SUBSTITUTED TRIAZOLINONES

DERIVES DE SUBSTITUTION DE TRIAZOLINONES

English Abstract

The invention relates to novel substituted triazolinones of the generalformula (I),
<IMG> (I)
Het represents a heterocycle of the formula
<IMG> or <IMG>,
and
R1, R2, R3, A, X1, R4, R5, R6, R7 and X2 have the meanings given in thedescription, to a number of processes for their preparation and to their
use as herbicides.

Claims

Patent Claims
1. Substituted triazolinones of the general formula (I)
<IMG> (I)
in which
Het represents a heterocycle of the formula
<IMG>
or <IMG>
R1, R2 and R3 independently of one another each represent halogen,
alkyl, alkenyl, alkinyl or alkoxy or represent in each case optionally
substituted arylalkyl, aryl or aryloxy,
A represents a divalent alkanediyl radical, and
X1 represents oxygen or sulphur, where
R4 represents hydrogen, halogen, cyano or nitro or represents optionally
substituted alkyl, or represents alkenyl, alkinyl, halogenoalkenyl,
halogenoalkinyl, alkoxy, alkylthio, alkylsulphinyl, alkylsulphonyl or
alkoxycarbonyl, or represents in each case optionally substituted
cycloalkyl, aryl or aryloxy, or represents a radical of the formula
-59-

<IMG>
R5 represents hydrogen or cyano, or represents optionally substituted
alkyl, or represents alkenyl, alkinyl, alkoxy, alkoxycarbonyl or
aminocarbonyl, or represents amino, N-alkylamino, N,N-
dialkylamino or alkylideneimino, or represents in each case option-
ally substituted cycloalkyl, aryl or aryloxy,
R6 represents alkyl, alkoxy or alkylthio, or represents a radical of the
formula <IMG> ,
R7 represents alkyl or cycloalkyl,
R8 and R9 either independently of one another each represent hydrogen,
alkyl, alkenyl, alkinyl or cycloalkyl or represent in each case
optionally substituted arylalkyl or aryl, or, together with the nitrogen
atom to which they are attached, represent an optionally substituted
heterocycle,
R10 and R11 either independently of one another each represent alkyl,
alkenyl, alkinyl, halogenoalkyl, halogenoalkenyl, halogenoalkinyl,
alkoxyalkyl, alkoxy, cycloalkyl or cycloalkylalkyl or represent in each
case optionally substituted aryl, arylalkyl or heteroaryl, or, together
with the nitrogen atom to which they are attached, represent an
optionally substituted heterocycle, and
X2 represents oxygen or sulphur.
- 60-

2. Substituted triazolinones of the general formula (I) according
to Claim 1, characterized in that
Het represents a heterocycle of the formula
<IMG> or <IMG> ,
R1, R2 and R3 independently of one another each represent fluorine,
chlorine, bromine or iodine, or represent straight-chain or branched
alkyl having 1 to 8 carbon atoms, or represent straight-chain or
branched alkenyl having 2 to 8 carbon atoms, or represent straight-
chain or branched alkinyl having 2 to 8 carbon atoms, or represent
straight-chain or branched alkoxy having 1 to 8 carbon atoms, or
represent arylalkyl, aryl or aryloxy having in each case 6 to 10 carbon
atoms in the aryl moiety and if appropriate 1 to 6 carbon atoms in
the straight-chain or branched alkyl moiety, each of which is
optionally monosubstituted or polysubstituted by identical or
different substituents, suitable substituents for aryl being in each
case:
halogen, cyano, nitro, in each case straight-chain or branched alkyl,
alkoxy or alkylthio having in each case 1 to 6 carbon atoms, in each
case straight-chain or branched halogenoalkyl, halogenoalkoxy or
halogenoalkylthio having in each case 1 to 6 carbon atoms and 1 to
13 identical or different halogen atoms, in each case straight-chain
or branched alkoxycarbonyl or alkoximinoalkyl having in each case
1 to 6 carbon atoms in the individual alkyl moieties, and phenyl
which is optionally monosubstituted or polysubstituted by identical
or different substituents consisting of halogen and/or straight-chain
or branched alkyl having 1 to 6 carbon atoms,
- 61 -

A represents a divalent alkanediyl radical having 1 to 8 carbon atoms,
and
X1 represents oxygen or sulphur, where
R4 represents hydrogen, fluorine, chlorine, bromine, iodine, cyano or
nitro, or represents straight-chain or branched alkyl which is
optionally monosubstituted or polysubstituted by identical or
different substituents, suitable substituents being:
fluorine, chlorine, bromine, iodine, hydroxyl, cyano, amino, in each
case straight-chain or branched alkoxy, alkylthio, N-alkylamino or
N,N-dialkylamino having in each case 1 to 8 carbon atoms in the
individual alkyl moieties;
R4 moreover represents in each case straight-chain or branched alkenyl
or alkinyl having in each case 2 to 8 carbon atoms, or represents in
each case straight-chain or branched halogenoalkenyl or
halogenoalkinyl having in each case 2 to 6 carbon atoms and 1 to 11
identical or different halogen atoms, in particular fluorine, chlorine,
bromine and/or iodine, or represents in each case straight-chain or
branched alkoxy, alkylthio, alkylsulphinyl, alkylsulphonyl or
alkoxycarbonyl having in each case 1 to 8 carbon atoms in the
individual alkyl moieties, or moreover represents cycloalkyl having 3
to 8 carbon atoms, each of which is optionally monosubstituted or
polysubstituted by identical or different substituents consisting of
halogen and/or straight-chain or branched alkyl having 1 to 4 carbon
atoms, or furthermore represents aryl or aryloxy having in each case
6 to 10 carbon atoms, each of which is optionally monosubstituted
or polysubstituted by identical or different substituents, suitable
substituents for aryl being in each case:
halogen, cyano, nitro, in each case straight-chain or branched alkyl,
alkoxy or alkylthio having in each case 1 to 6 carbon atoms, in each
- 62-

case straight-chain or branched halogenoalkyl, halogenoalkoxy or
halogenoalkylthio having in each case 1 to 6 carbon atoms and 1 to
13 identical or different halogen atoms, in each case straight-chain
or branched alkoxycarbonyl or alkoximinoalkyl having in each case
1 to 6 carbon atoms in the individual alkyl moieties, and phenyl
which is optionally monosubstituted or polysubstituted by identical
or different substituents consisting of halogen and/or straight-chain
or branched alkyl having 1 to 6 carbon atoms,
or R4 represents a radical of the formula <IMG> ,
R5 represents hydrogen, cyano, amino or aminocarbonyl, or represents
straight-chain or branched alkyl having 1 to 8 carbon atoms which is
optionally monosubstituted or polysubstituted by identical or
different substituents, suitable substituents being:
fluorine, chlorine, bromine, iodine, hydroxyl, cyano, amino, in each
case straight-chain or branched alkoxy, alkylthio, N-alkylamino or
N,N-dialkylamino having in each case 1 to 8 carbon atoms in the
individual alkyl moieties,
R5 moreover represents in each case straight-chain or branched alkenyl
or alkinyl having in each case 2 to 8 carbon atoms, or represents in
each case straight-chain or branched alkoxy, alkoxycarbonyl, N-
alkylamino, N,N-dialkylamino or alkylideneimino having in each
case 1 to 8 carbon atoms in the individual alkyl moieties, or
furthermore represents cycloalkyl having 3 to 8 carbon atoms, each
of which is optionally monosubstituted or polysubstituted by identical
or different substituents consisting of halogen and/or straight-chain
or branched alkyl having 1 to 4 carbon atoms, or furthermore
- 63-

represents aryl or aryloxy having in each case 6 to 10 carbon atoms,
each of which is optionally monosubstituted or polysubstituted by
identical or different substituents, suitable substituents for aryl being
in each case:
halogen, cyano, nitro, in each case straight-chain or branched alkyl,
alkoxy or alkythio having in each case 1 to 6 carbon atoms, in each
case straight-chain or branched halogenoalkyl, halogenoalkoxy or
halogenoalkylthio having in each case 1 to 6 carbon atoms and 1 to
13 identical of different halogen atoms, in each case straight-chain
or branched alkoxycarbonyl or alkoximinoalkyl having in each case
1 to 6 carbon atoms in the individual alkyl moieties, and phenyl
which is optionally monosubstituted or polysubstituted by identical
or different substituents consisting of halogen and/or straight-chain
or branched alkyl having 1 to 6 carbon atoms,
R6 represents in each case straight-chain or branched alkyl, alkoxy or
alkylthio having in each case 1 to 8 carbon atoms, or represents a
radical of the formula <IMG> ,
R7 represents straight-chain or branched alkyl having 1 to 8 carbon
atoms or represents cycloalkyl having 3 to 8 carbon atoms,
R8 and R9 either independently of one another each represent hydrogen,
or represent straight-chain or branched alkyl having 1 to 8 carbon
atoms, or each represent straight-chain or branched alkenyl or
alkinyl having in each case 2 to 8 carbon atoms, or represent
cycloalkyl having 3 to 8 carbon atoms, or represent arylalkyl or aryl
having in each case 6 to 10 carbon atoms in the aryl moiety and if
appropriate 1 to 6 carbon atoms in the straight-chain or branched
alkyl moiety, each of which is optionally monosubstituted or
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polysubstituted by identical or different substituents, suitable
substituents for aryl being in each case:
halogen, cyano, nitro, in each case straight-chain or branched alkyl,
alkoxy or alkylthio having in each case 1 to 6 carbon atoms, in each
case straight-chain or branched halogenoalkyl, halogenoalkoxy,
halogenoalkylthio having in each case 1 to 6 carbon atoms and 1 to
13 identical or different halogen atoms, in each case straight-chain
or branched alkoxycarbonyl or alkoximinoalkyl having in each case
1 to 6 carbon atoms in the individual alkyl moieties, and phenyl
which is optionally monosubstituted or polysubstituted by identical
or different substituents consisting of halogen and/or straight-chain
or branched alkyl having 1 to 6 carbon atoms;
or R8 and R9, together with the nitrogen atom to which they are
attached, represent a saturated five- to seven-membered heterocycle
which may optionally contain 1 to 2 further heteroatoms - in
particular nitrogen, oxygen or sulphur - and which is optionally
monosubstituted or polysubstituted by identical or different
substituents consisting of straight-chain or branched alkyl having 1 to
4 carbon atoms,
R10 and R11 either independently of one another each represent straight-
chain or branched alkyl having 1 to 8 carbon atoms, or represent in
each case straight-chain or branched alkenyl or alkinyl having in
each case 2 to 8 carbon atoms, or represent straight-chain or
branched halogenoalkyl having 1 to 6 carbon atoms and 1 to 13
identical or different halogen atoms, especially fluorine, chlorine,
bromine and/or iodine, or represent in each case straight-chain or
branched halogenoalkenyl or halogenoalkinyl having in each case 2
to 6 carbon atoms and 1 to 11 identical or different halogen atoms,
especially fluorine, chlorine, bromine and/or iodine, or represent in
each case straight-chain or branched alkoxyalkyl or alkoxy having in
each case 1 to 8 carbon atoms in the individual alkyl moieties, or
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represent cycloalkyl having 3 to 8 carbon atoms, or represent
cycloalkylalkyl having 3 to 8 carbon atoms in the cycloalkyl moiety
and 1 to 6 carbon atoms in the straight-chain or branched alkyl
moiety, or represent aryl or arylalkyl having in each case 6 to 10
carbon atoms in the aryl moiety and if appropriate 1 to 6 carbon
atoms in the straight-chain or branched alkyl moeity, each of which
is optionally monosubstituted or polysubstituted by identical or
different substituents, or represent heteroaryl having 2 to 9 carbon
atoms and 1 to 4 identical or different heteroatoms - in particular
nitrogen, oxygen and/or sulphur - which is optionally
monosubstituted or polysubstituted by identical or different
substituents, suitable substituents for aryl and heteroaryl being in
each case:
halogen, cyano, nitro, in each case straight-chain or branched alkyl,
alkoxy or alkylthio having in each case 1 to 6 carbon atoms, in each
case straight-chain or branched halogenoalkyl, halogenoalkoxy,
halogenoalkylthio having in each case 1 to 6 carbon atoms and 1 to
13 identical or different halogen atoms, in each case straight-chain
or branched alkoxycarbonyl or alkoximinoalkyl having in each case
1 to 6 carbon atoms in the individual alkyl moieties, and phenyl
which is optionally monosubstituted or polysubstituted by identical
or different substituents consisting of halogen and/or straight-chain
or branched alkyl having 1 to 6 carbon atoms;
or R10 and R11, together with the nitrogen atom to which they are
attached, represent a saturated five- to seven-membered heterocycle
which may optionally contain 1 to 2 further heteroatoms - in
particular nitrogen, oxygen and/or sulphur - which is optionally
monosubstituted or polysubstituted by identical or different
substituents consisting of straight-chain or branched alkyl having 1 to
4 carbon atoms, and
X2 represents oxygen or sulphur.
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3. Substituted triazolinones of the general formula (I) according
to Claim 1, characterized in that
Het represents a heterocycle of the formula
<IMG> or <IMG> ,
R1, R2 and R3 independently of one another each represent fluorine,
chlorine or bromine, or represent straight-chain or branched alkyl
having 1 to 6 carbon atoms, or represent straight-chain or branched
alkenyl having 2 to 6 carbon atoms, or represent straight-chain or
branched alkinyl having 2 to 6 carbon atoms, or represent straight-
chain or branched alkoxy having 1 to 6 carbon atoms, or represent
phenylalkyl, phenyl or phenoxy having if appropriate 1 to 4 carbon
atoms in the straight-chain or branched alkyl moiety, each of which
is optionally monosubstituted to trisubstituted by identical or
different substituents, suitable substituents for phenyl being in each
case:
halogen, cyano, nitro, in each case straight-chain or branched alkyl,
alkoxy or alkylthio having in each case 1 to 4 carbon atoms, in each
case straight-chain or branched halogenoalkyl, halogenoalkoxy or
halogenoalkylthio having in each case 1 to 4 carbon atoms and 1 to
9 identical or different halogen atoms, in each case straight-chain or
branched alkoxycarbonyl or alkoximinoalkyl having in each case 1 to
4 carbon atoms in the individual alkyl moieties, and phenyl which is
optionally monosubstituted to trisubstituted by identical or different
substituents consisting of halogen and/or straight-chain or branched
alkyl having 1 to 4 carbon atoms,
- 67-

A represents a divalent alkanediyl radical having 1 to 6 carbon atoms,
and
X1 represents oxygen or sulphur, where
R4 represents hydrogen, fluorine, chlorine, bromine, cyano or nitro, or
represents straight-chain or branched alkyl having 1 to 6 carbon
atoms which is optionally monosubstituted, suitable substituents
being:
hydroxyl, cyano, amino, in each case straight-chain or branched
alkoxy, alkylthio, N-alkylamino or N,N-dialkylamino having in each
case 1 to 6 carbon atoms in the individual alkyl moieties;
R4 moreover represents in each case straight-chain or branched alkenyl
or alkinyl having in each case 2 to 6 carbon atoms, or represents in
each case straight-chain or branched halogenoalkyl having 1 to 4
carbon atoms and 1 to 9 identical or different halogen atoms,
especially fluorine, chlorine, and/or bromine, or represents in each
case straight-chain or branched halogenoalkenyl or halogenoalkinyl
having in each case 2 to 4 carbon atoms and 1 to 7 identical or
different halogen atoms, especially fluorine, chlorine and/or
bromine, or represents in each case straight-chain or branched
alkoxy, alkylthio, alkylsulphinyl, alkylsulphonyl or alkoxycarbonyl
having in each case 1 to 6 carbon atoms in the individual alkyl
moieties, or furthermore represents cycloalkyl having 3 to 7 carbon
atoms, each of which is optionally monosubstituted to
pentasubstituted by identical or different substituents consisting of
chlorine, bromine, methyl and/or ethyl, or furthermore represents
phenyl or phenoxy each of which is optionally monosubstituted to
trisubstituted by identical or different substituents, suitable
substituents for phenyl being in each case:
halogen, cyano, nitro, in each case straight-chain or branched alkyl,
- 68-

alkoxy or alkylthio having in each case 1 to 4 carbon atoms, in each
case straight-chain or branched halogenoalkyl, halogenoalkoxy or
halogenoalkylthio having in each case 1 to 3 carbon atoms and 1 to
9 identical or different halogen atoms, in each case straight-chain or
branched alkoxycarbonyl or alkoximinoalkyl having in each case 1 to
4 carbon atoms in the individual alkyl moieties, and phenyl which is
optionally monosubstituted to trisubstituted by identical or different
substituents consisting of halogen and/or straight-chain or branched
alkyl having 1 to 4 carbon atoms,
or R4 represents a radical of the formula <IMG> ,
R5 represents hydrogen, cyano, amino or aminocarbonyl, or represents
straight-chain or branched alkyl having 1 to 6 carbon atoms which is
optionally monosubstituted or polysubstituted by identical or
different substituents, suitable substituents being:
fluorine, chlorine, bromine, hydroxyl, cyano, amino, in each case
straight-chain or branched alkoxy, alkylthio, N-alkylamino or N,N-
dialkylamino having in each case 1 to 4 carbon atoms in the
individual alkyl moieties;
R5 moreover represents in each case straight-chain or branched alkenyl
or alkinyl having in each case 2 to 6 carbon atoms, or represents in
each case straight-chain or branched alkoxy, alkoxycarbonyl, N-
alkylamino, N,N-dialkylamino or alkylideneimino having in each
case 1 to 6 carbon atoms in the individual alkyl moieties, or
furthermore represents cycloalkyl having 3 to 7 carbon atoms which
is in each case optionally monosubstituted to pentasubstituted by
identical or different substituents consisting of chlorine, bromine,
methyl and/or ethyl, or furthermore represents phenyl or phenoxy
- 69-

each of which is optionally monosubstituted to trisubstituted by
identical or different substituents, suitable substituents for phenyl
being in each case:
halogen, cyano, nitro, in each case straight-chain or branched alkyl,
alkoxy or alkythio having in each case 1 to 4 carbon atoms, in each
case straight-chain or branched halogenoalkyl, halogenoalkoxy or
halogenoalkylthio having in each case 1 to 4 carbon atoms and 1 to
9 identical or different halogen atoms, in each case straight-chain or
branched alkoxycarbonyl or alkoximinoalkyl having in each case 1 to
4 carbon atoms in the individual alkyl moieties, and phenyl which is
optionally monosubstituted to trisubstituted by identical or different
substituents consisting of halogen and/or straight-chain or branched
alkyl having 1 to 4 carbon atoms,
R6 represents in each case straight-chain or branched alkyl, alkoxy or
alkylthio having in each case 1 to 6 carbon atoms, or represents a
radical of the formula <IMG>,
R7 represents straight-chain or branched alkyl having 1 to 6 carbon
atoms or represents cycloalkyl having 3 to 7 carbon atoms,
R8 and R9 either independently of one another each represent hydrogen,
or represent straight-chain or branched alkyl having 1 to 6 carbon
atoms, or represent in each case straight-chain or branched alkenyl
or alkinyl having in each case 2 to 6 carbon atoms, or represent
cycloalkyl having 3 to 7 carbon atoms, or represent phenylalkyl or
phenyl having if appropriate 1 to 4 carbon atoms in the straight-
chain or branched alkyl moiety, each of which is optionally
monosubstituted to trisubstituted by identical or different
substituents, suitable substituents for phenyl being in each case:
- 70-

halogen, cyano, nitro, in each case straight-chain or branched alkyl,
alkoxy or alkythio having in each case 1 to 4 carbon atoms, in each
case straight-chain or branched halogenoalkyl, halogenoalkoxy or
halogenoalkylthio having in each case 1 to 4 carbon atoms and 1 to
9 identical or different halogen atoms, in each case straight-chain or
branched alkoxycarbonyl or alkoximinoalkyl having in each case 1 to
4 carbon atoms in the individual alkyl moieties, and phenyl which is
optionally monosubstituted to trisubstituted by identical or different
substituents consisting of halogen and/or straight-chain or branched
alkyl having 1 to 4 carbon atoms;
or R8 and R9, together with the nitrogen atom to which they are
attached, represent a saturated five- to seven-membered heterocycle
which may optionally contain 1 further heteroatom - in particular
nitrogen, oxygen or sulphur - which is optionally monosubstituted to
tetrasubstituted by identical or different substituents consisting of
straight-chain or branched alkyl having 1 to 3 carbon atoms,
R10 and R11 either independently of one another each represent straight-
chain or branched alkyl having 1 to 6 carbon atoms, or represent in
each case straight-chain or branched alkenyl or alkinyl having in
each case 2 to 6 carbon atoms, or represent straight-chain or
branched halogenoalkyl having 1 to 4 carbon atoms and 1 to 9
identical or different halogen atoms, especially fluorine, chlorine
and/orbromine, or represent in each case straight-chain or branched
halogenoalkenyl or halogenoalkinyl having in each case 2 to 4 carbon
atoms and 1 to 7 identical or different halogen atoms, especially
fluorine, chlorine and/or bromine, or represent in each case straight-
chain or branched alkoxyalkyl or alkoxy having in each case 1 to 6
carbon atoms in the individual alkyl moieties, or represent cycloalkyl
having 3 to 7 carbon atoms, or represent cycloalkylalkyl having 3 to
7 carbon atoms in the cycloalkyl moiety and 1 to 4 carbon atoms in
the straight-chain or branched alkyl moiety, or represent phenyl or
- 71 -

phenylalkyl having if appropriate 1 to 4 carbon atoms in the straight-
chain or branched alkyl moeity, each of which is optionally
monosubstituted to trisubstituted by identical or different sub-
stituents, or represent heteroaryl having 2 to 9 carbon atoms and 1 to
3 identical or different heteroatoms - in particular nitrogen, oxygen
and/or sulphur - which is optionally monosubstituted to
trisubstituted by identical or different substituents, suitable
substituents for aryl and heteroaryl being in each case:
halogen, cyano, nitro, in each case straight-chain or branched alkyl,
alkoxy or alkythio having in each case 1 to 4 carbon atoms, in each
case straight-chain or branched halogenoalkyl, halogenoalkoxy or
halogenoalkylthio having in each case 1 to 4 carbon atoms and 1 to
9 identical or different halogen atoms, in each case straight-chain or
branched alkoxycarbonyl or alkoximinoalkyl having in each case 1 to
4 carbon atoms in the individual alkyl moieties, and phenyl which is
optionally monosubstituted to trisubstituted by identical or different
substituents consisting of halogen and/or straight-chain or branched
alkyl having 1 to 4 carbon atoms;
or R10 and R11, together with the nitrogen atom to which they are
attached, represent a saturated five- to seven-membered heterocycle
which may optionally contain 1 further heteroatom - in particular
nitrogen, oxygen or sulphur - which is optionally monosubstituted to
tetrasubstituted by identical or different substituents consisting of
straight-chain or branched alkyl having 1 to 3 carbon atoms, and
X2 represents oxygen or sulphur.
4. Substituted triazolinones of the general formula (I) according
to Claim 1, characterized in that
Het represents a heterocycle of the formula
- 72-

<IMG> or <IMG> ,
R1, R2 and R3 independently of one another each represent fluorine,
chlorine or bromine, or represent straight-chain or branched alkyl
having 1 to 4 carbon atoms, or represent straight-chain or branched
alkenyl having 2 to 4 carbon atoms, or represent straight-chain or
branched alkinyl having 2 to 4 carbon atoms, or represent straight-
chain or branched alkoxy having 1 to 4 carbon atoms, or represent
phenylalkyl, phenyl or phenoxy having if appropriate 1 to 3 carbon
atoms in the straight-chain or branched alkyl moiety, each of which
is optionally monosubstituted or disubstituted by identical or
different substituents, suitable substituents for phenyl being in each
case:
fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, n- or i-
propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, n-, i-,
s- or t-butoxy, methylthio, ethylthio, trifluoromethyl,
difluoromethyl, trifluoromethoxy, difluoromethoxy,
trifluoromethylthio, - methoxycarbonyl, ethoxycarbonyl,
methoximinomethyl, methoximinoethyl, ethoximinomethyl,
ethoximinoethyl or phenyl which is optionally monosubstituted to
disubstituted by identical or different substituents consisting of
fluorine, chlorine, bromine, methyl and/or ethyl;
A represents a divalent alkanediyl radical having 1 to 4 carbon atoms,
and
X1 represents oxygen or sulphur, where
- 73 -

R4 represents hydrogen, fluorine, chlorine, bromine, cyano or nitro, or
represents straight-chain or branched alkyl having 1 to 4 carbon
atoms which is optionally monosubstituted, suitable substituents
being:
hydroxyl, cyano, amino, in each case straight-chain or branched
alkoxy, alkylthio, N-alkylamino or N,N-dialkylamino having in each
case 1 to 4 carbon atoms in the individual alkyl moieties;
R4 moreover represents in each case straight-chain or branched alkenyl
or alkinyl having in each case 2 to 4 carbon atoms, or represents
halogenoalkyl having 1 or 2 carbon atoms and 1 to 5 identical or
different halogen atoms, especially fluorine, chlorine and/or
bromine, or represents in each case straight-chain or branched
halogenoalkenyl or halogenoalkinyl having in each case 2 to 3 carbon
atoms and 1 to 5 identical or different halogen atoms, especially
fluorine, chlorine and/or bromine, or represents in each case
straight-chain or branched alkoxy, alkylthio, alkylsulphinyl,
alkylsulphonyl or alkoxycarbonyl having in each case 1 to 4 carbon
atoms in the individual alkyl moieties, or furthermore represents
cycloalkyl having 3 to 6 carbon atoms, or furthermore represents
phenyl or phenoxy, each of which is optionally monosubstituted or
disubstituted by identical or different substituents, suitable
substituents for phenyl being in each case:
fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, n- or i-
propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, n-, i-,
s- or t-butoxy, methylthio, ethylthio, trifluoromethyl,
difluoromethyl, trifluoromethoxy, difluoromethoxy,
trifluoromethylthio, methoxycarbonyl, ethoxycarbonyl,
methoximinomethyl, methoximinoethyl, ethoximinomethyl,
ethoximinoethyl or phenyl which is optionally monosubstituted to
disubstituted by identical or different substituents consisting of
fluorine, chlorine, bromine, methyl and/or ethyl;
- 74-

or R4 represents a radical of the formula <IMG> ,
R5 represents hydrogen, cyano, amino or aminocarbonyl, or represents
straight-chain or branched alkyl having 1 to 4 carbon atoms which is
optionally monosubstituted or polysubstituted by identical or
different substituents, suitable substituents being:
fluorine, chlorine, bromine, hydroxyl, cyano, amino, in each case
straight-chain or branched alkoxy, alkylthio, N-alkylamino or N,N-
dialkylamino having in each case 1 to 3 carbon atoms in the
individual alkyl moieties;
R5 moreover represents in each case straight-chain or branched alkenyl
or alkinyl having in each case 2 to 4 carbon atoms, or represents in
each case straight-chain or branched alkoxy, alkoxycarbonyl, N-
alkylamino, N,N-dialkylamino or alkylideneimino having in each
case 1 to 4 carbon atoms in the individual alkyl moieties, or
furthermore represents cycloalkyl having 3 to 6 carbon atoms, or
furthermore represents phenyl or phenoxy each of which is option-
ally monosubstituted or disubstituted by identical or different
substituents, suitable substituents for phenyl being in each case:
fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, n- or i-
propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, n-, i-,
s- or t-butoxy, methylthio, ethylthio, trifluoromethyl,
difluoromethyl, trifluoromethoxy, difluoromethoxy,
trifluoromethylthio, methoxycarbonyl, ethoxycarbonyl,
methoximinomethyl, methoximinoethyl, ethoximinomethyl,
ethoximinoethyl or phenyl which is optionally monosubstituted to
disubstituted by identical or different substituents consisting of
fluorine, chlorine, bromine, methyl and/or ethyl;
- 75-

R6 represents in each case straight-chain or branched alkyl, alkoxy or
alkylthio having in each case 1 to 4 carbon atoms, or represents a
radical of the formula <IMG>,
R7 represents straight-chain or branched alkyl having 1 to 4 carbon
atoms or represents cycloalkyl having 3 to 6 carbon atoms,
R8 and R9 either independently of one another each represent hydrogen,
or represent straight-chain or branched alkyl having 1 to 4 carbon
atoms, or represent in each case straight-chain or branched alkenyl
or alkinyl having in each case 2 to 4 carbon atoms, or represent
cycloalkyl having 3 to 6 carbon atoms, or represent phenylalkyl or
phenyl having if appropriate 1 to 3 carbon atoms in the straight-
chain or branched alkyl moiety, each of which is optionally
monosubstituted or disubstituted by identical or different
substituents, suitable substituents for phenyl being in each case:
fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, n- or i-
propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, n-, i-,
s- or t-butoxy, methylthio, ethylthio, trifluoromethyl,
difluoromethyl, trifluoromethoxy, difluoromethoxy,
trifluoromethylthio, methoxycarbonyl, ethoxycarbonyl,
methoximinomethyl, methoximinoethyl, ethoximinomethyl,
ethoximinoethyl or phenyl which is optionally monosubstituted to
disubstituted by identical or different substituents consisting of
fluorine, chlorine, bromine, methyl and/or ethyl;
or R8 and R9, together with the nitrogen atom to which they are
attached, represent a saturated five- to seven-membered heterocycle
which may optionally contain 1 further heteroatom - in particular
nitrogen, oxygen or sulphur - which is optionally monosubstituted or
- 76-

disubstituted by identical or different substituents consisting of
methyl and/or ethyl,
R10 and R11 either independently of one another each represent straight-
chain or branched alkyl having 1 to 4 carbon atoms, or represent in
each case straight-chain or branched alkenyl or alkinyl having in
each case 2 to 4 carbon atoms, or represent straight-chain or
branched halogenoalkyl having 1 to 3 carbon atoms and 1 to 7
identical or different halogen atoms, especially fluorine, chlorine
and/or bromine, or represent in each case straight-chain or branched
halogenoalkenyl or halogenoalkinyl having in each case 2 to 3 carbon
atoms and 1 to 5 identical or different halogen atoms, especially
fluorine, chlorine and/or bromine, or represent in each case straight-
chain or branched alkoxyalkyl or alkoxy having in each case 1 to 4
carbon atoms in the individual alkyl moieties, or represent cycloalkyl
having 3 to 6 carbon atoms, or represent cycloalkylalkyl having 3 to
6 carbon atoms in the cycloalkyl moiety and 1 or 2 carbon atoms in
the alkyl moiety, or represent phenyl or phenylalkyl having if appro-
priate 1 to 3 carbon atoms in the straight-chain or branched alkyl
moeity, each of which is optionally monosubstituted or disubstituted
by identical or different substituents, or represent heteroaryl having
2 to 5 carbon atoms and 1 to 3 identical or different heteroatoms -
in particular nitrogen, oxygen and/or sulphur - which is optionally
monosubstituted or disubstituted by identical or different sub-
stituents, suitable substituents for aryl and/or heteroaryl being in
each case:
fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, n- or i-
propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, n-, i-,
s- or t-butoxy, methylthio, ethylthio, trifluoromethyl,
difluoromethyl, trifluoromethoxy, difluoromethoxy,
trifluoromethylthio, methoxycarbonyl, ethoxycarbonyl,
methoximinomethyl, methoximinoethyl, ethoximinomethyl,
- 77 -

ethoximinoethyl or phenyl which is optionally monosubstituted to
disubstituted by identical or different substituents consisting of
fluorine, chlorine, bromine, methyl and/or ethyl;
or R10 and R11, together with the nitrogen atom to which they are
attached, represent a saturated five- to seven-membered heterocycle
which may optionally contain 1 further heteroatom - in particular
nitrogen, oxygen or sulphur - which is optionally monosubstituted or
disubstituted by identical or different substituents consisting methyl
and/or ethyl, and
X2 represents oxygen or sulphur.
5. Process for the preparation of substituted triazolinones of the
general formula (I)
<IMG>
(I)
Het represents a heterocycle of the formula
<IMG> or <IMG>,
R1, R2 and R3 independently of one another each represent halogen,
alkyl, alkenyl, alkinyl or alkoxy or represents in each case optionally
substituted arylalkyl, aryl or aryloxy,
A represents a divalent alkanediyl radical, and
- 78-

X1 represents oxygen or sulphur, where
R4 represents hydrogen, halogen, cyano or nitro or represents optionally
substituted alkyl, or represents alkenyl, alkinyl, halogenoalkenyl,
halogenoalkinyl, alkoxy, alkylthio, alkylsulphinyl, alkylsulphonyl or
alkoxycarbonyl, or represents in each case optionally substituted
cycloalkyl, aryl or aryloxy, or represents a radical of the formula
<IMG>
R5 represents hydrogen or cyano, or represents optionally substituted
alkyl, or represents alkenyl, alkinyl, alkoxy, alkoxycarbonyl or
aminocarbonyl, or represents amino, N-alkylamino, N,N-
dialkylamino or alkylideneimino, or represents in each case option-
ally substituted cycloalkyl, aryl or aryloxy,
R6 represents alkyl, alkoxy or alkylthio, or represents a radical of the
formula <IMG>,
R7 represents alkyl or cycloalkyl,
R8 and R9 either independently of one another each represent hydrogen,
alkyl, alkenyl, alkinyl or cycloalkyl or represent in each case
optionally substituted arylalkyl or aryl, or, together with the nitrogen
atom to wich they are attached, represent an optionally substituted
heterocycle,
- 79-

R10 and R11 either independently of one another each represent alkyl,
alkenyl, alkinyl, halogenoalkyl, halogenoalkenyl, halogenoalkinyl,
alkoxyalkyl, alkoxy, cycloalkyl or cycloalkylalkyl or represent in each
case optionally substituted aryl, arylalkyl or heteroaryl, or, together
with the nitrogen atom to which they are attached, represent an
optionally substituted heterocycle, and
X2 represents oxygen or sulphur,
characterized in that
a) 1-chloro(thio)carbonyltriazolinones of the formula (II)
<IMG> (II)
in which
Het and X1 have the meanings given above
are reacted with amines of the formula (III)
<IMG> (III)
in which
R1, R2, R3 and A have the meanings given above,
optionally in the presence of a diluent and optionally in the presence of
a reaction auxiliary,
or if
- 80-

b) 1-unsubstituted triazolinones of the formula (IV)
Het-H (IV)
in which
Het has the meaning given above
are reacted with iso(thio)cyanates of the formula (V)
<IMG> (V)
in which
R1, R2, R3, A and X1 have the meanings given above,
optionally in the presence of a diluent and optionally in the presence of
a reaction auxiliary.
6. Herbicidal compositions, characterize in that they contain at
least one substituted triazolinone of the general formula (I) according to
Claims 1 to 5.
7. Method of combating unwanted plants, characterized in that
substituted triazolinones of the general formula (I) according to Claims
1 to 5 are caused to act on plants and/or their habitat.
8. Use of substituted triazolinones of the general formula (I)
according to Claims 1 to 5 for combating unwanted plants.
9. Process for the preparation of herbicidal compositions,
- 81 -

characterized in that substituted triazolinones of the general formula (I)
according to Claims 1 to 5 are mixed with extenders and/or surface-
active substances.
- 82-

Description

-2~46~1
- BAYER AE~IENGESELLSCHA~T 51368 Leve~sen
Konzemvc~ RP
Patente Konzern
E. rlPI IN THIS ~4..l~LJL
T~XT TRANSLATION
Substituted triazolinones
5 The invention relates to novel substituted triazolinones, to a number of
processes for their preparation and to their use as herbicides.
It is known that certain substituted triazolinones, such as, for example, the
compound 2-methyl-3-dimethylamino- 1-[N-(2,2-dimethyl- 1-propyl)-
aminocarbonyl]- 1,2,~triazolin-5-one, possess herbicidal ~opellies (cf. e.g. EP
10 431 390).
However, the herbicidal activity of these previously known compounds with
respect to problem weeds, and their tolerance by important crop plants, is not
completely ~ti~ctory in all areas of application.
Novel substituted triazolinones have been found of the general formula (I)
~t Rl
Xl' ~N~A--S~R (I)
R3
15 in which
Het represents a heterocycle of the formula
Le A 29 399-PCT

~1~6fi~
R R5 R6
\~N
or R N~N>~
Rl, R2 and R3 independently of one another each rc~resellt halogen,
alkyl, alkenyl, alkinyl or alkoxy or represent in each case optionally
substituted arylalkyl, aryl or aryloxy,
S A represents a divalent alkanediyl radical, and
Xl represents oxygen or sulphur, where
R4 represents hydrogen, halogen, cyano or nitro or represents optionally
substituted alkyl, or represents alkenyl, alkinyl, halogenoalkenyl,
halogenoalkinyl, alkoxy, alkylthio, alkylsulphinyl, alkylsulphonyl or
alkoxycarbonyl, or represents in each case optionally substituted
cycloalkyl, aryl or aryloxy, or represents a radical of the formula
R
--N/,
R
R5 represents hydrogen or cyano, or represents optionally substituted
alkyl, or represents alkenyl, alkinyl, alkoxy, alkoxycarbonyl or
aminocarbonyl, or represents amino, N-alkylamino, N,N-
dialkylamino or alkylideneimino, or represents in each case
optionally substituted cycloalkyl, aryl or aryloxy,
R6 represents alkyl, alkoxy or alkylthio, or represents a radical of the
Le A 29 399-PCT - 2 -

- 214666l
RD
formula _~,
~Rn
R7 represents alkyl or cycloalkyl,
R8 and R9 either independently of one another each represent hydrogen,
alkyl, alkenyl, alkinyl or cycloalkyl or represent in each case
S optionally substituted arylalkyl or aryl, or, together with the nitrogen
atom to which they are attached, represent an optionally substituted
heterocycle,
Rl and Rll either independently of one another each represent alkyl,
alkenyl, alkinyl, halogenoalkyl, halogenoalkenyl, halogenoalkinyl,
alkoxyalkyl, alkoxy, cycloalkyl or cycloalk~alkyl or l~resent in each
case optionally substituted aryl, arylalkyl or heteroaryl, or, together
with the nitrogen atom to which they are attached, represent an
optionally substituted heterocycle, and
~2 represents oxygen or sulphur.
The compounds ofthe formula-(I) may if ~lo~liate, dependingon the nature
of the substituents, be present as geometrical and/ or optical isomers or isomermixtures of different composition. Both the pure isomers and the isomer
mixtures are claimed according to the invention.
It has furthermore been found that the novel substituted triazolinones of the
general formula (I)
R
X' `N~A--S~R (I)
R3
LeA29399 3

21~6~1
in which
Het represents a heterocycle of the formula
R4 R5 R6
\~N \~N
~N~X~ or R--N~N~X2
R', R2 and R3 independently of one another each represent halogen,
S alkyl, alkenyl, alkinyl or alkoxy or represellt in each case optionally
substituted arylalkyl, aryl or aryloxy,
A represents a divalent alkanediyl radical, and
Xl represents oxygen or sulphur, where
R4 represents hydrogen, halogen, cyano or nitro or represents optionally
substituted alkyl, or represents alkenyl, alkinyl, halogenoalkenyl,
halogenoalkinyl, alkoxy, alkylthio, alkylsulphinyl, alkylsulphonyl or
alkoxycarbonyl, or represents in each case optionally substituted
cycloalkyl, aryl or aryloxy, or replesellts a radical of the forrnula
R
R
R5 represents hydrogen or cyano, or represents optionally substituted
alkyl, or represents alkenyl, alkinyl, alkoxy, alkoxycarbonyl or
aminocarbonyl, or represents amino, N-alkylamino, N,N-
dialkylarnino or alkylideneimino, or represents in each case
optionally substituted cycloalkyl, aryl or aryloxy,
Le A 29 399 - 4 -

~1~6~l
- R6 re~lesellts alkyl, alkoxy or alkylthio, or represents a radical of the
R
formula ~
R7 replesellts alkyl or cycloalkyl,
R8 and R9 either independently of one another each re~resel~t hydrogen,
S alkyl, alkenyl, alkinyl or cycloalkyl or represent in each case
optionally substituted arylalkyl or aryl, or, together with the nitrogen
atom to which they are attached, represent an optionally sllkstitllted
heterocycle,
R~ and Rl~ either independently of one another each represellt alkyl,
alkenyl, alkinyl, halogenoalkyl, halogenoalkenyl, halogenoalkinyl,
alkoxyalkyl, alkoxy, cycloalkyl or cycloalkylalkyl or r~resellt in each
case optionally substituted aryl, arylalkyl or heteroaryl, or, together
with the nitrogen atom to which they are attached, represent an
optionally substituted heterocycle, and
x2 represents oxygen or sulphur,
are obtained if
a) l-chloro(thio)carbonyltriazolinones of the forrnula (II)
Xl, C~
in which
Het and X' have the me~nin~ given above
Le A 29 399 s -

~l466~l
- are reacted with amines of the formula (III)
,.
~N--
in which
Rl, R2, R3 and A have the me~nin~; given above,
optionally in the presence of a diluent and optionally in the presence of a
S reaction auxiliary,
or if
b) 1-unsubstituted triazolinones ofthe formula (IV~
Het-H (IV)
in which
Het has the meaning given above
are reacted with iso(thio)cyanates of the formula (V~ ~
X~N--~S~R (V)
R3
in which
R', R2, R3, A and X' have the me~nin~ given above,
optionally in the presence of a diluent and optionally in the presence of a
15 reaction auxiliary.
Le A 29 399 - 6 -

21~66~
Finally it has been found that the novel substituted triazolinones ofthe generalformula (I) possess herbicidal properties.
Surprisingly, the substituted triazolinones according to the invention, of the
general formula (I), display a considerably better herbicidal acitivity with
respect to problem weeds, while at the same time being tolerated to a markedly
increased extent by important crop plants, in comparison with the substituted
triazolinones known from the prior art, such as, for example, the compound 2-
methyl-3-dimethylamino- 1-rN-(2,2-dimethyl- 1-propyl)-aminocarbonyl]- 1,2,~
triazolin-5-one, which compounds are closely related chemically and in terms
of their mode of action.
A general definition of the substituted triazolinones according to the inventionis given by the formula (I). Preferred compounds of the formula (I) are those
in which
Het represents a heterocycle of the formula
R R R6
\ N' \~N
~N~X2 or R~N~X2
R', R2 and R3 independently of one another each represent fluorine, chlorine,
bromine or iodine, or represent straight-chain or branched alkyl having
1 to 8 carbon atoms, or represent straight-chain or branched alkenyl
having 2 to 8 carbon atoms, or represent straight-chain or branched
alkinyl having 2 to 8 carbon atoms, or represent straight-chain or
branched alkoxy having 1 to 8 carbon atoms, or represent arylalkyl, aryl
or aryloxy having in each case 6 to 10 carbon atoms in the aryl moiety
and ~ropliate 1 to 6 carbon atoms in the straight-chain or branched
alkyl moiety, each of which is optionally monosubstituted or
Le A 29 399 7

21 ~ 66~1
- polysubstituted by identical or different substituents, suitable substituents
for aryl being in each case:
halogen, cyano, nitro, in each case straight-chain or branched alkyl,
alkoxy or alkylthio having in each case 1 to 6 carbon atoms, in each case
straight-chain or branched halogenoalkyl, halogenoalkoxy or
halogenoalkylthio having in each cæ 1 to 6 carbon atoms and 1 to 13
identical or different halogen atoms, in each case straight-chain or
branched alkoxycarbonyl or alkoximinoalkyl having in each case 1 to 6
carbon atoms in the individual alkyl moieties, and phenyl which is
optionally monosubstituted or polysubstituted by identical or different
substituents con~i~ingofhalogen and/or straight-chain or branched alkyl
having 1 to 6 carbon atoms,
A represents a divalent alkanediyl radical having 1 to 8 carbon atoms, and
X~ re~resellts oxygen or sulphur, where
15 R4 represents hydrogen, fluorine, chlorine, bromine, iodine, cyano or nitro,
or represents straight-chain or branched alkyl which is optionally mono-
substituted or polysubstituted by identical or different substituents,
suitable substituents being:
fluorine, chlorine, bromine, iodine, hydroxyl, cyano, amino, in each case
straight-chain or branched alkoxy, alkylthio, N-alkylamino or N,N-
dialkylamino having in each case 1 to 8 carbon atoms in the individual
alkyl moieties;
R4 moreover represents in each case straight-chain or branched alkenyl or
alkinyl having in each case 2 to 8 carbon atoms, or represents in each
case straight-chain or branched halogenoalkenyl or halogenoalkinyl
having in each case 2 to 6 carbon atoms and 1 to 11 identical or different
halogen atoms, in particular fluorine, chlorine, bromine andtor iodine,
LeA29399 - 8-

21~66~
or represents in each case straight-chain or branched alkoxy, alkylthio,
alkylsulphinyl, alkylsulphonyl or alkoxycarbonyl having in each case 1 to
8 carbon atoms in the individual alkyl moieties, or moreover represents
cycloalkyl having 3 to 8 carbon atoms, each of which is optionally
monosubstituted or polysubstituted by identical or different substituents
con~i~ting of halogen and/or straight-chain or branched allyl having 1 to
4 carbon atoms, or fu~thermore re~resellts aryl or aryloxy having in each
case 6 to 10 carbon atoms, each of which is optionally monosubstituted
or polysubstituted by identical or ` dilI~rellt substituents, suitable
substituents for aryl being in each case:
halogen, cyano, nitro, in each case straight-chain or branched alkyl,
alkoxy or alkylthio having in each case 1 to 6 carbon atoms, in each case
straight-chain or branched halogenoalkyl, halogenoalkoxy or
halogenoalkylthio having in each case 1 to 6 carbon atoms and 1 to 13
identical or different halogen atoms, in each case straight-chain or
branched alkoxycarbonyl or alkoximinoalkyl having in each case 1 to 6
carbon atoms in the individual alkyl moieties, and phenyl which is
optionally monosubstituted or polysubstituted by identical or di~lellt
substituents con~i~tingofhalogen and/or straight-chain or branched alkyl
having 1 to 6 carbon atoms,
or R4 represents a radical of the formula ~
R
R5 represents hydrogen, cyano, amino or aminocarbonyl, or represents
straight-chain or branched alkyl having 1 to 8 carbon atoms which is
optionally monosubstituted or polysubstituted by identical or different
substituents, suitable substituents being:
fiuorine, chlorine, bromine, iodine, hydroxyl, cyano, amino, in each case
Le A 29 399 ~ 9 ~

2~666i
straight-chain or branched alkoxy, alkylthio, N-alkylamino or N,N-
dialkylamino having in each case 1 to 8 carbon atoms in the individual
alkyl moieties;
R5 moreover leplesellts in each case straight-chain or branched alkenyl or
alkinyl having in each case 2 to 8 carbon atoms, or represellt~ in each
case straight-chain or branched alkoxy, alkoxycarbonyl, N-alkylamino,
N,N-dialkylamino or alkylideneimino having in each case 1 to 8 carbon
atoms in the individual alkyl moieties, or furthermore represents
cycloalkyl having 3 to 8 carbon atoms, each of which is optionally
monosubstituted or polysubstituted by identical or different substituents
con~i~tingofhalogen and/or straight-chain or branched alkyl having 1 to
4 carbon atoms, or furthermore represents aryl or aryloxy having in each
case 6 to 10 carbon atoms, each of which is optionally monosubstituted
or polysubstituted by identical or di~lellt substituents, suitable
substituents for aryl being in each case:
halogen, cyano, nitro, in each case straight-chain or branched alkyl,
alkoxy or alk~thio having in each case 1 to 6 carbon atoms, in each case
straight-chain or branched halogenoalkyl, halogenoalkoxy or
halogenoalkylthio having in each case 1 to 6 carbon atoms and 1 to 13
identical or different halogen atoms, in each case straight-chain or
branched alkoxycarbonyl or alkoximinoalkyl having in each case 1 to 6
carbon atoms in the individual alkyl moieties, and phenyl which is
optionally monosubstituted or polysubstituted by identical or different
substituents con~i~ingofhalogen andl or straight-chain or branched alkyl
having 1 to 6 carbon atoms,
R6 represents in each case strai~ht-chain or branched alkyl, alkoxy or
alkylthio having in each case 1 to 8 carbon atoms, or represents a radical
RL
of the formula ~
Le A 29 399 - 10 -

~1~66~
R7 represents straight-chain or branched alkyl having 1 to 8 carbon atoms or
represents cycloalkyl having 3 to 8 carbon atoms,
R8 and R9 either independently of one another each lepresent hydrogen, or
represent straight-chain or branched alkyl having 1 to 8 carbon atoms, or
each represent straight-chain or branched alkenyl or alkinyl having in
each case 2 to 8 carbon atoms, or l~,esel~t cycloalkyl having 3 to 8
carbon atoms, or le~,lesellt arylalkyl or aryl having in each case 6 to 10
carbon atoms in the aryl moiety and if a,~,~ropliate 1 to 6 carbon atoms
in the straight-chain or branched alkyl moiety, each of which is
optionally monosubstituted or polysubstituted by identical or different
substituents, suitable substituents for aryl being in each case:
halogen, cyano, nitro, in each case straight-chain or branched alkyl,
alkoxy or alkylthio having in each case 1 to 6 carbon atoms, in each case
straight-chain or branched halogenoalkyl, halogenoalkoxy, halogeno-
alkylthio having in each case 1 to 6 carbon atoms and 1 to 13 identical
or different halogen atoms, in each case straight-chain or branched
alkoxycarbonyl or alkoximinoalkyl having in each case 1 to 6 carbon
atoms in the individual alkyl moieties, and phenyl which is optionally
monosubstituted or polysubstituted by identical or different substituents
con~i~tingofhalogen and/or straight-chain or branched alkyl having 1 to
6 carbon atoms;
or R8 and R9, together with the nitrogen atom to which they are
attached, represent a saturated five- to seven-membered heterocycle
which may optionally contain 1 to 2 filrther heteroatoms - in particular
nitrogen, oxygen or sulphur - and which is optionally monosubstituted or
polysubstituted by identical or different substituents consisting of
straight-chain or branched alkyl having 1 to 4 carbon atoms,
Rl and R~ ~ either independently of one another each represent straight-chain
or branched alkyl having 1 to 8 carbon atoms, or represent in each case
Le A 29 399 - 11 -

~14665~
straight-chain or branched alkenyl or alkinyl having in each case 2 to 8
carbon atoms, or represent straight-chain or branched halogenoalkyl
having 1 to 6 carbon atoms and 1 to 13 identical or different halogen
atoms, especially ~uorine, chlorine, bromine andlor iodine, or represent
S in each case straight-chain or branched halogenoalkenyl or
halogenoalkinyl having in each case 2 to 6 carbon atoms and 1 to 11
identical or di~lellt halogen atoms, especially ~uorine, chlorine,
bromine and/or iodine, or represent in each case straight-chain or
branched alkoxyalkyl or alkoxy having in each case 1 to 8 carbon atoms
in the individual alkyl moieties, or represent cycloalkyl having 3 to 8
carbon atoms, or represent cycloalkylalkyl having 3 to 8 carbon atoms in
the cycloalkyl moiety and 1 to 6 carbon atoms in the straight-chain or
branched alkyl moiety, or represent aryl or arylalkyl having in each case
6 to 10 carbon atoms in the aryl moiety and if a~ro~l;ate 1 to 6 carbon
atoms in the straight-chain or branched alkyl moeity, each of which is
optionally monosubstituted or polysubstituted by identical or different
substituents, or represellt heteroaryl having 2 to 9 carbon atoms and 1 to
4 identical or different heteroatoms - in particular nitrogen, oxygen
andlor sulphur - which is optionally monosubstituted or polysubstituted
by identical or different substituents, suitable substituents for aryl and
heteroaryl being in each case:
halogen, cyano, nitro, in each case straight-chain or branched alkyl,
alkoxy or alkylthio having in each case 1 to 6 carbon atoms, in each case
straight-chain or branched halogenoalkyl, halogenoalkoxy,
halogenoalkylthio having in each case 1 to 6 carbon atoms and 1 to 13
identical or different halogen atoms, in each case straight-chain or
branched alkoxycarbonyl or alkoximinoalkyl having in each case 1 to 6
carbon atoms in the individual alkyl moieties, and phenyl which is
optionally monosubstituted or polysubstituted by identical or different
substituentscon~i~tingofhalogenand/orstraight-chainorbranchedalkyl
having 1 to 6 carbon atoms;
Le A 29 399 - 12 -

2~6~
or Rl and R'l, together with the nitrogen atom to which they are
attached, l~resent a saturated five- to seven-membered heterocycle
which may optionally contain 1 to 2 further heteroatoms - in particular
nitrogen, oxygen and/or sulphur - which is optionally monosubstituted
S or polysubstituted by identical or different substituents con~i~ting of
strai ht-chain or branched alkyl having 1 to 4 carbon atoms, and
~2 represents oxygen or sulphur.
Particularly preferred compounds of the formula (I) are those in which
Het rc~rescllts a heterocycle of the formula
R R5 R6
~N>~X2 or R~
Rl, R2 and R3 independently of one another each represent fluorine, chlorine
or bromine, or represent straight-chain or branched alkyl having 1 to 6
carbon atoms, or represent straight-chain or branched alkenyl having 2
to 6 carbon atoms, or represent straight-chain or branched alkinyl having
2 to 6 carbon atoms, or represent straight-chain or branched alkoxy
having 1 to 6 carbon atoms, or represent phenylalkyl, phenyl or phenoxy
having if ~plopl;ate 1 to 4 carbon atoms in the straight-chain or
branched alkyl moiety, each of which is optionally monosubstituted to
trisubstituted by identical or different substituents, suitable substituents
for phenyl being in each case:
halogen, cyano, nitro, in each case straight-chain or branched alkyl,
alkoxy or alkylthio having in each case 1 to 4 carbon atoms, in each case
straight-chain or branched halogenoalkyl, halogenoalkoxy or
Le A 29 399 - 13 -

- ~146~6i
halogenoalkylthio having in each case 1 to 4 carbon atoms and 1 to 9
identical or different halogen atoms, in each case straight-chain or
branched alkoxycarbonyl or alkoximinoalkyl having in each case 1 to 4
carbon atoms in the individual alkyl moieties, and phenyl which is
S optionally monosubstituted to trisubstituted by identical or different
substituents con.ci.~tingofhalogen and/or straight-chain or branched alkyl
having 1 to 4 carbon atoms,
- A lc~lcsellt~ a divalent alkanediyl radical having 1 to 6 carbon atoms, and
Xl re~l~sellts oxygen or sulphur, where
R4 rc~lcsellls hydrogen, fluorine, chlorine, bromine, cyano or nitro, or
lc~csellt~ straight-chain or branched alkyl having 1 to 6 carbon atoms
which is optionally monosubstituted, suitable substituents being
hydroxyl, cyano, amino, in each case straight-chain or branched alkoxy,
alkylthio, N-alkylamino or N,N-dialkylamino having in each case 1 to
6 carbon atoms in the individual alkyl moieties;
R4 moreover represents in each case straight-chain or branched alkenyl or
alkinyl having in each case 2 to 6 carbon atoms, or represents in each
case straight-chain or branched halogenoalkyl having~ 1 to 4 carbon
atoms and 1 to 9 identical or different halogen atoms, especially fluorine,
chlorine, and/or bromine, or represents in each case straight-chain or
branched halogenoalkenyl or halogenoalkinyl having in each case 2 to 4
carbon atoms and 1 to 7 identical or different halogen atoms, especially
fluorine, chlroine and/or bromine, or represents in each case straight-
chain or branched alkoxy, alkylthio, alkylsulphinyl, alkylsulphonyl or
alkoxycarbonyl having in each case 1 to 6 carbon atoms in the individual
alkyl moieties, or furthermore represents cycloalkyl having 3 to 7 carbon
atoms, each of which is optionally monosubstituted to pentasubstituted
by identical or different substituents consisting of chlorine, bromine,
LeA29399 - 14-

2~6~1
methyl and/ or ethyl, or furthermore represents phenyl or phenoxy each
of which is optionally monosubstituted to trisubstituted by identical or
different substituents, suitable substituents for phenyl being in each case:
halogen, cyano, nitro, in each case straight-chain or branched alkyl,
S alkoxy or alkylthio having in each case 1 to 4 carbon atoms, in each case
straight-chain or branched halogenoalkyl, halogenoalkoxy or
halogenoalkylthio having in each case 1 to 4 carbon atoms and 1 to 9
identical or different halogen atoms, in each case strai~ht-chain or
branched alkoxycarbonyl or alkoximinoalkyl having in each case 1 to 4
carbon atoms in the individual alkyl moieties, and phenyl which is
optionally monosubstituted to trisubstituted by identical or different
substituentscon~i~tingofhalogen and/or straight-chain orbranched alkyl
having 1 to 4 carbon atoms,
or R4 represents a radical of the formula ~
R
15 R5 represents hydrogen, cyano, arnino or aminocarbonyl, or represents
straight-chain or branched alkyl having 1 to 6 carbon atoms which is
optionally monosubstituted or polysubstituted by identical or different
substituents, suitable substituents being:
fluorine, chlorine, bromine, hydroxyl, cyano, amino, in each case
straight-chain or branched alkoxy, alkylthio, N-alkylamino orN,N-
dialkylamino having in each case 1 to 4 carbon atoms in the individual
alkyl moieties;
R5 moreover represents in each case straight-chain or branched alkenyl or
alkinyl having in each case 2 to 6 carbon atoms, or represents in each
case straight-chain or branched alkoxy, alkoxycarbonyl, N-alkylamino,
Le A 29 399 - lS -

2146~61
N,N-dialkylamino or alkylideneimino having in each case 1 to 6 carbon
atoms in the individual alkyl moieties, or furthermore represents
cycloalkyl having 3 to 7 carbon atoms which is in each case optionally
monosubstituted to pentasubstituted by identical or different substituents
S con~i~ting of chlorine, bromine, methyl and/or ethyl, or furthermore
represents phenyl or phenoxy each of which is optionally
monosubstituted to trisubstituted by identical or different substituents,
suitable substituents for phenyl being in each case:
halogen, cyano, nitro, in each case straight-chain or branched alkyl,
alkoxy or allythio having in each case 1 to 4 carbon atoms, in each case
straight-chain or branched halogenoallyl, halogenoalkoxy or
halogenoalkylthio having in each case 1 to 4 carbon atoms and 1 to 9
identical or different halogen atoms, in each case straight-chain or
branched alkoxy~;all~nyl or alkoximinoalkyl having in each case 1 to 4
carbon atoms in the individual alkyl moieties, and phenyl which is
optionally monosubstituted to trisubstituted by identical or different
substituents con ~i ~ti n ~ of halogen and/ or straight- chain or branched alkylhaving 1 to 4 carbon atoms,
R6 represents in each case straight-chain or branched alkyl, alkoxy or
alkylthio having in each case 1 to 6 carbon atoms, or replesellts a radical
RD
of the formula ~
R
R7 represents straight-chain or branched alkyl having 1 to 6 carbon atoms or
represents cycloalkyl having 3 to 7 carbon atoms,
Rg and R9 either independently of one another each r~les~llt hydrogen, or
represent straight-chain or branched alkyl having 1 to 6 carbon atoms, or
represent in each case straight-chain or branched alkenyl or alkinyl
having in each case 2 to 6 carbon atoms, or represent cycloalkyl having
Le A 29 399 - 16 -

2146~6 1
3 to 7 carbon atoms, or represent phenylalkyl or phenyl having if
a~r~liate 1 to 4 carbon atoms in the straight-chain or branched alkyl
moiety, each of which is optionally monosubstituted to trisubstituted by
identical or different substituents, suitable substituents for phenyl being
S in each case:
halogen, cyano, nitro, in each case straight-chain or branched alkyl,
alkoxy or allythio having in each case 1 to 4 carbon atoms, in each case
straight-chain or branched halogenoalkyl, halogenoalkoxy or
halogenoalkylthio having in each case 1 to 4 carbon atoms and 1 to 9
identical or different halogen atoms, in each case straight-chain or
branched alkoxycarbonyl or alkoximinoalkyl having in each case 1 to 4
carbon atoms in the individual alkyl moieties, and phenyl which is
optionally monosubstituted to tri~lbstituted by identical or different
substituents con~i~tingofhalogen and/or straight-chain or branched alkyl
having 1 to 4 carbon atoms;
or R8 and R9, together with the nitrogen atom to which they are
attached, rc~lcsent a saturated five- to seven-membered heterocycle
which may optionally contain 1 further heteroatom - in particular nitro-
gen, oxygen or sulphur - which is optionally monosubstituted to
tetrasubstituted by identical or different substituents consisting of
straight-chain or branched alkyl having 1 to 3 carbon atoms,
R' and R" either independently of one another each represent straight-chain
or branched alkyl having 1 to 6 carbon atoms, or represent in each case
straight-chain or branched alkenyl or alkinyl having in each case 2 to 6
carbon atoms, or represent straight-chain or branched halogenoallyl
having 1 to 4 carbon atoms and 1 to 9 identical or different halogen
atoms, especially~uorine, chlorine and/or bromine, or represent in each
case straight-chain or branched halogenoalkenyl or halogenoalkinyl
having in each case 2 to 4 carbon atoms and 1 to 7 identical or different
halogen atoms, especially fluorine, chlorine and/ or bromine, or represent
LeA29399 - 17-

2146~61
in each case straight-chain or branched alkoxyalkyl or alkoxy having in
each case 1 to 6 carbon atoms in the individual alkyl moieties, or
represent cycloalkyl having 3 to 7 carbon atoms, or replesellt cycloalkyl-
alkyl having 3 to 7 carbon atoms in the cycloalkyl moiety and 1 to 4
S carbon atoms in the straight-chain or branched alkyl moiety, or represent
phenyl or phenylalkyl having if a~pro~liate 1 to 4 carbon atoms in the
straight-chain or branched alkyl moeity, each of which is optionally
monosubstituted to trisubstituted by identical or dil~rent substituents, or
represent heteroaryl having 2 to 9 carbon atoms and 1 to 3 identical or
di~rellt heteroatoms - in particular nitrogen, oxygen and/or sulphur -
which is optionally monosubstituted to trisubstituted by identical or
dilr~;lt;llt substituents, suitable substituents for aryl and heteroaryl being
in each case:
halogen, cyano, nitro, in each case strai ht-chain or branched alkyl,
alkoxy or allythio having in each case 1 to 4 carbon atoms, in each case
straight-chain or branched halogenoalkyl, halogenoalkoxy or
halogenoalkylthio having in each case 1 to 4 carbon atoms and 1 to 9
identical or different halogen atoms, in each case straight-chain or
branched alkoxycarbonyl or alkoximinoalkyl having in each case 1 to 4
carbon atoms in the individual alkyl moieties, and phenyl which is
optionally monosubstituted to trisubstituted by identical or different
substituentscon.~i~tingofhalogenand/orstraight-chainorbranchedalkyl
having 1 to 4 carbon atoms;
or R' and Rl~, together with the nitrogen atom to which they are
attached, represent a saturated five- to seven-membered heterocycle
which may optionally contain 1 further heteroatom - in particular nitro-
gen, oxygen or sulphur - which is optionally monosubstituted to
tetrasubstituted by identical or different substituents con~i~ting of
straight-chain or branched alkyl having 1 to 3 carbon atoms, and
30 X2 represents oxygen or sulphur.
Le A 29 399 - 18 -

2 1 ~
Very particularly preferred compounds of the formula (I) are those in which
Het represents a heterocycle of the formula
R R5 R6
\~ N ~N
~(~N~X2 or R--N~N)~X2
Rl, R2 and R3 independently of one another each represent fluorine, chlorine
S or bromine, or re~resel-t straight-chain or branched alkyl having 1 to 4
carbon atoms, or lc~lesellt straight-chain or branched alkenyl having 2
to 4 carbon atoms, or r~resellt straight-chain or branched alkinyl having
2 to 4 carbon atoms, or re~resent straight-chain or branched alkoxy
having 1 to 4 carbon atoms, or represent phenylalkyl, phenyl or phenoxy
having if a~plol,.iate 1 to 3 carbon atoms in the straight-chain or
branched alkyl moiety, each of which is optionally monosubstituted or
disubstituted by identical or dilr~.e.lt substituents, suitable substituents
for phenyl being in each case:
fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, n- or i-propyl,
n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-
butoxy, methylthio, ethylthio, trifluoromethyl, difluoromethyl,
trifluoromethoxy, difluoromethoxy, trifluoromethylthio,
methoxycarbonyl, ethoxycarbonyl, methoximinomethyl,
methoximinoethyl, ethoximinomethyl, ethoximinoethyl or phenyl which
is optionally monosubstituted to disubstituted by identical or different
substituents con~i~ting of ~uorine, chlorine, bromine, methyl and/or
ethyl;
A represents a divalent alkanediyl radical having 1 to 4 carbon atoms, and
Le A 29 399 - 19 -

21465~i
Xl represents oxygen or sulphur, where
R4 represents hydrogen, ~uorine, chlorine, bromine, cyano or nitro, orrepresents straight-chain or branched alkyl having 1 to 4 carbon atoms
which is optionally monosubstituted, suitable substituents being:
S hydroxyl, cyano, amino, in each case straight-chain or branched alkoxy,
alkylthio, N-alkylamino or N,N-dialkylamino having in each case 1 to
4 carbon atoms in the individual alkyl moieties;
R4 moreover r~res~llt~ in each case straight-chain or branched alkenyl or
alkinyl having in each case 2 to 4 carbon atoms, or r~ esellts halogenoa-
lkyl having 1 or 2 carbon atoms and 1 to 5 identical or different halogen
atoms, especially ~uorine, chlorine andlor bromine, or replesents in
each case straight-chain or branched halogenoalkenyl or halogenoallcinyl
having in each case 2 to 3 carbon atoms and 1 to 5 identical or dilr~rellt
halogen atoms, especially fluorine, chlorine and/or bromine, or
represents in each case straight-chain or branched alkoxy, alkylthio,
alkylsulphinyl, alkylsulphonyl or alkoxycarbonyl having in each case 1 to
4 carbon atoms in the individual alkyl moieties, or furthermore repres-
ents cycloalkyl having 3 to 6 carbon atoms, or fu~thermore l~resents
phenyl or phenoxy, each of which is optionally monosubstituted or
disubstituted by identical or different substituents, suitable substituents
for phenyl being in each case:
fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, n- or i-propyl,
n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-
butoxy, methylthio, ethylthio, triiluoromethyl, difluoromethyl,
trifluoromethoxy, difluoromethoxy, trifluoromethylthio,
methoxycarbonyl, ethoxycarbonyl, methoximinomethyl,
methoximinoethyl, ethoximinomethyl, ethoximinoethyl or phenyl which
is optionally monosubstituted to disubstituted by identical or different
substituents consisting of fluorine, chlorine, bromine, methyl and/or
Le A 29 399 - 20 -

~14S6~1
ethyl;
r
R
or R4 represents a radical of the formula ~
R
R5 r~lesellt~ hydrogen, cyano, amino or aminocarbonyl, or represents
straight-chain or branched alkyl having 1 to 4 carbon atoms which is
S optionally monosubstituted or polysubstituted by identical or different substituents, suitable substituents being
fluorine, chlorine, bromine, hydroxyl, cyano, amino, in each case
straight-chain or branched alkoxy, alkylthio, N-alkylamino or N,N-
dialkylamino having in each case 1 to 3 carbon atoms in the individual
alkyl moieties;
R5 moreover re~lesellts in each case straight-chain or branched alkenyl or
alkinyl having in each case 2 to 4 carbon atoms, or represents in each
case straight-chain or branched alkoxy, alkoxycarbonyl, N-alkylamino,
N,N-dialkylamino or alkylideneimino having in each case 1 to 4 carbon
atoms in the individual alkyl moieties, or furthermore represents
cycloalkyl having 3 to 6 carbon atoms, or furthermore represents phenyl
or phenoxy each of which is optionally monosubstituted or disubstituted
by identical or different substituents, suitable substituents for phenyl
being in each case:
fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, n- or i-propyl,
n-, i-, ~ or t-butyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-
butoxy, methylthio, ethylthio, trifluoromethyl, difluoromethyl,
trifluoromethoxy, difluoromethoxy, trifluoromethylthio,
methoxycarbonyl, ethoxycarbonyl, methoximinomethyl,
methoximinoethyl, ethoximinomethyl, ethoximinoethyl or phenyl which
is optionally monosubstituted to disubstituted by identical or different
Le A 29 399 - 21 -

- 214~6~1
- substituents con.ci~ing of fluorine, chlorine, bromine, methyl and/or
ethyl;
R6 represents in each case straight-chain or branched alkyl, alkoxy or
alkylthio having in each case 1 to 4 carbon atoms, or represents a radical
R
S ofthe formula~
R7 represents straight-chain or branched alkyl having 1 to 4 carbon atoms or
~lesen~s cycloalkyl having 3 to 6 carbon atoms,
R8 and R9 either independently of one another each r~resellt hydrogen, or
represent straight-chain or branched alkyl having 1 to 4 carbon atoms, or
represent in each case straight-chain or branched alkenyl or alkinyl
having in each case 2 to 4 carbon atoms, or replesellt cycloalkyl having
3 to 6 carbon atoms, or represellt phenylalkyl or phenyl having if
al~ropliate 1 to 3 carbon atoms in the straight-chain or branched alkyl
moiety, each of which is optionally monosubstituted or disubstituted by
identical or different substituents, suitable substituents for phenyl being
in each case:
fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, n- or i-propyl,
n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-
butoxy, methylthio, ethylthio, trifluoromethyl, difluoromethyl,
trifluoromethoxy, difluoromethoxy, trifluoromethylthio,
methoxycarbonyl, ethoxycarbonyl, methoximinomethyl,
methoximinoethyl, ethoximinomethyl, ethoximinoethyl or phenyl which
is optionally monosubstituted to disubstituted by identical or different
substituents consisting of fluorine, chlorine, bromine, methyl and/or
ethyl;
Le A 29 399 - 22 -

2146661
or R8 and R9, together with the nitrogen atom to which they are
attached, represent a saturated five- to seven-membered heterocycle
which may optionally contain 1 further heteroatom - in particular nitro-
gen, oxygen or sulphur - which is optionally monosubstituted or
disubstituted by identical or different substituents con~ in~ of methyl
and/or ethyl,
R~ and Rl~ either independently of one another each re~lesellt straight-chain
or branched alkyl having 1 to 4 carbon atoms, or r~reællt in each case
straight-chain or branched alkenyl or alkinyl having in each case 2 to 4
carbon atoms, or represent straight-chain or branched halogenoalkyl
having 1 to 3 carbon atoms and 1 to 7 identical or di~lellt halogen
atoms, especially iluorine, chlorine and/or bromine, or represent in each
case straight-chain or branched halogenoalkenyl or halogenoalkinyl
having in each case 2 to 3 carbon atoms and 1 to 5 identical or different
halogenatoms, especiallyfluorine, chlorineand/orbromine, orre~lesellt
in each case straight-chain or branched alkoxyalkyl or alkoxy having in
each case 1 to 4 carbon atoms in the individual alkyl moieties, or
represent cycloalkyl having 3 to 6 carbon atoms, or represent cycloalkyl-
alkyl having 3 to 6 carbon atoms in the cycloalkyl moiety and 1 or 2
carbon atoms in the alkyl moiety, or represent phenyl or phenylalkyl
having if a~ro~liate 1 to 3 carbon atoms in the straight-chain or
branched alkyl moeity, each of which is optionally monosubstituted or
disubstituted by identical or different substituents, or represent heteroaryl
having 2 to 5 carbon atoms and 1 to 3 identical or different heteroatoms
- in particular nitrogen, oxygen and/or sulphur - which is optionally
monosubstituted or disubstituted by identical or different substituents,
suitable substituents for aryl and/or heteroaryl being in each case:
~uorine, chlorine, bromine, cyano, nitro, methyl, ethyl, n- or i-propyl,
n-, i-, s- or t-butyl, metho~y, ethoxy, n- or i-propoxy, n-, i-, s- or t-
butoxy, methylthio, ethylthio, trifluoromethyl, di~uoromethyl,
trifluoromethoxy, difluoromethoxy, trifluoromethylthio,
Le A 29 399 - 23 -

-- - 2146661
methoxycarbonyl, ethoxycarbonyl, methoximinomethyl,
methoximinoethyl, ethoximinomethyl, ethoximinoethyl or phenyl ~ich
is optionally monosubstituted to disubstituted by identical or different
substituents con~i~ing of fluorine, chlorine, bromine, methyl and/or
ethyl;
or R~ and Rll, together with the nitrogen atom to which they are
attached, r~,esellt a saturated five- to seven-membered heterocycle
which may optionally contain 1 further heteroatom - in particular nitro-
gen, oxygen or sulphur - which is optionally monosubstituted or
disubstituted by identical or different substituents con~i~in~ of methyl
and/or ethyl, and
~2 represents oxygen or sulphur.
Apart from the compounds listed for the P~ lion Examples, specific
mention may be made of the following substituted triazolinones of the general
15 formula (I):
Le A 29 399 - 24 -

` ~14~661
R
Xl'C~N~A--S~R2 (I
R . -
Elet Rl R2 R3 A Xl
2-~ C~ CH3 CH3 C2H5 -CH2- 0
~0
~C~_ C~ CH3 CH3 n-c3H7 -CH2- 0
O
I
(CE~h~N~c~ CH3 CH3 n-C3H7-0- -CH2- 0
~N~O
(C~ CH3 CH3 n-C3H7 -(CH2)3- o
N~N~o
Le A 29 399 - 25 -

` 214666~
EIet Rl R2 R3 A Xl
~N C2H5 C2H5 C2H5 -CH2- 0
N~N~ O
I
CH3 C2H5 C2H5 -(CH2)3- o
~O
I
H3~S C6H5 C6H5 C6Hs -(CH2)3- o
\~N
H,C--~N~O
I
E~C~ CH3 CH3 CH3 -CH2- 0
~N
H,C--N~N~O
I
~N CH3 CH3 CH3 -CH2- 0
~S
I
Le A 29 399 - 26 -

-` 2l~666l
~Iet Rl R2 R3 ~ X
~0~ CH3 CH3 CH3 -CH2- S
~,~eo
~N~ C2H5-- C2H5-- Cl -(CH2)3- o
~0
I
H~C64~ ~ CH3 CH3 CH3 -CH2- 0
N/~o
I
~N~ CH3 CH3 CH3 -CH2- 0
~0
I
~C2~N,CE~ C2H5-- Cl Cl -CH2- 0
Le A 29 399 - 27 -

2~466~
l~et Rl R2 R3 A X
CE~ C2H5-0-C2H5-- CH3 -CH2- 0
~C,E~_ N=C
N~ IN>~O
~,~0 Cl C
Cx CH3 CH3 C2H5 -CH2- 0
~S
~ ~F CH3 -CH2- 0
~0
~C-O CH3 CH3 CH3 -CH2- 0
\tN
~,C--N~N~O
Le A 29 399 - 28 -

2 1 ~
Het Rl R2 R3 ~ Xl
~C2 ~ r~ ~CH3 CH3 C2H5 -CH2- 0
Nl/N~O
~C~ C~ CH3-0- CH3-0- CH3-0- -CH2- 0
~0
~C ~ ~N~K~CH3 CH3 C6H5 -CH2- 0
N ~ O
. ~ CH3 CH3 CH3 -CH2- 0
~N ~ O
I
CH3-0- CH3-0- CH3-0- ~CH2)3- 0
~N ~ O
Le A 29 399 - 29 -

21~66~
~Iet Rl R2 R3 A X
0/~ CH3CH3 -cH2-cH=cH2 -C~2-
~,~0
F3C~ C~ CH3CH3 CH3 -CH2- 0
' N/~o
CH3CH3 C2Hs -CH2- 0
O
~h CH3-0-CH3-0- CH3-0- -(CH2)3- o
N~O
Le A 29 399 30 -

-- ` 2146661
Het Rl . R2 R3 A X
H C~ CH3 CH3i-C3H7-0- -CH2- 0
N~O
\~N CH3 CH3CH3 -CH2- 0
N/ ~
I
CE~ CH3 CH3 CH3 -CH2- 0
~C~N~o
NC~_ C~ CH3 CH3 CH3 -CH2- 0
~0
~}~N~C~ CH3 CH3 CH3 -CH2- 0
N~N~O
Le A 29 399 - 31 -

21~5661
~ Het Rl. R2 R3 ~ X
C~ CH3CH3 CH3 -CH2- 0
~J N~O
~-o~o ~ o~ CH3CH3 CH3 -CH2- 0
`N ~ O
H2N~ H CH3 CH3 CH3 -CH2- 0
~N ~ O
(C~ ~ CN CH3CH3 CH3 -CH2- 0
~0
~C ~ CN CH3CH3 CH3 -CH2- 0
~0
LeA29399 - 32-

- ~14~
Het Rl R2 R3 ;~ Xl
~C~C~ CH3 CH3 CH3 -CH2- 0
~/~N~O
I
~,C~ C~-CN CH3 CH3 CH3 -CH2- 0
~,~0
CH3 CH3 CH3 -CH2- 0
>~O
I
\ N CH3 CH3 CH3 -CH2- 0
N/~NI ~
C~ CH3 CH3 CH3 -CH2- 0
N~N~
Le A 29 399 - 33 -

21466Sl
~et Rl R2 R3A X
N,NE~ CH3 CH3CH3 -CH2- 0
~N~O
I
Using, forexample, 1-chlorocarbonyl-3-dimethylamino-4-methyl-1,2,~
triazolin-S-one and trimethylsilylmethylamine as starting materials, the
course of reaction of process (a) according to the invention can be
represented by the following equation:
CE~
~N N'
~N~O + ~N--CE~ C~
0~ ~C-
~N/ CE~,
- HCI / base ~0
C CE~
0~ ~NE~CE~S' CE~
CE~ -
Using, for example, 3-dimethylamino-2-methyl-1,2,4-triazolin-5-one
and trimethylsilylmethyl isocyanate as starting materials, the course of
reaction of process (b) according to the invention can be represented by
the following equation:
I~e A 29 399 34

`- 2146~
~,C N~o 0=~'--N--CE~Si OEI3
CE~
~N~o
~c
O'`NE~C~S~
A general definition ofthe 1-chloro(thio)carbonyltriazolinones required
as starting materials for carrying out process (a) according to the
invention is given by the formula (II). In this formula (II) Het and X
~,er~lably represent those radicals which have already been mentioned,
in connection with the description of the compounds of the formula (I)
according to the invention, as being preferred for these substituents.
The 1-chloro(thio)carbonyltriazolinones ofthe formula (II) are known.
(cf. e.g. EP 431 390; EP 283 876; EP 298 371).
A general definition of the amines also required as starting materials for
carrying out process (a) according to the invention is given by the
formula (III). In this formula (III) Rl, R2, R3 and Ap~er~lably represent
those radicals which have already been mentioned, in connection with
the description of the compounds of the formula (I) according to the
invention, as being preferred for these substituents.
The amines of the formula (III) are known. or are obtainable in analogy
to known methods (cf. e.~ J. Arner. Chem. Soc., 73 3867 [1951]; Synth.
LeA29399 35

` 2~4666~
Comrnun., 18, (16-17) 1975-1978).
A general definition of the 1-lln.~lkstituted triazolinones required as
starting materials for carrying out process (b) according to the invention
is given by the forrnula (IV~. In this forrnula (IV~ Het pler~l~bly
represents those radicals which have already been mentioned, in
connection with the description of the substances of the formula (I)
according to the invention, as being pler~lled for these substituents.
The 1-unsubstituted triazolinones of the formula (IV~ are known or are
obtainable in analogy to known methods (c e.g. EP 283 876; EP 431
390; EP 298 371).
A general definition of the iso(thio)cyanates also required as starting
materials for carrying out process (b) according to the invention is given
by the formula (V). In this formula (V), R~, R2, R3, A and Xl preferably
replesent those radicals which have already been mentioned, in
connection with the description of the substances of the formula (I)
according to the invention, as being prer~lled for these substituents.
The iso(thio)cyanates of the formula (V) are known or are obtainable in
analogy to known methods (cf. e.~ Zh. Obshch. Khim. 38, 1179- 1185
[1968]; Zh. Obshch. Khim. 37, 1383-1385 [1967]; J. Or~ Chem. 49,
2688-2691 [1984]).
Suitable diluents for carrying out process (a) according to the invention
are inert organic solvents. These include, in particular, aliphatic,
alicyclic or aromatic, optionally halogenated hydrocarbons such as, for
example, benzine, benzene, toluene, xylene, chlorobenzene,
dichlorobenzene, petroleum ether, hexane, cyclohexane,
dichloromethane, chloroforrn or carbon tetrachloride; ethers such as
diethyl ether, diisopropyl ether, dioxane, tetrahydrofuran or ethylene
LeA29399 - 36-

21466~1
glycol dimethyl or diethyl ether; ketones such as acetone, butanone or
methyl isobutyl ketone; nitriles such as acetonitrile, propionitrile or
benzonitrile; amides such as N,N-dimethylformamide, N,N-dimethyl-
acetamide, N - methylformanilide, N- methylpyrrolidone or
hexamethylphosphoric triamide; esters such as methyl acetate or ethyl
acetate, or bases such as pyridine.
Process (a) according to the invention is plerel~bly carried out in thepresence of a suitable reaction auxiliary. Suitable such auxiliaries are all
conventional inorganic or organic bases. These include, for example,
alkaline earth metal or alkali metal hydroxides, such as sodium
hydroxide, calcium hydroxide, potassium hydroxide or else ammonium
hydroxide, alkali metal carbonates, such as sodium carbonate, potassium
carbonate, potassium hydrogen carbonate, sodium hydrogen carbonate,
or ammonium carbonate, alkali metal or alkaline earth metal ~cet~tes,
such as sodium acetate, potassium acetate, calcium ~cet~te, or
ammonium acetate, and tertiary amines, such as trimethylamine,
triethylamine, tributylamine, N,N-dimethylaniline, pyridine, piperidine,
N-methylpiperidine, N,N-dimethylaminopyridine, di~7~bicyclooctane
(DABCO), diazabicyclononene (DBN) or diazabicycloundecene (DBU).
It is also possible to emplQy the amine of the formula (III) used as
reactant, in a corresponding excess, simultaneously as reaction auxiliary.
When carrying out process (a) according to the invention the reaction
temperatures can be varied over a relatively wide range. The process is
in general carried out at temperatures of bet~veen 0C and + 150C,
preferably at temperatures of between + 10C and + 80C.
To carry out process (a) according to the invention, in general from 1.0
to 5.0 mol, preferably from 1.0 to 2 mol, of amine of the formula (III)
and, if appropl;ate, from 1.0 to 5.0 mol, preferably from 1.0 to 2 mol, of
LeA29399 37

21466~
base æ reaction auxiliary are employed per mole of 1-
chloro(thio)carbonyltriazolinone of the formula (II). The
implementation ofthe reaction and the working-up and isolation ofthe
reaction products are carried out by known methods (cf. in this respect,
for example, EP 283 876 or the P~alion Examples).
Suitable diluents for carrying out process (b) according to the invention
are inert organic solvents. It is prer~lled to use the solvents listed in the
description of the implementation of process (a) according to the
invention.
Process (b) according to the invention may if desired be carried out inthe presence of a suitable, bæic reaction auxiliary. Suitable such
auxiliaries are all conventional inorganic or or~nic bases. Plt;f~rellce is
given to using tertiary amines such æ trimethylamine, triethylamine,
tributylamine, N,N-dimethylaniline, pyridine, piperidine, N-
methylpiperidine, N,N-dimethylaminopyridine, diazabicyclooctane
(DABCO), diazabicyclononene (DBN) or diazabicycloundecene (DBU).
The addition of basic reaction auxiliaries, however, is not absolutely
necessary.
When carrying out process (b) according to the invention the reaction
temperatures can be varied over a relatively wide range. The process is
in general carried out at temperatures of between 0C and +lSOqC,
preferably at temperatures of between +40C and + 120C.
Process (b) according to the invention is usually carried out under
atmospheric pressure. However, it is also possible to work under
elevated or reduced pressure.
To carry out process (b) according to the invention, in general from 1.0
Le A 29 399 - 38 -

2146~5 1
to 5.0 mol, ~re~lably from 1.0 to 2.5 mol, of iso(thio)cyanate of the
formula (V) and, if a~lopliate, from 0.01 to 5.0 mol, pler~l~bly from
0.1 to 2.5 mol, of base as reaction auxiliary are employed per mole of 1-
unsubstituted tria_olinone ofthe formula (I~).
The implementation ofthe reaction and the workingup and isolation of
the reaction products are carried out by known methods (cf. in this
respect, for example, EP 283 876 or the Pr~alation Examples).
The end products of the formula (I) are purified with the aid of
conventional methods, for example by column chromatography or by
recryst~lli7~tion.
Characterization is made by means of the melting point or, in the case
of compounds which do not cryst~lli7~, with the aid of proton nuclear
magnetic resonance spectroscopy ('H-NMR).
The active compounds according to the invention can be used as
defoliants, desiccants, agents for destroying broad-leaved plants and,
especially, as weedkillers. By weeds, in the broadest sense, there are to be
understood all plants which grow in locations where they are not wanted.
Whether the substances according to the invention act as total or
selective herbicides depends essentially on the amount used.
The active compounds according to the invention can be used, for
example, in connection with the following plants:
Dicotyledon weeds ofthe ~enera: Sinapis, Lepidium, Galium, Stellaria,
Matricaria, Anthemis, Galinsoga, Chenopodium, Urtica, Senecio,
Amaranthus, Portulaca, Xanthium, Convolvulus, Ipomoea, Polygonum,
Sesbania, Ambrosia, Cirsium, Carduus, Sonchus, Solanum, Rorippa,
Rotala, Lindernia, Lamium, Veronica, Abutilon, Emex, Datura, ~lola,
LeA29399 - 39-

~14~66~
Galeopsis, Papaver, Centaurea, Trifolium, Ranunculus and Taraxacum.
Dicotyledonculturesofthe~nera:Gossypium,Glycine,Beta,Daucus,
Phaseolus, Pisum, Solanum, Linum, Ipomoea, Vlcia, Nicotiana,
Lycopersicon, Arachis, Brassica, Lactuca, Cucumis and Cucurbita.
Monocotyledon weeds of the _enera: Echinochloa, Setaria, Panicum,
Digitaria, Phleum, Poa, Festuca, Eleusine, Brachiaria, Lolium, Bromus,
Avena, Cyperus, Sorghum, Agropyron, Cynodon, Monochoria,
Fimbristylis, Sagittaria, Eleocharis, Scirpus, Paspalum, Ischaemum,
Sphenoclea, Dactyloctenium, Agrostis, Alopecurus and Apera.
Monocotyledon cultures ofthe ~nera: Oryza, Zea, Triticum, Hordeum,
Avena, Secale, Sorghum, Panicum, Saccharum, ~n~n~, Asparagus and
Allium.
However, the use ofthe active compounds according to the invention is
in no way restricted to these genera, but also extends in the same manner
to other plants.
The compounds are suitable, depending on the concentration, for the
total control of weeds, for e~ample on industrial terrain and rail tracks,
and on paths and squares with and without trees growing. Equally, the
compounds can be employed for combating weeds in perennial cultures,
for example afforestations, decorative tree plantings, orchards, vineyards,
citrus groves, nut orchards, b~n~n~ plantations, coffee plantations, tea
plantations, rubber plantations, oil palm plantations, cocoa plantations,
soft fruit plantings and hopfields, and for the selective combating of
weeds in annual cultures.
In this context the active compounds according to the invention can be
employed with particular success to combat mono- and dicotyledon
Le A 29 399 - 40 -

2146661
weeds in monocotyledon crops such as, for example, maize.
The active compounds can be converted into the customary
formulations, such as solutions, emulsions, suspensions, powders, foams,
pastes, granules, aerosols, natural and synthetic materials impre~te.l
with active compound, very fine capsules in polymeric substances.
These formulations are produced in a known manner, for example by
mixing the active compounds with extenders, that is, liquid solvents,
liquefied gases under pressure, and/ or solid carriers, optionally with the
use of surface-active agents, that is, emulsifyingagents and/or dispersing
agents, and/or foam-forming agents.
In the case of the use of water as an extender, organic solvents can, for
example, also be used as auxiliary solvents. Suitable liquid solvents are in
the main: aromatics, such as xylene, toluene or allyln~phth~lenes,
chlorinated aromatics or chlorinated aliphatic hydrocarbons, such as
chlorobenzenes, chloroethylenes or methylene chloride, aliphatic hydro-
carbons, such as cyclohexane or paraffins, for example mineral oil
fractions, mineral and vegetable oils, alcohols, such as butanol or glycol
as well as their ethers and esters, ketones, such as acetone, methyl ethyl
ketone, methyl isobutyl ketone or cyclohexanone, stronglypolar solvents,
such as dimethylformamide or dimethyl sulphoxide, as well as water.
Suitable solid carriers are: for example ammonium salts and ground
natural minerals, such as kaolins, clays, talc, chalk quartz, attapulgite,
montmorillonite or diatomaceous earth, and ground synthetic minerals,
such as highly disperse silica, alumina and silicates; suitable solid carriers
for granules are: for example crushed and fractionated natural rocks
such as calcite, marble, pumice, sepiolite and dolomite, as well as
synthetic granules of inorganic and or~nic meals, and granules of
organic material such as sawdust, coconut shells, maize cobs and tobacco
Le A 29 399 - 41 -

~4666:~
stalks; suitable emulsifying and/or foam-formingagents are: for exar.nple
nonionic and anionic emulsifiers, such as polyoxyethylene fatty acid
esters, polyoxyethylene fatty alcohol ethers, for example alkylaryl
polyglycol ethers, alkylsulphonates, alkyl sl-lph~te~, arylsulphonates as
well as albumen hydrolysis products; suitable dispersing agents are: for
example lignin sulphite waste liquors and methylcellulose.
Adhesives such as carboxyr.nethylcellulose and natural and synthetic
polymers in the form of powders, granules or latices, such as gum arabic,
polyvinyl alcohol and polyvinyl acetate, as well as natural phospholipids,
such as cephalins and lecithins, and synthetic phospholipids can be used
in the formulations. Further additives may be mineral and vegetable oils.
It is possible to use colorants such as inor~nic pigments, for example
iron oxide, titaniur.n oxide and Prussian Blue, and org~nic dyestuffs, such
as alizarin dyestuffl, azo dyestuffs and metal phthalocyanine dyestuffs,
and trace nutrients such as salts of iron, m~n~nese, boron, copper,
cobalt, molybdenum and zinc.
The formulations contain in general between 0.1 and 95 per cent by
weight of active compound, pler~lably between 0.5 and 90%.
The active compounds accordingto the invention, as such or in the form
oftheir formulations, can also be used, for combating weeds, as mixtures
with known herbicides, finished formulations or tank mixes being
possible.
Suitable herbicides for the mixtures are kno~ herbicides, such as, for
example, anilides, for example diflufenican and propanil; arylcarboxylic
acids such as dichloropicolinic acid, dicamba or picloram; aryloxy-
alkanoic acids such as 2,4-D, 2,~DB, 2,~DP, fluroxypyr, MCPA,
MCPP and triclopyr; aryloxy-phenoxy-alkanoic esters, such as
Le A 29 399 - 42 -

21~65~1
diclofopmethyl, fenoxaprop-ethyl, ~ua_ifop-butyl, haloxyfop-methyland
quizalofop-ethyl; azinones such as chlorida_one and norflurazone; car-
bam~tes such as chloll"opham, desmedipham, phenmedipham and
propham; chloroacetanilides such as alachlor, acetochlor, butachlor,
met~7~chlor, metolachlor, pretilachlor and propachlor; dinitroanilines
such as oryzalin, pendimethalin and trifluralin; diphenyl ethers such as
aci~luorfen, bifenox, fluoroglycofen, fomesafen, halosafen, lactofen and
oxyfluorfen; ureas such as chlorotoluron, diuron, fluometuron, iso-
proturon, linuron and methaben7tlli~7llron; hydroxylamines such as
alloxydim, clethodim, cycloxydim, sethoxydim and tralkoxydim;
imidazolinones, such as ima_ethapyr, im~7~methabenz, im~7~ryr and
im~7~quin; nitriles, such as bromoxynil, dichlobenil and ioxynil;
oxy~cet~mides, such as mefenacet; sulphonylureas, such as
amidosulfuron, ben~-lfilron-methyl, chlorimuron-ethyl, chlorsulfon,
cinosulfuron, mets~llfilron-methyl, nicosulfuron, primi~llfilron,
pyrazosulfuron-ethyl, tllifen~llfilron-methyl, tri~llfilron and tribenuron-
methyl; thiolcarb~m~tes, such as butylate, cycloate, (li~ te, EPTC,
esprocarb, molinate, prosulfocarb, thiobencarb and triallate; tri~7ines,
such as atrazine, cy~n~7in, ~im~7in~ simetryne, terbutryne and terbutyl-
a_ine; triazinones, such as hexazinon, met~mitron and metribuzine; and
others such as aminotriazole, benfuresate, bentazone, cinmethylin,
clomazone, clopyralid, difenzoquat, dithiopyr, ethofiumesate,
fluorochloridone, glufosinate, glyphosate, isoxaben, pyridate,
quinchlorac, quinmerac, sulphosate and tridiphane.
A mix~ures with other known active compounds, such as fungicides,
insecticides, acaricides, nematicides, bird repellants, plant nutrients and
agents which improve soil structure, is also possible.
The active compounds can be used as such, in the form of their
formulations or in the use forms ~repared therefrom by fiurther dilution,
such as ready-to-use solutions, suspensions, emulsions, powders, pastes
Le A 29 399 - 43 -

21~6~
and granules. They are used in the customary manner, for e~ample by
watering, spraying, atomi7ing or scattering.
The active compounds according to the invention can be applied either
before or a~er emergence of the plants.
They can also be incorporated into the soil before sowin~
The amount of active compound used can vary within a relatively wide
range. It depends essentially on the nature of the desired effect. In
general, the amounts used are between 0.01 and 10 kg of active
compound per hectare of soil surface, pr~r~lably between 0.05 and 5 kg
per hectare.
The ~r~alion and the use of the active compounds according to the
invention are evident from the following ea~amples.
Le A 29 399 44

211~
Preparation Examples:
Example 1:
, N
~/~N~O
O~C`~ ~
(Process a)
Asolution of 2.68 g(0.025 mol oftrimethylsilylmethylamine and 2.53 g
(0.025 mol) of triethylamine in 50 ml of acetonitrile is added dropwise
with stirring at room temperature to 5.1 g (0.025 mol) of 1-chloro-
carbonyl-3-dimethylamino-~methyl- 1,2,~triazolin-5-one in 100 ml of
acetonitrile and, after addition is complete, the mi~ure is stirred at room
tempelaLIlre for 60 minutes. For working up, precipitated triethylamine
hydrochloride is filtered of ~ the filtrate is concentrated in vacuo, and the
residue is taken up in 150 ml of dichloromethane, washed with three
times 50 ml of water, dried over sodium sulphate and again concentrated
in vacuo. The residue is recrystallized from cyclohexane.
4.0 g (59% of theory) are obtained of 3-dimethylamino-4-methyl-1-
(trimethylsilylmethyl-aminocarbonyl)- 1,2,4-triazolin-5-one with a
melting point of 79-81C.
LeA29399 45

` ~ 21465~1
Example 2:
O N
E~C--N~O
C
0~ `NE~CE~Si CE~
Process (b)
3.87 g (0.03 mol) of trimethylsilyl isocyanate and 3 drops of 1,8-
dia_abicyclo- [5.4.0]-undec-7-ene (DBU) are added at room te~ re
with stirringto 5.25 g(0.03 mol) of 2-methyl-3-(4-morpholinyl)-(lH)-
1,2,4-triazolin-S-one in 100 ml of acetonitrile, the mixture is
subsequently stirred at room temperature for 4 hours and is then
concentrated in vacuo, and the residue is recryst~lli7~1 from
cyclohexane/ethyl ~cet~te (1:1).
6.5 g (69% of theory) are obtained of 2-methyl-3-(4-morpholinyl)- 1-
(trimethylsilylmethyl-aminocarbonyl)- 1,2,4-tria_olin-S-one with a
melting point of 133-134C.
In a corresponding manner, and in accordance with the general
preparation data, the follo~ng substituted tria~linones of the general
formula (I) are obtained:
Le A 29 399 - 46 -

- 21~66~
X `N~A--g~R (I)
R
Ex. No. Het ~3 Xlphysical
3 ((~)2N\ C~ O~p. 99-100C
~N _C~
~C~ ~N>~0
I
4 C~-S C~ C~ O~p 130-132C
~o C~ C~
5(CE~)2N~ CE~ OC2H5 Om.p. 4647C
k~ _(~ s~o~
6 CE~-S CE~ O~ OlH-N~ )
N/~N _(C~ S~OC2~ 0.6-0.7;
>~O OC2H~ 1.18-1.23;
2.65; 3.20
Le A 29 399 47

21~6~1
l~x. I~o. ~et R' XlprYpSerties
7 C2Hs O CE~, CH3 o~p. 79-80C
~C~
8 ~O C~ CH3~ ~p 139-1400C
~N~O 1~
g ~C~ O~p. 140-141C
~ --C~Si CE~3
~C3~ C~ ~ O~p. 81-83C
~N~O
1 1 /~ CE~ O~p. 103-104C
~N>~O
12 ~C3~ ~ oIrLp. 63-64C
,~ --C~S~CE~
Le A 29 399 - 48 -

21 4666~
Ex. NoI~et R3X~ physic 1
13 H C~ O ~Lp 115-116C
gi C~
~N~O
I
14 ~ O~p. 79-.81C
`~N~O ~H
~C-O C2Hs C~ Om.p. 87-89C
~ ~O ~ CE~
16 Br t~4~ C~ O~p. 143-145C
~0
17 C~ OlH-N~ ):
N _C~i C~ 1.15-1.20; 3.0;
~N ~ 3.22
~c N~o
I
18 C~-S~ ,C~ C~ O ~p. 92-93C
~N ~ _C~
~O
I
Le A 29 399 49

- 2146661
Ex. No. Het A S R2 Xl physical
~;3
19 C~ O m.p. 167-168C
,CH3 CH3 O~p. 50-51C
~C~ ~C --CE~ CH3
~N~O
21 CH3 CX3 OlH N~.~):
-C4~ ~ 0 9-0.93;
~N~O 2.3-2.32
22 ,CH3 CH3 O~p. 68-69C
~N ~-C4~ ~
~0
23 ~ \ ~ CH3 m.p. 117-118C
~N _CH2 ~ CH3
Le A 29 399 50

- 2146G6:~
Ex. No Elet --~S~R Xl physical
24 ,(~(~ O lH-NMR 3:
(C~2N~ N=C ~ L C~, 2.0; 2.35-2.38;
~N \~C4E~ ~ 2.85
~O
I
(C~)2N\N~ O lH-N~. ):
0.8; 2 8-2.82;
~:O ~ 3.0
I
26 ~CjH, N~
\tN _C~i ~ 0.8;1.25-1.28;
N~o ~ 2.77-2.8
I
27 NC~ nCjH~ CE~ olH-N~ ):
~N --CE~ 0.85-0.92;
~N~O CE~ 2.7S-2.8;
3.63-3.7
28 F2(~ O~p. 88-90C
C~
29 ~C6 Nf~- C~ O~p. 158-160C
~0
Le A 29 399 - 51 -

. - 2146~
Ex. No.~et ~ Xlphysical
Br CE~ Om.p. 94-95C
~N~O (~
31 ~CO ~ Om.p. 112C
O ~ .
32 Cl ~ ~ Om.p. 121C
~N~O
33 ~,C\ ~ I Om.p. 125C
~IN>~O _~51 C~
~4 ~ ~M o
Le A 29 399 - 52 -

214~6~
Ex. No. ~et R3 Xl physlca
~N~ ~ Oll
36 (CO2N OC~ c~ S lH-N~*):
~N' _~S;- C~ 3.04;3.08-
~O ~ 3.10; 3.30;
11.0
The 'H-NMR spectra were recorded in deuterochloroform (CDCl3)
or hexadeuterodimethylsulphoxide (DMSO-d6) with
tetramethylsilane (TMS) as internal standard. The value given is the
chemical shi~, ~, in ppm.
Le A 29 399 - 53 -

- 21~6~61
Use Examples:
In the following Use Examples the compound indicated below ~s
employed as comparison substance:
E~,~N
)=N
~N~o
O~C`~C~(~ c~ (A)
2- Methyl- 3- dimethylamino- 1- [N- (2, 2- dimethyl- 1 -propyl)-
aminocarbonyl] - 1, 2, 4-triazolin- 5- one
(kno~ from EP 431 390)
LeA29399 54

2146~
Example A
P~emelgence tes;t
Solvent: 5 parts by weight of acetone
Emulsifier: 1 part by weight of alkylaryl polyglycol ether
To produce a suitable plepalalion of active compound, one part by
weight of active compound is mixed with the stated amount of solvent,
the stated amount of emulsifier is added and the concentrate is diluted
with water to the desired concentration.
Seeds of the test plants are sown in normal soil and, after 24 hours,
uatered with the ~ dlion of the active compound. It is expedient to
keep constant the amount of water per unit area. The concentration of
the active compound in the ~r~alation is of no importance, only the
amount of active compound applied per unit area being decisive. Afcer
three weeks, the degree of ~ ~ to the plants is rated in % ~ ~ in
comparison to the development of the untreated control.
The figures denote:
0% = no action (like untreated control)
100%= total destruction
In this test, for example, the compound according to Preparation
Example 3 exhibits a marked superiority in activity, and also a
considerably improved selectivity by crop plants, in relation to the prior
art.
Le A 29 399 5s -

2146~6 i
Table A
P~cme.~nce test/gteenhouse
~=N (~)2N~=
~O ~C--N~N~O
Actlve compound
~ ~N~C~C--C~3 ~ ~N~i C~
(A) (lmo~) (E~ample 3)
Application ~ate
in g/ha 125 125
l\Iaize 40 0
Echinochloa 60 95
Abuthilon 60 100
Cassia 0 95
Chenopodium 80 100
Galium 0 95
Sinapis 70 100
Solanum 70 95
Le A 29 399 - 56 -

21~6661
Example B:
Post-emelgence test
Solvent: 5 parts by weight of acetone
Emulsifier: 1 part by weight of alkylaryl polyglycol ether
To produce a suitable preparation of active compound, one part by
weight of active compound is mixed with the stated amount of solvent,
the stated amount of emulsifier is added and the concentrate is diluted
with water to the desired concentration.
Test plants which are 5 - 15 cm high are sprayed with the pr~afation ofthe active compound so as to apply the particular amounts of active
compound desired per unit area. Afcer three weeks, the degree of ~
to the plants is rated in % ~ ~ in co~ .alison to the development of
the untreated control.
The figures denote:
0%= no action (like untreated control)
100%= total destruction
In this test, for example, the compound according to Preparation
Example 3 exhibits a marked superiority in activity, and also a
considerably improved selectivity by crop plants, in relation to the prior
art.
Le A 29 399 - 57 -

21~6~:l
-~ Table B:
Post-emelgence test/Greenhouse
~N ~N
~,G~N~ O ~ ~O
Active compound
~ `N~C~C~ 0~ `~
(A) (kno~) (E~ample 3)
Application ~te
in g/ha 125 125
~ize 10 0
Galium 80 95
Stç!l~n~ 80 95
~lola 30 80
Le A 29 399 - 58 -

Representative Drawing