Herbicidal 1,2,4,6-thiatriazines

Details Herbicidal 1,2,4,6-thiatriazines Herbicidal 1,2,4,6-thiatriazines

1998-07-01

2002-03-26

Shah, Mukund J. (Department: 1611)

Plant protecting and regulating compositions

Plant growth regulating compositions

Plural active ingredients

C544S007000, C514S222500

Reexamination Certificate

active

06362134

ABSTRACT:

The present invention relates to novel, herbicidally active thiatriazine derivatives, processes for their preparation, compositions comprising these compounds, and their use for controlling weeds, in particular in crops of useful plants, for example cereals, maize, rice, cotton, soya, oilseed rape, sorghum, sugar cane, sugar beet, sunflower, vegetables and fodder plants, or for inhibiting plant growth.
Thiatriazine compounds are described, for example, in Z. Chem. 15(5), 193-194 (1975), ibid. 15(2), 57-58 (1975), Chem. Ber. 121, 383-386 (1988), Z. Naturforsch. 43, 763-768 (1988), Chem. Ber. 126, 2601-2607 (1993), J. Am. Chem. Soc. 111, 1180-1185 (1989), DD-A-113 006 and in the inaugural dissertation by W. Jürgler, Philipps-University Marburg/Lahn, 1988 (“1&lgr;
4
- and 1&lgr;
6
-2,4,6-thiatriazines from sulfodiimides”).
Novel and simple synthesis methods for preparing novel diversely substituted thiatriazine derivatives have now been found. In addition to the easy accessibility of diversely substituted thiatriazine derivatives, the low number of synthesis stages is another advantage of the synthesis methods. Herbicidal and growth-inhibiting properties have been found for these thiatriazine derivatives.
The present invention thus relates to compounds of the formula I
in which
R
1
is a group —OR
7
, —NR
90
R
91
or an N-heterocyclic radical, onto which 1 or 2 further carbocyclic, heterocyclic or aromatic rings can be fused and which contains or does not contain further heteroatoms;
R
7
is C
1
-C
16
alkyl, C
1
-C
16
alkyl substituted by halogen, NO
2
, CN, C
1
-C
5
alkoxy, C
1
-C
5
alkylthio, C
3
-C
8
cycloalkoxy, C
3
-C
8
cycloalkylthio, C
1
-C
3
trialkylsilyl, C
3
-C
10
alkenyloxy, C
3
-C
5
alkynyloxy, C
1
-C
5
alkylcarbonyloxy, C
1
-C
3
alkoxycarbonyl, C
1
-C
3
alkylcarbonyl, C
5
-C
7
cycloalkenyl or C
5
-C
7
cycloalkenyl substituted by C
1
-C
4
alkyl, or
R
7
is C
1
-C
16
alkyl substituted by C
3
-C
8
cycloalkyl, C
6
-C
12
bicycloalkyl, C
6
-C
12
chlorobicycloalkyl, C
6
-C
12
bicycloalkenyl or adamantyl, or
R
7
C
1
-C
16
alkyl substituted by substituted or unsubstituted aryl, aryloxy, arylmethyleneoxy, arylcarbonyl, arylcarbonyloxy or a heterocyclic ring, or
R
7
is C
3
-C
15
alkenyl, C
3
-C
15
alkenyl substituted by halogen, C
1
-C
3
alkoxy, C
3
-C
8
cycloalkyl, C
1
-C
3
trialkylsilyl or substituted or unsubstituted aryl or aryloxy, or
R
7
is C
3
-C
5
alkynyl, C
3
-C
12
cycloalkyl, C
3
-C
12
cycloalkyl substituted by halogen, CN, C
1
-C
3
trialkylsilyl, ═O, C
1
-C
6
alkyl, cyano-C
1
-C
5
alkyl, C
1
-C
5
alkyl-CONH—C
1
-C
5
alkyl, phenyl-CONH—C
1
-C
5
alkyl, C
1
-C
5
chloroalkyl, C
1
-C
3
alkoxy, C
1
-C
3
alkylthio, C
1
-C
3
alkoxycarbonyl, C
1
-C
3
alkoxycarbonyl-C
1
-C
5
alkyl, C
5
-C
7
cycloalkyl, C
2
-C
4
alkenyl, C
2
-C
4
alkynyl, benzyl or C
1
-C
3
halogenoalkyl, or
R
7
is C
5
-C
7
cycloalkenyl, C
5
-C
7
cycloalkenyl substituted by C
1
-C
3
alkyl, or
R
7
is C
6
-C
12
bicycloalkyl, C
6
-C
12
bicycloalkyl substituted by C
1
-C
3
alkyl, cyano or halogen, C
6
-C
12
bicycloalkenyl, C
6
-C
12
bicycloalkenyl substituted by C
1
-C
3
alkyl, or
R
7
is a substituted or unsubstituted non-aromatic heterocyclic ring or an alicyclic ring system;
R
90
and R
91
independently of one another are hydrogen, C
1
-C
12
alkyl, C
1
-C
12
alkyl substituted by halogen, NO
2
, CN, hydroxyl, C
1
-C
3
alkoxy, C
1
-C
3
alkoxycarbonyl, C
1
-C
3
trialkylsilyl, C
1
-C
6
alkylamino, di(C
1
-C
6
alkyl)amino, C
3
-C
7
cycloalkyl,
 or a heterocyclic ring, or C
3
-C
10
alkenyl, C
3
-C
10
alkynyl, C
6
-C
12
bicycloalkyl, C
6
-C
12
bicycloalkenyl, C
3
-C
12
cycloalkyl, C
3
-C
12
cycloalkyl substituted by C
1
-C
4
alkyl, C
5
-C
7
cycloalkenyl or C
5
-C
7
cycloalkenyl substituted by C
1
-C
4
alkyl, with the proviso that R
90
and R
91
are not simultaneously hydrogen; or
R
90
and R
91
, together with the nitrogen atom to which they are bonded, form a saturated heterocyclic ring which contains 2-12 carbon atoms and can contain, as further heteroatoms, a nitrogen, an oxygen or a sulfur atom and can be substituted by C
1
-C
4
alkyl, C
1
- or C
2
halogenoalkyl, C
1
- or C
2
hydroxyalkyl, methoxy-C
1
-C
4
alkyl, halogen, hydroxyl, CN, C
1
-C
4
alkoxy, C
1
-C
4
alkylcarbonyl, C
1
- or C
2
halogenoalkyl
 C
1
-C
3
alkoxycarbonyl, (C
1
-C
3
alkyl)
2
NCO, di(C
1
-C
4
alkyl)amino or ═O and can additionally be bridged by 1 or 2
 groups and onto which 1 or 2 further carbocyclic, heterocyclic or aromatic rings can be fused, or
R
90
and R
91
, together with the nitrogen atom to which they are bonded, form a mono- or diunsaturated heterocyclic ring which contains 5-7 carbon atoms and is substituted or unsubstituted by C
1
-C
4
alkyl, C
1
- or C
2
halogenoalkyl, halogen, hydroxyl, CN, amino, C
1
-C
4
alkylamino, di(C
1
-C
4
alkyl)amino, phenyl, C
1
-C
4
alkoxy or C
1
-C
3
alkoxycarbonyl and additionally bridged by 1 or 2
 groups and onto which 1 or 2 further carbocyclic, heterocyclic or aromatic rings can be fused;
the radicals R
24
independently of one another are hydrogen or methyl;
R
98
is hydrogen, fluorine, chlorine, bromine, CN, C
1
-C
3
alkoxy, C
1
-C
3
alkoxycarbonyl, C
1
-C
3
alkoxy-C
1
-C
3
alkyl, C
1
- or C
2
halogenoalkyl, C
1
-C
5
alkyl, NO
2
, C
3
-C
5
alkenyl, cyclopropyl or C
1
- or C
2
halogenoalkoxy;
R
2
is halogen, C
1
-C
10
alkoxy, C
1
-C
10
alkoxy substituted by halogen, CN, NO
2
, C
1
-C
6
alkoxy, C
1
-C
6
alkylthio, C
3
-C
6
alkenyloxy, C
1
-C
6
alkoxycarbonyl, heterocyclyl or substituted or unsubstituted aryl or aryloxy, C
3
-C
10
alkenyloxy, C
3
-C
10
alkenyloxy substituted by halogen, CN, NO
2
, C
1
-C
6
alkoxy, C
3
-C
6
alkenyloxy, C
1
-C
6
alkoxycarbonyl or substituted or unsubstituted aryl or aryloxy, C
1
-C
10
alkylthio, C
1
-C
10
alkylthio substituted by halogen, CN, NO
2
, C
1
-C
6
alkoxy, C
3
-C
6
alkenyloxy, C
1
-C
6
alkoxycarbonyl or substituted or unsubstituted aryl or aryloxy, C
3
-C
10
alkenylthio or C
3
-C
10
alkenylthio substituted by halogen, CN, NO
2
, C
1
-C
6
alkoxy, C
3
-C
6
alkenyloxy, C
1
-C
6
alkoxycarbonyl or substituted or unsubstituted aryl or aryloxy, or
R
2
is C
3
-C
5
alkynyloxy, C
3
-C
5
-alkynylthio, C
3
-C
8
cycloalkyl-X—, C
6
-C
12
bicycloalkyl-X—, heterocyclyl-X—, alicyclyl-X—, aryl-X—, phthalidyl-X—, biphenyl-X— or heteroaryl-X—;
X is —O—, —S—, —SO— or —SO
2
—, or
R
2
is a group R
88
R
89
N—,
R
88
and R
89
independently of one another are hydrogen, C
1
-C
6
alkyl, C
1
-C
6
alkyl substituted by halogen, CN, C
1
-C
3
alkoxy or
 C
3
-C
12
cycloalkyl, C
3
-C
10
alkenyl, C
3
-C
10
alkynyl, C
6
-C
12
bicycloalkyl or C
6
-C
12
bicycloalkyl substituted by C
1
-C
3
alkyl;
the radicals R
20
independently of one another are hydrogen or C
1
-C
4
alkyl;
n
7
is 4 or 5;
Y is —O—, —S—, —NH— or —NR
101
—;
R
101
is C
1
-C
4
alkyl, C
1
-C
4
alkylcarbonyl or C
1
-C
3
alkoxycarbonyl; and
R
98
is as defined above;
R
3
is halogen, hydroxyl, C
1
-C
10
alkoxy, C
1
-C
10
alkoxy substituted by halogen, CN, NO
2
, C
1
-C
6
alkoxy, C
1
-C
6
alkylthio, C
3
-C
6
alkenyloxy, C
1
-C
6
alkoxycarbonyl, heterocyclyl or substituted or unsubstituted aryl or aryloxy, C
3
-C
10
alkenyloxy, C
3
-C
10
alkenyloxy substituted by halogen, CN, NO
2
, C
1
-C
6
alkoxy, C
3
-C
6
alkenyloxy, C
1
-C
6
alkoxycarbonyl or substituted or unsubstituted aryl or aryloxy, C
1
-C
10
alkylthio, C
1
-C
10
alkylthio substituted by halogen, CN, NO
2
, C
1
-C
6
alkoxy, C
3
-C
6
alkenyloxy, C
1
-C
6
alkoxycarbonyl or substituted or unsubstituted aryl or aryloxy, C
3
-C
10
alkenylthio or C
3
-C
10
alkenylthio substituted by halogen, CN, NO
2
, C
1
-C
6
alkoxy, C
3
-C
6
alkenyloxy, C
1
-C
6
alkoxycarbonyl or substituted or unsubstituted aryl or aryloxy, or
R
3
is C
3
-C
5
alkynyloxy, C
3
-C
5
alkynylthio, C
3
-C
8
cycloalkyl-X—, C
6
-C
12
bicycloalkyl-X—, heterocyclyl-X—, alicyclyl-X—, aryl-X—, phthalidyl-X—, biphenyl-X— or heteroaryl-X—; and
X is as defined above,
and stereoisomers of the compounds of the formula I,
excluding the compounds of formulae I
1
to I
7
wherein
R
01
is hydrogen, methyl, ethyl, n-propyl, i-butyl, tert-butyl, allyl, cyclohexyl or benzyl;
R
02

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