Plant protecting and regulating compositions – Plant growth regulating compositions – Plural active ingredients
Reexamination Certificate
2000-01-31
2002-04-23
Raymond, Richard L. (Department: 1624)
Plant protecting and regulating compositions
Plant growth regulating compositions
Plural active ingredients
C544S310000
Reexamination Certificate
active
06376426
ABSTRACT:
BACKGROUND OF THE INVENTION
The present invention relates to heterocyclyl-uracils in which the 3-position of the uracil moiety is directly attached to the nitrogen of the heterocyclyl group.
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 superior or different activities, because the known herbicidal compounds either are not suitable for application in certain crops, or are not sufficiently selective or active.
Herbicidal heterocyclyl-uracils are known, for example, from JP-A 91-287 585, JP-A 93 202 031, WO 98/27082 and WO 98/27088.
However, heterocyclyl-uracils in which the heterocyclyl group is attached to the uracil group in the 3-position via the nitrogen atom have not yet been described.
SUMMARY OF THE INVENTION
The present invention provides novel 3-heterocycl-1-yluracil compounds of the formula (I)
wherein
R
1
and R
2
together with the interjacent nitrogen atom form an optionally substituted, optionally benzo-condensed 5-membered heterocyclic ring,
R
3
represents a hydrogen atom, or an amino, a cyano or a hydroxy group, or an alkyl or alkoxy group optionally substituted by one or more substituents selected from halogen atoms, cyano and alkoxy groups,
R
4
represents a halogen atom, or a formyl, a hydroxyiminomethyl, a cyano, a carboxy, an alkoxycarbonyl, a carbamoyl, a thiocarbamoyl, an alkyl, an alkoxy, an alkylthio, a haloalkyl, a haloalkoxy or a haloalkylthio group,
R
5
represents a hydrogen or halogen atom, or an alkyl group; or an agriculturally acceptable salt or N-oxide thereof.
The new compounds show 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 herein below, and from the appended claims.
DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS
It has surprisingly been found that the compounds of the formula (I)
wherein
R
1
through R
5
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 wheat, soybeans and rice, in pre- and post-emergence applications on both broadleaf and grassy weed species.
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. Alkyl groups preferably contain one to six carbon atoms, alkenyl and alkynyl groups contain preferably two to 8 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 12, preferably up to 6, e.g. methoxymethyl, methoxymethoxy, methoxyethyl, ethoxymethyl, ethoxyethoxy, dimethoxymethyl.
“Halogen” means a fluorine, chlorine, bromine or iodine atom, preferably fluorine, chlorine or bromine.
The term “heterocylyl” shall mean a heteroaromatic or heteroaliphatic ring containing at least one nitrogen atom. Examples include azoles such as imidazole, pyrrole, pyrazole and triazole as well as the corresponding hydrogenated groups.
The term “benzo-condensed” shall mean a bicyclic aromatic ring system, in which one ring is a benzene ring and the other is a heterocyclyl group. Examples include indole, indazol, isoindol, carbazol, benzimidazol and benzotriazol.
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.
Also included in the invention are the stereo and optical isomers of the compounds claimed and mixtures of these isomers in all proportions.
The terms herbicide and herbicidal are used to denote the inhibitive control or modification of undesired plant growth. Inhibitive control and modification include all deviations from natural development such as, for example, total killing, growth retardation, defoliation, desiccation, regulation, stunting, tillering, stimulation, leaf burn and dwarfing. The term herbicidally effective amount is used to denote any amount which achieves such control or modification when applied to the undesired plants themselves or the area in which these plants are growing. The term plants is intended to include germinated seeds, emerging seedlings and established vegetation, including both roots and above-ground portion.
The term agriculturally acceptable salts is used herein to denote a salt or salts which readily ionize in aqueous media and includes sodium, potassium, calcium, ammonium, and magnesium salts and acid salts such as hydrochloride, sulfate and nitrate.
The compounds according to formula I include oils, gums, or, predominantly, crystalline solid materials. They possess a high herbicidal activity within a wide concentration range can be used in agriculture or related fields for the control of undesired plants such as:
dicotyledoneous species: Abutilon, Amaranthus, Ambrosia, Anthemis, Brassica, Centaurea, Chenopodium, Chrysanthemum, Cirsium, Convolvus, Datura, Galeopsis, Galinsoga, Galium, Ipomoea, Lamium, Lepidium, Matricaria, Papaver, Pharbitis, Polygonum, Portulaca, Senecio, Sinapis, Sesbana, Solanum, Sonchus, Stellaria, Urtica, Veronica, Viola and Xantium;
monocotyledoneous species: Alopecurus, Apera, Avena, Brachiaria, Bromus, Cyperus, Digitada, Echinochloa, Eleocharis, Elymus, Fimbristylis, Ischaemum, Lolium, Monochoria, Panicum, Poa, Sagittaria, Setaria and Sorghum.
The compounds of formula I can be used in particular for the control of Alopecurus myosuroides,
Echinochloa crus-galli, Setaria vi
Newton Trevor
Scheiblich Stefan
Servaas Savio van Eijk Peter Johannes
Waldeck Isabel
Balasubramanian Venkataraman
BASF - Aktiengesellschaft
Maurer Barbara V.
Raymond Richard L.
LandOfFree
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