A849-B52	250	2	2	3	2	2	2	2	2
A10-B4	250	1	1	2	1	2	1	2	1
A850-B52	250	2	2	2	2	2	2	2	1
A10-C29	250	2	3	3	2	2	1	2	1
A10-B111	250	2	2	3	3	3	3	2	1
A3-C5	250	3	4	3	3	3	3	3	1
A851-B52	250	3	3	4	3	3	3	2	1
A852-B52	250	3	4	4	3	3	3	3	1
A10-B25	250	3	4	4	3	3	3	2	1
A27-B52	250	1	2	2	3	2	4	2	5
A864-C5	250	1	2	2	2	2	2	1	1
A864-B52	250	2	2	2	2	2	2	2	1

[0203] The same results are obtained when the compounds of the formula I are formulated according to the other examples of WO 97/34485.

Claims

1. A compound of the formula I

2. A process for preparing compounds of the formula I as claimed in claim 1, which comprises, to prepare compounds of the formula I, in which R1, R2, R3, R4 and X1 are as defined under formula I and Q is a group Q1, either a) reacting a compound of the formula Ia

3. A herbicidal and plant-growth-inhibiting composition, which contains a herbicidally effective amount of a compound of the formula I on an inert carrier.

4. A method for controlling undesirable plant growth, wherein a herbicidally effective amount of an active compound of the formula I or a composition which contains this active compound is applied to the plants or their habitat.

5. A method for inhibiting plant growth, wherein a herbicidally effective amount of an active compound of the formula I or a composition which contains this active compound is applied to the plants or their habitat.

6. A compound of the formula XX