Pesticidal thiadiazine compounds

Details Pesticidal thiadiazine compounds Pesticidal thiadiazine compounds

1999-01-12

2001-01-30

Levy, Neil S. (Department: 1617)

Drug, bio-affecting and body treating compositions

Preparations characterized by special physical form

Biocides; animal or insect repellents or attractants

C514S222500, C548S559000

Reexamination Certificate

active

06180126

ABSTRACT:

FIELD OF THE INVENTION
This invention relates to pesticidal thiadiazine derivatives. More particularly, this invention relates to thiadiazine derivatives which exhibit activity as insecticides and as miticides. This invention also relates to insecticidal and miticidal compositions comprising the thiadiazine derivatives as well as to methods of controlling insects and acarids employing such compounds or compositions.
BACKGROUND OF THE INVENTION
Destruction of crops by insects and acarids presents a serious problem to agriculture. A wide variety of field crops are in need of protection from acarids and insects. Particularly difficult types of acarids and insects 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 insecticides and miticides which are effective as ovicides, larvicides, and adulticides is desirable. Certain oxadiazine compounds have been described as useful as pesticides and as pharmaceutical agents. For example, U.S. Pat. No. 5,536,720 describes substituted 2-phenyl-1,3,4-oxadiazine-4-carbamide compounds useful as insecticides and acaricides. Trepanier et al, J. Med. Chem 9: 753-758 (1966) describe certain 2-substituted 4H-1,3,4-oxadiazines useful as anticonvulsants in mice. U.S. Pat. No. 3,420,826 describes certain 2,4,6-substituted 4H-1,3,4-oxadiazines, useful as sedatives, anticonvulsants, and as pesticides against nematodes, plants, and fungi. U.S. Pat. No. 3,420,825 describes methods for producing certain 2,4,6-substituted 4H-1,3,4-oxadiazines.
It is a purpose of this invention to provide novel thiadiazine derivatives useful as insecticides and miticides.
SUMMARY OF THE INVENTION
This invention relates to a compound of the formula
wherein R is hydrogen, halogen, nitro, C
1
-C
8
alkyl, C
1
-C
8
alkoxyl, or C
1
-C
8
haloalkyl. The compounds of this invention useful as plant protecting agents for the control of mite and insect pests.
The present invention also relates to a pesticidal composition comprising: a) an effective amount of a compound of formula I; and b) a suitable carrier.
The present invention further relates to a method for controlling insects or acarids which comprises applying an effective amount of the compound of formula I to the locus to be protected.
DETAILED DESCRIPTION OF THE INVENTION
It is preferred that the compound of formula I has the formula
wherein R is as defined above.
Preferably, in the compound of formula I (and accordingly, in the compounds of formulas IA and IB), R is hydrogen, halogen, nitro, C
1
-C
4
alkyl, C
1
-C
4
alkoxyl, or C
1
-C
4
trihaloalkyl. More preferably, R is hydrogen, methyl, ethyl, methoxy, ethoxy, trifluoromethyl, bromine, fluorine, iodine, or nitro.
The compounds of the present invention can be prepared by reacting a hydrazide of formula A below, wherein R is as defined above, and bromofluoroethane, in the presence of a base such as potassium or sodium hydroxide. The resulting intermediate of formula B is then reacted with Lawesson's reagent to produce the compound of formula I. Lawesson's reagent is [2,4-bis(4-methoxyphenyl)-1,3-dithia-2,4-diphosphetane-2,4-disulfide (available from Aldrich Chemical Company).
The compositions of the present invention can be prepared by formulating one or more compounds of the present invention with a suitable carrier.
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 compound of this invention is dissolved in a solvent and sprayed onto an inert mineral carrier such as attapulgite granules (10-100 mesh), and the solvent is then 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 compound of this invention can advantageously be released over an even longer time period, extending its effectiveness further than when used in non-encapsulated form.
Another method of applying the compound of this invention to the loci to be treated is by aerosol treatment, for which the compound can be dissolved in an aerosol carrier which 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 compound 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 art, such as those disclosed in U.S. Pat. No. 2,547,724 (columns 3 and 4). The compounds of this invention can be mixed with such surface-active dispersing agents, with or without an organic solvent, as concentrates for the subsequent addition of water, to yield aqueous suspensions of the compounds at desired concentration levels.
In addition, the compounds can be employed with carriers which themselves are pesticidally active, such as insecticides, acaricides, fungicides or bactericides.
It will be understood that the effective amount of a compound in a given formulation will vary depending, e.g., upon the specific pest to be combated, as well as upon the specific chemical composition and formulation of the compound being employed, the method of applying the compound/formulation and the locus of treatment. Generally, however, the effective amount of the compound of this invention can range from about 0.1 to about 95 percent by weight. Spray dilutions can be as low as a few parts per million, while at the opposite extreme, full strength concentrates of the compound can be usefully applied by ultra low volume techniques. When plants constitute the loci of treatment, concentration per unit area can range between about 0.01 and about 50 pounds per acre, with concentrations of between about 0.1 and about 10 pounds per acre preferably being employed for crops such as corn, tobacco, rice and the like.
To combat insects and mites, sprays of the compounds can be applied to any suitable locus, such as to the insects or mites directly and/or to plants upon which they feed or nest. The

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