Plant protecting and regulating compositions – Plant growth regulating compositions – Organic active compound containing
Reexamination Certificate
2000-11-30
2002-07-16
Ford, John M. (Department: 1624)
Plant protecting and regulating compositions
Plant growth regulating compositions
Organic active compound containing
C544S207000, C544S209000
Reexamination Certificate
active
06420313
ABSTRACT:
The invention relates to novel thienylalkylamino-1,3,5-triazines, to processes for their preparation and to their use as herbicides.
A number of thienylalkylaminotriazines are already known from the (patent) literature (cf. JP 63222166—cited in Chem. Abstracts 111:97288w). However, these compounds have hitherto not attained any particular importance.
This invention, accordingly, provides the novel thienylalkylamino-1,3,5-triazines of the general formula (I)
in which
A represents methylene (—CH
2
—) or dimethylene (—CH
2
CH
2
—),
R
1
represents hydrogen or represents optionally cyano-, halogen- or C
1
-C
4
-alkoxy-substituted alkyl having 1 to 4 carbon atoms,
R
2
represents hydrogen, represents formyl or represents in each case optionally cyano-, halogen- or C
1
-C
4
-alkoxy-substituted alkyl, alkylcarbonyl, alkoxy-carbonyl or alkylaminocarbonyl having in each case 1 to 4 carbon atoms in the alkyl groups,
R
3
represents hydrogen or represents optionally cyano-, halogen- or C
1
-C
4
-alkoxy-substituted alkyl having 1 to 4 carbon atoms or represents optionally cyano-, halogen- or C
1
-C
4
-alkyl-substituted cycloalkyl having 3 to 6 carbon atoms,
R
4
represents nitro, cyano, carbamoyl, thiocarbamoyl, halogen, represents in each case optionally halogen-substituted alkyl, alkoxy, alkylcarbonyl or alkoxy-carbonyl having in each case up to 4 carbon atoms, or—in the case that A represents dimethylene—also represents hydrogen,
R
5
represents hydrogen, halogen or represents in each case optionally halogen-substituted alkyl or alkoxy having in each case 1 to 4 carbon atoms, and
Z represents hydrogen, represents halogen, represents in each case optionally cyano-, halogen-, hydroxyl-, C
1
-C
4
-alkoxy- or C
1
-C
4
-alkylthio-substituted alkyl or alkoxy having in each case 1 to 6 carbon atoms, represents in each case optionally cyano-, halogen- or C
1
-C
4
-alkoxy-substituted alkylcarbonyl, alkoxycarbonyl, alkylthio, alkylsulphinyl or alkylsulphonyl having in each case 1 to 6 carbon atoms in the alkyl groups, represents in each case optionally halogen-substituted alkenyl or alkinyl having 2 to 6 carbon atoms, or represents optionally cyano-, halogen- or C
1
-C
4
-alkyl-substituted cyclo-alkyl having 3 to 6 carbon atoms.
The novel thienylalkylaminotriazines of the general formula (I) are obtained when
(a) biguanides of the general formula (II)
in which
A, R
1
, R
2
, R
3
, R
4
and R
5
are as defined above
and/or acid adducts of compounds of the general formula (II)—are reacted with alkoxycarbonyl compounds of the general formula (III)
Z—CO—OR (III)
in which
Z is as defined above and
R′ represents alkyl,
if appropriate in the presence of a reaction auxiliary and if appropriate in the presence of a diluent,
or when
(b) substituted halogenotriazines of the general formula (IV)
in which
A, R
3
, R
4
, R
5
and Z are as defined above and
X represents halogen,
are reacted with nitrogen compounds of the general formula (V)
in which
R
1
and R
2
are as defined above,
if appropriate in the presence of a reaction auxiliary and if appropriate in the presence of a diluent,
or when
(c) substituted aminotriazines of the general formula (VI)
in which
R
1
, R
2
and Z are as defined above and
Y
1
represents halogen or alkoxy,
are reacted with substituted alkylamines of the general formula (VII)
in which
A, R
3
, R
4
and R
5
are as defined above,
if appropriate in the presence of a reaction auxiliary and if appropriate in the presence of a diluent,
or when
(d) substituted 2,4-diamino-1,3,5-triazines of the general formula (Ia)
in which
A, R
1
, R
3
, R
4
, R
5
and Z are as defined above,
are reacted with alkylating or acylating agents of the general formula (VIII)
Y
2
—R
2
(VIII)
in which
R
2
is as defined above, except for hydrogen, and
Y
2
represents halogen, —O—R
2
or —O—CO—R
2
,
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 substituents are carried out by customary methods on the compounds of the general formula (I) obtained according to the processes described under (a), (b), (c) or (d).
The novel substituted 2,4-diamino-1,3,5-triazines of the general formula (I) have strong and selective herbicidal activity.
If appropriate, the compounds of the general formula (I) according to the invention contain an asymmetrically substituted carbon atom and can therefore be present in different enantiomeric (R- and S-configured forms) and/or diastereomeric forms. The invention relates both to the various possible individual enantiomeric or stereo-isomeric forms of the compounds of the general formula (I), and to the mixtures of these isomeric compounds.
In the definitions, the hydrocarbon chains, such as alkyl, are in each case straight-chain or branched, including in combination with hetero atoms, such as in alkoxy or alkylthio.
Halogen generally represents fluorine, chlorine, bromine or iodine, preferably fluorine, chlorine or bromine, in particular fluorine or chlorine.
The invention preferably provides compounds of the formula (I) in which
A represents methylene (—CH
2
—) or dimethylene (—CH
2
CH
2
—),
R
1
represents hydrogen or represents in each case optionally cyano-, fluorine-, chlorine-, methoxy- or ethoxy-substituted methyl, ethyl, n- or i-propyl,
R
2
represents hydrogen, represents formyl or represents in each case optionally cyano-, fluorine-, chlorine-, methoxy- or ethoxy-substituted methyl, ethyl, n- or i-propyl, acetyl, propionyl, n- or i-butyroyl, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, methylaminocarbonyl, ethylaminocarbonyl, n- or i-propylaminocarbonyl,
R
3
represents hydrogen or represents in each case optionally cyano-, fluorine-, chlorine-, methoxy- or ethoxy-substituted methyl, ethyl, n- or i-propyl, or represents in each case optionally cyano-, fluorine-, chlorine-, methyl- or ethyl-substituted cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl,
R
4
represents nitro, cyano, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, or represents in each case optionally fluorine- and/or chlorine-substituted methyl, ethyl, n- or i-propyl, methoxy, ethoxy, n- or i-propoxy and—in the case that A represents dimethylene—also represents hydrogen,
R
5
represents hydrogen, fluorine, chlorine, bromine, or represents in each case optionally fluorine- and/or chlorine-substituted methyl, ethyl, n- or i-propyl, methoxy, ethoxy, n- or i-propoxy, and
Z represents hydrogen, represents fluorine, chlorine, bromine, represents in each case optionally cyano-, fluorine-, chlorine-, bromine-, hydroxyl-, methoxy-, ethoxy-, methylthio- or ethylthio-substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, represents in each case optionally cyano-, fluorine-, chlorine-, methoxy- or ethoxy-substituted acetyl, propionyl, n- or i-butyroyl, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, methylthio, ethylthio, n- or i-propylthio, n-, i-, s- or t-butylthio, methylsulphinyl, ethylsulphinyl, n- or i-propylsulphinyl, methylsulphonyl, ethylsulphonyl, n- or i-propylsulphonyl, represents in each case optionally fluorine-, chlorine- and/or bromine-substituted ethenyl, propenyl butenyl, ethinyl, propinyl or butinyl, or represents optionally cyano-, fluorine-, chlorine-, bromine-, methyl- or ethyl-substituted cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl.
The invention relates in particular to compounds of the formula (I) in which
A represents methylene (—CH
2
—) or dimethylene (—CH
2
CH
2
—),
R
1
represents hydrogen,
R
2
represents hydrogen, formyl, acetyl, propionyl, n- or i-butyroyl, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl,
R
3
represents methyl, ethyl, n- or i-propyl,
R
4
represents nitro, cyano, fluorine, chlorine, bromine, or represents in each case optionally fluorine- and/or chlorine-substituted methyl, ethyl, n- or i-pro
Dollinger Markus
Drewes Mark Wilhelm
Goto Toshio
Kather Kristian
Kirsten Rolf
Bayer Aktiengesellschaft
Ford John M.
Gil Joseph C.
Mrozinski, Jr. John E.
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