Plant protecting and regulating compositions – Plant growth regulating compositions – Organic active compound containing
Reexamination Certificate
2000-11-03
2002-03-19
Ford, John M. (Department: 1624)
Plant protecting and regulating compositions
Plant growth regulating compositions
Organic active compound containing
C504S233000, C544S206000, C544S207000
Reexamination Certificate
active
06358886
ABSTRACT:
The invention relates to novel substituted, optically active aminotriazines having at least two asymmetrically substituted carbon atoms, to a process for their preparation and to their use as herbicides.
Substituted aminotriazines are already known from the (patent) literature (cf. U.S. Pat. No. 3,816,419, U.S. Pat. No. 3,932,167, EP-191 496, EP-273 328, EP-411 153/WO 90/09 378, WO 97/00 254, WO 97/08 156). However, these compounds—some of which also have asymmetrically substituted carbon atoms—have hitherto not attained any particular importance.
This invention, accordingly, provides the novel substituted, optically active aminotriazines having at least two asymmetrically substituted carbon atoms of the general formula (I)
in which
A represents a single bond or represents in each case straight-chain or branched alkanediyl or oxaalkanediyl having in each case up to 6 carbon atoms,
R
1
represents amino, represents formylamino or represents in each case optionally cyano-, halogen- or C
1
-C
4
-alkoxy-substituted alkylamino, dialkylamino, alkylcarbonylamino, N-alkyl-N-alkylcarbonylamino, alkoxycarbonylamino, N-alkyl-N-alkoxycarbonylamino, alkylaminoalkylideneamino or dialkylaminoalkylideneamino having in each case up to 6 carbon atoms in the alkyl groups or alkylidene groups,
R
2
represents hydrogen, halogen or optionally cyano-, halogen- or C
1
-C
4
-alkoxy-substituted alkyl having up to 6 carbon atoms,
R
3
represents hydrogen, halogen or optionally cyano-, halogen- or C
1
-C
4
-alkoxy-substituted alkyl having up to 6 carbon atoms, or together with R
2
represents optionally cyano-, halogen- or C
1
-C
4
-alkyl-substituted alkanediyl having 2 to 5 carbon atoms,
R
4
represents alkyl having up to 6 carbon atoms or represents cycloalkyl having 3 to 6 carbon atoms,
Y represents hydrogen, hydroxyl, mercapto, amino, cyano, halogen, or represents in each case optionally cyano-, halogen- or C
1
-C
4
-alkoxy-substituted alkyl, alkoxy, alkylcarbonyloxy, alkoxycarbonyloxy, alkylaminocarbonyloxy, dialkylaminocarbonyloxy, alkylthio, alkylamino or dialkylamino having in each case up to 6 carbon atoms in the alkyl groups, and
Z represents an optionally substituted monocyclic or bicyclic, carbocyclic or heterocyclic group from the group consisting of cyclopentyl, cyclohexyl, phenyl, naphthyl, tetralinyl, decalinyl, indanyl, indenyl, furyl, benzofuryl, di-hydrobenzofuryl, thienyl, benzothienyl, dihydrobenzothienyl, isobenzofuryl, dihydroisobenzofuryl, isobenzothienyl, dihydroisobenzothienyl, pyrrolyl, indolyl, isoindolyl, indolinyl, isoindolinyl, benzodioxolyl, oxazolyl, benzoxazolyl, thiazolyl, benzothiazolyl, benzimidazolyl, indazolyl, oxadiazolyl, thiadiazolyl, pyrazolyl, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, quinolyl, isoquinolyl, quinoxalinyl, cinnolinyl and phthalazinyl,
where the possible substituents are in each case preferably selected from the group below:
hydroxyl, amino, cyano, nitro, carbamoyl, sulphamoyl, halogen, in each case optionally hydroxyl-, cyano- or halogen-substituted alkyl, alkoxy, alkylamino or dialkylamino having in each case 1 to 6 carbon atoms in the alkyl groups, in each case optionally halogen-substituted alkylcarbonyl, alkoxycarbonyl, alkylcarbonylamino, alkylaminocarbonyl, dialkylaminocarbonyl, alkylthio, alkylsulphinyl, alkylsulphonyl, alkylsulphonylamino, alkylaminosulphonyl or dialkylaminosulphonyl having in each case 1 to 6 carbon atoms in the alkyl groups, in each case optionally hydroxyl-, cyano-, nitro-, halogen-, C
1
-C
4
-alkyl-, C
1
-C
4
-halogenoalkyl-, C
1
-C
4
-alkoxy- or C
1
-C
4
-halogenoalkoxy-substituted phenyl or phenoxy, and in each case optionally halogen-substituted methylenedioxy or ethylenedioxy,
with the proviso that in each individual case R
2
, R
3
and Y are different from one another and that the substituents at the two carbon atoms to which R
2
and R
3
or R
4
are attached are configured as follows:
(a) R configuration at the carbon atom to which R
2
and R
3
are attached and R configuration at the carbon atom to which R
4
is attached (“R,R-diastereomers”),
(b) R configuration at the carbon atom to which R
2
and R
3
are attached and S configuration at the carbon atom to which R
4
is attached (“R,S-diastereomers”),
(c) S configuration at the carbon atom to which R
2
and R
3
are attached and R configuration at the carbon atom to which R
4
is attached (“S,R-diastereomers”),
(d) S configuration at the carbon atom to which R
2
and R
3
are attached and S configuration at the carbon atom to which R
4
is attached (“S,S-diastereomers”),
(e) R configuration at the carbon atom to which R
2
and R
3
are attached and racemic configuration at the carbon atom to which R
4
is attached (“R,rac-diastereomers”),
(f) S configuration at the carbon atom to which R
2
and R
3
are attached and racemic configuration at the carbon atom to which R
4
is attached (“S,rac-diastereomers”).
Since the C atom to which R
2
, R
3
and Y are attached is not present in racemic form, all compounds according to the invention are optically active.
The novel substituted aminotriazines having at least two asymmetrically substituted carbon atoms of the general formula (I) are obtained when substituted biguanides of the general formula (II)
in which
A, R
1
, R
4
and Z are as defined above,
—and/or acid adducts of compounds of the general formula (II)— are reacted with (optically active) carboxylic acid derivatives of the general formula (III)
in which
R
2
, R
3
and Y are as defined above and
X represents halogen or alkoxy,
if appropriate in the presence of a reaction auxiliary and if appropriate in the presence of a diluent,
and, if appropriate, further conversions within the scope of the above definition of the substituents are carried out by customary methods on the resulting compounds of the general formula (I).
The compounds of the general formula (I) can be converted by customary methods into other compounds of the general formula (I) according to the above definition of the substituents, for example by acylation of compounds of the formula (I) in which R
1
represents amino and/or Y represents hydroxyl, for example using acetyl chloride or propionyl chloride, or, for example, by fluorination of compounds of the formula (I) in which Y represents hydroxyl, for example using diethylaminosulphur tri-fluoride (“DAST”)—cf. the Preparation Examples.
The novel substituted aminotriazines having at least two asymmetrically substituted carbon atoms of the general formula (I) have strong and selective herbicidal activity. To a certain extent, they also have fungicidal and insecticidal activity.
In the definitions, the hydrocarbon chains, such as in alkyl, are in each case straight-chain or branched—including in combination with heteroatoms, such as in alkoxy or alkylthio.
Halogen generally represents fluorine, chlorine, bromine or iodine, preferably represents fluorine, chlorine or bromine, in particular represents fluorine or chlorine.
The invention preferably provides compounds of the formula (I), in which
A represents a single bond, represents methylene (—CH
2
—), dimethylene (ethane-1,2-diyl, —CH
2
CH
2
—), ethylidene (ethane-1,1-diyl, —CH(CH
3
,)—), oxaethanediyl (—CH
2
O—), trimethylene (propane-1,3-diyl, —CH
2
CH
2
CH
2
—), propylidene (propane-1,1-diyl, —CH(C
2
H
5
)—), propane-2,3-diyl (—CH(CH
3
)CH
2
—), 2-methylpropane-1,3-diyl (—CH
2
CH(CH
3
)CH
2
—), 3-oxapropane-1,3-diyl (—CH
2
CH
2
O—), 2-oxapropane-1,3-diyl (—CH
2
OCH
2
—), tetramethylene (butane-1,4-diyl, —CH
2
CH
2
CH
2
CH
2
—), butane-2,4-diyl (—CH(CH
3
)CH
2
CH
2
—), butane-2,3-diyl (—CH(CH
3
)CH(CH
3
)—), 3-methylbutane-2,4-diyl (—CH(CH
3
)CH(CH
3
)CH
2
—), 4-oxabutane-2,4-diyl (—CH(CH
3
)CH
2
O—), pentane-3,5-diyl (—CH(C
2
H
5
)CH
2
CH
2
—), 5-oxa-pentane-3,5-diyl (—CH(C
2
H
5
)CH
2
O—), 4-oxapentane-2,5-diyl (—CH(CH
3
)CH
2
OCH
2
—) or 5-oxahexane-3,6-diyl (—CH(C
2
H
5
)CH
2
OCH
2
),
R
1
represents amino, represents formylamino or represents in each case optionally cyano-, fluorine-, chlorine-, methoxy- or ethoxy-substituted methylamino, ethylamino, dimethylamino,
Dollinger Markus
Drewes Mark Wilhelm
Goto Toshio
Lehr Stefan
Myers Randy Allen
Bayer Aktienegesellschaft
Ford John M.
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