Organic compounds -- part of the class 532-570 series – Organic compounds – Nitrogen attached directly or indirectly to the purine ring...
Reexamination Certificate
2001-08-29
2004-06-22
Nazario-Gonzalez, Porfirio (Department: 1621)
Organic compounds -- part of the class 532-570 series
Organic compounds
Nitrogen attached directly or indirectly to the purine ring...
C546S206000, C549S443000, C564S299000, C564S308000, C564S341000, C564S347000, C514S277000, C514S278000, C514S649000, C514S657000
Reexamination Certificate
active
06753429
ABSTRACT:
FIELD OF THE INVENTION
The present invention relates to methods for controlling insects. In particular, it relates to control by the application of certain novel substituted benzenes.
BACKGROUND OF THE INVENTION
The present invention relates to methods for controlling insects. In particular, it relates to control by the application of certain novel substituted benzenes. More particularly, it pertains to 1,4-disubstituted benzene compounds and compositions containing the same which are useful for controlling insects in agricultural crops. Even more particularly, this invention relates 1,4-disubstituted benzene compounds and compositions and their uses as insecticides against a variety of insects, including larvae, such as tobacco budworm.
SUMMARY OF THE INVENTION
It has now been found that certain substituted benzenes, particularly 1,4-disubstituted benzenes, and their agriculturally acceptable salts, are effective as insecticides. These benzenes may be represented by the following formula I:
in which:
A is hydrogen; aryl; alkylheterocyclyl; alkenylaminopolycyclyl; alkenylaminoheterocyclyl; alkylaminopolycyclyl; carbonylaminopolycyclyl; and Formula III, where Formula III is
—(CH
2
)
n
—U—R
2
III
where
n is 0 or 1;
U is —CH
2
—, —O—CH
2
—, oxygen, sulfur, sulfonyl, alkyl, oxyalkyloxy, alkenylamino, cabonylamino and —NR
5
, where R
5
is hydrogen, hydroxy, alkyl, haloalkyl, sulfonylalkyl, cabonylamino, and carbonylalkyl;
R
2
is aryl; alkylpolycyclyl; heterocyclyl; polycyclyl; 1-R
3
; 1-R
4
; and 2-R
4
, where:
R
3
is
where
J, L, and W are independently hydrogen, halogen, cyano, nitro, amino, carboxyl, alkyl, haloalkyl, alkenyl, alkoxy, haloalkoxy, aminoalkoxy, nitrilyl, carbonyl, alkylcarbonyl, haloalkylcarbonyl, alkoxycarbonyl, haloalkoxycarbonyl, aryl, aryloxy, and heterocyclyl;
R
4
is
where
X, Y, and Z are independently hydrogen, halogen, cyano, nitro, amino, azido, carboxyl, alkyl, alkynyl, haloalkyl, haloalkylthio, nitrilyl, alkenyl, alkoxy, haloalkoxy, carbonyl, alkylcarbonyl, haloalkylcarbonyl, alkoxycarbonyl, haloalkoxycarbonyl, phenyl, aryl, aryloxy, and heterocyclyl;
B and D are independently hydrogen, halogen, alkyl, haloalkyl, alkoxy, haloalkoxy, alkoxyaminoalkyl, 2-(Formula III), 3-(Formula III), 5-(Formula III), and 6-(Formula III), where Formula III, n, U, R
2
, R
3
, R
4
, R
5
, J, L, W, X, Y, and Z are as defined above;
R is —T—(CH
2
)
m
—R
1
, —N(R
6
)(R
7
) or heterocyclyl;
T is —CH
2
—, carbonyl, oxygen, nitrogen, and sulfur;
m is 0, 1, 2, 3, or 4;
R
1
is —N(R
8
)(R
9
); alkyl; aryl; —C(O)N(R
12
)(R
13
); oxyalkyl; haloalkyl; heterocyclyl; cycloalkyl; —N(O)(R
14
)(R
15
); —P(O)(R
14
)(R
15
); —P(S)(R
14
)(R
15
); alkylamino, where the cyclohexyl, aryl and heterocyclyl moieties may be optionally substituted with halogen, hydroxy, alkyl, haloalkyl, alkoxy, haloalkoxy, alkoxycarbonyl, aryl, arylcarbonyl, alkylamino; where
R
6
, R
7
, R
8
, R
9
, R
12
, R
13
, R
14
and R
15
are independently hydrogen, alkyl, alkoxy, alkylthio, acetyl, alkoxycarbonyl, alkoxyalkyl, aminoalkyl, carbonylamino, and —(CH
2
)
p
—N(R
16
)(R
17
), where
p is 1 or 2; and
R
16
and R
17
are independently hydrogen, alkyl, alkoxy, alkoxyalkyl, and aminoalkyl.
The present invention is also directed to a composition containing an insecticidally effective amount of a compound of Formula I in admixture with at least one agriculturally acceptable extender or adjuvant, wherein A, B, D, and R are as defined above.
In addition, the present invention relates to a method of controlling insects that comprises applying to locus on crops, such as cotton, vegetables, fruits, where control is desired an insecticidally effective amount of a the above composition.
DETAILED DESCRIPTION OF THE INVENTION
In one aspect of the present invention, certain substituted benzenes, particularly 1,4-disubstituted benzenes, and the agriculturally acceptable salts thereof, have now been found to be effective as insecticides. These benzenes may be represented by the following formula I:
in which:
A is selected from the group consisting of hydrogen; aryl; alkylheterocyclyl; alkenylaminopolycyclyl; alkenylaminoheterocyclyl; alkylaminopolycyclyl; carbonylaminopolycyclyl; where the aryl, heterocyclyl and polycyclyl moieties are optionally substituted with one or more of the following: halogen, cyano, nitro, amino, carboxyl, alkyl, haloalkyl, alkoxy, haloalkoxy, carbonyl, alkylcarbonyl, haloalkylcarbonyl, alkoxycarbonyl, haloalkoxycarbonyl, or aryl; and Formula III, where Formula III is
—(CH
2
)
n
—U—R
2
III
wherein
n is 0 or 1;
U is selected from the group consisting of —CH
2
—, —O—CH
2
—, oxygen, sulfur, sulfonyl, alkyl, oxyalkyloxy, alkenylamino, cabonylamino and —NR
5
, where R
5
is selected from the group consisting of hydrogen, hydroxy, alkyl, haloalkyl, sulfonylalkyl, cabonylamino, and carbonylalkyl;
R
2
is selected from aryl; alkylpolycyclyl; heterocyclyl; polycyclyl; where the aryl, heterocyclyl and polycyclyl moieties are optionally substituted with one or more of the following: halogen, cyano, nitro, amino, carboxyl, alkyl, haloalkyl, alkoxy, haloalkoxy, carbonyl, alkylcarbonyl, haloalkylcarbonyl, alkoxycarbonyl, haloalkoxycarbonyl, or aryl; 1-R
3
; 1-R
4
; and 2-R
4
, wherein:
R
3
is
where
J, L, and W are independently selected from the group consisting of hydrogen, halogen, cyano, nitro, amino, carboxyl, alkyl, haloalkyl, alkenyl, alkoxy, haloalkoxy, aminoalkoxy, nitrilyl, carbonyl, alkylcarbonyl, haloalkylcarbonyl, alkoxycarbonyl, haloalkoxycarbonyl, aryl, aryloxy, and heterocyclyl, where the aryl and heterocyclyl moieties may be optionally substituted with halogen, alkyl, haloalkyl, alkoxy, or haloalkoxy;
R
4
is
where
X, Y, and Z are independently selected from the group consisting of hydrogen, halogen, cyano, nitro, amino, azido, carboxyl, alkyl, alkynyl, haloalkyl, haloalkylthio, nitrilyl, alkenyl, alkoxy, haloalkoxy, carbonyl, alkylcarbonyl, haloalkylcarbonyl, alkoxycarbonyl, haloalkoxycarbonyl, phenyl, aryl, aryloxy, and heterocyclyl, where the phenyl, aryl, and heterocyclyl moieties may be optionally substituted with halogen, haloalkyl, haloalkyl, alkoxy, or haloalkoxy;
B and D are independently selected from hydrogen, halogen, alkyl, haloalkyl, alkoxy, haloalkoxy, alkoxyaminoalkyl, 2-(Formula III), 3-(Formula III), 5-(Formula III), and 6-(Formula III), wherein Formula III, n, U, R
2
, R
3
, R
4
, R
5
, J, L, W, X, Y, and Z are as defined above;
R is —T—(CH
2
)
m
—R
1
, —N(R
6
)(R
7
) or heterocyclyl, where
the heterocyclyl moiety may be optionally substituted with halogen, hydroxy, alkyl, haloalkyl, alkoxy, haloalkoxy, alkoxycarbonyl, aryl, alkylaza, arylcarbonyl, benzyl, allyl, propargyl, alkylamino; where the aryl moiety may be optionally substituted with halogen, hydroxy, alkyl, haloalkyl, alkoxy, haloalkoxy, alkoxycarbonyl, aryl, arylcarbonyl
T is selected from the group consisting of —CH
2
—, carbonyl, oxygen, nitrogen, and sulfur;
m is 0, 1, 2, 3, or 4;
R
1
is selected from the group consisting of —N(R
8
)(R
9
); alkyl; aryl; —C(O)N(R
12
)(R
13
); oxyalkyl; haloalkyl; heterocyclyl; cycloalkyl; —N(O)(R
14
)(R
15
); —P(O)(R
14
)(R
15
); —P(S)(R
14
)(R
15
); alkylamino, where the cycloalkyl, aryl and heterocyclyl moieties may be optionally substituted with halogen, hydroxy, alkyl, haloalkyl, alkoxy, haloalkoxy, alkoxycarbonyl, aryl, arylcarbonyl, alkylamino; where
R
6
, R
7
, R
8
, R
9
, R
12
, R
13
, R
14
and R
15
are independently selected from the group consisting of hydrogen, alkyl, alkoxy, alkylthio, acetyl, alkoxycarbonyl, alkoxyalkyl, aminoalkyl, carbonylamino, and —(CH
2
)
p
—N(R
16
)(R
17
), where
p is 1 or 2;
R
16
and R
17
are independently selected from the group consisting of hydrogen, alkyl, alkoxy, alkoxyalkyl, and aminoalkyl.
Agriculturally acceptable salts of the 1,4-disubstituted benzenes include, but are not limited to, for example, the salts of hydrochloric acid, sulfonic acid, ethanesulfonic acid, trifluoroacetic acid, methylbenzenesulfonic acid, phosphoric acid, gluconic, acid, and pamoic acid.
Some preferred compounds are those in wh
Ali Syed F.
Barron Edward
Cohen Daniel H.
Crawford Ellen M.
Cullen Thomas G.
FMC Corporation
FMC Corporation
Nazario-Gonzalez Porfirio
Zucker Paul A.
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