Substituted pyridine herbicides

Details Substituted pyridine herbicides Substituted pyridine herbicides

2003-01-07

2004-01-06

Davis, Zinna Northington (Department: 1625)

Organic compounds -- part of the class 532-570 series

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

C546S315000

Reexamination Certificate

active

06673938

ABSTRACT:

The present invention relates to novel, herbicidally active pyridine ketones, to their preparation, to compositions comprising these compounds, and to their use for controlling weeds, especially in crops of useful plants, or for inhibiting plant growth.
Herbicidally active pyridine ketones are described, for example, in WO 97/46530. There have now been found novel pyridine ketones which have herbicidal and growth-inhibitory properties.
The present invention therefore relates to compounds of the formula I
in which
p is 0 or 1;
R
5
is C
1
-C
6
haloalkyl; R
2
is hydrogen, C
1
-C
6
alkyl, C
1
-C
6
haloalkyl, C
2
-C
6
alkenyl, C
2
-C
6
haloalkenyl, vinyl which is substituted by C
1
-C
2
alkoxycarbonyl or phenyl, or is C
2
-C
6
alkynyl, C
2
-C
6
haloalkynyl, ethynyl which is substituted by trimethylsilyl, hydroxyl, C
1
-C
2
alkoxy, C
1
-C
2
alkoxycarbonyl or phenyl, or is C
3
-C
6
allenyl, C
3
-C
6
cycloalkyl, C
3
-C
6
cycloalkyl which is substituted by halogen, or is 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, cyano-C
1
-C
4
alkoxy, C
1
-C
4
alkoxy-C
1
-C
4
alkoxy, C
1
-C
4
alkylthio-C
1
-C
4
alkoxy, C
1
-C
4
alkylsulfinyl-C
1
-C
4
alkoxy, C
1
-C
4
alkylsulfonyl-C
1
-C
4
alkoxy, C
1
-C
4
alkoxycarbonyl-C
1
-C
4
alkoxy, C
1
-
6
alkylthio, C
1
-C
6
alkylsulfinyl, C
1
-C
6
alkylsulfonyl, C
1
-C
6
haloalkylthio, C
1
-C
6
haloalkylsulfinyl, C
1
-C
6
haloalkylsulfonyl, 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, benzyl-S(O)
n1
—, C
1
-C
6
alkylamino, C
2
-C
6
dialkylamino, C
1
-C
6
alkylaminosulfonyl, di-(C
1
-C
6
alkylamino)sulfonyl, benzyloxy, benzyl, phenyl, phenoxy, phenylthio, phenylsulfinyl or phenylsulfonyl, it being possible for the phenyl-containing groups, in turn, to 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 or R
2
is OS(O)
n2
—R
21
, N(R
23
)—S(O)
n3
—R
22
, cyano, carbamoyl, C
1
-C
4
alkoxycarbonyl, formyl, halogen, thiocyanato, amino, hydroxy-C
1
-C
4
alkyl, C
1
-C
4
alkoxy-C
1
-C
4
alkyl, C
1
-C
4
alkyl-S(O)
n4
—C
1
-C
4
alkyl, cyano-C
1
-C
4
alkyl, C
1
-C
6
alkylcarbonyloxy-C
1
-C
4
alkyl, C
1
-C
4
alkoxycarbonyl-C
1
-C
4
alkyl, C
1
-C
4
alkoxycarbonyloxy-C
1
-C
4
alkyl, C
1
-C
4
thiocyanato-C
1
-C
4
alkyl, benzoyloxy-C
1
-C
4
alkyl, C
2
-C
6
oxiranyl, C
1
-C
4
alkylamino, C
1
-C
4
alkyl, di-(C
1
-C
4
alkyl)amino-C
1
-C
4
alkyl, C
1
-C
12
alkylthiocarbonyl-C
1
-C
4
alkyl or formyl-C
1
-C
4
alkyl, or R
2
is a five- to ten-membered monocyclic or fused bicyclic ring system which can be aromatic or partially saturated and can contain 1 to 4 hetero atoms selected from the group consisting of nitrogen, oxygen and sulfur, the ring system being bonded to the pyridine ring via a C
1
-C
4
alkylene, —CH═CH—, —C≡C—, —CH
2
O—, —CH
2
N(C
1
-C
4
alkyl)—, —CH
2
SO—, or —CH
2
SO
2
group and it not being possible for each ring system to contain more than 2 oxygen atoms and not more than 2 sulfur atoms, and it being possible for the ring system itself to 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
2
alkylaminosulfonyl, di-(C
1
-C
2
alkyl)aminosulfonyl, di-(C
1
-C
4
alkyl)amino, halogen, cyano, nitro, phenyl and benzylthio, it being possible for phenyl and benzylthio, in turn, to 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 substituents on the nitrogen in the heterocyclic ring being other than halogen;
R
3
is hydrogen, C
1
-C
6
alkyl, C
1
-C
6
haloalkyl, C
2
-C
6
alkenyl, C
2
-C
6
haloalkenyl, C
-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
haloalkylthio, C
1
-C
6
haloalkylsulfinyl, C
1
-C
6
haloalkylsulfonyl, C
1
-C
6
alkylamino, C
2
-C
6
dialkylamino, C
1
-C
6
alkylaminosulfonyl, C
2
-C
6
dialkylaminosulfonyl, phenyl, phenylthio, phenylsulfinyl, phenylsulfonyl or phenoxy, it being possible for phenyl, in turn, to 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, or R
3
is —N(R
23
)—S(O)
n
—R
22
, cyano, halogen, amino, C
1
-C
4
alkoxy-C
1
-C
4
alkyl or C
1
-C
4
alkyl-S(O)
n
—C
1
-C
4
alkyl;
R
4
is hydrogen, C
1
-C
6
alkyl, hydroxyl, C
1
-C
6
alkoxy, C
1
-C
6
haloalkoxy, C
3
-C
6
alkenyloxy, C
3
-C
6
haloalkenyloxy, C
3
-C
6
alkynyloxy, C
1
-C
4
alkylcarbonyloxy, C
1
-C
4
alkylsulfonyloxy, tosyloxy, C
1
-C
4
alkylthio, C
1
-C
4
alkylsulfinyl, C
1
-C
4
alkylsulfonyl, C
1
-C
4
alkylamino, C
1
-C
4
dialkylamino, C
1
-C
4
alkoxycarbonyl, C
1
-C
4
haloalkyl, formyl, cyano, halogen, phenyl or phenoxy, it being possible for phenyl, in turn, to 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;
or R
4
is a five to ten-membered monocyclic or R
3
-fused bicyclic ring system which can contain 1 to 4 hetero atoms selected from the group consisting of nitrogen, oxygen and sulfur, the ring system, unless fused, being bonded to the pyridine ring directly or via a C
1
-C
4
alkylene, —CH═CH—, —C≡C—, —CH
2
O—, —CH
2
N(C
1
-C
4
alkyl)—, —CH
2
S—, —CH
2
SO—, or —CH
2
SO
2
— group and it not being possible for the ring system to contain more than 2 oxygen atoms and not more than two sulfur atoms, and it being possible for the ring system itself to be mono-, di- or trisubstituted by C
1
-C
6
alkyl, C
1
-C
6
haloalkyl, C
2
-C
6
alkenyl, C
2
-C
6
haloalkenyl, C
2
-C
6
alkynyl, C
2
-C
6
haloalkynyl, C
1
-C
6
alkoxy, C
1
-C
6
haloalkoxy, C
3
-C
6
alkenyloxy, C
3
-C
6
alkynyloxy, C
1
-C
6
alkylthio, C
1
-C
6
haloalkylthio, C
3
-C
6
alkenylthio, C
3
-C
6
haloalkenyl C
3
-C
6
alkynylthio, C
1
-C
4
alkoxy-C
1
-C
2
alkylthio, C
1
-C
4
alkylcarbonyl-C
1
-C
2
alkylthio, C
1
-C
4
alkoxycarbonyl-C
1
-C
2
alkylthio, cyano-C
1
-C
4
alkylthio, C
1
-C
6
alkylsulfinyl, C
1
-C
6
haloalkylsulfinyl, C
1
-C
6
alkylsulfonyl, C
1
-C
6
haloalkylsulfonyl, aminosulfonyl, C
1
-C
2
alkylaminosulfonyl, di-(C
1
-C
2
alkyl)aminosulfonyl, di-(C
1
-C
4
alkyl)amino, halogen, cyano, nitro, phenyl and benzylthio, it being possible for phenyl and benzylthio, in turn, to 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 substituents on the nitrogen in the heterocyclic ring being other than halogen;
R
21
is C
1
-C
4
alkyl or C
1
-C
4
haloalkyl;
R
22
is C
1
-C
4
alkyl, C
1
-C
4
haloalkyl or di-(C
1
-C
4
alkyl)amino;
R
23
R
24
, R
25
independently of one another are hydrogen or C
1
-C
4
alkyl;
n, n
1
, n
2
, n
3
and n
4
independently of one another are 0, 1 or 2;
Q is Q
1
 in which
R
6
, R
7
, R
8
and R
9
independently of one another are hydrogen, C
1
-C
6
alkyl, C
1
-C
6
haloalkyl, C
2
-C
6
alkenyl, C
2
-C
6
alkynyl, C
1
-C
6
alkoxycarbonyl, C
1
-C
6
alkylcarbonyl, C
1
-C
6
alkyl-S(O)
n17
, C
1
-C
6
alkyl-NHS(O)
2
, C
1
-C
6
alkylamino, di-(C
1
-C
6
alkyl)amino, hydroxyl, C
1
-C
6
alkoxy, C
3
-C
6
alkenyloxy, C
3
-C
6
alkynyloxy, hydroxy-C
1
-C
6
alkyl, C
1
-C
4
alkylsulfonyloxy-C
1
-C
6
alkyl, tosyloxy-C
1
-C
6
alkyl, C
1
-C
6
alkoxy-C
1
-C
6
alkyl, C
1
-C
6
alkyl-S(O)
n4
-C
1
-C
6
alkyl, cyano-C
1
-C
6
alkyl, C
1
-C
6
alkoxy-C
1
-C
6
alkoxy, benzyloxy-C
1
-C
6
alkyl, C
1
-C
6
alkoxycarbonyl-C
1
-C
6
alkyl, C
1
-C
6
alkoxycarbonyloxy-C
1
-C
6
alkyl, thiocyanato-C
1
-C
6
alkyl, oxiranyl, C
1
-C
6
alkylamino-

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