# Patent

## Title
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.

## Background
This application is a Division of U.S. Ser. No. 10/297,685, filed Dec. 6, 2002 now U.S. Pat. No. 6,838,564 which is a 371 of International Application No. PCT/EP01/06430, filed Jun. 7, 2001, the contents of which are incorporated herein by reference.


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.
Pyridine ketones having herbicidal action are described, for example, in WO 00/15615 and WO/0039094.
We have now found novel pyridine ketones having herbicidal and growth-inhibiting properties.
The present invention thus provides compounds of the formula I




in which

p is 0 or 1;

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; with the proviso that R1 is different from methylen if R2 is unsubstituted phenyl and X1 is —O(CO)—;

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

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, R10,ON(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

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

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

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-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; or

R2 is hydrogen or unsubstituted C1-C8alkyl if

a) R1 is substituted by the group R5, or

b) Q is the group Q2, or

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

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

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

R3 is C1-C3haloalkyl;

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

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

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;

Q is Q1





in which

A1 is C(R14R15), NR16 or oxygen;

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;

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

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

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

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;

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;

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

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;

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

R22 and R18 together form a C2-C4alkylene chain;

or R18 together with R22 or R14 forms a direct bond;

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

R13 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, 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;

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;

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;

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

or R23 and R24 together or R25 and R26 together or R27 and R28 together or R29 and R30 together are pyrrolidino, piperidino, morpholino, thiomorpholino, which may be mono- or polysubstituted by methyl groups;

or Q is Q2





in which

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;

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;

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, R4, R42NC(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

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,

or R36 is a group Het7-thio, Het7-sulfinyl, Hetg-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;

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

R37 and R38 together or R39 and R40 together or R41 and R42 together or R43 and R44 together are pyrrolidino, piperidino, morpholino, thiomorpholino, which may be mono- or polysubstituted by methyl groups;

or Q is Q3





in which

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

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; or R50 is phenyl, where the phenyl-containing group for its part may be substituted by one or more C1-C6alkyl, C1-C6haloalkyl, C1-C6alkoxy, C1-C6haloalkoxy, halogen, cyano, hydroxyl or nitro, or R50 is C3-C6cycloalkyl, C1-C6alkoxy- or C1-C6alkyl-substituted C3-C6cycloalkyl, 3-oxetanyl or C1-C6alkyl-substituted 3-oxetanyl; and n is 0, 1 or 2;

and agronomically acceptable salts/N-oxides/isomers/enantiomers of these compounds, with the exception of the compounds 3-hydroxy-2-(2-methoxy-methoxymethyl-6-chlorodifluoromethyl-pyrdine-3-carbonyl)-4,4-dimethyl-cyclohex-2-en-1-one, 3-hydroxy-2-(2-methoxy-methoxymethyl-6-difluoromethyl-pyridine-3-carbonyl)-4,4-dimethyl-cyclohex-2-en-1-one, 3-hydroxy-2-(2-methoxy-methoxymethyl-6-pentafluoroethyl-pyridine-3-carbonyl)-4,4-dimethyl-cyclohex-2-en-1-one, 3-hydroxy-2-(2-methoxy-methoxymethyl-6-trifluoromethyl-1-oxy-pyridine-3-carbonyl)-4,4-dimethyl-cyclohex-2-en-1-one.

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.
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.
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 trichloromethyl, difluorochloromethyl, difluoromethyl, trifluoromethyl and dichlorofluoromethyl.
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.
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.
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.
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.
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.
The compounds of the formula I may occur in different tautomeric forms, for example, if R13 is hydroxyl, in the preferred formulae I′ and I′′′′




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.
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.
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, methylnonylamine, 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.
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.
Compounds of formula I, wherein p is 0, are preferred.
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.
Preference is furthermore given to those compounds of the formula I, in which X1 is oxygen, sulfonyl or a group —NR52SO2—, in particular oxygen.
Of particular interest are compounds of the formula I, in which R2 is —CH2OCH3, —CH2OCH2CH3, —CH2CH2OCH3, —CH2CH2SO2CH3 or —CH2CH2OCH2CH2OCH3, preferably —CH2CH2OCH3, those compounds standing out in which X, is oxygen and R1 is —CH2—.
Among this group, preference is given to those compounds in which Q is Q. and R13 is hydroxyl.
Emphasis is furthermore given to the compounds of the formula I in which R2










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





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

In a further preferred group of compounds of the formula I, R3 is CF3, CF2CF3, CF2C1, CF2H or CCl3, particularly preferably CF3, where R4 is preferably hydrogen or methyl, particularly preferably hydrogen.
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.
Very particularly preferably, Q is Q. and R13 is hydroxyl or halogen, in particular hydroxyl. Among this group, emphasis is given to those compounds in which
a) A1 is C(R14R15) or NR16 and A2 is C(R17R18), C(O) or oxygen, or
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 R2, are particularly preferably hydrogen; or
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
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
e) A2 is C(R17R18) and A1 is C(R14R15) and R18 and R14 together form a C2-C3alkylene chain.
In a further outstanding group of compounds of the formula I, Q is Q3, R49 is cyclopropyl and R50—S(O), is methylthio, ethylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl.
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,




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





by, for example, either

a) reacting a compound of the formula Ia





in which R1, R2, R3, R4 and X, 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





in which R22, R21, A2 and A1 are as defined under formula I, to give the compounds of the formulae IIIa and IIIb





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

b) reacting a compound of the formula Ib





in which R1, R2, R3, R4 and X, are as defined under formula I, with a compound of the formula II





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





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

Compounds of the formula I, in which Q is a group




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

a) a compound of the formula Ia





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





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





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

b) a compound of the formula Ib





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





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





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

The compounds of the formula I, in which Q is a group




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 00/1 5615, WO/0039094 or WO 97/43270), wherein either

a) a compound of the formula IV





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),

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





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





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.

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




in which

Q is hydroxyl, halogen, cyano or C1-C6alkoxy, or is a group of the formula





or —CH2(CO)R49; and

R1, R3, R4, R49, R50, XI 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, benzylsutfinyl, benzylsulfonyl, C1-C6alkylamino, di(C1-C6alkyl)amino, R9S(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

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

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

or

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

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.

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




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.




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.
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




(formed from dicyclohexxylcarbodiimide (DCC) and the corresponding carboxylic acid) or





(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 IIa, IIIb or IIIc. This esterification can be carried out at temperatures of from 0° C. to 110° C.

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.
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, IIIb 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 Y1 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.
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




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).

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




in which R1, R2, R3, R4, and X1 are as defined above and Y. 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





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

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 00/15615) 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:




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.




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.
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.
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.




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.
The required intermediates of the formula Ib (or Ik, II or Im) are synthesized similarly to known processes as described, for example, in WO 00/15615, WO/00/39094 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):




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:




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 II, 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.
Intermediates of the formula Ib, in which R1 is C1-C2alkyl and R2, R3, R4 and X, 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, R5, 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:




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.
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.
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.
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.
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.
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.
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.
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 New Jersey, 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.
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.
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.
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, Ipomoea, Chrysanthemum, Galium, Viola and Veronica. 
The examples which follow illustrate the invention in greater detail without limiting it.


PREPARATION EXAMPLES
Example H1
Preparation of ethyl 2-bromomethyl-6-trifluoromethylnicotinate
434.4 g (1.866 mol) of ethyl 2-methyl-6-trifluoromethylnicotinate (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
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
24.9 g (0.1 mol) of 2-(2-methoxyethoxymethyl)-6-trifluoromethylnicotinic 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.
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
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
5g (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.
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-trifluoromethylpyridin-3-yl]methanone
1.0 g (0.004 mol) of 2-(2-methoxyethoxymethyl)-6-trifluoromethylnicotinic 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-trifluoromethylnicotinoyl 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, 8 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.
Preferred compounds of the formula I and their intermediates are listed in the tables below.
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




the point of attachment is at the “CH” carbon atom.

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

A-Q

where the formula A





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




H
CF3
O
0


 


A22 
CH2




H
CF3
O
0


 


A23 
CH2




H
CF3
O
0


 


A24 
CH2




H
CF3
O
0


 


A25 
CH2




H
CF3
O
0


 


A26 
CH2




H
CF3
O
0


 


A27 
CH2




H
CF3
O
0


 


A28 
CH2




H
CF3
O
0


 


A29 
CH2




H
CF3
O
0


 


A30 
CH2




H
CF3
O
0


 


A31 
CH2




H
CF3
O
0


 


A32 
CH2




H
CF3
O
0


 


A33 
CH2




H
CF3
O
0


 


A34 
CH2




H
CF3
O
0


 


A35 
CH2




H
CF3
O
0


 


A36 
CH2




H
CF3
O
0


 


A37 
CH2




H
CF3
O
0


 


A38 
CH2




H
CF3
O
0


 


A39 
CH2




H
CF3
O
0


 


A40 
CH2




H
CF3
O
0


 


A41 
CH2




H
CF3
O
0


 


A42 
CH2




H
CF3
O
0


 


A43 
CH2




H
CF3
O
0


 


A44 
CH2




H
CF3
O
0


 


A45 
CH2




H
CF3
O
0


 


A46 
CH2




H
CF3
O
0


 


A47 
CH2




H
CF3
O
0


 


A48 
CH2




H
CF3
O
0


 


A49 
CH2




H
CF3
O
0


 


A50 
CH2




H
CF3
O
0


 


A51 
CH2




H
CF3
O
0


 


A52 
CH2




H
CF3
O
0


 


A53 
CH2




H
CF3
O
0


 


A54 
CH2




H
CF3
O
0


 


A55 
CH2




H
CF3
O
0


 


A56 
CH2




H
CF3
O
0


 


A57 
CH2




H
CF3
O
0


 


A58 
CH2




H
CF3
O
0


 


A59 
CH2




H
CF3
O
0


 


A60 
CH2




H
CF3
O
0


 


A61 
CH2




H
CF3
O
0


 


A62 
CH2




H
CF3
O
0


 


A63 
CH2




H
CF3
O
0


 


A64 
CH2




H
CF3
O
0


 


A65 
CH2




H
CF3
O
0


 


A66 
CH2




H
CF3
O
0


 


A67 
CH2




H
CF3
O
0


 


A68 
CH2




H
CF3
O
0


 


A69 
CH2




H
CF3
O
0


 


A70 
CH2




H
CF3
O
0


 


A71 
CH2




H
CF3
O
0


 


A72 
CH2




H
CF3
O
0


 


A73 
CH2




H
CF3
O
0


 


A74 
CH2




H
CF3
O
0


 


A75 
CH2




H
CF3
O
0


 


A76 
CH2




H
CF3
O
0


 


A77 
CH2




H
CF3
O
0


 


A78 
CH2




H
CF3
O
0


 


A79 
CH2




H
CF3
O
0


 


A80 
CH2




H
CF3
O
0


 


A81 
CH2




H
CF3
O
0


 


A82 
CH2




H
CF3
O
0


 


A83 
CH2




H
CF3
O
0


 


A84 
CH2




H
CF3
O
0


 


A85 
CH2




H
CF3
O
0


 


A86 
CH2




H
CF3
O
0


 


A87 
CH2




H
CF3
O
0


 


A88 
CH2




H
CF3
O
0


 


A89 
CH2




H
CF3
O
0


 


A90 
CH2




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




H
CF3
O
0


 


A113
CH2CH2




H
CF3
O
0


 


A114
CH2CH2




H
CF3
O
0


 


A115
CH2CH2




H
CF3
O
0


 


A116
CH2CH2




H
CF3
O
0


 


A117
CH2CH2




H
CF3
O
0


 


A118
CH2CH2




H
CF3
O
0


 


A119
CH2CH2




H
CF3
O
0


 


A120
CH2CH2




H
CF3
O
0


 


A121
CH2CH2




H
CF3
O
0


 


A122
CH2CH2




H
CF3
O
0


 


A123
CH2CH2




H
CF3
O
0


 


A124
CH2CH2




H
CF3
O
0


 


A125
CH2CH2




H
CF3
O
0


 


A126
CH2CH2




H
CF3
O
0


 


A127
CH2CH2




H
CF3
O
0


 


A128
CH2CH2




H
CF3
O
0


 


A129
CH2CH2




H
CF3
O
0


 


A130
CH2CH2




H
CF3
O
0


 


A131
CH2CH2




H
CF3
O
0


 


A132
CH2CH2




H
CF3
O
0


 


A133
CH2CH2




H
CF3
O
0


 


A134
CH2CH2




H
CF3
O
0


 


A135
CH2CH2




H
CF3
O
0


 


A136
CH2CH2




H
CF3
O
0


 


A137
CH2CH2




H
CF3
O
0


 


A138
CH2CH2




H
CF3
O
0


 


A139
CH2CH2




H
CF3
O
0


 


A140
CH2CH2




H
CF3
O
0


 


A141
CH2CH2




H
CF3
O
0


 


A142
CH2CH2




H
CF3
O
0


 


A143
CH2CH2




H
CF3
O
0


 


A144
CH2CH2




H
CF3
O
0


 


A145
CH2CH2




H
CF3
O
0


 


A146
CH2CH2




H
CF3
O
0


 


A147
CH2CH2




H
CF3
O
0


 


A148
CH2CH2




H
CF3
O
0


 


A149
CH2CH2




H
CF3
O
0


 


A150
CH2CH2




H
CF3
O
0


 


A151
CH2CH2




H
CF3
O
0


 


A152
CH2CH2




H
CF3
O
0


 


A153
CH2CH2




H
CF3
O
0


 


A154
CH2CH2




H
CF3
O
0


 


A155
CH2CH2




H
CF3
O
0


 


A156
CH2CH2




H
CF3
O
0


 


A157
CH2CH2




H
CF3
O
0


 


A158
CH2CH2




H
CF3
O
0


 


A159
CH2CH2




H
CF3
O
0


 


A160
CH2CH2




H
CF3
O
0


 


A161
CH2CH2




H
CF3
O
0


 


A162
CH2CH2




H
CF3
O
0


 


A163
CH2CH2




H
CF3
O
0


 


A164
CH2CH2




H
CF3
O
0


 


A165
CH2CH2




H
CF3
O
0


 


A166
CH2CH2




H
CF3
O
0


 


A167
CH2CH2




H
CF3
O
0


 


A168
CH2CH2




H
CF3
O
0


 


A169
CH2CH2




H
CF3
O
0


 


A170
CH2CH2




H
CF3
O
0


 


A171
CH2CH2




H
CF3
O
0


 


A172
CH2CH2




H
CF3
O
0


 


A173
CH2CH2




H
CF3
O
0


 


A174
CH2CH2




H
CF3
O
0


 


A175
CH2CH2




H
CF3
O
0


 


A176
CH2CH2




H
CF3
O
0


 


A177
CH2CH2




H
CF3
O
0


 


A178
CH2CH2




H
CF3
O
0


 


A179
CH2CH2




H
CF3
O
0


 


A180
CH2CH2




H
CF3
O
0


 


A181
CH2CH2




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




H
CF3
O
0


 


A204
CH(OCH3)CH2




H
CF3
O
0


 


A205
CH(OCH3)CH2




H
CF3
O
0


 


A206
CH(OCH3)CH2




H
CF3
O
0


 


A207
CH(OCH3)CH2




H
CF3
O
0


 


A208
CH(OCH3)CH2




H
CF3
O
0


 


A209
CH(OCH3)CH2




H
CF3
O
0


 


A210
CH(OCH3)CH2




H
CF3
O
0


 


A211
CH(OCH3)CH2




H
CF3
O
0


 


A212
CH(OCH3)CH2




H
CF3
O
0


 


A213
CH(OCH3)CH2




H
CF3
O
0


 


A214
CH(OCH3)CH2




H
CF3
O
0


 


A215
CH(OCH3)CH2




H
CF3
O
0


 


A216
CH(OCH3)CH2




H
CF3
O
0


 


A217
CH(OCH3)CH2




H
CF3
O
0


 


A218
CH(OCH3)CH2




H
CF3
O
0


 


A219
CH(OCH3)CH2




H
CF3
O
0


 


A220
CH(OCH3)CH2




H
CF3
O
0


 


A221
CH(OCH3)CH2




H
CF3
O
0


 


A222
CH(OCH3)CH2




H
CF3
O
0


 


A223
CH(OCH3)CH2




H
CF3
O
0


 


A224
CH(OCH3)CH2




H
CF3
O
0


 


A225
CH(OCH3)CH2




H
CF3
O
0


 


A226
CH(OCH3)CH2




H
CF3
O
0


 


A227
CH(OCH3)CH2




H
CF3
O
0


 


A228
CH(OCH3)CH2




H
CF3
O
0


 


A229
CH(OCH3)CH2




H
CF3
O
0


 


A230
CH(OCH3)CH2




H
CF3
O
0


 


A231
CH(OCH3)CH2




H
CF3
O
0


 


A232
CH(OCH3)CH2




H
CF3
O
0


 


A233
CH(OCH3)CH2




H
CF3
O
0


 


A234
CH(OCH3)CH2




H
CF3
O
0


 


A235
CH(OCH3)CH2




H
CF3
O
0


 


A236
CH(OCH3)CH2




H
CF3
O
0


 


A237
CH(OCH3)CH2




H
CF3
O
0


 


A238
CH(OCH3)CH2




H
CF3
O
0


 


A239
CH(OCH3)CH2




H
CF3
O
0


 


A240
CH(OCH3)CH2




H
CF3
O
0


 


A241
CH(OCH3)CH2




H
CF3
O
0


 


A242
CH(OCH3)CH2




H
CF3
O
0


 


A243
CH(OCH3)CH2




H
CF3
O
0


 


A244
CH(OCH3)CH2




H
CF3
O
0


 


A245
CH(OCH3)CH2




H
CF3
O
0


 


A246
CH(OCH3)CH2




H
CF3
O
0


 


A247
CH(OCH3)CH2




H
CF3
O
0


 


A248
CH(OCH3)CH2




H
CF3
O
0


 


A249
CH(OCH3)CH2




H
CF3
O
0


 


A250
CH(OCH3)CH2




H
CF3
O
0


 


A251
CH(OCH3)CH2




H
CF3
O
0


 


A252
CH(OCH3)CH2




H
CF3
O
0


 


A253
CH(OCH3)CH2




H
CF3
O
0


 


A254
CH(OCH3)CH2




H
CF3
O
0


 


A255
CH(OCH3)CH2




H
CF3
O
0


 


A256
CH(OCH3)CH2




H
CF3
O
0


 


A257
CH(OCH3)CH2




H
CF3
O
0


 


A258
CH(OCH3)CH2




H
CF3
O
0


 


A259
CH(OCH3)CH2




H
CF3
O
0


 


A260
CH(OCH3)CH2




H
CF3
O
0


 


A261
CH(OCH3)CH2




H
CF3
O
0


 


A262
CH(OCH3)CH2




H
CF3
O
0


 


A263
CH(OCH3)CH2




H
CF3
O
0


 


A264
CH(OCH3)CH2




H
CF3
O
0


 


A265
CH(OCH3)CH2




H
CF3
O
0


 


A266
CH(OCH3)CH2




H
CF3
O
0


 


A267
CH(OCH3)CH2




H
CF3
O
0


 


A268
CH(OCH3)CH2




H
CF3
O
0


 


A269
CH(OCH3)CH2




H
CF3
O
0


 


A270
CH(OCH3)CH2




H
CF3
O
0


 


A271
CH(OCH3)CH2




H
CF3
O
0


 


A272
CH(OCH3)CH2




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




H
CF3
O
0


 


A295
CH2CH(OCH3)CH2




H
CF3
O
0


 


A296
CH2CH(OCH3)CH2




H
CF3
O
0


 


A297
CH2CH(OCH3)CH2




H
CF3
O
0


 


A298
CH2CH(OCH3)CH2




H
CF3
O
0


 


A299
CH2CH(OCH3)CH2




H
CF3
O
0


 


A300
CH2CH(OCH3)CH2




H
CF3
O
0


 


A301
CH2CH(OCH3)CH2




H
CF3
O
0


 


A302
CH2CH(OCH3)CH2




H
CF3
O
0


 


A303
CH2CH(OCH3)CH2




H
CF3
O
0


 


A304
CH2CH(OCH3)CH2




H
CF3
O
0


 


A305
CH2CH(OCH3)CH2




H
CF3
O
0


 


A306
CH2CH(OCH3)CH2




H
CF3
O
0


 


A307
CH2CH(OCH3)CH2




H
CF3
O
0


 


A308
CH2CH(OCH3)CH2




H
CF3
O
p


 


A309
CH2CH(OCH3)CH2




H
CF3
O


 


A310
CH2CH(OCH3)CH2




H
CF3
O
0


 


A311
CH2CH(OCH3)CH2




H
CF3
O
0


 


A312
CH2CH(OCH3)CH2




H
CF3
O
0


 


A313
CH2CH(OCH3)CH2




H
CF3
O
0


 


A314
CH2CH(OCH3)CH2




H
CF3
O
0


 


A315
CH2CH(OCH3)CH2




H
CF3
O
0


 


A316
CH2CH(OCH3)CH2




H
CF3
O
0


 


A317
CH2CH(OCH3)CH2




H
CF3
O
0


 


A318
CH2CH(OCH3)CH2




H
CF3
O
0


 


A319
CH2CH(OCH3)CH2




H
CF3
O
0


 


A320
CH2CH(OCH3)CH2




H
CF3
O
0


 


A321
CH2CH(OCH3)CH2




H
CF3
O
0


 


A322
CH2CH(OCH3)CH2




H
CF3
O
0


 


A323
CH2CH(OCH3)CH2




H
CF3
O
0


 


A324
CH2CH(OCH3)CH2




H
CF3
O
0


 


A325
CH2CH(OCH3)CH2




H
CF3
O
0


 


A326
CH2CH(OCH3)CH2




H
CF3
O
0


 


A327
CH2CH(OCH3)CH2




H
CF3
O
0


 


A328
CH2CH(OCH3)CH2




H
CF3
O
0


 


A329
CH2CH(OCH3)CH2




H
CF3
O
0


 


A330
CH2CH(OCH3)CH2




H
CF3
O
0


 


A331
CH2CH(OCH3)CH2




H
CF3
O
0


 


A332
CH2CH(OCH3)CH2




H
CF3
O
0


 


A333
CH2CH(OCH3)CH2




H
CF3
O
0


 


A334
CH2CH(OCH3)CH2




H
CF3
O
0


 


A335
CH2CH(OCH3)CH2




H
CF3
O
0


 


A336
CH2CH(OCH3)CH2




H
CF3
O
0


 


A337
CH2CH(OCH3)CH2




H
CF3
O
0


 


A338
CH2CH(OCH3)CH2




H
CF3
O
0


 


A339
CH2CH(OCH3)CH2




H
CF3
O
0


 


A340
CH2CH(OCH3)CH2




H
CF3
O
0


 


A341
CH2CH(OCH3)CH2




H
CF3
O
0


 


A342
CH2CH(OCH3)CH2




H
CF3
O
0


 


A343
CH2CH(OCH3)CH2




H
CF3
O
0


 


A344
CH2CH(OCH3)CH2




H
CF3
O
0


 


A345
CH2CH(OCH3)CH2




H
CF3
O
0


 


A346
CH2CH(OCH3)CH2




H
CF3
O
0


 


A347
CH2CH(OCH3)CH2




H
CF3
O
0


 


A348
CH2CH(OCH3)CH2




H
CF3
O
0


 


A349
CH2CH(OCH3)CH2




H
CF3
O
0


 


A350
CH2CH(OCH3)CH2




H
CF3
O
0


 


A351
CH2CH(OCH3)CH2




H
CF3
O
0


 


A352
CH2CH(OCH3)CH2




H
CF3
O
0


 


A353
CH2CH(OCH3)CH2




H
CF3
O
0


 


A354
CH2CH(OCH3)CH2




H
CF3
O
0


 


A355
CH2CH(OCH3)CH2




H
CF3
O
0


 


A356
CH2CH(OCH3)CH2




H
CF3
O
0


 


A357
CH2CH(OCH3)CH2




H
CF3
O
0


 


A358
CH2CH(OCH3)CH2




H
CF3
O
0


 


A359
CH2CH(OCH3)CH2




H
CF3
O
0


 


A360
CH2CH(OCH3)CH2




H
CF3
O
0


 


A361
CH2CH(OCH3)CH2




H
CF3
O
0


 


A362
CH2CH(OCH3)CH2




H
CF3
O
0


 


A363
CH2CH(OCH3)CH2




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
CH═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
CF3
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




H
CF3
O
0


 


A386
CH═CHCH2




H
CF3
O
0


 


A387
CH═CHCH2




H
CF3
O
0


 


A388
CH═CHCH2




H
CF3
O
0


 


A389
CH═CHCH2




H
CF3
O
0


 


A390
CH═CHCH2




H
CF3
O
0


 


A391
CH═CHCH2




H
CF3
O
0


 


A392
CH═CHCH2




H
CF3
O
0


 


A393
CH═CHCH2




H
CF3
O
0


 


A394
CH═CHCH2




H
CF3
O
0


 


A395
CH═CHCH2




H
CF3
O
0


 


A396
CH═CHCH2




H
CF3
O
0


 


A397
CH═CHCH2




H
CF3
O
0


 


A398
CH═CHCH2




H
CF3
O
0


 


A399
CH═CHCH2




H
CF3
O
0


 


A400
CH═CHCH2




H
CF3
O
0


 


A401
CH═CHCH2




H
CF3
O
0


 


A402
CH═CHCH2




H
CF3
O
0


 


A403
CH═CHCH2




H
CF3
O
0


 


A404
CH═CHCH2




H
CF3
O
0


 


A405
CH═CHCH2




H
CF3
O
0


 


A406
CH═CHCH2




H
CF3
O
0


 


A407
CH═CHCH2




H
CF3
O
0


 


A408
CH═CHCH2




H
CF3
O
0


 


A409
CH═CHCH2




H
CF3
O
0


 


A410
CH═CHCH2




H
CF3
O
0


 


A411
CH═CHCH2




H
CF3
O
0


 


A412
CH═CHCH2




H
CF3
O
0


 


A413
CH═CHCH2




H
CF3
O
0


 


A414
CH═CHCH2




H
CF3
O
0


 


A415
CH═CHCH2




H
CF3
O
0


 


A416
CH═CHCH2




H
CF3
O
0


 


A417
CH═CHCH2




H
CF3
O
0


 


A418
CH═CHCH2




H
CF3
O
0


 


A419
CH═CHCH2




H
CF3
O
0


 


A420
CH═CHCH2




H
CF3
O
0


 


A421
CH═CHCH2




H
CF3
O
0


 


A422
CH═CHCH2




H
CF3
O
0


 


A423
CH═CHCH2




H
CF3
O
0


 


A424
CH═CHCH2




H
CF3
O
0


 


A425
CH═CHCH2




H
CF3
O
0


 


A426
CH═CHCH2




H
CF3
O
0


 


A427
CH═CHCH2




H
CF3
O
0


 


A428
CH═CHCH2




H
CF3
O
0


 


A429
CH═CHCH2




H
CF3
O
0


 


A430
CH═CHCH2




H
CF3
O
0


 


A431
CH═CHCH2




H
CF3
O
0


 


A432
CH═CHCH2




H
CF3
O
0


 


A433
CH═CHCH2




H
CF3
O
0


 


A434
CH═CHCH2




H
CF3
O
0


 


A435
CH═CHCH2




H
CF3
O
0


 


A436
CH═CHCH2




H
CF3
O
0


 


A437
CH═CHCH2




H
CF3
O
0


 


A438
CH═CHCH2




H
CF3
O
0


 


A439
CH═CHCH2




H
CF3
O
0


 


A440
CH═CHCH2




H
CF3
O
0


 


A441
CH═CHCH2




H
CF3
O
0


 


A442
CH═CHCH2




H
CF3
O
0


 


A443
CH═CHCH2




H
CF3
O
0


 


A444
CH═CHCH2




H
CF3
O
0


 


A445
CH═CHCH2




H
CF3
O
0


 


A446
CH═CHCH2




H
CF3
O
0


 


A447
CH═CHCH2




H
CF3
O
0


 


A448
CH═CHCH2




H
CF3
O
0


 


A449
CH═CHCH2




H
CF3
O
0


 


A450
CH═CHCH2




H
CF3
O
0


 


A451
CH═CHCH2




H
CF3
O
0


 


A452
CH═CHCH2




H
CF3
O
0


 


A453
CH═CHCH2




H
CF3
O
0


 


A454
CH═CHCH2




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




H
CF3
O
0


 


A477
C≡CCH2




H
CF3
O
0


 


A478
C≡CCH2




H
CF3
O
0


 


A479
C≡CCH2




H
CF3
O
0


 


A480
C≡CCH2




H
CF3
O
0


 


A481
C≡CCH2




H
CF3
O
0


 


A482
C≡CCH2




H
CF3
O
0


 


A483
C≡CCH2




H
CF3
O
0


 


A484
C≡CCH2




H
CF3
O
0


 


A485
C≡CCH2




H
CF3
O
0


 


A486
C≡CCH2




H
CF3
O
0


 


A487
C≡CCH2




H
CF3
O
0


 


A488
C≡CCH2




H
CF3
O
0


 


A489
C≡CCH2




H
CF3
O
0


 


A490
C≡CCH2




H
CF3
O
0


 


A491
C≡CCH2




H
CF3
O
0


 


A492
C≡CCH2




H
CF3
O
0


 


A493
C≡CCH2




H
CF3
O
0


 


A494
C≡CCH2




H
CF3
O
0


 


A495
C≡CCH2




H
CF3
O
0


 


A496
C≡CCH2




H
CF3
O
0


 


A497
C≡CCH2




H
CF3
O
0


 


A498
C≡CCH2




H
CF3
O
0


 


A499
C≡CCH2




H
CF3
O
0


 


A500
C≡CCH2




H
CF3
O
0


 


A501
C≡CCH2




H
CF3
O
0


 


A502
C≡CCH2




H
CF3
O
0


 


A503
C≡CCH2




H
CF3
O
0


 


A504
C≡CCH2




H
CF3
O
0


 


A505
C≡CCH2




H
CF3
O
0


 


A506
C≡CCH2




H
CF3
O
0


 


A507
C≡CCH2




H
CF3
O
0


 


A508
C≡CCH2




H
CF3
O
0


 


A509
C≡CCH2




H
CF3
O
0


 


A510
C≡CCH2




H
CF3
O
0


 


A511
C≡CCH2




H
CF3
O
0


 


A512
C≡CCH2




H
CF3
O
0


 


A513
C≡CCH2




H
CF3
O
0


 


A514
C≡CCH2




H
CF3
O
0


 


A515
C≡CCH2




H
CF3
O
0


 


A516
C≡CCH2




H
CF3
O
0


 


A517
C≡CCH2




H
CF3
O
0


 


A518
C≡CCH2




H
CF3
O
0


 


A519
C≡CCH2




H
CF3
O
0


 


A520
C≡CCH2




H
CF3
O
0


 


A521
C≡CCH2




H
CF3
O
0


 


A522
C≡CCH2




H
CF3
O
0


 


A523
C≡CCH2




H
CF3
O
0


 


A524
C≡CCH2




H
CF3
O
0


 


A525
C≡CCH2




H
CF3
O
0


 


A526
C≡CCH2




H
CF3
O
0


 


A527
C≡CCH2




H
CF3
O
0


 


A528
C≡CCH2




H
CF3
O
0


 


A529
C≡CCH2




H
CF3
O
0


 


A530
C≡CCH2




H
CF3
O
0


 


A531
C≡CCH2




H
CF3
O
0


 


A532
C≡CCH2




H
CF3
O
0


 


A533
C≡CCH2




H
CF3
O
0


 


A534
C≡CCH2




H
CF3
O
0


 


A535
C≡CCH2




H
CF3
O
0


 


A536
C≡CCH2




H
CF3
O
0


 


A537
C≡CCH2




H
CF3
O
0


 


A538
C≡CCH2




H
CF3
O
0


 


A539
C≡CCH2




H
CF3
O
0


 


A540
C≡CCH2




H
CF3
O
0


 


A541
C≡CCH2




H
CF3
O
0


 


A542
C≡CCH2




H
CF3
O
0


 


A543
C≡CCH2




H
CF3
O
0


 


A544
C≡CCH2




H
CF3
O
0


 


A545
C≡CCH2




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




H
CF2Cl
O
0


 


A568
CH2




H
CF2Cl
O
0


 


A569
CH2




H
CF2Cl
O
0


 


A570
CH2




H
CF2Cl
O
0


 


A571
CH2




H
CF2Cl
O
0


 


A572
CH2




H
CF2Cl
O
0


 


A573
CH2




H
CF2Cl
O
0


 


A574
CH2




H
CF2Cl
O
0


 


A575
CH2




H
CF2Cl
O
0


 


A576
CH2




H
CF2Cl
O
0


 


A577
CH2




H
CF2Cl
O
0


 


A578
CH2




H
CF2Cl
O
0


 


A579
CH2




H
CF2Cl
O
0


 


A580
CH2




H
CF2Cl
O
0


 


A581
CH2




H
CF2Cl
O
0


 


A582
CH2




H
CF2Cl
O
0


 


A583
CH2




H
CF2Cl
O
0


 


A584
CH2




H
CF2Cl
O
0


 


A585
CH2




H
CF2Cl
O
0


 


A586
CH2




H
CF2Cl
O
0


 


A587
CH2




H
CF2Cl
O
0


 


A588
CH2




H
CF2Cl
O
0


 


A589
CH2




H
CF2Cl
O
0


 


A590
CH2




H
CF2Cl
O
0


 


A591
CH2




H
CF2Cl
O
0


 


A592
CH2




H
CF2Cl
O
0


 


A593
CH2




H
CF2Cl
O
0


 


A594
CH2




H
CF2Cl
O
0


 


A595
CH2




H
CF2Cl
O
0


 


A596
CH2




H
CF2Cl
O
0


 


A597
CH2




H
CF2Cl
O
0


 


A598
CH2




H
CF2Cl
O
0


 


A599
CH2




H
CF2Cl
O
0


 


A600
CH2




H
CF2Cl
O
0


 


A601
CH2




H
CF2Cl
O
0


 


A602
CH2




H
CF2Cl
O
0


 


A603
CH2




H
CF2Cl
O
0


 


A604
CH2




H
CF2Cl
O
0


 


A605
CH2




H
CF2Cl
O
0


 


A606
CH2




H
CF2Cl
O
0


 


A607
CH2




H
CF2Cl
O
0


 


A608
CH2




H
CF2Cl
O
0


 


A609
CH2




H
CF2Cl
O
0


 


A610
CH2




H
CF2Cl
O
0


 


A611
CH2




H
CF2Cl
O
0


 


A612
CH2




H
CF2Cl
O
0


 


A613
CH2




H
CF2Cl
O
0


 


A614
CH2




H
CF2Cl
O
0


 


A615
CH2




H
CF2Cl
O
0


 


A616
CH2




H
CF2Cl
O
0


 


A617
CH2




H
CF2Cl
O
0


 


A618
CH2




H
CF2Cl
O
0


 


A619
CH2




H
CF2Cl
O
0


 


A620
CH2




H
CF2Cl
O
0


 


A621
CH2




H
CF2Cl
O
0


 


A622
CH2




H
CF2Cl
O
0


 


A623
CH2




H
CF2Cl
O
0


 


A624
CH2




H
CF2Cl
O
0


 


A625
CH2




H
CF2Cl
O
0


 


A626
CH2




H
CF2Cl
O
0


 


A627
CH2




H
CF2Cl
O
0


 


A628
CH2




H
CF2Cl
O
0


 


A629
CH2




H
CF2Cl
O
0


 


A630
CH2




H
CF2Cl
O
0


 


A631
CH2




H
CF2Cl
O
0


 


A632
CH2




H
CF2Cl
O
0


 


A633
CH2




H
CF2Cl
O
0


 


A634
CH2




H
CF2Cl
O
0


 


A635
CH2




H
CF2Cl
O
0


 


A636
CH2




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




H
CHF2
O
0


 


A658
CH2




H
CHF2
O
0


 


A659
CH2




H
CHF2
O
0


 


A660
CH2




H
CHF2
O
0


 


A661
CH2




H
CHF2
O
0


 


A662
CH2




H
CHF2
O
0


 


A663
CH2




H
CHF2
O
0


 


A664
CH2




H
CHF2
O
0


 


A665
CH2




H
CHF2
O
0


 


A666
CH2




H
CHF2
O
0


 


A667
CH2




H
CHF2
O
0


 


A668
CH2




H
CHF2
O
0


 


A669
CH2




H
CHF2
O
0


 


A670
CH2




H
CHF2
O
0


 


A671
CH2




H
CHF2
O
0


 


A672
CH2




H
CHF2
O
0


 


A673
CH2




H
CHF2
O
0


 


A674
CH2




H
CHF2
O
0


 


A675
CH2




H
CHF2
O
0


 


A676
CH2




H
CHF2
O
0


 


A677
CH2




H
CHF2
O
0


 


A678
CH2




H
CHF2
O
0


 


A679
CH2




H
CHF2
O
0


 


A680
CH2




H
CHF2
O
0


 


A681
CH2




H
CHF2
O
0


 


A682
CH2




H
CHF2
S
0


 


A683
CH2




H
CHF2
SO
0


 


A684
CH2




H
CHF2
SO2
0


 


A685
CH2




H
CHF2
O
0


 


A686
CH2




H
CHF2
O
0


 


A687
CH2




H
CHF2
O
0


 


A688
CH2




H
CHF2
O
0


 


A689
CH2




H
CHF2
O
0


 


A690
CH2




H
CHF2
O
0


 


A691
CH2




H
CHF2
O
0


 


A692
CH2




H
CHF2
O
0


 


A693
CH2




H
CHF2
O
0


 


A694
CH2




H
CHF2
O
0


 


A695
CH2




H
CHF2
O
0


 


A696
CH2




H
CHF2
O
0


 


A697
CH2




H
CHF2
O
0


 


A698
CH2




H
CHF2
O
0


 


A699
CH2




H
CHF2
O
0


 


A700
CH2




H
CHF2
O
0


 


A701
CH2




H
CHF2
O
0


 


A702
CH2




H
CHF2
O
0


 


A703
CH2




H
CHF2
O
0


 


A704
CH2




H
CHF2
O
0


 


A705
CH2




H
CHF2
O
0


 


A706
CH2




H
CHF2
O
0


 


A707
CH2




H
CHF2
O
0


 


A708
CH2




H
CHF2
O
0


 


A709
CH2




H
CHF2
O
0


 


A710
CH2




H
CHF2
O
0


 


A711
CH2




H
CHF2
O
0


 


A712
CH2




H
CHF2
O
0


 


A713
CH2




H
CHF2
O
0


 


A714
CH2




H
CHF2
O
0


 


A715
CH2




H
CHF2
O
0


 


A716
CH2




H
CHF2
O
0


 


A717
CH2




H
CHF2
O
0


 


A718
CH2




H
CHF2
O
0


 


A719
CH2




H
CHF2
O
0


 


A720
CH2




H
CHF2
O
0


 


A721
CH2




H
CHF2
O
0


 


A722
CH2




H
CHF2
O
0


 


A723
CH2




H
CHF2
O
0


 


A724
CH2




H
CHF2
O
0


 


A725
CH2




H
CHF2
O
0


 


A726
CH2




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




H
CF3
O
1


 


A748
CH2




H
CF3
O
1


 


A749
CH2




H
CF3
O
1


 


A750
CH2




H
CF3
O
1


 


A751
CH2




H
CF3
O
1


 


A752
CH2




H
CF3
O
1


 


A753
CH2




H
CF3
O
1


 


A754
CH2




H
CF3
O
1


 


A755
CH2




H
CF3
O
1


 


A756
CH2




H
CF3
O
1


 


A757
CH2




H
CF3
O
1


 


A758
CH2




H
CF3
O
1


 


A759
CH2




H
CF3
O
1


 


A760
CH2




H
CF3
O
1


 


A761
CH2




H
CF3
O
1


 


A762
CH2




H
CF3
O
1


 


A763
CH2




H
CF3
O
1


 


A764
CH2




H
CF3
O
1


 


A765
CH2




H
CF3
O
1


 


A766
CH2




H
CF3
O
1


 


A767
CH2




H
CF3
O
1


 


A768
CH2




H
CF3
O
1


 


A769
CH2




H
CF3
O
1


 


A770
CH2




H
CF3
O
1


 


A771
CH2




H
CF3
O
1


 


A772
CH2




H
CF3
O
1


 


A773
CH2




H
CF3
O
1


 


A774
CH2




H
CF3
O
1


 


A775
CH2




H
CF3
O
1


 


A776
CH2




H
CF3
O
1


 


A777
CH2




H
CF3
O
1


 


A778
CH2




H
CF3
O
1


 


A779
CH2




H
CF3
O
1


 


A780
CH2




H
CF3
O
1


 


A781
CH2




H
CF3
O
1


 


A782
CH2




H
CF3
O
1


 


A783
CH2




H
CF3
O
1


 


A784
CH2




H
CF3
O
1


 


A785
CH2




H
CF3
O
1


 


A786
CH2




H
CF3
O
1


 


A787
CH2




H
CF3
O
1


 


A788
CH2




H
CF3
O
1


 


A789
CH2




H
CF3
O
1


 


A790
CH2




H
CF3
O
1


 


A791
CH2




H
CF3
O
1


 


A792
CH2




H
CF3
O
1


 


A793
CH2




H
CF3
O
1


 


A794
CH2




H
CF3
O
1


 


A795
CH2




H
CF3
O
1


 


A796
CH2




H
CF3
O
1


 


A797
CH2




H
CF3
O
1


 


A798
CH2




H
CF3
O
1


 


A799
CH2




H
CF3
O
1


 


A800
CH2




H
CF3
O
1


 


A801
CH2




H
CF3
O
1


 


A802
CH2




H
CF3
O
1


 


A803
CH2




H
CF3
O
1


 


A804
CH2




H
CF3
O
1


 


A805
CH2




H
CF3
O
1


 


A806
CH2




H
CF3
O
1


 


A807
CH2




H
CF3
O
1


 


A808
CH2




H
CF3
O
1


 


A809
CH2




H
CF3
O
1


 


A810
CH2




H
CF3
O
1


 


A811
CH2




H
CF3
O
1


 


A812
CH2




H
CF3
O
1


 


A813
CH2




H
CF3
O
1


 


A814
CH2




H
CF3
O
1


 


A815
CH2




H
CF3
O
1


 


A816
CH2




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




H
CF3
S
0


 


A830
CH2




H
CF3
S
0


 


A831
CH2




CH3
CF3
S
0


 


A832
CH2




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




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




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




H
CF3
O
0


 


A849
CH2
N≡CCH2CH2
H
CF3
O
0


A850
CH2
ClCH2CH2
H
CF3
O
0


 


A851
CH2




H
CF3
O
0


 


A852
CH2




H
CF3
O
0


 


A853
CH2
CH3OCH2C(Br)HCH2
H
CF3
O
0


 


A854
CH2




H
CF3
O
0


 


A855
CH2




H
CF3
O
0


 


A856
CH2
HOCH2CH2
H
CF3
O
0


 


A857
CH2




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




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









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




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





In the formula A-Q, Q denotes Q1




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
CH3O
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




CH2
0
H
H
OH


 


B17




CH2
0
H
H
OH


 


B18




CH2
0
CH3
H
OH


 


B19




CH2
0
CH3
CH3
OH


 


B20




CH2
0
H
H
OH


 


B21




CH2
0
CH3
H
OH


 


B22




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




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
OH
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




C═O
0
CH3
CH3
OH


 


B42




C═O
0
CH2
CH2
OH


 


B43
(CH3)2C




0
CH3
CH3
OH


 


B44
(CH3)2C




0
CH3
CH3
OH


 


B45
(CH3)2C




0
CH3
CH3
OH


 


B46
(CH3)2C




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═O
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
OH


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






 


B74
CH
CH2
1
H
CH2






 


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






 


B92
(CH3)2C
C═O
0
CH3
CH3






 


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






 


 B110
(CH3)2C
CH2
0
H
H






 


 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









or Q in the formula A-Q denotes Q2





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 




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
PhC(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






 


C27
H
CH3






 


C28
H
CH3
CH3SO2O


C29
H
CH3
p-TolylSO2O









or Q in the formula A-Q denotes Q3





and Q3 denotes the following radicals D (the point of attachment of R49 to the heterocycle is the “CH” group):








TABLE 1







Intermediates for preparing the


compounds of the formula I, represented as formula A—Q












Radical
R49
R50
n







D1




CH3
0



 



D2




CH3
1



 



D3




CH3
2



 



D4




CF3
0



 



D5




CF3
1



 



D6




CF3
2



 



D7




Ph
0



 



D8




Ph
1



 



D9




Ph
2



 



 D10




PhCH2
0



 



 D11




PhCH2
1



 



 D12




PhCH2
2










in which Q denotes hydroxyl:








TABLE 2







Compounds of the formula I, represented as compounds of the formula A—Q


















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
—
—
—
—
—
—
—
—
















TABLE 3







Compounds of the formula I, represented as compounds of the formula A—Q


















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
—
—
—
—
—
—
—
—









in which Q denotes Q1 and Q2 denotes the radical B39:








TABLE 4







Compounds of the formula I, represented as compounds of the formula A—Q


















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
—
—
—
—
—
—
—
—









in which Q denotes Q1 and Q1 denotes the radical B3:








TABLE 5







Compounds of the formula I, represented as compounds of the formula A—Q


















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
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
—
—
—
—
—
—
—
—









in which Q denotes Q2 and Q2 denotes the radical C5:








TABLE 6







Compounds of the formula I, represented as compounds of the formula A—Q


















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
—
—
—
—
—
—
—
—









in which Q denotes Q2 and Q2 denotes the radical C2:








TABLE 7







Compounds of the formula I, represented as compounds of the formula A—Q


















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
—
—
—
—
—
—
—
—









Table 7: Compounds of the formula I, represented as compounds of the formula

in which Q denotes Q2 and Q2 denotes the radicals D1, D2 or D3:








TABLE 8







Compounds of the formula Ip:









(Ip)








 


















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
—
—
—
—
—
—
—
—









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:








TABLE 9







Compounds of the formula I, represented as compounds of the formula A—Q


















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
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
—
—
—
—
—
—
—
—









in which A denotes A10:








TABLE 10







Compounds of the formula I, represented as compounds of the formula A—Q


















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
—
—
—
—
—
—
—
—
—
—









in which A denotes A10:








TABLE 11







Compounds of the formula I, represented as compounds of the formula A—Q


















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
—
—
—
—
—
—
—
—
—









in which A denotes A10:








TABLE 12







Compounds of the formula I, represented as compounds of the formula A—Q


















A10
A10
A10
A10
A10
A10
A10
A10
A10
A10
A10
A10





—
—
—
D4
D5
D6
D7
D8
D9
D10
D11
D12









in which A denotes A556:








TABLE 13







Compounds of the formula I, represented as compounds of the formula A—Q


















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
—
—
—
—
—
—
—
—
—
—









in which A denotes A556:








TABLE 14







Compounds of the formula I, represented as compounds of the formula A—Q


















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
—
—
—
—
—
—
—
—
—









in which A denotes A556:








TABLE 15







Compounds of the formula I, represented as compounds of the formula A—Q


















A556
A556
A556
A556
A556
A556
A556
A556
A556
A556
A556
A556





—
—
—
D4
D5
D6
D7
D8
D9
D10
D11
D12









in which A denotes A646:








TABLE 16







Compounds of the formula I, represented as compounds of the formula A—Q


















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
—
—
—
—
—
—
—
—
—
—









in which A denotes A646:








TABLE 17







Compounds of the formula I, represented as compounds of the formula A—Q


















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
—
—
—
—
—
—
—
—
—









in which A denotes A646:








TABLE 18







Physical data for the compounds of the formula I given in the tables


above: (the melting points are given in ° C.)


















A646
A646
A646
A646
A646
A646
A646
A646
A646
A646
A646
A646





—
—
—
D4
D5
D6
D7
D8
D9
D10
D11
D12
















TABLE 19







Physical data for the compounds of the formula I given in the tables


above: (the melting points 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










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




can be also drawn as





and





can be also drawn as

















Comp.

m.p. (range)


No.
Corresponding Formula
Phys. state







1.001




138-140crystalline


 


1.002




145-150crystalline


 


1.003




oil


 


1.004




oil


 


1.005




oil


 


1.006




oil


 


1.007




54-56crystalline


 


1.008




crystalline


 


1.009




viscous, 1HNMR; 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




viscous


 


1.011




viscous


 


1.012




99-100crystalline


 


1.013




100-102crystalline


 


1.014




viscous


 


1.015




54-56crystalline


 


1.016




71-74crystalline


 


1.017




95-98crystalline


 


1.018




53-55crystalline


 


1.019




32-34crystalline


 


1.020




32-33crystalline


 


1.021




resin


 


1.022




38-39crystalline


 


1.023




resin


 


1.024




crystalline


 


1.025




viscous


 


1.026




viscous


 


1.027




viscous


 


1.028




113-115crystalline


 


1.029




crystalline


 


1.030




viscous


 


1.031




106-107crystalline


 


1.032




viscous


 


1.033




viscous


 


1.034




crystalline


 


1.035




crystalline


 


1.036




viscous


 


1.037




resin


 


1.038




solid


 


1.039




resin


 


1.040




crystalline


 


1.041




viscous


 


1.042




viscous


 


1.043




viscous


 


1.044




viscous


 


1.045




crystalline


 


1.046




viscous


 


1.047




viscous


 


1.048




viscous


 


1.049




viscous


 


1.050




90-93


 


1.051




oil


 


1.052




41-43


 


1.053




viscous


 


1.054




viscous


 


1.055




96-98


 


1.056




viscous


 


1.057




viscous


 


1.058




viscous


 


1.059




79-81


 


1.060




viscous


 


1.061




viscous


 


1.062




resin


 


1.063




crystalline


 


1.064




viscous


 


1.065




102-105crystalline


 


1.066




40-44crystalline


 


1.067




viscous


 


1.068




68-69crystalline


 


1.069




78-80crystalline


 


1.070




40-42


 


1.071




crystalline


 


1.072




viscous


 


1.073




46-47crystalline


 


1.074




vitreous


 


1.075




vitreous


 


1.076




75-76


 


1.077




viscous


 


1.078




viscous


 


1.079




viscous


 


1.080




63-64crystalline


 


1.081




resin


 


1.082




76-78crystalline


 


1.083




resin


 


1.084




resin


 


1.085




vitreous


 


1.086




viscous


 


1.087




oil


 


1.088




viscous


 


1.089




oil


 


1.090




149-150crystalline


 


1.091




110-112crystalline


 


1.092




crystalline









BIOLOGICAL EXAMPLES
Example B1
Herbicidal Action Before Emergence of the Plants (Pre-Emergence Action)
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.
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









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
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.
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









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 having the formula:




and agronomically acceptable salts/N-oxides/isomers/enantiomers thereof wherein:
R2 is —CH2OCH3, —CH2OCH2CH3, —CH2CH2OCH3, —CH2CH2SO2CH3 or —CH2CH2OCH2CH2OCH3;
R3 is CF3, CF2CF3, CF2C1, CF2H or CCl3; and
R4 is hydrogen or methyl.

2. A compound according to claim 1 wherein:
R2 is —CH2CH2OCH3;
R3 is CF3; and
R4 is hydrogen.

3. A method of controlling growth of plants, comprising the step of applying a herbicidally effective amount of said compound according to claim 1, or a composition containing said compound, to said plants to be controlled or their habitat.

4. A method of inhibiting plant growth, comprising the step of applying a herbicidally effective amount of said compound according to claim 1, or a composition containing said compound, to said plants or their habitat.

5. A herbicidal composition comprising:
(A) an herbicidally effective amount of a compound having the formula:





wherein:
R2 is —CH2OCH3, —CH2OCH2CH3, —CH2CH2OCH3, —CH2CH2SO2CH3 or —CH2CH2OCH2CH2OCH3;
R3 is CF3, CF2CF3, CF2C1, CF2H or CCl3; and
R4 is hydrogen or methyl; and
(B) a selected inert carrier.