Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Reexamination Certificate
2001-11-13
2002-09-17
Ramsuer, Robert W. (Department: 1626)
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
C548S377100
Reexamination Certificate
active
06451835
ABSTRACT:
BACKGROUND OF THE INVENTION
1. Field of the Invention
The present invention relates to pesticidal fluoroethyl pyrazole derivatives. More particularly, this invention relates to fluoroethyl pyrazole derivatives that exhibit activity as insecticides, acaricides, fungicides, and nematocides. This invention also relates to insecticidal, acaricidal, fungicidal, and nematocidal compositions comprising the fluoroethyl pyrazole derivatives, and to methods of controlling insects, nematodes, fungi, and acarids using such compounds or compositions.
2. Description of Related Art
Destruction of crops by insects, acarids, fungi, and nematodes presents a serious problem to agriculture and a wide variety of field crops are in need of protection from them. Particularly difficult types of these pests to control are those which, at one or more stages of their life, inhabit the soil and cause destruction to the roots of plants. Accordingly, the development of fungicides and of insecticides, nematocides, and acaricides that are effective as ovicides, larvicides, and adulticides is desirable.
Baklouti and Hedhli,
Journal of Fluorine Chemistry
45:255-263 (1989) (CA 112:198205), reported the preparation of certain fluoroethyl pyrazoles, but the 4-substitution of the instant invention was absent. In addition, they did not report biological properties of the compounds.
Japanese patent JP 59053468 1984 (CA 101:90922) refers to phenyl pyrazoles with fungicidal activity.
It is a purpose of this invention to provide novel fluoroethyl pyrazole derivatives and physiologically acceptable salts thereof that are useful as insecticides, nematocides, fungicides, and acaricides.
SUMMARY OF THE INVENTION
This invention relates to fluoroethyl pyrazole compounds of the formula:
wherein X and Y are independently selected from the group consisting of hydrogen, halogen, alkyl, haloalkyl, nitro, alkylthio, alkylsulfinyl, alkylsulfonyl, and haloalkoxy. Where X and/or Y comprises an alkyl moiety, it is preferred that it be lower alkyl, e.g., alkyl of from 1 to 4 carbon atoms, such as, methyl, ethyl, propyl, butyl, or an isomer of the foregoing.
The compounds of the present invention are useful as plant protecting agents for the control of acarid, nematode, fungus, and insect pests. Thus, the present invention also relates to a pesticidal composition comprising: a) an effective amount of a compound of formula 1; and b) a suitable carrier. The present invention further relates to a method for controlling insects, nematodes, fungi, or acarids that comprises applying an effective amount of the compound of formula I to the locus to be protected.
More particularly, the present invention is directed to fluoroethyl pyrazole compounds of the formula:
wherein X and Y are independently selected from the group consisting of hydrogen, halogen, alkyl, haloalkyl, nitro, alkylthio, alkylsulfinyl, alkylsulfonyl, and haloalkoxy.
In another aspect, the present invention is directed to a pesticidal composition comprising:
A) at least one fluoroethyl pyrazole compounds of the formula:
wherein X and Y are independently selected from the group consisting of hydrogen, halogen, alkly, haloalkyl, nitro, alkylthio, alkylsulfinyl, alkylsulfonyl, and haloalkoxy; and
B) a suitable carrier.
In still another aspect, the present invention is directed to a method for controlling pests comprising applying an effective amount of at least one fluoroethyl pyrazole compound of the formula:
wherein X and Y are independently selected from the group consisting of hydrogen, halogen, alkyl, haloalkyl, nitro, alkylthio, alkylsulfinyl, alkylsulfonyl, and haloalkoxy, to the locus to be protected.
DESCRIPTION OF THE PREFERRED EMBODIMENTS
As stated above, the present invention is directed to fluoroethyl pyrazole compounds of the formula:
wherein X and Y are independently selected from the group consisting of hydrogen, halogen, alkyl, haloalkyl, nitro, alkylthio, alkylsulfinyl, alkylsulfonyl, and haloalkoxy. Preferably, where X and/or Y comprise an alkyl moiety, it is one of from 1 to 4 carbon atoms. Particularly preferred are the fluoroethyl pyrazole compounds of formula I wherein X and/or Y are hydrogen, halogen, haloalkyl, or haloalkoxy.
The compounds of the present invention can be prepared by reacting a substituted pyrazole with bromofluoroethane and an equivalent of a hydrogen halide, e.g.,HBr, acceptor, such as potassium carbonate or sodium hydride, in a solvent, such as acetonitrile or dimethylsulfoxide. Following the reaction, the product (I) is either precipitated by the addition of water or, if a liquid is formed, extracted into an organic solvent, such as diethyl ether or dichloromethane.
The following equation is illustrative of the process:
The present invention farther relates to a pesticidal composition comprising a) an effective amount of a fluoroethyl pyrazole derivative of formula I; and (b) a suitable carrier. Such suitable carriers may be solid or liquid in nature.
Suitable liquid carriers can comprise water, alcohols, ketones, phenols, toluene, and xylenes. In such formulations, additives conventionally employed in the art can be utilized, such as one or more surface active agents and/or inert diluents, to facilitate handling and application of the resulting insecticidal composition.
Alternatively, the compounds of this invention can be applied as a liquid or in sprays when utilized in a liquid carrier, such as a solution comprising a compatible solvent, such as acetone, benzene, toluene, or kerosene, or a dispersion comprising a suitable non-solvent medium such as water.
The compositions of this invention can alternatively comprise solid carriers taking the form of dusts, granules, wettable powders, pastes, aerosols, emulsions, emulsifiable concentrates, and water-soluble solids. For example, the compounds of this invention can be applied as dusts when admixed with or absorbed onto powdered solid carriers, such as mineral silicates, talc, pyrophyllite and clays, together with a surface-active dispersing agent so that a wettable powder is obtained which then is applied directly to the loci to be treated. Alternatively, the powdered solid carrier containing the compound admixed therewith can be dispersed in water to form a suspension for application in such form.
Granular formulations of the compounds are preferred for field treatment and are suitable for application by broadcasting, side dressing, soil incorporation, or seed treatment, and are suitably prepared using a granular or pelletized form of carrier, such as granular clays, vermiculite, charcoal, or corn cobs. The compounds of this invention can be dissolved in a solvent and sprayed onto an inert mineral carrier, such as attapulgite granules (10-100 mesh), whereupon the solvent is evaporated. Such granular compositions can contain from 2-25% of a compound of this invention, based on carrier plus compound, preferably, 3-15%. In addition, the compounds of this invention can also be incorporated into a polymeric carrier, such as polyethylene, polypropylene, butadiene-styrene, styrene-acryonitrile resins, polyamides, poly(vinyl acetates), and the like. When encapsulated, the compounds of this invention can advantageously be released over an even longer time period, extending their effectiveness further than when used in non-encapsulated form.
Another method of applying the compounds of this invention to the loci to be treated is by aerosol treatment, for which the compounds can be dissolved in an aerosol carrier that is a liquid under pressure, but which is a gas at ordinary temperature (e.g., 20° C.) and atmospheric pressure. Aerosol formulations can also be prepared by first dissolving the compounds in a less volatile solvent and then admixing the resulting solution with a highly volatile liquid aerosol carrier.
For treatment of plants (such term including plant parts), the compounds of the invention preferably are applied in aqueous emulsions containing a surface-active dispersing agent, which can be non-ionic, cationic, or anionic. Suitable surface-active agents are well known in the
Dekeyser Mark A.
McDonald Paul T.
Ramsuer Robert W.
Reitenbach Daniel
Uniroyal Chemical Company, Inc.
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