WO2006037553A1

WO2006037553A1 - Insecticidal active ingredient combinations containing halogen alkyl nicotinic acid derivatives and pyrethroids

Info

Publication number: WO2006037553A1
Application number: PCT/EP2005/010521
Authority: WO
Inventors: Erich Sanwald; Waltraud Hempel; Koichi Araki; Tetsuya Murata
Original assignee: Bayer Cropscience Gmbh
Priority date: 2004-10-06
Filing date: 2005-09-29
Publication date: 2006-04-13
Also published as: DE102004048527A1

Abstract

The invention relates to active ingredient combinations made from compounds having formula (1) wherein R1 and A have the meanings cited in the description, and pyrethroids possessing very good insecticidal and acaricidal properties, in addition to the use thereof and a method for the production thereof.

Description

INSECTICIDAL ACTIVE COMPOUNDS CONTAINING HALOGENAL CYLNICOTINIC ACID DERIVATIVES AND PYRETHROIDS

The present invention relates to new active compound combinations which consist of known haloalkyl nicotinic acid derivatives on the one hand and other known insecticidal active compounds on the other hand and are very suitable for controlling animal pests such as insects and unwanted acarids.

It is already known that certain haloalkyl nicotinic acid derivatives have insecticidal properties (EP-A 0 580 374, JP-A 7-010841, JP-A 7-025853, JP-A 10-101648, JP-A 10-195072, JP-A 11-180957, JP-A 2002-205991, JP-A 2003-113179, JP-A 2004-035439, JP-A 2004-083415, WO 98/57969, WO 99/59993, WO 00/35912, WO 00 / 35913, WO 01/09104, WO 01/14373, WO 01/47918, WO 01/70692, WO 02/12229, WO 03/028458, WO 03/028459, WO 03/043990, WO 03/044013, WO 03 / 097604, WO 03/097605). The effectiveness of these substances is good, but leaves at low application rates in some cases to be desired.

Furthermore, it is already known that numerous heterocycles, organotin compounds, benzoylureas and pyrethroids possess insecticidal and acaricidal properties (compare WO 93-22 297, WO 93-10 083, DE-A 2 641 343, EP-A-347 488, EP-A-210 487, US-A 3,264,177 and EP-A-234045). However, the effect of these substances is not always satisfactory.

Furthermore, mixtures of haloalkyl nicotinic acid derivatives with other insecticides are already known (see WO 2002/034050, WO 2002/037964).

It has now been found that haloalkyl nicotinic acid derivatives of the formula (I)

in which

A for the groups

stands in which

R ^{1 is} C _r C ₄ -haloalkyl,

R ² and R ³ independently of one another represent hydrogen or hydroxyl, in each case optionally mono- or polysubstituted, identically or differently, by R ⁴ ,

Oximino or hydrazono substituted Ci-C ₈ alkyl, C ₃ -C ₆ alkenyl, C ₃ -C ₆ alkynyl, C _r C ₆ alkoxy, C ₃ -C ₃ cycloalkyl, or cycloalkyl-Q-CRCG Cβ- alkyl, where the substituents oximino and hydrazono are each in turn unsubstituted or by C 1 -C ₈ -alkyl, C ₃ -C ₆ -alkenyl, C ₃ -C ₆ -alkynyl, C ₃ -C ₈ -cycloalkyl, C ₃ - C ₈ -cycloalkyl-C _r C ₆ alkyl, CRCG-alkoxy-Ci-Cs-alkyl, cyano-QQ-alkyl, C _r C ₈ alkylthio

Substituted amino-carbonyl, aryl or -CH ₂ -aryl - _Ci-C8 alkyl, Ci-Q-alkyl-carbonyl, (C _r C ₈ alkoxy) carbonyl, di- (C _r -C ₈ alkyl) may be aryl, heterocyclyl, -CH ₂ -aryl or -CH ₂ -heterocyclyl, -C (= X) -Y, or in each case optionally mono- or polysubstituted, identically or differently, by R ⁵ ,

or

R ² and R ³ together with the nitrogen atom to which they are attached form a 3- to 8-membered saturated, unsaturated or aromatic heterocyclic ring optionally containing up to three further heteroatoms from the group of nitrogen, sulfur and oxygen, and which is unsubstituted or identical or different substituents from the one or more radicals R ^4, C _r C ₆ alkyl, QC ₆ -

Haloalkyl, C ₃ -C ₆ -alkenyl, C ₃ -C ₆ -alkynyl, oxo, oximino or hydrazono, wherein the substituents oximino and hydrazono are in turn unsubstituted or by C ₁ -C ₈ -alkyl, C ₃ -C ₆ -alkenyl, C ₃ -C ₆ alkynyl, C ₃ -C ₈ cycloalkyl, C ₃ -C ₈ cycloalkyl-C _r C ₆ alkyl, C _r C ₈ alkoxy-Ci-C ₈ alkyl, cyano-Ci-C ₈ - alkyl, Q-Cs-alkylthio-Ci-Cs-alkyl, Q-Cs-alkyl-carbonyl, Ci-Cg-alkoxy-carbonyl, di- (C _r C ₈ alkyl) amino-carbonyl,

Aryl or -CH ₂ -aryl can be substituted,

R ⁴ is halogen, Ci-C ₆ alkoxy, C _r C ₆ haloalkoxy, -S (O) _n -C-C ₆ -alkyl, -S (O) _n -C ₁ -C ₆ -

Haloalkyl, hydroxy, cyano, carboxy, azido, C ₁ -C ₆ -alkoxycarbonyl, nitro, di-

(Ci-C ₆ alkyl) amino, or optionally monosubstituted or polysubstituted by identical or comparable secreted by Ci-C ₆ alkyl, Ci-C ₆ haloalkyl and / or halogen-substituted

Phenoxy stands,

n is 0, 1 or 2, R ⁵ is ₆ haloalkyl for R ^4, Ci-Ce-alkyl or C _r C,

X is oxygen or sulfur,

Y is R ⁶ , OR ⁶ , SR ⁶ , NR ⁷ R ⁸ ,

W is oxygen or sulfur,

R ^{6 is} in each case optionally mono- or polysubstituted, identically or differently by R ^4, substituted Cj-Cg-alkyl, C ₃ -C ₈ -cycloalkyl or GrCg-cycloalkyl-Q-Ce-alkyl, or in each case optionally mono- or polysubstituted, the same or aryl, heterocyclyl, -CH ₂ -aryl or -CH ₂ -heterocyclyl which is differently substituted by R ⁵ ,

R ⁷ represents hydroxyl, represents in each case optionally monosubstituted or polysubstituted by identical or different substituted by the R ⁴ C _r C ₈ alkyl, C ₃ -C ₆ alkenyl, C ₃ -C ₆ -Alkmyl, C ₁ -C ₈ - Alkoxy, hydroxyC _r C ₈ alkyl, C ₃ -C ₆ alkenyloxy, C ₃ -C ₆ alkynyloxy, C ₃ -C ₈ cycloalkyl,

Q-C ₆ -cycloalkyl-C ₁ -C ₆ -alkyl, -O-C ₂ -C ₃ -cycloalkyl, in each case optionally mono- or polysubstituted, identically or differently, by R ⁵ -substituted aryl,

Heterocyclyl, aryloxy, heterocyclyloxy, -CH ₂ -aryl, -O-CH ₂ -aryl, -CH ₂ -heterocyclyl or -O-CHr-heterocyclyl,

R ^{8 represents} hydrogen, for each optionally mono- or polysubstituted, identical or different R ⁴ -substituted C _r C ₈ -alkyl, C ₃ -C ₈ -cycloalkyl or C ₃ -C ₈ -cycloalkyl-C ₁ -C ₆ alkyl, cyclyl represents in each case optionally monosubstituted or polysubstituted by identical or different substituents R ⁵ substituted aryl, heterocyclyl, -CH ₂ aryl or -CH ₂ -Hetero-,

R ⁹ and R ¹⁰ independently of one another in each case optionally monosubstituted or polysubstituted by identical or different substituents R ⁴ is substituted C _r C ₈ alkyl, C ₃ -C ₆ alkenyl, C ₃ -C ₆ -Alkmyl,

QrQ-cycloalkyl or GrCs-cycloalkyl-d-Ce-alkyl, for -G (= X) -Y, in each case optionally mono- or polysubstituted, identically or differently by R ⁵ -substituted aryl, heterocyclyl, -CH ₂ -aryl or -CH _2- heterocyclyl is

or

R ⁹ and R ¹⁰ together with the sulfur atom to which they are attached form a 3- to 8-membered saturated or unsaturated heterocyclic ring which optionally contains up to three further heteroatoms from the group of nitrogen, sulfur and oxygen, and which is unsubstituted or the same or different is substituted by one or more radicals R ⁴ , Ci-C ₆ alkyl, C _r C ₆ haloalkyl, oxo, oximino or hydrazono, wherein the substituents oximino and hydrazono are in turn unsubstituted or by C _r C ₈ alkyl, C ₃ -C ₆ alkenyl, C ₃ -C ₆ alkynyl, Cs-Cg-cycloalkyl, C ₃ -C ₈ cycloalkyl-Ci-C ₆ alkyl, C, -C ₈ alkoxy-C _r C ₈ alkyl, cyano Ci-C ₈ alkyl, C _r C ₈ alkylthio-Ci-C ₈ alkyl, C _r C ₈ alkyl-carbonyl, Ci-C ₈ alkoxy carbonyl, di- (C _r C ₈ alkyl ) -amino-carbonyl, aryl or -CH ₂ -aryl can be substituted,

Het / heterocyclyl is a cyclic radical which may be completely saturated, partially unsaturated or completely unsaturated or aromatic and which is substituted by at least one or more identical or different atoms from the group of nitrogen,

However, not two oxygen atoms may be directly adjacent and still at least one carbon atom must be present in the ring, wherein the cyclic radical is unsubstituted or substituted by one or more radicals R ⁴ , C ₁ -C ₆ - AllCyI, Ci-C ₆ -haloalkyl, Ci-C ₈ -alkoxy- C] -C ₈ -alkyl, Ci-C ₈ -alkylthio-Ci-C ₈ -alkyl, oxo, oximino or hydrazono, wherein the

Substituents oximino and hydrazono in turn are unsubstituted or substituted by Ci-C ₈ - alkyl, C ₃ -C ₆ alkenyl, C ₃ -C ₆ alkynyl, C ₃ -C ₈ cycloalkyl, C ₃ -C ₈ cycloalkyl-C ₁ -C ₆ alkyl, C ₈ alkoxy-C, -C ₈ alkyl, cyano-C _r C ₈ alkyl, C, -C ₈ alkylthio-Ci-C ₈ alkyl, C _r C ₈ - Alkylcarbonyl, Q-Cg-alkoxycarbonyl, di- (C 1 -C ₈ -alkyl) -amino-carbonyl, aryl or -CH ₂ -aryl can be substituted,

or salts of a compound of formula (I) and pyrethroids

1. Acrinathrin

bekanntausEP-A-048 186

and or 2. Alpha-cypermethrin

known from EP-A-067 461

and or

3. Betacyfluthrin

known from EP-A-206149

and or

4. Cyhalothrin

known from DE-A-2 802 962

and or 5. cypermethrin

known from DE-A-2 326 077

and or

6. deltamethrin

known from DE-A-2 326 077

and or

7. Esfenvalerat

known from DE-A-2 737 297

and or

8. Ethofen Prox

known from DE-A-3 117 510 and or

9. Fenpropathrin

known from DE-A-2 231 312

and or

10. Fenvalerate

bekanntausDE-A-2335347

and or

11. Flucythrinate

known from DE-A-2 757 066

and or 12. Lambda cyhalothrin

known from EP-A-106469

and or

13. Permethrin

known from DE-A-2 326 077

and or

14. Baptized Luvalinate

known from EP-A-038 617

and or 15. Tralomethrin

known from DE-A-2 742 546

and or

16. Zeta cypermethrin

known from EP-A-026 542

and or

17. Cyfluthrin

known from DE-A-27 09 264

and or

18. Bifenthrin

known from EP-A-049 977 and or

19. Cycloprotein

bekanntausDE-A-2653189

and or

20. Eflusilanate

bekanntausDE-A-3604781

and or

21. Fubfenprox

bekanntausDE-A-3708231

and or 22. Pyrethrin

R = -CH ₃ or -CO ₂ CH ₃

R ₁ = -CH = CH ₂ or -CH ₃ or -CH ₂ CH ₃

known from The Pesticide Manual, 1997, 11th edition, p.1056

and or

23. Resmethrin

from GB-A-1 168 797

possess very good insecticidal and acaricidal properties.

Surprisingly, the insecticidal and acaricidal activity of the combination of active substances according to the invention is substantially higher than the sum of the effects of the individual active substances. There is an unpredictable true synergistic effect and not just an effect supplement.

The active compound combinations according to the invention contain, in addition to at least one active substance of the formula (I) or a salt of the active compound of the formula (T), at least one active compound of the compounds 1 to 23.

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

R ¹ preferably represents mono- or polysubstituted, identically or differently by fluorine and / or chlorine-substituted C 1 -C ₄ -alkyl, particularly preferably CF ₃ , CHF ₂ or CF ₂ Cl, very particularly preferably CF ₂ ; R ² and R ³ independently of one another preferably represent hydrogen or hydroxyl, in each case optionally mono- or polysubstituted, identically or differently, by R ⁴ or

Oximino-substituted C _r C ₆ alkyl, C ₃ -C ₆ alkenyl, C ₃ -C ₆ alkynyl, Ci-C ₄ alkoxy, C ₃ -C ₈ -

Cycloalkyl or C ₃ -C ₈ -cycloalkyl-C ₁ -C ₆ -alkyl, where the substituent oximino is in turn unsubstituted or by C ₁ -C ₈ -alkyl, C ₃ -C ₆ -alkenyl, C ₃ -C ₆ -alkynyl, C C ₃ -C ₈ cycloalkyl,

QQ-QQ-cycloalkyl-alkyl, Cj -C ₈ -alkoxy-C ₁ -C ₈ alkyl, cyano-QQ-alkyl, C ₁ -C ₈ -

Alkylthio-C _r C ₈ alkyl, dQ-alkyl-carbonyl, d-Cs-alkoxy-carbonyl, di- (C _r -C ₈ alkyl) - amino-carbonyl, aryl or -CH ₂ -aryl which may be substituted, for -C (= X) -Y, or for each optionally mono- or polysubstituted, identically or differently, R ⁵ -substituted aryl, heterocyclyl, -CH ₂ -aryl or -CH ₂ -heterocyclyl,

or

R ² and R ³ , together with the nitrogen atom to which they are attached, preferably form a 3- to 8-membered saturated, unsaturated or aromatic heterocyclic ring which optionally contains up to three further heteroatoms from the group of nitrogen, sulfur and oxygen, and which is unsubstituted or substituted by one or more radicals

R ^4, Ci-C ₆ alkyl, Ci-C ₆ haloalkyl or oximino wherein the substituent oximino turn is unsubstituted or substituted by QC ₈ alkyl, C ₃ -C ₆ alkenyl, C ₃ -C ₆ -alkynyl, C ₃ -C ₈ - cycloalkyl, C ₃ -C ₈ cycloalkyl-C _r C ₆ alkyl, C _r C ₈ alkoxy-C, -C ₈ alkyl, cyano-C, -C ₈ alkyl, C ₁ - C ₈ alkylthio-Ci-C ₈ alkyl, d-Cg-alkyl-carbonyl, C _r C ₈ -alkoxy-carbonyl, di- (C ₁ -C ₈ -alkyl> amino-carbonyl, aryl or -CH ₂ - Aryl may be substituted,

R ⁴ is preferably halogen, C _r C ₆ alkoxy, C _r C ₆ haloalkoxy, -S (O) _n -C _r C ₆ alkyl, cyano, carboxy, azido, C ₆ alkoxy-carbonyl, nitro or Di (C 1 -C ₆ alkyl) amino,

n is preferably 0, 1 or 2,

R ⁵ is preferably R ⁴ , C ₁ -C ₆ -alkyl or C ₁ -C ₆ -haloalkyl,

X is preferably oxygen,

X is also preferably sulfur,

Y is preferably R ⁶ , OR ⁶ , SR ⁶ , NR ⁷ R ⁸ ,

W is preferably oxygen,

W is also preferably sulfur, R ⁶ is preferably in each case optionally mono- or polysubstituted by identical or different substituents R ⁴ -substituted Q-Cg-alkyl, C ₃ -C ₈ -cycloalkyl or C ₃ -C ₈ -cycloalkyl-C _r C ₆ -alkyl, or for each optionally mono- or polysubstituted, identically or differently, R ⁵ -substituted aryl, heterocyclyl, -CH ₂ -aryl or -CH ₂ -heterocyclyl,

R ⁷ preferably represents hydroxyl, in each case optionally mono- or polysubstituted by identical or different substituents R ⁴ -substituted Q-Cg-alkyl, C ₃ -C ₆ -alkenyl, C ₃ -C ₆ -alkynyl, QC ₈ -alkoxy, hydroxyl Q-Cg-alkyl, C ₃ -C ₆ -alkenyloxy, C ₃ -C ₆ -alkynyloxy, C ₃ -C ₈ -cycloalkyl, C ₃ -C ₈ -cycloalkyl-QC ₆ -alkyl, -O-CH ₂ -C C ₃ -C ₈ -cycloalkyl, in each case optionally mono- or polysubstituted, identically or differently, by R ⁵ -substituted aryl, heterocyclyl, aryloxy, heterocyclyloxy, -CH ₂ -aryl, -O-CH ₂ -aryl, -CH ₂ -heterocycly or OC ^ heterocyclyl

R ⁸ preferably represents hydrogen, in each case optionally monosubstituted or polysubstituted by identical or different substituents by R ⁴ substituted QC ₈ alkyl, C ₃ -C ₈ cycloalkyl or C ₃ -C ₈ - cycloalkyl-Ci-C ₆ alkyl, for in each case optionally mono- or polysubstituted, identical or differentiated by R ⁵ -substituted aryl, heterocyclyl, -CH ₂ -aryl or -CH ₂ heterocyclyl,

R ⁹ and R ¹⁰ independently of one another preferably in each case optionally monosubstituted or polysubstituted by identical or different substituents R ⁴ substituted C ₈ alkyl, C ₃ -C ₆ - alkenyl, C ₃ -C ₆ - alkynyl, C ₃ -C ₈ -cycloalkyl or C ₃ -C ₈ -cycloalkyl-C, -C ₆ -alkyl, for -C (= X) -Y, in each case optionally mono- or polysubstituted, identically or differently by R ⁵ -substituted aryl, heterocyclyl, -CH ₂ -aryl or -CHH-heterocyclyl

or

R ⁹ and R ¹⁰ , together with the sulfur atom to which they are attached, preferably form a 3- to 8-membered saturated or unsaturated heterocyclic ring which optionally contains up to three further heteroatoms from the group of nitrogen, sulfur and oxygen, and is unsubstituted or substituted by one or more radicals R ⁴ , Ci-C ₆ alkyl, Q- C ₆ haloalkyl, oxo, oximino or hydrazono, wherein the substituents oximino and

Hydrazono are in turn unsubstituted or by Q-Cg-alkyl, C ₃ -C ₆ alkenyl, C ₃ -C ₆ - alkynyl, C ₃ -C ₈ -cycloalkyl, C ₃ -C ₈ -cycloalkyl-C _r C ₆ -alkyl , Q-Cg-alkoxy-Q-Cs-alkyl, cyano-QC ₈ -alkyl, C 1 -C 9 -alkylthio-QQ-alkyl, C 1 -C ₈ -alkylcarbonyl, C 1 -C ₈ -alkoxycarbonyl, di (QC ₈ -alkyl) - amino-carbonyl, aryl or -CH ₂ -aryl can be substituted,

Hefeterocyclyl preferably represents a cyclic radical from the series thiophene, furan, pyrrole, thiazole, oxazole, imidazole, isothiazole, isoxazole, pyrazole, 1,3,4-oxadiazole, 1,3,4-thiadiazole, 1,3,4- Triazole, 1,2,4-oxadiazole, 1,2,4-thiadiazole, 1,2,4-triazole, 1,2,3-triazole, 1,2,3,4-tetrazole, benzo [b] thiophene, benzo [b] furan, indole, benzo [c] thiophene, benzo [c] furan, isoindole, benzoxazole, benzothiazole, benzimidazole, benzisoxazole, benzisothiazole, benzopyrazole, Benzothiadiazole, benzotriazole, dibenzofiαran, dibenzothiophene, carbazole, pyridine, pyrazine, pyrimidine, pyridazine, 1,3,5-triazine, 1,2,4-triazine, 1,2,4,5-tetrazine, quinoline, isoquinoline, quinoxaline, Quinazoline, cinnoline, 1,8-naphthyridine, 1,5-naphthyridine,

1,6-naphthyridine, 1,7-naphthyridine, phthalazine, pyridopyrimidine, purine, pteridine, 4H-quinolizine, piperidine, pyrrolidine, oxazoline, tetrahydrofibran, tetrahydropyran, isoxazolidine or thiazolidine, wherein the cyclic group is unsubstituted or substituted by one or more more radicals R ^4, C _r C ₆ alkyl, C _r C ₆ haloalkyl, Q-Cs-alkylthio-C] - C ₈ alkyl, oxo, oximino or hydrazono, wherein the substituents oximino and hydrazono in turn are unsubstituted or substituted by dC ₈ alkyl, C ₃ -C ₆ alkenyl, C ₃ -C ₆ alkynyl, C ₃ -C ₈ - cycloalkyl, C ₃ -C ₈ cycloalkyl-Ci-C ₆ alkyl, Ci-Cg-alkoxy Cj-Cs-alkyl, cyano-C _r C ₈ alkyl, C _r C ₈ alkylthio-Ci-C ₈ alkyl, C, -C ₈ alkyl-carbonyl, Ci-C ₈ -alkoxy-carbonyl, di- (C _r -C ₈ alkyl) - amino-carbonyl, aryl or -CH ₂ -aryl may optionally be substituted,

R ² and R ³ independently of one another particularly preferably represent hydrogen or hydroxyl, in each case optionally monosubstituted or polysubstituted, identically or differently by R ^4, substituted methyl, ethyl, n- or iso-propyl, n-, iso-, secondary or tertiary Butyl, propenyl, butenyl, propynyl, butynyl, methoxy, ethoxy, n- or isopropoxy, n-, iso-, secondary- or tertiary-butyloxy, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, for -C (= X) - Y, or for each optionally mono- or polysubstituted, identically or differently, R ⁵ -substituted phenyl or benzyl,

R ⁴ is particularly preferably fluorine, chlorine, methoxy, ethoxy, n- or iso-propyloxy, n-, iso-, secondary- or tertiary-butyloxy, trifluoromethoxy, thiomethyl, thioethyl, sulfonylmethyl, sulfonylethyl, sulfonylmethyl or sulfonylethyl,

R ⁵ particularly preferably represents R ⁴ , methyl, ethyl, n- or iso-propyl, n-, iso-, secondary- or tert-butyl or for trifluoromethyl,

R ⁶ particularly preferably represents in each case optionally mono- or polysubstituted by identical or different R ⁴ -substituted methyl, ethyl, n- or iso-propyl, n-, iso-, secondary- or tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, Cyclohexyl, or for each optionally mono- or polysubstituted by identical or different substituents by R ⁵

Phenyl, heterocyclyl, benzyl or -CBk heterocyclyl,

R ⁷ particularly preferably represents hydroxyl, in each case optionally monosubstituted or polysubstituted, identically or differently by R ^4, substituted methyl, ethyl, n- or iso-propyl, n-, iso-, secondary or tertiary-butyl propenyl, butenyl, propynyl, butynyl, methoxy, ethoxy, n- or iso-propyloxy, n-, iso-, secondary or tertiary-butyloxy, propenyloxy, butenyloxy, propinyloxy, butinyloxy, or for each optionally simple or multiply, identically or differently by R ⁵ substituted phenyl, phenyloxy, benzyl or benzyloxy,

R ⁸ particularly preferably represents hydrogen, in each case optionally mono- or polysubstituted, identically or differently by R ^4, substituted methyl, ethyl, n- or iso-propyl, n-, iso-, secondary or tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl , Cyclohexyl, or for each optionally mono- or polysubstituted by identical or different substituents R ⁵ -substituted phenyl or bercyl,

R ⁹ and R ¹⁰ independently of one another particularly preferably represent substituted methyl, ethyl, n- or iso-propyl, n-, iso-, secondary- or tertiary-butyl, propenyl, each optionally mono- or polysubstituted, identically or differently by R ⁴ Butenyl, propynyl, butynyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, or for in each case optionally mono- or polysubstituted by identical or different substituents R ⁵ -substituted phenyl or benzyl,

Het / heterocylyl particularly preferably represents a cyclic radical from the series thiophene, furan, pyrrole, thiazole, oxazole, imidazole, isothiazole, isoxazole, pyrazole, 1,3,4-oxadiazole, 1,3,4-thiadiazole, 1,3, 4-triazole, 1,2,4-oxadiazole, 1,2,4-thiadiazole, 1,2,4-triazole, 1,2,3-triazole, benzo [b] thiophene, benzo [b] furan, Indole, benzo [c] thiophene, benzo [c] furan, isoindole, benzoxazole, benzothiazole, benzimidazole, benzisoxazole, benzisothiazole, benzopyrazole, benzothiadiazole, benzotriazole, dibenzofuran, dibenzothiophene, pyridine, pyrazine, pyrimidine,

Pyridazine, piperidine, pyrrolidine, oxazoline, tetrahydrofuran, tetrahydropyran, isoxazolidine or thiazolidine, where the cyclic radical is unsubstituted or substituted by one or more radicals R ⁴ , methyl, ethyl, n- or iso-propyl, n-, iso-, secondary or tertiary butyl, trifluoromethyl, methylthiomethyl, ethylthiomethyl, ethylthiomethyl, ethylthioethyl.

The general or preferred radical definitions or explanations given above can be combined as desired with one another, ie also between the respective ranges and preferred ranges.

The following groups of compounds of the formula are particularly emphasized:

Group 1:

Compounds of the formula (I) in which A is Het and Het is a 1,2,4-oxadiazole radical, where the 1,2,4-oxadiazole radical is unsubstituted or substituted by one or a plurality of radicals selected from R ⁴ , methyl, ethyl, n- or iso-propyl, n-, iso-, secondary or tertiary-butyl, trifluoromethyl, methylthiomethyl, ethylthiomethyl, ethylthiomethyl, ethylthioethyl.

Group 2:

Compounds of formula (I), where A is the group

stands,

W is oxygen and R and R .10 are particularly preferred.

Group 3:

Compounds of formula (I) ₅ which A is the group

stands,

W is oxygen, R ^{2 is} hydrogen, R ^{3 is} -C (= X) -Y, X is oxygen and Y is -OR ⁶ , where R ^{6 is} in each case optionally mono- or polysubstituted, identical or different R ^{5 is} substituted benzyl, furylmethyl or thienylmethyl and R ^{5 has} the particularly preferred condition.

Group 4:

Compounds of formula (I), where A is the group

stands,

W is oxygen, R ^{2 is} hydrogen, R ^{3 is} -C (= X) -Y, X is oxygen and Y is -NR ⁷ R ⁸ , wherein R ^{7 is} methoxy, ethoxy, n- or iso -Propyloxy, n-, iso-, secondary- or tertiary-butyloxy, propenyloxy, butenyloxy, propinyloxy or butinyloxy and R ^{8 is} methyl, ethyl, n- or iso-propyl, n-, iso-, secondary or tertiary-butyl stands.

As salts of the active compounds of the formula (I) which can be used as alternatives according to the invention, the sodium, potassium, magnesium, calcium, ammonium, C 1 -C 4 -alkylammonium, di (C 1 -C 4) alkyl) -ammonium, Tn- (C _j -C 4 -alkyl) -ammonium, Tefra (Ci-C4-alkyl) -ammonium, Tn- (C 1 -C 4 -alkyl) sulfonium, C5 or Cg -Cycloalkyl-ammomum- and di- (Ci-C2-alkyl) -benzyl-amrnonium- called salts of these drugs.

Particularly preferred are combinations of active substances containing the active ingredient of the formula (I-a-1)

Particularly preferred are combinations of active substances containing the active ingredient of the formula (I-b-1)

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

or its sodium salt

(Ic-2) or its sodium salt

or its sodium salt

or its sodium salt

Na (I-c-4) -Na,

(Ic-5) or its sodium salt

Na (I-c-5) -Na,

or its sodium salt

(I-c-ό) -Na,

or its sodium salt

(Ic-7) -Na,

or its sodium salt

According to the invention, therefore, the following active ingredient combinations should be emphasized:

(Ia-1) + acrinathrin, (Ia-1) + alpha-cypermethrin, (Ia-1) + betacyfluthrin, (Ia-1) + cyhalothrin, (Ia-1) + cypermethrin, (Ia-1) + deltamethrin, (Ia-1) + esfenvalerate, (Ia-1) + etofenprox, (Ia-1) + fenpropathrin, (Ia-1) + fenvalerate, (Ia-1) + flucythrinate, (Ia-1) + lambda-cyhalothrin, (Ia-1) + permethrin, (Ia-1) + tau-fluvalinate, (Ia-1) + tralomethrin, (Ia-1) + zeta-cypermethrin, (Ia-1) + cyfluthrin, (Ia-1) + Bifenthrin, (Ia-1) + Cycloprothrin, (Ia-1) + Eflusilanate, (Ia-1) + Fubfenprox, (Ia-1) + Pyrethrin, (Ia-1) + Resmethrin.

(Ib-1) + acrinathrin, (Ib-1) + alpha-cypermethrin, (Ib-1) + betacyfluthrin, (Ib-1) + cyhalothrin, (Ib-1) + cypermethrin, (Ib-1) + deltamethrin, (Ib-1) + esfenvalerate, (Ib-1) + etofenprox, (Ib-1) + fenpropathrin, (Ib-1) + fenvalerate, (Ib-1) + flucythrinate, (Ib-1) + lambda-cyhalothrin, (Ib-1) + permethrin, (Ib-1) + tau-fluvalinate, (Ib-1) + tralomethrin, (Ib-1) + zeta-cypermethrin, (Ib-1) + cyfluthrin,, (Ib-1) + Bifenthrin, (Ib-1) + cycloprothrin, (Ib-1) + eflusilanate, (Ib-1) + Fubfenprox, (Ib-1) + pyrethrin, (Ib-1) + resmethrin.

(Ic-1) + acrinathrin, (Ic-1) + alpha-cypermethrin, (Ic-1) + betacyfluthrin, (Ic-1) + cyhalothrin, (Ic-1) + cypermethrin, (Ic-1) + deltamethrin, (Ic-1) + esfenvalerate, (Ic-1) + etofenprox, (Ic-1) + fenpropathrin, (Ic-1) + fenvalerate, (Ic-1) + flucythrinate, (Ic-1) + lambda-cyhalothrin, (Ic-1) + permethrin, (Ic-1) + tau-fluvalinate, (Ic-1) + tralomethrin, (Ic-1) + zeta-cypermethrin, (Ic-1) + cyfluthrin, (Ic-1) + Bifenthrin, (Ic-1) + Cycloprothrin, (Ic-1) + Eflusilanate, (Ic-1) + Fubfenprox, (Ic-1) + Pyrethrin, (Ic-1) + Resmethrin.

(I-c-2) + acrinathrin, (I-c-2) + alpha-cypermethrin, (I-c-2) + betacyfluthrin, (I-c-2) + cyhalothrin,

(Ic-2) + cypermethrin, (Ic-2) + deltamethrin, (Ic-2) + esfenvalerate, (Ic-2) + etofenprox, (Ic-2) + fenpropathrin, (Ic-2) + fenvalerate, (Ic -2) + flucythrinate, (Ic-2) + lambda-cyhalothrin, (Ic-2) + Permethrin, (Ic-2) + tau-fluvalinate, (Ic-2) + tralomethrin, (Ic-2) + zeta-cypermethrin, (Ic-2) + cyfluthrin, (Ic-2) + bifenthrin, (Ic 2) + cycloprothrin, (Ic-2) + eflusilanate, (Ic-2) + Fubfenprox, (Ic-2) + pyrethrin, (Ic-2) + resmethrin.

(Ic-3) + acrinathrin, (Ic-3) + alpha-cypermethrin, (Ic-3) + betacyfluthrin, (Ic-3) + cyhalothrin, (Ic-3) + cypermethrin, (Ic-3) + deltamethrin, (Ic-3) + esfenvalerate, (Ic-3) + etofenprox, (Ic-3) + fenpropathrin, (Ic-3) + fenvalerate, (Ic-3) + flucythrinate, (Ic-3) + lambda-cyhalothrin, (Ic-3) + permethrin, (Ic-3) + tau-fluvalinate, (Ic-3) + tralomethrin, (Ic-3) + zeta-cypermethrin, (Ic-3) + cyfluthrin, (Ic-3) + Bifenthrin, (Ic-3) + Cycloprothrin, (Ic-3) + Eflusilanate, (Ic-3) + Fubfenprox, (Ic-3) + Pyrethrin, (Ic-3) + Resmethrin.

(Ic-4) + acrinathrin, (Ic-4) + alpha-cypermethrin, (Ic-4) + betacyfluthrin, (Ic-4) + cyhalothrin, (Ic-4) + cypermethrin, (Ic-4) + deltamethrin, (Ic-4) + esfenvalerate, (Ic-4) + etofenprox, (Ic-4) + fenpropathrin, (Ic-4) + fenvalerate, (Ic-4) + flucythrinate, (Ic-4) + lambda-cyhalothrin, (Ic-4) + permethrin, (Ic-4) + tau-fluvalinate, (Ic-4) + tralomethrin, (Ic-4) + zeta-cypermethrin, (Ic-4) + cyfluthrin, (Ic-4) + Bifenthrin, (Ic-4) + Cycloprothrin, (Ic-4) + Eflusilanate, (Ic-4) + Fubfenprox, (Ic-4) + Pyrethrin, (Ic-4) + Resmethrin.

(Ic-5) + acrinathrin, (Ic-5) + alpha-cypermethrin, (Ic-5) + betacyfluthrin, (Ic-5) + cyhalothrin, (Ic-5) + cypermethrin, (Ic-5) + deltamethrin, (Ic-5) + esfenvalerate, (Ic-5) + etofenprox, (Ic-5) + fenpropathrin, (Ic-5) + fenvalerate, (Ic-5) + flucythrinate, (Ic-5) + lambda-cyhalothrin, (Ic-5) + permethrin, (Ic-5) + tau-fluvalinate, (Ic-5) + tralomethrin, (Ic-5) + zeta-cypermethrin, (Ic-5) + cyfluthrin, (Ic-5) + Bifenthrin, (Ic-5) + Cycloprothrin, (Ic-5) + Eflusilanate, (Ic-5) + Fubfenprox, (Ic-5) + Pyrethrin, (Ic-5) + Resmethrin.

(Ic-6) + acrinathrin, (Ic-6) + alpha-cypermethrin, (Ic-6) + betacyfluthrin, (Ic-6) + cyhalothrin, (Ic-6) + cypermethrin, (Ic-6) + deltamethrin, (Ic-6) + esfenvalerate, (Ic-6) + etofenprox, (Ic-6) + fenpropathrin, (Ic-6) + fenvalerate, (Ic-6) + flucythrinate, (Ic-6) + lambda-cyhalothrin, (Ic-6) + permethrin, (Ic-6) + tau-fluvalinate, (Ic-6) + tralomethrin, (Ic-6) + zeta-cypermethrin, (Ic-6) + cyfluthrin, (Ic-6) + Bifenthrin, (Ic-6) + Cycloprothrin, (Ic-6) + Eflusilanate, (Ic-6) + Fubfenprox, (Ic-6) + Pyrethrin, (Ic-6) + Resmethrin.

(Ic-7) + acrinathrin, (Ic-7) + alpha-cypermethrin, (Ic-7) + betacyfluthrin, (Ic-7) + cyhalothrin, (Ic-7) + cypermethrin, (Ic-7) + deltamethrin, (Ic-7) + esfenvalerate, (Ic-7) + etofenprox, (Ic-7) + fenpropathrin, (Ic-7) + fenvalerate, (Ic-7) + flucythrinate, (Ic-7) + lambda-cyhalothrin, (Ic-7) + permethrin, (Ic-7) + tau-fluvalinate, (Ic-7) + tralomethrin, (Ic-7) + zeta-cypermethrin, (Ic-7) + cyfluthrin, (Ic-7) + Bifenthrin, (Ic-7) + Cycloprothrin, (Ic-7) + Eflusilanate, (Ic-7) + Fubfenprox, (Ic-7) + Pyrethrin, (Ic-7) + Resmethrin. (Ic-8) + acrinathrin, (IC-8) + alpha-cypermethrin, (IC-8) + betacyfluthrin, (IC-8) + cyhalothrin, (IC-8) + cypermethrin, (IC-8) + deltamethrin, (Ic-8) + esfenvalerate, (Ic-8) + etofenprox, (Ic-8) + fenpropathrin, (Ic-8) + fenvalerate, (Ic-8) + flucythrinate, (Ic-8) + lambda-cyhalothrin, (Ic-8) + peraiethrin, (Ic-8) + tau-fluvalinate, (Ic-8) + tralomethrin, (Ic-8) + zeta-cypermethrin, (Ic-8) + cyfluthrin, (Ic-8) + Bifenthrin, (Ic-8) + Cycloprothrin, (Ic-8) + Eflusilanate, (Ic-8) + Fubfenprox, (Ic-8) + Pyrethrin, (Ic-8) + Resmethrin.

(Icl) -Na + acrinathrin, (Icl) -Na + alpha-cypermethrin, (Icl) -Na + betacyfluthrin, (Icl) -Na + cyhalothrin, (Icl) -Na + cypermethrin, (Icl) -Na + deltamethrin, (Icl) -Na + esfenvalerate, (Icl) -Na + etofenprox, (Icl) -Na + fenpropathrin, (Icl) -Na + fenvalerate, (Icl) -Na + flucythrinate, (Icl) -Na + lambda-cyhalothrin, (Icl) -Na + permethrin, (Icl) -Na + taufluvalinate, (Icl) -Na + tralomethrin, (Icl) -Na + zeta-cypermethrin, (Icl) -Na + cyfluthrin, (I-CI) - Na + bifenthrin, (Icl) -Na + cycloprothrin, (Icl) -Na + eflusilanate, (Icl) -Na + Fubfenprox, (Ic-I) -Na + pyrethrin, (Ic-I) -Na + resmethrin.

(Ic-2) -Na + acrinathrin, (Ic-2) -Na + alpha-cypermethrin, (Ic-2) -Na + betacyfluthrin, (Ic-2) -Na + cyhalothrin, (Ic-2) -Na + Cypermethrin, (Ic-2) -Na + deltamethrin, (Ic-2) -Na + esfenvalerate, (Ic-2) -Na + etofenprox, (Ic-2) -Na + fenpropathrin, (Ic-2) -Na + Fenvalerate, (Ic-2) -Na + flucythrinate, (Ic-2) -Na + lambda-cyhalothrin, (Ic-2) -Na + permethrin, (Ic-2) -Na + taufluvalinate, (Ic-2 ) -Na + tralomethrin, (Ic-2) -Na + zeta-cypermethrin, (Ic-2) -Na + cyfluthrin, (I-c-2) -Na + bifenthrin, (Ic-2) -Na + cycloprothrin, (Ic-2) -Na + Eflusilanate, (Ic-2) -Na + Fubfenprox, (Ic-2) -Na + Pyrethrin, (Ic-2) -Na + Resmethrin.

(Ic-3) Na + acrinathrin, (Ic-3) Na + alpha cypermethrin, (Ic-3) Na + betacyfluthrin, (Ic-3) Na + Cyhalothrin, (Ic-3) Na + Cypermethrin, (Ic-3) -Na + deltamethrin, (Ic-3) -Na + esfenvalerate, (Ic-3) -Na + etofenprox, (Ic-3) -Na + fenpropathrin, (Ic-3) -Na + Fenvalerate, (Ic-3) -Na + flucythrinate, (Ic-3) -Na + lambda-cyhalothrin, (Ic-3) -Na + permethrin, (Ic-3) -Na + taufluvalinate, (Ic-3 ) -Na + tralomethrin, (Ic-3) -Na + zeta-cypermethrin, (Ic-3) -Na + cyfluthrin, (I-c-3) -Na + bifenthrin, (Ic-3) -Na + cycloprothrin, (Ic-3) -Na + Eflusilanate, (Ic-3) -Na + Fubfenprox, (Ic-3) -Na + Pyrethrin, (Ic-3) -Na + Resmethrin.

(Ic-4) -Na + acrinathrin, (Ic-4) -Na + alpha-cypermethrin, (Ic-4) -Na + betacyfluthrin, (Ic-4) -Na + cyhalothrin, (Ic-4) -Na + Cypermethrin, (Ic-4) -Na + deltamethrin, (Ic-4) -Na + esfenvalerate, (Ic-4) -Na + etofenprox, (Ic-4) -Na + fenpropathrin, (Ic-4) -Na + Fenvalerate, (Ic-4) -Na + flucythrinate, (Ic-4) -Na + lambda-cyhalothrin, (Ic-4) -Na + permethrin, (Ic-4) -Na + taufluvalinate, (Ic-4 ) -Na + tralomethrin, (Ic-4) -Na + zeta-cypermethrin, (Ic-4) -Na + cyfluthrin, (I- c-4) -Na + Bifenthrin, (Ic-4) -Na + Cycloprothrin, (Ic-4) -Na + Eflusilanate, (Ic-4) -Na + Fubfenprox, (Ic-4) -Na + Pyrethrin, ( Ic-4) -Na + resmethrin.

(Ic-5) -Na + acrinathrin, (Ic-5) -Na + alpha-cypermethrin, (Ic-5) -Na + betacyfluthrin, (Ic-5) -Na + cyhalothrin, (Ic-5) -Na + Cypermethrin, (Ic-5) -Na + deltamethrin, (Ic-5) -Na + esfenvalerate, (Ic-5) -Na + etofenprox, (Ic-5) -Na + fenpropathrin, (Ic-5) -Na + Fenvalerate, (Ic-5) -Na + flucythrinate, (Ic-5) -Na + lambda-cyhalothrin, (Ic-5) -Na + permethrin, (Ic-5) -Na + taufluvalinate, (Ic-5 ) -Na + tralomethrin, (Ic-5) -Na + zeta-cypermethrin, (Ic-5) -Na + cyfluthrin, (I-c-5) -Na + bifenthrin, (Ic-5) -Na + cycloprothrin, (Ic-5) -Na + Eflusilanate, (Ic-5) -Na + Fubfenprox, (Ic-5) -Na + Pyrethrin, (Ic-5) -Na + Resmethrin.

(Ic-ό) -Na + acrinathrin, (Ic-6) -Na + alpha-cypermethrin, (Ic-β) -Na + betacyfluthrin, (Ic-β) -Na + cyhalothrin, (Ic-6) -Na + Cypermethrin, (Ic-6) -Na + deltamethrin, (Ic-6) -Na + esfenvalerate, (Ic-β) -Na + etofenprox, (Ic-O) -Na + fenpropathrin, (Ic-β) -Na + Fenvalerate, (Ic-ό) -Na + flucythrinate, (Ic-ό) -Na + lambda-cyhalothrin, (Ic-ό) -Na + permethrin, (Ic-6) -Na + tau-fiuvalinate, (Ic-ö ) -Na + tralomethrin, (Ic-6) -Na + zeta-cypermethrin, (Ic-β) -Na + cyfluthrin, (I-c-6) -Na + bifenthrin, (Ic-ό) -Na + cycloprothrin, (Ic-ό) -Na + eflusilanate, (Ic-ό) -Na + Fubfenprox, (Ic-ό) -Na + pyrethrin, (Ic-ö) -Na + resmethrin.

(Ic-7) -Na + acrinathrin, (Ic-7) -Na + alpha-cypermethrin, (Ic-7) -Na + betacyfluthrin, (Ic-7) -Na + cyhalothrin, (Ic-7) -Na + Cypermethrin, (Ic-7) -Na + deltamethrin, (Ic-7) -Na + esfenvalerate, (Ic-7) -Na + etofenprox, (Ic-7) -Na + fenpropathrin, (Ic-7) -Na + Fenvalerate, (Ic-7) -Na + flucythrinate, (Ic-7) -Na + lambda-cyhalothrin, (Ic-7) -Na + permethrin, (Ic-7) -Na + taufluvalinate, (Ic-7 ) -Na + tralomethrin, (Ic-7) -Na + zeta-cypermethrin, (Ic-7) -Na + cyfluthrin, (I-c-7) -Na + bifenthrin, (Ic-7) -Na + cycloprothrin, (Ic-7) -Na + Eflusilanate, (Ic-7) -Na + Fubfenprox, (Ic-7) -Na + Pyrethrin, (Ic-7) -Na + Resmethrin.

(Ic-8) -Na + acrinathrin, (Ic-8) -Na + alpha-cypermethrin, (IcS) -Na + betacyfluthrin, (Ic-8) -Na + cyhalothrin, (Ic-δ) -Na + cypermethrin, (Ic-8) -Na + deltamethrin, (Ic-8) -Na + esfenvalerate,

(I-c-8) -Na + etofenprox, (I-c-8) -Na + fenpropathrin, (I-c-8) -Na + fenvalerate, (I-c-8) -Na +

Flucythrinate, (lc-8) -Na + lambda-cyhalothrin, (lc-8) -Na + permethrin, (lc-8) -Na + taufluvalinate, (lc-8) -Na + tralomethrin, (lc-8 ) -Na + zeta-cypermethrin, (Ic-8) -Na + cyfluthrin, (I-c-8) -Na + bifenthrin, (Ic-8) -Na + cycloprothrin, (Ic-8) -Na + eflusilanate, (Ic-8) -Na + Fubfenprox, (Ic-8) -Na + pyrethrin, (Ic-8) -Na + resmethrin.

The active ingredient combinations may also contain other fungicidal, acaricidal or insecticidal Zumischkomponenten beyond. 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 active ingredients in the drug combinations can be varied within a relatively wide range. In general, the combinations according to the invention comprise active compounds of the formula (I) or salts thereof and the mixing partner in the preferred and particularly preferred mixing ratios indicated in the table below:

* the mixing ratios are based on weight ratios. The ratio is to be understood as active ingredient of the formula (I): Mischpartner

The active compound combinations according to the invention are suitable for controlling animal pests, preferably arthropods and nematodes, in particular insects and spider animals, which occur in agriculture, animal health, in forests, in the protection of stored products and in the hygiene sector. 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 Isopoda, for example, Oniscus asellus, Armadillidium vulgare, Porcellio scaber. From the order of Diplopoda eg Blaniulus guttulatus.

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

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

From the order of Thysanura e.g. Lepisma saccharina.

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

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

From the order of the Blattaria e.g. Blatta orientalis, Periplaneta americana, Leucophaea maderae, Blattella germanica.

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

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

From the order of Phthiraptera e.g. Pediculus humanus corporis, Haematopinus spp., Linognathus spp., Trichodectes spp., Damalinia spp.

From the order of Thysanoptera e.g. Herculothrips femoralis, Thrips tabaci, Thrips palmi, Frankliniella accidentalis.

From the order of Heteroptera, e.g. Eurygaster spp., Dysdercus intermedius, Piesma quadrata, Cirnex lectularius, Rhodnius prolixus, Triatoma spp.

From the order of Homoptera e.g. Aleurodes brassicae, Bemisia tabaci, Trialeurodes vaporariorum, 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., Coccus spp., Psylla spp.

From the order of Lepidoptera, for example, Pectinophora gossypiella, Bupalus piniarius, Cheimatobia brumata, 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, Hofmannophila pseudospretella, Cacoecia podana, Capua reticulana, Choristoneura furniferana, Clysia ambiguella, Homona magnanima, Tortrix viridana, Cnaphalocerus spp., Oulema oryzae.

From the order of Coleoptera e.g. Anobium punctatum, Pvhizopertha dominica, Bruchidius obtectus, Acanthoscelides obtectus, Hylotrupes bajulus, Agelastica alni, Leptinotarsa decemlineata, Phaedon cochleariae, Diabrotica spp., Psylliodes chrysocephala, Epilachna varvestis, 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 Hymenoptera e.g. Diprion spp., Hoplocampa spp., Lasius spp., Monomorium pharaonis, Vespa spp.

From the order of Diptera e.g. 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., Pegomyia hyoscyami, Ceratitis capitata, Dacus oleae, Tipula paludosa, Hylemyia spp., Liriomyza spp.

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

From the class of arachnids, e.g. Scorpio maurus, Latrodectus mactans, Acarus siro, Argas spp., Ornithodoros 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 e.g. 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 substance combinations can be converted into the customary formulations, such as solutions, emulsions, wettable powders, suspensions, powders, dusts, pastes, soluble powders, Granules, suspension-emulsion concentrates, active substance-impregnated natural and synthetic substances as well as ultrafine encapsulations in polymeric substances.

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 with the use of surface-active agents, ie emulsifiers and / or dispersants and / or foam-forming agents.

In the case of using water as an extender, e.g. also organic solvents can 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, e.g. Petroleum 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, 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 finely divided silica, alumina and silicates, as solid carriers for granules come into question: 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 sawdust, coconut shells, corncobs and tobacco stems; 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: e.g. Lignin-sulphite liquors and methylcellulose.

Adhesives such as carboxymethylcellulose, natural and synthetic powdery, granular or latex-like polymers can be used in the formulations, such as gum arabic, polyvinyl alcohol, polyvinyl acetate, as well as natural phospholipids such as cephalins and lecithins and synthetic phospholipids. Other additives may be mineral and vegetable oils. It is possible to use dyes such as inorganic pigments, for example 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.

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

The active compound combinations according to the invention can be present in commercially available 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 esters, carbamates, carboxylic esters, chlorinated hydrocarbons, phenylureas, substances produced by microorganisms, 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 can furthermore be present when used as insecticides in their commercial formulations and in the formulations prepared from these formulations in admixture with synergists. Synergists are compounds by which the effect of the active ingredients is increased without the added synergist itself having to be actively 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 0.0000001 to 95% by weight of active ingredient, preferably between 0.0001 and 1% by weight.

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

When used against hygiene and storage pests, the Wirkstoffkombina¬ tions are characterized by an excellent residual effect on wood and clay and by a good alkali stability on limed documents.

The active compound combinations of the invention not only against plant, hygiene and storage pests, but also in the veterinary sector against animal parasites (ectoparasites) such as ticks, leather ticks, mange mites, 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 soλvie Ischnocerina e.g. 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 e.g. 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. Wohlfabrtia 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 Acaria (Acarida) and the orders of Meta and Mesostigmata e.g. Argas spp., Omithodorus 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, 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 the case of meat, milk, wool, hides, eggs, honey, etc.) are to be reduced so that a more economical and simpler animal husbandry is possible through the use of the active substance combinations according to the invention.

The application of the active compound combinations according to the invention in the veterinary sector in a known manner by enteral administration in the form of, for example, tablets, capsules, infusions, Drenchen, granules, pastes, BoIi, the feed-through process, suppositories, by parenteral administration, such as by Injections (intramuscular, subcutaneous, intravenous, intraperitoneal, etc.), implants, by nasal application, by dermal application in the form of, for example, dipping or bathing (dipping), spraying (spray), pouring on (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, Markierungsvor¬ directions, 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:

Beetle like

Hylotrupes bajulus, Chlorophorus pilosis, Anobium punctatum, Xestobium rufovillosum, Ptilinus pecticomis, Dendrobium pertinex, Ernobius mollis, Priobium carpini, Lyctus brunneus, Lyctus afncanus, 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 like

Sirex juvencus, Urocerus gigas, Urocerus gigas taignus, Urocerus augur. Termites like

Kalotermes flavicollis, Cryptotermes brevis, Heterotermes indicola, Reticulitermes flavipes, Reticuliteπnes 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.

Most preferably, the material to be protected from insect attack is wood and woodworking products.

By wood and woodworking products, which can be protected by the composition according to the invention or mixtures containing it, is to be understood by way of example:

Lumber, wooden beams, railway sleepers, bridge parts, boat bridges, wooden vehicles, crates, pallets, containers, telephone poles, wooden cladding, wooden windows and doors, plywood, chipboard, carpentry or wood products, which are generally used in building or in carpentry ,

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 formulations mentioned can be prepared in a manner known per se, e.g. by mixing the active compounds with at least one solvent or diluent, emulsifier, dispersing and / or binding or fixing agent, water repellent, optionally siccatives and UV stabilizers and optionally dyes and pigments and other processing aids.

The insecticidal agents or concentrates used for the protection of wood and wood-based materials contain the active ingredient according to the invention in a concentration of 0.0001 to 95 wt .-%, in particular 0.001 to 60 wt .-%.

The amount of agents or concentrates used depends on the type and occurrence of

Insects and dependent on the medium. The optimal amount used can be determined in each case by test series. In general, however, it is sufficient 0.0001 to 20 wt .-%, preferably 0.001 to 10 wt .-%, of the active ingredient, based on the material to be protected, use.

The solvent and / or diluent used is an organic-chemical solvent or solvent mixture and / or an oily or oily, volatile organic-chemical solvent or solvent mixture and / or a polar organic-chemical solvent or solvent mixture and / or water and optionally one Emulsifier and / or wetting agent.

As organic-chemical solvents are preferably oily or oil-like solvents having an evaporation number above 35 and a flash point above 30 ⁰ C, preferably above 45 ° C used. As such low-volatility, water-insoluble, oily and oil-like solvents, suitable mineral oils or their aromatic fractions or mineral oil-containing solvent mixtures, preferably white spirit, petroleum and / or alkylbenzene are used.

Mineral oils having a boiling range of 170 to 220 ⁰ C, white spirit having a boiling range of 170 to 220 ⁰ C., spindle oil with a boiling range of 250 to 350 ⁰ C, petroleum and aromatics with a boiling range of 160 to 280 ⁰ C, oil of turpentine and Like. For use.

In a preferred embodiment, liquid aliphatic hydrocarbons having a boiling range of 180 to 210 ⁰ C or high-boiling mixtures of aromatic and aliphatic hydrocarbons having a boiling range of 180 to 22O ⁰ C and / or spindle oil and / or monochloronaphthalene, preferably α-Monochlornaphthalin used.

The organic low volatile oily or oily solvents having an evaporation number above 35 and a flash point above 30 ⁰ C, preferably above 45 ⁰ C, can be partially replaced by light or medium volatile organic chemical solvents, with the Maß¬ task that the solvent mixture is also a Evaporation rate above 35 and a flash point above 30 ⁰ C, preferably above 45 ⁰ C, and that the mixture is soluble or emulsifiable in this solvent mixture.

In a preferred embodiment, a portion of the organic chemical solvent or solvent mixture or an aliphatic polar organic chemical solvent or solvent mixture is replaced. Preferably, aliphatic organic chemical solvents containing hydroxyl and / or ester and / or ether groups are used, for example glycol ethers, esters or the like. In the context of the present invention, the organic-chemical binders used are the water-dilutable and / or soluble or dispersible or emulsifiable synthetic resins and / or binding drying oils, in particular binders consisting of or containing Acrylate resin, a vinyl resin, for example polyvinyl acetate, polyester resin, polycondensation or polyaddition resin, polyurethane resin, alkyd resin or modified alkyd resin, phenolic resin, hydrocarbon resin such as indene coumarone resin, silicone resin, drying vegetable and / or drying oils and / or physically drying binders used on the basis of a natural and / or synthetic resin.

The synthetic resin used as the binder may be used in the form of an emulsion, dispersion or solution. Bitumen or bituminous substances up to 10% by weight can also be used as binders. In addition, known dyes, pigments, water-repellent agents, odor correctors and inhibitors or corrosion inhibitors and the like can be used.

According to the invention, as organic-chemical binders it is preferred to contain at least one alkyd resin or modified alkyd resin and / or one drying vegetable oil in the middle or in the concentrate. Alkyd resins with an oil content of more than 45% by weight, preferably 50 to 68% by weight, are preferably used according to the invention.

The mentioned binder can be completely or partially replaced by a fixing agent (mixture) or a plasticizer (mixture). These additives are intended to volatilize the active ingredients and crystallize or precipitate! prevent. Preferably, they replace 0.01 to 30% of the binder (based on 100% of the binder used).

The plasticizers are derived from the chemical classes of phthalic acid esters such as dibutyl, di-ethyl or benzyl butyl phthalate, phosphoric esters such as tributyl phosphate, adipic acid 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 acid esters.

Fixing agents are chemically based on polyvinyl alkyl ethers such as e.g. Polyvinyl ether or ketones such as benzophenone, ethylene benzophenone.

Particularly suitable solvents or diluents are also water, optionally in admixture with one or more of the abovementioned organochemical solvents or diluents, emulsifiers and dispersants.

A particularly effective wood protection is achieved by large-scale impregnation, eg vacuum, double vacuum or printing process. 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, screens, nets, structures, quays and signal systems, which come into contact with seawater or brackish water.

Growth by sessile Oligochaeten, like Kalkröhrenwmer as well as by shells and kinds of the group Ledamorpha (barnacles), like different Lepas and Scalpellum kinds, or by kinds of the group Balanomorpha (barnacles), like Baianus or Pollicipes species, increases the frictional resistance of As a result of increased energy consumption and, moreover, frequent dry docking, the result is a significant increase in operating costs.

In addition to the vegetation by algae, for example Ectocarpus sp. and Ceramium sp., is particularly the fouling by sessile Entomostraken groups, which are summarized under the name cirripedia (cirripeds), particular importance.

It has now surprisingly been found that the active ingredient combinations according to the invention have an excellent antifouling (anti-fouling) action.

By using the active compound combinations according to the invention, the use of heavy metals, such as, for example, in bis (trialkyltin) sulfides, tri-w-butyltin laurate, tri-n-butyltin chloride, copper (I) oxide, triethyltin chloride, tri-7z-butyl (2-phenyl-4-chlorophenoxy) tin, tributyltin oxide, molybdenum disulfide, Antimony oxide, polymeric butyl titanate, phenyl (bispyridine) bismuth chloride, tri-n-butyltin fluoride, manganese ethylene bis-thiocarbamate, zinc dimethyldithiocarbamate, zinc ethylene bisthiocarbamate, zinc and copper salts of 2-pyridinethiol-l-oxide, bisdimethyldithiocarbamoylzinc ethylene bisthiocarbamate, zinc oxide, copper (I) Ethylene-bisdithiocarbamate, copper thiocyanate, copper naphthenate and Tributylzinnhalogemden be omitted or the concentration of these compounds are significantly reduced.

The ready-to-use antifouling paints may optionally contain other active substances, preferably algicides, fungicides, herbicides, molluscicides or other antifouling active ingredients.

Suitable combination partners for the antifouling agents according to the invention are preferably:

Algicides like

2-/er / -butylamino-4-cyclopropylamino-6-methylthio-l, 3,5-triazm, dichlorophene, diuron, endothal, fentin acetate, isoproturon, methabenzthiazuron, oxyfluorfen, quinoclamine and terbutryn; Fungicides like

BenzofέJthiophencarbonsäurecyclohexylamid _j-S S-dioxide, dichlofluanid, fluorfolpet, 3-iodo-2-pro pinyl-butylcarbamate, tolylfluanid and azoles such as

Azaconazole, cyproconazole, epoxyconazole, hexaconazole, metconazole, propiconazole and terbuconazole;

Molluscicides like

Fentin acetate, metaldehyde, methiocarb, niclosamide, thiodicarb and trimethacarb;

or conventional antifouling agents such as

4,5-dichloro-2-octyl-4-isothiazolin-3-one, diiodomethylparatrylsulfone, 2- (N, N-dimethylthiocarbamoylthio) -5-nitrothiazyl, potassium, copper, sodium and zinc salts of 2-pyridinethiol -l-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 agents used contain the active compound combinations according to the invention in a concentration of 0.001 to 50 wt .-%, in particular from 0.01 to 20 wt .-%.

The antifouling agents of the invention further contain the usual ingredients, e.g. in Ungerer, Chem. Ind. 1985, 37, 730-732 and Williams, Antifouling Marine Coatings, Noyes, Park Ridge, 1973.

In addition to the algicidal, erucicidal, molluscicidal and insecticidal active compounds according to the invention, antifouling paints contain 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, especially 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, rosin esters or modified hard resins in combination with tar or bitumens, asphalt and epoxy compounds, small amounts of chlorinated rubber, chlorinated polypropylene and vinyl resins.

Optionally, paints also contain inorganic pigments, organic pigments or dyes which are preferably insoluble in seawater. Further, paints may contain materials such as rosin to allow for controlled release of the active ingredients enable. The paints may further include plasticizers, rheology modifiers, and other conventional ingredients. The compounds according to the invention or the above-mentioned mixtures can also be incorporated in silk-polishing antifouling systems.

The active ingredient combinations are also suitable for controlling animal pests, in particular insects, arachnids and mites, which are used in closed rooms, such as, for example, apartments, factory halls, offices, vehicle cabins and the like. occurrence. They can be used to control these pests 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 diplopoda e.g. Blaniulus guttulatus, Polydesmus spp.

From the order of Chilopoda e.g. 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 eg Forfϊcula auricularia. From the order of the Isoptera eg Kalotermes spp., Reticulitermes spp.

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

From the order of Coleptera 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, Phthirus pubis.

From the order of Heteroptera, e.g. Cimex hemipterus, Cimex lectularius, Rhodinus prolixus, Triatoma infestans.

Application is in aerosols, non-pressurized sprays, e.g. Pump and atomizer sprays, fog machines, foggers, foams, gels, evaporator products with evaporator plates of cellulose or plastic, liquid evaporators, gel and membrane evaporators, propellergetrie¬ benen evaporators, energy-less or passive evaporation systems, moth papers, mantle bags and moth gels, as granules or dusts, in straw baits or bait stations.

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 ¹ , including the transgenic plants and including lent to plant variety protection or non-protectable plant varieties. 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 being leaves, needles, stems, stems, flowers, fruiting bodies, fruits and seeds, and roots, tubers and rhizomes be listed. The plant parts also include crops as well as vegetative and generative propagation material, for example cuttings, tubers, rhiomes, offshoots and seeds.

The treatment according to the invention of the plants and plant parts with the active ingredients is carried out directly or by acting on their environment, habitat or storage space according to the usual treatment methods, e.g. by dipping, spraying, vaporizing, atomizing, spreading, spreading and in propagation material, in particular in seeds, further by single or multi-layer wrapping.

As already mentioned above, all plants and their parts can be treated according to the invention. 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, the transgenic plants and plant cultivars which have been obtained by genetic engineering methods, if appropriate in combination with conventional methods (Genetically Modified Organisms), and their parts are treated. The term "parts" or "parts of plants" or "plant parts" has been explained above.

It is particularly preferred according to the invention to treat plants of the respective commercially available or in use plant cultivars.

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 that 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 efficiency, easier harvesting, 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 possible, which go beyond the actual expected effects.

The preferred plants or plant varieties to be treated according to the invention to be treated include all plants produced by 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 water or soil salt content, increased flowering efficiency, 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, such as against insects, mites, phytopathogenic fungi, bacteria and / or viruses and an increased tolerance of the plants to certain herbicidal active compounds. Examples of transgenic plants include the important crops such as cereals (wheat, rice), corn, soy, potato, cotton, rapeseed and fruit plants (with the fruits apples, pears, citrus fruits and grapes), with corn, soy, potato, cotton and rapeseed should be highlighted. Traits which are particularly emphasized are the increased defense of the plants against insects by toxins formed in the plants, in particular those produced by the genetic material from Bacillus thuringiensis (for example by the genes CryΙA (a), CryIA (b), CryΙA (c), CryllA, CrylHA, CryIIIB2, Cry9c Cry2Ab, Cry3Bb and CryEF and combinations thereof) are produced in the plants (hereinafter "Bt plants"). Properties ("traits") which are furthermore particularly emphasized are the increased tolerance of the plants to certain herbicidal 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 sold under the trade names YTELD GARD® (eg corn, cotton, soya), KnockOut® (eg corn), 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 to Imidazolinone) and STS® (tolerance to sulfonylureas eg corn). Herbicide-resistant plants (plants grown in a conventional manner with herbicide tolerance) also include the varieties marketed under the name Clearfield® (eg maize). Of course, these statements also apply to future developed or future marketed plant varieties with these or future ent developed genetic traits ("Traits"). The listed plants can be treated particularly advantageously according to the invention with the erfindungs¬ according drug mixtures. The preferred ranges given above for the mixtures also apply to the treatment of these plants. Particularly emphasized is the plant treatment with the mixtures specifically mentioned in the present text.

The expected effect for a given combination of two drugs can be calculated (see Colby, S.R., "Calculating Synergistic and Antagonistic Responses of Herbicidal Combinations", Weeds 15, pages 20-22, 1967) as follows:

If X is the kill rate, expressed in% of the untreated control, using the

Active ingredient A at a rate of m ppm, Y the kill rate, expressed in% of the untreated control, when using the

Active ingredient B at a rate of n ppm,

E means the degree of killing, expressed in% of the untreated control, when using the active compound A and B at application rates of m and n ppm,

X x Y then E X + Y 100

If the actual insecticidal kill rate is greater than calculated, the combination is over-additive in its kill, 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.

applications

Example A

Metopolophium dirhodum test

To prepare a suitable spray solution, a corresponding part by weight of formulated product is mixed with water to obtain the desired concentration.

Barley plants (Hordeum vulgare), which are infected with cereal aphids (Metopolophium dirhodum), are treated by spraying with the preparation solution in 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.

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:

Table A

Plant damaging insects Metopolophium dirhodum - test

Active substance concentration killing in g ai / ha in% after l ^d

deltamethrin

5 37 3.75 30

(I-b-1)

40 27

(I-b-1) + deltamethrin (10.7: 1) invented according to the invention. **

40 + 3.75 90 48.9

Sodium salt of (I-c-6)

40 18 sodium salt of (I-c-6) + deltamethrin (8: 1) according to the invention.

40 + 5 70 48.34

(I-c-7)

40 (I-c-7) + deltamethrin (10.7: 1) according to the invention.

40 + 3.75 60 30

(I-c-8)

40

(I-c-8) + deltamethrin (8: 1) invented according to the invention. **

40 + 5 67 38.89

* Found. = found effect

** calc. = calculated according to the Colby formula Table A

Plant damaging insects Metopolophium dirhodum - test

Active substance concentration killing in g ai / ha in% after 4 ^d

(I-c-6)

40

deltamethrin

3.75 33

(I-c-6) + deltamethrin (10.7: 1) invented according to the invention. **

40 + 3.75 98 33

* Found. = effect found ** calc. = calculated according to the Colby formula

Claims

claims

1. A composition comprising a mixture of a compound of the formula (I)

in which

A for the groups

or - ^Het stands

in which

R ^{1 is} C _r C ₄ -haloalkyl,

R ² and R ³ independently of one another are hydrogen or hydroxyl, in each case optionally monosubstituted or polysubstituted, identically or differently by R ⁴ , oximino or hydrazono-substituted C ₁ -C ₈ -alkyl, C ₃ -C ₆ -alkenyl, C ₃ -C ₆ alkynyl, C _r C ₆ alkoxy, C ₃ -C ₈ cycloalkyl or C ₃ -C ₈ - cycloalkyl-Ci-C ₆ alkyl, wherein the substituents oximino and hydrazono are in turn each unsubstituted or by Ci-C ₈ alkyl, C ₃ - Ce alkenyl, C ₃ -C ₆ alkynyl, C ₃ -C ₈ cycloalkyl, C ₃ -C ₈ cycloalkyl-C _r C ₆ alkyl,

Q-Cs-alkoxy-Ci-Cs-alkyl, cyano-C, -C ₈ alkyl, Ci-C ₈ alkylthio-Ci-C ₈ alkyl, Ci-Cs-alkyl-carbonyl, (C _r C ₈ - Alkoxy) carbonyl, di- (C 1 -C ₈ -alkyl) -aminocarbonyl, aryl or -CH ₂ -aryl can be substituted,

for -C (= X) -Y, or for each optionally mono- or polysubstituted, identically or differently by R ⁵ substituted aryl, heterocyclyl, -CH ₂ -aryl or

Are -CHa-heterocyclyl,

or R ² and R ³ together with the nitrogen atom to which they are attached form a 3- to 8-membered saturated, unsaturated or aromatic heterocyclic ring optionally containing up to three further heteroatoms from the group of nitrogen, sulfur and oxygen, and which is unsubstituted or is the same or different substituted by one or more radicals

R ⁴ , C ₁ -C ₆ -AlkVl, C _r C ₆ haloalkyl, C ₃ -C ₆ alkenyl, C ₃ -C ₆ alkynyl, oxo, oximino or hydrazono, wherein the substituents oximino and hydrazono are in turn unsubstituted or by C ₁ -C ₈ -alkyl, C ₃ -C ₆ -alkenyl, C ₃ -C ₆ -alkynyl, C ₃ -C ₈ -cycloalkyl, C ₃ -C ₈ -cycloalkyl-C ₁ -C ₆ -alkyl, C ₁ -C ₄ -alkyl ₈ -alkoxy-C ₁ - C ₈ alkyl, cyano-QC ₈ alkyl, C _r C ₈ alkylthio-C _r C ₈ alkyl, QC ₈ alkyl carbόnyl, Ci-C ₈ -alkoxy-carbonyl, di - (C 1 -C ₈ -alkyl) -amino-carbonyl, aryl or -CH ₂ -aryl can be substituted,

R ⁴ is halogen, C, -C ₆ alkoxy, QC ₆ haloalkoxy, -S (O) "- C _r C ₆ alkyl, -S (O)" - Ci-C ₆ haloalkyl, hydroxy, cyano, Carboxy, azido, QC ₆ - alkoxycarbonyl, nitro, di- (Ci-C ₆ -alkyl) -amino, or optionally mono- or polysubstituted, identically or differently by Ci-C ₆ alkyl, QC ₆ - haloalkyl and / or Halogen substituted phenoxy,

n is 0, 1 or 2,

R ^{5 is} R ⁴ , QQ-alkyl or QC ₆ -haloalkyl,

X is oxygen or sulfur,

Y is R ⁶ , OR ⁶ , SR ⁶ , NR ⁷ R ⁸ ,

W is oxygen or sulfur,

R ⁶ represents in each case optionally monosubstituted or polysubstituted by identical or different substituents R ⁴ is substituted QC ₈ alkyl, C ₃ -C 8 cycloalkyl or C ₃ -C ₈ - alkyl is cycloalkyl-QC _6, or represents in each case optionally mono- or polysubstituted, identically or differently R ⁵ -substituted aryl, heterocyclyl, -CH ₂ -aryl or -CH ₂ -heterocyclyl,

R ^{7 represents} hydroxy, in each case optionally mono- or polysubstituted by identical or different substituents R ⁴ -substituted QC ₈ -alkyl, C ₃ -C ₆ -alkenyl, C ₃ -C ₆ -alkynyl, QC ₈ -alkoxy, hydroxy-QC ₈ - alkyl, C ₃ -C ₆ -alkenyloxy, C ₃ -C ₆ - Alkynyloxy, C ₃ -C ₈ -cycloalkyl, C ₃ -C ₈ -cycloalkyl-C, -C ₆ -alkyl, -O-C ₂ -C ₃ -C ₈ -cycloalkyl,

in each case optionally monosubstituted or polysubstituted by identical or different substituents R ⁵ substituted aryl, heterocyclyl, aryloxy, heterocyclyloxy, -CH ₂ - aryl, -O-CH ₂ -aryl, heterocyclyl or -CHR-CH ₂ -O-heterocyclyl group,

R ^{8 represents} hydrogen, in each case optionally mono- or polysubstituted, identically or differently by R ⁴ -substituted C ₁ -C ₈ -alkyl, C ₃ -Q-cycloalkyl or

Q-Cs-cycloalkyl-Q-Cβ-alkyl, represents in each case optionally monosubstituted or polysubstituted by identical or different substituents R ⁵ substituted aryl, heterocyclyl, -CH ₂ aryl or -CH _Σ heterocyclyl,

R ⁹ and R ¹⁰ independently of one another are each optionally mono- or polysubstituted, identically or differently by R ⁴ -substituted C ₁ -C ₈ -alkyl, C ₃ -Q-alkenyl, C ₃ -C ₆ -alkyl, C ₃ -C ₈ -cycloalkyl or C ₃ -C ₈ -cycloalkyl-C _r C ₆ -alkyl, for -C (= X) -Y, in each case optionally mono- or polysubstituted, identically or differently by R ⁵ -substituted aryl, heterocyclyl, -CH ₂ -

Aryl or -CH ₂ -heterocyclyl,

or

R ⁹ and R ¹⁰ together with the sulfur atom to which they are attached, a 3- to 8-membered saturated or unsaturated heterocyclic ring, which may optionally contain up to three further heteroatoms from the group nitrogen,

Contains sulfur and oxygen, and is unsubstituted or substituted identically or differently by one or more radicals R ⁴ , C ₁ -C ₆ -alkyl, C ₁ -C ₆ -haloalkyl, oxo, oximino or hydrazono, wherein the substituents oximino and hydrazono in turn unsubstituted or are C _r C ₈ alkyl, C ₃ -C ₆ alkenyl, C ₃ -C ₆ alkynyl, C ₃ -C ₈ cycloalkyl, C ₃ -C ₈ -

Cycloalkyl-d-Cβ-alkyl, CrC ₈ -alkoxy-C _r C ₈ alkyl, cyano-C, -C ₈ alkyl, Q- C ₈ alkylthio-Ci-C ₈ alkyl, Ci-C ₈ alkyl carbonyl, C 1 -C ₈ -alkoxycarbonyl, di- (C 1 -C ₈ -alkyl) -amino-carbonyl, aryl or -CH ₂ -aryl can be substituted,

Het / heterocyclyl is a cyclic radical which may be fully saturated, partially unsaturated or fully unsaturated or aromatic and which is characterized by at least one or more identical or different atoms of the

Group nitrogen, sulfur or oxygen may be interrupted, however not two oxygen atoms must be directly adjacent and still at least one carbon atom in the ring must be present, wherein the cyclic radical is unsubstituted or substituted by one or more radicals R ⁴ , QC ₆ - alkyl, C _r C ₆ haloalkyl, qQ alkoxy C 1 -C 8 -alkyl, C 1 -C 5 -alkylthio-C 1 -C 5 -alkyl, oxo, oximino or hydrazono, where the substituents are oximino and

Hydrazono are in turn unsubstituted or by Cj-Q-alkyl, C ₃ -C ₆ alkenyl, C ₃ -C ₆ alkynyl, C ₃ -C ₈ cycloalkyl, C ₃ -C ₈ cycloalkyl-C _r C ₆ alkyl , Cj-C ₈ -alkoxy-C ₁ - C ₈ alkyl, cyano-Ci-C ₈ alkyl, C _r C ₈ alkylthio-C _r C ₈ alkyl, C _r C ₈ alkyl-carbonyl, QC ₈ Alkoxy-carbonyl, di- (C 1 -C ₈ -alkyl) -amino-carbonyl, aryl or -CH ₂ -aryl can be substituted,

and / or a salt of a compound of the formula (I)

and

at least one of the following compounds

acrinathrin

Alpha-cypermethrin

beta-cyfluthrin

cyhalothrin

cypermethrin

deltamethrin

esfenvalerate

etofenprox

fenpropathrin

fenvalerate

flucythrinate

Lambda-cyhalothrin

permethrin

Tau-fluvalinate

tralomethrine

Zeta-cypermethrin

cyfluthrin

bifenthrin

cycloprothrin

Eflusilanat

fubfenprox Pyrethrin Resmethrin.

2. Use of mixtures as defined in claim 1, for controlling animal pests.

3. A method for controlling animal pests, characterized in that mixtures, as defined in claim 1, act on animal pests and / or their habitat.

4. A process for the preparation of insecticidal and acaricidal agents, characterized in that mixing mixtures as defined in claim 1, with extenders and / or oberflächen¬ active substances.