Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Reexamination Certificate
1999-01-22
2001-05-22
Weddington, Kevin E. (Department: 1614)
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
Reexamination Certificate
active
06235754
ABSTRACT:
BACKGROUND OF THE INVENTION
Arthropod and helminth parasites cause hundreds of millions of dollars in economic damage annually on a global basis. In particular, flies, fleas, lice, mosquitoes, gnats, mites, ticks and helminths cause tremendous losses to the livestock and companion animal sectors. Arthropod parasites also are a nuisance to humans and can vector disease-causing organisms in humans and animals.
In spite of the commercial parasiticides available today, damage to humans, livestock and companion animals still occurs. Accordingly, there is ongoing research to create new and more effective parasiticides.
It is, therefore, an object of the present invention to provide a method for treating animals and humans, and for controlling, preventing and protecting animals and humans from infestation and infection by arthropod and helminth parasites.
It is also an object of the present invention to provide a composition for treating animals and humans, and for controlling, preventing and protecting animals and humans from infestation and infection by arthropod and helminth parasites.
These and other objects of the present invention will become more apparent from the detailed description thereof set forth below.
SUMMARY OF THE INVENTION
The present invention provides a method of treatment for controlling, preventing and protecting animals and humans from infestation and infection by arthropod and helminth parasites which comprises administering or applying to the animals, humans or their environment a parasiticidally effective amount of a 1,4-diaryl-2-fluoro-2-butene or 1,4-diaryl-2,3-difluoro-2-butene compound having the structural formula I
wherein
Ar is phenyl optionally substituted with any combination of from one to three halogen, C
1
-C
4
alkyl, C
1
-C
4
haloalkyl, C
1
-C
4
alkoxy or C
1
-C
4
haloalkoxy groups,
1- or 2-naphthyl optionally substituted with any combination of from one to three halogen, C
1
-C
4
alkyl, C
1
-C
4
haloalkyl, C
1
-C
4
alkoxy or C
1
-C
4
haloalkoxy groups, or
a 5- or 6-membered heteroaromatic ring optionally substituted with any combination of from one to three halogen, C
1
-C
4
alkyl, C
1
-C
4
haloalkyl, C
1
-C
4
alkoxy or C
1
-C
4
haloalkoxy groups;
R and R
1
are each independently hydrogen, C
1
-C
4
alkyl, C
1
-C
4
haloalkyl, C
3
-C
6
cycloalkyl or C
3
-C
6
halocycloalkyl, or R and R
1
taken together with the carbon atom to which they are attached form a C
3
-C
6
cycloalkyl ring optionally substituted with any combination of from one to three halogen or C
1
-C
4
alkyl groups, provided that when Z is F, R
1
is hydrogen;
Z is hydrogen or F;
R
2
is hydrogen, Cl, Br, cyano or OR
3
;
R
3
is hydrogen or C
1
-C
4
alkyl; and
Ar
1
is phenoxyphenyl optionally substituted with any combination of from one to six halogen, C
1
-C
4
alkyl, C
1
-C
4
haloalkyl, C
1
-C
4
alkoxy or C
1
-C
4
haloalkoxy groups,
phenyl optionally substituted with any combination of from one to five halogen, C
1
-C
4
alkyl, C
1
-C
4
haloalkyl, C
1
-C
4
alkoxy or C
1
-C
4
haloalkoxy groups,
biphenyl optionally substituted with any combination of from one to five halogen, C
1
-C
4
alkyl, C
1
-C
4
haloalkyl, C
1
-C
4
alkoxy or C
1
-C
4
haloalkoxy groups,
phenoxypyridyl optionally substituted with any combination of from one to five halogen, C
1
-C
4
alkyl, C
1
-C
4
haloalkyl, C
1
-C
4
alkoxy or C
1
-C
4
haloalkoxy groups,
benzylpyridyl optionally substituted with any combination of from one to five halogen, C
1
--C
4
alkyl, C
1
-C
4
haloalkyl, C
1
-C
4
alkoxy or C
1
-C
4
haloalkoxy groups,
benzylphenyl optionally substituted with any combination of from one to five halogen, C
1
-C
4
alkyl, C
1
-C
4
haloalkyl, C
1
-C
4
alkoxy or C
1
-C
4
haloalkoxy groups,
benzoylphenyl optionally substituted with any combination of from one to five halogen, C
1
-C
4
alkyl, C
1
-C
4
haloalkyl, C
1
-C
4
alkoxy or C
1
-C
4
haloalkoxy groups,
1- or 2-naphthyl optionally substituted with any combination of from one to three halogen, C
1
-C
4
alkyl, C
1
-C
4
haloalkyl, C
1
-C
4
alkoxy or C
1
-C
4
haloalkoxy groups, or
a 5- or 6-membered heteroaromatic ring optionally substituted with any combination of from one to three halogen, C
1
-C
4
alkyl, C
1
-C
4
haloalkyl, C
1
-C
4
alkoxy or C
1
-C
4
haloalkoxy groups, and
the optical isomers thereof, and
the (E)- and (Z)-isomers thereof.
This invention also provides compositions for treating animals and humans, and controlling, preventing and protecting animals and humans from infestation and infection by arthropod and helminth parasites. The compositions of the present invention comprise an agronomically or pharmaceutically acceptable carrier and an arthropod or helminth parasiticidally effective amount of a formula I compound. Advantageously, it has been found that the 1,4-diaryl-2-fluoro-2-butene and 1,4-diaryl-2,3-difluoro-2-butene compounds of this invention, and compositions containing them, are especially useful in the practice of the invention against infestation and infection by flies, fleas, lice, mosquitoes, gnats, mites and ticks.
DETAILED DESCRIPTION OF THE INVENTION
The 1,4-diaryl-2-fluoro-2-butene and 1,4-diaryl-2,3-difluoro-2-butene compounds which are useful in the methods and compositions of this invention have the structural formula I
wherein R, R
1
, R
2
, Z, Ar and Ar
1
are as described hereinabove for formula I.
Preferred formula I compounds for use in the methods and compositions of this invention are those wherein
Ar is phenyl optionally substituted with any combination of from one to three halogen, C
1
-C
4
alkyl, C
1
-C
4
haloalkyl, C
1
-C
4
alkoxy or C
1
-C
4
haloalkoxy groups;
R and R
1
are each independently hydrogen, C
1
-C
4
alkyl, C
1
-C
4
haloalkyl, C
3
-C
6
cycloalkyl or C
3
-C
6
halocycloalkyl provided that at least one of R and R
1
is other than hydrogen, or R and R
1
taken together with the carbon atom to which they are attached form a C
3
-C
6
cycloalkyl ring optionally substituted with any combination of from one to three halogen or C
1
-C
4
alkyl groups, provided that when Z is F, R
1
is hydrogen;
Z is hydrogen or F;
R
2
is hydrogen, Cl, Br, cyano or OR
3
;
R
3
is hydrogen or C
1
-C
4
alkyl; and
Ar
1
is 3-phenoxyphenyl optionally substituted with any combination of from one to six halogen, C
1
-C
4
alkyl, C
1
-C
4
haloalkyl, C
1
-C
4
alkoxy or C
1
-C
4
haloalkoxy groups,
3-biphenyl optionally substituted with any combination of from one to five halogen, C
1
-C
4
alkyl, C
1
-C
4
haloalkyl, C
1
-C
4
alkoxy or C
1
-C
4
haloalkoxy groups, or
3-benzylphenyl optionally substituted with any combination of from one to five halogen, C
1
-C
4
alkyl, C
1
-C
4
haloalkyl, C
1
-C
4
alkoxy or C
1
-C
4
haloalkoxy groups.
More preferred formula I compounds are those wherein
Ar is phenyl optionally substituted with any combination of from one to three halogen, C
1
-C
4
alkyl, C
1
-C
4
haloalkyl, C
1
-C
4
alkoxy or C
1
-C
4
haloalkoxy groups;
R is isopropyl or cyclopropyl and R
1
is hydrogen, or R and R
1
are methyl, or R and R
1
taken together with the carbon atom to which they are attached form a cyclopropyl ring, provided that when Z is F, R
1
is hydrogen;
Z is hydrogen or F;
R
2
is hydrogen; and
Ar
1
is 3-phenoxyphenyl optionally substituted with any combination of from one to six halogen, C
1
-C
4
alkyl, C
1
-C
4
haloalkyl, C
1
-C
4
alkoxy or C
1
-C
4
haloalkoxy groups.
Another group of more preferred formula I compounds for use in the present invention are 1,4-diaryl-2-fluoro-2-butene compounds wherein
Ar is phenyl optionally substituted with any combination of from one to three halogen, C
1
-C
4
alkyl, C
1
-C
4
haloalkyl, C
1
-C
4
alkoxy or C
1
-C
4
haloalkoxy groups;
R is isopropyl or cyclopropyl and R
1
is hydrogen, or R and R
1
are methyl, or R and R
1
taken together with the carbon atom to which they are attached form a cyclopropyl ring;
Z is hydrogen;
R
2
is hydrogen; and
Ar
1
is 3-phenoxyphenyl optionally substituted with any combination of from one to six halogen, C
1
-C
4
alkyl, C
1
-C
4
haloalkyl, C
1
-C
4
alkoxy or C
1
-C
4
haloalko
Heaney Kathleen
Schwinghammer Kurt
Watson David Wesley
American Cyanamid Company
Mazzarese Joseph M.
Weddington Kevin E.
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