2,4-diamino-1,3,5-triazines, processes for their preparation...

Details 2,4-diamino-1,3,5-triazines, processes for their preparation... 2,4-diamino-1,3,5-triazines, processes for their preparation...

1996-08-22

2001-05-29

Shah, Mukund J. (Department: 1611)

Plant protecting and regulating compositions

Plant growth regulators with soil life extenders

C504S234000, C544S208000, C544S209000

Reexamination Certificate

active

06239071

ABSTRACT:

The invention relates to the technical field of herbicides and plant growth regulators, in particular of herbicides for the selective control of weeds and grass weeds in crops of useful plants.
It has been disclosed that 2-amino-4-(phenoxyalkylamino)-1,3,5-triazines substituted in the 6-position have herbicidal and plant growth-regulating properties; cf. WO 94/24086, EP-A-509544, EP-A-492,615. Furthermore, 2-amino-4-[arylamino- or (hetero)arylalkylamino]-6-haloalkyl-1,3,5-triazines having herbicidal action have already been disclosed; cf. U.S. Pat. No. 3,816,419, WO 90/09378, WO 88/02368.
The known active compounds having a 4-[(hetero)arylalkylamino] group in this case each contain a methylene bridge as “alkyl”, which is optionally additionally branch-substituted.
The known active compounds in some cases have disadvantages in their use, be it inadequate herbicidal action against harmful plants, too narrow a spectrum of harmful plants which can be controlled using an active compound, or too low a selectivity in crops of useful plants. Other active compounds cannot be prepared economically on the industrial scale because of poorly accessible precursors and reagents or only have inadequate chemical stabilities.
It is an object of the invention to provide alternative active compounds of the 2,4-diamino-1,3,5-triazines type, which can be employed as herbicides or plant growth regulators.
In German Patent Application No. 19 522 137.0, herbicides of the type mentioned, inter alia, are proposed which in the 6-position on the triazine ring contain an optionally substituted cycloalkyl radical or a heterocycle having an oxygen, nitrogen or sulfur atom and in the 4-position have a phenylalkyl radical having a linear propylene bridge which is optionally additionally branch-substituted.
The present invention relates to compounds of the formula I and their salts
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, 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, (C
3
-C
9
)cycloalkyl which is unsubstituted or substituted, and phenyl which is unsubstituted or substituted, and heterocyclyl having 3 to 6 ring atoms and 1 to 3 hetero ring atoms from the group consisting of N, O and S, the ring being unsubstituted or substituted, or phenyl which is unsubstituted or substituted,
R
2
and R
3
each independently of one another are hydrogen, amino or alkylamino or dialkylamino each having 1 to 6 carbon atoms in the alkyl radical, an acyclic or cyclic hydrocarbon radical or hydrocarbon-oxy radical each having 1 to 10 carbon atoms, preferably having 1 to 6 carbon atoms, or a heterocyclyl radical, heterocyclyloxy radical or heterocyclylamino radical each having 3 to 6 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, 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, in addition to the nitrogen atom the possible further hetero ring atoms being selected from the group consisting of N, O and S and the radical being unsubstituted or substituted,
R
4
is hydrogen, amino, alkylamino or dialkylamino each having 1 to 6 carbon atoms in the alkyl radical, an acyclic or cyclic hydrocarbon radical or hydrocarbon-oxy radical each having 1 to 10 carbon atoms, preferably having 1 to 6 carbon atoms, or a heterocyclyl radical, heterocyclyloxy radical or heterocyclylamino radical each having 3 to 6 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
is hydrogen, halogen, nitro, cyano, thiocyanato or a radical of the formula —B
1
—Y
1
, B
1
and Y
1
being as defined below,
A is an alkylene radical having 1 to 5 linearly linked carbon atoms or alkenylene or alkynylene each having 2 to 5 linearly linked carbon atoms, each of the three last mentioned diradicals being unsubstituted or substituted by one or more radicals from the group consisting of halogen, nitro, cyano, thiocyanato and a radical of the formula —B
2
—Y
2
,
(X)
n
is n substituents X and in this case X in each case independently of one another is halogen, OH, NH
2
, NO
2
, CHO, COOH, CN, SCN or a radical of the formula —B
0
—R, B
0
being as defined below and R being an acyclic hydrocarbon radical having 1 to 6 carbon atoms, which is unsubstituted or substituted, or a radical of the formula —B
0
—R
0
, B
0
being as defined below and R
0
being an aromatic, saturated or partially saturated carbocyclic or heterocyclic radical, the cyclic radical being substituted or unsubstituted, or two adjacent radicals X together are a fused cyclic system 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, preferably X in each case independently of one another is halogen, (C
1
-C
6
)alkyl, (C
2
-C
6
)alkenyl, (C
2
-C
6
)alkynyl, (C
1
-C
6
)alkoxy, (C
2
-C
6
)alkenyloxy, (C
2
-C
6
)alkynyloxy, (C
1
-C
6
)alkylthio, [(C
1
-C
4
)alkyl]carbonyl, [(C
1
-C
4
)alkoxy]carbonyl or [(C
1
-C
4
)alkylthio]carbonyl, the hydrocarbon-containing moieties in the last mentioned 9 radicals being unsubstituted or substituted,
n is 0, 1, 2, 3, 4 or 5, preferably 0, 1, 2, 3 or 4, in particular 2 or 3,
B
0
,B
1
,B
2
in each case independently of one another are a direct bond or a divalent group of the formula —O—, —S(O)
p
—, —S(O)
p
—O—, —O—S(O)
p
—, —CO—, —O—CO—, —CO—O—, —S—CO—, —CO—S—, —S—CS—, —CS—S—, —O—CO—O—, —NR′—, —O—NR′—, —NR′—O—, —NR′—CO—, —CO—NR′—, —O—CO—NR′—, —NR′—CO—O—or —NR′—CO—NR″—, where p=0, 1 or 2 and R′ and R″ independently of one another are 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,
Y
1
,Y
2
each independently of one another are H or an acyclic hydrocarbon radical, for example having 1 to 20 carbon atoms, preferably having 1 to 10 carbon atoms, or a cyclic hydrocarbon radical having 3 to 8 carbon atoms, preferably 3 to 6 carbon atoms, or a heterocyclic radical having 3 to 9 ring atoms and 1 to 3 hetero ring atoms from the group consisting of N, O and S, each of the three last mentioned radicals being unsubstituted or substituted.
The compounds of the formula (I) can form salts by addition of a suitable inorganic or organic acid, such as, for example, HCl, HBr, H
2
SO
4
or HNO
3
, but also oxalic acid or sulfonic acids, to a basic group, such as, for example, amino or alkylamino. Suitable substituents which are present in deprotonated form, such as, for example, sulfonic acids or carboxylic acids, can form internal salts with groups which, for their part, can be protonated, such as amino groups. Salts can likewise be formed by replacing the hydrogen in suitable substituents, such as, for example, sulfonic acids or carboxylic acids, by a cation which is suitable for agriculture. These salts are, for example, metal salts, in particular alkali metal salts or alkaline earth metal salts, in particular sodium and potassium salts, or alternatively ammonium salts or salts with organic amines.
In formula (I) and all following formulae, the radicals alkyl, alkoxy, haloalkyl, haloalkoxy, alkylamino and alkylthio and also the corresponding unsaturated and/or substituted radicals in the hydrocarbon structure can each be straight-chain or branched. If not specifically stated, in these radicals the lower hydrocarbon structures, e.g. having 1 to 6 carbon atoms or, in unsaturated groups, having 2 to 6 carbon atoms, are preferred. Alkyl rad

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