PatentDe  


Dokumentenidentifikation EP1161148 07.08.2003
EP-Veröffentlichungsnummer 1161148
Titel SYNERGISTISCHE INSEKTIZIDE ZUSAMMENSETZUNGEN
Anmelder BASF AG, 67063 Ludwigshafen, DE
Erfinder TREACY, Frank, Michael, Newtown, US;
BORYSEWICZ, Frank, Raymond, Hamilton Square, US;
RENSNER, Erich, Paul, Yardley, US
DE-Aktenzeichen 60003640
Vertragsstaaten AT, BE, CH, CY, DE, DK, ES, FI, FR, GB, GR, IE, IT, LI, LU, MC, NL, PT, SE
Sprache des Dokument EN
EP-Anmeldetag 07.03.2000
EP-Aktenzeichen 009137894
WO-Anmeldetag 07.03.2000
PCT-Aktenzeichen PCT/US00/05951
WO-Veröffentlichungsnummer 0000054592
WO-Veröffentlichungsdatum 21.09.2000
EP-Offenlegungsdatum 12.12.2001
EP date of grant 02.07.2003
Veröffentlichungstag im Patentblatt 07.08.2003
IPC-Hauptklasse A01N 47/34
IPC-Nebenklasse A01N 47/38   A01N 47/40   A01N 43/56   A01N 37/50   A01N 43/36   

Beschreibung[en]
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. 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 NR6;

   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, C1-C3haloalkoxy, C3-C6cycloalkyl, C2-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; C2-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, C2-C6alkenyl, C2-C6alkynyl, C1-C6alkylcarbonyl, C1-C6alkoxycarbonyl, C1-C6alkylthio, or C1-C6haloalkylthio;

   R7 and R8 are each independently H; halogen; C1-C6alkyl; C1-C6alkylcarbonyloxy; or phenyl optionally substituted with one or more

         halogen, CN, NO2, C1-C6alkyl, C2-C6haloalkyl, C1-C6alkoxy or C1-C6haloalkoxy groups;

   R9 and R10 are each independently H, or C1-C4alkyl;

   R11 is H, C1-C6alkyl, C1-C6haloalkyl, C1-C4alkylcarbonyl, C1-C6alkoxycarbonyl, 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-C6haloalkoxy, CN, NO2S(O)uR14, COR15, CO2R16, phenyl or C3-C6cycloalkyl groups;

      C1-C6alkoxy; C1-C6haloalkoxy; CN; NO2; S(O)uR17; COR18;

      CO2R19; phenyl optionally substituted

         with one or more halogen, CN, C1-C3haloalkyl, or C1-C3haloalkoxy groups;

      C3-C6cycloalkyl; or phenylthio;

   Q is phenyl optionally substituted with one or more halogen, CN, SCN, NO2, S(O)uR20, C1-C4alkyl, C1-C4haloalkyl, C1-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-C6alkyl;

   R17 and R20 are each independently C1-C6alkyl or C1-C6haloalkyl;

   R33 is CO2R34;

   R34 is H, C1-C6alkyl, C1-C6haloalkyl, 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 formula 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 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 CH2; n is 0; m, p and q are each 1; R and R1 are each H; Z' is Cl; 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

wherein W is O or S;

   X" and Y" are each independently H; halogen; CN; SCN; C1-C6alkyl optionally substituted with one or more halogen, NO2, CN, C1-C4alkoxy, C1-C4alkylthio, phenyl, halophenyl, C1-C4alkylsulfonyl, C1-C4haloalkylsulfonyl, or C1-C4alkoxycarbonyl groups;

   C2-C4alkenyl; C2-C4haloalkenyl; C2-C4alkynyl; C2-C4haloalkynyl; C3-C6cycloalkyl; C3-C6halocycloalkyl; phenyl optionally substituted

      with one or more halogen, CN, NO2, C1-C4alkyl, C1-C4haloalkyl, C1-C4alkoxy, C1-C4haloalkoxy, C1-C4alkylthio, C1-C4alkylsulfonyl or C1-C4haloalkylsulfonyl groups;

   C1-C4alkylcarbonyl; C1-C4haloalkylcarbonyl; 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-C3alkoxy, C1-C6alkoxycarbonyl, or phenyl optionally substituted with one or more halogen, CN, NO2, C1-C4alkyl, C1-C4haloalkyl, C1-C4alkylsulfonyl or C1-C4alkylsulfinyl groups;

   C2-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 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 formula 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 IV 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

wherein Ar is
   Hal is Cl 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, C2-C6alkenylcarbonyloxy, phenylcarbonyloxy, halophenylcarbonyloxy, phenoxy, halophenoxy, phenyl, halophenyl or C1-C3alkylphenyl groups,

      C2-C6alkenyl; C2-C6haloalkenyl; CN; C2-C6alkynyl; C2-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-C4haloalkylsulfonyl, 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 attached to form a ring in which MM1 represents -OCH2O-, -OCF2O- or -CH=CH-CH=CH-;

   A' is O 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 R31R32 represent
   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 H or C1-C4alkyl,

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 formula I or formula III compound 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 independently 1; R and R1 are each independently H; Z' is Cl;, 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 R1 are each H; Z' is Cl;, 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 term haloalkyl designates an alkyl group CxH2x+1 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 Cl, 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-form 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 formula I, II, III, IV or V or a mixture thereof may be formulated 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 formulation 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 formulated 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 Arylpyrrrole Insecticide

In this evaluation, the Heliothis zea (cotton bollworm), Heliothis virescens (tobacco budworm) 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.


Anspruch[de]
  1. Synergistische insektizide Zusammensetzung, enthaltend eine synergistisch wirksame Menge eines Neuronen-Natriumkanalantagonisten und eines Arylpyrrolinsektizids, wobei die Natriumkanalantagonistenverbindung die Struktur der folgenden Formel aufweist
    in der A CR4R5 oder NR6 bedeutet,

    W O oder S bedeutet,

    X, Y, Z, X', Y' und Z' jeweils unabhängig H, Halogen, OH, CN, NO2, C1-C6-Alkyl, das gegebenenfalls durch eine oder mehrere Halogen-, C1-C3-Alkoxy-, C1-C3-Halogenalkoxy-, C3-C6-Cycloalkyl-, C2-C6-Alkenyloxy- oder Sulfonyloxy-Gruppen substituiert ist,

    C1-C6-Alkoxy, das gegebenenfalls durch eine oder mehrere Halogen-, C1-C3-Alkoxy- oder C3-C6-Cycloalkyl-Gruppen substituiert ist,

    C1-C6-Alkoxycarbonyl, C3-C6-Cycloalkylcarbonyloxy oder Phenyl, die gegebenenfalls durch eine oder mehrere Halogen-, C1-C4-Alkyl- oder C1-C4-Alkoxy-Gruppen substituiert sind,

    Aminocarbonyloxy, das gegebenenfalls durch eine oder mehrere C1-C3-Alkyl-Gruppen substituiert ist,

    C1-C6-Alkoxycarbonyloxy, C1-C6-Alkylsulfonyloxy, C2-C6-Alkenyl oder NR12R13 bedeuten,

    m, p und q jeweils unabhängig eine ganze Zahl 1, 2, 3, 4 oder 5 bedeuten,

    n eine ganze Zahl 0, 1 oder 2 bedeutet,

    r eine ganze Zahl 1 oder 2 bedeutet,

    t eine ganze Zahl 1, 2, 3 oder 4 bedeutet,

    R, R1, R2, R3, R4 und R5 jeweils unabhängig H oder C1-C4-Alkyl bedeuten,

    R6 H, C1-C6-Alkyl, C1-C6-Halogenalkyl, C1-C6-Alkoxyalkyl, C1-C6-Alkoxy, C1-C6-Halogenalkoxy, C2-C6-Alkenyl, C2-C6-Alkinyl, C1-C6-Alkylcarbonyl, C1-C6-Alkoxycarbonyl, C1-C6-Alkylthio oder C1-C6-Halogenalkylthio bedeutet,

    R7 und R8 jeweils unabhängig H, Halogen, C1-C6-Alkyl, C1-C6-Alkylcarbonyloxy, oder Phenyl, das gegebenenfalls durch eine oder mehrere Halogen-, CN-, NO2-, C1-C6-Alkyl-, C2-C6-Halogenalkyl-, C1-C6-Alkoxy- oder C1-C6-Halogenalkoxy-Gruppen substituiert ist, bedeuten,

    R9 und R10 jeweils unabhängig H oder C1-C4-Alkyl bedeuten,

    R11 H, C1-6-Alkyl, C1-C6-Halogenalkyl, C1-C4-Alkylcarbonyl, C1-C6-Alkoxycarbonyl oder C1-C6-Halogenalkoxycarbonyl bedeutet,

    R12 und R13 jeweils unabhängig H oder C1-C6-Alkyl bedeuten,

    G H, C1-C6-Alkyl, das gegebenenfalls durch eine oder mehrere Halogen-, C1-C4-Alkoxy-, C1-C6-Halogenalkoxy-, CN-, NO2S(O)uR14-, COR15-, CO2R16-, Phenyl- oder C3-C6-Cycloalkyl-Gruppen substituiert ist,

    C1-C6-Alkoxy, C1-C6-Halogenalkoxy, CN, NO2, S(O)uR17, COR18, CO2R19, Phenyl, das gegebenenfalls durch eine oder mehrere Halogen-, CN-, C1-C3-Halogenalkyl- oder C1-C3-Halogenalkoxy-Gruppen substituiert ist,

    C3-C6-Cycloalkyl oder Phenylthio bedeutet,

    Q Phenyl, das gegebenenfalls durch eine oder mehrere Halogen-, CN-, SCN-, NO2-, S(O)uR20-, C1-C4-Alkyl-, C1-C4-Halogenalkyl-, C1-C4-Alkoxyalkyl-, C1-C6-Alkoxy-, C1-C6-Halogenalkoxy- oder NR21R22-Gruppen substituiert ist, bedeutet,

    u eine ganze Zahl 0, 1 oder 2 bedeutet,

    R14, R15, R16, R18, R19, R21 und R22 jeweils unabhängig H oder C1-C6-Alkyl bedeuten,

    R17 und R20 jeweils unabhängig C1-C6-Alkyl oder C1-C6-Halogenalkyl bedeuten,

    R33 CO2R34 bedeutet,

    R34 H, C1-C6-Alkyl, C1-C6-Halogenalkyl, Phenyl oder Halogenphenyl bedeutet,

    X' und Y' jeweils unabhängig H, Halogen, CN, SCN, C1-C6-Alkyl, das gegebenenfalls durch eine oder mehrere Halogen-, NO2-, CN-, C1-C4-Alkoxy-, C1-C4-Alkylthio-, Phenyl-, Halogenphenyl-, C1-C4-Alkylsulfonyl-, C1-C4-Halogenalkylsulfonyl- oder C1-C4-Alkoxycarbonyl-Gruppen substituiert ist,

    C2-C4-Alkenyl, C2-C4-Halogenalkenyl, C2-C4-Alkinyl, C2-C4-Halogenalkinyl, C3-C6-Cycloalkyl, C3-C6-Halogencycloalkyl, Phenyl, das gegebenenfalls durch eine oder mehrere Halogen-, CN-, NO2-, C1-C4-Alkyl-, C1-C4-Halogenalkyl-, C1-C4-Alkoxy-, C1-C4-Halogenalkoxy-, C1-C4-Alkylthio-, C1-C4-Alkylsulfonyl- oder C1-C4-Halogenalkylsulfonyl-Gruppen substituiert ist,

    C1-C4-Alkylcarbonyl, C1-C4-Halogenalkylcarbonyl oder NR28R29 bedeuten,

    G' Phenyl, das gegebenenfalls durch eine oder mehrere, gleiche oder verschiedene Gruppen aus der Reihe X' substituiert ist,

    einen 5-gliedrigen heteroaromatischen Ring, der ein oder zwei Heteroatome aus der Gruppe 0 oder 1 Sauerstoffatom, 0 oder 1 Schwefelatom und 0, 1 oder 2 Stickstoffatome enthält, wobei der 5-gliedrige heteroaromatische Ring über Kohlenstoff gebunden und gegebenenfalls durch eine oder mehrere, gleiche oder verschiedene Gruppen aus der Reihe X' substituiert ist, oder

    einen 6-gliedrigen heteroaromatischen Ring, der ein oder zwei Heteroatome aus der Reihe 0 oder 1 Sauerstoffatom, 0 oder 1 Schwefelatom und 0, 1 oder 2 Stickstoffatome enthält, wobei der 6-gliedrige heteroaromatische Ring über Kohlenstoff gebunden und gegebenenfalls durch eine oder mehrere, gleiche oder verschiedene Gruppen aus der Reihe X' substituiert ist, bedeutet,

    Q' H, C1-C6-Alkyl, das gegebenenfalls durch einen oder mehrere Substituenten aus der Reihe Halogen, CN, C1-C3-Alkoxy, C1-C6-Alkoxycarbonyl oder Phenyl, das gegebenenfalls durch eine oder mehrere Halogen-, CN-, NO2-, C1-C4-Alkyl-, C1-C4-Halogenalkyl-, C1-C4-Alkylsulfonyl- oder C1-C4-Alkylsulfinyl-Gruppen substituiert ist,

    C2-C6-Alkenyl, C2-C6-Alkinyl oder Phenyl, das gegebenenfalls durch eine bis drei gleiche oder verschiedene Gruppen aus der Reihe X' substituiert ist, bedeutet,

    R23, R24, R25, R26, R27, R28 und R29 jeweils unabhängig H oder C1-C4-Alkyl bedeuten,

    und die Konfiguration C---N mit der gebrochenen Linie eine Doppelbindung oder Einfachbindung bedeutet, oder

    eines ihrer Stereoisomeren,

    und wobei es sich bei dem Arylpyrrolinsektizid um eine Verbindung der Formel VI handelt
    in der Ar
    bedeutet,

    Hal Cl oder Br bedeutet,

    x eine ganze Zahl 1, 2, 3, 4, 5 oder 6 bedeutet,

    D H, C1-C6-Alkyl, das gegebenenfalls durch eine oder mehrere Halogen-, CN-, OH-, C1-C4-Alkoxy-, C1-C4-Halogenalkoxy-, C1-C5-Alkylthio-, C1-C4-Alkylcarbonyloxy-, C1-C4-Halogenalkylthio-, C2-C6-Alkenylcarbonyloxy-, Phenylcarbonyloxy-, Halogenphenylcarbonyloxy-, Phenoxy-, Halogenphenoxy-, Phenyl-, Halogenphenyl- oder C1-C3-Alkylphenyl-Gruppen substituiert ist,

    C2-C6-Alkenyl, C2-C6-Halogenalkenyl, CN, C2-C6-Alkinyl, C2-C6-Halogenalkinyl, Di-(C1-C4-alkyl)-aminocarbonyl oder C3-C6-Polymethyleniminocarbonyl bedeutet,

    L H oder Halogen bedeutet,

    M und M1 jeweils unabhängig H, Halogen, CN, NO2, C1-C4-Alkyl, C1-C4-Halogenalkyl, C1-C4-Alkoxy, C1-C4-Halogenalkoxy, C1-C4-Alkylthio, C1-C4-Halogenalkylthio, C1-C4-Alkylsulfonyl, C1-C4-Halogenalkylsulfonyl, C1-C4-Alkylcarbonyl, C1-C4-Halogenalkylcarbonyl oder NR35R36 bedeuten, oder, wenn M und M1 an benachbarte Kohlenstoffatome gebunden sind, sie gemeinsam mit den Kohlenstoffatomen, an die sie gebunden sind, einen Ring bilden können, in dem MM1 -OCH2O-, -OCF2O- oder -CH=CH-CH=CH- darstellt,

    A' O oder S bedeutet,

    R30, R31 und R32 jeweils unabhängig Wasserstoff, Halogen, NO2, CHO bedeuten, oder R31 und R32 gemeinsam mit den Kohlenstoffatomen, an die sie gebunden sind, einen Ring bilden können, in dem R31R32
    darstellt,

    L', L", T und V jeweils unabhängig H, Halogen, CN oder NO2 bedeuten, mit der Maßgabe, daß nicht mehr als zwei Symbole aus der Gruppe L', L", T oder V NO2 bedeuten, und

    R35 und R36 jeweils unabhängig H oder C1-C4-Alkyl bedeuten.
  2. Zusammensetzung nach Anspruch 1, wobei das Verhältnis Neuronen-Natriumkanalantagonist zu Arylpyrrolinsektizid ungefähr 1:10 bis 1:50 beträgt.
  3. Zusammensetzung nach Anspruch 2, wobei der Neuronen-Natriumkanalantagonist und das Arylpyrrolinsektizid in einem inerten festen oder flüssigen Verdünnungsmittel dispergiert sind.
  4. Zusammensetzung nach Anspruch 1 mit einer Verbindung der Formel I oder Formel III, in der die Konfiguration C---N mit der gebrochenen Linie eine Doppelbindung bedeutet.
  5. Zusammensetzung nach Anspruch 4, in der W O bedeutet, X Trifluormethoxy bedeutet und in 4-Stellung vorliegt, Y Trifluormethyl bedeutet und in 3-Stellung vorliegt, Z CN bedeutet und in 4-Stellung vorliegt, A CH2 bedeutet, n 0 bedeutet, m, p und q jeweils unabhängig 1 bedeuten, R und R1 jeweils unabhängig H bedeuten, Z' Cl bedeutet, R33 und G jeweils unabhängig CO2CH3 bedeuten und Q p-(Trifluormethoxy)phenyl bedeutet.
  6. Zusammensetzung nach Anspruch 1 mit einem Arylpyrrolinsektizid der Formel VI, in der D H oder Ethoxymethyl bedeutet, Ar Phenyl, das durch eine oder zwei Halogen- oder Halogenmethyl-Gruppen substituiert ist, bedeutet, und x 1 bedeutet.
  7. Verfahren zur synergistischen Bekämpfung von Insekten, bei dem das Insekt mit einer synergistisch wirksamen Menge einer wie in Anspruch 1 beschriebenen Kombination aus einem Neuronen-Natriumkanalantagonisten und einem Arylpyrrolinsektizid in Kontakt gebracht wird.
  8. Verfahren nach Anspruch 7, wobei der Neuronen-Natriumkanalantagonist im Verhältnis von ungefähr 1:10 bis 1:50 zu dem Arylpyrrolinsektizid vorhanden ist und eine Neuronen-Natriumkanalantagonistenverbindung der Formel I oder Formel III aufweist, wobei die Konfiguration C---N mit der gebrochenen Linie eine Doppelbindung bedeutet und W O bedeutet, X Trifluormethoxy bedeutet und in 4-Stellung vorliegt, Y Trifluormethyl bedeutet und in 3-Stellung vorliegt, Z CN bedeutet und in 4-Stellung vorliegt, A CH2 bedeutet, n 0 bedeutet, m, p und q jeweils unabhängig 1 bedeuten, R und R1 jeweils unabhängig H bedeuten, Z' Cl bedeutet, R33 und G jeweils unabhängig CO2CH3 bedeuten und Q p-(Trifluormethoxy)phenyl bedeutet.
  9. Verfahren nach Anspruch 7 mit einem Arylpyrrolinsektizid der Formel VI, in der D H oder Ethoxymethyl bedeutet, Ar Phenyl, das durch eine oder zwei Halogen- oder Halogenmethyl-Gruppen substituiert ist, bedeutet, und x 1 bedeutet.
  10. Verfahren zum Schützen einer Pflanze gegen Besiedlung und Befall durch Insekten, dadurch gekennzeichnet, daß man eine synergistisch wirksame Menge einer Verbindung nach Anspruch 1 auf das Blattwerk oder den Stengel dieser Pflanze aufbringt.
Anspruch[en]
  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 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, C1-C3haloalkoxy, C3-C6cycloalkyl, C2-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; C2-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,C2-C6alkenyl, C2-C6alkynyl, C1-C6alkylcarbonyl, C1-C6alkoxycarbonyl, C1-C6alkylthio, or C1-C6haloalkylthio;

       R7 and R8 are each independently H; halogen; C1-C6alkyl; C1-C6alkylcarbonyloxy; or phenyl optionally substituted with one or more

             halogen, CN, NO2, C1-C6alkyl, C2-C6haloalkyl, C1-C6alkoxy or C1-C6haloalkoxy groups;

       R9 and R10 are each independently H, or C1-C4alkyl;

       R11 is H, C1-C6alkyl, C1-C6haloalkyl, C1-C4alkylcarbonyl, C1-C6alkoxycarbonyl, 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-C6haloalkoxy, CN, NO2S(O)uR14, COR15, CO2R16, phenyl or C3-C6cycloalkyl groups;

          C1-C6alkoxy; C1-C6haloalkoxy; CN; NO2; S(O)uR17; COR18; CO2R19; phenyl optionally substituted

             with one or more halogen, CN, C1-C3haloalkyl, or C1-C3haloalkoxy groups;

          C3-C6cycloalkyl; or phenylthio;

       Q is phenyl optionally substituted with one or more halogen, CN, SCN, NO2, S(O)uR20, C1-C4alkyl, C1-C4haloalkyl, C1-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-C6alkyl;

       R17 and R20 are each independently C1-C6alkyl or C1-C6haloalkyl;

       R33 is CO2R34;

       R34 is H, C1-C6alkyl, C1-C6haloalkyl, phenyl or halophenyl;

       X" and Y" are each independently H; halogen; CN; SCN; C1-C6alkyl optionally substituted with one or

             more halogen, NO2, CN, C1-C4alkoxyl C1-C4alkylthio, phenyl, halophenyl, C1-C4alkylsulfonyl, C1-C4haloalkylsulfonyl, or C1-C4alkoxycarbonyl groups;

          C2-C4alkenyl; C2-C4haloalkenyl; C2-C4alkynyl; C2-C4haloalkynyl; C3-C6cycloalkyl; C3-C6halocycloalkyl; phenyl optionally substituted

             with one or more halogen, CN, NO2, C1-C4alkyl, C1-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 X";

       Q' is H; C1-C6alkyl optionally substituted with one or more halogen, CN, C1-C3alkoxy, C1-C6alkoxycarbonyl, or phenyl optionally

             substituted with one or more halogen, CN, NO2, C1-C4alkyl, C1-C4haloalkyl, C1-C4alkylsulfonyl or C1-C4alkylsulfinyl groups;

          C2-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 and 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 formula VI
    wherein Ar is
       Hal is Cl 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, C2-C6alkenylcarbonyloxy, phenylcarbonyloxy, halophenylcarbonyloxy, phenoxy, halophenoxy, phenyl, halophenyl or C1-C3alkylphenyl groups, C2-C6alkenyl, C2-C6haloalkenyl, CN, C2-C6alkynyl, C2-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-C4haloalkylsulfonyl, 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 attached to form a ring in which MM1 represents -OCH2O-, -OCF2O- or -CH=CH-CH=CH-;

       A' is O 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 R31R32 represent
       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 H or C1-C4alkyl.
  2. The composition according to 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 according to claim 2 wherein said neuronal sodium channel antagonist and said arylpyrrole insecticide are dispersed in an inert solid or liquid diluent.
  4. The composition according to claim 1 having a compound of formula I or formula III wherein the dotted line configuration C---N represents a double bond.
  5. The composition according to 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 R1 are each independently H; Z' is Cl; R33 and G are each independently CO2CH3; and Q is p-(trifluoromethoxy)phenyl.
  6. The composition according to claim 1 having 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 described in claim 1.
  8. The method according to 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; Z' is Cl; R33 and G are each independently CO2CH3; and Q is p-(trifluoromethoxy)phenyl.
  9. The method according to claim 7 having 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.
  10. A method for protecting a plant from infestation and attack by insects which comprises applying to the foliage or stem of said plant a synergistically effective amount of a composition according to claim 1.
Anspruch[fr]
  1. Composition insecticide synergique comprenant une quantité synergiquement efficace d'un antagoniste des canaux sodiques neuronaux et d'un insecticide de type arylpyrrole dans laquelle le composé antagoniste des canaux sodiques a la structure de formule
       où A est CR4R5 ou NR6 ;

       W est O ou S ;

       X, Y, Z, X', Y' et Z' sont chacun indépendamment H ; un halogène ; OH ; CN ; NO2 ; un groupe (C1-C6)alkyle éventuellement substitué par un ou plusieurs halogènes, groupes (C1-C3)-alcoxy, (C1-C3)halogénoalcoxy, (C3-C6)cycloalkyle, (C2-C6)alcényloxy ou sulfonyloxy ;

          (C1-C6)alcoxy éventuellement substitué par un ou plusieurs halogènes, groupes (C1-C3)alcoxy ou (C3-C6)cycloalkyle ;

          (C1-C6)alcoxycarbonyle, (C3-C6)cycloalkylcarbonyloxy, phényle éventuellement substitué par un ou plusieurs halogènes, groupes (C1-C4)alkyle, ou (C1-C4)-alcoxy ;

          aminocarbonyloxy éventuellement substitué par un ou plusieurs groupes (C1-C3)alkyle ;

          (C1-C6)alcoxycarbonyloxy ; (C1-C6)alkylsulfonyloxy ; (C2-C6)-alcényle ; ou NR12R13 ;

       m, p et q sont chacun indépendamment un entier valant 1, 2, 3, 4, ou 5 ;

       n est un entier valant 0, 1 ou 2 ;

       r est un entier valant 1 ou 2 ;

       t est un entier valant 1, 2, 3 ou 4 ;

       R, R1, R2, R3, R4 et R5 sont chacun indépendamment H ou un groupe (C1-C4)alkyle ;

       R6 est H, un groupe (C1-C6)alkyle, (C1-C6)halogénoalkyle, (C1-C6)-alcoxyalkyle, (C1-C6)alcoxy, (C1-C6)halogénoalcoxy, (C2-C6)-alcényle, (C2-C6)alcynyle, (C1-C6)alkylcarbonyle, (C1-C6)-alcoxycarbonyle, (C1-C6)alkylthio, ou (C1-C6)halogénoalkylthio ;

       R7 et R8 sont chacun indépendamment H ; un halogène ; un groupe (C1-C6)alkyle ; (C1-C6)alkylcarbonyloxy ; ou phényle éventuellement substitué par un ou plusieurs halogènes, CN, NO2, groupes (C1-C6)alkyle, (C2-C6)-halogénoalkyle, (C1-C6)alcoxy ou (C1-C6)halogénoalcoxy ;

       R9 et R10 sont chacun indépendamment H, ou un groupe (C1-C4)alkyle ;

       R11 est H, un groupe (C1-C6)alkyle, (C1-C6)halogénoalkyle, (C1-C4)alkylcarbonyle, (C1-C6)alcoxycarbonyle, ou (C1-C6)-halogénoalcoxycarbonyle ;

       R12 et R13 sont chacun indépendamment H ou un groupe (C1-C6)-alkyle ;

       G est H ; un groupe (C1-C6)alkyle éventuellement substitué par un ou plusieurs halogènes, groupes (C1-C4)alcoxy, (C1-C6)-halogénoalcoxy, CN, NO2S(O)uR14, COR15, CO2R16, phényle ou (C3-C6)cycloalkyle ;

          (C1-C6)alcoxy ; (C1-C6)halogénoalcoxy ; CN ; NO2 ; S(O)uR17 ; COR18 ; CO2R19 ; phényle éventuellement substitué par un ou plusieurs halogènes, CN, groupes (C1-C3)halogénoalkyle, ou (C1-C3)halogénoalcoxy ;

          (C3-C6)cycloalkyle ; ou phénylthio ;

       Q est un groupe phényle éventuellement substitué par un ou plusieurs halogènes, CN, SCN, NO2, S(O)uR20, (C1-C4)alkyle, (C1-C4)halogénoalkyle, (C1-C4)alcoxyalkyle, (C1-C6)alcoxy, (C1-C6)halogénoalcoxy, ou NR21R22 ;

       u est un entier valant 0, 1 ou 2 ;

       R14, R15, R16, R18, R19, R21 et R22 sont chacun indépendamment H ou un groupe (C1-C6)alkyle ;

       R17 et R20 sont chacun indépendamment un groupe (C1-C6)alkyle ou (C1-C6)halogénoalkyle ;

       R33 est CO2R34 ;

       R34 est H, un groupe (C1-C6)alkyle, (C1-C6)halogénoalkyle, phényle ou halogénophényle ;

       X" et Y" sont chacun indépendamment H ; un halogène ; CN ; SCN ;

          un groupe (C1-C6)alkyle éventuellement substitué par un ou plusieurs halogènes, NO2, CN, groupes (C1-C4)alcoxy, (C1-C4)alkylthio, phényle, halogénophényle, (C1-C4)-alkylsulfonyle, (C1-C4)halogénoalkylsulfonyle, ou (C1-C4)-alcoxycarbonyle ;

          (C2-C4)alcényle ; (C2-C4)halogénoalcényle ; (C2-C4)alcynyle ; (C2-C4)halogénoalcynyle ; (C3-C6)cycloalkyle ; (C3-C6)-halogénocycloalkyle ; phényle éventuellement substitué

             par un ou plusieurs halogènes, CN, NO2, groupes (C1-C4)alkyle, (C1-C4)halogénoalkyle, (C1-C4)alcoxy, (C1-C4)-halogénoalcoxy, (C1-C4)alkylthio, (C1-C4)alkylsulfonyle ou (C1-C4)halogénoalkylsulfonyle ; (C1-C4)alkylcarbonyle ; (C1-C4)halogénoalkylcarbonyle ; ou NR28R29 ;

       G' est un groupe phényle éventuellement substitué par un ou plusieurs groupes qui peuvent être identiques ou différents choisis parmi X" ;

          un noyau hétéroaromatique à cinq membres contenant un ou deux hétéroatomes choisis parmi 0 ou 1 atome d'oxygène, 0 ou 1 atome de soufre et 0, 1 ou 2 atomes d'azote, ledit noyau hétéroaromatique à cinq membres étant attaché via un carbone et étant éventuellement substitué par un ou plusieurs groupes qui peuvent être identiques ou différents choisis parmi X" ; ou

          un noyau hétéroaromatique à six membres contenant un ou deux hétéroatomes choisis parmi 0 ou 1 atome d'oxygène, 0 ou 1 atome de soufre et 0, 1 ou 2 atomes d'azote, ledit noyau hétéroaromatique à six membres étant attaché via un carbone et étant éventuellement substitué par un ou plusieurs groupes qui peuvent être identiques ou différents choisis parmi X" ;

       Q' est H ; un groupe (C1-C6)alkyle éventuellement substitué par un ou plusieurs halogènes, CN, groupes (C1-C3)alcoxy, (C1-C6)-alcoxycarbonyle, ou phényle éventuellement substitué par un ou plusieurs halogènes, CN, NO2, groupes (C1-C4)alkyle, (C1-C4)halogénoalkyle, (C1-C4)-alkylsulfonyle ou (C1-C4)alkylsulfinyle ;

          (C2-C6)alcényle ; (C2-C6)alcynyle ; ou phényle éventuellement substitué par un à trois groupes, qui peuvent être identiques ou différents, choisis parmi X" ;

       R23, R24, R25, R26, R27, R28 et R29 sont chacun indépendamment H ou un groupe (C1-C4)alkyle ;

       et la configuration en ligne pointillée C
    N représente une double liaison ou une liaison simple ; ou

       un de ses stéréoisomères

    et dans laquelle l'insecticide de type arylpyrrole est un composé de formule VI
    dans laquelle Ar est
    Hal est Cl ou Br ;

    x est un entier valant 1, 2, 3, 4, 5 ou 6 ;

    D est H, un groupe (C1-C6)alkyle éventuellement substitué par un ou plusieurs halogènes, CN, OH, groupes (C1-C4)alcoxy, (C1-C4)halogénoalcoxy, (C1-C5)alkylthio, (C1-C4)-alkylcarbonyloxy, (C1-C4)-halogénoalkylthio, (C2-C6)-alcénylcarbonyloxy, phénylcarbonyloxy, halogénophénylcarbonyloxy, phénoxy, halogénophénoxy, phényle, halogénophényle ou (C1-C3)alkylphényle,

       (C2-C6)alcényle, (C2-C6)halogénoalcényle, CN, (C2-C6)alcynyle, (C2-C6)halogénoalcynyle, di[(C1-C4)alkyle]aminocarbonyle ou (C3-C6)polyméthylèneiminocarbonyle ;

    L est H ou un halogène ;

    M et M1 sont chacun indépendamment H, un halogène, CN, NO2, un groupe (C1-C4)alkyle, (C1-C4)halogénoalkyle, (C1-C4)alcoxy, (C1-C4)-halogénoalcoxy, (C1-C4)alkylthio, (C1-C4)halogénoalkylthio, (C1-C4)-alkylsulfonyle, (C1-C4)halogénoalkylsulfonyle, (C1-C4)alkylcarbonyle, (C1-C4)halogénoalkylcarbonyle, NR35R36 ou lorsque M et M1 sont attachés à des atomes de carbone adjacents, ils peuvent être pris ensemble avec les atomes de carbone auxquels ils sont attachés pour former un cycle dans lequel MM1 représente

       -OCH2O-, -OCF2O- ou -CH=CH-CH=CH- ;

    A' est O ou s;

    R30, R31 et R32 sont chacun indépendamment un hydrogène, un halogène, NO2, CHO ou R31 et R32 peuvent être pris ensemble avec les atomes de carbone auxquels ils sont attachés pour former un cycle dans lequel R31 R32 représentent
    L', L", T et V sont chacun indépendamment H, un halogène, CN ou NO2 à condition que pas plus de deux parmi L', L", T ou V soient NO2 ; et

    R35 et R35 sont chacun indépendamment H ou un groupe (C1-C4)alkyle.
  2. Composition selon la revendication 1 dans laquelle le rapport de l'antagoniste des canaux sodiques neuronaux à l'insecticide de type arylpyrrole est d'environ 1:10 à 1:50.
  3. Composition selon la revendication 2 dans laquelle ledit antagoniste des canaux sodiques neuronaux et ledit insecticide de type arylpyrrole sont dispersés dans un diluant liquide ou solide inerte.
  4. Composition selon la revendication 1 ayant un composé de formule I ou de formule III dans lequel la configuration en ligne pointillée CN représente une double liaison.
  5. Composition selon la revendication 4 dans laquelle W est O ; X est un groupe trifluorométhoxy et est en position 4; Y est un groupe trifluorométhyle et est en position 3 ; Z est CN et est en position 4 ; A est CH2 ; n vaut 0 ; m, p, et q valent chacun indépendamment 1 ; R et R1 sont chacun indépendamment H ; Z' est Cl ; R33 et G sont chacun indépendamment CO2CH3 ; et Q est un groupe p-(trifluorométhoxy)phényle.
  6. Composition selon la revendication 1 ayant un insecticide de type arylpyrrole de formule VI dans laquelle D est H ou un groupe éthoxyméthyle ; Ar est un groupe phényle substitué par un ou deux halogènes ou groupes halogénométhyle ; et x vaut 1.
  7. Procédé pour la lutte synergique contre des insectes qui consiste à mettre en contact ledit insecte avec une quantité synergiquement efficace d'une combinaison d'un antagoniste des canaux sodiques neuronaux et d'un insecticide de type arylpyrrole comme décrit dans la revendication 1.
  8. Procédé selon la revendication 7 dans lequel l'antagoniste des canaux sodiques neuronaux est présent dans un rapport avec l'insecticide de type arylpyrrole d'environ 1:10 à 1:50 et ayant un composé antagoniste des canaux sodiques neuronaux de formule I ou de formule III dans lequel la configuration en ligne pointillée CN représente une double liaison et W est O ; X est un groupe trifluorométhoxy et est en position 4 ; Y est un groupe trifluorométhyle et est en position 3 ; Z est CN et est en position 4 ; A est CH2 ; n vaut 0 ; m, p, et q valent chacun indépendamment 1 ; R et R1 sont chacun indépendamment H ; Z' est Cl ; R33 et G sont chacun indépendamment CO2CH3 ; et Q est un groupe p-(trifluorométhoxy)phényle.
  9. Procédé selon la revendication 7 ayant un insecticide de type arylpyrrole de formule VI dans laquelle D est H ou un groupe éthoxyméthyle ; Ar est un groupe phényle substitué par un ou deux halogènes ou groupes halogénométhyle ; et x vaut 1.
  10. Procédé pour protéger une plante contre une infestation et une attaque par des insectes qui consiste à appliquer sur le feuillage ou la tige de ladite plante une quantité synergiquement efficace d'une composition selon la revendication 1.






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