AU2001262344A1 - Substituted pyridine herbicides - Google Patents

Description

SUBSTITUTED PYRIDINE HERBICIDES

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

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

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

The present invention thus provides compounds of the formula I

in which p is 0 or 1 ;

Ri is a CrC₆alkylene, C₃-C₆alkenylene or C₃-C₆alkynylene chain which may be mono- or polysubstituted by halogen or R_5> where the unsaturated bonds of the chain are not attached directly to the substituent X^

X_T is oxygen, -O(CO)-, -(CO)O-, -O(CO)O-, -N(R₆)-O-, -O-NR₅₁-, thio, sulfinyl, sulfonyl,

-SO₂NR₇-, -NR₅₂SO₂- or -NR₈-;

R₂ is a CτC₈alkyl, C₃-C₆alkenyl or C₃-C₆alkynyl group which is mono- or polysubstituted by halogen, hydroxyl, amino, formyl, nitro, cyano, mercapto, carbamoyl, d-Cealkoxy,

Cι-C₆alkoxycarbonyl, C₂-C₆alkenyl, C₂-C₆haloalkenyl, C₂-C₆alkynyl, C₂-C₆haloalkynyl,

C₃-C₆cycloalkyl, by halogen-substituted C₃-C₆cycloalkyl, or by C₃-C₆alkenyloxy,

C₃-C₆alkynyloxy, CrC₆haloalkoxy, C₃-C₆haloalkenyloxy, cyano-C C₆alkoxy, d-Cβalkoxy-

CrC₆alkoxy, d-Cealkoxy-d-Cealkoxy-Ci-Cealkoxy, CrC₆alkylthio-Cι-C₆aikoxy, C^Cealkyl- sulfinyl-CrC₆alkoxy, CrCealkylsulfonyl-C Cβalkoxy, Cι-C₆alkoxycarbonyl-CrC₆alkoxy, CrC₆alkoxycarbonyl, d-C₆alkylcarbonyl, d-C₆alkylthio, Cι-C₆alkylsulfinyl, d-C₆alkylsulfonyl, C C₆haloalkylthio, d-C₆haloalkylsulfinyl, d-C₆haloalkyIsulfonyl, oxiranyl, which for its part may be substituted by d-C₆alkyl, or by (3-oxetanyl)oxy, which for its part may be substituted by C C₆alkyl, or by benzylthio, benzylsulfinyl, benzylsulfonyl, Cι-C₆alkylamino, di(d-C₆alkyl)amino, R₉S(0)₂0, R₁₀N(R₁₁)SO₂-_J thiocyanato, phenyl, phenoxy, phenylthio, phenylsulfinyl or phenylsulfonyl; where the phenyl- or benzyl-containing groups for their part may be substituted by one or more d-C₆alkyl, C C₆haloalkyl, d-C₆alkoxy, d-C₆haloalkoxy, halogen, cyano, hydroxyl or nitro groups, or

R₂ is phenyl which may be mono- or polysubstituted by d-C₆alkyl, C C₆haloalkyl, d-C₆alkoxy, C C₆haloalkoxy, halogen, cyano, hydroxyl or nitro; or R₂ is C₃-C₆cycIoalkyl, Cι-C₆aIkoxy- or d-C₆alkyl-substituted C₃-C₆cycloalkyl, 3-oxetanyl or d -C₆alkyl-substituted 3-oxetanyl; or, if Q is Q₂ or Q₃, or is Qi in which Rι and R₂₂ are a C₂-C₃alkylene chain, R₂ is additionally also a five- to ten-membered monocyclic or fused bicyclic ring system which may be aromatic, saturated or partially saturated and may contain 1 to 4 heteroatoms selected from the group consisting of nitrogen, oxygen and sulfur, where the ring system is attached directly or via a d-C₄alkylene, C₂-C₄alkenyl-C C₄alkylene, C₂-C₄alkynyl-C C₄alkylene, -N(R₁₂)-CrC₄alkylene, -SO-Cι-C₄alkylene or -SO₂-C C₄alkylene group to the substituent Xi and where each ring system may not contain more than two oxygen atoms and not more than two sulfur atoms and the ring system for its part may be mono-, di- or trisubstituted by d-C₆alkyl, d-C₆haloalkyl, C₂-C₆alkenyl, C₂-C₆haloaikenyl, C₂-C₆alkynyl, C₂-C₆haloalkynyl, d-C₆alkoxy, hydroxyl, C C₆haloalkoxy, C₃-C₆aikenyloxy, C₃-C₆alkynyloxy, mercapto, C C₆alkylthio, Cι-C₆haloalkylthio, C₃-C₆alkenylthio, C₃-C₆haloalkenylthio, C₃-C₆alkynylthio, C₂-C₅alkoxyalkylthio, C₃-C₅acetylalkylthio, C₃-C₆alkoxycarbonylalkylthio, C₂-C₄cyanoalkylthio, CrC₆alkylsulfinyl, C C₆haloalkylsulfinyl, d-C₆alkylsulfonyl, C C₆ha!oalkylsulfonyl, aminosulfonyl, d-C₂alkylaminosulfonyl, di(d-C₂alkyl)aminosulfonyl, di(Cι-C₄alkyl)amino, halogen, cyano, nitro, phenyl and benzylthio, where phenyl and benzylthio for their part may be substituted on the phenyl ring by d-C₃alkyl, d-C₃haloalkyl, C_rC₃alkoxy, C C₃haloalkoxy, halogen, cyano or nitro, and where the substituents on the nitrogen in the heterocyclic ring are different from halogen; or R₂ is hydrogen or unsubstituted d-C₈alkyl if a) Ri is substituted by the group R₅, or b) Q is the group Q₂, or c) Q is the group Q₃ in which Xi is -O(CO)-, -(CO)O-, -N(R₆)-O-, -O-NR₅₁-, -SO₂NR₇-, -NR₅₂SO₂- or -NR₈-; or d) Q is the group Q_T in which X_T is -N(R₆)-O-, -O-NR₅₁-, -SO₂NR₇-, -NR₅₂SO₂- or -NR₈-, or e) Q is the group Q, in which Ru and R₂₂ in Q^ are a C₂-C₃alkylene chain and X^ is -O(CO)- or -(CO)O-,

R₃ is C C₃haloalkyl;

R₄ is hydrogen, halogen, d-C₃alkyl, Cι-C₃haloalkyl, Cι-C₃alkoxy, d-C₃alkoxy-d-C₃alkyI or

C C₃alkoxy-CrC₃alkoxy;

R₅ is hydroxyl, C C₆alkoxy, C₃-C₆cycloalkyloxy, CrCealkoxy-C Cealkoxy,

C Cealkoxy-d-Cβalkoxy-d-Cealkoxy or d-C₂alkylsulfonyloxy;

R₆, R₇, R₈, R₉, R₁₀, R₁₁, R₁₂, R5₁ and R₅₂ independently of one another are hydrogen,

C C₆alkyl, d-C₆haloalkyl, d-C₆alkoxycarbonyl, CrC₆alkylcarbonyl, CrC-βalkoxy-d-Cealkyl,

C Cealkoxy-C Csalkyl substituted by C C₆alkoxy, benzyl or phenyl, where phenyl and benzyl for their part may be mono- or polysubstituted by C C₆alkyl, C C₆haloalkyl,

C C₆alkoxy, d-C₆haloalkoxy, halogen, cyano, hydroxyl or nitro; where R₆ and R₉ are not simultaneously hydrogen and hydrogen, d-C₆alkoxycarbonyl or d-Cβaikylcarbonyl, respectively;

Q is Q_!

in which

A₁ is C(R₁ R₁₅), NR₁₆ or oxygen;

A₂ is C(R-ι₇R₁₈), C(O), -C=N-O-Rι_9> oxygen, thio, sulfinyl, sulfonyl, -NR₂₀ or ethylene; with the provisos that A-, is different from oxygen if A₂ is oxygen, C(O), thio, sulfinyl, -C=N-O-R₁₉,

NR₂₀ or C(R₁₇R ₈), where R₁₇ and R₁₈ independently of one another are d-C₄alkoxy, d-C alkylthio, C C₄alkylsulfinyl, d-C₄alkylsulfonyl; and A^ is different from NR ₆ if A₂ is thio, sulfinyl or C(R-|₇R₁₈), where R₁ and R₁₈ independently of one another are d-C alkoxy, d-C₄alkylthio, C C₄alkylsulfinyl, d-C₄alkylsulfonyl; R₁₄and R₂₂ independently of one another are hydrogen, d-C₄alkyl, Cι-C₄haloalkyl, C₃-C₄alkenyl, C₃-C₄alkynyl, d-C₄alkylthio, C C₄alkylsulfinyl, C-,-C₄alkylsulfonyl, C C₄alkylsulfonyloxy, C C₄alkoxy, d-C₄alkoxycarbonyl or Cι-C₄alkylcarbonyl;

R₁₅ and R₂ι independently of one another are hydrogen, d-C₄alkyl, d-C₄haloalkyl,

C₃-C₄alkenyl or C₃-C₄alkynyl;

R₁₇ is hydrogen, C-ι-C₄alkyl, d-C₄haloaIkyl, Cι-C₄alkoxy, d-C₄alkylthio, d-C₄alkylsulfinyl or

C C₄alkylsulfonyl;

R₁₈ is hydrogen, C C₄alkyl, Cι-C₄haloalkyl, C₃-C₄alkenyl, C₃-C₄alkynyl, d-C alkoxy,

C C₄alkylthio, CrC₄alkylsulfinyl, d-C alkylsulfonyl or C C₄dialkoxyalkyl-CrC₄alkyl;

R₂₀ is d-C₄alkyl, C₃-C₆cycloalkyl, C₃-C₄alkenyl, C₃-C₄alkynyl, d-C alkylcarbonyl, C C₄alkyl- carbonyloxy, di(d-C₄alkyl)aminocarbonyl or benzyl, where the phenyl group may be mono- or polysubstituted by C C₆alkyl, d-C₆haloalkyl, Cι-C₆alkoxy, C C₆haloalkoxy, halogen, cyano, hydroxyl or nitro;

R₁₉ and Rι₆ independently of one another are hydrogen, d-C alkyl, C₃-C₆cycloalkyl,

C₃-C₄alkenyl, C₃-C₄alkynyl, benzyl or phenyl, where phenyl and benzyl for their part may be mono- or polysubstituted by d-C₆alkyl, d-C₆haloalkyl, d-C₆alkoxy, d-C₆haloalkoxy, halogen, cyano, hydroxyl or nitro; or R ₄ and R₂₂ together form a C₂-C₃alkylene chain; or R₁₄ and R₁₅ together and/or R₁₇ and R-ι₈ together and/or R₂₁ and R₂₂ together form a

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

R₂₂ and R₁₈ together form a C₂-C₄alkylene chain; or R₁₈ together with R₂₂ or R₁₄ forms a direct bond; or R₁₆ and Rι₈ together form a C₂-C₄alkylene chain;

R₁₃ is hydroxyl, O^"M\ where M⁺ is an alkali metal cation or ammonium cation, halogen, d-C₁₂alkylsulfonyloxy, amino, C C₄alkylthio, d-Cι₂alkylsulfinyl, d-C₁₂alkylsulfonyl,

C C₁₂haloalkylthio, d-C₁₂haloaikylsulfinyl, d-C₁₂haloalkylsulfonyl, d-C₆alkoxy- d-C₆alkyrιhio, d-Cealkoxy-d-Cealkylsulfinyl, d-C₆alkoxy-d-C₆alkylsulfonyl, C₃-C₁₂alkenyl- thio, C₃-C₁₂alkenylsulfinyl, C₃-C₁₂alkenylsulfonyl, C₃-C₁₂alkynylthio, C₃-C₁₂alkynylsulfinyl,

C₃-C₁₂alkynylsulfonyl, C C₄alkoxycarbonyl-C C₄alkylthio, CrC₄alkoxycarbonyl-d-C₄alkyl- sulfinyl, CrC₄alkoxycarbonyl-Cι-C₄aIkylsulfonyl, (C C₄alkoxy)₂P(O)O, C₁-C₄alkyl-

(d-C₄alkoxy)P(O)O, H(C C₄alkoxy)P(O)O, R₂₃R₂₄N, R₂₅R₂₆NNH, R₂₇R₂₈NC(O)O-,

R₂₉R₃₀NC(O)NH-, C C₁₈alkylcarbonyloxy, C₂-Cι₈alkenylcarbonyloxy, C₂-C₁₈alkynyl- carbonyloxy, C₃-C₆cycloalkylcarbonyloxy, d-Cι₂alkoxycarbonyloxy, d-C₁₂alkylthio- carbonyloxy, d-Cι₂alkylthiocarbamoyl, where the alkyl, alkenyl and alkynyl groups may be substituted by halogen, d-C₆alkoxy, d-C₆alkylthio, d-C₆alkylsulfinyl, CrC₆alkylsulfonyl or cyano; or R₁₃ is phenoxy, phenylthio, phenylsulfinyl, phenylsulfonyl, phenylsulfonylamino, phenylsulfonyloxy or benzoyloxy, where the phenyl groups for their part may be substituted by one or more halogen, nitro, cyano, d-C₄alkyl, d-C haloalkyl, Cι-C₄alkoxy or d-C₄halo- alkoxy groups; or R₁₃ is a group Het-i-thio, Het₂-sulfinyl, Het₃-sulfonyl, Het₄-(CO)O or Het₅-N(R₃₃); in which

Het-i, Het₂, Het₃, Het₄ and Het₅ independently of one another are a five- to ten-membered monocyclic or fused bicyclic ring system which may be aromatic or partially saturated and may contain 1 to 4 heteroatoms selected from the group consisting of nitrogen, oxygen and sulfur, and where each ring system may not contain more than 2 oxygen atoms and not more than 2 sulfur atoms, and where the ring system itself can be substituted by d-C₆alkyl, d-Cehaloalkyl, C C₆alkoxy, d-C₆haloalkoxy, d-C₆alkylthio, d-C₆alkylsulfinyl, C C₆alkyl- sulfonyl, di(C -C alkyl)aminosulfonyl, di(C₁-C₄alkyl)amino, halogen, cyano, nitro or phenyl, and where the substituents on the nitrogen in the heterocyclic ring are different from halogen;

R23, R2₄. R25, 26, R27, 28, R29, R30 and R₃₃ independently of one another are hydrogen or d-C₆alkyl; or R₂3 and R₂₄ together or R₂₅ and R₂₆ together or R₂₇ and R₂₈ together or R₂₉ and R₃₀ together are pyrolidino, piperidino, morpholino, thiomorphoiino, which may be mono- or polysubstituted by methyl groups; or Q is Q₂

in which

R₃ is hydrogen, d-C₄alkyl, C C₄haloalkyl, C₃-C₆cycloalkyl, C₂-C₄alkenyl, C₂-C₄alkynyl or benzyl, where the phenyl group may be mono- or polysubstituted by d-C₆alkyl, d-C₆halo- alkyl, C C₆alkoxy, C-|-C₆haloalkoxy, halogen, cyano, hydroxyl or nitro; R₃₅ is hydrogen, Cι-C₄alkyl, C C₄haIoalkyl, C₃-C₆cycloalkyl, C₃-C₄alkenyl, C₃-C₄alkynyl or benzyl, where the phenyl group may be mono- or polysubstituted by Cι-C₆alkyl, d-C₆halo- alkyl, d-C₆alkoxy, C-,-C₆haloalkoxy, halogen, cyano, hydroxyl or nitro; R₃₆ is hydroxyl, O^"M⁺, where M⁺ is an alkali metal cation or ammonium cation, halogen, d-C₁₂alkylsulfonyloxy, amino, d-C₄alkylthio, d-C₁₂alkylsulfinyl, CrCeaikylsulfonyl, Cι-C₁₂haloalkylthio, d-C₁₂haloalkylsulfinyl, d-C ₂haloalkylsulfonyl, Cι-C₆alkoxy- CrC₆alkylthio, d-Cβalkoxy-d-Cealkylsulfinyl, d-Cealkoxy-d-Cealkylsulfonyl, C₃-C₁₂alkenyl- thio, C₃-C₁₂alkenylsulfinyl, C₃-C₁₂alkenylsulfonyl, C₃-C₁₂alkynylthio, C₃-C₁₂alkynylsulfinyl, C₃-C₁₂alkynylsulfonyl, C C₄alkoxycarbonyl-Cι-C alkylthio, d-C₄alkoxycarbonyl-Cι-C₄alkyl- sulfinyl, C C₄alkoxycarbonyl-d-C₄alkylsulfonyl, (C C₄alkoxy)₂P(0)O, d-C alkyl- (d-C₄alkoxy)P(O)O, H(C C₄alkoxy)P(O)O, R₃₇R₃₈N, R₃₉R₄₀NNH, R₄₁R₄₂NC(O)O-, R ₃R₄ NC(O)NH-, d-Cι₈alkylcarbonyloxy, C₂-C₁₈alkenylcarbonyloxy, C₂-C₁₈alkynyl- carbonyloxy, C₃-C₆cycloalkylcarbonyloxy, d-Cι₂alkoxycarbonyloxy, d-C₁₂alkylthio- carbonyloxy or d-C₁₂alkylthiocarbamoyl, where the alkyl, alkenyl and alkynyl groups may be substituted by halogen, d-C₆alkoxy, d-C₆alkylthio, Crdialkylsulfinyl, d-C₆alkylsulfonyl or cyano; or

R₃₆ is phenoxy, phenylthio, phenylsulfinyl, phenylsulfonyl, phenylsulfonylamino, phenylsulfonyloxy or benzoyloxy, where the phenyl groups for their part may be mono- or polysubstituted by halogen, nitro, cyano, d-C alkyl, d-C₄haloalkyl, C-ι-C₄alkoxy, C C₄halo- alkoxy, or R₃₆ is a group Het₇-thio, Het₈-sulfinyl, Het₉-sulfonyl, Het₁₀-(CO)O or Het_ι N(R₄₇); in which Het₇, Het₈, Het₉, Het₁₀ and Het^ independently of one another are a five- to ten-membered monocyclic or fused bicyclic ring system which may be aromatic or partially saturated and may contain 1 to 4 heteroatoms selected from the group consisting of nitrogen, oxygen and sulfur, and where each ring system may not contain more than 2 oxygen atoms and not more than 2 sulfur atoms, and where the ring system for its part may be substituted by C C₆alkyl, d-C₆haloalkyl, C C₆alkoxy, d-C₆haloalkoxy, d-C₆alkylthio, C C₆alkylsulfinyl, d-C-₆alkylsulfonyl, di(d-C₄alkyl)aminosulfonyl, di(C₁-C₄alkyl)amino, halogen, cyano, nitro or phenyl, and where the substituents on the nitrogen in the heterocyclic ring are different from halogen;

R37. R38, R39_> R o, R ι , ₄2_> R₄3, R^ and R₄₇ independently of one another are hydrogen or d-C₆alkyl; or R₃₇ and R₃₈ together or R₃₉ and R₄₀ together or R₄₁ and R₄₂ together or R₄₃ and R^ together are pyrolidino, piperidino, morpholino, thiomorpholino, which may be mono- or polysubstituted by methyl groups; or Q is Q₃

in which

R₄₉ is C C₄alkyl, C_rC haloalkyl, C₃-C₆cycloalkyl or halogen-substituted C₃-C₆cycloalkyl;

R₅₀ is d-C₃alkylene which may be substituted by halogen, hydroxyl, C^Cealkoxy,

C₂-C₆alkenyl, C₂-C₆alkynyl, C₃-C₆cycloalkyl, Cι-C₆alkoxy-d-C₆alkoxy, C C₆alkoxy-

C Cealkoxy-C Cealkoxy, (3-oxetanyl)oxy, or by C C₆alkyl-substituted (3-oxetanyl)oxy, or by benzylthio, benzylsulfinyl, benzylsulfonyl, phenyl, phenoxy, phenylthio, phenylsulfinyl or phenylsulfonyl, where the phenyl- and benzyl-containing groups for their part may be substituted by one or more C C₆alkyl, d-C₆haloalkyl, CrCealkoxy, C C₆haloalkoxy, halogen, cyano, hydroxyl or nitro groups; or R₅₀ is phenyl, where the phenyl-containing group for its part may be substituted by one or more d-C₆alkyl, d-C₆haloalkyl, C C₆alkoxy, C Cehaloalkoxy, halogen, cyano, hydroxyl or nitro, or R₅₀ is C₃-C₆cycloalkyl, C C₆alkoxy- or d-C₆alkyl-substituted C₃-C₆cycloalkyl, 3-oxetanyl or C C₆alkyl-substituted 3-oxetanyl; and n is 0, 1 or 2; and agronomically acceptable salts/N-oxides/isomers/enantiomers of these compounds.

The alkyl groups occurring in the definitions of the substituents can be straight-chain or branched and are, for example, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, iso- butyl, tert-butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl and dodecyl and their branched isomers. Alkoxy, alkenyl and alkynyl radicals are derived from the alkyl radicals mentioned. The alkenyl and alkynyl groups can be mono- or polyunsaturated. Halogen is generally fluorine, chlorine, bromine or iodine, preferably fluorine and chlorine. This also applies, correspondingly, to halogen in combination with other meanings, such as haloalkyl or halophenyl.

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

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

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

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

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

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

The compounds of the formula I may occur in different tautomeric forms, for example, if R₁₃ is hydroxyl, in the preferred formulae I' and I""

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

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

Examples of amines suitable for ammonium salt formation are both ammonia and primary, secondary and tertiary d-Cι₈alkylamines, C C₄hydroxyalky!amines and C₂-C alkoxy- alkylamines, for example methylamine, ethylamine, n-propylamine, isopropylamine, the four isomeric butylamines, n-amylamine, isoamylamine, hexylamine, heptylamine, octylamine, nonylamine, decylamine, pentadecylamine, hexadecylamine, heptadecylamine, octadecylamine, methylethylamine, methylisopropylamine, methylhexylamine, methylnonyl- amine, methylpentadecylamine, methyloctadecylamine, ethylbutylamine, ethylheptylamine, ethyloctylamine, hexylheptylamine, hexyloctylamine, dimethylamine, diethylamine, di-n- propylamine, diisopropylamine, di-n-butylamine, di-n-amylamine, diisoamylamine, dihexylamine, diheptylamine, dioctylamine, ethanolamine, n-propanolamine, isopropanol- amine, N,N-diethanolamine, N-ethylpropanolamine, N-butylethanolamine, allylamine, n-butenyl-2-amine, n-pentenyl-2-amine, 2,3-dimethylbutenyl-2-amine, dibutenyl-2-amine, n-hexenyl-2-amine, propylenediamine, trimethylamine, triethylamine, tri-n-propylamine, triisopropylamine, tri-n-butylamine, triisobutylamine, tri-sec-butylamine, tri-n-amylamine, methoxyethylamine and ethoxyethylamine; heterocyclic amines, for example pyridine, quinoline, isoquinoline, morpholine, piperidine, pyrrolidine, indoline, quinuclidine and azepine; primary arylamines, for example anilines, methoxyanilines, ethoxyanilines, o,m,p-toluidines, phenylenediamines, benzidines, naphthylamines and o,m,p-chloroanilines; but in particular triethylamine, isopropylamine and diisopropylamine.

Preferred quartemary ammonium bases which are suitable for salt formation correspond, for example, to the formula [N(R_a RbRcRa )]OH, in which R_a, R_b, Re and R_d independently of one another are C-ι-C₄alkyl. Other suitable tetraalkylammonium bases with other anions can be obtained, for example, by anion exchange reactions.

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

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

Preference is furthermore given to those compounds of the formula I, in which X-i is oxygen, sulfonyl or a group -NR₅₂SO₂-, in particular oxygen.

Of particular interest are compounds of the formula I, in which R₂ is -CH₂OCH₃, -CH₂OCH₂CH₃, -CHgCH≥OCHa, -CH₂CH₂SO₂CH₃ or -CH₂CH₂OCH₂CH₂OCH₃, preferably -CH₂CH₂OCH₃, those compounds standing out in which X_T is oxygen and R^ is -CH₂-. Among this group, preference is given to those compounds in which Q is Q^ and R₁₃ is hydroxyl.

Emphasis is furthermore given to the compounds of the formula I in which R₂

OCH, , or . If, in these preferred meanings of R₂, no free valency is indicated, as, for

CH example, in the case of ° , the point of attachment is the carbon atom indicated by "CH".

In a further preferred group of compounds of the formula I, R₃ is CF₃, CF₂CF₃, CF₂CI, CF₂H or CCI₃, particularly preferably CF₃, where R₄ is preferably hydrogen or methyl, particularly preferably hydrogen.

Re, 7, Re, R9, R-io, R11, R12. R51 and R₅₂ independently of one another are in particular hydrogen, d-C₄alkyl, CrCealkoxy-d-Cealkyl or d-Cealkoxy-C Cealkyl which is substituted by d-C₆alkoxy, where in a preferred group of compounds of the formula I additionally Q is Q₂ and Ri is methylene.

Very particularly preferably, Q is Qt and R₁₃ is hydroxyl or halogen, in particular hydroxyl. Among this group, emphasis is given to those compounds in which a) A_T is C(R₁₄R₁₅) or NR₁₆ and A₂ is C(R₁₇R₁₈), C(O) or oxygen, or b) A-i is C(R₁₄Rι₅) and A₂ is C(R₁₇Rι₈) and R₁₄ and R₂₂ together form a C₂-C₃alkylene chain, preferably an ethylene chain, where R₁₅, R₁₇, R₁₈ and R₂₁ are particularly preferably hydrogen; or c) A₂ is C(O) or C(Rι₇Rι₈), A is C(R₁₄R₁₅) and R₁₄, R₁₅, R₁₇ and R₁₈ independently of one another are hydrogen, methyl, ethyl, methoxycarbonyl or ethoxycarbonyl; or d) R₁₄ and R₁₅ or R₂₁ and R₂₂ together form a C₂alkylene chain (cyclopropyl ring), A₂ is CH₂ and R₂₁ and R₂₂ or R₁ and R₁₅ independently of one another are hydrogen, C C₄alkyl, methoxycarbonyl or ethoxycarbonyl; or e) A₂ is C(R₁₇R₁₈) and is C(R₁₄Rι₅) and R₁₈ and R₁ together form a C₂-C₃alkylene chain.

In a further outstanding group of compounds of the formula I, Q is Q₃, R₄₉ is cyclopropyl and R_S0-S(O)_n is methylthio, ethylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl.

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

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

by, for example, either a) reacting a compound of the formula la

in which R_{1 (} R₂, R₃, R and Xt are as defined under formula I and Yi is a leaving group, for example halogen or cyano, in an inert organic solvent in the presence of a base with a compound of the formula II

in which R₂₂, R₂ , A₂ and A^ are as defined under formula I, to give the compounds of the formulae Ilia and lllb

Ilia lllb

and then isomerizing these for example in the presence of a base and a catalytic amount of dimethylaminopyridine (DMAP) or a source of cyanide, for example acetone cyanohydrin; or b) reacting a compound of the formula lb

in which R^ R₂, R₃, R₄ and Xi are as defined under formula I, with a compound of the formula II

in which R₂₂, R₂₁, Ai and A₂ are as defined under formula I, in an inert organic solvent in the presence of a base and a coupling agent to give the compounds of the formula Ilia or lllb

Ilia lllb

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

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

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

a) a compound of the formula la

in which R^ R₂, R₃, R₄ and Xi are as defined under formula I and Y is a leaving group, for example halogen or cyano, is reacted with a compound of the formula I la

in which R₃₄ and R₃₅ are as defined, in an inert organic solvent in the presence of a base to give the compound of the formula lllc

lllc

in which R_{1 ;} R₂, R₃, R₄, R₃ , R35 and X^ are as defined under formula I, and this compound is then isomerized, for example in the presence of a base and a catalytic amount of a source of cyanide; or

b) a compound of the formula lb

in which Ri, R₂, R₃, R₄ and X^ are as defined under formula I, is reacted with a compound of the formula I la

R 35 in which R₃ and R₃₅ are as defined above, in an inert organic solvent in the presence of a base and a coupling agent to give the compound of the formula lllc

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

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

(0)n

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

a) a compound of the formula IV

in which Xi, R_{1 ;} R₂, R₃, R and R₄₉ are as defined above, is converted in the presence of a base, carbon disulfide and an alkylating agent of the formula V

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

in which R_{1 f} R₂, R₃, R₄, R₅₀, X₁ and R₄₉ are as defined above, and this compound is then cyclized with hydroxylamine hydrochloride, if appropriate in a solvent, in the presence of a base, for example sodium acetate, to give the isomeric compounds of the formulae Ic and Id

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

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

in which

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

or -CH₂(CO)R₄₉; and Ri, R₃, R₄, R₄₉, R₅₀, X₁ and p are as defined under formula I and R₂ is a d-C₈alkyl, C₃-C₆alkenyl or C₃-C₆alkynyl group which is mono- or polysubstituted by halogen, hydroxyl, amino, formyl, nitro, cyano, mercapto, carbamoyl, d-C₆alkoxy, C C₆alkoxycarbonyl, C₂-C₆alkenyl, C₂-C₆haloalkenyl, C₂-C₆alkynyl, C₂-C₆haloalkynyl, C₃-C₆cycloalkyl, by halogen- substituted C₃-C₆cycloaIkyl, or by C₃-C₆alkenyloxy, C₃-C₆alkynyloxy, d-C₆haloalkoxy, C₃-C₆haloalkenyloxy, cyano-d-C₆alkoxy, C C₆alkoxy-CrC₆alkoxy, d-Cealkoxy-d-Cβalkoxy- Cι-C₆alkoxy, Cι-C₆alkylthio-d-C₆alkoxy, C Cealkylsulfinyl-d-Cealkoxy, d-C₆alkylsulfonyl- d-C₆alkoxy, Cι-C₆alkoxycarbonyl-d-C₆alkoxy, d-C₆alkoxycarbonyl, d-C₆alkylcarbonyl, d-C₆alkylthio, C C₆aIkylsulfinyl, d-C₆alkylsulfonyl, d-Cehaloalkylthio, C C₆haloalkylsulfinyl, d-C₆-haloalkylsulfonyl, oxiranyl, which for its part may be substituted by d-C₆alkyl, or by (3-oxetanyl)oxy, which for its part may be substituted by d-C₆alkyl, or by benzylthio, benzylsulfinyl, benzylsulfonyl, C C₆alkylamino, di(d-C₆alkyl)amino, R₉S(O)₂O, RιoN(Rn)SO₂-, thiocyanato, phenyl, phenoxy, phenylthio, phenylsulfinyl or phenylsulfonyl; where the phenyl- or benzyl-containing groups for their part may be substituted by one or more d-C₆alkyl, C C₆haloalkyl, d-C₆alkoxy, d-C₆haloalkoxy, halogen, cyano, hydroxyl or nitro groups, or

R₂ is phenyl which may be mono- or polysubstituted by C C₆alkyl, C C₆haloalkyl, d-C₆alkoxy, d-C₆haloalkoxy, halogen, cyano, hydroxyl or nitro; or R₂ is C₃-C₆cycloalkyl, Cι-C₆alkoxy- or d-C₆alkyl-substituted C₃-C₆cycloalkyl, 3-oxetanyl or d-C₆alkyl-substituted 3-oxetanyl; or if Xi is -N(R₆)-O-, -O-NR5₁, SO₂NR₇- or -NR₅₂SO₂- and R₆, R₇, R₅₁ and R₅₂ are as defined under formula I,

R₂ may additionally be hydrogen, unsubstituted d-C₆alkyl, or a five- to ten-membered monocyclic or fused bicyclic ring system which may be aromatic, saturated or partially saturated and may contain 1 to 4 heteroatoms selected from the group consisting of nitrogen, oxygen and sulfur, where the ring system is attached directly or via a d-C₄alkylene, C₂-C₄alkenyl-C C₄alkylene, C₂-C₄alkynyl-d-C₄alkylene, -N(Rι₂)- d-C₄alkylene, -SO-C C₄alkylene or -SO₂-C C₄alkylene group to the substituent X_{1 τ} 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, Cι-C₆haloalkyl, C₂-C₆alkenyl, C₂-C₆haloalkenyl, C₂-C₆alkynyl, C₂-C₆haloalkynyl, d-C₆alkoxy, hydroxyl, d-C₆haloalkoxy, C₃-C₆alkenyloxy, C₃-C₆alkynyloxy, mercapto, d-C₆alkylthio, d-C₆-haloalkylthio, C₃-C₆alkenylthio, C₃-C₆haloalkenylthio, C₃-C₆alkynylthio, C₂-C₅alkoxyalkylthio, C₃-C₅acetylalkylthio, C₃-C₆alkoxycarbonylalkylthio, C₂-C₄cyanoalkylthio, d-C₆alkylsulfinyl, C C₆haloalkylsulfinyl, C C₆alkylsulfonyl, C Cehaloalkylsulfonyl, aminosulfonyl, C C₂alkylaminosulfonyI, di(d-C₂alkyl)aminosu!fonyl, di(CrC₄alkyl)amino, halogen, cyano, nitro, phenyl and benzylthio, where phenyl and benzylthio for their part may be substituted on the phenyl ring by C C₃alkyl, d-C₃haloalkyl, CrC₃alkoxy, d-C₃haloalkoxy, halogen, cyano or nitro, and where the substituents on the nitrogen in the heterocyclic ring are different from halogen.

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

Reaction scheme 1

Route b):

solvent e.g. CH₃CN,

Reaction scheme 1 is preferably used to prepare the compounds of the formula I having the group Q_{1 (} in which R₁₃ is hydroxyl, and the compounds of the formula I having the group Q₂, in which R₃₆ is hydroxyl. Reaction scheme 2

If (if n = 1 or 2) I d (if n = 0)

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

According to reaction scheme 1 , route a), the carboxylic acid derivatives of the formula la in which Y_T is a leaving group such as halogen, for example iodine, bromine, and in particular chlorine, N-oxyphthalimide or N,O-dimethylhydroxylamino or part of an activated ester, for example (formed from dicyclohexylcarbodiimide (DCC) and the corresponding carboxylic acid) or ^{2 5} ι ^{3 3 2} (formed from N-ethyl N'-(3-

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

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

According to reaction scheme 1 , route b), the desired derivatives of the formula I (in which R₁₃ and R₃₆ are hydroxyl) can be obtained, for example, similarly to E. Haslem, Tetrahedron, 2409-2433, 36, 1980, by esterifying the carboxylic acids of the formula lb with the dione derivatives of the formula II or pyrazoles of the formula lla in an inert solvent such as a halogenated hydrocarbon, for example dichloromethane, a nitrile, for example acetonitrile, or an aromatic hydrocarbon, for example toluene, in the presence of a base such as an alkylamine, for example triethylamine, and a coupling agent such as 2-chloro-1 -methyl- pyridinium iodide. Depending on the solvent used, this esterification is carried out at temperatures of from 0°C to 1 10°C, giving initially, as described under route a), the isomeric ester of the formula Ilia, lllb or lllc, which can be isomerized as described under route a), for example in the presence of a base and a catalytic amount of DMAP, or a source of cyanide, for example acetone cyanohydrin, to give the desired derivative of the formula I (R₁₃ and R₃₆ = hydroxyl). The activated carboxylic acid derivatives of the formula la in reaction scheme 1 (route a), in which Y, is a leaving group such as halogen, for example bromine, iodine or, in particular, chlorine, can be prepared by known standard processes, for example those described in C. Ferri "Reaktionen der organischen Synthese" [Reactions of organic sythesis], Georg Thieme Verlag, Stuttgart, 1978, page 460 ff. Such reactions are generally known and described in the literature in different variations with respect to the leaving group

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

CH_g-<\ — S0₂0- • This reaction is expediently carried out in a solvent such as an

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

The compounds of the formula IV in reaction scheme 2 can be obtained by standard processes for example from the corresponding compounds of the formula la

(la), in which R _f R₂, R₃, R₄, and Xi are as defined above and Y, is a leaving group, for example halogen, for example by Claisen condensation, or from the compounds of the formula la by reaction with a ketocarboxylic acid salt of the formula VII

COO M^"

H₂C (VII),

\

COR 49 in which R g is as defined under formula I and M⁺ is an alkali metal ion (cf., for example, WO 96/26192).

Compounds of the formula I, in which R-, is, in particular d-C₂alkyl, can, for example, also be prepared by heating an N-oxide of the formula IX under known reaction conditions in the presence of an acid anhydride (see, for example, Konno, K.; Hashimoto, K.; Shirahama, H.; Matsumoto, T.; Heterocyctes 1986, 24, 2169, or WO 00/15615) and hydrolyzing the resulting products (Ig) in a protic solvent, for example water or a water/methanol mixture, if appropriate in the presence of a base (for example lithium hydroxide or sodium hydroxide), and then converting the resulting alcohol X in the presence of a base, for example sodium hydride or potassium hydroxide, if appropriate in the presence of a phase-transfer catalyst or a crown ether, and an alkylating agent R₂-Y3, in which R₂ is as defined under formula I and Y₃ is a leaving group, for example halogen or methyl sulfonate, in an aprotic solvent, for example, tetrahydrofuran or dimethylformamide, into the corresponding derivatives of the formula Ih (in which X^ is oxygen). Compounds of the formula I, in which R₂ is CrC₆alkoxymethyl or 2-tetrahydropyranyl or 2-tetrahydrofuryl, can be prepared, for example, by treating an alcohol of the formula X with a vinyl ether of the formula VE₁, in which R₀₃, R₀₄, and R₀₅ are d-C₆alkyl or R₀₃ together with R₀₅ forms a C₂-C₃alkylene chain, in the presence of an acidic catalyst, for example para-toluenesulphonic acid, in an inert solvent, for example methylene chloride. Such reactions are generally known in the literature (see, for example, Synthesis, p. 169, 1973). The two reaction sequences are demonstrated using the example below: Reaction scheme 3

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

Reaction scheme 4

R₀₁ = H, C₁-C₄alkyl 01 CI, Br; X₀₂ = H, X,

1. Z-R₂, base e.g. NaH solvent e.g. DMF

2. aqueous work-up

X₀₁ = H, CI, Br

R₀₁ = H, C C₄alkyl

Z = S, O, N(R₈), N(R₅₂)S0₂, N(R_β)0, ON(R₅₁), O(CO)

Compounds of the formula I, in which Q denotes Q^ or Q₂ and in which R₁₃ or R₃₆ are different from hydroxyl or halogen, can be prepared by conversion processes generally known from the literature, for example acylations or carbamoylations with appropriate acid chlorides from compounds of the formula I, in which Rι₃ or R₃₆ is hydroxyl, in the presence of a suitable base, or they can be prepared by nucleophilic substitution reactions on chlorides of the formula I, in which R₁₃ and R₃₆ are chlorine, the chlorides likewise being obtainable according to known processes by reaction with a chlorinating agent, such as phosgene, thionyl chloride or oxalyl chloride. The starting materials used are, for example, appropriately substituted amines, or hydroxylamines directly, or alkylsulfonamides, mercaptans, thiophenols, phenols, heterocyclic amines or heterocyclic thiols in the presence of a base, for example 5-ethyl-2-methylpyridine, diisopropylethylamine, triethylamine, sodium bicarbonate, sodium acetate or potassium carbonate.

Compounds of the formula I, in which R₁₃ and R₃₆ contain thio groups, can be oxidized similarly to known standard processes using, for example, peracids, for example meta- chloroperbenzoic acid (m-CPBA) or peracetic acid, to give the corresponding sulfones and sulfoxides of the formula I. The degree of oxidation at the sulfur atom (SO- or S0₂-) can be controlled by the amount of oxidizing agent.

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

The compounds of the formulae I) and lla are known and can be prepared similarly as described, for example, in WO 92/07837, JP 10265441 , DE-A-3818958, EP-A-0 338 992, DE-A-3902818, EP-A-0 278 742, WO 98/29412, JP 02059566, US-A-5,089,046, GB-A- 2205316, WO 00/27821 or EP-A-0 384 736.

The required intermediates of the formula lb (or Ik, II or Im) are synthesized similarly to known processes as described, for example, in WO 00/15615, WO/00/39094 or WO 97/46530, or they can be prepared for example, according to generally known conversion methods such as the Stille (see, for example Angew. Chem. 1986, 98(6), 504- 19), Heck (see, for example, Angew. Chem. 1994, 106 (23/24), 2473-506), Sonogashira (see, for example, "Comprehensive Organometallic Synthesis", Pergamon Verlag, Oxford, Vol 3, 1991, page 521 ff.) or Wittig (for example C. Ferri "Reaktionen der organischen Synthese", Georg Thieme Verlag, Stuttgart, 1978, p. 354 ff.) reactions, starting from halogen derivatives of the formula XIV (preparation as described in WO 00/15615 or WO/0039094) or XVII (preparation similar to EP 522392) (reaction scheme 5): Reaction scheme 5

r^eaction

Intermediates of the formula lb, in which R_{1 (} R₂, R₃, R₄ and X are as defined under formula I, can also be prepared by the method according to reaction scheme 6:

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

Intermediates of the formula lb, in which R-, is Cι-C₂alkyl and R₂, R₃, R₄and X-, are as defined under formula I, can also be prepared by reacting a compound of the formula XlVa, in which R₃ and R₄ are as defined above under formula I and Y is halogen, with a nucleophile R₂-Z, in which Z is -SH, -OH, -C(O)OH, -O-N(R₅₁)H, -N(R₆)-OH -SO₂N(R₅₂)H or - N(R₈)H and R₂, Rs₂, Rs, Re, R5₁ are as defined above under formula I, in the presence of a base such as sodium hydride or an alkaline earth metal oxide or carbonate in an inert solvent such as dimethylformamide or THF at temperatures between -5 and 160°C, or, to prepare the corresponding sulfinyl or sulfonyl derivatives of the formula lu, by reacting with an oxidizing agent such as m-chloroperbenzoic acid or sodium periodate, or sodium perborate, with, depending on the degree of oxidation, temperature control known to the person skilled in the art (for example -30°C-+50°C for n=1 and -20°C-+100°C for n=2 respectively) , in an inert solvent such as dichloromethane, to give compound of the formula Iv. In reaction scheme 7 below, this is illustrated in more detail for the case Z = OH, SH, SO₂N(R₅₂)H and N(R₈)H:

Reaction scheme 7

Intermediates of the formula I, in which Q denotes a group OR₀₂ (R0₂ = CrC₆alkyl), can be converted by hydrolysis using, for example, a base, for example LiOH, in a protic solvent, for example H₂O or H₂O/methanol mixtures, into products of the formula lb.

For preparing all further compounds of the formula I functionalized according to the definitions of R_{1 ;} R₂, R₃, R₄ and X_{1 ?} there are a large number of suitable known standard methods, for example alkylation, halogenation, acylation, amidation, oximation, oxidation and reduction, the choice of the preparation methods which are suitable depending on the properties (reactivity) of the substituents in the intermediates.

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

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

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

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

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

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

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

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

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

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

Preparation examples:

Example H1 : Preparation of ethyl 2-bromomethyl-6-trifluoromethylnicotinate:

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

Example H2: 2-(2-Methoxyethoxymethyl)-6-trifluoromethylnicotinic acid:

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

Example H3: 4-Hvdroxy-3-f2-(2-methoxyethoxymethyl)-6-trifluoromethylpyridine-3-carbonvn- bicyclof3.2.1 loct-3-en-2-one:

24.9 g (0.1 mol) of 2-(2-methoxyethoxymethyl)-6-trifluoromethylnicotinic acid are dissolved in 200 ml of methylene chloride and 20 ml of oxalyl chloride, and 0.1 ml of dimethylformamide is then added dropwise. After the strong evolution of gas has ceased, triethylamine (27.9 ml, 0.2 mol), dimethylaminopyridine (1.22 g, 0.01 mol) and 15.2 g (0.1 1 mol) of bicyclo[3.2.1]octane-2,4-dione are added at a temperature of from 0 to 5°C. After 3 hours at 22°C, the reaction mixture is extracted with 2 N hydrochloric acid. The methylenechloride phase is separated off, washed with water and then extracted with 10% aqueous sodium bicarbonate solution, dried over sodium sulfate and concentrated. This gives 36.9 g (100% of theory) of 4-oxobicyclo[3.2.1]oct-2-en-2-yl 2-(2-methoxyethoxymethyl)-6-trifluoromethyl- nicotininate as an oil, which can be used further without purification.

36.9 g (0.1 mol) of 4-oxobicyclo[3.2.1]oct-2-en-2-yl 2-(2-methoxyethoxymethyl)-6-trifluoro- methylnicotinate and 27.9 ml (0.2 mol) of triethylamine are dissolved in 400 ml of acetonitrile. At a temperature of 22°C, 0.92 ml (0.01 mol) of acetone cyanohydrin is added. After 18 hours at 22°C, the reaction mixture is poured into a water/2 N hydrochloric acid mixture and extracted with ethyl acetate. The ethyl acetate phase is washed with water and then with concentrated sodium chloride solution, dried over sodium sulfate and concentrated, and the residue is triturated with hexane. Filtration gives 27.9 g (75.6% of theory) of 4-hydroxyl-3- [2-(2-methoxyethoxymethyl)-6-trifluoromethylpyridine-3-carbonyl]bicyclo[3.2.1]oct-3-en-2-one in the form of white crystals (m.p. 55-56°C). Example H4: 3-(2-Hvdroxy-4-oxobicvclo[3.2.noct-2-en-3-carbonyl)-6-trifluoromethylpyridin-2- yl methyl acetate:

5.0 g (1 mmol) of 4-hydroxy-3-(2-methyl-1 -oxy-6-trifluoromethylpyridin-3-carbonyl)- bicyclo[3.2.1 ]oct-3-en-2-one (preparation as described in WO 00/15615) are dissolved in 100 ml of toluene and, in the presence of 6.9 ml (0.073 mol) of acetic anhydride, heated at reflux temperature for 10 hours. The mixture is then partitioned between water and ethyl acetate and the organic phase is dried over sodium sulfate and concentrated under reduced pressure. The residue that remains is chromatographed on silica gel. The viscous oil obtained by eluting with a mixture of toluene, ethyl alcohol, dioxane, triethylamine and water (100:40:20:20:5 parts by volume) is dissolved in ethyl acetate and washed successively with 10% hydrochloric acid and water. The organic solution is dried over Na₂SO₄ and concentrated, giving 2.14 g (38%) of pure 3-(2-hydroxy-4-oxobicyclo[3.2.1]oct-2-ene-3- carbonyl)-6-trifluoromethylpyridin-2-ylmethyl acetate in the form of an oil. ¹H-NMR (250 MHz, CDCI₃): 17.06 (s), 1 H; 7.67 (s), 2H; 5.27 (d, J = 12.5 Hz), 1 H; 5.20 (d, J = 12.5 Hz), 1 H; 3.18, (t, J = 5.0 Hz), 1 H; 2.92, (t, J = 5.0 Hz), 1 H; 2.29-1.98 (m), 4H; 2.00, (s), 3H; 1.81 -1.73 ppm (m), 2H.

Example H5: 4-Hvdroxy-3-(2-oxiranylmethoxymethyl-6-trifluoromethylpyridine-3-carbonyl)- bicyclo[3.2.1 loct-3-en-2-one:

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

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

Example H6: (5-Hydroxy-1 ,3-dimethyl-1 H-pyrazol-4-yl)-|^"2-(2-methoxyethoxymethyl)- 6-trifluoromethylpyridin-3-vHmethanone:

1.0 g (0.004 mol) of 2-(2-methoxyethoxymethyl)~6-trifluoromethylnicotinic acid is dissolved in 10 ml of oxalyl chloride. Three drops of dimethylformamide are added, and the mixture is stirred at room temperature for 1 hour. The mixture is then concentrated using a rotary evaporator, and the residue (2-(2-methoxyethoxymethyl)-6-trifluoromethylnicotinoyl chloride) is taken up in 10 ml of methylene chloride. At a temperature of 0°C, 0.84 ml (0.006 mol) of triethylamine and 0.45 g (0.004 mol) of 2,5-dimethyl-2,4-dihydropyrazol-3-one are added. After 2 hours at a temperature of 22°C, the solvent is removed using a vacuum rotary evaporator, and the residue that remains is dissolved in 10 ml of acetonitrile and, to rearrange the intermediate (2,5-dimethyl-2H-pyrazol-3-yl 2-(2-methoxyethoxymethyl)-6- trifluoromethylnicotinate), admixed with 0.1 ml of acetone cyanohydrin and 1.13 ml (0.008 mol) of triethylamine. The reaction solution is stirred at room temperature for four hours and then concentrated. The syrup that remains is chromatographed on silica gel. The viscous oil obtained by eluting with a mixture of toluene, ethyl alcohol, dioxane, triethylamine and water (100:40:20:20:5 parts by volume) is dissolved in ethyl acetate and washed successively with 10% hydrochloric acid and water. The organic solution is dried over Na₂SO₄ and concentrated, giving 0.93 g of (5-hydroxy-1 ,3-dimethyl-1 H-pyrazol-4-yl)-[2-(2- methoxyethoxymethyl)-6-trifluoromethylpyridin-3-yl]methanone in the form of a viscous oil. ¹H NMR (300 MHz, CDCI₃, δ in ppm): 7.81 , (d, J = 6 Hz), 1 H; 7.74, (d, J = 6 Hz), 1 H; 4.84, (s), 2H; 2H: 3.71 , (s), 3H; 3.59, (t, J= 6 Hz) 2H; 3.38, (dd, J 4.0, 3.0 Hz), 1 H; 3.26, (s), 3H; 1.82 ppm, (s), 1 H. Preferred compounds of the formula I and their intermediates are listed in the tables below.

In the table below, the left-hand valency of the radical Ri is attached to the pyridine ring. If

CH no free valency is indicated in the substituent R₂, as, for example, in the case of ° , the point of attachment is at the "CH" carbon atom.

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

A-Q

where the formula A

denotes the following radicals:

Radical Ri R₂ R₄ R₃ Xi P

A2 CH₂ CH₂CH₃ H CF₃ O 0

A3 CH₂ (CH₃)₂CH H CF₃ O 0

A4 CH₂ PhCH₂ H CF₃ O 0

A5 CH₂ CH₃ H CF₃ s 0

A6 CH₂ CH₃ H CF₃ SO 0

A7 CH₂ CH₃ H CF₃ SO₂ 0

A8 CH₂ CH₃OCH₂ H CF₃ O 0

A9 CH₂ CH₃CH₂OCH₂ H CF₃ O 0

A10 CH₂ CH₃OCH₂CH₂ H CF₃ O 0 Radical i R₂ R₄ R₃ Xi P

A11 CH₂ CH₃CH2OCH₂CH2 H CF₃ O 0

A12 CH₂ CH₃OC(CH₃)₂CH₂ H CF₃ O 0

A13 CH₂ CH₃OCH(CH₃)CH₂ H CF₃ O 0

A14 CH₂ CH₃OCH₂CH(CH₃) H CF₃ O 0

A15 CH₂ CH₃OCH₂C(CH₃)₂ H CF₃ O 0

A16 CH₂ CH₃OCH(CH₃) H CF₃ O 0

A17 CH₂ CH₃OC(CH₃)₂ H CF₃ O 0

A18 CH₂ HC≡CCH₂ H CF₃ O 0

A19 CH₂ H₂C=CHCH₂ H CF₃ O 0

A20 CH₂ CH₃C≡CCH₂ H CF₃ O 0

A21 CH₂ ^• [ H H CF₃ O 0

A22 CH₂ ° CH H CF₃ O 0

A23 CH₂ H CF₃ O

0^CH 0

A24 CH₂ Λ^{^}CH H CF₃ O 0

A25 CH₂ r H CF₃ O 0

A26 CH₂ H CF₃ O 0

C^CH

A29 CH₂ H CF₃ O 0

O^_/CH

A31 CH₂ H CF₃ O 0 Q.CH Radical Ri Xi

A43 CH₂ H CF₃ O 0

N^ Radical R^ R₂ R₄ Ra Radical Ri R R₃ Xt

A58 CH_{2 A}^CH₂ H CF₃ O 0

A60 CH₂ /\^CH₂ H CF₃ O 0

A61 CH₂ /\ _^CH₂ H CF₃ O 0

A62 CH₂ CH, H CF₃ O 0

Radical R_? R_Λ Xi

A73 CH, J OCH_pCH_p H CF₃ O

Radical Ri Rp X

A91 CH₂CH₂ CH₃ H CF₃ O 0

A92 CH2CH2 CH₃CH₂ H CF₃ O 0

A93 CH₂CH₂ (CH₃)₂CH H CF₃ O 0

A94 CH₂CH₂ PhCH₂ H CF₃ O 0

A95 CH₂CH₂ CH₃ H CF₃ S 0

A96 CH₂CH CH₃ H CF₃ SO 0

A98 CH₂CH₂ (CH₃) CHCH₂ H CF₃ O

Radical Ri Xi

A133 CH₂CH₂ H CF₃ O 0 Radical R_n R₂ RA Xi Radical Ri Rp R₃ Xi

A147 CH₂CH₂ [>-CH₂ H CF₃ O 0

A149 CH₂CH₂ Λv-^CH2 H CF₃ O 0

A151 CH₂CH₂ ^N-CH₂ H CF₃ O 0

A152 CH₂CH₂ ^^CH₂ H CF₃ O 0 o—l

A158 CH₂CH₂ H CF₃ O 0 Radical Ri Rp R4 R₃ X1

A159 CH₂CH₂ H CF₃ O 0

OCH,

A164 CH CH₂ H CF₃ O 0

A168 CHPCHP H CF₃ O 0

Radical R₁ R₂ R₄ R₃ Xi p

A175 CH₂CH₂ ^OH H CF₃ O 0

ΓΎ^CHZ

A177 CH₂CH₂ ^HH2₂ HH CCFF₃₃ O 0

A182 CH(OCH₃)CH₂ CCHH₃₃ HH CCFF₃₃ O 0

A183 CH(OCH₃)CH₂ CCHH₃₃CCHH₂₂ HH CCFF₃₃ O 0

A184 CH(OCH₃)CH₂ ((CCHH₃₃))₂₂CCHH HH CCFF₃₃ O 0

Radical R R₂ R₄ R₃ X₁ p

_____ _____________ ^ _ __ _ _

O^CH

A212 CH(OCH₃)CH_{2 Q}^ H CF₃ O 0

,CH

A213 CH(OCH₃)CH₂ H CF₃ O 0

A214 CH(OCH₃)CH₂ H CF₃ O 0

A215 CH(OCH₃)CH₂ H CF₃ O 0

A216 CH(OCH₃)CH₂ H CF₃ O 0

A217 CH(OCH₃)CH₂ H CF₃ O 0

A218 CH(OCH₃)CH₂ H CF₃ O 0

A219 CH(OCH₃)CH₂ H CF₃ O 0

A220 CH(OCH₃)CH₂ H CF₃ O 0

A221 CH(OCH₃)CH₂ H CF₃ O 0

A222 CH(OCH₃)CH₂ n H CF₃ O 0

I CH₃ Radical Ri R₂ R R₃ Xi p

A224 CH(OCH₃)CH₂ H CF₃ O 0

0

A232 CH(OCH₃)CH₂ H CF₃ O 0 A233 CH(OCH₃)CH₂ / H CF₃ O 0

o A234 CH(OCH₃)CH₂ H CF₃ O 0 Radical Ri Rp R₄ Xi

A238 CH(OCH₃)CH₂ ^-CH₂ H CF₃ O 0

A239 CH(OCH₃)CH₂ H CF₃ O 0

A240 CH(OCH₃)CH₂ ^CH₂ H CF₃ O 0

A241 CH(OCH₃)CH₂ CH, H CF₃ O 0

O

A242 CH(OCH₃)CH₂ CH, H CF₃ O 0

A243 CH(OCH₃)CH₂ CH, H CF₃ O 0 o

A244 CH(OCH₃)CH₂ H CF₃ O 0

A246 CH(OCH₃)CH₂ H CF₃ O 0

A247 CH(OCH₃)CH₂ H CF₃ O 0

A248 CH(OCH₃)CH₂ H CF₃ O 0

^° O1 CH, Radical Ri R_{2 4} R₃ Xi F

CH(OCH₃)CH₂ H CF₃ O 0

C

A253 CH(OCH₃)CH₂ H CF₃ O 0 A254 CH(OCH₃)CH₂ /^CH2 H CF₃ O 0

A255 CH(OCH₃)CH₂ 0 H CF₃ O 0

A256 CH(OCH₃)CH₂ H CF₃ O 0

A257 CH(OCH₃)CH₂ H CF₃ O 0

A258 CH(OCH₃)CH₂ H CF₃ O 0

A259 CH(OCH₃)CH₂ H CF₃ O 0

A260 CH(OCH₃)CH₂ ^^^CH2 H CF₃ O 0 Radical R_n R₂ R₄ R₃ X_! p

A262 CH(OCH₃)CH₂ H CF₃ O 0

A263 CH(OCH₃)CH₂ H CF₃ O 0

A264 CH(OCH₃)CH₂ H CF₃ O 0

A265 CH(OCH₃)CH₂ ^0CH ₃ H CF₃ O 0

CΎ^CHZ

A266 CH(OCH₃)CH₂ ^OH H CF₃ O 0 fy^CH_

A267 CH(OCH₃)CH₂ X^H2 H CF₃ O 0

A268 CH(OCH₃)CH_{2 /}CH₂ H CF₃ O 0

O

A269 CH(OCH₃)CH₂ H CF₃ O 0

A270 CH(OCH₃)CH₂ H CF₃ O 0

A271 CH(OCH₃)CH₂ H CF₃ O 0

A272 CH(OCH₃)CH₂ H CF₃ O 0

Radical R₁ R₂ R₄ R₃ X, p

^~ A300 CH₂CH(OCH₃)CH₂ H CY₃ O 0^~

A301 CH₂CH(OCH₃)CH₂ ^\ H CF₃ O 0

V^CH

A302 CH₂CH(OCH₃)CH₂ ^\ H CF₃ O 0

O^_/CH

A303 CH₂CH(OCH₃)CH_{2 Q}^ H CF₃ O 0

,CH

A304 CH₂CH(OCH₃)CH₂ H CF₃ O 0

A305 CH₂CH(OCH₃)CH₂ H CF₃ O 0

A306 CH₂CH(OCH₃)CH₂ H CF₃ O 0

A307 CH₂CH(OCH₃)CH₂ H CF₃ O 0

A308 CH₂CH(OCH₃)CH₂ H CF₃ O

A309 CH₂CH(OCH₃)CH₂ H CF₃ O

A310 CH₂CH(OCH₃)CH₂ H CF₃ O 0

A311 CH₂CH(OCH₃)CH₂ H CF₃ O 0

A312 CH₂CH(OCH₃)CH₂ H CF₃ O 0 Radical R, R₂ R₄ R₃ X₁ p

A314 CH₂CH(OCH₃)CH₂ H CF₃ O

A315 CH₂CH(OCH₃)CH₂ H CF₃ O

A316 CH₂CH(OCH₃)CH₂ (^^ ^{H CF;3} °

A317 CH₂CH(OCH₃)CH_{2 H} CF₃ O

A318 CH₂CH(OCH₃)CH₂ H CF₃ O 0

A319 CH₂CH(OCH₃)CH₂ H CF₃ O 0

A320 CH₂CH(OCH₃)CH₂ H CF₃ O 0

A321 CH₂CH(OCH₃)CH₂ H CF₃ O 0

A322 CH₂CH(OCH₃)CH₂ H CF₃ O 0

A323 CH₂CH(OCH₃)CH₂ H CF₃ O 0

A324 CH₂CH(OCH₃)CH₂ / H CF₃ O 0 Radical Ri Xi

A325 CH₂CH(OCH₃)CH₂ H CF₃ O

A326 CH₂CH(OCH₃)CH₂ H CF₃ O

A327 CH₂CH(OCH₃)CH₂ H CF₃ O 0

A328 CH₂CH(OCH₃)CH₂ H CF₃ O

A329 CH₂CH(OCH₃)CH₂ H CF₃ O 0

A330 CH₂CH(OCH₃)CH₂ o~. H CF₃ O 0

A331 CH₂CH(OCH₃)CH₂ H CF₃ O 0

A332 CH₂CH(OCH₃)CH₂ -CH, H CF₃ O 0 o.

A333 CH₂CH(OCH₃)CH₂ -CH, H CF₃ O 0

A334 CH₂CH(OCH₃)CH₂ -CH, H CF₃ O 0

A335 CH₂CH(OCH₃)CH₂ H, H CF₃ O 0

A336 CH₂CH(OCH₃)CH₂ H CF₃ O 0

A337 CH₂CH(OCH₃)CH₂ H CF₃ O 0

A338 CH₂CH(OCH₃)CH₂ O H CF₃ O 0

CH, Radical Ri R₄ Xi

A340 CH₂CH(OCH₃)CH₂ CH,

A341 CH₂CH(OCH₃)CH₂ r^* H CF₃ O 0

A343 CH₂CH(OCH₃)CH₂ H CF₃ O 0

A344 CH₂CH(OCH₃)CH₂ H CF₃ O 0 A345 CH₂CH(OCH₃)CH_{2 y} ^CH2 H CF₃ O 0

A346 CH₂CH(OCH₃)CH₂ H CF₃ O 0

A347 CH₂CH(OCH₃)CH₂ H CF₃ O 0

A348 CH₂CH(OCH₃)CH₂ H CF₃ O 0

A349 CH₂CH(OCH₃)CH₂ H CF₃ O 0

A350 CH₂CH(OCH₃)CH₂ H CF₃ O 0 Radical R R₂ R₄ R₃ p

A352 CH₂CH(OCH₃)CH₂ H CF₃ O 0

A353 CH₂CH(OCH₃)CH₂ H CF₃ O 0

A354 CH₂CH(OCH₃)CH₂ H CF₃ O 0

A355 CH₂CH(OCH₃)CH₂ H CF₃ O 0

A356 CH₂CH(OCH₃)CH₂ ^OCH3 H CF₃ O 0 c"²

A357 CH₂CH(OCH₃)CH₂ ?^H H CF₃ O 0 rγ^0H'

A358 CH₂CH(OCH₃)CH₂ H CF₃ O 0

A359 CH₂CH(OCH₃)CH₂ H CF₃ O

A360 CH₂CH(OCH₃)CH₂ H CF₃ O

A361 CH₂CH(OCH₃)CH₂ H CF₃ O 0

A362 CH₂CH(OCH₃)CH₂ H CF₃ O 0

Radical Rp R₃ Xi P

A390 CH=CHCH₂ CH H CF₃ O o-

A394 CH=CHCH₂ H CF₃ O 0

L^CH

A402 CH=CHCH₂ H CF₃ O 0 Radical R Rp R₄ Xi Radical Ri Rp R₃ Xi

A420 CH=CHCH₂ [ -CH₂ H CF₃ O 0

A422 CH=CHCH₂

A423 CH=CHCH₂ r -CH, H CF₃ O 0

CH, H CF₃ O 0 o

A425 CH=CHCH₂ ^N-_CH₂ H CF₃ 0 o—l

Radical Ri R₄ R₃

A432 CH=CHCH₂ H CF₃ O 0

Radical Ri Xi

A442 CH=CHCH₂ .CH, H CF₃ O 0

o o O O O O O O O O o III OIII O O O O O O O O O O O O O o o o O O O O O O O O O O O O O O O O O O O O O O O O O O O O O O O O O O O O O O O O O O O O ro X ro X ^~ X ^~X~ ^~X ^~X ^_ X^{~ ~}X^~ X X X X X X X X X X X X X X X

x X X X X X X X X X X X X X X X X X X X X X X o o Tl o Ti o Tl o o o o o

o O O O O O O O O O O O O O O O θ n ^ω O O O O O

Radical R R₂ R₄ R₃ Xi p

___ _ __ _ _

A479 C≡CCH₂

A480 C≡CCH₂ CH H CF₃ O 0

A481 C≡CCH₂ CH H CF₃ O

A484 C≡CCH₂ /\ H CF₃ O 0

O^^CH

A485 C≡CCH₂ o^ H CF₃ O 0

XH

A492 C≡CCH₂ / H CF₃ O 0

Q Radical R₁ Rp R₃ Xi Radical Ri Rp R₄ R₃ Xi

A51 1 C≡CCH₂ P>-CH₂ H CF₃ O 0

A513 C≡CCH₂ H CF₃ O 0

A514 C≡CCH₂ CH, H CF₃ O 0 o

A515 C≡CCH₂ CH, H CF₃ O 0

A516 C≡CCH₂ CH, H CF₃ O 0 o

Radical R₁ R₂ R₄ R₃ X_n p Radical Ri R₂

A532 C≡CCH_P ,CH, H CF₃ O

Radical Ri Rp R₄ R₃ P

A546 CH₂ CH₃ H CF₂CI O 0

A547 CH₂ CH₃CH₂ H CF₂CI O 0

A548 CH₂ (CH₃)₂CH H CF₂CI O 0

A549 CH₂ PhCH₂ H CF₂Cl O 0

A550 CH₂ CH₃ H CF₂Cl S 0

A551 CH₂ CH₃ H CF₂CI SO 0

A552 CH₂ CH₃ H CF₂CI SO₂ 0

A553 CH₂ CH₃CH₂CH₂ H CF₂CI O 0

A554 CH₂ CH₃OCH₂ H CF₂CI O 0

A555 CH₂ CH3CH2OCH2 H CF₂CI O 0

A556 CH₂ CH₃OCH CH₂ H CF₂CI O 0

A557 CH₂ CH₃CH₂OCH₂CH₂ H CF₂CI O 0

A558 CH₂ CH₃OC(CH₃)₂CH₂ H CF₂CI O 0

A559 CH₂ CH₃OCH(CH₃)CH₂ H CF₂CI O 0

A560 CH₂ CH₃OCH₂CH(CH₃) H CF₂CI O 0

A561 CH₂ CH₃OCH₂C(CH₃)₂ H CF₂CI O 0

A562 CH₂ CH₃OCH(CH₃) H CF₂CI O 0

A563 CH₂ CH₃OC(CH₃)₂ H CF₂CI O 0

A564 CH₂ HC≡CCH₂ H CF₂CI O 0

A565 CH₂ H₂C=CHCH₂ H CF₂CI O 0

A566 CH₂ CH₃C=CCH₂ H CF₂CI O 0

A568 CH₂ ° CH H CF₂CI O 0 Radical R^ R₂ R₄ R₃ Xi p

A571 CH₂ CH H CF₂CI O 0

A572 CH₂ CH H CF₂CI O 0

O-

A574 CH₂ ^\ H CF₂CI O 0

V^CH

A575 CH₂ /\ H CF₂CI O 0

O^_^CH

A576 CH₂ p^ H CF₂CI O 0

CH

Radical Ri R₃ Xi

A594 CHp H CF₂CI O 0 Radical Ri Xi P

A598 CHp H CFoCI O

A602 CH₂ >-CH₂ H CF₂CI O 0

A603 CH₂ O

L -CH₂ H CF_PCI O

A604 CH₂ CH, H CF₂CI O 0

A605 CH₂ -CH, H CF₂CI O

O.

A606 CH₂ CH, H CF,CI O

A607 CH_P H CFPCI O

A608 CH₂ H CF₂CI O Radical Ri R₂ R₄ Radical R₄ R₃ Xi

A621 CH₂ H CF₂CI O

~OCH₂CH₂

CH,

Radical R R₃ P

A637 CH₂ CH₃ H CHF₂ O 0

A638 CH CH₂CH₃ H CHF₂ O 0

A639 CH₂ (CH₃)₂CH H CHF₂ O 0

A640 CH₂ PhCH₂ H CHF₂ O 0

A641 CH₂ CH₃ H CHF₂ S 0

A642 CH₂ CH₃ H CHF₂ O 0

A643 CH₂ CH₃ H CHF₂ O 0

A644 CH₂ CH₃OCH₂ H CHF₂ O 0

A645 CH₂ CH₃CH2OCH2 H CHF₂ O 0

A646 CH₂ CH₃OCH2CH₂ H CHF₂ O 0

A647 CH₂ CH₃CH₂OCH₂CH₂ H CHF₂ O 0

A648 CH₂ CH₃OC(CH₃)₂CH₂ H CHF₂ O 0

A649 CH₂ CH₃OCH(CH₃)CH₂ H CHF₂ O 0

A650 CH₂ CH₃OCH₂CH(CH₃) H CHF₂ O 0

A651 CH₂ CH₃OCH₂C(CH₃)₂ H CHF₂ O 0

A652 CH₂ CH₃OCH(CH₃) H CHF₂ O 0

A653 CH₂ CH₃OC(CH₃)₂ H CHF₂ O 0

A654 CH₂ HC≡CCH₂ H CHF₂ O 0

A655 CH₂ H₂C=CHCH₂ H CHF₂ O 0

A656 CH₂ CH₃C=CCH₂ H CHF₂ O 0

A657 CH₂ ^CH H CHF₂ O 0 Radical R^ R₂ R₄ R₃ X^ p

^_ _ _ ___ _ __

A658 CH₂

A661 CH₂ CH H CHF₂ O

A662 CH₂ CH H CHF₂ O

O-

A665 CH₂ /\ H CHF₂ O 0

O^ H

A666 CH₂ -^ H CHF₂ O 0

XH

Radical Ri Rp Xi Radical Ri R? R₃ Xi

A692 CH₂ [^CH₂ H CHF₂ O 0

A694 CH₂ CH, H CHF₂ O 0

A695 CH₂ CH, H CHF₂ O 0

O

Radical R, R₂ R₄ R₃ X, p

A704 CH₂ XH₂ r H CHF₂ O 0

K ^{^}OCH₃ Radical Ri R₂ R₃ Xi Radical Ri R^p R₄ R₃ X1

A727 CH₂ CH₃ H CF₃ O 1

A728 CH₂ CH₂CH₃ H CF₃ O 1

A729 CH₂ (CH₃)₂CH H CF₃ O 1

A730 CH₂ PhCH₂ H CF₃ O 1

A731 CH₂ CH₃ H CF₃ S 1

A732 CH₂ CH₃ H CF₃ SO 1

A733 CH₂ CH₃ H CF₃ SO₂ 1

A734 CH₂ CH₃OCH₂ H CF₃ O 1

A735 CH₂ CH₃CH₂OCH₂ H CF₃ O 1

A736 CH₂ CH3OCH2CH2 H CF₃ O 1

A737 CH₂ CH3CH2OCH2CH2 H CF₃ O 1

A738 CH₂ CH₃OC(CH₃)2CH₂ H CF₃ O 1

A739 CH₂ CH₃OCH(CH₃)CH₂ H CF₃ O 1

A740 CH₂ CH₃OCH₂CH(CH₃) H CF₃ O 1

A741 CH₂ CH₃OCH₂C(CH₃)₂ H CF₃ O 1

A742 CH₂ CH₃OCH(CH₃) H CF₃ O 1

A743 CH₂ CH₃OC(CH₃)₂ H CF₃ O 1

A744 CH₂ HC≡CCH₂ H CF₃ O 1

A745 CH₂ H₂C=CHCH₂ H CF₃ O 1

A746 CH₂ CH₃C≡CCH₂ H CF₃ O 1 Radical R R₂ R R₃ X p

A747 CH₂ [>H H CF₃ O

A748 CH₂ ° CH H CF, O

A749 CH₂ H CF₃ O

C^CH

A751 CH₂ H CF₃ O

Cf"

A752 CH₂ CH H CF₃ O

O-

A755 CH₂ /\ H CF₃ O

O^ H

A756 CH_{2 Q}^\ H CF₃ O

CH

Radical Ri R₂ R₃ Xi Radical R₃ Xi P

A782 CH₂ [>-CH₂ H CF₃ O

A784 CH₂ ^CH₂ H CF₃ O

A787 CH₂ ^^CH₂ H CF₃ O o— ' Radical R^ R₂ R₄ R₃ Xi i

A793 CH₂ ^^CH₂ H CF₃ O 1

A799 CH₂ CH₃. /O^CH ₂CH₂ H CF₃ 0 1 ^CH, Radical Ri R₃ Xi Radical Ri R₂ R₄ R3 X1 P

A817 CH₂ CH₃SCH₂CH₂ H CF₃ O 0

A818 CH₂ CH₃SOCH₂CH₂ H CF₃ O 0

A819 CH₂ CH₃SO₂CH₂CH₂ H CF₃ O 0

A820 CH₂ CH3OCH2CH2 H CF₂CI O 1

A821 CH₂ CH₃OCH₂CH2 H CF₂H O 1

A822 CH₂ CH₃OCH₂CH₂ F CF₃ O 0

A823 CH₂ CH₃OCH₂CH₂ CH₃ CF₃ O 0

A824 CH₂ CH₃OCH₂CH2 CH₃ CF₃ O 1

A825 CH₂ CH3OCH2CH2 H CF₃ s 0

A826 CH₂ CH₃OCH₂CH₂ H CF₃ SO 0

A827 CH₂ CH₃OCH₂CH₂ CH₃ CF₃ SO₂ 0

A828 CH₂ CH₃SO₂CH₂CH₂ CH₃ CF₃ O 0

Radical i X! P

A833 CH₂ CH₃C(O) H CF₃ O 0

A834 CH₂ CF₃CH₂ H CF₃ O 0

A835 CH₂ CH₃OCH₂CH2θCH₂CH2 H CF₃ O 0

A836 CH₂ HC≡CCH2CH2 H CF₃ O 0

A837 CH₂ H CF₃ O 0

Or

A838 CH₂ CH₃CH₂C(OCH3)HOCH₂CH2 H CF₃ O 0

A839 CH₂ (CH₃)₃CC(O) H CF₃ O 0

A840 CH₂ CH₂=CHCH₂OCH₂CH₂ H CF₃ O 0

A841 CH₂ CH₃CH₂CH₂OCH₂CH₂ H CF₃ O 0

A843 CH₂ n-Heptyl-C(O) H CF₃ O 0

A844 CH₂ Phenyl-C(O) H CF₃ O 0

A845 CH₂ CF3CH2OCH2CH2 H CF₃ O 0

A846 CH₂ CH₃OCH2CH2CH2 H CF₃ O 0

A847 CH₂ HOCH2CH2CH2 H CF₃ O 0

A849 CH₂ N≡CCH₂CH₂ H CF₃ O 0

A850 CH₂ CICH2CH2 H CF₃ O 0

A851 CH₂ p-\ H CF₃ O 0

CH o __/

A852 CH, O H CF, O

CH,

-o

A853 CH, CH₃OCH₂C(Br)HCH₂ H CF₃ O Radical Rp R₃ Xi P

A854 CH, O H CF₃ O ^~0

CH,

-s

A856 CH₂ HOCH₂CH₂ H CF₃ O 0

A858 CH₂ CH₃(OCH₂CH₂)₃ H CF₃ O 0

A859 CH₂ CH₃CH₂OC(CH₃)HOCH₂CH₂ H CF₃ O 0

A860 CH₂ n-Heptyl-C(O)OCH₂CH₂ H CF₃ O 0

A861 CH₂ CH₃C(O)OCH₂CH₂ H CF₃ O 0

A862 CH₂ CH₃SO₂OCH₂CH₂ H CF₃ O 0

A864 CH₂ CH₃ H CF₃ -NCH3SO2- 0

A865 CH₂ HOCH₂C(OH)HCH₂ H CF₃ O 0

A866 CH₂ Phenyl-C(O)OCH₂CH₂ H CF₃ O 0

A867 CH₂ t-Butyl-C(O)OCH₂CH₂ H CF₃ O 0

A868 CH₂ CH₃OC(O)CH₂ H CF₃ O 0

In the table below, in the case of rings, the ring attachment points for the substituents A^ and A₂ are at the carbon atom which is marked "C", for example

he

^ , in the case of open-chain structures, "(CH₃)₂C" denotes, for example, ^H:i0

In the formula A-Q, Q denotes Q

and Qi denotes the following radicals B:

Radical A_T A₂ n R21 R22 l3

B1 CH₂ CH₂ 0 H H OH

B2 CH₂ CH₂ 0 CH₃ H OH

B3 CH₂ CH₂ 0 CH₃ CH₃ OH

B4 (CH₃)CH CH₂ 0 CH₃ CH₃ OH

B5 (CH₃)₂C CH₂ 0 CH₃ CH₃ OH

B6 CH CH 0 CH₃ - OH

B7 CH₂ CH₂ 0 CH₃ CH₂=CHCH₂ OH

B8 CH₂ CH₂ 0 CH₃ HC≡CCH₂ OH

B9 CH₂ CH₂ 0 CH₃ CH₃S OH

B10 CH₂ CH₂ 0 CH₃ CH₃SO OH

B11 CH₂ CH₂ 0 CH₃ CH₃SO₂ OH

B12 CH₂ CH₂ 0 CH₃ CH₃O OH

B13 CH₂ CH₂ 0 CH₃ CH₃OC(O) OH

B14 CH₂ CH₂ 0 CH₃ CH₃CH₂OC(O) OH

B15 CH₂ (CH₃)₂C 0 H H OH

B16 O CH₂ 0 H H OH

B17 l CH₂ 0 H H OH

B20 CH₂ 0 H H OH

B21 CH₂ 0 CH₃ H OH

B22 CH₂ 0 CH₃ CH₃ OH

B23 (CH₃)₂C O 0 CH₃ CH₃ OH

B24 CH₂ O 0 CH₃ CH₃ OH Radical A_T A₂ n R21 R22 ι₃

B25 CH₃N O 0 CH₃ CH₃ OH

B28 CH₃N (CH₃)CH 0 H H OH

B29 CH₃N (CH₃)CH 0 CH₃ H OH

B30 NH (CH₃)C 0 H - OH

B31 NH CH 0 CH₃ - OH

B32 CH₃N (CH₃)C 0 H - OH

B33 CH₃N CH 0 CH₃ - OH

B34 O (CH₃)₂C 0 H - OH

B35 O (CH₃)₂C 0 CH₃ CH₃ OH

B36 O (CH₃)₂C 0 CH₃ H OH

B37 O (CH₃)C 0 H - OH

B38 O CH 0 CH₃ - OH

B39 (CH₃)₂C C=O 0 CH₃ CH₃ OH

B40 (CH₃)₂C (OH)CH 0 CH₃ CH₃ OH

B41 C=O 0 CH₃ CH₃ OH

B42 [ C=O 0 CH₂ CH₂ OH

B43 (CH₃)₂C 0 CH₃ CH₃ OH

V^c

B44 (CH₃)₂C CH₃O_χ 0 CH₃ CH₃ OH CH₃0^^C

B47 (CH₃)₂C HON=C 0 CH₃ CH₃ OH

B48 (CH₃)₂C CH₃ON=C 0 CH₃ CH₃ OH

B49 (CH₃)₂C BnON=C 0 CH₃ CH₃ OH

B50 CH O 1 H CH₂ OH

B51 CH C=O 1 H CH₂ OH

Radical A, A₂ n R21 R22 Rl3

B1 11 CH₂ (CH₃)CH 0 H H OH

B112 CH₂ CH₂ 1 H CH₂ t-Butyl-C(O)O

B113 CH₂ CH₂ 1 H CH₂ t-Heptyl-C(O)O

or Q in the formula A-Q denotes Q₂

and Q₂ denotes the following radicals C:

Radical R₃₄ R35 R36

C1 CH₃ H OH

C2 CH₃ CH₃ OH

C3 H HC≡CCH₂ OH

C4 H CH₃SO₂ OH

C5 H CH₃ OH

C6 H PhCH₂ OH

C7 CF₃ CH₃ OH

C9 CH₃OCH₂CH₂OCH₂ CH₃ OH

C10 H CH₃ CI

C11 H CH₃ NH₂

C12 H CH₃ CH₃SO₂NH

C13 H CH₃ CH₃OCH₂CH₂S

C14 H CH₃ CH₃OCH₂CH₂SO

C15 H CH₃ CH₃OCH₂CH2SO₂ Radical R₃ R35 R36

C16 H CH₃ (CH₃)₂NC(O)NH

C17 H CH₃ PhC(O)O

C18 H CH₃ CH₃OC(O)O

C19 H CH₃ CH₃(CH₂)₇S

C20 H CH₃ CH₃(CH₂)₇SO

C21 H CH₃ CH₃(CH₂)₇SO₂

C22 H CH₃ (CH₃)₂NSO₂NH

C23 H CH₃ PhS

C24 H CH₃ PhSO

C25 H CH₃ PhSO₂

C28 H CH₃ CH₃SO₂O

C29 H CH₃ p-ToiylSO₂O

or Q in the formula A-Q denotes Q₃

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

Radical R₄₉ R₅₀ n

D1 ^_CH CH₃ 0 Radical R 9 R50 n

D2 [ H CH₃ 1

D5 ^CH CF₃ 1

D6 [ H CF₃ 2

D7 [ H Ph 0

D8 [ H Ph 1

D9 ^CH Ph 2

D10 CH PhCH₂ 0

D11 [ H PhCH₂ 1

D12 [ H PhCH₂ 2

Table 1 : Intermediates for preparing the compounds of the formula I, represented as formula

A-Q in which Q denotes hydroxyl:

OH OH OH OH OH OH OH OH OH OH OH OH

A8 A9 A10 A11 A12

A13 A14 A15 A16 A17 A18 A19 A20 A21 A22 A23 A24

A25 A26 A27 A28 A29 A30 A31 A32 A33 A34 A35 A36

A37 A38 A39 A40 A41 A42 A43 A44 A45 A46 A47 A48

A49 A50 A51 A52 A53 A54 A55 A56 A57 A58 A59 A60

A61 A62 A63 A64 A65 A66 A67 A68 A69 A70 A71 A72

A73 A74 A75 A76 A77 A78 A79 A80 A81 A82 A83 A84 OH OH OH OH OH OH OH OH OH OH OH OH

A85 A86 A87 A88 A89 A90 - - ^'- - - -

A99 A100 A101 A102 A103 A104 A105 A106 A107 A108

A109 A110 A111 A112 A113 A114 A115 A116 A117 A118 A119 A120

A121 A122 A123 A124 A125 A126 A127 A128 A129 A130 A131 A132

A133 A134 A135 A136 A137 A138 A139 A140 A141 A142 A143 A144

A145 A146 A147 A148 A149 A150 A151 A152 A153 A154 A155 A156

A157 A158 A159 A160 A161 A162 A163 A164 A165 A166 A167 A168

A169 A170 A171 A172 A173 A174 A175 A176 A177 A178 A179 A180

A181 A182 A183 A184 A185 A186 A187 A188 A189 A190 A191 A192

A193 A194 A195 A196 A197 A198 A199 A200 A201 A202 A203 A204

A205 A206 A207 A208 A209 A210 A211 A212 A213 A214 A215 A216

A217 A218 A219 A220 A221 A222 A223 A224 A225 A226 A227 A228

A229 A230 A231 A232 A233 A234 A235 A236 A237 A238 A239 A240

A241 A242 A243 A244 A245 A246 A247 A248 A249 A250 A251 A252

A253 A254 A255 A256 A257 A258 A259 A260 A261 A262 A263 A264

A265 A266 A267 A268 A269 A270 A271 A272 A273 A274 A275 A276

A277 A278 A279 A280 A281 A282 A283 A284 A285 A286 A287 A288

A289 A290 A291 A292 A293 A294 A295 A296 A297 A298 A299 A300

A301 A302 A303 A304 A305 A306 A307 A308 A309 A310 A311 A312

A313 A314 A315 A316 A317 A318 A319 A320 A321 A322 A323 A324

A325 A326 A327 A328 A329 A330 A331 A332 A333 A334 A335 A336

A337 A338 A339 A340 A341 A342 A343 A344 A345 A346 A347 A348

A349 A350 A351 A352 A353 A354 A355 A356 A357 A358 A359 A360

A361 A362 A363 A364 A365 A366 A367 A368 A369 A370 A371 A372

A373 A374 A375 A376 A377 A378 A379 A380 A381 A382 A383 A384

A385 A386 A387 A388 A389 A390 A391 A392 A393 A394 A395 A396

A397 A398 A399 A400 A401 A402 A403 A404 A405 A406 A407 A408

A409 A410 A411 A412 A413 A414 A415 A416 A417 A418 A419 A420

A421 A422 A423 A424 A425 A426 A427 A428 A429 A430 A431 A432

A433 A434 A435 A436 A437 A438 A439 A440 A441 A442 A443 A444

A445 A446 A447 A448 A449 A450 A451 A452 A453 A454 A455 A456

A457 A458 A459 A460 A461 A462 A463 A464 A465 A466 A467 A468

A469 A470 A471 A472 A473 A474 A475 A476 A477 A478 A479 A480 OH OH OH OH OH OH OH OH OH OH OH OH

A481 A482 A483 A484 A485 A486 A487 A488 A489 A490 A491 A492

A493 A494 A495 A496 A497 A498 A499 A500 A501 A502 A503 A504

A505 A506 A507 A508 A509 A510 A511 A512 A513 A514 A515 A516

A517 A518 A519 A520 A521 A522 A523 A524 A525 A526 A527 A528

A529 A530 A531 A532 A533 A534 A535 A536 A537 A538 A539 A540

A541 A542 A543 A544 A545 - -

A554 A555 A556 A557 A558 A559 A560 A561 A562 A563 A564

A565 A566 A567 A568 A569 A570 A571 A572 A573 A574 A575 A576

A577 A578 A579 A580 A581 A582 A583 A584 A585 A586 A587 A588

A589 A590 A591 A592 A593 A594 A595 A596 A597 A598 A599 A600

A601 A602 A603 A604 A605 A606 A607 A608 A609 A610 A611 A612

A613 A614 A615 A616 A617 A618 A619 A620 A621 A622 A623 A624

A625 A626 A627 A628 A629 A630 A631 A632 A633 A634 A635 A636

A644 A645 A646 A647 A648

A649 A650 A651 A652 A653 A654 A655 A656 A657 A658 A659 A660

A661 A662 A663 A664 A665 A666 A667 A668 A669 A670 A671 A672

A685 A686 A687 A688 A689 A690 A691 A692 A693 A694 A695 A696

A697 A698 A699 A700 A701 A702 A703 A704 A705 A706 A707 A708

A709 A710 A711 A712 A713 A714 A715 A716 A717 A718 A719 A720

A721 A722 A723 A724 A725 A726 - - - - - -

A733 A734 A735 A736 A737 A738 A739 A740 A741 A742 A743 A744

A745 A746 A747 A748 A749 A750 A751 A752 A753 A754 A755 A756

A757 A758 A759 A760 A761 A762 A763 A764 A765 A766 A767 A768

A769 A770 A771 A772 A773 A774 A775 A776 A777 A778 A779 A780

A781 A782 A783 A784 A785 A786 A787 A788 A789 A790 A791 A792

A793 A794 A795 A796 A797 A798 A799 A800 A801 A802 A803 A804

A805 A806 A807 A808 A809 A810 A811 A812 A813 A814 A815 A816

A817 A818 A819 A820 A821 A822 A823 A824 A825 A826 A827 A828

A829 A830 A831 A832 - - - - - - - -

Table 2: Compounds of the formula I, represented as compounds of the formula A-Q

in which Q denotes Q_f and Q^ denotes the radical B52:

B52 B52 B52 B52 B52 B52 B52 B52 B52 B52 B52 B52

A1 A2 A3 A4 A5 A6 A7 A8 A9 A10 A11 A12

A13 A14 A15 A16 A17 A18 A19 A20 A21 A22 A23 A24

A25 A26 A27 A28 A29 A30 A31 A32 A33 A34 A35 A36

A37 A38 A39 A40 A41 A42 A43 A44 A45 A46 A47 A48

A49 A50 A51 A52 A53 A54 A55 A56 A57 A58 A59 A60

A61 A62 A63 A64 A65 A66 A67 A68 A69 A70 A71 A72

A73 A74 A75 A76 A77 A78 A79 A80 A81 A82 A83 A84

A85 A86 A87 A88 A89 A90 A91 A92 A93 A94 A95 A96

A97 A98 A99 A100 A101 A102 A103 A104 A105 A106 A107 A108

A109 A110 A111 A112 A113 A114 A115 A116 A117 A118 A119 A120

A121 A122 A123 A124 A125 A126 A127 A128 A129 A130 A131 A132

A133 A134 A135 A136 A137 A138 A139 A140 A141 A142 A143 A144

A145 A146 A147 A148 A149 A150 A151 A152 A153 A154 A155 A156

A157 A158 A159 A160 A161 A162 A163 A164 A165 A166 A167 A168

A169 A170 A171 A172 A173 A174 A175 A176 A177 A178 A179 A180

A181 A182 A183 A184 A185 A186 A187 A188 A189 A190 A191 A192

A193 A194 A195 A196 A197 A198 A199 A200 A201 A202 A203 A204

A205 A206 A207 A208 A209 A210 A211 A212 A213 A214 A215 A216

A217 A218 A219 A220 A221 A222 A223 A224 A225 A226 A227 A228

A229 A230 A231 A232 A233 A234 A235 A236 A237 A238 A239 A240

A241 A242 A243 A244 A245 A246 A247 A248 A249 A250 A251 A252

A253 A254 A255 A256 A257 A258 A259 A260 A261 A262 A263 A264

A265 A266 A267 A268 A269 A270 A271 A272 A273 A274 A275 A276

A277 A278 A279 A280 A281 A282 A283 A284 A285 A286 A287 A288

A289 A290 A291 A292 A293 A294 A295 A296 A297 A298 A299 A300

A301 A302 A303 A304 A305 A306 A307 A308 A309 A310 A311 A312

A313 A314 A315 A316 A317 A318 A319 A320 A321 A322 A323 A324 B52 B52 E352 B52 H£ B52 B52 B52 B52 B52 B52 B52

A325 A326 A327 A328 A329 A330 A331 A332 A333 A334 A335 A336

A337 A338 A339 A340 A341 A342 A343 A344 A345 A346 A347 A348

A349 A350 A351 A352 A353 A354 A355 A356 A357 A358 A359 A360

A361 A362 A363 A364 A365 A366 A367 A368 A369 A370 A371 A372

A373 A374 A375 A376 A377 A378 A379 A380 A381 A382 A383 A384

A385 A386 A387 A388 A389 A390 A391 A392 A393 A394 A395 A396

A397 A398 A399 A400 A401 A402 A403 A404 A405 A406 A407 A408

A409 A410 A411 A412 A413 A414 A415 A416 A417 A418 A419 A420

A421 A422 A423 A424 A425 A426 A427 A428 A429 A430 A431 A432

A433 A434 A435 A436 A437 A438 A439 A440 A441 A442 A443 A444

A445 A446 A447 A448 A449 A450 A451 A452 A453 A454 A455 A456

A457 A458 A459 A460 A461 A462 A463 A464 A465 A466 A467 A468

A469 A470 A471 A472 A473 A474 A475 A476 A477 A478 A479 A480

A481 A482 A483 A484 A485 A486 A487 A488 A489 A490 A491 A492

A493 A494 A495 A496 A497 A498 A499 A500 A501 A502 A503 A504

A505 A506 A507 A508 A509 A510 A511 A512 A513 A514 A515 A516

A517 A518 A519 A520 A521 A522 A523 A524 A525 A526 A527 A528

A529 A530 A531 A532 A533 A534 A535 A536 A537 A538 A539 A540

A541 A542 A543 A544 A545 A546 A547 A548 A549 A550 A551 A552

A553 A554 A555 A556 A557 A558 A559 A560 A561 A562 A563 A564

A565 A566 A567 A568 A569 A570 A571 A572 A573 A574 A575 A576

A577 A578 A579 A580 A581 A582 A583 A584 A585 A586 A587 A588

A589 A590 A591 A592 A593 A594 A595 A596 A597 A598 A599 A600

A601 A602 A603 A604 A605 A606 A607 A608 A609 A610 A611 A612

A613 A614 A615 A616 A617 A618 A619 A620 A621 A622 A623 A624

A625 A626 A627 A628 A629 A630 A631 A632 A633 A634 A635 A636

A637 A638 A639 A640 A641 A642 A643 A644 A645 A646 A647 A648

A649 A650 A651 A652 A653 A654 A655 A656 A657 A658 A659 A660

A661 A662 A663 A664 A665 A666 A667 A668 A669 A670 A671 A672

A673 A674 A675 A676 A677 A678 A679 A680 A681 A682 A683 A684

A685 A686 A687 A688 A689 A690 A691 A692 A693 A694 A695 A696

A697 A698 A699 A700 A701 A702 A703 A704 A705 A706 A707 A708

A709 A710 A711 A712 A713 A714 A715 A716 A717 A718 A719 A720 B52 B52 B52 B52 B52 B52 B52 |δ2 £352 BK B52 B52

^~A721 A722 A723 A724 A725 A726 A727 A728 A729 A730 A731 A732^~

A733 A734 A735 A736 A737 A738 A739 A740 A741 A742 A743 A744

A745 A746 A747 A748 A749 A750 A751 A752 A753 A754 A755 A756

A757 A758 A759 A760 A761 A762 A763 A764 A765 A766 A767 A768

A769 A770 A771 A772 A773 A774 A775 A776 A777 A778 A779 A780

A781 A782 A783 A784 A785 A786 A787 A788 A789 A790 A791 A792

A793 A794 A795 A796 A797 A798 A799 A800 A801 A802 A803 A804

A805 A806 A807 A808 A809 A810 A811 A812 A813 A814 A815 A816

A817 A818 A819 A820 A821 A822 A823 A824 A825 A826 A827 A828 A829 A830 A831 A832 - - - - - - - -

Table 3: Compounds of the formula I, represented as compounds of the formula

A-Q

in which Q denotes Qi and Q-i denotes the radical B39:

B39 B39 B39 B39 B39 B39 B39 B39 B39 B39 B39 B39

A1 A2 A3 A4 A5 A6 A7 A8 A9 A10 A11 A12

A13 A14 A15 A16 A17 A18 A19 A20 A21 A22 A23 A24

A25 A26 A27 A28 A29 A30 A31 A32 A33 A34 A35 A36

A37 A38 A39 A40 A41 A42 A43 A44 A45 A46 A47 A48

A49 A50 A51 A52 A53 A54 A55 A56 A57 A58 A59 A60

A61 A62 A63 A64 A65 A66 A67 A68 A69 A70 A71 A72

A73 A74 A75 A76 A77 A78 A79 A80 A81 A82 A83 A84

A85 A86 A87 A88 A89 A90 A91 A92 A93 A94 A95 A96

A97 A98 A99 A100 A101 A102 A103 A104 A105 A106 A107 A108

A109 A110 A111 A112 A113 A114 A115 A116 A117 A118 A119 A120

A121 A122 A123 A124 A125 A126 A127 A128 A129 A130 A131 A132

A133 A134 A135 A136 A137 A138 A139 A140 A141 A142 A143 A144

A145 A146 A147 A148 A149 A150 A151 A152 A153 A154 A155 A156 B39 B39 B39 B39 B39 B39 B39 B39 B39 B39 B39 B39

A157 A158 A159 A160 A161 A162 A163 A164 A165 A166 A167 A168

A169 A170 A171 A172 A173 A174 A175 A176 A177 A178 A179 A180

A181 A182 A183 A184 A185 A186 A187 A188 A189 A190 A191 A192

A193 A194 A195 A196 A197 A198 A199 A200 A201 A202 A203 A204

A205 A206 A207 A208 A209 A210 A211 A212 A213 A214 A215 A216

A217 A218 A219 A220 A221 A222 A223 A224 A225 A226 A227 A228

A229 A230 A231 A232 A233 A234 A235 A236 A237 A238 A239 A240

A241 A242 A243 A244 A245 A246 A247 A248 A249 A250 A251 A252

A253 A254 A255 A256 A257 A258 A259 A260 A261 A262 A263 A264

A265 A266 A267 A268 A269 A270 A271 A272 A273 A274 A275 A276

A277 A278 A279 A280 A281 A282 A283 A284 A285 A286 A287 A288

A289 A290 A291 A292 A293 A294 A295 A296 A297 A298 A299 A300

A301 A302 A303 A304 A305 A306 A307 A308 A309 A310 A311 A312

A313 A314 A315 A316 A317 A318 A319 A320 A321 A322 A323 A324

A325 A326 A327 A328 A329 A330 A331 A332 A333 A334 A335 A336

A337 A338 A339 A340 A341 A342 A343 A344 A345 A346 A347 A348

A349 A350 A351 A352 A353 A354 A355 A356 A357 A358 A359 A360

A361 A362 A363 A364 A365 A366 A367 A368 A369 A370 A371 A372

A373 A374 A375 A376 A377 A378 A379 A380 A381 A382 A383 A384

A385 A386 A387 A388 A389 A390 A391 A392 A393 A394 A395 A396

A397 A398 A399 A400 A401 A402 A403 A404 A405 A406 A407 A408

A409 A410 A411 A412 A413 A414 A415 A416 A417 A418 A419 A420

A421 A422 A423 A424 A425 A426 A427 A428 A429 A430 A431 A432

A433 A434 A435 A436 A437 A438 A439 A440 A441 A442 A443 A444

A445 A446 A447 A448 A449 A450 A451 A452 A453 A454 A455 A456

A457 A458 A459 A460 A461 A462 A463 A464 A465 A466 A467 A468

A469 A470 A471 A472 A473 A474 A475 A476 A477 A478 A479 A480

A481 A482 A483 A484 A485 A486 A487 A488 A489 A490 A491 A492

A493 A494 A495 A496 A497 A498 A499 A500 A501 A502 A503 A504

A505 A506 A507 A508 A509 A510 A511 A512 A513 A514 A515 A516

A517 A518 A519 A520 A521 A522 A523 A524 A525 A526 A527 A528

A529 A530 A531 A532 A533 A534 A535 A536 A537 A538 A539 A540

A541 A542 A543 A544 A545 A546 A547 A548 A549 A550 A551 A552 B39 B39 B39 B39 H B39 B39 U9 B39 B39 B39 B39

A553 A554 A555 A556 A557 A558 A559 A560 A561 A562 A563 A564

A565 A566 A567 A568 A569 A570 A571 A572 A573 A574 A575 A576

A577 A578 A579 A580 A581 A582 A583 A584 A585 A586 A587 A588

A589 A590 A591 A592 A593 A594 A595 A596 A597 A598 A599 A600

A601 A602 A603 A604 A605 A606 A607 A608 A609 A610 A611 A612

A613 A614 A615 A616 A617 A618 A619 A620 A621 A622 A623 A624

A625 A626 A627 A628 A629 A630 A631 A632 A633 A634 A635 A636

A637 A638 A639 A640 A641 A642 A643 A644 A645 A646 A647 A648

A649 A650 A651 A652 A653 A654 A655 A656 A657 A658 A659 A660

A661 A662 A663 A664 A665 A666 A667 A668 A669 A670 A671 A672

A673 A674 A675 A676 A677 A678 A679 A680 A681 A682 A683 A684

A685 A686 A687 A688 A689 A690 A691 A692 A693 A694 A695 A696

A697 A698 A699 A700 A701 A702 A703 A704 A705 A706 A707 A708

A709 A710 A711 A712 A713 A714 A715 A716 A717 A718 A719 A720

A721 A722 A723 A724 A725 A726 A727 A728 A729 A730 A731 A732

A733 A734 A735 A736 A737 A738 A739 A740 A741 A742 A743 A744

A745 A746 A747 A748 A749 A750 A751 A752 A753 A754 A755 A756

A757 A758 A759 A760 A761 A762 A763 A764 A765 A766 A767 A768

A769 A770 A771 A772 A773 A774 A775 A776 A777 A778 A779 A780

A781 A782 A783 A784 A785 A786 A787 A788 A789 A790 A791 A792

A793 A794 A795 A796 A797 A798 A799 A800 A801 A802 A803 A804

A805 A806 A807 A808 A809 A810 A81 1 A812 A813 A814 A815 A816

A817 A818 A819 A820 A821 A822 A823 A824 A825 A826 A827 A828

A829 A830 A831 A832

Table 4: Compounds of the formula I, represented as compounds of the formula

A-Q

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

B3 B3 B3 B3 B3 B3 B3 B3 B3 B3 B3 B3 ____ _ __ __ _ _ __ _ _ _ _ __ A8 A9 A10 A11 A12

A13 A14 A15 A16 A17 A18 A19 A20 A21 A22 A23 A24

A25 A26 A27 A28 A29 A30 A31 A32 A33 A34 A35 A36

A37 A38 A39 A40 A41 A42 A43 A44 A45 A46 A47 A48

A49 A50 A51 A52 A53 A54 A55 A56 A57 A58 A59 A60

A61 A62 A63 A64 A65 A66 A67 A68 A69 A70 A71 A72

A73 A74 A75 A76 A77 A78 A79 A80 A81 A82 A83 A84

A85 A86 A87 A88 A89 A90

A99 A100 A101 A102 A103 A104 A105 A106 A107 A108

A109 A110 A111 A112 A113 A114 A115 A116 A117 A118 A119 A120

A121 A122 A123 A124 A125 A126 A127 A128 A129 A130 A131 A132

A133 A134 A135 A136 A137 A138 A139 A140 A141 A142 A143 A144

A145 A146 A147 A148 A149 A150 A151 A152 A153 A154 A155 A156

A157 A158 A159 A160 A161 A162 A163 A164 A165 A166 A167 A168

A169 A170 A171 A172 A173 A174 A175 A176 A177 A178 A179 A180

A181 A182 A183 A184 A185 A186 A187 A188 A189 A190 A191 A192

A193 A194 A195 A196 A197 A198 A199 A200 A201 A202 A203 A204

A205 A206 A207 A208 A209 A210 A211 A212 A213 A214 A215 A216

A217 A218 A219 A220 A221 A222 A223 A224 A225 A226 A227 A228

A229 A230 A231 A232 A233 A234 A235 A236 A237 A238 A239 A240

A241 A242 A243 A244 A245 A246 A247 A248 A249 A250 A251 A252

A253 A254 A255 A256 A257 A258 A259 A260 A261 A262 A263 A264

A265 A266 A267 A268 A269 A270 A271 A272 A273 A274 A275 A276

A277 A278 A279 A280 A281 A282 A283 A284 A285 A286 A287 A288

A289 A290 A291 A292 A293 A294 A295 A296 A297 A298 A299 A300

A301 A302 A303 A304 A305 A306 A307 A308 A309 A310 A311 A312

A313 A314 A315 A316 A317 A318 A319 A320 A321 A322 A323 A324

A325 A326 A327 A328 A329 A330 A331 A332 A333 A334 A335 A336

A337 A338 A339 A340 A341 A342 A343 A344 A345 A346 A347 A348

A349 A350 A351 A352 A353 A354 A355 A356 A357 A358 A359 A360

A361 A362 A363 A364 A365 A366 A367 A368 A369 A370 A371 A372

A373 A374 A375 A376 A377 A378 A379 A380 A381 A382 A383 A384 ___ _ _ __ __ _ __ _ __ __ _ gg

A385 A386 A387 A388 A389 A390 A391 A392 A393 A394 A395 A396

A397 A398 A399 A400 A401 A402 A403 A404 A405 A406 A407 A408

A409 A410 A411 A412 A413 A414 A415 A416 A417 A418 A419 A420

A421 A422 A423 A424 A425 A426 A427 A428 A429 A430 A431 A432

A433 A434 A435 A436 A437 A438 A439 A440 A441 A442 A443 A444

A445 A446 A447 A448 A449 A450 A451 A452 A453 A454 A455 A456

A457 A458 A459 A460 A461 A462 A463 A464 A465 A466 A467 A468

A469 A470 A471 A472 A473 A474 A475 A476 A477 A478 A479 A480

A481 A482 A483 A484 A485 A486 A487 A488 A489 A490 A491 A492

A493 A494 A495 A496 A497 A498 A499 A500 A501 A502 A503 A504

A505 A506 A507 A508 A509 A510 A511 A512 A513 A514 A515 A516

A517 A518 A519 A520 A521 A522 A523 A524 A525 A526 A527 A528

A529 A530 A531 A532 A533 A534 A535 A536 A537 A538 A539 A540

A541 A542 A543 A544 A545 - - - - - - -

A554 A555 A556 A557 A558 A559 A560 A561 A562 A563 A564

A565 A566 A567 A568 A569 A570 A571 A572 A573 A574 A575 A576

A577 A578 A579 A580 A581 A582 A583 A584 A585 A586 A587 A588

A589 A590 A591 A592 A593 A594 A595 A596 A597 A598 A599 A600

A601 A602 A603 A604 A605 A606 A607 A608 A609 A610 A611 A612

A613 A614 A615 A616 A617 A618 A619 A620 A621 A622 A623 A624

A625 A626 A627 A628 A629 A630 A631 A632 A633 A634 A635 A636

A644 A645 A646 A647 A648

A649 A650 A651 A652 A653 A654 A655 A656 A657 A658 A659 A660

A661 A662 A663 A664 A665 A666 A667 A668 A669 A670 A671 A672

A685 A686 A687 A688 A689 A690 A691 A692 A693 A694 A695 A696

A697 A698 A699 A700 A701 A702 A703 A704 A705 A706 A707 A708

A709 A710 A711 A712 A713 A714 A715 A716 A717 A718 A719 A720

A721 A722 A723 A724 A725 A726

A733 A734 A735 A736 A737 A738 A739 A740 A741 A742 A743 A744

A745 A746 A747 A748 A749 A750 A751 A752 A753 A754 A755 A756

A757 A758 A759 A760 A761 A762 A763 A764 A765 A766 A767 A768

A769 A770 A771 A772 A773 A774 A775 A776 A777 A778 A779 A780

A781 A782 A783 A784 A785 A786 A787 A788 A789 A790 A791 A792 B3 U B3 B3 U B3 U B3 U B3 B3 B3

A793 A794 A795 A796 A797 A798 A799 A800 A801 A802 A803 A804

A805 A806 A807 A808 A809 A810 A81 1 A812 A813 A814 A815 A816

A817 A818 A819 A820 A821 A822 A823 A824 A825 A826 A827 A828

A829 A830 A831 A832 -

Table 5: Compounds of the formula I. represented as compounds of the formula

A-Q

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

C5 C5 C5 C5 C5 C5 C5 C5 C5 C5 C5 C5

A1 A2 A3 A4 A5 A6 A7 A8 A9 A10 A11 A12

A13 A14 A15 A16 A17 A18 A19 A20 A21 A22 A23 A24

A25 A26 A27 A28 A29 A30 A31 A32 A33 A34 A35 A36

A37 A38 A39 A40 A41 A42 A43 A44 A45 A46 A47 A48

A49 A50 A51 A52 A53 A54 A55 A56 A57 A58 A59 A60

A61 A62 A63 A64 A65 A66 A67 A68 A69 A70 A71 A72

A73 A74 A75 A76 A77 A78 A79 A80 A81 A82 A83 A84

A85 A86 A87 A88 A89 A90 A91 A92 A93 A94 A95 A96

A97 A98 A99 A100 A101 A102 A103 A104 A105 A106 A107 A108

A109 A110 A111 A112 A113 A114 A115 A116 A117 A118 A119 A120

A121 A122 A123 A124 A125 A126 A127 A128 A129 A130 A131 A132

A133 A134 A135 A136 A137 A138 A139 A140 A141 A142 A143 A144

A145 A146 A147 A148 A149 A150 A151 A152 A153 A154 A155 A156

A157 A158 A159 A160 A161 A162 A163 A164 A165 A166 A167 A168

A169 A170 A171 A172 A173 A174 A175 A176 A177 A178 A179 A180

A181 A182 A183 A184 A185 A186 A187 A188 A189 A190 A191 A192

A193 A194 A195 A196 A197 A198 A199 A200 A201 A202 A203 A204

A205 A206 A207 A208 A209 A210 A211 A212 A213 A214 A215 A216

A217 A218 A219 A220 A221 A222 A223 A224 A225 A226 A227 A228 C5 C5 C5 C5 C5 C5 C5 C5 C5 C5 C5 C5

A229 A230 A231 A232 A233 A234 A235 A236 A237 A238 A239 A240

A241 A242 A243 A244 A245 A246 A247 A248 A249 A250 A251 A252

A253 A254 A255 A256 A257 A258 A259 A260 A261 A262 A263 A264

A265 A266 A267 A268 A269 A270 A271 A272 A273 A274 A275 A276

A277 A278 A279 A280 A281 A282 A283 A284 A285 A286 A287 A288

A289 A290 A291 A292 A293 A294 A295 A296 A297 A298 A299 A300

A301 A302 A303 A304 A305 A306 A307 A308 A309 A310 A311 A312

A313 A314 A315 A316 A317 A318 A319 A320 A321 A322 A323 A324

A325 A326 A327 A328 A329 A330 A331 A332 A333 A334 A335 A336

A337 A338 A339 A340 A341 A342 A343 A344 A345 A346 A347 A348

A349 A350 A351 A352 A353 A354 A355 A356 A357 A358 A359 A360

A361 A362 A363 A364 A365 A366 A367 A368 A369 A370 A371 A372

A373 A374 A375 A376 A377 A378 A379 A380 A381 A382 A383 A384

A385 A386 A387 A388 A389 A390 A391 A392 A393 A394 A395 A396

A397 A398 A399 A400 A401 A402 A403 A404 A405 A406 A407 A408

A409 A410 A411 A412 A413 A414 A415 A416 A417 A418 A419 A420

A421 A422 A423 A424 A425 A426 A427 A428 A429 A430 A431 A432

A433 A434 A435 A436 A437 A438 A439 A440 A441 A442 A443 A444

A445 A446 A447 A448 A449 A450 A451 A452 A453 A454 A455 A456

A457 A458 A459 A460 A461 A462 A463 A464 A465 A466 A467 A468

A469 A470 A471 A472 A473 A474 A475 A476 A477 A478 A479 A480

A481 A482 A483 A484 A485 A486 A487 A488 A489 A490 A491 A492

A493 A494 A495 A496 A497 A498 A499 A500 A501 A502 A503 A504

A505 A506 A507 A508 A509 A510 A511 A512 A513 A514 A515 A516

A517 A518 A519 A520 A521 A522 A523 A524 A525 A526 A527 A528

A529 A530 A531 A532 A533 A534 A535 A536 A537 A538 A539 A540

A541 A542 A543 A544 A545 A546 A547 A548 A549 A550 A551 A552

A553 A554 A555 A556 A557 A558 A559 A560 A561 A562 A563 A564

A565 A566 A567 A568 A569 A570 A571 A572 A573 A574 A575 A576

A577 A578 A579 A580 A581 A582 A583 A584 A585 A586 A587 A588

A589 A590 A591 A592 A593 A594 A595 A596 A597 A598 A599 A600

A601 A602 A603 A604 A605 A606 A607 A608 A609 A610 A611 A612

A613 A614 A615 A616 A617 A618 A619 A620 A621 A622 A623 A624 C5 C5 C5 C5 C5 C5 C5 C5 C5 C5 C5 C5

A625 A626 A627 A628 A629 A630 A631 A632 A633 A634 A635 A636

A637 A638 A639 A640 A641 A642 A643 A644 A645 A646 A647 A648

A649 A650 A651 A652 A653 A654 A655 A656 A657 A658 A659 A660

A661 A662 A663 A664 A665 A666 A667 A668 A669 A670 A671 A672

A673 A674 A675 A676 A677 A678 A679 A680 A681 A682 A683 A684

A685 A686 A687 A688 A689 A690 A691 A692 A693 A694 A695 A696

A697 A698 A699 A700 A701 A702 A703 A704 A705 A706 A707 A708

A709 A710 A71 1 A712 A713 A714 A715 A716 A717 A718 A719 A720

A721 A722 A723 A724 A725 A726 A727 A728 A729 A730 A731 A732

A733 A734 A735 A736 A737 A738 A739 A740 A741 A742 A743 A744

A745 A746 A747 A748 A749 A750 A751 A752 A753 A754 A755 A756

A757 A758 A759 A760 A761 A762 A763 A764 A765 A766 A767 A768

A769 A770 A771 A772 A773 A774 A775 A776 A777 A778 A779 A780

A781 A782 A783 A784 A785 A786 A787 A788 A789 A790 A791 A792

A793 A794 A795 A796 A797 A798 A799 A800 A801 A802 A803 A804

A805 A806 A807 A808 A809 A810 A811 A812 A813 A814 A815 A816

A817 A818 A819 A820 A821 A822 A823 A824 A825 A826 A827 A828

A829 A830 A831 A832

Table 6: Compounds of the formula I, represented as compounds of the formula

A-Q

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

C2 C2 C2 C2 C2 C2 C2 C2 C2 C2 C2 C2

A1 A2 A3 A4 A5 A6 A7 A8 A9 A10 A11 A12

A13 A14 A15 A16 A17 A18 A19 A20 A21 A22 A23 A24

A25 A26 A27 A28 A29 A30 A31 A32 A33 A34 A35 A36

A37 A38 A39 A40 A41 A42 A43 A44 A45 A46 A47 A48

A49 A50 A51 A52 A53 A54 A55 A56 A57 A58 A59 A60 _____ ___ _ _ __ _ _ _ _ _ __ __

A61 A62 A63 A64 A65 A66 A67 A68 A69 A70 A7Ϊ A72

A73 A74 A75 A76 A77 A78 A79 A80 A81 A82 A83 A84

A85 A86 A87 A88 A89 A90 A91 A92 A93 A94 A95 A96

A97 A98 A99 A100 A101 A102 A103 A104 A105 A106 A107 A108

A109 A110 A111 A112 A113 A114 A115 A116 A117 A118 A119 A120

A121 A122 A123 A124 A125 A126 A127 A128 A129 A130 A131 A132

A133 A134 A135 A136 A137 A138 A139 A140 A141 A142 A143 A144

A145 A146 A147 A148 A149 A150 A151 A152 A153 A154 A155 A156

A157 A158 A159 A160 A161 A162 A163 A164 A165 A166 A167 A168

A169 A170 A171 A172 A173 A174 A175 A176 A177 A178 A179 A180

A181 A182 A183 A184 A185 A186 A187 A188 A189 A190 A191 A192

A193 A194 A195 A196 A197 A198 A199 A200 A201 A202 A203 A204

A205 A206 A207 A208 A209 A210 A211 A212 A213 A214 A215 A216

A217 A218 A219 A220 A221 A222 A223 A224 A225 A226 A227 A228

A229 A230 A231 A232 A233 A234 A235 A236 A237 A238 A239 A240

A241 A242 A243 A244 A245 A246 A247 A248 A249 A250 A251 A252

A253 A254 A255 A256 A257 A258 A259 A260 A261 A262 A263 A264

A265 A266 A267 A268 A269 A270 A271 A272 A273 A274 A275 A276

A277 A278 A279 A280 A281 A282 A283 A284 A285 A286 A287 A288

A289 A290 A291 A292 A293 A294 A295 A296 A297 A298 A299 A300

A301 A302 A303 A304 A305 A306 A307 A308 A309 A310 A311 A312

A313 A314 A315 A316 A317 A318 A319 A320 A321 A322 A323 A324

A325 A326 A327 A328 A329 A330 A331 A332 A333 A334 A335 A336

A337 A338 A339 A340 A341 A342 A343 A344 A345 A346 A347 A348

A349 A350 A351 A352 A353 A354 A355 A356 A357 A358 A359 A360

A361 A362 A363 A364 A365 A366 A367 A368 A369 A370 A371 A372

A373 A374 A375 A376 A377 A378 A379 A380 A381 A382 A383 A384

A385 A386 A387 A388 A389 A390 A391 A392 A393 A394 A395 A396

A397 A398 A399 A400 A401 A402 A403 A404 A405 A406 A407 A408

A409 A410 A411 A412 A413 A414 A415 A416 A417 A418 A419 A420

A421 A422 A423 A424 A425 A426 A427 A428 A429 A430 A431 A432

A433 A434 A435 A436 A437 A438 A439 A440 A441 A442 A443 A444

A445 A446 A447 A448 A449 A450 A451 A452 A453 A454 A455 A456 C2 C2 C2 C2 C2 C2 C2 C2 C2 C2 C2 C2

A457 A458 A459 A460 A461 A462 A463 A464 A465 A466 A467 A468

A469 A470 A471 A472 A473 A474 A475 A476 A477 A478 A479 A480

A481 A482 A483 A484 A485 A486 A487 A488 A489 A490 A491 A492

A493 A494 A495 A496 A497 A498 A499 A500 A501 A502 A503 A504

A505 A506 A507 A508 A509 A510 A511 A512 A513 A514 A515 A516

A517 A518 A519 A520 A521 A522 A523 A524 A525 A526 A527 A528

A529 A530 A531 A532 A533 A534 A535 A536 A537 A538 A539 A540

A541 A542 A543 A544 A545 A546 A547 A548 A549 A550 A551 A552

A553 A554 A555 A556 A557 A558 A559 A560 A561 A562 A563 A564

A565 A566 A567 A568 A569 A570 A571 A572 A573 A574 A575 A576

A577 A578 A579 A580 A581 A582 A583 A584 A585 A586 A587 A588

A589 A590 A591 A592 A593 A594 A595 A596 A597 A598 A599 A600

A601 A602 A603 A604 A605 A606 A607 A608 A609 A610 A611 A612

A613 A614 A615 A616 A617 A618 A619 A620 A621 A622 A623 A624

A625 A626 A627 A628 A629 A630 A631 A632 A633 A634 A635 A636

A637 A638 A639 A640 A641 A642 A643 A644 A645 A646 A647 A648

A649 A650 A651 A652 A653 A654 A655 A656 A657 A658 A659 A660

A661 A662 A663 A664 A665 A666 A667 A668 A669 A670 A671 A672

A673 A674 A675 A676 A677 A678 A679 A680 A681 A682 A683 A684

A685 A686 A687 A688 A689 A690 A691 A692 A693 A694 A695 A696

A697 A698 A699 A700 A701 A702 A703 A704 A705 A706 A707 A708

A709 A710 A711 A712 A713 A714 A715 A716 A717 A718 A719 A720

A721 A722 A723 A724 A725 A726 A727 A728 A729 A730 A731 A732

A733 A734 A735 A736 A737 A738 A739 A740 A741 A742 A743 A744

A745 A746 A747 A748 A749 A750 A751 A752 A753 A754 A755 A756

A757 A758 A759 A760 A761 A762 A763 A764 A765 A766 A767 A768

A769 A770 A771 A772 A773 A774 A775 A776 A777 A778 A779 A780

A781 A782 A783 A784 A785 A786 A787 A788 A789 A790 A791 A792

A793 A794 A795 A796 A797 A798 A799 A800 A801 A802 A803 A804

A805 A806 A807 A808 A809 A810 A811 A812 A813 A814 A815 A816

A817 A818 A819 A820 A821 A822 A823 A824 A825 A826 A827 A828

A829 A830 A831 A832 - - - - - - - - Table 7: Compounds of the formula I, represented as compounds of the formula

A-Q

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

D1/D2/ D1/D2/ D1/D2/ D1/D2/ D1/D2/ D1/D2/ D1/D2/ D1/D2/ D1/D2/ D1/D2/ D1/D2/ D1/D2/

D3 D3 D3 D3 D3 D3 D3 D3 D3 D3 D3 D3

. _ _ _ A8 A9 A10 A11 A12

A13 A14 A15 A16 A17 A18 A19 A20 A21 A22 A23 A24

A25 A26 A27 A28 A29 A30 A31 A32 A33 A34 A35 A36

A37 A38 A39 A40 A41 A42 A43 A44 A45 A46 A47 A48

A49 A50 A51 A52 A53 A54 A55 A56 A57 A58 A59 A60

A61 A62 A63 A64 A65 A66 A67 A68 A69 A70 A71 A72

A73 A74 A75 A76 All A78 A79 A80 A81 A82 A83 A84

A85 A86 A87 A88 A89 A90 - - - - - -

- - A99 A100 A101 A102 A103 A104 A105 A106 A107 A108

A109 A110 A111 A112 A113 A114 A115 A116 A117 A118 A119 A120

A121 A122 A123 A124 A125 A126 A127 A128 A129 A130 A131 A132

A133 A134 A135 A136 A137 A138 A139 A140 A141 A142 A143 A144

A145 A146 A147 A148 A149 A150 A151 A152 A153 A154 A155 A156

A157 A158 A159 A160 A161 A162 A163 A164 A165 A166 A167 A168

A169 A170 A171 A172 A173 A174 A175 A176 A177 A178 A179 A180

A181 A182 A183 A184 A185 A186 A187 A188 A189 A190 A191 A192

A193 A194 A195 A196 A197 A198 A199 A200 A201 A202 A203 A204

A205 A206 A207 A208 A209 A210 A211 A212 A213 A214 A215 A216

A217 A218 A219 A220 A221 A222 A223 A224 A225 A226 A227 A228

A229 A230 A231 A232 A233 A234 A235 A236 A237 A238 A239 A240

A241 A242 A243 A244 A245 A246 A247 A248 A249 A250 A251 A252

A253 A254 A255 A256 A257 A258 A259 A260 A261 A262 A263 A264

A265 A266 A267 A268 A269 A270 A271 A272 A273 A274 A275 A276

A277 A278 A279 A280 A281 A282 A283 A284 A285 A286 A287 A288 D1/D2/ D1/D2/ DVD2I D1/D2/ D1/D2/ D1/D2/ D1/D2/ D1/D27 D1/D27 D1/D2/ D1/D2/ D1/D2/

D3 D3 D3 D3 D3 D3 D3 D3 D3 D3 D3 D3

A289 A290 A291 A292 A293 A294 A295 A296 A297 A298 A299 A300

A301 A302 A303 A304 A305 A306 A307 A308 A309 A310 A311 A312

A313 A314 A315 A316 A317 A318 A319 A320 A321 A322 A323 A324

A325 A326 A327 A328 A329 A330 A331 A332 A333 A334 A335 A336

A337 A338 A339 A340 A341 A342 A343 A344 A345 A346 A347 A348

A349 A350 A351 A352 A353 A354 A355 A356 A357 A358 A359 A360

A361 A362 A363 A364 A365 A366 A367 A368 A369 A370 A371 A372

A373 A374 A375 A376 A377 A378 A379 A380 A381 A382 A383 A384

A385 A386 A387 A388 A389 A390 A391 A392 A393 A394 A395 A396

A397 A398 A399 A400 A401 A402 A403 A404 A405 A406 A407 A408

A409 A410 A411 A412 A413 A414 A415 A416 A417 A418 A419 A420

A421 A422 A423 A424 A425 A426 A427 A428 A429 A430 A431 A432

A433 A434 A435 A436 A437 A438 A439 A440 A441 A442 A443 A444

A445 A446 A447 A448 A449 A450 A451 A452 A453 A454 A455 A456

A457 A458 A459 A460 A461 A462 A463 A464 A465 A466 A467 A468

A469 A470 A471 A472 A473 A474 A475 A476 A477 A478 A479 A480

A481 A482 A483 A484 A485 A486 A487 A488 A489 A490 A491 A492

A493 A494 A495 A496 A497 A498 A499 A500 A501 A502 A503 A504

A505 A506 A507 A508 A509 A510 A511 A512 A513 A514 A515 A516

A517 A518 A519 A520 A521 A522 A523 A524 A525 A526 A527 A528

A529 A530 A531 A532 A533 A534 A535 A536 A537 A538 A539 A540

A541 A542 A543 A544 A545 - - - - - - -

- A554 A555 A556 A557 A558 A559 A560 A561 A562 A563 A564

A565 A566 A567 A568 A569 A570 A571 A572 A573 A574 A575 A576

A577 A578 A579 A580 A581 A582 A583 A584 A585 A586 A587 A588

A589 A590 A591 A592 A593 A594 A595 A596 A597 A598 A599 A600

A601 A602 A603 A604 A605 A606 A607 A608 A609 A610 A611 A612

A613 A614 A615 A616 A617 A618 A619 A620 A621 A622 A623 A624

A625 A626 A627 A628 A629 A630 A631 A632 A633 A634 A635 A636

- - - - - - - A644 A645 A646 A647 A648

A649 A650 A651 A652 A653 A654 A655 A656 A657 A658 A659 A660 D1/D2/ D1/D2/ D1/D2 D1/D2/ D1/D2/ D1/D2/ D1/D2/ D1/D2/ D1/D2/ D1/D2/ D1/D2 D1/D2/

D3 D3 D3 D3 D3 D3 D3 D3 D3 D3 D3 D3

A661 A662 A663 A664 A665 A666 A667 A668 A669 A670 A671 A672

A685 A686 A687 A688 A689 A690 A691 A692 A693 A694 A695 A696

A697 A698 A699 A700 A701 A702 A703 A704 A705 A706 A707 A708

A709 A710 A711 A712 A713 A714 A715 A716 A717 A718 A719 A720

A721 A722 A723 A724 A725 A726 - - - - - -

A733 A734 A735 A736 A737 A738 A739 A740 A741 A742 A743 A744

A745 A746 A747 A748 A749 A750 A751 A752 A753 A754 A755 A756

A757 A758 A759 A760 A761 A762 A763 A764 A765 A766 A767 A768

A769 A770 A771 A772 A773 A774 A775 A776 A777 A778 A779 A780

A781 A782 A783 A784 A785 A786 A787 A788 A789 A790 A791 A792

A793 A794 A795 A796 A797 A798 A799 A800 A801 A802 A803 A804

A805 A806 A807 A808 A809 A810 A811 A812 A813 A814 A815 A816

A817 A818 A819 A820 A821 A822 A823 A824 A825 A826 A827 A828

A829 A830 A831 A832 ~ ~ " ^_ ~ ~ "

Table 8: Compounds of the formula Ip:

in which R_{1 ?} R₂, R₃, R_4l Xi and p have the same meaning as given for the radical A, and n is 0, 1 or 2: A8 A9 A10 A11 A12

A13 A14 A15 A16 A17 A18 A19 A20 A21 A22 A23 A24

A25 A26 A27 A28 A29 A30 A31 A32 A33 A34 A35 A36

A37 A38 A39 A40 A41 A42 A43 A44 A45 A46 A47 A48

A49 A50 A51 A52 A53 A54 A55 A56 A57 A58 A59 A60

A61 A62 A63 A64 A65 A66 A67 A68 A69 A70 A71 A72

A73 A74 A75 A76 A77 A78 A79 A80 A81 A82 A83 A84

A85 A86 A87 A88 A89 A90 -

A99 A100 A101 A102 A103 A104 A105 A106 A107 A108

A109 A110 A111 A112 A113 A114 A115 A116 A117 A118 A119 A120

A121 A122 A123 A124 A125 A126 A127 A128 A129 A130 A131 A132

A133 A134 A135 A136 A137 A138 A139 A140 A141 A142 A143 A144

A145 A146 A147 A148 A149 A150 A151 A152 A153 A154 A155 A156

A157 A158 A159 A160 A161 A162 A163 A164 A165 A166 A167 A168

A169 A170 A171 A172 A173 A174 A175 A176 A177 A178 A179 A180

A181 A182 A183 A184 A185 A186 A187 A188 A189 A190 A191 A192

A193 A194 A195 A196 A197 A198 A199 A200 A201 A202 A203 A204

A205 A206 A207 A208 A209 A210 A211 A212 A213 A214 A215 A216

A217 A218 A219 A220 A221 A222 A223 A224 A225 A226 A227 A228

A229 A230 A231 A232 A233 A234 A235 A236 A237 A238 A239 A240

A241 A242 A243 A244 A245 A246 A247 A248 A249 A250 A251 A252

A253 A254 A255 A256 A257 A258 A259 A260 A261 A262 A263 A264

A265 A266 A267 A268 A269 A270 A271 A272 A273 A274 A275 A276

A277 A278 A279 A280 A281 A282 A283 A284 A285 A286 A287 A288

A289 A290 A291 A292 A293 A294 A295 A296 A297 A298 A299 A300

A301 A302 A303 A304 A305 A306 A307 A308 A309 A310 A311 A312

A313 A314 A315 A316 A317 A318 A319 A320 A321 A322 A323 A324

A325 A326 A327 A328 A329 A330 A331 A332 A333 A334 A335 A336

A337 A338 A339 A340 A341 A342 A343 A344 A345 A346 A347 A348

A349 A350 A351 A352 A353 A354 A355 A356 A357 A358 A359 A360

A361 A362 A363 A364 A365 A366 A367 A368 A369 A370 A371 A372

A373 A374 A375 A376 A377 A378 A379 A380 A381 A382 A383 A384 A385 A386 A387 A388 A389 A390 A391 A392 A393 A394 A395 A396

A397 A398 A399 A400 A401 A402 A403 A404 A405 A406 A407 A408

A409 A410 A411 A412 A413 A414 A415 A416 A417 A418 A419 A420

A421 A422 A423 A424 A425 A426 A427 A428 A429 A430 A431 A432

A433 A434 A435 A436 A437 A438 A439 A440 A441 A442 A443 A444

A445 A446 A447 A448 A449 A450 A451 A452 A453 A454 A455 A456

A457 A458 A459 A460 A461 A462 A463 A464 A465 A466 A467 A468

A469 A470 A471 A472 A473 A474 A475 A476 A477 A478 A479 A480

A481 A482 A483 A484 A485 A486 A487 A488 A489 A490 A491 A492

A493 A494 A495 A496 A497 A498 A499 A500 A501 A502 A503 A504

A505 A506 A507 A508 A509 A510 A511 A512 A513 A514 A515 A516

A517 A518 A519 A520 A521 A522 A523 A524 A525 A526 A527 A528

A529 A530 A531 A532 A533 A534 A535 A536 A537 A538 A539 A540

A541 A542 A543 A544 A545

A554 A555 A556 A557 A558 A559 A560 A561 A562 A563 A564

A565 A566 A567 A568 A569 A570 A571 A572 A573 A574 A575 A576

A577 A578 A579 A580 A581 A582 A583 A584 A585 A586 A587 A588

A589 A590 A591 A592 A593 A594 A595 A596 A597 A598 A599 A600

A601 A602 A603 A604 A605 A606 A607 A608 A609 A610 A611 A612

A613 A614 A615 A616 A617 A618 A619 A620 A621 A622 A623 A624

A625 A626 A627 A628 A629 A630 A631 A632 A633 A634 A635 A636 A644 A645 A646 A647 A648

A649 A650 A651 A652 A653 A654 A655 A656 A657 A658 A659 A660

A661 A662 A663 A664 A665 A666 A667 A668 A669 A670 A671 A672

A685 A686 A687 A688 A689 A690 A691 A692 A693 A694 A695 A696

A697 A698 A699 A700 A701 A702 A703 A704 A705 A706 A707 A708

A709 A710 A711 A712 A713 A714 A715 A716 A717 A718 A719 A720

A721 A722 A723 A724 A725 A726 - - - - - -

A733 A734 A735 A736 A737 A738 A739 A740 A741 A742 A743 A744

A745 A746 A747 A748 A749 A750 A751 A752 A753 A754 A755 A756

A757 A758 A759 A760 A761 A762 A763 A764 A765 A766 A767 A768

A769 A770 A771 A772 A773 A774 A775 A776 A777 A778 A779 A780

A781 A782 A783 A784 A785 A786 A787 A788 A789 A790 A791 A792 _ _ _ _ _ _ __ _ _ __ _ _

A793 A794 A795 A796 A797 A798 A799 A800 A801 A802 A803 A804

A805 A806 A807 A808 A809 A810 A811 A812 A813 A814 A815 A816

A817 A818 A819 A820 A821 A822 A823 A824 A825 A826 A827 A828

A829 A830 A831 A832 - - - - - - - -

Table 9: Compounds of the formula I, represented as compounds of the formula

A-Q in which A denotes A10:

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

B1 B2 . B4 B5 B6 B7 B8 B9 B10 B11 B12

B13 B14 B15 B16 B17 B18 B19 B20 B21 B22 B23 B24

B25 B26 B27 B28 B29 B30 B31 B32 B33 B34 B35 B36

B37 B38 - B40 B41 B42 B43 B44 B45 B46 B47 B48

B49 B50 B51 - B53 B54 B55 B56 B57 B58 B59 B60

B61 B62 B63 B64 B65 B66 B67 B68 B69 B70 B71 B72

B73 B74 B75 B76 B77 B78 B79 B80 B81 B82 B83 B84

B85 B86 B87 B88 B89 B90 B91 B92 B93 B94 B96

B97 B98 B99 B100 B101 B102 B103 B104 B105 B106 B107 B108

B109 B110 - - - - - - - - - -

Table 10: Compounds of the formula I, represented as <compounds of the formula

A-Q

in which A denotes A10: A10 A10 A10 A10 A10 A10 A10 A10 A10 A10 A10 A10

C1 - C3 C4 - C6 C7 C8 C9 C10 C11 C12 C13 C14 C15 C16 C17 C18 C19 C20 C21 C22 C23 C24 C25 C26 C27 - - - - - - - - -

Table 11 : Compounds of the formula I, represented as compounds of the formula

A-Q

in which A denotes A10:

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

D4 D5 D6 D7 D8 D9 D10 D11 D12

Table 12: Compounds of the formula I, represented as compounds of the formula

A-Q

in which A denotes A556:

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

B1 B2 . B4 B5 B6 B7 B8 B9 B10 B11 B12

B13 B14 B15 B16 B17 B18 B19 B20 B21 B22 B23 B24

B25 B26 B27 B28 B29 B30 B31 B32 B33 B34 B35 B36

B37 B38 - B40 B41 B42 B43 B44 B45 B46 B47 B48

B49 B50 B51 - B53 B54 B55 B56 B57 B58 B59 B60

B61 B62 B63 B64 B65 B66 B67 B68 B69 B70 B71 B72

B73 B74 B75 B76 B77 B78 B79 B80 B81 B82 B83 B84

B85 B86 B87 B88 B89 B90 B91 B92 B93 B94 B96

B97 B98 B99 B100 B101 B102 B103 B104 B105 B106 B107 B108 A556 A556 A556 A556 A556 A556 A556 A556 A556 A556 A556 A556

____________ _ _ _ . . . . . _ _

Table 13: Compounds of the formula I, represented as compounds of the formula

A-Q

in which A denotes A556:

A556 A556 A556 A556 A556 A556 A556. A556 A556 A556 A556 A556

C1 - C3 C4 - C6 C7 C8 C9 C10 C11 C12

C13 C14 C15 C16 C17 C18 C19 C20 C21 C22 C23 C24 C25 C26 C27 - - - - - - - - -

Table 14: Compounds of the formula I, represented as compounds of the formula

A-Q in which A denotes A556:

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

D4 D5 D6 D7 D8 D9 D10 D11 D12

Table 15: Compounds of the formula I, represented as compounds of the formula

A-Q

in which A denotes A646: A646 A646 A646 A646 A646 A646 A646 A646 A646 A646 A646 ______

B1 B2 _ B4 B5 B6 B7 B8 B9 B10 B11 B12

B13 B14 B15 B16 B17 B18 B19 B20 B21 B22 B23 B24

B25 B26 B27 B28 B29 B30 B31 B32 B33 B34 B35 B36

B37 B38 - B40 B41 B42 B43 B44 B45 B46 B47 B48

B49 B50 B51 - B53 B54 B55 B56 B57 B58 B59 B60

B61 B62 B63 B64 B65 B66 B67 B68 B69 B70 B71 B72

B73 B74 B75 B76 B77 B78 B79 B80 B81 B82 B83 B84

B85 B86 B87 B88 B89 B90 B91 B92 B93 B94 B96

B97 B98 B99 B100 B101 B102 B103 B104 B105 B106 B107 B108

B109 B110 - - - - - - - - - -

Table 16: Compounds of theι formula I, represented as compounds of the formula

A-Q

in which A denotes A646:

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

C1 - C3 C4 - C6 C7 C8 C9 C10 C11 C12 C13 C14 C15 C16 C17 C18 C19 C20 C21 C22 C23 C24

C25 C26 C27 -

Table 17: Compounds of the formula I, represented as compounds of the formula

A-Q

in which A denotes A646: A646 A646 A646 A646 A646 A646 A646 A646 A646 A646 A646 A646

D4 D5 D6 D7 D8 D9 D10 D11 D12

Table 18: Physical data for the compounds of the formula I given in the tables above: (the melting points are given in °C.)

Compound m.p. (range) Phys. state

A1 -C2 138-140 crystalline

A2-C2 138-140 crystalline

A833-B52 (K⁺) 145-150 crystalline

A833-B52 (H4) - oil

A830-B52 - amorphous/liquid

A829-B52 - oil

A829-B1 - oil

A10-B52 (H3) 54-56 crystalline

A10-B1 71 -73 crystalline

A10-B3 - viscous

A10-B14 - viscous

A10-B39 99-100 crystalline

A736-B52 100-102 crystalline

A10-C2 (H6) - viscous

A57-B52 (H5) 54-56 crystalline

A18-B52 71-74 crystalline

A8-B52 95-98 crystalline

A19-B52 53-55 crystalline

A1 -C5 32-34 crystalline

A2-C5 32-33 crystalline

A10-C5 - resin

A11 -C5 38-39 crystalline

A11-B52 - resin

A834-B52 - crystalline

A835-B52 - viscous

A854-B52 - viscous

A90-B52 - viscous Compound m.p. (range) Phys. state

A33-B52 113-115 crystalline

A556-B52 - crystalline

A646-B52 - viscous

A868-B52 106-107 crystalline

A855-B52 - viscous

A817-B52 - viscous

A819-B52 - crystalline

A856-B52 - solid

A857-B52 - viscous

A63-B52 - resin

A20-B52 - solid

A858-B52 - resin

A836-B52 - crystalline

A859-B52 - viscous

A818-B52 - viscous

A837-B52 - viscous

A28-B52 - viscous

A28-B52 (Et₃NH⁺) - crystalline

A838-B52 - viscous

A839-B52 - viscous

A860-B52 - viscous

A860-B1 13 - viscous

A861-B52 90-93 crystalline

A840-B52 - oil

A841 -B52 41 -43 crystalline

A842-B52 - viscous

A843-B52 - viscous

A866-B100 96-98 crystalline

A844-B52 - viscous

A866-B112 - viscous

A867-B112 - viscous

A856-B112 79-81 crystalline

A20-C5 - viscous

A10-C28 - resin

A11-C28 - resin Compound m.p. (range) Phys. state

A10-B52 (Et₃NH⁺) - viscous

A862-B52 - viscous

A24-B52 102-105 crystalline

A845-B52 40-44 crystalline

A837-B52 - viscous

(Et₃NH⁺)

A67-B52 68-69 crystalline

A863-B52 80-80 crystalline

A10-B17 40-42 crystalline

A846-B52 - crystalline

A847-B52 - viscous

A848-B52 - crystalline

A56-B52 - vitreous

A26-B52 - vitreous

A849-B52 - viscous

A10-B4 - viscous

A865-B52 - viscous

A850-B52 63-64 crystalline

A10-C29 - resin

A10-B111 76-78 crystalline

A3-C5 - resin

A834-C5 - resin

A851 -B52 - vitreous

A852-B52 - viscous

A10-B25 - amorphous/liquid

A853-B52 - viscous

A27-B52 - oil

A864-C5 149-150 crystalline

A864-B52 1 10-112 crystalline

A834-B39 - oil

A-852-OH - oil

A-851-OH 102-103 crystalline

A-835-OH - oil

A-24-OH - solid

A-858-OH - oil Compound m.p. (range) Phys. state

A-859-OH - oil

A-864-OH - solid

A-851 -OH 73-74 crystalline

A-848-OH 81 -82 crystalline

A-27-OH - oil

A-855-OH 102-104 crystalline

A-90-OH 111-114 crystalline

A-124-OH 117-1 19 crystalline

A-834-OH - crystalline

A-852-OH - oil

A-851 -OH 102-103 crystalline

A-835-OH - oil

A10-OH 62-63 crystalline

A830-OH 157-158 crystalline

A831 -OH 188-189 crystalline

A829-OH 131 -134 crystalline

A832-OH 1 10-112 crystalline

Table 19: Physical data for the compounds of the formula I given in the tables above: (the melting points given in °C):

In the following formulas, end-standing valences denote methyl groups (in all cases except alkyne or alkene groups) or hydrogen (in the case of alkyne or alkene groups), for example

and CH

Comp. Corresponding Formula m.p. (range) No. Phys. state

Comp. Corresponding Formula m.p. (range) No. Phys. state

(m);3.57-

3.60(m); 3.71 (s); 4.84 (s); 7.74 (d);

7.82 (d) Comp. Corresponding Formula m.p. (range) No. Phys. state o^

1.010 ° ° J° VISCOUS

I r°

OH O «-° 95-98

1.017

< _F crystalline Comp. Corresponding Formula m.p. (range) No. Phys. state

e

e

e

e

e Comp. Corresponding Formula m.p. (range) No. Phys. state

Comp. Corresponding Formula m.p. (range) No. Phys. state

Comp. Corresponding Formula m.p. (range) No. Phys. state

resin

solid

resin

crystalline

₀J

1.041 o^

OHO ^υ viscous Comp. Corresponding Formula m.p. (range) No. Phys. state

viscous

viscous

viscous

crystalline

VISCOUS

VISCOUS Comp. Corresponding Formula m.p. (range) No. Phys. state

S S

S Comp. Corresponding Formula m.p. (range) No. Phys. state

S

S S

Comp. Corresponding Formula m.p. (range) No. Phys. state

VISCOUS

VISCOUS

resin

crystalline

1.064 s

OH O VISCOUS

Comp. Corresponding Formula m.p. (range) No. Phys. state

e

e

e

e Comp. Corresponding Formula m.p. (range) No. Phys. state

Comp. Corresponding Formula m.p. (range) No. Phys. state

Comp. Corresponding Formula m.p. (range) No. Phys. state

s

s

s

Comp. Corresponding Formula m.p. (range) No. Phys. state

Biological examples

Example B1 : Herbicidal action before emergence of the plants (pre-emergence action) Monocotyledonous and dicotyledonous test plants are sown in standard soil in pots. Immediately after sowing, the test substances are sprayed on at an optimum dosage (500 I of water/ha) as an aqueous suspension (prepared from a wettable powder (example F3, b) according to WO 97/34485) or emulsion (prepared from an emulsion concentrate (example F1 , c) according to WO 97/34485). The test plants are then grown under optimum conditions in a greenhouse.

After a test period of 4 weeks, the test is evaluated using a 9-level scale of ratings (1 = complete damage, 9 = no effect). Ratings of 1 to 4 (in particular 1 to 3) mean good to very good herbicidal action. Table B1 : Pre-emergence action: ("NT" means "not tested"):

Compound g/ha Panicum Digitaria Echino. Abutilon Amaranthus Chenop.

A10-B1 250 2 2 2 1

A10-B52, (H3) 250 1 1 1 1

A830-B52 250 4 9 3 4

A1 -C2 250 6 3 3 3

A833-B52 (K+) 250 2 2 2

A833-B52, (H4) 250 1 1 1

A10-B1 250 2 2 2 1

A10-B3 250 1 1 1

A10-B14 250 3 6 3 1

A10-B39 250 1 1 1

A736-B52 250 4 2 1

A10-C2 (H6) 250 3 3 3 2

A57-B52 (H5) 250 1 1 1

A18-B52 250 1 1 2 NT

A8-B52 250 1 1 1 NT

A19-B52 250 1 1 2 NT

A1-C5 250 2 2 1 2

A2-C5 250 2 2 1

A10-C5 250 2 3 1 1

A11-C5 250 2 1 1

A11-B52 250 1 1 2

A834-B52 250 1 1 2

A835-B52 250 2 1 1

A556-B52 250 1 1 2

A646-B52 250 1 1 2

A819-B52 250 7 9 7 2

A63-B52 250 2 3 1 5 3 NT

A20-B52 250 1 1 3 3 NT

A836-B52 250 2 1 5 2 3

A837-B52 250 2 2 1 2 NT

A28-B52 250 2 2 2 3 NT

A28-B52 (Et3NH+) 250 2 2 3 1 NT Compound g/ha Panicum Digitaria Echino. Abutilon Amaranthus Chenop.

A838-B52 250 1 3 2 1

A839-B52 250 1 3 2 1

A840-B52 250 1 2 2 2 2 1

A841 -B52 250 1 2 1 1

A842-B52 250 1 6 2 2 2 1

A843-B52 250 1 2 2 1

A844-B52 250 1 2 2 1

A20-C5 250 1 2 2 1

A10-C28 250 1 3 2 1

A11-C28 250 ; I 2 1 2

A10-B52 (Et3NH+) 250 1 1 2 1

A24-B52 250 I 1 1

A845-B52 250 1 1 1

A837-B52 (Et3NH+) 250 1 1 2 1

A67-B52 250 I 2 2 3 2 1

A10-B17 250 I 1 4 2 1

A846-B52 250 1 1 2

A847-B52 250 1 3 2 4 1 4

A848-B52 250 1 1 7

A56-B52 250 I 2 3

A26-B52 250 I 1 1

A849-B52 250 I 2 2 2

A10-B4 250 i . 3 3

A850-B52 250 1 2 2 1

A10-C29 250 ; . 2 1 NT

A10-B111 250 1 1 1 NT

A3-C5 250 I 2 2 1 NT

A834-C5 250 l 3 2 NT

A851 -B52 250 1 1 1

A852-B52 250 1 4 1 2

A10-B25 250 1 2 1 1

A853-B52 250 1 2 1 2

A27-B52 250 2 3 4 1 3 The same results are obtained when the compounds of the formula I are formulated according to the other examples of WO 97/34485.

Example B2: Post-emergence herbicidal action

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

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

Table B2: Post-emergence action

Compound g/ha Panicum Digitaria Echino. Abutilon Xanth. Ipopur. Amaranth Chenop.

A10-B1 250 2 2 2 2 2 2 2 1

A10-B52, (H3) 250 1 1 2 1 2 2 2 1

A830-B52 250 4 9 3 5 4 5 4 4

A829-B52 250 2 6 4 3 6 4 2 2

A829-B1 250 7 9 7 7 4 6 2 2

A1 -C2 250 7 8 4 3 4 3 2 4

A833-B52 (K+) 250 3 3 4 3 2 3 3 3

A833-B52, (H4) 250 3 3 4 3 1 2 2 3

A10-B3 250 1 1 3 1 1 2 1

A10-B14 250 2 2 3 2 2 2 2

A10-B39 250 1 3 3 1 2 2

A736-B52 250 1 1 2 1 2 2

A10-C2 (H6) 250 2 4 3 2 1 3

A57-B52 (H5) 250 1 1 2 1 2 2

A18-B52 250 1 1 2 1 2 2

A8-B52 250 1 1 1 1 2 1

A19-B52 250 1 1 2 1 2 1 Compound g/ha Panicum Digitaria Echino. Abutilon Xanth. Ipopur. Amaranth Chenop.

A1 -C5 250 4 2 2 2 4 2 2 1

A2-C5 250 1 2 2 2 2 2 1 1

A10-C5 250 2 2 2 2 2 2 1 1

A11-C5 250 1 2 2 2 2 2 2 1

A11-B52 250 1 1 2 2 2 2 1 1

A834-B52 250 1 1 2 2 2 2 1 1

A835-B52 250 1 1 2 2 3 2 2 1

A854-B52 250 1 2 2 2 2 2 1 1

A90-B52 250 2 2 3 2 3 4 3 1

A33-B52 250 2 2 2 2 3 2 2 1

A556-B52 250 1 2 2 1 2 2 2 1

A646-B52 250 1 2 2 2 2 2 2 1

A855-B52 250 2 2 2 2 2 2 2 1

A817-B52 250 1 2 2 2 2 2 2 1

A819-B52 250 2 3 2 2 2 2 2 1

A856-B52 250 2 2 2 2 2 1 2 1

A857-B52 250 2 2 2 2 2 2 2 1

A63-B52 250 1 2 2 2 2 2 2 2

A20-B52 250 1 2 2 2 2 2 2 1

A858-B52 250 2 2 2 2 2 2 1 2

A836-B52 250 2 2 2 2 3 3 2 1

A859-B52 250 1 2 2 2 2 2 2 1

A818-B52 250 2 2 3 2 2 2 2 1

A837-B52 250 1 2 2 2 2 2 1 1

A28-B52 250 1 2 2 2 3 4 1 1

A28-B52

(Et3NH+) 250 1 2 2 2 3 2 2 1

A838-B52 250 2 2 3 1 2 2 2 1

A839-B52 250 2 2 2 2 2 2 2 1

A860-B52 250 2 1 2 2 2 2 2 1

A861-B52 250 2 3 5 3 2 2 2 1

A840-B52 250 2 3 4 3 3 3 2 1

A841 -B52 250 2 4 4 3 3 3 1 1

A842-B52 250 3 3 5 3 3 3 2 1

A843-B52 250 2 3 3 3 3 6 3 1 Compound g/ha Panicum Digitaria Echino. Abutilon Xanth. Ipopur. Amaranth Chenop.

A844-B52 250 2 3 4 3 3 3 3 1

A856-B112 250 3 3 5 2 3 3 3 1

A20-C5 250 2 3 4 3 3 3 2 1

A10-C28 250 4 4 4 3 3 3 2 1

A11 -C28 250 3 4 4 3 3 3 2 1

A10-B52

(Et3NH+) 250 2 2 2 2 2 2 2 1

A862-B52 250 2 2 3 3 2 5 2 1

A24-B52 250 2 2 2 2 2 2 2 1

A845-B52 250 2 2 2 2 2 2 2 1

A837-B52

(Et3NH+) 250 2 2 2 2 2 2 2 1

A67-B52 250 2 2 2 2 2 3 2 1

A863-B52 250 2 2 3 2 2 3 2 1

A10-B17 250 2 1 2 2 2 2 2 1

A846-B52 250 1 2 2 2 2 1 2 2

A847-B52 250 1 2 1 2 2 4 3 1

A848-B52 250 2 2 2 2 2 2 1 1

A56-B52 250 1 2 2 2 2 2 1 1

A26-B52 250 2 2 2 2 2 2 2 1

A849-B52 250 2 2 3 2 2 2 2 2

A10-B4 250 1 1 2 1 2 1 2 1

A850-B52 250 2 2 2 2 2 2 2 1

A10-C29 250 2 3 3 2 2 1 2 1

A10-B111 250 2 2 3 3 3 3 2 1

A3-C5 250 3 4 3 3 3 3 3 1

A851 -B52 250 3 3 4 3 3 3 2 1

A852-B52 250 3 4 4 3 3 3 3 1

A10-B25 250 3 4 4 3 3 3 2 1

A27-B52 250 1 2 2 3 2 4 2 5

A864-C5 250 1 2 2 2 2 2 1 1

A864-B52 250 2 2 2 2 2 2 2 1

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

Claims (6)

WHAT IS CLAIMED IS:

1. A compound of the formula I

in which p is 0 or 1 ;

R_T is a C-|-C₆alkylene, C₃-C₆alkenylene or C₃-C₆a!kynylene chain which may be mono- or polysubstituted by halogen or R₅, where the unsaturated bonds of the chain are not attached directly to the substituent X-i;

X_! is oxygen, -O(CO)-, -(CO)O-, -O(CO)O-, -N(R₆)-O-, -O-NR₅r, thio, sulfinyl, sulfonyl,

-SO₂NR₇-, -NR₅₂SO₂- or -NR₈-;

R₂ is a C C₈alkyl, C₃-C₆alkenyl or C₃-C₆alkynyl group which is mono- or polysubstituted by halogen, hydroxyl, amino, formyl, nitro, cyano, mercapto, carbamoyl, C-|-C₆alkoxy,

C C₆alkoxycarbonyl, C₂-C₆alkenyl, C₂-C₆haloalkenyl, C₂-C₆alkynyl, C₂-C₆hafoaIkynyl,

C₃-C₆cycloalkyl, by halogen-substituted C₃-C₆cycloalkyl, or by C₃-C₆alkenyloxy,

C₃-C₆alkynyloxy, d-C₆haloalkoxy, C₃-C₆haloalkenyloxy, cyano-Cι-C₆alkoxy,

C Cealkoxy-C Cealkoxy, d-Cealkoxy-d-Cealkoxy-d-Cealkoxy, d-Cealkylthio-d-Cεalkoxy,

C Cealkylsulfinyl-CrCβalkoxy, C C₆alkylsulfonyl-Cι-C₆alkoxy, d-C₆alkoxycarbonyl-

C C₆alkoxy, CrC₆alkoxycarbonyl, C C₆alkylcarbonyl, CrC₆alkylthio, CrC₆alkylsulfinyl,

C C₆alkylsulfonyl, Cι-C₆haloalkylthio, CrC₆haloalkylsulfinyl, d-C₆haloalkylsulfonyl, oxiranyl, which for its part may be substituted by Cι-C₆alkyl, or by (3-oxetanyl)oxy, which for its part may be substituted by C C₆alkyl, or by benzylthio, benzylsulfinyl, benzylsulfonyl, d-C₆alkylamino, di(CrC₆alkyl)amino, R₉S(O)₂O, R₁₀N(Rn)SO₂-, thiocyanato, phenyl, phenoxy, phenylthio, phenylsulfinyl or phenylsulfonyl; where the phenyl- or benzyl-containing groups for their part may be substituted by one or more d-C₆alkyl, d-C₆haloalkyl, C-ι-C₆alkoxy, d-C₆haloalkoxy, halogen, cyano, hydroxyl or nitro groups, or R₂is phenyl which may be mono- or polysubstituted by d-C₆alkyl, d-Cβhaloalkyl, d-C₆alkoxy, d-C₆haloaIkoxy, halogen, cyano, hydroxyl or nitro; or R₂ is C₃-C₆cycloalkyl, d-C₆alkoxyl- or d-C₆alkyl-substituted C₃-C₆cycloalkyl, 3-oxetanyl or CrC₆alkyl-substituted 3-oxetanyI; or, if Q is Q₂ or Q₃, or is Qi in which R₁₄ and R₂₂ are a C₂-C₃alkylene chain, R₂ is additionally also a five- to ten-membered monocyclic or fused bicyclic ring system which may be aromatic, saturated or partially saturated and may contain 1 to 4 heteroatoms selected from the group consisting of nitrogen, oxygen and sulfur, where the ring system is attached directly or via a d-C₄alkylene, C₂-C₄alkenyl-C C₄alkylene, C₂-C₄alkynyl-C C₄alkylene, -N(R₁₂)-C C₄alkylene, -SO-C C₄alkylene or -SO₂-C_rC₄alkylene group to the substituent X-i and where each ring system may not contain more than two oxygen atoms and not more than two sulfur atoms and the ring system for its part may be mono-, di- or trisubstituted by d-C₆alkyl, d-C₆haloalkyl, C₂-C₆alkenyl, C₂-C₆haloalkenyl, C₂-C₆alkynyl, C₂-C₆haloalkynyl, d-Cealkoxy, hydroxyl, d-C₆haloalkoxy, C₃-C₆alkenyloxy, C₃-C₆alkynyloxy, mercapto, d-C₆alkylthio, d-C₆haloalkylthio, C₃-C₆alkenylthio, C₃-C₆haloalkenylthio, C₃-C₆alkynylthio, C₂-C₅alkoxyalkylthio, C₃-C₅acetylalkylthio, C₃-C₆alkoxycarbonylalkylthio, C₂-C₄cyanoalkylthio, CrC₆alkylsulfinyl, d-C₆haloalkylsulfinyl, Cι-C₆alkylsulfonyl, Cι-C₆haloalkylsulfonyl, aminosulfonyl, d-C₂alkylaminosulfonyl, di(Cι-C₂alkyl)aminosulfonyl, di(CrC alkyl)amino, halogen, cyano, nitro, phenyl and benzylthio, where phenyl and benzylthio for their part may be substituted on the phenyl ring by d-C₃alkyl, d-C₃ha!oalkyl, d-C₃alkoxy, d-C₃haloalkoxy, halogen, cyano or nitro, and where the substituents on the nitrogen in the heterocyclic ring are different from halogen; or R₂ is hydrogen or unsubstituted d-C₈alkyl if a) Ri is substituted by the group R₅, or b) Q is the group Q₂, or c) Q is the group Q₃ in which X^ is -O(CO)-, -(CO)O-, -N(R₆)-O-, -O-NR₅r, -SO₂NR₇-, -NR₅₂SO₂- or -NR₈-; or d) Q is the group Q_ή in which X is -N(R₆)-O-, -O-NR₅₁-, -SO₂NR₇-, -NR₅₂SO₂- or -NR₈-, or e) Q is the group Qi in which R₁₄ and R₂₂ in Q^ are a C₂-C₃alkylene chain and X^ is -O(CO)- or -(CO)O-,

R₃ is C C₃haloalkyl;

R₄ is hydrogen, halogen, C C₃alkyl, C C₃haloalkyl, d-C₃alkoxy, d-dalkoxy-d-Csalkyl or d-C₃alkoxy-CrC₃alkoxy; R₅ is hydroxyl, d-C₆alkoxy, C₃-C₆cycloaIkyloxy, d-C₆alkoxy-Cι-C₆alkoxy, C C₆alkoxy-

C C₆alkoxy-d-C₆alkoxy or d-C₂alkylsulfony!oxy;

Re, R7_> Re, Rg, R10, R11, R12, R51 and R₅₂ independently of one another are hydrogen,

C C₆alkyf, d-C₆haloalkyI, CrC₆alkoxycarbonyl, d-C₆alkyIcarbonyl, Cι-C₆alkoxy-d-C₆alkyI, d-Cealkoxy-d-Cealkyl substituted by d-C₆alkoxy, benzyl or phenyl, where phenyl and benzyl for their part may be mono- or polysubstituted by C C₆alkyl, d-C₆haloalkyl,

C C₆alkoxy, C C₆haloalkoxy, halogen, cyano, hydroxyl or nitro; where R₆ and R₉ are not simultaneously hydrogen and hydrogen, C C₆alkoxycarbonyf or d-C₆alkylcarbonyl, respectively;

in which

A-, is C(R₁₄R₁₅), NR₁₆ or oxygen;

A₂ is C(R₁₇R₁₈), C(O), -C=N-O-R₁₉, oxygen, thio, sulfinyl, sulfonyl, -NR₂₀ or ethylene; with the provisos that A^ is different from oxygen if A₂ is oxygen, C(O), thio, sulfinyl, -C=N-O-R₁₉,

NR₂₀ or C(Rι₇R₁₈), where R₁₇ and R₁₈ independently of one another are C_rC₄alkoxy, d-C alkylthio, C C alkylsulfinyl, Cι-C₄alkylsulfonyl; and A-i is different from NRι₆ if A₂ is thio, sulfinyl or C(R₁₇R₁₈), where R₁₇ and R₁₈ independently of one another are Cι-C₄alkoxy,

Cι-C₄alkylthio, d-C₄alkylsulfinyl, d-C alkylsulfonyl; R₁₄and R₂₂ independently of one another are hydrogen, d-C₄alkyl, C C₄haloalkyl, C₃-C₄alkenyl, C₃-C₄alkynyl, d-C₄alkylthio,

C C₄alkylsulfinyl, d-C₄alkylsulfonyl, d-C₄alkylsulfonyloxy, C C₄alkoxy,

C C₄alkoxycarbonyl or d-C₄alkylcarbonyl;

R₁₅ and R₂₁ independently of one another are hydrogen, C₁-C alkyl, d-C₄haloalkyl,

C₃-C₄alkenyl or C₃-C alkynyl;

R₁₇ is hydrogen, d-C₄alkyl, C C₄haloalkyl, d-C alkoxy, d-C₄alkylthio, C C₄alkylsulfinyl or

C C₄alkylsulfonyl;

R₁₈ is hydrogen, d-C₄alkyl, d-C haloalkyl, C₃-C₄alkenyl, C₃-C₄alkynyl, C C₄alkoxy,

C-,-C₄alkylthio, C -C alkylsulfinyl, C C₄alkylsulfonyl or C C₄dialkoxyalkyl-C C alkyl; R₂₀ is d-C₄alkyl, C₃-C₆cycloalkyl, C₃-C₄alkenyl, C₃-C₄alkynyl, d-C₄alkylcarbonyl, C C₄alkyl- carbonyloxy, di(CrC₄alkyl)aminocarbonyl or benzyl, where the phenyl group may be mono- or polysubstituted by d-C₆alkyl, d-C₆haloalkyl, d-C₆alkoxy, d-C₆haloalkoxy, halogen, cyano, hydroxyl or nitro;

R-_I9 and R ₆ independently of one another are hydrogen, Cι-C₄alkyl, C₃-C₆cycIoalkyl,

C₃-C₄alkenyl, C₃-C₄alkynyl, benzyl or phenyl, where phenyl and benzyl for their part may be mono- or polysubstituted by d-C₆alkyl, Cι-C₆haloalkyl, d-C₆alkoxy, d-C₆haloalkoxy, halogen, cyano, hydroxyl or nitro; or R₁₄ and R₂₂ together form a C₂-C₃alkylene chain; or R₁₄ and R₁₅ together and/or Rι₇ and Rι₈ together and/or R₂₁ and R₂₂ together form a .

C₂-C alkylene chain which may be interrupted by oxygen and/or carbonyl and/or sulfur, with the proviso that the oxygen and sulfur atoms are separated by at least one methylene group; or R ₄ and R₁₈ together form a C₂-C₄alkylene chain; or

R₂₂ and R-|₈ together form a C₂-C₄alkylene chain; or R₁₈ together with R₂₂ or R₁₄ forms a direct bond; or R₁₆ and R₁₈ together form a C₂-C alkylene chain;

R₁₃ is hydroxyl, O^"M⁺, where M⁺ is an alkali metal cation or ammonium cation, halogen, d~Cι₂alkylsulfonyloxy, amino, Cι-C₄alkylthio, C C₁₂alkylsulfinyl, d-Cι₂alkylsulfonyl,

Cι-Cι₂haloalkylthio, d-C₁₂haloalkylsulfinyl, d-Cι₂haloalkylsulfonyl,

CrC_δalkoxy-CrCealkylthio, d-Cβalkoxy-d-Cealkylsulfinyl, d-Cealkoxy-d-Cealkylsulfonyl,

C₃-C₁₂alkenylthio, C₃-Cι₂alkenylsulfinyl, C₃-Cι₂alkenylsulfonyl, C₃-d₂alkynylthio,

C₃-C₁₂alkynylsulfinyl, C₃-C₁₂alkynylsulfonyl, CrC₄alkoxycarbonyl-C C₄alkylthio,

Cι-C₄alkoxycarbonyl-d-C₄alkylsulfinyl, d-C₄alkoxycarbonyl-d-C₄alkylsulfonyl,

(C C₄alkoxy)₂P(O)0, d-C₄alkyl-(C C₄alkoxy)P(O)O, H(C₁-C₄alkoxy)P(O)O_>

R₂₃R₂₄NR₂₅R₂₆N, NH, R₂₇R₂₈NC(O)O-, R₂₉R₃₀NC(O)NH-, d-C₁₈alkylcarbonyloxy,

C₂-C₁₈alkenylcarbonyloxy, C₂-C₁₈alkynylcarbonyloxy, C₃-C₆cycloaikylcarbonyloxy,

C C₁₂alkoxycarbonyloxy, d-Cι₂alkylthiocarbonyloxy, d-dgalkylthiocarbamoyl, where the alkyl, alkenyl and alkynyl groups may be substituted by halogen, d-C₆alkoxy, d-C₆alkylthio, d-C₆alkylsulfinyl, C-|-C₆alkylsulfonyl or cyano; or R₁₃ is phenoxy, phenylthio, phenylsulfinyl, phenylsulfonyl, phenylsulfonylamino, phenylsulfonyloxy or benzoyloxy, where the phenyl groups for their part may be substituted by one or more halogen, nitro, cyano, C C₄alkyl, d-C₄haloa!kyl, Cι-C₄alkoxy or C C₄halo- alkoxy groups; or R₁₃ is a group Het thio, Het₂-sulfinyl, Het₃-sulfonyl, Het₄-(CO)O or Het₅-N(R₃₃); in which Het-i, Het₂, Het₃, Het₄ and Het₅ independently of one another are a five- to ten-membered monocyclic or fused bicyclic ring system which may be aromatic or partially saturated and may contain 1 to 4 heteroatoms selected from the group consisting of nitrogen, oxygen and sulfur, and where each ring system may not contain more than 2 oxygen atoms and not more than 2 sulfur atoms, and where the ring system itself can be substituted by d-C₆alkyl,

C C₆haloalkyl, C C₆alkoxy, d-C₆haloalkoxy, d-C₆alkylthio, C C₆alkylsulfinyl, C C₆alkyl- sulfonyl, di(C C alkyl)aminosulfonyl, di(d-C₄alkyl)annino, halogen, cyano, nitro or phenyl, and where the substituents on the nitrogen in the heterocyclic ring are different from halogen;

R₂₃, R₂₄, R₂5, R₂6, R_27> R28, R29, R₃o and R₃₃ independently of one another are hydrogen or

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

in which

R₃₄ is hydrogen, d-C₄alkyl, C₁-C₄haloalkyl, C₃-C₆cycloalkyl, C₂-C₄alkenyl, C₂-C₄alkynyl or benzyl, where the phenyl group may be mono- or polysubstituted by d-C₆alkyl, C C₆halo- alkyl, d-C₆alkoxy, CrC₆haloalkoxy, halogen, cyano, hydroxyl or nitro;

R₃₅ is hydrogen, C C alkyl, d-C₄haloalkyl, C₃-C₆cycloalkyl, C₃-C alkenyl, C₃-C₄alkynyl or benzyl, where the phenyl group may be mono- or polysubstituted by d-C₆alkyl, C C₆halo- alkyl, d-C₆alkoxy, C C₆haloalkoxy, halogen, cyano, hydroxyl or nitro;

R₃₆ is hydroxyl, O^"M⁺, where M⁺ is an alkali metal cation or ammonium cation, halogen, d-Cι₂alkylsuIfonyloxy, amino, d-C₄alkylthio, C C₁₂alkylsulfinyl, d-C₁₂alkylsulfonyl, d-Cι₂haloalkylthio, d-d₂haloalkylsulfinyl, d-C₁₂haloalkylsulfonyl, d-Cealkoxy-d-Cealkylthio, d-Cealkoxy-d-Cealkylsulfinyl, d-C₆alkoxy-d-C₆alkylsulfonyl,

C₃-Cι₂alkenylthio, C₃-C₁₂alkenylsulfinyl, C₃-C_l2alkenylsulfonyl, C₃-C-|₂alkynylthio,

C₃-C₁₂alkynylsulfinyl, C₃-C₁₂alkynylsulfonyl, d-dalkoxycarbonyl-d-dalkylthio, d-C₄alkoxycarbonyl-C C₄alkylsulfinyl, d-C₄alkoxycarbonyl-C C alkylsulfonyl, (d-C₄alkoxy)₂P(O)O, C₁-C₄aikyl-(C₁-C₄alkoxy)P(O)0_J H(C C₄alkoxy)P(O)O, R₃₇R₃₈ ,

R₃₉R₄₀NNH, R₄₁R₄₂NC(O)O-, R₄₃R ₄NC(0)NH-, C C₁₈alkylcarbonyloxy,

C₂-C₁₈alkenylcarbonyloxy, C₂-C₁₈alkynylcarbonyloxy, C₃-C₆cycloalkylcarbonyloxy, d-C₁₂alkoxycarbonyloxy, d-Cι₂alkylthiocarbonyloxy or d-Cι₂alkylthiocarbamoyl, where the alkyl, alkenyl and alkynyl groups may be substituted by halogen, d-C₆alkoxy, d-C₆alkylthio, d-C₆alkylsulfinyl, d-C₆alkylsulfonyl or cyano; or

R₃₆ is phenoxy, phenylthio, phenylsulfinyl, phenylsulfonyl, phenylsulfonylamino, phenylsuifonyloxy or benzoyloxy, where the phenyl groups for their part may be mono- or polysubstituted by halogen, nitro, cyano, d-C₄alkyl, C -C₄haloalkyl, C C₄alkoxy, d-C₄halo- alkoxy, or R₃₆ is a group Het₇-thio, Het₈-sulfinyl, Het₉-sulfonyl, Het₁₀-(CO)O or Het_ι N(R₄₇); in which

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

R37, 38, R39. R₄o, R₄ι, R 2, R₄₃, R t and R₄₇ independently of one another are hydrogen or d-C₆alkyl; or

R₃₇ and R₃₈ together or R₃₉ and R ₀ together or R ₁ and R₄₂ together or R₄₃ and Rψ* together are pyrolidino, piperidino, morpholino, thiomorpholino, which may be mono- or polysubstituted by methyl groups; or Q is Q₃

in which

R₄₉ is d-C₄alkyl, Cι-C₄haloalkyl, C₃-C₆cycloalkyl or halogen-substituted C₃-C₆cycloalkyl; R₅₀ is d-C₃alkylene which may be substituted by halogen, hydroxyl, d-C₆alkoxy,

C₂-C₆alkenyl, C₂-C₆alkynyl, C₃-C₆cycloalkyl, d-Cealkoxy-d-dalkoxy,

C Cealkoxy-CrCealkoxy-C Cealkoxy, (3-oxetanyl)oxy, or by C C₆alkyl-substituted (3- oxetanyl)oxy, or by benzylthio, benzylsulfinyl, benzylsulfonyl, phenyl, phenoxy, phenylthio, phenylsulfinyl or phenylsulfonyl, where the phenyl- and benzyl-containing groups for their part may be substituted by one or more d-C₆alkyl, d-C₆haloalkyl, d-C₆alkoxy, d-C₆haloalkoxy, halogen, cyano, hydroxyl or nitro groups; or R₅₀ is phenyl, where the phenyl-containing group for its part may be substituted by one or more d-C₆alkyl, d-C₆haloalkyl, CrC₆alkoxy, C C₆haloalkoxy, halogen, cyano, hydroxyl or nitro, or R₅₀ is C₃-C₆cycloalkyl, C C₆alkoxy- or C C₆alkyl-substituted C₃-C₆cycloalkyl, 3-oxetanyl or d-C₆alkyl-substituted 3-oxetanyl; and n is 0, 1 or 2; and agronomically acceptable salts/N-oxides/isomers/enantiomers of this compound.

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

in which R^ R₂, R₃, R₄ and X^ are as defined under formula I and Y, is a leaving group, in an inert organic solvent in the presence of a base with a compound of the formula II

(ll), in which R₂₂, R₂-ι, A₂ and A-i are as defined under formula I, to give the compounds of the formulae Ilia and lllb

lib

and then isomerizing these in the presence of a base and a catalytic amount of dimethylaminopyridine (DMAP) or a source of cyanide, for example acetone cyanohydrin; or b) reacting a compound of the formula lb

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

in which R₂₂, R₂₁, A-i and A₂ are as defined under formula I, in an inert organic solvent in the presence of a base and a coupling agent to give the compound of the formula Ilia or lllb, and then isomerizing these as described under route a); or, to prepare the compounds of the formula I, in which Q is a group Q₂, either a) reacting a compound of the formula la

in which R-i, R₂₎ R₃, R and Xi are as defined under formula I and Yi is a leaving group, with a compound of the formula lla

in which R₃₄ and R₃₅ are as defined under formula I, in an inert organic solvent in the presence of a base to give the compound of the formula lllc

lllc

in which R-i, R₂, R₃, R₄, R₃₄, R₃₅ and Xi are as defined under formula I, and then isomerizing this compound in the presence of a base and a catalytic amount of a source of cyanide; or b) reacting a compound of the formula lb

in which Ri, R₂, R₃, R₄ and Xi are as defined under formula I, with a compound of the formula lla

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

and then isomerizing this compound as described under route a); or, to prepare compounds of the formula I, in which Q is a group

in which n is 0 and R₅₀ and R ₉ are as defined above, either a) converting a compound of the formula IV

in which Xi, Ri, R₂, R₃, R₄ and R ₉ are as defined above, in the presence of a base, carbon disulfide and an alkylating agent of the formula V

in which R₅o is as defined under formula I, and Y₂ is a leaving group, into the compound of the formula VI

in which Ri, R₂, R₃, R₄, R₅₀, Xi and R₄₉ are as defined under formula I, and then cyclizing this compound with hydroxylamine hydrochloride in the presence of a base to give the isomeric compounds of the formulae Ic and Id

and then oxidizing these compounds with an oxidizing agent, for example with peracids, to give the corresponding sulfoxides (n = 1) and sulfones (n = 2) of the formulae Ie and If, respectively.

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

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

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

6. A compound of the formula XX

in which

Q is hydroxyl, halogen, cyano or Cι-C₆alkoxy, or is a group of the formula i, R3, R₄, R 9, R50, Xi and p are as defined under formula I and R₂ is a CrC₈alkyl, C₃-C₆alkenyl or C₃-C₆alkynyl group which is mono- or polysubstituted by halogen, hydroxyl, amino, formyl, nitro, cyano, mercapto, carbamoyl, d-C₆alkoxy, CrC₆alkoxycarbonyl, C₂-C₆alkenyl, C₂-C₆haloalkenyl, C₂-C₆alkynyl, C₂-C₆haloalkynyl, C₃-C₆cycloalkyl, by halogen- substituted C₃-C₆cycloaIkyl, or by C₃-C₆alkenyloxy, C₃-C₆alkynyloxy, CrC₆haloalkoxy, C₃-C₆haloalkenyloxy, cyano-CrC₆alkoxy, CrC₆alkoxy-CrC₆alkoxy, d-C₆alkoxy- C -C₆alkoxy-d -C₆alkoxy, C₁ -C₆alkylthio-Cι -C₆alkoxy, d -C₆alkylsulf inyl-d -C₆alkoxy, CrC₆alkylsulfonyl-CrC₆alkoxy, CrC₆alkoxycarbonyl-CrC₆alkoxy, CrC₆alkoxycarbonyl, CrC₆alkylcarbonyl, CrC₆alkylthio, d-C₆alkylsulfinyl, d-C₆alkylsulfonyl, C C₆haloalkylthio, CrC₆haloalkylsulfinyl, CrC₆-haloalkylsuifonyl, oxiranyl, which for its part may be substituted by CrC₆alkyl, or by (3-oxetanyl)oxy, which for its part may be substituted by d-C₆alkyl, or by benzylthio, benzylsulfinyl, benzylsulfonyl, d-Cβalkylamino, di(CrC₆alkyl)amino, R₉S(O)₂O, Rι₀N(Rιι)SO₂-, thiocyanato, phenyl, phenoxy, phenylthio, phenylsulfinyl or phenylsulfonyl; where the phenyl- or benzyl-containing groups for their part may be substituted by one or more d-C₆alkyl, C C₆haloalkyl, d-C₆alkoxy, C C₆haloalkoxy, halogen, cyano, hydroxyl or nitro groups, or

R₂ is phenyl which may be mono- or polysubstituted by CrC₆alkyl, d-C₆haloalkyl, d-C₆alkoxy, d-C₆haloalkoxy, halogen, cyano, hydroxyl or nitro; or R₂ is C₃-C₆cycloalkyl, CrC₆alkoxy- or d-C₆alkyl-substituted C₃-C₆cycloalkyl, 3-oxetanyl or CrC₆alkyl-substituted 3-oxetanyl; or if Xi is -N(R₆)-O-, -O-NR₅₁, SO₂NR₇- or -NR₅₂SO₂- and R₆, R₇, R₅ι and R₅₂ are as defined under formula I,

R₂ may additionally be hydrogen, unsubstituted d-C₆alkyl, or a five- to ten-membered monocyclic or fused bicyclic ring system which may be aromatic, saturated or partially saturated and may contain 1 to 4 heteroatoms selected from the group consisting of nitrogen, oxygen and sulfur, where the ring system is attached directly or via a CrC₄alkylene, C₂-C alkenyl-d-C₄alkylene, C₂-C₄alkynyl-CrC₄alkylene, -N(Rι₂)-CrC₄alkylene, -SO-d-C alkylene or -S0₂-CrC₄alkylene group to the substituent Xi, 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, CrC₆haloalkyl, C₂-C₆alkenyl, C₂-C₆haloalkenyl, C₂-C₆alkynyl, C₂-C₆haloalkynyl, d-C₆alkoxy, hydroxyl, CrC₆haloalkoxy, C₃-C₆alkenyloxy, C₃-C₆alkynyloxy, mercapto, d-C₆alkylthio, C C₆-haloalkylthio, C₃-C₆alkenylthio, C₃-C₆haloalkenylthio, C₃-C₆alkynylthio, C₂-C₅alkoxyalkylthio, C₃-C₅acetylalkylthio, C₃-C₆alkoxycarbonylalkylthio, C₂-C₄cyanoalkylthio, CrC₆alkylsulfinyl, CrC₆haloalkylsulfinyl, CrC₆alkylsulfonyl, Ci-Cehaloalkylsulfonyl, aminosulfonyl, d-dalkylaminosulfonyl, di(C C₂alkyl)aminosulfonyl, di(CrC₄alkyl)amino, halogen, cyano, nitro, phenyl and benzylthio, where phenyl and benzylthio for their part may be substituted on the phenyl ring by CrC₃alkyl, d-C₃haloalkyl, d-C₃alkoxy, d-C₃haloalkoxy, halogen, cyano or nitro, and where the substituents on the nitrogen in the heterocyclic ring are different from halogen.