Synergistic insecticidal compositions

Details Synergistic insecticidal compositions Synergistic insecticidal compositions

2002-01-29

2003-10-07

Qazi, Sabiha (Department: 1616)

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

Heterocyclic carbon compounds containing a hetero ring...

C514S228800, C514S229200, C514S229500, C514S229800, C424S405000

Reexamination Certificate

active

06630465

ABSTRACT:

BACKGROUND OF THE INVENTION
Although insecticidal agents and compositions have been developed to control insect pests such as agrohorticultural pests or hygienic pests, and in practice have been used as a single or a mixed agent, economically efficient and ecologically safe insect control compositions are still being sought. Insecticidal compositions which allow for reduced effective dosage rates, increased environmental safety and lower the incidence of insect resistance are highly desirable. The rotational application of insect control agents having different modes of action may be adopted for good pest management practice, however, this approach does not necessarily give satisfactory insect control. Combinations of insect control agents have been studied, however, a high synergistic action has not always been found. Obtaining an insecticidal composition which demonstrates no cross-resistance to existing insecticidal agents, no toxicity problems and little negative impact on the environment is extremely difficult.
Therefore, it is an object of this invention to provide a synergistic insecticidal composition which demonstrates a high controlling effect with concomittant reduced crop production cost and reduced environmental load.
It is another object of this invention to provide methods for synergistic insect control and enhanced crop protection.
SUMMARY OF THE INVENTION
The present invention provides a synergistic insecticidal composition comprising as essential active ingredients a synergistically effective amount of a neuronal sodium channel antagonist and an arylpyrrole insecticide.
The present invention also provides a method for synergistic insect control which comprises contacting said insect with a synergistically effective amount of a combination of a neuronal sodium channel antagonist and an arylpyrrole insecticide.
The present invention further provides a method for the enhanced protection of plants from infestation and attack by insects.
DETAILED DESCRIPTION OF THE INVENTION
When two or more substances in combination demonstrate unexpectedly high biological activity, for example, insecticidal activity, the resulting phenomenon may be referred to as synergism. The mechanism of synergism is not fully understood, and quite possibly may differ with different combinations. However, the term synergism, as used in this application designates a cooperative action encountered in a combination of two or more biologically active components in which the combined activity of the two or more components exceeds the sum of the activity of each component alone.
Surprisingly, it has now been found that a composition which comprises a combination of a neuronal sodium channel antagonist and an arylpyrrole insecticide provides superior insect control at lower levels of the combined active agents than may be achieved when the neuronal sodium channel antagonist or the arylpyrrole insecticide is applied alone.
As used in this application, the term neuronal sodium channel antagonist designates a compound which is capable of preventing the ability of a neuron cell to transfer sodium ions across the cell membrane. A neuron cell thus affected is unable to fire, resulting in paralysis, and ultimately mortality, in the target host. Descriptions of neuronal sodium channel antagonists and their mode of action may be found in Pesticide Biochemistry and Physiology, 60: 177-185 or Archives of Insect Biochemistry and Physiology, 37: 91-103, both of which are hereby incorporated by reference.
Neuronal sodium channel antagonists include compounds such as those described in U.S. Pat. Nos. 5,543,573; 5,708,170; 5,324,837 and 5,462,938, among other publications. Exemplary of the neuronal sodium channel antagonist compounds useful in the composition of this invention are those compounds having the structural formula
wherein
A is CR
4
R
5
or NR
6
;
W is O or S;
X, Y, Z, X′, Y′ and Z′ are each independently H; halogen; OH; CN; NO
2
; C
1
-C
6
alkyl optionally substituted with one or more halogen, C
1
-C
3
alkoxy, C
1
-C
3
haloalkoxy, C
3
-C
6
cycloalkyl, C
2
-C
6
alkenyloxy or sulfonyloxy groups;
C
1
-C
6
alkoxy optionally substituted with one or more halogen, C
1
-C
3
alkoxy or C
3
-C
6
cycloalkyl groups;
C
1
-C
6
alkoxycarbonyl, C
3
-C
6
cycloalkylcarbonyloxy, phenyl optionally substituted with one or more halogen, C
1
-C
4
alkyl, or C
1
-C
4
alkoxy groups;
aminocarbonyloxy optionally substituted with one or more C
1
-C
3
alkyl groups;
C
1
-C
6
alkoxycarbonyloxy; C
1
-C
6
alkylsulfonyloxy;
C
2
-C
6
alkenyl; or NR
12
R
13
;
m, p and q are each independently an integer of 1, 2, 3, 4, or 5;
n is an integer of 0, 1 or 2;
r is an integer of 1 or 2;
t is an integer of 1, 2, 3 or 4;
R, R
1
, R
2
, R
3
, R
4
and R
5
are each independently H or C
1
-C
4
alkyl;
R
6
is H, C
1
-C
6
alkyl, C
1
-C
6
haloalkyl, C
1
-C
6
alkoxyalkyl, C
1
-C
6
alkoxy, C
1
-C
6
haloalkoxy, C
2
-C
6
alkenyl, C
2
-C
6
alkynyl, C
1
-C
6
alkylcarbonyl, C
1
-C
6
alkoxycarbonyl, C
1
-C
6
alkylthio, or C
1
-C
6
haloalkylthio;
R
7
and R
8
are each independently H; halogen; C
1
-C
6
alkyl; C
1
-C
6
alkylcarbonyloxy; or phenyl optionally substituted with one or more halogen, CN, NO
2
, C
1
-C
6
alkyl, C
2
-C
6
haloalkyl, C
1
-C
6
alkoxy or C
1
-C
6
haloalkoxy groups;
R
9
and R
10
are each independently H, or C
1
-C
4
alkyl;
R
11
is H, C
1
-C
6
alkyl, C
1
-C
6
haloalkyl, C
1
-C
4
alkylcarbonyl, C
1
-C
6
alkoxycarbonyl, or C
1
-C
6
haloalkoxycarbonyl;
R
12
and R
13
are each independently H or C
1
-C
6
alkyl;
G is H; C
1
-C
6
alkyl optionally substituted with one or more halogen, C
1
-C
4
alkoxy, C
1
-C
6
haloalkoxy, CN, NO
2
S(O)
u
R
14
, COR
15
, CO
2
R
16
, phenyl or C
3
-C
6
cycloalkyl groups;
C
1
-C
6
alkoxy; C
1
-C
6
haloalkoxy; CN; NO
2
; S(O)
u
R
17
; COR
18
; CO
2
R
19
; phenyl optionally substituted with one or more halogen, CN, C
1
-C
3
haloalkyl, or C
1
-C
3
haloalkoxy groups;
C
3
-C
6
cycloalkyl; or phenylthio;
Q is phenyl optionally substituted with one or more halogen, CN, SCN, NO
2
, S(O)
u
R
20
, C
1
-C
4
alkyl, C
1
-C
4
haloalkyl, C
1
-C
4
alkoxyalkyl, C
1
-C
6
alkoxy, C
1
-C
6
haloalkoxy, or NR
21
R
22
groups;
u is an integer of 0, 1 or 2;
R
14
, R
15
, R
16
, R
18
, R
19
, R
21
and R
22
are each independently H or C
1
-C
6
alkyl;
R
17
and R
20
are each independently C
1
-C
6
alkyl or C
1
-C
6
haloalkyl;
R
33
is CO
2
R
34
;
R
34
is H, C
1
-C
6
alkyl, C
1
-C
6
haloalkyl, phenyl or halophenyl; and the dotted line configuration
represents a double bond or a single bond (i.e. C—N or C═N); or
a stereoisomer thereof.
Preferred neuronal sodium channel antagonists suitable for use in the composition of the invention are those compounds of formula I, II or III wherein the dotted line configuration
represents a double bond.
More preferred neuronal sodium channel antagonists suitable for use in the inventive composition are those compounds of formula I or formula III wherein the dotted line configuration represents a double bond.
Particularly preferred neuronal sodium channel antagonists useful in the composition of the invention are those compounds of formula I or formula III wherein W is O; X is trifluoromethoxy and is in the 4-position; Y is trifluoromethyl and is in the 3-position; Z is CN and is in the 4-position; A is CH
2
; n is 0; m, p and q are each 1; R and R
1
are each H; Z′ is Cl; R
33
and G are each CO
2
CH
3
; Q is p-(trifluoromethoxy)phenyl; and the dotted line configuration
represents a double bond; or a stereoisomer thereof.
Further neuronal sodium channel antagonist compounds include those described in U.S. Pat. Nos. 5,116,850 and 5,304,573, among other publications. Exemplary of further neuronal sodium channel antagonist compounds suitable for use in the composition of the invention are those compounds having structural formula
wherein
W is O or S;
X″ and Y″ are each independently H; halogen; CN; SCN; C
1
-C
6
alkyl optionally substituted with one or more halogen, NO
2
, CN, C
1
-C
4
alkoxy, C
1
-C
4
alkylthio, phenyl, halophenyl, C
1
-C
4
alkylsulfonyl, C
1

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