Herbicidal pyridine compounds

Details Herbicidal pyridine compounds Herbicidal pyridine compounds

2000-08-25

2002-07-16

Fan, Jane (Department: 1625)

Plant protecting and regulating compositions

Plant growth regulating compositions

Organic active compound containing

C546S280400

Reexamination Certificate

active

06420315

ABSTRACT:

BACKGROUND OF THE INVENTION
Selective herbicidal compounds play an important role in agriculture and related fields. Growers seek herbicides that kill pest plants, but do not reduce crop yield. Although numerous selective herbicides have been described, there is nevertheless a considerable interest in new compounds having a superior or different activities, because the known herbicidal compounds either are not suitable for application in certain crops, or are not sufficiently selective.
Selective herbicides the active ingredients of which are pyridine derivatives, and particularly 2,6-substituted pyridines, are known from WO 94/22833.
The European patent application EP 0 109 751 discloses herbicidal 6-difluormethoxy- and 6-tetrafluorethoxy-2-phenyloxypyridines.
However, 2,6-disubstituted pyridine derivatives in which a haloalkylmethoxy or a haloalkenyloxy group is attached to the pyridine group in the 2-position have not yet been described.
SUMMARY OF THE INVENTION
The present invention provides novel compounds of the general formula (I)
wherein
one of the groups X
1
, X
2
and X
3
represents N or CR
1
and the others represent CR
1
;
R
1
each independently represent a hydrogen or halogen atom or an optionally substituted alkyl, alkenyl, alkinyl, alkoxy, alkoxyalkyl, alkoxyalkoxy, group or a haloalkyl, haloalkoxy, cyano, nitro or SF
5
group; or —S(O)
p
—R
1
, in which p is 0, 1 or 2, and R
1
represents an alkyl or haloalkyl group; or —NR
2
R
3
, in which R
2
and R
3
each independently represent a hydrogen atom, an alkyl, alkenyl, aralkyl or aryl group, or R
4
O—CY—, in which R
4
represents an alkyl group, and Y represents O or S;
A represents an optionally substituted aryl group, an optionally substituted 5- or 6-membered nitrogen-containing heteroaromatic group or an optionally substituted thienyl group;
R represents an optionally substituted haloalkyl or haloalkenyl group;
m is 0, 1, 2 or 3;
Z represents an oxygen or sulfur atom,
and the agronomically acceptable salts or N-oxides thereof;
with the proviso that R represents an optionally substituted haloalkenyl group, in the event that m is 0.
The new compounds show an excellent selective herbicidal activity in various crops.
It is an object of the present invention to provide novel, selective herbicidal compounds.
It is also an object of the invention to provide methods for controlling undesired plant growth by contacting said plants with a herbicidally effective amount of the new compounds.
It is another object of the invention to provide selective herbicidal compositions containing the new compounds as active ingredients.
These and other objects and features of the invention will be more apparent from the detailed description set forth hereinbelow, and from the appended claims.
DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS
It has surprisingly been found that the compounds of the general formula (I)
wherein
A, R, m, X
1
through X
3
and Z are as described above and the agronomically acceptable salts or N-oxides thereof, show considerable herbicidal activity and high selectivity in certain crops, such as maize and rice, in pre- and post-emergence applications on both broadleaf and grassy weed species.
In the definitions of the new compounds, an aryl group is suitably an optionally substituted phenyl or naphthyl group. Within the definition of A, the 5- or 6-membered nitrogen-containing heteroaryl groups comprise optionally substituted 5- or 6-membered heterocycles containing one or more nitrogen and/or oxygen and/or sulphur atoms, 1 to 3 nitrogen atoms being preferred. Examples of such groups are pyrazolyl, imidazolyl, triazolyl, tetrazolyl, pyridyl, pyrazinyl, pyrimidyl, pyridazinyl, isoxazolyl, isothiazolyl and triazinyl groups. A also includes optionally substituted thienyl groups.
Generally, in compounds of the present invention, alkyl, alkenyl or alkynyl groups, unless otherwise specified, may be linear or branched and may contain up to 12, preferably up to 6, and most preferably up to 4, carbon atoms. Examples of such groups are methyl, ethyl, propyl, vinyl, allyl, propargyl, isopropyl, butyl, isobutyl and tertiary-butyl groups. The alkyl portion of a haloalkyl, haloalkenyl, haloalkoxy, alkylthio, haloalkylthio or alkoxy group suitably has up to 12 carbon atoms, preferably up to 6, and most preferably up to 4, carbon atoms. The double bond of the alkenyl and haloalkenyl groups is as a rule located in the 1- or 2-position with respect to the point of their attachment. The number of carbon atoms in the alkoxyalkyl, alkoxyalkoxy or dialkoxyalkyl groups is up to 6, preferably up to 4, e.g. methoxymethyl, methoxymethoxy, methoxyethyl, ethoxymethyl, ethoxyethoxy, dimethoxymethyl.
“Halogen” means a fluorine, chlorine, bromine or iodine atom, preferably fluorine, chlorine or bromine.
m is preferably 1 or 2.
Haloalkyl, haloalkenyl, haloalkylthio and haloalkoxy are preferably mono-, di-, tri-, tetra- or pentafluoroalkyl, -alkenyl, -alkylthio and -alkoxy, or monochloro- or dichloroalkenyl, or monobromoalkenyl, especially preferred are trifluoromethyl, tetrafluoroethyl, pentafluoroethyl, octafluorobutyl, 3,3,3-trifluoroprop-1-enyl, 2-methyl-3,3,3-trifluoroprop-1-enyl, 4,4,4-trifluorobut-1-enyl, 1,2-difluorobuta-1,3-dienyl, 1- or 2-chlorovinyl, 2,2-dichlorovinyl, 1,2-dichlorovinyl, 1,2-dichloroprop-1-enyl, 3,3,3-trichloroprop-1-enyl, 2-bromoallyl, difluoromethoxy, trifluoromethylthio, difluoromethylthio and trifluoromethoxy.
When any groups are designated as being optionally substituted, the substituent groups which are optionally present may be any of those customarily employed in the modification and/or development of pesticidal compounds and are especially substituents that maintain or enhance the herbicidal activity associated with the compounds of the present invention, or influence persistence of action, soil or plant penetration, or any other desirable property of such herbicidal compounds.
There may be one or more of the same or different substituents present in each part of the molecules. In relation to moieties defined above as comprising an optionally substituted alkyl group, including alkyl parts of haloalkyl, alkoxy, alkylthio, haloalkoxy, haloalkylthio, alkylamino and dialkylamino groups, specific examples of such substituents include phenyl, halogen atoms, nitro, cyano, hydroxyl, C
1-4
-alkoxy, C
1-4
-haloalkoxy, C
1-4
-haloalkylthio and C
1-4
-alkoxycarbonyl groups.
In relation to moieties defined above as comprising an optionally substituted aryl or heteroaryl group, optional substituents include halogen, nitro, cyano, amino, hydroxyl, C
1-4
-alkyl, C
1-4
-alkoxy, C
1-4
-haloalkyl, C
1-4
-haloalkylthio, C
1-4
-haloalkoxy, C
2-4
haloalkenyl, and halosulfanyl groups having 1-5 halogen atoms, such as SF
5
. From 1 to 5 substituents may be present, 1 to 2 substituents being preferred. Typically, haloalkyl, haloalkenyl, haloalkoxy and haloalkylthio groups are trifluoromethyl, difluoromethoxy, trifluoromethoxy, difluoromethylthio and trifluoromethylthio groups.
Preferred compounds within the above definitions are those in which A represents a phenyl, pyridyl or pyrazolyl group, unsubstituted or substituted by one or more identical or different substituents selected from halogen atoms, alkyl, alkoxy, haloalkyl, haloalkylthio, haloalkoxy and pentahalosulfanyl groups. Preferably, at least one substituent is attached in the 3-position with respect to the carbon atom attached to the group Z. Most preferred A is a group of formula A,
in which
R
8
represents a halogen atom, or an alkyl, alkoxy, haloalkyl, haloalkylthio, haloalkoxy or pentahalosulfanyl group;
V represents CH or NCH
3
;
W represents N, S, N—CH or CH—CH.
X
1
and X
3
preferably represent CH or C-Halogen, in particular C—F, and X
2
represents CR
1
, in which R
1
has the meaning given and is preferably alkyl or alkoxy.
Preferred embodiments of the present invention are:
(a) A compound of formula I, wherein Z represents an oxygen atom.
(b) A compound of formula I, wherein R represents a group of formula 1:
(c) in which
R
5
through R
7
represent

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