Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Reexamination Certificate
1999-11-05
2001-05-22
Gerstl, Robert (Department: 1613)
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
C514S364000, C548S136000, C548S143000
Reexamination Certificate
active
06235762
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 and southern armyworms are especially devastating to crops.
Tobacco budworms cause tremendous economic losses in agronomic crops. In particular, budworms devastate cotton crops by feeding on green bolls. Control of budworms is complicated by their resistance to many common insecticides, including organophosphates, carbamates and pyrethroids.
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 N-carbamoyl-3-carboxyaryl-heterocyclic and hydrazinecarboximidamidohydrazone compounds which are useful as herbicidal agents are described in U.S. Pat. No. 5,670,456. However, that patent does not describe any insecticidal or acaricidal activity.
Certain cyclic 1,3,4-oxadiazoline compounds are described by D. Kochetov et al in Ukrainskii Khimicheskii Zhurnal, 57(2), pp. 215-217 (1991). However, D. Kochetov et al do not disclose any utility for their cyclic 1,3,4-oxadiazoline compounds
It is, therefore, an object of the present invention to provide compounds which are useful 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.
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 comprises 2-aryl-&Dgr;
2
-1,3,4-(oxa and thia)diazoline compounds which are useful for the control of insect and acarid pests. Those compounds are also useful for protecting plants from damage caused by insect and acarid attack and infestation.
The pesticidal 2-aryl-&Dgr;
2
-1,3,4-(oxa and thia)diazoline compounds of the present invention have the structural formula I
wherein
X is 0 or S(O)
m
;
Z is
C(X
1
)R
5
, C
1
-C
6
alkyl, C
1
-C
6
haloalkyl,
benzyl optionally substituted on the phenyl ring with any combination of from one to three halogen, C
1
-C
6
alkyl, C
1
-C
6
haloalkyl, C
1
-C
6
alkoxy, C
1
-C
6
haloalkoxy, C
1
-C
6
alkylthio or C
1
-C
6
haloalkyl-thio groups, or
phenyl optionally substituted with any combination of from one to three halogen, C
1
-C
6
alkyl, C
1
-C
6
haloalkyl, C
1
-C
6
alkoxy, C
1
-C
6
haloalkoxy, C
1
-C
6
alkylthio or C
1
-C
6
haloalkylthio groups,
provided that when X is O, Z is
n and p are each independently 0, 1, 2 or 3;
X
1
is O or S;
R and R
4
are each independently halogen, C
1
-C
6
alkyl, C
1
-C
6
haloalkyl, OR
6
, S(O)
q
R
7
, nitro, cyano, NR
8
R
9
, CO
2
R
10
, C(O)R
11
or
phenyl optionally substituted with any combination of from one to three halogen, C
1
-C
6
alkyl, C
1
-C
6
haloalkyl, C
1
-C
6
alkoxy, C
1
-C
6
haloalkoxy, C
1
-C
6
alkylthio or C
1
-C
6
haloalkylthio groups, or
two adjacent R groups or R
4
groups may be taken together to form a ring wherein RR or R
4
R
4
is represented by: —OCH
2
O—, —OCF
2
O— or —CH═CH—CH═CH—;
R
6
and R
7
are each independently hydrogen, C
1
-C
6
alkyl, C
1
-C
6
haloalkyl or
phenyl optionally substituted with any combination of from one to three halogen, C
1
-C
6
alkyl, C
1
-C
6
haloalkyl, C
1
-C
6
alkoxy, C
1
-C
4
haloalkoxy, C
1
-C
6
alkylthio or C
1
-C
6
haloalkylthio groups;
R
8
, R
9
, R
13
and R
14
are each independently hydrogen, C
1
-C
6
alkyl, C
1
-C
6
alkylcarbonyl or
phenyl optionally substituted with any combination of from one to three halogen, C
1
-C
6
alkyl, C
1
-C
6
haloalkyl, C
1
-C
6
alkoxy, C
1
-C
6
haloalkoxy, C
1
-C
6
alkylthio or C
1
-C
6
haloalkylthio groups;
R
10
and R
11
are each independently hydrogen, C
1
-C
6
alkyl or C
1
-C
6
haloalkyl;
R
1
and R
2
are each independently hydrogen, C
3
-C
7
cycloalkyl, C
1
-C
6
haloalkyl, C
3
-C
6
alkenyl, C
3
-C
6
haloalkenyl, C
3
-C
6
alkynyl, C
3
-C
6
haloalkynyl, C
2
-C
6
alkoxyalkyl, (CH
2
)
v
C(O)R
12
,
C
1
-C
6
alkyl optionally substituted with one phenoxy or phenyl group wherein the phenyl ring of each group is independently, optionally substituted with from one to three halogen, C
1
-C
6
alkyl, C
1
-C
6
haloalkyl, C
1
-C
6
alkoxy, C
1
-C
6
haloalkoxy, C
1
-C
6
alkylthio or C
1
-C
6
haloalkylthio groups,
phenyl optionally substituted with from one to three halogen, C
1
-C
6
alkyl, C
1
-C
6
haloalkyl, C
1
-C
6
alkoxy, C
1
-C
6
haloalkoxy, C
1
-C
6
alkylthio or C
1
-C
6
haloalkylthio groups, or
a 5- or 6-membered heteroaromatic ring optionally substituted with any combination of from one to three halogen, C
1
-C
6
alkyl, C
1
-C
6
haloalkyl, C
1
-C
6
alkoxy, C
1
-C
6
haloalkoxy, C
1
-C
6
alkylthio or C
1
-C
6
haloalkylthio groups, and
when R
1
and R
2
are taken together with the atom to which they are attached they may form a C
3
-C
6
cycloalkyl ring wherein R
1
R
2
is represented by: —(CH
2
)
t
— where t is 2, 3, 4 or 5;
m, q and v are each independently 0, 1 or 2;
R
12
is hydrogen, C
1
-C
6
alkyl, C
1
-C
6
haloalkyl, C
1
-C
6
alkoxy, C
1
-C
6
haloalkoxy, C
1
-C
6
alkylthio, C
1
-C
6
haloalkylthio or NR
13
R
14
;
R
3
is hydrogen, C
1
-C
6
alkyl, C
1
-C
6
haloalkyl or C(O)R
15
;
R
15
is C
1
-C
6
alkyl, C
1
-C
6
haloalkyl, C
1
-C
6
alkoxy or C
1
-C
6
haloalkoxy; and
R
5
is C
1
-C
6
alkyl,
phenyl optionally substituted with any combination of from one to three halogen, C
1
-C
6
alkyl, C
1
-C
6
haloalkyl, C
1
-C
6
alkoxy, C
1
-C
6
haloalkoxy, C
1
-C
6
alkylthio or C
1
-C
6
haloalkylthio groups, or
benzyl optionally substituted on the phenyl ring with any combination of from one to three halogen, C
1
-C
6
alkyl, C
1
-C
6
haloalkyl, C
1
-C
6
alkoxy, C
1
-C
6
haloalkoxy, C
1
-C
6
alkylthio or C
1
-C
6
haloalkylthio groups; and
the optical isomers thereof and the agriculturally acceptable salts thereof.
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 2-aryl-&Dgr;
2
-1,3,4-(oxa or thia)diazoline 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 2-aryl-&Dgr;
2
-1,3,4-(oxa or thia)diazoline compound of formula I
The pesticidal 2-aryl-&Dgr;
2
-1,3,4-(oxa and thia)diazoline compounds of the present invention have the structural formula I
wherein n, R, R
1
, R
2
, X and Z are as described hereinabove for formula I.
Preferred 2-aryl-&Dgr;
2
-1,3,4-oxadiazoline compounds of the present invention are those having the structural formula II
wherein
R is halogen, C
1
-C
4
haloalkyl, C
1
-C
4
haloalkoxy or
phenoxy 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
4
is C
1
-C
4
haloalkyl, C
1
-C
4
haloalkoxy or C
1
-C
4
haloalkylthio;
R
1
is C
1
-C
4
alkyl;
R
2
is C
1
-C
4
alkyl, C
1
-C
4
haloalkyl, (CH
2
)
v
C(O)R
12
or
2-pyridyl 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;
v is 0 or 1;
R
12
is C
1
-C
4
alkoxy or C
1
-C
4
haloalkoxy;
R
3
is hydrogen or C(O)R
15
; and
R
15
is C
1
-C
4
alkoxy.
More preferred insecticidal and acaricidal agents of the present invention are those having the structural formula II wherein
R is F, Br, Cl or phenoxy;
R
4
is CF
3
, OCF
3
or SCF
3
;
R
1
is CH
3
;
R
2
is CH
3
, CH
2
Cl, CH
2
CF
3
, CF
3
, CH
2
CO
2
CH
3
or 2-pyridyl; and
R
3
is hydro
Buckwalter Brian Lee
Takasugi James Jan
American Cyanamid Company
Costello Charles F.
Gerstl Robert
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