Pyridine ketones having herbicidal action are described, for example, in WO 97/46530. 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 each R independently is Ci-Cgatkyt, C2-C6alkenyl, C2-C6haloalkenyl, C2-C6alkynyl, C2-C6 haloalkynyl, C3-C6cycloalkyl, C1-C6alkoxy, C1-C6haloalkoxy, C1-C6alkylthio, C1- C6alkylsulfinyl, C,-C6alkylsulfonyl, C,-C6haloalkyl, C,-C6haloalkylthio, C,-C6haloalkylsulfinyl, C,-C6 haloalkyfsutfonyl, C,-C6alkoxycarbonyl, C,-C6alkylcarbonyl, C,-Csalkylamino, di-C,-C6 alkylamino, C,-C6alkylaminosutfonyl, di-C,-C6alkylaminosulfonyl,-N (R,)-S-R2,-N (R3)-SO-R4, -N (R5)-S02-R6, nitro, cyano, halogen, hydroxyl, amino, formyl, hydroxy-C,-C6alkyl, C,-C6 alkoxy-C,-C6alkyl, C,-C6alkoxycarbonyloxy-C,-C6alkyl, C,-C6alkylthio-C,-Cealkyl, C,-C6 alkylsulfinyl-C,-Csalkyl, C,-C6alkylsulfonyl-C,-Csalkyl, thiocyanato-C,-Csalkyl, cyano-C,-C6 alkyl, oxiranyl, C3-C6alkenyloxy, C3-C6alkynyloxy, C,-C6alkoxy-C,-C6alkoxy, cyano-C,-C6 alkenyloxy, C,-C6alkoxycarbonyloxy-C,-C6alkoxy, C3-C6alkynyloxy, cyano-C,-C6alkoxy, C,- <BR> <BR> C6 alkoxycarbonyl-C,-C6alkoxy, C,-C6alkylthio-C,-C6alkoxy, alkoxycarbonyl-C,-C6alkylthio, alkoxycarbonyl-C,-C6alkylsulfinyl, alkoxycarbonyl-C,-C6alkylsulfonyl, C,-C6alkylsulfonyloxy, C1-C6haloalkylsulfonyloxy, phenyl, benzyl, phenoxy, phenylthio, phenyisulfinyl, phenylsulfonyl, benzylthio, benzylsulfinyl or benzylsulfonyl, where the phenyl groups may be mono-or polysubstituted by halogen, methyl, ethyl, trifluoromethyl, methoxy or nitro, or R is 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, where the ring system is either attached directly to the pyridine ring or attached to the pyridine ring via a C,-C4alkylene group, 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 C,- C6alkyl, C,-C6haloalkyl, C3-C6alkenyl, C3-C6haloalkenyl, C3-C6alkynyl, C3-C6haloalkynyl, C,- C6alkoxy, C,-C6 haloalkoxy, C3-C6alkenyloxy, C3-C6alkynyloxy, mercapto, C,-C6alkylthio, C,- C6haloalkylthio, C3-C6alkenylthio, C3-C6haloalkenylthio, C3-C6alkynylthio, C2- Csalkoxyalkylthio, C3-C5acetytalkylthio, C3-C6alkoxycarbonylalkylthio, C2-C4cyanoalkylthio, C,-C6alkylsulfinyl, C,-C6 haloalkylsulfinyl, C,-C6alkylsulfonyl, C,-C6haloalkylsulfonyl, aminosulfonyl, C,-C2alkylaminosulfonyl, C2-C4dialkylaminosulfonyl, C,-C3alkylene-R7, NR8R9, halogen, cyano, nitro, phenyl and benzylthio, where phenyl and benzylthio for their part may be substituted on the phenyl ring by C,-C3alkyl, C,-C3haloalkyl, C,-C3alkoxy, C,- C3haloalkoxy, halogen, cyano or nitro, and where substituents on the nitrogen in the heterocyclic ring are different from halogen; m is 1, 2, 3 or 4; p is 0 or 1; Ri, R3 and R5 independently of one another are hydrogen or C,-C6alkyl; R2 is NR, oR", C,-C6alkoxy, C,-C6hafoalkoxy, C,-C6alkyl, C,-C6haloalkyl, C3-C6alkenyl, C3-C6 haloalkenyl, C3-C6alkynyl, C3-C6haloalkynyl, C3-C6cycloalkyl or phenyl, where phenyl for its part may be substituted by C,-C3alkyl, C,-C3haloalkyl, C,-C3alkoxy, C,-C3haloalkoxy, halogen, cyano or nitro; R4 is NR, 2R, 3, C,-C6alkoxy, C,-C6haloalkoxy, C,-C6alkyl, C,-C6hatoalkyl, C3-C6alkenyl, C3-C6 haloalkenyl, C3-C6alkynyl, C3-C6haloalkynyl, C3-C6cycloalkyl or phenyl, where phenyt for its part may be substituted by C,-C3alkyl, C,-C3haloalkyl, C,-C3alkoxy, C,-C3haloalkoxy, halogen, cyano or nitro; R6 is NR, 4R, 5, C,-C6alkoxy, C,-C6haloalkoxy, C,-C6alkyl, C,-C6haloalkyl, C3-C6alkenyl, C3-C6 haloalkenyl, C3-C6alkynyl, C3-C6haloalkynyl, C3-C6cycloalkyl or phenyt, where phenyl for its part may be substituted by C,-C3alkyl, C,-C3haloalkyl, C,-C3alkoxy, C,-C3haioalkoxy, halogen, cyano or nitro; R7 is C,-C3alkoxy, C2-C4alkoxycarbonyl, C1-C3alkylthio, C,-C3alkylsutfinyl, C,-C3alkylsulfonyl or phenyl, where phenyl for its part may be substituted by C,-C3alkyl, C,-C3haloalkyl, C1-C3 alkoxy, C,-C3haloalkoxy, halogen, cyano or nitro; RB, R, o, R, 2 and R, 4 independently of one another are hydrogen or C,-C6alkyl; Rg, R", Pis and R15 independently of one another are C,-C6alkyl or C,-C6alkoxy; Q is the group Q1 in which R16, R17, R18 and R19 independently of one another are hydrogen, hydroxyl, C1-C4alkyl, C2-C6 alkenyl, C2-C6alkynyl, C1-C4alkoxycarbonyl, C1-C6alkylthio, C1-C6alkylsulfinyl, C1-C6 alkylsulfonyl, C1-C4alkyl-NHS(O)2, C1-C4haloalkyl, -NH-C1-C4alkyl, -N(C1-C4alkyl)2, C1-C6 alkoxy, cyano, nitro, halogen or phenyl, which for its part may be substituted by C,-C4alkyl, C1-C4haloalkyl, C1-C4alkoxy, C1-C4haloalkoxy, C1-C4alkylcarbonyl, C1-C4alkoxycarbonyl, amino, C1-C4alkylamino, di-C1-C4alkylamino, C1-C6alkylthio, C1-C6alkylsulfinyl, C1-C6 alkylsulfonyl, C,-C4alkyl-S (0) 20, C,-C4haloalkylthio, C,-C4hafoalkylsulfinyl, C,-C4 haloalkylsulfonyl, C,-C4haloalkyl-S (0) 20, C,-C4alkyl-S (0) 2NH, C1-C4alkyl-S(O)2N(C1-C4 alkyl), halogen, nitro, COOH or cyano; or two adjacent substituents from the group consisting of R16, R17, R18 and R19 form a C2-C6alkylene bridge; R2o is hydroxyl, O'M+, halogen, cyano, SCN, OCN, C1-C12alkoxy, C1-C4alkoxycarbonyl-C1-C4 alkoxy, C-C, 2alkylthio, C,-C, 2alkylsulfinyl, C,-C, 2alkylsulfonyl, C,-C, 2haloalkylthio, C,-C, 2 haloalkylsulfinyl, C,-C, 2hatoalkylsulfonyl, C,-C6alkoxy-C,-C6alkylthio, C,-C6atkoxy-C,-C6 alkylsulfinyl, C,-C6alkoxy-C,-C6alkylsulfonyl, C2-C, 2alkenylthio, C2-C, 2alkenylsulfinyl, C2-C, 2 alkenylsutfonyl, C2-C, 2alkynylthio, C2-C, zalkynylsulfinyl, C2-C, 2alkynylsulfonyl, C2-C, 2 haloalkenylthio, C2-C, 2haloalkenylsulfinyl, C2-C,2haloalkenylsulfonyl, C,-C4alkoxycarbonyl- C,-C4alkylthio, C,-C4alkoxycarbonyl-C,-C4alkylsulfinyl, C,-C4alkoxycarbonyl-C,- C4alkylsuSfonyl, (C1-C4alkoxy)2P (O) O, C,-C4alkyl- (C,-C4alkoxy) P (Q) O, H (C,- C4alkoxy) P (O) O, R37R38N, R7RR72NNH-, R2, R22NC (O) O-, R73R74NC (O) NH-, C1-C4alkyl-S(O)2NR39, C,-C4 haloalkyl-S (0) 2NR4o, C1-C4alkyl-S(O)2O, C1-C4haloalkyl-S(O)2O, C,-C, ealkylcarbonyloxy, where the alkyl group may be substituted by halogen, C1-C6alkoxy, C,. C6alkylthio or cyano, C2-C, ealkenylcarbonyloxy, C2-C, salkynylcarbonyloxy, C3-C6cycloalkyicarbonyloxy, C,-C, 2 alkoxycarbonyloxy, C,-C, Zalkylthiocarbonyloxy, C,-C, 2alkylthiocarbamoyi, C,-C6alkyl- NH (CS) N (C,-C6alkyl)-NH-, di-C,-C6alkyl-N (CS) N (C,-C6alkyl)-NH-, benzyloxy, benzytthio, benzylsulfinyl, benzylsulfonyl, phenoxy, phenylthio, phenylsulfinyl, phenylsulfonyl, phenyisulfonyloxy or benzoyloxy, where the phenyl groups for their part may each be substituted by C,-C4alkyl, C,-C4haloalkyl, C,-C4alkoxy, C,-C4haloalkoxy, C,-C4alkylcarbonyl, C,-C4alkoxycarbonyl, C,-C4alkylamino, di-C,-C4alkylamino, C,-C4alkylthio, C,-C4alkylsulfinyl, C,-C4alkylsulfonyl, C,-C4alkyl-S (0) 20, C,-C4haloalkylthio, C,-C4haloalkylsulfinyl, C,-C4 haloalkylsulfonyl, C,-C4haloalkyl-S (0) 20, C,-C4alkyl-S (0) 2NH, C,-C4alkyl-S (0) 2N (C,-C4 alkyl), halogen, nitro or cyano, or a group Ar,-thio, Ar2-sulfinyl, Ar3-sulfonyl,-OCO-Ar4 or NH-Ars in which Ari, Ars, Ara, Ar4 and Ars 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 in which each ring system may not contain more than 2 oxygen atoms and not more than two sulfur atoms, and in which the ring system for its part may be mono-, di-or trisubstituted by C,-C6alkyl, C1-C6haloalkyl, C3-C6alkenyl, C3-C6haloalkenyl, C3-C6alkynyl, C3-C6haloalkynyl, C1-C6alkoxy,C1-C6haloalkoxy, C3-C6alkenyloxy, C3-C6alkynyioxy, mercapto, C1-C6alkylthio, C,-C6haloalkylthio, C3-C6alkenylthio, C3-C6haloalkenylthio, C3-C6alkynylthio, C2-C5 alkoxyalkylthio, C3-C5acetylalkylthio, C3-C6alkoxycarbonylalkylthio, C2-C4cyanoalkylthio, C1- C6alkylsulfinyl, C1-C6haloalkylsulfinyl, C,-C6alkylsulfonyl, C1-C6haloalkylsulfonyl, aminosulfonyl, C,-C2alkylaminosulfonyl, C2-C4dialkylaminosulfonyl, C,-C3alkylene-R4,, NR42R43, halogen, cyano, nitro, phenyl and benzylthio, where phenyl and benzylthio for their part may be substituted on the phenyl ring by C1-C3alkyl, C,-C3haloalkyl, C1-C3alkoxy, C1- C3haloalkoxy, halogen, cyano or nitro, and where substituents on the nitrogen in the heterocyclic ring are different from halogen; R4, is C1-C3alkoxy, C2-C4alkoxycarbonyl, C,-C3alkylthio, C,-C3alkylsulfinyl, C,-C3 alkylsulfonyl or phenyl, where phenyl for its part may be substituted by C,-C3alkyl, C,-C3 haloalkyl, C,-C3alkoxy, C,-C3haloalkoxy, halogen, cyano or nitro; R42 is hydrogen or C1-C6alkyl ; R43 is C,-C6alkyl or C,-C6alkoxy; R2,, R37, R39, R4o, R7, and R73 independently of one another are hydrogen or C,-C4alkyl; Rz2, R38, R72 and R74 independently of one another are hydrogen, C,-C, 2alkyl, hydroxyl, C,- C, 2alkoxy, C3-C6alkenyloxy or C3-C6alkynyloxy; or R2, and R22 together or R37 and R38 together or R7, and R72 together or R73 and R74 together are pyrrolidino, piperidino, morpholino, thiomorpholino, which may be mono-or polysubstituted by methyl groups; or are the group Q2 in which Y is a chemical bond, an alkylene group A,, carbonyl, oxygen, sulfur, sulfinyl, sulfonyl, -NHR248 or NH (CO) R249; A, is C (R246R247) Mol A is C (R244R24s)r; r and mol independently of one another are 0,1 or 2; R240 is hydrogen, methyl or C,-C3alkoxycarbonyl; R241, R242, R243, R244, R245, R246 and R247 independently of one another are hydrogen, halogen or methyl, or R243 together with an adjacent group R245 or R247 is a chemical bond; R248 and R249 independently of one another are hydrogen or C,-C4alkyl; R23 is hydroxyl, O'M', halogen, cyano, SCN, OCN, C,-C, Zalkoxy, C,-C4alkoxycarbonyl-C,-C4 alkoxy, C1-C12alkylthio, C1-C12alkylsulfinyl, C1-C12alkylsulfonyl, C1-C12haloalkylthio, C1-C12 haloalkylsulfinyl, C1-C12haloalkylsulfonyl, C1-C6alkoxy-C1-C6alkylthio, C1-C6alkoxy-C1-C6 alkylsulfinyl, C,-C6alkoxy-C,-C6alkylsulfonyl, C2-C, 2alkenylthio, C2-C, 2alkenylsulfinyl, C2-C, 2 alkenyfsulfonyl, C2-C12alkynylthio, C2-C12alkynylsulfinyl, C2-C12alkynylsulfonyl, C2-C12 haloalkenylthio, C2-C, 2haloalkenylsulfinyl, C2-C,2haloalkenylsulfonyl, C,-C4alkoxycarbonyl- C1-C4alkylthio, C1-C4alkoxycarbonyl-C1-C4alkylsulfinyl, C1-C4alkoxycarbonyl-C1- C4alkylsulfonyl, (C,-C4alkoxy) 2P (O) O, C,-C4alkyl- (C,-C4alkoxy) P (O)O, H(C1- C4alkoxy)P(O)O, R44R45N, R7sR76NNH-, R46R47NC(O)O-, RnR7eNC (O) NH-, C1-C4alkyl-S(O)2NR48, C1-C4 haloalkyl-S (0) 2NR49, C1-C4alkyl-S(O)2O, C1-C4haloalkyl-S Ci-Cieatkytcarbonytoxy, where the alkyl group may be substituted by halogen, C,-C6alkoxy, C,-C6alkylthio or cyano, C2-C,8alkenylcarbonyloxy, C2-C, 8alkynylcarbonyloxy, C3-C6cycloalkylcarbonyloxy, C,-C, 2 alkoxycarbonyloxy, C,-C, 2alkylthiocarbonyloxy, C,-C, 2alkylthiocarbamoyl, C,-C6alkyl- NH (CS) N (C,-C6alkyl)-NH-, di-C,-C6alkyl-N (CS) N (C,-C6alkyl)-NH-, benzyloxy, benzylthio, benzylsulfinyi, benzylsulfonyl, phenoxy, phenylthio, phenylsulfinyl, phenyisulfonyl, phenyisulfonyloxy or benzoyloxy, where the phenyl groups for their part may each be substituted by C1-C4alkyl, C1-C4haloalkyl, C1-C4alkoxy, C1-C4haloalkoxy, C1-C4alkylcarbonyl, C,-C4alkoxycarbonyl, C,-C4alkylamino, di-C,-C4alkylamino, C,-C4alkylthio, C,-C4alkylsulfinyl, C,-C4alkylsulfonyl, C,-C4alkyl-S (0) 20, C,-C4haloalkylthio, C,-C4haloalkylsulfinyl, C,-C4 haloalkylsulfonyl, C,-C4haloalkyl-S (0) 20, C,-C4alkyl-S (0) 2NH, C,-C4alkyl-S (0) 2N (C,-C4 alkyl), halogen, nitro or cyano, or a group Ar6-thio, Ar7-sulfinyl, Are-sulfonyl,-OCO-Arg or NH-Ar10 in which Ar6, Ar7, Ar8, Arg and Ar, o independently of one another are a five-to ten-membered monocyclic or fused bicyclic ring system which may be aromatic or partial saturated and may contain 1 to 4 heteroatoms selected from the group consisting of nitrogen, oxygen and sulfur, and in which each ring system may not contain more than 2 oxygen atoms and not more than two sulfur atoms, and in which the ring system for its part may be mono-, di-or trisubstituted by C,-C6alkyl, C,-C6haloalkyl, C3-C6alkenyl, C3-C6haloalkenyl, C3-C6alkynyl, C3-C6haloalkynyl, C,-C6alkoxy, C,-C6haloalkoxy, C3-C6alkenyloxy, C3-C6alkynyloxy, mercapto, C,-C6alkylthio, C,-C6haloalkylthio, C3-C6alkenylthio, C3-C6haloalkenylthio, C3-C6alkynylthio, C2-Cs alkoxyalkylthio, C3-C5acetylalkylthio, C3-C6alkoxycarbonylalkylthio, C2-C4cyanoalkylthio, C,- C6alkylsulfinyl, C,-C6haloalkylsulfinyl, C,-C6alkylsulfonyl, C,-C6haloalkylsulfonyl, aminosulfonyl, C,-C2alkylaminosulfonyl, C2-C4dialkylaminosulfonyl, C,-C3alkylene-RsO, NRsiRs2, hatogen, cyano, nitro, phenyl and benzylthio, where phenyl and benzylthio for their part may be substituted on the phenyl ring by C,-C3alkyl, C,-C3haloalkyl, C1-C3alkoxy, C,- C3haloalkoxy, halogen, cyano or nitro, and where substituents on the nitrogen in the heterocyclic ring are different from halogen; R50 is C1-C3alkoxy, C2-C4alkoxycarbonyl, C1-C3alkylthio, C1-C3alkylsulfinyl, C1-C3alkylsulfonyl or phenyl, where phenyl for its part may be substituted by C,-C3alkyl, C,-C3haloalkyl, C,-C3 alkoxy, Cl-C3haloalkoxy, halogen, cyano or nitro; R5, is hydrogen or C,-C6alkyl; R52 is C1-C6alkyl or C1-C6alkoxy; R46, R44, R48, R49, R75 and R77 independently of one another are hydrogen or C,-C4alkyl; R47, R45, R76 and R78 independently of one another are hydrogen, ,-C, Zalkyl, hydroxyl, C,- C, 2alkoxy, C3-C6alkenyloxy or C3-C6alkynyloxy; or R44 and R45 together or R46 and R47 together or R75 and Rye together or R77 and R78 together are pyrrolidino, piperidino, morpholino, thiomorpholino, which may be mono-or polysubstituted by methyl groups; or are the group Q3 in which R26 is hydroxyl, O'M', halogen, cyano, SCN, OCN, C,-C, 2alkoxy, C,-C4alkoxycarbonyl-C,-C4 alkoxy, C1-C12alkylthio, C1-C12alkylsulfinyl, C1-C12alkylsulfonyl, C1-C12haloalkylthio, C1-C12 haloalkylsulfinyl, C,-C, 2haloalkylsulfonyl, C,-C6alkoxy-C,-C6alkylthio, C,-C6alkoxy-C,-C6 alkylsulfinyl, C,-C6alkoxy-C,-C6alkylsulfonyl, C2-C, 2alkenylthio, C2-C, aaikenyfsulfinyl, C2-C, z alkenylsulfonyl, C2-C, 2alkynylthio, C2-C, 2alkynylsulfinyl, C2-C, 2alkynylsulfonyl, C2-C, 2 haloalkenylthio, C2-C, 2haloalkenyisulfinyl, C2-C, 2haloalkenyisulfonyl, C,-C4alkoxycarbonyl- C,-C4alkylthio, C,-C4alkoxycarbonyl-C,-C4alkylsulfinyl, C,-C4alkoxycarbonyl-C,- C4alkylsulfonyl, (C,-Caalkoxy) 2P (O) O, C,-C4alkyl- (C,-C4alkoxy) P (O) O, H (C,- C4alkoxy) P (O) O, R53R54N, R79R80NNH-, R55R56NC(O)O-, R81R82NC(O)NH-, C1-C4alkyl-S(O)2NR57, C1-C4 haloalkyl-S (0) 2NR58, C,-C4alkyl-S (0) 20, C,-C4haloalkyl-S (0) 20, C,-C, 8alkylcarbonyloxy, where the alkyl group may be substituted by halogen, C,-C6alkoxy, C1-C6alkylthio or cyano, C2-C18alkenylcarbonyloxy, C2-C18alkynylcarbonyloxy, C3-C6cycloalkylcarbonyloxy, C,-C, 2 alkoxycarbonyloxy, C,-C, Zalkylthiocarbonyloxy, C,-C, 2alkylthiocarbamoyl, C,-C6alkyl- NH (CS) N (C,-C6alkyl)-NH-, di-C,-C6alkyl-N (CS) N (C,-C6alkyl)-NH-, benzyloxy, benzylthio, benzylsulfinyl, benzylsulfonyl, phenoxy, phenylthio, phenylsulfinyl, phenylsulfonyl, phenylsuifonyloxy or benzoyloxy, where the phenyl groups for their part may each be substituted by C,-C4alkyl, C,-C4haloalkyl, C,-C4alkoxy, C-C4haloalkoxy, C,-C4alkylcarbonyl, C,-C4alkoxycarbonyl, C,-C4alkylamino, di-C,-C4alkylamino, C,-C4alkylthio, C,-C4alkylsulfinyl, C,-C4alkylsulfonyl, C,-C4alkyl-S (0) 20, C,-C4haloalkylthio, C,-C4haloalkylsulfinyl, C,-C4 haloalkylsulfonyl, C,-C4haloalkyl-S (0) 20, C,-C4alkyl-S (0) 2NH, C1-C4alkyl-S(O)2N (Ci-C4 alkyl), halogen, nitro or cyano, or a group Ar"-thio, Ar, 2-sulfinyl, Ar, 3-sulfonyl,-OCO-Ar, 4 or NH-A, r, 5 in which Ar", Ar, 2, Ar, 3, Ar, 4 and Ar15 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 in which each ring system may not contain more than 2 oxygen atoms and not more than two sulfur atoms, and in which the ring system for its part may be mono-, di-or trisubstituted by C,-C6alkyl, C,-C6haloalkyl, C3-C6alkenyl, C3-C6haloalkenyl, C3-C6alkynyl, C3-C6haloalkynyl, C,-Csalkoxy, C,-C6haloalkoxy, C3-C6alkenyloxy, C3-C6alkynyloxy, mercapto, C,-C6alkylthio, C1-C6haloalkylthio, C3-C6alkenylthio, C3-C6haloalkenylthio, Cs-Ceatkynytthio, C2-C5 alkoxyalkylthio, C3-Csacetylalkylthio, C3-C6alkoxycarbonylalkylthio, C2-C4cyanoalkylthio, C,- C6alkylsulfinyl,C,-C6haloalkylsulfinyl, C,-C6alkylsulfonyl, C,-C6haloalkylsulfonyl, aminosulfonyl, C,-C2alkylaminosulfonyl, C2-C4dialkylaminosulfonyl, C,-C3alkylene-R59, NR60R61, halogen, cyano, nitro, phenyl and benzylthio, where phenyl and benzylthio for their part may be substituted on the phenyl ring by C,-C3alkyl, C,-C3haloalkyl, C,-C3alkoxy, C,- C3haloalkoxy, halogen, cyano or nitro, and where substituents on the nitrogen in the heterocyclic ring are different from halogen; R59 is C,-C3alkoxy, C2-C4alkoxycarbonyl, C,-C3alkylthio, C,-C3alkylsulfinyl, C,-C3alkylsulfonyl or phenyl, where phenyl for its part may be substituted by C,-C3alkyl, C,-C3haloalkyl, C,-C3 alkoxy, C,-C3haloalkoxy, halogen, cyano or nitro; R60 is hydrogen or C,-C6alkyl; R6, is C,-C6alkyl or C,-C6alkoxy; R55, R53, R57, R58, R79 and R81 independently of one another are hydrogen or C,-C4alkyl; Rse. R54, Reo and R82 independently of one another are hydrogen, C,-C, 2alkyl, hydroxyl, C,- C, 2alkoxy, C3-C6alkenyloxy or C3-C6alkynyloxy; or R53 and R54 together or R55 and R56 together or R79 and R80 together or R8, and R82 together are pyrrolidino, piperidino, morpholino, thiomorpholino, which may be mono-or polysubstituted by methyl groups; R29 is hydrogen, C1-C6alkyl, C,-C4alkylcarbonyl, C,-C4alkoxycarbonyl, (C,-C4alkyl) NHCO, phenylaminocarbonyl, benzylaminocarbonyl or (C,-C4alkyl) 2NCO, where the phenyl and benzyl groups for their part may each be substituted by C,-C4alkyl, C,-C4haloalkyl, C,-C4 alkoxy, C,-C4haloalkoxy, C,-C4alkylcarbonyl, C,-C4alkoxycarbonyl, C,-C4alkylamino, di-C,-C4 alkylamino, C1-C4alkylthio, C,-C4alkylsulfinyl, C,-C4alkylsulfonyl, C,-Caalky !-S (0) 20, C,-C4 haloalkylthio, C,-C4haloalkylsulfinyl, C,-C4haloalkylsulfonyl, C,-C4haloalkyl-S (0) 20, C,-C4 alkyl-S(O)2NH, C1-C4alkyl-S(O)2N(C1-C4alkyl), halogen, nitro or cyano; or is the group Q4 in which R30 is hydroxyl, O-M+, halogen, cyano, SCN, OCN, C1-C12alkoxy, C1-C4alkoxycarbonyl-C1-C4 alkoxy, C,-C, 2alkyithio, C,-C, Zalkyisulfinyl, C,-C, 2alkylsulfonyl, C,-C, 2haloalkylthio, C,-C, z haloalkylsulfinyl, C,-C, 2haloalkylsulfonyl, C,-Cealkoxy-C,-C6alkylthio, C,-C6alkoxy-C,-C6 alkylsulfinyl, C,-Csalkoxy-C,-C6alkylsulfonyl, C2-C, 2alkenylthio, C2-C, 2alkenylsulfinyl, C2-C, 2 alkenylsulfonyl, C2-C2alkynylthio, C2-C, 2alkynylsulfinyl, C2-C, 2alkynylsulfonyl, C2-C, 2 haloalkenylthio, C2-C, 2haloalkenylsulfinyl, C2-C, 2haloalkenylsulfonyl, C,-C4alkoxycarbonyl- C,-C4alkylthio, C,-C4alkoxycarbonyl-C,-C4alkylsulfinyl, C,-C4alkoxycarbonyl-C,- C4alkylsulfonyl, (C,-C4alkoxy) 2P (O) O, C,-C4alkyl- (C,-C4alkoxy) P (O) O, H (C,- C4alkoxy) P (O) O, R62R63N, R83R84NNH-, R64R65NC (O) O-, R85R86NC (O) NH-, C,-C4alkyl-S (0) 2NR66, C,-C4 haloalkyl-S (0) 2NR67, C,-C4alkyl-S (0) 20, C,-C4haloalkyl-S (0) 20, C,-C, ealkylcarbonyloxy, where the alkyl group may be substituted by halogen, C,-C6alkoxy, C,-C6alkylthio or cyano, C2-C18alkenylcarbonyloxy, C2-C, ealkynylcarbonyloxy, C3-C6cycfoalkylcarbonyloxy, C,-C,2 alkoxycarbonyloxy, C1-C12alkylthiocarbonyloxy, C1-C12alkylthiocarbamoyl, C1-C6alkyl- NH (CS) N (C,-C6alkyl)-NH-, di-C,-C6alkyl-N (CS) N (C,-C6alkyl)-NH-, benzyloxy, benzylthio, benzylsulfinyl, benzylsulfonyl, phenoxy, phenylthio, phenylsulfinyl, phenylsulfonyl, phenylsulfonyloxy or benzoyloxy, where the phenyl groups for their part may each be substituted by C,-C4alkyl, C,-C4haloalkyl, C1-C4alkoxy, C1-C4haloalkoxy, C1-C4alkylcarbonyl, C,-C4alkoxycarbonyl, C,-C4alkylamino, di-C,-C4alkylamino, C,-C4alkylthio, C,-C4alkylsulfinyl, C,-C4alkylsulfonyl, C,-C4alkyl-S (0) 20, C,-C4haloalkylthio, C,-C4haloalkylsulfinyl, C,-C4 haloalkylsulfonyl, C,-C4haloalkyl-S (0) 20, C,-C4alkyl-S (0) 2NH, C,-C4alkyl-S (0) 2N (C,-C4 alkyl), halogen, nitro or cyano, or a group Ar16-thio, Ar17-sulfinyl, Ar18-sulfonyl, -OCO-Ar19 or NH-Ar20 in which Ar, 6, Ar, 7, Ar, 8, Ar, 9 and Ar20 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 in which each ring system may not contain more than 2 oxygen atoms and not more than two sulfur atoms, and in which the ring system for its part may be mono-, di-or trisubstituted by C,-C6alkyl, C,-C6haloalkyl, C3-C6aikenyl, C3-C6haloalkenyl, C3-C6alkynyt, C3-C6haloalkynyl, C,-C6alkoxy, C,-C6haloalkoxy, C3-C6alkenyloxy, C3-Csalkynyloxy, mercapto, C,-C6alkylthio, C,-C6haloalkytthio, C3-C6alkenylthio, C3-C6haloalkenylthio, C3-C6alkynylthio, C2-C5 alkoxyalkylthio, C3-C5acetylalkylthio, C3-C6alkoxycarbonylalkylthio, C2-C4cyanoalkylthio, C,- C6alkylsulfinyl, C,-C6hatoalkylsulfinyl, C,-C6alkylsulfonyl, C,-C6hatoalkylsulfonyl, aminosulfonyl, C,-C2alkytaminosulfonyl, C2-C4dialkylaminosulfonyl, C,-C3alkylene-R63, NR69R70, halogen, cyano, nitro, phenyl and benzylthio, where phenyl and benzylthio for their part may be substituted on the phenyl ring by C,-C3alkyl, C1-C3haloalkyl, C1-C3alkoxy, C1- C3haloalkoxy, halogen, cyano or nitro, and where substituents on the nitrogen in the heterocyclic ring are different from halogen; R68 is C,-C3alkoxy, C2-C4alkoxycarbonyl, C,-C3alkylthio, C1-C3alkylsulfinyl, C,-C3alkylsulfonyl or phenyl, where phenyl for its part may be substituted by C,-C3alkyl, C,-C3haloalkyl, C,-C3 alkoxy, C,-C3haloalkoxy, halogen, cyano or nitro; R70 is hydrogen or C,-C6alkyl; R6, is C,-C6alkyl or C,-C6alkoxy; R64. R62, R66, R67, R83 and R85 independently of one another are hydrogen or C,-C4alkyl; R65, R63, R84 and R86 independently of one another are hydrogen, C,-C, 2alkyl, hydroxyl, C,- C, 2alkoxy, C3-C6alkenyloxy or C3-C6alkynyloxy; or R62 and R63 together or R64 and R65 together or R83 and R84 together or R85 and R86 together are pyrrolidino, piperidino, morpholino, thiomorpholino, which may be mono-or polysubstituted by methyl groups; R33 and R34 independently of one another are hydrogen, C,-C4alkyl, C2-C6alkenyl, C2-C6 alkynyl, C,-C4alkoxycarbonyl, C,-C6alkylthio, C,-C6alkylsulfinyl, C,-C6alkylsulfonyl, C,-C4 alkyl-NHS (0) 2, C,-C4haloalkyl,-NH-C,-C4alkyl,-N (C,-C4alkyl) 2, C,-C6alkoxy or phenyl, which for its part may be substituted by C,-C4alkyl, C1-C4haloalkyl, C1-C4alkoxy, C1-C4haloalkoxy, C,-C4alkylcarbonyl, C,-C4alkoxycarbonyl, amino, C,-C4alkylamino, di-C,-C4alkylamino, C1-C6 alkylthio, C,-C6alkylsulfinyl, C,-C6alkylsulfonyl, C,-C4alkyl-S (0) z0, C,-C4haloalkylthio, C,-C4 haloalkylsulfinyl, C1-C4haloalkylsulfonyl, C1-C4haloalkyl-S(O)2O, C1-C4alkyl-S(O)2NH, C1-C4 alkyl-S (0) 2N (C,-C4alkyl), halogen, nitro, COOH or cyano; or R33 and R34 together form a C2- C6alkylene bridge; and R35 is hydrogen, C1-C6alkyl, C3-C6alkenyl, C3-C6alkynyl or benzyl, which for its part may be substituted by halogen, methyl or methoxy, or is C,-C4alkoxycarbonyl or phenyl, which for its part may be substituted by C,-C4alkyl, C,-C4haloalkyl, C,-C4aikoxy, C1-C4haloalkoxy, C,-C4 alkylcarbonyl, C1-C4alkoxycarbonyl, amino, C1-C4alkylamino, di-C1-C4alkylamino, C1-C4 alkylthio, C,-C4alkylsulfinyl, C,-C4alkylsulfonyl, C,-C4alkyl-S (0) 20, C1-C4haloalkylthio, C1-C4 haloalkylsulfinyl, C,-C4haloalkylsulfonyl, C,-C4haloalkyl-S (0) 20, C1-C4alkyl-S(O)2NH, C1-C4 alkyl-S (0) 2N (C,-C4alkyl), halogen, nitro, COOH or cyano; or is the group Q5 in which Z is S, SO or S02; Roi is hydrogen, C,-Csalkyl, C,-Cealkyl substituted by halogen, C1-C4alkoxy, C1-C4alkylthio, C,-C4alkylsulfonyl, C,-C4alkylsulfinyl,-C02Ro2,-CORo3,-COSRo4,-NRosR06, CONR036R037 or phenyl, which for its part may be substituted by C,-C4alkyl, C1-C6haloalkyl, C1-C4alkoxy, C1- C4haloalkoxy, C2-C6alkenyl, C3-C6alkynyl, C3-C6alkenyloxy, C3-C6alkynyloxy, halogen, nitro, cyano,-COOH, COOC1-C4alkyl, COOphenyl, C1-C4alkoxy, phenoxy, (C,-C4alkoxy)-C,-C4 alkyl, (C,-C4alkylthio)-C,-C4alkyl, (C,-C4alkylsulfinyl)-C,-C4alkyl, (C,-C4alkylsulfonyl)-C,-C4 alkyl, NHSO2-C,-C4alkyl, NHSOz-phenyl, N (C,-C6alkyl) S02-C,-C4alkyl, N(C1-C6alkyl)SO2- phenyl, N (C2-C6alkenyl) S02-C,-C4alkyl, N(C2-C6alkenyl)SO2-phenyl, N(C3-C6alkynyl)SO2-C1- C4alkyl, N (C3-C6alkynyl) SO2-phenyl, N (C3-C7cycloalkyl) S02-C,-Caalkyl, N (C3-C7 cycloalkyl) S02-phenyl, N (phenyl) S02-C,-C4alkyl, N (phenyl) S02-phenyl, OSO2-C,-C4alkyl, CONR25R26, OS02-C,-C4haloalkyl, OS02-phenyl, C,-C4alkylthio, C,-C4haloalkylthio, phenylthio, C1-C4alkylsulfonyl, C1-C4haloalkylsulfonyl, phenylsulfonyl, C1-C4alkylsulfinyl, C1- C4haloalkylsulfinyl, phenylsulfinyl, C,-C4alkylene-phenyl or-NRo, SC02Ro27; or Roi is C2-Cealkenyl or C2-Cealkenyl substituted by halogen, C,-C4alkoxy, C,-C4alkylthio, C,-C4alkylsulfonyl, C,-C4alkylsulfinyl,-CONRo32Ro33, cyano, nitro,-CHO,-C02Ro38,-CORo39, -COS-C,-C4alkyl,-NRo34Ro3s or phenyl which for its part may be substituted by C,-C4alkyl, C1-C6haloalkyl, C,-C4alkoxy, C,-C4haloalkoxy, C2-C6alkenyl, C3-C6alkynyl, C3-C6alkenyloxy, C3-C6alkynyloxy, halogen, nitro, cyano,-COOH, COOC,-C4alkyl, COOphenyl, C1-C4alkoxy, phenoxy, (C,-C4alkoxy)-C,-C4alkyl, (C,-Caalkylthio)-C,-C4alkyl, (C,-Caalkylsulfinyl)-C,-Caalkyl, (C,-C4alkylsulfonyl)-C,-C4alkyl, NHS02-C,-C4alkyl, NHSO2-phenyl, N(C1-C6alkyl)SO2-C1-C4 alkyl, N (C,-C6alkyl) SO2-phenyl, N (C2-C6alkenyl) S02-C,-C4alkyl, N (C2-C6alkenyl) SO2-phenyl, N (C3-C6alkynyl) S02-C,-C4alkyl, N (C3-C6alkynyl) SO2-phenyl, N (C3-C7cycloalkyl) SO2-C,-C4 alkyl, N (C3-C7cycloalkyl) S02-phenyl, N (phenyi) S02-C,-C4alkyl, N (phenyl) SO2-phenyl, OS02- C1-C4alkyl, CONR040R041, OSO2-C1-C4haloalkyl, OSO2-phenyl, C1-C4alkylthio, C1-C4 haloalkylthio, phenylthio, C,-C4alkylsulfonyl, C,-C4haloalkylsulfonyl, phenylsulfonyl, C,-C4 alkylsulfinyl, C,-C4haloalkylsulfinyl, phenylsulfinyl, C,-C, alkylene-phenyl or-NRO43C02RO42; or Roi is C3-C6alkynyl or C3-C6alkynyl substituted by halogen, C,-C4haloalkyl, cyano, -C02Ro44 or phenyl, which for its part may be substituted by C1-C4alkyl, C1-C6haloalkyl, C1-C4 alkoxy, C,-C4haloalkoxy, C2-C6alkenyl, C3-C6alkynyl, C3-Csalkenyloxy, C3-C6alkynyloxy, halogen, nitro, cyano,-COOH, COOC,-C4alkyl, COOphenyl, C,-C4alkoxy, phenoxy, (C,-C4 alkoxy)-C,-C4alkyl, (C,-C4alkylthio)-C,-C4alkyl, (C,-C4alkylsulfinyl)-C,-C4alkyl, (C,-C4 alkylsulfonyl)-C,-C4alkyl, NHS02-C,-C4alkyl, NHS02-phenyl, N (C,-C6alkyl) S02-C,-C4alkyl, N (C,-C6alkyl) S02-phenyl, N (C2-C6alkenyl) SO2-C,-Caalkyl, N(C2-C6alkenyl)SO2-phenyl, N(C3- C6alkynyl)SO2-C1-C4alkyl, N (C3-C6alkynyl) SO2-phenyl, N (C3-C7cycloalkyl) S02-C,-C4alkyl, N (C3-C7cycloalkyl) S02-phenyl, N (phenyl)SO2-C1-C4alkyl, N (phenyl) S02-phenyl, OS02-C,-C4 alkyl, CONRo28Ro29, OSO2-C,-C4haloalkyl, OS02-phenyl, C,-C4atkylthio, C,-C4haloalkylthio, phenylthio, C,-C4alkylsulfonyl, C,-C4haloalkylsulfonyl, phenylsulfonyl, C,-C4alkylsulfinyl, C,- C4haloalkylsulfinyl, phenylsulfinyl, C,-C4alkylene-phenyl or-NRo3, C02Ro3o; or Roi is C3-C, cycloalkyl, C3-C7cycloalkyl substituted by C,-C4alkyl, C,-C4alkoxy, C,-C4 alkylthio, C,-C4alkylsulfinyl, C,-C4alkylsulfonyl or phenyl, which for its part may be substituted by halogen, nitro, cyano, C,-C4alkoxy, C1-C4haloalkoxy, C1-C4alkylthio, C1- C4haloalkylthio, C,-C4alkyl and C,-C4haloalkyl; or Roi is C,-C4alkylene-C3-C7cycloalkyl, phenyl, or phenyl which is substituted by C,-C4alkyl, C,-C6haloalkyl, C,-C4alkoxy, C,-C4haloalkoxy, C2-C6alkenyl, C3-C6alkynyl, C3-C6alkenyloxy, C3-C6alkynyloxy, halogen, nitro, cyano,-COOH, COOC1-C4alkyl, COOphenyl, C1-C4alkoxy, phenoxy, (C1-C4alkoxy)-C1-C4alkyl, (C1-C4alkylthio)-C1-C4alkyl, (C1-C4alkylsulfinyl)-C1-C4alkyl, (C,-C4alkylsulfonyl)-C,-C4alkyl, NHS02-C,-C4alkyl, NHSO2-phenyl, N(C1-C6alkyl)SO2-C1-C4 alkyl, N (C,-C6alkyl) S02-phenyl, N (C2-C6alkenyl) S02-C,-C4alkyl, N (C2-C6alkenyl) SO2-phenyl, N (C3-C6alkynyl) SO2-C1-C4alkyl, N(C3-C6alkynyl)SO2-phenyl, N (C3-C7cycloalkyl) SO2-C,-C4 alkyl, N (C3-C7cycloalkyl) S02-phenyl, N (phenyl) S02-C,-C4alkyl, N (phenyl) S02-phenyl, OS02- C,-C4alkyl, CONRo45Ro46, OS02-C,-C4haloalkyl, OSO2-phenyl, C,-C4alkylthio, C,- C4haloalkylthio, phenylthio, C,-C4alkylsulfonyl, C,-C4haloalkylsulfonyl, phenylsulfonyl, C,-C4 alkylsulfinyl, C,-C4haloalkylsulfinyl, phenylsulfinyl, or-NROeC02RO47; or R01 is C1-C4alkylene-phenyl, COR07 or 4-6-membered heterocyclyl; Ro2, Ro38, Ro44 and Roee independently of one another are hydrogen, C,-C4alkyl, phenyl, or phenyl which is substituted by C,-C4alkyl, C1-C6haloalkyl, C,-C4alkoxy, C,-C4hatoalkoxy, C2- C6alkenyl, C3-C6alkynyl, C3-C6alkenyloxy, C3-C6alkynyloxy, halogen, nitro, cyano,-COOH, COOC1-C4alkyl, COOphenyl, C,-C4alkoxy, phenoxy, (C,-C4alkoxy)-C,-C4alkyi, (C,-C4 alkylthio)-C1-C4alkyl, (C1-C4alkylsulfinyl)-C1-C4alkyl, (C1-C4alkylsulfonyl)-C1-C4alkyl, NHSO2- C,-C4alkyl, NHS02-phenyl, N(C1-C6alkyl)SO2-C1-C4alkyl, N(C,-C6alkyl)SO2-phenyl, N (C2-C6 alkenyl) S02-C,-C4alkyl, N(C2-C6alkenyl)SO2-phenyl, N(C3-C6alkynyl)SO2-C1-C4alkyl, N (C3-C6 alkynyl) SO2-phenyl, N (C3-C7cycloalkyl) S02-C,-C4alkyl, N (C3-C7cycloalkyl) S02-phenyl, N (phenyl) S02-C,-C4alkyl, N (phenyl) S02-phenyl, OSO2-C1-C4alkyl, CONR049R050, OSO2-C1- C4 haloalkyl, OSO2-phenyl, C,-C4alkylthio, C,-C4haloalkyithio, phenylthio, C,-C4alkylsulfonyl, C1-C4haloalkylsulfonyl, phenylsulfonyl, C1-C4alkylsulfinyl, C1-C4haloalkylsulfinyl, phenylsulfinyl, C,-C4alkylene-phenyl or-NRo52C02Ro53; R03, R039 and Ro67 independently of one another are C,-C4alkyl, phenyl or phenyl which is substituted by C,-C4alkyl, C1-C6haloalkyl, C1-C4alkoxy, C1-C4haloalkoxy, C2-C6alkenyl, C3-C6 alkynyl, C3-C6alkenyloxy, C3-C6alkynyloxy, halogen, nitro, cyano,-COOH, COOC1-C4alkyl, COOphenyl, C,-C4alkoxy, phenoxy, (C1-C4alkoxy)-C1-C4alkyl, (C1-C4alkylthio)-C1-C4alkyl, (C,-C4alkylsulfinyl)-C,-C4alkyl, (C,-C4alkylsulfonyl)-C,-C4alkyl, NHSO2-C,-C4alkyl, NHS02- phenyl, N (C,-C6alkyl)SO2-C1-C4alkyl, N (C,-C6alkyl) SO2-phenyl, N (C2-C6alkenyl)SO2-C1- C4alkyl, N(C2-C6alkenyl)SO2-phenyl, N (C3-C6alkynyl)SO2-C1-C4alkyl, N (C3-C6alkynyl) SO2- phenyl, N (C3-C7cycloalkyl) S02-C,-C4alkyl, N (C3-C7cycloalkyl) S02-phenyl, N (phenyl) S02-C,- C4alkyl, N (phenyl) SO2-phenyl, OS02-C,-C4alkyl, CONROo7oRo54, OS02-C,-C4haloalkyl, OSO2-phenyl, C,-C4alkylthio, C,-C4haloalkylthio, phenylthio, C,-C4alkylsulfonyl, C,- C4haloalkylsulfonyl, phenylsulfonyl, C,-C4alkylsulfinyl, C,-C4haloalkylsulfinyl, phenylsulfinyl, C,-Caalkylene-phenyl or-NRos6C02Ross; Ro4 is C,-C4alkyl; Ros is hydrogen, C,-C4alkyl, C2-C6alkenyl, C3-C6alkynyl, C3-C7cyctoalkyl, phenyl or phenyl which is substituted by C1-C4alkyl, C,-C6haloalkyl, C-Caalkoxy, C,-C4haloalkoxy, C2-C6 alkenyl, C3-C6alkynyl, C3-C6alkenyloxy, C3-C6alkynyloxy, halogen, nitro, cyano,-COOH, COOC1-C4alkyl, COOphenyl, C1-C4alkoxy, phenoxy, (C1-C4alkoxy)-C1-C4alkyl, (C1-C4 alkylthio)-C,-C4alkyl, (C,-C4alkylsulfinyl)-C,-C4alkyl, (C,-C4alkylsulfonyl)-C,-C4alkyl, NHS02- C,-C4alkyl, NHS02-phenyl, N (C,-C6alkyl)SO2-C1-C4alkyl, N(C,-C6alkyl)SO2-phenyl, N (C2-C6 alkenyl)SO2-C1-C4alkyl, N(C2-C6alkenyl)SO2-phenyl, N (C3-C6alkynyl) SO2H, N (C3-C6 alkynyl) S02-C,-C4alkyl, N (C3-C6alkynyl)SO2-phenyl, N(C3-C7cycloalkyl)SO2H, N(C3-C7 cycloalkyl)SO2-C1-C4alkyl, N(C3-C7cycloalkyl)SO2-phenyl, N (phenyl)SO2-C1-C4alkyl, N (phenyl)SO2-phenyl, OSO2-C1-C4alkyl, CONR057R058, OSO2-C1-C4haloalkyl, OSO2-phenyl, C1-C4alkylthio, C,-C4haloalkylthio, phenylthio, C,-C4alkylsulfonyl, C,-C4haloalkylsulfonyl, phenyisulfonyl, C,-C4alkylsulfinyl, C,-C4haloalkylsulfinyi, phenylsulfinyl, C,-C4alkylene- phenyl or-NRo6oC02Ross: R06 is hydrogen, C,-C4alkyl, C2-C6alkenyl, C3-C6alkynyl, C3-Ccycloalkyl, phenyl or phenyl which is substituted by C1-C4alkyl, C,-C6haloalkyl, C-C4alkoxy, C,-C4haloalkoxy, C2-C6 alkenyl, C3-C6alkynyl, C3-C6aikenyloxy, C3-C6alkynyloxy, halogen, nitro, cyano,-COOH, COOC,-C4alkyl, COOphenyl, C,-C4alkoxy, phenoxy, (C,-C4alkoxy)-C,-C4alkyl, (C,-C4 alkylthio)-C,-C4alkyl, (C,-C4alkyisulfinyl)-C,-C4alkyl, (C,-Caalkylsulfonyl)-C,-C4alkyl, NHS02- C,-C4aikyl, NHSO2-phenyl, N (C,-. C6alkyl) S02-C,-C4alkyl, N (C,-C6alkyl) S02-phenyl, N (C2-C6 alkenyl) S02-C,-C4alkyl, N (C2-C6alkenyl) SO2-phenyl, N (C3-C6alkynyl) SO2-C,-C4alkyl, N (C3-C6 alkynyl)SO2-phenyl, N(C3-C7cycloalkyl)SO2-C1-C4alkyl, N (C3-C7cycloalkyl) SO2-phenyi, N (phenyl) S02-C,-C4alkyl, N (phenyl) SO2-phenyl, OS02-C,-C4alkyl, CONRo61Roz, OS02-C,- C4 haloalkyl, OS02-phenyl, C,-C4aikylthio, C,-C4hatoalkylthio, phenylthio, C,-C4aikylsulfonyl, C,-C4haloalkylsulfonyl, phenylsulfonyl, C,-C4alkylsulfinyl, C,-C4haloalkylsulfinyl, phenylsulfinyl, C1-C4alkylene-phenyl or -NR064CO2R063; Ro7 is phenyl, substituted phenyl, C,-C4alkyl, C,-Caalkoxy or-NRosRos; ROB and Rog independently of one another are C,-C4alkyl, phenyl or phenyl which is substituted by halogen, nitro, cyano, C1-C4alkyl, C,-C4alkoxy, C,-C4thioalkyl,-C02R, -COR067, C,-C4alkylsulfonyl, C,-C4alkylsulfinyl, C,-C4haloalkyl; or ROB and Rog together form a 5-6-membered ring which may be interrupted by oxygen, NRo65 or S, R015, R031, R043, R048, R052, R056, R060 and Ro64 independently of one another are hydrogen, C,-C4alkyl, C2-C6alkenyl, C3-C6alkynyl or C3-C7cycloalkyl ; R025, R026, R027, R028, R029, R030, R032, R033, R034, R035, R036, R037, R040, R041, R042, R045, R046, R047, R049, R050, R053, R054, R055, R057, R058, R059, R061, R062, R063, R065 and R070 independently of one another are hydrogen, C1-C4alkyl, C2-C6alkenyl, C3-C6alkynyl, C3-C7cycloalkyl, phenyl, or phenyl which is substituted by halogen, nitro, cyano, C,-C4alkoxy, C,- C4haloalkoxy, C,-C4 alkylthio, C,-C4haloalkylthio, C,-C4alkyl or C,-C4haloalkyl; and R36 is C,-C4alkyl, C,-C4haloalkyl, C3-C6alkenyl, C3-C6haloalkenyl, C3-C6alkynyl, C3-C6 haloalkynyl, C3-C6cycfoalkyl or C3-C6cycloalkyl which is substituted by halogen, C1-C4alkyl, C,-C4haloalkyl, C3-C6alkenyl, C3-C6haloalkenyl, C3-C6alkynyl, C3-C6haloalkynyl, C,-C4 alkoxycarbonyl, C,-C4alkylthio, C1-C4alkylsulfinyl, C1-C4alkylsulfonyl, C1-C4haloalkylthio, C1- C4haloalkylsulfinyl, C,-C4haloalkylsulfonyl, C,-C4alkylcarbonyl, di-C,-C4alkylamino, C,- C4alkoxy, C,-C4haloalkoxy, C,-C4alkyl-S (0) 20, C1-C4haloalkyl-S(O)2O or phenyl which for its part may be substituted by halogen, C,-C4alkyl, C,-C4haloalkyl, C3-C6alkenyl, C3-Csalkynyl, cyano, nitro or COOH; and agronomically acceptable salts M and all stereoisomers and tautomers of the compounds of the formula 1.

The compounds of the formula I can be present in different isomeric forms which can be isolated in pure form. The invention therefore also embraces all stereoisomeric forms of the compound of the formula 1. Examples of these isomeric forms are the formulae Ix, Ixx, Ixxx and Ixxxx below, in which Q is the group Q2- 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 and octyl 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. This also appiies, correspondingly, to halogen in combination with other meanings, such as haloalkyl or halophenyl.

Haloalkyl groups preferably have a chain length of from 1 to 8 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 preferably trichloromethyl, difluorochloromethyl, difluoromethyl, trifluoromethyl and dichlorofluoromethyl.

Suitable haloaikenyl 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-trichioropropenyl 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- trifluoropropynyl 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.

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. Aikoxycarbonyl 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-trichioroethoxy; 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. Aikytsutfinyi 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-butylsuffonyl or tert-butylsulfonyt; preferably methylsulfonyi 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 have a chain length of preferably from 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, iso-propylthioethyl, 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 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.

Heterocyclyl is to be understood as meaning ring systems which, in addition to carbon atoms, contain at least one heteroatom, such as nitrogen, oxygen and/or sulfur. They can be saturated or unsaturated. In the context of the present invention, heterocyclyl ring systems may also be substituted. Suitable substituents are, for example, C,-C4alkyl, C,- C4haloalkyl, C,-C4alkoxy, cyano, nitro, C,-C4alkylsulfonyl, C,-C4alkylsulfinyl, C,-C4aikylthio or C3-C6cycloalkyl.

Heterocyclyl may be, for example, furyl, thiophenyl, pyrrolidyl, piperidinyi, morpholinyl, pyridyl, imidazolyl, tetrahydrofuryl, tetrahydropyranyl, dihydrofuryl, dihydropyranyl, isoxazolyl, oxazolyl, isothiazolyl, 1,2,3-thiadiazolyl, 1,2,4-thiadiazolyl, thiazolyl, pyrazolyl, 1,2,4-triazolyl, 1,2,3-triazolyl, tetrazolyl, pyrimidyl, pyrazinyl, sym. or unsym. triazinyl, piperazinyl, oxazolinyl (for example: oxazolidinyl, imidazolinyl, imidazolidinyl, dioxanyl, oxetanyl, in particular 2-oxetanyl, or phthalimidyl.

The invention also embraces the salts M+ which can be formed by the compounds of the formula 1, in particular the compounds of the formula I in which R20, R23, R26 and R30 are hydroxyl, preferably with amines, alkali metal and alkaline earth metal bases or quaternary ammonium bases. Among the alkali metal and alkaline earth metal bases, the hydroxides of lithium, sodium, potassium, magnesium or calcium, in particular those of sodium or potassium, may be especially emphasized as salt formers. Examples of amines suitable for ammonium salt formation are both ammonia and primary, secondary and tertiary C,- C, 8alkylamines, C,-C4hydroxyalkylamines and C2-C4alkoxyalkylamines, 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, methyinonylamine, methylpentadecylamine, methyloctadecylamine, ethylbutylamine, ethylheptylamine, ethyloctylamine, hexylheptyl- amine, hexyloctylamine, dimethylamine, diethylamine, di-n-propylamine, diisopropylamine, di-n-butylamine, di-n-amylamine, diisoamylamine, dihexytamine, diheptylamine, dioctyl- amine, ethanolamine, n-propanolamine, isopropanolamine, N, N-diethanoiamine, 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, propylene- diamine, trimethylamine, triethylamine, tri-n-propylamine, triisopropylamine, tri-n-butylamine, triisobutylamine, tri-sec-butylamine, tri-n-amytamine, methoxyethylamine and ethoxyethylamine; heterocyclic amiines, for example pyridine, quinoline, isoquinoline, morpholine, piperidine, pyrrolidine, indoline, quinuclidine and azepine; primary arylamines, for example anilines, methoxyanilines, ethoxyanilines, o, m, p-toluidines, phenylenediamines, naphthylamines and o, m, p-chloroanilines; but in particular triethylamine, isopropylamine and diisopropylamine. Quaternary ammonium bases which are suitable for salt formation are, for example, [N (Rao, Rbo, Rcoi Rdoi) where Rao,, Rbo,, Ro) and R do, independently of one anotheer are C1-C4alkyl. Further suitable tetraalkylammonium bases with other anions can be obtained, for example, by anion exchange reactions.

Preferred compounds of the formula I correspond to the formula lb in which each R independently is C,-C6alkyl, C,-C6alkoxy, C,-C6haloalkoxy, C,-C6alkylthio, C,-C6- alkylsulfinyl, C,-C6alkylsulfonyl, C,-C6haloalkyl, C,-C6haloalkylthio, C,-C6haloalkylsulfinyl, C,- C6haloalkylsulfonyl, C1-C6alkoxycarbonyl, C,-C6alkylcarbonyl, C,-C6alkylamino, di-C,-C6- alkylamino, C,-C6alkylaminosulfonyl, di-C,-C6alkylaminosulfonyl,-N (R,)-S-R2,-N (R3)-SO-R4, -N (R5)-S02-R6, nitro, cyano, halogen, hydroxyl, amino, or a five-to ten-membered monocyciic 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, where the ring system is either attached directly to the pyridine ring or attached via a C,-C4alkylene group to the pyridine ring, and each ring system may not contain more than 2 oxygen atoms and not more than two sulfur atoms, and the ring system for its part may be mono-, di-or trisubstituted by C,-C6alkyl, C,-C6haloalkyl, C3-C6alkenyl, C3-C6haloalkenyl, C3- C6alkynyl, C3-C6haloalkynyl, C,-Csalkoxy, C,-C6haloalkoxy, C3-C6alkenyloxy, C3- C6alkynyloxy, mercapto, C,-C6alkylthio, C,-C6haloalkylthio, C3-C6alkenylthio, C3- C6haloalkenylthio, C3-C6alkynylthio, C2-Csalkoxyalkylthio, C3-Csacetylalkylthio, C3- C6alkoxycarbonylalkyithio, C2-C4-cyanoalkylthio, C,-C6alkylsulfinyl, C,-C6haloalkylsulfinyl, C,-C6alkylsulfonyl, C,-C6-haloalkylsulfonyl, aminosulfonyl, C,-C2alkylaminosulfonyl, Cz- C4dialkylaminosulfonyl, C,-C3-alkylene-R7, NR8R9, halogen, cyano, nitro, phenyl and benzylthio where phenyl and benzylthio for their part may be substituted on the phenyl ring by C,-C3alkyl, C,-C3haloalkyl, C,-C3alkoxy, C,-C3haloalkoxy, hatogen, cyano or nitro, and where substituents on the nitrogen in the heterocyclic ring are different from halogen; Q is the group Q, in which R20 is hydroxyl, C1-C4alkoxy, C1-C4alkylcarbonyloxy, C1-C4alkoxycarbonyloxy, R21R22N- C (O) O, phenylthio, C1-C4alkylthio, C1-C4alkyl-S(O)2O, (C1-C4alkoxy)2P(O)O, C1-C4alkyl(C1- C4alkoxy)P(O)O, H (C1-C4alkoxy)P(O)O or benzoyloxy; and R2, and R22 independently of one another are hydrogen or C1-C4alkyl; or the group Q2a in which R23 is hydroxyl, C1-C4alkoxy, C1-C4alkylcarbonyloxy, C1-C4alkoxycarbonyloxy, R24R25N-C (O) O, phenylthio, C,-C4alkylthio, C,-C4alkyl-S (0) 20, (C1-C4alkoxy)2P(O)O, C1-C4- alkyl(C,-C4alkoxy)P(O)O, H (C,-C4atkoxy) P (O) O or benzoyloxy; and R24 and R25 independently of one another are hydrogen or C,-C4alkyl; and Y is oxygen, sulfur, a chemical bond or a C1-C4alkylene bridge; or the group Q3 in which R26 is hydroxyl, C1-C4alkoxy, C,-C4alkylcarbonyloxy, C,-C4alkoxycarbonyloxy, R27R28N-C(O)O, phenylthio, C1-C4alkylthio, C1-C4alkyl-S (O)2O, C1-C4-C1-C4- alkyl(C1-C4alkoxy)P(O)O, H (C,-C4alkoxy) P (O) O or benzoyloxy; and R27 and R28 independently of one another are hydrogen or C,-C4aikyl and R29 is hydrogen, C1-C6alkyl, C1-C4alkylcarbonyl, C,-C4alkoxycarbonyl, (C,-C4alkyl) NHCO or (C,-C4aikyl) 2NCO; or the group Q4 in which R30 is hydroxyl, C,-C4alkoxy, C,-C4alkylcarbonyloxy, C,-Caalkoxycarbonyloxy, R31R32N-C(O)O, phenylthio, C1-C4alkylthio, C1-C4alkyl-S(O)2O, (C1-C4alkoxy)2P(O), C1-C4- alkyl (C,-C4alkoxy) P(O)O, H (C,-C4alkoxy) P (O) O or benzoyloxy; and R3, and R32 independently of one another are hydrogen or C,-C4alkyl; R33 and R34 independently of one another are hydrogen, C,-C4alkyl, C2-C6alkenyl, Cz- C6alkynyl, C,-C4-alkoxycarbonyl, C,-C6alkylthio, C,-C6alkylsulfinyl, C,-C6alkylsulfonyl, C,- C4alkyl-NHS (0) 2, C,-C4haloalkyl,-NH-C,-C4alkyl,-N (C,-C4alkyl) 2, C1-C6alkoxy, or phenyl which for its part may be substituted by C,-C4alkyl, C,-C4haloalkyl, C1-C4alkoxy, C,- C4haloalkoxy, C,-C4alkyfcarbonyl, C,-C4alkoxycarbonyl, amino, C,-C4alkylamino, di-C,- C4alkylamino, G,-C6alkylthio, C,-C6-alkylsulfinyl, C,-C6alkylsulfonyl, C,-C4alkyl-S (0) 20, C,- C4haloalkylthio, C,-C4haloalkylsulfinyl, C,-C4haloalkylsulfonyl, C,-C4haloalkyl-S (0) 20, C,- C4alkyl-S (0) 2NH, C,-Caalkyl-S (O)2N(C1-C4-alkyl), COOHCOOH or cyano; or R33 and R34 together form a C2-C6alkylene bridge; and R35 is hydrogen, C,-C4alkyi, C1-c4alkoxycarbonyi or phenyl which for its part may be substituted by C,-C4alkyl, C,-C4haloalkyl, C,-C4alkoxy, C,-C4haloalkoxy, C,-C4alkytcarbonyl, C,-C4alkoxycarbonyl, amino, C,-C4alkylamino, di-C,-C4alkylamino, C,-Caalkylthio, C,-C4- alkylsulfinyl, C,-C4alkylsulfonyl, C,-C4alkyl-S (0) 20, C,-C4haloalkylthio, C,-C4haloalkylsulfinyl, C,-C4hatoalkylsulfonyl, C,-C4hatoalkyl-S (0) 20, C,-C4alkyl-S (0) 2NH, C,-C4alkyl-S (0) 2N (C,- C4-alkyl), halogen, nitro, COOH or cyano; or the group Q5, and also agronomically acceptable salts of these compounds, the other substituents being defined as under formula I in claim 1. Among the compounds of the formula lb, preference is furthermore given to those in which the group -C (O)-Q is located in the 3 position on the pyridine ring, or in which Q is Q2, R23 being, in particular, hydroxyl, Y being a methylene bridge and m being the number 2. Preference is further given to compounds of the formula Ib in which R is C,-C6alkyl or C,-C6haloalkyl.

Preferred compounds of the formula I are characterized in that the group-C (O) Q is in the ortho position to a group R. Preference is furthermore given to compounds of the formula I in which a group R is C,-C6haloalkyl and in the ortho position to the pyridyl nitrogen. Of particular interest are furthermore compounds of the formula I in which the group-C (O) Q is in the 3 position to the pyridyl nitrogen. In the formula 1, p is preferably the number 0. Also to be emphasized are compounds of the formula I in which m is 2 and R is C,-C3alkyl, C,- C3-haloalkyl, C1-C2alkoxymethyl, C1-C2alkythiomethyl, hydroxymethyl, C1- C6alkylcarbonyloxymethyl, benzoyloxymethyl, C,-C4alkoxycarbonyloxymethyl, chlorine, cyano, C,-C3alkoxy, C,-C3haloalkoxy, allyloxy, propargyloxy, C,-Csalkylthio, C,- C3alkylsulfinyl, C,-C3alkylsulfonyl, C,-C3alkylsulfonyloxy, C,-C2alkylsulfinylmethyl or C,- C2alkylsulfonylmethyl. A further group of preferred compounds of the formula I is formed by those compounds in which at least one group R is trifluoromethyl, difluorochloromethyl, pentafluoroethyl or heptafluoro-n-propyl.

Particularly noteworthy compounds of the formula I are those in which Q is a group Q, and R16, R18 and Rig are C,-C3alkyl and R17 is hydrogen, or Q is a group Q2 and Y is-CH2-, -CH2CH2-or oxygen, A is-CH2-and R240, R241, R242 and R243 are each hydrogen, or Q is a group Q3 and R29 is C, C4alkylcarbonyl, C,-C4alkoxycarbonyl or C,-C4alkylaminocarbonyl or di (C,-C2-alkyl)aminocarbonyl, or Q is a group Q4 in which R33, R34 and R35 are C,-C3alkyl. In these noteworthy compounds of the formula 1, R20, R23, R26 and R30 independently of one another are halogen, thiocyanato, C,-C, Zalkoxy, C,-C4alkoxycarbonyl-C,-C2alkoxy, C,-C, 2- alkylthio, C1-C12alkylsulfinyl, C1-C12alkylsulfonyl, C1-C12haloalkylthio, C1-C12haloalkylsulfinyl, C1-C12haloalkylsulfonyl, C1-C12alkenylthio, C2-C12alkenylsulfinyl, C2-C12alkenylsulfonyl, C2-C,2-haloalkenylthio, C2-C, 2haloaikenyisulfinyl, C2-C, 2haloalkenylsulfonyl, C2-CX2alkynylthio, C2-c12alkynylsulfinyls C2-C, 2alkynylsulfonyl, C,-C4alkoxycarbonyl-C,-C2- alkylthio, C,-C4-alkoxycarbonyl-C,-C2alkylsulfinyl, C,-C4alkoxycarbonyl-C,-C2alkylsulfonyl, C,-C4alkyl-S (0) 2NH, C,-C4haloalkyl-S (0) 2NH, C,-C4alkyl-S(O)2O, C1-C18alkylcarbonyloxy, C2-C, 8-alkenylcarbonyloxy, C3-C6cycloalkylcarbonyloxy, C,-C, 2alkoxycarbonyloxy, C,-C, 2- alkylthiocarbonyloxy, C,-C,2alkylthiocarbamoyl, C,-C6alkyl-NH (CS) N (C,-C6alkyl)-NH-, di-C,-C6alkyl-N (CS)N(C1-C6alkyl)-NH-, benzyloxy, benzylthio, benzylsulfinyl, benzylsulfonyl, phenoxy, phenylthio, phenylsulfinyl, phenylsulfonyl, phenylsulfonyloxy or benzoyloxy, where the phenyl groups for their part may in each case be substituted by C,-C4alkyl, C,-C4- haloalkyl, C,-C4alkoxy, C,-C4haloalkoxy, C,-C4alkylcarbonyl, C,-C4alkoxycarbonyl, C,-C4- alkylamino, di-C,-C4alkylamino, C,-C4alkylthio, C,-C4alkylsulfinyl, C,-C4alkylsulfonyl, C,-C4- alkyl-S(O)2O, C1-C4haloalkylthio, C,-C4haloalkylsulfinyl, C,-C4haloalkylsulfonyl, C,-C4- haloalkyl-S (0) 20, C,-C4alkyl-S (0) 2NH, C,-C4alkyl-S (0) 2N (C,-Caalkyl), halogen, nitro or cyano, or R20, R23, R26 and R30 independently of one another are thienylcarbonyloxy or furylcarbonyloxy which for their part may be substituted by methyl or halogen, or are pyridylcarbonyloxy which for its part may be substituted as stated in claim 1, or R20 is R37R38N, R71R72NNH-, R21R22NC(O)O- or R73R74NC(O)NH-; or R23 is R44R45N, R75R76NNH-, R46R47NC(O)O-(O)O- or R77R78NC(O)NH-; or R26 is R53R54N, R79R8oNNH-, Rs5Rs6NC (0) 0- or R8, R82NC (O) NH-; or R30 is R62R63N, R83R84NNH-, R64R65NC (O)O- R85R86NC(O)NH-. Very particuiarly preferably, R2o, R23, R26 or R3o are hydroxyl or O'M.

A further preferred group is formed by those compounds of the formula I in which Q is a group Q5, R36 is C,-C4alkyl, C,-C4haloalkyl or cyclopropyl and Roi is C,-C6alkyl, C,-C4- alkoxycarbonylmethyl, C3-Cealkenyl, is benzyl or phenyl substituted by methyl, halogen, trifluoromethyl, methoxy, and at least one group R is trifluoromethyl, difluorochloromethyl, pentafluoroethyl or heptafluoro-n-propyl located in the ortho position to the pyridyl nitrogen.

The process according to the invention for preparing compounds of the formula I in which R and m are as defined under formula 1; p is 0 and Q is the group is carried out analogously to known processes (for example those described in WO 97/46530 and EP-A-0 353 187) and comprises a) reacting a compound of the formula 11 in which R and m are as defined under formula I and X is a leaving group, for example halogen, in an inert organic solvent in the presence of a base with compounds of the formula III, IV, V or VI in which R, 6, R", R, B, R,g, R29, R33, R34, R35, R24o, R243, R242, R241, A and Y are as defined under formula I to give the compounds of the formula VII, VIII, IX or X and then isomerizing these compounds, for example in the presence of a base and a catalytic amount of dimethylaminopyridine (DMAP) or a source of cyanide; or b) reacting a compound of the formula XI in which R and m are as defined under formula I with compounds of the formula lil, IV, V or vi in which R16, R17, R18, R19, R29, R33, R34, R35, R240, R243, R242, R241, A and Y are as defined under formula I in an inert organic solvent in the presence of a base and a coupling agent to give a compound of the formula VII, VIII, IX or X and then isomerizing these compounds, for example as described under route a).

Compounds of the formula I in which R20, R23, R26 and R30 are different from hydroxyl or halogen can be prepared by converesion methods which are generally known from the literature, for example acyclations or carbamoylations with appropriate acyl chlorides, from compounds in which R20, R23, R26 or Rsois hydroxy ! in the presence of a suitable base, or they can be prepared by nucleophilic substitution reactions on chlorides of the formula I in which R20, R23, R26 or R30 is halogen, which are likewise obtainable by known processes by reaction with a chlorinating agent, such as phosgene, thionyl chloride or oxalyl chloride.

Here, for example, suitably substituted amines, or hydroxylamines directly, or alkyfsulfonamides, mercaptans, thiophenols, phenols, Ar,-NH2 or Ar,-SH, are employed 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 R20, R23, R26 or R30 comprise thio groups can be oxidized analogously to known standard processes, for example using peracids, for example meta-chloroperbenzoic acid (m-CPBA) or peracetic acid, to give the corresponding sulfones and sulfoxides of the formula 1. Here, the degree of oxidation at the sulfur atom (SO-or S02-) can be controlled by the amount of oxidizing agent.

The process according to the invention for preparing compounds of the formula I in which R and m are as defined under formula I and Q is a group in which Z is sulfur, q is 0 and R36 and Roi are as defined under formula I is carried out analogously to known processes (for example those described in WO 97/43270) and comprises converting a compound of the formula XII in which R36, R and m are as defined under formula I in the presence of a base, carbon disulfide and an alkylating agent of the formula Xlil Roi-Xi (XlIl), in which Ro, is as defined under formula I and X, is a leaving group, for example halogen or sulfonate, into the compound of the formula XIV in which Z is sulfur and R, Roi, R36 and m are as defined above and then cyclizing this compound using hydroxylamine hydrochloride, in the presence or absence of a solvent, in the presence of a base to give the compounds of the formulae in which Z is sulfur and R, R36, Roi and m are as defined above, and then oxidizing these compounds with an oxidizing agent, for example meta-chloroperbenzoic acid (m-CPBA).

The isomers of the formulae le and If can be separated using column chromatography and a suitable mobile phase and then purified.

The preparation of the compounds of the formula I in which p is 0 is illustrated in more detail in the reaction schemes 1 and 2 below. Reaction scheme 1 Route a): 0 fy X Base e. g. (CzHs) 3N, (R) m x + III, IV, V or VI VII, VIII, IX) o X w Solvent e. g. CH2Ci2, 0-1 1 0°C I I Isomerization: ° Base e. g. (C2H5) 3N, /n KCN cat. I Routeb): 0 ß Base e. g. (C2H) N, coupiing (R)OH IIi) IV, V or VI VII, VIIi, IX, or X (R) m I agent e. g. \N + I p N + CI CH3 Solvent e. g. CH2C12. 0-110°C Isomerization : ° Base e. g. (C2H5) 3N, Q 0 (R) m KCNcat t N W N According to this reaction scheme, the compounds of the formula I with the group Q, in which R20 is hydroxyl, the compounds of the formula I with the group Q2 in which R23 is hydroxyl, the compounds of the formula I with the group Q3 in which R26 is hydroxyl and the compounds of the formula I with the group Q4 in which R30 is hydroxyl can preferably be prepared.

Reaction scheme 2 00 0 0 0 t K2COCS2, Ro-X, O O XIII Rm/ R (m) H2 solvent e. g. DMF, or p 36 N KF/AI/CS2, Ro1-X, S R 0, o N XIII N S R oSR m Solvent e. g. CH3CN, or xiv xii NaH/CS2'Rol-xl, Xlil Solvent e. g. DMSO NR (R) z--R o, O e. g. m-CPBA NH20H HCI, base e.g. < R J+N p wN and Ras N--1 NaOAc/C2H50H N R 0/O Solvent e. g. CH2CI2 36 J (R)m J if Z=S (R)m O R o1 S Z-R o, 36'N /O N 0 (R)m- J N If if Z = SO-or S02 For preparing the compounds of the formula I in which Q is the groups Q, to Q4 and R20, R23, R26 and R3o are hydroxyl, in accordance with reaction scheme 1, route a), the carboxylic acid derivatives of the formula 11 in which X is a leaving group, for example 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 dicyclohexylcarbodiimide (DCC) and the corresponding carboxylic acid) or (formed from N-ethyl-N'- (3-dimethylaminopropyl) carbodiimide (EDC) and the corresponding carboxylic acid) are employed. These compounds are reacted in an inert organic solvent, for example 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, for example an alkylamine, for example triethylamine, an aromatic amine, for example pyridine or 4-dimethylaminopyridine (DMAP), with the dione derivatives of the formula III, IV, V or VI to give the isomeric enol ethers of the formulae VII, VIII, IX and X. This esterification is carried out at temperatures of from 0°C to 110°C.

The isomerization of the ester derivatives of the formulae VII, VIII, IX and X to the dione derivatives of the formula I (in which R20, R23, R26 and R30 are hydroxyl) can be carried out, for example, analogously to EP 369 803 in the presence of a base, for example an alkylamine, for example triethylamine, a carbonate, for example potassium carbonate, and a catalytic amount of DMAP or a cyanide source, for example acetone cyanohydrin or potassium cyanide.

According to reaction scheme 1, route b), the desired diones of the formula I (in which R2o, R23, R26 and R3o are hydroxyl) can be obtained, for example, in analogy to Chem. Lett.

1975,1045 by esterifying the carboxylic acids of the formula XI with the dione derivatives of the formula III, IV. V or VI in an inert solvent, for example a halogenated hydrocarbon, for example dichloromethane, a nitrile, for example acetonitrile, or an aromatic hydrocarbon, for example toluene, in the presence of a base, for example an alkylamine, for example triethylamine, and a coupling agent, for example 2-chloro-1-methylpyridinium iodide.

Depending on the solvent used, this esterification is carried out at temperatures of from 0°C to 110°C, affording initially, as described under route a), the isomeric ester of the formula I 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 cyanide source, to give the desired dione derivative of the formula I (R20, R23, R26 and R3o are hydroxyl).

The preparation of the compounds of the formula I in which Q is the group Q5 can be carried out in accordance with reaction scheme 2 by reacting the P-diketone derivative of the formula XII, for example in anaiogy to Synthesis 1991,301; ibid. 1988,793; or Tetrahedron 32,3055 (1976) with carbon disulfide in the presence of a base, for example a carbonate, for example potassium carbonate, a metal hydride, for example sodium hydride, or potassium fluoride on aluminium, and an alkylating agent of the formula XIII in which X, is a leaving group, for example halogen, for example iodine, bromine and in particular chlorine, R250SO20-, CH3S020-or This reaction is preferably carried out in the presence of a solvent, for example an amide, for example N, N- dimethylformamide (DMF), a sulfoxide, for example dimethylsulfoxide (DMSO), or a nitrile, for example acetonitrile. The ketene thioacetal of the formula XIV which is formed is cyclized with the aid of hydroxylamine hydrochloride in the presence of a base, for example sodium acetate, in a solvent, for example an alcool, for example ethanol, or an ether, for example tetrahydrofuran, to give the compound of the formula le in which Z is sulfur. This cyclization reaction is carried out at temperatures of from 0°C to 100°C. If appropriate, compounds of the formulae le and If (Z is sulfur) can be oxidized analogously to known standard processes, for example with peracids, for example meta-chloroperbenzoic acid (m- CPBA) or peracetic acid, to give the corresponding sulfones and sulfoxides of the formulae le and If (Z = SO-or S02-). Here, the degree of oxidation at the sulfur atom (Z = SO-or S02-) can be controlled by the amount of oxidizing agent.

Oxidations to the compounds of the formulae le and If (Z is SO-or SOz-) are carried out as described, for example, in H. O. House,"Modern Synthetic Reactions"W. A. Benjamin, Inc., Menlo Park, California, 1972, pages 334-335 and 353-354.

The activated carboxytic acid derivatives of the formula li in reaction scheme 1 (route a) in which X is a leaving group, for example halogen, for example bromine, iodine or in particular chlorine, can be prepared by known standard processes, as described, for example, in C. Ferri"Reaktionen der organischen Synthese" [Reactions of Organic Synthesis], Georg Thieme Verlag, Stuttgart, 1978, page 461 ff. This is shown in reaction scheme 3 below.

Reaction scheme 3 According to reaction scheme 3, the compounds of the formula 11 (X=leaving group) or 11 (X=halogen) are prepared, for example, by employing a haiogenating agent, for example a thionyl halide, for example thionyl chloride or thionyl bromide; a phosphorus halide or phosphorus oxyhalide, for example phosphorus pentachloride or phosphorus oxychloride or phosphorus pentabromide or phosphoryl bromide; or an oxalyl halide, for example oxalyl chloride, or by employing a reagent for the formation of activated esters, for example N, N'- dicyclohexylcarbodiimide (DCC) or N-ethyl-N'- (3-dimethylaminopropyi) carbodiimide (EDC) of the formula X. For the compound of the formula X used as halogenating agents, X is a leaving group, for example halogen, for example fluorine, bromine or iodine and in particular chlorine, and W, is, for example, PCIz, SOCI, SOBr or CICOCO.

The reaction is carried out in the presence or absence of an inert organic solvent, for example in aliphatic, halogenated aliphatic, aromatic or halogenated aromatic hydrocarbons, for example n-hexane, benzene, toluene, xylenes, dichioromethane, 1,2- dichloroethane or chlorobenzene, at reaction temperatures in the range of from-20°C to the reflux temperature of the reaction mixture, preferably at 40-150°C, and in the presence of a catalytic amount of N, N-dimethylformamide. Such reactions are generally known and described in the literature in various variations with respect to the leaving group X.

The compounds of the formulae III, IV, V and VI are known and can be prepared analogously to the methods described, for example, in WO 92/0737, DE-A-3818958, EP- A-0 338 992 and DE-A-3902818.

The compounds of the formula XII in reaction scheme 2 can be obtained by standard processes, for example from the corresponding compounds of the formula 11 in which R and m are as defined above and X is a leaving group, for example halogen, for example via Claisen condensation, or from the compounds of the formula 11 by reaction with a ketocarboxylic acid salt of the formula XV in which R36 is as defined under formula I and M+ is an alkali metal ion (cf., for example, WO 96/26192).

The compounds of the formulae 11 and Xi are known and can be prepared analogously to the methods described, for example, in WO 97/46530, EP-A-0 353 187, Heterocycles, 48, 779 (1998), Heterocycles, 46,129 (1997), or Tetrahedron Letters, 1749 (1998).

For preparing all other compounds of the formula I functionalized according to the definition of (R) m, there is a large number of known standard processes available, for example alkylation, halogenation, acylation, amidation, oximation, oxidation and reduction, and the choice of the suitable preparation processes depends on the properties (reactivities) of the substituents in the intermediates in question.

All further compounds originating from the scope of the formula I can be prepared in a simple manner, taking into account the chemicat properties of the pyridyl or Q moiety.

The end products of the formula I can be isolated in a customary manner by concentration or evaporation of the solvent and be purified by recrystallization or trituration of the solid residue in solvents in which they are only sparingly soluble, such as ethers, aromatic hydrocarbons or chlorinated hydrocarbons, by distillation or by means of column chromatography and a suitable mobile phase.

Furthermore, it is known to the person skilled in the art in which order certain reactions have to be carried out advantageously to avoid possible side reactions. Unless a targeted synthesis is carried out for isolating pure isomers, the product may be obtained as a mixture of two or more isomers. The isomers can be separated by methods known per se.

Compounds of the formula I in which p is 1, i. e. the corresponding N-oxides of the formula 1, can be prepared by reacting a compound of the formula I in which p is 0 with a suitable oxidizing agent, for example with the H202 urea adduct, in the presence of an acid anhydride, for example trifluoroacetic anhydride. This reaction sequence is demonstrated using the example of group Q2 below: R 2s R 23 R 240 Oxidizing agent R //e. g. H202. H2NCONH2 (R) m A (R) IM-0 y Y \NJ Solvent R 241/+R 243 e. g CH2C12 ° R 242 R 242 "242 Compounds of the formula I in which R in the ortho position to the pyridine nitrogen is 1-chloro-C,-C2alkyl, 1-hydroxy-C,-C2alkyl, 1-(C,-C6alkylcarbonyloxy)-C,-C2alkyl, 1- benzoyloxy-C,-C2alkyl, 1-(C,-C4alkoxycarbonyloxy)-C,-C2alkyl, 1-(C,-C4alkylthio)-C,-C2alkyl, 1- (C,-C4-alkylsulfinyl)-C,-C2alkyl, 1- (C,-C4alkylsulfonyl)-C,-C2alkyl, 1-thiocyanato-C,-C2alkyl, 1-cyano-C,-C2alkyl, can also be prepared, for example, by heating an N-oxide of the formula I under known reaction conditions, for example in the presence of tosyl chloride (see, for example, Parham, W. E.; Sloan, K. B.; Reddy, K. R.; Olson, P. E.; J Org Chem 1973,38,927) or in the presence of an acid anhydride (see, for example, Konno, K.; Hashimoto, K.; Shirahama, H.; Matsumoto, T.; Heterocycles 1986,24,2169), followed, if appropriate, by subsequent conversion.

The compounds of the formula XXlla are synthesized analogously to known processes, for example those mentioned in Heterocycles, 46,129 (1997) or Helvetica Chimica Acta 71, 596 (1988), and comprises either a) acylating a compound of the formula XVI in which Rsci is hydrogen or C,-C6alkyl; R40, is hydrogen, C,-C6alkyi, C2-C6alkenyl, C3-C6cycloalkyl, C1-C6alkoxy, C1-C6alkylthio, C1- C6alkylsulfinyl, C1-C6haloalkyl, 1- (C,-C6alkylcarbonyloxy)-C,-C6alkyl, 1- (C,-C6alkylthio)-C,- C6-alkyl, 1-(C,-C6alkylsulfinyl)-C,-C6alkyl, 1-(C,-C6alkylsulfonyl)-C,-C6alkyl, 1-thiocyanato-C,- C6-alkyl, 1-cyano-C1-C6alkyl, phenyl, where the phenyl groups may be mono-or polysubstituted by halogen, methyl, ethyl, trifluoromethyl, methoxy or nitro, or is 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, where the ring system is either attached directly or via a C,- C4alkylene group to the double bond, and each ring system may not contain more than 2 oxygen atoms and not more than two sulfur atoms and the ring system for its part may be mono-, di-or trisubstituted by C,-C6alkyl, C,-C6haloalkyl, C3-C6alkenyl, C3-C6haloalkenyl, C3- C6aikynyl, C3. C6haloalkynyl, C,-C6alkoxy, C,-C6haloalkoxy, C3-C6alkenyloxy, C3- C6aikynyloxy, mercapto, C,-C6alkylthio, C,-C6haloalkylthio, C3-C6alkenylthio, C3- C6haioalkenylthio, C3-C6alkynylthio, Cz-Csaikoxyatkytthio, C3-Csacetylalkylthio, C3- C6alkoxycarbonylalkylthio, C2-C4cyanoalkylthio, C,-C6alkylsulfinyl, C,-C6haloalkyisulfinyl, C,- C6alkylsulfonyl, C,-C6haloalkylsulfonyl, aminosulfonyl, C1-C2alkylaminosulfonyl, C2- C4dialkylaminosulfonyl, C,-C3alkylene-RB7, NReBR89, hatogen, cyano, nitro, phenyl and benzylthio, where phenyl and benzylthio for their part may be substituted on the phenyl ring by C,-C3alkyl, C,-C3haloalkyl, C,-C3alkoxy, C,-C3-haloalkoxy, halogen, cyano or nitro and where substituents on nitrogen in the heterocyclic ring are different from halogen; R87 is C,-C3alkoxy, C2-C4alkoxycarbonyl, C1-C3alkylthio, C1-C3alkylsulfinyl, C1-C3alkylsulfonyl or phenyl, where phenyt for its part may be substituted by C,-C3alkyl, C,-C3haloalkyl, Cl-C3- alkoxy, C,-C3haloalkoxy, halogen, cyano or nitro; R88 is hydrogen or C,-C6alkyl and R89 is C,-C6alkyl or C,-C6alkoxy; with a compound of the formula XVII in which R5ol is C,-C6haloaikyl and X2 is O (CO) Rso, or halogen to give the compound of the formula XVIII in which R30"R40"Rso1 and R, 4 are as defined above, in the presence of a base, for example an aromatic amine, for example pyridine, and subsequently replacing the alkoxy group by the amino group using ammonia in an organic solvent, for example a halogenated hydrocarbon, for example dichloromethane, or a nitrile, for example acetonitrite. The resulting compound of the formula XIX is subsequently condensed with a compound of the formula XX in which R20, is C,-C6alkyl, C2-C6alkenyl, C2-C6haloalkenyl, C2-C6alkynyl, C2-C6-haloalkynyl, C3-C6cycloalkyl, C,-C6haloalkyl, 1- (C,-C6alkylcarbonyloxy)-C,-C6alkyl, 1- (C,-C6alkylthio)-C,- C6alkyl,1- (C,-C6alkylsulfinyl)-C,-C6alkyl, 1- (C,-C6alkylsulfonyl)-C,-C6alkyl, 1-thiocyanato-C,- C6alkyl, 1-cyano-C,-C6alkyl, C,-C6alkoxy-C,-C6alkyl, C1-C6alkoxycarbonyl-C1-C6alkoxy, C,- C6alkylthio-C,-C6alkoxy, phenyl, benzyl, phenoxy, phenylthio, phenylsulfinyl, phenylsulfonyl, benzylthio, benzylsulfinyl or benzylsulfonyl, where the phenyl grog s may be mono-or polysubstituted at least by halogen, methyl, ethyl, trifluoromethyl, methoxy or nitro, or is 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, where the ring system is attached either directly or via a C,- C4-aikylene group and each ring system may not contain more than 2 oxygen atoms and not more than two sulfur atoms, and the ring system for its part may be mono-, di-or trisubstituted by C,-C6alkyl, C,-C6haloalkyl, C3-C6alkenyl, Cs-C6haloalkenyl, C3-C6alkynyl, C3-C6hatoalkynyl, C,-Csalkoxy, C,-C6haloalkoxy, C3-C6alkenyloxy, C3-C6alkynyioxy, mercapto, C,-C6alkylthio, C,-C6haloalkylthio, C3-C6alkenylthio, C3-C6haloalkenylthio, C3- C6alkynylthio, C2-C5alkoxyalkylthio, C3-CSacetylalkylthio, C3-Csalkoxycarbonylalkylthio, C2- C4cyanoalkylthio, C,-C6alkylsulfinyl, C,-C6haloalkylsulfinyl, C,-C6alkylsulfonyl, C,- C6haloalkylsulfonyl, aminosulfonyl, C1-C2alkylaminosulfonyl, C2-C4dialkylaminosulfonyl, C,- C3-Rgo, NR91R92, halogen, cyano, nitro, phenyl and benzylthio, where phenyl and benzylthio for their part may be substituted on the phenyl ring by C,-C3alkyl, C,-C3haloalkyl, C,- C3alkoxy, C,-C3-haloalkoxy, halogen, cyano or nitro, and where substituents on nitrogen in the heterocyclic ring are different from halogen; R9o is C,-C3alkoxy, C2-C4alkoxycarbonyl, C,-C3alkylthio, C,-C3alkylsulfinyl, C,-C3alkylsulfonyl or phenyl, where phenyl for its part may be substituted by C,-C3-alkyl, C,-C3haloalkyl, C,-C3- alkoxy, C1-C3haloalkoxy, halogen, cyano or nitro; Rgt is hydrogen or Ci-Ceatky) and R92 is C1-C6alkyl or Ci-Cgatkoxy and Ri4 is as defined above, and the resulting compound of the formula XXIa is subsequently hydrolyse to give the compound of the formula XXlla in which R201, R301, R401 and Rsot are as defined above, or b) condensing a compound of the formula XXIII in which R, 4 is as defined above with a compound of the formula XXIV and chlorinating the resulting compound of the formula XXV in which Rsoi. R4oi and R50 are as defined above and Ri4 is C,-C4alkyl to give compounds of the formula XXVI in which R301, R401, R501 and R14 are as defined above (using, for example, POCI3), and subsequently reacting this compound with a nucleophile of the formula XXVII Z-Riso (XXVII) In which Z is SH, OH or amino and Rise is C1-C6alkyl, C3-Ceatkenyt, C3-C6halogenalkenyl, C3. C6alkynyl, C3-C6haloalkynyl, C,-C6alkylsulfonyl, C,-C6haloalkyl, phenyl, benzyl, where the phenyl and benzyl groups for their part may be substituted by Ct-C3alkyl, d-Cshatoatkyt, Ct C3alkoxy, C,-C3haloalkoxy, haiogen, cyano or nitro, is C,-C4alkoxy-C,-C4alkyl or Ci-C4- alkylthio-C1-C4alkyl, C1-C4alkylsulfinyl-C1-C4alkyl, C1-C4alkylsulfonyl-C1-C4alkyl, or 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 each ring system may not contain more than 2 oxygen atoms and not more than two sulfur atoms, and the ring system for its part may be mono-, di-or trisubstituted by C,-C6alkyl, C,-Cehaloalkyl, C3-C6alkenyl, C3-C6haloalkenyl, C3-C6- alkynyl, C3-C6haloalkynyl, C,-C6alkoxy, C,-C6haloalkoxy, C3-C6alkenyloxy, C3-Csalkynyloxy, mercapto, C,-C6alkylthio, C,-C6haloalkylthio, C3-C6alkenylthio, C3-C6haloalkenylthio, C3-C6- alkynylthio, C2-Csalkoxyalkylthio, C3-C5acetylalkylthio, C3-C6alkoxycarbonylalkylthio, C2-C4- cyanoalkylthio, C,-C6alkylsulfinyl, C,-C6haloalkylsulfinyl, C,-C6alkylsulfonyl, C,-C6- haloalkylsulfonyl, aminosulfonyl, C,-C2alkylaminosulfonyl, C2-C4dialkylaminosulfonyl, C,-C3- alkylene-R93, NR94R95, halogen, cyano, nitro, phenyl and benzylthio, where phenyl and benzylthio for their part may be substituted on the phenyl ring by Ct-C3alkyl, Ct-C3-haloalkyl, Ct-C3alkoxy, C,-C3haloalkoxy, halogen, cyano or nitro, and where substituents on nitrogen in the heterocyclic ring are different from halogen; R93 is C :-C3alkoxy, C2-C4alkoxyzarbonyl, C,-C3alkylthio, C,-C3alkylsulfinyl, C,-C3alkylsulfonyl or phenyl, where phenyl for its part may be substituted by C,-C3alkyl, C,-C3haloalkyl, C,-C3- alkoxy, C1-C3haloalkoxy, halogen, cyano or nitro; R94 is hydrogen or C,-C6alkyl and R95 is C1-C6alkyl or C,-C6alkoxy; in the presence of a base to give compounds of the formula XXIb in which R14, Rlso, R301, R40, and Rso, are as defined above, and subsequently hydrolysing the resulting compound to give the compound of the formula XXIIb in which R1so, R30"R40, and Rso, are as defined.

Compounds of the formula XXlb in which Rise is fluorine are prepared by reacting a compound of the formula XXVI in the presence of a polar aprotic solvent, for example acetonitrile, dimethylformamide or sulfolane, with potassium fluoride in the presence or absence of a catalytic amount of 18-crown-6. Compounds of the formula XXIc in which Rise 5o is hydrogen are preparerd by reducing the chlorine group in the formula XXVI, for example using hydrogen in the presence of a suitable metal catalyst or using ammonium formate in a suitable solvent. The preparation of the compounds of the formula XXlla, or XXllb and XXIIc is illustrated in more detail in the reaction schemes 4 and 5 below.

Reaction scheme 4 R 0 o, Acylation: Substitution R Q R, a R 501 NH3 R 30, R so, 'Solvent R XIX XVI R°' XVIII e. g CH3CN o ° XViI 20-50°C Base Solvent Cyclization 201 Solvent XX golvent e. g. CH2CI2 -20-50°C e. g. toluene 20-150 OC 0 R 201 8 tR 201 HO N 1) Hydrolysis R 140 IN XXlla W XXIa \ LiOH R R R 301 R 501 MEOH/H20 R 20-80°C °, Reaction scheme 5 : OH 9 HOHydrolysis N IN R so, LiOH R, \ R so MeOH/H20 R zou XXllc 20-80°C XXlc Reduction e. g. MeOH/NH4HCO2 MeOH R3o, O OH O CI OR14 Cyclization : R 0/N Chlorination R4 N IN R p \ e. g. POCI3 R \ R XXIII R so R so 3°'S° 1 1\ R 20-150°C R40 v NHZ aoi XXIV Base XXV Z-R, SO XXVII e. g. NaOMe Base Solvent e. g. K2CO3 Substitution e. g. MeOH Solvent 20-150°C e. g. DMF s r -20-150 °C 0 ZR 150 0 ZRiso 1) Hydrolysis HO N R 140 COOH R 30 ; R so, MeOH/H20 R 301 R 501 R 20-80°C R 4o1 XXIb XX XX For preparing all other compounds of the formula I which are functionalized according to the definition of R20, (Rise) to Rsci, a large number of known standard processes is suitable, for example alkylation, halogenation, acylation, amidation, oximation, oxidation and reduction, the choice of the suitable preparation processes depending on the properties (reactivities) of the substituents in the intermediates in question.

The novel compounds of the formula Hb in which Rf is trifluoromefhyl, difluorochloromethyl, pentafluoroethyl, heptafluoro-n-propyl or trichloromethyl, Rx, is C,-C6alkyl and Q and R are as defined under formula I can be prepared by generally known processes via 3-alkoxycarbonyl-4-perhaloalkylpyridine N-oxides of the formula XXVIII according to reaction scheme 5 by preparing, using suitable chlorination conditions and separation processes, the 6-chloro-4-haloalkyl-3-nicotinic esters of the formula XXX and then converting these compounds with a nucleophile of the formula XXXI Z01-R151 (XXXI) in which Zo, is SH, hydroxyl, halogen or amino and R1s1 is hydrogen, C,-C6alkyl, C3-C6- alkenyl, C3-C6haioalkenyl, C3-C6alkynyl, halogen, C3-C6haloalkynyl, C,-C6alkylsulfonyl, C,- C6-haloalkyl, phenyl, benzyl, where the phenyl and benzyl groups for their part may be substituted by C,-C3alkyl, C,-C3hatoalkyl, C,-C3alkoxy, C,-C3haloalkoxy, halogen, cyano or nitro, is C,-C4alkoxy-C,-Caalkyl or C1-C4alkylthio-C1-C4alkyl, C,-C4alkylsulfinyl-C,-C4alkyl, C,-C4alkylsulfonyl-C,-C4alkyl, or 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 each ring system may not contain more than 2 oxygen atoms and not more than two sulfur atoms, and the ring system for its part may be mono-, di-or trisubstituted by C,-C6alkyl, C,-C6haloalkyl, C3-C6alkenyl, C3-C6haloalkenyl, C3-C6alkynyl, C3-C6-haloalkynyl, C,-C6alkoxy, C,-C6haloalkoxy, C3-C6alkenyloxy, C3-C6alkynyloxy, mercapto, C,-C6alkylthio, C,-C6haloalkylthio, C3-C6alkenylthio, C3-C6haloalkenylthio, C3-C6alkynylthio, C2-Csalkoxy- alkylthio, C3-Csacetylalkylthio, C3-C6alkoxycarbonylalkylthio, C2-C4cyanoalkylthio, C,-C6- alkylsulfinyl, C,-C6haloalkytsulfinyl, C,-C6alkylsulfonyl, C,-C6haloalkylsulfonyl, aminosulfonyl, C,-Czalkylaminosulfonyl, C2-C4dialkylaminosulfonyl, C,-C3alkylene-R, NRg7R98, halogen, cyano, nitro, phenyl or benzylthio, where phenyl and benzylthio for their part may be substituted on the phenyl ring by C1-C3alkyl, C1-C3haloalkyl, C1-C3alkoxy, C1-C3-haloalkoxy, halogen, cyano or nitro, R96 is C,-C3alkoxy, C2-C4alkoxycarbonyl, C-C3alkytthio, C,-C3alkylsutfinyl, C,-C3alkylsutfonyl or phenyl, where phenyl for its part may be substituted by C,-C3alkyl, C,-C3haloalkyl, C,-C3- alkoxy, C,-C3haloalkoxy, halogen, cyano or nitro; R97 is hydrogen or C,-C6alkyl and R9B S C,-C6alkyl or C,-C6alkoxy; and where substituents on nitrogen in the heterocyclic ring are different from halogen, using reaction processses which are generally known to the person skilled in the art, into the 6- substituted 4-perhaloalkylnicotinic acids of the formula XXXII and their subsequent products of the formulae llb and 1b as described in reaction scheme 1. This is shown in reaction scheme 6 below.

Reaction scheme 6: Rf p) KOWH20 Rt O 2) (COCI) z 3) Conversion 0"Rx, reactions I R'si XN RISIZOXN' ' A HZ. R Ilb 1) Zu,'R, s, XXXI 2) if appropriate oxidation atS Rf 0 ?'9 rif O Ru HZpZ, urea IY POCIiRX N XXVIII (CF3CO) 2 0 Ci XXX 0 1) KOH/H20 2) (COCI) 2 3) Conversion reactions i Rf O Rf 0 1) Zol-Rlsl XXX' J-J R, s, Zo, N 2) if apprapriateI N itb dation lob au S According to this reaction scheme, it is preferably possible to prepare the compounds of the formula I with the group Q, in which R2o is hydroxyl, the compounds of the formula I with the group Q2 in which R23 is hydroxyl, the compounds of the formula I with the group Q3 in which R26 is hydroxyl and the compounds of the formula I with the group Q4 in which Rao is hydroxyl.

6-substituted 2-haloalkylnicotinic acid compounds of the formula Ic can be prepared, for example, from the corresponding 2-haloalkyl-3-alkoxycarbonyl-2-pyridines XXXIII in which Rf is trifluoromethyl, difluorochloromethyl, pentafluoroethyl, heptafluoro-n-propyl or trichloromethyl and R, x is C,-C6alkyl and R is as defined under formula 1, by hydrolysis into the corresponding carboxylic acids and their subsequent activation, for example by conversion into an acyl halide (llc). (Reaction scheme 7).

Reaction scheme 7: 0 0 0 R Coupling R /zRxX 1) KOH/H20 <CI reactlon <Q ZO1-III I 1- ZD, N Rf XXXIII llC Ic Their precursors of the formulae XXXllla, XXXlllb, XXXllic, XXXllid, XXXllle, XXXlllf, XXXIIIg and XXXIIIh are likewise accessible by conversion processes known to the person skilled in the art (reaction scheme 7). 2-Trifluoromethyl-3-ethoxycarbonyl-2-pyridone (formula XXXllla in which R is hydrogen, Rx is ethyl and Rf is trifluoromethyl) in particular is known from Org. Process Research & Development, 1,370 (1997). hou RR ORx R R, x R x R<O thionatingagent g 590 alkyiating agent XoRx Rf P2s5 or base I Lawesson's S H Rf inert solvent RSS N Rf XXXllla reagent XXXlllb XXXllic R, 5, SH/base/ hatogenating agent or RSSalkali 0-220 C e_g. POCI3 0'rf appropriate oxidizing agent e. g. inert oxidation at S m-CI-pBA, Na104 with or PhOP (o) CI2 solventw without solvent O O Rx I O Rx \R'X RsoH/base R i R i i orRts, O alkaii Hal N Rf '_Rf Hal N Rf metal sait/R, 5, O N Rf R5s (O) mo1 N Rf inertsolvent XXXllld XXXllle XXXlllf (C,-C6-Alkyl) 4Sn or e. g. KCN inertsolvent Grignard reagent (C,-C6-alkyl-MgHal) O 0 k ! ! \ R R fr° X"o Alkyl-C,-C6 N-'Rt NC N Rf XXXIIlg XXXlllh Reaction scheme 8 (intermediates of the formulae XXXllla-XXXlllh) Intermediates of the formulae XXXllla to XXXIIIH can be obtained by reacting, for example for preparing a 6-halo derivative of the formula XXXllid, a pyridone of the formula XXXllla (preparation according to Org. Process Research & Development, 1,370 (1997) or scheme 8) with a halogenating agent, for example phosphorus oxychloride, phosphorus oxybromide or phenyl dichlorophosphate, in the presence or absence of added base, such as a dialkylaniline, in the presence or absence of solvent, if desired in a pressure vessel, at temperatures between 0 and 220°C (preferably 60-200°C). It is known to the person skilled in the art how to convert chloro derivatives by nucleophilic substitution, for example using an alkali metal iodide in an inert solvent into the corresponding iodides, or using gaseous hydrobromic acid in lower carboxylic acids, for example conc. acetic acid, into the corresponding bromo derivatives (for example according to US-A-3,974,166) or using alkali metal fluoride in a dipolar solvent, such as sulfolane, into the corresponding fluoro derivatives.

The compound of the formula XXXllle can be prepared by reacting a halo derivative of the formula XXXllld obtained as described above with an alcohol of the formula R, 5,-OH in the presence of a base, such as sodium hydride, or an alkali metal oxide or carbonate, or directly with an alkali metal alkoxide, in an inert solvent such as dimethylformamide or in an excess of the alcohol of the formula R151-OH which corresponds to the group to be introduced, at temperatures between-5 and 160°C, or by reacting, to prepare a corresponding 6-thioether of the formula XXXlllc, analogously to what was described above, either the halide of the formula XXXllld with a thiol of the formula R1s1-SH in the presence of a base such as sodium hydride or with an alkali metal salt of a thiol in an inert solvent at-10-150°C, or by preparing, starting from a pyridone XXXllla and using a thionating agent, for example Lawesson's reagent, in an inert solvent, such as toluene or acetonitrile, a pyrithione of the formula XXXlllb and alkylating this with an alkylating agent R, 5,-X, where X is a leaving group, such as halide (Cl, Br, I) or ROS03-or RSO2-, at 20- 120°C in an inert solvent, such as tetrahydrofuran, to give the thioether of the formula XXXlllc, or, to prepare the corresponding sulfinyl or sulfonyl derivative of the formula XXXlllf, reacting with an oxidizing agent, such as m-chloroperbenzoic acid or sodium periodate, or sodium perborate, under temperature control known to the person skilled in the art, depending on the degree of oxidation (for example-30°C-+50°C for mol =1 or- 20°C-+100°C for moi=2) in an inert solvent, such as dichloromethane, to give XXXlllf, or, to prepare 6-alkyl derivatives XXXIlIg according to the invention, reacting a sulfone of the formula XXXlllf (mol =2) or a halo derivative of the formula XXXllld in the presence or absence of a Pd (0) catalyst such as Pd (PPh3) 2CI2 with a tetra-C,-C6alkyltin or with a Grignard reagent C,-C6alkyl-MgHal at temperatures between-10° and 180°C, for example analogously to Synlett 1998 (1185), or as described in Organocopper Reagents, R. J. K. Taylor, Oxford University Press 1994, or in Transition Metals in Organic Synthesis, S.

Gibson, Oxford Univ. Press, 1997, or in Org. React. 50,1 (Stille reaction), or, to prepare 6- cyano derivatives of the formula XXXlllh, reacting a halide of the formula XXXllld or a sulfone of the formula XXXlllf (moi=2) with an alkali metal or tetraalkylammonium cyanide or copper cyanide in an inert solvent, such as dichloromethane, tetrahydrofuran or dimethylformamide, at temperatures between 0°C and 220°C.

Some of the compounds of the formula XXXllle are also obtainable from the pyridone of the formula XXXllla by reacting them analogously to Org. React. 42,2 with an alcohol R, S, OH in the presence of an azodicarboxylic ester (for example diethyl ester) and triphenylphosphine in an inert solvent, such as tetrahydrofuran or dioxane. (Scheme 9) Reaction scheme 9: R 0 R-OH/PPh 11 ! 5 ORx I ON Rf Azodicarboxylic ester R N Rf R1510 N Rf 151 inertsolvent XXXI I la 20-120°C XXXllle The intermediates of the formula XXXllla required in reaction scheme 8 as starting materials are obtainable according to Scheme 10 route A or route B (Org. Process Research & Development, 1,370 (1997)) or route C. '" OiR, x R R O-1- I 0 O CI H N I Rf NHZ HO Rf 2 elimination of water Route A in the presence or absence CaL such as H2SO) or TsOH Route B of an inert solvent inert solvent -10°G250°C in the presence \/30-250C or absence of a base, e. g. tert-amine 0 R R R, x opdizing agent e. g. Mn02- O N Rt inert solvent, e. g. O N Rt H Cl-benzene H 5G250°C XXXVIII XXXlila elimination of water \ cat. such as H2SO, inert solvent Route C 30-250*c NHZ R, x R, x or NH, OCOCH3 alkylation R or HN (SiCH,Rx O ORX (O base. e. g. R R' O H N Rf p HO R of an inert soNent in the vvv « n Hatogen presence or absence of a XXXVIIXXXIX XXXX cat such as H2SO4 XXXXI Reaction scheme 10 Intermediates of the formula XXXllla are obtainable by route A by reacting, to prepare the 3,4-dihydro-5-aikoxycarbonyl-6-haloalkylpyridin-2-ones of the formula XXXVIII, an enamine of the formula XXXV in the presence or, preferably, in the absence of a solvent either in an excess of enamine or in the presence of a base, such as a tert-amine, with an acryloyl chloride of the formula XXXIV at temperatures between-10° and + 200°C, or by reacting a keto ester of the formula XXXVII with an acrylamide of the formula XXXVI in the presence of a catalyst such as p-toluenesulfonic acid (=HOTs) in an inert solvent, such as toluene, at temperatures between 30 and 200°C, with removal of the water of reaction formed (for example azeotropic distillation), or by reacting a keto ester of the formula XXXVII in the presence of a base, such as an alkali metal alkoxide or magnesium alkoxide, with a 4-halo- keto ester of the formula XXXIX in an inert solvent, such as ethanol, at 0-180°C to give the intermediate of the formula XXXX, converting this with ammonia or an ammonium salt, such as ammonium acetate, or with a bis-silylamine such as hexamethyldisilazane, in the presence or absence of an acidic catalyst, such as sulfuric acid or p-toluenesulfonic acid or an organic carboxylic acid (for example conc. acetic acid), in an inert solvent and at temperatures between 0° and 180°C into the corresponding enamine of the formula XXXXI, subsequently cyclizing in the presence of a catalyst, such as p-toluenesulfonic acid or sulfuric acid, if desired with continuous removal of the water of reaction formed in an inert solvent, such as toluene, to give the dihydropyridone of the formula XXXVIII, and finally treating with an oxidizing agent, such as manganese dioxide, in an inert solvent, such as chlorobenzene, at temperatures between 50 and 250°C, to prepare the pyridones XXXllla.

The intermediates of the formula Ila in which Qa is hydroxyl, halogen, cyano, or a group-CH2 (CO) R36 or Rb is hydrogen, C1-C4alkyl or halogen; R, is trifluoromethyl, difluorochloromethyl, pentafluoroethyl, heptafluoro-n-propyl or trichloromethyl; Rais C,-C3alkyl, C,-C3haloalkyl, C3-C4cycloalkyl, C,-C2alkoxy-C,-C4alkyl, C,-C2- alkylthiomethyl, hydroxyl, halogen, cyano, C,-C3alkoxy, C,-C3haloalkoxy, allyloxy, propargyloxy, C,-C3alkylthio, C,-C3alkylsulfinyl, C,-C3alkylsulfonyl or C,-C3alkylsulfonyloxy, and Roi and R36 are as defined under group Os of the formula 1, except for the compounds 2,6-bistrifluoromethylnicotinic acid, 2,6-bistrifluoromethyl-5-methoxynicotinic acid and 2-hydroxy-6-trifluoromethylnicotinic acid, are novel and therefore likewise form part of the subject matter of the present invention.

Compounds of the formula llb in which Qb is hydroxyl, halogen, cyano or a group-CH2 (CO) R99 or Rg9 is C,. C4alkyl, C,. C4haloalkyl, C3. C4cycloalkyl or C,-C4alkoxy; Rf is trifluoromethyl, difluorochloromethyl, pentafluoroethyl or heptafluoro-n-propyl; and Ré is C,-C3alkyl, C,-C3haloalkyl, C,-C2alkoxymethyl, C,-C2alkylthiomethyl, hydroxyl, halogen, cyano, C,-C3alkoxy, C,-C3haloalkoxy, allyloxy, propargyloxy, C,-C3alkylthio, C1-C3- alkylsulfinyl, C,-C3alkylsulfonyl or C,-C3alkylsulfonyloxy and Roi is as defined under formula I are novel and therefore likewise form part of the subject matter of the present invention.

Preferred compounds of the formula Ila correspond to the formula la in which Qa is hydroxyl, halogen, cyano or a group-CH2 (CO) R36 or Ro, and R36 are as defined in claim 1 and Ra is C,-C3alkyl.

The compounds of the formula I or compositions comprising them can be used according to the invention in all the application methods customary in agriculture, for example pre- emergence application, postemergence application and seed dressing, and various methods and techniques, for example controlled release of active compounds. To this end, the active compound is absorbed in solution onto mineral granule carriers or poiymerized granules (urea/formaldehyde) and dried. If appropriate, a coating which allows the active compound to be released in metered form over a certain period of time can addition be applied (coated granules).

The compounds of the formula I can be employed as herbicides in unchanged form, i. e. as they are obtained in the synthesis, but they are preferably processed in a customary manner 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 methods of application, such as spraying, atomizing, dusting, wetting, scattering or watering, in the same way as the nature of the compositions, are chosen according to the aims striven for and the given circumstances.

The formulations, i. e. the compositions, formulations or preparations comprising the active compound of the formula I or at least one active compound of the formula I and as a rule one or more solid or liquid formulation auxiliaries, are prepared in a known manner, for example by intimate mixing and/or grinding of the active compounds with the formulation auxiliaries, for example solvents or solid carriers. Surface-active compounds (surfactants) can furthermore additionally be used during the preparation of the formulations. Examples of solvents and solid carriers are given, for example, in WO 97/34485 on page 6.

Depending on the nature of the active compound of the formula I to be formulated, suitable surface-active compounds are nonionic, cationic and/or anionic surfactants and surfactant mixtures having good emulsifying, dispersing and wetting properties.

Examples of suitable anionic, nonionic and cationic surfactants are listed, for example, in WO 97/34485 on pages 7 and 8.

The surfactants conventionally used in the art of formulation and which are suitable to prepare the herbicidal compositions according to the invention are described, inter alia, in "Mc Cutcheon's Detergents and Emulsifiers Annual", MC Publishing Corp., Ridgewood New Jersey, 1981, Stache, H.,"Tensid-Taschenbuch" [Surfactant handbook, Carl Hanser Verlag, Munich/Vienna, 1981 and M. and J. Ash,"Encyclopedia of Surfactants", Vol l-lil, Chemical Publishing Co., New York, 1980-81.

The herbicidal formulations as a rule 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 rather preferred as commercial goods, the end user as a rule uses 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), defoamers, for example silicone oil, preservatives, viscosity regulators, binders, tackifiers and fertilizers or other active compounds.

The active compounds of the formula I are as a rule applied to the plants or their habitat, at application rates of 0.001 to 4 kg/ha, in particular 0.005 to 2 kg/ha. The dosage required for the desired effect can be determined by tests. It depends on the nature of the effect, the development stage of the crop plant and the weed and on the application (location, time, process) and can, as a function of these parameters, vary within wide ranges.

The compounds of the formula I have herbicidal and growth-inhibiting properties, owing to which they can be used in crops of useful plants, in particular in cereals, cotton, soya, sugar beet, sugar cane, plantings, rapeseed, maize and rice, and for the non-selective controt of weeds. Crops include those which have been rendered tolerant towards herbicides or herbicide classes by conventional breeding methods or genetical engineering methods. The weeds to be controlled can be both monocotyledonous and dicotyledonous weeds, for example Stellaria, Nasturtium, Agrostis, Digitaria, Avena, Setaria, vSinapis, 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 below illustrate the invention in more detail, without limiting it.

Preparation Examples: Example H1: Preparation of 2-difluoromethoxv-6-trifluoromethvinicotinic acid: At 70°C, 25 g (0.106 mol) of (3-(ethoxycarbonyl)-6-trifluoromethyl) pyrid-2-one (Helv. Chim.

Acta (1988), 71 (3), 596-601) in a mixture of 50 ml of dimethylformamide and 20 ml of water are treated, in the presence of 16 g (0.116 mol) of finely powdered potassium carbonate and with efficient stirring, with a continuous stream of gaseous Freon-22. After 6 hours, a further 16 g of potassium carbonate and 20 ml of dimethyl sulfoxide are added, and the mixture is stirred with continuous introduction of Freon-22 gas at a temperature of 100°C for another 4 hours. The mixture is then treated with water and ice and extracted with diethyl ether. The aqueous phase is adjusted to pH 2 using conc. HCI and extracted with ethyl acetate. Diethyl ether is added to the extract, and some (3- (carboxy)-6- trifluoromethyl) pyrid-2-one crystals which have precipitated out are removed by filtration.

The filtrate is filtered through a silica gel column (mobile phase ethyl acetate/hexane 1: 1) giving, as a crystalline product, pure 2-difluoromethoxy-6-trifluoromethylnicotinic acid:'H NMR (CDCI3, ppm): 8.60, d, J=9 Hz, 1 H; 7.62, d, J=9 Hz, 1 H ; 7.62, t, J=67 Hz, 1 H.

Example H2: Preparation of 4-methyl-6-trifluoromethvinicotinic acid: In the presence of 5.8 ml of phenyl dichlorophosphate, 7.5 g (0.03 mol) of ( (3- ethoxycarbonyl)-4-methyl-6-trifluoromethyl) pyrid-2-one (Helv. Chim. Acta (1988), 71 (3), 596-601) are heated in a pressure vessel at a temperature of 170°C for 3 hours. The cold reaction solution is filtered directly through a short silica gel column (mobile phase: ethyl acetate/hexane 1: 9), giving, as an oily product, ethyl 2-chtoro-4-methyl-6-trifluoromethyl- pyridin-3-ylcarboxylate: 'H NMR (CDCI3, ppm): 7.49, s, 1 H; 4.48, q, 2H; 2.43, s, 3H, 1.43, t, 3H.

3.0 g (16.8 mmol) of the above product and, in 2 portions, a total of 5 g of ammonium formate are added to a suspension of 0.55 g of 10% Pd/C in 20 rnl of methanol, and the mixture is stirred at room temperature for 24 hours. The reaction mixture is then filtered through Celite and, after addition of sodium chloride solution, extracted with ethyl acetate.

Chromatographic purification (mobile phase 1: 9) gives the 4-methyl-6-trifluoromethylpyridin- 3-yl ethyl ester as an oil:'H NMR (CDC13, ppm): 9.11, s, 1 H; 7.56, s, 1 H, 4.44, q, 2H; 2.72, s, 3H, 1.42, t, 3H. This is hydrolysed at 40°C in the presence of aqueous potassium hydroxide solution in dioxane. Extraction with ethyl acetate gives, after acidification to pH 2.7,4-methyl-6-trifluoromethyinicotinic acid as a crystalline product:'H NMR (CDCI3, ppm): 7.49, s, 1 H; 4.48, q, 2H; 2.43, s, 3H, 1.43, t, 3H; 9.32, s, 1 H, 7.62, s, 1 H, 2.79, s, 3H.

Example H3: Preparation of 6-chloro-4-trifluoromethylnicotinic acid: 9.6 g (0.047 mol) of methyl 4-trifluoromethylpyridin-3-ylcarboxylate, dissolved in 50 mi of dichloromethane, are treated with 30% hydrogen peroxide/urea adduct and 17 ml of trifluoroacetic anhydride. The reaction solution is stirred at temperature of 20°C for 20 hours and then washed once each with dilute sodium hydroxide solution and half-saturated sodium chloride solution. The product obtained is 3-methoxycarbonyl-4-trifluoromethyl-3- pyridine N-oxide;'H NMR (CDCI3, ppm): 8.55, s, 1H; 8.31, d, 1H; 7.6, d, 1H; 3.98, s, 3H.

4.85 g (0.022 mol) of the above product are then added to a mixture of 5 ml of phosphorus oxychloride and 4.3 ml of ethyidiisopropylamine in 15 ml of 1,2-dichloroethane, and the mixture is heated to a temperature of 60°C. After about 2 hours, another 2 ml of phosphorus oxychloride and 2.8 ml of ethyldiisopropylamine are added, and the mixture is stirred at this temperature for 20 hours. The reaction mixture is subsequently added to ice- water, adjusted to pH 3 using 30% NaOH and then extracted with dichloromethane.

Filtration through a little silica gel gives an approximately 5: 1 product mixture of the two 6- chioro-and 2-chloro-4-trifluoromethylpyridin-3-yl methyl esters, which can be separated by HPLC into the pure components. Thus, pure methyl 6-chloro-4-trifluoromethylpyridin-3- ylcarboxylate is obtained as the main product; rH NMR (CDCI3, ppm): 8.91, s, 1H; 7.68, s, 1 H; 3.98, s, 3H, and pure methyl 2-chloro-4-trifluoromethylpyridin-3-ylcarboxylate is obtained as the byproduct;'H NMR (CDCI3, ppm): 8.64, d, 1 H; 7.52, d, 1 H; 4.01, s, 3H.

In the presence of 0.073 g of potassium hydroxide, 0.22 g of pure methyl 6-chloro-4- trifluoromethylpyridin-3-ylcarboxylate are hydrolyse at room temperature in a 1: 1 mixture of 6 ml of dioxane/water. Recrystallization gives the pure 6-chloro-4-trifluoromethylnicotinic acid: m. p. 11 5-117°C ; 1H NMR (CDCi3, ppm): 9.12, s, 1 H; 7.24, s, 1 H.

Example H4: Preparation of 6-methylthio-4-trifluoromethvinicotinic acid: In boiling acetone, 0.70 g (2.9 mol) of methyl 6-chloro-4-trifluoromethylpyridin-3- ylcarboxylate is treated in the presence of a catalytic amount of 18-crown-6 with methanethiolate (0.33 g) until no further conversion can be detected by gas chromatographic analysis. The mixture is then filtered through silica gel and evaporated.

This gives 0.73 9 of methyl 6-methylthio-4-trifluoromethylpyridin-3-ylcarboxylate ;'H NMR (CDC13, ppm): 8.98, s, 1 H; 7.48, s, 1 H; 3.94, s, 3H; 2.64, s, 3H.

Hydrolysis under the conditions mentioned above gives 6-methylthio-4-trifluoromethyl- nicotinic acid:'H NMR (CDC13, ppm): 9.02, s, 1 H; 7.46, s, 1 H; 2.64, s, 3H.

Example H5: 6-Hvdroxv-2-trifluoromethrlpvridin-3-vl ethvl ester: Under an atmosphere of nitrogen and with stirring, 33.4 g of 3,4-dihydro-5-ethoxycarbonyl- 6-trifluoromethylpyridin-2-one (Org. Res. & Devel. 1,370 (1997)) and 34 g of manganese dioxide in 250 mi of 1,2-dichiorobenzene are heated under reflux for 24 hours. In intervals of about 20 hours, manganese dioxide (total amount of Mn02 used: 213 g) is added six more times over a period of 3 days, and the mixture is in each case heated further under reflux. The mixture is then cooled, diluted with ethyl acetate, and filtered through silica gel, the filtercake is washed with ethyl ester and the filtrate is concentrated. The solid residue (26.7 g, i. e. 80%), which may still contain about 6% of starting material, is directly reacted further. For complete purification, it is possible to purify, for example, over silica gel (hexane/ethyl acetate 7: 3) ('H NMR, CDC13, ppm): 8.02 (d, 1 H); 6.85 (d, 1 H); 4.86 (q, 2H); 1.37 (t, 1 H).

Example H6: Preparation of ethvl 6-chloro-2-trifluoromethylpyridin-3-ylcarboxylate : In a bomb tube, 23.5 g of ethyl 6-hydroxy-2-trifluoromethylpyridin-3-ylcarboxylate and 23.5 mi of phenyl dichlorophosphate are heated at 170°C for 3 hours, and the mixture is, after cooling, added to ice-water, stirred for a few minutes and subsequently taken up in ethyl acetate and made slightly alkaline using sodium bicarbonate and then washed neutral with water. The extracts are admixed with a little hexane and filtered through silica gel. The filtrate is evaporated, leaving 21.6 g (85%) of the title compound in the form of a dark oil with nD30 1. 4679. 1H NMR (CDCI3, ppm): 8.09 (d, 1H); 7.60 (d, 1H); 4.43 (q, 2H); 1.43 (t, 3H).

Example H7: Preparation of 6-chloro-2-trifluoromethvipvridin-3-vlcarboxvlic acid : 2.5 g of the ethyl 6-chloro-2-trifluoromethyipyridin-3-ylcarboxylate obtained above are dissolved in the smallest possible amount of tetrahydrofuran, treated with approximately 20 g of ice and 11 mi of 1 N lithium hydroxide and stirred at room temperature until hydrolysed completely. The mixture is then washed with a little ether and the aqueous phase is acidified using 4N hydrochloric acid and extracted with ethyl acetate. The extracts are washed with sodium chloride solution, dried and evaporated. This gives 1.8 g of the title compound of m. p. 154-156°C. The other free carboxylic acids are likewise obtained from their esters in this manner.

Example H8: Preparation of ethyl 6-methytthio-2-trifluoromethyipvridin-3-vlcarbox I: Under an atmosphere of nitrogen and with stirring, a solution of 1.7 g of 6-chloro-2- trifluoromethylpyridin-3-yi ethyl ester in 60 ml of dimethylformamide is treated a little at a time with 0.52 g of sodium methanethioiate and stirred at room temperature until the reaction has gone to completion. The reaction mixture is then poured into ice-water, made neutral by addition of a little dilute hydrochloric acid and extracted with ethyl acetate. The extracts are diluted with a little hexane, washed with water, dried over sodium sulfate, filtered and, after filtration through a little silica gel, evaporated. This gives 1.4 g (79%) of the title compound in the form of an oil with nD25 1. 5100, 1H NMR (CDCI3, ppm): 7.90 (d, 1 H); 7.40 (d, 1 H); 1.40 (q, 2H); 2.60 (s, 3H); 1.49 (t, 3H).

Example H9: Preparation of ethyl 6-ethylthio-2-trifluoromethylpyridin-3-ylcarboxylate : In an apparatus previously flushed with nitrogen, a solution of 1.8 mi of ethanethiol in 40 ml of dimethylformamide, which had been cooled to 0°C, is treated a little at a time with 0.96 g of sodium hydride oil dispersion (60%), and the mixture is stirred at room temperature. After evolution of hydrogen has ceased, the mixture is cooled to-20°C, and a solution of 5.07 g of 6-chloro-2-trifluoromethylpyridin-3-yl ethyl ester in 10 mi of dimethylformamide is added dropwise at this temperature, and the mixture is stirred slowly until room temperature has been reached. After the reaction has ended (approximately 3 hours), the reaction mixture is added to ice-water and extracted with ethyl acetate. The extracts are washed with water, dried, filtered, evaporated and dried under high vacuum. This gives 5.0 g (89%) of the title compound as a brownish oil.'H NMR (CDCI3, ppm): 7.90 (d, 1H); 7.35 (d, 1H); 4.40 (q, 2H); 3.25 (q, 2H); 1. 38 (2t, 6H).

Example H10: Preparation of ethvl 6-ethvisulfinyl-2-trifluoromethviDyridin-3-vlcarboxviate: Under an atmosphere of nitrogen and with stirring and cooling, a solution of 2.5 g of m- chloroperbenzoic acid in 40 ml of methylene chloride is added dropwise at a temperature of -20°C to a solution of 2.8 g of ethyl 6-ethylthio-2-trifluoromethylpyridin-3-ylcarboxylate, which had been charged initially, and the mixture is stirred at a temperature of +5°C for 20 hours. The mixture is then evaporated gently and purified over silica gel (hexane/ethyl acetate 7: 3). This gives 2.48 g (84%) of 6-ethylsulfinyl-2-trifluoromethylpyridin-3-yl-ethyl ester.'H NMR (CDCI3, ppm): 8.38 (d, 1H); 8.30 (d, 1H); 4.45 (q, 2H); 3.26-3.00 (m, 2H); 1.43 (t, 3H); 1.26 (t, 3H).

Ethyl 6-methylsulfinyl-2-trifluoromethylpyridin-3-ylcarboxylate is obtained in an analogous manner.

Example H11: Preparation of ethyl 6-methVlsulfonvl-2-trifluoromethvlpyridin-3-vicarboXviate: Under an atmosphere of nitrogen and with stirring and cooling, 21 g of m-chloroperbenzoic acid are introduced a little at a time over a period of 30 minutes at a temperature of-20°C into a solution of 3.6 g of 6-methylthio-2-trifluoromethylpyridin-3-yl ethyl ester, which had been charged initially, and the reaction mixture is stirred at room temperature for 5 hours.

The mixture is then evaporated and filtered through silica gel (ethyl acetate/methanoi/ triethylamine 85: 10: 5). This gives 3.95 g (97%) of ethyl 6-methylsulfonyl-2- trifluoromethylpyridin-3-ylcarboxylate as a brownish solid with m. p. 70-72°C.'H NMR (CDCI3, ppm): 8.40 (1 H, d); 8.33 (1 H, d); 4.47 (2H, q); 1.43 (3H, t).

Example H12: Preparation of ethyl 6-cvano-2-trifluoromethlpvridin-3-ylcarboxylate: Under an atmosphere of nitrogen and with stirring, a solution of 0.596 g of ethyl 6- methylsulfonyl-2-trifluoromethylpyridin-3-ylcarboxylate in 5 ml of dimethylformamide is treated with 160 mg of solid potassium cyanide and a spatula tipful of 18-crown-6, and the mixture is heated at 80°C for 3 hours. The mixture is cooled overnight, and the next day another 30 mg of potassium cyanide are added and the mixture is heated further until the starting material has disappeared (approximately 2 hours). The mixture is then cooled, added to ice-water and extracted with ethyl acetate. The extracts are washed with water, dried, evaporated and freed from traces of dimethylformamide under high vacuum at approximately 40°C. This gives 480 mg (yield virtually quantitative) of ethyl 6-cyano-2- trifluoromethylpyridin-3-ylcarboxylate in the form of an oil which slowly solidifies.'H NMR (CDCI3, ppm): 8.29 (1 H, d); 7.97 (1 H, d); 4.48 (2H, d); 1.43 (3H, t).

Example H13: Preparation of ethvl 6-methyl-2-trifluoromethylDvridin-3-vlcarboxylate: Under an atmosphere of nitrogen and with stirring, a solution of 3.6 g of 6-chloro-2- trifluoromethylpyridin-3-yl ethyl ester in 20 mi of dimethylacetamide is treated with 4.5 mi of tetramethyltin and 200 mg of dichloro (bistriphenylphosphine) palladium, and the mixture is heated to a temperature of 80-90°C for 24 hours. Then another 1.5 ml of tetramethyltin and 30 mg of dichloro (bistriphenylphosphine) palladium are added and the mixture is heated for another 6 hours. The reaction mixture is then freed from excess tetramethyltin using reduced pressure (destruction by passing through ethanolic sodium hydroxide solution), cooled and added to ice-water. The mixture is extracted with diethyl ether and the extract is washed with water, dried over sodium sulfate, filtered through a little silica gel, evaporated and dried under reduced pressure. This gives the title compound (2.4 g, 73%), which still contains traces of dimethylacetamide, in the form of a dark oil.

'H NMR (CI3, ppm): 8.00 (1 H, d); 7.42 (1 H, d); 4.42 (2H, d); 2.68 (3H, s); 1.41 (3H, t).

Hydrolysis analogously to the description already mentioned above affords 6-methyl-2- trifluoromethylpyridin-3-ylcarboxylic acid (brown resin) which is directly converted further into the carbonyl chloride.

Example H14: Preparation of 6-methyl-2-trifluoromethvlpvridin-3-vicarbonvl chloride: A solution of 0.45 g of 6-methyl-2-trifluoromethylpyridin-3-ylcarboxylic acid in 20 ml of dichloromethane is charged initially, 3 drops of dimethylformamid& are added and the mixture is subsequently treated with 1.6 mi of oxalyl chloride. After the intensive evolution of gas has ceased, the mixture is kept at a bath temperature of 40°C for another 1.5 hours and then evaporated. The crude product (0.56 g) that remains as residue can be directly reacted further. 1H NMR (CDCI3, ppm): 8.20 (1 H, d); 7.51 (1 H, d); 2.65 (3H, s).

Example H15: PreRaration of 4-oxqbicvclof3.2.11Oct-2-en-2-vl 6-methvl-2-trifluorometh nicotinate : Under an atmosphere of nitrogen and with stirring and cooling, a solution of 0.56 g of 6- methyl-2-trifluoromethylpyridin-3-ylcarbonyt chloride in 10 mi of methylene chloride is added dropwise at 0°C to a solution of 0.4 g of bicyclo 3.2.1 octane-2,4-dione and 0.72 g of triethylamine in 10 ml of methylene chloride, and the mixture is stirred for 5 hours until room temperature has been reached. The mixture is then diluted with methylene chloride, washed with cold 1 N hydrochloric acid, dried and evaporated to give the desired enol ester (0.8 g) as a brown resin which is directly reacted further.'H NMR (CDCI3, ppm): 8.17 (1H, d); 7.51 (1 H, d); 5.96 (1 H, s); 3.04 (2H, m); 2.75 (3H, s); 2.32-1.30 (m).

Examote H16: Preparation of 4-h rdroxv-3(6-methyl-2-trifluoromethylpyridin-3-carbonl)- bicvclof3.2.1 loct-3-en-2-one: Under an atmosphere of nitrogen and with stirring, 0.8 g of the above enol ester is dissolved in 30 mi of acetonitrile at 25 °C, and the mixture is treated with 0.5 ml of triethylamine and 0.4 mi of acetone cyanohydrin and stirred at room temperature for 20 hours. The mixture is then diluted with solvent and washed with dilute hydrochloric acid, dried and evaporated, and the residue is purified through a little silica gel (ethyl acetate/methanol/triethylamine 85: 10: 5). This gives 371 mg (46%) of the title compound (triethylamine salt) in the form of a yellowish resin. 1H NMR (CDCI3, ppm): 7.45 (1H, d); 7.25 (1H, d); 3.80-3.43 (4H, m); 3.18 (6H, m); 2.80 (2H, s (br)); 2.62 (3H, s); 2.20-1.54 (m).

Example H17: Preparation of ethyl 6-methoxy-2-trifluoromethvlpyridin-3-vicarboxylate: A suspension of 5.65 g of ethyl 6-hydroxy-2-trifluoromethylpyridin-3-ylcarboxylate, 6.0 g of potassium carbonate and 2.7 mi of methyl iodide is, together with a spatula tipful of 18- crown-6, heated to a temperature of 60-70°C until the reaction has gone to completion. The mixture is then filtered, the filtration residue is washed with acetonitriie and the filtrate is concentrated under reduced pressure. The residue is cooled, admixed with ice-water, neutralized with dilute sulfuric acid and extracted with ethyl acetate. The extracts are washed with water, dried, diluted with a little hexane and filtered through a little silica gel.

The resulting residue is the title compound (3.7 g, 65%) in the form of slightly orange crystals of m. p. 150-152°C.

'H NMR (CDC13, ppm): 8.00 (1H, d); 6.83 (1 H, d); 4.38 (2H, q); 4.01 (3H, s); 1.39 (3H, t).

Example H18: Preparation of 4-hVdroxy-3-(2-methvl-6-trifluoromethvlpvridin-3-carbonVl)- bicyclof3.2.1 loct-3-en-2-one: 6.68 g (0.0305 mol) of methyl 2-methyl-6-trifluoromethylnicotinate (prepared as described in Heterocycles, 46,129 (1997)) are dissolved in 250 ml of methanoUwater (3: 1 mixture), and 1.92 g (0.046 mol) of lithium hydroxide hydrate are added a little at a time at 22°C. After 4 hours at 22°C, the reaction mixture is poured into ethyl acetate and 2 N hydrochloric acid, the organic phase is washed three times with water, dried with sodium sulfate and evaporated and the residue is triturated with a little hexane. Filtration gives 5.69 g (90% of theory) of the expected 2-methyl-6-trifluoromethyinicotinic acid of m. p. 147-149°C.

The 2-methyl-6-trifluoromethyinicotinic acid obtained (2.0 g, 0.0098 mol) is dissolved in 20 ml of oxalyl chloride. Three drops of dimethylformamide are added, and the mixture is heated under reflux for 1 hour. The mixture is then concentrated using a rotary evaporator, and the residue (2-methyl-6-trifluoromethyinicotinoyl chloride) is taken up in 30 ml of methylene chloride. At 0°C, 2.7 ml (0.0196 mol) of triethylamine and 0.12 g (0.00098 mol) of dimethylaminopyridine are added. 1.49 g (0.0108 mol) of bicyclo [3.2.1] octane-2,4-dione, dissolved in 20 ml of methyiene chloride, are then added dropwise. After 3 hours at 22°C, the reaction mixture is extracted with 2 N hydrochloric acid. The methylene chloride phase is separated off, washed with water and subsequently extracted with 10% aqueous sodium bicarbonate solution, dried over sodium sulfate and evaporated. This gives 3.18 g (100% of theory) of 4-oxobicyclo [3.2.1] oct-2-en-2-yl 2-methyl-6-trifluoromethyinicotinate as an oil, which can be processed further without purification.

3.02 g (0.0093 mol) of 4-oxobicyclo [3.2.1] oct-2-en-2-yl 2-methyl-6-trifluoromethyinicotinate and 1.9 ml (0.0136 mol) of triethylamine are dissolved in 45 ml of acetonitrile. At 22°C, 0.01 ml of acetone cyanohydrin are added. After 18 hours at 22°C, the reaction mixture is poured into dilute hydrochloric acid and extracted with ethyl acetate. The ethyl acetate phase is washed with water and then with brine, dried over sodium sulfate and evaporated, and the residue is dissolved in a little warm acetone. The product crystallizes on standing.

Filtration gives 0.99 g (33% of theory) of the expected 4-hydroxy-3- (2-methyl-6- trifluoromethylpyridine-3-carbonyl)bicyclo [3.2.1]oct-3-en-2-one as white crystals (m. p. 75- 77°C).

Example H19: Preparation of 3-i (2-methyl-6-trifluoromethvlpvridine-3-carbonvl)-4-oxo- bicvclof3.2.11oct-2-en-2-vl benzoate : At 0°C, a solution of 0.562 g (0.0004 mol) of benzoyl chloride in 1 ml of tetrahydrofuran is added to a solution of 1.14 g (0.0035 mol) of 4-hydroxy-3- (2-methyl-6- trifluoromethylpyridine-3-carbonyl) bicyclo [3.2.1] oct-3-en-2-one and 0.517 g (0.004 mol) of ethyidiisopropylamine in 15 ml of tetrahydrofuran. The reaction mixture is stirred at 25°C for 2 hours, evaporated and purified over silica gel (hexane/ethyl acetate 1: 1). This gives 0.9 g (60%) of the titte compound in the form of a yellowish resin.'H NMR (CDCI3, ppm): 7.91-7.87, m, 3H; 7.64, t, J=7.5 Hz, 1 H; 7.50-7.40, m, 3H; 3.24, br t, J=4 Hz, 1 H; 3.14, br t, J=4 Hz, 1 H; 2.70, s, 3H; 2.47, d, J=13.5Hz, 1H; 2.40,2.15, m, 3H; 1.95-1.8, m, 2H.

Example H20: Preparation of 4-hx-3- (2-methvl-1y-6-trifluoromethylayridine-3- carbonyl) bicyclof3.2.11oct-3-en-2-one: 16.25 g (0.05 mol) of 4-hydroxy-3- (2-methyl-6-trifluoromethylpyridine-3-carbonyl)- bicyclo [3.2.1]oct-3-en-2-one and 9.4 g (0.1 mol) of urea/hydrogen peroxide complex are dissolved in 150 mi of methylene chloride, and 20.5 ml (0.15 mol) of trifluoroacetic anhydride are added dropwise at 25°C. After 14 hours at 25°C, the reaction mixture is added to ethyl acetate and water, and the organic phase is washed twice with water, dried with sodium sulfate and evaporated. The residue is chromatographed over silica gel (mobile phase: ethyl acetate/methanol 9/1). This gives 6.8 g (40%) of the desired product as white crystals (m. p. 109-110°C).

Example H21: Preparation of 4-chloro-3- (2-methyl-6-triftuoromethylpyridine-3-carbonLrl ; bicyclo[3.2.1]oct-3-en-2-one : 20.15 g (0.062 mol) of 4-hydroxy-3- (2-methyl-6-trifluoromethylpyridine-3-carbonyl)- bicyclo [3.2.1] oct-3-en-2-one are suspended in 50 mi of oxalyl chloride, and 0.1 ml of dimethylformamide are added dropwise. After the intensive evolution of gas has ceased, the mixture is kept at a bath temperature of 45°C for another 1.5 hours and then evaporated, and the residue is suspended in a little ethyl acetate and admixed with stirring at 0°C with hexane. Filtration gives 19.19 g (90% of theory) of 4-chloro-3- (2-methyl-6- triftuoromethyl-pyridine-3-carbonyl) bicycio [3.2.1] oct-3-en-2-one of m. p. 137-138°C.

Exampte H22: Preparation of 4-amino-3-(2-methvl-6-trifluoromethvlpvridine-3-carbonVl)- bicycle 3.2.1 loct-3-en-2-one: 1.0 g (0.0029 mol) of 4-chloro-3-(2-methyl-6-trifluoromethylpyridine-3-carbonyl)- bicyclo [3.2.1]oct-3-en-2-one are dissolved in 10 ml of tetrahydrofuran and, at 25°C, treated with 2.0 ml of aqueous ammonia (30%). After 0.5 hours at 000 the reaction mixture is added to ethyl acetate and water, the organic phase is washed twice with water, dried with sodium sulfate and evaporated and the residue is triturated with a iittie ethyl acetate.

Filtration gives 0.81 g (86% of theory) of 4-amino-3- (2-methyl-6-trifluoromethylpyridine-3- carbonyl)bicyclo [3.2.1]oct-3-en-2-one in the form of white crystals (m. p. 262-263°C).'H NMR(CDCl3, ppm): 10.62 br s 1 H; 8.223 br s 1 H; 7.41, d, J= 8.1 Hz, 1 H; 7.35, d, J= 8.1 Hz, 1 H; 3.03, br t, J= 4.8 Hz, 1 H; 2.70, br t, J= 4.8 Hz, 1 H; 2.41, s, 3H; 1.97-2.14, m, 3H; 1.77-1.812, m, 1 H; 1.47-1.70, m, 2H.

Example H23: Preparation of 4-(4-chlorophenvisulfanvl)-3-(2-methvl-6-trifluoromethyl- pyridine-3-carbonyl)bicyclo [3.2.1]oct-3-en-2-one: 2.0 g (0.0058 mol) of 4-chloro-3- (2-methyl-6-trifluoromethylpyridine-3-carbonyl)- bicyclo [3.2.1] oct-3-en-2-one, 0.07 g of dimethylaminopyridine (0.00058 mol) and 1.61 mi of triethylamine are dissolved in 15 ml of methylene chloride. At 25°C, 0.092 g (0.0064 mol) of 4-chlorothiophenol are added. After 2 hours at 22°C, the reaction mixture is evaporated and purified over silica gel (hexane/ethyl acetate 2: 1). Recrystallization (hexane/acetic acid at -25°C) gives pure 4- (4-chlorophenylsulfanyl)-3- (2-methyl-6-trifluoromethytpyridine-3- carbonyl) bicyclo [3.2.1]oct-3-en-2-one : m. p. 130-131 °C.

Example H24: Preparation of 4-(4-chlorobenzenesulfonvl)-3-(2-methvl-6-trifluoromethVl- pvridine-3-carbonyl) bicyclof3.2.1 1oct-3-en-2-one: 0.6 g (0.00133 mol) of the 4- (4-chlorophenylsulfanyl)-3- (2-methyl-6-trifluoromethylpyridine- 3-carbonyl) bicyclo [3.2.1] oct-3-en-2-one obtained above is dissolved in methylene chloride, and 0.9 ml of peracetic acid (39% in acetic acid, 0.0053 mol) are added dropwise at 25°C.

After 5 hours at 25°C, the reaction mixture is added to ethyl acetate and water, the organic phase is washed with water, dried with sodium sulfate and evaporated and the residue is triturated with a little hexane. Filtration gives 0.56 g (84% of theory) of 4- (4- chlorobenzenesulfonyl)-3- (2-methyl-6-trifluoromethylpyridine-3-carbonyl) bicyclo [3.2.1] oct-3- en-2-one in the form of white crystals (m. p. 166-167°C).

Example H25: Preparation of (5-cycloDropyl-3-methylsulfanvlisoxazol-4-vl)- (2-methyl-6- trifluoromethvlpyridin-3-vlWmethanone and cvcloproDvl-l3-methvisulfanvl-5-(2-methvl-6- trifiuoromethypvridin-3-y isoxazol-4-y methanone : 14.8 g (0.080 mol) of tert-butyl 3-cyclopropyl-3-oxopropionic acid ester are dissolved in 25 ml of MeOH, and 1.93 g (0.080 mol) of magnesium are added. With ice-bath cooling, 7 ml of carbon tetrachloride are added dropwise, and the reaction mixture is stirred at a temperature of 22°C for one hour. After evaporation, the residue is suspended in 100 mi of acetonitrile, and 16.31 g (0.073 mol) of 2-methyl-6-trifluoromethyinicotinoyl chloride (prepared as described in Example H18), dissolved in 50 mi of acetonitrile, are added dropwise at a temperature of 22°C. After 6 hours, the reaction mixture is taken up in ethyl acetate and washed with saturated sodium bicarbonate solution. The ethyl acetate phase is separated off, washed with water, dried over sodium sulfate and evaporated. The residue is dissolved in 160 mi of methyiene chloride, and 10 ml of trifluoroacetic acid are added dropwise at a temperature of 22°C. After 18 hours, the reaction mixture is poured into water and extracted with methylene chloride. The methylene chloride phase is washed with water and then with saturated aqueous sodium chloride solution, dried over sodium sulfate and evaporated. This gives 17.3 g (88% of theory) of 1-cyclopropyl-3- (2-methyl-6- trifluoromethylpyridin-3-yl) propane-1,3-dione as an oil, which is processed further without purification. The 1-cyclopropyl-3- (2-methyl-6-trifluoromethylpyridin-3-yl) propane-1,3-dione obtained above (15.0 g, 0.055 mol) is dissolved in 150 mi of dimethylformamide, and 50 g of potassium fluoride on an aluminium oxide support (alumina) (0.0055 mol/g, 0.276 mol) are added a little at a time at a temperature of 0°C. After 5 minutes, 6.7 g (0.088 mol) of carbon disulfide are added dropwise. After 2 hours, 23.6 g (0.166 mol) of methyl iodide are added dropwise, and the reaction mixture is warmed to a temperature of 22°C. After a further 2 hours, the alumina is filtered off, the filtrate is added to water and the mixture is extracted with ethyl acetate. The ethyl acetate phase is washed with water and then with saturated aqueous sodium chloride solution, dried over sodium sulfate and evaporated. The residue is chromatographed over silica gel (mobile phase: ethyl acetate/hexane 15/1). This gives 12.0 g (60% of theory) of 2- (bismethylsulfanylmethylene)-1-cyclopropyl-3- (2-methyl-6- trifluoromethylpyridin-3-yl)-propane-1,3-dione as a solid.

12.0 g (0.033 mol) of the product obtained above are, together with 5.4 g (0.066 mol) of anhydrous sodium acetate, suspended in 120 mi of ethanol. 4.6 g (0.066 mol) of hydroxylamine hydrochloride are added, and the reaction mixture is kept at a temperature of 22°C for 5 hours. Another 2.7 g of anhydrous sodium acetate and 2.3 g of hydroxylamine hydrochioride are then added. After 18 hours, the reaction mixture is diluted with water and extracted with ethyl acetate. The ethyl acetate phase is washed with water and then with saturated aqueous sodium chloride solution, dried over sodium sulfate and evaporated.

Trituration with a little ethyl acetate gives 9.0 g (79.5%) of the desired product as a 2: 1 isomer mixture in the form of white crystals (m. p. 103-104°C).

Main isomer:'H NMR (CDCI3, ppm) ( (5-cyclopropyl-3-methylsulfanylisoxazol-4-yl)- (2-methyl- 6-trifluoromethylpyridin-3-yl) methanone) 7.98, d, J=7.8 Hz, 1 H; 7.61, d, J=7.8 Hz, 1 H; 2.67, s, 3H; 2.50, s, 3H; 2.02-1.93, m, 1 H ; 1.34-1.28, m, 2H; 1.18-1.09, m, 2H.

'H NMR (CDCI3, ppm) (cyclopropyl- 3-methylsulfanyl-5- (2-methyl-6-trifluoromethylpyridin-3- yl) isoxazol-4-yl methane): 7.95, d, J=7.8 Hz, 1 H; 7.69, d, J=7.8 Hz, 1 H; 2.67, s, 3H; 2.66, s, 3H; 1.74-1.64, m, 1 H; 1.28-1.18, m, 2H; 0.89-0.80, m, 2H.

Example H26: Preparation of (5-c clopyl-3-methylsulfinylisoxazol-4-y(2-meth6- trif luoromethylgyridin-3-yl) methanone and cycloproDyl-f3-methanesulfinvl-5- (2-methyl-6- trifluoromethylpvridin-3-vl) isoxazol-4-vllmethanone: 1.50 g (0.0043 mol) of the isomer mixture obtained above are dissolved in 30 mi of acetone/water (2: 1 mixture), and 1.02 g (0.0048 mol) of sodium metaperiodate are added a little at a time at 22°C. After 5 hours, the reaction mixture is evaporated using a rotary evaporator. The residue is taken up in water and ethyl acetate. The ethyl acetate phase is dried over sodium sulfate and evaporated. The residue is chromatographed over silica gel (mobile phase: ethyl acetate/hexane 3/1). This gives initially 0.8 g (51 % of theory) of (5- cyclopropyl-3-methylsulfinylisoxazol-4-yl)-(2-methyl-6-trifl uoromethylpyridin-3-yl)(2-methyl-6-trifluoromethylpyridin-3- yl) methanone as white crystals (m. p. 96-97°C).'H NMR (CDCI3, ppm): 7.86, d, J=7.8 Hz, 1 H; 7.59, d, J=7.8 Hz, 1 H; 3.078, s, 3H; 2.66, s, 3H; 1.54-1.49, m, 1 H; 1.32-1.25, m, 2H; 1.13-1.072, m, 2H.

The second product that elutes consists of 0.34 g (22% of theory) of cyclopropyl- 3- methanesulfinyl-5- (2-methyl-6-triftuoromethylpyridin-3-yl) isoxazol-4-yl methanone as white crystals (m. p. 112-113°C).'H NMR (CDCI3, ppm): 7.97, d, J=7.8 Hz, 1H; 7.67, d, J=7.8 Hz, 1H; 3.128, s, 3H; 2.62, s, 3H; 1.69-1.64, m, 1H; 1.26-1.18, m, 2H; 0.90-0.85, m, 2H.

Example H27: Preparation of (5-cyclopropvl-3-methanesulfonvlisoxazol-4-Lr (2-isoprop, rl-6- trifluoromethylpvridin-3-vl) methanone: 0.15 g (0.0045 mol) of (5-cyclopropyl-3-methylsulfanylisoxazol-4-yl)-(2-isopropyl-6 - trifluoromethylpyridin-3-yl) methanone is dissolved in methylene chloride, and 0.28 mi of peracetic acid (39% in acetic acid, 0.0016 mol) are added dropwise at a temperature of 5°C.

After 15 hours at 25°C, the reaction mixture is added to ethyl acetate and water, and the organic phase is washed with water, dried with sodium sulfate and evaporated. The residue is chromatographed over silica gel (mobile phase: ethyl acetate/hexane 5/1). This gives 0.121 g (74% of theory) of the expected product as white crystals (m. p. 105-106°C).

In an analogous manner, and according to the methods shown in the general reaction schemes 1-10 and in the references mentioned therein, it is also possible to prepare the compounds listed in the tables below. In these tables, CCH is the ethynyl group, Ph is the phenyl group and Me is the methyl group.

Table 1: Comp. R, R2 R3 R4 Rs P No.

Comp. R, R2 R3 R4 Rs P No.

1.001H CF3 H H OH 0 1.002 F CF3 H H OH 0 1.003 Cl CF3 H H OH 0 1.004 Br CF3 H H OH 0 1.005 CHF2 CF3 H H OH 0 1.006 CCI3 CF3 H H OH 0 1.007 CCIF2 CF3 H H OH 0 1.008 CF3 CF3 H H OH 0 1.009 CH3 CF3 H H OH 0 1.01 CH2CH3 CF3 H H OH 0 1.011 CH (CH3) 2 CF3 H H OH 0 1.012 (CH2) 2CH3 CF3 H H OH 0 1.013C(CH3)3 CF3 H H OH 0 1.014 Ph CF3 H H OH 0 1.015 CH2F CF3 H H OH 0 1.016 CH2CI CF3 H H OH 0 1.017CH2Br CF3 H H OH 0 1.018CH2OH CF3 H H OH 0 1.019CH2OCOCH3 CF3 H H OH 0 1.02CH2OCOPh CF3 H H OH 0 1.021CH2OCH3 CF3 H H OH 0 1.022 CH2OCH2CH3 CF3 H H OH ° 1.023CH2CH2OCH3 CF3 H H OH 0 1.024 CH2SMe CF3 H H OH 0 1.025 CH2SOMe CF3 H H OH 0 1.026CH2SO2Me CF3 H H OH 0 1.027CH2SO2Ph CF3 H H OH 0 1.028SCH2Ph CF3 H H OH 0 1.029 SOCH2Ph CF3 H H OH 0 1.03 SO2CH2PhCF3 H H OH 0 1.031 SCH3 CF3 H H OH 0 Comp. R, R2 R3 R4 Rs P No.

1.032 SOCH3 CF3 H H OH 0 1.033SO2CH3 CF3 H H OH 0 1.034 SPh CF3 H H OH 0 1.035 SOPh CF3 H H OH 0 1.036SO2Ph CF3 H H OH 0 1.037 N (CH3) 2 CF3 H H OH 0 1.038 CH=CH2 CF3 H H OH 0 1.039 CH2CH=CH2 CF3 H H OH 0 1.04 S02N (CH3) 2 CF3 H H OH 0 1.041 ethynyl CF3 H H OH 0 1.042cyclopropyl CF3 H H OH 0 1.043 OCH3 CF3 H H OH 0 1.044 OPh CF3 H H OH 0 1.045 OCHF2 CF3 H H OH 0 1.046CO2Me CF3 H H OH 0 1.047 2-furyl CF3 H H OH 0 1.048 OCH2ethynyl CF3 H H OH 0 1.049 2-pyridyl CF3 H H OH 0 1.05 3-pyridyl CF3 H H OH 0 1.051 4-pyridyl CF3 H H OH 0 1.052 H CF3 H H OH 1 1.053F CF3 H H OH 1 1.054 Cl CF3 H H OH 1 1.055Br CF3 H H OH 1 1.056 CHF2 CF3 H H OH 1.057CCl3 CF3 H H OH 1 1.058CCIF2 CF3 H H OH 1 1.059CF3 CF3 H H OH 1 1.06 CH3CF3 H H OH 1 1.061CH2CH3 CF3 H H OH 1 1.062 CH (CH3) 2 CF3 H H OH 1 Comp. R, R2 R3 R4 Rs P No.

1.063 (CH2) 2CH3 CF3 H H OH 1.064 C (CH3) 3 CF3 H H OH 1 1.065Ph CF3 H H OH 1 1.066CH2F CF3 H H OH 1 1.067CH2Cl CF3 H H OH 1 1.068CH2Br CF3 H H OH 1 1.069CH2OH CF3 H H OH 1 1.07 CH2OCOCH3CF3 H H OH 1 1.071CH2OCOPh CF3 H H OH 1 1.072CH2OCH3 CF3 H H OH 1 1.073CH2OCH2CH3 CF3 H H OH 1 1.074CH2CH2OCH3 CF3 H H OH 1 1.075CH2SMe CF3 H H OH 1 1.076CH2SOMe CF3 H H OH 1 1.077 CH2SO2Me CF3 H H OH 1.078CH2SO2Ph CF3 H H OH 1 1.079 SCH2Ph CF3 H H OH 1 1.08SOCH2Ph CF3 H H OH 1 1.081 SO2CH2Ph CF3 H H OH 1.082SCH3 CF3 H H OH 1 1.083 SOCH3 CF3 H H OH 1 1.084SO2CH3 CF3 H H OH 1 1.085 SPh CF3 H H OH 1 1.086SOPh CF3 H H OH 1 1.087SO2Ph CF3 H H OH 1 1.088N(CH3)2 CF3 H H OH 1 1.089CH=CH2 CF3 H H OH 1 1.09CH2CH=CH2 CF3 H H OH 1 1.091SO2N(CH3)2 CF3 H H OH 1 1.092 ethynyl CF3 H H OH 1.093cyclopropyl CF3 H H OH 1 Comp. R1 R2 R3 R4 Rs P No.

1.094 OCH3 CF3 H H OH 1 1.095OPh CF3 H H OH 1 1.096OCHF2 CF3 H H OH 1 1.097CO2Me CF3 H H OH 1 1.0982-furyl CF3 H H OH 1 1.099OCH2CCH CF3 H H OH 1 1.1 2-pyridyl CF3 H HOH 1 1.1013-pyridyl CF3 H H OH 1 1.1024-pyridyl CF3 H H OH 1 1.103 H CF2CF3 H H OH 0 1.104 Cl CF2CF3 H H OH 0 1.105 CHF2 CF2CF3 H H OH 0 1.106 CCI3 CF2CF3 H H OH 0 1.107 CClF2CF2CF3 H H OH 0 1.108 CF3CF2CF3 H H OH 0 1.109 CH3 CF2CF3 H H OH 0 1.11 CH2CH3 CF2CF3 H H OH 0 1.111 CH (CH3) 2 CF2CF3 H H OH 0 1.112 (CH2) 2CH3 CF2CF3 H H OH 0 1.113 C (CH3) 3 CF2CF3 H H OH 0 1.114 CH2FCF2CF3 H H OH 0 1.115 CH2CI CF2CF3 H H OH 0 1.116 CH2OH CF2CF3 H H OH 0 1.117 CH2OCOCH3CF2CF3 H H OH 0 1.118 CH2OCOPhCF2CF3 H H OH 0 1.119 CH2OCH3CF2CF3 H H OH 0 1.12 CH2OCH2CH3 CF2CF3 H H OH 0 1.121 CH2SMe CF2CF3 H H OH 0 1.122 CH2SOMe CF2CF3 H H OH 0 1.123 CH2SO2MeCF2CF3 H H OH 0 1.124 CH2SO2PhCF2CF3 H H OH 0 Comp. R, R2 R3 R4 Rs P No.

1.125 N (CH3)2 CF2CF3 H H OH 0 1.126 CH=CH2 CF2CF3 H H OH 0 1.127 CH2CH=CH2CF2CF3 H H OH 0 1.128 SO2N (CH3)2 CF2CF3 H H OH 0 1.129 CCH CF2CF3 H H OH 0 1.13 cyclopropyl CF2CF3 H H OH 0 1.131 OPh CF2CF3 H H OH 0 1.132 OCH3 CF2CF3 H H OH 0 1.133 CO2MeCF2CF3 H H OH 0 1.134 OCH2CCHCF2CF3 H H OH 0 1.135 2-pyridyl CF2CF3 H H OH 0 1.136 3-pyridyl CF2CF3 H H OH 0 1.137 4-pyridyl CF2CF3 H H OH 0 1.138 H CF2CF3 H H OH 1 1.139 Cl CF2CF3 H H OH 1.14 CHF2CF2CF3 H H OH 1 1.141 CCI3 CF2CF3 H H OH 1.142 CCIF2 CF2CF3 H H OH 1 1.143CF3 CF2CF3 H H OH 1 1.144 CH3 CF2CF3 H H OH 1.145 CH2CH3 CF2CF3 H H OH 1 1.146 CH (CH3)2 CF2CF3 H H OH 1 1.147 (CH2) 2CH3 CF2CF3 H H OH 1 1.148 C (CH3) 3 CF2CF3 H H OH 1 1.149 CH2FCF2CF3 H H OH 1 1.15 CH2CI CF2CF3 H H OH 1.151 CH2OHCF2CF3 H H OH 1 1.152 CH2OCOCH3CF2CF3 H H OH 1 1.153 CH2OCOPhCF2CF3 H H OH 1 1.154 CH2OCH3CF2CF3 H H OH 1 1.155 CH2OCH2CH3CF2CF3 H H OH 1 Comp. R, R2 R3 R4 Rs P No.

1.156 CH2SMeCF2CF3 H H OH 1 1.157 CH2SOMeCF2CF3 H H OH 1 1.158 CH2SO2Me CF2CF3 H H OH 1.159 CH2SO2Ph CF2CF3 H H OH 1.16 N (CH3) 2 CF2CF3 H H OH 1.161 CH=CH2CF2CF3 H H OH 1 1.162CH2CH=CH2 CF2CF3 H H OH 1 1.163 SO2N (CH3) 2 CF2CF3 H H OH 1 1.164 CCHCF2CF3 H H OH 1 1.165 cyclopropylCF2CF3 H H OH 1 1.166 OPhCF2CF3 H H OH 1 1.167 OCH3 CF2CF3 H H OH 1 1.168 CO2MeCF2CF3 H H OH 1 1.169OCH2CCH CF2CF3 H H OH 1 1.17 2-pyridyi CF2CF3 H H OH 1.171 3-pyridyl CF2CF3 H H OH 1 1.172 4-pyridylCF2CF3 H H OH 1 1.173 HCF2CF2CF3 H H OH 0 1.174 CHF2 CF2CF2CF3 H H OH 0 1.175 CF3 CF2CF2CF3 H H OH 0 1.176 CH3 CF2CF2CF3 H H OH 0 1.177 CH2CH3 CF2CF2CF3 H H OH 0 1.178 (CH2) 2CH3 CF2CF2CF3 H H OH 0 1.179 CH2CI CF2CF2CF3 H H OH 0 1.18 CH2OCH3CF2CF2CF3 H H OH 0 1.181 HCF2CF2CF3 H H OH 1 1.182 CHF2CF2CF2CF3 H H OH 1 1.183 CF3 CF2CF2CF3 H H OH 1.184 CH3CF2CF2CF3 H H OH 1 1.185 CH2CH3CF2CF2CF3 H H OH 1 1.186 (CH2) 2CH3 CF2CF2CF3 H H OH 0 Comp. R, R2 R3 R4 R5 p No.

1.187 CH2CI CF2CF2CF3 H H OH 1.188 CH20CH3 CF2CF2CF3 H H OH 1.189 H CF2CI H H OH 0 1.19 ClCF2Cl H H OH 0 1.191 CHF2CF2Cl H H OH 0 1.192 CCI3 CF2CI H H OH 0 1.193 CCIF2 CF2CI H H OH 0 1.194 CF3CF2Cl H H OH 0 1.195 CH3 CF2CI H H OH 0 1.196 CH2CH3CF2Cl H H OH 0 1.197 CH (CH3)2 CF2Cl H H OH 0 1.198 (CH2) 2CH3 CF2CI H H OH 0 1.199 C (CH3) 3 CF2CI H H OH 0 1.2 CH2FCF2Cl H H OH 0 1.201 CH2CI CF2CI H H OH 0 1.202CH2OH CF2Cl H H OH 0 1.203 CH2OCOCH3 CF2CI H H OH ° 1.204CH2OCOPh CF2Cl H H OH 0 1.205 CH20CH3 CF2CI H H OH 0 1.206CH2OCH2CH3 CF2Cl H H OH 0 1.207CH2SMe CF2Cl H H OH 0 1.208 CH2SOMe CF2CI H H OH 0 1.209CH2SO2Me CF2Cl H H OH 0 1.21 CH2SO2PhCF2Cl H H OH 0 1.211 N (CH3) 2 CF2CI H H OH 0 1.212CH=CH2 CF2Cl H H OH 0 1.213 CH2CH=CH2 CF2CI H H OH 0 1.214SO2N(CH3)2 CF2CI H H OH 0 1.215 CCH CF2CI H H OH 0 1.216 cyciopropyl CF2CI H H OH 0 1.217 OPh CF2CI H H OH 0 Comp. R1 R2 R3 R4 R5 p No.

1.218 OCH3 CF2CI H H OH 0 1.219CO2Me CF2Cl H H OH 0 1.22 OCH2CCH CF2CI H H OH 0 1.221 2-pyridyl CF2CI H H OH 0 1.222 3-pyridyl CF2CI H H OH 0 1.223 4-pyridyl CF2CI H H OH 0 1.224 H CF2CI H H OH 1 1.225 ClCF2Cl H H OH 1 1.226CHF2 CF2Cl H H OH 1 1.227 CCI3 CF2CI H H OH 1 1.228 CCIF2 CF2CI H H OH 1 1.229 CF3CF2Cl H H OH 1 1.23 CH3 CF2CI H H OH 1 1.231CH2CH3 CF2Cl H H OH 1 1.232 CH (CH3) 2 CF2CI H H OH 1.233 (CH2) 2CH3 CF2CI H H OH 1 1.234 C (CH3) 3 CF2CI H H OH 1.235CH2F CF2Cl H H OH 1 1.236CH2Cl CF2Cl H H OH 1 1.237CH2OH CF2Cl H H OH 1 1.238 CH2OCOCH3 CF2CI H H OH 1.239CH2OCOPh CF2Cl H H OH 1 1.24 CH2OCH3 CF2CI H H OH 1.241CH2OCH2CH3 CF2Cl H H OH 1 1.242CH2SMe CF2Cl H H OH 1 1.243CH2SOMe CF2Cl H H OH 1 1.244 CH2SO2Me CF2CI H H OH 1.245CH2SO2Ph CF2Cl H H OH 1 1.246 N (CH3) 2 CF2CI H H OH 1.247 CH=CH2 CF2CI H H OH 1 1.248CH2CH=CH2 CF2Cl H H OH 1 Comp. R1 R2 R3 R4 R5 p No.

1.249SO2N(CH3)2 CF2Cl H H OH 1 1.25 CCHCF2Cl H H OH 1 1.251 cyclopropylCF2Cl H H OH 1 1.252 OPhCF2Cl H H OH 1 1.253OCH3 CF2Cl H H OH 1 1.254CO2Me CF2Cl H H OH 1 1.255OCH2CCH CF2Cl H H OH 1 1.256 HCCl3 H H OH 0 1.257 ClCCl3 H H OH 0 1.258 CH3CCl3 H H OH 0 1.259 CH2CH3 CCI3 H H OH 0 1.26 CH (CH3) 2 CCI3 H H OH 0 1.261 (CH2)2CH3 CCl3 H H OH 0 1.262 CH2F CCI3 H H OH 0 1.263 CH2CI CCI3 H H OH 0 1.264CH2OH CCl3 H H OH 0 1.265CH20COCH3CCbHHOH0 1.266 CH20COPh CCI3 H H OH 0 1.267CH2OCH3 CCl3 H H OH 0 1.268CH2OCH2CH3 CCl3 H H OH 0 1.269 CH2SMe CCI3 H H OH 0 1.27 CH2SOMe CCI3 H H OH 0 1.271CH2SO2Me CCl3 H H OH 0 1.272CH2SO2Ph CCl3 H H OH 0 1.273 cyclopropylCCl3 H H OH 0 1.274 OPh CCI3 H H OH 0 1.275 OCH3CCl3 H H OH 0 1.276CO2Me CCl3 H H OH 0 1.277 OCH2CCH CCI3 H H OH 0 1.278 HCCl3 H H OH 1 1.279Cl CCl3 H H OH 1 Comp. R1 R2 R3 R4 R5 p No.

1.28 CH3CCl3 H H OH 1 1.281 CH2CH3 CCI3 H H OH 1 1.282CH(CH3)2 CCl3 H H OH 1 1.283 (CH2) 2CH3 CCI3 H H OH 1 1.284CH2F CCl3 H H OH 1 1.285 CH2CI CCI3 H H OH 1 1.286CH2OH CCl3 H H OH 1 1.287CH2OCOCH3 CCl3 H H OH 1 1.288CH2OCOPh CCl3 H H OH 1 1.289CH2OCH3 CCl3 H H OH 1 1.29 CH20CH2CH3 CCI3 H H OH 1 1.291CH2SMe CCl3 H H OH 1 1.292 CH2SOMe CCI3 H H OH 1.293CH2SO2Me CCl3 H H OH 1 1.294CH2SO2Ph CCl3 H H OH 1 1.295cyclopropyl CCl3 H H OH 1 1.296OPh CCl3 H H OH 1 1.297OCH3 CCl3 H H OH 1 1.298CO2Me CCl3 H H OH 1 1.299OCH2CCH CCl3 H H OH 1 1.3 CF3 CHF2 H H OH 0 1.301 CH3 CHF2 H H OH 0 1.302 CH20CH3 CHF2 H H OH 0 1.303 CH2CI CHF2 H H OH 0 1.304 CH2F CHF2 H H OH 0 1.305CF3 CHF2 H H OH 1 1.306CH3 CHF2 H H OH 1 1.307CH2OCH3 CHF2 H H OH 1 1.308CH2Cl CHF2 H H OH 1 1.309CH2F CHF2 H H OH 1 1.31 CH3 CF3 H CH3 OH 0 Comp. R, R2 R3 R4 Rs P No.

1.311 CH3 CF3 H CH3 OH 1.312 Cl CF3 H CH3 OH 0 1.313 CH3 CF3 CH3 H OH 0 1.314 CH3 CF3 Ph H OH 0 1.315CH3 CF3 Cl H OH 0 1.316 CH3 CF3 CO2CH2CH3 H OH 0 1.317 CH3 CF3 C02CH2Ph H OH 0 1.318 CH3 CF3 CH3 H OH 1 1.319 CH3 CF3 Ph H OH 1 1.32 CH3 CF3 Cl H OH 1.321 CH3 CF3 C02CH2CH3 H OH 1 1.322CH3 CF3 CO2CH2Ph H OH 1 1.323 OCH3 CF3 CH3 H OH 0 1.324 CH20CH3 CF3 CH3 H OH 0 1.325 CH20CH3 CF3 Ph H OH 0 1.326 CH2OCH3 CF3 Cl H OH 0 1.327 CH20CH3 CF3 C02CH2CH3 H OH 0 1.328CH2OCH3 CF3 CO2CH2Ph H OH 0 1.329 CH2OCH3 CF3 CH3 H OH 1.33 CH2OCH3 CF3 Ph H OH 1.331 CH2OCH3 CF3 Cl H OH 1.332 CH20CH3 CF3 C02CH2CH3 H OH 1 1.333 CH20CH3 CF3 C02CH2Ph H OH 1 1.334 COOCH3 H H H OH 0 1.335 CF3 SCH3 H H OH 0 1.336 CH3 SCH3 H H OH 0 1.337 CF3 SOCH3 H H OH 0 1.338 CH3 SOCH3 H H OH 0 1.339CF3 SO2CH3 H H OH 0 1.34CH3 SO2CH3 H H OH 0 1.341CF3 SCH2CH3 H H OH 0 Comp. R, R2 R3 R4 Rs p No.

1.342 CH3 SCH2CH3 H H OH 0 1.343 CF3 SOCH2CH3 H H OH 0 1.344 CH3 SOCH2CH3 H H OH 0 1.345 CF3 SO2CH2CH3 H H OH 0 1.346CH3 SO2CH2CH3 H H OH 0 1.347 CF3 OCH3 H H OH 0 1.348 CH3 OCH3 H H OH 0 1.349CF3 OCH2CF3 H H OH 0 1.35CH3 OCH2CF3 H H OH 0 1.351 CF3 OCH2CCH H H OH 0 1.352CH3 OCH2CCH H H OH 0 1.353 CF3 CN H H OH 0 1.354 CH3 CN H H OH 0 1.355 CF3 Cl H H OH 0 1.356 CF3 Cl H H O-NEt3+ 0 1.357CH3 Cl H H OH 0 1.358 H Cl H H OH 0 1.359 CF3 OCH3 H H OH 0 1.36 CH3 OCH3 H H OH 0 1.361 CF3 CH3 H H OH 0 1.362 H CF3 H CH3 OH 0 1.363 H CF3 H CF3 OH 0 1.364 H CF3 H CH2CH3 OH 0 1.365 H CF3 H CF3 OH 0 1.366 H CF3 H SCH3 OH 0 1.367 H CF3 H SOCH3 OH 0 1.368H CF3 H SO2CH3 OH 0 1.369 H CF3 H Cl OH 0 1.37 H CF3 H OCH3 OH 0 1.371 H CH3 H CF3 OH 0 1.372 H Cl H CF3 OH 0 Comp. R, R2 R3 R4 R5 p No.

1.373 H OCH3 H CF3 OH 0 1.374 H SCH3 H CF3 OH 0 1.375 H SOCH3 H CF3 OH 0 1.376 CH3 CF3 H H O-K+ 0 1.377CH3 CF3 H H S(CH2)7CH3 0 1.378CH3 CF3 H H S(CH2)7CH3 0 1.379CH3 CF3 H H SO(CH2)7CH3 0 1.38 CH3 CF3 H H SO2(CH2)7CH3 0 1.381 CH3 CF3 H H SPh 0 1.382 CH3 CF3 H H SOPh 0 1.383 CH3 CF3 H H SO2Ph 0 1.384 CH3 CF3 H H NOCH3 0 1.385 CH3 CF3 H H NOCH2Ph 0 1.386CH3 CF3 H H NOCH2CH=CH2 0 1.387 CH3 CF3 H H NOC (CH3) 3 0 1.388 CH3 CF3 H H NOCH2CH3 0 1.389 CH3 CF3 H H NCH2CH2SH 0 1.39 CH3 CF3 H HNN(CH3)2 0 1.391 CH3 CF3 H H NN (CH3) C (S) NH2 0 1.392 CH3 CF3 H H N-morpholino 0 1.393 CH3 CF3 H H NHCOCH3 0 1.394CH3 CF3 H H NHCO(CH2)7CH3 0 1.395 CH3 CF3 H H NHCOPh 0 1.396 CH3 CF3 H H NHSO2CH3 0 1.397 CH3 CF3 H H NH (CO)S(CH2)7CH3 0 1.398 CH3 CF3 H H Cl 0 1.399CH3 CF3 H H NH2 0 1.4 CH3 CF3 H H OCOC (CH3) 3 0 1.401 CH3 CF3 H H OCOCH3 0 1.402 CH3 CF3 H H OCOPh 0 1.403CH3 CF3 H H OCO-cyclopropyl 0 Comp. R, R2 R3 R4 Rs P No. 1.404 CH3 CF3 H H OCOCH2CH3 0 1.405 CH3 CF3 H H OCOCH=CH2 0 1.406 CH3 CF3 H H OCOCH=CHCH3 0 1.407 CH3 CF3 H H O (CO) SCH3 0 1.408 CH3 CF3 H H O (CO) S (CH2) 7CH3 0 1.409 CH3 CF3 H H O (CO) OCH2CH3 0 1.41 CH3 CF3 H H O (CO) N (CH2CH3) 2 0 1.411 CH3 (CF2) 3CF3 H H OH 0 1.412 CH3 CF3 H H S-(4-CI-phenyl) 0 1.413 CH3 CF3 H H SO-(4-CI-phenyl) 0 1.414 CH3 CF3 H H SO2-(4-CI-phenyl) 0 1.415 CH3 CF3 H H S- (4-CF3-phenyl) 0 1.416 CH3 CF3 H H SO- (4-CF3-phenyl) 0 1.417 CH3 CF3 H H S02- (4-CF3-phenyl) 0 1.418 CH3 CF3 H H S-(4-NO2-phenyl) 0 1.419 CH3 CF3 H H SO-(4-NO2-phenyl) 0 1.42 CH3 CF3 H H SO2-(4-NO2-phenyl) 0 1.421 CH3 CF3 H H s 0 0 u 1.422CHsCFsHHsH0 T N 1.423 CH3 CF3 H H SYY 0 NU 1.424 CH3 CF3 H H s (SCH3 il 1.425 CF2H SCH3 H H OH 0 1.426 CF2CI SCH3 H H OH 0 1.427 CF2H SOCH3 H H OH 0 1.428 CF2CI SOCH3 H H OH 0 1.429 CF2H S02CH3 H H OH 0 1.43 CF2CI SO2CH3 H H OH 0 Comp. R, R2 R3 R4 Rs P No.

1.431 CF2H SCH2CH3 H H OH 0 1.432 CF2Ci SCH2CH3 H H OH 0 1.433 CF2H SOCH2CH3 H H OH 0 1.434 CF2CI SOCH2CH3 H H OH 0 1.435 CF2HSO2CH2CH3 H H OH 0 1.436 CF2CI SO2CH2CH3 H H OH 0 1.437 CF2H OCH3 H H OH 0 1.438 CF2ClOCH3 H H OH 0 1.439 CF2H OCH2CF3 H H OH 0 1.44 CF2CI OCH2CF3 H H OH 0 1.441 CF2H OCH2CCH H H OH 0 1.442 CF2CI OCH2CCH H H OH 0 1.443 CF2H CN H H OH 0 1.444 CF2CI CN H H OH 0 1.445CF2H Cl H H OH 0 1.446CF2Cl Cl H H OH 0 1.447 CF2H OCH3 H H OH 0 1.448 CF2CI OCH3 H H OH 0 1.449 CF3 CH2OCH3 H H OH 0 1.45 CF3CH2OCH3 H H OH 1 1.451 CF2ClCH2OCH3 H H OH 0 1.452 CF2CI CH2OCH3 H H OH 1.453 CF2HCH2OCH3 H H OH 0 1.454 CF2H CH2OCH3 H H OH 1.455 CN CF3 H H OH 0 Table2: Comp. No. R, R2 R3 R4 2.001 H CF3 H H 2.002 F CF3 H H 2.003Cl CF3 H H 2.004 Br CF3 H H 2.005 CHF2 CF3 H H 2.006CCl3 CF3 H H 2.007 CCIF2 CF3 H H 2.008 CF3 CF3 H H 2.009 CH3 CF3 H H 2.01 CH2CH3 CF3 H H 2.011 CH (CH3) 2 CF3 H H 2.012 (CH2) 2CH3 CF3 H H 2.013 Ph CF3 H H 2.014 CH2F CF3 H H 2.015 CH2CI CF3 H H 2.016 CH2Br CF3 H H 2.017 CH20H CF3 H H 2.018 CH20COCH3 CF3 H H 2.019 CH20COPh CF3 H H 2.02 CH20CH3 CF3 H H 2.021 CH20CH2CH3 CF3 H H 2.022 CH2CH20CH3 CF3 H H 2.023CH2SMe CF3 H H 2.024 CH2SOMe CF3 H H 2.025 CH2S02Me CF3 H H 2.026CH2SO2Ph CF3 H H Comp. No. R, R2 R3 R4 2.027 SCH2Ph CF3 H H 2.028 SOCH2Ph CF3 H H 2.029 S02CH2Ph CF3 H H 2.03 SCH3 CF3 H H 2.031 SOCH3 CF3 H H 2.032 S02CH3 CF3 H H 2.033 N (CH3) 2 CF3 H H 2.034 CH=CH2 CF3 H H 2.035 CH2CH=CH2 CF3 H H 2.036 S02N (CH3) 2 CF3 H H 2.037 CCH CF3 H H 2.038 OCH3 CF3 H H 2.039 OPh CF3 H H 2.04 OCHF2 CF3 H H 2.041 C02Me CF3 H H 2.042 OCH2CCH CF3 H H 2.043 OCH2CF3 CF3 H H 2.044 H CF3 H Cl 2.045 ClX OCHF2 F H Cl N N 2.046 CN CF3 H H 2.047 H CHF2 H H 2.048 CH3 CHF2 H H 2.049 CH2CH3 CHF2 H H 2.05 CH20CH3 CHF2 H H 2.051 H CF2CI H H 2.052 CH3 CF2CI H H 2.053 CH2CH3 CF2CI H H 2.054 CH2OCH3 CF2CI H H Table 3: Comp. No. R, R2 R3 R4 3.001 H CF3 H H 3.002 F CF3 H H 3.003Cl CF3 H H 3.004 Br CF3 H H 3.005 CHF2 CF3 H H 3.006CCl3 CF3 H H 3.007CClF2 CF3 H H 3.008 CF3 CF3 H H 3.009 CH3 CF3 H H 3.01 CH2CH3 CF3 H H 3.011 CH (CH3) 2 CF3 H H 3.012 (CH2) 2CH3 CF3 H H 3.013 Ph CF3 H H 3.014 CH2F CF3 H H 3.015 CH2CI CF3 H H 3.016 CH2Br CF3 H H 3.017CH2OH CF3 H H 3.018 CH20COCH3 CF3 H H 3.019 CH20COPh CF3 H H 3.02CH2OCH3 CF3 H H 3.021 CH20CH2CH3 CF3 H H 3.022 CH2CH20CH3 CF3 H H 3.023 CH2SMe CF3 H H 3.024 CH2SOMe CF3 H H 3.025 CH2SO2Me CF3 H H Comp. No. R, R2 R3 R4 3.026 CH2SO2Ph CF3 H H 3.027 SCH2Ph CF3 H H 3.028 SOCH2Ph CF3 H H 3.029 So2CH2Ph CF3 H H 3.03 SCH3 CF3 H H 3.031 SOCH3 CF3 H H 3.032 S02CH3 CF3 H H 3.033 N (CH3) 2 CF3 H H 3.034 CH=CH2 CF3 H H 3.035 CH2CH=CH2 CF3 H H 3.036 SO2N (CH3) 2 CF3 H H 3.037 CCH CF3 H H 3.038 OCH3 CF3 H H 3.039 OPh CF3 H H 3.04 OCHF2 CF3 H H 3.041 C02Me CF3 H H 3.042 OCH2CCH CF3 H H 3.043 OCH2CF3 CF3 H H 3.044 H CF3 H H 3.045 CN CF3 H H 3.046 H CHF2 H H 3.047 CH3 CHF2 H H 3.048 CH2CH3 CHF2 H H 3.049 CH20CH3 CHF2 H H 3.05 H CF2CI H H 3.051 CH3 CF2CI H H 3.052 CH2CH3 CF2CI H H 3.053 CH20CH3 CF2CI H H 3.054 Cl CH3 H H 3.055 CN SCH3 H H 3.056 CN S02CH3 H H Table 4: Comp. R, R2 R3 R4 Rs P No.

4.001 H CF3 H H OH 0 4.002 F CF3 H H OH 0 4.003Cl CF3 H H OH 0 4.004 Br CF3 H H OH 0 4.005 CHF2 CF3 H H OH 0 4.006 CCI3 CF3 H H OH 0 4.007 CCIF2 CF3 H H OH 0 4.008 CF3 CF3 H H OH 0 4.009 CH3 CF3 H H OH 0 4.01 CH2CH3CF3 H H OH 0 4.011 CH (CH3) 2 CF3 H H OH 0 4.012 (CH2) 2CH3 CF3 H H OH 0 4.013 C (CH3) 3 CF3 H H OH 0 4.014 Ph CF3 H H OH 0 4.015 CH2F CF3 H H OH 0 4.016 CH2CI CF3 H H OH 0 4.017 CH2Br CF3 H H OH 0 4.018CH2OH CF3 H H OH 0 4.019CH2OCOCH3 CF3 H H OH 0 4.02CH2OCOPh CF3 H H OH 0 4.021CH2OCH3 CF3 H H OH 0 4.022 CH2OCH2CH3 CF3 H H OH 0 4.023 CH2CH2OCH3 CF3 H H OH 0 Comp. R1 R2 R3 R4 Rs P No.

4.024 CH2SMe CF3 H H OH 0 4.025 CH2SOMe CF3 H H OH 0 4.026CH2SO2Me CF3 H H OH 0 4.027CH2SO2Ph CF3 H H OH 0 4.028 N (CH3) 2 CF3 H H OH 0 4.029 CH=CH2 CF3 H H OH 0 4.03 CH2CH=CH2CF3 H H OH 0 4.031 SO2N (CH3) 2 CF3 H H OH 0 4.032 CCH CF3 H H OH 0 4.033 cyclopropyl CF3 H H OH 0 4.034 OCH3 CF3 H H OH 0 4.035 OPh CF3 H H OH 0 4.036 OCHF2 CF3 H H OH 0 4.037CO2Me CF3 H H OH 0 4.038OCH2CCH CF3 H H OH 0 4.039H CF3 H H OH 1 4.04 F CF3 H H OH 1 4.041 Cl CF3 H H OH 4.042Br CF3 H H OH 1 4.043CHF2 CF3 H H OH 1 4.044CCl3 CF3 H H OH 1 4.045CClF2 CF3 H H OH 1 4.046CF3 CF3 H H OH 1 4.047CH3 CF3 H H OH 1 4.048 CH2CH3 CF3 H H OH 4.049 CH (CH3)2 CF3 H H OH 1 4.05 (CH2)2CH3 CF3 H H OH 1 4.051C(CH3)3 CF3 H H OH 1 4.052Ph CF3 H H OH 1 4.053 CH2F CF3 H H OH 4.054CH2Cl CF3 H H OH 1 Comp. RiR2R3RtRsP No.

4.055 CH2Br CF3 H H OH 4.056 CH20H CF3 H H OH 4.057 CH2OCOCH3 CF3 H H OH 1 4.058 CH2OCOPh CF3 H H OH 1 4.059CH2OCH3 CF3 H H OH 1 4.06 CH2OCH2CH3CF3 H H OH 1 4.061CH2CH2OCH3 CF3 H H OH 1 4.062 CH2SMe CF3 H H OH 1 4.063CH2SOMe CF3 H H OH 1 4.064 CH2SO2Me CF3 H H OH 4.065CH2SO2Ph CF3 H H OH 1 4.066 N (CH3) 2 CF3 H H OH 4.067CH=CH2 CF3 H H OH 1 4.068 CH2CH=CH2 CF3 H H OH 4.069SO2N(CH3)2 CF3 H H OH 1 4.07 CCH CF3 H H OH 1 4.071cyclopropyl CF3 H H OH 1 4.072OCH3 CF3 H H OH 1 4.073 OPh CF3 H H OH 1 4.074OCHF2 CF3 H H OH 1 4.075CO2Me CF3 H H OH 1 4.0762-furyl CF3 H H OH 1 4.077OCH2CCH CF3 H H OH 1 4.078 H CF2CF3 H H OH 0 4.079 ClCF2CF3 H H OH 0 4.08 CHF2CF2CF3 H H OH 0 4.081 CCl3CF2CF3 H H OH 0 4.082 CClF2CF2CF3 H H OH 0 4.083 CF3 CF2CF3 H H OH 0 4.084 CH3 CF2CF3 H H OH 0 4.085 CH2CH3 CF2CF3 H H OH 0 Comp. R, R2 R3 R4 Rs P No.

4.086 CH (CH3)2 CF2CF3 H H OH 0 4.087 (CH2) 2CH3 CF2CF3 H H OH 0 4.088 C (CH3) 3 CF2CF3 H H OH 0 4.089 CH2F CF2CF3 H H OH 0 4.09 CH2ClCF2CF3 H H OH 0 4.091 CH2OHCF2CF3 H H OH 0 4.092 CH2OCOCH3CF2CF3 H H OH 0 4.093 CH2OCOPhCF2CF3 H H OH 0 4.094 CH2OCH3 CF2CF3 H H OH 0 4.095 CH2OCH2CH3CF2CF3 H H OH 0 4.096 CH2SMe CF2CF3 H H OH 0 4.097 CH2SOMe CF2CF3 H H OH 0 4.098 CH2SO2MeCF2CF3 H H OH 0 4.099 CH2SO2PhCF2CF3 H H OH 0 4.1 N (CH3) 2 CF2CF3 H H OH 0 4.101 CH=CH2 CF2CF3 H H OH 0 4.102 CH2CH=CH2 CF2CF3 H H OH ° 4.103 S02N (CH3) 2 CF2CF3 H H OH 0 4.104 CCH CF2CF3 H H OH 0 4.105 cyclopropyl CF2CF3 H H OH 0 4.106 OPh CF2CF3 H H OH 0 4.107 OCH3 CF2CF3 H H OH 0 4.108 CO2Me CF2CF3 H H OH 0 4.109 OCH2CCHCF2CF3 H H OH 0 4.11 H CF2CF2CF3 H H OH 0 4.111 CHF2 CF2CF2CF3 H H OH 0 4.112 CF3 CF2CF2CF3 H H OH 0 4.113 CH3 CF2CF2CF3 H H OH 0 4.114 CH2CH3 CF2CF2CF3 H H OH 0 4.115 (CH2) 2CH3 CF2CF2CF3 H H OH 0 4.116 CH2ClCF2CF2CF3 H H OH 0 Comp. R1 R2 R3 R4 R5 P<BR> No.

4.117 CH2OCH3CF2CF2CF3 H H OH 0 4.118 H CF2CI H H OH 0 4.119 Cl CF2CI H H OH 0 4.12 CHF2 CF2CI H H OH 0 4.121 CCI3 CF2CI H H OH 0 4.122CClF2 CF2Cl H H OH 0 4.123 CF3 CF2CI H H OH 0 4.124 CH3CF2Cl H H OH 0 4.125 CH2CH3 CF2CI H H OH 0 4.126 CH (CH3)2 CF2Cl H H OH 0 4.127 (CH2) 2CH3 CF2CI H H OH 0 4.128 C (CH3) 3 CF2CI H H OH 0 4.129 CH2F CF2CI H H OH 0 4.13 CH2CI CF2CI H H OH 0 4.131 CH2OHCF2Cl H H OH 0 4.132CH2OCOCH3 CF2Cl H H OH 0 4.133 CH20COPh CF2CI H H OH 0 4.134CH2OCH3 CF2Cl H H OH 0 4.135CH2OCH2CH3 CF2Cl H H OH 0 4.136 CH2SMe CF2CI H H OH 0 4.137 CH2SOMe CF2CI H H OH 0 4.138 CH2SO2Me CF2CI H H OH 0 4.139 CH2SO2Ph CF2CI H H OH 0 4.14 N (CH3)2 CF2Cl H H OH 0 4.141 CH=CH2 CF2CI H H OH 0 4.142 CH2CH=CH2 CF2CI H H OH 0 4.143 SO2N (CH3) 2 CF2CI H H OH 0 4.144 CCHCF2Cl H H OH 0 4.145 cyclopropyl CF2CI H H OH 0 4.146 OPh CF2CI H H OH 0 4.147 OCH3 CF2CI H H OH 0 Comp. R1 R2 R3 R4 R5 P<BR> No.

4.148 C02Me CF2CI H H OH 0 4.149 OCH2CCH CF2CI H H OH 0 4.15 CH3CF2Cl H H OH 1 4.151 CH2OCH3CF2Cl H H OH 1 4.152 HCCl3 H H OH 0 4.153 ClCCl3 H H OH 0 4.154 CH3CCl3 H H OH 0 4.155 CH2CH3CCl3 H H OH 0 4.156 CH (CH3) 2 CCI3 H H OH 0 4.157 (CH2) 2CH3 3HHOH0 4.158 CH2FCCl3 H H OH 0 4.159 CH2CI CCI3 H H OH 0 4.16 CH20H CCI3 H H OH 0 4.161 CH2OCOCH3CCl3 H H OH 0 4.162 CH20COPh CCI3 H H OH 0 4.163CH2OCH3 CCl3 H H OH 0 4.164 CH20CH2CH3 CCI3 H H OH 0 4.165 CH2SMe CCI3 H H OH 0 4.166 CH2SOMeCCl3 H H OH 0 4.167 CH2SO2MeCCl3 H H OH 0 4.168 CH2SO2PhCCl3 H H OH 0 4.169 cyclopropyl CCI3 H H OH 0 4.17 OPhCCl3 H H OH 0 4.171 OCH3CCl3 H H OH 0 4.172CO2Me CCl3 H H OH 0 4.173 OCH2CCHCCl3 H H OH 0 4.174 CF3CHF2 H H OH 0 4.175 CH3CHF2 H H OH 0 4.176 CH20CH3 CHF2 H H OH 0 4.177 CH2ClCHF2 H H OH 0 4.178 CH2FCHF2 H H OH 0 Comp. RiRzRsRtRsP No.

4.179CF3 CHF2 H H OH 1 4.18 CH3CHF2 H H OH 1 4.181 CH2OCH3CHF2 H H OH 1 4.182 CH2CI CHF2 H H OH 1 4.183 CH2FCHF2 H H OH 1 4.184 CH3 CF3 H CH3 OH 0 4.185 CH3 CF3 H CH3 OH 1 4.186 Cl CF3 H CH3 OH 0 4.187 CH3 CF3 CH3 H OH 0 4.188 CH3 CF3 Ph H OH 0 4.189 CH3 CF3 Cl H OH 0 4.19 CH3 CF3 C02CH2CH3 H OH 0 4.191 CH3 CF3 C02CH2Ph H OH 0 4.192 CH3 CF3 CH3 H OH 1 4.193 CH3 CF3 Ph H OH 1 4.194 CH3 CF3 Cl H OH 4.195CH3 CF3 CO2CH2CH3 H OH 1 4.196 CH3 CF3 CO2CH2Ph H OH 1 4.197 OCH3 CF3 CH3 H OH 0 4.198 CH20CH3 CF3 CH3 H OH 0 4.199 CH20CH3 CF3 Ph H OH 0 4.2CH2OCH3 CF3 Cl H OH 0 4.201 CH20CH3 CF3 C02CH2CH3 H OH 0 4.202 CH20CH3 CF3 C02CH2Ph H OH 0 4.203CH2OCH3 CF3 CH3 H OH 1 4.204CH2OCH3 CF3 Ph H OH 1 4.205 CH20CH3 CF3 CI H OH 1 4.206CH2OCH3 CF3 CO2CH2CH3 H OH 1 4.207 CH20CH3 CF3 C02CH2Ph H OH 1 4.208 COOCH3 H H H OH 0 4.209 CF3 SCH3 H H OH 0 Comp. R, R2 R3 R4 R5 p No.

4.21 CH3 SCH3 H H OH 0 4.211 CF3 SOCH3 H H OH 0 4.212 CH3 SOCH3 H H OH 0 4.213 CF3SO2CH3 H H OH 0 4.214 CH3SO2CH3 H H OH 0 4.215 CF3SCH2CH3 H H OH 0 4.216 CH3 SCH2CH3 H H OH 0 4.217 CF3SOCH2CH3 H H OH 0 4.218 CH3 SOCH2CH3 H H OH 0 4.219 CF3SO2CH2CH3 H H OH 0 4.22 CH3 SO2CH2CH3 H H OH 0 4.221 CF3 OCH3 H H OH 0 4.222 CH3 OCH3 H H OH 0 4.223 CF3 OCH2CF3 H H OH 0 4.224 CH3 OCH2CF3 H H OH 0 4.225 CF3 OCH2CCH H H OH 0 4.226 CH3 OCH2CCH H H OH 0 4.227 CF3 CN H H OH 0 4.228 CH3 CN H H OH 0 4.229 CF3 Cl H H OH 0 4.23 CH3 Cl H H OH 0 4.231 H Cl H H OH 0 4.232 CF3 OCH3 H H OH 0 4.233 CH3 OCH3 H H OH 0 4.234 CF3 CH3 H H OH 0 4.235 H CF3 H CH3 OH 0 4.236 H CF3 H CF3 OH 0 4.237 H CF3 H CH2CH3 OH 0 4.238 H CF3 H CF3 OH 0 4.239 H CF3 H SCH3 OH 0 4.24 H CF3 H SOCH3 OH 0 Comp. RiR2RsFLtRsP No.

4.241 H CF3 H SO2CH3 OH 0 4.242 H CF3 H Cl OH 0 4.243 H CF3 H OCH3 OH 0 4.244 H CH3 H CF3 OH 0 4.245 H Cl H CF3 OH o 4.246 H OCH3 H CF3 OH 0 4.247 H SCH3 H CF3 OH 0 4.248 H SOCH3 H CF3 OH 0 4.249 CH3 CF3 H HS(CH2)7CH3 0 4.25 CH3 CF3 H HS(CH2)7CH3 0 4.251 CH3 CF3 H HSO(CH2)7CH3 0 4.252 CH3 CF3 H HSO2(CH2)7CH3 0 4.253 CH3 CF3 H H SPh 0 4.254 CH3 CF3 H H SOPh 0 4.255 CH3 CF3 H HSO2Ph 0 4.256 CH3 CF3 H H NOCH3 0 4.257 CH3 CF3 H H NOCH2Ph 0 4.258 CH3 CF3 H HNOCH2CH=CH2 0 4.259 CH3 CF3 H H NOC (CH3) 3 0 4.26 CH3 CF3 H H NOCH2CH3 0 4.261 CH3 CF3 H H NCH2CH2SH 0 4.262 CH3 CF3 H HNN(CH3)2 0 4.263 CH3 CF3 H H NN (CH3) C (S) NH2 0 4.264 CH3 CF3 H H N-morpholino 0 4.265 CH3 CF3 H H NHCOCH3 0 4.266 CH3 CF3 H HNHCO(CH2)7CH3 0 4.267 CH3 CF3 H H NHCOPh 0 4.268 CH3 CF3 H H NHS02CH3 0 4.269 CH3 CF3 H H NH (CO) S (CH2) 7CH3 0 4.27 CH3 CF3 H H Cl 0 4.271CH3 CF3 H H NH2 0 Comp. Ri R2 R3 R4 Rs P No. 4.272 CH3 CF3 H H OCOC (CH3) 3 0 4.273 CH3 CF3 H H OCOCH3 0 4.274 CH3 CF3 H H OCOPh 0 4.275 CH3 CF3 H H OCO-cyclopropyl 0 4.276 CH3 CF3 H H OCOCH2CH3 0 4.277 CH3 CF3 H H OCOCH=CH2 0 4.278 CH3 CF3 H H OCOCH=CHCH3 0 4.279 CH3 CF3 H H O (CO) SCH3 0 4.28 CH3 CF3 H H O (CO) S (CH2) 7CH3 0 4.281 CH3 CF3 H H O (CO) OCH2CH3 0 4.282 CH3 CF3 H H O (CO) N (CH2CH3) 2 0 4.283 CH3 (CF2) 3CF3 H H OH 0 4.284 CH3 CF3 H H S- (4-CI-phenyl) 0 4.285 CH3 CF3 H H SO- (4-Cl-phenyl) 0 4.286 CH3 CF3 H H S02- (4-CI-phenyl) 0 4.287 CH3 CF3 H H S- (4-CF3-phenyl) 0 4.288 CH3 CF3 H H SO- (4-CF3-phenyl) 0 4.289 CH3 CF3 H H S02- (4-CF3-phenyl) 0 4.29 CH3 CF3 H H S- (4-NO2-phenyl) 0 4.291 CH3 CF3 H H SO- (4-NO2-phenyl) 0 4.292 CH3 CF3 H H S02- (4-NO2-phenyl) 0 4.293 CH3 CF3 H H s 0 0 u 4.294 CH3 CF3 H H s HN ° 4.295 CH3 CF3 H H s irN 0 N 4.296 CH3 CF3 H H S S 0 --SCH3 NON 4.297 CF2H SCH3 H H OH 0 Comp. R, R2 R3 R4 Rs P No.

4.298 CF2CI SCH3 H H OH 0 4.299 CF2H SOCH3 H H OH 0 4.3 CF2CI SOCH3 H H OH 0 4.301 CF2HSO2CH3 H H OH 0 4.302 CF2CI SO2CH3 H H OH 0 4.303 CF2H SCH2CH3 H H OH 0 4.304 CF2ClSCH2CH3 H H OH 0 4.305 CF2H SOCH2CH3 H H OH 0 4.306 CF2CI SOCH2CH3 H H OH 0 4.307 CF2HSO2CH2CH3 H H OH 0 4.308 CF2ClSO2CH2CH3 H H OH 0 4.309 CF2H OCH3 H H OH 0 4.31 CF2CI OCH3 H H OH 0 4.311 CF2HOCH2CF3 H H OH 0 4.312 CF2CI OCH2CF3 H H OH ° 4.313 CF2H OCH2CCH H H OH 0 4.314 CF2ClOCH2CCH H H OH 0 4.315 CF2H CN H H OH 0 4.316 CF2CI CN H H OH 0 4.317 CF2H Cl H H OH 0 4.318 CF2CI Cl H H OH 0 4.319 CF2H OCH3 H H OH 0 4.32 CF2CI OCH3 H H OH 0 4.321CF3 CH2OCH3 H H OH 0 4.322CF3 CH2OCH3 H H OH 1 4.323 CF2ClCH2OCH3 H H OH 0 4.324 CF2ClCH2OCH3 H H OH 1 4.325 CF2H CH2OCH3 H H OH 0 4.326 CF2HCH2OCH3 H H OH 1 4.327 CN CF3 H H OH 0 4.328 SCH3 H H H OH 0 Table5 Comp. No. R, R2 R3 R4 Rs 5.001 H CF3 H H CH3 5.002 F CF3 H H CH3 5.003 Cl CF3 H H CH3 5.004 CHF2 CF3 H H CH3 5.005 CCI3 CF3 H H CH3 5.006 CCIF2 CF3 H H CH3 5.007 CF3 CF3 H H CH3 5.008 CH3 CF3 H H CH3 5.009CH2CH3 CF3 H H CH3 5.01 CH (CH3) 2 CF3 H H CH3 5.011 (CH2) 2CH3 CF3 H H CH3 5.012 CH2F CF3 H H CH3 5.013 CH2CI CF3 H H CH3 5.014CH2Br CF3 H H CH3 5.015CH2OCOCH3 CF3 H H CH3 5.016 CH20CH3 CF3 H H CH3 5.017CH2CH2OCH3 CF3 H H CH3 5.018 CH2SMe CF3 H H CH3 5.019 CH2SOMe CF3 H H CH3 5.02CH2SO2Me CF3 H H CH3 5.021 N (CH3) 2 CF3 H H CH3 5.022CH=CH2 CF3 H H CH3 5.023 CH2CH=CH2 CF3 H H CH3 5.024SO2N(CH3)2 CF3 H H CH3 Comp. No. R, R2 R3 R4 R5 5.025 CCH CF3 H H CH3 5.026 cyclopropyl CF3 H H CH3 5.027 OCH3 CF3 H H CH3 5.028 OPh CF3 H H CH3 5.029OCHF2 CF3 H H CH3 5.03 CO2Me CF3 H H CH3 5.031 OCH2CCH CF3 H H CH3 5.032 CF3 SCH3 H H CH3 5.033 CH3 SCH3 H H CH3 5.034 CF3 SOCH3 H H CH3 5.035 CH3 SOCH3 H H CH3 5.036CF3 SO2CH3 H H CH3 5.037 CH3 SO2CH3 H H CH3 5.038 CF3 OCH3 H H CH3 5.039 CH3 OCH3 H H CH3 5.04 CF3 OCH2CF3 H H CH3 5.041 CH3 OCH2CF3 H H CH3 5.042 CF3OCH2CCH H H CH3 5.043 CH3 OCH2CCH H H CH3 5.044 CF3 CN H H CH3 5.045 CH3 CN H H CH3 5.046 CF3 Cl H H CH3 5.047 CH3 Cl H H CH3 5.048 H Cl H H CH3 5.049 CF3 OCH3 H H CH3 5.05 CH3 OCH3 H H CH3 5.051 CF3 CH3 H H CH3 5.052 H CF3 H CH3 CH3 5.053 H CF3 H CF3 CH3 5.054 H CF3 H CH2CH3 CH3 5.055 H CF3 H CF3 CH3 5.056 H CF3 H SCH3 CH3 Comp. No. R, R2 R3 R4 Rs 5.057 H CF3 H SOCH3 CH3 5.058 H CF3 H S02CH3 CH3 5.059 H CF3 H Cl CH3 5.06 H CF3 H OCH3 CH3 5.061 H CH3 H CF3 CH3 5.062 H Cl H CF3 CH3 5.063 H OCH3 H CF3 CH3 5.064 H SCH3 H CF3 CH3 5.065 H SOCH3 H CF3 CH3 5.066 CF2CI CH3 H H CH3 5.067 CF2CI CH2CH3 H H CH3 5.068 CF2CI SCH3 H H CH3 5.069 CF2CI SOCH3 H H CH3 5.07 CF2ClSO2CH3 H H CH3 5.071 CF2CI OCH3 H H CH3 5.072 CF2CI OCH2CF3 H H CH3 5.073 CF2CI OCH2CCH H H CH3 5.074 CF2CI CN H H CH3 5.075 CF2CI Cl H H CH3 5.076 CF2CI OCH3 H H CH3 5.077 CF3CH2OCH3 H H CH3 5.078 CF2ClCH2OCH3 H H CH3 5.079 CF2HCH2OCH3 H H CH3 5.08 CN CF3 H H CH3 5.081 CH3 CF3 H H CH2CH3 5.082 CH3 CF3 H H SCH3 5.083 CH3 CF3 H H SOCH3 5.084CH3 CF3 H H SO2CH3 5.085 CH3 CF3 H H H Table 6: Comp. No. R, R2 R3 R4 R5 6.001 Cl CF3 H H CH2CH3 6.002 CHF2 CF3 H H CH2CH3 6.003 CCI3 CF3 H H CH2CH3 6.004 CCIF2 CF3 H H CH2CH3 6.005CF3 CF3 H H CH2CH3 6.006 CH3 CF3 H H CH2CH3 6.007 CH2CH3 CF3 H H CH2CH3 6.008 (CH2) 2CH3 CF3 H H CH2CH3 6.009 CH2F CF3 H H CH2CH3 6.01 CH2CI CF3 H H CH2CH3 6.011CH2OCH3 CF3 H H CH2CH3 6.012CH2SMe CF3 H H CH2CH3 6.013CH2SO2Me CF3 H H CH2CH3 6.014CH=CH2 CF3 H H CH2CH3 6.015 CH2CH=CH2 CF3 H H CH2CH3 6.016CCH CF3 H H CH2CH3 6.017 CF3 SCH3 H H CH2CH3 6.018 CF3 SOCH3 H H CH2CH3 6.019 CF3 SO2CH3 H H CH2CH3 6.02 CF3 OCH3 H H CH2CH3 6.021 CF3 CN H H CH2CH3 6.022 CF3 Cl H H CH2CH3 6.023 CF3 OCH3 H H CH2CH3 6.024 CF3 CH3 H H CH2CH3 Comp. No. R, R2 R3 R4 R5 6.025 H CF3 H CH3 CH2CH3 6.026 H CF3 H CF3 CH2CH3 6.027 H CF3 H SCH3 CH2CH3 6.028 H CF3 H SOCH3 CH2CH3 6.029 H CF3 H S02CH3 CH2CH3 6.03 H CF3 H Cl CH2CH3 6.031 H CF3 H OCH3 CH2CH3 6.032 H CH3 H CF3 CH2CH3 6.033 H CI H CF3 CH2CH3 6.034 H OCH3 H CF3 CH2CH3 6.035 CN CF3 H H CH2CH3 6.036 Cl CF3 H H CH (CH3) 2 6.037 CHF2 CF3 H H CH (CH3) z 6.038 CCI3 CF3 H H CH (CH3) 2 6.039 CCIF2 CF3 H H CH (CH3) 2 6.04 CF3 CF3 H H CH (CH3) 2 6.041 CH3 CF3 H H CH (CH3) 2 6.042 CH2CH3 CF3 H H CH (CH3) 2 6.043 (CH2) 2CH3 CF3 H H CH (CH3) 2 6.044 CH2F CF3 H H CH (CH3) 2 6.045 CH2Cl CF3 H HCH(CH3)2 6.046 CH2OCH3 CF3 H H CH(CH3)2 6.047 CH2SMe CF3 H H CH (CH3) 2 6.048 CH2SO2Me CF3 H H CH(CH3)2 6.049 CH=CH2 CF3 H H CH (CH3) 2 6.05 CH2CH=CH2 CF3 H HCH(CH3)2 6.051 CCH CF3 H H CH (CH3) 2 6.052 CF3 SCH3 H H CH (CH3) 2 6.053 CF3 SOCH3 H H CH (CH3) 2 6.054 CF3 SO2CH3 H HCH(CH3)2 6.055 CF3 OCH3 H H CH (CH3) 2 6.056 CF3 CN H H CH (CH3) 2 Comp. No. R, R2 R3 R4 Rs 6.057 CF3 Cl H H CH(CH3)2 6.058 CF3 OCH3 H H CH (CH3) 2 6.059 CF3 CH3 H H CH (CH3) 2 6.06 H CF3 H CH3 CH (CH3) 2 6.061 H CF3 H CF3 CH (CH3) 2 6.062 H CF3 H SCH3 CH (CH3) 2 6.063 H CF3 H SOCH3 CH (CH3) 2 6.064 H CF3 H SO2CH3CH(CH3)2 6.065 H CF3 H Cl CH(CH3)2 6.066 H CF3 H OCH3 CH (CH3) 2 6.067 H CH3 H CF3 CH (CH3) 2 6.068 H Cl H CF3 CH (CH3) 2 6.069 H OCH3 H CF3 CH (CH3) 2 6.07 CN CF3 H H CH (CH3) 2 6.071 Cl CF3 H H HNPh 6.072CHF2CF3HHHNPh 6.073CCl3 CF3 H H HNPh 6.074 CCIF2 CF3 H H HNPh 6.075 CF3 CF3 H H HNPh 6.076 CH3 CF3 H H HNPh 6.077 CH2CH3 CF3 H H HNPh 6.078 (CH2) 2CH3 CF3 H H HNPh 6.079CH2F CF3 H H HNPh 6.08 CH2CI CF3 H H HNPh 6.081CH2OCH3 CF3 H H HNPh 6.082 CH2SMe CF3 H H HNPh 6.083CH2SO2Me CF3 H H HNPh 6.084CH=CH2 CF3 H H HNPh 6.085CH2CH=CH2 CF3 H H HNPh 6.086CCH CF3 H H HNPh 6.087CF3 SCH3 H H HNPh 6.088CF3 SOCH3 H H HNPh Comp. No. R, R2 R3 R4 Rs 6.089CF3 SO2CH3 H H HNPh 6.09 CF3 OCH3 H H HNPh 6.091 CF3 CN H H HNPh 6.092CF3 Cl H H HNPh 6.093 CF3 OCH3 H H HNPh 6.094CF3 CH3 H H HNPh 6.095 H CF3 H CH3 HNPh 6.096 H CF3 H CF3 HNPh 6.097 H CF3 H SCH3 HNPh 6.098 H CF3 H SOCH3 HNPh 6.099H CF3 H SO2CH3 HNPh 6.1H CF3 H Cl HNPh 6.101 H CF3 H OCH3 HNPh 6.102 H CH3 H CF3 HNPh 6.103 H Cl H CF3 HNPh 6.104 H OCH3 H CF3 HNPh 6.105CN CF3 H H HNPh 6.106 Cl CF3 H HHNC(CH3)3 6.107 CHF2 CF3 H HHNC(CH3)3 6.108 CCl3 CF3 H H HNC(CH3)3 6.109 CCIF2 CF3 H H HNC (CH3) 3 6.11 CF3 CF3 H H HNC (CH3) 3 6.111 CH3 CF3 H H HNC (CH3) 3 6.112 CH2CH3 CF3 H H HNC (CH3) 3 6.113 (CH2) 2CH3 CF3 H H HNC (CH3) 3 6.114 CH2F CF3 H H HNC (CH3) 3 6.115 CH2CI CF3 H H HNC (CH3) 3 6.116 CH2OCH3 CF3 H H HNC(CH3)3 6.117 CH2SMe CF3 H H HNC(CH3)3 6.118 CH2SO2Me CF3 H H HNC(CH3)3 6.119 CH=CH2 CF3 H H HNC(CH3)3 6.12 CH2CH=CH2 CF3 H H HNC (CH3) 3 Comp. No. R1 R2 R3 R4 R5<BR> 6.121 CCH CF3 H HHNC(CH3)3 6.122 CF3 SCH3 H H HNC (CH3) 3 6.123 CF3 SOCH3 H H HNC (CH3) 3 6.124 CF3 SO2CH3 H H HNC (CH3) 3 6.125 CF3 OCH3 H H HNC (CH3) 3 6.126 CF3 CN H H HNC (CH3) 3 6.127 CF3 Cl H H HNC (CH3) 3 6.128 CF3 OCH3 H H HNC (CH3) 3 6.129 CF3 CH3 H H HNC (CH3) 3 6.13 H CF3 H CH3 HNC (CH3) 3 6.131 H CF3 H CF3 HNC (CH3) 3 6.132 H CF3 H SCH3 HNC (CH3) 3 6.133 H CF3 H SOCH3 HNC (CH3) 3 6.134 H CF3 H SO2CH3 HNC (CH3) 3 6.135 H CF3 H ClHNC(CH3)3 6.136 H CF3 H OCH3 HNC (CH3) 3 6.137 H CH3 H CF3 HNC (CH3) 3 6.138 H Cl H CF3 HNC (CH3) 3 6.139 H OCH3 H CF3 HNC (CH3) 3 6.14 CN CF3 H H HNC (CH3) 3 Table 7: Comp. No. R, R2 R3 R4 p 7.001 H CF3 H H 0 7.002 F CF3 H H 0 7.003Cl CF3 H H 0 7.004 Br CF3 H H 0 7.005 CHF2 CF3 H H 0 7.006CCl3 CF3 H H 0 7.007 CCIF2 CF3 H H 0 7.008 CF3 CF3 H H 0 7.009 CH3 CF3 H H 0 7.01 CH2CH3 CF3 H H 0 7.011 CH (CH3) 2 CF3 H H o 7.012 (CH2) 2CH3 CF3 H H 0 7.013 C (CH3) 3 CF3 H H 0 7.014 Ph CF3 H H 0 7.015 CH2F CF3 H H 0 7.016 CH2CI CF3 H H 0 7.017 CH2Br CF3 H H 0 7.018 CH20H CF3 H H 0 7.019CH2OCOCH3 CF3 H H 0 7.02CH2OCOPh CF3 H H 0 7.021CH20CH3CF3HH0 7.022 CH2OCH2CH3 CF3 H H 0 Comp. No. R, R2 R3 R4 P 7.023 CH2CH20CH3 CF3 H H 0 7.024CH2SMe CF3 H H 0 7.025 CH2SOMe CF3 H H 0 7.026 CH2SO2Me CF3 H H 0 7.027 CH2SO2Ph CF3 H H o 7.028 SCH3 CF3 H H 0 7.029 SOCH3 CF3 H H 0 7.03SO2CH3 CF3 H H 0 7.031N(CH3)2 CF3 H H 0 7.032 CH=CH2 CF3 H H 0 7.033 CH2CH=CH2 CF3 H H 0 7.034SO2N(CH3)2 CF3 H H 0 7.035 CCH CF3 H H 0 7.036cyclopropyl CF3 H H 0 7.037 OCH3 CF3 H H 0 7.038 OCHF2 CF3 H H 0 7.039 OCH2CCH CF3 H H 0 7.04 H CF2CF3 H H 0 7.041 Cl CF2CF3 H H 0 7.042 CHF2CF2CF3 H H 0 7.043 CCI3 CF2CF3 H H 0 7.044 CCIF2 CF2CF3 H H 0 7.045 CF3 CF2CF3 H H 0 7.046 CH3 CF2CF3 H H 0 7.047 CH2CH3 CF2CF3 H H 0 7.048 CH (CH3)2 CF2CF3 H H 0 7.049 (CH2) 2CH3 CF2CF3 H H 0 7.05 C (CH3) 3 CF2CF3 H H 0 7.051 CH2F CF2CF3 H H 0 7.052 CH2ClCF2CF3 H H 0 7.053 CH2OHCF2CF3 H H 0 7.054 CH2OCOCH3CF2CF3 H H 0 Comp. No. R, R2 R3 R4 p 7.055 CH2OCOPh CF2CF3 H H o 7.056 CH20CH3 CF2CF3 H H 0 7.057 CH2OCH2CH3CF2CF3 H H 0 7.058 CH2SMe CF2CF3 H H 0 7.059 CH2SOMe CF2CF3 H H 0 7.06 CH2SO2MeCF2CF3 H H 0 7.061 CH2SO2PhCF2CF3 H H 0 7.062 N (CH3) 2 CF2CF3 H H 0 7.063 CH=CH2 CF2CF3 H H 0 7.064 CH2CH=CH2 CF2CF3 H H 0 7.065 SO2N (CH3)2 CF2CF3 H H 0 7.066 CCH CF2CF3 H H 0 7.067 cyclopropyl CF2CF3 H H 0 7.068 OCH3 CF2CF3 H H 0 7.069 CO2MeCF2CF3 H H 0 7.07 OCH2CCH CF2CF3 H H 0 7.071 H CF2CI H H 0 7.072 ClCF2Cl H H 0 7.073 CHF2 CF2CI H H 0 7.074 CCI3 CF2CI H H 0 7.075 CCIF2 CF2CI H H 0 7.076 CF3 CF2CI H H 0 7.077 CH3 CF2CI H H 0 7.078 CH2CH3CF2Cl H H 0 7.079 CH (CH3) 2 CF2CI H H 0 7.08 (CH2)2CH3 CF2Cl H H 0 7.081 C (CH3) 3 CF2CI H H 0 7.082 CH2FCF2Cl H H 0 7.083 CH2CI CF2CI H H 0 7.084 CH20H CF2CI H H 0 7.085 CH2OCOCH3 CF2CI H H 0 7.086 CH2OCOPh CF2CI H H 0 Comp. No. R, R2 R3 R4 P 7.087 CH2OCH3CF2Cl H H 0 7.088 CH2OCH2CH3CF2Cl H H 0 7.089 CH2SMe CF2CI H H 0 7.09 CH2SOMeCF2Cl H H 0 7.091 CH2SO2Me CF2CI H H 0 7.092 CH2SO2PhCF2Cl H H 0 7.093 N (CH3) 2 CF2CI H H 0 7.094 CH=CH2CF2Cl H H 0 7.095 CH2CH=CH2 CF2CI H H 0 7.096 SO2N (CH3)2 CF2Cl H H 0 7.097 CCH CF2CI H H 0 7.098 cyclopropylCF2Cl H H 0 7.099 OCH3 CF2CI H H 0 7.1 OCH2CCH CF2CI H H 0 7.101 CF3 CHF2 H H 0 7.102 CH3 CHF2 H H 0 7.103CH2OCH3 CHF2 H H 0 7.104 CH2ClCHF2 H H 0 7.105 CH2FCHF2 H H 0 7.106 CH3 CF3 H CH3 0 7.107 Cl CF3 H CH3 0 7.108 CH3 CF3 CH3 H 0 7.109 CH3 CF3 Cl H 0 7.11 OCH3 CF3 CH3 H 0 7.111 CH2OCH3 CF3 CH3 H 0 7.112 CH2OCH3 CF3 Cl H 0 7.113 COOCH3 H H H 0 7.114 CF3 SCH3 H H 0 7.115 CH3 SCH3 H H 0 7.116 CF3 SOCH3 H H 0 7.117 CH3 SOCH3 H H 0 7.118 CF3 SO2CH3 H H 0 Comp. No. R, R2 R3 R4 P 7.119 CH3SO2CH3 H H 0 7.12 CF3 OCH3 H H 0 7.121 CH3 OCH3 H H 0 7.122 CF3 OCH2CF3 H H 0 7.123 CH3 OCH2CF3 H H 0 7.124 CF3 OCH2CCH H H 0 7.125 CH3 OCH2CCH H H 0 7.126 CF3 CN H H 0 7.127 CH3 CN H H 0 7.128CF3 Cl H H 0 7.129CF3 Cl H H 0 7.13CH3 Cl H H 0 7.131HaHH0 7.132 CF3 OCH3 H H 0 7.133 CH3 OCH3 H H 0 7.134 CF3 CH3 H H 0 7.135 H CF3 H CH3 0 7.136 H CF3 H CF3 0 7.137 H CF3 H CH2CH3 0 7.138 H CF3 H CF3 0 7.139 H CF3 H SCH3 0 7.14 H CF3 H SOCH3 0 7.141 H CF3 H SO2CH3 0 7.142 H CF3 H Cl 0 7.143 H CF3 H OCH3 0 7.144 H CH3 H CF3 0 7.145 H Cl H CF3 0 7.146 H OCH3 H CF3 0 7.147 H SCH3 H CF3 0 7.148 H SOCH3 H CF3 0 7.149 CH3 (CF2) 3CF3 H H 0 7.15 CF2H SCH3 H H 0 Comp. No. R, R2 R3 R4 p 7.151 CF2CI SCH3 H H 0 7.152CF2H SOCH3 H H 0 7.153 CF2CI SOCH3 H H 0 7.154 CF2HSO2CH3 H H 0 7.155 CF2ClSO2CH3 H H 0 7.156 CF2H OCH3 H H 0 7.157 CF2ClOCH3 H H 0 7.158 CF2H OCH2CF3 H H 0 7.159 CF2CI OCH2CF3 H H 0 7.16 CF2H OCH2CCH H H 0 7.161 CF2CI OCH2CCH H H 0 7.162 CF2H CN H H 0 7.163 CF2CI CN H H 0 7.164CF2H Cl H H 0 7.165 CF2CI Cl H H 0 7.166 CF2H OCH3 H H 0 7.167 CF2CI OCH3 H H 0 7.168 CF3CH2OCH3 H H 0 7.169 CF2ClCH2OCH3 H H 0 7.17 CF2H CH2OCH3 H H 0 7.171 CN CF3 H H 0 7.172H CF3 H H 2 7.173 F CF3 H H 2 7.174 Cl CF3 H H 2 7.175 Br CF3 H H 2 7.176 CHF2 CF3 H H 2 7.177 CCI3 CF3 H H 2 7.178CClF2 CF3 H H 2 7.179 CF3 CF3 H H 2 7.18 CH3 CF3 H H 2 7.181 CH2CH3 CF3 H H 2 7.182 CH (CH3) 2 CF3 H H 2 Comp. No. R, R2 R3 R4 P 7.183 (CH2) 2CH3 CF3 H H 2 7.184C(CH3)3 CF3 H H 2 7.185 Ph CF3 H H 2 7.186 CH2F CF3 H H 2 7.187 CH2CI CF3 H H 2 7.188 CH2Br CF3 H H 2 7.189CH2OH CF3 H H 2 7.19CH2OCOCH3 CF3 H H 2 7.191CH2OCOPh CF3 H H 2 7.192CH2OCH3 CF3 H H 2 7.193 CH20CH2CH3 CF3 H H 2 7.194 CH2CH20CH3 CF3 H H 2 7.195 CH2SMe CF3 H H 2 7.196 CH2SOMe CF3 H H 2 7.197 CH2SO2Me CF3 H H 2 7.198 CH2SO2Ph CF3 H H 2 7.199 SCH3 CF3 H H 2 7.2 SOCH3 CF3 H H 2 7.201SO2CH3 CF3 H H 2 7.202N(CH3)2 CF3 H H 2 7.203 CH=CH2 CF3 H H 2 7.204 CH2CH=CH2 CF3 H H 2 7.205 SO2N (CH3) 2 CF3 H H 2 7.206 CCH CF3 H H 2 7.207cyclopropyl CF3 H H 2 7.208 OCH3 CF3 H H 2 7.209 OCHF2 CF3 H H 2 7.21 OCH2CCH CF3 H H 2 Table 8 Comp. No. R, R2 R3 R4 8.001 H CF3 H H 8.002 F CF3 H H 8.003Cl CF3 H H 8.004 Br CF3 H H 8.005 CHF2 CF3 H H 8.006 CCI3 CF3 H H 8.007 CCIF2 CF3 H H 8.008 CF3 CF3 H H 8.009 CH3 CF3 H H 8.01 CH2CH3 CF3 H H 8.011 CH (CH3) 2 CF3 H H 8.012 (CH2) 2CH3 CF3 H H 8.013 C (CH3) 3 CF3 H H 8.014 Ph CF3 H H 8.015 CH2F CF3 H H 8.016 CH2CI CF3 H H 8.017 CH2Br CF3 H H 8.018 CH20H CF3 H H 8.019 CH20COCH3 CF3 H H 8.02 CH20COPh CF3 H H 8.021 CH20CH3 CF3 H H 8.022 CH20CH2CH3 CF3 H H 8.023 CH2CH2OCH3 CF3 H H 8.024 CH2SMe CF3 H H Comp. No. R, R2 R3 R4 8.025CH2SOMe CF3 H H 8.026 CH2SO2Me CF3 H H 8.027CH2SO2Ph CF3 H H 8.028 SCH3 CF3 H H 8.029 SOCH3 CF3 H H 8.03 S02CH3 CF3 H H 8.031 N (CH3) 2 CF3 H H 8.032 CH=CH2 CF3 H H 8.033 CH2CH=CH2 CF3 H H 8.034SO2N(CH3)2 CF3 H H 8.035 CCH CF3 H H 8.036 cyclopropyl CF3 H H 8.037 OCH3 CF3 H H 8.038 OCHF2 CF3 H H 8.039 OCH2CCH CF3 H H Table9: Comp. No. R, R2 R3 R4 9.001 H CF3 H H 9.002 F CF3 H H 9.003 Cl CF3 H H 9.004 Br CF3 H H 9.005 CHF2 CF3 H H 9.006 CCI3 CF3 H H Comp. No. R1 R2 R3 R4 9.007 CCIF2 CF3 H H 9.008 CF3 CF3 H H 9.009 CH3 CF3 H H 9.01 CH2CH3 CF3 H H 9.011 CH (CH3) 2 CF3 H H 9.012 (CH2) 2CH3 CF3 H H 9.013 C (CH3) 3 CF3 H H 9.014 Ph CF3 H H 9.015 CH2F CF3 H H 9.016 CH2CI CF3 H H 9.017 CH2Br CF3 H H 9.018CH2OH CF3 H H 9.019 CH20COCH3 CF3 H H 9.02 CH20COPh CF3 H H 9.021 CH20CH3 CF3 H H 9.022 CH20CH2CH3 CF3 H H 9.023 CH2CH20CH3 CF3 H H 9.024 CH2SMe CF3 H H 9.025 CH2SOMe CF3 H H 9.026 CH2SO2Me CF3 H H 9.027 CH2SO2Ph CF3 H H 9.028 SCH3 CF3 H H 9.029 SOCH3 CF3 H H 9.03SO2CH3 CF3 H H 9.031 N (CH3) 2 CF3 H H 9.032 CH=CH2 CF3 H H 9.033 CH2CH=CH2 CF3 H H 9.034SO2N(CH3)2 CF3 H H 9.035 CCH CF3 H H 9.036 cyclopropyl CF3 H H 9.037 OCH3 CF3 H H 9.038 OCHF2 CF3 H H Comp. No. R, R2 R3 R4 9.039 OCH2CCH CF3 H H Physical data (melting points in°C): Comp. No.

1.001resin 1.005 crystals m. p. 61-62 1.008oil 1.009 crystals m. p. 75-77 1.01oil 1.011 crystals m. p. 111-112 1.012 crystals m. p. 87-88 1.013 crystals m. p. 112-114 1.014 oil 1.021 crystals m. p. 128-129 1.023 crystals m. p. 91-92 1.024 oil 1.026 amorphous 1.028 amorphous 1.03 resin 1.031 crystals m. p. 145-146 1.042 oil 1.043 crystals m. p. 107-110 1.047 crystals m. p. 155-156 1.048 viscous 1.05 crystals m. p. 51-53 1.06 crystals m. p. >220 1.109 oil 1.195 oil 1.258 crystals m. p. 119-121 1.31 crystals m. p. 92-94 1.312 viscous 1.313 crystals m. p. 137-138 1.314 oil 1.316 resin 1.323 oil 1.334resin 1.335 crystals m. p. 140-142 1.339 crystals m. p. 137-139 1.341resin 1.343 crystals m. p. 97-99 1.347 crystals m. p. 135-137 1.349 oil, nD 1.4965 1.351 crystals m. p. 125-127 1.353 resin, nD 1.5289 1.355 crystals m. p. 90-92 1.356 resin 1.358resin 1.361oil 1.362 crystals m. p. 139-142 1.371 crystals m. p. 96-97 1.372 resin 1.373resin 1.374 crystals m. p. 116-1199 1.375resin 1.376 crystals m. p. >270 1.381 crystals m. p. 117-118 1.383 crystals m. p. 172-173 1.384resin 1.385resin 1.386 resin 1.387resin 1.388 crystals m. p. 102-104 1.389 crystals m. p. 143-145 1.39 crystals m. p. 195-197 1.391 solid 1.392 crystals m. p. 202-206 1.398 crystals m. p. 137-138 1.399 crystals m. p. 262-263 1.4 oil 1.401 oil 1.402 oil 1.403oil 1.404oil 1.405 viscous 1.406 oil 1.408oil 1.409oil 1.41oil 1.411 crystals m. p. 98-100 1.412 crystals m. p. 130-131 1.413 crystals m. p. 167-170 1.414 crystals m. p. 166-167 1.415 crystals m. p. 91-93 1.418 crystals m. p. 149-150 1.421 crystals m. p. 88-89 1.422 crystals m. p. 175-177 1.423 crystals m. p. 45-47 1.424 crystals m. p. 102-104 2.001 resin 2.003oil 2.03 crystals m. p. 107-110 2.038 crystals m. p. 111-113 2.043resin 2.044 crystals m. p. 105-106 2.045 amorphous 3.001 crystals m. p. 95-97 3.054 oil 3.055 crystals m. p. 108-110 3.056 resin, nD 1.5509 4.009 crystals m. p. 107-109 4.01 oil 4.011 oil 4.014 crystals m. p. 148-149 4.021 crystals m. p. 44-45 4.033 crystals m. p. 46-48 4.124 crystals m. p. 46-48 4.328 oil 5.008 resin 5.081resin 5.083 crystals m. p. 161-162 5.084 crystals m. p. 215-216 5.085resin 6.006 crystals m. p. 176-177 6.041 crystals m. p. 186-187 6.076 crystals m. p. 195-196 6.111 crystals m. p. 163-164 7.009 ratio A: B = 2: 1. H-NMR(CDCl3, ppm) SCH3: A: 2.50; B: 2.66.

7.01 ratio A: B = 5: 1. H-NMR(CDCl3, ppm) SCH3: A: 2.50; B: 2.64.

7.011 ratio A: B = 9: 1. H-NMR (CDCI3, ppm) SCH3: A: 2.46; B: 2.59.

7.021 ratio A: B = 3: 1. H-NMR(CDCl3, ppm) SCH3: A: 2.50; B: 2.62.

7.18 ratio A: B = 2:. H-NMR(CDCl3, ppm) S02CH3: A: 3.40; B: 3.58.

7.182 ratio A: B = 9: 1. H-NMR(CDCl3, ppm) SO2CH3: A: 3.32; B: 3.50.

7.192 ratio A: B = 3: 1. H-NMR(CDCl3, ppm) S02CH3: A: 3.40; B: 3.58.

8.009 crystals m. p. 96-97 8.01 amorphous 8.011 oil 8.021 oil 9.009 crystals m. p. 112-113 9.01 amorphous 9.011 amorphous 9.021 oil Biotoqica ! Examotes Examale B1: Herbical action before emeraence of the ptants (pre-emerqence action) Monocotyledonous and dicotyledonous test plants are sown in standard soil in plastic pots.

Immediately after sowing, the test substances are sprayed on (500 1 of water/ha) as an aqueous suspension (prepared from a 25% wettable powder (Example F3, b) according to WO 97/34485) or emulsion (prepared from a 25% emulsion concentrate (Example F1, c)), corresponding to a dosage of 2 kg of AS/ha. The test plants are then grown under optimum conditions in a greenhouse. After a test period of 3 weeks, the test is evaluated with a nine- 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: Test plant Avena Cyperus Setaria Sinapis Solanum Stellaria Active compound No.

1.009 2 1 1 2 1 2 1.376 2 1 1 2 1 2 4.009 1 2 1 2 1 3 7.009 4 2 1 3 1 2 1.381 4 1 2 2 1 1 1.011 2 1 1 1 1 1 5.008 2 1 1 2 1 2 4.021 2 1 2 2 1 2 1.010 2 1 1 1 1 2 1.021 4 2 1 1 1 3 1.398 2 1 1 1 1 1 1.195 2 1 1 1 1 2 4.124 2 1 2 2 1 2 1.411 3 2 1 2 1 2 1.042 4 2 2 1 1 4 1.023 2 2 2 1 1 2 1.109 2 2 2 2 1 3 1.313 3 1 2 1 1 2 1.401 2 1 1 2 1 2 1.404 2 1 1 2 1 2 1.400 2 1 1 2 1 2 1.403 2 1 1 1 1 2 1.405 2 1 1 1 1 2 1.406 2 1 1 1 1 2 1.402 2 1 1 2 1 2 1.005 4 1 1 1 1 1 1.043 4 2 1 2 1 2 1.409 1 1 1 1 1 1 1.41 2 1 1 1 1 1 1.06 2 1 1 2 1 1 7.192 4 2 2 3 2 2 7.021 1 1 1 1 1 1 The same results are obtained when the compounds of the formula I are formulated according to Examples F2 and F4 to F8 according to WO 97/34485.

Example B2: Post-emeraence herbicidal action Monocotyledonous and dicotyledonous test plants are grown in plastic pots with standard soil in a greenhouse and, in the 4-to 6-leaf stage, are sprayed with an aqueous suspension of the test substances of the formula 1, prepared from a 25% wettable powder (Example F3, b) according to WO 97/34485) or with an emulsion of the test substances of the formula 1, prepared from a 25% emulsion concentrate (Example F1, c) according to WO 97/34485), corresponding to a dosage of 2 kg of AS/ha (500 1 of water/ha). The test plants are then grown further under optimum conditions in a greenhouse. After a test period of about 18 days, the test is evaluated with a nine-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. In this test, the compounds of the formula I show strong herbicidal action.

Table B2: post-emeraence action: Test plant Avena Setaria Solanum Sinapis Stellaria Active compound No.

1.009 1 1 1 1 2 1.376 1 2 2 1 2 4.009 1 1 1 1 1 1.026 3 1 1 1 2 7.009 3 2 1 1 1.381 2 2 2 2 2 1.011 2 2 2 2 2 5.008 2 3 1 1 2 5.085 3 2 2 1 2 4.021 2 2 1 1 2 1.012 3 2 2 1 2 1.010 2 2 2 1 4 4.010 3 3 2 2 2 1.021 2 4 2 1 2 1.398 2 2 2 1 2 1.195 2 2 2 1 2 4.124 2 2 1 1 2 1.411 2 2 2 1 2 1.008 2 2 2 1 2 6.006 2 5 2 2 2 5.081 3 2 1 1 2 1.042 2 2 2 1 2 1.023 2 2 2 1 2 1.109 2 2 2 1 2 1.313 2 2 2 1 2 1.401 2 2 2 2 2 1.404 2 2 1 1 2 1.400 2 2 2 1 2 1.403 2 2 2 1 2 1.403 2 2 2 1 2 1.405 2 2 2 1 2 1.406 2 2 1 1 2 1.402 2 2 2 1 2 1.001 3 2 2 1 2 1.005 2 2 2 1 2 1.362 3 2 2 1 2 1.043 2 2 2 1 2 1.409 2 1 1 1 2 1.410 1 1 1 1 1 1.060 2 1 1 1 2 7.192 2 3 3 2 2 7.021 1 2 1 1 2 1.048 2 1 1 1 2 The same results are obtained when the compounds of the formula i are formulated according to Examples F2 and F4 to F8 according to WO 97/34485.

Example B3: Herbicidal action before emergence of the p ! ants (pre-emergence action) Monocotyledonous and dicotyledonous test plants are sown in pots in standard soil.

Immediately after sowing, the test substances are sprayed on (500 1 of spray liquor/ha) as an aqueous suspension, prepared from a wettable powder WP10 corresponding to the desired dosage (250 g of a. i./ha).

The test plants are then grown under optimum conditions in a greenhouse.

After a test period of 3 weeks, the test is evaluated with a nine-tevel 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, 7-9 mean good tolerance.

Table B3 : Pre-emerqen-ce action : Test plant Abutilon Amar-Cheno-Kochia Sida Stellaria Dose anthus podium g of AS/ha Active compound No.

1.355 1 1 1 1 2 2 250 1.347 2 2 1 1 4 1 250 1.335 1 2 1 5 2 7 250 1.349 1 3 1 4 2 5 250 1.339 2 1 1 7 2 1 250 1.341 3 9 1 9 4 1 250 1.343 1 4 1 9 3 5 250 The same results are obtained when the compounds of the formula I are formulated according to Examples F2 and F4 to F8 according to WO 97/34485.

Example B4: Herbicidal action after the emergence of the ptants (post-emergence action) Monocotyledonous and dicotyledonous test plants are sown in pots in standard soil. In the 2-3-leaf stage of the test plants, the test substances are sprayed on (500 1 of spray liquor/ha) as an aqueous suspension, prepared from a wettable powder WP10 according to the desired dosage (250 g of a. i./ha). 0.2% of X77 is added as wetting agent to the spray liquor. The test plants are then grown under optimum conditions in a greenhouse.

After a test period of 3 weeks, the test is evaluated with a nine-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, 7-9 mean good tolerance.

Table B4: Post-emeraence action : Test plant Abutilon Amar-Cheno-Kochia Setaria Stellaria Dose anthus podium [g of AS/ha] Active compound No.

1.355 2 2 2 3 2 3 250 1.347 3 2 2 2 3 3 250 1.335 3 2 2 2 2 3 250 1.349 2 2 2 2 2 3 250 1.339 2 2 3 1 4 3 250 1.351 5 2 3 3 3 3 250 1.341 5 2 3 4 5 4 250 1.343 3 2 2 3 9 3 250 1.361 2 2 2 2 2 3 250 The same results are obtained when the compounds of the formula I are formulated according to Examples F2 and F4 to F8 according to WO 97/34485.