2,4-diamino-1,3,5-triazines, their preparation and their use...

Details 2,4-diamino-1,3,5-triazines, their preparation and their use... 2,4-diamino-1,3,5-triazines, their preparation and their use...

2003-01-24

2003-11-11

Ford, John M. (Department: 1624)

Plant protecting and regulating compositions

Plant growth regulating compositions

Organic active compound containing

C544S206000, C544S207000, C544S113000

Reexamination Certificate

active

06645916

ABSTRACT:

It is known that some 2-amino4-(phenoxyethylamino)-1,3,5-triazines substituted in position 6 have herbicidal and plant growth-regulating properties; cf. WO 90/09378 (U.S. Pat. No. 5,290,754 and U.S. Pat. No. 5,403,815), WO 94/24086 (U.S. Pat. No. 5,527,954), WO 96/25404.
Some of the known compounds have disadvantages when being used, be it insufficient herbicidal activity against harmful plants, too small a spectrum of harmful plants which can be controlled by one active compound, or inadequate selectivity in crops of useful plants.
It is an object of the present invention to provide alternative or improved active compounds of the type of the 2,4-diamino-1,3,5-triazines which can be used as herbicides or plant growth regulators.
The resent invention provides compounds of the formula (I) and salts thereof
in which
R
1
is (C
1
-C
6
)alkyl,
which is unsubstituted or substituted by one or more radicals from the group consisting of halogen, hydroxyl, cyano, nitro, thiocyanato, (C
1
-C
4
)alkoxy, (C
1
-C
4
)alkylthio, (C
1
-C
4
)alkylsulfinyl, (C
1
-C
4
)alkylsulfonyl, (C
2
-C
4
)alkenyl, (C
2
-C
4
)alkynyl and phenyl which is unsubstituted or substituted, or
is phenyl which is unsubstituted or substituted,
R
2
and R
3
in each case independently of one another are hydrogen,
amino, (C
1
-C
6
)alkyl-amino or di-[(C
1
-C
6
)alkyl]amino, a hydrocarbon radical or hydrocarbonoxy radical having in each case 1 to 10 carbon atoms, preferably having 1 to 6 carbon atoms, or a heterocyclyl radical, heterocyclyloxy radical or heterocyclylamino radical having in each case 3 to 9 ring atoms and 1 to 3 hetero-ring atoms from the group consisting of N, O and S, each of the five last-mentioned radicals being unsubstituted or substituted, or are an acyl radical, or
R
2
and R
3
, together with the nitrogen atom of the group NR
2
R
3
, are a heterocyclic radical having 3 to 6 ring atoms and 1 to 4 hetero-ring atoms, any further hetero-ring atoms in addition to the nitrogen atom being selected from the group consisting of N, O and S, and the radical being unsubstituted or substituted,
R
4
is hydrogen, amino, (C
1
-C
6
)alkylamino, di-[(C
1
-C
6
)alkyl]amino, a hydrocarbon radical or hydrocarbonoxy radical having in each case 1 to 10 carbon atoms, preferably having 1 to 6 carbon atoms, or a heterocyclyl radical, heterocyclyloxy radical or heterocyclylamino radical having in each case 3 to 9 ring atoms and 1 to 3 hetero-ring atoms from the group consisting of N, O and S, each of the five last-mentioned radicals being unsubstituted or substituted, or an acyl radical,
R
5
and R
6
in each case independently of one another are halogen, nitro, cyano, thiocyanato or a radical of the formula —X
1
—A
1
in which X
1
is a direct bond or a bivalent group of the formula —O—, —S(O)
p
—O—, —O—S(O)
p
—, —CO—, —O—CO—, —CO—O—, —NR′—, —O—NR′—, —NR′—O—, —NR′—CO— or —CO—NR′—, p in the formulae being 0, 1 or 2 and R′ being hydrogen, alkyl having 1 to 6 carbon atoms, phenyl, benzyl, cycloalkyl having 3 to 6 carbon atoms or alkanoyl having 1 to 6 carbon atoms, and
in which A
1
is hydrogen or a hydrocarbon radical or a heterocyclic radical, each of the two last-mentioned radicals being unsubstituted or substituted, or
R
5
and R
6
together are an alkylene chain having 2 to 4 carbon atoms which is unsubstituted or substituted by one or more radicals from the group consisting of halogen, (C
1
-C
4
)alkyl and oxo,
R
7
independently of other radicals R
7
is in each case halogen, nitro, cyano, thiocyanato or a radical of the formula —X
2
—A
2
,
in which X
2
is a direct bond or a bivalent group of the formula —O—, —S(O)
q
—, —S(O)
q
—O—, —O—S(O)
q
—, —CO—, —O—CO—, —CO—O—, —NR″—, —O—N—R″—, —NR″—O—, —NR″—CO— or —CO—NR″—, q in the formulae being 0, 1 or 2 and R′ being hydrogen, (C
1
-C
6
)-alkyl, phenyl, (C
3
-C
6
)-cycloalkyl, and A
2
is hydrogen or a hydrocarbon radical or a heterocyclic radical, each of the two last-mentioned radicals being unsubstituted or substituted,
or two adjacent radicals R
7
together are a fused-on cycle having 4 to 6 ring atoms, which is carbocyclic or contains hetero-ring atoms from the group consisting of O, S and N, and which is unsubstituted or substituted by one or more radicals from the group consisting of halogen, (C
1
-C
4
)alkyl and oxo,
X is a group of the formula —O—, —S(O)
r
—, —NR*— or —N(O)—, in which r is 0, 1 or 2 and R* is hydrogen or alkyl having 1 to 4 carbon atoms, and
n is 0, 1, 2, 3, 4 or 5,
except for compounds of the formula (I) or salt thereof
a) in which
R
1
is 1-haloethyl, 1-halo-1-methyl-ethyl or 1-halo-1 -methyl-propyl,
R
2
, R
3
, R
4
, R
6
are each hydrogen,
R
5
is methyl,
R
7
is (C
1
-C
4
)alkyl, CF
3
, OCH
3
or fluorine, where in the case of n=2 both radicals R
7
are defined the same,
n is the number 0, 1 or 2 and
X is an oxygen atom, and
b) in which
R
1
is (C
1
-C
10
)alkyl, which is unsubstituted or substituted by 1 to 4 substituents from the group consisting of (C
1
-C
4
)alkoxy and hydroxyl,
R
2
, R
3
, R
4
, R
6
are each hydrogen,
R
5
is methyl,
R
7
independently of other radicals R
7
is in each case (C
1
-C
4
)alkyl or halogen,
n is the, number 0, 1, 2, 3 or 4 and
X is an oxygen atom.
The compounds of formula (I) can form salts by adding on an appropriate inorganic or organic acid, for example HCl, HBr, H
2
SO
4
or HNO
3
, or else oxalic acid or sulfonic acids, to a basic group, for example amino or alkylamino. Suitable substituents, which may be in deprotonated form, such as, for example, sulfonic acids or carboxylic acids, may form inner salts with groups which are in turn protonateable, such as amino groups. Salts can likewise be formed by replacing the hydrogen in appropriate substituents, for example sulfonic acids or carboxylic acids, by an agriculturally useful cation. Examples of these salts are metal salts, in particular alkali metal salts, or alkaline earth metal salts, in particular sodium salts and potassium salts, or else ammonium salts or salts with organic amines.
In formula (I) and all subsequent formulae, the radicals alkyl, alkoxy, haloalkyl, haloalkoxy, alkylamino and alkylthio and the corresponding unsaturated and/or substituted radicals can in each case be straight-chain or branched in the carbon skeleton. Unless indicated specifically, the lower carbon skeletons, for example those having 1 to 6 carbon atoms or, in the case of unsaturated groups, having 2 to 6 carbon atoms, are preferred for these radicals.
(C
1
-C
6
)alkyl is the short notation for alkyl having 1 to 6 carbon atoms. Halo-(C
1
-C
6
)alkyl and (C
1
-C
6
)haloalkyl are both haloalkyl having 1 to 6 carbon atoms in the alkyl moiety; this applies correspondingly to other (substituted) radicals. Alkyl radicals, also in the composite meanings such as alkoxy, haloalkyl, etc., are, for example, methyl, ethyl, n- or i-propyl, n-, i-, t- or 2-butyl, pentyls, hexyls, such as n-hexyl, i-hexyl and 1,3-dimethylbutyl, heptyls, such as n-heptyl, 1-methylhexyl and 1,4-dimethylpentyl; alkenyl and alkynyl radicals have the meaning of the possible unsaturated radicals corresponding to the alkyl radicals; alkenyl is, for example, ethenyl, allyl, 1-methylprop-2-en-1-yl, 2-methyl-prop-2-en-1-yl, but-2-en-1-yl, but-3-en-1-yl, 1-methyl-but-3-en-1-yl and 1-methyl-but-2-en-1-yl; alkynyl is, for example, ethynyl, propargyl, but-2-in-1-yl, but-3-in-1-yl, 1-methyl-but-3-in-1-yl. Cycloalkyl is a carbocyclic saturated ring system preferably having 3-6 carbon atoms, for example cyclopropyl, cyclopentyl or cyclohexyl.
Halogen is, for example, fluorine, chlorine, bromine, or iodine. Haloalkyl, haloalkenyl and haloalkynyl are alkyl, alkenyl and alkynyl, respectively, which are fully or partially substituted by halogen, preferably by fluorine, chlorine and/or bromine, in particular by fluorine or chlorine, for example monohaloalkyl (=monohalogenoalkyl), perhaloalkyl, CF
3
, CHF
2
, CH
2
F, CF
3
CF
2
, CHF
2
CF
2
, CH
2
FCHCl, CCl
3
, CHCl
2
, CH
2
CH
2
Cl; haloalkoxy is, for example, OCF
3

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