Title of Invention

SYNERGISTIC INSECTICIDAL COMPOSITIONS

Abstract ABSTRACT IN/PCT/2001/1241/CHE "SYNERGISTIC INSECTICIDAL COMPOSITIONS" The present invention provides a synergistic insecticidal composition comprising as essential active ingredients a neuronal sodium channel antagonist and an arylpyrrole insecticide. Also provided are methods for synergistic insect control and crop protection.
Full Text

SYNERGISTIC INSECTICIDAL COMPOSmONS
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 synergisticaliy effective amount of a neuronal sodium channel antagonist and an aryipyrrole insecticide.
The present invention also provides a method for synergistic insect control which comprises contacting said insect with a synergisticaliy effective amount of a combination of a neuronal sodium channel antagonist and an aryipyrrole 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 tenn "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 aryipyrrole 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 aryipyrrole 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. 5,543,573; U.S. 5,708,170; U.S. 5,324,837 and U.S. 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 CR4R5 or NR,; W is O or S;
X, Y, Z, X', Y and Z' are each independently H; halogen; OH; CN; NO2; C1-C6alkyl optionally substituted with one or more halogen, C1-C3alkoxy, C,-
Cjhaloalkoxy, C3-C6CycloalkyI, C1-Cgaikenyloxy or
sulfonyloxy groups; C1-C6alkoxy optionally substituted with one or more halogen,
C1-C3alkoxy or C3-C6CycloalkyI groups; C1-C6alkoxycarbonyl, C3-C6Cycloalkylcarbonyloxy, phenyl optionally substituted with one or
more halogen, C1-C4alkyl, or C1-C4alkoxy groups; aminocarbonyloxy optionally substituted with one or more
C3-C6salkyl groups; C1-Cealkoxycarbonyloxy; C1-C6alkylsulfonyloxy; C3-C6alkenyl;
orNR12R13; 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, R1, R2, R3, R4 and R5 are each independently H or C1-C4alkyl; R6 Is H, C1-C6alkyI, C1-Cehaloalkyl, C1-C6alkoxyalkyl,
C1-C6alkoxy, C1-C6haloalkoxy,C2-Cealkenyl, C1-Cealkynyl, C1-
Cealkylcarbonyl, C1-C6alkoxycarbonyl, C1-C6alkylthio, or C,-
Cghaloalkylthio; R7 and R8 are each independently H; halogen; C1-C6alkyl; C,-
Cealkylcarbonyloxy; or phenyl optionally substituted with one
or more


halogen, CN, NO2, CrCgalkyl, C1-C6haloalkyl, C,-C6alkoxy or C1-C6haloalkoxy groups; R9 and R10 are each independently H, or C1-C4alkyl; R11 is H, C1-C6aikyl, C1-C6haloalkyI, C1-C4alkylcarbonyl, C,-
C6alkoxycarbonyl, or C1-Cehaloalkoxycarbonyl; R12 and R13 are each independently H or C1-Cgalkyl; G is H; C1-C6alkyl optionally substituted with one or more halogen, C1-C4alkoxy, C1-C6haloalkoxy, CN, N02S(0)„R14, COR15, CO2R16, phenyl or Ca-CeCycloalkyl groups; C1-C6alkoxy; C1-C6haloalkoxy; CN; NO2 S(O)R17, COR18; CO2R19! phenyl optionally substituted
with one or more halogen, CN, C1-Cahaloalkyl, or C1-C6haloalkoxy groups; C3-C6Cycloalkyl; or phenylthio; Q is phenyl optionally substituted with one or more halogen, CN, SCN, NO2, S(0),R2o, C1-C4alkyl, CrC4haloalkyl, C,-C4alkoxyalkyl, C1-C6alkoxy, C1-C6haloalkoxy, or NR21R22 groups; u is an integer of 0,1 or 2; R14, R15, R16. R18. R19. R21 and R22 are each independently H or C1
Cealkyl; R17 and R20 are each independently C1-C6alkyl or
C1-Cehaloalkyl; R33 is CO2R34; R34 is H, C1-Cfialkyl, C1-Cehaioalkyl, phenyl or
halophenyl; and the dotted line configuration c—N 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 fonnula I, II or III wherein the dotted line configuration c—N 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 fonnula I or fonnula 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 CH2; n is 0; m, p and q are each 1; R and R1 are each H; Z' is CI; R33 and G are each CO2CH3; Q is p-(trifluoromethoxy)phenyl; and the dotted line configuration c—N represents a double bond; or a stereoisomer
thereof.
Further neuronal sodium channel antagonist compounds include those described in U.S. 5,116,850 and U.S. 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


more halogen, NO2. CN. C1-C4alkoxy, C1-rC4alkylthio, phenyl, halophenyl, C1-C4alkylsulfonyl, C1-C4haloalkylsulfonyl, or C1-C4aIkoxycarbonyl groups;
C2-C4alkenyl; C2-C4haloalkenyl; C2-C4alkynyl; C1-
C4haloalkynyl; C3-C6CycloalkyI; Ca-CehalocycloalkyI; phenyl
optionally substituted
with one or more halogen, CN, NO2, C1-C4alkyl, C,-C4haloalkyl, C1-C4alkoxy, C1-C4haloalkoxy, C1-C4aIkylthio, C1-C4alkyIsulfonyl or C1-C4haloalkylsulfonyl groups;
C1-C4alkylcarbonyl; C1-C4haIoalkylcarbonyl; or NR28R29; m is an integer of 1, 2, 3,4 or 5;
G' is phenyl optionally substituted with one or more groups which may be the same or different selected from X';
a 5-membered heteroaromatic ring containing one or two heteroatoms selected from 0 or 1 oxygen, 0 or 1 sulfur and 0,1 or 2 nitrogen atoms said 5-membered heteroaromatic ring being attached via carbon and being optionally substituted with one or more groups which may be the same or different selected from X'; or
a 6-membered heteroaromatic ring containing one or two heteroatoms selected from 0 or 1 oxygen, 0 or 1 sulfur and 0,1 or 2 nitrogen atoms said 6-membered heteroaromatic ring being attached via carbon and being optionally substituted with one or more groups which may be the same or different selected from X'; Q' is H; C1-C6alkyl optionally substituted with one or more halogen, CN, C1-C6alkoxy, C1-C6alkoxycarbonyl, or phenyl optionally

substituted with one or more halogen, CN, NO2, C1-C4alkyl, C,-C4haloalkyl, C,-C4alkylsulfonyl or C1-C4alkylsulfinyl groups; C1-C6alltenyl; C1-C6alkynyl; or phenyl optionally substituted
with one to three groups, which may be the same or
different, selected from X';
R23, R24, R25i ,R26, R27,R28 and R29 are each
independently H or C1-C4alkyl; and the dotted line
configuration c—N represents a double bond or a single bond (i.e.
C-N or C=N); or a stereoisomer thereof.
Further preferred neuronal sodium channel antagonist compounds of the invention are those compounds of fonnula IV or V wherein the dotted line configuration c—N represents a double bond.
Other preferred neuronal sodium channel antagonist compounds suitable for use in the composition of the invention are those compounds of formula JV or V wherein W is O; X" and Y" are each independently H or C1-C6haloalkyl; m is 1; R23, R24, R25, R26 and R27 are each H; G is phenyl optionally substituted with one or more halogen atoms; Q' is halophenyl or C1-C4alkyl optionally substituted with one phenyl or halophenyl group; and the dotted line configuration c—N represents a double bond; or a stereoisomer thereof.
Arylpyrrole insecticides include those described in U.S. 5,010,098; U.S. 5,492,925; U.S. 5,484,807 and U.S. 5,284,863, among other publications. Exemplary of the arylpyrrole insecticides suitable for use in the composition of the invention are those arylpyrroles having the structural formula


Hal is CI or Br;
X is an integer of 1, 2, 3, 4, 5 or 6;
D is H; C1-C6alkyl optionally substituted with one or more halogen, CN, OH, C1-C4alkoxy, C1-C4haloalkoxy, C1-C5alkylthio, C1-C4alkylcarbonyloxy, C1-C4haloalkylthio, C1-C6alkenylcarbonyloxy, phenylcarbonyloxy, halophenylcarbonyloxy, phenoxy, halophenoxy, phenyl, halophenyl or C1-Cgalkylphenyl groups, C1-Cealkenyl; C1-C6haloalkenyl; CN; C2-Cgalkynyl; C1-C6haloalkynyl; di-(C1-C4alkyl)aminocarbonyl; or C3-C6polymethyleneiminocarbonyl; L is H or halogen;
M and M1 are each independently H, halogen, CN, NO2, C1-C4alkyl, C1-C4haloalkyl, C1-C4alkoxy, C1-C4haloalkoxy, C1-C4alkylthio, C1-C4haloalkylthio, C1-C4alkylsufonyl, C1-C4haloa!kylsulfonyl, C1-C4alkylcarbonyl, C1-C4haloalkylcarbonyl, NR35R36 or when M and M1 are attached to adjacent carbon atoms, they may be taken together with the carbon atoms to which they are


Preferred arylpyrroles suitable for use as one essential active ingredient in the composition of the invention are those arylpyrroles of formula VI wherein D is H or ethoxymethyl; Ar is phenyl substituted with one or more halogen or halomethyl groups; and n is 1.
Preferred embodiments of the invention are those having a neuronal sodium channel antagonist compound of formula I or formula III and an arylpyrrole compound of formula VI as active ingredients.
More preferred embodiments of the invention are those having a fomriula I or fomiula III compound wherein W is 0; 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 CH3; n is 0; m, p and q are each independently 1; R and R1 are each Independently H; Z is CI;, R33 and G are each independently CO2CH3; Q is p-(trifluoromethoxy)phenyl; and the dotted line configuration c—N represents a double bond and a formula VI arylpyrrole wherein D is H or ethoxymethyl; Ar is phenyl substituted with one or more halogen or halomethyl groups; and x is 1.

Particularly preferred embodiments of the invention are those having as the active ingredients a compound of formula I or 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 CH3; n is 0; m, p and q are each 1; R and R, are each H; Z' is CI;, R33 and G are each CO2CH3; and Q is p-(trifluoromethoxy)phenyl, and the dotted line configuration c—N represents a double bond and an arylpyrrole of formula VI wherein D is H or ethoxymethyl; Ar is p-chlorophenyl or 3,5-dichlorophenyl; and x is 1.
In the specification and claims the tenn haloalkyl designates an alkyl group CxHax+i having 1 to 2x+1 halogen atoms which may be the same or different. Similarly, the terms haloalkenyl, haloalkynyl, haloalkoxy, halophenyl and the like designate mono- to perhalogen substitution wherein the halogens may be the same or different. Halogen designates CI, Br, I or F.
Each of the compounds of formula I, II, III, IV and V embody assymetric centers which may be represented in the stereoisomeric R-form or S-form. The present invention also includes the R-form, the S-form or mixtures comprising the R-fonn and the S-form in any ratio. For compounds of formula III, the S-form is preferred.
Advantageously, the neuronal sodium-channel antagonist compound of fonnula I, II, III, IV or V or a mixture thereof may be fomrulated with an arylpyrrole insecticide. Said formulation may then be dispersed in a solid or liquid diluent for application to the insect, its food supply, breeding ground or habitat as a dilute spray or as a solid dust or dust concentrate. Customary formuiation adjuvants as well as additional agriculturally acceptable active ingredients may be added and are within the scope of the invention.

The active ingredients of the inventive composition may also be formulated separately as a wettable powder, emulsifiable concentrate, aqueous or liquid flowable, suspension concentrate or any one of the conventional formulations used for insect control agents and tank mixed in the field with water or other inexpensive liquid for application as a liquid spray mixture. The separately fomiulated compositions may also be applied sequentially.
In actual practice, the composition of the invention is applied to the plant foliage or plant stem or insect habitat as a dilute spray prepared from any of the above-said formulations. In practice it has been found that the active ingredients of the composition of the invention are highly synergistic when present at a ratio of neuronal sodium channel antagonist compound to arylpyrrole insecticide of about 1:10 to 1:50.
The compositions of the invention are superior insecticidal compositions and are especially useful for protecting growing and harvested plants including: leguminous crops such as soybeans, snap beans, peas, wax beans and the like as well as cotton, forage crops, cole crops, leafy vegetables, tobacco, hops, tomatoes, potatoes, flowering ornamentals such as chrysanthemums, vine crops such as grapes, squash, pumpkin or melon and fruit trees such as cherry, peach, apple or citrus, from the ravages of insects.
The synergistic insecticidal composition of the invention is found to be highly active against a wide variety of lepidopteran and coleopteran insects such as Helicoverpa zea (cotton bollworm), Heliothis virescens (tobacco budworm), Leptinotarsa decemlineata{Colorado potato beetle), Diabrotica spp. (corn rootworm) and the like.
Further, the composition of the invention may be useful in the prevention and control of public health pests such as houseflies, mosquitoes, cockroaches, ants, termites or the like.

These and other advantages of the invention may become more apparent from the examples set forth herein below. These examples are provided merely as illustrations of the invention and are not intended to be construed as a limitation thereof.

EXAMPLE 1
Evaluation of the Synergistic Insecticidal Effect Of A Combination Of A Neuronal Sodium Channel Antagonist Plus An Arvlpvrrole Insecticide
In this evaluation, the Heliothis zea (cotton bollworm), Heliothis virescens (tobacco budwomn) and pyrethroid-resistant Heliothis virescens larvae used are obtained from laboratory colonies. Pyrethroid-resistant H. virescens are derived from the PEG-strain [Campannola & Plapp, Proceedings of Beltwide Cotton Conference (1988)].
Cotton leaves are immersed in 1:1 v/v, acetone/water solutions of test compound, or solutions of a combination of test compounds for a period of about 3 seconds. Following immersion, leaves are allowed to air-dry for 2-3 hours. Plastic bioassay trays containing multiple open-faced wells (4.0 X 4.0 x 2.5 cm) are used as the test arenas. Cut portions of a treated leaf, a moistened cotton dental wick and a single third-instar larva are placed into each well, covered with an adhesive vented clear plastic sheet and held under constant fluorescent light at about 27°C for a predetermined period of time. Larval mortality/morbidity is evaluated at 5 days after treatment. All treatments are replicated 4-5 fold in a randomized complete block design with 16-32 larvae per treatment. A log-probit analysis is applied to all data obtained. The results are summarized in Tables I, II and III hereinbelow.



WE CLAIM:
1. A synergistic insecticidal composition comprising a synergistically effective amount of a neuronal sodium channel antagonist and an arylpyrrole insecticide wherein the sodium channel antagonist compound has the structure of formula



wherein A is CR4R5 or NR6; W is 0 or S;
X, Y, Z, X', Y' and Z" are each independently H; halogen; OH; CN; NO2; C1-C6alkyl optionally substituted with one or more halogen, C1-C3alkoxy, C4-
C6haloalkoxy, C3-C6Cycloalkyl, C1-C6alkenyloxy or
sulfonyloxy groups; C1-C6alkoxy optionally substituted with one or more halogen,
C1-C3alkoxy or C3-C6cycloalkyl groups; C1-C6alkoxycarbonyl, C3-C6Cycloalkylcarbonyloxy, phenyl optionally substituted with one or
more halogen, C1-C4alkyl, or C1-C4alkoxy groups; aminocarbonyloxy optionally substituted with one or more
C1-C3alkyl groups; C1-C6alkoxycarbonyloxy; C1-C6alkylsulfonyloxy; C1-C6alkenyl;
or NR12R13; 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, R1, R2, R3, R4 and R5 are each independently H or C1-C4alkyl; R6 is H, C1-C6alkyl, C1-C6haloalkyl, C1-C6alkoxyalkyl,

C1-C6alkoxy, C1-C6haloalkoxy.C1-C6alkenyl, C1-C6alkynyl, C1-Cgalkylcarbonyl, C1-C6alkoxycarbonyl, C1-C6alkylthio, or C,-Cehaloalkylthio; R7 and Rgare each independently H; halogen; C1-C6alkyl; C,-
Cealkylcarbonyioxy; or phenyl optionally substituted with one or more
halogen, CN, NO2, C1-C6alkyl, C1-C6haloalkyl, C,-C6alkoxy or C1-C6haloalkoxy groups; R9 and R10 are each independently H, or C1-C4alkyl; R11 is H, C1-C6alkyl, C1-C6haloalkyl, C1-C4alkylcarbonyl, C,-
Cgalkoxycarbonyl, or C1-C6haloalkoxycarbonyl; R12 and R13 are each independently H or C1-C6alkyl; G is H; C1-C6alkyl optionally substituted with one or more halogen, C1-C4alkoxy, C1-Cahaloalkoxy, CN, N02S(0)i,Ri4, COR15, CO2R16, phenyl or C1-C6cycloalkyl groups; C1-C6alkoxy; C1-C6haloalkoxy; CN; NO2; S(0)uRi7; CORie; CO2R19; phenyl optionally substituted
with one or more halogen, CN, C1-Chaloalkyl, or C,-Cjhaloalkoxy groups; Ca-C6Cycloalkyl; or phenylthio; Q is phenyl optionally substituted with one or more halogen, CN, SCN, NO2, S(0)uR2o. C1-C4alkyl, C1-C4haloalkyl, C,-C4alkoxyalkyl, C1-C6alkoxy, C1-C6haloalkoxy, or NR21R22 groups; u is an integer of 0,1 or 2; Ri4, Ri5, R16, RIB. R19. R21 and R22 are each independently H or C1-
Cgalkyl; R17 and R20 are each independently C1-C6alkyl or C1-C6haloalkyl;

R33 is CO2R34I
R34 is H, C1-C6alkyl, C1-C6haloalkyI, phenyl or
halophenyl; X' and Y are each independently H; halogen; CN; SCN; C1-C6alkyl
optionally substituted with one or
more halogen, NOj, CN, C1-C4alkoxy, C1-C4alkylthio, phenyl, halophenyl, C,-C4alkylsulfonyl, C4-C4haloalkylsulfonyl, or C1-C4alkoxycarbonyl groups;
C2-C4alkenyl; C2-C4haloalkenyl; C2-C4alkynyl; C2-
C4haloalkynyl; C3-C6CycloalkyI; Cs-C6halocycloalkyl; phenyl
optionally substituted
with one or more halogen, CN, NO2, C1-C4alkyl, C,-C4haloalkyl, C1-C4alkoxy, C1-C4haloalkoxy, C1-C4alkylthio, C1-C4alkylsulfonyl or C1-C4haloalkylsulfonyl groups;
C1-C4alkylcarbonyl; C1-C4haloalkylcarbonyl; or NR28R29; G' is phenyl optionally substituted with one or more groups which may be the same or different selected from X';
a 5-membered heteroaromatic ring containing one or two heteroatoms selected from 0 or 1 oxygen, 0 or 1 sulfur and 0,1 or 2 nitrogen atoms said 5-membered heteroaromatic ring being attached via carbon and being optionally substituted with one or more groups which may be the same or different selected from X'; or
a 6-membered heteroaromatic ring containing one or two heteroatoms selected from 0 or 1 oxygen, 0 or 1 sulfur and 0,1 or 2 nitrogen atoms said 6-membered heteroaromatic ring being attached via carbon and

being optionally substituted with one or more groups
which may be the same or different selected from X1; Q' is H; C1-C6alkyl optionally substituted with one or more halogen,
CN, C1-C6alkoxy, C1-C6alkoxycarbonyl, or phenyl
optionally
substituted with one or more halogen, CN, NO2, C1-C4alkyl, C1-C4haloalkyl, C,-C4alkylsulfonyl or C1-C4alkylsulfinyl groups; C1-C6alkenyl; C2-C6alkynyl; or phenyl optionally substituted
with one to three groups, which may be the same or
different, selected from X';
R23, R24, R25, R26, R27, R28, ancl R29 are® each
independently H or C1-C4alkyl;
and the dotted line configuration c—N represents a double bond or a single bond; or a stereoisomer thereof and wherein the arylpyrrole insecticide is a compound of fomnula VI


Hal is CI or Br;
X is an integer of 1, 2, 3, 4, 5 or 6;
D is H, C1-C6alkyl optionally substituted with one or more halogen, CN, OH, C1-C4alkoxy, C1-C4haloalkoxy, C1-C5alkylthio, C1-C4alkylcarbonyloxy, C1-C4haloalkylthio, C1-C6alkenylcarbonyloxy, phenylcarbonyloxy, halophenylcarbonyloxy, phenoxy, haiophenoxy, phenyl, halophenyl or C1-C6alkylphenyl groups, C1-C6alkenyl, C1-C6haloalkenyl, CN, C2-C6alkynyl, C1-C8haloalkynyl, di-(C1-C4alkyl)aminocarbonyl or C3-Cepolymethyleneiminocarbonyl; L is H or halogen;
M and M1 are each independently H, halogen, CN, NO2, C1-C4alkyl, C1-C4haloalkyl, C1-C4alkoxy, C1-C4haloalkoxy, C1-C4alkylthio, C1-C4haloalkylthio, C1-C4alkylsufonyl, C1-C4haloaIkylsulfonyl, C1-C4alkylcarbonyl, C1-C4haloalkylcarbonyl, NR35R36 or when M and M^ are attached to adjacent carbon atoms, they may be taken together with the carbon atoms to which they are attached to form a ring in which MM1 represents -OCH2O-. -OCFjO- or-CH=CH-CH=CH-; A' is 0 or S;
R30, R31 and R32 are each independently hydrogen, halogen, NO2, CHO or R31 and R32 may be taken together with the carbon atoms to which they are attached to form a ring in which


L ,L T and V are each independently H, halogen, CN or NO2 with the proviso that no more than two of L ,L T or V are NO2; and R35 and R36 are each independently HorC1-C4alkyl.
2. The composition as claimed in claim 1, wherein the ratio of the neuronal sodium channel antagonist to the arylpyrrole insecticide is about 1; 10 to 1:50.
3. The composition as claimed in claim 2, wherein said neuronal sodium channel antagonist and said arylpyrrole insecticide are dispersed in an inert solid or liquid siluent.
4. The composition as claimed in claim 1, comprises a compound of formula I or formula III wherein the dotted line configuration C—N represents a double bond.
5. The composition as claimed in claim 4, 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 CH2; n is 0; m, p and q are each independently 1; R and Rl are each independently H; Z is C1; R33 and G are each independently CO2CH3; and Q is P-(trifluoromethoxy)phenyl.
6. The composition as claimed in claim 1, comprises an arylpyrrole insecticide of formula VI wherein d is H or ethoxymethyl; Ar is phenyl substituted with one or two halogen or halomethyl groups; and x is 1.

7. 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 as claimed in claim 1.
8. The method as claimed in claim 7, wherein the neuronal sodium channel
antagonist is present in a ratio to the arylpyrrole insecticide of about 1:10 to 1:50
and having a neuronal sodium channel antagonist compound of formula I or
formula III wherein the dotted line configuration C—N represents a double bond
and 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 CH2; n is 0; m, p and q
are each independently 1; R and R1 are each independently H; X is CI; R33 and G
are each independently CO2CH3; and Q is/'-(trifluoromethoxy) phenyl.
9. The method as claimed in claim 7, having an arylpyrrole insecticide of
formula VI wherein d is H or ethyoxymethyl; Ar is phenyl substituted with one or
two halogen or halomethyl groups; and x is 1.
10. A method of preventing a plant from infestation, which comprises applying
to the foliage or stem of, said plant a synergistically effective amount of a
composition as claimed in claim 1.


Documents:

in-pct-2001-1241-che abstract-duplicate.pdf

in-pct-2001-1241-che abstract.pdf

in-pct-2001-1241-che claims-duplicate.pdf

in-pct-2001-1241-che claims.pdf

in-pct-2001-1241-che correspondence-others.pdf

in-pct-2001-1241-che correspondence-po.pdf

in-pct-2001-1241-che description(complete)-duplicate.pdf

in-pct-2001-1241-che description(complete).pdf

in-pct-2001-1241-che form-1.pdf

in-pct-2001-1241-che form-19.pdf

in-pct-2001-1241-che form-26.pdf

in-pct-2001-1241-che form-3.pdf

in-pct-2001-1241-che form-5.pdf

in-pct-2001-1241-che others.pdf

in-pct-2001-1241-che pct search report.pdf

in-pct-2001-1241-che pct.pdf

in-pct-2001-1241-che petition.pdf


Patent Number 220616
Indian Patent Application Number IN/PCT/2001/1241/CHE
PG Journal Number 29/2008
Publication Date 18-Jul-2008
Grant Date 29-May-2008
Date of Filing 06-Sep-2001
Name of Patentee BASF AKTIENGESELLSCHAFT
Applicant Address
Inventors:
# Inventor's Name Inventor's Address
1 RENSNER, PAUL, ERICH
2 BORYSEWICZ, RAYMOND, FRANK
3 TREACY, MICHAEL, FRANK
PCT International Classification Number A01N43/36
PCT International Application Number PCT/US2000/05951
PCT International Filing date 2000-03-07
PCT Conventions:
# PCT Application Number Date of Convention Priority Country
1 60/124,228 1999-03-12 U.S.A.
2 60/158,202 1999-10-07 U.S.A.