Pesticidal and parasiticidal use of 1-aryl-1-(substituted...

Details Pesticidal and parasiticidal use of 1-aryl-1-(substituted... Pesticidal and parasiticidal use of 1-aryl-1-(substituted...

2001-08-01

2002-11-19

Seaman, D. Margaret (Department: 1625)

Organic compounds -- part of the class 532-570 series

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

C549S444000, C504S296000

Reexamination Certificate

active

06482962

ABSTRACT:

BACKGROUND OF THE INVENTION
Nematode, insect and acarid pests destroy growing and harvested crops. In the United States, agronomic crops must compete with thousands of those pests. In addition, helminth parasites cause hundreds of millions of dollars in economic damage to the livestock and companion animal sectors annually on a global basis.
In spite of the commercial pesticides and parasiticides available today, damage to crops, livestock, companion animals and humans still occurs. Accordingly, there is ongoing research to create new and more effective pesticides and parasiticides.
Certain &bgr;-nitrophenethyl derivatives which are useful as fungicidal agents are described in JP 62039563. However, that application does not describe or suggest any nematicidal, insecticidal and acaricidal utility for the &bgr;-nitrophenethyl derivatives described therein.
It is, therefore, an object of the present invention to provide a method for the control of helminth, nematode, insect and acarid pests and parasites.
It is also an object of the present invention to provide a method for the protection of growing and harvested crops from damage caused by nematode, insect and acarid attack and infestation.
It is a further object of this invention to provide a method for treating, controlling, preventing and protecting warm-blooded animals, fish and humans against infestation and infection by helminths.
These and other objects of the present invention will become more apparent from the description thereof set forth below.
SUMMARY OF THE INVENTION
The present invention provides a method for the control of helminth, nematode, insect or acarid pests or parasites which comprises contacting said pests or parasites or their food supply, habitat or breeding grounds with a pesticidally or parasiticidally effective amount of a 1-aryl-1-(substituted thio, sulfinyl or sulfonyl)-2-nitroethane compound having the structural formula I
wherein
Ar is phenyl optionally substituted with any combination of one to five halogen atoms, one or two cyano groups, one or two nitro groups, one to three C
1
-C
4
alkyl groups, one to three C
1
-C
4
haloalkyl groups, one to three C
1
-C
4
alkoxy groups, one to three C
1
-C
4
haloalkoxy groups, one to three C
1
-C
4
alkylthio groups, one to three C
1
-C
4
haloalkylthio groups, one benzylthio group or one SCH
2
CO
2
R
2
group,
1- or 2-naphthyl optionally substituted with any combination of one to five halogen atoms, one or two cyano groups, one or two nitro groups, one to three C
1
-C
4
alkyl groups, one to three C
1
-C
4
haloalkyl groups, one to three C
1
-C
4
alkoxy groups, one to three C
1
-C
4
haloalkoxy groups, one to three C
1
-C
4
alkylthio groups or one to three C
1
-C
4
haloalkylthio groups,
piperonyl optionally substituted with any combination of one to three halogen atoms, one or two cyano groups, one or two nitro groups, one to three C
1
-C
4
alkyl groups, one to three C
1
-C
4
haloalkyl groups, one to three C
1
-C
4
alkoxy groups, one to three C
1
-C
4
haloalkoxy groups, one to three C
1
-C
4
alkylthio groups or one to three C
1
-C
4
haloalkylthio groups,
2-, 3- or 4-pyridyl optionally substituted with any combination of one to four halogen atoms, one or two cyano groups, one or two nitro groups, one to three C
1
-C
4
alkyl groups, one to three C
1
-C
4
haloalkyl groups, one to three C
1
-C
4
alkoxy groups, one to three C
1
-C
4
haloalkoxy groups, one to three C
1
-C
4
alkylthio groups or one to three C
1
-C
4
haloalkylthio groups,
2- or 3-furyl optionally substituted with any combination of one to three halogen atoms, one or two cyano groups, one or two nitro groups, one to three C
1
-C
4
alkyl groups, one to three C
1
-C
4
haloalkyl groups, one to three C
1
-C
4
alkoxy groups, one to three C
1
-C
4
haloalkoxy groups, one to three C
1
-C
4
alkylthio groups or one to three C
1
-C
4
haloalkylthio groups, or
2- or 3-thienyl optionally substituted with any combination of one to three halogen atoms, one or two cyano groups, one or two nitro groups, one to three C
1
-C
4
alkyl groups, one to three C
1
-C
4
haloalkyl groups, one to three C
1
-C
4
alkoxy groups, one to three C
1
-C
4
haloalkoxy groups, one to three C
1
-C
4
alkylthio groups or one to three C
1
-C
4
haloalkylthio groups;
R is hydrogen, CO
2
R
3
, C(O)NR
4
R
5
, (CH
2
)
n
CR
2
(NR
4
R
5
)CO
2
R
3
, CH(OR
6
)CH
2
OR
7
, CH(CH
2
OR
8
)SCH(R
9
)CH
2
NO
2
, C
1
-C
4
alkyl, C
1
-C
4
haloalkyl, C
2
-C
4
alkenyl, C
2
-C
4
haloalkenyl,
phenyl optionally substituted with any combination of one to five halogen atoms, one or two cyano groups, one or two nitro groups, one to three C
1
-C
4
alkyl groups, one to three C
1
-C
4
haloalkyl groups, one to three C
1
-C
4
alkoxy groups, one to three C
1
-C
4
haloalkoxy groups, one to three C
1
-C
4
alkylthio groups or one to three C
1
-C
4
haloalkylthio groups,
2- or 3-furyl optionally substituted with any combination of one to three halogen atoms, one or two cyano groups, one or two nitro groups, one to three C
1
-C
4
alkyl groups, one to three C
1
-C
4
haloalkyl groups, one to three C
1
-C
4
alkoxy groups, one to three C
1
-C
4
haloalkoxy groups, one to three C
1
-C
4
alkylthio groups or one to three C
1
-C
4
haloalkylthio groups, or
2- or 3-thienyl optionally substituted with any combination of one to three halogen atoms, one or two cyano groups, one or two nitro groups, one to three C
1
-C
4
alkyl groups, one to three C
1
-C
4
haloalkyl groups, one to three C
1
-C
4
alkoxy groups, one to three C
1
-C
4
haloalkoxy groups, one to three C
1
-C
4
alkylthio groups or one to three C
1
-C
4
haloalkylthio groups;
R
2
, R
6
, R
7
and R
8
are each independently hydrogen or C
1
-C
6
alkyl;
m is 0, 1 or 2;
n is 0 or 1;
R
9
is phenyl optionally substituted with any combination of one to five halogen atoms, one or two cyano groups, one or two nitro groups, one to three C
1
-C
4
alkyl groups, one to three C
1
-C
4
haloalkyl groups, one to three C
1
-C
4
alkoxy groups, one to three C
1
-C
4
haloalkoxy groups, one to three C
1
-C
4
alkylthio groups or one to three C
1
-C
4
haloalkylthio groups;
R
3
is hydrogen, C
1
-C
10
alkyl, CH
2
(C
1
-C
10
haloalkyl), C
3
-C
10
alkenyl, C
3
-C
10
haloalkenyl, a cation,
benzyl optionally substituted on the ring with any combination of one to five halogen atoms, one or two cyano groups, one or two nitro groups, one to three C
1
-C
4
alkyl groups, one to three C
1
-C
4
haloalkyl groups, one to three C
1
-C
4
alkoxy groups, one to three C
1
-C
4
haloalkoxy groups, one to three C
1
-C
4
alkylthio groups or one to three C
1
-C
4
haloalkylthio groups, or
phenyl optionally substituted with any combination of one to five halogen atoms, one or two cyano groups, one or two nitro groups, one to three C
1
-C
4
alkyl groups, one to three C
1
-C
4
haloalkyl groups, one to three C
1
-C
4
alkoxy groups, one to three C
1
-C
4
haloalkoxy groups, one to three C
1
-C
4
alkylthio groups or one to three C
1
-C
4
haloalkylthio groups;
R
4
and R
5
are each independently hydrogen, C
1
-C
10
alkyl, CH
2
(C
1
-C
10
haloalkyl), C
3
-C
10
alkenyl, C
3
-C
10
haloalkenyl,
benzyl optionally substituted on the ring with any combination of one to five halogen atoms, one or two cyano groups, one or two nitro groups, one to three C
1
-C
4
alkyl groups, one to three C
1
-C
4
haloalkyl groups, one to three C
1
-C
4
alkoxy groups, one to three C
1
-C
4
haloalkoxy groups, one to three C
1
-C
4
alkylthio groups or one to three C
1
-C
4
haloalkylthio groups, or
phenyl optionally substituted with any combination of one to five halogen atoms, one or two cyano groups, one or two nitro groups, one to three C
1
-C
4
alkyl groups, one to three C
1
-C
4
haloalkyl groups, one to three C
1
-C
4
alkoxy groups, one to three C
1
-C
4
haloalkoxy groups, one to three C
1
-C
4
alkylthio groups or one to three C
1
-C
4
haloalkylthio groups, and
when R
4
and R
5
are taken together with the atom to which they are attached, they may form a five- or six-membered ring wherein R
4
R
5
is represented by: —(CH
2
)
4
—, —(CH
2
)
5
— or —(CH
2
)
2
O(CH
2
)
2
—; and
R
1
is hydrogen, C
1
-C
4
alkyl or
pheny

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