Herbicides

Details Herbicides Herbicides

1999-05-07

2001-03-20

Fan, Jane (Department: 1612)

Plant protecting and regulating compositions

Plant growth regulating compositions

Organic active compound containing

C546S275400, C546S276100

Reexamination Certificate

active

06204221

ABSTRACT:

The present invention relates to novel herbicidally active substituted pyrazole derivatives, a process 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, sugarcane, sugarbeet, sunflowers, vegetables, plantations and fodder plants, or for inhibiting plant growth. Phenyl-pyrazole compounds having a herbicidal action are known and are described, for example, in EP-A-0 361 114, U.S. Pat. No. 5,032,165, WO 92/02509, WO 92106962, WO 95133728 and WO 96/01254. It has now been found, surprisingly, that substituted pyridyl-pyrazole derivatives have outstanding herbicidal and growth-inhibiting properties.
The present invention therefore relates to compounds of the formula I
in which
A is ═N— or
n
13
is 1, 2 or 3;
R
1
is hydrogen, C
1
-C
4
alkyl, C
1
-C
4
halogenoalkyl, cyano-C
1
-C
4
alkyl, C
3
- or C
4
alkenyl, C
3
- or C
4
halogenoalkenyl, C
3
- or C
4
alkynyl or C
3
-C
6
cycloalkyl;
R
2
is hydrogen, C
1
-C
4
alkyl, C
1
-C
4
halogenoalkyl, C
3
-C
6
alkenyl, C
3
-C
6
halogenoalkenyl, C
3
-C
6
alkynyl, C
1
-C
4
alkylsulfonyl, C
1
-C
4
halogenoalkylsulfonyl, C
2
-C
4
alkenylsulfonyl or C
2
-C
4
halogenoalkenylsulfonyl;
R
3
is hydrogen, C
1
-C
4
alkyl, C
1
-C
4
halogenoalkyl, C
1
-C
4
hydroxyalkyl, C
2
-C
6
alkenyl, C
2
-C
6
-halogenoalkenyl, C
2
-C
6
alkynyl, halogen, cyano, NH
2
C(S)—, nitro, OHC— or R
18
R
19
N—;
R
18
and R
19
independently of one another are hydrogen, C
1
-C
4
alkyl, C
1
-C
4
halogenoalkyl, C
3
-C
4
alkenyl, C
3
-C
4
halogenoalkenyl, C
3
-C
4
cycloalkyl, C
3
-C
6
alkynyl, C
1
-C
6
alkylcarbonyl, C
1
-C
6
halogenoalkylcarbonyl, C
2
-C
6
alkenylcarbonyl, C
2
-C
6
halogenoalkenylcarbonyl, C
1
-C
6
alkylsulfonyl or C
1
-C
6
halogenoalkylsulfonyl;
n, is 0, 1 or 2;
R
4
is hydrogen, C
1
-C
4
alkyl, C
1
-C
4
halogenoalkyl, C
3
-C
6
alkenyl, C
3
-C
4
halogenoalkenyl, C
3
-C
6
alkynyl or C36ecycloalkyl;
R
5
is hydrogen, halogen, C
1
-C
4
alkyl, C
1
-C
4
halogenoalkyl, cyano, nitro, amino, NH
2
C(S)—, C
1
-C
4
alkylcarbonyl, C
1
-C
4
halogenoalkylcarbonyl, C
2
-C
4
alkenylcarbonyl, C
2
-C
4
halogenoalkenylcarbonyl or C
2
-C
4
alkynylcarbonyl;
R
11
is hydrogen, fluorine, chlorine, bromine or methyl;
R
13
is hydrogen, halogen, cyano, CIS(O)
2
—, CIC(O)—, nitro, amino,
R
20
NH— or R
20
R
21
N—;
R
20
and R
21
independently of one another are C
1
-C
8
alkyl, C
3
-C
8
alkenyl, C
3
-C
9
alkynyl, C
3
-C
6
cycloalkyl, C
1
-C
8
halogenoalkyl, C
3
-C
8
halogenoalkenyl, C
1
-C
4
alkylcarbonyl, C
1
-C
4
-halogenoalkylcarbonyl, C
1
-C
4
alkylsuffonyl, C
1
-C
4
halogenalkylsulfonyl, benzyl or benzyl which is substituted on the phenyl ring once to three times by halogen, C
1
-C
4
alkyl or C
1
-C
4
halogenoalkyl; or
R
13
is R
30
O—;
R
30
is hydrogen, C
1
-C
8
alkyl, C
3
-C
8
alkenyl, C
3
-C
8
alkynyl, C
3
-C
6
cycloalkyl, C
1
-C
8
halogenoalkyl, C
3
-C
8
halogenoalkenyl, C
1
-C
4
alkoxy-C
1
-C
4
alkyl, C
3
-C
6
alkenyloxy-C
1
-C
4
alkyl, C
3
-C
6
lkynyloxy-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
8
alkoxycarbonyl, C
3
-C
8
alkenyloxycarbonyl, benzyloxycarbonyl, phenyl, benzyl, pyridyl, pyrimidinyl, pyrazinyl or pyridazinyl, where these aromatic and heteroaromatic rings mentioned can be unsubstituted or substituted once to three times by halogen, C
1
-C
4
alkyl or C
1
-C
4
halogenoalkyl; or
R
30
is R
31
X
1
C(O)—C
1
-C
9
alkyl- or
X
1
is oxygen, sulfur or
R
3
, is hydrogen, C
1
-C
8
alkyl, C
3
-C
8
alkenyl, C
3
-C
8
alkynyl, C
3
-C
6
cycloalkyl, C
1
-C
8
-halogenoalkyl, C
3
-C
8
halogenoalkenyl, C
1
-C
4
alkoxy-C
1
-C
4
alkyl, C
3
-C
6
alkenyloxy-C
1
-C
4
alkyl, C
1
-C
4
alkyl-thio-C
1
-C
4
alkyl, phenyl, phenyl which is substituted once to three times by halogen, C
1
-C
4
alkyl or C
1
-C
4
halogenoalkyl, benzyl or benzyl which is substituted once to three times on the phenyl ring by halogen, C
1
-C
4
alkyl or C
1
-C
4
halogenoalkyl;
R
32
is hydrogen, C
1
-C
8
alkyl, C
3
-G
8
alkenyl, C
3
-C
8
alkynyl, C
3
-C
6
cycloalkyl or C
1
-C
8
-halogenoalkyl; or
R
13
is R
33
S(O)
n2
—;
n
2
is 0, 1 or 2;
R
33
is C
1
-C
8
alkyl, C
3
-C
8
alkenyl, C
3
-C
8
alkynyl, C
3
-C
6
cycloalkyl, C
1
-C
8
halogenoalkyl, C
3
-C
8
halogenoalkenyl, C
1
-C
4
alkoxy-C
1
-C
4
alkyl, C
3
-C
6
alkenyloxy-C
1
-C
4
alkyl, C
1
-C
4
alkylthio-C
1
-C
4
alkyl, phenyl, phenyl which is substituted once to three times by halogen, C
1
-C
4
alkyl or C
1
-C
4
halogenoalkyl, benzyl or benzyl which is substituted once to three times on the phenyl ring by halogen, C
1
-C
4
alkyl or C
1
-C
4
halogenoalkyl, and, if n
2
is 0,
R33 is hydrogen, C
1
-C
8
alkylcarbonyl or R
34
X
2
C(O)—;
X
2
is oxygen, sulfur or
R
34
is hydrogen, C
1
-C
8
alkyl, C
3
-C
8
alkenyl, C
3
-C
8
alkynyl, C
3
-C
6
cycloalkyl, C
1
-C
8
-halogenoalkyl, C
3
-C
8
halogenoalkenyl, C
1
-C
4
alkoxy-C
1
-C
4
alkyl, C
3
-C
6
alkenyloxy-C
1
-C
4
alkyl, C
1
-C
4
alkyl-thio-C
1
-C
4
alkyl, phenyl, phenyl which is substituted once to three times by halogen, C
1
-C
4
alkyl or C
1
-C
4
halogenoalkyl, benzyl or benzyl which is substituted once to three times on the phenyl ring by halogen, C
1
-C
4
alkyl or C
1
-C
4
halogenoalkyl;
R
35
is hydrogen, C
1
-C
8
alkyl or C
3
-C
8
alkenyl; or
R
13
is R
36
R
37
NS(O)
2
—;
R
36
is hydrogen, C
1
-C
8
alkyl, C
2
-C
8
alkenyl, C
3
-C
8
alkynyl or C
3
-C
8
cycloalkyl;
R
37
is hydrogen, C
1
-C
8
alkyl, C
3
-C
8
alkenyl, C
3
-C
8
alkynyl, C
1
-C
8
halogenoalkyl, C
1
-C
4
-alkylcarbonyl, C
1
-C
4
halogenoalkylcarbonyl, benzoyl or benzoyl which is substituted once to three times on the phenyl ring by halogen, C
1
-C
4
alkyl or C
1
-C
4
halogenoalkyl;
R
13
is R
40
C(O)—;
R
40
is hydrogen, fluorine, chlorine, C
1
-C
8
alkyl, C
2
-C
8
alkenyl, C
2
-C
8
alkynyl, C
3
-C
6
cycloalkyl, C
1
-C
8
halogenoalkyl, cyano-C
1
-C
4
alkyl, C
2
—C
8
alogenoalkenyl, C
1
-C
4
alkoxy-C
1
-C
4
alkyl, C
3
-C
6
alkenyloxy-C
1
-C
4
alkyl, C
1
-C
4
alkylthio-C
1
-C
4
alkyl, phenyl, phenyl which is substituted once to three times by halogen, C
1
-C
4
alkyl or C
1
-C
4
halogenoalkyl, benzyl or benzyl which is substituted once to three times on the phenyl ring by halogen, C
1
-C
4
alkyl or C
1
-C
4
halogenoalkyl; or
R
13
is R
50
X
3
C(O)—;
X
3
is oxygen, sulfur,
R
50
is hydrogen, C
1
-C
8
alkyl, C
3
-C
8
alkenyl, C
3
-C
8
alkynyl, C
3
-C
6
cycloalkyl, C
1
-C
8
-halogenoalkyl, C
3
-C
8
halogenoalkenyl, cyano-C
1
-C
4
alkyl, C
1
-C
4
alkoxy-C
1
-C
4
alkyl, C
3
-C
6
alkenyloxy-C
1
-C
4
alkyl, (oxiranyl)—CH
2
—, oxetanyl-, C
1
-C
4
alkylthio-C
1
-C
4
alkyl, phenyl, phenyl which is substituted once to three times by halogen, C
1
-C
4
alkyl or C
1
-C
4
halogenoalkyl, benzyl or benzyl which is substituted once to three times on the phenyl ring by halogen, C
1
-C
4
alkyl or C
1
-C
4
halogenoalkyl, phenyl-C
2
-C
6
alkyl, C
1
-C
6
alkyl-CO—C
1
-C
4
alkyl,
R
53
X
4
C(O)—C
1
-C
6
alkyl,
or R
53
X
4
C(O)—C
3
-C
6
cycloalkyl;
X
4
oxygen, sulfur,
R
53
is hydrogen, C
1
-C
8
alkyl, C
3
-C
8
alkenyl, C
3
-C
8
alkynyl, C
3
-C
6
cycloalkyl, C
1
-C
8
-halogenoalkyl, C
3
-C
8
halogenoalkenyl, cyano-C
1
-C
4
alkyl, C
1
-C
4
alkoxy-C
1
-C
4
alkyl, C
3
-C
6
-alkenyloxy-C
1
-C
4
alkyl, (oxiranyl)—CH
2
—, oxetanyl-, C
1
-C
4
alkylthio-C
1
-C
4
alkyl, phenyl, phenyl which is substituted once to three times by halogen, C
1
-C
4
alkyl or C
1
-C
4
halogenoalkyl, benzyl, benzyl which is substituted once to three times on the phenyl ring by halogen, C
1
-C
4
alkyl or C
1
-C
4
halogenoalkyl, or phenyl-C
2
-C
6
alkyl;
R
51
, R
52
, R
54
and R
55
independently of one another are hydrogen, C
1
-C
8
alkyl, C
3
-C
8
alkenyl, C
3
-C
8
alkynyl, C
1
-C
8
halogenoalkyl or benzyl; or
R
13
is B
1
-C
1
-C
8
alkyl, B
1
-C
2
-C
8
alkenyl, B
1
-C
2
-C
8
alkynyl, B
1
-C
1
-Calogenoalkyl, B
1
-C
2
-C
8
halogenoalkenyl, B
1
-C
1
-C
4
alkoxy-C
1
-C
4
alkyl, B
1
-C
1
-C
4
alkylthio-C
1
-C
4
alkyl or B
1
-C
3
-C
6
cycloalkyl;
B
1
is hydrogen, cyano, hydroxyl, C
1
-C
4
alkoxy, C
3
-C
8
alkenyloxy, R
60
X
5
C(O)—, C
1
-C
4
-alkylcarbonyl or C
1
-C
4
halogenoalkylca

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