Pyrazole derivatives as herbicides

Details Pyrazole derivatives as herbicides Pyrazole derivatives as herbicides

1999-09-07

2001-08-14

Fan, Jane (Department: 1612)

Plant protecting and regulating compositions

Plant growth regulating compositions

Organic active compound containing

C504S246000, C546S275400, C546S276100, C546S113000, C546S115000

Reexamination Certificate

active

06274536

ABSTRACT:

The present invention relates to novel, herbicidally active substituted pyridone derivatives, to a process for the preparation thereof, to compositions comprising those compounds, and to the use thereof in the control of weeds, especially in crops of useful plants, for example, cereals, maize, rice, cotton, soybean, rape, sorghum, sugar cane, sugar beet, sunflowers, vegetables, plantation crops and fodder plants, or in the inhibition of plant growth. Phenyl-pyrazole compounds having herbicidal activity are known and are described, for example, in EP-A-0 361 114, U.S. Pat. No. 5,032,165, WO 92,02509, WO 92,06962, WO 95/33728, WO 96/01254 and WO 97/00246.
Surprisingly, it has now been found that substituted pyridono-pyrazole derivatives have excellent herbicidal and growth-inhibiting properties.
The present invention accordingly relates to compounds of formula I
wherein
R
1
is hydrogen, C
1
-C
4
alkyl, C
1
-C
4
haloalkyl, cyano-C
1
-C
4
alkyl, C
3
- or C
4
-alkenyl, C
3
- or C
4
-haloalkenyl, 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
haloalkyl, C
3
-C
6
alkenyl, C
3
-C
6
haloalkenyl, C
3
-C
6
alkynyl, C
1
-C
4
alkyl-S(O)
2
— or C
1
-C
4
haloalkyl-S(O)
2
—;
R
3
is hydrogen, C
1
-C
4
alkyl, C
1
-C
4
haloalkyl, C
2
-C
6
alkenyl, C
2
-C
6
haloalkenyl, C
2
-C
6
alkynyl, halogen, cyano, NH
2
C(S)—, nitro or amino;
n
1
is 0, 1 or 2;
R
4
is hydrogen, C
1
-C
4
alkyl, C
1
-C
4
haloalkyl, C
3
-C
6
alkenyl, C
3
-C
6
haloalkenyl, C
3
-C
6
alkynyl or C
3
-C
6
cycloalkyl;
R
5
is hydrogen, halogen, C
1
-C
4
alkyl, C
1
-C
4
haloalkyl, cyano, nitro, amino, NH
2
C(O)—, NH
2
C(S)—, C
1
-C
4
alkylcarbonyl, C
1
-C
6
alkoxycarbonyl, C
1
-C
4
haloalkylcarbonyl, C
2
-C
4
alkenylcarbonyl, C
1
-C
3
alkyl-CH(OH)—, OHC—, HOC(O)—, ClC(O)—, HON═CH—, C
1
-C
4
alkoxy-N═CH—, C
2
-C
4
haloalkenylcarbonyl or C
2
-C
4
alkynylcarbonyl;
R
11
is hydrogen, fluorine, chlorine, bromine or methyl;
R
12
is hydrogen, halogen, methyl, halomethyl, nitro, amino, hydroxy, OHC—, HOC(O)—, cyano, C
1
-C
4
alkoxycarbonyl or halomethoxy;
X
1
is O, S, R
20
N═ or R
25
ON═;
R
13
is hydroxy, C
1
-C
6
alkoxy, C
3
-C
6
alkenyloxy, C
3
-C
6
alkynyloxy, C
1
-C
6
haloalkoxy, C
3
-C
6
-haloalkenyloxy, C
1
-C
6
alkoxy-C
1
-C
6
alkyl, C
3
-C
6
alkenyloxy-C
1
-C
6
alkyl, C
3
-C
6
alkynyloxy-C
1
-C
6
alkyl, C
1
-C
6
alkoxy-C
1
-C
6
alkoxy-C
1
-C
6
alkyl, B
1
—C
1
-C
6
alkoxy, R
21
(R
22
)N—, C
1
-C
6
alkyl, C
3
-C
6
alkenyl, C
3
-C
6
alkynyl, C
2
-C
6
haloalkyl, C
3
-C
6
haloalkenyl, C
3
-C
6
cycloalkyl, C
3
-C
6
halocycloalkyl, B
1
—C
1
-C
6
alkyl, OHC—, C
1
-C
6
alkylcarbonyl, C
1
-C
6
alkylcarbonyloxy, C
1
-C
6
haloalkylcarbonyl, C
2
-C
6
alkenylcarbonyl, C
1
-C
6
alkoxycarbonyl, C
1
-C
6
alkyl-S(O)
2
—, C
1
-C
6
haloalkyl-S(O)
2
—, (C
1
-C
6
alkyl)
2
N—N═CH—,
B
1
—CH═N—, (CH
3
)
2
N—CH═N—, (C
1
-C
5
hydroxyalkyl)—CH
2
—, (B
1
—C
1
-C
5
hydroxyalkyl)—CH
2
—, (B
1
—C
1
-C
5
haloalkyl)—CH
2
—, (hydroxy-C
1
-C
5
alkyl)—O— or (B
1
—C
1
-C
5
hydroxyalkyl)—O—;
B
1
is cyano, OHC—, HOC(O)—, C
1
-C
6
alkylcarbonyl, C
1
-C
6
alkoxycarbonyl, C
3
-C
6
alkenyloxycarbonyl, C
3
-C
6
alkynyloxycarbonyl, benzyloxycarbonyl, benzyloxycarbonyl mono- to tri-substituted at the phenyl ring by halogen, C
1
-C
4
alkyl or by C
1
-C
4
haloalkyl, benzylthio-C(O)—, benzylthio-C(O)— mono- to tri-substituted at the phenyl ring by halogen, C
1
-C
4
alkyl or by C
1
-C
4
haloalkyl, C
1
-C
6
haloalkoxycarbonyl, C
1
-C
6
alkylthio-C(O)—, R
26
(R
27
)NC(O)—, phenyl, phenyl mono- to tri-substituted by halogen, C
1
-C
4
alkyl or by C
1
-C
4
haloalkyl, C
1
-C
6
-alkyl-S(O)
2
—, C
1
-C
6
alkyl-S(O)—, C
1
-C
6
alkylthio, C
3
-C
6
cycloalkyl, C
1
-C
6
alkoxy, C
3
-C
6
alkenylthio or C
3
-C
6
alkynylthio;
R
20
is hydrogen, C
1
-C
6
alkyl, C
3
-C
6
alkenyl, C
3
-C
6
alkynyl, C
2
-C
6
haloalkyl, cyano, R
23
(R
24
)N—, C
1
-C
6
alkoxycarbonyl, C
3
-C
6
alkenyloxycarbonyl, C
3
-C
6
alkynyloxycarbonyl, C
2
-C
6
haloalkoxycarbonyl, OHC—, C
1
-C
6
alkylcarbonyl, C
1
-C
6
haloalkylcarbonyl, C
1
-C
6
alkyl-S(O)
2
—, C
1
-C
6
haloalkyl-S(O)
2
—, phenyl, phenyl mono- to tri-substituted by halogen, C
1
-C
4
alkyl or by C
1
-C
4
haloalkyl, phenyl-C
1
-C
6
alkyl, or phenyl-C
1
-C
6
alkyl mono- to tri-substituted at the phenyl ring by halogen, C
1
-C
4
alkyl or by C
1
-C
4
haloalkyl;
R
21
and R
22
are each independently hydrogen, C
1
-C
6
alkyl, C
3
-C
6
alkenyl, C
3
-C
6
alkynyl, C
1
-C
6
-haloalkyl, C
3
-C
6
haloalkenyl, C
3
-C
6
cycloalkyl, C
1
-C
6
alkoxy-C
1
-C
6
alkyl, OHC—, C
1
-C
6
alkylcarbonyl, C
1
-C
6
haloalkylcarbonyl, C
1
-C
6
alkyl-S(O)
2
— or C
1
-C
6
haloalkyl-S(O)
2
—;
R
23
and R
24
are each independently as defined for R
21
;
R
25
is hydrogen, C
1
-C
6
alkyl, C
3
-C
6
alkenyl, C
3
-C
6
alkynyl, C
1
-C
6
haloalkyl, C
3
-C
6
haloalkenyl, C
1
-C
6
alkoxy-C
1
-C
6
alkyl, benzyl, C
1
-C
6
alkyl-S(O)
2
— or C
1
-C
6
haloalkyl-S(O)
2
—;
R
26
and R
27
are each independently hydrogen, C
1
-C
6
alkyl, C
3
-C
6
alkenyl, C
3
-C
6
alkynyl, C
1
-C
6
haloalkyl, C
3
-C
6
haloalkenyl, phenyl, phenyl mono- to tri-substituted by halogen, C
1
-C
4
alkyl or by C
1
-C
4
haloalkyl, benzyl, or benzyl mono- to tri-substituted at the phenyl ring by halogen, C
1
-C
4
alkyl or by C
1
-C
4
haloalkyl; or
X
1
and R
13
together form a group ═N—Y— wherein Y is bonded to the ring nitrogen atom;
Y is —C(R
31
)(R
32
)—CH
2
—, —C(R
31
)(R
32
)—O—, —C(R
31
)(R
32
)—CH
2
—CH
2
—, —C(R
31
)(R
32
)—CH
2
—O—, —O—CH
2
—, —O—CH
2
—CH
2
—, —O—CH═CH—, —N(R
33
)—CH
2
—, —N(R
33
)—CH
2
—CH
2
—, —N(R
33
)—CH═CH—, —N(R
33
)—C(X
3
)—CH
2
—, —C(X
3
)—CH
2
—, —C(X
3
)—CH
2
—CH
2
—, —C(X
3
)—CH
2
—O—, —C(X
3
)—O—, —C(R
34
)═CH—, —C(R
31
)(R
32
)—CH═CH—, —C(R
34
) N—, —C(R
31
)(R
32
)—CH═N—, —C(R
31
)(R
32
)—N═CH—, —C(X
3
)—CH═CH—, —N═N—, —C(R
31
)(R
32
)—C(O)—, —C(R
31
) (R
32
)—C(S)—, —C(R
31
)(R
32
)—CH
2
—C(O)—, —C(R
31
)(R
32
)—CH
2
—C(S)—, —N (R
33
)—C(O)—, —N (R
33
)—C(S)—, —N(R
33
)—CH
2
—C(O)—, —N(R
33
)—CH
2
—C(S)—, —O—C(O)—, —O—C(S)—, —C(R
34
)═CH—C(O)— or —C(R
34
)═CH—C(S)—, the right-hand end of the bridge members in the above definitions of Y being bonded to the ring nitrogen atom;
R
31
is hydrogen, C
1
-C
6
alkyl or C
1
-C
6
haloalkyl;
R
32
is hydrogen, C
1
-C
6
alkyl, C
2
-C
6
alkenyl, C
2
-C
6
alkynyl, C
1
-C
6
haloalkyl, C
2
-C
6
haloalkenyl, cyano-C
1
-C
6
alkyl, hydroxy-C
1
-C
6
alkyl, C
1
-C
6
alkoxy-C
1
-C
6
alkyl, C
3
-C
6
alkenyloxy-C
1
-C
6
alkyl, C
3
-C
6
alkynyloxy-C
1
-C
6
alkyl, C
1
-C
6
alkylcarbonyloxy-C
1
-C
6
alkyl, C
1
-C
6
haloalkylcarbonyloxy-C
1
-C
6
alkyl, carboxyl, C
1
-C
6
alkoxycarbonyl, C
3
-C
6
alkenyloxycarbonyl, C
3
-C
6
alkynyloxycarbonyl, C
1
-C
6
haloalkoxycarbonyl, C
3
-C
6
cycloalkoxycarbonyl, C
1
-C
4
alkoxy-C
1
-C
6
alkoxycarbonyl, C
1
-C
6
alkyl-NHC(O)—, (C
1
-C
6
alkyl)
2
NC(O)—, C
3
-C
6
alkenyl-NHC(O)—, C
1
-C
6
alkyl-(C
3
-C
6
-alkenyl)NC(O)—, C
3
-C
6
alkynyl-NHC(O)—, aminocarbonyl, C
1
-C
6
alkylthio-C(O)—, C
3
-C
6
-alkenylthio-C(O)—, C
3
-C
6
alkynylthio-C(O)—, benzyloxycarbonyl, benzyloxycarbonyl mono- to tri-substituted at the phenyl ring by halogen, C
1
-C
4
alkyl or by C
1
-C
4
haloalkyl, phenoxycarbonyl, C
1
-C
6
alkyl-S(O)
2
NHC(O)—, C
1
-C
6
alkyl-S(O)
2
(C
3
-C
6
alkenyl)N—C(O)—, C
1
-C
6
haloalkyl-S(O)
2
NHC(O)—, HON═CH—, C
1
-C
6
alkoxy-N═CH—, C
3
-C
6
alkenyloxy-N═CH—, C
3
-C
6
alkynyloxy-N═CH—, HOC(O)—C
1
-C
6
alkyl, C
1
-C
6
alkoxycarbonyl-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
alkylcarbonyl, ClC(O)—, H
2
NC(S)—, OHC—, cyano, phenyl, phenyl mono- to tri-substituted by halogen, C
1
-C
4
alkyl or by C
1
-C
4
-haloalkyl, phenyl-C
1
-C
6
alkyl, or phenyl-C
1
-C
6
alkyl mono- to tri-substituted at the phenyl ring by halogen, C
1
-C
4
alkyl or by C
1
-C
4
haloalkyl;
X
3
is O, S, R
20
N═ or R
25
ON═;
R
33
is hydrogen, C
1
-C
6
alkyl, C
3
-C
6
alkenyl, C
3
-C
6
alkynyl, C
1
-C
6
haloalkyl, C
3
-C
6
haloalkenyl, C
3
-C
6
cycloalkyl, C
1
-C
6
alkylcarbonyl, C
1
-C
6
haloalkylcarbonyl, C
1
-C
6
alkyl-S(O)
2
— o

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