Plant protecting and regulating compositions – Plant growth regulating compositions – Organic active compound containing
Reexamination Certificate
1999-07-19
2002-02-26
Morris, Patricia L. (Department: 1612)
Plant protecting and regulating compositions
Plant growth regulating compositions
Organic active compound containing
C548S263200, C548S263400, C548S263800, C548S264400
Reexamination Certificate
active
06350720
ABSTRACT:
The invention relates to new substituted phenyltriazolin(ethi)ones, to processes for their preparation and to their use as herbicides.
It has already been disclosed that certain substituted phenyltriazolin(ethi)ones have herbicidal properties (cf. EP 609734/U.S. Pat. No. 5,464,810). However, the substituted phenyltriazolin(ethi)ones which have been disclosed have not gained any particular significance.
There have now been found new substituted phenyltriazolin(ethi)ones of the general formula (I)
in which
Q
1
and Q
2
are identical or different and represent O or S,
R
1
represents hydrogen, cyano, halogen or one of the radicals —R
6
, —O—R
6
, —SR
6
, —SO—R
6
or —SO
2
—R
6
,
R
2
represents hydrogen, hydroxyl, amino or one of the radicals —R
6
, —O—R
6
or —N═CR
6
R
7
,
R
3
represents hydrogen, halogen, alkyl or halogenoalkyl,
R
4
represents hydrogen, alkoxycarbonyl or one of the radicals —R
6
, —O—R
6
, —SR
6
, —NH—R
6
or —NR
6
R
7
,
R
5
represents amino, hydroxyl or one of the radicals —R
6
or —NR
6
R
7
,
R
6
represents a radical from amongst alkyl, alkenyl, alkinyl, cycloalkyl, aryl, arylalkyl, aryloxyalkyl, arylalkoxyalkyl, heterocyclyl or heterocyclylalkyl, each of which is optionally substituted, and
R
7
represents hydrogen or a radical from amongst alkyl, alkenyl, alkinyl or cycloalkyl, each of which is optionally substituted.
Furthermore, it has been found that the new substituted phenyltriazolin(ethi)ones of the general formula (I) are obtained when phenyltriazolin(ethi)ones of the general formula (II)
in which
Q
1
, R
1
, R
2
, R
3
and R
5
have the abovementioned meanings,
are reacted with halogeno(thio)carbonyl compounds of the general formula (III)
in which
Q
2
and R
4
have the abovementioned meanings and
X represents halogen,
if appropriate in the presence of a reaction auxiliary and if appropriate in the presence of a diluent.
Furthermore, it has been found that the new substituted phenyltriazolin(ethi)ones of the general formula (I) are distinguished by a potent and selective herbicidal activity. Formula (I) provides a general definition of the substituted phenyltriazolin(ethi)ones according to the invention. Preferred compounds of the formula (I) are those in which
Q
1
and Q
2
are identical or different and represent O or S,
R
1
represents hydrogen, cyano, fluorine, chlorine, bromine, iodine or one of the radicals —R
6
, —O—R
6
, —S—R
6
, —SO—R
6
or —SO
2
—R
6
,
R
2
represents hydrogen, hydroxyl, amino or one of the radicals —R
6
, —O—R
6
or —N═CR
6
R
7
,
R
3
represents hydrogen, fluorine, chlorine, bromine, iodine, or represents straight-chain or branched alkyl having 1 to 4 carbon atoms or straight-chain or branched halogenoalkyl having 1 to 4 carbon atoms and 1 to 3 identical or different halogen atoms—in particular fluorine, chlorine or bromine,
R
4
represents hydrogen, alkoxycarbonyl having 1 to 6 carbon atoms in the alkoxy group, or one of the radicals —R
6
, —O—R
6
, —S—R
6
, —NH—R
6
or —NR
6
R
7
,
R
5
represents amino, hydroxyl or one of the radicals —R
6
or —NR
6
R
7
,
R
6
represents straight-chain or branched alkyl having 1 to 10 carbon atoms which is optionally monosubstituted or polysubstituted by identical or different substituents, preferred substituents being:
halogen—in particular fluorine, chlorine and/or bromine, cyano, carboxyl, carbamoyl, thiocarbamoyl, in each case straight-chain or branched alkoxy, alkoxyalkoxy, alkylthio, alkylsulphinyl, alkylsulphonyl, alkoxycarbonyl, N-alkyl-amninocarbonyl, N,N-dialkyl-aminocarbonyl, trialkylsilyl or alkylsulphonylaminocarbonyl, each of which has 1 to 6 carbon atoms in the individual alkyl moieties, or heterocyclyl, the heterocyclyl radical being a five- to seven-membered saturated or unsaturated heterocycle which has 1 to 3 identical or different hetero atoms—in particular nitrogen, oxygen and/or sulphur—and which is optionally benzo-fused;
R
6
furthermore represents alkenyl or alkini, each of which has 2 to 8 carbon atoms and each of which is optionally monosubstituted or polysubstituted by identical or different halogen substituents—in particular fluorine, chlorine and/or bromine;
R
6
furthermore represents cycloalkyl having 3 to 7 carbon atoms which is optionally monosubstituted or polysubstituted by identical or different halogen substituents—in particular fluorine, chlorine and/or bromine—and/or straight-chain or branched alkyl having 1 to 4 carbon atoms;
R
6
furthermore represents aryl, arylalkyl, aryloxyalkyl or arylalkoxyalkyl, each of which has 6 to 10 carbon atoms in the aryl moiety and, if appropriate, 1 to 4 carbon atoms in the straight-chain or branched alkyl moiety and each of which is optionally monosubstituted or polysubstituted in the aryl moiety by identical or different substituents, or represents a saturated or unsaturated, five- to seven-membered heterocyclyl radical which has 1 to 3 identical or different hetero atoms—in particular nitrogen, oxygen and/or sulphur—and which is optionally monosubstituted or polysubstituted by identical or different substituents and/or benzo-fused, preferred aryl or heterocyclyl substituents being:
halogen, cyano, nitro, amino, N-acetyl-amino, in each case straight-chain or branched alkyl, alkoxy, alkylthio, alkylsulphinyl or alkylsulphonyl, each of which has 1 to 6 carbon atoms, in each case straight-chain or branched halogenoalkyl, halogenoalkoxy, halogeroalkylthio, halogenoalkylsulphinyl or halogenoalkylsulphonyl, each of which has 1 to 6 carbon atoms and 1 to 3 identical or different halogen atoms, in each case straight-chain or branched alkoxycarbonyl or alkoximinoalkyl, each of which has 1 to 6 carbon atoms in the individual alkyl moieties, and phenyl which is optionally monosubstituted or polysubstituted by identical or different substituents from amongst halogen and/or straight-chain or branched alkyl or alkoxy, each of which has 1 to 6 carbon atoms, and/or straight-chain or branched halogenoalkyl or halogenoalkoxy, each of which has 1 to 6 carbon atoms and 1 to 3 identical or different halogen atoms;
R
7
represents hydrogen, or represents alky having 1 to 8 carbon atoms which is optionally monosubstituted or polysubstituted by identical or different substituents, suitable substituents being:
halogen—in particular fluorine, chlorine and/or bromine, cyano, carboxyl, carbamoyl, thiocarbamoyl, in each case straight-chain or branched alkoxy, alkoxyalkoxy, alkylthio, alkylsulphinyl, alkylsulphonyl, alkoxycarbonyl, N-alkyl-aminocarbonyl, N,N-dialkyl-aminocarbonyl, trialkylsilyl or alkylsulphonylaminocarbonyl, each of which has 1 to 8 carbon atoms in the individual alkyl moieties, or heterocyclyl, and the heterocyclyl being a five- to seven-membered saturated or unsaturated heterocycle which has 1 to 3 identical or different hetero atoms—in particular nitrogen, oxygen and/or sulphur—and which is optionally benzo-fused;
R
7
furthermore represents alkenyl or alkinyl, each of which has 2 to 8 carbon atoms and each of which is optionally monosubstituted or polysubstituted by identical or different halogen substituents—in particular fluorine, chlorine and/or bromine;
R
7
furthermore represents cvcloalkyl having 3 to 7 carbon atoms which is optionally monosubstituted or polysubstituted by identical or different substituents from amongst halogen—in particular fluorine, chlorine and/or bromine—and/or straight-chain or branched alkyl having 1 to 4 carbon atoms.
Especially preferred compounds of the formula (I) are those in which
Q
1
and Q
2
are identical or different and represent O or S,
R
1
represents hydrogen, fluorine, chlorine, bromine or one of the radicals —R
6
, —O—R
6
, —SR
6
, —SO—R
6
or —SO
2
—R
6
,
R
2
represents hydrogen, hydroxyl, amino or one of the radicals —R
6
, —O—R
6
or —N═CR
6
R
7
,
R
3
represents hydrogen, fluorine, chlorine, bromine, straight-chain or branched alkyl having 1 to 3 carbon atoms or straisght-chain or branched halogenoalkyl having 1 to 3 carbon atoms and 1 to 3 identical or different halogen atoms—in particular fluorine or chlorine,
R
4
represents hydrogen, al
Dollinger Markus
Haas Wilhelm
Linker Karl-Heinz
Schallner Otto
Bayer Aktiengesellschaft
Gil Joseph C.
Morris Patricia L.
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