Drug – bio-affecting and body treating compositions – Preparations characterized by special physical form – Biocides; animal or insect repellents or attractants
Reexamination Certificate
1999-12-23
2001-03-13
Dees, Jose′ G. (Department: 1616)
Drug, bio-affecting and body treating compositions
Preparations characterized by special physical form
Biocides; animal or insect repellents or attractants
C514S529000, C514S549000
Reexamination Certificate
active
06200584
ABSTRACT:
BACKGROUND OF THE INVENTION
1. Field of the Invention
This invention lies in the field of insect growth regulators and methods of application for the control of insects.
2. Description of the Prior Art
Insect growth regulators (including juvenile hormones) are well known for their use and efficacy in controlling or eliminating insect infestation in humans, in animals, and in both residential and industrial environments. Many types of insects are controllable by insect growth regulators, including fleas, flour beetles, cigarette beetles, and cockroaches. The regulators vary widely in chemical composition, and two of the more prominent classes are are 2,4-dienoic acids and phenoxyphenoxy compounds, particularly phenoxyphenoxyalkoxyheterocyclics, as well as benzoylureas and triazine derivatives. Examples of 2,4-dienoic acids and related compounds are methoprene, hydroprene, neotenin, and epiphenonane. Examples of phenoxyphenoxy compounds are fenoxycarb and pyriproxyfen. Examples of benzoylureas are lufenuron, diflubenzuron, terflubenzuron, triflumaron, hexaflumaron, and flucycloxuron. An example of a triazine derivative is 2-cyclopropylamino-4,6-bis(dimethylamino)-s-triazine.
Insect growth regulators are typically applied in liquid form, either as emulsifiable concentrates that are diluted and then sprayed, or as aerosols. The propellants and solvents that are needed to facilitate these methods of application, however, are increasingly subject to regulatory control, and in many cases this has resulted in a reduction in the performance and the aesthetics of the use of these materials.
SUMMARY OF THE INVENTION
It has now been discovered that insect growth regulators can be applied in a volatilized form to diffuse through air to regions where potential insect infestation exists, and still achieve effective results in insect control. In particular, it has been discovered that a liquid formulation of an insect growth regulator when heated by simple means, such as by being placed on the surface of or in close proximity to an incandescent light bulb or by conventional heating elements of various kinds, will generate a volatilized form of the insect growth regulator that will broadcast itself through a room or other spatial region to effectively condition the region to prevent or at least substantially reduce the maturation of insects from pre-adult stages. Once treated in this manner, insect control will be maintained in the room for an extended period of time. Objects in the room such as carpets, draperies, upholstered furniture, cushions and the like will no longer be active sites for insect growth, even though they may be several feet removed from the volatilization source or at the opposite side of the room.
These and other objects, advantages, features and embodiments of the invention will be more readily apparent from the descriptions below.
DETAILED DESCRIPTION OF THE INVENTION AND SPECIFIC EMBODIMENTS
One class of compounds that can be volatilized for effective broadcast application in accordance with this invention are 2,4-dienoic acids, including salts and esters of the acids, having the formula
in which:
R
1
is C
1
-C
6
alkyl;
R
2
is either H, methyl, or ethyl;
R
3
is either H or methyl;
R
4
is either methyl or ethyl;
R
5
is either H or methyl;
R
6
is either H or methyl;
R
7
is either methyl or ethyl;
R
8
is either H, C
1
-C
6
alkyl, C
3
-C
6
alkenyl, C
3
-C
6
alkynyl, C
3
-C
8
cycloalkyl, phenyl, naphthyl, C
7
-C
12
aralkenyl, or a cation of lithium, sodium, potassium, calcium, strontium, copper, manganese, or zinc;
X is either Br, Cl, Fl, or OR
9
, in which R
9
is either H, C
1
-C
6
alkyl or C
1
-C
6
alkanoyl;
m is either zero, 1, 2, or 3; and
n is either zero, 1, 2, or 3.
In this specification and the appended claims, the term “cycloalkyl” refers to a saturated hydrocarbon ring, including rings with one or more alkyl groups branching off from a ring carbon. Examples are cyclopropyl, cyclopentyl, cyclohexyl, methylcyclohexyl, and cyclohexylmethyl. Preferred cycloalkyl groups are C
3
-C
6
cycloalkyl, with cyclopentyl and cyclohexyl particularly preferred. The term “aralkyl” refers to an alkyl group substituted with an aromatic group both with and without one or more additional alkyl groups branching off from a ring carbon. Examples of aralkyl groups are benzyl, phenylethyl, naphthylmethyl, and ethylbenzyl. Preferred aralkyl groups are C
7
-C
9
aralkyl, with benzyl and phenylethyl particularly preferred. The term “alkanoyl” refers to an alkyl group bonded to a carboxy group. Examples are acetyl, propionyl, butyryl, and hexanoyl. Preferred alkanoyl groups are C
1
-C
3
alkanoyl, with acetyl and propionyl particularly preferred.
Within the scope of the above formula for 2,4-dienoic acids, salts and esters, certain groups of compounds of preferred. One such group is that in which the double bonds are in an E,E or Z,E configuration, preferably an E,E configuration. Another group that in which: R
1
is methyl or ethyl; R
2
is methyl or ethyl; R
7
is methyl; R
8
is C
1
-C
6
alkyl or C
3
-C
6
alkynyl; X is chloro or R
9
; m is zero or 1; and n is 1; all other variables as defined above. A third group is that in which: R
1
is methyl or ethyl; R
2
is methyl; R
3
is H; R
4
is methyl; R
5
is H; R
6
is H; R
7
is methyl; R
8
is C
1
-C
4
alkyl or C
3
-C
4
alkynyl; X is chloro or R
9
; m is 1; and n is 1; all other variables as defined above. A fourth group is the same as the third, except that R
9
is H, methyl, ethyl, isopropyl, t-butyl, or acetyl. A fifth group is also the same as the third, except that R
9
is methyl, ethyl, isopropyl, or t-butyl. Specific examples of known compounds within the scope of this formula are 11-methoxy-3,7,11-trimethyldodeca-2,4-dienoate, isopropyl ester (known by the generic name methoprene, and preferably the isomer trans(2), trans(4)-isopropyl 11-methoxy-3,7,11-trimethyldodeca-2,4-dienoate, or (E,E)-(7S)-11-methoxy-3,7,11-trimethyldodeca-2,4-dienoate, isopropyl ester, known as S-methoprene); 3,7,11-trimethyldodeca-2,4-dienoate, ethyl ester (known by the generic name hydroprene, and preferably the isomer (E,E)-(7S)-3,7,11-trimethyldodeca-2,4-dienoate, ethyl ester, known as S-hydroprene); and 2-propynyl (E,E)-3,7, 11-trimethyldodeca-2,4-dienoate (known by the generic name kinoprene). Methoprene and particularly (S)-methoprene are of particular interest. In the case of hydroprene, the preferred optical configurations are (R,S) and (S), while for kinoprene the preferred configuration is (S).
Another class of compounds that can be volatilized for effective broadcast application in accordance with this invention are 2-pyridyloxy-(lower alkylene)oxy-phenoxy compounds of the formula
in which:
R
11
is either an oxygen atom, a sulfur atom, or a methylene group;
R
12
is either a hydrogen atom or a methyl group;
R
13
is either a hydrogen atom or a methyl group;
R
14
is either an oxygen atom, a sulfur atom, or a methylene group;
R
15
is either an oxygen atom, a sulfur atom, or a methylene group;
R
16
is either a hydrogen atom or a fluorine atom; and
R
17
is either a hydrogen atom or a fluorine atom.
Within this formula as well, certain groups of compounds are preferred. In one such group, R
11
, R
14
, and R
15
are either oxygen or sulfur atoms, and preferably all are oxygen atoms. In another group, R
16
and R
17
are both hydrogen atoms. A specific example of an insect growth regulator within the scope of this formula is 2-pyridyloxy-(lower alkylene)oxyphenoxy compound is 2-{1-methyl-2-(4-phenoxyphenoxy)-ethoxy}pyridine (known by the generic name pyriproxifen).
In the practice of this invention, the insect growth regulator is volatilized from a liquid form such as a solution, an emulsion, or the undiluted active compound itself. Liquid solutions are particularly convenient, since a properly selected solvent can facilitate the absorption of the active ingredient by a solid absorbent matrix. The matrix may for example be a filter pad or a piece of fabric, or any such material that is readily wetted with the soluti
Duffey Eric
Rudolph Robin
Dees Jose′ G.
Pryor Alton
Townsend and Townsend / and Crew LLP
Wellmark International
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