Herbicidal S-substituted 1,2,4,6-thiatriazines

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

1999-12-17

2001-07-31

Raymond, Richard L. (Department: 1611)

Plant protecting and regulating compositions

Plant growth regulating compositions

Organic active compound containing

C544S007000

Reexamination Certificate

active

06268308

ABSTRACT:

The present invention relates to novel herbicidally active thiatriazine derivatives, processes for their preparaiton, compositions which comprise these compounds, and their use for controlling weeds, in particular in crops of useful plants, or for inhibiting plant growth.
Thiatriazine compounds are described, for example in Chem. Ber. 121, 383-386 (1988), Z. Naturforsch. 43, 763-768 (1988), Chem. Ber. 126, 2601-2607 (1993), J. Am. Chem. Soc. 1989, 111, 1180-1185, DD 113 006 and in WO 96/01814. Novel thiatriazine derivatives having herbicidal and growth-inhibiting properties have now been found.
The present invention thus relates to compounds of the formula I
in which
Q
i
is the group
R
2
and R
3
independently of one another are hydrogen, C
1
-C
6
alkyl or C
1
-C
6
alkyl substituted by S(O)
n
R
6
, halogen, cyano, nitro, C
1
-C
8
alkoxy, C
3
-C
6
trialkylsilyl, hydroxyl, amino, ammonium, tri-C
1
-C
4
alkylammonium, —COOH, —COOM, in which M is ammonium or an alkali metal or alkaline earth metal atom, C
3
-C
8
cycloalkyl, C
1
-C
5
alkylcarbonyloxy, phenylcarbonyloxy, naphthylcarbonyloxy, C
1
-C
6
alkylamino, C
1
-C
5
alkylcarbonyl, C
2
-C
12
dialkylamino, phenyl, naphthyl, phenoxy, naphthoxy, biphenyl, biphenyloxy, phenthio or naphthio, it being possible for the aromatic rings mentioned to be substituted by halogen, cyano, nitro, —OR
5
, —NR
10
R
11
, C
1
-C
4
alkyl, formyl, C
1
-C
4
alkylcarbonyl, COOR
7
, C
1
-C
4
alkylthio, C
1
-C
4
alkylsulfonyl or —CONR
8
R
9
, or
R
2
and R
3
independently of one another are C
2
-C
6
alkenyl or C
2
-C
6
alkenyl substituted by halogen, cyano, nitro, C
1
-C
8
alkoxy, C
3
-C
6
trialkylsilyl, hydroxyl, amino, ammonium, tri-C
1
-C
4
alkylammonium, —COOH, —COOM, in which M is ammonium or an alkali metal or alkaline earth metal atom, C
3
-C
8
cycloalkyl, C
2
-C
5
alkylcarbonyloxy, phenylcarbonyloxy, naphthylcarbonyloxy, C
1
-C
6
alkylamino, C
2
-C
5
alkoxycarbonyl, C
2
-C
2
dialkylamino, phenyl, naphthyl, phenoxy, naphthoxy, biphenyl, biphenyloxy, phenthio or naphthio, it being possible for the aromatic rings mentioned to be substituted by halogen, cyano, nitro, —OR
5
, —NR
10
R
11
, C
1
-C
4
alkyl, formyl, C
1
-C
4
alkylcarbonyl, COOR
7
, C
1
-C
4
alkylthio, C
1
-C
4
alkylsulfonyl or —CONR
8
R
9
, or
R
2
and R
3
independently of one another are C
3
-C
6
alkynyl or C
3
-C
6
alkynyl substituted by halogen, cyano, nitro, C
1
-C
8
alkoxy, C
3
-C
6
trialkylsilyl, hydroxyl, amino, ammonium, tri-C
1
-C
4
alkylammonium, —COOH, —COOM, in which M is ammonium or an alkali metal or alkaline earth metal atom, C
3
-C
8
cycloalkyl, C
1
-C
5
alkylcarbonyloxy, phenylcarbonyloxy, naphthylcarbonyloxy, C
1
-C
6
alkylamino, C
1
-C
5
alkoxycarbonyl, C
2
-C
12
dialkylamino, phenyl, naphthyl, phenoxy, naphthoxy, biphenyl, biphenyloxy, phenthio or naphthio, it being possible for the aromatic rings mentioned to be substituted by halogen, cyano, nitro, —OR
5
, —NR
10
R
11
, C
1
-C
4
alkyl, formyl, C
1
-C
4
alkylcarbonyl, COOR
7
, C
1
-C
4
alkylthio, C
1
-C
4
alkylsulfonyl or —CONR
8
R
9
, or
R
2
and R
3
independently of one another are formyl, C
1
-C
15
alkylcarbonyl, C
2
-C
15
alkenylcarbonyl, C
4
-C
9
cycloalkylcarbonyl, C
6
-C
9
cycloalkenylcarbonyl or C
3
-C
8
cycloalkyl-C
1
-C
6
alkylcarbonyl, it being possible for these substituents to be substituted by halogen, cyano, nitro, hydroxyl, amino, C
1
-C
6
alkylamino, C
2
-C
12
dialkylamino, —COOH, —COOM, in which M is ammonium or an alkali metal or alkaline earth metal atom, C
1
-C
8
alkoxycarbonyl, C
4
-C
10
cycloalkoxycarbonyl, C
1
-C
8
alkylaminocarbonyl or C
2
-C
12
dialkylaminocarbonyl, or
R
2
and R
3
independently of one another are heterocyclyl, heterocyclylcarbonyl, heterocyclyl substituted by halogen, cyano, nitro, C
1
-C
5
alkyl, C
1
-C
5
alkoxy, C
1
-C
5
alkylcarbonyl, C
1
-C
5
alkylcarbonyloxy, C
1
-C
6
alkoxycarbonyl, aminocarbonyl, C
1
-C
6
alkylaminocarbonyl or C
2
-C
11
dialkylaminocarbonyl, or heterocyclylcarbonyl substituted by halogen, cyano, nitro, C
1
-C
5
alkyl, C
1
-C
5
alkoxy, C
1
-C
5
alkylcarbonyl, C
1
-C
6
alkoxycarbonyl, aminocarbonyl, C
1
-C
6
alkylamino or C
1
-C
5
alkylcarbonyloxy, or
R
2
and R
3
independently of one another are phenylcarbonyl, biphenylcarbonyl, naphthylcarbonyl, phenyl-C
1
-C
6
alkylcarbonyl, biphenyl-C
1
-C
6
alkylcarbonyl, naphthyl-C
1
-C
6
alkylcarbonyl, phenyl-C
2
-C
6
alkenylcarbonyl, biphenyl-C
2
-C
6
alkenylcarbonyl, naphthyl-C
2
-C
6
alkenylcarbonyl, phenyl-C
3
-C
6
alkynylcarbonyl, biphenyl-C
3
-C
6
alkynylcarbonyl or naphthyl-C
3
-C
6
alkynylcarbonyl, it being possible for these substituents to be substituted by C
1
-C
5
alkyl, C
1
-C
5
alkoxy, C
1
-C
5
alkylthio, C
1
-C
5
halogenoalkyl, C
1
-C
5
alkylcarbonyl, halogen, cyano, amino, nitro, —COOR
7
, C
1
-C
8
alkoxycarbonyl, hydroxyl, C
1
-C
5
alkylsulfinyl, C
1
-C
5
alkylsulfonyl, C
1
-C
6
alkylaminocarbonyl or C
2
-C
12
dialkylaminocarbonyl, or
R
2
and R
3
independently of one another are phenyl or naphthyl, it being possible for there substituents to be substituted by halogen, cyano, nitro, C
1
-C
5
alkyl, C
1
-C
5
alkoxy, C
1
-C
5
alkylthio, —COOH, —CONH
2
, C
1
-C
6
alkylaminocarbonyl, C
2
-C
10
dialkylaminocarbonyl, C
1
-C
5
alkylcarbonyl or C
1
-C
5
alkoxycarbonyl, or
R
2
and R
3
, together with the nitrogen atom to which they are bonded, form a heterocyclic ring, which can be substituted by C
1
-C
5
alkyl, C
1
-C
5
alkoxy, halogen, cyano or nitro, or
R
2
and R
3
independently of one another are amino, C
1
-C
6
alkylamino, C
2
-C
8
dialkylamino, phenylamino, naphthylamino, C
1
-C
6
alkylcarbonylamino, C
1
-C
10
alkoxycarbonylamino, hydroxyl, C
1
-C
6
alkoxy, C
1
-C
6
alkylcarbonyloxy, phenoxy, biphenyloxy or naphthoxy, X is oxygen or S(O)
x
, in which x is the number 0, 1 or 2, and
R
4
is C
1
-C
8
alkyl, C
2
-C
8
alkenyl, C
3
-C
8
alkynyl, C
3
-C
8
cycloalkyl, C
5
-C
8
cycloalkenyl, C
3
-C
8
cycloalkyl-C
1
-C
4
alkyl or C
1
-C
4
alkyl-C
3
-C
8
cycloalkyl, it being possible for these substituents to be substituted by halogen, cyano, nitro, ═O or —OR
5
, or
R
4
is phenyl, biphenyl, naphthyl, heterocyclyl, C
1
-C
4
alkylphenyl, C
1
-C
4
alkylnaphthyl, phenyl-C
1
-C
4
alkyl or naphthyl-C
1
-C
4
alkyl, it being possible for these substituents to be substituted by halogen, cyano, nitro, amino, —COOH, hydroxyl, C
1
-C
10
alkyl, C
1
-C
10
alkyloxy, C
1
-C
6
alkylamino, di-C
2
-C
8
alkylamino, C
1
-C
10
alkylthio, C
1
-C
10
halogenoalkyl, C
1
-C
10
halogenoalkoxy, C
1
-C
10
halogenoalkylthio, C
2
-C
10
alkoxycarbonylalkoxy, C
1
-C
6
alkylsulfinyl, C
1
-C
6
alkylsulfonyl, C
1
-C
6
alkyloxycarbonyl, C
1
-C
6
alkylcarbonyl, —CONH
2
, formyl, C
1
-C
7
alkylaminocarbonyl, C
2
-C
11
dialkylaminocarbonyl, C
3
-C
6
trialkylsilyl, C
1
-C
10
alkylcarbonylamino, C
1
-C
10
alkylcarbonyloxy, phenoxy, halophenoxy, pyridyloxy or by pyridyloxy substituted by halogen, C
1
-C
4
alkyl, C
1
-C
4
alkoxy, cyano, nitro or amino, or two substituents adjacent to each other on the phenyl or naphthyl ring R
4
form a carbocyclic or heterocyclic ring, which can be substituted by halogen, cyano, nitro, amino, —COOH, oxo, C
1
-C
10
alkyl, C
1
-C
10
alkoxy, C
1
-C
10
alkylthio, C
1
-C
10
halogenoalkyl, hydroxyl, C
3
-C
10
alkoxycarbonylalkoxy, C
1
-C
6
alkylsulfinyl, C
1
-C
6
alkylsulfonyl, C
2
-C
6
alkyloxycarbonyl, C
2
-C
6
alkylcarbonyl, —CONH
2
, formyl, C
2
-C
7
alkylaminocarbonyl, C
3
-C
11
dialkylaminocarbonyl, C
3
-C
6
trialkylsilyl, C
2
-C
10
alkylcarbonylamino, C
2
-C
10
alkylcarbonyloxy, phenoxy, pyridyloxy or by pyridyloxy substituted by halogen, C
1
-C
4
alkyl, C
1
-C
4
alkoxy, cyano, nitro or amino, R
5
is hydrogen, C
1
-C
6
alkyl, C
1
-C
6
halogenoalkyl, C
2
-C
5
alkoxyalkyl, C
1
-C
6
cyanoalkyl, phenyl, phenyl-C
1
-C
4
alkyl, formyl, C
2
-C
7
alkylcarbonyl, C
2
-C
7
alkoxycarbonyl, C
1
-C
6
alkylaminocarbonyl, C
2
-C
8
dialkylaminocarbonyl, benzoyl, halogenobenzoyl, C
1
-C
6
alkylamino, C
2
-C
8
dialkylamino, —N═CH
2
, —N═CH—C
1
-C
4
alkyl, —N═C(C
1
-C
4
alkyl)
2
, tri(C
1
-C
4
alkyl)silyl, C
3
-C
7
cycloalkyl, C
2
-C
7
alkenyl, C
3
-C
7
alkynyl or heterocyclyl,
n is the number 0, 1 or 2

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