Plant protecting and regulating compositions – Plant growth regulating compositions – Organic active compound containing
Reexamination Certificate
2000-12-04
2003-03-04
Ford, John M. (Department: 1624)
Plant protecting and regulating compositions
Plant growth regulating compositions
Organic active compound containing
C546S279100, C546S256000, C504S250000
Reexamination Certificate
active
06528456
ABSTRACT:
BACKGROUND OF THE INVENTION
This invention relates to certain novel 2-pyrazolyl-6-aryloxypyri(mi)dines, to the preparation of such compounds, to certain novel intermediates, to herbicidal compositions containing such compounds, and to a method of combating undesired plant growth using such compounds.
Pyridines, pyrimidines and their derivatives have many uses in the pharmaceutical area as well as in agriculture (herbicides, fungicides, acaricides, anthelmintics, bird repellents), as reagents, intermediates and chemicals for the polymer and textile industry.
The U.S. Pat. No. 5,750,470 discloses 2-azol-2-yl-5-aryloxypyridines in which the azolyl moiety contains at least two heteroatoms in the 1- and 3-position.
Similar 2-phenyl-6-aryloxypyri(mi)dines are disclosed by EP 0 723 960.
The broad generic formula of the International patent application WO 98/21199 embraces 2-pyrazol-5-yl-6-phenyloxypyridines, in which a hydrogen or halogen atom or a methyl group is attached in the 3-position of the pyridine ring.
The broad generic formula of the International patent application WO 98/56789 embraces 2-heteroar-2-yl-4-aryloxypyrimidines in which the heteroaryl moiety is a 5-membered ring containing at least one heteroatoms in the 1-position.
However, none of these documents discloses 2-pyrazol-5-yl-6-heteroaryloxypyridines nor 2-pyrazol-5-yl-6-(hetero)aryloxypyri(mi)dines.
Although many of the known compounds show considerable activity against various weeds, they are not completely satisfying with regard to their selectivity or because of their persistence.
The compounds according to the present invention combine high herbicidal activity with good selectivity and a desirable rate of degradation in soil.
SUMMARY OF THE INVENTION
The present invention provides novel compounds of the general formula I
wherein
A represents an optionally substituted aryl group or an optionally substituted 5- or 6-membered nitrogen- or sulfur-containing heteroaromatic group or a difluorobenzodioxolyl group;
Z represents N or CR
6
;
X represents an —O—, —S—, —CH
2
O— or —CH
2
S— atom;
R
1
and R
2
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 group; or —S(O)
n
—R
7
, in which n is 0, 1 or 2, and R
7
represents an alkyl or haloalkyl group; or —NR
8
R
9
, in which R
8
and R
9
each independently represent a hydrogen atom, an alkyl, alkenyl, aralkyl or aryl group, or R
10
O—CY—, in which R
10
represents an alkyl group, and Y represents O or S;
R
3
represents a hydrogen or halogen atom, or an alkyl, alkenyl, alkinyl, alkoxyalkyl, haloalkyl, cyano or nitro group, or —NR
11
R
12
, in which R
11
and R
12
each independently represent a hydrogen atom, an alkyl, alkenyl, aralkyl or aryl group,
R
4
represents a hydrogen or halogen atom, or an alkyl, alkenyl, alkinyl, alkoxy, alkoxyalkyl, alkoxyalkoxy, haloalkyl, haloalkoxy, cyano, nitro group,
or —S(O)
m
—R
13
, in which m is 0, 1 or 2, and R
13
represents an alkyl or haloalkyl group; and
R
5
represents a hydrogen atom, or an alkyl, alkenyl, alkinyl, alkoxyalkyl, cycloalkyl, haloalkyl, haloalkenyl, cyanoalkyl or cyano group;
or an agriculturally acceptable salt or N-oxide thereof;
with the proviso that
a) R
1
and R
6
both represent a hydrogen atom, and/or
b) R
2
represents a halogen atom, or an optionally substituted alkyl, alkenyl, alkinyl, alkoxy, alkoxyalkyl, alkoxyalkoxy group, or a haloalkyl, haloalkoxy, cyano, nitro group; or —S(O)
n
—R
7
, in which n is 0, 1 or 2, and R
7
represents an alkyl or haloalkyl group; or —NR R
9
, in which R
8
and R
9
each independently represent a hydrogen atom, an alkyl, alkenyl, aralkyl or aryl group, or R
10
O—CY—, in which R
10
represents an alkyl group, and Y represents O or S;
in the event that Z represents CR
5
and A represents an optionally substituted aryl group or an optionally substituted 6-membered nitrogen- or sulfur-containing heteroaromatic group.
The new compounds show an excellent selective herbicidal activity in certain crops, such as maize and rice, and degrade well in soil.
It is an object of the present invention to provide novel herbicidal compounds.
It is another 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.
It is another object of the invention to provide new processes for the preparation of the new compounds.
These and other objects and features of the invention will become more apparent from the detailed description set forth hereinbelow.
REFERENCES:
patent: 5032165 (1991-07-01), Miura et al.
patent: 5750470 (1998-05-01), Morimoto et al.
patent: 5840654 (1998-11-01), Kleemann et al.
patent: 5922738 (1999-07-01), Maier et al.
patent: 6204221 (2001-03-01), Nebel et al.
patent: 6310006 (2001-10-01), Maier et al.
patent: 0361114 (1990-04-01), None
patent: 0887343 (1998-12-01), None
patent: 0 955 292 (1999-11-01), None
patent: 0 955 300 (1999-11-01), None
patent: 2317384 (1998-03-01), None
patent: 94/22833 (1994-10-01), None
patent: WO 98/21199 (1998-05-01), None
patent: 98/40379 (1998-09-01), None
patent: WO 98/56789 (1998-12-01), None
patent: 99/59990 (1999-11-01), None
Kleemann Axel
Maier Thomas
BASF - Aktiengesellschaft
Ford John M.
Keil & Weinkauf
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