Pyridine ketones useful as herbicides

Details Pyridine ketones useful as herbicides Pyridine ketones useful as herbicides

2001-03-12

2002-12-24

Davis, Zinna Northington (Department: 1625)

Plant protecting and regulating compositions

Plant growth regulating compositions

Plural active ingredients

C504S138000, C544S063000, C546S272100, C546S340000

Reexamination Certificate

active

06498125

ABSTRACT:

The present invention relates to novel herbicidally active pyridine ketones, to processes for their preparation, to compositions which comprise these compounds, and to their use for controlling weeds, in particular in crops of useful plants, or for inhibiting plant growth.
Pyridine ketones having herbicidal action are described, for example, in WO 97/46530. We have now found novel pyridine ketones having herbicidal and growth-inhibiting properties.
The present invention thus provides compounds of the formula I
in which
each R independently is C
1
-C
6
alkyl, C
2
-C
6
alkenyl, C
2
-C
6
haloalkenyl, C
2
-C
6
alkynyl, C
2
-C
6
haloalkynyl, C
3
-C
6
cycloalkyl, C
1
-C
6
alkoxy, C
1
-C
6
haloalkoxy, C
1
-C
6
alkylthio, C
1
-C
6
alkylsulfinyl, C
1
-C
6
alkylsulfonyl, C
1
-C
6
haloalkyl, C
1
-C
6
haloalkylthio, C
1
-C
6
haloalkylsulfinyl, C
1
-C
6
haloalkylsulfonyl, C
1
-C
6
alkoxycarbonyl, C
1
-C
6
alkylcarbonyl, C
1
-C
6
alkylamino, di-C
1
-C
6
alkylamino, C
1
-C
6
alkylaminosulfonyl, di-C
1
-C
6
alkylaminosulfonyl, —N(R
1
)—S—R
2
, —N(R
3
)—SO—R
4
, —N(R
5
)—SO
2
—R
6
, nitro, cyano, halogen, hydroxy, amino, formyl, hydroxy-C
1
-C
6
alkyl, C
1
-C
6
alkoxy-C
1
-C
6
alkyl, C
1
-C
6
alkoxycarbonyloxy-C
1
-C
6
alkyl, C
1
-C
6
alkylthio-C
1
-C
6
alkyl, C
1
-C
6
alkylsulfinyl-C
1
-C
6
alkyl, C
1
-C
6
alkylsulfonyl-C
1
-C
6
alkyl, thiocyanato-C
1
-C
6
alkyl, cyano-C
1
-C
6
alkyl, oxiranyl, C
3
-C
6
alkenyloxy, C
3
-C
6
alkynyloxy, C
1
-C
6
alkoxy-C
1
-C
6
alkoxy, cyano-C
1
-C
6
alkenyloxy, C
1
-C
6
alkoxycarbonyloxy-C
1
-C
6
alkoxy, C
3
C
6
alkynyloxy, cyano-C
1
-C
6
alkoxy, C
1
-C
6
alkoxycarbonyl-C
1
-C
6
alkoxy, C
1
-C
6
alkylthio-C
1
-C
6
alkoxy, alkoxycarbonyl-C
1
-C
6
alkylthio, alkoxycarbonyl-C
1
-C
6
alkylsulfinyl, alkoxycarbonyl-C
1
-C
6
alkylsulfonyl, C
1
-C
6
alkylsulfonyloxy, C
1
-C
6
haloalkylsulfonyloxy, phenyl, benzyl, phenoxy, phenylthio, phenylsulfinyl, phenylsulfonyl, benzylthio, benzylsulfinyl or benzylsulfonyl, where the phenyl groups may be mono- or polysubstituted by halogen, methyl, ethyl, trifluoromethyl, methoxy or nitro, or R is a five- to ten-membered monocyclic or fused bicyclic ring system, which may be aromatic or partially saturated and may contain 1 to 4 heteroatoms selected from the group consisting of nitrogen, oxygen and sulfur, where the ring system is either attached directly to the pyridine ring or attached to the pyridine ring via a C
1
-C
4
alkylene group, and where each ring system may not contain more than 2 oxygen atoms and not more than two sulfur atoms, and where the ring system for its part may be mono-, di- or trisubstituted by C
1
-C
6
alkyl, C
1
-C
6
haloalkyl, C
3
-C
6
alkenyl, C
3
-C
6
haloalkenyl, C
3
-C
6
alkynyl, C
3
-C
6
haloalkynyl, C
1
-C
6
alkoxy, C
1
-C
6
haloalkoxy, C
3
-C
6
alkenyloxy, C
3
-C
6
alkynyloxy, mercapto, C
1
-C
6
alkylthio, C
1
-C
6
haloalkylthio, C
3
-C
6
alkenylthio, C
3
-C
6
haloalkenylthio, C
3
-C
6
alkynylthio, C
2
-C
5
alkoxyalkylthio, C
3
-C
5
acetylalkylthio, C
3
-C
6
alkoxycarbonylalkylthio, C
2
-C
4
cyanoalkylthio, C
1
-C
6
alkylsulfinyl, C
1
-C
6
haloalkylsulfinyl, C
1
-C
6
alkylsulfonyl, C
1
-C
6
haloalkylsulfonyl, aminosulfonyl, C
1
-C
6
alkylaminosulfonyl, C
1
-C
6
dialkylaminosulfonyl, C
1
-C
6
alkylene-R
7
, NR
8
R
9
, halogen, cyano, nitro, phenyl and benzylthio, where phenyl and benzylthio for their part may be substituted on the phenyl ring by C
1
-C
3
alkyl, C
1
-C
3
haloalkyl, C
1
-C
3
alkoxy, C
1
-C
3
haloalkoxy, halogen, cyano or nitro, and where substituents on the nitrogen in the heterocyclic ring are different from halogen;
m is 1, 2, 3 or 4;
p is 0 or 1;
R
1
, R
3
and R
5
independently of one another are hydrogen or C
1
-C
6
alkyl;
R
2
is NR
10
R
11
, C
1
-C
6
alkoxy, C
1
-C
6
haloalkoxy, C
1
-C
6
alkyl, C
1
-C
6
haloalkyl, C
3
-C
6
alkenyl, C
3
-C
6
haloalkenyl, C
3
-C
6
alkynyl, C
3
-C
6
haloalkynyl, C
3
-C
6
cycloalkyl or phenyl, where phenyl for its part may be substituted by C
1
-C
3
alkyl, C
1
-C
6
haloalkyl, C
1
-C
6
alkoxy, C
1
-C
3
haloalkoxy, halogen, cyano or nitro;
R
4
is NR
12
R
13
, C
1
-C
6
alkoxy, C
1
-C
6
haloalkoxy, C
1
-C
6
alkyl, C
1
-C
6
haloalkyl, C
3
-C
6
alkenyl, C
3
-C
6
haloalkenyl, C
3
-C
6
alkynyl, C
3
-C
6
haloalkynyl, C
3
-C
6
cycloalkyl or phenyl, where phenyl for its part may be substituted by C
1
-C
3
alkyl, C
1
-C
3
haloalkyl, C
1
-C
3
alkoxy, C
1
-C
3
haloalkoxy, halogen, cyano or nitro;
R
6
is NR
14
R
15
, C
1
-C
6
alkoxy, C
1
-C
6
haloalkoxy, C
1
-C
6
alkyl, C
1
-C
6
haloalkyl, C
3
-C
6
alkenyl, C
3
-C
6
haloalkenyl, C
3
-C
6
alkynyl, C
3
-C
6
haloalkynyl, C
3
-C
6
cycloalkyl or phpnyl, where phenyl for its part may be substituted by C
1
-C
3
alkyl, C
1
-C
3
haloalkyl, C
1
-C
3
alkoxy, C
1
-C
3
haloalkoxy, halogen, cyano or nitro;
R
7
is C
1
-C
3
alkoxy, C
2
-C
4
alkoxycarbonyl, C
1
-C
3
alkylthio, C
1
-C
3
alkylsulfinyl, C
1
-C
3
alkylsulfonyl or phenyl, where phenyl for its part may be substituted by C
1
-C
3
alkyl, C
1
-C
3
haloalkyl, C
1
-C
3
alkoxy, C
1
-C
3
haloalkoxy, halogen, cyano or nitro;
R
8
, R
10
, R
12
and R
14
independently of one another are hydrogen or C
1
-C
6
alkyl;
R
9
, R
11
, R
13
and R
15
is independently of one another are C
1
-C
6
alkyl or C
1
-C
6
alkoxy;
Q is the group Q
1
in which
R
16
, R
17
, R
18
and R
19
independently of one another are hydrogen, hydroxyl, C
1
-C
4
alkyl, C
2
-C
6
alkenyl, C
2
-C
6
alkynyl, C
1
-C
4
alkoxycarbonyl, C
1
-C
6
alkylthio, C
1
-C
6
alkylsulfinyl, C
1
-C
6
alkylsulfonyl, C
1
-C
4
alkyl-NHS(O)
2
, C
1
-C
4
haloalkyl, —NH—C
1
-C
4
alkyl, —N(C
1
-C
4
alkyl)
2
, C
1
-C
6
alkoxy, cyano, nitro, halogen or phenyl, which for its part may be substituted by C
1
-C
4
alkyl, C
1
-C
4
haloalkyl, C
1
-C
4
alkoxy, C
1
-C
4
haloalkoxy, C
1
-C
4
alkylcarbonyl, C
1
-C
4
alkoxycarbonyl, amino, C
1
-C
4
alkylamino, di-C
1
-C
4
alkylamino, C
1
-C
6
alkylthio, C
1
-C
6
alkylsulfinyl, C
1
-C
6
alkylsulfonyl, C
1
-C
4
alkyl-S(O)
2
O, C
1
-C
4
haloalkylthio, C
1
-C
4
haloalkylsulfinyl, C
1
-C
4
haloalkylsulfonyl, C
1
-C
4
haloalkyl-S(O)
2
O, C
1
-C
4
alkyl-S(O)
2
NH, C
1
-C
4
alkyl-S(O)
2
N(C
1
-C
4
alkyl), halogen, nitro, COOH or cyano; or two adjacent substituents from the group consisting of R
16
, R
17
, R
18
and R
19
form a C
2
-C
6
alkyiene bridge;
R
20
is hydroxyl, O
−
M
+
, halogen, cyano, SCN, OCN, C
1
-C
12
alkoxy, C
1
-C
4
alkoxycarbonyl-C
1
-C
4
alkoxy, C
1
-C
12
alkylthio, C
1
-C
12
alkylsulfinyl, C
1
-C
12
alkylsulfonyl, C
1
-C
12
haloalkylthio, C
1
-C
12
haloalkylsulfinyl, C
1
-C
12
haloalkylsulfonyl, C
1
-C
6
alkoxy-C
1
-C
6
alkylthio, C
1
-C
6
alkoxy-C
1
-C
6
alkylsulfinyl, C
1
-C
6
alkoxy-C
1
-C
6
alkylsulfonyl, C
2
-C
12
alkenylthio, C
2
-C
12
alkeny isulfinyl, C
2
-C
12
alkenylsulfonyl, C
2
-C
12
alkynylthio, C
2
-C
12
alkynylsulfinyl, C
2
-C
12
alkynylsulfonyl, C
2
-C
12
haloalkenylthio, C
2
-C
12
haloalkenylsulfinyl, C
2
-C
12
haloalkenylsulfonyl, C
1
-C
4
alkoxycarbonyl-C
1
-C
4
alkylthio, C
1
-C
4
alkoxycarbonyl-C
1
-C
4
alkylsulfinyl, C
1
-C
4
alkoxycarbonyl-C
1
-C
4
alkylsulfonyl, (C
1
-C
4
alkoxy)
2
P(O)O, C
1
-C
4
alkyl-(C
1
-C
4
alkoxy)P(Q)O, H(C
1
-C
4
alkoxy)P(O)O,
R
37
R
38
N, R
71
R
72
NNH—, R
73
R
74
NC(O)NH—, C
1
-C
4
alkyl-S(O)
39
, C
1
-C
4
haloalkyl-S(O)
2
NR
40
, C
1
-C
6
alkyl-S(O)
2
O, C
1
-C
4
haloalkyl-S(O)
2
O, C
1
-C
18
alkylcarbonyloxy, where the alkyl group may be substituted by halogen, C
1
-C
6
alkoxy, C
1
-C
6
alkylthio or cyano, C
2
-C
18
alkenylcarbonyloxy, C
2
-C
18
alkynylcarbonyloxy, C
3
-C
6
cycloalkylcarbonyloxy, C
1
-C
12
alkoxycarbonyloxy, C
1
-C
12
alkylthiocarbonyloxy, C
1
-C
12
alkylthiocarbamoyl, C
1
-C
6
alkyl-NH(CS)N(C
1
-C
6
alkyl)—NH—, di-C
1
-C
6
alkyl-N(CS)N(C
1
-C
6
alkyl)-NH—, benzyloxy, benzylthio, benzylsulfinyl, benzyisulfonyl, phenoxy, phenylthio, phenylsulfinyl, phenylsulfonyl, phenylsulfonyloxy or benzoyloxy, where the phenyl groups for their part may each be substituted by C
1
-C
4
alkyl, C
1
-C
4
haloalkyl, C
1
-C
4
alkoxy, C
1
-C
4
haloalkoxy, C
1
-C
4
alkylcarbonyl, C
1
-C
4
alkoxycarbonyl, C
1
-C
4
alkylamino, di-C
1
-C
4
alkylamino, C
1
-C
4
alkylthio, C
1
-C
4
alkylsulfinyl, C
1
-C
4
alkylsulfonyl, C
1
-C

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