High concentration topical insecticide

Details High concentration topical insecticide High concentration topical insecticide

2002-09-12

2003-07-08

Abbott, Yvonne (Department: 3644)

Animal husbandry

Antivermin treating or cleaning

Process

C424S403000, C424S405000

Reexamination Certificate

active

06588374

ABSTRACT:

BACKGROUND OF INVENTION
The invention relates generally to insecticides and more particularly to a topical insecticide, such as one suitable to use on house pets such as cats and dogs.
The infestation of animals with fleas, ticks, flies and the like is highly undesirable. Accordingly, it has become common to administer both topical and internal insecticides to livestock and pets. Topical applications can be desirable, in that many insecticides are acceptably safe when used topically, but not when used internally.
Various topical insecticides have drawbacks. Some require a large volume to be applied to the animal. This can cause considerable mess and can lead to an unpleasant smell. Also, when the animal is a house pet, there is a further complication in that the insecticide should be safe for human contact. It should also not lead to staining of furniture, carpeting and the like. Finally, even if safe, topical insecticides for house pets should not be irritating or lead to rashes, hair loss or exhibit other unpleasant side effects.
Accordingly, it is desirable to provide an improved topical insecticide, which overcomes drawbacks of the prior art.
SUMMARY OF THE INVENTION
Generally speaking, in accordance with the invention, a topical insecticide is provided which can be safe to use and avoids many common deleterious side effects of conventional topical insecticides. In one preferred embodiment of the invention, the active ingredient of the insecticide formulation is an amine derivative, having a nitro-methylene group, a nitroamino group or a cyanoamino group, which can be formulated to have low toxicity and excellent insecticidal activity. Active ingredients of insecticides and their method of formation in accordance with the preferred embodiments of the invention are discussed in U.S. Pat. Nos. 5,532,365 and 5,434,181, the contents of which are incorporated herein by reference. One particularly suitable insecticide is 1-{(tetrahydro-3-furanyl)methyl}-2-nitro-3-methylguanidine (dinotefuran). Dinotefuran is an aldulticide that will kill adult fleas.
In one preferred embodiment of the invention, the active portion of the insecticide formulation comprises (tetrahydro-3-furanyl)methylamine derivatives of following formula (1).
Active ingredients and insecticides in accordance with preferred embodiments of the invention are generally available as crystals and solids. Therefore, they need to be dissolved or otherwise put into a liquid form for use as topical spot products on animals. Topical spot products are more advantageous if the amount of liquid applied can be minimized. This must be balanced with the need for appropriate dosage to achieve the desired insecticidal effect. Therefore, it is desirable to use a solvent that will allow the solubilization of a high concentration of insecticide.
It has been determined that the insecticidal materials of the invention are advantageously dissolved in alcohols, but to relatively low concentrations. Phenyl methanol, is an alcohol, also known as benzyl alcohol, and is a liquid, somewhat soluble in water. It is routinely used in perfumes, flavors, photographi-c developers, dyes, films and inks and has other uses. It was surprisingly discovered that a relatively high concentration of the insecticide can be solubilized in phenyl methanol.
In one aspect of the current invention, the compound is dissolved in solvent to a concentration range of 2-20%, more preferably 4-17% and most preferably about 8 to 14%, with 12.5% as a preferred example. All percentages, unless otherwise evident, are on a weight basis.
In another preferred embodiment of the invention, the preferred solvent component comprises a mixture comprising water, ethyl lactate and ethanol, wherein the final concentration of ethyl lactate ranges from 5-20% and the final concentration of ethanol ranges from 30-45%, more preferably 7-15% ethyl lactate and 35-43% ethanol and most preferable a final concentration of 10% ethyl lactate and 40% ethanol. The remainder can be water. Isopropanol can also be added to ethanol to improve solubility.
Accordingly, it is an object of the invention to provide an improved topical insecticide, which overcomes drawbacks of the prior art.
DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS
The novel (tetrahydro-3-furanyl)methylamine derivatives of the formula (1) have an excellent insecticidal activity even in the absence of a pyridylmethyl group or a thiazolylmethyl group in their molecular structure. According to the present invention, there are provided (tetrahydro-3-furanyl)methylamine derivatives represented by formula (1), where X
1
, X
2
, X
3
, X
4
, X
5
, X
6
and X
7
represent each a hydrogen atom or an alkyl group having from 1 to 4 carbon atoms; R
1
represents a hydrogen atom, an alkyl group having from 1 to 5 carbon atoms, an alkenyl group having 3 carbon atoms, a benzyl group, an alkoxyalkyl group having from 2 to 4 carbon atoms (in its whole group), an alkyloxycarbonyl group having from 1 to 3 carbon atoms, a phenoxy carbonyl group, an alkylcarbonyl group having from 1 to 6 carbon atoms, an alkenylcarbonyl group having from 2 to 3 carbon atoms, a cycloalkylcarbonyl group having from 3 to 6 carbon atoms, a benzoyl group, a benzoyl group substituted by alkyl group(s) having from 1 to 4 carbon atoms, a benzoyl group substituted by halogen atom(s), a 2-furanylcarbonyl group or an N,N-dimethylcarbamoyl group; R
2
represents a hydrogen atom, an amino group, a methyl group, an alkylamino group having from 1 to 5 carbon atoms, a di-substituted alkylamino group having from 2 to 5 carbon atoms (in its whole group), a 1-pyrrolidinyl group, an alkenylamino group having 3 carbon atoms, an alkynylamino group having 3 carbon atoms, a methoxyamino group, an alkoxyalkylamino group having from 2 to 4 carbon atoms (in its whole group), a methylthio group or —N(Y
1
)Y
2
(where Y
1
represents an alkyloxycarbonyl group having from 1 to 3 carbon atoms, a phenoxycarbonyl group, an alkylcarbonyl group having from 1 to 6 carbon atoms, an alkenylcarbonyl group having from 2 to 3 carbon atoms, a cycloalkylcarbonyl group having from 3 to 6 carbon atoms, a benzoyl group, a benzoyl group substituted by alkyl group(s) having from 1 to 4 carbon atoms, a benzoyl group substituted by halogen atom(s), a 2-furanylcarbonyl group, an N,N-dimethylcarbamoyl group, a (tetrahydro-3-furanyl)methyl group or a benzyl group, and Y
2
represents a hydrogen atom or an alkyl group having from 1 to 5 carbon atoms); and Z represents ═N—NO
2
, ═CH—NO
2
or ═N—CN; insecticides containing the derivatives as an effective ingredient; and intermediates for producing the compounds of the formula (1) represented by a formula (2):
where X
1
, X
2
, X
3
, X
4
, X
5
, X
6
and X
7
represent each a hydrogen atom or an alkyl group having from 1 to 4 carbon atoms; R
10
represents an alkyl group having from 1 to 5 carbon atoms or a benzyl group; and R
11
represents an alkyl group having from 1 to 5 carbon atoms or a benzyl group.
The novel (tetrahydro-3-furanyl)methylamine derivatives of the formula (1) and formula (2) according to the invention are excellent compounds having a high insecticidal power and broad insecticidal spectrum. Further, agricultural chemicals containing the novel (tetrahydro-3-furanyl) methylamine derivatives of the formula (1) and (2) according to the invention have outstanding characteristics as insecticides and hence are useful.
Specific examples of the alkyl group for X
1
, X
2
, X
3
, X
4
, X
5
, X
6
and X
7
in the above formulae (1) and (2) include a methyl group, an ethyl group, an n-propyl group, an iso-propyl group, a tert-butyl group, and the like, preferably a methyl group.
Specific examples of the alkyl group for R
1
include a methyl group, an ethyl group, an n-propyl group, an iso-propyl group, an n-butyl group, an iso-butyl group, a sec-butyl group, a tert-butyl group, an n-pentyl group, and the like.
Specific examples of the alkenyl group for R
1
include a 1-propenyl group, a 2-propenyl group, and the like.
Specific examples of the

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