Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Reexamination Certificate
1999-07-13
2001-11-06
Robinson, Allen J. (Department: 1616)
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
C514S404000, C514S406000
Reexamination Certificate
active
06313157
ABSTRACT:
This application claims priority under 35 U.S.C. §119 of Application No. 99 1107095, filed in the European Patent Office on Jun. 4, 1999, incorporated by reference herein.
The present invention relates to a new insecticidal method.
It is well-known to kill insects by means of pyrazole derivatives with insecticidal properties, see inter alia European Patent Publication EP 0295117 and U.S. Pat. No. 5,232,940.
It has also been disclosed to use SF
5
-phenylpyrazoles against insects connected with public health and resistant to lindane or dieldrin. See International Patent Publications WO 93/06089 and WO 94/21606.
An object of the present invention is to provide a new method of control of fleas which is highly effective.
Another object of the present invention is to provide a method of cleaning animals or animal hair or skin which are or might be infested by fleas.
Another object of the present invention is to provide a method of control of fleas which are not resistant to the insecticides lindane or dieldrin.
These objects are met in whole or in part by the present invention.
The present invention provides a method of control of fleas by applying a 1-arylpyrazole of formula (I) to a locus where the fleas are located or expected to be located, the 1-arylpyrazole being a compound of the formula:
wherein:
R
1
is CN or methyl;
R
2
is S(O)
n
R
3
,
R
3
is alkyl or haloalkyl;
R
4
is selected from the group comprising a hydrogen atom, a halogen atom, and a radical which may be —NR
5
R
6
, —C(O)R
7
, —C(O)OR
7
, —S(O)
m
R
7
, alkyl, haloalkyl, —OR
8
, or —N═C(R
9
)(R
10
);
R
5
and R
6
are independently selected from a hydrogen atom, alkyl, haloalkyl, —C(O)R
7
, —C(O)OR
7
, —S(O)
r
CF
3
;
R
7
is selected from alkyl or haloalkyl;
R
8
is selected from alkyl, haloalkyl or the hydrogen atom;
R
9
is selected from the hydrogen atom and alkyl;
R
10
selected from phenyl or heteroaryl that is optionally substituted by one or more hydroxy, a halogen atom, —O—alkyl, —S-alkyl, cyano, or alkyl or combinations thereof;
X is selected from the nitrogen atom and the radical C—R
12
;
R
11
and R
12
are independently selected from a halogen atom or the hydrogen atom;
R
13
is —SF
5
;
m, n, and r are independently selected from 0, 1, and 2.
The alkyl and alkoxy groups of the formula (I) are preferably lower alkyl and alkoxy groups, that is, radicals having one to four carbon atoms. The haloalkyl and haloalkoxy groups likewise preferably have one to four carbon atoms. The haloalkyl and haloalkoxy groups can bear one or more halogen atoms; preferred groups of this type include —CF
3
and —OCF
3
.
A preferred group of 1-arylpyrazoles for use in the present invention are those of formula (1) having one or more of the following features wherein:
R
1
is CN;
R
4
is —NR
5
R
6
;
R
5
and R
6
are independently selected from the hydrogen atom, alkyl, haloalkyl, —C(O)R
7
, —C(O)OR
7
; or
X is C—R
12
.
A particularly preferred group of 1-arylpyrazoles for use in the present invention is that wherein:
R
1
is CN;
R
4
is —NR
5
R
6
;
R
5
and R
6
are independently selected from the hydrogen atom, alkyl, haloalkyl, —C(O)R
7
, —C(O)OR
7
; and
X is C—R
12
.
It is preferred that R
4
is amino.
Specific 1-arylpyrazoles which are preferred include 5-amino-3-cyano-1-(2,6-dichloro-4-pentafluorosulfenylphenyl)-4-trifluoromethysulfinylpyrazole, herein referred to as Compound A; 5-amino-3-cyano-1-(2,6-dichloro-4-pentafluorosulfenylphenyl)-4-trifluoromethylsulfenylpyrazole, herein referred to as Compound B; and 5-amino-3-cyano-1-(2,6-dichloro-4-pentafluorosulfenylphenyl)-4-trifluoromethylsulfonylpyrazole, herein referred to as Compound C.
The locus is preferably a dog or a cat, or the hair or the skin thereof. The arylpyrazole is preferably administered by dermal application, by injection or by oral administration of a bolus or a pill. Dermal administration is preferred, more preferably the so-called spot-on method whereby a small amount of liquid formulation is applied; the application being advantageously made such that the animal cannot reach the place of application with its limbs or tongue, the place being preferably the area between its forward legs and on its back between the shoulder blades.
The dose of the arylpyrazole is from 0.15 mg to 30 mg per kg of body weight of the treated animal, preferably from 0.6 to 15 mg/kg, most preferably from 1.2 to 10 mg/kg.
Compositions for oral administration comprise the active ingredient in association with pharmaceutically acceptable carriers or coatings and include, for example, tablets, pills, capsules, gels, drenches, medicated feeds, medicated drinking water, medicated dietary supplements, slow-release boluses or other slow-release devices intended to be retained within the gastrointestinal tract. Any of these may incorporate the active ingredients contained within microcapsules or coated with acid-labile or alkali-labile or other pharmaceutically acceptable enteric coatings. Feed premixes or concentrates containing compounds of the present invention for use in preparation of medicated diets, drinking water or other materials for consumption by animals may also be used.
For oral administration, generally the arylpyrazole of formula (I) is administered to an animal at a rate of from 0.1 to 100 mg/kg, preferably from 0.5 to 50 mg/kg and most preferably from 1 to 30 mg/kg.
The present invention also relates to a use of a 1-arylpyrazole of formula (I) as hereinbefore defined to manufacture a composition for the control of parasites, particularly fleas, in or on an animal.
The present invention also relates to a method of cleaning animals in good health comprising the application to the animal of a 1-arylpyrazole of formula (I) or a composition comprising the 1-arylpyrazole to the animal.
The method of cleaning an animal is not a method of treatment of the animal body per se because:
(a) the animal is in good health and requires no substantial treatment to correct a deficiency of health;
(b) the cleaning of the animal is not intended to be done by veterinary personnel, but by persons interested in the cleaning of the animal; and
(c) the purpose of such cleaning is to avoid unpleasant conditions for humans and the environment which humans inhabit so as to not infest the said humans with arthropods carried by the animal.
The present invention also provides the use of a composition comprising the 1-arylpyrazole as described supra as an active veterinary substance.
The arylpyrazole is most advantageously administered by use of compositions known to those skilled in the art.
REFERENCES:
patent: 5885607 (1999-03-01), Jeannin
patent: 6096329 (2000-08-01), Jeannin
Burns Doane Swecker & Mathis L.L.P.
Rhone-Poulenc Agro
Robinson Allen J.
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