Active compound combinations having insecticidal properties

The invention relates to novel insecticidal active compound combinations comprising, firstly, anthrlamides (group 1) and, secondly, further insecticidal active compounds selected from the group of the (thio)phosphates (group 2) and/or the group of the carbamates (group 3), which combinations are highly suitable for controlling animal pests, such as insects.

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Description

The present invention relates to novel active compound combinations comprising, firstly, known anthranilamides and, secondly, further known insecticidally active compounds, which combinations are highly suitable for controlling animal pests, such as insects.

It is already known that certain anthranilamides have insecticidal properties (WO 01/70671, WO 02/094791, WO 03/015519, WO 03/016284, WO 03/015518, WO 03/024222, WO 03/016282, WO 03/016283, WO 03/062226, WO 03/027099).

The generic formulae and definitions described in these publications, and the individual compounds described therein, are expressly incorporated herein by way of reference.

Furthermore, it is already known than numerous heterocycles, organotin compounds, benzoylureas and pyrethroids have insecticidal and acaricidal properties (cf. WO 93/22297, WO 93/10083, DE-A 26 41 343, EP-A 347 488, EP-A 210 487, U.S. Pat. No. 3,364,177 and EP-A 234 045). However, the activity of these compounds is likewise not always satisfactory.

It has now been found that mixtures of anthranilamides of the formula (I) (group 1)
in which

    • A1 and A2 independently of one another represent oxygen or sulfur,,
    • X1 represents N or CR10,
    • R1 represents hydrogen or represents C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl or C3-C6-cycloalkyl, each of which is optionally mono- or polysubstituted, where the substituents independently of one another may be selected from the group consisting of R6, halogen, cyano, nitro, hydroxyl, C1-C4-alkoxy, C1-C4-alkylthio, C1-C4-alkylsulfinyl, C1-C4-alkylsulfonyl, C2-C4-alkoxycarbonyl, C1-C4-alkylamino, C2-C8-dialkylamino, C3-C6-cycloalkylamino, (C1-C4-alkyl)-C3-C6-cycloalkylamino and R11,
    • R2 represents hydrogen, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-Cycloalkyl, C1-C4-alkoxy, C1-C4-alkylamino, C2-C8-dialkylamino, C3-C6-cycloalkylamino, C2-C6-alkoxycarbonyl or C2-C6-alkylcarbonyl,
    • R3 represents hydrogen, R11 or represents C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkyl, C3-C6-cycloalkyl, each of which is optionally mono- or polysubstituted, where the substituents independently of one another may be selected from the group consisting of R6, halogen, cyano, nitro, hydroxyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C1-C4-alkylthio, C1-C4-alkylsulfinyl, C1-C4-alkylsulfonyl, C2-C6-alkoxycarbonyl, C2-C6-alkylcarbonyl, C3-C6-trialkylsilyl, R11, phenyl, phenoxy and a 5- or 6-membered heteroaromatic ring, where each phenyl, phenoxy and 5- or 6-membered heteroaromatic ring may optionally be substituted and where the substituents independently of one another may be selected from one to three radicals W or one or more radicals R12, or
    • R2 and R3 may be attached to one another and form-the ring M,
    • R4 represents hydrogen, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl, C1-C6-haloalkyl, C2-C6-haloalkenyl, C2-C6-haloalkynyl, C3-C6-halocycloalkyl, halogen, cyano, nitro, hydroxyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C1-C4-alkylthio, C1-C4-alkylsulfinyl, C1-C4-alkylsulfonyl, C1-C4-haloalkylthio, C1-C4-haloalkylsulfinyl, C1-C4-haloalkylsulfonyl, C1-C4-alkylamino, C2-C8-dialkylamino, C3-C6Cycloalkylamino, C3-C6-trialkylsilyl or represents phenyl, benzyl or phenoxy, each of which is optionally mono or polysubstituted, where the substituents independently of one another may be selected from the group consisting of C1-C4-alkyl, C2-C4-alkenyl, C2-C4-alkynyl, C3-C6-cycloalkyl, C1-C4-haloalkyl, C2-C4-haloalkenyl, C2-C4-haloalkynyl, C3-C6-halocycloalkyl, halogen, cyano, nitro, C1-C4-alkoxy, C1-C4-haloalkoxy, C1-C4-alkylthio, C1-C4-alkylsulfinyl, C1-C4-alkylsulfonyl, C1-C4-alkylamino, C2-C8-dialkylamino, C3-C6-cycloalkylamino, C3-C6-allyl)cycloalkylamino, C2-C4-alkylcarbonyl, C2-C6-alkoxycarbonyl, C2-C6-alkylaminocarbonyl, C3-C8-dialkylaminocarbonyl and C3-C6-trialkylsilyl,
    • R5 and R8 in each case independently of one another represent hydrogen, halogen or represent in each case optionally substituted C1-C4-alkyl, C1-C4-haloallyl, R12, G, J, —OJ, —OG, —S(O)p-J, —S(O)p-G G, —S(O)p-phenyl, where the substituents independently of one another may be selected from one to three radicals -W or from the group consisting of R12, C1-C10-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C4-alkoxy and C1-C4-alkylthio, where each substituent may be substituted by one or more substituents independently of one another selected from the group consisting of G, J, R6, halogen, cyano, nitro, amino, hydroxyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C1-C4-alkylthio, C1-C4-alkylsulfinyl, C1-C4-alkylsulfonyl, C1-C4-haloalkylthio, C1-C4-haloalkylsulfinyl, C1-C4-haloalkylsulfonyl, C1-C4-alkylamino, C2-C8-dialkylamino, C3-C6-trialkylsilyl, phenyl and phenoxy, where each phenyl or phenoxy ring may optionally be substituted and where the substituents independently of one another may be selected from one to three radicals W or one or more radicals R12,
    • G in each case independently of one another represent a 5- or 6membered non-aromatic carbocyclic or heterocyclic ring which may optionally contain one or two ring members from the group consisting of C(═O), SO and S(═O)2 and which may optionally be substituted by one to four substituents independently of one another selected from the group consisting of C1-C2-alkyl, halogen, cyano, nitro and C1-C2-alkoxy, or independently of one another represent C2-C6-alkenyl, C2-C6-alkynyl, C3-C7-cycloalkyl, (cyano-C3-C7-cycloalkyl, (C1-C4-(alkyl)-C3-C6-Cycloalkyl, (C3-C6-cycloalkyl)-C1-C4-alkyl, where each cycloalkyl, (alkyl)cycloalkyl and (cycloalkyl)alkyl may optionally be substituted by one or more halogen atoms,
    • J in each case independently of one another represent an optionally substituted 5- or 6-membered heteroaromatic ring, where the substituents independently of one another may be selected from one to three radicals W or one or more radicals R12,
    • R6 independently of one another represent —C(=E1)R19, -LC(=E1)R19, —C(=E1)LR19, -LC(=E1)LR19, —OP(=Q)(OR19)2, —SO2LR18 or -LSO2LR19, where each E1 independently of one another represents O, S, N—R15, N—OR15, N—N(R15)2, N—S═O, N—CN or N—NO2,
    • R7 represents hydrogen, C1-C4-alkyl, C1-C4-haloalkyl, halogen, C1-C4-alkoxy, C1-C4-haloalkoxy, C1-C4-alkylthio, C1-C4-alkylsulfinyl, C1-C4-alkylsulfonyl, C1-C4-haloalkylthio, C1-C4-haloalkylsulfinyl, C1-C4-haloalkylsulfonyl,
    • R9 represents C1-C4-haloalkyl, C1-C4-haloalkoxy, C1-C4-haloalkylsulfinyl or halogen,
    • R10 represents hydrogen, C1-C4-alkyl, C1-C4-haloalkyl, halogen, cyano or C1-C4-haloalkoxy,
    • R11 in each case independently of one another represents in each case optionally mono- to trisubstituted C1-C6-alkylthio, C1-C6-alkylsulfenyl, C1-C6-haloalkythio, C1-C6-haloalkylsulfenyl, phenylthio or phenylsulfenyl, where the substituents independently of one another may be selected from the list W, —S(O)nN(R16)2, —C(═O)R13, -L(C═O)R14, —S(C═O)LR14, —C(═O)LR13, —S(O)nNR13C(═O)R13, —S(O)nNR13C(═O)LR14 or —S(O)nNR13S(O)2LR14,
    • L in each case independently of one another represents O, NR18 or S,
    • R12 in each case independently of one another represents —B(OR17)2, amino, SH, thiocyanato, C3-C8-trialkylsilyloxy, C1-C4-alkyl disulfide, —SF5, —C(=E1)R19, -LC(=E1)R19, —C(=E1)LR19, -LC(=E1)LR19, —OP(=Q)(OR19)2, —SO2LR19 or -LSO2LR19,
    • Q represents O or S,
    • R13 in each case independently of one another represent hydrogen or represent in each case optionally mono- or polysubstituted C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl or C3-C6-cycloalkyl, where the substituents independently of one another may be selected from the group consisting of R6, halogen, cyano, nitro, hydroxyl, C1-C4-alkoxy, C1-C4-alkylsulfinyl, C1-C4-alkylsulfonyl, C1-C4-alkylamino, C2-C8-dialkylamino, C3-C6-cycloalkylamino or (C1-C4-alkyl)-C3-C6-cycloalkylamino,
    • R14 in each case independently of one another represent in each case optionally mono- or polysubstituted C1-C20-alkyl, C2-C20-alkenyl, C2-C20-alkynyl or C3-C6-cycloalkyl, where the substituents independently of one another may be selected from the group consisting of R6, halogen, cyano, nitro, hydroxyl, C1-C4-alkoxy, C1-C4-alkylsulfinyl, C1-C4-alkylsulfonyl, C1-C4-alkylamino, C2-C8-dialkylamino, C3-C6-cycloalkylamino and (C1-C4-alkyl)-C3-C6-cycloalkylamino or represent optionally substituted phenyl, where the *substituents independently of one another may be selected from one to three radicals W or one or more radicals R12,
    • R15 in each case independently of one another represent hydrogen or represent in each case optionally mono- or polysubstituted C1-C6-haloaikyl or C1-C6-alkyl, where the substituents independently of one another may be selected from the group consisting of cyano, nitro, hydroxyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C1-C4-alkylthio, C1-C4-alkylsulfinyl, C1-C4-alkylsulfonyl, C1-C4-haloalkylthio, C1-C4-haloalkylsulfinyl, C1-C4-haloalkylsulfonyl, C1-C4-alkylamino, C2-C9-dialkylamino, C2-C6-alkoxycarbonyl, C2-C6-alkylcarbonyl, C3-C6-trialkylsilyl and optionally substituted phenyl, where the substituents independently of one another may be selected from one to three radicals W or one or more radicals R12, or N(R15)2 represents a cycle which forms the ring M,
    • R16 represents C1-C2-alkyl or C1-C12-haloalkyl, or N(R16)2 represents a cycle which forms the ring M,
    • R17 in each case independently of one another represent hydrogen or C1-C4-alkyl, or B(OR17)2 represents a ring in which the two oxygen atoms are attached via a chain having two to three carbon atoms which are optionally substituted by one or two substituents independently of one another selected from the group consisting of methyl and C2-C6-alkoxycarbonyl,
    • R18 in each case independently of one another represent hydrogen, C1-C6-alkyl or C1-C6-haloalkyl, or N(R3)(R18) represents a cycle which forms the ring M,
    • R19 in each case independently of one another represent hydrogen or represent in each case mono- or polysubstituted C1-C6-alkyl, where the substituents independently of one another may be selected from the group consisting of cyano, nitro, hydroxyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C1-C4-alkylthio, C1-C4-alkylsulfinyl, C1-C4-alkylsulfonyl, C1-C4-haloalkylthio, C1-C4-haloalkylsulfinyl, C1-C4-haloalkylsulfonyl, C1-C4-alkylamino, C2-C8-dialkylamino, CO2H, C2-C6-carboxycarbonyl, C2-C6-alkylcarbonyl, C3-C6-trialkylsilyl and optionally substituted phenyl, where the substituents independently of one another may be selected from one to three radicals W, C1-C6-haloalkyl, C3-C6-cycloalkyl or phenyl or pyridyl, each of which is optionally mono- to trisubstituted by W,
    • M in each case represents an optionally mono- to tetrasubstituted ring which, in addition to the nitrogen atom attached to the substituent pair R13 and R18, (R15)2 or (R16)2, contains two to six carbon atoms and optionally additionally a further nitrogen, sulfur or oxygen atom, where the substituents independently of one another may be selected from the group consisting of C1-C2-alkyl, halogen, cyano, nitro and C1-C2-alkoxy,
    • W in each case independently of one another represent C1-C4-alkyl, C2-C4-alkenyl, C2-C4-alkynyl, C3-C6-cycloalkyl, C1-C4-haloalkyl, C2-C4-haloalkenyl, C2-C4-haloalkynyl, C3-C6-halocycloalkyl, halogen, cyano, nitro, C1-C4-alkoxy, C1-C4-haloalkoxy, C1-C4-alkylthio, C1-C4-alkylsulfinyl, C1-C4-alkylsulfonyl, C1-C4-alkylamino, C2-C8-dialkylamino, C3-C6-cycloalkylamino, (C1-C4-alkyl)-C3-C6-cycloalkylamino, C2-C4-alkylcarbonyl, C2-C6-alkoxycarbonyl, CO2H, C2-C6-alkylaminocarbonyl, C3-C8-dialkylaminocarbonyl or C3-C6-trialkylsilyl,
    • n in each case independently of one another represent 0 or 1,
    • p in each case independently of one another represent 0, 1 or 2,
    • where, if (a) R5 represents hydrogen, C1-C6-alkyl, C1-C6-haloalkyl, C2-C6-haloalkenyl, C2-C6-haloalkynyl, C1-C4-haloalkoxy, C1-C4-haloalkylthio or halogen and (b) R8 represents hydrogen, C1-C6-alkyl, C1-C6-haloalkyl, C2-C6-haloalkenyl, C2-C6-haloalkynyl, C1-C4-haloalkoxy, C1-C4-haloalkylthio, halogen, C2-C4-alkylcarbonyl, C2-C6-alkoxycarbonyl, C2-C6-alkylaminocarbonyl or C3-C8 dialkylaminocarbonyl, (c) at least one substituent selected from the group consisting of R6, R11 and R12 is present and (d) if R12 is not present, at least one of the radicals R6 and R11 is different from C2-C6-alkylcarbonyl, C2-C6 alkoxycarbonyl, C2-C6-alkylaminocarbonyl and C3-C8-dialkylaminocarbonyl, and
    • where the compound of the general formula (I) may also be an N-oxide or salt,
    • and at least one insecticidally active compound of groups 2 and 3 below selected from
    • A) (thio)phosphates (group 2), preferably
      • (2-1) azinphos-methyl (known from U.S. Pat. No. 2,758,115)
      • and/or
      • (2-2) chlorpyrifos (known from U.S. Pat. No. 3,244,586)
      • and/or
      • (2-3) diazinon (known from U.S. Pat. No. 2,754,243)
      • and/or
      • (2-4) dimethoate (known from U.S. Pat. No. 2,494,283)
      • and/or
      • (2-5) disulfoton (known from DE-A 91 76 68)
      • and/or
      • (2-6) ethion (known from U.S. Pat. No. 2,873,228)
      • and/or
      • (2-7) fenitrothion (known from BE-A 0 594 669)
      • and/or
      • (2-8) fenthion (known from DE-A 11 16656)
      • and/or
      • (2-9) isoxathion (known from DE-A 15 67 137)
      • and/or
      • (2-10) malathion (known from U.S. Pat. No. 2,578,562)
      • and/or
      • (2-11) methidathion (known from DE-A 16 45 982)
      • and/or
      • (2-12) oxydemeton-methyl (known from DE-A 94 73 68)
      • and/or
      • (2-13) parathion (known from DE-A 81 41 52)
      • and/or
      • (2-14) parathion-methyl (known from DE-A 81 41 42)
      • and/or
      • (2-15) phenthoate (known from GB-A 834 814)
      • and/or
      • (2-16) phorate (known from U.S. Pat. No. 2,586,655)
      • and/or
      • (2-17) phosalone (known from DE-A 24 31 192)
      • and/or
      • (2-18) phosmet (known from U.S. Pat. No. 2,767,194)
      • and/or
      • (2-19) phoxim (known from DE-A 12 38 902)
      • and/or
      • (2-20) pirimiphos-methyl (known from DE-A 14 45 949)
      • and/or
      • (2-21) profenophos (known from DE-A 22 49 462)
      • and/or
      • (2-22) prothiophos (known from DE-A 21 11 414)
      • and/or
      • (2-23) tebupirimphos (known from DE-A 33 17 824)
      • and/or
      • (2-24) triazophos (known from DE-A 12 99 924)
      • and/or
      • (2-25) chlorfenvinphos (known from U.S. Pat. No. 2,956,073)
      • and/or
      • (2-26) dichlorphos (known from GB-A 775 085)
      • and/or
      • (2-27) dicrotophos (known from BE-A 55 22 84)
      • and/or
      • (2-28) mevinphos (known from U.S. Pat. No. 2,685,552)
      • and/or
      • (2-29) monocrotophos (known from DE-A 19 64 535)
      • and/or
      • (2-30) phosphamidon (known from U.S. Pat. No. 2,908,605)
      • and/or
      • (2-31) acephate (known from DE-A 20 14 027)
      • and/or
      • (2-32) methamidophos (known from U.S. Pat. No. 3,309,266)
      • and/or
      • (2-33) trichlorfon (known from U.S. Pat. No. 2,701,225)
        and/or
    • B) carbamates (group 3), preferably
      • (3-1) carbaryl (known from U.S. Pat. No. 2,903,478)
      • and/or
      • (3-2) fenoxycarb (known from EP-A 0 004 334)
      • and/or
      • (3-3) formetanate (known from DE-A 11 69 194)
      • and/or
      • (3-4) formetanate hydrochloride (known from DE-A 11 69 194)
      • and/or
      • (3-5) methiocarb (known from DE-A 11 62 352)
      • and/or
      • (3-6) methomyl (known from U.S. Pat. No. 3,639,620)
      • and/or
      • (3-7) oxamyl (known from DE-A 17 68 623)
      • and/or
      • (3-8) pirimicab (=Pirimor) (known from GB-A 1 181 657)
      • and/or
      • (3-9) propoxur (known from DE-A 11 08 202)
      • and/or
      • (3-10) thiodicarb (known from DE-A 25 30 439)
        are synergistically effective and suitable for controlling animal pests.

Surprisingly, the insecticidal and acaricidal activity of the active compound combination according to the invention is considerably higher than the sum of the activities of the individual active compounds. An unforeseeable true synergistic effect is present, and not just an addition of activities.

In addition to at least one active compound of the formula (I), the active compound combinations according to the invention comprise at least one active compound of group 2 [selected from the compounds (2-1) to (2-33)] and/or group 3 [selected from the compounds (3-1) to (3-10)].

Depending inter alia on the nature of the substituents, the compounds of the formula (I) can be present as geometrical and/or optical isomers or isomer mixtures of varying composition which, if appropriate, can be separated in a customary manner. The present invention provides both the pure isomers and the isomer mixtures, their preparation and use and compositions comprising them. However, hereinbelow, for the sake of simplicity, only compounds of the formula (I) are referred to, although what is meant are both the pure compounds and, if appropriate, also mixtures having varying proportions of isomeric compounds.

Preference is given to active compound combinations comprising compounds of the formula (I-1)
in which

    • R2 represents hydrogen or C1-C6-alkyl,
    • R3 represents C1-C6-alkyl which is optionally substituted by one R6,
    • R4 represents C1-C4-alkyl, C1-C2-haloalkyl, C1-C2-haloalkoxy or halogen,
    • R5 represents hydrogen, C1-C4-alkyl, C1-C2-haloalkyl, C1-C2-haloalkoxy or halogen,
    • R6 represents —C(=E2)R19, -LC(=E2)R19, —C(=E2)LR19 or -LC(=E2)LR19, where each E2 independently of one another represents O, S, N—R15, N—OR15, N—N(R15)2, and each L independently of one another represents O or NR18,
    • R7 represents C1-C4-haloalkyl or halogen,
    • R9 represents C1-C2-haloalkyl, C1-C2-haloalkoxy, S(O)p-C1-C2-haloalkyl or halogen,
    • R15 in each case independently of one another represent hydrogen or represent in each case optionally substituted C1-C6-haloalkyl or C1-C6-alkyl, where the substituents independently of one another may be selected from the group consisting of cyano, C1-C4-alkoxy, C1-C4-haloalkoxy, C1-C4-alkylthio, C1-C4-alkylsulfinyl, C1-C4-alkylsulfonyl, C1-C4-haloalkylthio, C1-C4-haloalkylsulfinyl and C1-C4-haloalkylsulfonyl,
    • R18 in each case represents hydrogen or C1-C4-alkyl,
    • R19 in each case independently of one another represent hydrogen or C1-C6-alkyl,
    • p independently of one another represent 0, 1, 2,
    • and at least one active compound of group 2 [selected from the compounds (2-1) to (2-33)] and/or of group 3 [selected from the compounds (3-1) to (3-10)].

In the radical definitions mentioned as being preferred, halogen represents fluorine, chlorine, bromine and iodine, in particular fluorine, chlorine and bromine.

Particular preference is given to active compound combinations comprising compounds of the formula (I-1) in which

    • R2 represents hydrogen or methyl,
    • R3 represents C1-C4-alkyl (in particular methyl,-ethyl, n-, isopropyl, n-, iso-, sec-, tert-butyl),
    • R4 represents methyl, trifluoromethyl, trifluoromethoxy, fluorine, chlorine, bromine or iodine,
    • R5 represents hydrogen, fluorine, chlorine, bromine, iodine, trifluoromethyl or trifluoromethoxy,
    • R7 represents chlorine or bromine,
    • R9 represents trifluoromethyl, chlorine, bromine, difluoromethoxy or trifluoroethoxy, and at least one active compound of group 2 [selected from the compounds (2-1) to (2-33)] and/or of group 3 [selected from the compounds (3-1) to (3-10)].

Very particular preference is given to active compound combinations comprising the following compounds of the formula (I-1):

(I-1) Example m.p. No. R2 R3 R4 R5 R7 R9 (° C.) I-1-1 H Me Me Cl Cl CF3 185-186 I-1-2 H Me Me Cl Cl OCH2CF3 207-208 I-1-3 H Me Me Cl Cl Cl 225-226 I-1-4 H Me Me Cl Cl Br 162-164 I-1-5 H Me Cl Cl Cl CF3 155-157 I-1-6 H Me Cl Cl Cl OCH2CF3 192-195 I-1-7 H Me Cl Cl Cl Cl 205-206 I-1-8 H Me Cl Cl Cl Br 245-246 I-1-9 H i-Pr Me Cl Cl CF3 195-196 I-1-10 H i-Pr Me Cl Cl OCH2CF3 217-218 I-1-11 H i-Pr Me Cl Cl Cl 173-175 I-1-12 H i-Pr Me Cl Cl Br 159-161 I-1-13 H i-Pr Cl Cl Cl CF3 200-201 I-1-14 H i-Pr Cl Cl Cl OCH2CF3 232-235 I-1-15 H i-Pr Cl Cl Cl Cl 197-199 I-1-16 H i-Pr Cl Cl Cl Br 188-190 I-1-17 H Et Me Cl Cl CF3 163-164 I-1-18 H Et Me Cl Cl OCH2CF3 205-207 I-1-19 H Et Me Cl Cl Cl 199-200 I-1-20 H Et Me Cl Cl Br 194-195 I-1-21 H Et Cl Cl Cl CF3 201-202 I-1-22 H Et Cl Cl Cl Cl 206-208 I-1-23 H Et Cl Cl Cl Br 214-215 I-1-24 H t-Bu Me Cl Cl CF3 223-225 I-1-25 H t-Bu Me Cl Cl Cl 163-165 I-1-26 H t-Bu Me Cl Cl Br 159-161 I-1-27 H t-Bu Cl Cl Cl CF3 170-172 I-1-28 H t-Bu Cl Cl Cl Cl 172-173 I-1-29 H t-Bu Cl Cl Cl Br 179-180 I-1-30 H Me Me Br Cl CF3 222-223 I-1-31 H Et Me Br Cl CF3 192-193 I-1-32 H i-Pr Me Br Cl CF3 197-198 I-1-33 H t-Bu Me Br Cl CF3 247-248 I-1-34 H Me Me Br Cl Cl 140-141 I-1-35 H Et Me Br Cl Cl 192-194 I-1-36 H i-Pr Me Br Cl Cl 152-153 I-1-37 H t-Bu Me Br Cl Cl 224-225 I-1-38 H Me Me Br Cl Br 147-149 I-1-39 H Et Me Br Cl Br 194-196 I-1-40 H i-Pr Me Br Cl Br 185-187 I-1-41 H t-Bu Me Br Cl Br 215-221 I-1-42 H Me Me I Cl CF3 199-200 I-1-43 H Et Me I Cl CF3 199-200 I-1-44 H i-Pr Me I Cl CF3 188-189 I-1-45 H t-Bu Me I Cl CF3 242-243 I-1-46 H Me Me I Cl Cl 233-234 I-1-47 H Et Me I Cl Cl 196-197 I-1-48 H i-Pr Me I Cl Cl 189-190 I-1-49 H t-Bu Me I Cl Cl 228∝229 I-1-50 H Me Me I Cl Br 229-230 I-1-51 H iPr Me I Cl Br 191-192 I-1-52 H Me Br Br Cl CF3 162-163 I-1-53 H Et Br Br Cl CF3 188-189 I-1-54 H i-Pr Br Br Cl CF3 192-193 I-1-55 H t-Bu Br Br Cl CF3 246-247 I-1-56 H Me Br Br Cl Cl 188-190 I-1-57 H Et Br Br Cl Cl 192-194 I-1-58 H i-Pr Br Br Cl Cl 197-199 I-1-59 H t-Bu Br Br Cl Cl 210-212 I-1-60 H Me Br Br Cl Br 166-168 I-1-61 H Et Br Br Cl Br 196-197 I-1-62 H i-Pr Br Br Cl Br 162-163 I-1-63 H t-Bu Br Br Cl Br 194-196 I-1-64 H t-Bu Cl Br Cl CF3 143-145 I-1-65 Me Me Br Br Cl Cl 153-155 I-1-66 Me Me Me Br Cl CF3 207-208 I-1-67 Me Me Cl Cl Cl Cl 231-232 I-1-68 Me Me Br Br Cl Br 189-190 I-1-69 Me Me Cl Cl Cl Br 216-218 I-1-70 Me Me Cl Cl Cl CF3 225-227 I-1-71 Me Me Br Br Cl CF3 228-229 I-1-72 H i-Pr Me H Cl CF3 237-239

and at least one active compound of group 2 [selected from the compounds (2-1) to (2-33)] and/or of group 3 [selected from the compounds (3-1) to (3-10)].

Especially preferred are active compound combinations comprising a compound of the formulae below
and at least one active compound of group 2 [selected from the compounds (2-1) to (2-33)] and/or of group 3 [selected from the compounds (3-1) to (3-10)].

Preference is given to active compound combinations which preferably comprise the following active compounds of group 2:

(2-2) chlorpyrifos,

(2-31) acephate,

(2-32) methamidophos.

Preference is given to active compound combinations according to the invention which preferably comprise the following active compounds of group 3:

(3-1) carbaryl,

(3-5) methiocarb,

(3-10) thiodicarb.

Emphasis is given to the following specifically mentioned active compound combinations (2-component mixtures) comprising a compound of the formula (I-1) and the stated active compound of group 2 or of group 3:

Active compound combination No. comprising  1a) (I-1-1) and (2-2) chlorpyrifos  1b) (I-1-1) and (2-31) acephate  1c) (I-1-1) and (2-32) methamidophos  1d) (I-1-1) and (3-1) carbaryl  1e) (I-1-1) and (3-5) methiocarb  1f) (I-1-1) and (3-10) thiodicarb  2a) (I-1-2) and (2-2) chlorpyrifos  2b) (I-1-2) and (2-31) acephate  2c) (I-1-2) and (2-32) methamidophos  2d) (I-1-2) and (3-1) carbaryl  2e) (I-1-2) and (3-5) methiocarb  2f) (I-1-2) and (3-10) thiodicarb  3a) (I-1-3) and (2-2) chlorpyrifos  3b) (I-1-3) and (2-31) acephate  3c) (I-1-3) and (2-32) methamidophos  3d) (I-1-3) and (3-1) carbaryl  3e) (I-1-3) and (3-5) methiocarb  3f) (I-1-3) and (3-10) thiodicarb  4a) (I-1-4) and (2-2) chlorpyrifos  4b) (I-1-4) and (2-31) acephate  4c) (I-1-4) and (2-32) methamidophos  4d) (I-1-4) and (3-1) carbaryl  4e) (I-1-4) and (3-5) methiocarb  4f) (I-1-4) and (3-10) thiodicarb  5a) (I-1-5) and (2-2) chlorpyrifos  5b) (I-1-5) and (2-31) acephate  5c) (I-1-5) and (2-32) methamidophos  5d) (I-1-5) and (3-1) carbaryl  5e) (I-1-5) and (3-5) methiocarb  5f) (I-1-5) and (3-10) thiodicarb  6a) (I-1-6) and (2-2) chlorpyrifos  6b) (I-1-6) and (2-31) acephate  6c) (I-1-6) and (2-32) methamidophos  6d) (I-1-6) and (3-1) carbaryl  6e) (I-1-6) and (3-5) methiocarb  6f) (I-1-6) and (3-10) thiodicarb  7a) (I-1-7) and (2-2) chlorpyrifos  7b) (I-1-7) and (2-31) acephate  7c) (I-1-7) and (2-32) methamidophos  7d) (I-1-7) and (3-1) carbaryl  7e) (I-1-7) and (3-5) methiocarb  7f) (I-1-7) and (3-10) thiodicarb  8a) (I-1-8) and (2-2) chlorpyrifos  8b) (I-1-8) and (2-31) acephate  8c) (I-1-8) and (2-32) methamidophos  8d) (I-1-8) and (3-1) carbaryl  8e) (I-1-8) and (3-5) methiocarb  8f) (I-1-8) and (3-10) thiodicarb  9a) (I-1-9) and (2-2) chlorpyrifos  9b) (I-1-9) and (2-31) acephate  9c) (I-1-9) and (2-32) methamidophos  9d) (I-1-9) and (3-1) carbaryl  9e) (I-1-9) and (3-5) methiocarb  9f) (I-1-9) and (3-10) thiodicarb 10a) (I-1-11) and (2-2) chlorpyrifos 10b) (I-1-11) and (2-31) acephate 10c) (I-1-11) and (2-32) methamidophos 10d) (I-1-11) and (3-1) carbaryl 10e) (I-1-11) and (3-5) methiocarb 10f) (I-1-11) and (3-10) thiodicarb 11a) (I-1-12) and (2-2) chlorpyrifos 11b) (I-1-12) and (2-31) acephate 11c) (I-1-12) and (2-32) methamidophos 11d) (I-1-12) and (3-1) carbaryl 11e) (I-1-12) and (3-5) methiocarb 11f) (I-1-12) and (3-10) thiodicarb 12a) (I-1-13) and (2-2) chlorpyrifos 12b) (I-1-13) and (2-31) acephate 12c) (I-1-13) and (2-32) methamidophos 12d) (I-1-13) and (3-1) carbaryl 12e) (I-1-13) and (3-5) methiocarb 12f) (I-1-13) and (3-10) thiodicarb 13a) (I-1-15) and (2-2) chlorpyrifos 13b) (I-1-15) and (2-31) acephate 13c) (I-1-15) and (2-32) methamidophos 13d) (I-1-15) and (3-1) carbaryl 13e) (I-1-15) and (3-5) methiocarb 13f) (I-1-15) and (3-10) thiodicarb 14a) (I-1-16) and (2-2) chlorpyrifos 14b) (I-1-16) and (2-31) acephate 14c) (I-1-16) and (2-32) methamidophos 14d) (I-1-16) and (3-1) carbaryl 14e) (I-1-16) and (3-5) methiocarb 14f) (I-1-16) and (3-10) thiodicarb 15a) (I-1-19) and (2-2) chlorpyrifos 15b) (I-1-19) and (2-31) acephate 15c) (I-1-19) and (2-32) methamidophos 15d) (I-1-19) and (3-1) carbaryl 15e) (I-1-19) and (3-5) methiocarb 15f) (I-1-19) and (3-10) thiodicarb 16a) (I-1-21) and (2-2) chlorpyrifos 16b) (I-1-21) and (2-31) acephate 16c) (I-1-21) and (2-32) methamidophos 16d) (I-1-21) and (3-1) carbaryl 16e) (I-1-21) and (3-5) methiocarb 16f) (I-1-21) and (3-10) thiodicarb 17a) (I-1-22) and (2-2) chlorpyrifos 17b) (I-1-22) and (2-31) acephate 17c) (I-1-22) and (2-32) methamidophos 17d) (I-1-22) and (3-1) carbaryl 17e) (I-1-22) and (3-5) methiocarb 17f) (I-1-22) and (3-10) thiodicarb 18a) (I-1-23) and (2-2) chlorpyrifos 18b) (I-1-23) and (2-31) acephate 18c) (I-1-23) and (2-32) methamidophos 18d) (I-1-23) and (3-1) carbaryl 18e) (I-1-23) and (3-5) methiocarb 18f) (I-1-23) and (3-10) thiodicarb 19a) (I-1-24) and (2-2) chlorpyrifos 19b) (I-1-24) and (2-31) acephate 19c) (I-1-24) and (2-32) methamidophos 19d) (I-1-24) and (3-1) carbaryl 19e) (I-1-24) and (3-5) methiocarb 19f) (I-1-24) and (3-10) thiodicarb 20a) (I-1-26) and (2-2) chlorpyrifos 20b) (I-1-26) and (2-31) acephate 20c) (I-1-26) and (2-32) methamidophos 20d) (I-1-26) and (3-1) carbaryl 20e) (I-1-26) and (3-5) methiocarb 20f) (I-1-26) and (3-10) thiodicarb 21a) (I-1-27) and (2-2) chlorpyrifos 21b) (I-1-27) and (2-31) acephate 21c) (I-1-27) and (2-32) methamidophos 21d) (I-1-27) and (3-1) carbaryl 21e) (I-1-27) and (3-5) methiocarb 21f) (I-1-27) and (3-10) thiodicarb 22a) (I-1-29) and (2-2) chlorpyrifos 22b) (I-1-29) and (2-31) acephate 22c) (I-1-29) and (2-32) methamidophos 22d) (I-1-29) and (3-1) carbaryl 22e) (I-1-29) and (3-5) methiocarb 22f) (I-1-29) and (3-10) thiodicarb 23a) (I-1-30) and (2-2) chlorpyrifos 23b) (I-1-30) and (2-31) acephate 23c) (I-1-30) and (2-32) methamidophos 23d) (I-1-30) and (3-1) carbaryl 23e) (I-1-30) and (3-5) methiocarb 23f) (I-1-30) and (3-10) thiodicarb 24a) (I-1-31) and (2-2) chlorpyrifos 24b) (I-1-31) and (2-31) acephate 24c) (I-1-31) and (2-32) methamidophos 24d) (I-1-31) and (3-1) carbaryl 24e) (I-1-31) and (3-5) methiocarb 24f) (I-1-31) and (3-10) thiodicarb 25a) (I-1-32) and (2-2) chlorpyrifos 25b) (I-1-32) and (2-31) acephate 25c) (I-1-32) and (2-32) methamidophos 25d) (I-1-32) and (3-1) carbaryl 25e) (I-1-32) and (3-5) methiocarb 25f) (I-1-32) and (3-10) thiodicarb 26a) (I-1-33) and (2-2) chlorpyrifos 26b) (I-1-33) and (2-31) acephate 26c) (I-1-33) and (2-32) methamidophos 26d) (I-1-33) and (3-1) carbaryl 26e) (I-1-33) and (3-5) methiocarb 26f) (I-1-33) and (3-10) thiodicarb 27a) (I-1-38) and (2-2) chlorpyrifos 27b) (I-1-38) and (2-31) acephate 27c) (I-1-38) and (2-32) methamidophos 27d) (I-1-38) and (3-1) carbaryl 27e) (I-1-38) and (3-5) methiocarb 27f) (I-1-38) and (3-10) thiodicarb 28a) (I-1-39) and (2-2) chlorpyrifos 28b) (I-1-39) and (2-31) acephate 28c) (I-1-39) and (2-32) methamidophos 28d) (I-1-39) and (3-1) carbaryl 28e) (I-1-39) and (3-5) methiocarb 28f) (I-1-39) and (3-10) thiodicarb 29a) (I-1-40) and (2-2) chlorpyrifos 29b) (I-1-40) and (2-31) acephate 29c) (I-1-40) and (2-32) methamidophos 29d) (I-1-40) and (3-1) carbaryl 29e) (I-1-40) and (3-5) methiocarb 29f) (I-1-40) and (3-10) thiodicarb 30a) (I-1-42) and (2-2) chlorpyrifos 30b) (I-1-42) and (2-31) acephate 30c) (I-1-42) and (2-32) methamidophos 30d) (I-1-42) and (3-1) carbaryl 30e) (I-1-42) and (3-5) methiocarb 30f) (I-1-42) and (3-10) thiodicarb 31a) (I-1-43) and (2-2) chlorpyrifos 31b) (I-1-43) and (2-31) acephate 31c) (I-1-43) and (2-32) methamidophos 31d) (I-1-43) and (3-1) carbaryl 31e) (I-1-43) and (3-5) methiocarb 31f) (I-1-43) and (3-10) thiodicarb 32a) (I-1-44) and (2-2) chlorpyrifos 32b) (I-1-44) and (2-31) acephate 32c) (I-1-44) and (2-32) methamidophos 32d) (I-1-44) and (3-1) carbaryl 32e) (I-1-44) and (3-5) methiocarb 32f) (I-1-44) and (3-10) thiodicarb 33a) (I-1-50) and (2-2) chlorpyrifos 33b) (I-1-50) and (2-31) acephate 33c) (I-1-50) and (2-32) methamidophos 33d) (I-1-50) and (3-1) carbaryl 33e) (I-1-50) and (3-5) methiocarb 33f) (I-1-50) and (3-10) thiodicarb 34a) (I-1-51) and (2-2) chlorpyrifos 34b) (I-1-51) and (2-31) acephate 34c) (I-1-51) and (2-32) methamidophos 34d) (I-1-51) and (3-1) carbaryl 34e) (I-1-51) and (3-5) methiocarb 34f) (I-1-51) and (3-10) thiodicarb 35a) (I-1-52) and (2-2) chlorpyrifos 35b) (I-1-52) and (2-31) acephate 35c) (I-1-52) and (2-32) methamidophos 35d) (I-1-52) and (3-1) carbaryl 35e) (I-1-52) and (3-5) methiocarb 35f) (I-1-52) and (3-10) thiodicarb 36a) (I-1-53) and (2-2) chlorpyrifos 36b) (I-1-53) and (2-31) acephate 36c) (I-1-53) and (2-32) methamidophos 36d) (I-1-53) and (3-1) carbaryl 36e) (I-1-53) and (3-5) methiocarb 36f) (I-1-53) and (3-10) thiodicarb 37a) (I-1-54) and (2-2) chlorpyrifos 37b) (I-1-54) and (2-31) acephate 37c) (I-1-54) and (2-32) methamidophos 37d) (I-1-54) and (3-1) carbaryl 37e) (I-1-54) and (3-5) methiocarb 37f) (I-1-54) and (3-10) thiodicarb 38a) (I-1-55) and (2-2) chlorpyrifos 38b) (I-1-55) and (2-31) acephate 38c) (I-1-55) and (2-32) methamidophos 38d) (I-1-55) and (3-1) carbaryl 38e) (I-1-55) and (3-5) methiocarb 38f) (I-1-55) and (3-10) thiodicarb 39a) (I-1-56) and (2-2) chlorpyrifos 39b) (I-1-56) and (2-31) acephate 39c) (I-1-56) and (2-32) methamidophos 39d) (I-1-56) and (3-1) carbaryl 39e) (I-1-56) and (3-5) methiocarb 39f) (I-1-56) and (3-10) thiodicarb 40a) (I-1-57) and (2-2) chlorpyrifos 40b) (I-1-57) and (2-31) acephate 40c) (I-1-57) and (2-32) methamidophos 40d) (I-1-57) and (3-1) carbaryl 40e) (I-1-57) and (3-5) methiocarb 40f) (I-1-57) and (3-10) thiodicarb 41a) (I-1-58) and (2-2) chlorpyrifos 41b) (I-1-58) and (2-31) acephate 41c) (I-1-58) and (2-32) methamidophos 41d) (I-1-58) and (3-1) carbaryl 41e) (I-1-58) and (3-5) methiocarb 41f) (I-1-58) and (3-10) thiodicarb 42a) (I-1-60) and (2-2) chlorpyrifos 42b) (I-1-60) and (2-31) acephate 42c) (I-1-60) and (2-32) methamidophos 42d) (I-1-60) and (3-1) carbaryl 42e) (I-1-60) and (3-5) methiocarb 42f) (I-1-60) and (3-10) thiodicarb 43a) (I-1-61) and (2-2) chlorpyrifos 43b) (I-1-61) and (2-31) acephate 43c) (I-1-61) and (2-32) methamidophos 43d) (I-1-61) and (3-1) carbaryl 43e) (I-1-61) and (3-5) methiocarb 43f) (I-1-61) and (3-10) thiodicarb 44a) (I-1-62) and (2-2) chlorpyrifos 44b) (I-1-62) and (2-31) acephate 44c) (I-1-62) and (2-32) methamidophos 44d) (I-1-62) and (3-1) carbaryl 44e) (I-1-62) and (3-5) methiocarb 44f) (I-1-62) and (3-10) thiodicarb 45a) (I-1-64) and (2-2) chlorpyrifos 45b) (I-1-64) and (2-31) acephate 45c) (I-1-64) and (2-32) methamidophos 45d) (I-1-64) and (3-1) carbaryl 45e) (I-1-64) and (3-5) methiocarb 45f) (I-1-64) and (3-10) thiodicarb 46a) (I-1-65) and (2-2) chlorpyrifos 46b) (I-1-65) and (2-31) acephate 46c) (I-1-65) and (2-32) methamidophos 46d) (I-1-65) and (3-1) carbaryl 46e) (I-1-65) and (3-5) methiocarb 46f) (I-1-65) and (3-10) thiodicarb 47a) (I-1-66) and (2-2) chlorpyrifos 47b) (I-1-66) and (2-31) acephate 47c) (I-1-66) and (2-32) methamidophos 47d) (I-1-66) and (3-1) carbaryl 47e) (I-1-66) and (3-5) methiocarb 47f) (I-1-66) and (3-10) thiodicarb 48a) (I-1-67) and (2-2) chlorpyrifos 48b) (I-1-67) and (2-31) acephate 48c) (I-1-67) and (2-32) methamidophos 48d) (I-1-67) and (3-1) carbaryl 48e) (I-1-67) and (3-5) methiocarb 48f) (I-1-67) and (3-10) thiodicarb 49a) (I-1-68) and (2-2) chlorpyrifos 49b) (I-1-68) and (2-31) acephate 49c) (I-1-68) and (2-32) methamidophos 49d) (I-1-68) and (3-1) carbaryl 49e) (I-1-68) and (3-5) methiocarb 49f) (I-1-68) and (3-10) thiodicarb 50a) (I-1-69) and (2-2) chlorpyrifos 50b) (I-1-69) and (2-31) acephate 50c) (I-1-69) and (2-32) methamidophos 50d) (I-1-69) and (3-1) carbaryl 50e) (I-1-69) and (3-5) methiocarb 50f) (I-1-69) and (3-10) thiodicarb 51a) (I-1-70) and (2-2) chlorpyrifos 51b) (I-1-70) and (2-31) acephate 51c) (I-1-70) and (2-32) methamidophos 51d) (I-1-70) and (3-1) carbaryl 51e) (I-1-70) and (3-5) methiocarb 51f) (I-1-70) and (3-10) thiodicarb 52a) (I-1-71) and (2-2) chlorpyrifos 52b) (I-1-71) and (2-31) acephate 52c) (I-1-71) and (2-32) methamidophos 52d) (I-1-71) and (3-1) carbaryl 52e) (I-1-71) and (3-5) methiocarb 52f) (I-1-71) and (3-10) thiodicarb 53a) (I-1-72) and (2-2) chlorpyrifos 53b) (I-1-72) and (2-31) acephate 53c) (I-1-72) and (2-32) methamidophos 53d) (I-1-72) and (3-1) carbaryl 53e) (I-1-72) and (3-5) methiocarb 53f) (I-1-72) and (3-10) thiodicarb

However, the general or preferred radical definitions or illustrations given above can also be combined with one another as desired, i.e. including combinations between the respective ranges and preferred ranges. They apply both to the end products and, correspondingly, to precursors and intermediates.

Preference according to the invention is given to active compound combinations comprising the compounds of the formula (I) and active compounds of the formulae (2-1) to (2-23) in which the individual radicals are a combination of the meanings listed above as being preferred (preferable).

Particular preference according to the invention is given to active compound combinations comprising the compounds of the formula (I) and active compounds of the formulae (2-1) to (2-23) in which the individual radicals are a combination of the meanings listed above as being particularly preferred.

Very particular preference according to the invention is given to active compound combinations comprising the compounds of the formula (I) and active compounds of the formulae (2-1) to (2-23) in which the individual radicals are a combination of the meanings listed above as being very particularly preferred.

Saturated or unsaturated hydrocarbon radicals, such as alkyl or alkenyl, can in each case be straight-chain or branched as far as this is possible, including in combination with heteroatoms, such as, for example, in alkoxy.

Optionally substituted radicals can be mono- or polysubstituted, where in the case of polysubstitutions the substituents can be identical or different.

In addition, the active compound combinations may also comprise further fungicidally, acaricidally or insecticidally active cocomponents.

If the active compounds in the active compound combinations according to the invention are present in certain weight ratios, the synergistic effect is particularly pronounced. The mixing ratios required for finding the synergism are not necessarily the preferred mixing ratios relevant for 100% activity. However, the weight ratios of the active compounds in the active compound combinations can be varied within a relatively wide range. In general, the combinations according to the invention comprise active compounds of the formula (I) and the mixing partner of group 2 or of group 3 in the stated preferred and particularly preferred mixing ratios:

The mixing ratios are based on weight ratios. The ratio is to be understood as meaning active compound of the formula (I): mixing partner

Particularly Preferred preferred Mixing partner mixing ratio mixing ratio (2-1) azinphosmethyl 10:1 to 1:10 5:1 to 1:5 (2-2) chlorpyrifos 10:1 to 1:10 5:1 to 1:5 (2-3) diazinon 10:1 to 1:10 5:1 to 1:5 (2-4) dimethoate 10:1 to 1:10 5:1 to 1:5 (2-5) disulfoton 10:1 to 1:10 5:1 to 1:5 (2-6) ethion 10:1 to 1:10 5:1 to 1:5 (2-7) fenitrothion 10:1 to 1:10 5:1 to 1:5 (2-8) fenthion 20:1 to 1:10 5:1 to 1:5 (2-9) isoxathion 10:1 to 1:10 5:1 to 1:5 (2-10) malathion 10:1 to 1:10 5:1 to 1:5 (2-11) methidathion 10:1 to 1:10 5:1 to 1:5 (2-12) oxydemeton-methyl 10:1 to 1:10 5:1 to 1:5 (2-13) parathion 10:1 to 1:10 5:1 to 1:5 (2-14) parathion-methyl 10:1 to 1:10 5:1 to 1:5 (2-15) phenthoate 10:1 to 1:10 5:1 to 1:5 (2-16) phorate 10:1 to 1:10 5:1 to 1:5 (2-17) phosalone 10:1 to 1:10 5:1 to 1:5 (2-18) phosmet 10:1 to 1:10 5:1 to 1:5 (2-19) phoxim 10:1 to 1:10 5:1 to 1:5 (2-20) pirimiphos-methyl 10:1 to 1:10 5:1 to 1:5 (2-21) profenophos 10:1 to 1:10 5:1 to 1:5 (2-22) prothiophos 10:1 to 1:10 5:1 to 1:5 (2-23) tebupyrimphos 10:1 to 1:10 5:1 to 1:5 (2-24) triazophos  5:1 to 1:20 1:1 to 1:10 (2-25) chlorfenvinphos 10:1 to 1:10 5:1 to 1:5 (2-26) dichlorphos 10:1 to 1:10 5:1 to 1:5 (2-27) dicrotophos 10:1 to 1:10 5:1 to 1:5 (2-28) mevinphos 10:1 to 1:10 5:1 to 1:5 (2-29) monocrotophos 10:1 to 1:10 5:1 to 1:5 (2-30) phosphamidon 10:1 to 1:10 5:1 to 1:5 (2-31) acephate 10:1 to 1:10 5:1 to 1:5 (2-32) methamidophos 10:1 to 1:10 5:1 to 1:5 (2-33) trichlorfon 10:1 to 1:10 5:1 to 1:5 (3-1) carbaryl 10:1 to 1:10 5:1 to 1:5 (3-2) fenoxycarb 10:1 to 1:10 5:1 to 1:5 (3-3) formetanate 10:1 to 1:10 5:1 to 1:5 (3-4) fonnetanate hydrochloride 10:1 to 1:10 5:1 to 1:5 (3-5) methiocarb 10:1 to 1:10 5:1 to 1:5 (3-6) methomyl 10:1 to 1:10 5:1 to 1:5 (3-7) oxamyl  5:1 to 1:100 1:1 to 1:20 (3-8) pirimicarb 10:1 to 1:10 5:1 to 1:5 (3-9) propoxur 10:1 to 1:10 5:1 to 1:5 (3-10) thiodicarb 5:1 to 1:20 1:1 to 1:10

The active compound combinations of the invention are suitable for controlling animal pests, preferably arthropods and nematodes, in particular insects and arachnids, found in agriculture, in animal health, in forests, in the protection of stored products and materials and in the hygiene sector. They are active against normally sensitive and resistant species, and against all or individual developmental stages. The abovementioned pests include:

From the order of the Isopoda, for example, Oniscus asellus, Armadilfidium vulgare, Porcellio scabr.

From the order of the Diplopoda, for example, Blaniulus guttulatus.

From the order of the Chilopoda, for example, Geophilus carpophagus, Scutigera spp.

From the order of the Symphyla, for example, Scutigerella immaculate.

From the order of the Thysanura, for example, Lepisma saccharina.

From the order of the Collembola, for example, Onychiurus armatus.

From the order of the Orthoptera, for example, Acheta domesticus, Gryllotalpa spp., Locusta migratoria migratorioides, Melanoplus spp., Schistocerca gregaria

From the order of the Blattaria, for example, Blatta orientalis, Periplaneta americana, Leucophaea maderea, Blattella germanica.

From the order of the Dermaptera, for example, Forficula auricularia

From the order of the Isoptera, for example, Reticulitermes spp.

From the order of the Phthiraptera, for example, Pediculus humanus corporis, Haematopinus spp., Linognathus spp., Trichodectes spp., Damalinia spp.

From the order of the Thysanoptera, for example, Hercinothrips femoralis, Thrips tabaci, Thrips palmi, Frankliniella accidentalis.

From the order of the Heteroptera, for example, Eurygaster spp., Dysdercus intermedius, Piesma quadrata, Cimex lectularius, Rhodnius prolixus, Triatoma spp.

From the order of the Homoptera, for example, Aleurodes brassicae, Bemisia tabaci, Trialeurodes vaporarionim, Aphis gossypii, Brevicoryne brassicae, Cryptomyzus ribis, Aphis fabae, Aphis pomi, Eriosoma lanigerum, Hyalopterus arundinis, Phylloxera vastatrix, Pemphigus spp., Macrosiphum avenae, Myzus spp., Phorodon humuli, Rhopalosiphum padi, Empoasca spp., Euscelis bilobatus, Nephotettix cincticeps, Lecanium corni, Saissetia oleae, Laodelphax striatellus, Nilaparvata lugens, Aonidiella aurantii, Aspidiotus hederae, Pseudococcus spp., Psylla spp.

From the order of the Lepidoptera, for example, Pectinophora gossypiella, Bupalus piniarius, Cheimatobia brunata, Lithocolletis blancardella, Hyponomeuta padella, Plutella xylostella, Malacosoma neustria, Euproctis chrysorrhoea, Lymantria spp., Bucculatrix thurberiella, Phyllocnistis citrella, Agrotis spp., Euxoa spp., Feltia spp., Earias insulana, Heliothis spp., Mamestra brassicae, Panolis flammea, Spodoptera spp., Trichoplusia ni, Carpocapsa pomonella, Pieris spp., Chilo spp., Pyrausta nubilalis, Ephestia kuehniella, Galleria mellonella, Tineola bisselliella, Tinea pellionella, Hofinannophila pseudospretella, Cacoecia podana, Capua reticulana, Choristoneura fumiferana, Clysia ambiguella, Homona magnanima, Tortrix viridana, Cnaphalocerus spp., Oulema oryzae.

From the order of the Coleoptera, for example, Anobium punctatum, Rhizopertha dominica, Bruchidius obtectus, Acanthoscellides obtectus, Hylotrupes bajulus, Agelastica alni, Leptinotarsa decemlineata, Phaedon cochleariae, Diabrotica spp., Psylliodes chrysocephala, Epilachna varivestis, Atomaria spp., Oryzaephilus surinamensis, Anthonomus spp., Sitophilus spp., Otiorrhynchus sulcatus, Cosmopolites sordidus, Ceuthorrhynchus assimilis, Hypera postica, Dermestes spp., Trogoderma spp., Anthrenus spp., Attagenus spp., Lyctus spp., Meligethes aeneus, Ptinus spp., Niptus hololeucus, Gibbium psylloides, Tribolium spp., Tenebrio molitor, Agriotes spp., Conoderus spp., Melolontha melolontha, Amphimallon solstitialis, Costelytra zealandica, Lissorhoptrus oryzophilus.

From the order of the Hymenoptera, for example, Diprion spp., Hoplocampa spp., Lasius spp., Monomorium pharaonis, Vespa spp.

From the order of the Diptera, for example, Aedes spp., Anopheles spp., Culex spp., Drosophila melanogaster, Musca spp., Fannia spp., Calliphora erythrocephala, Lucilia spp., Chrysomyia spp., Cuterebra spp., Gastrophilus spp., Hyppobosca spp., Stomoxys spp., Oestrus spp., Hypoderma spp., Tabanus spp., Tannia spp., Bibio hortulanus, Oscinella frit, Phorbia spp., Pegonyia hyoscyami, Ceratitis capitata, Dacus oleae, Tipula paludosa, Hylemyia spp., Liriomyza spp.

From the order of the Siphonaptera, for example, Xenopsylla cheopis, Ceratophyllus spp.

From the class of the Arachnida, for example, Scorpio maurus, Latrodectus mactans, Acarus siro, Argas spp., Omithodoros spp., Dermanyssus gallinae, Eriophyes ribis, Phyllocoptruta oleivora, Boophilus spp., Rhipicephalus spp., Amblyomma spp., Hyalomma spp., Ixodes spp., Psoroptes spp., Chorioptes spp., Sarcoptes spp., Tarsonemus spp., Bryobia praetiosa, Panonychus spp., Tetranychus spp., Hemitarsonemus spp., Brevipalpus spp.

The plant-parasitic nematodes include, for example, Pratylenchus spp., Radopholus similis, Ditylenchus dipsaci, Tylenchulus semipenetrans, Heterodera spp., Globodera spp., Meloidogyne spp., Aphelenchoides spp., Longidorus spp., Xiphinema spp., Trichodorus spp., Bursaphelenchus spp.

The active compound combinations can be converted into the customary formulations such as solutions, emulsions, wettable powders, suspensions, powders, dusts, pastes, soluble powders, granules, suspension-emulsion concentrates, natural and synthetic materials impregnated with active compound, and microencapsulations in polymeric materials.

These formulations are produced in a known manner, for example by mixing the active compounds with extenders, that is, liquid solvents and/or solid carriers, optionally with the use of surfactants, that is, emulsifiers and/or dispersants, and/or foam formers.

If the extender used is water, it is also possible, for example, to use organic solvents as cosolvents. The following are essentially suitable as liquid solvents: aromatics such as xylene, toluene or alkylnaphthalenes, chlorinated aromatics or chlorinated aliphatic hydrocarbons such as chlorobenzenes, chloroethylenes or methylene chloride, aliphatic hydrocarbons such as cyclohexane or paraffins, for example mineral oil fractions, mineral and vegetable oils, alcohols such as butanol or glycol and their ethers and esters, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents such as dimethylformamide and dimethyl sulfoxide, or else water.

Suitable solid carriers are: for example ammonium salts and ground natural minerals such as kaolins, clays, talc, chalk quartz, attapulgite, montmorillonite or diatomaceous earth, and ground synthetic materials such as finely divided silica, alumina and silicates; suitable solid carriers for granules are: for example crushed and fractionated natural rocks such as calcite, marble, pumice, sepiolite and dolomite, or else synthetic granules of inorganic and organic meals, and granules of organic material such as sawdust, coconut shells, maize cobs and tobacco stalks; suitable emulsifiers and/or foam formers are: for example nonionic and anionic emulsifiers such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, for example alkylaryl polyglycol ethers, alkylsulfonates, alkyl sulfates, arylsulfonates, or else protein hydrolysates; suitable dispersants are: for example lignin-sulfite waste liquors and methylcellulose.

Tackifiers such as carboxymethylcellulose and natural and synthetic polymers in the form of powders, granules or latices, such as gum arabic, polyvinyl alcohol and polyvinyl acetate, or else natural phospholipids such as cephalins and lecithins and synthetic phospholipids can be used in the formulations. Other additives can be mineral and vegetable oils.

It is possible to use colorants such as inorganic pigments, for example iron oxide, titanium oxide and Prussian Blue, and organic colorants such as alizarin colorants, azo colorants and metal phthalocyanine colorants, and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc.

The formulations generally comprise between 0.1 and 95% by weight of active compound, preferably between 0.5 and 90%.

The active compound combinations of the invention can be present in their commercially available formulations and in the use forms, prepared from these formulations, as a mixture with other active compounds, such as insecticides, attractants, sterilants, bactericides, acaricides, nematicides, fungicides, growth-regulating substances or herbicides. The insecticides include for example, phosphates, carbamates, carboxylates, chlorinated hydrocarbons, phenylureas and substances produced by microorganisms, inter alia.

Mixtures with other known active compounds such as herbicides or with fertilizers and growth regulators are also possible.

When used as insecticides, the active compound combinations of the invention can furthermore be present in their commercially available formulations and in the use forms, prepared from these formulations, as a mixture with synergists. Synergists are compounds which increase the action of the active compounds, without it being necessary for the synergist added to be active itself.

The active compound content of the use forms prepared from the commercially available formulations can vary within wide limits. The active compound concentration of the use forms can be from 0.0000001 to 95% by weight of active compound, preferably between 0.0001 and 1% by weight.

The compounds are employed in a customary manner appropriate for the use forms.

When used against hygiene pests and stored-product pests, the active compound combinations are distinguished by an excellent residual action on wood and clay as well as good stability to alkali on limed substrates.

The active compound combinations of the invention are not only active against plant pests, hygiene pests and stored-product pests, but also, in the veterinary medicine sector, against animal parasites (ectoparasites) such as hard ticks, soft ticks, mange-mites, harvest mites, flies (stinging and licking), parasitizing fly larvae, lice, head lice, bird lice and fleas. These parasites include:

From the order of the Anoplurida, for example, Haematopinus spp., Linognathus spp., Pediculus spp., Phtirus spp., Solenopotes spp.

From the order of the Mallophagida and the suborders Amblycerina and Ischnocerina, for example, Trimenopon spp., Menopon spp., Trinoton spp., Bovicola spp., Werneckiella spp., Lepikentron spp., Damalina spp., Trichodectes spp., Felicola spp.

From the order Diptera and the suborders Nematocerina and Brachycerina, for example, Aedes spp., Anopheles spp., Culex spp., Simulium spp., Eusimulium spp., Phlebotomus spp., Lutzomyia spp., Culicoides spp., Chrysops spp., Hybomitra spp., Atylotus spp., Tabanus spp., Haematopota spp., Philipomyia spp., Braula spp., Musca spp., Hydrotaea spp., Stomoxys spp., Haematobia spp., Morellia spp., Fannia spp., Glossina spp., Calliphora spp., Lucilia spp., Chrysomyia spp., Wohlfahrtia spp., Sarcophaga spp., Oestrus spp., Hypoderma spp., Gasterophilus spp., Hippobosca spp., Lipoptena spp., Melophagus spp.

From the order of the Siphonapterida, for example, Pulex spp., Ctenocephalides spp., Xenopsylla spp., Ceratophyllus spp.

From the order of the Heteropterida, for example, Cimex spp., Triatoma spp., Rhodnius spp., Panstrongylus spp.

From the order of the Blattarida, for example, Blatta orientalis, Periplaneta americana, Blattella germanica, Supella spp.

From the subclass of the Acaria (Acarida) and the orders of the Meta- and Mesostigmata, for example; Argas spp., Ornithodoms spp., Otobius spp., Ixodes spp., Amblyomma spp., Boophilus spp., Dermacentor spp., Haemophysalis spp., Hyalomma spp., Rhipicephalus spp., Dermanyssus spp., Raillietia spp., Pneumonyssus spp., Sternostoma spp., Varroa spp.

From the order of the Actinedida (Prostigmata) and Acaridida (Astigmata), for example, Acarapis spp., Cheyletiella spp., Ornithocheyletia spp., Myobia spp., Psorergates spp., Demodex spp., Trombicula spp., Listrophorus spp., Acarus spp., Tyrophagus spp., Caloglyphus spp., Hypodectes spp., Pterolichus spp., Psoroptes spp., Chorioptes spp., Otodectes spp., Sarcoptes spp., Notoedres spp., Knemidocoptes spp., Cytodites spp., Laminosioptes spp.

The active compound combinations of the invention are also suitable for controlling arthropods which attack agricultural livestock such as, for example, cattle, sheep, goats, horses, pigs, donkeys, camels, buffaloes, rabbits, chickens, turkeys, ducks, geese, honey-bees, other domestic animals such as, for example, dogs, cats, caged birds, aquarium fish and soled experimental animals such as, for example, hamsters, guinea pigs, rats and mice. By controlling these arthropods, cases of death and reductions in productivity (for meat, milk, wool, hides, eggs, honey and the like) should be diminished, so that more economical and simpler animal husbandry is possible by the use of the active compound combinations of the invention.

The active compound combinations of the invention are used in the veterinary sector in a known manner by enteral administration in the form of, for example, tablets, capsules, potions, drenches, granules, pastes, boluses, the feed-through method, suppositories, by parenteral administration such as, for example, by injections (intramuscularly, subcutaneously, intravenously, intraperitoneally and the like), implants, by nasal administration, by dermal administration in the form of, for example, immersing or dipping, spraying, pouring-on, spotting-on, washing, dusting, and with the aid of active-compound-comprising molded articles such as collars, ear tags, tail tags, limb bands, halters, marking devices and the like.

When used for cattle, poultry, domestic animals and the like, the active compound combinations can be applied as formulations (for example powders, emulsions, flowables) comprising the active compounds in an amount of 1 to 80% by weight, either directly or after 100- to 10 000fold dilution, or they may be used as a chemical dip.

Moreover, it has been found that the active compound combinations of the invention show a potent insecticidal action against insects which destroy industrial materials.

The following insects may be mentioned by way of example and with preference, but not by way of limitation:

Beetles such as Hylotrupes bajulus, Chlorophorus pilosis, Anobium punctatum, Xestobium rufovillosum, Ptilinus pecticomis, Dendrobium pertinex, Ermobius mollis, Priobium carpini, Lyctus brunneus, Lyctus africanus, Lyctus planicollis, Lyctus linearis, Lyctus pubescens, Trogoxylon aequale, Minthes rugicollis, Xyleborms spec., Tryptodendron spec., Apate monachus, Bostrychus capucins, Heterobostrychus brunneus, Sinoxylon spec., Dinoderus minutus.

Dernapterans such as Sirex juvencus, Urocerus gigas, Urocerus gigas taignus, Urocerus augur.

Termites such as Kalotermes flavicollis, Cryptotermes brevis, Heterotenmes indicola, Reticulitermes flavipes, Reticulitermes santonensis, Reticulitermes lucifugus, Mastotermes darwiniensis, Zootermopsis nevadensis, Coptotermes formosanus.

Bristle-tails such as Lepisma saccharina.

Industrial materials in the present context are understood as meaning non-living materials such as, preferably, polymers, adhesives, glues, paper and board, leather, wood, timber products and paints.

The material which is to be protected from insect attack is very particularly preferably wood and timber products.

Wood and timber products which can be protected by the composition of the invention, or mixtures comprising it, are to be understood as meaning, for example:

Construction timber, wooden beams, railway sleepers, bridge components, jetties, vehicles made of wood, boxes, pallets, containers, telephone poles, wood lagging, windows and doors made of wood, plywood, chipboard, joinery, or timber products which quite generally are used in house construction or building joinery.

The active compound combinations can be used as such, in the form of concentrates or generally customary formulations such as powders, granules, solutions, suspensions, emulsions or pastes.

The abovementioned formulations can be prepared in a manner known per se, for example by mixing the active compounds with at least one solvent or diluent, emulsifier, dispersant and/or binder or fixative, water repellant, if desired desiccants and UV stabilizers, and if desired colorants and pigments and other processing auxiliaries.

The insecticidal compositions or concentrates used for protecting wood and timber products comprise the active compound of the invention in a concentration of 0.0001 to 95% by weight, in particular 0.001 to 60% by weight.

The amount of composition or concentrate employed depends on the species and the abundance of the insects and on the medium. The optimal quantity to be employed can be determined in each case by test series upon application. In general, however, it will suffice to employ 0.0001 to 20% by weight, preferably 0.001 to 10% by weight, of the active compound, based on the material to be protected.

A suitable solvent and/or diluent is an organochemical solvent or solvent mixture and/or an oily or oil-type organochemical solvent or solvent mixture of low volatility and/or a polar organochemical solvent or solvent mixture and/or water and, if appropriate, an emulsifier and/or wetter.

Organochemical solvents which are preferably employed are oily or oil-type solvents with an evaporation number of above 35 and a flash point of above 30° C., preferably above 45° C. Such oily and oil-type solvents which are insoluble in water and of low volatility and which are used are suitable mineral oils or their aromatic fractions or mineral-oil-containing solvent mixtures, preferably white spirit, petroleum and/or alkylbenzene.

Mineral oils with a boiling range of 170 to 220° C., white spirit with a boiling range of 170 to 220° C., spindle oil with a boiling range of 250 to 350° C., petroleum and aromatics with a boiling range of 160 to 280° C., oil of turpentine, and the like are advantageously used.

In a preferred embodiment, liquid aliphatic hydrocarbons with a boiling range of 180 to 210° C. or high-boiling mixtures of aromatic and aliphatic hydrocarbons with a boiling range of 180 to 220° C. and/or spindle oil and/or monochloronaphthalene, preferably a-monochloronaphthalene, are used.

The organic oily or oil-type solvents of low volatility and with an evaporation number of above 35 and a flash point of above 30° C., preferably above 45° C., can be replaced in part by organochemical solvents of high or medium volatility, with the proviso that the solvent mixture also has an evaporation number of above 35 and a flash point of above 30° C., preferably above 45° C., and that the mixture is soluble or emulsifiable in this solvent mixture.

In a preferred embodiment, some of the organochemical solvent or solvent mixture an aliphatic polar organochemical solvent or solvent mixture is replaced. Aliphatic organochemical solvents which contain hydroxyl and/or ester and/or ether groups are preferably used, such as, for example, glycol ethers, esters or the like.

Organochemical binders used for the purposes of the present invention are the synthetic resins and/or binding drying oils which are known per se and which can be diluted in water and/or dissolved or dispersed or emulsified in the organochemical solvents employed, in particular binders composed of, or comprising, an acrylate resin, a vinyl resin, for example polyvinyl acetate, polyester resin, polycondensation or polyaddition resin, polyurethane resin, alkyd resin or modified alkyd resin, phenol resin, hydrocarbon resin such as indene/coumarone resin, silicone resin, drying vegetable and/or drying oils and/or physically drying binders based on a natural and/or synthetic resin.

The synthetic resin employed as binder can be employed in the form of an emulsion, dispersion or solution. Bitumen or bituminous substances may also be used as binders, in amounts of up to 10% by weight. In addition, colorants, pigments, water repellants, odor-masking agents, and inhibitors or anticorrosive agents and the like, all of which are known per se, can be employed.

In accordance with the invention, the composition or the concentrate preferably comprises, as organochemical binders, at least one alkyd resin or modified alkyd resin and/or a drying vegetable oil. Alkyd resins which are preferably used in accordance with the invention are those with an oil content of over 45% by weight, preferably 50 to 68% by weight.

Some or all of the abovementioned binder can be replaced by a fixative (mixture) or plasticizer (mixture). These additives are intended to prevent volatilization of the active compounds, and also crystallization or precipitation. They preferably replace 0.01 to 30% of the binder (based on 100% of binder employed).

The plasticizers are from the chemical classes of the phthalic esters, such as dibutyl phthalate, dioctyl phthalate or benzyl butyl phthalate, phosphoric esters such as tributyl phosphate, adipic esters such as di(2-ethylhexyl)adipate, stearates such as butyl stearate or amyl stearate, oleates such as butyl oleate, glycerol ethers or higher-molecular-weight glycol ethers, glycerol esters and p-toluenesulfonic esters.

Fixatives are based chemically on polyvinyl alkyl ethers such as, for example, polyvinyl methyl ether, or ketones such as benzophenone and ethylenebenzophenone.

Other suitable solvents or diluents are, in particular, water, if appropriate as a mixture with one or more of the abovementioned organochemical solvents or diluents, emulsifiers and dispersants.

Particularly effective timber protection is achieved by industrial-scale impregnating processes, for example the vacuum, double-vacuum or pressure processes.

The active compound combinations of the invention can at the same time be employed for protecting objects which come into contact with saltwater or brackish water, such as hulls, screens, nets, buildings, moorings and signaling systems, against fouling.

Fouling by sessile Oligochaeta, such as Serpulidae, and by shells and species from the Ledamorpha group (goose barnacles), such as various Lepas and Scalpellum species, or by species from the Balanomorpha group (acorn barnacles), such as Balanus or Pollicipes species, increases the frictional drag of ships and, as a consequence, leads to a marked increase in operation costs owing to higher energy consumption and additionally frequent stops in the dry dock.

Apart from fouling by algae, for example Ectocarpus sp. and Ceramium sp., fouling by sessile Entomostraka groups, which come under the generic term Cirripedia (cirriped crustaceans), is of particular importance.

Surprisingly, it has now been found that the active compound combinations of the invention have an outstanding antifouling action.

Using the active compound combinations of the invention allows the use of heavy metals such as, for example, in bis(trialkyltin) sulfides, tri-n-butyltin laurate, tri-n-butyltin chloride, copper(l) oxide, triethyltin chloride, tri-n-butyl(2-phenyl-4-chlorophenoxy)tin, tributyltin oxide, molybdenum disulfide, antimony oxide, polymeric butyl titanate, phenyl(bispyridine)bismuth chloride, tri-n-butyltin fluoride, manganese ethylenebisthiocarbamate, zinc dimethyldithiocarbamate, zinc ethylenebisthiocarbamate, zinc salts and copper salts of 2-pyridinethiol 1-oxide, bisdimethyldithiocarbamoylzinc ethylenebisthiocarbamate, zinc oxide, copper(l) ethylenebisdithiocarbamate, copper thiocyanate, copper naphthenate and tributyltin halides to be dispensed with, or the concentration of these compounds to be substantially reduced.

If appropriate, the ready-to-use antifouling paints can additionally comprise other active compounds, preferably algicides, fungicides, herbicides, molluscicides, or other antifouling active compounds.

Preferable suitable components in combinations with the antifouling compositions according to the invention are:

algicides such as 2-tert-butylamino-4-cyclopropylamino-6-methylthio-1,3,5-triazine, dichlorophen, diuron, endothal, fentin acetate, isoproturon, methabenzthiazuron, oxyfluorfen, quinoclamine and terbutryn;

fungicides such as benzo[b]thiophenecarboxylic acid cyclohexylamide S,S-dioxide, dichlofluanid, fluorfolpet, 3-iodo-2-propinyl butylcarbamate, tolylfluanid and azoles such as azaconazole, cyproconazole, epoxyconazole, hexaconazole, metconazole, propiconazole and jebuconazole; molluscicides such as fentin acetate, metaldehyde, methiocarb, niclosamid, thiodicarb and trimethacarb;

or conventional antifouling active compounds such as 4,5-dichloro-2-octy-4-isothiazolin-3-one, diiodomethylparatryl sulfone, 2-(N,N-dimethylthiocarbamoylthio)-5-nitrothiazyl, potassium, copper, sodium and zinc salts of 2-pyridinethiol 1-oxide, pyridine/triphenylborane, tetrabutyldistannoxane, 2,3,5,6-tetrachloro-4-methylsulfonyl)pyridine, 2,4,5,6-tetrachloroisophthalonitrile, tetramethylthiuram disulfide and 2,4,6-trichlorophenylmaleimide.

The antifouling compositions used comprise the active compound combinations of the invention in a concentration of 0.001 to 50% by weight, in particular 0.01 to 20% by weight.

Moreover, the antifouling compositions of the invention comprise the customary components such as, for example, those described in Ungerer, Chem Ind. 1985, 37, 730-732 and Williams, Antifouling Marine Coatings, Noyes, Park Ridge, 1973.

Besides the algicidal, fungicidal, molluscicidal active compounds and insecticidal active compounds of the invention, antifouling paints comprise, in particular, binders.

Examples of recognized binders are polyvinyl chloride in a solvent system, chlorinated rubber in a solvent system, acrylic resins in a solvent system, in particular in an aqueous system; vinyl chloride/vinyl acetate copolymer systems in the form of aqueous dispersions or in the form of organic solvent systems, butadiene/styrene/acrylonitrile rubbers, drying oils such as linseed oil, resin esters or modified hardened resins in combination with tar or bitumens, asphalt and epoxy compounds, small amounts of chlorine rubber, chlorinated polypropylene and vinyl resins.

If appropriate, paints also comprise inorganic pigments, organic pigments or colorants which are preferably insoluble in salt water. Paints may furthermore comprise materials such as colophonium to allow controlled release of the active compounds. Furthermore, the paints may comprise plasticizers, modifiers which affect the rheological properties and other conventional constituents. The compounds of the invention or the abovementioned mixtures may also be incorporated into self-polishing antifouling systems.

The active compound combinations are also suitable for controlling animal pests, in particular insects, arachnids and mites, which are found in enclosed spaces such as, for example, dwellings, factory halls, offices, vehicle cabins and the like. They can be employed in domestic insecticide products for controlling these pests. They are active against sensitive and resistant species and against all developmental stages. These pests include:

From the order of the Scorpionidea, for example, Buthus occitanus.

From the order of the Acarina, for example, Argas persicus, Argas reflexus, Bryobia ssp., Dermanyssus gallinae, Glyciphagus domesticus, Ornithodorus moubat, Rhipicephalus sanguineus, Trombicula alfreddugesi, Neutrombicula autumnalis, Dermatophagoides pteronissimus, Dermatophagoides forinae.

From the order of the Araneae, for example, Aviculariidae, Araneidae.

From the order of the Opiliones, for example, Pseudoscorpiones chelifer, Pseudoscorpiones cheiridium, Opiliones phalangium.

From the order of the Isopoda, for example, Oniscus asellus, Porcellio scaber.

From the order of the Diplopoda, for example, Blaniulus guttulatus, Polydesmus spp.

From the order of the Chilopoda, for example, Geophilus spp.

From the order of the Zygentoma, for example, Ctenolepisma spp., Lepisma saccharina, Lepismodes inquilinus.

From the order of the Blattaria, for example, Blatta orientalies, Blattella germanica, Blattella asahinai, Leucophaea maderae, Panchlora spp., Parcoblatta spp., Periplaneta australasiae, Periplaneta americana, Periplaneta brunnea, Periplaneta fuliginosa, Supella longipalpa.

From the order of the Saltatoria, for example, Acheta domesticus.

From the order of the Dermaptera, for example, Forficula auricularia.

From the order of the Isoptera, for example, Kalotermes spp., Reticulitermes spp.

From the order of the Psocoptera, for example, Lepinatus spp., Liposcelis spp.

From the order of the Coleptera, for example, Anthrenus spp., Attagenus spp., Dermestes spp., Latheticus oryzae, Necrobia spp., Ptinus spp., Rhizopertha dominica, Sitophilus granarius, Sitophilus oryzae, Sitophilus zeamais, Stegobium paniceum.

From the order of the Diptera, for example, Aedes aegypti, Aedes albopictus, Aedes taeniorhynchus, Anopheles spp., Calliphora erythrocephala, Chrysozona pluvialis, Culex quinquefasciatus, Culex pipiens, Culex tarsalis, Drosophila spp., Fannia canicularis, Musca domestica, Phlebotomus spp., Sarcophaga carnaria, Simulium spp., Stomoxys calcitrans, Tipula paludosa.

From the order of the Lepidoptera, for example, Achroia grisella, Galleria mellonella, Plodia interpunctella, Tinea cloacella, Tinea pellionella, Tineola bisselliella

From the order of the Siphonaptera, for example, Ctenocephalides canis, Ctenocephalides felis, Pulex irritans, Tunga penetrans, Xenopsylla cheopis.

From the order of the Hymenoptera, for example, Camponotus herculeanus, Lasius fuliginosus, Lasius niger, Lasius umbratus, Monomorium pharaonis, Paravespula spp., Tetramorium caespitum.

From the order of the Anoplura, for example, Pediculus humanus capitis Pediculus humanus corporis, Phthirus pubis.

From the order of the Heteroptera, for example, Cimex hemipterus, Cimex lectularius, Rhodinus prolixus, Triatoma infestans.

They are used as aerosols, pressureless spray products, for example pump and atomizer sprays, automatic fogging systems, foggers, foams, gels, evaporator products with evaporator tablets made of cellulose or polymer, liquid evaporators, gel and membrane evaporators, propeller-driven evaporators, energy-free, or passive, evaporation systems, moth papers, moth bags and moth gels, as granules or dusts, in baits for spreading or in bait stations.

According to the invention, it is possible to treat all plants and parts of plants. Plants are to be understood here as meaning all plants and plant populations such as desired and undesired wild plants or crop plants (including naturally occurring crop plants). Crop plants can be plants which can be obtained by conventional breeding and optimization methods or by biotechnological and genetic engineering methods or combinations of these methods, including the transgenic plants and including the plant cultivars which can or cannot be protected by plant breeders' certificates. Parts of plants are to be understood as meaning all above-ground and below-ground parts and organs of plants, such as shoot, leaf, flower and root, examples which may be mentioned being leaves, needles, stems, trunks, flowers, fruit-bodies, fruits and seeds and also roots, tubers and rhizomes. Parts of plants also include harvested plants and vegetative and generative propagation material, for example seedlings, tubers, rhizomes, cuttings and seeds.

The treatment of the invention of the plants and parts of plants with the active compounds is carried out directly or by action on their environment, habitat or storage area according to customary treatment methods, for example by dipping, spraying, evaporating, atomizing, broadcasting, brushing-on and, in the case of propagation material, in particular in the case of seeds, furthermore by one- or multi-layer coating.

As already mentioned above, it is possible to treat all plants and their parts according to the invention. In a preferred embodiment, wild plant species and plant cultivars, or those obtained by conventional biological breeding methods, such as crossing or protoplast fusion, and parts thereof, are treated. In a further preferred embodiment, transgenic plants and plant cultivars obtained by genetic engineering, if appropriate in combination with conventional methods (Genetically Modified Organisms), and parts thereof are treated. The terms “parts”, “parts of plants” and “plant parts” have been explained above.

Particularly preferably, plants of the plant cultivars which are in each case commercially available or in use are treated according to the invention.

Depending on the plant species or plant cultivars, their location and growth conditions (soils, climate, vegetation period, diet), the treatment of the invention may also result in superadditive (“synergistic”) effects. Thus, for example, reduced application rates and/or a widening of the activity spectrum and/or an increase in the activity of the substances and compositions which can be used according to the invention, better plant growth, increased tolerance to high or low temperatures, increased tolerance to drought or to water or soil salt content, increased flowering performance, easier harvesting, accelerated maturation, higher harvest yields, better quality and/or a higher nutritional value of the harvested products, better storage stability and/or processability of the harvested products are possible which exceed the effects which were actually to be expected.

The transgenic plants or plant cultivars (i.e. those obtained by genetic engineering) which are preferred and to be treated according to the invention include all plants which, in the genetic modification, received genetic material which imparts particularly advantageous useful traits to these plants. Examples of such traits are better plant growth, increased tolerance to high or low temperatures, increased tolerance to drought or to water or soil salt content, increased flowering performance, easier harvesting, accelerated maturation, higher harvest yields, better quality and/or a higher nutritional value of the harvested products, better storage stability and/or processability of the harvested products. Further and particularly emphasized examples of such traits are a better defense of the plants against animal and microbial pests, such as against insects, mites, phytopathogenic fungi, bacteria and/or viruses, and also increased tolerance of the plants to certain herbicidally active compounds. Examples of transgenic plants which may be mentioned are the important crop plants, such as cereals (wheat, rice), maize, soya beans; potatoes, cotton, tobacco, oilseed rape and also fruit plants (with the fruits apples, pears, citrus fruits and grapes), and particular emphasis is given to maize, soya beans, potatoes, cotton, tobacco and oilseed rape. Traits that are particularly emphasized are the increased defense of the plants against insects, arachnids, nematodes and worms by toxins formed in the plants, in particular those formed in the plants by the genetic material from Bacillus thuringiensis (for example by the genes CryIA(a), CryIA(b), CryIA(c), CryIIA, CryIIIA, CryIIIB2, Cry9c Cry2Ab, Cry3Bb and CryIF and also combinations thereof) (hereinbelow referred to as “Bt plants”). Traits that are also particularly emphasized are the increased defense of plants against-fungi, bacteria and viruses by systemic acquired resistance (SAR), systemin, phytoalexins, elicitors and also resistance genes and correspondingly expressed proteins and toxins. Traits that are furthermore particularly emphasized are the increased tolerance of the plants to certain herbicidally active compounds, for example imidazolinones, sulphonylureas, glyphosate or phosphinotricin (for example the “PAT” gene). The genes in question which impart the desired traits can also be present in combination with one another in the transgenic plants. Examples of “Bt plants” which may be mentioned are maize varieties, cotton varieties, soya bean varieties and potato varieties which are sold under the trade names YIELD GARD® (for example maize, cotton, soya beans), KnockOut® (for example maize), StarLink® (for example maize), Bollgard® (cotton), Nucotn® (cotton) and NewLeaf® (potato). Examples of herbicide-tolerant plants which may be mentioned are maize varieties, cotton varieties and soya bean varieties which are sold under the trade names Roundup Ready® (tolerance to glyphosate, for example maize, cotton, soya beans), Liberty Link® (tolerance to phosphinotricin, for example oilseed rape), IMI® (tolerance to imidazolinones) and STS® (tolerance to sulfonylureas, for example maize). Herbicide-resistant plants (plants bred in a conventional manner for herbicide tolerance) which may be mentioned include the varieties sold under the name Clearfield® (for example maize). Of course, these statements also apply-to plant cultivars having these or still-to-be-developed genetic traits, which plants will be developed and/or marketed in the future.

The plants listed can be treated according to the invention in a particularly advantageous manner with the active compound mixtures of the invention. The preferred ranges stated above for the mixtures also apply to the treatment of these plants. Particular emphasis is given to the treatment of plants with the mixtures specifically mentioned in the present text.

The good insecticidal and acaricidal action of the active compound combinations of the invention can be seen from the examples which follow. While the individual active compounds show weaknesses in their action, the combinations show an action which exceeds a simple sum of actions.

A synergistic effect in insecticides and acaricides is always present when the action of the active compound combinations exceeds the total of the actions of the active compounds when applied individually.

The expected action for a given combination of two active compounds can be calculated according to S. R. Colby, Weed, 15 (1967), 20-22):

If

    • X is the kill rate, expressed as a percentage of the untreated control, when employing active compound A at an application rate of m g/ha or in a concentration of m ppm,
    • Y is the kill rate, expressed as a percentage of the untreated control, when employing active compound B at an application rate of n g/ha or in a concentration of n ppm and
    • E is the kill rate, expressed as a percentage of the untreated control, when employing active compounds A and B at application rates of m and n g/ha or in a concentration of m and n ppm,
    • then E = X + Y - X · Y 100

If the actual insecticidal kill rate exceeds the calculated value, the action of the combination is superadditive, i.e. a synergistic effect is present. In this case, the actually observed kill rate must exceed the value calculated using the above formula for the expected kill rate (E).

After the desired period of time, the kill in % is determined. 100% means that all animals have been killed; 0% means that none of the animals have been killed.

USE EXAMPLES Example A

    • Myzus persicae test
    • Solvent: 7 parts by weight of dimethylformamide
    • Emulsifier: 2 parts by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amounts of solvent and emulsifier, and the concentrate is diluted with emulsifier-containing water to the desired concentration.

Cabbage leaves (Brassica oleracea) which are heavily infested by the green peach aphid (Myzus persicae) are treated by being dipped into the preparation of active compound of the desired concentration.

After the desired period of time, the kill in % is determined. 100% means that all aphids have been killed; 0% means that none of the aphids have been killed. The determined kill ratios are entered into Colby's formula (see page 42).

In this test, for example, the following active compound combination according to the present application shows a synergistically enhanced activity compared to the active compounds applied on their own:

TABLE A Plant-damaging insects Myzus persicae test Kill rate in % after Concentration of active 1d Active compounds compound in ppm found* calc.** 4 0 0.8 65 (I-1-9) + (2-2) chlorpyrifos (5:1) 4 + 0.8 85 65
*found. = activity found

**calc. = activity calculated using Colby's formula

Claims

1. A composition comprising a synergistically effective combination of compounds of the formula (I) in which

A1 and A2 independently of one another represent oxygen or sulfur,
X1 represents N or CR10,
R1 represents hydrogen or represents C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl or C3-C6-cycloalkyl, each of which is optionally mono- or polysubstituted, where the substituents independently of one another may be selected from the group consisting of R6, halogen, cyano, nitro, hydroxyl, C1-C4-alkoxy, C1-C4-alkylthio, C1-C4-alkylsulfinyl, C1-C4-alkylsulfonyl, C2-C4-alkoxycarbonyl, C1-C4-alkylamino, C2-C8-dialkylamino, C3-C6-cycloalkylamino, (C1-C4-alkyl)-C3-C6-cycloalkylamino and R11,
R2 represents hydrogen, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl, C1-C4-alkoxy, C1-C4-alkylamino, C2-C8-dialkylamino, C3-C6-cycloalkylamino, C2-C6-alkoxycarbonyl or C2-C6-alkylcarbonyl,
R3 represents hydrogen, R11 or represents C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl, each of which is optionally mono- or polysubstituted, where the substituents independently of one another may be selected from the group consisting of R6, halogen, cyano, nitro, hydroxyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C1-C4-alkylthio, C1-C4-alkylsulfinyl, C1-C4-alkylsulfonyl, C2-C6-alkoxycarbonyl, C2-C6-alkylcarbonyl, C3-C6-trialkylsilyl, R11, phenyl, phenoxy and a 5- or 6-membered heteroaromatic ring, where each phenyl, phenoxy and 5- or 6-membered heteroaromatic ring may optionally be substituted and where the substituents independently of one another may be selected from one to three radicals W or one or more radicals R12, or
R2 and R3 may be attached to one another and form the ring M,
R4 represents hydrogen, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl, C1-C6-haloalkyl, C2-C6-haloalkenyl, C2-C6-haloalkynyl, C3-C6-halocycloalkyl, halogen, cyano, nitro, hydroxyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C1-C4-alkylthio, C1-C4-alkylsulfinyl, C1-C4-alkylsulfonyl, C1-C4-haloalkylthio, C1-C4-haloalkylsulfinyl, C1-C4-haloalkylsulfonyl, C1-C4-alkylamino, C2-C8-dialkylamino, C3-C6-cycloalkylamino, C3-C6-trialkylsilyl or represents phenyl, benzyl or phenoxy, each of which is optionally mono- or polysubstituted, where the substituents independently of one another may be selected from the group consisting of C1-C4-alkyl, C2-C4-alkenyl, C2-C4-alkynyl, C3-C6-cycloalkyl, C1-C4-haloalkyl, C2-C4-haloalkenyl, C2-C4-haloalkynyl, C3-C6-halocycloalkyl, halogen, cyano, nitro, C1-C4-alkoxy, C1-C4-haloalkoxy, C1-C4-alkylthio, C1-C4-alkylsulfinyl, C1-C4-alkylsulfonyl, C1-C4-alkylamino, C2-C8-dialkylamino, C3-C6-cycloalkylamino, C3-C6-(alkyl)cycloalkylamino, C2-C4-alkylcarbonyl, C2-C6-alkoxycarbonyl, C2-C6-alkylaminocarbonyl, C3-C8-dialkylaminocarbonyl and C3-C6-trialkylsilyl,
R5 and R8 in each case independently of one another represent hydrogen, halogen or represent in each case optionally substituted C1-C4-alkyl, C1-C4-haloalkyl, R12, G, J, —OJ, —OG, —S(O)p-J, —S(O)p-G, —S(O)p-phenyl, where the substituents independently of one another may be selected from one to three radicals W or from the group consisting of R12, C1-C10-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C4-alkoxy and C1-C4-alkylthio, where each substituent may be substituted by one or more substituents independently of one another selected from the group consisting of G, J, R6, halogen, cyano, nitro, amino, hydroxyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C1-C4-alkylthio, C1-C4-alkylsulfinyl, C1-C4-alkylsulfonyl, C1-C4-haloalkylthio, C1-C4-haloalkylsulfinyl, C1-C4-haloalkylsulfonyl, C1-C4-alkylamino, C2-C8-dialkylamino, C3-C6-trialkylsilyl, phenyl and phenoxy, where each phenyl or phenoxy ring may optionally be substituted and where the substituents independently of one another may be selected from one to three radicals W or one or more radicals R12,
G in each case independently of one another represent a 5- or 6-membered non-aromatic carbocyclic or heterocyclic ring which may optionally contain one or two ring members from the group consisting of C(═O), SO and S(═O)2 and which may optionally be substituted by one to four substituents independently of one another selected from the group consisting of C1-C2-alkyl, halogen, cyano, nitro and C1-C2-alkoxy, or independently of one another represent C2-C6-alkenyl, C2-C6-alkynyl, C3-C7-cycloalkyl, (cyano)-C3-C7-cycloalkyl, (C1-C4-alkyl)-C3-C6-cycloalkyl, (C3-C6-cycloalkyl)-C1-C4-alkyl, where each cycloalkyl, (alkyl)cycloalkyl and (cycloalkyl)alkyl may optionally be substituted by one or more halogen atoms,
J in each case independently of one another represent an optionally substituted 5- or 6-membered heteroaromatic ring, where the substituents independently of one another may be selected from one to three radicals W or one or more radicals R12,
R6 independently of one another represent —C(=E1)R19, -LC(=E1)R19, —C(=E1)LR19, -LC(=E1)LR19, —OP(=Q)(OR19)2, —SO2LR18 or -LSO2LR19, where each E1 independently of one another represents O, S, N—R15, N—OR15, N—N(R15)2, N—S═O, N—CN or N—NO2,
R7 represents hydrogen, C1-C4-alkyl, C1-C4-haloalkyl, halogen, C1-C4-alkoxy, C1-C4-haloalkoxy, C1-C4-alkylthio, C1-C4-alkylsulfinyl, C1-C4-alkylsulfonyl, C1-C4-halo-alkylthio, C1-C4-haloalkylsulfinyl, C1-C4-haloalkylsulfonyl,
R9 represents C1-C4-haloalkyl, C1-C4-haloalkoxy, C1-C4-haloalkylsulfinyl or halogen,
R10 represents hydrogen, C1-C4-alkyl, C1-C4-haloalkyl, halogen, cyano or C1-C4-haloalkoxy,
R11 in each case independently of one another represents in each case optionally mono- to trisubstituted C1-C6-alkylthio, C1-C6-alkylsulfenyl, C1-C6-haloalkythio, C1-C6-haloalkylsulfenyl, phenylthio or phenylsulfenyl, where the substituents independently of one another may be selected from the list W, —S(O)nN(R16)2, —C(═O)R13, -L(C═O)R14, —S(C═O)LR14, —C(═O)LR13, —S(O)nNR13C(=O)R13, —S(O)nNR13C(═O)LR14 or —S(O)nNR13S(O)2LR14,
L in each case independently of one another represents O, NR18 or S,
R12 in each case independently of one another represents —B(OR17)2, amino, SH, thiocyanato, C3-C8-trialkylsilyloxy, C1-C4-alkyl disulfide, —SF5, —C(=E1)R19, -LC(=E1)R19, —C(=E1)LR19, -LC(=E1)LR19, —OP(=Q)(OR19)2, —SO2LR19 or -LSO2LR19,
Q represents O or S,
R13 in each case independently of one another represent hydrogen or represent in each case optionally mono- or polysubstituted C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl or C3-C6-cycloalkyl, where the substituents independently of one another may be selected from the group consisting of R6, halogen, cyano, nitro, hydroxyl, C1-C4-alkoxy, C1-C4-alkylsulfinyl, C1-C4-alkylsulfonyl, C1-C4-alkylamino, C2-C8-dialkylamino, C3-C6-cycloalkylamino or (C1-C4-alkyl)-C3-C6-cycloalkylamino,
R14 in each case independently of one another represent in each case optionally mono- or polysubstituted C1-C20-alkyl, C2-C20-alkenyl, C2-C20-alkynyl or C3-C6-cycloalkyl, where the substituents independently of one another may be selected from the group consisting of R6, halogen, cyano, nitro, hydroxyl, C1-C4-alkoxy, C1-C4-alkylsulfinyl, C1-C4-alkylsulfonyl, C1-C4-alkylamino, C2-C8-dialkylamino, C3-C6-cycloalkylamino and (C1-C4-alkyl)-C3-C6-cycloalkylamino or represent optionally substituted phenyl, where the substituents independently of one another may be selected from one to three radicals W or one or more radicals R12,
R15 in each case independently of one another represent hydrogen or represent in each case optionally mono- or polysubstituted C1-C6-haloalkyl or C1-C6-alkyl, where the substituents independently of one another may be selected from the group consisting of cyano, nitro, hydroxyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C1-C4-alkylthio, C1-C4-alkylsulfinyl, C1-C4-alkylsulfonyl, C1-C4-haloalkylthio, C1-C4-haloalkylsulfinyl, C1-C4-haloalkylsulfonyl, C1-C4-alkylamino, C2-C8-dialkylamino, C2-C6-alkoxycarbonyl, C2-C6-alkylcarbonyl, C3-C6-trialkylsilyl and optionally substituted phenyl, where the substituents independently of one another may be selected from one to three radicals W or one or more radicals R12, or N(R5)2 represents a cycle which forms the ring M,
R16 represents C1-C12-alkyl or C1-C12-haloalkyl, or N(R16)2 represents a cycle which forms the ring M,
R17 in each case independently of one another represent hydrogen or C1-C4-alkyl, or B(OR17)2 represents a ring in which the two oxygen atoms are attached via a chain having two to three carbon atoms which are optionally substituted by one or two substituents independently of one another selected from the group consisting of methyl and C2-C6-alkoxycarbonyl,
R18 in each case independently of one another represent hydrogen, C1-C6-alkyl or C1-C6-haloalkyl, or N(R13)(R8) represents a cycle which forms the ring M,
R19 in each case independently of one another represent hydrogen or represent in each case mono- or polysubstituted C1-C6-alkyl, where the substituents independently of one another may be selected from the group consisting of cyano, nitro, hydroxyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C1-C4-alkylthio, C1-C4-alkylsulfinyl, C1-C4-alkylsulfonyl, C1-C4-haloalkylthio, C1-C4-haloalkylsulfinyl, C1-C4-haloalkylsulfonyl, C1-C4-alkylamino, C2-C8-dialkylamino, CO2H, C2-C6-alkoxycarbonyl, C2-C6-alkylcarbonyl, C3-C6-trialkylsilyl and optionally substituted phenyl, where the substituents independently of one another may be selected from one to three radicals W, C1-C6-haloalkyl, C3-C6-cycloalkyl or phenyl or pyridyl, each of which is optionally mono- to trisubstituted by W,
M in each case represents an optionally mono- to tetrasubstituted ring which, in addition to the nitrogen atom attached to the substituent pair R13 and R18, (R15)2 or (R16)2, contains two to six carbon atoms and optionally additionally a further nitrogen, sulfur or oxygen atom, where the substituents independently of one another may be selected from the group consisting of C1-C2-alkyl, halogen, cyano, nitro and C1-C2-alkoxy,
W in each case independently of one another represent C1-C4-alkyl, C2-C4-alkenyl, C2-C4-alkynyl, C3-C6-cycloalkyl, C1-C4-haloalkyl, C2-C4-haloalkenyl, C2-C4-haloalkynyl, C3-C6-halocycloalkyl, halogen, cyano, nitro, C1-C4-alkoxy, C1-C4-haloalkoxy, C1-C4-alkylthio, C1-C4-alkylsulfinyl, C1-C4-alkylsulfonyl, C1-C4-alkylamino, C2-C8-dialkylamino, C3-C6-cycloalkylamino, (C1-C4-alkyl)-C3-C6-cycloalkylamino, C2-C4-alkylcarbonyl, C2-C6-alkoxycarbonyl, CO2H, C2-C6-alkylaminocarbonyl, C3-C8-dialkylaminocarbonyl or C3-C6-trialkylsilyl,
n in each case independently of one another represent 0 or 1,
p in each case independently of one another represent 0, 1 or 2,
where, if (a) R5 represents hydrogen, C1-C6-alkyl, C1-C6-haloalkyl, C2-C6-haloalkenyl, C2-C6-haloalkynyl, C1-C4-haloalkoxy, C1-C4-haloalkylthio or halogen and (b) R8 represents hydrogen, C1-C6-alkyl, C1-C6-haloalkyl, C2-C6-haloalkenyl, C2-C6-haloalkynyl, C1-C4-haloalkoxy, C1-C4-haloalkylthio, halogen, C2-C4-alkylcarbonyl, C2-C6-alkoxycarbonyl, C2-C6-alkylaminocarbonyl or C3-C8 dialkylaminocarbonyl, (c) at least one substituent selected from the group consisting of R6, R11 and R12 is present and (d) if R12 is not present, at least one of the radicals R6 and R11 is different from C2-C6-alkylcarbonyl, C2-C6 alkoxycarbonyl, C2-C6-alkylaminocarbonyl and C3-C8-dialkylaminocarbonyl, and where the compound of the general formula (I) may also be an N-oxide or salt,
and at least one insecticidally active compound of groups 2 and 3 below selected from
A) (group 2), (2-1) azinphos-methyl and/or (2-2) chlorpyrifos and/or (2-3) diazinon and/or (2-4) dimethoate and/or (2-5) disulfoton and/or (2-6) ethion and/or (2-7) fenitrothion and/or (2-8) fenthion and/or (2-9) isoxathion and/or (2-10) malathion and/or (2-11) methidathion and/or (2-12) oxydemeton-methyl and/or (2-13) parathion and/or (2-14) parathion-methyl and/or (2-15) phenthoate and/or (2-16) phorate and/or (2-17) phosalone and/or (2-18) phosmet and/or (2-19) phoxim and/or (2-20) pirimiphos-methyl and/or (2-21) profenophos and/or (2-22) prothiophos and/or (2-23) tebupirimphos and/or (2-24) triazophos and/or (2-25) chlorfenvinphos and/or (2-26) dichlorphos and/or (2-27) dicrotophos and/or (2-28) mevinphos and/or (2-29) monocrotophos and/or (2-30) phosphamidon and/or (2-31) and/or (2-32) methamidophos and/or (2-33) trichlorfon and/or
B) (group 3), (3-1) carbaryl and/or (3-2) fenoxycarb and/or (3-3) formetanate and/or (3-4) formetanate hydrochloride and/or (3-5) methiocarb and/or (3-6) methomyl and/or (3-7) oxamyl and/or (3-8) pirimicarb and/or (3-9) propoxur and/or (3-10) thiodicarb

2. The composition as claimed in claim 1 comprising at least one compound of the formula (I-1) in which: in which

R2 represents hydrogen or C1-C6-alkyl,
R3 represents C1-C6-alkyl which is optionally substituted by one R6,
R4 represents C1-C4-alkyl, C1-C2-haloalkyl, C1-C2-haloalkoxy or halogen,
R5 represents hydrogen, C1-C4-alkyl, C1-C2-haloalkyl, C1-C2-haloalkoxy or halogen,
R6 represents —C(=E2)R19, -LC(=E2)R19, —C(=E2)LR19 or -LC(=E2)LR19, where each E2 independently of one another represents O, S, N—R15, N—OR15, N—N(R5)2, and each L independently of one another represents O or NR18,
R7 represents C1-C4-haloalkyl or halogen,
R9 represents C1-C2-haloalkyl, C1-C2-haloalkoxy, S(O)p—C1-C2-haloalkyl or halogen,
R15 in each case independently of one another represent hydrogen or represent in each case optionally substituted C1-C6-haloalkyl or C1-C6-alkyl, where the substituents independently of one another may be selected from the group consisting of cyano, C1-C4-alkoxy, C1-C4-haloalkoxy, C1-C4-alkylthio, C1-C4-alkylsulfinyl, C1-C4-alkylsulfonyl, C1-C4-haloalkylthio, C1-C4-haloalkylsulfinyl and C1-C4-haloalkylsulfonyl,
R18 in each case represents hydrogen or C1-C4-alkyl,
R19 in each case independently of one another represent hydrogen or C1-C6-alkyl,
and
p independently of one another represent 0, 1, 2.

3. The composition as claimed in claim 1 or 2 comprising at least one compound selected from the group consisting of

(2-2) chlorpyrifos,
(2-31) acephate,
(2-32) methamidophos,
(3-1) carbaryl,
(3-5) methiocarb, and
(3-10) thiodicarb.

4. The composition as claimed in claim 1, comprising at least one compound of formula (I) and at least one compound from group 2 and/or group 3 in a ratio of 50:1 to 1:50.

5. (canceled)

6. A process for preparing pesticides, comprising contacting a synergistically effective mixture as defined in claim 1, with extenders and/or surfactants.

7. A method for controlling animal pests, comprising allowing a synergistically effective mixture as defined in claim 1, to act on animal pests and/or their habitat.

Patent History
Publication number: 20070142327
Type: Application
Filed: Nov 20, 2004
Publication Date: Jun 21, 2007
Applicant: BAYER CROPSCIENCE AKTIENGESELLSCHAFT (Monheim)
Inventors: Christian Funke (Leichlingen), Reiner Fischer (Monheim), Rudiger Fischer (Pulheim), Heike Hungenberg (Langenfeld), Wolfram Andersch (Bergisch Gladbach), Wolfgang Thielert (Odenthal), Anton Kraus (Leichlingen)
Application Number: 10/581,346
Classifications
Current U.S. Class: 514/63.000; 514/341.000; 514/406.000; 514/80.000; 514/89.000; 514/85.000; 514/102.000; 514/114.000
International Classification: A01N 57/00 (20060101); A01N 55/00 (20060101); A01N 43/56 (20060101); A01N 43/40 (20060101);