Indian Patents
Title of Invention

HETEROAROYL-SUBSTITUTED SERINE AMIDES
Abstract The present invention relates to heteroaroyl-substituted serineamides of the formula I in which the variables A and R1 to R6 are as defined in the description, and to their agriculturally useful salts, to processes and intermediates for their preparation, and to the use of these compounds or of the compositions comprising these compounds for controlling unwanted plants.
Full Text Description
The present invention relates to heteroaroyl-substituted serineamides of formula I

in which the variables are as defined below:
A is 5- or 6-membered heteroaryl having one to four nitrogen atoms, or one to
three nitrogen atoms and one oxygen or sulfur atom, or one oxygen or sulfur
atom, which heteroaryl may be partially or fully halogenated and/or may carry 1
to 3 radicals from the group consisting of cyano, C1-C6-alkyl, C3-C6-cycloalkyl,
C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy and C1-C6-alkoxy-C1-C4alkyl;
R1, R2 are hydrogen, hydroxyl or C1-C6-alkoxy;
R3 is C1-C6-alkyl, C1-C4-cyanoalkyl or C1-C6-haloalkyl;
R4 is hydrogen, C1-C6-alkyl, C3-C6-cycloalkyl, C3-C6-alkenyl, C3-C6-alkynyl, C3-C6-
haloalkenyl, C3-C6-haloalkynyl, formyl, C1-C6-alkylcarbonyl, C3-C6-cycloalkyl-
carbonyl, C2-C6-alkenylcarbonyl, C2-C6-alkynylcarbonyl, C1-C6-alkoxycarbonyl,
C3-C6-alkenyloxycarbonyl, C3-C6-alkynyloxycarbonyl, C1-C6-alkylaminocarbonyl,
C3-C6-alkenylaminocarbonyl, C3-C6-alkynylaminocarbonyl, C1-C6-alkylsulfonyl-
aminocarbonyl, di-(C1-C6-alkyl)aminocarbonyl, N-(C3-C6-alkenyl)-N-(C1-C6-alkyl)-
aminocarbonyl, N-(C3-C6-alkynyO-N-(C1-C6-alkyl)aminocarbonyl, N-(C1-C6-
alkoxy)-N-(C1-C6-alkyl)aminocarbonyl, N-(C3-C6-alkenyl)-N-(C1-C6-alkoxy)-
aminocarbonyl, N-(C3-C6-alkynyl)-N-(C1-C6-alkoxy)aminocarbonyl, di-(C1-C6-
alkyl)aminothiocarbonyl, (C1-C6-alkyl)cyanoimino, (amino)cyanoimino, [(C1-C6-
alkyl)amino]cyanoimino, [di(C1-C6-alkyl)amin6]cyanoimino, C1-C6-alkylcarbonyl-
C1-C6-alkyl, C1-C6 alkoxylmino-C1-C6-alkyl, N-(C1-C6-alkylamino)imino-C1--C6-
alkyl, N-(di-C1-C6-alkylamino)imino-C1-C6-alkyl or tri-C1-C4-alkylsilyl,
where the alkyl, cycloalkyl and alkoxy radicals mentioned may be partially
or fully halogenated and/or may carry one to three of the following groups:
cyano, hydroxyl, C3-C6-cycloalkyl, C1-C6-alkoxy-C1-C4-alkyl, C1-C4-alkoxy-
C1-C4-alkoxy-C1-C4-alkyl, C1-C4-alkoxy, C1-C4alkylthio, di-(C1-C4-alkyl)-
amino, C1-C4-alkyl-C1-C4-alkoxycarbonylamino, C1-C4-alkylcarbonyl,
hydroxycarbonyl, C1-C4-alkoxycarbonyl, aminocarbonyl, C1-C4alkylamino-

carbonyl, di-(C1-C4-alkyl)aminocarbonyl or C1-C4-alkylcarbonyloxy;
phenyl, phenyl-C1-C6-alkyl, phenylcarbonyl, phenylcarbonyl-C1-C6-alkyl,
phenoxycarbonyl, phenylaminocarbonyl, phenylsulfonylaminocarbonyl, N-(C1-C6-
alkyl)-N-(phenyl)aminocarbonyl, phenyl-C1-C6-alkylcarbonyl,
where the phenyl radical may be partially or fully halogenated and/or may
carry 1 to 3 of the following groups: nitro, cyano, C1-C4-alkyl, C1-C4-
haloalkyl, C1-C4-alkoxy or C1-C4-haloalkoxy; or
S02R7;
R5 is hydrogen or C1-C6-alkyl;
R6 is C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-haloalkyl, C2-C6-haloalkenyl,
C2-C6-haloalkynyl, C1-C6-cyanoalkyl, C2-C6-cyanoalkenyl, C2-C6-cyanoalkynyl,
C1-C6-hydroxyalkyl, C2-C6-hydroxyalkenyl, C2-C6-hydroxyalkynyl, C3-C6-
cycloalkyl, C3-C6-cycloalkenyl, 3- to 6-membered heterocyclyl, 3- to 6-membered
heterocyciyl-C1-C4-alkyl,
where the cycloalkyl, cycloalkenyl or 3- to 6-membered heterocyclyl
radicals mentioned above may be partially or fully halogenated and/or may
carry one to three radicals from the group consisting of oxo, cyano, nitro,
C1--C6-alkyl, C1-C6-haloalkyl, hydroxyl, C1-C6-alkoxy, C1-C6-haloalkoxy,
hydroxycarbonyl, C1-C6-alkoxycarbonyl, hydroxycarbonyl-C1-C6-alkoxy,
C1-C6-alkoxycarbonyl-C1-C6-alkoxy, amino, C1-C6-alkylamino, di(C1-C6-
alkyl)amino, C1-C6-alkylsulfonylamino, C1-C6-haloalkylsulfonylamino,
aminocarbonylamino, (C1-C6-alkylamino)carbonylamino, di(C1-C6-alkyl)-
aminocarbonylamino, aryl and aryl(C1-C6-alkyl);
C1-C6-alkoxy-C1-C6-alkyl, C2-C6-alkenyloxy-C1-C6-alkyl, C2-C6-alkynyloxy-C1-C4-
alkyl, C1-C6-haloalkoxy-C1-C6-alkyl, C2-C6-haloalkenyloxy-C1-C4-alkyl, C2-C6-
haloalkynyloxy-C1-C4-alkyl, C1-C6-alkoxy-C1-C6-alkoxy-C1-C6-alkyl, C1-C6-
alkylthio-C1-C6-alkyl, C2-C6-alkenylthio-C1-C6-alkyl, C2-C6-alkynylthio-C1-C4-alkyl,
C1-C6-haloalkyl-C1-C6-thioalkyl, C2-C6-haloalkenyl-C1-C6-thioalkyl, C2-C6-
haloalkynyl-C1-C6-thioalkyl, C1-C6-alkylsulfinyl-C1-C4-alkyl, C1-C6-haloalkyl-
sulfinyl-C1-C4-alkyl, C1-C6-alkylsulfonyl-C1-C6-alkyl, C1-C6-haloalkylsulfonyl-
C1-C4-alkyl, amino-C1-C6-alkyl, C1-C6-alkylamino-C1-C6-alkyl, di(C1-C6-
alkyl)amino-C1-C6-alkyl, C1-C6-alkylsulfonylamino-C1-C6-alkyl, C1-C6-alkyl-
sulfonyl-(C1-C6-alkylamino)-C1-C4-alkyl, C1-C6-alkylcarbonyl, hydroxycarbonyl,
C1-C6-alkoxycarbonyl, aminocarbonyl, C1-C6-alkylaminocarbonyl, di(C1-C6-
alkyl)aminocarbonyl, C1-C6-alkylcarbonyl-C1-C6-alkyl, hydroxycarbonyl-C1-C6-
alkyl, C1-C6-alkoxycarbonyl-C1-C6-alkyl, C1-C6-haloalkoxycarbonyl-C1-C6-alkyl,
C1-C6-alkylcarbonyloxy-C1-C4-alkyl, aminocarbonyl-C1-C6-alkyl, C1-C6-alkyl-
aminocarbonyl-C1-C6-alkyl, di(C1-C6-alkyl)aminocarbonyl-C1-C4-alkyl, d-dr
alkylcarbonylamino-C1-C4-alkyl, formylamino-C1-C6-alkyl, C1-C6-alkoxycarbonyl-
amino-C1-C6-alkyl, C1-C6-alkylcarbonyl-(C1-C6-alkylamino)-C1-C6-alkyl, [(C1-C6-

alkyl)aminocarbonyloxyl-C1-C4-alkyl, [di(C1-C6-alkyl)aminocarbonyloxy]C1--C4
alkyl, {di[di(C1-C6-alkyl)amino]carbonyloxy}C1-C4-alkyl, [(C1-C6-alkyl)amino-
carbonylamino]C1-C4-alkyl, [di(C1-C6-alkyl)aminocarbonylamino]-C1-C4-alkyl;
phenyl-C1-C4-alkyl, phenyl-C2-C4-alkenyl, phenyl-C2-C4-alkynyl, phenyl-C1-C4-
haloalkyl, phenyl-C2-C4-haloalkenyl, phenyl-C2-C4-haloalkynyl, phenyl-C1-C4
hydroxyalkyl, phenyl-C2-C4-hydroxyalkenyl, phenyl-C2-C4-hydroxyalkynyl,
phenylcarbonyl-C1-C4-alkyl, phenylcarbonylamino-C1-C4-alkyl, phenylcarbonyl-
oxy-C1-C4-alkyl, phenyloxycarbonyl-C1-C4-alkyl, phenyloxy-C1-C4alkyl,
phenylthio-C1-C4alkyl, phenylsulfinyl-C1-C4-alkyl, phenylsulfonyl-C1-C4-alkyl,
heteroaryl-C1-C4-alkyl, heteroaryl-C2-C4-alkenyl, heteroaryl-C2-C4-alkynyl,
heteroaryl-C1-C4-haloalkyl, heteroaryl-C2-C4-haloalkenyl, heteroaryl-C2-C4-
haloalkynyl, heteroaryl-C1-C4-hydroxyalkyl, heteroaryl-C2-C4-hydroxyaIkenyl,
heteroaryl-C2-C4-hydroxyalkynyl, heteroarylcarbonyl-C1-C4alkyl,
heteroarylcarbonyloxy-C1-C4alkyl, heteroaryloxycarbonyl-C1-C4-alkyl,
heteroaryloxy-C1-C4-alkyl, heteroarylthio-C1-C6-alkyl, heteroarylsulfinyl-C1-C4-
alkyl, heteroarylsulfonyl-C1-C4-alkyl,
where the phenyl and heteroaryl radicals mentioned above may be partially
or fully halogenated and/or may carry one to three radicals from the group
consisting of cyano, nitro, C1-C6-alkyl, C1-C6-haloalkyl, hydroxy, C1-C6-
alkoxy, C1-C6-haloalkoxy, hydroxycarbonyl, C1-C6-alkoxycarbonyl,
hydroxycarbonyl-C1-C6-alkoxy, C1-C6-alkoxycarbonyl-C1-C6-alkoxy, amino,
C1-C6-alkylamino, di(C1-C6-alkyl)amino, C1-C6-alkylsulfonylamino, C1C6-
haloalkylsulfonylamino, (C1-CValkylaminoJcarbonylamino, di(C1-C6-
alkyl)aminocarbonylamino, aryl and aryl(C1-C6-alkyl);
R7 is C1-C6-alkyl, C1-C6-haloalkyl or phenyl,
where the phenyl radical may be partially or fully halogenated and/or may
carry one to three of the following groups: C1-C6-alkyl, C1-C6-haloalkyl or
C1-C6-alkoxy;
and their agriculturally useful salts.
Moreover, the invention relates to processes and intermediates for preparing
compounds of the formula I, to compositions comprising them and to the use of these
derivatives or of the compositions comprising them for controlling harmful plants.
Fungicidally effective thienyl-substituted amino acid derivatives which carry an
optionally hydroxyl- or alkoxy-substituted alkyl radical in the α-position are described
inter alia in EP 450 355.
Also known from the literature, for example from US 5,346,907, WO 96/012499 and
WO 02/069905, are serine derivatives having pharmaceutical activity which may carry

in the α-position an optionally hydroxyl- or alkoxy-substituted alkyl radical, inter alia.
However, the herbicidal properties of the prior-art compounds and/or their compatibility
with crop plants are not entirely satisfactory.
Accordingly, it is an object of the present invention to provide novel, in particular
herbicidally active, compounds having improved properties.
We have found that this object is achieved by the heteroaroyl-substituted serineamides
of the formula I and their herbicidal action.
Furthermore, we have found herbicidal compositions which comprise the compounds I
and have very good herbicidal action. Moreover, we have found processes for
preparing these compositions and methods for controlling unwanted vegetation using
the compounds I.
Depending on the substitution pattern, the compounds of the formula I comprise two or
more centers of chiralty, in which case they are present as enantiomers or
diastereomer mixtures. The invention provides both the pure enantiomers or
diastereomers and their mixtures.
The compounds of the formula I may also be present in the form of their agriculturally
useful salts, the nature of the salt generally being immaterial. Suitable salts are, in
general, the cations or the acid addition salts of those acids whose cations and anions,
respectively, have no adverse effect on the herbicidal action of the compounds I.
Suitable cations are in particular the ions of the alkali metals, preferably lithium, sodium
and potassium, of the alkaline earth metals, preferably calcium and magnesium, and of
the transition metals, preferably manganese, copper, zinc and iron, and also
ammonium, where, if desired, one to four hydrogen atoms may be replaced by C1-C4-
alkyl, hydroxy-C1-C4-alkyl, C1-C4-alkoxy-C1-C4-alkyl, hydroxy-C1-C4alkoxy-C1-C4alkyl,
phenyl or benzyl, preferably ammonium, dimethylammonium, diisopropylammonium,
tetramethylammonium, tetrabutylammonium, 2-(2-hydroxyeth-1 -oxy)eth-1 -yl-
ammonium, di-(2-hydroxyeth-1-yl)ammonium, trimethylbenzylammonium, furthermore
phosphonium ions, sulfonium ions, preferably tri(C1-C4-alkyl)sulfonium, and
sulfoxonium ions, preferably tri(C1-C4alkyl)sulfoxonium.
Anions of useful acid addition salts are primarily chloride, bromide, fluoride,
hydrogensulfate, sulfate, dihydrogenphosphate, hydrogenphosphate, nitrate,
bicarbonate, carbonate, hexafluorosilicate, hexafluorophosphate, benzoate, and the
anions of C1-C4-alkanoic acids, preferably formate, acetate, propionate and butyrate.

The organic moieties mentioned for the substituents R1-R6 or as radicals on phenyl,
aryl, heteroaryl or heterocyclyl rings are collective terms for individual enumerations of
the specific group members. All hydrocarbon chalns, i.e. all alkyl, alkylsilyl, alkenyl,
alkynyl, cyanoalkyl, haloalkyl, haloalkenyl, haloalkynyl, alkoxy, haloalkoxy, alkoxyalkyl,
alkoxyalkoxyalkyl, alkylcarbonyl, alkenylcarbonyl, alkynylcarbonyl, alkoxycarbonyl,
alkenyloxycarbonyl, alkynyloxycarbonyl, alkylamino, alkylsulfonylamino, haloalkyl-
sulfonylamino, alkylalkoxycarbonylamino, alkylaminocarbonyl, alkenylaminocarbonyl,
alkynylaminocarbonyl, alkylsulfonylaminocarbonyl, dialkylaminocarbonyl, N-alkenyl-
N-alkylaminocarbonyl, N-alkynyl-N-alkylamino-carbonyl, N-alkoxy-N-alkylamino-
carbonyl, N-alkenyl-N-alkoxyaminocarbonyl, N-alkynyl-N-alkoxyaminocarbonyl,
dialkylaminothiocarbonyl, alkylcarbonylalkyl, alkoximinoalkyl, N-(alkylamino)iminoalkyl,
N-(dialkylamino)iminoalkyl, alkylcyanoimino, alkylaminocyanoimino, dialkylamino-
cyanoimino, formylaminoalkyl, alkoxycarbonylaminoalkyl, (alkylamino)carbonyloxyalkyl,
(alkylamino)carbonylaminoalkyl, (dialkylamino)carbonylaminoalkyl, phenylcarbonyl-
aminoalkyl, phenylalkyl, phenylcarbonylalkyl, N-alkyl-N-phenylaminocarbonyl,
phenylalkylcarbonyl, arylalkyl, heterocyciylalkyl, heterocyclylcarbonylalkyl, N-alkyl-N-
heterocyclylaminocarbonyl, heterocyclylalkylcarbonyl, alkylthio and alkylcarbonyloxy
moieties may be stralght-chaln or branched.
Unless indicated otherwise, halogenated substituents preferably carry one to five
identical or different halogen atoms. The term halogen denotes in each case fluorine,
chlorine, bromine or iodine.
Examples of other meanings are:
- C1-C4-alkyl and also the alkyl moieties of tri-C1-C4-alkylsilyl, C1-C4-alkylcarbonyloxy,
C1-C6-alkyl-C1-C6-alkoxycarbonylamino, C1-C6-alkyliminooxy-C1-C4alkyl, C1-C4-
alkoxy-C1-C4-alkoxy-C1-C4-alkyl, C1-C6-alkoxy-C1-C6-alkyl, C2-C6-alkenyloxy-C1-C4-
alkyl, C2-C6-alkynyloxy-C1-C4-alkyl, C1-C6-haloalkoxy-C1-C4-alkyl, C2-C6-
haloalkenyloxy-C1-C4-alkyl, C2-C6-haloalkynyloxy-C1-C4-aIkyl, C1-C6-alkoxy-C1-C6-
alkoxy-C1-C4-alkyl, C1-C6-alkylthio-C1-C6-alkyl, C2-C6-alkenylthio-C1-C4-alkyl, C2-C6-
alkynylthio-C1-C6-alkyl, C1-C6-alkylsulfinyl-C1-C6-alkyl, C1-C6-haloalkylsulfinyl-C1-C4-
alkyl, C1-C6-alkylsulfonyl-C1-C6-alkyl, C1-C6-ha!oalkylsurfonyl-C1-C6-alkyl, amino-C1-
C4-alkyl, C1-C6-alkylamino-C1-C6-alkyl, di(C1-C6-alkyl)amino-C1-C4-alkyl, formyl-
amino-C1-C6-alkyl, C1-C6-alkoxycarbonylamino-C1-C6-alkyl, C1-C6-alkylsulfonyl-
amino-C1-C6-alkyl, C1-C6-alkylsulfonyl-(C1-C6-alkylamino)-C1-C6-alkyl, hydroxyl-
carbonyl-C1-C6-alkyl, C1-C6-alkoxycarbonyl-C1-C6-alkyl, C1-C6-haloalkoxycarbonyl-
C1-C6-alkyl, C1-C6-alkylcarbonyloxy-C1-C6-alkyl, aminocarbonyl-C1-C4-alkyl, C1-C6-
alkylaminocarbonyl-C1-C6-alkyl, di(C1-C6-alkyl)aminocarbonyl-C1-C6-alkyl, [(C1-C6-
alkyl)aminocarbonylamino]-C1-C4-alkyl, [di(C1-C6-alkyl)aminocarbonylamino]-C1-C6-
alkyl, C1-C6-alkylcarbonylamino-C1-C6-alkyl, C1-C6-alkylcarbonyl-(C1-C6-alkylamino)-

C1-C6-alkyl, [(C1-C6-alkyl)aminocarbonyloxy]C1-C6-alkyl, [di(C1-C6-alkyl)amino-
carbonyloxy]C1-C4-alkyl, {di[di(C1-C6-alkyl)amino]carbonyloxy}C1-C4-alkyll hetero-
cyclyl-C1-C4-alkyl, phenyl-C1-C4-alkyl, phenylcarbonylamino-C1-C4-alkyl, phenyl-
C1-C4-alkyl, phenylcarbonyl-GrC4-alkyl, heteroarylcarbonyl-C1-C6-alkyl, heteroaryl-
carbonyloxy-C1-C4-alkyl, heteroaryloxycarbonyl-C1-C6-alkyl, heteroaryloxy-C1-C6-
alkyl, heteroarylthio-Ct-C4-alkyl, heteroarylsulfinyl-C1-C4-alkyl, heteroarylsulfonyl-
C1-C6-alkyl, and aryl-(C1-C4-alkyl): for example methyl, ethyl, n-propyl, 1-methyl-
ethyl, n-butyl, 1-methylpropyl, 2-methylpropyl and 1,1-dimethylethyl;
C1-C6-alkyl and also the alkyl moieties of C1-C6-cyanoalkyl, d-d>-alkoxycarbonyl-
C1-C6-alkyl, C1-C6-alkylsulfonylamino, C1-C6-alkylsulfonylaminocarbonyl, N-(C3-C6-
alkenyl)-N-(C1-C6-alkyl)aminocarbonyl, (C3-C6-alkynyl)-N-(C1-C6-alkyl)-
aminocarbonyl, N-(C-,-C6-alkoxy)-N-(C1-C6-alkyl)aminocarbonyl, C1-C6-alkyl-
carbonyl-C1-C6-alkyl, C1-C6-alkoxylmino--C1--C6--alkyl, N-(C1-C6-alkylamino)-
imino-C1-C6-alkyl, N-(di-C1-C6-alkylamino)imino-C1-C6-alkyl, (C1-C6-alkyl)-
cyanoimino, phenyl-C1-C6-alkyl, phenylcarbonyl-C1-C6-alkyl, N-(C1-C6-alkyl)-N-
phenylaminocarbonyl, heterocyclyl-C1-C6-alkyl, heterocyclylcarbonyl-C1-C6-alkyl
and N-(C1-C6-alkyl)-N-heterocyclylaminocarbonyl:
C1-C6-alkyl as mentioned above, and also, for example, n-pentyl, 1-methylbutyl,
2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl, n-hexyl,
1,1-dimethylpropyl, 1,2-dimethylpropyl, 1-methylpentyl, 2-methylpentyl, 3-methyl-
pentyl, 4-methylpentyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-di-methylbutyl,
2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl,
1,1,2-trimethylpropyl, 1-ethyl-1-methylpropyl and 1-ethyl-3-methylpropyl;
C1-C4-alkylcarbonyl: for example methylcarbonyl, ethylcarbonyl, propylcarbonyl,
1-methylethylcarbonyl, butylcarbonyl, 1-methylpropylcarbonyl, 2-methylpropyl-
carbonyl or 1,1-dimethylethylcarbonyl;
C1-C6-alkylcarbonyl and also the alkylcarbonyl radicals of C1-C6-alkylcarbonyl-C1-C6-
alkyl, Ct-Ce-alkylcarbonyloxy-C1-C6-alkyl, C1-C6-alkylcarbonylamino-C1-C4-alkyl,
phenyl-C1-C6-alkylcarbonyl and heterocyclyl-C1-C6-alkylcarbonyl, C1-C6-
alkylcarbonyl-(C1-C6-alkylarnino)-C1-C6-alkyl:
C1-C6-alkylcarbonyl as mentioned above, and also, for example, pentylcarbonyl,
1-methylbutylcarbonyl, 2-methylbutylcarbonyl, 3-methylbutylcarbonyI, 2,2-
dimethylpropylcarbonyl, 1-ethylpropylcarbonyl, hexylcarbonyl, 1,1-
dimethylpropylcarbonyl, 1,2-dimethylpropylcarbonyl, 1-methylpentylcarbonyl, 2-
methylpentylcarbonyl, 3-methylpentylcarbonyl, 4-methylpentylcarbonyl, 1,1-
dimethylbutylcarbonyl, 1,2-dimethylbutylcarbonyl, 1,3-dimethylbutylcarbonyl, 2,2-
dimethylbutylcarbonyl, 2,3-dimethylbutylcarbonyl, 3,3-dimethylbutylcarbonyl, 1-
ethylbutylcarbonyl, 2-ethylbutylcarbonyl, 1,1,2-trimethylpropylcarbonyl, 1,2,2-
trimethylpropylcarbonyl, 1-ethyl-1-methylpropylcarbonyl or 1-ethyl-2-

methylpropylcarbonyl;
C3-C6-cycloalkyl and also the cycloalkyl moieties of C3-C6-cycloalkylcarbonyl:
monocyclic saturated hydrocarbons having 3 to 6 ring members, such as
cyclopropyl, cyciobutyl, cyclopentyl and cyclohexyl;
C3-C6-cycloalkenyl: for example 1-cyclopropenyl, 2-cyclopropenyl, 1-cyclobutenyl, 2-
cyclobutenyl, 1-cyclopentenyl, 2-cyclopentenyl, 1,3-cyclopentadienyl, 1,4-
cyclopentadienyl, 2,4-cyciopentadienyl, 1-cyclohexenyl, 2-cyclohexenyl, 3-
cyclohexenyl, 1,3-cyclohexadienyl, 1,4-cyclohexadienyl, 2,5-cyclohexadienyl;
C3-C6-alkenyl and also the alkenyl moieties of C3-C6-alkenyloxycarbonyl, C3-C6-
alkenylaminocarbonyl, N-(C3-C6-alkenyl)-N-(C1-C6-alkyl)aminocarbonyl and
N-(C3-C6-alkenyl)-N-(C1-C6-alkoxy)aminocarbonyl: for example 1-propenyl,
2-propenyl, 1-methylethenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl-1-propenyl, 2-
methyl-1-propenyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl, 1-pentenyl, 2-
pentenyl, 3-pentenyl, 4-pentenyl, 1-methyl-1-butenyl, 2-methyl-1-butenyl, 3-methyl-
1-butenyl, 1-methyl-2-butenyl, 2-methyl-2-butenyl, 3-methyl-2-butenyl, 1-methyl-3-
butenyl, 2-methyl-3-butenyl, 3-methyl-3-butenyl, 1,1-dimethyl-2-propenyl, 1,2-
dimethyl-1-propenyl, 1,2-dimethyl-2-propenyl, 1-ethyl-1-propenyl, 1 -ethyl-2-
propenyl, 1-hexenyl, 2-hexenyl, 3-hexenyI, 4-hexenyl, 5-hexenyl, 1-methyl-1-
pentenyl, 2-methyl-1-pentenyl, 3-methyl-1-pentenyl, 4-methyl-1-pentenyl, 1-methyl-
2-pentenyl, 2-methyl-2-pentenyl, 3-methyl-2-pentenyl, 4-methyl-2-pentenyl, 1-
methyl-3-pentenyl, 2-methyl-3-pentenyl, 3-methyl-3-pentenyl, 4-methyl-3-pentenyl,
1-methyl-4-pentenyl, 2-methyl-4-pentenyl, 3-methyl-4-pentenyl, 4-methyl-
4-pentenyl, 1,1-dimethyl-2-butenyl, 1,1-dimethyl-3-butenyl, 1,2-dimethyl-1-butenyl,
1,2-dimethyl-2-butenyl, 1,2-dimethyl-3-butenyl, 1,3-dimethyl-1-butenyl, 1,3-dimethyl-
2-butenyl, 1,3-dimethyl-3-butenyl, 2,2-dimethyl-3-butenyl, 2,3-dimethyl-1-butenyl,
2,3-dimethyl-2-butenyl, 2,3-dimethyl-3-butenyl, 3,3-dimethyl-l-butenyl, 3,3-dimethyl-
2-butenyl, 1-ethyl-1-butenyl, 1-ethyl-2-butenyl, 1-ethyl-3-butenyl, 2-ethyl-1-butenyl,
2-ethyl-2-butenyl, 2-ethyl-3-butenyl, 1,1,2-trimethyl-2-propenyl, 1-ethyl-1-methyl-
2-propenyl, 1-ethyl-2-methyl-1-propenyl and 1-ethyl-2-methyl-2-propenyl;
C2-C6-alkenyl and also the alkenyl moieties of C2-C6-alkenylcarbonyl, C2-C6-
alkenyloxy-C1-C4-alkyl, C2-C6-alkenylthio-C1-C4-alkyl, phenyl-C2-C4-alkenyl,
heteroaryl-C2-C4-alkenyl: C3-C6-alkenyl as mentioned above, and also ethenyl;
- C3-C6-alkynyl and also the alkynyl moieties of C3-C6-alkynyloxycarbonyl, C3-C6-
alkynylaminocarbonyl, N-(C3-C6-alkynyl)-N-(C1-C6-alkyl)aminocarbonyl, N-(C3-C6-
alkynyl)-N-(C1-C6-alkoxy)aminocarbonyl: for example 1-propynyl, 2-propynyl, 1-
butynyl, 2-butynyl, 3-butynyl, 1-methyl-2-propynyl, 1-pentynyl, 2-pentynyl, 3-
pentynyl, 4-pentynyl, 1-methyl-2-butynyl, 1-methyl-3-butynyl, 2-methyl-3-butynyl, 3-

methyl-1-butynyl, 1,1-dimethyl-2-propynyl, 1-ethyl-2-propynyl, 1-hexynyl, 2-hexynyl,
3-hexynyl, 4-hexynyl, 5-hexynyl, 1-methyl-2-pentynyl, 1-methyl-3-pentynyl,
1-methyl-4-pentynyl, 2-methyl-3-pentynyl, 2-methyl-4-pentynyl, 3-methyl-1-pentynyl,
3-methyl-4-pentynyl, 4-methyl-1-pentynyl, 4-methyl-2-pentynyl, 1,1 -dimethyl-
2-butynyl, 1,1-dimethyl-3-butynyl, 1,2-dimethyl-3-butynyl, 2,2-dimethyl-3-butynyl,
3,3-dimethyl-1-butynyl, 1-ethyl-2-butynyl, 1-ethyl-3-butynyl, 2-ethyl-3-butynyl and
1 -ethyl-1 -methyl-2-propynyl;
C2-C6-alkynyl and also the alkynyl moieties of C2-C6-alkynylcarbonyl, C2-C2-
alkynyloxy-C1-C4-alkyl, C2-C6-alkynylthio-C1-C4-alkyl, phenyl-C2-C4-alkynyl,
heteroaryl-C2-C4-alkynyl: C3-C6-alkynyl as mentioned above, and also ethynyl;
C1-C4-cyanoalkyl: for example cyanomethyl, 1-cyanoeth-1-yl, 2-cyanoeth-1-yl,
1-cyanoprop-1-yl, 2-cyanoprop-1-yl, 3-cyanoprop-1-yl, 1-cyanoprop-2-yl, 2-cyano-
prop-2-yl, 1-cyanobut-1-yl, 2-cyanobut-1-yl, 3-cyanobut-1-yl, 4-cyanobut-1-yl,
1-cyanobut-2-yl, 2-cyanobut-2-yl, 1-cyanobut-3-yl, 2-cyanobut-3-yl, 1-cyano-
2-methylprop-3-yl, 2-cyano-2-methylprop-3-yl, 3-cyano-2-methylprop-3-yl and
2-cyanomethylprop-2-yl;
C1-C4-hydroxyalkyl and also the C1-C4-hydroxyalkyl moieties of phenyl-C1-C4-
hydroxyalkyl, heteroaryl-C1-C4-hydroxyalkyl: for example hydroxymethyl, 1-
hydroxyeth-1-yl, 2-hydroxyeth-1-yl, 1-hydroxyprop-1-yl, 2-hydroxyprop-1-yl, 3-
hydroxyprop-1-yl, 1-hydroxyprop-2-yl, 2-hydroxyprop-2-yl, 1-hydroxybut-1-yl, 2-
hydroxybut-1-yl, 3-hydroxybut-1-yl, 4-hydroxybut-1-yl, 1-hydroxybut-2-yl, 2-
hydroxybut-2-yl, 1-hydroxybut-3-yl, 2-hydroxybut-3-yl, 1-hydroxy-2-methylprop-3-yl,
2-hydroxy-2-methylprop-3-yl, 3-hydroxy-2-methylprop-3-yl and 2-hydroxymethyl-
prop-2-yl, 1,2-dihydroxyethyl, 1,2-dihydroxyprop-3-yl, 2,3-dihydroxyprop-3-yl,
1,2-dihydroxyprop-2-yl, 1,2-dihydroxybut-4-yl, 2,3-dihydroxybut-4-yl, 3,4-dihydroxy-
but-4-yl, 1,2-dihydroxybut-2-yl, 1,2-dihydroxybut-3-yl, 2,3-dihydroxybut-3-yl,
1,2-dihydroxy-2-methylprop-3-yl, 2,3-dihydroxy-2-methylprop-3-yl;
C1-C6-hydroxyalkyl: C1-C4-hydroxya!kyl as stated above, and also for example
1-hydroxypent-5-yl, 2-hydroxypent-5-yl, 3-hydroxypent-5-yl, 4-hydroxypent-5-yl,
5-hydroxypent-5-yl, 1-hydroxypent-4-yl, 2-hydroxypent-4-yl, 3-hydroxypent-4-yl,
4-hydroxypent-4-yl, 1-hydroxypent-3-yl, 2-hydroxypent-3-yl, 3-hydroxypent-3-yl,
1 -hydroxy-2-methylbut-3-yl, 2-hydroxy-2-methylbut-3-yl, 3-hydroxy-2-methylbut-3-yl,
1 -hydroxy-2-methylbut-4-yl, 2-hydroxy-2-methylbut-4-yl, 3-hydroxy-2-methylbut-4-yl,
4-hydroxy-2-methylbut-4-yl, 1 -hydroxy-3-methylbut-4-yl, 2-hydroxy-3-methylbut-4-yl,
3-hydroxy-3-methylbut-4-yl, 4-hydroxy-3-methylbut-4-yl, 1 -hydroxyhex-6-yl,
2-hydroxyhex-6-yl, 3-hydroxyhex-6-yl, 4-hydroxyhex-6-yl, 5-hydroxyhex-6-yl,
6-hydroxyhex-6-yl, 1-hydroxy-2-methylpent-5-yl, 2-hydroxy-2-methylpent-5-yl,
3-hydroxy-2-methylpent-5-yl, 4-hydroxy-2-methylpent-5-yl, 5-hydroxy-2-methylpent-

5-yI, 1-hydroxy-3-methylpent-5-yl, 2-hydroxy-3-methylpent-5-yl, 3-hydroxy-3-methyl-
pent-5-yl, 4-hydroxy-3-methylpent-5-yl, 5-hydroxy-3-methylpent-5-yl, 1-hydroxy-4-
methylpent-5-yl, 2-hydroxy-4-methylpent-5-yl, 3-hydroxy-4-methylpent-5-yl,
4-hydroxy-4-methylpent-5-yl, 5-hydroxy-4-methylpent-5-yl, 1 -hydroxy-5-methylpent-
5-yl, 2-hydroxy-5-methylpent-5-yl, 3-hydroxy-5-methylpent-5-yl, 4-hydroxy-5-methyl-
pent-5-yl, 5-hydroxy-5-methylpent-5-yl, 1-hydroxy-2,3-dimethylbut-4-yl, 2-hydroxy-
2,3-dimethylbut-4-yl, 3-hydroxy-2,3-dimethylbut-4-yl, 4-hydroxy-2,3-dimethylbut-4-yl,
1,2-dihydroxypent-5-yl, 2,3-dihydroxypent-5-yl, 3,4-dihydroxypent-5-yl, 4,5-
dihydroxypent-5-yl, 1,2-dihydroxypent-4-yl, 2,3-dihydroxypent-4-yl, 3,4-dihydroxy-
pent-4-yl, 4,5-dihydroxypent-4-yl, 1,2-dihydroxypent-3-yl, 2,3-dihydroxypent-3-yl,
1,2-dihydroxy-2-methylbut-3-yl, 2,3-dihydroxy-2-methylbut-3-yl, 3,4-dihydroxy-2-
methylbut-3-yl, 2-hydroxy-2-hydroxymethylbut-3-yl, 1,2-dihydroxy-2-methylbut-4-yl,
2,3-dihydroxy-2-methylbut-4-yl, 3,4-dihydroxy-2-methylbut-4-yl, 1,2-dihydroxy-3-
methylbut-4-yl, 2,3-dihydroxy-3-methylbut-4-yl, 3,4-dihydroxy-3-methylbut-4-yl, 3-
hydroxy-3-hydroxymethylbut-4-yl, 1,2-dihydroxyhex-6-yl, 2,3-dihydroxyhex-6-yl, 3,4-
dihydroxyhex-6-yl, 4,5-dihydroxyhex-6-yl, 5,6-dihydroxyhex-6-yl, 1,2-dihydroxy-2-
methylpent-5-yl, 2,3-dihydroxy-2-methylpent-5-yl, 3,4-dihydroxy-2-methylpent-5-yl,
4,5-dihydroxy-2-methylpent-5-yl, 2-hydroxy-2-hydroxymethylpent-5-yl, 1,2-
dihydroxy-3-methylpent-5-yl, 2,3-dihydroxy-3-methylpent-5-yl, 3,4-dihydroxy-3-
methylpent-5-yl, 4,5-dihydroxy-3-methylpent-5-yl, 3-hydroxy-3-hydroxymethylpent-5-
yl, 1,2-dihydroxy-4-methylpent-5-yl, 2,3-dihydroxy-4-methylpent-5-yl, 3,4-dihydroxy-
4-methylpent-5-yl, 4,5-dihydroxy-4-methylpent-5-yl, 4-hydroxy-4-hydroxymethylpent-
5-yl, 1,2-dihydroxy-5-methylpent-5-yl, 2,3-dihydroxy-5-methylpent-5-yl, 3,4-
dihydroxy-5-methylpent-5-yl, 4,5-dihydroxy-5-methylpent-5-yl, 5-hydroxy-5-
hydroxymethylpent-5-yl, 1,2-dihydroxy-2,3-dimethylbut-4-yl, 2,3-dihydroxy-2,3-
dimethylbut-4-yl, 3,4-dihydroxy-2,3-dimethylbut-4-yl, 2-hydroxy-2-hydroxymethyl-3-
methylbut-4-yl, 3-hydroxy-3-hydroxymethyl-2-methylbut-4-yl;
C1-C4haloalkyl and also the haloalkyl moieties of phenyl-C1-C4-haloalkyl,
heteroaryl-C1-C4-haloalkyl: a C1-C4-alkyl radical as mentioned above which is
partially or fully substituted by fluorine, chlorine, bromine and/or iodine, i.e., for
example, chloromethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl,
trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl,
bromomethyl, iodomethyl, 2-fluoroethyl, 2-chloroethyl, 2-bromoethyl, 2-iodoethyl,
2,2-difluoroethyI, 2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl, 2-chloro-2,2-difluoro-
ethyl, 2,2-dichloro-2-fluoroethyl, 2,2,2-trichloroethyl, pentafluoroethyl, 2-fluoropropyl,
3-fluoropropyl, 2,2-difluoropropyl, 2,3-difluoropropyl, 2-chloropropyl, 3-chloropropyl,
2,3-dichloropropyl, 2-bromopropyl, 3-bromopropyl, 3,3,3-trifluoropropyl,
3,3,3-trichloropropyl, 2,2,3,3,3-pentafluoropropyl, heptafluoropropyl,
1-(fluoromethyl)-2-fluoroethyl, 1-(chloromethyl)-2-chloroethyl, l-(bromomethyl)-
2-bromoethyl, 4-fluorobutyl, 4-chlorobutyl, 4-bromobutyl, nonafluorobutyl, 1,1,2,2,-
tetrafluoroethyl and 1-trifluoromethyl-1,2,2,2-tetrafluoroethyl;

C1-CVhaloalkyl and also the haloalkyl moieties of C1-C6-haloalkylsulfonylamino,
C1-C6-haloalkyl-C1-C4-thioalkyl: C1-C4-haloalkyl as mentioned above, and also, for
example, 5-fluoropentyl, 5-chloropentyl, 5-bromopentyl, 5-iodopentyl,
undecafluoropentyl, 6-fluorohexyl, 6-chlorohexyl, 6-bromohexyl, 6-iodohexyl and
dodecafluorohexyl;
C3-C6-haloalkenyl: a C3-C6-alkenyl radical as mentioned above which is partially or
fully substituted by fluorine, chlorine, bromine and/or iodine, for example 2-chloro-
prop-2-en-1-yl, 3-chloroprop-2-en-1 -yl, 2,3-dichloroprop-2-en-1-yl, 3,3-dichioroprop-
2-en-1-yl, 2,3,3-trichloro-2-en-1-yl, 2,3-dichlorobut-2-en-1-yl, 2-bromoprop-2-en-1-yl,
3-bromoprop-2-en-1-yl, 2,3-dibromoprop-2-en-1-yl, 3,3-dibromoprop-2-en-1-yl,
2,3,3-tribromo-2-en-1-yl or 2,3-dibromobut-2-en-1-yl;
C2-C6-haloalkenyl and also the C2-C6-haloalkenyl moieties of C2-C6-haloalkenyloxy-
C1-C4-alkyl, C2-C6-haloalkenyl-C1-C4-thioalkyl, phenyl-C2-C4-haloalkenyI, heteroaryl-
C2-C4-haIoalkenyl: a C2-C6-alkenyl radical as mentioned above which is partially or
fully substituted by fluorine, chlorine, bromine and/or iodine, for example 2-chloro-
vinyl, 2-chloroallyl, 3-chloroallyl, 2,3-dichloroallyl, 3,3-dichloroallyl, 2,3,3-
trichloroallyl, 2,3-dichlorobut-2-enyl, 2-bromovinyl, 2-bromoallyl, 3-bromoallyl, 2,3-
dlbromoallyl, 3,3-dibromoallyl, 2,3,3-tribromoallyl or 2,3-dibromobut-2-enyl;
C2-C6-cyanoalkenyl: for example 2-cyanovinyl, 2-cyanoallyl, 3-cyanoallyl, 2,3-
dicyanoallyl, 3,3-dicyanoallyl, 2,3,3-tricyanoallyl, 2,3-dicyanobut-2-enyl;
C2-C6-hydroxyalkenyl and also the hydroxy moieties of phenyl-C1-C4-
hydroxyalkenyl, heteroaryl-C1-C4-hydroxyalkenyr. for example 2-hydroxyvinyl, 2-
hydroxyallyl, 3-hydroxyallyl, 2,3-dihydroxyallyl, 3,3-dihydroxyallyl, 2,3,3-
trihydroxyallyl, 2,3-dihydroxybut-2-enyl;
C3-C6-haloalkynyl: a C3-C6-alkynyl radical as mentioned above which is partially or
fully substituted by fluorine, chlorine, bromine and/or iodine, for example
1,1-difluoroprop-2-yn-1-yl, 3-iodoprop-2-yn-1-yl, 4-fluorobut-2-yn-1-yl, 4-chlorobut-
2-yn-1-yl, 1,1-difluorobut-2-yn-1-yl, 4-iodobut-3-yn-1-yl, 5-fluoropent-3-yn-1-yl,
5-iodopent-4-yn-1-yl, 6-fluorohex-4-yn-1-yl or 6-iodohex-5-yn-1-yl;
C2-C6-haloalkynyl and also the C2-C6-haloalkynyl moieties of C2-C6-haloalkynyloxy-
C-,-C4-alkyl, C^-Ce-haloalkynyl-C^-thioalkyl, phenyl-C2-C4-haloalkynyl, heteroaryl-
C2-C4-haloalkynyl: a C2-C6-alkynyl radical as mentioned above which is partially or
fully substituted by fluorine, chlorine, bromine and/or iodine, for example 1,1-di-
fluoroprop-2-yn-1-yl, 3-iodoprop-2-yn-1-yl, 4-fluorobut-2-yn-1-yl, 4-chlorobut-2-yn-1-
yl, 1,1-difluorobut-2-yn-1-yl, 4-iodobut-3-yn-1-yl, 5-fluoropent-3-yn-1-yl, 5-iodopent-

4-yn-1-yl, 6-fluorohex-4-yn-1-yl or 6-iodohex-5-yn-1-yl;
- C2-C6-cyanoalkynyl: for example 1,1-dicyanoprop-2-yn-1-yl, 3-cyanoprop-2-yn-1-yl,
4-cyano-but-2-yn-1-yl, 1,1-dicyanobut-2-yn-1-yl, 4-cyanobut-3-yn-1-yl, 5-cyanopent-
3-yn-1-yl, 5-cyanopent-4-yn-1-yl, 6-cyanohex-4-yn-1-yl or6-cyanohex-5-yn-1-yl;
- C2-C6-hydroxyalkynyl and also the hydroxy moieties of phenyl-C2-C4-hydroxyalkynyl
for example 1,1-dihydroxyprop-2-yn-1-yl, 3-hydroxyprop-2-yn-1-yl, 4-hydroxybut-2-
yn-1-yl, 1,1-dihydroxybut-2-yn-1-yl, 4-hydroxybut-3-yn-1-yl, 5-hydroxypent-3-yn-1-yl
5-hydroxypent-4-yn-1-yl, 6-hydroxyhex-4-yn-1-yl or 6-hydroxyhex-5-yn-1-yl;
- C1-C6-alkylsulfinyl (C1-C6-akyl-S(=0)-) and also the d-dr-alkylsulfinyl moieties
of C1-C6-alkylsulfinyl-C1-C6-alkyl: for example methylsulfinyl, ethylsulfinyl,
propylsulfinyl, 1-methylethylsulfinyl, butylsulfinyl, 1-methylpropylsulfinyl, 2-
methylpropylsulfinyl, 1,1-dimethylethylsulfinyl, pentylsulfinyl, 1-methylbutylsulfinyl,
2-methylbutylsutfinyl, 3-methylbutylsuifinyl, 2,2-dimethylpropylsuIfinyl, 1-
ethylpropylsulfinyl, 1,1-dimethylpropylsulfinyl, 1,2-dimethylpropylsulfinyl, hexyl-
sulfinyl, 1-methylpentylsulfinyl, 2-methylpentylsulfinyI, 3-methylpentylsulfinyl, 4-
methylpentylsulfinyl, 1,1-dimethylbutylsulfinyl, 1,2—dimethylbutylsulfinyl, 1,3-
dimethylbutylsulfinyl, 2,2-dimethylbutylsulfinyl, 2,3-dimethylbutylsulfinyl, 3,3-
dimethylbutylsulfinyl, 1-ethylbutylsu!finyl, 2-ethylbutylsulfinyl, 1,1,2-trimethyl-
propylsulfinyl, 1,2,2-trimethylpropylsulfinyl, 1-ethyl-1-methylpropylsulfinyl and 1-
ethyl-2-methylpropylsulfinyl;
C1-C6-haloalkylsulfinyl and also the C1-C6-haloalkylsulfinyl moieties of C1-C6-
haloalkylsulfinyl-C1-C6-alkyl: Cn—C6—alkylsulfinyl radical as mentioned above which
is partially or fully substituted by fluorine, chlorine, bromine and/or iodine, i.e. for
example fluoromethylsulfinyl, difluoromethylsulfinyl, trifluoromethylsulfinyl,
chlorodifluoromethylsulfinyl, bromodifiuoromethylsulfinyl, 2-fluoroethylsulfinyl, 2-
chloroethylsulfinyl, 2-bromoethylsulfinyl, 2-iodoethylsulfinyl, 2,2-
difluoroethylsuifinyl, 2,2,2—trifluoroethylsuifinyl, 2,2,2-trichloroethylsulfinyl, 2-
chloro-2-fluoroethylsulfinyl, 2-chloro-2,2-difluoroethylsulfinyl, 2,2-dichioro-2-
fluoroethylsulfinyl, pentafluoroethylsulfinyl, 2-fluoropropylsulfinyl, 3-
fluoropropylsulfinyl, 2-chloropropylsu!finyl, 3-chloropropylsulfinyl, 2-
bromopropylsulfinyl, 3-bromopropylsulfinyl, 2,2-difluoropropylsulfinyl, 2,3-difluoro-
propylsulfinyl, 2,3-dichloropropylsulfinyl, 3,3,3-trifluoropropylsulfinyl, 3,3,3-trichloro-
propylsulfinyl, 2,2,3,3,3-pentafluoropropylsulfinyl, heptafluoropropylsulfinyl, 1-
(fluoromethyl)-2-fluoroethylsulfiny(, 1-(chloromethyl)-2-chloroethylsulfinyl, 1-
(bromomethyl)-2-bromoethylsulfinyl, 4-fluorobutylsulfinyl, 4-chlorobutylsuIfinyl, 4-
bromobutylsulfinyl, nonafiuorobutylsulfinyl, 5-fluoropentylsulfinyl, 5-chloropentyl-
sulfinyl, 5-bromopentylsulfinyl, 5-iodopentylsulfinyl, undecafluoropentylsulfinyl, 6-
fluorohexylsulfinyl, 6-chlorohexylsulfinyl, 6-bromohexylsulfinyl, 6-iodohexylsulfinyl

and dodecafluorohexylsulfinyl;
C1--Ce-alkylsulfonyl (C1-C6-alkyl-S(0)2-) and also the C1-C6-alkylsulfonyl moieties
of C1-C6-alkylsulfonyl-C1-C6-alkyl, C1-C6-alkylsulfonylamino, C1-C6-
alkylsulfonylamino-C1-C4-alkyl, C1-C6-alkylsulfonyl-(C1-C6-alkylamino)-C1-C4-alkyl:
for example methylsulfonyl, ethylsulfonyl, propylsulfonyl, 1-methylethylsulfonyl,
butylsulfonyl, 1-methylpropylsulfonyl, 2-methylpropylsulfonyl, 1,1-
dimethylethytsulfonyt, pentylsulfonyl, 1-methylbutylsulfonyl, 2-methylbutylsulfonyl,
3-methylbutylsulfonyl, 1,1-dimethylpropylsulfonyl, 1,2-dimethylpropylsulfonyl, 2,2-
dimethylpropylsulfonyl, 1-ethylpropylsulfonyl, hexylsulfonyl, 1-methylpentylsulfonyl,
2-methylpentylsulfonyl, 3-methylpentylsulfonyl, 4-methylpentylsulfonyl, 1,1-
dimethylbutylsulfonyl, 1,2-dimethylbutylsulfonyl, 1,3-dimethylbutylsulfonyl, 2,2-
dimethylbutylsulfonyl, 2,3-dimethylbutylsulfonyl, 3,3-dimethylbutylsulfonyl, 1-
ethylbutylsulfonyl, 2-ethylbutylsulfonyl, 1,1,2-trimethylpropylsulfonyl, 1,2,2-
trimethylpropylsulfonyl, 1-ethyl-1-methylpropylsulfonyl and 1 —ethyl—2—
methylpropylsulfonyl;
C1-C6-haloalkylsulfonyl and also the C1-C6-haloalkylsulfonyl moieties of C-,-C6-
haloalkylsulfonyl-C1-C6-alkyl, C1-C6-haloalkylsulfonylamino: a C1-C6-alkylsulfonyl
radical as mentioned above which is partially or fully substituted by fluorine,
chlorine, bromine and/or iodine, i.e. for example fiuoromethylsulfonyl,
difluoromethylsulfonyl, trifluoromethylsulfonyl, chlorodifluoromethylsulfonyl,
bromodifluoromethylsulfonyl, 2-fluoroethylsulfonyl, 2-chloroethylsulfonyI, 2-
bromoethylsulfonyl, 2-iodoethylsulfonyl, 2,2-difluoroethyl-sulfonyl, 2,2,2-
trifluoroethylsulfonyl, 2-chloro-2-fluoroethylsulfonyl, 2-chloro-2,2-
difluoroethylsulfonyl, 2,2-dichloro-2-fluoroethylsulfonyl, 2,2,2-trichloroethylsulfonyl,
pentafluoroethylsulfonyl, 2-fluoropropylsulfonyl, 3-fluoropropylsulfonyl, 2-
chloropropylsulfonyl, 3-chloropropylsulfonyl, 2-bromopropylsulfonyl, 3-
bromopropylsulfonyl, 2,2-difiuoropropylsuifonyl, 2,3-difluoropropylsulfonyl, 2,3-
dichloropropylsulfonyl, 3,3,3-trifiuoropropylsulfonyl, 3,3,3-trichloropropylsulfonyl,
2,2,3,3,3-pentafluoropropylsulfonyl, heptafluoropropylsulfonyl, 1-(fluoromethyl)-2-
fluoroethylsulfonyl, 1-(chloromethyl)-2-chloroethylsulfonyI, 1-(bromomethyl)-2-
bromoethylsulfonyl, 4-fluorobutylsulfonyl, 4-chlorobutylsulfonyl, 4-
bromobutylsulfonyl, nonafluorobutylsulfonyl, 5-fluoropentylsulfonyl, 5-
chloropentylsulfonyl, 5-bromopentylsulfonyl, 5-iodopentylsulfonyl, 6-
fluorohexylsulfonyl, 6-bromohexylsulfonyl, 6-iodohexylsulfonyl and
dodecafluorohexylsulfonyl;
C^d-a'koxy and also the alkoxy moieties of hydroxycarbonyl-C1-C6-a'koxy, crd-
alkoxycarbonyl-C1-C6-alkoxy, C1-C6-alkoxy-C1-C6-alkoxy-C1-C6-alkyl and C1--C4-
alkyl-C1-C6-alkoxycarbonylamino: for example methoxy, ethoxy, propoxy, 1-
methylethoxy, butoxy, 1-methylpropoxy, 2-methylpropoxy and 1,1-dimethylethoxy;

C1-C6-alkoxy and also the alkoxy moieties of hydroxycarbonyl-CVCValkoxy, C1-C6-
alkoxycarbonyl-C1-C6-alkoxy, N-(C1-C6-alkoxy)-N-(C1-C6-alkyl)aminocarbonyl,
N-(C3-C6-alkenyl)-N-(C1-C6-alkoxy)aminocarbonyl, N-(C3-C6-alkynyl)-N-(C1-C6-
alkoxy)aminocarbonyl and CVCfralkoxylmino-C-rCValkyl: C1-C4-alkoxy as
mentioned above, and also, for example, pentoxy, 1-methylbutoxy, 2-methylbutoxy,
3-methoxylbutoxy, 1,1-dimethylpropoxy, 1,2-dimethylpropoxy, 2,2-dimethylpropoxy,
1-ethylpropoxy, hexoxy, 1-methylpentoxy, 2-methylpentoxy, 3-methylpentoxy,
4-methylpentoxy, 1,1-dimethylbutoxy, 1,2-dimethylbutoxy, 1,3-dimethylbutoxy,
2,2-dimethylbutoxy, 2,3-dimethylbutoxy, 3,3-dimethylbutoxy, 1-ethylbutoxy,
2-ethylbutoxy, 1,1,2-trimethylpropoxy, 1,2,2-trimethylpropoxy, 1-ethyl-1-methyl-
propoxy and 1-ethyl-2-methylpropoxy;
C1-C4-haloalkoxy: a C1-C4-alkoxy radical as mentioned above which is partially or
fully substituted by fluorine, chlorine, bromine and/or iodine, i.e., for example,
fluoromethoxy, difluoromethoxy, trifluoromethoxy, chlorodifluoromethoxy, bromo-
difluoromethoxy, 2-fluoroethoxy, 2-chloroethoxy, 2-bromomethoxy, 2-iodoethoxy,
2,2-difluoroethoxy, 2,2,2-trifluoroethoxy, 2-chloro-2-fluoroethoxy, 2-chloro-
2,2-difluoroethoxy, 2,2-dichloro-2-fluoroethoxy, 2,2,2-trichloroethoxy, pentafluoro-
ethoxy, 2-fluoropropoxy, 3-fluoropropoxy, 2-chloropropoxy, 3-chloropropoxy,
2-bromopropoxy, 3-bromopropoxy, 2,2-difluoropropoxy, 2,3-difluoropropoxy,
2,3-dichloropropoxy, 3,3,3-trifluoropropoxy, 3,3,3-trichloropropoxy, 2,2,3,3,3-penta-
fluoropropoxy, heptafluoropropoxy, 1 -(fluoromethyl)-2-fluoroethoxy,
1 -(chloromethyl)-2-chloroethoxy, 1 -(bromomethyl)-2-bromoethoxy, 4-fluorobutoxy,
4-chlorobutoxy, 4-bromobutoxy and nonafluorobutoxy;
C^-Ce-haloalkoxy and also the C-pCe-haloalkoxy moieties of C1-CVhaloalkoxy-Cr
C4-alkyl, C1-C6-haloalkoxycarbonyl-C1-C4-alkyl: C1-C4-haloalkoxy as mentioned
above, and also, for example, 5-fiuoropentoxy, 5-c'nioropentoxy, 5-bromopentoxy, 5-
iodopentoxy, undecafluoropentoxy, 6-fluorohexoxy, 6-chlorohexoxy, 6-
bromohexoxy, 6-iodohexoxy and dodecafluorohexoxy;
C1-C6-alkoxy-C1-C4-alkyl and also the C1-C6-alkoxy-C1-C4-alkyl moieties of C1-C6-
alkoxy-C1-C4-alkoxy-C1-C4-alkyr. C1-C4-alkyl which is substituted by C1-C6-alkoxy as
mentioned above, i.e., for example, methoxymethyl, ethoxymethyl, propoxymethyl,
(l-methylethoxy)methyl, butoxymethyl, (l-methylpropoxy)methyl, (2-methyl-
propoxy)methyl, (1,1-dimethylethoxy)methyl, 2-(methoxy)ethyl, 2-(ethoxy)ethyl,
2-(propoxy)ethyl, 2-(1-methylethoxy)ethyl, 2-(butoxy)ethyl, 2-(1-methylpropoxy)-
ethyl, 2-(2-methylpropoxy)ethyl, 2-(1,1-dimethylethoxy)ethyl, 2-(methoxy)propyl,
2-(ethoxy)propyl, 2-(propoxy)propyl, 2-(1-methylethoxy)propyl, 2-(butoxy)propyl,
2-(1-methylpropoxy)propyl, 2-(2-methylpropoxy)propyl, 2-(1,1-dimethylethoxy)-
propyl, 3-(methoxy)propyl, 3-(ethoxy)propyl, 3-(propoxy)propyl, 3-(1-methylethoxy)-

propyl, 3-(butoxy)propyl, 3-(1-methylpropoxy)propyl, 3-(2-methylpropoxy)propyl,
3-(1,1-dimethylethoxy)propyl, 2-(methoxy)butyl, 2-(ethoxy)butyl, 2-(propoxy)butyl,
2-(1-methylethoxy)butyl, 2-(butoxy)butyl, 2-(1-methylpropoxy)butyl, 2-(2-methyl-
propoxy)butyl, 2-(1,1-cSimethylethoxy)butyl, 3-(methoxy)butyl, 3-(ethoxy)butyl,
3-(propoxy)butyl, 3-(1-methylethoxy)butyl, 3-(butoxy)butyl, 3-(1-methylpropoxy)-
butyl, 3-(2-methylpropoxy)butyl, 3-(1,1-dimethylethoxy)butyl, 4-(methoxy)butyl,
4-(ethoxy)butyl, 4-(propoxy)butyl, 4-(1-methylethoxy)butyl, 4-(butoxy)butyl,
4-(1-methylpropoxy)butyl, 4-(2-methylpropoxy)butyl and 4-(1,1-dimethylethoxy)butyl;
C1-C4-alkoxycarbonyl and also the alkoxycarbonyl moieties of C1-C4-alkoxycarbonyl-
C1-CA-alkoxy, C1-C4alkoxy-C1-C4alkoxycarbonyl and di^C1-C4alkyl)amino-C^C^
alkoxycarbonyl: for example methoxycarbonyl, ethoxycarbonyl, propoxycarbonyl,
1-methylethoxycarbonyl, butoxycarbonyl, 1-methylpropoxycarbonyl, 2-
methylpropoxycarbonyl or 1,1-dimethylethoxycarbonyl;
C1-C6-alkoxycarbonyl and also the alkoxycarbonyl moieties of C1-C6-alkoxycarbonyl-
CTC6-alkoxy and C1-C6-alkoxycarbonylamino-C1-C4-alkyl: C1-C4-alkoxycarbonyl as
mentioned above, and also, for example, pentoxycarbonyl, 1-methylbutoxycarbonyl,
2-methylbutoxycarbonyl, 3-methylbutoxycarbonyl, 2,2-dimethylpropoxycarbonyl, 1-
ethylpropoxycarbonyl, hexoxycarbonyl, 1,1-dimethylpropoxycarbonyl, 1,2-
dimethylpropoxycarbonyl, 1-methylpentoxycarbonyl, 2-methylpentoxycarbonyl, 3-
methylpentoxycarbonyl, 4-methylpentoxycarbonyl, 1,1-dimethylbutoxycarbonyl, 1,2-
dimethylbutoxycarbonyl, 1,3-dimethylbutoxycarbonyl, 2,2-dimethylbutoxycarbonyl,
2,3-dimethylbutoxycarbonyl, 3,3-dimethylbutoxycarbonyl, 1-ethylbutoxycarbonyl, 2-
ethylbutoxycarbonyl, 1,1,2-trimethylpropoxycarbonyl, 1,2,2-
trimethylpropoxycarbonyl, 1-ethyl-1-methylpropoxycarbonyl or 1-ethyl-2-
m ethyl propoxyca rbony I ;
C^-C^-alkylthio and also the C1-C4-alkylthio moieties of C1-C6-haloalkyl-C^C^
thioalkyl, C2-C6-haloalkenyl-C1-C4-thioalkyl, C2-C6-haloalkynyl-C1-C4-thioalkyl: for
example methylthio, ethylthio, propylthio, 1-methylethylthio, butylthio, 1-
methylpropylthio, 2-methylpropylthio and 1,1-dimethylethylthio;
C1-C6-alkylthio and also the C1-C6-alkylthio moieties of C1-C6-alkylthio-C1-C4-alkyl:
C^C^alkylthio as mentioned above, and also, for example, pentylthio, 1-
methylbutylthio, 2-methylbutylthio, 3-methylbutylthio, 2,2-dimethylpropylthio, 1-
ethylpropylthio, hexylthio, 1,1-dimethylpropylthio, 1,2-dimethylpropylthio, 1-
methylpentylthio, 2-methylpentylthio, 3-methylpentylthio, 4-methylpentylthio, 1,1-
dimethylbutylthio, 1,2-dimethylbutylthio, 1,3-dimethylbutylthio, 2,2-dimethylbutyI-
thio, 2,3-dimethylbutylthio, 3,3-dimethylbutylthio, 1-ethylbutylthio, 2-ethylbutylthio,
1,1,2-trimethylpropylthio, 1,2,2-trimethylpropylthio, 1-ethyl-1-methylpropylthio and
1 -ethyl-2-methylpropylthio;

C1-C6-alkylamino and also the C1-C6-alkylamino radicals of N-(C1-C6-alkylamino)-
imino-C1-C6-alkyl, C1-C6-alkylamino-C1-C4-alkyl, C1-C6-alkylsulfonyl-(C1-C6-
alkylamino)-C1-C4-alkyl, C1-C6-alkylcarbonyl-(C1-C6-alkylamino)-C1-C4-alkyl and
[(C1-C6-alkyl)amino-cyanoimino: for example methylamino, ethylamino, propylamino,
1-methylethylamino, butylamino, 1-methylpropylamino, 2-methylpropylamino, 1,1-
dimethylethylamino, pentylamino, 1-methylbutylamino, 2-methylbutylamino, 3-
methylbutylamino, 2,2-dimethylpropylamino, 1-ethylpropylamino, hexylamino, 1,1-
dimethylpropylamino, 1,2-dimethylpropylamino, 1-methylpentylamino, 2-
methylpentylamino, 3-methylpentylamino, 4-methylpentylamino, 1,1-
dimethylbutylamino, 1,2-dimethylbutylamino, 1,3-dimethylbutylamino, 2,2-
dimethylbutylamino, 2,3-dimethylbutylamino, 3,3-dimethylbutylamino, 1-
ethylbutylamino, 2-ethylbutylamino, 1,1,2-trimethylpropylamino, 1,2,2-
trimethylpropylamino, 1-ethyl-1-methylpropylamino or 1-ethyl-2-methylpropylamino;
di-(C1-C4-alkyl)amino: for example N,N-dimethylamino, N,N-diethylamino,
N,N-dipropylamino, N,N-di-(1-methylethyl)amino, N,N-dibutylamino,
N,N-di-(1-methylpropyl)amino, N,N~di-(2-methylpropyl)amino, N,N-di-(1,1-dimethyl-
ethyl)amino, N-ethyl-N-methylamino, N-methyl-N-propylamino, N-methyl-
N-(1-methylethyl)amino, N-butyl-N-methylamino, N-methyl-N-(l-methylpropyl)-
amino, N-methyl-N-(2-methylpropyl)amino, N-(1,1-dimethylethyl)-N-methylamino,
N-ethyl-N-propylamino, N-ethyl-N-(1 -methylethyl)amino, N-butyl-N-ethylamino,
N-ethyl-N-(1 -methylpropyl)amino, N-ethyl-N-(2-methylpropyl)amino, N-ethyl-
N-(1,1-dimethylethyl)amino, N-(1-methylethyl)-N-propylamino, N-butyl-N-propyl-
amino, N-(1-methylpropyl)-N-propylamino, N-(2-methylpropyl)-N-propylamino,
N-( 1,1 -dimethylethyl)-N-propylamino, N-butyl-N-(1 -methylethyl)amino, N-(1 -methyl-
ethyl)-N-(1 -methylpropyl)amino, N-(1 -methylethyl)-N-(2-methylpropyl)amino,
N-(1,1-dimethylethyl)-N-(1-methylethyl)amino, N-butyl-N-(1-methylpropyl)amino,
N-butyl-N-(2-methylpropyl)amino, N-butyl-N-(1,1-dimethylethyl)amino, N-(1-methyl-
propyI)-N-(2-methylpropyl)amino, N-(1,1-dimethylethyl)-N-(1-methylpropyl)amino
and N-(1,1-dimethylethyl)-N-(2-methylpropyl)amino;
di(C1-C6-alkyl)amino and also the dialkylamino radicals of N-(di-C1-C6-
alkylamino)imino-C1-C6-alkyl, di(C1-C6-alkyl)amino-C1-C4-alkyl, [di(C1-C6-
alkyl)aminocabonyloxy]-C1-C4-alkyl, {di[di(C1-C6-alkyl)amino]cabonyloxy}-C1-C4-alkyl
and ^((C1-C6-alkyl)aminoJcyanoimino: di(C1-C4-alkyl)amino as mentioned above,
and also, for example, N,N-dipentylamino, M,N-dihexylamino, N-methyl-N-
pentylamino, N-ethyl-N-pentylamino, N-methyl-N-hexylamino and N-ethyl-N-
hexylamino; (C1-C4-alkylamino)carbonyl: for example methylaminocarbonyl,
ethylaminocarbonyl, propylaminocarbonyl, 1 -methylethylaminocarbonyl,
butylaminocarbonyl, 1-methylpropylaminocarbonyl, 2-methylpropylaminocarbonyl or
1,1-dimethylethylaminocarbonyl;

(C^CValkylamino^arbonyl and also the (C1-C4-alkylamino)carbonyl moieties of
(C1-C4-alkylamino)carbonylamino: for example methylaminocarbonyl,
ethylaminocarbonyl, propylaminocarbonyl, 1-methylethylaminocarbonyl,
butylaminocarbonyl, 1-methylpropylaminocarbonyl, 2-methylpropylaminocarbonyl or
1,1 -dimethylethylaminocarbonyl;
di(C1-C4-alkyl)aminocarbonyl and also the di(C1-C4-alkyl)aminocarbonyl moieties of
di(C1-C4-alkyl)aminocarbonylamino: for example N,N-dimethylaminocarbonyl,
N,N-diethylaminocarbonyl, N,N-di-(1-methylethyl)aminocarbonyl, N,N-dipropyl-
aminocarbonyl, N,N-dibutylaminocarbonyl, N,N-di-(1-methylpropyl)aminocarbonyl,
N,N-di-(2-methylpropyl)aminocarbonyl, N,N-di-(1,1-dimethylethyl)aminocarbonyl,
N-ethyl-N-methylaminocarbonyl, N-methyl-N-propylaminocarbonyl, N-methyl-
N-( 1 -methylethyl)aminocarbonyl, N-butyl-N-methylaminocarbonyl, N-methyl-
N-(1-methylpropyl)aminocarbonyl, N-methyl-N-(2-methylpropyl)aminocarbonyl,
N-(1,1-dimethylethyl)-N-methylaminocarbonyl, N-ethyl-N-propylaminocarbonyl,
N-ethyl-N-(1-methylethyl)aminocarbonyl, N-butyl-N-ethylaminocarbonyl, N-ethyl-
N-(1-methylpropyl)aminocarbonyl, N-ethyl-N-(2-methylpropyl)aminocarbonyl,
N-ethyl-N-(1,1-dimethylethyl)aminocarbonyl, N-(1-methylethyl)-N-propylamino-
carbonyl, N-butyl-N-propylaminocarbonyl, N-(1-methylpropyl)-N-propylamino-
carbonyl, N-(2-methylpropyl)-N-propylaminocarbonyl, N-(1,1-dimethylethyl)-
N-propylaminocarbonyl, N-butyl-N-(1-methylethyl)aminocarbonyl, N-(l-methylethyl)-
N-(1-methylpropyl)aminocarbonyl, N-(1-methylethyl)-N-(2-methylpropyl)amino-
carbonyl, N-(1,1-dimethylethyl)-N-(1-methylethyl)aminocarbonyl, N-butyl-
N-(1-methylpropyl)aminocarbonyl, N-butyl-N-(2-methylpropyl)aminocarbonyl,
N-butyl-N-(1,1-dimethylethyl)aminocarbonyl, N-(1-methylpropyl)-N-(2-methyl-
propyl)aminocarbonyl, N-(1,1-dimethylethyl)-N-(1-methylpropyl)aminocarbonyl or
N-(1,1 -dimethylethyl)-N-(2-methylpropyl)aminocarbonyl;
(C1-C6-alkylamino)carbonyl and also the (C1-C6-alkylamino)carbonyl moieties of
(C1-C6-alkylamino)carbonylamino, (C1-C6-alkylamino)carbonyloxy-C1-C4-alkyl,
C1-C6-alkylaminocarbonyl-C1-C4-alkyl and [(C1-C6-alkyl)aminocarbonylaminol-C1-C,,-
alkyl: (C1-C4alkylaminoJcarbonyl as mentioned above, and also, for example,
pentylaminocarbonyl, 1 -methylbutylaminocarbonyl, 2-methylbutylaminocarbonyl,
3-methylbutylaminocarbonyl, 2,2-dimethylpropylaminocarbonyl, 1 -ethylpropylamino-
carbonyl, hexylaminocarbonyl, 1,1-dimethylpropylaminocarbonyl, 1,2-dimethyl-
propylaminocarbonyl, 1 -methylpentylaminocarbonyl, 2-methylpentylaminocarbonyl,
3-methylpentylaminocarbonyl, 4-methylpentylaminocarbonyl, 1,1-dimethylbutyl-
aminocarbonyl, 1,2-dimethylbutylaminocarbonyl, 1,3-dimethylbutylaminocarbonyl,
2,2-dimethylbutylaminocarbonyl, 2,3-dimethylbutylaminocarbonyl, 3,3-dimethylbutyl-
aminocarbonyl, 1-ethylbutylaminocarbonyl, 2-ethylbutylaminocarbonyl, 1,1,2-
trimethylpropylaminocarbonyl, 1,2,2-trimethylpropylaminocarbonyl, 1-ethyl-1-

methylpropylaminocarbonyl or 1 -ethyl-2-methylpropylaminocarbonyl;
■ di(C1-C6-alky[)aminocarbonyl and also the di(C1-C6-alkyl)aminocarbonyl moieties of
di(C1-C6-alkyl)aminocarbonylamino, di^rCe-alkyl)aminocarbonyl-C1-CA-alkyl and
[di(C1-C6-alkyl)aminocarbonylamino]-C1-C4-alkyl: dKC1-C4alkyl)aminocarbonyl as
mentioned above, and also, for example, N-methyl-N-pentylaminocarbonyl, N-
methyl-N-(1-methylbutyl)aminocarbonyl, N-methyl-N-(2-methylbutyl)aminocarbonyl,
N-methyl-N-(3-methylbutyl)aminocarbonyl, N-methyl-N-(2,2-dimethylpropyl)amino-
carbonyl, N-methyl-N-(1-ethylpropyl)aminocarbonyl, N-methyl-N-hexylamino-
carbonyl, N-methyl-N-(1,1-dimethylpropyl)aminocarbonyl, N-methyl-N-(1,2-dirnethyl-
propyl)aminocarbonyl, N-methyl-N-(1-methylpentyl)aminocarbonyl, N-methyl-
N-(2-methylpentyl)aminocarbonyl, N-methyl-N-(3-methylpentyl)aminocarbonyl,
N-methyl-N-(4-methylpentyl)aminocarbonyl, N-methyl-N-(1,1-dimethylbutyl)amino-
carbonyl, N-methyl-N-(1,2-dimethylbutyl)aminocarbonyl, N-methyl-N-(1,3-dimethyl-
butyl)aminocarbonyl, N-methyl-N-(2,2-dimethylbutyl)aminocarbonyl, N-methyl-
N-(2,3-dimethylbutyl)aminocarbonyl, N-methyl-N-(3,3-dimethylbutyl)aminocarbonyl,
N-methyl-N-(1-ethylbutyl)aminocarbonyl, N-methyl-N-(2-ethylbutyl)aminocarbonyl,
N-methyl-N-(1,1,2-trimethylpropyl)aminocarbonyl, N-methyl-N-(1,2,2-trimethyl-
propyl)aminocarbonyl, N-methyl-N-(1-ethyl-1-methylpropyl)aminocarbonyl,
N-methyl-N-(1-ethyl-2-methylpropyl)aminocarbonyl, N-ethyl-N-pentylaminocarbonyl,
N-ethyl-N-(1-methylbutyl)aminocarbonyl, N-ethyl-N-(2-methylbutyl)aminocarbonyl,
N-ethyl-N-(3-methylbutyl)aminocarbonyl, N-ethyl-N-(2,2-dimethylpropyl)amino-
carbonyl, N-ethyl-N-(1-ethylpropyl)aminocarbonyl, N-ethyl-N-hexylaminocarbonyl,
N-ethyl-N-(1,1-dimethylpropyl)aminocarbonyl, N-ethyl-N-(1,2-dimethylpropyl)amino-
carbonyl, N-ethyl-N-(1-methylpentyl)aminocarbonyl, N-ethyl-N-(2-methylpentyl)-
aminocarbonyl, N-ethyl-N-(3-methylpentyl)aminocarbonyl, N-ethyl-N-(4-methyl-
pentyl)aminocarbonyl, N-ethyl-N-(1,1-dimethylbutyl)aminocarbonyl, N-ethyl-
N-(1,2-dimethylbutyl)aminocarbonyl, N-ethyl-N-(1,3-dimethylbutyl)aminocarbonyl,
N-ethyl-N-(2,2-dimethylbutyl)aminocarbonyl, N-ethyl-N-(2,3-dimethylbutyl)amino-
carbonyl, N-ethyl-N-(3,3-dimethylbutyl)aminocarbonyl, N-ethyl-N-(l-ethylbutyl)-
aminocarbonyl, N-ethyl-N-(2-ethylbutyl)aminocarbonyl, N-ethyl-N-(1,1,2-trimethyl-
propyl)aminocarbonyl, N-ethyl-N-(1,2,2-trimethylpropyl)aminocarbonyI, N-ethyl-
N-(1-ethyl-1-methylpropyl)aminocarbonyl, N-ethyl-N-(1-ethyl-2-methylpropyl)-
aminocarbonyl, N-propyl-N-pentylaminocarbonyl, N-butyl-N-pentylaminocarbonyl,
N,N-dipentylaminocarbonyl, N-propyl-N-hexylaminocarbonyl, N-butyl-N-hexylamino-
carbonyl, N-pentyl-N-hexylaminocarbonyl or N,N-dihexylaminocarbonyl;
di(C1-C6-alkyl)aminothiocarbonyl: for example N,N-dimethylaminothiocarbonyl,
N,N-diethylaminothiocarbonyl, N,N-di-(1-methylethyl)aminothiocarbonyl,
N.N-dipropylaminothiocarbonyl, N,N-dibutylaminothiocarbonyl, N,N-di-(1-methyl-
propyl)aminothiocarbonyl, N,N-di-(2-methylpropyl)aminothiocarbonyl,
N,N-di-(1,1-dimethylethyl)aminothiocarbonyl, N-ethyl-N-methylaminothiocarbonyl,

N-methyl-N-propylaminothiocarbonyl, N-methyl-N-(1-methylethyl)aminothiocarbonyl,
N-butyl-N-methylaminothiocarbonyl, N-methyl-N-(1-methylpropyl)aminothiocarbonyl,
N-methyl-N-(2-methylpropyl)aminothiocarbonyl, N-(1,1-dimethylethyl)-N-methyl-
aminothiocarbonyl, N-ethyl-N-propylaminothiocarbonyl, N-ethyl-N-(1 -methylethyl)-
aminothiocarbonyl, N-butyl-N-ethylaminothiocarbonyl, N-ethyl-N-(l-methylpropyl)-
aminothiocarbonyl, N-ethyl-N-(2-methylpropyl)aminothiocarbonyI, N-ethyl-
N-(1,1-dimethylethyl)aminothiocarbonyl, N-(1-methylethyl)-N-propylaminothio-
carbonyl, N-butyl-N-propylaminothiocarbonyl, N-(1-methylpropyl)-N-propylamino-
thiocarbonyl, N-(2-methylpropyl)-N-propylamino-thiocarbonyl, N-(1,1-dimethylethyl)-
N-propylaminothiocarbonyl, N-butyl-N-(1-methylethyl)aminothiocarbonyl,
N-(1-methylethyl)-N-(1-methylpropyl)aminothiocarbonyl, N-(1-methylethyl)-N-(2-
methylpropyl)aminothiocarbonyl, N-(1,1-dimethylethyl)-N-(1-methylethyl)amino-
thiocarbonyl, N-butyl-N-(1 -methylpropyl)aminothiocarbonyl, N-butyl-N-(2-methyl-
propyl)aminothiocarbonyl, N-butyl-N-(1,1-dimethylethyl)aminothiocarbonyl,
N-(1-methylpropyl)-N-(2-methylpropyl)aminothiocarbonyl, N-(1,1-dimethylethyl)-
N-(1-methylpropyl)aminothiocarbonyl, N-(1,1-dimethylethyl)-N-(2-methylpropyl)-
aminothiocarbonyl, N-methyl-N-pentylaminothiocarbonyl, N-methyl-N-(1 -methyl-
butyl)aminothiocarbonyl, N-methyl-N-(2-methylbutyl)aminothiocarbonyl, N-methyl-
N-(3-methylbutyl)aminothiocarbonyl, N-methyl-N-(2,2-dimethylpropyl)amino-
thiocarbonyl, N-methyl-N-(1 -ethylpropyl)aminothiocarbonyl, N-methyl-N-hexylamino-
thiocarbonyl, N-methyl-N-(1,1-dimethylpropyl)aminothiocarbonyl, N-methyl-
N-(1,2-dimethylpropyl)aminothiocarbonyl, N-methyl-N-(l-methylpentyl)-
aminothiocarbonyl, N-methyl-N-(2-methylpentyl)aminothiocarbonyI, N-methyl-
N-(3-methylpentyl)aminothiocarbonyl, N-methyl-N-(4-methylpentyl)aminothio-
carbonyl, N-methyl-N-(1,1-dimethylbutyl)aminothiocarbonyl, N-methyl-
N-(1,2-dimethylbutyl)aminothiocarbonyl, N-methyl-N-(1,3-dimethylbutyl)amino-
thiocarbonyl, N-methyl-N-(2,2-dimethylbutyl)aminothiocarbonyl, N-methyl-
N-(2,3-dimethylbutyl)aminothiocarbonyl, N-methyl-N-(3,3-dimethylbutyl)aminothio-
carbonyl, N-methyl-N-(i-ethylbutyl)aminothiocarbonyl, N-methyl-N-(2-ethylbutyl)-
aminothiocarbonyl, N-methyl-N-ethyl-N-(1,1,2-trimethylpropyl)aminothiocarbonyl,
N-methyl-N-(1,2,2-trimethylpropyl)aminothiocarbonyl, N-methyl-N-(1-ethyl-1-methyl-
propyl)aminothiocarbonyl, N-methyl-N-(1-ethyl-2-methylpropyl)aminothiocarbonyl,
N-ethyl-N-pentylaminothiocarbonyl, N-ethyl-N-(1-methylbutyl)aminothiocarbonyl,
N-ethyl-N-(2-methylbutyl)aminothiocarbonyl, N-ethyl-N-(3-methylbutyl)aminothio-
carbonyl, N-ethyl-N-(2,2-dimethylpropyl)aminothiocarbonyl, N-ethyl-N-(1-ethyl-
propyl)aminothiocarbonyl, N-ethyl-N-hexylaminothiocarbonyl, N-ethyl-
N-(1,1-dimethylpropyl)aminothiocarbonyl, N-ethyl-N-(1,2-dimethylpropyl)amino-
thiocarbonyl, N-ethyl-N-(1 -methylpentyl)aminothiocarbonyl, N-ethyl-N-(2-methyl-
pentyl)aminothiocarbonyl, N-ethyl-N-(3-methylpentyl)aminothiocarbonyl, N-ethyl-
N-(4-methylpentyl)aminothiocarbonyl, N-ethyl-N-(1,1 -dimethylbutyl)aminothio-
carbonyl, N-ethyl-N-(1,2-dimethylbutyl)aminothiocarbonyl, N-ethyl-N-(1,3-dimethyl-
butyl)aminothiocarbonyl, N-ethyl-N-(2,2-dimethylbutyl)aminothiocarbonyl, N-ethyl-

N-(2,3-dimethylbutyl)aminothiocarbonyl, N-ethyl-N-(3,3-dimethylbutyl)amino-
thiocarbonyl, N-ethyl-N-(1 -ethylbutyl)aminothiocarbonyl, N-ethyl-N-(2-ethylbutyl)-
aminothiocarbonyl, N-ethyl-N-(1,1,2-trimethylpropyl)aminothiocarbonyl, N-ethyl-
N-(1,2,2-trimethylpropyl)aminothiocarbonyl, N-ethyl-N-(1 -ethyl-1 -methylpropyl)-
aminothiocarbonyl, N-ethyl-N-(1 -ethyl-2-methylpropyl)aminothiocarbonyl, N-propyl-
N-pentylaminothiocarbonyl, N-butyl-N-pentylaminothiocarbonyl, N,N-dipentyl-
aminothiocarbonyl, N-propyl-N-hexylaminothiocarbonyl, N-butyl-N-hexylaminothio-
carbonyl, N-pentyl-N-hexylaminothiocarbonyl or N,N-dihexylaminothiocarbonyl;
three- to six-membered heterocyclyl and also the three- to six-membered
heterocyclyl moieties of three- to six-membered heterocyclyl-C1-C4-alkyl: monocyclic
saturated or partially unsaturated hydrocarbons having three to six ring members as
mentioned above which, in addition to carbon atoms, may contaln one to four
nitrogen atoms or one to three nitrogen atoms and one oxygen or sulfur atom or one
to three oxygen atoms or one to three sulfur atoms and which may be attached via a
carbon atom or a nitrogen atom, for example
for example 2-oxrianyl, 2-oxetanyl, 3-oxetanyl, 2-aziridinyl, 3-thiethanyl, 1-azetidinyl,
2-azetidinyl,
for example 2-tetrahydrofuranyl, 3-tetrahydrofuranyl, 2-tetrahydrothienyl, 3-tetra-
hydrothienyl, 2-pyrrolidinyl, 3-pyrrolidinyl, 3-isoxazolidinyl, 4-isoxazolidinyl, 5-
isoxazolidinyl, 3-isothiazolidinyl, 4-isothiazolidinyl, 5-isothiazolidinyl, 3-pyrazolidinyl,
4-pyrazolidinyl, 5-pyrazolidinyl, 2-oxazolidinyl, 4-oxazolidinyl, 5-oxazolidinyl, 2-
thiazolidinyl, 4-thiazolidinyl, 5-thiazolidinyl, 2-imidazoiidinyl, 4-imidazolidinyl, 1,2,4-
oxadiazolidin-3-yl, 1,2,4-oxadiazolidin-5-yl, 1,2,4-thiadiazolidin-3-yl, 1,2,4-
thiadiazolidin-5-yl, 1,2,4-triazolidin-3-yl, 1,3,4-oxadiazolidin-2-yl, 1,3,4-thiadiazolidin-
2-yl, 1,3,4-triazolidin-2-yl, 1,2,3,4-tetrazolidin-5-yl;
for example 1-pyrrolidinyl, 2-isothiazolidinyl, 2-isothiazolidinyl, 1-pyrazolidinyl, 3-
oxazolidinyl, 3-thiazolidinyl, 1-imidazolidinyl, 1,2,4-triazolidin-1-yl, 1,2,4-
oxadiazoiidin-2-yl, 1,2,4-oxadiazolidin-4-yl, 1,2,4-thiadiazolidin-2-yl, 1,2,4-
thiadiazolidin-4-yl, 1,2,3,4-tetrazolidin-1-yl,
for example 2,3-dihydrofur-2-yl, 2,3-dihydrofur-3-yl, 2,4-dihydrofur-2-yl, 2,4-
dihydrofur-3-yl, 2,3-dihydrothien-2-yl, 2,3-dihydrothien-3-yl, 2,4-dihydrothien-2-yl,
2,4-dihydrothien-3-yl, 4,5-dihydropyrrol-2-yl, 4,5-dihydropyrrol-3-yl, 2,5-
dihydropyrrol-2-yl, 2,5-dihydropyrrol-3-yl, 4,5-dihydroisoxazol-3-yl, 2,5-
dihydroisoxazol-3-yl, 2,3-dihydroisoxazol-3-yl, 4,5-dihydroisoxazol-4-yl, 2,5-
dihydroisoxazol-4-yl, 2,3-dihydroisoxazol-4-yl, 4,5-dihydroisoxazol-5-yl, 2,5-
dihydroisoxazol-5-yl, 2,3-dihydroisoxazol-5-yl, 4,5-dihydroisothiazol-3-yl, 2,5-
dihydroisothiazol-3-yl, 2,3-dihydroisothiazol-3-yl, 4,5-dihydroisothiazol-4-yl, 2,5-

dihydroisothiazol-4-yl, 2,3-dihydroisothiazol-4-yl, 4,5-dihydroisothiazol-5-yl, 2,5-
dihydroisothiazol-5-yl, 2,3-dihydroisothiazol-5-yl, 2,3-dihydropyrazol-2-yl, 2,3-
dihydropyrazol-3-yl, 2,3-dihydropyrazol-4-yl, 2,3-dihydropyrazol-5-yl, 3,4-
dihydropyrazol-3-yl, 3,4-dihydropyrazol-4-yl, 3,4-dihydropyrazol-5-yl, 4,5-
dihydropyrazol-3-yl, 4,5-dihydropyrazol-4-yl, 4,5-dihydropyrazol-5-yl, 2,3-
dihydroimidazol-2-yl, 2,3-dihydroimidazol-3-yl ,2,3-dihydroimidazol-4-yl, 2,3-
dihydroimidazol-5-yl, 4,5-dihydroimidazol-2-yl, 4,5-dihydroimidazol-4-yl, 4,5-
dihydroimidazol-5-yl, 2,5-dihydroimidazol-2-yl, 2,5-dihydroimidazol-4-yl, 2,5-
dihydroimidazol-5-yl, 2,3-dihydrooxazol-3-yl, 2,3-dihydrooxazol-4-yl, 2,3-
dihydrooxazol-5-yl, 3,4-dihydrooxazol-3-yl, 3,4-dihydrooxazol-4-yl, 3,4-
dihydrooxazol-5-yl, 2,3-dihydrothiazol-3-yl, 2,3-dihydrothiazol-4-yl, 2,3-di-
hydrothiazol-5-yl, 3,4-dihydrothiazol-3-yl, 3,4-dihydrothiazol-4-yl, 3,4-dihydrothiazol-
5-yl, 3,4-dihydrothiazol-2-yl, 3,4-dihydrothiazol-3-yl, 3,4-dihydrothiazol-4-yl,
for example 4,5-dihydropyrrol-1-yl, 2,5-dihydropyrrol-1-yl, 4,5-dihydroisoxazol-2-yl,
2,3-dihydroisoxazoi-1-yl, 4,5-dihydroisothiazol-1-yl, 2,3-dihydroisothiazoi-1-yl, 2,3-
dihydropyrazol-1-yl, 4,5-dihydropyrazol-1-yl, 3,4-dihydropyrazol-1-yl, 2,3-dihydro-
imidazol-1-yl, 4,5-dihydroimidazol-1-yl, 2,5-dihydroimidazol-1-yl, 2,3-dihydrooxazol-
2-yl, 3,4-dihydrooxazol-2-yl, 2,3-dihydrothiazol-2-yl, 3,4-dihydrothiazol-2-yl;
for example 2-piperidinyI, 3-piperidinyl, 4-piperidinyl, 1,3-dioxan-2-yl, 1,3-dioxan-4-
yl, 1,3-dioxan-5-yl, 1,4-dioxan-2-yl, 1,3-dithion-2-yl, 1,3-dithion-3-yl, 1,3-dithion-4-
yl, 1,4-dithion-2-yl, 1,3-dithian-5-yl, 2-tetrahydropyranyl, 3-tetrahydropyranyl,
4-tetrahydropyranyl, 2-tetrahydrothiopyranyl, 3-tetrahydrothiopyranyl, 4-tetrahydro-
thiopyranyl, 3-hexahydropyridazinyl, 4-hexahydropyridazinyl, 2-hexahydropyrimidi-
nyl, 4-hexahydropyrimidinyl, 5-hexahydropyrimidinyl, 2-piperazinyl, 1,3,5-hexa-
hydrotriazin-2-yl, 1,2,4-hexahydrotriazin-3-yl, tetrahydro-1,3-oxazin-2-yl, tetrahydro-
1,3-oxazin-6-yl, 2-morpholinyl, 3-morpholinyl, 1,3,5-trioxan-2-yl;
for example 1-piperidinyl, 1-hexahydropyridazinyl, 1-hexahydropyrimidinyl, 1-
piperazinyl, 1,3,5-hexahydrotriazin-1-yl, 1,2,4-hexahydrotriazin-1-yl, tetrahydro-1,3-
oxazin-1-yl, 1-morpholinyl;
for example 2H-pyran-2-yl, 2H-pyran-3-yl, 2H-pyran-4-yl, 2H-pyran-5-yl, 2H-pyran-
6-yl, 3,6-dihydro-2H-pyran-2-yl, 3,6-dihydro-2H-pyran-3-yl, 3,6-dihydro-2H-pyran-4-
yl, 3,6-dihydro-2H-pyran-5-yl, 3,6-dihydro-2H-pyran-6-yl, 3,4-dihydro-2H-pyran-3-yl,
3,4-dihydro-2H-pyran-4-yl, 3,4-dihydro-2H-pyran-6-yl, 2H-thiopyran-2-yl, 2H-
thiopyran-3-yl, 2H-thiopyran-4-yl, 2H-thiopyran-5-yl, 2H-thiopyran-6-yl, 5,6-dihydro-
4H-1,3-oxazin-2-yl;
aryl and the aryl moiety of aryl-(C1-C6-alkyl): a monocyclic to tricyclic aromatic
carbocycle having 6 to 14 ring members, such as, for example, phenyl, naphthyl

and anthracenyl;
heteroaryl and also the heteroaryl radicals in heteroaryl-C1-C4-alkyl, heteroaryl-d-
C4-alkyl, heteroaryl-C2-C4-alkenyl, heteroaryl-C2-C4-alkynyl, heteroaryl-C1-C4-
halogenalkyl, heteroaryl-C2-C4-halogenalkenyl, heteroaryl-C2-C4-halogenalkynyl,
heteroaryl-C1-C4hydroxyalkyl, heteroaryl-C2-C4-hydroxyalkenyl, heteroaryl-C2-C4-
hydroxyalkynyl, heteroarylcarbonyl-C1-C4-alkyl, heteroarylcarbonyloxy-C1-C4-alkyl,
heteroaryloxycarbonyl-C1-C4-alkyl, heteroaryloxy-C1-C4-alkyl, heteroarylthio-C1-C4-
alkyl, heteroarylsulfinyl-C1-C4-alkyl, heteroarylsulfonyl-C1-C4-alkyl:
mono- or bicyclic aromatic heteroaryl having 5 to 10 ring members which, in addition
to carbon atoms, contalns 1 to 4 nitrogen atoms, or 1 to 3 nitrogen atoms and an
oxygen or sulfur atom, or an oxygen or a sulfur atom, for example
monocycles, such as furyl (for example 2-furyl, 3-furyl), thienyl (for example 2-
thienyl, 3—thienyl), pyrrolyl (for example pyrrol—2—yl, pyrrol-3-yl), pyrazolyl (for
example pyrazol-3-yl, pyrazol-4-yl), isoxazolyl (for example isoxazol-3-yl,
isoxazol-4-yl, isoxazol-5-yl), isot'niazolyl (for example isothiazol-3-yl, isothiazol-
4-yl, isothiazol-5-yl), imidazolyl (for example imidazol-2-yl, imidazol-4-yl),
oxazolyl (for example oxazol-2-yl, oxazol-4-yl, oxazol-5-yl), thiazolyl (for example
thiazol-2-yl, thiazol-4-yl, thiazol-5-yl), oxadiazolyl (for example 1,2,3-oxadiazol-
4—yl, 1,2,3-oxadiazol-5-yl, 1,2,4-oxadiazol-3-yl, 1,2,4,-oxadiazol-5-yl, 1,3,4-
oxadiazoi-2-yl), thiadiazolyl (for example 1,2,3-thiadiazol-4-yl, 1,2,3-thiadiazol-5-
yl, 1,2,4-thiadiazol-3-yl, 1,2,4-thiadiazol-5-yl, 1,3,4-thiadiazolyl-2-yl), triazolyl
(for example 1,2,3-triazol-4-yI, 1,2,4-triazol-3-yl), tetrazol-5-yl, pyridyl (for
example pyridin-2-yl, pyridin-3-yl, pyridin-4-yl), pyrazinyl (for example pyridazin-
3-yl, pyridazin-4-yl), pyrimidinyl (for example pyrimidin—2-yl, pyrimidin-4-yl,
pyrimidin-5-yl), pyrazin-2-yl, triazinyl (for example 1,3,5—triazin—2—yl, 1,2,4-
triazin-3-yl, 1,2,4—triazin-5-yl, 1,2,4-triazin—6—yl), tetrazinyl (for example 1,2,4,5-
tetrazin-3-yl); and also
bicycles such as the benzo-fused derivatives of the abovementioned monocycles,
for example quinolinyl, isoquinolinyl, indolyl, benzothienyl, benzofuranyl,
benzoxazolyl, benzothiazolyl, benzisothiazolyl, benzimidazoiyl, benzopyrazolyl,
benzothiadiazolyl, benzotriazolyl.
5- or 6-membered heteroaryl having one to four nitrogen atoms or one to three
nitrogen atoms and one oxygen or sulfur atom or having one oxygen or sulfur atom:
for example aromatic 5-membered heterocycles which are attached via a carbon
atom and which, in addition to carbon atoms, may contaln one to four nitrogen
atoms or one to three nitrogen atoms and one sulfur or oxygen atom or one sulfur or
oxygen atom as ring members, for example 2-furyl, 3-furyl, 2-thienyl, 3-thienyl,
2-pyrrolyl, 3-pyrrolyl, 3-isoxazolyl, 4-isoxazolyl, 5-isoxazolyl, 3-isothiazolyl,
4-isothiazolyl, 5-isothiazolyl, 3-pyrazolyl, 4-pyrazolyl, 5-pyrazolyl, 2-oxazolyl,
4-oxazolyl, 5-oxazolyl, 2-thiazolyl, 4-thiazolyl, 5-thiazolyl, 2-imidazolyl, 4-imidazolyl,

1,2,4-oxadiazol-3-yl, 1,2,4-oxadiazol-5-yl, 1,2,4-thiadiazol-3-yl, 1,2,4-thiadiazol-5-yl,
1,2,4-triazol-3-yl, 1,3,4-oxadiazo!-2-yl, 1,3,4-thiadiazoi-2-yl and 1,3,4-triazo!-2-yl;
for example aromatic 6-membered heterocycles which are attached via a carbon
atom and which, in addition to carbon atoms, may contaln one to four, preferably
one to three, nitrogen atoms as ring members, for example 2-pyridinyl, 3-pyridinyl,
4-pyridinyl, 3-pyridazinyl, 4-pyridazinyl, 2-pyrimidinyl, 4-pyrimidinyl, 5-pyrimidinyl,
2-pyrazinyl, 1,3,5-triazin-2-yl and 1,2,4-triazin-3-yl.
All phenyl and aryl rings or heterocyclyl and heteroaryl radicals and all phenyl
components in phenyl-C1-C6-alkyl, phenylcarbonyl, phenylcarbonyl-C1-C6-alkyl, phenyl-
carbonylamino-C1--C4-alkyl, phenoxycarbonyl, phenylaminocarbonyl, phenylsulfonyl-
aminocarbonyl, N-(C1-C6-alkyl)-N-phenylaminocarbonyl and phenyl-C1-C6-alkyl-
carbonyl, all aryl components in aryKC1-C4alkyl), all heteroaryl components in mono-
or bicyclic heteroaryl and all heterocyclyl components in heterocyclyl, heterocyclyl-
C1-C6-alkyl, heterocyclylcarbonyl, heterocyclylcarbonyl-C1-C6-alkyl, heterocyclyloxy-
carbonyl, heterocyclylaminocarbonyl, heterocyclylsulfonylaminocarbonyl, N-(C1-C6-
alkyl)-N-heterocyclylaminocarbonyl and heterocyclyl-C1-C6-alkylcarbonyl are, unless
indicated otherwise, preferably unsubstituted or carry one to three halogen atoms
and/or one nitro group, one cyano radical and/or one or two methyl, trifluoromethyl,
methoxy or trifluoromethoxy substituents.
In a particular embodiment, the variables of the heteroaroyl-substituted serineamides of
the formula I are as defined below, these definitions being, both on their own and in
combination with one another, particular embodiments of the compounds of the
formula I:
Preference is given to the heteroaroyl-substituted serineamides of the formula I in
which
A is 5-membered heteroaryl having one to four nitrogen atoms or one to three
nitrogen atoms and one oxygen or sulfur atom or having one oxygen or sulfur
atom;
particularly preferably 5-membered heteroaryl selected from the group consisting
of thienyl, furyl, pyrazolyl, imidazolyl, thiazolyl and oxazolyl;
especially preferably 5-membered heteroaryl selected from the group consisting
of thienyl, furyl, pyrazolyl and imidazolyl;
where the heteroaryl radicals mentioned are substituted by a C1-C6-haloalkyl
radical, preferably in the 2-position by a C1-C6-haloalkyl radical, and may carry 1

to 3 radicals from the group consisting of halogen, cyano, C1-C6-alkyl, C3-C6-
cycloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy and C1--Ce-alkoxy-CVC^alkyl.
Preference is likewise given to the heteroaroyl-substituted serineamides of the formula
I in which
A is 5-membered heteroaryl having one to four nitrogen atoms or one to three
nitrogen atoms and one oxygen or sulfur atom or having one oxygen or sulfur
atom;
particularly preferably 5-membered heteroaryl selected from the group consisting
of thienyl, furyl, pyrazolyl, imidazotyl, thiazolyl and oxazolyl;
especially preferably 5-membered heteroaryl selected from the group consisting
of thienyl, furyl, pyrazolyl and imidazolyl;
where the heteroaryl radicals mentioned may be partially or fully
halogenated and/or may carry 1 to 3 radicals from the group consisting
of cyano, C1-C6-alkyl, C3-C6-cycloalkyl, C1-C6-haloalkyl, C1-C6-alkoxy, Cr
C6-haloalkoxy and C1-C6-alkoxy-C1-C4-alkyl.
Preference is likewise given to the heteroaroyl-substituted serineamides of the formula
I in which
A is 5-membered heteroaryl having one to four nitrogen atoms or one to three
nitrogen atoms and one oxygen or sulfur atom or having one oxygen atom;
particularly preferably 5-membered heteroaryl selected from the group consisting
of furyl, pyrazolyl, imidazolyl, thiazolyl and oxazolyl;
especially preferably 5-membered heteroaryl selected from the group consisting
of furyl, pyrazolyl and imidazolyl;
where the heteroaryl radicals mentioned may be partially or fully
halogenated and/or may carry 1 to 3 radicals from the group consisting
of cyano, C1-C6-alkyl, C3-C6-cycloalkyl, C1-C6-haloalkyl, C1-C6-alkoxy, Cr
C5-haloalkoxy and C1-C6-alkoxy-C1-C4-alkyl.
Preference is likewise given to the heteroaroyl-substituted serineamides of the formula
I in which
A is 6-membered heteroaryl having one to four nitrogen atoms;
particularly preferably pyridyl or pyrimidyl;
especially preferably pyrimidyl;
where the heteroaryl radicals mentioned may be partially or fully
halogenated and/or may carry 1 to 3 radicals from the group consisting
of cyano, C^Cg-alkyl, C3-C6-cycloalkyl, C1-C6-haloalkyl, C1-C6-alkoxy, d-
C6-haloalkoxy and C1-C6-alkoxy-C1-C-alkyl.

Preference is likewise given to the heteroaroyl-substituted serineamides of the formula
I in which
A is 5- or 6-membered heteroaryl having one to four nitrogen atoms or one to three
nitrogen atoms and one oxygen or sulfur atom or having one oxygen or sulfur
atom
which is substituted by a C1-C6-haloalkyl radical, preferably in the 2-
position by a C1-C6-haloalkyl radical, and may carry 1 to 3 radicals from
the group consisting of cyano, C1-C6-alkyl, C3-C6-cycloalkyl, (VC6-
alkoxy, C1-C6-haloalkoxy and C1-C6-alkoxy-C1-C4alkyl.
Preference is likewise given to the heteroaroyl-substituted serineamides of the formula
I in which
A is 5- or 6-membered heteroaryl selected from the group consisting of pyrrolyl,
thienyl, furyl, pyrazolyl, imidazolyl, thiazolyl, oxazolyl, tetrazolyl, pyridyl and
pyrimidinyl;
where the heteroaryl radicals mentioned may be partially or fully
halogenated and/or may carry 1 to 3 radicals from the group consisting
of cyano, C1-C6-alkyl, C3-C6-cycloalkyl, C1-C6-haloalkyl, C1-C6-alkoxy, Cr
C6-haloalkoxy and C1-CValkoxy-C1-C4alkyl;
particularly preferably 5- or 6-membered heteroaryl selected from the group
consisting of thienyl, furyl, pyrazolyl, imidazolyl, thiazolyl, oxazolyl and pyridyl;
where the heteroaryl radicals mentioned may be partially or fully
halogenated and/or may carry 1 to 3 radicals from the group consisting
of C1-C6-alkyl, C3-C6-cycloalkyl and C1--C6-haloalkyl;
especially preferably 5-membered heteroaryl selected from the group consisting
of thienyl, furyl, pyrazolyl, imidazolyl, thiazoiyl and oxazolyl;
where the heteroaryl radicals mentioned may be partially halogenated
and/or may carry 1 to 2 radicals from the group consisting of C1-C6-alkyl
and C1-C4-haloalkyl;
most preferably 5-membered heteroaryl selected from the group consisting of
thienyl, furyl, pyrazolyl and imidazolyl;
where the heteroaryl radicals mentioned may be partially halogenated
and/or may carry 1 to 2 radicals from the group consisting of C1-C6-alkyl
and C1-C4-haloalkyl.
Preference is likewise given to the heteroaroyl-substituted serineamides of the formula
I in which
A is 5- or 6-membered heteroaryl selected from the group consisting of pyrrolyl,

furyl, pyrazolyl, imidazolyl, thiazolyl, oxazolyl, tetrazolyl, pyridyl and pyrimidinyl;
where the heteroaryl radicals mentioned may be partially or fully
halogenated and/or may carry 1 to 3 radicals from the group consisting
of cyano, C1-C6-alkyl, C3-C6-cycloalkyl, C1-C6-haloalkyl, C1-C6-alkoxy, Cr
C6-haloalkoxy and C1-C6-alkoxy-C1-C4alkyl;
particularly preferably 5- or 6-membered heteroaryl selected from the group
consisting of furyl, pyrazolyl, imidazolyl, thiazolyl, oxazolyl and pyridyl;
where the heteroaryl radicals mentioned may be partially or fully
halogenated and/or may carry 1 to 3 radicals from the group consisting
of C1-C6-alkyl, C3-C6-cycloalkyl and C1-C6-haloalkyl;
especially preferably 5-membered heteroaryl selected from the group consisting
of furyl, pyrazolyl, imidazolyl, thiazolyl and oxazolyl;
where the heteroaryl radicals mentioned may be partially halogenated
and/or may carry 1 to 2 radicals from the group consisting of C1-C6-alkyl
and C1-C4-haloalkyl;
most preferably 5-membered heteroaryl selected from the group consisting of
furyl, pyrazolyl and imidazolyl;
where the heteroaryl radicals mentioned may be partially halogenated
and/or may carry 1 to 2 radicals from the group consisting of C.|-C6-alkyl
and C1-C4-haloalkyl.
Preference is likewise given to the heteroaroyl-substituted serineamides of the formula
I in which
A is 5- or 6-membered heteroaryl which is attached via carbon and selected from
the group consisting of Ai to A14 where



where the arrow indicates the point of attachment and
R8 is hydrogen, halogen, C1-C6-alkyl or C1-C6-haloalkyl;
particularly preferably hydrogen, C1-C4-alkyl or C1-C4-haloalkyl;
especially preferably hydrogen or C1-C4-alkyl;
most preferably hydrogen;
R9 is halogen, C1-C6-alkyl, C1-C6-haloalkyI or C1-C6-haloalkoxy;
particularly preferably halogen, C1-C4alkyl or C1-C6-haloalkyl;
especially preferably halogen or C1-C6-haloalkyl;
very preferably C1-C6-haloalkyl;
most preferably C1--C4-haloalkyl;
with utmost preference CF3;
R10 is hydrogen, halogen, C1-C6-alkyl or C1-C6-haloalkyl;
particularly preferably hydrogen, halogen or C1-C4-haloalkyl;
especially preferably hydrogen or halogen;
most preferably hydrogen; and
R11 is hydrogen, C1-C6-alkyl, C3-C6-cycloalkyl, C1-C6-haloalkyl or C1-C6-
alkoxy-C1-C4-alkyl;
particularly preferably C1-C4-alkyl, C3-C6-cycloalkyl, C1-C4-haloalkyl or
C1-C4-alkoxy-C1-C4-alkyl;
especially preferably C1-C4-alkyl or C1-C4-haloalkyl;
most preferably C1-C4-alkyl;
with utmost preference CH3;
particularly preferably A1, A2, A3, A4, A5, A6, A8 or A9;
where R8 to R11 are as defined above;

most preferably A1, A2, A5 or A6;
where R8 to R11 are as defined above.
Preference is likewise given to the heteroaroyl-substituted alanines of the formula I in
which
R1 is hydrogen.
Preference is likewise given to the heteroaroyl-substituted alanines of the formula I in
which
R2 is hydrogen or hydroxyl;
particularly preferably hydrogen.
Preference is likewise given to the heteroaroyl-substituted serineamides of the
formula I in which
R1 is hydrogen; and
R2 is hydrogen or hydroxyl;
particularly preferably hydrogen.
Preference is likewise given to the heteroaroyl-substituted serine amides of the formula
I in which
R3 is C1-C6-alkyl or C1-C6-haloalkyl;
particularly preferably C1-C6-alkyl;
especially preferably C-rC4-alkyl;
most preferably CH3.
Preference is likewise given to the heteroaroyl-substituted serineamides of the formula
I in which
R4 is hydrogen, C1-C6-alkyl, C3-C6-alkenyl, C3-C6-alkynyl, formyl, C1-C6-alkyl-
carbonyl, C2-C6-alkenylcarbonyl, C3-C6-cycloalkylcarbonyl, C1-C6-alkoxycarbonyl,
C1-C6-alkylaminocarbonyl, C1-C6-alkylsulfonylaminocarbonyl, di-(C1-C6-
alkyl)aminocarbonyl, N-(C1-C6-alkoxy)-N-(C1-C6-alkyl)aminocarbonyl, di-(C1-C6-
alkyl)-aminothiocarbonyl, C1-CValkoxylmino-CVCe-alkyl,
where the alkyl, cycloalkyl and alkoxy radicals mentioned may be partially
or fully halogenated and/or may carry one to three of the following groups:
cyano, hydroxyl, C3-C6-cycloalkyl, C1-C4alkoxy, C1-C4-alkylthio, di-(C1--C4-
alkyl)amino, C1-C4-alkylcarbonyl, hydroxycarbonyl, C1-C4-alkoxycarbonyl,
aminocarbonyl, C1--C4-alkylaminocarbonyl, di-(C1-C4-alkyl)aminocarbonyl, or
C1-C4-alkylcarbonyloxy;
phenyl, phenyl-C1-CValkyl, phenylcarbonyl, phenylcarbonyl-C1-C6-alkyl,
phenylsulfonylaminocarbonyl or phenyl-C1-C6-alkylcarbonyl,

where the phenyl radical may be partially or fully halogenated and/or may
carry one to three of the following groups: nitro, cyano, C1-C4-alkyl, C1-C4-
haloalkyl, C1-C4-alkoxy or C1-C4-haloalkoxy; or
S02R7;
particularly preferably hydrogen, C1-C6-alkyl, C3-C6-alkenyl, C3-C6-alkynyl, formyl,
C1-CB-alkylcarbonyl, C2-C6-alkenylcarbonyl, C1-C6-alkoxycarbonyl, C1-C6-alkyl-
sulfonylaminocarbonyl, di-(C1-C6-alkyl)aminocarbonyl, N-(C1-C6-alkoxy)-
N-(C1-C6-alkyl)aminocarbonyl or di-(C1-C6-alkyl)aminothiocarbonyl,
where the alkyl or alkoxy radicals mentioned may be partially or fully
halogenated and/or may carry one to three of the following groups: cyano,
C1-C4-alkoxy, C1--CValkaxycarbonyl, C1-C4-alkylaminocarbonyl, di-(C.|-C4-
alkyl)aminocarbonyl or C1-C4-alkylcarbonyloxy;
phenyl-C1-C6-alkyl, phenylcarbonyl, phenylcarbonyl-C1-C6-alkyl, phenylsulfonyl-
aminocarbonyl or phenyl-C1-C6-alkylcarbonyl,
where the phenyl ring may be partially or fully halogenated and/or may carry
one to three of the following groups: nitro, cyano, C1-C4-alkyl, C1-C4-halo-
alkyl, C1-C4-alkoxy or C1-C4-halooxy; or
S02R7;
especially preferably hydrogen, C.rC6-alkyl, C3-C6-alkenyl, C3-C6-alkynyl, formyl,
C1-C6-alkylcarbonyl, C2-C6-alkenylcarbonyl, C1-C6-alkoxycarbonyl, di-(C1-C6-
alkyl)aminocarbonyl, N-(C1-C6-alkoxy)-N-(C1-C6-alkyl)aminocarbonyl, di-(C1--C6-
alkyl)aminothiocarbonyl, phenyl-CVCe-alkyl, phenylcarbonyl, phenylcarbonyl-Cr
C6-alkyl or phenyl-C1-C6-alkylcarbonyl
where the phenyl ring may be partially or fully halogenated and/or may carry
one to three of the following groups: nitro, cyano, C1-C4-alkyl, C1-C4-
haloalkyl, C1-C4-alkoxy or C1-C4-haloalkoxy; or
S02R7.
Preference is likewise given to the heteroaroyl-substituted serineamides of the formula
I in which
R4 is hydrogen, C1-C6-alkyl, C3-C6-alkenyl, C3-C6-alkynyl, formyl, C1-C6-
alkylcarbonyl, C2-C6-alkenylcarbonyl, C3-C6-cycloalkylcarbonyl, C1-C6-
alkoxycarbonyl, C1-CB-alkylaminocarbonyl, di-(C1-C6-alkyl)aminocarbonyl, N-(Cr
C6-alkoxy)-N-(C1-C6-alkyl)aminocarbonyl, di-(C1-C6-alkyl)aminothiocarbonyl, Cr
C6-alkoxylmino-C1-C5-alkyl,
where the alkyl, cycloalkyl or alkoxy radicals mentioned may be partially or
fully halogenated and/or may carry one to three of the following groups:
cyano, hydroxyl, C3-C6-Cycioalkyl, C1-C4-alkoxy, C1-C4-alkylthio, di-(C1-C4-
alkyl)amino, C1-C4-alkylcarbonyl, hydroxycarbonyl, C1-C4-alkoxycarbonyl,
aminocarbonyl, C1-C4-alkylaminocarbonyl, di-(C1-C4-alkyl)aminocarbonyl or

C1-C4-alkylcarbonyloxy; or
S02R7.
Preference is likewise given to the heteroaroyl-substituted serineamides of the formula
I in which
R4 is hydrogen, C1-C6-alkyl, C3-C6-alkenyl, C3-C6-alkynyl, formyl, C1-C6-alkyl-
carbonyl, C1-C6-alkoxycarbonyl, C1-C6-alkylaminocarbonyl, dKC1-C6-alkyl)-
aminocarbonyl, N-(C1-C6-alkoxy)-N-(C1-C6-alkyl)aminocarbonyl,
where the alkyl and alkoxy radicals mentioned may be partially or fully
halogenated and/or may carry one to three of the following groups: cyano,
C1-C4-alkoxy, C1-C4-alkylaminocarbonyl or di-(C1-C4-alkyl)aminocarbonyl;
phenyl-C1-CValkyl, phenylcarbonyl, phenylcarbonyl-C1-C6-alkyl, phenyl-
aminocarbonyl or N-(C1-C6-alkyl)-N-(phenyl)aminocarbonyl,
where the phenyl ring may be partially or fully halogenated and/or may carry
one to three of the following groups: cyano, C1-C4-alkyl or C1-C4-haloalkyl;
or
S02R?;
particularly preferably hydrogen, formyl, CVC^alkylcarbonyl, C1-C4-alkylamino-
carbonyl, di^Ci^-alkyl)aminocarbonyl, phenylaminocarbonyl, N-(C1-C4-alkyl)-
N-(phenyl)aminocarbonyl, S02CH3, S02CF3 or S02(C6H5).
Preference is likewise given to the heteroaroyl-substituted serineamides of the formula
I in which
R5 is hydrogen or C1-C4-alkyl;
preferably hydrogen or CH3;
especially preferably hydrogen.
Preference is likewise given to the heteroaroyl-substituted serineamides of the formula
I in which
R6 is C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-haloalkyl, C2-C6-haloalkenyl,
C2-C6-haloalkynyl, C1-C6-cyanoalkylt C1-C6-hydroxyalkyl, C2-C6-hydroxyalkenyl,
C2-C6-hydroxyalkynyl, C3-C6-cycloalkyl, C3-C6-cycloalkenyl, 3- to 6-membered
heterocyclyl-C1-C4-alkyl,
where the cycloalkyl, cycloalkenyl or 3- to 6-membered heterocycyl radicals
mentioned above may be partially or fully halogenated and/or may carry
one to three radicals from the group consisting of oxo, C1-C6-alkyl, C1-C6-
haloalkyl, hydroxycarbonyl and C1-C6-alkoxycarbonyl,
C1-C6-alkoxy-C1-C4-alkyl, C1-C6-haloalkoxy-C1-C4-alkyl, C1-C6-alkoxy-C1-C4-
alkoxy-C1-C4-alkyl, C1-C6-alkylthio-C1-C4-alkyl, C1-CB-alkylsulfonylamino-C1-C4-
alkyl, hydroxycarbonyl, C-pCe-alkoxycarbonyl, hydroxycarbonyl-C1-C4-alkyl, Cr
C6-alkoxycarbonyl-C1-C4-alkyl, C1-C6-haloalkoxycarbonyl-C1-C4-alkyl, C-,-C6-

alkylcarbonyloxy-C1-C4-alkyl, C1-C6-alkylcarbonylamino-C1-C4-alkyl, di(C1-C6-
alkyl)carbonylamino-C1-C4-alkyl, di(C1-C6-alkyl)aminocarbonyl-amino-C1-C4-alkyl,
[(C1-C6-alkyl)aminocarbonyHamino-Ci^-alkyl, [di(C1-C6-alkyl)aminocarbonyl-
oxy]-C1-C4-alkyl, {di[di(C1-C6-alkyl)amino]carbonyloxy}-C1-C4-alkyl, formylamino-
C1-C4-alkyl,
phenyl-C1-C4-alkyl, phenyl-C2-C4-alkenyl, phenyl-C2-C4-alkynyl, phenyl-C1-C4-
haloalkyl, phenyl-C2-C4-haloalkenyl, phenyl-C1-C4-hydroxyalkyl, phenyloxy-C1-C4-
alkyl, phenylthio-C1-C4-alkyl, phenylsulfinyl-C1-C4alkyl, phenylsulfonyl-C1-C4-
alkyl,
heteroaryl-C1-C4-alkyl, heteroaryl-C1-C4-hydroxyalkyl, heteroaryloxy-C1-C4-alkyl,
heteroarylthio-C1-C4-alkyl, heteroarylsulfinyl-C1-C4-alkyl or heteroarylsulfonyl-Cr
C4-alkyl,
where the phenyl and heteroaryl radicals mentioned above may be partially
or fully halogenated and/or may carry one to three radicals from the group
consisting of cyano, nitro, C1-C6-alkyl, C1-C6-haloalkyl, hydroxy, C^-Ce;-
alkoxy, C1-C6-haloalkoxy, hydroxycarbonyl, C1-C6-alkoxycarbonyl,
hydroxycarbonyl-C1-C6-alkoxy, C1-C6-alkylsulfonylamino and C1-C6-
haloalkylsulfonylamino;
particularly preferably C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-haloalkyl,
C2-C6-haloalkenyl, C1-C6-hydroxyalkyl, C1-C6-alkoxy-C1-C4-alkyl, crC6-
haloalkoxy-C1-C4-alkyl, hydroxycarbonyl-C1-C4-alkyl, C1-CB-alkoxycarbonyl-
CVCValkyl, C^Ce-alkylcarbonyloxy-C1-C4alkyl, C1-C6-alkylcarbonylamino-C1-C4-
alkyl, [di(C1-C6-alkyl)aminocarbonyloxy]-C1-C4-alkyl, {di[di(C1-C6-alkyl)amino]-
carbonyloxy}-C1-C4-alkyl, forrnylamino-C1-C4-alkyl;
phenyl-C1-C4-alkyl, phenyl-C2-C4-alkenyl, phenyl-C2-C4-alkynyl, phenyl-C^Cr
haloalkyl, phenyl-C2-C4-haloa!kenyl, phenyl-C1-C4-hydroxyalkyl, phenyloxy-C1-C4-
alkyl, phenylthio-C1-C4-alkyl, phenylsulfinyl-C1-C4-alkyl or phenylsulfonyl-C1-C4-
alkyl,
where the phenyl radicals mentioned above may be partially or fully
halogenated and/or may carry one to three radicals from the group
consisting of C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, hydroxycarbonyl,
C1-C6-alkoxycarbonyl, C1-C6-alkylsulfonylamino and C1-C6-haloalkyl-
sulfonylamino;
especially preferably C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-CB-haloalkyl,
C2-C5-haloalkenyl, C1-C6-hydroxyalkyl, hydroxycarbonyl-C1-C4-alkyl, C1-C6-
alkoxycarbonyl-C1-C4-alkyl, [di(C1-C6-alkyl)aminocarbonyloxy]-C1-C4-alkyl,
{di[di(C1-C6-alkyl)amino]carbonyloxy}-C1-C4-alkyl, formylamino-C1-C4-alkyl;
phenyl-C1-C4-alkyl, phenyl-C2-C4-alkenyl, phenyl-C1-C4-hydroxyalkyl or
phenylthio-C1-C4-alkyl;

most preferably C1-C6-alkyl, C2-C6-alkenyl, C1-C6-haloalkyl, C2-C6-haloalkenyl,
C1-C6-hydroxyalkyl, hydroxycarbonyl-C1-C4-alkyl, formylamino-C1-C4-alkyl,
phenyl-C1-C6-alkyl or phenyl-C1-C4-hydroxyalkyl.
Preference is likewise given to the heteroaroyl-substituted serineamides of the formula
I in which
R6 is C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-haloalkyl, C2-C6-haloalkenyl,
C2-C6-haloalkynyl, C1-C6-cyanoalkyl, C1-C6-hydroxyalkyl, C2-C6-hydroxyalkenyl,
C2-C6-hydroxyalkynyl, C3-C6-cycloalkyl, C3-C6-cycloalkenyl, 3-to 6-membered
heterocyclyl,
where the cycloalkyl, cycloalkenyl or 3- to 6-membered heterocycyl radicals
mentioned above may be partially or fully halogenated and/or may carry
one to three radicals from the group consisting of oxo, C1-C6-alkyl, C1-C6-
haloalkyl, hydroxycarbonyl and C1-C8-alkoxycarbonyl,
C1-C6-alkoxy-C1-C4-alkyl, C1-C6-haloalkoxy-C1-C6-alkyl, C1-C6-alkoxy-C1-C4-
alkoxy-C1-C4-alkyl, C1-C6-alkylthio-C1-C6-alkyl, C1-C6-a!kylsulfonylamino-C1-C6-
alkyl, hydroxycarbonyl, C1-C6-alkoxycarbonyl, hydroxycarbonyl-C1-C4-alkyl, Cr
C6-alkoxycarbonyl-C1-C4-alkyl, C1-C6-haloalkoxycarbonyl-C1-C6-alkyl, C1-C6-
alkylcarbonyloxy-C1-C6-alkyl, C1-C6-alkylcarbonylamino-C1-C6-alkyl, di(C1-C6-
alkyl)carbonylamino-Ci-d-alkyl, di(C1-C6-alkyl)aminocarbonylamino-C1-C4-alkyl,
[(C1-C6-alkyl)aminocarbonyl]amino-Ci-d-alkyl, [di(C1-C6-alkyl)aminocarbonyl-
oxy]-C1-C4-alkyl, formylamino-C1-C4-alkyl,
phenyl-C1-C6-alkyl, phenyl-C2-C4-alkenyl, phenyl-C2-C4-alkynyl, phenyl-C1-C4-
haloalkyl, phenyl-C1-C6-haloalkenyl, phenyl-C1-C4-hydroxyalkyl, phenyloxy-C1-C6-
alkyl, phenylthio-C1-C6-alkyl, phenylsulfinyl-C1-C6-alkyl, phenylsulfonyl-C1-C4-
alkyl,
heteroaryl-C1-C4-alkyl, heteroaryl-C1-C4-hydroxyalkyl, heteroaryloxy-C1-C4-alkyl,
heteroarylthio-C1-C6-alkyl, heteroarylsulfinyl-Ci-d-alkyl or heteroarylsulfonyl-d-
d-alkyl,
where the phenyl and heteroaryl radicals mentioned above may be partially
or fully halogenated and/or may carry one to three radicals from the group
consisting of cyano, nitro, C1-C6-alkyl, C1-C6-haloalkyl, hydroxy, C1-C6-
alkoxy, C1-C6-haloalkoxy, hydroxycarbonyl, C1-C6-alkoxycarbonyl,
hydroxycarbonyl-C1-C6-alkoxy, C1-C6-alkylsulfonylamino and C1-C6-
haloalkylsulfonylamino;
particularly preferably C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-haloalkyl,
C2-Cs-haloalkenyl, C1--C6-hydroxyalkyl, 3-to 6-membered heterocyclyl, C1-C6-
alkoxy-C1-C4-alkyl, C1-C6-alkoxy-C1-C6-alkoxy-C1-C6-alkyl, C1-C6-haloalkoxy-
C1-C6-alkyl, hydroxycarbonyl-C1-C4-alkyl, C1-C6-alkoxycarbonyl-C1-C6-alkyl,
CT-Ce-alkylcarbonyloxy-C1-C6-alkyl, C1-C6-alkylcarbonylamino-C-rd-alkyl,
[di(C1-C6-a!kyl)aminocarbonyloxy]C1-C6-alkyl, formylamino-C1-C4-alkyl;

phenyl-C1-C4-alkyl, phenyl-C2-C4-alkenyl, phenyl-C2-C4-alkynyl, phenyl-C1-C4-
haloalkyl, phenyl-C2-C4-haloalkenyl, phenyl-C1-C4-hyciroxyalkyl, phenyloxy-CVCr
alkyl, phenylthio-C1-C4-alkyl, phenylsulfinyl-C-rCU-alkyl or phenylsuIfonyl-C1-C4-
alkyl,
where the phenyl radicals mentioned above may be partially or fully
halogenated and/or may carry one to three radicals from the group
consisting of C1-C6-a!kyl, C1-C6-haloalkyl, C1-C6-alkoxy, hydroxycarbonyl,
C1-C6-alkoxycarbonyl, C1-C6-alkylsulfonylamino and C1-CB-haloalkyl-
sulfonylamino;
especially preferably C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-haloalkyl,
C2-C6-haloalkenyl, CVCB-hydroxyalkyl, 3- to 6-membered heterocyclyl, C1-C6-
alkoxy-C1-C4-alkyl, CVCe-alkoxy-C1-CXralkoxy-C1-CA-alkyI, hydroxycarbonyl-
C1-C4-alkyl, (VCe-alkoxycarbonyl-C-rCValkyl, [di(C1-C6-alkyl)aminocarbonyl-
oxyJC1-C4alkyl, formylamino-C1-C4-alkyl;
phenyl-C1-C4-alkyl, phenyl-C2-C4-alkenyl, phenyl-C1-C4-hydroxyalkyl or
phenylthio-C1-C4-alkyl;
most preferably C1-C6-alkyl, C2-C6-alkenyl, C1-C6-haloalkyl, C2-C6-haloalkenyl,
C1-C6-hydroxyalkyl, 3- to 6-membered heterocyclyl, C1-C6-alkoxy-C1-C4-alkyl,
C1-C6-alkoxy-C1-C4-alkoxy-C1-C4-alkyl, hydroxycarbonyl-C1-C4-alkyl,
formylamino-C-rCU-alkyl, phenyl-C1-CA-alkyI or phenyl-C1-C4-hydroxyalkyl.
Preference is likewise given to the heteroaroyl-substituted serineamides of the formula
I in which
R7 is C^CValkyl, C1-C6-haloalkyl or phenyl,
where the phenyl radical may be partially or partially halogenated and/or
may be substituted by C1-C4-alkyl;
particularly preferably C1-C4-alkyl, C1-C4-haloalkyl or phenyl;
especially preferably methyl, trifluoromethyl or phenyl.
Particular preference is given to the heteroaroyl-substituted serineamides of the
formula I in which
A is 5- or 6-membered heteroaryl selected from the group consisting of thienyl,
furyl, pyrazolyl, imidazolyl, thiazolyl, oxazolyl and pyridyl;
where the heteroaryl radicals mentioned may be partially or fully
halogenated and/or may carry 1 to 3 radicals from the group consisting of
C1-C6-alkyl, C3-C6-cycloalkyl and C-pCVhaloalkyl;

R1 and R2 are hydrogen;
R3 is C1-C4alkyl,
particularly preferably CH3;
R4 is hydrogen, formyl, C1-C4-alkylcarbonyl, C1-C4-alkylaminocarbonyl, di-(C1-C4-
alkyl)aminocarbonyl, phenylaminocarbonyl, N-(C1-C4-alkyl)-N-
(phenyl)aminocarbonyl, S02CH3, S02CF3or S02(C6H5); and
R5 is hydrogen; and
R6 is C1-C6-alkyl, C2-C6-alkenyl, C1-C6-haloalkyl, C2-C6-haloalkenyl, C1-C6-
hydroxyalkyl, C1-C6-alkoxy-C-rC^alkyl, C1-C6-alkoxy-C1-C4alkoxy-C1-C4alkyl, 3-
to 6-membered heterocyclyl, hydroxycarbonyl-C1-C4-alkyl, phenyl-C1-C4-alkyl,
phenyl-C1-C4-hydroxyalkyl.
Most preference is given to the compounds of the formula I.a (corresponds to formula I
where A = A-1 where R8 = H, R9 = CF3, R1, R2 and R6 = H; R3 = CH3), in particular to
the compounds of the formulae l.a.1 to l.a.138 of Table 1, where the definitions of the
variables A and R1 to R6 are of particular importance for the compounds according to
the invention not only in combination with one another, but in each case also on their
own.










Most preference is given to the compounds of the formula l.b, in particular to the
compounds of the formulae l.b.1 to l.b. 138, which differ from the corresponding
compounds of the formulae l.a.1 to l.a.138 in that A is A1 where RB = CH3 and R9 =
CF3.

Most preference is given to the compounds of the formula l.c, in particular to the
compounds of the formulae l.c. 1 to l.c. 138, which differ from the corresponding
compounds of the formulae l.a.1 to l.a.138 in that A is A2 where R8 = H and R9 =CF3.

Most preference is given to the compounds of the formula l.d, in particular to the
compounds of the formulae l.d.1 to l.d.138, which differ from the corresponding
compounds of the formulae l.a.1 to l.a.138 in that A is A3 where RB = H and R9 = CF3.

Most preference is given to the compounds of the formula I.e. in particular to the
compounds of the formulae l.e.1 to l.e.138, which differ frorti the corresponding
compounds of the formulae l.e.1 to l.e.138 in that A is A3 where R8 = CH3 and R9 =
CF3.


Most preference is given to the compounds of the formula l.f, in particular to the
compounds of the formulae l.f.1 to l.f.138, which differ from the corresponding
compounds of the formulae l.a.1 to I.a.138 in that A is A4 where R8 = H and R9 = CF3.

Most preference is given to the compounds of the formula l.g, in particular to the
compounds of the formulae l.g.1 to l.g.138, which differ from the corresponding
compounds of the formulae l.a.1 to I.a.138 in that A is A5 where R11 = H, R9 = CF3 and
R10 = H.

Most preference is given to the compounds of the formula I.h, in particular to the
compounds of the formulae l.h.1 to I.h.138, which differ from the corresponding
compounds of the formulae l.a.1 to l.a.138 in that A is A5 where R11 = CH3, Ra = CF3
and R10 = H.

Most preference is given to the compounds of the formula l.j, in particular to the
compounds of the formulae l.j.1 to l.j.138, which differ from the corresponding
compounds of the formulae l.a.1 to I.a.138 in that A is A8 where R8 = H and R9 = CF3.


Most preference is given to the compounds of the formula l.k, in particular to the
compounds of the formulae l.k.1 to l.k. 138, which differ from the corresponding
compounds of the formulae l.a.1 to l.a.138 in that A is A8 where R8 = CH3 and R9 =
CF3.

The heteroaroyl-substituted serineamides of the formula I can be obtalned by different
routes, for example by the following processes:
Process A
Serine derivatives of the formula V are initially reacted with heteroaryl acids/heteroaryl
acid derivatives of the formula IV to give the corresponding heteroaroyl derivatives of
the formula III which are then reacted with amines of the formula II to give the desired
heteroaroyl-substituted serineamides of the formula I:

L1 is a nucleophilically replaceable leaving group, for example hydroxyl or C1-C6-alkoxy.
L2 is a nucleophilically replaceable leaving group, for example hydroxyl, halogen,
C1-C6-alkylcarbonyl, C1-C6-alkoxycarbonyl, C1-C4alkylsulfonyf, phosphoryl or isoureyl.
The reaction of the serine derivatives of the formula V with heteroaryl acids/heteroaryl
acid derivatives of the formula IV where L2 is hydroxyl to give heteroaroyl derivatives of
the formula III is carried out in the presence of an activating reagent and a base,

usually at temperatures of from 0°C to the boiling point of the reaction mixture,
preferably from 0°C to 110°C, particularly preferably at room temperature, in an inert
organic solvent [cf. Bergmann, E. D.; et al., J Chem Soc 1951, 2673; Zhdankin, V. V.;
et al., Tetrahedron Lett. 2000, 41 (28), 5299-5302; Martin, S. F. et al., Tetrahedron
Lett.1998, 39 (12), 1517-1520; Jursic, B. S. et al., Synth Commun 2001, 31 (4),
555-564; Albrecht, M. et al., Synthesis 2001, (3), 468-472; Yadav, L. D. S. et al., Indian
J. Chem B. 41(3), 593-595(2002); Clark, J. E. et al., Synthesis (10), 891-894 (1991)].
Suitable activating reagents are condensing agents, such as, for example, polystyrene-
bound dicyclohexylcarbodiimide, diisopropylcarbodiimide, carbonyldiimidazole,
chloroformic esters, such as methyl chloroformate, ethyl chloroformate, isopropyl
chloroformate, isobutyl chloroformate, sec-butyl chloroformate or allyl chloroformate,
pivaloyl chloride, polyphosphoric acid, propanephosphonic anhydride, bis(2-oxo-
3-oxazolidinyl)phosphoryl chloride (BOPCI) or sulfonyl chlorides, such as methane-
sulfonyl chloride, toluenesulfonyl chloride or benzenesulfonyl chloride.
Suitable solvents are aliphatic hydrocarbons, such as pentane, hexane, cyclohexane
and mixtures of C5-CB-alkanes, aromatic hydrocarbons, such as benzene, toluene, o-,
m- and p-xylene, halogenated hydrocarbons, such as methylene chloride, chloroform
and chlorobenzene, ethers, such as diethyl ether, diisopropyl ether, tert-butyl methyl
ether, dioxane, anisole and tetrahydrofuran (THF), nitriles, such as acetonitrile and
propionitrile, ketones, such as acetone, methyl ethyl ketone, diethyl ketone and tert-
butyl methyl ketone, and also dimethyl sulfoxide, dimethylformamide (DMF), dimethyl-
acetamide (DMA) and N-methylpyrrolidone (NMP), or else in water; particular
preference is given to methylene chloride, THF and water.
It is also possible to use mixtures of the solvents mentioned.
Suitable bases are, in general, inorganic compounds, such as alkali metal and alkaline
earth metal hydroxides, such as lithium hydroxide, sodium hydroxide, potassium
hydroxide and calcium hydroxide, alkali metal and alkaline earth metal oxides, such as
lithium oxide, sodium oxide, calcium oxide and magnesium oxide, alkali metal and
alkaline earth metal hydrides, such as lithium hydride, sodium hydride, potassium
hydride and calcium hydride, alkali metal and alkaline earth metal carbonates, such as
lithium carbonate, potassium carbonate and calcium carbonate, and also alkali metal
bicarbonates, such as sodium bicarbonate, moreover organic bases, for example
tertiary amines, such as trimethylamine, triethylamine, diisopropylethylamine, N-methyl-
morpholine and N-methylpiperidine, pyridine, substituted pyridines, such as collidine,
lutidine and 4-dimethylaminopyridine, and also bicyclic amines. Particular preference is
given to sodium hydroxide, triethylamine and pyridine.
The bases are generally employed in equimolar amounts. However, they can also be

used in excess or, if appropriate, as solvent.
The starting materials are generally reacted with one another in equimolar amounts. It
may be advantageous to use an excess of IV, based on V.
The reaction mixtures are worked up in a customary manner, for example by mixing
with water, separating the phases and, if appropriate, chromatographic purification of
the crude products. Some of the intermediates and end products are obtalned in the
form of viscous oils which are purified or freed from volatile components under reduced
pressure and at moderately elevated temperature. If the intermediates and end
products are obtalned as solids, purification can also be carried out by recrystallization
or digestion.
The reaction of the serine derivatives of the formula V with heteroaryl acids/heteroaryl
acid derivatives of the formula IV where L2 is halogen, CVCe-alkylcarbonyl, CVC6-
alkoxycarbonyl, C1-C4-alkylsulfonyl, phosphoryl or isoureyl to give heteroaroyl
derivatives of the formula III is carried out in the presence of a base, usually at
temperatures of from 0°C to the boiling point of the reaction mixture, preferably at from
0°C to 100°C, particularly preferably at room temperature, in an inert organic solvent
[cf. Bergmann, E. D.; et al., J Chem Soc 1951, 2673; Zhdankin, V. V.; et al.,
Tetrahedron Lett. 2000, 41 (28), 5299-5302; Martin, S. F. et al., Tetrahedron Lett. 1998,
39 (12), 1517-1520; Jursic, B. S. et al., Synth Commun 2001, 31 (4), 555-564;
Albrecht, M. et al., Synthesis 2001, (3), 468-472; Yadav, L. D. S. et al., Indian J. Chem
B. 41(3), 593-595(2002); Clark, J. E. et al., Synthesis (10), 891-894 (1991)].
Suitable solvents are aliphatic hydrocarbons, such as pentane, hexane, cyclohexane
and mixtures of C5-C8-alkanes, aromatic hydrocarbons, such as benzene, toluene, o-,
m- and p-xylene, halogenated hydrocarbons, such as methylene chloride, chloroform
and chiorobenzene, ethers, such as diethyl ether, diisopropyl ether, tert-butyl methyl
ether, dioxane, anisole and tetrahydrofuran (THF), nitriles, such as acetonitrile and
propionitrile, ketones, such as acetone, methyl ethyl ketone, diethyl ketone and tert-
butyl methyl ketone, and also dimethyl sulfoxide, dimethylformamide (DMF),
dimethylacetamide (DMA) and N-methylpyrrolidone (NMP), or else in water; particular
preference is given to methylene chloride, THF and water.
It is also possible to use mixtures of the solvents mentioned.
Suitable bases are, in general, inorganic compounds, such as alkali metal and alkaline
earth metal hydroxides, such as lithium hydroxide, sodium hydroxide, potassium
hydroxide and calcium hydroxide, alkali metal and alkaline earth metal oxides, such as
lithium oxide, sodium oxide, calcium oxide and magnesium oxide, alkali metal and
alkaline earth metal hydrides, such as lithium hydride, sodium hydride, potassium

hydride and calcium hydride, alkali metal and alkaline earth metal carbonates, such as
lithium carbonate, potassium carbonate and calcium carbonate, and also alkali metal
bicarbonates, such as sodium bicarbonate, moreover organic bases, for example
tertiary amines, such as trimethylamine, triethylamine, diisopropylethylamine, N-methyl-
morpholine and N-methylpiperidine, pyridine, substituted pyridines, such as collidine,
lutidine and 4-dimethylaminopyridine, and also bicyclic amines. Particular preference is
given to sodium hydroxide, triethylamine and pyridine.
The bases are generally employed in equimolar amounts. However, they can also be
used in excess or, if appropriate, as solvent.
The starting materials are generally reacted with one another in equimolar amounts. It
may be advantageous to use an excess of IV, based on V.
Work-up and isolation of the products can be carried out in a manner known per se.
It is, of course, also possible to initially react the serine derivatives of the formula V in
an analogous manner with amines of the formula II to give the corresponding amides
which are then reacted with heteroaryl acids/heteroaryl acid derivatives of the formula
IV to give the desired heteroaroyl-substituted serineamides of the formula I.
The serine derivatives of the formula V (for example where L1 = hydroxyl or C1-C6-
alkoxy) required for preparing the heteroaroyl derivatives of the formula III are known
from the literature, even in enantiomerically and diastereomerically pure form, or they
can be prepared in accordance with the literature cited:
- by condensation of glycine enolate equivalents with aldehydes or ketones [Blaser,
D. et al., Liebigs Ann. Chem. 10, 1067-1078 (1991); Seethaler, T. et al., Liebigs
Ann. Chem. 1, 11-17 (1991); Weltenauer, G. et al., Gazz. Chim. Ital. 81,162 (1951);
Dalia Croce, P. et al., Heterocycles 52(3), 1337-1344 (2000); Van der Werf, A. W. et
al., J. Chem. Soc. Chem. Commun. 100, 682-683 (1991); Caddick, S. et al.,
Tetrahedron 57 (30), 6615-6626 (2001); Owa, T. et al., Chem. Lett. 1, 83-86 (1988);
Alker, D. et al., Tetrahedron 54 (22), 6089-6098 (1998); Rousseau, J. F. et al., J.
Org. Chem. 63 (8), 2731-2737 (1998); Saeed, A. et al., Tetrahedron 48 (12), 2507-
2514 (1992); Dong, L. et al., J. Org. Chem. 67 (14), 4759-4770 (2002)].
- by aminohydroxylation of acrylic acid derivatives [Zhang, H. X. et al., Tetrahedron
Asymmetr. 11(16), 3439-3447 (2000); Fokin, V. V. et al., Angew. Chem. Int. Edit.
40(18), 3455 (2001); Sugiyama, H. et al., Tetrahedron Lett. 43(19), 3489-3492
(2002); Bushey, M. L. et al., J. Org. Chem. 64(9), 2984-2985 (1999); Raatz, D. et
al., Synlett (12), 1907-1910 (1999)].
- by nucleophilic substitution of leaving groups in the 2-position of 3-hydroxypropionic

acid derivatives [Owa, T. et al., Chem. Lett. (11), 1873-1874 (1988); Boger, D. L et
al., J. Org. Chem. 57(16), 4331-4333 (1992); Alcalde, B. et a!., Tetrahedron Lett.
36(30), 5417-5420(1995)].
- by condensation of aldehydes with nucleophiles with formation of oxazolines and
subsequent hydrolysis [Evans, D. A. et al., Angew. Chem. Int. Edit. 40(10), 1884-
1888 (2001); Ito, Y. et al., Tetrahedron Lett. 26(47), 5781-5784 (1985); Togni, A. et
al., J. Organomet. Chem. 381(1), C21-5 (1990); Longmire, J. M. et al.,
Organometallics 17(20), 4374-4379 (1998); Suga, H. et al., J. Org. Chem. 58(26),
7397-7405(1993)].
- by oxidative cyclization of 2-acylamino-propionic acid derivatives to give oxazoiines
and subsequent hydrolysis (JP10101655).
- by Diels-Alder reactions of vinylimines with aldehydes to give the oxazines and
subsequent hydrolysis [Bongini, A. et al., Tetrahedron Asym. 12(3), 439-454
(2001)].
The heteroaryl acids/heteroaryl acid derivatives of the formula IV required for preparing
the heteroaroyl derivatives of the formula III are commercially avallable or can be
prepared analogously to procedures known from the literature from the corresponding
halide by a Grignard reaction [for example A. Mannschuk et al., Angew. Chem. 100,
299(1988)].
The reaction of the heteroaroyl derivatives of the formula III where L1 = hydroxyl or
salts thereof with amines of the formula II to give the desired heteroaroyl-substituted
serineamides of the formula I is carried out in the presence of an activating reagent
and, if appropriate, in the presence of a base, usually at temperatures of from 0°C to
the boiling point of the reaction mixture, preferably at from 0°C to 100°C, particularly
preferably at room temperature, in an inert organic solvent [cf. Perich, J. W., Johns, R.
B., J. Org. Chem. 53 (17), 4103-4105 (1988); Somlal, C. et al., Synthesis (3), 285-287
(1992); Gupta, A. et al., J. Chem. Soc. Perkin Trans. 2, 1911 (1990); Guan et al., J.
Comb. Chem. 2, 297 (2000)].
Suitable activating reagents are condensing agents, such as, for example, polystyrene-
bound dicyclohexylcarbodiimide, diisopropylcarbodiimide, carbonyldiimidazole,
chloroformic esters, such as methyl chloroformate, ethyl chloroformate, isopropyl
chloroformate, isobutyl chloroformate, sec-butyl chloroformate or allyl chloroformate,
pivaloyl chloride, polyphosphoric acid, propanephosphonic anhydride, bis(2-oxo-
3-oxazolidinyl)phosphoryl chloride (BOPCI) or sulfonyl chlorides, such as methane-
sulfonyl chloride, toluenesulfonyl chloride or benzenesulfonyl chloride.

Suitable solvents are aliphatic hydrocarbons, such as pentane, hexane, cyclohexane
and mixtures of C5-C8-alkanes, aromatic hydrocarbons, such as benzene, toluene, o-,
m- and p-xylene, halogenated hydrocarbons, such as methylene chloride, chloroform
and chlorobenzene, ethers, such as diethyl ether, diisopropyl ether, tert-butyl methyl
ether, dioxane, anisole and tetrahydrofuran (THF), nitriles, such as acetonitrile and
propionitrile, ketones, such as acetone, methyl ethyl ketone, diethyl ketone and tert-
butyl methyl ketone, alcohols, such as methanol, ethanol, n-propanol, isopropanol,
n-butanol and tert-butanol, and also dimethyl sulfoxide, dimethylformamide (DMF),
dimethylacetamide (DMA) and N-methylpyrrolidone (NMP), or else in water; particular
preference is given to methylene chloride, THF, methanol, ethanol and water.
It is also possible to use mixtures of the solvents mentioned.
Suitable bases are, in general, inorganic compounds, such as alkali metal and alkaline
earth metal hydroxides, such as lithium hydroxide, sodium hydroxide, potassium
hydroxide and calcium hydroxide, alkali metal and alkaline earth metal oxides, such as
lithium oxide, sodium oxide, calcium oxide and magnesium oxide, alkali metal and
alkaline earth metal hydrides, such as lithium hydride, sodium hydride, potassium
hydride and calcium hydride, alkali metal and alkaline earth metal carbonates, such as
lithium carbonate, potassium carbonate and calcium carbonate, and also alkali metal
bicarbonates, such as sodium bicarbonate, moreover organic bases, for example
tertiary amines, such as trimethylamine, thethylamine, diisopropylethylamine, N-methyl-
morpholine and N-methylpiperidine, pyridine, substituted pyridines, such as collidine,
lutidine and 4-dimethylaminopyridine, and also bicyclic amines. Particular preference is
given to sodium hydroxide, triethylamine, ethyldiisopropylamine, N-methylmorpholine
and pyridine.
The bases are generally employed in catalytic amounts; however, they can also be
employed in equimolar amounts, in excess or, if appropriate, as solvent.
The starting materials are generally reacted with one another in equimolar amounts. It
may be advantageous to use an excess of II, based on III.
Work-up and isolation of the products can be carried out in a manner known per se.
The reaction of the heteroaroyl derivatives of the formula III where L1 = C1-C6-alkoxy
with amines of the formula II to give the desired heteroaroyl-substituted serineamides
of the formula I is usually carried out at temperatures of from 0°C to the boiling point of
the reaction mixture, preferably from 0°C to 100°C, particularly preferably at room
temperature, in an inert organic solvent, if appropriate in the presence of a base [cf.

Kawahata, N. H. et a!., Tetrahedron Lett. 43 (40), 7221-7223 (2002); Takahashi, K. et
al., J. Org. Chem. 50 (18), 3414-3415 (1985); Lee, Y. et al., J. Am. Chem. Soc. 121
(36), 8407-8408(1999)].
Suitable solvents are aliphatic hydrocarbons, such as pentane, hexane, cydohexane
and mixtures of C5-C8-alkanes, aromatic hydrocarbons, such as benzene, toluene, o-,
m- and p-xylene, halogenated hydrocarbons, such as methylene chloride, chloroform
and chlorobenzene, ethers, such as diethyl ether, diisopropyl ether, tert-butyl methyl
ether, dioxane, anisole and tetrahydrofuran (THF), nitriles, such as acetonitriie and
propionitrile, ketones, such as acetone, methyl ethyl ketone, diethyl ketone and tert-
butyl methyl ketone, alcohols, such as methanol, ethanol, n-propanol, isopropanol,
n-butanol and tert-butanol, and also dimethyl sulfoxide, dimethylformamide (DMF),
dimethylacetamide (DMA) and N-methylpyrrolidone (NMP), or else in water; particular
preference is given to methylene chloride, THF, methanol, ethanol and water.
It is also possible to use mixtures of the solvents mentioned.
If appropriate, the reaction can be carried out in the presence of a base. Suitable bases
are, in general, inorganic compounds, such as alkali metal and alkaline earth metal
hydroxides, such as lithium hydroxide, sodium hydroxide, potassium hydroxide and
calcium hydroxide, alkali metal and alkaline earth metal oxides, such as lithium oxide,
sodium oxide, calcium oxide and magnesium oxide, alkali metal and alkaline earth
metal hydrides, such as lithium hydride, sodium hydride, potassium hydride and
calcium hydride, alkali metal and alkaline earth metal carbonates, such as lithium
carbonate, potassium carbonate and calcium carbonate, and also alkali metal
bicarbonates, such as sodium bicarbonate, moreover organic bases, for example
tertiary amines, such as trimethylamine, triethylamine, diisopropylethylamine, N-methyl-
morpholine and N-methylpiperidine, pyridine, substituted pyridines, such as collidine,
lutidine and 4-dimethylaminopyridine, and also bicyclic amines. Particular preference is
given to sodium hydroxide, triethylamine, ethyldiisopropylamine, N-methylmorpholine
and pyridine.
The bases are generally employed in catalytic amounts; however, they can also be
employed in equimolar amounts, in excess or, if appropriate, as solvent.
The starting materials are generally reacted with one another in equimolar amounts. It
may be advantageous to use an excess of II, based on 111.
Work-up and isolation of the products can be carried out in a manner known per se.
The amines of the formula II required for preparing the heteroaroyl-substituted
serineamides of the formula I are commercially avallable.

Process B
Heteroaroyl derivatives of the formula III where R4 = hydrogen can also be obtalned by
condensing acylated glycine derivatives of the formula VIII where the acyl group may
be a cleavable protective group, such as benzyloxycarbonyl (cf. Villa where E = benzyl)
or tert-butyloxycarbonyl (cf. Villa where I = tert-butyl), with carbonyl compounds VII to
give the corresponding aldol products VI. The protective group is then cleaved and the
resulting serine derivative of the formula V where R4= hydrogen is acylated using
heteroaryl acid derivatives of the formula IV.
Analogously, it is also possible to convert an acylated glycine derivative of the formula
VIII where the acyl group is a substituted heteroaroyl radical (cf. Vlllb) in the presence
of a base with a carbonyl compound VII into the heteroaroyl derivative III where R4 =
hydrogen:

L1 is a nucleophilically displaceable leaving group, for example hydroxyl or C1-C6-
alkoxy.
L2 is a nucleophilically displaceable leaving group, for example hydroxyl, halogen,
C1-C6-alkylcarbonyl, C1-C6-alkoxycarbonyl, C1-C4-alkylsulfonyl, phosphoryl or isoureyl.
The reaction of the glycine derivatives VIII with carbonyl compounds VII to give the
corresponding aldol product VI or heteroaroyl derivative III where R4 = hydrogen is
usually carried out at temperatures of from -100°C to the boiling point of the reaction
mixture, preferably at from -80°C to 20°C, particularly preferably at from -80°C to

-20°C, in an inert organic solvent in the presence of a base [cf. J.-F. Rousseau et al., J.
Org. Chem. 63, 2731-2737 (1998)].
Suitable solvents are aliphatic hydrocarbons, such as pentane, hexane, cyclohexane
and mixtures of C5-C8-alkanes, aromatic hydrocarbons, such as toluene, o-, m- and
p-xylene, ethers, such as diethyl ether, diisopropyl ether, tert-butyl methyl ether,
dioxane, anisole and tetrahydrofuran, and also dimethyl sulfoxide, dimethylformamide
and dimethylacetamide, particularly preferably diethyl ether, dioxane and
tetrahydrofuran.
It is also possible to use mixtures of the solvents mentioned.
Suitable bases are, in general, inorganic compounds, such as alkali metal and alkaline
earth metal hydrides, such as lithium hydride, sodium hydride, potassium hydride and
calcium hydride, alkali metal azides, such as lithium diisopropylamide, lithium
hexamethyldisilazide, organometallic compounds, in particular alkali metal alkyls, such
as methyllithium, butyllithium and phenyllithium, and also alkali metal and alkaline earth
metal alkoxides, such as sodium methoxide, sodium ethoxide, potassium ethoxide,
potassium tert-butoxide, potassium tert-pentoxide and dimethoxymagnesium, moreover
organic bases, for example tertiary amines, such as trimethylamine, triethylamine,
diisopropylethylamine and N-methylpiperidine, pyridine, substituted pyridines, such as
collidine, lutidine and 4-dimethylaminopyridine, and also bicyclic amines. Particular
preference is given to sodium hydride, lithium hexamethyldisilazide and lithium
diisopropylamide.
The bases are generally employed in equimolar amounts; however, they can also be
used catalytically, in excess or, if appropriate, as solvents.
The starting materials are generally reacted with one another in equimolar amounts. It
may be advantageous to employ an excess of base and/or carbonyl compounds VII,
based on the glycine derivatives VIII.
Work-up and isolation of the products can be carried out in the manner known per se.
The glycine derivatives of the formula VIII required for preparing the compounds I are
commercially avallable, known from the literature [for example H. Pessoa-Mahana et
al., Synth. Comm. 32, 1437 (2002)] or can be prepared in accordance with the
literature cited.
The protective group is cleaved off by methods known from the literature, giving serine
derivatives of the formula V where R4 = hydrogen [cf. J.-F. Rousseau et al., J. Org.
Chem. 63, 2731-2737 (1998); J. M. Andres, Tetrahedron 56, 1523 (2000)]; in the case

of I = benzyl by hydrogenolysis, preferably using hydrogen and Pd/C in methanol; in
the case of E = tert-butyl using acid, preferably hydrochloric acid in dioxane.
The reaction of the serine derivatives V where R4 = hydrogen with heteroaryl
acids/heteroaryl acid derivatives IV where R4 = hydrogen to give heteroaroyl
derivatives III where R4 = hydrogen is usually carried out analogously to the reaction of
the serine derivatives of the formula V with heteroaryl acids/heteroaryl acid derivatives
of the formula III to give heteroaroyl derivatives III mentioned in process A.
Analogously to process A, the heteroaroyl derivatives of the formula III where
R4 = hydrogen can then be reacted with amines of the formula II to give the desired
heteroaroyl-substituted serineamides of the formula I where R4 = hydrogen which can
then be derivatized with compounds of the formula IX to give heteroaroyl-substituted
serineamides of the formula I [cf., for example, Yokokawa, F.'et al., Tetrahedron Lett.
42 (34), 5903-5908 (2001); Arrault, A. et al., Tetrahedron Lett. 43 (22), 4041-4044
(2002)].
It is also possible to derivatize the heteroaroyl derivatives of the formula III where
R4= hydrogen initially with compounds of the formula IX to give further heteroaroyl
derivatives of the formula II! [cf., for example, Troast, D. et al., Org. Lett. 4 (6), 991-994
(2002); Ewing W. et al., Tetrahedron Lett., 30 (29), 3757-3760 (1989); Paulsen, H. et
al., Liebigs Ann. Chem. 565 (1987)], followed by reaction with amines of the formula II
analogously to process A, giving the desired heteroaroyl-substituted serineamides of
the formula I:

L1 is a nucleophilically displaceable leaving group, for example hydroxyl or C1-C6-
alkoxy.

L3 is a nucleophilically displaceable leaving group, for example halogen, hydroxyl, or
CVCs-alkoxy.
The reaction of the heteroaroyl derivatives of the formula III (where, if appropriate,
R4= hydrogen) with amines of the formula II to give heteroaroyl-substituted
serineamides of the formula I (where, if appropriate, R4 = hydrogen) is usually carried
out analogously to the reaction of the heteroaroyl derivatives of the formula III with
amines of the formula II described in process A.
The reaction of the heteroaroyl derivatives of the formula III where R4 = hydrogen or of
the heteroaroyl-substituted serineamides of the formula I where R4 = hydrogen with
compounds of the formula IX to give heteroaroyl derivatives of the formula III or
heteroaroyl-substituted serineamides of the formula I is usually carried out at
temperatures of from 0°C to 100°C, preferably from 10°C to 50°C, in an inert organic
solvent in the presence of a base [cf., for example, Troast, D. et al., Org. Lett. 4 (6),
991-994 (2002); Ewing W. et al., Tetrahedron Lett., 30 (29), 3757-3760 (1989);
Paulsen, H. et al., Liebigs Ann. Chem. 565 (1987)].
Suitable solvents are aliphatic hydrocarbons, such as pentane, hexane, cyclohexane
and mixtures of C5-C8-alkanes, aromatic hydrocarbons, such as toluene, o-, m- and
p-xylene, halogenated hydrocarbons, such as methylene chloride, chloroform and
chlorobenzene, ethers, such as diethyl ether, diisopropyl ether, tert-butyl methyl ether,
dioxane, anisole and tetrahydrofuran, nitriles, such as acetonitrile and propionitrile,
ketones, such as acetone, methyl ethyl ketone, diethyl ketone and tert-butyl methyl
ketone, alcohols, such as methanol, ethanol, n-propanol, isopropanol, n-butanol and
tert-butanol, and also dimethyl sulfoxide, dimethylformamide and dimethylacetamide,
particularly preferably dichloromethane, tert-butyl methyl ether, dioxane and
tetrahydrofuran.
It is also possible to use mixtures of the solvents mentioned.
Suitable bases are, in general, inorganic compounds, such as alkali metal and alkaline
earth metal hydroxides, such as lithium hydroxide, sodium hydroxide, potassium
hydroxide and calcium hydroxide, alkali metal and alkaline earth metal oxides, such as
lithium oxide, sodium oxide, calcium oxide and magnesium oxide, alkali metal and
alkaline earth metal hydrides, such as lithium hydride, sodium hydride, potassium
hydride and calcium hydride, alkali metal amides, such as lithium amide, sodium amide
and potassium amide, alkali metal and alkaline earth metal carbonates, such as lithium
carbonate, potassium carbonate and calcium carbonate, and also alkali metal
bicarbonates, such as sodium bicarbonate, organometallic compounds, in particular
alkali metal alkyls, such as methyllithium, butyllithium and phenyllithium,

alkylmagnesium halides, such as methylmagnesium chloride, and also alkali metal and
alkaline earth metal alkoxides, such as sodium methoxide, sodium ethoxide, potassium
ethoxide, potassium tert-butoxide, potassium tert-pentoxide and dimethoxymagnesium,
moreover organic bases, for example tertiary amines, such as trimethylamine,
triethylamine, diisopropylethylamine and N-methylpiperidine, pyridine, substituted
pyridines, such as collidine, lutidine and 4-dimethylaminopyridine, and also bicyclic
amines. Particular preference is given to sodium hydroxide, sodium hydride and
triethylamine.
The bases are generally employed in equimolar amounts; however, they can also be
employed catalytically, in excess or, if appropriate, as solvents.
The starting materials are generally reacted with one another in equimolar amounts. It
may be advantageous to use an excess of base and/or IX, based on III or I.
Work-up and isolation of the products can be carried out in a manner known per se.
The required compounds of the formula VIII are commercially avallable.
Process C
Heteroaroyl derivatives of the formula III where R4 = hydrogen can also be obtalned by
initially acylating aminomalonyl compounds of the formula XI with heteroaryl
acids/heteroaryl acid derivatives of the formula IV to give the corresponding N-acyl-
aminomalonyl compounds of the formula X, followed by condensation with a carbonyl
compound of the formula VII with decarboxylation:

L1 is a nucleophilically displaceable leaving group, for example hydroxyl or C1-C6-
alkoxy.
L2 is a nucleophilically displaceable leaving group, for example hydroxyl, halogen,
C1-CValkylcarbonyl, C1-C6-alkoxycarbonyl, C1-C6-alkylsulfonyl, phosphoryl or isoureyl.
L4 is a nucleophilically displaceable leaving group, for example hydroxyl or C1-C6-

alkoxy.
The acylation of the aminomalonyl compounds of the formula XI with heteroaryl
acids/heteroaryl acid derivatives of the formula IV to give the corresponding N-acyl-
aminomalonyl compounds of the formula X is usually carried out analogously to the
reaction, mentioned in process A, of the serine derivatives of the formula V with
heteroaryl acids/heteroaryl acid derivatives of the formula IV to give the corresponding
heteroaroyl derivatives of the formula III.
The reaction of the N-acylaminomalonyl compounds of the formula X with carbonyl
compounds of the formula VII give heteroaroyl derivatives of the formula III where R4 =
hydrogen is usually carried out at temperatures of from 0°C to 100°C, preferably from
10°C to 50°C, in an inert organic solvent in the presence of a base [cf., for example,
US 4904674; Hellmann, H. et a!., Liebigs Ann. Chem. 631, 175-179 (1960)].
If L4 in the N-acylaminomalonyl compounds of the formula X is C1-C6-akoxy, it is
advantageous to initially convert L4 by ester hydrolysis [for example Hellmann, H. et al.,
Liebigs Ann. Chem. 631, 175-179 (1960)] into a hydroxyl group.
Suitable solvents are aliphatic hydrocarbons, such as pentane, hexane, cyclohexane
and mixtures of C5-C8-alkanes, aromatic hydrocarbons, such as toluene, o-, m- and
p-xylene, halogenated hydrocarbons, such as methylene chloride, chloroform and
chlorobenzene, ethers, such as diethyl ether, diisopropyl ether, tert-butyl methyl ether,
dioxane, anisole and tetrahydrofuran, nitriles, such as acetonitrile and propionitrile,
ketones, such as acetone, methyl ethyl ketone, diethyl ketone and tert-butyl methyl
ketone, alcohols, such as methanol, ethanol, n-propanoi, isopropanol, n-butanol and
tert-butanol, and also dimethyl sulfoxide, dimethylformamide and dimethylacetamide,
particularly preferably diethyl ether, dioxane and tetrahydrofuran.
It is also possible to use mixtures of the solvents mentioned.
Suitable bases are, in general, inorganic compounds, such as alkali metal and alkaline
earth metal hydroxides, such as lithium hydroxide, sodium hydroxide, potassium
hydroxide and calcium hydroxide, alkali metal and alkaline earth metal oxides, such as
lithium oxide, sodium oxide, calcium oxide and magnesium oxide, alkali metal and
alkaline earth metal hydrides, such as lithium hydride, sodium hydride, potassium
hydride and calcium hydride, alkali metal amides, such as lithium amide, sodium amide
and potassium amide, alkali metal and alkaline earth metal carbonates, such as lithium
carbonate, potassium carbonate and calcium carbonate, and also alkali metal
bicarbonates, such as sodium bicarbonate, organometallic compounds, in particular

alkali metal alkyls, such as methyllithium, butyllithium and phenyllithium,
alkylmagnesium halides, such as methylmagnesium chloride, and also alkali metal and
alkaline earth metal alkoxides, such as sodium methoxide, sodium ethoxide, potassium
ethoxide, potassium tert-butoxide, potassium tert-pentoxide and dimethoxymagnesium,
moreover organic bases, for example tertiary amines, such as trimethylamine,
triethylamine, diisopropylethylamine and N-methylpiperidine, pyridine, substituted
pyridines, such as collidine, lutidine and 4-dimethylaminopyridine, and also bicyclic
amines. Particular preference is given to triethylamine and diisopropylethylamine.
The bases are generally employed in catalytic amounts; however, they can also be
used in equimolar amounts, in excess or, if appropriate, as solvents.
The starting materials are generally reacted with one another in equimolar amounts. It
may be advantageous to employ an excess of base, based on X.
Work-up and isolation of the products can be carried out in a manner known per se.
According to the process A or B mentioned above, the resulting heteroaroyl derivatives
of the formula III where R4 = hydrogen can then be converted into the desired
heteroaroyl-substituted serineamides of the formula I.
The required aminomalonyl compounds of the formula XI are commercially avallable
and/or known from the literature [for example US 4904674; Hellmann, H. et al., Liebigs
Ann. Chem. 631, 175-179 (1960)], or they can be prepared in accordance with the
literature cited.
The required heterocyclic compounds of the formula VII are commercially avallable.
Process D
Heteroaroyl derivatives of the formula III where R4 and R5 = hydrogen can also be
obtalned by initially reducing keto compounds of the formula XIII with heteroaryl
acids/heteroaryl acid derivatives of the formula IV to give the corresponding N-acyl keto
compounds of the formula XII, followed by reduction of the keto group [Girard A,
Tetrahedron Lett. 37 (44), 7967-7970(1996); Nojori R., J. Am. Chem. Soc. 111 (25),
9134-9135(1989); Schmidt U., Synthesis (12), 1248-1254 (1992); Bolhofer, A.; J. Am.
Chem. Soc. 75, 4469 (1953)]:


L1 is a nucleophilically displaceable leaving group, for example hydroxyl or C1-CV
alkoxy.
L2 is a nucleophilically displaceable leaving group, for example hydroxyl, halogen,
C1-C6-alkylcarbonyl, C1-C6-alkoxycarbonyl, C1-C6-alkylsulfonyl, phosphoryl or isoureyl.
The acylation of the keto compounds of the formula XIII with heteroaryl acids/heteroaryl
acid derivatives of the formula IV to give N-acyl keto compounds of the formula XII is
usually carried out analogously to the reaction, mentioned in process A, of the serine
derivatives of the formula V with heteroaryl acids/heteroaryl acid derivatives of the
formula IV to give the corresponding heteroaroyl derivatives of the formula III.
The keto compounds of the formula XIII required for preparing the heteroaroyl
derivatives of the formula III where R4 and R5 = hydrogen are known from the literature
[WO 02/083111; Boto, A. et al., Tetrahedron Letters 39 (44), 8167-8170 (1988); von
Geldem, T. et al., J. of Med. Chem. 39(4), 957-967 (1996); Singh, J. et al., Tetrahedron
Letters 34 (2), 211-214 (1993); ES 2021557; Maeda, S: et al., Chem. & Pharm. Bull. 32
(7), 2536-2543 (1984); Ito, S. et al., J. of Biol. Chem. 256 (15), 7834-4783 (1981);
Vinograd, L. et al., Zhurnal Organicheskoi Khimii 16 (12), 2594-2599 (1980); Castro, A.
et a!., J. Org. Chem. 35 (8), 2815-2816 (1970); JP 02-172956; Suzuki, M. et al., J. Org.
Chem. 38 (20), 3571-3575 (1973); Suzuki, M. et al, Synthetic Communications 2 (4),
237-242 (1972)] or can be prepared according to the literature cited.
The reduction of the N-acyl keto compounds of the formula XII to heteroaroyl
derivatives of the formula III where R4 and R5 = hydrogen is usually carried out at
temperatures of from 0°C to 100°C, preferably from 20°C to 80°C, in an inert organic
solvent in the presence of a reducing agent.
Suitable solvents are aliphatic hydrocarbons, such as pentane, hexane, cyclohexane
and mixtures of C5-C8-alkanes, aromatic hydrocarbons, such as toluene, o-, m- and p-
xylene, halogenated hydrocarbons, such as methylene chloride, chloroform and
chlorobenzene, ethers, such as diethyl ether, diisopropyl ether, tert-butyl methyl ether,
dioxane, anisole and tetrahydrofuran, nitriles, such as acetonitrile and propionitrile,
ketones, such as acetone, methyl ethyl ketone, diethyl ketone and tert-butyl methyl

ketone, alcohols, such as methanol, ethanol, n-propanol, isopropanol, n-butanol and
tert-butanol, and also dimethyl sulfoxide, dimethyl formamide and dimethyl acetamide,
particularly preferably toluene, methylene chloride or tert-butyl methyl ether.
It is also possible to use mixtures of the solvents mentioned.
Suitable reducing agents are, for example, sodium borohydride, zinc borohydride,
sodium cyanoborohydride, lithium triethylborohydride (Superhydrid®), lithium tri-sec-
butylborohydride (L-Selectrid®), lithium aluminum hydride or borane [cf., for example,
WO 00/20424; Marchi, C. et al., Tetrahedron 58 (28), 5699 (2002); Blank, S. et al.,
Liebigs Ann. Chem. (8), 889-896 (1993); Kuwano, R. et al., J. Org .Chem. 63 (10),
3499-3503 (1998); Clariana, J. et al., Tetrahedron 55 (23), 7331-7344 (1999)].
Furthermore, the reduction can also be carried out in the presence of hydrogen and a
catalyst. Suitable catalysts are, for example, [Ru(BINAP)Ci2] or Pd/C [cf. Noyori, R. et
al., J. Am. Chem. Soc. 111 (25), 9134-9135 (1989); Bolhofer, A. et al., J. Am. Chem.
Soc. 75, 4469(1953)].
In addition, the reduction can also be carried out in the presence of a microorganism.
The suitable microorganism is, for example, Saccharomyces rouxii [cf. Soukup, M. et
a!., Helv. Chim. Acta 70, 232 (1987)].
The N-acyl keto compounds of the formula XII and the reducing agent in question are
generally reacted with one another in equimolar amounts. It may be advantageous to
employ an excess of reducing agent, based on XII.
Work-up and isolation of the products can be carried out in the manner known per se.
The resulting heteroaroyl derivatives of the formula III where R4 and R5 = hydrogen can
then, according to the processes A and B mentioned above, be converted into the
desired heteroaroyl-substituted serineamides of the formula I.
Process E
Heteroaroyl derivatives of the formula III where R4 = hydrogen and R6 = -C(OH)R'R"
can also be obtalned by dihydroxylating vinylglycines of the formula XIV with an
oxidizing agent such as osmium tetroxide or permanganate:


L1 is a nucleophilically dispiaceable leaving group, for example hydroxyl or CVCer
alkoxy.
R' is hydrogen, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-hydroxyalkyl, phenyl or C1-C6-
alkoxycarbonyl.
R" is hydrogen, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-hydroxyalkyl, phenyl or C1-C6-
alkoxycarbonyl.
This reaction is usually carried out at temperatures of from -78 °C to the boiling point of
the reaction mixture, preferably from -10 °C to 120 °C, particularly preferably from
0 °C to 50 °C, in an inert organic solvent, if appropriate in the presence of a reoxidazing
agent, such as, for example, N-methylmorpholine N-oxide (D. Johnson et al.,
Tetrahedron 2000, 56, 5, 781).
Suitable solvents are halogenated hydrocarbons, such as methylene chloride,
chloroform and chlorobenzene, ethers, such as diethyl ether, diisopropyl ether, tert-
butyl methyl ether, dioxane, anisole and tetrahydrofuran, nitriles, such as acetonitrile
and propionitrile, ketones, such as acetone, methyl ethyl ketone, diethyl ketone and
tert-butyl methyl ketone,
alcohols, such as methanol, ethanol, n-propanol, isopropanoi, n-butanol and tert.-
butanoi,
and also dimethyl sulfoxide, dimethylformamide, dimethylacetamide and water;
particularly preferably acetone or water.
It is also possible to use mixtures of the solvents mentioned.
The starting materials are generally reacted with one another in equimolar amounts. It
may be advantageous to employ an excess of oxidizing agent, based on XIV.
The reaction mixtures are worked up in a customary manner, for example by mixing
with water, separation of the phases and, if required, chromatographic purification of
the crude products. Some of the intermediates and end products are obtalned in the
form of viscous oils which are purified or freed from volatile components under reduced
pressure and at moderately elevated temperature. If the intermediates and end

products are obtalned as solids, purification may also be carried out by recrystallization
or digestion.
The vinylglycines of the formula XIV required for preparing the heteroaroyl derivatives
of the formula III where R4 = hydrogen and R6 = -C(OH)R'R" are known from the
literature [ D. B. Berkowitz et al., J. Org. Chem. 2000, 65, 10, 2907; M. Koen et al., J.
Chem. Soc. Perkin I 1997, 4, 487] or can be prepared in accordance to the literature
cited.
Analogously to process A, the heteroaroyl derivatives of the formula III where R4 =
hydrogen and R6 = -C(OH)R'R" can then be reacted with amines of the formula II to
give the desired heteroaroyl-substituted serineamides of the formula I where R4 =
hydrogen and R6 = -C(OH)R'R", which can then be derivatized with compounds of the
formula IX to give heteroaroyl-substituted serineamides of the formula I where R6 = -
C(OR4)R!R" [cf., for example, Yokokawa, F. et al., Tetrahedron Lett. 42 (34), 5903-
5908 (2001); Arrault, A. et al., Tetrahedron Lett. 43( 22), 4041-4044 (2002)];
also, the heteroaroyl derivatives of the formula III where R4 = hydrogen can initially be
derivatized analogously to process B with compounds of the formula IX to give further
heteroaroyl derivatives of the formula III where R6 = -C(OR4)R'R" [cf., for example,
Troast, D. et al., Org. Lett. 4 (6), 991-994 (2002); Ewing W. et al., Tetrahedron Lett., 30
(29), 3757-3760 (1989); Paulsen, H. et al., Liebigs Ann. Chem. 565 (1987)] and then
be reacted analogously to process A with amines of the formula II to give the desired
heteroaroyl-substituierted serineamides of the formula I where R6 = -C(OR4)R'R":


I_1 is a nucleophilically displaceable leaving group, for example hydroxyl or C^Ce-
alkoxy.
L3 is a nucleophilically displaceable leaving group, for example halogen, hydroxyl or Cr
C6-alkoxy.
R' is hydrogen, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-hydroxyalkyl, phenyl or (VC6-
alkoxycarbonyl.
R" is hydrogen, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-hydroxyalkyl, phenyl or U1-U6-
alkoxycarbonyl.
Process F
Heteroaroyl derivatives of the formula III where R4 = hydrogen and R6 = -C(Nuc)R'R"
can also be obtalned by epoxidizing vinylglycines of the formula XIV with an
epoxidizing agent to give epoxyglycines of the formula XV, followed by nucleophilic
opening of the epoxide:


L1 is a nucleophilically displaceable leaving group, for example hydroxyl or C1--C6-
alkoxy.
R' is hydrogen, C1-C6-alkyl, C1-C6-haloall alkoxycarbonyl.
R" is hydrogen, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-hydroxyalkyl, phenyl or C1C6-
alkoxycarbonyl.
Nuc_M+is, for example, a thiolate, such as, for example, sodium thiophenolate, an
alcoxide, such as potassium phenoxide, or an amide, such as sodium imidazolate.
The epoxidation is usually carried out at temperatures of from -78 °C to the boiling
point of the reaction mixture, preferably from -20 °C to 50 °C, in particular from 0 °C to
30 °C, in an inert organic solvent [cf. P. Meffre et al., Tetrahedron Lett. 1990, 31, 16,
2291].
Suitable epoxidizings agent are peracids and peroxides (for example meta-
chloroperbenzoic acid, peracetic acid, dimethyldioxirane, hydrogen peroxide).
Suitable solvents are halogenated hydrocarbons, such as methylene chloride,
chloroform and chiorobenzene, alcohols, such as methanol, ethanol, n-propanol,
isopropanol, n-butanol and tert-butanol, and also water,
particularly preferably halogenated hydrocarbons and water.
It is also possible to use mixtures of the solvents mentioned.
The starting materials are generally reacted with one another in equimolar amounts. It
may be advantageous to employ an excess of epoxidizing agent, based on XIV.
The reaction mixtures are worked up in a customary manner, for example by mixing
with water, separation of the phases and, if required, chromatographic purification of
the crude products. Some of the intermediates and end products are obtalned in the
form of viscous oils which are purified or freed from volatile components under reduced
pressure and at moderately elevated temperature. If the intermediates and end
products are obtalned as solids, purification may also be carried out by recrystallization
or digestion.
The vinylglycines of the formula XIV required for preparing the heteroaroyl derivatives
of the formula III where R4 = hydrogen and R6 = -C(OH)R'R" are known from the
literature [D. B. Berkowitz et al., J. Org. Chem. 2000, 65, 10, 2907; M. Koen et al., J.
Chem. Soc. Perkin I 1997, 4, 487] or can be prepared in accordance with the literature
cited.

The opening of the epoxide is usually carried out at temperatures of from -78 °C to the
boiling point of the reaction mixture, preferably from -20 °C to 100 °C, particularly
preferably from 0 °C to 50 °C, in an inert organic solvent, if appropriate in the presence
of a catalyst [cf. P. Meffre et at., Tetrahedron Lett. 1990, 31, 16, 2291; M. R. Paleo et
al., J. Org. Chem. 2003, 68, 1, 130].
Suitable solvents are alcohols, such as methanol, ethanol, n-propanol, isopropanol, n-
butanol and tert-butanol, and also dimethyl sulfoxide, dimethylformamide and
dimethylacetamide and water, particularly preferably methanol and water.
It is also possible to use mixtures of the solvents mentioned.
Suitable acid catalysts are Lewis acids, such as boron trifluoride, aluminum trichloride,
iron(lll) chloride, tin(iV) chloride, titanium(IV) chloride, zinc(ll) chloride and magnesium
perchlorate.
The catalyst is usually employed in an amount of from 1 to 100 mol%, preferably from 1
to 10 mol%, based on the compound XV.
The starting materials are generally reacted with one another in equimolar amounts. It
may be advantageous to employ an excess of Nuc~M+, based on XV.
The reaction mixtures are worked up in a customary manner, for example by mixing
with water, separation of the phases and, if required, chromatographic purification of
the crude products. Some of the intermediates and end products are obtalned in the
form of viscous oils which are purified or freed from volatile components under reduced
pressure and at moderateiy elevated temperature. If the intermediates and end
products are obtalned as solids, purification may also be carried out by recrystallization
or digestion.
Analogously to process A, the heteroaroyl derivatives of the formula III where R4 =
hydrogen and R6 = -C(Nuc)R'R" can then be reacted with amines of the formula II to
give the desired benzoyl-substituted serineamides of the formula I where R4 =
hydrogen and R6 = -C(Nuc)R'R", which can then be derivatized with compounds of the
formula IX to give heteroaroyl-substituted serineamides of the formula I where R6 = -
C(OR4)R'R" [cf., for example, Yokokawa, F. et al., Tetrahedron Lett. 42 (34), 5903-
5908 (2001); Arrault, A. et al., Tetrahedron Lett. 43( 22), 4041-4044 (2002)];
also, the heteroaroyl derivatives of the formula III where R4 = hydrogen can initially be
derivatized analogously to process B with compounds of the formula IX to give further

benzoyl derivatives of the formula III where R6 = -C(Nuc)R'R" [cf., for example, Troast,
D. et al., Org. Lett. 4 (6), 991-994 (2002); Ewing W. et al., Tetrahedron Lett., 30 (29),
3757-3760 (1989); Paulsen, H. et al., Liebigs Ann. Chem. 565 (1987)] and then be
reacted analogously to process A with amines of the formula II to give the desired
heteroaroyl-substituierted serineamides of the formula I where R6 = -C(Nuc)R'R":

L1 is a nucleophilically displaceable leaving group, for example hydroxyl or C1-C6-
alkoxy.
L3 is a nucleophilically displaceable leaving group, for example halogen, hydroxyl or Cr
C6-alkoxy.
R' is hydrogen, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-hydroxya!kyl, phenyl or C1-C6-
alkoxycarbonyl.
R" is hydrogen, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-hydroxyaIkyl, phenyl or C1-C6-
alkoxycarbonyl.
Nuc~M+ is, for example, a thiolate, such as, for example, sodium thiophenolate, an
alcoxide, such as potassium phenoxide, or an amide, such as sodium imidazolate.
The present invention also provides heteroaroyl derivatives of the formula 111


where A, R1 and R4, R5 and R6 are as defined above and L1 is hydroxyl or C1-C6-
alkoxy.
The particularly preferred embodiments of the intermediates with respect to the
variables correspond to those of the radicals A, R1 and R4 to R6 of the formula I.
Particular preference is given to heteroaroyl derivatives of the formula III in which
A is 5- or 6-membered heteroaryl selected from the group consisting of thienyl,
furyl, pyrazolyl, imidazolyl, thiazolyl, oxazolyl and pyridyl; where the
heteroaryl radicals mentioned may be partially or fully halogenated and/or
may carry 1 to 3 radicals from the group consisting of C1-C6-alkyl, C3-C6-
cycloalkyl and C1-C6-haloalkyl;
R1 is hydrogen;
R4 is hydrogen, formyl, C1-C4-alkylcarbonyl, C1-C4alkylaminocarbonyl, di-(C1-C4-
alkyl)-aminocarbonyl, phenylaminocarbonyl, N-(C1-C4-alkyl)-N-
(phenyl)aminocarbonyl, S02CH3,S02CF3 or S02(C6H5);
R5 is hydrogen; and
R6 is C1-C6-alkyl, C2-C6-alkenyl, C1-C6-haloalkyl, C2-C6-haloalkenyl, C1-C6-
hydroxyalkyl, hydroxycarbonyl-C.,-C4-alkyl, phenyl-C1-C4-alkyl or phenyl-C1-C4-
hydroxyalkyl.
The examples below serve to illustrate the invention.
Preparation examples
Example 1
l-dvlethvlcarbamovl-rd-methvl-S-trifiuoromethyl-IH-pyrazol-A-carbonvDaminolmethvll-
allvl acetate (Tab. 3 No. 3.10)
1.1) Ethyl ff 1-methyl-3-trifluoromethvl-1 H-pyrazole-4-carbonvl)amino1acetate


3.63 g (25.8 mmol) of ethyl glycinate hydrochloride were dissolved in CH2CI2, and THF,
5.00 g (25.8 mmol) of 1-methyl-3-trifluoromethyl-4-carboxylic acid and 7.82 g of
triethylamine (77.3 mmol) were added at RT and 6.56 g (25.8 mmol) of bis-(2-oxo)-3-
oxazolidinyl)phosphonyl chloride were added at 0°C. The mixture was stirred at 0°C for
3 h and then at RT for 16 h. The solvents were then removed, the residue was taken
up in ethyl acetate, washed and dried and the solvent was removed. This gave 3.88 g
(54 % of theory) of the title compound as a red oil.
1H-NMR (DMSO): 5 = 1.20 (t,3H); 3.95 (s, 6H); 4.15 (q, 2H); 8.35 (s, 1H); 8.65 (t, 1H).
1.2) Ethyl 3-hydroxv-2-f(1-methvl-3-trifluoromethyl-1 H-pvrazole-4-carbonvl)aminolpent-
4-enoate (Tab. 2, No. 2.2)

At -50°C, 3.45g (12.4 mmol) of ethyl [(1-methyl-3-trifluoromethyl-1H-pyrazole-4-
carbonyl)amino]acetate dissolved in THF were added dropwise to 18.5 ml (37.0 mmol)
of a 2M solution of lithium diisopropylamide in THF/heptane/ethylbenzene. After 1.5 h
of stirring at -50°C, the mixture was cooled to -78 °C and 0.83 g (14.8 mmol) of
acrolein dissolved in THF were added dropwise. After 2 h of stirring at -78 °C, the
mixture was hydrolyzed with sat. NH4CI solution and warmed to RT. After separation of
the phases, the organic phase was dried and the solvent was removed. The residue
was purified chromatographicaliy (Si02, cyclohexane/ethyl acetate). This gave 1.65 g
(40 % of theory) of the title compound as a colorless solid (about 1:1 diastereomer
mixture) which was used without further purification.
1.3) N-(2-Hydroxy-1 -methvlcarbamoylbut-3-envl)-1 -methyl-3-trifluoromethyl-1 H-
pyrazole-4-carboxamide (Tab. 3, No. 3.4)


1.65 g (4.92 mmol) of ethyl 3-hydroxy-2-[(1-methyl-3-trifluoromethyl-1 H-pyrazole-4-
carbonyl)amino]pent-4-enoate were dissolved in methanol. At 0°C, methylamine gas
was introduced for 1 h. After 16 h of stirring at RT, the solvent was removed and the
residue was recrystallized from acetone. The precipitate gave 0.65 g of erythro title
compound as a colorless powder, the filtrate contalned 0.75 g of isomer mixture.
Accordingly, the total yleld was 1.40 g (89 % of theory).
'H-NMR (DMSO) (erythro isomer): 5 = 2.55 (d, 3H); 4.95 (s, 3H); 4.25 (m, 1H); 4.35 (t,
1H); 5.10 (d, 1H); 5.25 (d, 1H); 5.35 (d, 1H); 5.80 (m, 1H); 7.95 (d, 1H); 8.10 (d, 1H);
8.45 (s,1H).
1.4) 1-{Methvlcarbamovl-r(1-methvl-3-trifluoromethvl-1 H-pvrazole-4-carbonvl)amino1-
methvDallyl acetate (Tab. 3 No. 3.10)

134 mg (0.42 mmol) of N-(2-hydroxy-1-methylcarbamoylbut-3-enyl)-1-methyl-3-
trifluoromethyl-1H-pyrazole-4-carboxamide, 28 mg (0.46 mmol) of acetic acid and
20 mg (0.17 mmol) of dimethylaminopyhdine were dissolved in CH2CI2. At 0°C, 88 mg
(0.46 mmol) of 1-(3-dimethylaminopropyl)-3-(ethylcarbodiimide) hydrochloride were
added. After 16 h of stirring at RT, the reaction solution was washed and the solvent
was removed. This gave 0.10 g (66 % of theory) of the title compound as a colorless
powder (M+ (m/z)=362).
In addition to the above compounds, further heteroaroyl derivatives of the formula III
and heteroaroyl-substituted serineamides of the formula I which were prepared or are
preparable in a manner analogously to the processes described above are listed in
Tables 2 and 3 below.











Biological activity
The heteroaroyl-substituted serineamides of the formula I and their agriculturally useful
salts are suitable, both in the form of isomer mixtures and in the form of the pure
isomers, as herbicides. The herbicidal compositions comprising compounds of the
formula I control vegetation on non-crop areas very efficiently, especially at high rates
of application. They act agalnst broad-leaved weeds and grass weeds in crops such as
wheat, rice, malze, soya and cotton without causing any significant damage to the crop
plants. This effect is malnly observed at low rates of application.
Depending on the application method in question, the compounds of the formula I, or
herbicidal compositions comprising them, can additionally be employed in a further
number of crop plants for eliminating undesirable plants. Examples of suitable crops
are the following:
Allium cepa, Ananas comosus, Arachis hypogaea, Asparagus officinalis, Beta vulgaris
spec, altissima, Beta vulgaris spec, rapa, Brassica napus var. napus, Brassica napus
var. napobrassica, Brassica rapa var. silvestris, Camellia sinensis, Carthamus
tinctorius, Carya illinoinensis, Citrus limon, Citrus sinensis, Coffea arabica (Coffea
canephora, Coffea liberica), Cucumis sativus, Cynodon dactylon, Daucus carota,
Elaeis guineensis, Fragaria vesca, Glycine max, Gossypium hirsutum, (Gossypium
arboreum, Gossypium herbaceum, Gossypium vitifolium), Helianthus annuus, Hevea
brasiliensis, Hordeum vulgare, Humulus lupulus, Ipomoea batatas, Juglans regia, Lens
culinaris, Linum usitatissimum, Lycopersicon lycopersicum, Malus spec, Manihot
esculenta, Medicago sativa, Musa spec, Nicotiana tabacum (N.rustica), Olea
europaea, Oryza sativa, Phaseolus lunatus, Phaseolus vulgaris, Picea abies, Pinus
spec, Pisum sativum, Prunus avium, Prunus persica, Pyrus communis, Ribes
sylvestre, Ricinus communis, Saccharum officinarum, Secale cereale, Solanum
tuberosum, Sorghum bicolor (s. vulgare), Theobroma cacao, Trifolium pratense,
Triticum aestivum, Triticum durum, Vicia faba, Vitis vinifera and Zea mays.
In addition, the compounds of the formula I may also be used in crops which tolerate
the action of herbicides owing to breeding, including genetic engineering methods.
In addition, the compounds of the formula I may also be used in crops which tolerate
attack by fungi or insects owing to breeding, including genetic engineering methods.
The compounds of the formula I, or the herbicidal compositions comprising them, can
be used for example in the form of ready-to-spray aqueous solutions, powders,
suspensions, also highly concentrated aqueous, oily or other suspensions or
dispersions, emulsions, oil dispersions, pastes, dusts, materials for broadcasting, or
granules, by means of spraylng, atomizing, dusting, spreading or watering. The use
forms depend on the intended purpose; in any case, they should guarantee the finest
possible distribution of the active ingredients according to the invention.

The herbicidal compositions comprise a herbicidally effective amount of at least one
compound of the formula i or an agriculturally useful salt of I, and auxiliaries which are
customary for the formulation of crop protection agents.
Suitable as inert auxiliaries are essentially the following:
mineral oil fractions of medium to high boiling point, such as kerosene and diesel oil,
furthermore coal tar oils and oils of vegetable or animal origin, aliphatic, cyclic and
aromatic hydrocarbons, e.g. paraffin, tetrahydronaphthalene, alkylated naphthalenes
and their derivatives, alkylated benzenes and their derivatives, alcohols such as
methanol, ethanol, propanol, butanol and cyclohexanol, ketones such as
cyclohexanone, strongly polar solvents, e.g. amines such as N-methylpyrrolidone, and
water.
Aqueous use forms can be prepared from emulsion concentrates, suspensions, pastes,
wettable powders or water-dispersible granules by adding water. To prepare
emulsions, pastes or oil dispersions, the substrates, either as such or dissolved in an
oil or solvent, can be homogenized in water by means of a wetting agent, tackifier,
dispersant or emulsifier. Alternatively, it is also possible to prepare concentrates
comprising active substance, wetting agent, tackifier, dispersant or emulsifier and, if
desired, solvent or oil, which are suitable for dilution with water.
Suitable surfactants (adjuvants) are the alkali metal salts, alkaline earth metal salts and
ammonium salts of aromatic sulfonic acids, e.g. ligno-, phenol-, naphthalene- and
dibutylnaphthalenesulfonic acid, and of fatty acids, alkyl- and alkylarylsulfonates, alkyl
sulfates, lauryl ether sulfates and fatty alcohol sulfates, and salts of sulfated hexa-,
hepta- and octadecanols, and also of fatty alcohol glycol ethers, condensates of
sulfonated naphthalene and its derivatives with formaldehyde, condensates of
naphthalene or of the naphthalenesulfonic acids with phenol and formaldehyde,
polyoxyethylene octylphenol ether, ethoxylated isooctyl-, octyl- or nonylphenol,
alkylphenyl or tributylphenyl polyglycoi ether, alkylaryl polyether alcohols, isotridecyl
alcohol, fatty alcohol/ethylene oxide condensates, ethoxylated castor oil,
polyoxyethylene alkyl ethers or polyoxypropylene alkyl ethers, iauryl alcohol polyglycoi
ether acetate, sorbitol esters, lignosulfite waste liquors or methylcellulose.
Powders, materials for broadcasting and dusts can be prepared by mixing or grinding
the active ingredients together with a solid carrier.
Granules, e.g. coated granules, impregnated granules and homogeneous granules,
can be prepared by binding the active ingredients to solid carriers. Solid carriers are
mineral earths such as silicas, silica gels, silicates, talc, kaolin, limestone, lime, chalk,
bole, loess, clay, dolomite, diatomaceous earth, calcium sulfate, magnesium sulfate
and magnesium oxide, ground synthetic materials, fertilizers such as ammonium
sulfate, ammonium phosphate, ammonium nitrate and ureas, and products of
vegetable origin, such as cereal meal, tree bark meal, wood meal and nutshell meal,
cellulose powders, or other solid carriers.

The concentrations of the compounds of the formula I in the ready-to-use preparations
can be varied within wide ranges. In general, the formulations comprise approximately
from 0.001 to 98% by weight, preferably 0.01 to 95% by weight of at least one active
ingredient. The active ingredients are employed in a purity of from 90% to 100%,
preferably 95% to 100% (according to NMR spectrum).
The formulation examples below illustrate the preparation of such compositions:
I. 20 parts by weight of an active compound of the formula I are dissolved in a
mixture composed of 80 parts by weight of alkylated benzene, 10 parts by weight
of the adduct of from 8 to 10 mol of ethylene oxide to 1 mol of oleic acid N-
monoethanolamide, 5 parts by weight of calcium dodecylbenzenesulfonate and
5 parts by weight of the adduct of 40 mol of ethylene oxide to 1 mol of castor oil.
Pouring the solution into 100 000 parts by weight of water and finely distributing it
therein gives an aqueous dispersion which comprises 0.02% by weight of the
active ingredient of the formula I.
II. 20 parts by weight of an active compound of the formula I are dissolved in a
mixture composed of 40 parts by weight of cyclohexanone, 30 parts by weight of
isobutanol, 20 parts by weight of the adduct of 7 mol of ethylene oxide to 1 mol of
isooctylphenol and 10 parts by weight of the adduct of 40 mol of ethylene oxide
to 1 mol of castor oil. Pouring the solution into 100 000 parts by weight of water
and finely distributing it therein gives an aqueous dispersion which comprises
0.02% by weight of the active ingredient of the formula I.
III. 20 parts by weight of an active compound of the formula I are dissolved in a
mixture composed of 25 parts by weight of cyclohexanone, 65 parts by weight of
a mineral oil fraction of boiling point 210 to 280°C and 10 parts by weight of the
adduct of 40 mol of ethylene oxide to 1 mol of castor oil. Pouring the solution into
100 000 parts by weight of water and finely distributing it therein gives an
aqueous dispersion which comprises 0.02% by weight of the active ingredient of
the formula I.
IV. 20 parts by weight of an active compound of the formula I are mixed thoroughly
with 3 parts by weight of sodium diisobutylnaphthalenesulfonate, 17 parts by
weight of the sodium salt of a lignosulfonic acid from a sulfite waste liquor and 60
parts by weight of pulverulent silica gel, and the mixture is ground in a hammer
mill. Finely distributing the mixture in 20 000 parts by weight of water gives a
spray mixture which comprises 0.1% by weight of the active ingredient of the
formula I.
V. 3 parts by weight of an active compound of the formula I are mixed with 97 parts
by weight of finely divided kaolin. This gives a dust which comprises 3% by

weight of the active ingredient of the formula I.
VI. 20 parts by weight of an active compound of the formula I are mixed intimately
with 2 parts by weight of calcium dodecylbenzenesulfonate, 8 parts by weight of
fatty alcohol polyglycol ether, 2 parts by weight of the sodium salt of a
phenol/urea/formaldehyde condensate and 68 parts by weight of a paraffinic
mineral oil. This gives a stable oily dispersion.
VII. 1 part by weight of an active compound of the formula I is dissolved in a mixture
composed of 70 parts by weight of cyclohexanone, 20 parts by weight of
ethoxylated isooctylphenol and 10 parts by weight of ethoxylated castor oil. This
gives a stable emulsion concentrate.
VIII. 1 part by weight of an active compound of the formula I is dissolved in a mixture
composed of 80 parts by weight of cyclohexanone and 20 parts by weight of
Wettol® EM 31 (= nonionic emulsifier based on ethoxylated castor oil). This gives
a stable emulsion concentrate.
The compounds of the formula I or the herbicidal compositions can be applied pre- or
post-emergence. If the active ingredients are less well tolerated by certaln crop plants,
application techniques may be used in which the herbicidal compositions are sprayed,
with the ald of the spraylng equipment, in such a way that as far as possible they do
not come into contact with the leaves of the sensitive crop plants, while the active
ingredients reach the leaves of undesirable plants growing underneath, or the bare soil
surface (post-directed, lay-by).
The rates of application of the compound of the formula I are from 0.001 to 3.0,
preferably 0.01 to 1.0, kg/ha of active substance (a.s.), depending on the control target,
the season, the target plants and the growth stage.
To widen the spectrum of action and to achieve synergistic effects, the heteroaroyl-
substituted serineamides of the formula I may be mixed with a large number of
representatives of other herbicidal or growth-regulating active ingredient groups and
then applied concomitantly. Suitable components for mixtures are, for example, 1,2,4-
thiadiazoles, 1,3,4-thiadiazoles, amides, aminophosphoric acid and its derivatives,
aminotriazoles, anilides, (hetero)aryloxyalkanoic acids and their derivatives, benzoic
acid and its derivatives, benzothiadiazinones, 2-(het)aroyl-1,3-cyclohexanediones,
heteroaryl aryl ketones, benzylisoxazolidinones, meta-CF3-phenyl derivatives,
carbamates, quinolinecarboxylic acid and its derivatives, chloroacetanilides,
cyclohexenone oxime ether derivatives, diazines, dichloropropionic acid and its
derivatives, dihydrobenzofurans, dihydrofuran-3-ones, dinitroanilines, dinitrophenols,
diphenyl ethers, dipyridyls, halocarboxylic acids and their derivatives, ureas, 3-

phenyluracils, imidazoles, imidazolinones, N-phenyl-3,4,5,6-tetrahydrophthalimides,
oxadiazoles, oxiranes, phenols, aryloxy- and heteroaryloxyphenoxypropionic esters,
phenylacetic acid and its derivatives, 2-phenylpropionic acid and its derivatives,
pyrazoles, phenylpyrazoles, pyridazines, pyridinecarboxylic acid and its derivatives,
pyrimidyl ethers, sulfonamides, sulfonylureas, triazines, triazinones, triazolinones,
triazolecarboxamides and uracils.
It may furthermore be beneficial to apply the compounds of the formula I alone or in
combination with other herbicides, or in the form of a mixture with other crop protection
agents, for example together with agents for controlling pests or phytopathogenic fungi
or bacteria. Also of interest is the miscibility with mineral salt solutions, which are
employed for treating nutritional and trace element deficiencies. Non-phytotoxic oils
and oil concentrates may also be added.
Use examples
The herbicidal activity of the heteroaroyl-substituted serineamides of the formula I was
demonstrated by the following greenhouse experiments:
The culture contalners used were plastic flowerpots contalning loamy sand with
approximately 3.0% of humus as the substrate. The seeds of the test plants were sown
separately for each species.
For the pre-emergence treatment, the active ingredients, which had been suspended or
emulsified in water, were applied directly after sowing by means of finely distributing
nozzles. The contalners were irrigated gently to promote germination and growth and
subsequently covered with transparent plastic hoods until the plants had rooted. This
cover causes uniform germination of the test plants, unless this has been impalred by
the active ingredients.
For the post-emergence treatment, the test plants were first grown to a height of 3 to
15 cm, depending on the plant habit, and only then treated with the active ingredients
which had been suspended or emulsified in water. For this purpose, the test plants
were either sown directly and grown in the same contalners, or they were first grown
separately as seedlings and transplanted into the test contalners a few days prior to
treatment. The rate of application for the post-emergence treatment was 1.0 kg/ha of
a.s. (active substance).

Depending on the species, the plants were kept at 10 - 25°C or 20 - 35°C. The test
period extended over 2 to 4 weeks. During this time, the plants were tended, and their
response to the individual treatments was evaluated.
Evaluation was carried out using a scale from 0 to 100. 100 means no emergence of
the plants, or complete destruction of at least the aerial parts, and 0 means no
damage, or normal course of growth.
The plants used in the greenhouse experiments belonged to the following species:

At application rates of 1 kg/ha, the compound 3.7 (Table 3) showed very good post-
emergence action agalnst the unwanted plants Amaranthus retroflexus and
Chenopodium album.
Furthermore, compound 3.12 (Table 3), applied by the post-emergence method,
effected, at application rates of 1 kg/ha, very good control of the harmful plants
Amaranthus retroflexus, Chenopodium album and Polygonum convolvulus.

We Clalm:
1. A heteroaroyl-substituted serineamide of the formula I

in which the variables are as defined below:
A is 5- membered heteroaryl selected from the group consisting of thienyl,
furyl, pyrazolyl, imidazolyl, thiazolyl and oxazolyl which heteroaryl may be
partially or fully halogenated and/or may carry 1 to 2 substituents from the
group C1-C6alkyl and C1-C4 halogenalkyl;
R1, R2 are hydrogen,
R3 is C1-C6-alkyl,
R4 is hydrogen,
C1-C6-alkylcarbonyl, C1-C6-alkoxycarbonyl, C1-C6-alkylaminocarbonyl, di(C1-C6-
alkyl)aminocarbonyl, N-(C1-C6-alkoxy)-N-(C1-C6-alkyl)aminocarbonyl, tri-
C1-C4-alkylsilyl, or
phenylaminocarbonyl,
R5 is hydrogen;
R6 is C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-haloalkyl, C1-C6-
hydroxyalkyl, C3-C6-cycloalkyl, 3 to 6-membered heterocyclyl,
where the cycloalkyl or 3- to 6-membered heterocyclyl radicals
mentioned above may be partially or fully halogenated and/or may
carry one to three radicals from the group consisting of C1-C6-alkyl;
C1-C6-alkoxy-C1-C4-alkyl, amino-C1-C4-alkyl, C1-C6-alkoxycarbonylamino-
C1-C4-alkyl, C1-C6-alkylcarbonylamino-C1-C4-alkyl, {di[di(C1-C6-alkyl)
amino]carbonyloxy}C1-C4-alkyl, [(C1-C6-alkylarnino)carbonylamino]-C1-C4-
alkyl, phenyl-C1-C4-alkyl, phenyl-C2-C4-alkenyl, phenyl-C1-C4-hydroxyalkyl,
phenylcarbonylamino-C1-C4-alkyl, phenyloxy-C1-C4-alkyl, heteroaryl-C2-C4-
alkenyl, heteroaryl-C1-C4-hydroxyalkyl,
where the phenyl and heteroaryl radicals mentioned above may be
partially or fully halogenated and/or may carry one to three radicals
from the group consisting of cyano, nitro, C1-C6-alkoxy,

or an agriculturally useful salt thereof.
2. A process for preparing heteroaroyl-substituted serineamides of the formula I as
clalmed in clalm 1, wherein serine derivatives of the formula V

where R1, R4, R5 and R6 are as defined in clalm 1 and L1 is hydroxyl or C1-C6-al-
koxy
are reacted with heteroaryl acids/heteroaroyl acid derivatives of the formula IV

where A is as defined in clalm 1 and L2 is a hydroxyl, halogen, C1-C6-
alkylcarbonyl, C1-C6-alkoxycarbonyl, C1-C4-alkylsulfonyl, phosphoryl or isoureyl
to give the corresponding heteroaroyl derivatives of the formula III

where A, R1, R4, R5 and R6 are as defined in clalm 1 and L1 is hydroxyl or C1-C6-
alkoxy,
and the resulting heteroaroyl derivatives of the formula III are then reacted with
an amine of the formula II
HNR2R3 II,
where R2 and R3 are as defined in clalm 1.
3. A process for preparing heteroaroyl-substituted serineamides of the formula I as
clalmed in clalm 2 where R4 and R5 are hydrogen, wherein heteroaroyl
derivatives of the formula III where R4 and R5 are hydrogen are prepared by
acylation of keto compounds of the formula XIII


where R1 is as defined in clalm 1 and L1 is hydroxyl or C1-C6-alkoxy
with heteroaryl acids/heteroaroyl acid derivatives of the formula IV to give N-acyl
keto compounds of the formula XII

where A, R1 and R6 are as defined in clalm 1 and L1 is hydroxyl or C1-C6-alkoxy
and subsequent reduction of the keto group.
4. A heteroaroyl derivative of the formula III

in which
A is 5- or 6-membered heteroaryl which is attached via carbon and selected from
the group consisting of A1, A2, A3, A4, A5, A6, A8 and A9 where



where the arrow indicates the point of attachment and
R8 is hydrogen, halogen, C1-C6-alkyl or C1-C6-haloalkyl;
R9 is halogen, C1-C6-alkyl, C1-C6-haloalkyl or C1-C6-haloalkoxy;
R10 is hydrogen, halogen, C1-C6-alkyl or C1-C6-haloalkyl; and
R11 is hydrogen, C1-C6-alkyl, C3-C6-cycloalkyl, C1-C6-haloalkyl orC1-C6-
alkoxy-C1-C4-alkyl;
5. A composition, comprising a herbicidally effective amount of at least one
heteroaroyl-substituted serineamide of the formula I or an agriculturally useful
salt of I as clalmed in clalm 1 and auxiliaries customary for formulating crop
protection agents.
6. A process for preparing compositions according to clalm 5, wherein a
herbicidally effective amount of at least one heteroaroyl-substituted serineamide
of the formula I or an agriculturally useful salt of I as clalmed in clalm 1 and
auxiliaries customary for formulating crop protection agents are mixed.


Abstract

HETEROAROYL-SUBSTITUTED SERINE AMIDES
The present invention relates to heteroaroyl-substituted serineamides of the formula I

in which the variables A and R1 to R6 are as defined in the description,
and to their agriculturally useful salts,
to processes and intermediates for their preparation, and to the use of these
compounds or of the compositions comprising these compounds for controlling
unwanted plants.

Documents:

04625-kolnp-2007-abstract.pdf

04625-kolnp-2007-claims.pdf

04625-kolnp-2007-correspondence others.pdf

04625-kolnp-2007-description complete.pdf

04625-kolnp-2007-form 1.pdf

04625-kolnp-2007-form 3.pdf

04625-kolnp-2007-form 5.pdf

04625-kolnp-2007-international exm report.pdf

04625-kolnp-2007-international publication.pdf

04625-kolnp-2007-international search report.pdf

04625-kolnp-2007-others pct form.pdf

04625-kolnp-2007-pct request form.pdf

04625-kolnp-2007-translated copy of priority document.pdf

4625-KOLNP-2007-(02-12-2011)-ABSTRACT.pdf

4625-KOLNP-2007-(02-12-2011)-AMANDED CLAIMS.pdf

4625-KOLNP-2007-(02-12-2011)-CORRESPONDENCE.pdf

4625-KOLNP-2007-(02-12-2011)-DESCRIPTION (COMPLETE).pdf

4625-KOLNP-2007-(02-12-2011)-FORM-1.pdf

4625-KOLNP-2007-(02-12-2011)-FORM-13.pdf

4625-KOLNP-2007-(02-12-2011)-FORM-2.pdf

4625-KOLNP-2007-(02-12-2011)-FORM-3.pdf

4625-KOLNP-2007-(02-12-2011)-OTHER PATENT DOCUMENT.pdf

4625-KOLNP-2007-(02-12-2011)-OTHERS.pdf

4625-KOLNP-2007-(02-12-2011)-PA-CERTIFIED COPIES.pdf

4625-KOLNP-2007-(19-04-2012)-EXAMINATION REPORT REPLY RECIEVED.PDF

4625-KOLNP-2007-ABSTRACT.pdf

4625-KOLNP-2007-CLAIMS.pdf

4625-KOLNP-2007-CORRESPONDENCE 1.2.pdf

4625-KOLNP-2007-CORRESPONDENCE OTHERS 1.1.pdf

4625-KOLNP-2007-DESCRIPTION (COMPLETE).pdf

4625-KOLNP-2007-EXAMINATION REPORT.pdf

4625-KOLNP-2007-FORM 1.pdf

4625-KOLNP-2007-FORM 13 1.1.pdf

4625-KOLNP-2007-FORM 13.pdf

4625-KOLNP-2007-FORM 18 1.1.pdf

4625-kolnp-2007-form 18.pdf

4625-KOLNP-2007-FORM 2.pdf

4625-KOLNP-2007-FORM 3 1.2.pdf

4625-KOLNP-2007-FORM 3-1.1.pdf

4625-KOLNP-2007-FORM 5 1.1.pdf

4625-KOLNP-2007-FORM 5.pdf

4625-KOLNP-2007-GPA.pdf

4625-KOLNP-2007-GRANTED-ABSTRACT.pdf

4625-KOLNP-2007-GRANTED-CLAIMS.pdf

4625-KOLNP-2007-GRANTED-DESCRIPTION (COMPLETE).pdf

4625-KOLNP-2007-GRANTED-FORM 1.pdf

4625-KOLNP-2007-GRANTED-FORM 2.pdf

4625-KOLNP-2007-GRANTED-SPECIFICATION.pdf

4625-KOLNP-2007-INTERNATIONAL PRELIMINARY EXAMINATION REPORT.pdf

4625-KOLNP-2007-INTERNATIONAL PUBLICATION.pdf

4625-KOLNP-2007-INTERNATIONAL SEARCH REPORT.pdf

4625-KOLNP-2007-OTHERS PCT FORM.pdf

4625-KOLNP-2007-OTHERS.pdf

4625-KOLNP-2007-PCT REQUEST FORM.pdf

4625-KOLNP-2007-REPLY TO EXAMINATION REPORT.pdf

4625-KOLNP-2007-SPECIFICATION.pdf

4625-KOLNP-2007-TRANSLATED COPY OF PRIORITY DOCUMENT 1.1.pdf

4625-KOLNP-2007-TRANSLATED COPY OF PRIORITY DOCUMENT.pdf

abstract-04625-kolnp-2007.jpg


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Patent Number 253606
Indian Patent Application Number 4625/KOLNP/2007
PG Journal Number 32/2012
Publication Date 10-Aug-2012
Grant Date 06-Aug-2012
Date of Filing 29-Nov-2007
Name of Patentee BASF AKTIENGESELLSCHAFT
Applicant Address 67056 LUDWIGSHAFEN, GERMANY
Inventors:
# Inventor's Name Inventor's Address
1 ZAGAR CYRILL NO.1 AUSTIN ROAD WEST, KOWLOON, HONG KONG, CHINA
2 EHRHARDT THOMAS MAULBRONNER HOF 49, 67346 SPEYER, GERMANY
3 WITSCHEL MATTHIAS HOHENWEG 12B, 67098 BAD DURKHEIN, GERMANY
4 HUPE EIKE BERGSTR. 13 E, 67067 LUDWIGSHAFEN, GERMANY
5 KUHN TORALF MEISTERSINGERSTR. 1, 68199 MANNHEIM, GERMANY
6 MOBERG WILLIAM KARL MECKENHEIMER STRASSE 34, 67454 HASSLOCH, GERMANY
7 PARRA RAPADO LILIANA ZELLER STR. 14, 77654 OFFENBURG, GERMNAY
8 STELZER FRANK IDA-DEHMEL-RING 40, 68309 MANNHEIM, GERMANY
9 VESCOVI ANDREA MAX-JOSEPH-STR. 23, 68167 MANN HEIM, GERMANY
10 RACK MICHAEL HILDASTR. 11/1, 69214 EPPELHEIM,GERMANY
11 REINHARD ROBERT BERWARTSTEINSTR. 6, 67117 LIMBURGERHOF, GERMANY
12 SIEVERNICH BERND BERTOLT-BRECHT-STR. 18A, 67454 HASSLOCH, GERMANY
13 GROSSMANN KLAUS MAINSTR. 1, 67141 NEUHOFEN, GERMANY
PCT International Classification Number C07D 231/14
PCT International Application Number PCT/EP2006/061128
PCT International Filing date 2006-03-29
PCT Conventions:
# PCT Application Number Date of Convention Priority Country
1 102005024599.4 2005-05-25 Germany