WO2007101546A2

WO2007101546A2 - Combinations of active ingredients with insecticidal and acaricidal properties, containing phthalic acid diamides

Info

Publication number: WO2007101546A2
Application number: PCT/EP2007/001465
Authority: WO
Inventors: Rüdiger Fischer; Reiner Fischer; Christian Funke; Thomas Bretschneider; Heike Hungenberg; Wolfgang Thielert; Anton Kraus; Hiroshi Kodama; Shingo Tamura; Fumiaki Hakuno
Original assignee: Bayer Cropscience Ag
Priority date: 2006-03-06
Filing date: 2007-02-21
Publication date: 2007-09-13
Also published as: DE102006010208A1; AR059884A1; WO2007101546A3; TW200810692A

Abstract

The invention relates to novel combinations of active ingredients consisting of specific cyclic ketoenols of formula (I), in which A, B, D, G, W, X, Y and Z are defined as cited in the description and/or tetronic acid derivatives of formula (II), in which A', B', G', X', Y', Z' and n' are defined as cited in the description and phthalic acid diamides of formula (III), in which Hal represents chlorine, bromine or iodine and * represents a carbon atom with an R- or S-configuration, preferably an S-configuration. Said combinations have excellent insecticidal and acaricidal properties.

Description

Drug combinations with insecticidal and acaricidal properties

The present invention relates to novel drug combinations which consist of at least one known compound from the class of tetronic or tetramic acids on the one hand and at least one other known active ingredient from the class of phthalic diamides on the other hand and are very suitable for controlling animal pests such as insects and unwanted acarids ,

Pharmaceutical properties of 3-acylpyrrolidine-2,4-diones are described above (Suzuki, S. et al., Chem. Pharm. Bull, supra, 1120 (1967)). Furthermore, N-phenylpyrrolidine-2,4-diones were synthesized by R. Schmierer and H. Mildenberger (Liebigs Ann. Chem. 1985, 1095). Biological activity of these compounds has not been described.

EP-A-0 262 399 and GB-A-2 266 888 disclose similarly structured compounds (3-arylpyrrolidine-2,4-diones), of which, however, no herbicidal, insecticidal or acaricidal action has become known. Unsubstituted, bicyclic 3-arylpyrrolidine-2,4-dione derivatives (EP-A-355 599, EP-A-415 211 and JP-A-12-053 670) are known to have herbicidal, insecticidal or acaricidal activity and substituted monocyclic 3-arylpyrrolidine-2,4-dione derivatives (EP-A-377 893 and EP-A-442 077).

Also known are polycyclic 3-arylpyrrolidine-2,4-dione derivatives (EP-A-442 073) and 1H-arylpyrrolidine-dione derivatives (EP-A-456 063, EP-A-521 334, EP-A- 596 298, EP-A-613 884, EP-A-613 885, WO 95/01 997, WO 95/26 954, WO 95/20 572, EP-A-0 668 267, WO 96/25 395, WO 96 / 35,664, WO 97/01 535, WO 97/02 243, WO 97/36868, WO 97/43275, WO 98/05638, WO 98/06721, WO 98/25928, WO 99/16748, WO 99/24437 WO 99/43649, WO 99/48869 and WO 99/55673, WO 01/17972, WO 01/23354, WO 01/74770, WO 03/013249, WO 04/007448, WO 04/024688, WO 04/065366 WO 04/080962, WO 04/111042, WO 05/044791, WO 05/044796, WO 05/048710, WO 05/049596, WO 05/066125, WO 05/092897, WO 06/000355, WO 06/029799 , WO 06/056281, WO 06/056282, WO 06/089633.

It is known that certain substituted Δ ^-dihydrofuran-2-one derivatives have herbicidal properties (cf DE-A-4 014420). The synthesis of the tetronic acid derivatives used as starting compounds (such as, for example, 3- (2-methylphenyl) -4-hydroxy-5- (4-fluoro-phenyl) -Δ-dihydro-hydrofuranone (2)) is likewise described in DE-A- 4 014 420. Similarly structured compounds without indication of an insecticidal and / or acaricidal activity are known from the publication Campbell et al., J.Chem.Soc, Perkin Trans. 1, 1985, (8) 1567-76. Furthermore, 3-aryl-Δ ^ -dihydrofuranone derivatives having herbicidal, acaricidal and insecticidal properties are described in EP-A-528 156. EP-A-0 647 637. WO 95/26 345. WO 96/20 196, WO 96/25 395 , WHERE 96/35 664, WO 97/01 535, WO 97/02 243, WO 97/36 868, WO 98/05638, WO 98/25928, WO 99/16748, WO 99/43649, WO 99/48869, WO 99 And / or No. 55673, WO 01/17972, WO 01/23354 and WO 01/74770, WO 03/013249, WO 04/024688, WO 04/080962, WO 04/111042, WO 05/092897, WO 06/000355, WO 06 / 029799 and WO 06/089633.

It is also already known that phthalic diamides of the formula (EQ) have insecticidal activity. This applies to the racemic form of the compounds (EP-A 1 006 107) and, to an even greater degree, to the (S) -configured enantiomers (published Japanese patent application JP 2006-089469).

The generic formulas and definitions described in these publications as well as the individual compounds described therein are hereby incorporated by reference.

It has now been found that mixtures comprising at least one compound of the formula (I)

in which

X is halogen, alkyl, alkoxy, haloalkyl, haloalkoxy or cyano,

W, Y and Z independently of one another represent hydrogen, halogen, alkyl, alkoxy, haloalkyl, haloalkoxy or cyano,

A is hydrogen, in each case optionally halogen-substituted alkyl, alkoxyalkyl, saturated, optionally substituted cycloalkyl in which optionally at least one ring atom is replaced by a heteroatom,

B is hydrogen or alkyl,

A and B, together with the carbon atom to which they are attached, represent a saturated or unsaturated unsubstituted or substituted cycle, optionally containing at least one heteroatom, D is hydrogen or an optionally substituted radical from the series alkyl,

Alkenyl, alkoxyalkyl, saturated cycloalkyl in which optionally one or more ring members are replaced by heteroatoms,

A and D together with the atoms to which they are bonded represent a saturated or unsaturated and optionally at least one heteroatom-containing, unsubstituted or substituted in the A, D-part cycle,

G is hydrogen (a) or one of the groups

o _L R ⁴

^ R ¹ (b), ^ M ' ^R2 <O. ^{/ SO} ^ ^{R3 (d),} -J ^ (e),

E (f) or ^ - N '(g) _, L ^κ

stands,

wherein

E is a metal ion or an ammonium ion,

L is oxygen or sulfur,

M is oxygen or sulfur,

R! in each case optionally halogen-substituted alkyl, alkenyl, alkoxyalkyl, alkylthioalkyl, polyalkoxyalkyl or optionally substituted by halogen, alkyl or alkoxy-substituted cycloalkyl which may be interrupted by at least one heteroatom, in each case optionally substituted phenyl, phenylalkyl,

Hetaryl, phenoxyalkyl or hetaryloxyalkyl,

R 1 is in each case optionally halogen-substituted alkyl, alkenyl, alkoxyalkyl, polyalkoxyalkyl or in each case optionally substituted cycloalkyl,

Phenyl or benzyl,

R 1 represents optionally halogen-substituted alkyl or optionally substituted phenyl, R 1 and R 5 independently of one another are each optionally halogen-substituted alkyl, alkoxy, alkylamino, dialkylamino, alkylthio, alkenylthio, cycloalkylthio or in each case optionally substituted phenyl, benzyl, phenoxy or phenylthio, and

R ^ and R ^ independently of one another for hydrogen, in each case optionally

Halogen substituted alkyl, cycloalkyl, alkenyl, alkoxy, alkoxyalkyl, optionally substituted phenyl, optionally substituted BenΣyl or together with the N-atom to which they are attached, represent an optionally substituted by oxygen or sulfur optionally substituted ring

and or

at least one tetronic acid derivative of the formula (II)

in which

X ^{1 is} C i -Cg-alkyl, halogen, C y -Cg -alkoxy or Ci-C3-haloalkyl,

Y 'is hydrogen, C 1 -C 6 -alkyl, halogen, C 1 -CG-alkoxy, C 1 -C 6 -haloalkyl,

Z 'is C 1 -C 6 -alkyl, halogen, C 1 -C 6 -alkoxy,

n 'is a number from 0-3,

A 'is hydrogen or in each case optionally halogen-substituted straight-chain or branched C ₁ -C ₁₂ -alkyl, C ₂ -C ₆ -alkenyl, C ₂ -C 6 -alkyl, C ₁ -C ₁₀ -alkoxy-C ₁ -C ₆ -alkyl, C ₁ -C ₄ -alkyl-C ₁ -C ₄ -alkyl, C ₁ -C ₁ 0-alkylthio-C ₂ -C 6 -alkyl, cycloalkyl having 3 to 8 ring atoms, which may be interrupted by oxygen and / or sulfur or in each case optionally by halogen, C ₁ - Cg-AIlCyI, C ^ Cg haloalkyl, C ₁ -CG-AIkOXy-, C ₁ - Cg haloalkoxy, nitro-substituted phenyl or phenyl- ^ is -CG alkyl, B ^{1 is} hydrogen, C 1 -C 6 alkyl or C 1 -C 6 alkoxy C 1 -C ₄ alkyl

or in which

A 'and B' together with the carbon atom to which they are attached are saturated or unsaturated, optionally interrupted by oxygen and / or sulfur and optionally substituted by halogen, C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, C _j - C 1-4 haloalkyl, C 1 -C 4

Form halogenoalkoxy, C 1 -C 4 -alkylthio or optionally substituted phenyl-substituted or optionally benzo-fused 3 to 8-membered ring,

G 'for hydrogen (a) or for the groups

-CO-R ^{1 '} (b)

(C) -SO ₂ -R ^{3 '} (d)

in which

R.1 'is in each case optionally halogen-substituted C 1 -C 2 ₍₎ -alkyl, C 2 -C 20 -alkenyl, C 1 -CG-alkoxy-C 6 -C 6 -alkyl, C 1 -C 6 -alkylthio-C 1 -CG- Alkyl, C \ -Cg-polyalkoxy ^ -Cg- alkyl or cycloalkyl having 3-8 ring atoms, which may be interrupted by oxygen and / or sulfur atoms, is,

is optionally substituted by halogen, nitro, C _j -Cβ-alkyl, C ^ -Cg-alkoxy, C _j -Cg -haloalkyl, Ci-Cg-haloalkoxy-substituted phenyl

represents phenyl-Ci-Cg-alkyl optionally substituted by halogen, C _j -Cg-alkyl, C 1 -C 6 -alkoxy, Ci-Cg-haloalkyl, Ci-Cg-haloalkoxy-substituted,

is in each case optionally substituted by halogen and / or C 1 -C 6 -alkyl-substituted pyridyl, pyrimidyl, thiazolyl or pyrazolyl,

represents phenoxy-C 1 -C -alkyl optionally substituted by halogen and / or C 1 -C 6 -alkyl, R 2 'is in each case optionally halogen-substituted C 1 -C 2 ₍₎ -alkyl, C 2 -C 2 ( ₎ -alkenyl, C 1 -C 6 -alkoxy-C 2 -C 6 -alkyl or C 1 -C 6 -alkoxy-C 1 -C 4 -alkyl,

is in each case optionally halogen, nitro, C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -halogenoalkyl-substituted phenyl or benzyl,

R.3 ^{1 represents} optionally substituted by halogen C ^ -Cg-alkyl, in each case optionally by Ci-C4-alkyl, halogen, Ci-C4-haloalkyl, Ci-C ^ alkoxy, Ci-C4-haloalkoxy, nitro or Cyano is substituted phenyl or benzyl,

R4 'and RS' independently of one another in each case optionally halogen-substituted C _j -Cg-alkyl, Ci -Cg alkoxy, C _j -Cg alkylamino, di (C i -Cg) alkylamino, Ci-Cg-alkylthio, C 2 -C 5 -alkenylthio, C 2 -C 5 -alkynylthio, C 3 -C 5 -cycloalkylthio, in each case optionally by halogen, nitro, cyano, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, C 1 -C 4 -alkylthio, C 1 -C 4 -alkoxy Halogenoalkylthio, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl-substituted phenyl, phenoxy or phenylthio,

R "and R 'independently of one another in each case optionally substituted by halogen Cj- Ci _Q alkyl, Ci-Cio-alkoxy, Cβ-Cg-alkenyl, Ci-Cg-alkoxy-Ci-Cg-alkyl, optionally substituted by halogen, Cj -Cg-haloalkyl, Ci-Cg-alkyl or

substituted phenyl, benzyl optionally substituted by halogen, C ^ -Cg-alkyl, Ci-Cg-haloalkyl or C ^ - Cg-alkoxy or together represent an optionally interrupted by oxygen or sulfur 5- to 6-membered ring, the may optionally be substituted by Cj-Cg-alkyl,

and

at least one active substance of the formula (IH)

in which

Hal is chlorine, bromine or iodine, * denotes a carbon atom in the R or S configuration, preferably in the S configuration,

have insecticidal and / or acaricidal activity. Surprisingly, the insecticidal and / or acaricidal activity of the active compound combinations according to the invention is substantially higher than the sum of the effects of the individual active compounds. So there is an unpredictable, true synergistic effect and not just an effect supplement.

The compounds of the formula (I) or (II) can also be present, depending on the nature of the substituents, as geometric and / or optical isomers or mixtures of isomers in different compositions, which can optionally be separated in a customary manner , Both the pure isomers and the mixtures of isomers, their preparation and use and agents containing them are the subject of the present invention. In the following, however, for the sake of simplicity, reference is always made to compounds of the formula (I) or (EQ), although both the pure compounds and, if appropriate, mixtures with different proportions of isomeric compounds are meant.

Preference is given to active compound combinations comprising compounds of the formula (I) in which the radicals have the following meaning:

W is preferably hydrogen, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, chlorine, bromine or fluorine,

X is preferably C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkyl, fluorine, chlorine or bromine,

Y and Z independently of one another are preferably hydrogen, C 1 -C 4 -alkyl, halogen, C 1 -C 4 -alkoxy or C 1 -C 4 -haloalkyl,

A is preferably hydrogen or in each case optionally halogen-substituted C ₁ -C ₆ -alkyl or C ₃ -C 9 -cycloalkyl,

B is preferably hydrogen, methyl or ethyl,

A, B and the carbon atom to which they are attached are preferably saturated CyC ₆ -cycloalkyl, in which optionally one ring member is replaced by oxygen or sulfur and which is optionally mono- or disubstituted by C 1 -C ₄ -alkyl, trifluoromethyl or C 1 -C ₄ -alkyl _4- alkoxy is substituted, D is preferably hydrogen, in each case optionally fluorine- or chlorine-substituted C ₁ -C ₆ -alkyl, C ₃ -C ₄ -alkenyl or C ₃ -C ₆ -cycloalkyl,

A and D together preferably represent optionally methyl-substituted C ₃ -C ₄ -alkanediyl, in which optionally a methylene group is replaced by sulfur,

G is preferably hydrogen (a) or one of the groups

o _L R ⁴ '(b), - ^ (C), - ^SO ^ ^R3 <* 7 _/ V (e).

E / Λ or /} N ₇ ^ in particular for (a), (b), (c) or (g)

in which

E is a metal ion or an ammonium ion,

L stands for oxygen or sulfur and

M is oxygen or sulfur,

R ¹ preferably represents in each case optionally halogen-substituted C _r Ci ₀ alkyl, _C2 - Cio-alkenyl, _{Ci-C4-alkoxy-Ci-C} ₄ alkyl, C _r C ₄ alkylthio-Ci-C ₄ - C ₃ -C ₆ -cycloalkyl optionally substituted by fluorine, chlorine, C ₁ -C ₄ -alkyl or C ₁ -C ₂ -alkoxy,

is optionally substituted by fluorine, chlorine, bromine, cyano, nitro, Ci-C ₄ alkyl, C _r C ₄ alkoxy, or Triflourmethyl Triflourmethoxy substituted phenyl,

each optionally substituted by chlorine or methyl substituted pyridyl or thienyl,

R ² preferably represents in each case optionally substituted by fluorine or chlorine, Ci-Ci ₀ - alkyl, C ₂ -C ₁₀ alkenyl, C _r C ₄ -alkoxy-C ₂ -C ₄ alkyl,

for optionally substituted by methyl or methoxy C ₅ -C ₆ -cycloalkyl or

in each case optionally substituted by fluorine, chlorine, bromine, cyano, nitro, Ci-C ₄ alkyl, C] -C ₄ -

Alkoxy, trifluoromethyl or trifluoromethoxy substituted phenyl or benzyl, R ³ is preferably C 1 -C ₄ -alkyl optionally substituted by fluorine or phenyl optionally substituted by fluorine, chlorine, bromine, C 1 -C ₄ -alkyl, C 1 -C ₄ -alkoxy, trifluoromethyl, trifluoromethoxy, cyano or nitro,

R ⁴ preferably independently represent in each case optionally substituted by fluorine or chlorine, _Ci-C4-alkyl, Ci-C ₄ alkoxy, Ci-C ₄ alkylamino, C] -C ₄ -alkylthio or represents in each case optionally fluorine-, chlorine , Bromine, nitro, cyano, QC ₄ -alkoxy,

Trifluoromethoxy, C _r C ₄ alkylthio, C _r C ₄ haloalkylthio, C _r C ₄ alkyl or

Trifluoromethyl-substituted phenyl, phenoxy or phenylthio,

R ⁵ is preferably C 1 -C ₄ -alkoxy or C 1 -C ₄ -thioalkyl,

R ⁶ is preferably C ₁ -C ₆ -alkyl, C ₃ -C ₆ -cycloalkyl, C ₁ -C ₆ -alkoxy, C ₃ -C ₆ -alkenyl, C ₁ -C ₄ -alkoxy-C _r C ₄ - alkyl,

R ⁷ is preferably C ₁ -C ₆ -alkyl, C ₃ -C ₆ -alkenyl or C ₁ -C ₄ -alkoxy-C ₁ -C ₄ -alkyl,

R ⁶ and R ⁷ together preferably represent an optionally substituted by methyl or ethyl C ₃ -C ₆ alkylene, in which optionally a carbon atom is replaced by oxygen or sulfur

and / or at least one active ingredient of the formula (II) and at least one active ingredient of the formula

(M).

Particularly preferred are combinations of active substances containing compounds of the formula (I) in which the radicals have the following meaning:

W is particularly preferably hydrogen, methyl, ethyl, chlorine, bromine or methoxy,

X is particularly preferably chlorine, bromine, methyl, ethyl, propyl, isopropyl, methoxy, ethoxy or trifluoromethyl,

Y and Z are more preferably independently of one another hydrogen, fluorine, chlorine, bromine, methyl, ethyl, propyl, isopropyl, trifluoromethyl or methoxy,

A particularly preferably represents methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, cyclopropyl, cyclopentyl or cyclohexyl,

B is particularly preferably hydrogen, methyl or ethyl, A, B and the carbon atom to which they are attached are particularly preferably saturated C ₆ -cycloalkyl, in which optionally one ring member is replaced by oxygen and which is optionally monosubstituted by methyl, ethyl, methoxy, ethoxy, propoxy or butoxy,

D is particularly preferably hydrogen, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, allyl, cyclopropyl, cyclopentyl or cyclohexyl,

A and D together are particularly preferably C ₃ -C ₄ -alkanediyl optionally substituted by methyl,

G is particularly preferably hydrogen (a) or one of the groups

< ^β >

in which

M is oxygen or sulfur,

R ¹ particularly preferably represents C ₁ -C ₈ -alkyl, C ₂ -C ₄ -alkenyl, methoxymethyl, ethoxymethyl, ethylthiomethyl, cyclopropyl, cyclopentyl or cyclohexyl,

optionally once to twice by fluorine, chlorine, bromine, cyano, nitro, methyl,

Ethyl, methoxy, trifluoromethyl or trifluoromethoxy substituted phenyl,

for each optionally mono- to disubstituted by chlorine or methyl-substituted pyridyl or thienyl,

R ² particularly preferably represents C ₁ -C ₈ -alkyl, C ₂ -C ₄ -alkenyl, methoxyethyl, ethoxyethyl or phenyl or benzyl,

R ⁶ and R ⁷ independently of one another particularly preferably represent methyl, ethyl or together represent a C ₅ -alkylene radical in which the C ₃ -methylene group is replaced by oxygen

and / or at least one active ingredient of the formula (II) and at least one active ingredient of the formula (ED).

Very particular preference is given to active compound combinations comprising compounds of the formula (I) in which the radicals have the following meaning: W is very particularly preferably hydrogen or methyl,

X very particularly preferably represents chlorine, bromine or methyl,

Y and Z are very particularly preferably each independently hydrogen, chlorine, bromine or methyl,

A, B and the carbon atom to which they are attached very particularly preferably represent saturated C ₆ -cycloalkyl in which optionally one ring member is replaced by oxygen and which is optionally monosubstituted by methyl, methoxy, ethoxy, propoxy or butoxy,

D is very particularly preferably hydrogen,

G is very particularly preferably hydrogen (a) or one of the groups

oo \ _/ ^R6

^ R ¹ _(b) , ^ M ^'R2 (C) ^{, or} </ - V <*>

in which

M is oxygen or sulfur,

R ¹ very particularly preferably represents C ₁ -C ₈ -alkyl, C ₂ -C ₄ -alkenyl, methoxymethyl, ethoxymethyl, ethylmethylthio, cyclopropyl, cyclopentyl, cyclohexyl or optionally just by fluorine, chlorine, bromine, methyl, methoxy, trifluoromethyl,

Trifluoromethoxy, cyano or nitro-substituted phenyl, each optionally substituted by chlorine or methyl, pyridyl or thienyl,

R ² very particularly preferably represents C 1 -C ₈ -alkyl, C ₂ -C ₄ -alkenyl, methoxyethyl, ethoxyethyl, phenyl or benzyl,

R ⁶ and R ⁷ independently of one another very particularly preferably represent methyl, ethyl or together represent a C ₅ -alkylene radical in which the C ₃ -methylene group has been replaced by oxygen.

Particular preference is given to mixtures comprising spirotetramat (Ic-1)

and / or at least one active ingredient of the formula (H) and at least one active ingredient of the formula m, and mixtures containing the compound (I-a-1)

(M).

Preference is given to active ingredient combinations containing compounds of the formula (II) in which

X ^{1 is} C ¹ -C 4 -alkyl, chlorine, bromine, C 1 -C 4 -alkoxy or C 1 -C 6 -haloalkyl,

Y ^{1 is} hydrogen, C 1 -C 4 -alkyl, fluorine, chlorine, bromine, C 1 -C 4 -alkoxy, C 1 -C 3 -haloalkyl,

Z ^{1 is} C ¹ -C ₄ -alkyl, chlorine, bromine, C 1 -C ₄ -alkoxy,

n ^{1 is} a number from 0-2,

A 'is hydrogen or in each case optionally mono- to trisubstituted by fluorine-substituted straight-chain or branched C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 1 -C 4 -alkoxy-C 1 -C 2 -alkyl,

Cycloalkyl having 3-8 ring atoms, which may optionally be interrupted by oxygen and / or sulfur or represents optionally mono- to disubstituted by fluorine, chlorine, bromine, Ci-C2-alkyl, Q ^ haloalkyl, C _j ^ alkoxy, C _j ^ haloalkoxy, nitro-substituted phenyl or benzyl, B 'is hydrogen, C 1 -C 2 -alkyl or C j -C 2 -alkoxy-C 1 -C 2 -alkyl

or in which

A 'and B' together with the carbon atom to which they are bonded are a saturated or unsaturated, optionally interrupted by oxygen and / or sulfur and optionally mono- to disubstituted by fluorine, chlorine, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, Ci-C2-haloalkyl, Ci-C2-haloalkoxy or Ci-C2-alkylthio substituted 3- to 7-membered ring form,

G 'for hydrogen (a) or for the groups

- CO-R ^{1 '} (b)' - O - - FT (C) - SO _r R ^J (d)

in which

R.1 'is in each case optionally mono- to trisubstituted by fluorine or chlorine-substituted C 1 -C ₁₆ -alkyl, C 2 -C ₁₆ -alkenyl, C 1 -C ₄ -alkoxy-C 1 -C ₄ -alkyl, C 1 -C ₄ -alkylthio-C 1 -C ₄ -alkyl, C ₄ alkyl or cycloalkyl having 3-6 ring atoms which may be interrupted by oxygen and / or sulfur atoms,

optionally once to twice by fluorine, chlorine, bromine, nitro, C 1 -C 4 -alkyl,

C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkyl, C 1 -C 4 -halogeno-oxy-substituted phenyl,

represents optionally mono- to disubstituted by fluorine, chlorine, bromine, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkyl-, C 1 -C 4 -haloalkoxy-substituted benzyl,

represents in each case optionally mono- to disubstituted by chlorine, bromine and / or C 1 -C 4 -alkyl-substituted pyridyl, pyrimidyl, thiazolyl or pyrazolyl,

_J R ^ 'represents in each case optionally mono- to pentasubstituted by fluorine or chlorine by-substituted C - C2o alkyl, C2-C20 "alkenyl, Ci-Cg-alkoxy ^ -Ce-alkyl, Ci-C6-polyalkoxy-C2-Cg-alkyl represents . each optionally optionally mono- to disubstituted by fluorine, chlorine, bromine, nitro, C ^ -Cg-alkyl, C ^ -Cg-alkoxy, Ci-C4-haloalkyl-substituted phenyl or benzyl,

R ^ 'for optionally mono- to trisubstituted by fluorine or chlorine-substituted Ci-C4-alkyl, each optionally optionally once or twice by C _j -C ^ alkyl, fluorine, chlorine, bromine, Ci-C ^ haloalkyl, C ^ -C ^ Alkoxy, Cj-C4-haloalkoxy, nitro or cyano substituted phenyl or benzyl,

R ^ and R ^ independently of one another in each case optionally monosubstituted to trisubstituted by fluorine or chlorine, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -alkylamino, di- (C γ -C 4) -alkylamino, C 1 -C 4 Alkylthio, C 2 -C 4 -alkenylthio, C 3 -C 6 -cycloalkylthio, in each case optionally mono- to disubstituted by fluorine, chlorine, bromine, nitro, cyano, C 1 -C 2

Alkoxy, C ₁ -C ₂ -haloalkoxy, C ₁ -C ₂ -alkylthio, C ₁ -C ₂ -haloalkylthio, C ₁ -C ₂ -alkyl, C ₁ -C ₂ -haloalkyl-substituted phenyl, phenoxy or phenylthio,

Rr and R 'independently of one another are each optionally mono- to trisubstituted by fluorine or chlorine-substituted Ci-Cg-alkyl, C ^ -Cg-alkoxy, Cß-Cg-alkenyl, Ci-C4-alkoxy-Cj-C2-alkyl, optionally simply up to twice by fluorine, chlorine, bromine, C1-C2-

Haloalkyl, Ci-C4-alkyl or Ci-C4-alkoxy substituted benzyl or together represent an optionally interrupted by oxygen or sulfur 5- to 6-membered ring, which may optionally be substituted by Ci-C2-alkyl.

For the halogens mentioned in the preferred ranges with halogen, halogen is preferably chlorine and fluorine.

Particularly preferred are combinations of active substances containing compounds of the formula (II) in which

X 'is C 1 -C 4 -alkyl, chlorine, bromine, C 1 -C 4 -alkoxy or trifluoromethyl,

Y 'is hydrogen, C 1 -C 4 -alkyl, chlorine, bromine, C 1 -C 4 -alkoxy, C 1 -C 2 -haloalkyl,

Z 'is C 1 -C 4 -alkyl, chlorine, bromine, C _j -C 4 -alkoxy,

n ^{1 is} 0 or 1,

A 'and B' are saturated by C ^ -C 4 alkyl or C _j -C 4 alkoxy substituted 5- to 6-glie- drigen ring which is optionally mono-, together with the carbon atom to which they are attached, G 'for hydrogen (a) or for the groups

CO-R (b) ^* OR '(c) stands,

in which

RI 'is in each case optionally monosubstituted to trisubstituted by fluorine or chlorine, C 1 -C 12 -alkyl, C 2 -C 12 -alkenyl, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, or cycloalkyl having 3 to 6

Ring atoms, which may be interrupted by 1 to 2 oxygen atoms,

or optionally monosubstituted by fluorine, chlorine, bromine, nitro, C _j ^ -C alkyl, C1-C4 alkoxy, trifluoromethyl or trifluoromethoxy-substituted phenyl,

R ² 'is C 1 -C 12 -alkyl, C ₂ -C-γ ₂ -alkenyl, C γ -C 4 -alkoxy-C ₂ -C 4 -alkyl,

each optionally optionally substituted by fluorine, chlorine, bromine, nitro, Cj-C4-alkyl, C1-C4-

Alkoxy or trifluoromethyl substituted phenyl or benzyl, and at least one active ingredient of the formula (II).

Very particular preference is given to active ingredient combinations containing compounds of the formula (II) in which

X 'is methyl, ethyl, chlorine, bromine, methoxy, ethoxy or trifluoromethyl,

Y 'is hydrogen, methyl, ethyl, chlorine, bromine, methoxy or trifluoromethyl,

Z 'is methyl, ethyl, chlorine, bromine or methoxy,

n ^{1 is} 0 or 1,

A 'and B' together with the carbon atom to which they are attached form a saturated 5- to 6-membered ring which is optionally substituted by methyl, ethyl, propyl, methoxy, ethoxy, propoxy, butoxy or isobutoxy,

G 'for hydrogen (a) or for the groups

-CO-R ^{1 '} (b)

(C) in which

R.1 'is in each case optionally mono- to trisubstituted by fluorine or chlorine, C 1 -C 6 -alkyl, C 2 -C -alkenyl, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, or cycloalkyl having 3 to 6 ring atoms, which is substituted by 1 to 2 oxygen atoms can be interrupted, stands,

represents optionally monosubstituted by fluorine, chlorine, bromine, methyl, methoxy, trifluoromethyl or trifluoromethoxy phenyl,

R ² 'is Ci-Cg-alkyl, C2-Cg-alkenyl, Ci-C ^ alkoxy ^ -Cß-alkyl,

each optionally optionally substituted by fluorine, chlorine, bromine, nitro, methyl, methoxy or trifluoromethyl substituted phenyl or benzyl.

Particularly preferred are combinations of active compounds containing compounds of the formula (II-b-1) or (Η-b-2).

(π-b-1) spirodiclofen

(π-b-2) spiromesifen

Preference is given to mixtures comprising at least one of the compounds (IIa), (IIIb) or (IIIc). (IHa): (S) -S-IOd-N ¹ - {2-methyl-4- [1,2,2,2-tetrafluoro-1 - (trifluoromethyl) ethyl] phenyl} -N ² - (1-methyl -2-methylsulfonylethyl) phthalamide

(mb): (S) -3-Chloro-N ¹ - {2-methyl-4- [l, 2,2,2-tetrafluoro-1 - (trifluoromethyl) ethyl] phenyl} -N ² - (1-methyl -2-methylsulphonylethyl) phthalamide

(mc): (S) -3-bromo-N ¹ - {2-methyl-4- [l, 2,2,2-tetrafluoro-1 - (trifluoromethyl) ethyl] phenyl} -N ² - (1-methyl -2-methylsulphonylethyl) phthalamides

The active compound combinations according to the invention contain, in addition to at least one active compound of the formula (III) in enantiomerically pure form or as a mixture of the two enantiomers in any ratio, at least one compound of the formula (I) and / or of the formula (II).

The active compound combinations according to the invention preferably contain one of the active compounds (HIa), (HIb) or (lue) and a compound of the formula (I) or a compound of the formula (II).

Particular preference is given to active ingredient combinations containing the compound of the formula (II-b-1)

and at least one active ingredient of the formula (LT).

Also particularly preferred are combinations of active substances containing the compound of the formula (II-c-2)

and at least one active ingredient of the formula (JE).

Also particularly preferred are combinations of active substances containing the compound of the formula (I-c-2)

and at least one active ingredient of the formula (HQ;

Active substance combinations containing spitotetramat (Ic-1)

or the compound (I-a-1)

and at least one active ingredient of the formula (III).

Very particularly preferred is a mixture containing the compound (IIIa) and the compound (I-c-2).

Furthermore, very particularly preferred is a mixture containing the compound (IHa) and the compound (I-c-1).

Furthermore, very particularly preferred is a mixture containing the compound (HIa) and the compound (I-a-1).

Furthermore, very particularly preferred is a mixture containing the compound (HIa) and the compound (II-b-1).

Furthermore, very particularly preferred is a mixture containing the compound (HIa) and the compound (Hb-2). Furthermore, very particularly preferred is a mixture containing the compound (HIb) and the compound (Ic-2).

Furthermore, very particularly preferred is a mixture containing the compound (HIb) and the compound (I-c-1).

Furthermore, very particularly preferred is a mixture containing the compound (DIb) and the compound (I-a-1).

Furthermore, very particularly preferred is a mixture containing the compound (DIb) and the compound (D-b-1).

Furthermore, very particularly preferred is a mixture containing the compound (DIb) and the compound (D-b-2).

Furthermore, very particularly preferred is a mixture containing the compound (DIc) and the compound (I-c-2).

Furthermore, very particularly preferred is a mixture containing the compound (DIc) and the compound (I-c-1).

Furthermore, very particularly preferred is a mixture containing the compound (DIc) and the compound (I-a-1).

Furthermore, very particularly preferred is a mixture containing the compound (DIc) and the compound (D-b-1).

Furthermore, very particularly preferred is a mixture containing the compound (DIc) and the compound (D-b-2).

Particularly preferred is a mixture containing the compound (DIb) and the compound (I-c-2).

Also particularly preferred is a mixture containing the compound (DIb) and the compound (I-c-1).

Also particularly preferred is a mixture containing the compound (DIb) and the compound (Ia-1). Also particularly preferred is a mixture containing the compound (DIb) and the compound (II-b-1).

Also particularly preferred is a mixture containing the compound (HIb) and the compound (II-b-2).

If the active ingredients in the active compound combinations according to the invention are present in certain weight ratios, the synergistic effect is particularly pronounced. However, the weight ratios of the drugs in the drug combinations can be varied in a relatively wide range. In general, the combinations according to the invention contain an active ingredient of the formula (I) or an active ingredient of the formula (II) and an active ingredient of the formula (II) in the following preferred and particularly preferred mixing ratios:

Preferred mixing ratio: 125: 1 to 1: 125

Particularly preferred mixing ratio: 25: 1 to 1:25

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

The active compound combinations according to the invention are suitable for good plant tolerance, favorable toxicity to warm-blooded animals and good environmental compatibility for the protection of plants and plant organs, for increasing crop yields, improving the quality of the crop and for controlling animal pests, in particular insects, arachnids, helminths, nematodes and mollusks in agriculture, horticulture, livestock, forests, gardens and recreational facilities, in the protection of materials and materials and in the hygiene sector. They can preferably be used as crop protection agents. They are effective against normally sensitive and resistant species as well as against all or individual stages of development. The above mentioned pests include:

From the order of the Anoplura (Phthiraptera) e.g. Damalinia spp., Haematopinus spp., Linognathus spp., Pediculus spp., Trichodectes spp.

From the class of the Arachnida eg Acarus siro, Aceria sheldoni, Aculops spp., Aculus spp., Amblyomma spp., Argas spp., Boophilus spp., Brevipalpus spp., Bryobia praetiosa, Chorioptes spp., Dermanyssus gallinae, Eotetranychus spp. Epitrimerus pyri, Eutetranychus spp., Eriophyes spp., Hemitarsonemus spp., Hyalomma spp., Ixodes spp., Latrodectus mactans, Metatetranychus spp., Oligonychus spp., Ornithodoros spp., Panonychus spp., Phyllocoptruta oleivora, Polyphagotarsonemus latus, Psoroptes spp., Rhipicephalus spp., Rhizoglyphus spp., Sarcoptes spp., Scorpio maurus, Stenotarsonemus spp., Tarsonemus spp., Tetranychus spp., Vasates lycopersici.

From the class of bivalva, e.g. Dreissena spp.

From the order of Chilopoda e.g. Geophilus spp., Scutigera spp.

From the order of Coleoptera e.g. Acanthoscelides obtectus, Adoretus spp., Agelastica alni, Agriotes spp., Amphimallon solstitialis, Anobium punctatum, Anoplophora spp., Anthonomus spp., Anthrenus spp., Apogonia spp., Atomaria spp., Attagenus spp., Bruchidius obtectus, Bruchus spp. , Ceuthorhynchus spp., Cleonus mendicus, Conoderus spp., Cosmopolites spp., Costelytra zealandica, Curculio spp., Cryptorhynchus lapathi, Dermestes spp., Diabrotica spp., Epilachna spp., Faustinus cubae, Gibbium psylloides, Heteronychus arator, Hylamorpha elegans, Hylotrupes bajulus, Hypera postica, Hypothenemus spp., Lachnosterna consanguinea, Leptinotarsa decemlineata, Lissorhoptrus oryzophilus, Lixus spp., Lyctus spp., Meligethes aeneus, Melolontha melolontha, Migdolus spp., Monochamus spp., Naupactus xanthographus, Niptus hololeucus, Oryctes rhinoceros, Oryzaephilus surinamensis, Otiorrhynchus sulcatus, Oxycetonia jucunda, Phaedon cochleariae, Phyllophaga spp., Popillia japonica, Premnotrypes spp., Psylliodes chrysoccephala, Ptinus spp , Rhizobius ventralis, Rhizopertha dominica, Sitophilus spp., Sphenophorus spp., Starchus spp., Symphyletes spp., Tenebrio molitor, Tribolium spp., Trogoderma spp., Tychius spp., Xylotrechus spp., Zabrus spp.

From the order of Collembola e.g. Onychiurus armatus.

From the order of the Dermaptera e.g. Forficula auricularia.

From the order of diplopoda e.g. Blaniulus guttulatus.

From the order of Diptera e.g. Aedes spp., Anopheles spp., Bibio hortulanus, Calliphora erythrocephala, Ceratitis capitata, Chrysomyia spp., Cochliomyia spp., Cordylobia anthropophaga, Culex spp., Cuterebra spp., Dacus oleae, Dermatobia hominis, Drosophila spp., Fannia spp. Gastrophilus spp., Hylemyia spp., Hyppobosca spp., Hypoderma spp., Liriomyza spp. Lucilia spp., Musca spp., Nezara spp., Oestrus spp., Oscinella frit, Pegomyia hyoscyami, Phorbia spp., Stomoxys spp. Tabanus spp., Tannia spp., Tipula paludosa, Wohlfahrtia spp.

From the class Gastropoda eg Arion spp., Biomphalaria spp., Bulinus spp., Deroceras spp., Galba spp., Lymnaea spp., Oncomelania spp., Succinea spp. From the class of helminths, for example, Ancylostoma duodenale, Ancylostoma ceylanicum, Acylostoma braziliensis, Ancylostoma spp., Ascaris lubricoides, Ascaris spp., Brugia malayi, Brugia timori, Bunostomum spp., Chabertia spp., Clonorchis spp., Cooperia spp., Dicrocoelium spp , Dictyocaulus filaria, Diphyllobothrium latum, Dracunculus medinensis, Echinococcus granulosus, Echinococcus multilocularis, Enterobius vermicularis, Faciola spp., Haemonchus spp., Heterakis spp., Hymenolepis nana, Hyostrongulus spp., Loa Loa, Nematodirus spp., Oesophagostomum spp., Opisthorchis spp., Onchocerca volvulus, Ostertagia spp., Paragonimus spp., Schistosome spp, Strongyloides fuelleborni, Strongyloides stercoralis, Stronyloides spp., Taenia saginata, Taenia solium, Trichinella spiralis, Trichinella nativa, Trichinella britovi, Trichinella nelsoni, Trichinella pseudopsiralis, Trichostrongulus spp ., Trichuris trichuria, Wuchereria bancrofti.

Furthermore, protozoa, such as Eimeria, can be combated.

From the order of Heteroptera, e.g. Anasa tristis, Antestiopsis spp., Blissus spp., Calocoris spp., Campylomma livida, Cavelerius spp., Cimex spp., Creontiades dilutus, Dasynus piperis, Dichelops furcatus, Diconocoris hewetti, Dysdercus spp., Euschistus spp., Eurygaster spp. Heliopeltis spp., Horcias nobilellus, Leptocorisa spp., Leptoglossus phyllopus, Lygus spp., Macropes excavatus, Miridae, Nezara spp., Oebalus spp., Pentomidae, Piesma quadrata, Piezodorus spp., Psallus seriatus, Pseudacysta persea, Rhodnius spp. Sahlbergella singularis, Scotinophora spp., Stephanitis nashi, Tibraca spp., Triatoma spp.

From the order of Homoptera eg Acyrthosipon spp., Aeneolamia spp., Agonoscena spp., Aleurodes spp., Aleurolobus barodensis, Aleurothrixus spp., Amrasca spp., Anuraphis cardui, Aonidiella spp., Aphanostigma piri, Aphis spp., Arboridia apicalis, Aspidiella spp., Aspidiotus spp., Atanus spp., Aulacorthum solani, Bemisia spp., Brachycaudus helichrysii, Brachycolus spp., Brevicoryne brassicae, Calligypona marginata, Carneocephala fulgida, Ceratovacuna lanigera, Cercopidae, Ceroplastes spp., Chaetosiphon fragaefolii, Chionetis tegalensis, Chlorita onukii, Chromaphis juglandicola, Chrysomphalus ficus, Cicadulina mbila, Coccomytilus halli, Coccus spp., Cryptomyzus ribis, Dalbulus spp., Dialeurodes spp., Diaphorina spp., Diaspis spp., Doralis spp., Drosicha spp., Dysaphis spp. Dysmicoccus spp., Empoasca spp., Eriosoma spp., Erythroneura spp., Euscelis bilobatus, Geococcus coffeae, Homalodisca coagulata, Hyalopterus arundinis, Icerya spp., Idiocerus spp., Idioscopus spp., Laodelphax striatel lusoids, Lecanium spp., Lepidosaphes spp., Lipaphis erysimi, Macrosiphum spp., Mahanarva fϊmbriolata, Melanaphis sacchari, Metcalfiella spp., Metopolophium dirhodum, Monellia costalis, Monelliopsis pecanis, Myzus spp., Nasonovia ribisnigri, Nephotettix spp., Nilaparvata lugens, Oncometopia spp., Orthezia praelonga, Parabemisia myricae, Paratrioza spp., Parlatoria spp., Pemphigus spp., Pere- Grinus maidis, Phenacoccus spp., Phloeomyzus passerinii, Phorodon humuli, Phylloxera spp., Pinnaspis aspidistrae, Planococcus spp., Protopulvinaria pyriformis, Pseudaulacaspis pentagona, Pseudococcus spp., Psylla spp., Pteromalus spp., Pyrilla spp., Quadraspidiotus spp. Quesada gigas, Rastrococcus spp., Rhopalosiphum spp., Saissetia spp., Scaphoides titanus, Schizaphis graminum, Selenaspidus articulatus, Sogata spp., Sogatella furcifera, Sogatodes spp., Stictocephala festina, Tenalaphara malayensis, Tinocallis caryaefoliae, Tomaspis spp., Toxoptera spp , Tri- aleurodes vaporariorum, Trioza spp., Typhlocyba spp., Unaspis spp., Viteus vitifolii.

From the order of Hymenoptera e.g. Diprion spp., Hoplocampa spp., Lasius spp., Monomorium pharaonis, Vespa spp.

From the order of isopods e.g. Armadillidium vulgaris, Oniscus asellus, Porcellio scaber.

From the order of Isoptera e.g. Reticulitermes spp., Odontotermes spp.

From the order of Lepidoptera e.g. Acronicta major, Aedia leucomelas, Agrotis spp., Alabama argillacea, Anticarsia spp., Barathra brassicae, Bucculatrix thurberiella, Bupalus pinarius, Cacoecia podana, Capua reticulana, Carpocapsa pomonella, Cheimatobia brumata, Chilo spp., Choristoneura fumiferana, Clysia ambiguella, Cnaphalocerus spp , Earias insulana, Ephestia kuehniella, Euproctis chrysorrhoea, Euxoa spp., Feltia spp., Galleria mellonella, Helicoverpa spp., Heliothis spp., Hofmannophila pseudospretella, Homona magnanima, Hyponomeuta padella, La phygma spp., Lithocolletis blancardella, Lithophane antennata , Loxagrotis albicosta, Lymantria spp., Malacosoma neustria, Mamestra brassicae, Mocis repanda, Mythimna separata, Oria spp., Oulema oryzae, Panolis flammea, Pectinophora gossypiella, Phyllocnistis citrella, Pieris spp., Plutella xylostella, Prodenia spp., Pseudaletia spp. , Pseudoplusia includens, Pyrausta nubilalis, Spodoptera spp., Thermesia gemmatalis, Tinea pellionella, Tineola bisselliella, Tortrix viridana, Trichoplusia spp.

From the order of Orthoptera e.g. Acheta domesticus, Blatta orientalis, Blattella germanica, Gryllotalpa spp., Leucophaea maderae, Locusta spp., Melanoplus spp., Periplaneta americana, Schistocerca gregaria.

From the order of siphonaptera e.g. Ceratophyllus spp., Xenopsylla cheopis.

From the order of Symphyla e.g. Scutigerella immaculata.

From the order of the Thysanoptera eg Baliothrips biformis, Enneothrips flavens, Frankliniella spp., Heliothrips spp., Hercinothrips femoralis, Kakothrips spp., Rhipiphorothrips cruentatus, Scirtothrips spp., Taeniothrips cardamoni, Thrips spp. From the order of Thysanura eg Lepisma saccharina.

The plant parasitic nematodes include e.g. Anguina spp., Aphelenchoides spp., Belonoaimus spp., Bursaphelenchus spp., Ditylenchus dipsaci, Globodera spp., Heliocotylenchus spp., Heterodera spp., Longidorus spp., Meloidogyne spp., Pratylenchus spp., Radopholus similis, Rotylenchus spp. Trichodorus spp., Tylenchorhynchus spp., Tylenchulus spp., Tylenchulus semipenetrans, Xiphinema spp.

The active compound combinations according to the invention may optionally also be used in certain concentrations or application rates as herbicides, safeners, growth regulators or agents for improving plant properties, or as microbicides, for example as fungicides, antimycotics, bactericides, viricides (including anti-viral agents) or as anti-MLO agents ( Mycoplasma-like-organism) and RLO (Rickettsia-like-organism). If appropriate, they can also be used as intermediates or precursors for the synthesis of further active ingredients.

The active compound combinations according to the invention may optionally also be used in certain concentrations or application rates with at least one herbicide, safener, waxy regulator or plant properties improver, or with at least one microbicide, for example fungicide, antimycotic, bactericide, viricide (including anti-viral agents) or with agents against MLO (Mycoplasma-like-organism) and RLO (Rickettsia-like-organism) or mixtures thereof.

According to the invention, all plants and parts of plants can be treated. In this context, plants are understood 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 varieties which can or can not be protected by plant breeders' rights. Plant parts are to be understood as meaning all aboveground and underground parts and organs of the plants, such as shoot, leaf, flower and root, examples of which include leaves, needles, stems, stems, flowers, fruiting bodies, fruits and seeds, as well as roots, tubers and rhizomes. The plant parts also include crops and vegetative and generative propagation material, such as cuttings, tubers, rhizomes, offshoots and seeds. The treatment according to the invention of the plants and plant parts with the active substance combinations takes place directly or by acting on their environment, habitat or storage space according to the customary treatment methods, eg by dipping, spraying, evaporating, atomizing, spreading, spreading, injecting and in propagation material, in particular in seed, furthermore by single or multi-layer wrapping.

The active compound combinations can be converted into the customary formulations, such as solutions, emulsions, wettable powders, water- and oil-based suspensions, powders, dusts, pastes, soluble powders, soluble granules, scattering granules, suspension-emulsion concentrates, active substance-impregnated natural products, active ingredient Impregnated synthetic materials, fertilizers and Feinstverkapselungen in polymeric materials.

These formulations are prepared in a known manner, e.g. by mixing the active compounds with extenders, ie liquid solvents and / or solid carriers, if appropriate using surface-active agents, ie emulsifiers and / or dispersants and / or foam-forming agents. The preparation of the formulations is carried out either in suitable systems or before or during use.

Excipients which can be used are those which are suitable for imparting special properties to the composition itself and / or preparations derived therefrom (for example spray liquor, seed dressing), such as certain technical properties and / or specific biological properties. Typical auxiliaries are: extenders, solvents and carriers.

As extender, e.g. Water, polar and non-polar organic chemical liquids e.g. from the classes of aromatic and non-aromatic hydrocarbons (such as paraffins, alkylbenzenes, alkylnaphthalenes, chlorobenzenes), alcohols and polyols (which may also be substituted, etherified and / or esterified), ketones (such as acetone, cyclohexanone), Esters (also fats and oils) and (poly) ethers, the simple and substituted amines, amides, lactams (such as N-alkylpyrrolidones) and lactones, the sulfones and sulfoxides (such as dimethylsulfoxide).

In the case of using water as extender, for example, organic solvents can also be used as auxiliary solvents. Suitable liquid solvents are essentially: aromatics, such as xylene, toluene, or alkylnaphthalenes, chlorinated aromatics and chlorinated aliphatic hydrocarbons, such as chlorobenzenes, chloroethylenes or methylene chloride, aliphatic hydrocarbons, such as cyclohexane or paraffins, for example petroleum fractions, mineral acids. vegetable 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 dimethyl sulfoxide, and water.

Suitable solid carriers are:

e.g. Ammonium salts and ground natural minerals, such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth, and ground synthetic minerals, such as fumed silica, alumina and silicates, as solid carriers for granules are suitable: e.g. crushed and fractionated natural rocks such as calcite, marble, pumice, sepiolite, dolomite and synthetic granules of inorganic and organic flours and granules of organic material such as paper, sawdust, coconut shells, corn cobs and tobacco stalks; suitable emulsifiers and / or foam formers are: e.g. nonionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, e.g. Alkylaryl polyglycol ethers, alkylsulfonates, alkyl sulfates, arylsulfonates and protein hydrolysates; suitable dispersants are non-ionic and / or ionic substances, e.g. from the classes of alcohol POE and / or POP ethers, acid and / or POP POE esters, alkyl aryl and / or POP POE ethers, fatty and / or POP POE adducts, POE and / or POP polyol derivatives, POE and / or POP sorbitol or sugar adducts, alkyl or aryl sulfates, sulfonates and phosphates or the corresponding PO ether adducts. Further suitable oligo- or polymers, e.g. starting from vinylic monomers, from acrylic acid, from EO and / or PO alone or in combination with e.g. (poly) alcohols or (poly) amines. Furthermore, find use lignin and its sulfonic acid derivatives, simple and modified celluloses, aromatic and / or aliphatic sulfonic acids and their adducts with formaldehyde.

Adhesives such as carboxymethylcellulose, natural and synthetic powdery, granular or latex-type polymers such as gum arabic, polyvinyl alcohol, polyvinyl acetate, and natural phospholipids such as cephalins and lecithins and synthetic phospholipids may be used in the formulations.

Dyes such as inorganic pigments such as iron oxide, titanium oxide, ferrocyan blue and organic dyes such as alizarin, azo and metal phthalocyanine dyes and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc can be used. Other additives may be fragrances, mineral or vegetable optionally modified oils, waxes and nutrients (also trace nutrients), such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc.

Stabilizers such as cold stabilizers, preservatives, antioxidants, light stabilizers or other chemical and / or physical stability-improving agents may also be present.

The formulations generally contain between 0.01 and 98% by weight of active ingredient, preferably between 0.5 and 90%.

The active compound combinations according to the invention can be present in commercial formulations as well as in the formulations prepared from these formulations in admixture with other active ingredients such as insecticides, attractants, sterilants, bactericides, acaricides, nematicides, fungicides, growth-regulating substances or herbicides. The insecticides include, for example, phosphoric acid esters, carbamates, carboxylic esters, chlorinated hydrocarbons, phenylureas, microorganism-produced substances and the like.

A mixture with other known active substances, such as herbicides or with fertilizers and growth regulators is possible.

The active compound combinations according to the invention may also be present when used as insecticides in their commercial formulations as well as in the formulations prepared from these formulations in admixture with synergists. Synergists are compounds that increase the effect of the active ingredients without the added synergist itself having to be active.

The active substance content of the application forms prepared from the commercial formulations can vary within wide ranges. The active ingredient concentration of the use forms may be from 0.00000001 up to 95% by weight of active compound, preferably between 0.00001 and 1% by weight.

The application is done in a custom forms adapted to the application forms.

As already mentioned above, according to the invention all plants and their parts can be treated. In a preferred embodiment, wild-type or plant species obtained by conventional biological breeding methods, such as crossing or protoplast fusion, and plant cultivars and their parts are treated. In a further preferred embodiment, transgenic plants and plant cultivars obtained by genetic engineering, optionally in combination with conventional methods, are obtained (Genetically Modified Organisms) and their parts. The terms "parts" or "parts of plants" or "plant parts" have been explained above.

It is particularly preferred according to the invention to treat plants of the respective commercially available or in use plant cultivars. Plant varieties are understood as meaning plants having new traits which have been bred by conventional breeding, by mutagenesis or by recombinant DNA techniques. These can be varieties, biotypes and genotypes.

Depending on the plant species or plant cultivars, their location and growth conditions (soils, climate, vegetation period, diet), the treatment according to the invention may also give rise to superadditive ("synergistic") effects. Thus, for example, reduced application rates and / or extensions of the spectrum of action and / or an increase in the effect of the substances and agents usable in 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 power facilitated harvest, acceleration of ripeness, higher crop yields, higher quality and / or higher nutritional value of the harvested products, higher shelf life and / or machinability of the harvested products, which exceed the actual expected effects.

The preferred plants or plant varieties to be treated according to the invention to be treated include all plants which, as a result of the genetic engineering modification, obtained genetic material which gives these plants particularly advantageous valuable properties ("traits"). Examples of such properties are better plant growth, increased tolerance to high or low temperatures, increased tolerance to dryness or to bottoms salt, increased flowering, easier harvesting, acceleration of ripeness, higher crop yields, higher quality and / or higher nutritional value of the harvested products , higher shelf life and / or workability of the harvested products. Further and particularly emphasized examples of such properties are an increased defense of the plants against animal and microbial pests, as against insects, mites, phytopathogenic fungi, bacteria and / or viruses as well as an increased tolerance of the plants against certain herbicidal active substances. Examples of transgenic plants are the important crops such as cereals (wheat, rice), corn, soybeans, potatoes, sugar beets, tomatoes, peas and other vegetables, cotton, tobacco, oilseed rape and fruit plants (with the fruits apples, pears, citrus fruits and Grapes), with special emphasis on maize, soya, potato, cotton, tobacco and oilseed rape. Traits that are particularly emphasized are the increased defense of the plants against insects, arachnids, Nematodes and snails by toxins produced in the plants, in particular those produced by the genetic material from Bacillus thuringiensis (eg by the genes CryΙA (a), CryIA (b), CryΙA (c), CryllA, CrylEA, CryIIIB2, Cry9c Cry2Ab, Cry3Bb and CryEF and their combinations) in the plants (hereinafter "Bt plants"). Traits also highlight the increased resistance of plants to fungi, bacteria and viruses by systemic acquired resistance (SAR), systemin, phytoalexins, elicitors and resistance genes and correspondingly expressed proteins and toxins. Traits which are furthermore particularly emphasized are the increased tolerance of the plants to certain herbicidally active compounds, for example imidazolinones, sulfonylureas, glyphosate or phosphinotricin (eg "PAT" gene). The genes which confer the desired properties ("traits") can also occur in combinations with one another in the transgenic plants. Examples of "Bt plants" are maize varieties, cotton varieties, soybean varieties and potato varieties which are sold under the trade names YIELD GARD® (eg corn, cotton, soya), KnockOut® (eg maize), StarLink® (eg maize), Bollgard® ( Cotton), Nucotn® (cotton) and NewLeaf® (potato). Examples of herbicide-tolerant plants are maize varieties, cotton varieties and soybean varieties, which are sold under the trade names Roundup Ready® (tolerance to glyphosate eg corn, cotton, soy), Liberty Link® (tolerance to phosphinotricin, eg rapeseed), IMI® (tolerance against imidazolinone) and STS® (tolerance to sulfonylureas eg corn). As herbicide-resistant (conventionally grown on herbicide tolerance) plants are also sold under the name Clearfϊeld® varieties (eg corn) mentioned. Of course, these statements also apply to future or future marketed plant varieties with these or future developed genetic traits.

The listed plants can be treated particularly advantageously with the active compound combinations according to the invention. The preferred ranges given above for the active substance combinations also apply to the treatment of these plants. Particularly emphasized is the plant treatment with the active ingredient combinations specifically mentioned in the present text.

The active compound combinations according to the invention not only act against plant, hygiene and storage pests, but also in the veterinary sector against animal parasites (ecto- and endoparasites) such as ticks, leather ticks, mange mites, running mites, flies (stinging and licking), parasitic fly larvae, lice , Hair pieces, featherlings and fleas. These parasites include: From the order of the Anoplurida eg Haematopinus spp., Linognathus spp., Pediculus spp., Phtirus spp., Solenopotes spp.

From the order of Mallophagida and 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 s of the order Diptera and the suborders Nematocerina and Brachycerina e.g. Aedes spp., Anopheles spp., Culex spp., Simulium spp., Eusimulium spp., Phlebotomus spp., Lutzomyia spp i., 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 siphonapterida e.g. Pulex spp., Ctenocephalides spp., Xenopsylla spp., Ceratophyllus spp.

From the order of the heteropterid e.g. Cimex spp., Triatoma spp., Rhodnius spp., Panstrongylus spp.

From the order of Blattarida e.g. Blatta orientalis, Periplaneta americana, Blattela germanica, Supella spp.

From the subclass of Acari (Acarina) and the orders of Meta and Mesostigmata e.g. Argas spp., Ornithodorus 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 Actinedida (Prostigmata) and Acaridida (Astigmata) e.g. 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 according to the invention are also suitable for controlling

Arthropods, the farm animals, such as cattle, sheep, goats, horses, pigs, donkeys, camels, buffaloes, rabbits, chickens, turkeys, ducks, geese, bees, other pets such as dogs, cats, caged birds, aquarium fish and so-called experimental animals , such as Hamsters, guinea pigs, rats and mice. By controlling these arthropods deaths and reductions in performance (in meat, milk, wool, hides, eggs, honey, etc.) are reduced, so that a more economical and easier animal husbandry is possible by the use of the active compound combinations according to the invention.

The application of the active compound combinations according to the invention takes place in the veterinary sector and in animal husbandry in a known manner by enteral administration in the form of, for example, tablets, capsules, infusions, drenches, granules, pastes, boilies, the feed-through process, suppositories, by parenteral administration, as by injections (intramuscular, subcutaneous, intravenous, intraperitoneal, etc.), implants, by nasal application, by dermal application in the form of, for example, diving or bathing (dipping), spraying, pouring (pour-on and spot-on ), washing, powdering and with the aid of active substance-containing moldings, such as collars, ear tags, tail marks, limb bands, holsters, marking devices, etc.

When used for livestock, poultry, pets, etc., the active ingredient combinations may be used as formulations (for example, powders, emulsions, flowables) containing the active ingredients in an amount of 1 to 80% by weight, directly or after 100 to 10,000 dilution or use as a chemical bath.

In addition, it has been found that the active compound combinations according to the invention have a high insecticidal activity against insects which destroy industrial materials.

By way of example and preferably without limiting however, the following insects are mentioned:

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

Hymenoptera such as Sirex juvencus, Urocerus gigas, Urocerus gigas taignus, Urocerus augur;

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

Bristle tails like Lepisma saccharina. Technical materials in the present context are non-living materials, such as preferably plastics, adhesives, glues, papers and cardboard, leather, wood, wood processing products and paints.

The ready-to-use agents may optionally contain further insecticides and, if appropriate, one or more fungicides.

With regard to possible additional admixing partners, reference is made to the above-mentioned insecticides and fungicides.

At the same time, the active compound combinations according to the invention can be used to protect against fouling of objects, in particular of hulls, sieves, nets, structures, quays and signal systems, which come into contact with seawater or brackish water.

Furthermore, the active compound combinations according to the invention can be used alone or in combinations with other active substances as antifouling agents.

The active ingredient combinations are also suitable for controlling animal pests in household, hygiene and storage protection, in particular of insects, arachnids and mites, which are used in closed rooms, such as apartments, factory buildings, offices, vehicle cabins u.a. occurrence. They can be used to control these pests, alone or in combination with other active ingredients and adjuvants in household insecticide products. They are effective against sensitive and resistant species and against all stages of development. These pests include:

From the order of Scorpionidea e.g. Buthus occitanus.

From the order of Acarina e.g. 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 e.g. Aviculariidae, Araneidae.

From the order of Opiliones e.g. Pseudoscorpiones chelifer, Pseudoscorpiones cheiridium, Opiliones phalangium.

From the order of isopods e.g. Oniscus asellus, Porcellio scaber.

From the order of the Diplopoda eg Blaniulus guttulatus, Polydesmus spp. From the order of Chilopoda eg Geophilus spp.

From the order of Zygentoma e.g. Ctenolepisma spp., Lepisma saccharina, Lepismodes inquilinus.

From the order of the Blattaria e.g. 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 Saltatoria e.g. Acheta domesticus.

From the order of the Dermaptera e.g. Forfϊcula auricularia.

From the order of Isoptera e.g. Kalotermes spp., Reticulitermes spp.

From the order of Psocoptera e.g. Lepinatus spp., Liposcelis spp.

From the order of Coleoptera e.g. 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 Diptera e.g. 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 Lepidoptera e.g. Achroia grisella, Galleria mellonella, Plodia interpunctella, Tinea cloacella, Tinea pellionella, Tineola bisselliella.

From the order of siphonaptera e.g. Ctenocephalides canis, Ctenocephalides felis, Pulex irritans, Tunga penetrans, Xenopsylla cheopis.

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

From the order of the Anoplura e.g. Pediculus humanus capitis, Pediculus humanus corporis, Pemphigus spp., Phylloera vastatrix, Phthirus pubis.

From the order of Heteroptera eg Cimex hemipterus, Cimex lectularius, Rhodinus prolixus, Triatoma infestans. The application in the field of household insecticides is carried out alone or in combination with other suitable active ingredients such as phosphoric acid esters, carbamates, pyrethroids, neonicotinoids, growth regulators or active compounds from other known classes of insecticides.

Application is in aerosols, non-pressurized sprays, e.g. Pump and atomizer sprays, fog machines, foggers, foams, gels, evaporator products with cellulose or plastic evaporator plates, liquid evaporators, gel and membrane evaporators, propeller driven evaporators, energyless or passive evaporation systems, moth papers, moth cakes and moth gels, as granules or dusts, in litter or bait stations.

The good insecticidal and / or acaricidal action of the active compound combinations according to the invention is evident from the examples below. While the individual active ingredients have weaknesses in effect, the combinations show an effect that goes beyond a simple action summation.

A synergistic effect is always present in insecticides and acaricides whenever the effect of the active ingredient combinations is greater than the sum of the effects of the individually applied active ingredients.

The expected effect for a given combination of two drugs can be calculated according to S.R. Colby, Weeds 15 (1967), 20-22 as follows:

If

X means the degree of killing, expressed in% of the untreated control, when using the active substance A at a rate of m g / ha or in a concentration of m ppm,

Y means the degree of killing, expressed in% of the untreated control, when using the active ingredient B in an application rate of n g / ha or in a concentration of n ppm, and

E the degree of kill, expressed in% of the untreated control, when using the

Active substances A and B in amounts of m and n g / ha or in a concentration of m and n ppm,

then

XYE = X + Y-100 If the actual insecticidal or acaricidal degree of killing is greater than calculated, the combination is over-additive in its killing, ie there is a synergistic effect. In this case, the actually observed kill rate must be greater than the expected kill rate (E) value calculated from the above formula.

Example A

Aphis gossypii test

Solvent: 7 parts by weight of dimethylformamide

Emulsifier: 2 parts by weight of alkylaryl polyglycol ether

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

Cotton leaves (Gossypium herbaceum), which are heavily infested by the cotton aphid {Aphis gossypii), are treated by being dipped into the preparation of active compound of the desired concentration.

After the desired time the kill is determined in%. 100% means that all aphids have been killed; 0% means that no aphids have been killed. The determined kill values are calculated according to the Colby formula (see page 1).

In this test, z. B. the following combination of active ingredients according to the present application a synergistically enhanced efficacy compared to the individually applied agents: (mb) and spirotetramat.

Table A

Plant damaging insects Aphis gossypii - test

Active substance concentration killing in ppm in% after 6 ^d

(DIb) 10

Spirotetramate (I-c-1) 0.8 15

(mb) + spirotetramate (I-c-1) (5: 1)

gef. * over. **

According to the invention 4 + 0.8 75 23.5

* gef. = found effect

** calc. = calculated according to the Colby formula

Example B

Myzus persicae test

Solvent: 7 parts by weight dimethylfibramide

Emulsifier: 2 parts by weight of alkylaryl polyglycol ether

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

In this test, z. B. the following combination of active ingredients according to the present application a synergistically enhanced efficacy compared to the individually applied agents: (IHb) and spirodiclofen.

Table B

Plant damaging insects Myzus persicae - test

Active substance concentration kill in ppm in% after l ^d

(UIb) 100 20

Spirodiclofen (II-b-1) 100 20

(IHb) + spirodiclofen (Η-b-1) (1: 1)

gef. * over. **

According to the invention 100 + 100 60 36

* gef. = found effect

** calc. = calculated according to the Colby formula

Example C

Phaedon cochleariae - larval test

Solvent: 7 parts by weight of dimethylformamide

Emulsifier: 2 parts by weight of alkylaryl polyglycol ether

Cabbage leaves (Brassica oleraceä) are treated by being dipped into the preparation of active compound of the desired concentration and are populated with larvae of the horseradish leaf beetle {Phaedon cochleariae) while the leaves are still moist.

After the desired time the kill is determined in%. 100% means that all beetle larvae have been killed; 0% means that no beetle larvae have been killed. The determined kill values are calculated according to the Colby formula (see page 1).

In this test, the following active ingredient combination according to the present application showed a synergistically enhanced effectiveness in comparison to the individual active ingredients used: (IHb) and spirodiclofen, (IHb) and spiromesifen.

Table C

Plant damaging insects Phaedon cochleariae larvae - test

Active substance concentration kill in ppm in% after 4 ^d

(πib) 4 35

Spirodiclofen (π-b-1) 100 0

Spiromesifen (II-b-2) 100 5

(DIb) + spirodiclofen (H-b-1) (1:25)

gef. * over. *

According to the invention 4 + 100 55 35

(mb) + spiromesifen (II-b-2) (1:25)

gef. * over. *

According to the invention 4 + 100 80 38.25

* g ^e f ⁼ found effect

** calc. = calculated according to the Colby formula

Claims

- Patent claims

1. agent containing a mixture

(a) at least one compound of the formula (I)

in which

X is halogen, alkyl, alkoxy, haloalkyl, haloalkoxy or cyano,

B is hydrogen or alkyl,

A and B, together with the carbon atom to which they are attached, represent a saturated or unsaturated unsubstituted or substituted cycle, optionally containing at least one heteroatom,

D is hydrogen or an optionally substituted radical from the group consisting of alkyl, alkenyl, alkoxyalkyl, saturated cycloalkyl, in which optionally one or more ring members are replaced by heteroatoms,

A and D together with the atoms to which they are bonded for a saturated or unsaturated and optionally containing at least one heteroatom, in the A, D-

Part unsubstituted or substituted cycle,

G is hydrogen (a) or one of the groups o _L R ⁴ ¹ R ¹ (b), ^ M ^'R2 <0. ^{/ SO} ^ ^{R3 (d)} . 7 ^ _(e) ,

L '

E (f) or ^ - N '(g),

"R ⁷

stands,

wherein

E is a metal ion or an ammonium ion,

L is oxygen or sulfur,

M is oxygen or sulfur,

R! in each case optionally halogen-substituted alkyl, alkenyl, alkoxyalkyl, alkylthioalkyl, polyalkoxyalkyl or optionally substituted by halogen, alkyl or alkoxy-substituted cycloalkyl which may be interrupted by at least one heteroatom, each optionally substituted

Phenyl, phenylalkyl, hetaryl, phenoxyalkyl or hetaryloxyalkyl,

R.2 is in each case optionally halogen-substituted alkyl, alkenyl, alkoxyalkyl, polyalkoxyalkyl or in each case optionally substituted cycloalkyl, phenyl or benzyl,

R ^{3 is} optionally halogen-substituted alkyl or optionally substituted phenyl,

R ^ and R ^ independently of one another are each optionally halogen-substituted alkyl, alkoxy, alkylamino, dialkylamino, alkylthio, alkenylthio, cycloalkylthio or in each case optionally substituted phenyl, benzyl, phenoxy or phenylthio and

R6 and R4 independently of one another represent hydrogen, in each case optionally halogen-substituted alkyl, cycloalkyl, alkenyl, alkoxy, alkoxyalkyl, optionally substituted phenyl, optionally substituted benzyl or together with the N-atom to which they are bonded, for a ge - optionally substituted by oxygen or sulfur interrupted optionally substituted ring,

and or

(b) at least one compound of the formula (IT)

in which

X 'is C ₁ -C 8 -alkyl, halogen, C ₁ -C 6 -alkoxy or C 1 -C 6 -haloalkyl,

Y ¹ is hydrogen, C ₁ -CG-AUCyI, halogen, C ₁ -CG -alkoxy, C _j ^ -haloalkyl,

Z 'is C i -Cg-alkyl, halogen, C γ -Cg-alkoxy,

n 'is a number from 0-3,

A ^{1 is} hydrogen or in each case optionally substituted by halogen straight-chain or branched

C2-Cg-alkenyl, C2-Cg alkynyl, C ₁ -C ₁ Q-alkoxy-C i--CG alkyl, C \ ^ -CG-polyalkoxy -CG alkyl, C ₁ -C ₁₀ -alkylthio-C2 Cg-alkyl, cycloalkyl having 3-8 ring atoms, which may be interrupted by oxygen and / or sulfur or in each case optionally substituted by halogen, C ₁ -CG-AIlCyI, C ₁ - Cg haloalkyl, C ₁ -CG-AIkOXy-, C 1 -C 9 -halogenalkoxy, nitro-substituted phenyl or phenyl-C 1 -C 6 -alkyl,

B 'is hydrogen, C ₁ -Cg -alkyl or C ₁ -C 6 -alkoxy-C ₁ -C 4 -alkyl

or in which

A 'and B' together with the carbon atom to which they are attached are a saturated or unsaturated, optionally interrupted by oxygen and / or sulfur and optionally by halogen, C ₁ -Cg-AllCyI, C ₁ -Cg -alkoxy, C ₁ - C4-haloalkyl, C ^ C ^ haloalkoxy, C ^ C ^ alkylthio or optionally form substituted phenyl-substituted or optionally benzo-fused 3- to 8-membered ring,

G 'for hydrogen (a) or for the groups

-CO-R ^{1 '} (b)

( _C ) _so _r R ^{3 "} ( _d )

stands in which

RI is in each case optionally halogen-substituted C 1 -C 20 -alkyl, C 2 -C 20 -alkenyl, C 1 -C 6 -alkoxy-C 1 -C 6 -alkyl, C 1 -C 6 -alkylthio-C 1 -C 6 -alkyl, C 1 -C 8 -polyalkoxy C2-C7-alkyl or cycloalkyl having 3-8 ring atoms which may be interrupted by oxygen and / or sulfur atoms,

optionally substituted by halogen, nitro, Cj-Cg-alkyl, Ci-Cg-alkoxy, C-Cg-

Haloalkyl, Ci-Cg-haloalkoxy-substituted phenyl;

represents optionally by halogen, Ci-Cg-Alkyl, Ci-Cg-Alkoxy, CJ-CÖ-haloalkyl, Ci-Cg-Halogenalkoxy-substituted Phenyl Ci-Cg-alkyl,

is in each case optionally substituted by halogen and / or C _j -Cg-alkyl-substituted pyridyl, pyrimidyl, thiazolyl or pyrazolyl,

is optionally substituted by halogen and / or Ci-Cg-alkyl-substituted phenoxy-Ci-Cg-alkyl,

R 1 'is in each case optionally halogen-substituted C ₁ -C 20 -alkyl, C ₂ -C 20 -alkenyl, C ₁ -C 6 -alkoxy-C ₂ -C 6 -alkyl or C ₁ -C 6 -alkoxy-C ₂ -C 6 -alkyl,

is each optionally substituted by halogen, nitro, Cj-Cg-alkyl, C ^ -Cg-alkoxy, C _j -Cg -haloalkyl-substituted phenyl or benzyl, R.3 'for optionally substituted by halogen C ₁ -Cg -AllCyI, each optionally substituted by Ci-C4-alkyl, halogen, C ₁ -C 4 -haloalkyl, Cj-C ^ alkoxy, C ₁ -C 4 -haloalkoxy, nitro or Cyano is substituted phenyl or benzyl,

R 4 and R 4 independently of one another are each C ₁ -C 9 -alkyl which is optionally substituted by halogen, C ₁ -C 6 -alkoxy, C ₁ -C 6 -alkylamino, di (C ₁ -CG) -alkyl-amino, C ₁ - C ₁ -C 6 -alkyl, C ₂ -C 5 alkenylthio, C ₂ -C 5 alkynylthio, C ₃ -C 7 cycloalkylthio, each optionally substituted by halo, nitro, cyano, C ₁ -C 4 alkoxy, C ₁ -C 4 haloalkoxy, C ₁ -C 4 Alkylthio, C ₁ -C 4 -haloalkylthio, C ₁ -C 4 -alkyl, C ₁ -C 4 -haloalkyl-substituted phenyl, phenoxy or phenylthio,

R6 'and R ^' are independently of one another represent in each case optionally halogen-substituted C ₁ -C _1Q -alkyl, C ₁ -C _1Q -alkoxy, C3-Cg alkenyl, C ₁ -CG -alkoxy-C ₁ - Cg alkyl-, optionally substituted by halogen, Ci-Cg-haloalkyl, C ₁ -Cg AIlCyI or C ₁ -Cg-AIkOXy substituted phenyl, optionally substituted by halogen, C ₁ -Cg AIlCyI, C ^ Cg-haloalkyl or C ₁ -Cg- AIkOXy substituted benzyl is or together represent a optionally interrupted by oxygen or sulfur 5- to 6-membered ring, which may optionally be substituted by C ₁ -Cg AIlCyI,

and

(c) at least one active substance of the formula (HI)

in which

Hal is chlorine, bromine or iodine,

denotes a carbon atom in the R or S configuration.

A composition according to claim 1, wherein the component of formula (I) is spirotetramate.

3. The composition according to claim 1 or 2, wherein the components of formula (II) are selected from spirodiclofen and spiromesifen.

4. Composition according to one or more of claims 1 to 3, wherein the compound of formula (HI) (S) -3-chloro-N ¹ - {2-methyl-4- [l, 2,2,2-tetrafluoro- 1- (trifluoromethyl) ethyl] phenyl} -N ² - (1-methyl-2-methylsulfonylethyl) phthalamide.

5. Use of compositions as defined in claims 1 to 4, for controlling animal pests.

6. Use of a composition according to one or more of claims 1 to 4 for the treatment of seed.

7. Use of compositions according to one or more of claims 1 to 4 for the treatment of transgenic plants.

8. Use of compositions according to one or more of claims 1 to 4 for the treatment of seed transgenic plants.

9. Seed which has been treated with a composition according to one or more of claims 1 to 4.

10. A method for controlling unwanted animal pests, characterized in that one applies composition according to one or more of claims 1 to 4 on the unwanted animal pests and / or their habitat and / or seed.

Process for the preparation of insecticidal and acaricidal agents, characterized in that compositions as defined in claims 1 to 4 are mixed with extenders and / or surface-active substances.