Plant protecting and regulating compositions – Plant growth regulating compositions – Organic active compound containing
Reexamination Certificate
1998-11-11
2001-09-11
Padmanabhan, Sreeni (Department: 1621)
Plant protecting and regulating compositions
Plant growth regulating compositions
Organic active compound containing
C568S639000, C568S635000, C568S637000, C568S638000, C504S351000, C570S128000, C514S717000, C514S718000, C514S720000, C514S721000
Reexamination Certificate
active
06288011
ABSTRACT:
BACKGROUND OF THE INVENTION
Insect and acarid pests destroy growing and harvested crops. In the United States, agronomic crops must compete with thousands of those pests. In particular tobacco budworms, southern armyworms and corn rootworms are especially devastating to crops. In spite of the commercial insecticides and acaricides available today, damage to crops, both growing and harvested, caused by insect and acarid pests still occurs. Accordingly, there is ongoing research to create new and more effective insecticidal and acaricidal agents.
Certain fluoroolefin compounds are known to possess insecticidal and acaricidal activity (see, e.g., U.S. Pat. No. 5,248,834; GB 2,288,803-A; WO 94/06741; WO 97/16067 and co-pending U.S. patent application Ser. No. 08/865,244 filed on May 29, 1997. However, the fluoroolefin compounds disclosed in those patents and patent applications are outside the scope of the present invention. U.S. Pat. No. 5,248,834 generically discloses certain 1-aryl-1-(3-aryl-1,2-difluoroprop-1-enyl)cyclopropane compounds. However, that patent does not provide a method to prepare those compounds. In fact, U.S. Pat. No. 5,248,834 does not provide a method to prepare any fluoroolefin compounds.
It is, therefore, an object of the present invention to provide compounds which are highly effective for the control of insect and acarid pests.
It is also an object of the present invention to provide a method for the control of insect and acarid pests.
It is a further object of this invention to provide a method for the protection of growing and harvested crops from damage caused by insect and acarid attack and infestation.
Those 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 comprises 1,4-diaryl-2,3-difluoro-2-butene compounds which are useful as insecticidal and acaricidal agents. Those compounds are also useful for protecting plants from damage caused by insect and acarid attack and infestation.
The 1,4-diaryl-2,3-difluoro-2-butene compounds of the present invention have 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, C
1
-C
4
haloalkoxy or hydroxy 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 is hydrogen, C
1
-C
4
alkyl, C
1
-C
4
haloalkyl, C
3
-C
6
cycloalkyl or C
3
-C
6
halocycloalkyl;
R
1
is hydrogen, F, Cl, Br, cyano or OR
2
;
R
2
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 comprises compositions containing those compounds and methods for using those compounds and compositions. Advantageously, it has been found that the 1,4-diaryl-2,3-difluoro-2-butene compounds of the present invention, and compositions containing them, are useful for the control of insect and acarid pests. The compounds of this invention are also useful for the protection of plants from damage caused by insect and acarid attack and infestation.
DETAILED DESCRIPTION OF THE INVENTION
The present invention provides a method for the control of insect or acarid pests which comprises contacting said pests or their food supply, habitat or breeding grounds with a pesticidally effective amount of a 1,4-diaryl-2,3-difluoro-2-butene compound of formula I.
The present invention also provides a method for the protection of growing plants from attack or infestation by insect or acarid pests which comprises applying to the foliage of the plants, or to the soil or water in which they are growing, a pesticidally effective amount of a 1,4-diaryl-2,3-difluoro-2-butene compound of formula I.
The 1,4-diaryl-2,3-difluoro-2-butene compounds of the present invention have the structural formula I
wherein Ar, Ar
1
, R and R
1
are as described hereinabove for formula I.
In formula I above, 5- and 6-membered heteroaromatic rings include, but are not limited to, pyridyl, pyrazolyl, imidazolyl, triazolyl, isoxazolyl, tetrazolyl, pyrazinyl, pyridazinyl, triazinyl, furanyl, thienyl and thiazolyl rings each optionally substituted as described in formula I above.
Exemplary of halogen hereinabove are fluorine, chlorine, bromine and iodine. The terms “C
1
-C
4
haloalkyl”, “C
3
-C
6
halocycloalkyl” and “C
1
-C
4
haloalkoxy” are defined as a C
1
-C
4
alkyl group, a C
3
-C
6
cycloalkyl group and a C
1
-C
4
alkoxy group substituted with one or more halogen atoms, respectively.
Preferred formula I pesticidal agents 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 is C
1
-C
4
alkyl, C
1
-C
4
haloalkyl, C
3
-C
6
cycloalkyl or C
3
-C
6
halocycloalkyl;
R
1
is hydrogen, F, Cl, Br, cyano or OR
2
;
R
2
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 1,4-diaryl-2,3-difluoro-2-butene compounds 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 is isopropyl, trifluoromethyl or cyclopropyl;
R
1
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.
Most preferred insecticidal and acaricidal agents of the present 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
hal
Barnes Keith Douglas
Bentley Terence James
American Cyanamid Co.
Maurer Barbara V.
Mazzarese Joseph M.
Padmanabhan Sreeni
Parsa J.
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