Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Reexamination Certificate
1999-09-20
2001-03-13
Dees, Jose′G. (Department: 1616)
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
C514S819000
Reexamination Certificate
active
06201012
ABSTRACT:
The present invention relates to a composition that comprises a combination of at least two parasiticidally active substances and that is suitable for controlling pests in and on animals, to a method of controlling these pests, to a process for the preparation of this composition, and to the use of this composition.
Certain compositions for controlling pests in and on animals are proposed in the literature. The properties of these known compositions are not always, however, entirely satisfactory, and, therefore, there is a need to make available further parasiticidally active compositions, especially for the control of insects, representatives of the order Acarina or parasitic worms, for example helminths. This problem is solved according to the invention by the provision of the instant composition.
The present invention accordingly relates to a composition for controlling parasites, in and on animals, which comprises, as active ingredient, a combination, in variable proportions, of at least one parasiticidally active compound, in free form or in salt form, selected from the N-phenyl-N′-benzoyl-urea class of substances, and at least one parasiticidally active compound, in free form or in salt form, selected from the milbemycin, avermectin, milbemycin oxime, moxidectin, ivermectin, abamectin and doramectin classes of substances and the derivatives thereof.
The invention relates preferably to a composition which comprises, as active ingredient, at least one compound of formula
wherein
R
1
is halogen, C
1
-C
8
alkyl, C
3
-C
8
cycloalkyl, halo-C
3
-C
8
cycloalkyl, halo-C
1
-C
8
alkyl, C
1
-C
8
alkoxy, C
1
-C
4
alkoxy-C
1
-C
4
alkyl or halo-C
1
-C
8
alkoxy;
R
2
is halogen, C
1
-C
8
alkyl, C
3
-C
8
cycloalkyl, halo-C
1
-C
8
alkyl, C
1
-C
8
alkoxy, C
3
-C
8
cycloalkoxy, halo-C
1
-C
8
alkoxy, aryloxy or heteroaryloxy, substituted aryloxy or heteroaryloxy or a group —CH
2
—O—N═C(R
3
)R
4
;
R
3
and R
4
are each independently of the other C
1
-C
4
alkyl, C
3
-C
8
cycloalkyl or aryl, each of which is unsubstituted or substituted;
m is 0 to 5, where, when m is greater than 1, the radicals R
1
are independent of one another; and
n is 0 to 5, where, when n is greater than 1, the radicals R
2
are independent of one another;
in free form or in salt form;
and at least one compound of formula
wherein
R
5
is C
1
-C
4
alkyl or C
2
-C
4
alkenyl;
the bond between the atoms 22 and 23 is a single bond or a double bond;
—X— is a group
R
6
is hydrogen, unsubstituted or substituted C
1
-C
8
alkyl, unsubstituted or substituted aryl, —C(═O)R
17
or —Si(R
18
)(R
19
)(R
20
);
R
7
is hydrogen or hydroxy, R
7
being hydrogen when the bond between the atoms 22 and 23 is a double bond;
R
8
is hydrogen, C
1
-C
8
alkyl, C
2
-C
8
alkenyl, aryl or a group —OR
9
or —SR
9
;
R
9
is C
1
-C
8
alkyl, C
2
-C
8
alkenyl, C
2
-C
8
alkynyl, aryl, C(═O)R
16
, substituted C
1
-C
8
alkyl, C
2
-C
8
alkenyl, C
2
-C
8
alkynyl or aryl, or an unsubstituted or substituted heterocyclic radical;
R
10
is hydrogen, unsubstituted or substituted C
1
-C
8
alkyl, aryl-C
1
-C
4
alkyl, —(CH
2
)
o
COR
11
or —SO
2
—R
15
;
R
11
is hydrogen, C
1
-C
8
alkyl, aryl-C
1
-C
8
alkyl, C
2
-C
8
alkenyl, C
2
-C
8
alkynyl, C
1
-C
8
alkoxy, C
2
-C
8
alkenyloxy, C
2
-C
8
alkynyloxy, aryl, aryloxy, —N(R
12
)R
13
, —(CH
2
)
p
COOR
14
, or C
1
-C
8
alkyl or C
1
-C
8
alkoxy substituted by C
1
-C
4
alkoxy, halogen or by nitro, or aryl, aryloxy or aryl-C
1
-C
8
alkyl substituted by C
1
-C
4
alkyl, halo-C
1
-C
4
alkyl, C
1
-C
4
alkoxy, halo-C
1
-C
4
alkoxy, halogen or by nitro;
R
12
and R
13
are each independently of the other hydrogen, C
1
-C
8
alkyl, phenyl, or C
1
-C
8
alkyl or phenyl substituted by C
1
-C
4
alkoxy, halogen or by nitro;
R
14
is hydrogen or unsubstituted or substituted C
1
-C
8
alkyl;
R
15
is C
1
-C
8
alkyl or aryl, each of which is unsubstituted or substituted;
R
16
is hydrogen, C
1
-C
8
alkyl, C
1
-C
8
alkoxy or aryl, each of which is unsubstituted or substituted;
R
17
is hydrogen, C
1
-C
8
alkyl, C
1
-C
8
alkoxy or aryl, each of which is unsubstituted or substituted;
R
18
, R
19
and R
20
are each independently of the others C
1
-C
8
alkyl, C
1
-C
8
alkoxy or aryl, each of which is unsubstituted or substituted;
o is 0, 1, 2, 3 or 4; and
p is 0, 1, 2, 3 or 4;
in free form or in salt form.
A compound I or II, which has at least one basic centre, can form, for example, acid addition salts. These acid addition salts are formed, for example, with strong inorganic acids, such as mineral acids, for example perchloric acid, sulfuric acid, nitric acid, nitrous acid, a phosphoric acid or a hydrohalic acid, with strong organic carboxylic acids, such as unsubstituted or substituted, for example halogen-substitutled, C
1
-C
4
alkanecarboxylic acids, for example acetic acid, or unsaturated or saturated dicarboxylic acids, for example oxalic acid, malonic acid, succinic acid, maleic acid, fumaric acid or phthalic acid, or hydroxycarboxylic acids, for example ascorbic acid, lactic acid, malic acid, tartaric acid or citric acid, or benzoic acid, or with organic sulfonic acids, such as unsubstituted or substituted, for example halogen-substituted, C
1
-C
4
alkane- or arylsulfonic acids, for example methane- or p-toluenesulfonic acid. A compound I or II, which has at least one acidic group, can form salts with bases. Suitable salts with bases are, for example, metal salts such as alkali metal salts or alkaline earth metal salts, for example sodium salts, potassium salts or magnesium salts, or salts with ammonia or with an organic amine, such as morpholine, piperidine, pyrrolidine, a mono-, di- or tri-lower-alkylamine, for example ethyl-, diethyl-, triethyl- or dimethylpropylamine, or a mono-, di- or trihydroxy-lower-alkylamine, for example mono-, di- or triethanolamine. Moreover, corresponding internal salts may also be formed, where possible. Preferred salts within the scope of the invention are veterinarily advantageous salts. Due to the close relationship between a compound I or II in free form and in the form of the salts thereof, a free compound I or II, or the salts thereof, respectively, are to be understood analogously hereinabove and hereinafter as meaning, if appropriate, also the corresponding salts and the free compounds I or II, respectively. Generally preferred is, in each case, the free form.
The compounds of formula II wherein X is
may occur as syn-isomers or anti-isomers in respect of the double bond. According to the invention, both forms are included, both the pure isomers and mixtures of isomers being meant.
Unless defined otherwise, the general terms used hereinbefore and hereinafter have the meanings given below.
Halogen—as a group per se and as a structural unit of other groups and compounds, such as of haloalkyl and haloalkoxy, —is fluorine, chlorine, bromine or iodine, especially fluorine, chlorine or bromine, more especially fluorine or chlorine.
Unless defined otherwise, groups and compounds containing carbon each preferably contain from 1 up to and including 20, preferably from 1 up to and including 18, most preferably from 1 up to and including 10, especially from 1 up to and including 6, most especially from 1 up to and including 4, especially from 1 up to and including 3, carbon atoms.
Alkyl—as a group per se and as a structural unit of other groups and compounds, such as of haloalkyl, alkoxy and haloalkoxy, —is either straight-chained, e.g. methyl, ethyl, n-propyl, n-butyl, n-hexyl, n-octyl, n-decyl, n-dodecyl, n-hexadecyl or n-octadecyl, or branched, e.g. isopropyl, isobutyl, sec-butyl, tert-butyl, isopentyl, neopentyl or isohexyl.
Alkenyl—as a group per se and as a structural unit of other groups, such as of alkenyloxy, —is straight-chained or branched alkenyl, e.g. vinyl, 1-methylvinyl, allyl, but-1-enyl or isopropenyl, especially allyl.
Alkynyl—as a group per se and as a structural unit of other groups and compounds, such as of alkynyloxy, —is e.g. ethynyl, prop-1-ynyl or but-1-ynyl, especially propargyl.
Halo-substituted carbon-containing groups and compounds, such as haloalkyl, ha
Hepler Douglas Irvin
Kemmethmuller Stefan
Lowndes Philip Anthony
Parks Steven Craig
Dees Jose′G.
Morris Michael P.
Novartis Animal Health US Inc.
Pryor Alton
Teoli William A.
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