Pyrazde herbicides

Details Pyrazde herbicides Pyrazde herbicides

1997-10-28

2002-01-15

Ramsuer, Robert W. (Department: 1626)

Plant protecting and regulating compositions

Plant growth regulating compositions

Organic active compound containing

C548S375100

Reexamination Certificate

active

06339046

ABSTRACT:

The present invention relates to novel herbicidally active substituted pyrazole derivatives, to processes for their preparation, to compositions comprising these compounds, and to 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, sunflowers, vegetables and fodder plants, or for inhibiting the growth of plants.
Herbicidally active pyrozole compounds have been disclosed and are described, for example, in JP-A-03 093 774, JP-A-02 300 173, JP-A-03 072 460, EP-A-0 361 114 and WO 96/01254.
There have now been found novel substituted pyrazole derivatives which have herbicidal and growth-inhibiting properties.
The present invention thus relates to compounds of the formula I
in which
R
1
is C
1
-C
4
alkyl;
R
2
is cyano or NH
2
C(S)—;
R
3
is hydrogen, C
1
-C
4
alkyl, C
1
-C
4
haloalkyl, C
3
- or C
4
alkenyl, C
3
- or C
4
alkynyl, C
3
-C
8
haloalkenyl, NC—CH
2
—, HOC(O)—CH
2
- or C
1
-C
4
alkoxy-C(O)—CH
2
—;
W is a group
R
4
is hydrogen, fluorine, chlorine, bromine or methyl;
R
5
is hydrogen, halogen, methyl, ethyl, cyano, trifluoromethyl, nitro, amino, hydroxy, C
1
-C
4
haloalkoxy, HOC(O)—C
1
-C
4
alkoxy, CIC(O)—C
1
-C
4
alkoxy, C
1
-C
4
alkoxycarbonyl-C
1
-C
4
alkoxy, mercapto, C
1
-C
4
alkylthio, HOC(O)—C
1
-C
4
alkylthio, C
1
-C
4
alkoxycarbonyl-C
1
-C
4
alkylthio, benzyloxy or benzyloxy which is mono- to trisubstituted by halogen, C
1
-C
4
alkyl or C
1
-C
4
haloalkyl;
R
6
is hydrogen, halogen, cyano, nitro, amino, CIS(O)
2
—, R
10
NH or R
10
R
11
N;
R
10
and R
11
independently of one another are C
1
-C
8
alkyl, C
3
-C
8
alkenyl, C
3
-C
8
alkynyl, C
3
-C
6
cycloalkyl, C
1
-C
8
haloalkyl, C
3
-C
8
haloalkenyl, C
1
-C
4
alkylcarbonyl, C
1
-C
4
haloalkylcarbonyl, C
1
-C
4
alkylsulfonyl, C
1
-C
4
haloalkylsulfonyl, benzoyl, benzoyl which is mono- to trisubstituted by C
1
-C
4
alkyl, C
1
-C
4
haloalkyl or halogen, or are benzyl or benzyl which is mono- to trisubstituted by C
1
-C
4
alkyl, C
1
-C
4
haloalkyl or halogen; or
R
6
is —OR
20
;
R
20
is hydrogen, C
1
-C
8
alkyl, C
3
-C
8
alkenyl, C
3
-C
8
alkynyl, C
1
-C
8
haloalkyl,
 C
3
-C
8
haloalkenyl, C
3
-C
6
cycloalkyl,
 C
1
-C
4
alkoxy-C
1
-C
4
alkyl, C
1
-C
4
alkenyloxy-C
1
-C
4
alkyl, C
1
-C
4
alkylamino-C
1
-C
4
alkyl, di-C
1
-C
4
alkylamino-C
1
-C
4
alkyl, C
1
-C
4
alkoxy-C
1
-C
4
alkoxy-C
1
-C
4
alkyl, C
1
-C
4
alkylthio-C
1
-C
4
alkyl, C
1
-C
4
alkyl-C(O)—C
1
-C
8
alkyl,
 C
1
-C
4
alkyl-C(O—C
1
-C
4
alkyl)
2
-C
1
-C
8
alkyl,
 phenyl, benzyl, pyridyl, pyrimidinyl, pyrazinyl or
 pyridazinyl, it being possible for these abovementioned aromatic and heteroaromatic rings to be mono- to trisubstituted by C
1
-C
4
alkyl, C
1
-C
4
haloalkyl or halogen; or
R
20
is R
21
XC(O)—C
1
-C
8
alkyl or
X is oxygen, sulfur, or R
22
N;
R
21
is hydrogen, C
1
-C
8
alkyl, C
3
-C
8
alkenyl, C
3
-C
8
alkynyl, C
1
-C
8
haloalkyl, C
3
-C
6
cycloalkyl, C
1
-C
4
alkoxy-C
1
-C
4
alkyl, C
1
-C
4
alkylthio-C
1
-C
4
alkyl, phenyl, phenyl which is mono- to trisubstituted by C
1
-C
4
alkyl, C
1
-C
4
haloalkyl or halogen, or is benzyl or benzyl which is mono- to trisubstituted by C
1
-C
4
alkyl or halogen; and
R
22
is hydrogen, C
1
-C
8
alkyl or C
3
-C
8
alkenyl, or
R
6
is —S(O)
m
R
30
;
m is 0, 1 or 2;
R
30
is hydrogen, C
1
-C
8
alkyl, C
3
-C
8
alkenyl, C
3
-C
8
alkynyl, C
1
-C
8
haloalkyl, C
3
-C
8
haloalkenyl, C
3
-C
6
cycloalkyl, C
1
-C
4
alkoxy-C
1
-C
4
alkyl, C
1
-C
4
alkylthio-C
1
-C
4
alkyl, C
1
-C
4
alkylC(O)—C
1
-C
8
alkyl, phenyl, phenyl which is mono- to trisubstituted by C
1
-C
4
alkyl, C
1
-C
4
haloalkyl or halogen, benzyl, benzyl which is mono- to trisubstituted by C
1
-C
4
alkyl, C
1
-C
4
haloalkyl or halogen, or R
31
VC(O)—C
1
-C
4
alkyl;
V is oxygen, sulfur or R
32
N;
R
31
is hydrogen, C
1
-C
8
alkyl, C
3
-C
8
alkenyl, C
3
-C
8
alkynyl, C
1
-C
8
haloalkyl, C
3
-C
6
cycloalkyl, C
1
-C
4
alkoxy-C
1
-C
4
alkyl, C
1
-C
4
alkylthio-C
1
-C
4
alkyl, phenyl, phenyl which is mono- to trisubstituted by C
1
-C
4
alkyl, C
1
-C
4
haloalkyl or halogen, or is benzyl, or benzyl which is mono- to trisubstituted by C
1
-C
4
alkyl, C
1
-C
4
haloalkyl or halogen;
R
32
is hydrogen, C
1
-C
8
alkyl or C
3
-C
8
alkenyl; or
R
33
is hydrogen, C
1
-C
8
alkyl, C
3
-C
8
alkenyl or C
3
-C
8
alkynyl;
R
34
is hydrogen, C
1
-C
8
alkyl, C
3
-C
8
alkenyl, C
3
-C
8
alkynyl or C
1
-C
4
alkylcarbonyl; or
R
6
is —COR
40
;
R
40
is hydrogen, chlorine, C
1
-C
8
alkyl, C
2
-C
8
alkenyl, C
2
-C
8
alkynyl, C
1
-C
8
haloalkyl, C
2
-C
8
haloalkenyl, C
3
-C
6
cycloalkyl, C
1
-C
4
alkoxy-C
1
-C
4
alkyl, C
1
-C
4
alkylthio-C
1
-C
4
alkyl, phenyl, phenyl which is mono- to trisubstituted by C
1
-C
4
alkyl, C
1
-C
4
haloalkyl or halogen, or is benzyl or benzyl which is mono- to trisubstituted by C
1
-C
4
alkyl, C
1
-C
4
haloalkyl or halogen; or
R
6
is —COYR
50
;
Y is oxygen, sulfur, R
51
N or R
54
ON;
R
50
is hydrogen, C
1
-C
8
alkyl, C
3
-C
8
alkenyl, C
3
-C
8
alkynyl, C
1
-C
8
haloalkyl,
 C
3
-C
8
haloalkenyl, cyano-C
1
-C
4
alkyl, C
3
-C
6
cycloalkyl,
 C
1
-C
4
alkoxy-C
1
-C
4
alkyl, C
1
-C
4
alkylthio-C
1
-C
4
alkyl, phenyl,
 phenyl which is mono- to trisubstituted by C
1
-C
4
alkyl, C
1
-C
4
haloalkyl or halogen, benzyl, benzyl which is mono- to trisubstituted by C
1
-C
4
alkyl, C
1
-C
4
haloalkyl or halogen, or is C
1
-C
8
alkylcarbonyl-C
1
-C
4
alkyl, R
52
ZC(O)—C
1
-C
6
alkyl or R
52
ZC(O)—C
3
-C
6
cycloalkyl;
Z is oxygen, sulfur, R
53
N or R
55
ON;
R
52
is hydrogen, C
1
-C
8
alkyl, C
3
-C
8
alkenyl, C
3
-C
8
alkynyl, C
1
-C
8
haloalkyl,
 C
3
-C
8
haloalkenyl, C
3
-C
6
cycloalkyl,
 C
1
-C
4
alkoxy-C
1
-C
4
alkyl, C
1
-C
4
alkoxy-C
1
-C
4
alkoxy-C
1
-C
4
alkyl, C
1
-C
4
alkylthio-C
1
-C
4
alkyl, phenyl, phenyl which is mono- to trisubstituted by C
1
-C
4
alkyl, C
1
-C
4
haloalkyl or halogen, or is benzyl or benzyl which is mono- to trisubstituted by C
1
-C
4
alkyl, C
1
-C
4
haloalkyl or halogen;
R
51
and R
53
independently of one another are C
1
-C
8
alkyl, C
3
-C
8
alkenyl, C
3
-C
8
alkynyl, C
1
-C
8
haloalkyl, C
1
-C
4
alkylcarbonyl, C
1
-C
4
haloalkylcarbonyl, C
1
-C
4
alkylsulfonyl, C
1
-C
4
haloalkylsulfonyl, benzoyl, benzoyl which is mono- to trisubstituted by C
1
-C
4
alkyl, C
1
-C
4
haloalkyl or halogen, or are benzyl or benzyl which is mono- to trisubstituted by C
1
-C
4
alkyl, C
1
-C
4
haloalkyl or halogen;
R
54
and R
55
independently of one another are C
1
-C
4
alkyl; or
R
6
is B—C
1
-C
8
alkyl, B—C
1
-C
8
haloalkyl, B—C
2
-C
8
alkenyl, B—C
2
-C
8
alkynyl, B—C
2
-C
8
haloalkenyl, B—C
1
-C
4
alkoxy-C
1
-C
4
alkyl or B—C
1
-C
4
alkylthio-C
1
-C
4
alkyl; and
B is hydrogen, R
52
ZC(O)—, cyano or C
1
-C
4
alkylcarbonyl;
X
1
and X
2
independently of one another are oxygen or sulfur;
R
60
is hydrogen or C
1
-C
4
alkyl;
R
61
is hydrogen, C
1
-C
6
alkyl, C
3
-C
6
cycloalkyl, C
3
-C
6
alkenyl, C
3
-C
6
alkynyl, benzyl, benzyl substituted by halogen, C
1
-C
6
haloalkyl, C
3
-C
6
haloalkenyl, C
1
-C
4
alkyl-C(O)—C
1
-C
4
alkyl, C
1
-C
4
alkoxy-C
1
-C
4
alkyl, C
1
-C
4
alkoxy-C
1
-C
4
alkoxy-C
1
-C
4
alkyl, HOC(O)—C
1
-C
6
alkyl, CIC(O)—C
1
-C
6
alkyl, C
1
-C
6
alkoxycarbonyl-C
1
-C
6
alkyl, C
1
-C
6
haloalkoxycarbonyl-C
1
-C
6
alkyl, C
3
-C
6
alkenyloxycarbonyl-C
1
-C
6
alkyl, C
3
-C
6
alkynyloxycarbonyl-C
1
-C
6
alkyl, C
1
-C
6
alkylthio-C(O)—C
1
-C
6
alkyl, C
3
-C
6
alkenylthio-C(O)—C
1
-C
6
alkyl, C
3
-C
6
alkynylthio-C(O)—C
1
-C
6
alkyl, C
1
-C
6
haloalkylthio-C(O)—C
1
-C
6
alkyl,
R
62
R
63
NC(O)—C
1
-C
6
alkyl,
 C
1
-C
4
alkoxycarbonyl, C
3
-C
6
alkenyloxycarbonyl, C
3
-C
6
alkynyloxycarbonyl, oxetanyloxycarbonyl, HOC(O)—C
3
-C
6
cycloalkyl, C
1
-C
4
alkoxycarbonyl-C
3
-C
6
cycloalkyl, C
3
-C
6
alkenyloxycarbonyl-C
3
-C
6
cycloalkyl, C
3
-C
6
alkynyloxycarbonyl-C
3
-C
6
cycloalkyl, C
1
-C
6
alkylthio-C
1
-C
6
alkyl, C
3
-C
6
alkenylthio-C(O)—C
3
-C
6
cycloalkyl or CIC(O)—C
3
-C
6
cycloalkyl;
R
62
is hydrogen, C
1
-C
6
alkyl, C
3
-C
6
alkenyl, C
3
-C
6
alkynyl, C
1
-C
6
haloalkyl, benzyl, phenyl, or phenyl which is mono- to trisubstituted by halogen, C
1
-C
4
alkyl or C
1
-C
4

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