EP1646283A1

EP1646283A1 - Active agents combination exhibiting insecticidal and acaricide properties

Info

Publication number: EP1646283A1
Application number: EP04740322A
Authority: EP
Inventors: Reiner Fischer; Thomas Bretschneider; Rüdiger Fischer; Christian Funke; Wolfgang Thielert
Original assignee: Bayer CropScience AG
Current assignee: Bayer Intellectual Property GmbH
Priority date: 2003-07-08
Filing date: 2004-06-25
Publication date: 2006-04-19
Also published as: AU2004255411A1; CN1845672A; WO2005004604A1; US20070142463A1; KR101122102B1; DE10330723A1; CN100464635C; US7795303B2; BRPI0412357A; BRPI0412357B1; BRPI0412357B8; IL172806A0; IL172806A; TWI338563B; JP2009513500A; ZA200600098B; TW200514507A; JP4733026B2; MXPA06000201A; KR20060032995A

Abstract

The invention relates to a novel active agent combinations consisting of cyclic ceto-enols of formula (I) and active agents of formula (II) specified in description which exhibits excellent insecticidal and acaricide properties.

Description

Active substance combinations with insecticidal and acaricidal properties

The present invention relates to new combinations of active substances which consist of known cyclic ketoenols on the one hand and other known insecticidal active substances on the other hand and are very well suited for controlling animal pests such as insects and unwanted acarids.

It is already known that certain cyclic ketoenols have fungicidal, insecticidal and acaricidal properties (EP-A-528 156, EP-A-0 647 637, WO 95/26 345, WO 96/20 196, WO 96/25 395, WO 96/35 664, WO 97/01 535, WO97 / 02243, WO 97/36 868, WO 98/05 638, WO 98/25 928, WO 99/16748, WO 99/43 649, WO 99/48 869 , WO 99/55 673, WO 01/23 354 and WO 01/74770). The effectiveness of these substances is good, but leaves something to be desired in some cases at low application rates.

It is also known that mixtures of phthalic acid diamides and other bioactive compounds have an insecticidal and or acaricidal action (WO 02/087334). The effect of these mixtures is not always optimal.

Furthermore, it is already known that numerous heterocycles, organotin compounds, benzoylureas and pyrethroids have insecticidal and acaricidal properties (cf. WO 93-22297, WO 93-10 083, DE-A 2 641 343, EP-A-347 488) , EP-A-210487, US-A 3 264 177 and EP-A-234045). However, the effects of these substances are not always satisfactory.

It has now been found that compounds of the formula (I)

in which

X represents C 1 -C 6 alkyl, bromine, C 1 -C 6 alkoxy or C 3 -C 3 haloalkyl,

Y represents hydrogen, Cj-Cö-alkyl, halogen, Cj-Cö-alkoxy, Cι-C3-haloalkyl,

Z represents Ci-Cg-alkyl, halogen, Ci-Cg-alkoxy,

n stands for a number from 0-3, A for hydrogen or in each case optionally substituted by halogen, straight-chain or branched C 1 -C 2 -Al 1, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 1 -C 6 -alcohol y-C 1 -C 6 -alkyl, Cycloalkyl with 3-8 ring atoms, which can be interrupted by oxygen and / or sulfur or in each case optionally by halogen, Ci-Cg-alkyl, Ci-Cg-haloalkyl-, Ci-Cg-alkoxy-, C _j - Cg-haloalkoxy, Nitro substituted phenyl or phenyl-Ci-Cg-alkyl,

B represents hydrogen, C \ -Cg-alkyl or C \ -Cg-alkoxy-C -C4-alkyl

or in what

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 by halogen, Ci-Cg-alkyl, Ci-Cg-alkoxy, Cj-C ^ -haloalkyl, Form C1-C4-haloalkoxy, Cι-C4_-al ylthio 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: r-Fr (d)

in which

Rl for each optionally substituted by halogen -CC20-Al l, C2-C20-lken l, Ci-Cg-alkoxy-C ^ -Cg-alkyl, C ^ Cg-alkylthio-Ci-Cg-alkyl, Cj-Cg- Polyalkoxy ^ -Cg-alkyl or cycloalkyl with 3-8 ring atoms, which can be interrupted by oxygen and / or sulfur atoms, is optionally halogen, nitro, Ci-Cg-alkyl, Ci-Cg-alkoxy, Ci-Cg -Halogen- alk l, Ci-Cg-haloalkoxy-substituted phenyl; represents phenyl-Ci-Cg-alkyl optionally substituted by halogen, Cj-Cg-alkyl, Ci-Cg-alkoxy, Ci-Cg-haloalkyl, Ci-Cg-haloalkoxy, represents in each case optionally substituted by halogen and or Ci-Cg-Al yl pyridyl, pyrimidyl, thiazolyl or pyrazolyl, represents optionally substituted by halogen and / or Ci-Cg-A kyl-substituted phenoxy-Ci-Cg-alkyl,

R ^ represents in each case optionally substituted by halogen -C-C2 () - Alk l, C2-C2o-alkenyl, -C-Cg-alkoxy-C2-Cg-alkyl or Cι-Cg-polyalkoxy-C2-Cg-alkyl, for each substituted haloalkyl optionally substituted by halogen, nitro, Ci -CG alkyl, Cj-Cg-alkoxy, C _j -Cg- phenyl or benzyl,

R ^ is optionally substituted by halogen, Cj-Cg-alkyl, represents in each case optionally Cι-C4 alk l, halogen, Cj-C4-Halogenalk l, C _j-C4-alkoxy, Cι-C4-halo- alkoxy, nitro or Cyano substituted phenyl or benzyl,

R ^ and R independently of one another each optionally substituted by halogen C - Cg-alkyl, Ci-Cg-alkoxy, Ci-Cg-alkylamino, di- (-C-Cg) alkylamino, C ^ -Cg-alkylthio, C-2 "C5-alkenylthio, C2-C5-AlMnylthio, C3-C7-cycloalkylthio, for each optionally by halogen, nitro, cyano, C -C-alkoxy, Cι-C4-haloalkoxy, Cι-C4-alkylthio, Cι-C4-haloalkylthio , -C-C4-Alk l, -C-C4-haloalkyl substituted phenyl, phenoxy or phenylthio,

R "and R ^ independently of one another for each optionally substituted by halogen C _] - Ci Q-alkyl, Ci-C _j o-Al oy, C3-Cg-alkenyl, Cj-Cg-Altoxy-Ci-Cg-alkyl, for - Phenyl substituted by halogen, Ci-Cg-haloalkyl, C ^ -Cg-alkyl or Ci -Cß-alkoxy, for optionally by halogen, C _j -Cg-alkyl, Cj-Cg-haloalkyl or C _] -Cg-alkoxy substituted benzyl or 6-membered together represent an optionally interrupted by oxygen or sulfur, 5- to ring, which may optionally be substituted by C _j -CG alkyl,

and at least one phthalic acid diamide of the formula (II) are synergistically active and are suitable for controlling animal pests.

The phthalic acid diamides of the formula (II) are likewise known compounds which are known from or are included in the following publications (cf. EP-A-0 919 542, EP-A-1 006 107, WO 01/00 575, WO 01/00 599, WO 01/46 124, JP 2001-33 555 9, WO 01/02354, WO 01/21 576, WO 02/08 8074, WO 02/08 8075, WO 02/09 4765, WO 02/09 4766, WO 02/06 2807). Reference is hereby expressly made to the generic formulas and definitions described in these publications and to the individual compounds described therein.

The phthalic acid diamides can be summarized under the formula (II):

in which

K represents halogen, cyano, alkyl, haloalkyl, alkoxy or haloalkoxy,

Re *, Re ^, Re ^ each independently of one another for hydrogen, cyano, for C3-Cg-cycloalkyl optionally substituted by halogen or for a group of the formula

Ml-Q _k

stand in which

M ^ represents optionally substituted alkylene, alkenylene or alkynylene,

Q represents hydrogen, halogen, cyano, nitro, haloalkyl, in each case optionally substituted C3-Cg-cycloalkyl, alkylcarbonyl or alkoxycarbonyl, in each case optionally substituted phenyl, hetaryl or for a group T-Re ⁴ ,

in which

T stands for -0-, -S (0) _m - or - N -, Re

Re ^{4 represents} hydrogen, in each case optionally substituted alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, alkoxyalkyl, alkylcarbonyl, alkoxycarbonyl, phenyl, phenylalkyl, phenylalkoxy, hetaryl, hetarylalkyl,

Re ^{5 represents} hydrogen, in each case optionally substituted alkylcarbonyl, alkoxycarbonyl, phenylcarbonyl or phenylalkoxycarbonyl, k represents the numbers 1 to 4,

m represents the numbers 0 to 2,

Re and Re ² together form an optionally substituted four- to seven-membered ring which can optionally be interrupted by heteroatoms,

L * and 1? independently of one another represent hydrogen, halogen, cyano or in each case optionally substituted alkyl, alkoxy, alk-S (0) _m -, phenyl, phenoxy or hetaryloxy,

1-2 represents hydrogen, halogen, cyano, in each case optionally substituted alkyl, alkenyl, alkynyl, haloalkyl, cycloalkyl, phenyl, hetaryl or for the group M ² -Re ⁶ ,

in which

M ^{2 represents} -O- or -S (0) _m -,

and

Re * represents in each case optionally substituted alkyl, alkenyl, alkynyl, cycloalkyl, phenyl or hetaryl,

IA and \ A or

1,1 and L ² together form an optionally substituted five- to six-membered ring which can optionally be interrupted by heteroatoms.

These are preferably compounds of the formula (H)

in which

K preferably represents fluorine, chlorine, bromine, iodine, cyano, Ci-Cg-alkyl, C _j -Cg-haloalkyl, Ci-Cg-alkoxy or Ci-Cg-haloalkoxy,

Rel, Re ² and Re3 preferably each independently of one another for hydrogen, cyano, for C3-Cg-cycloalkyl optionally substituted by halogen or for a group of the formula

Ml-Q _k stand in which

M * preferably represents Ci-Cg-alkylene, C3-Cg-alkenylene or C3-Cg-alkynylene,

Q is preferred for hydrogen, halogen, cyano, nitro, haloalkyl or for C3-Cg-cycloalkyl optionally substituted by fluorine, chlorine, C 1 -C 6 -alkyl or C 1 -C 6 -alkoxy, in which one or two ring members which are not directly adjacent are formed by Oxygen and / or sulfur are replaced or for in each case optionally substituted by halogen Ci-Cg-alkylcarbonyl or C; [- Cg-alkoxycarbonyl or for in each case optionally by halogen, Ci-Cg-alkyl, Ci-Cg-haloalkyl, Cj-Cg- Alkoxy, Ci-C - haloalkoxy, cyano or nitro substituted phenyl or hetaryl with 5 to 6 ring atoms (for example furanyl, pyridyl, imidazolyl, triazolyl, pyrazolyl, pyrimidyl, thiazolyl or thienyl) or for a group

T-Re ⁴ stands,

in which

T preferably represents -0-, -S (0) _m - or - N -, Re ⁵

Re ^{4 is} preferred for hydrogen, for in each case optionally substituted by fluorine and / or chlorine Ci-Cg-alkyl, C3-Cg-alkenyl, C3-Cg-alkynyl. C ₃ -Cg-Cycloalkyl, C ₃ -Cg-Cycloalkyl-Cι-C2-alkyl, Ci-Cg-Alkylcafbonyl, Ci-Cg-Alkoxycarbonyl, for each optionally up to four times by halogen, Ci-Cg-alkyl, Cj-Cg -Alkoxy, C1-C4-haloalkyl, Cι-C4-haloalkoxy, nitro or cyano substituted phenyl, C1-C4-phenylalkyl, Ci-Qj-phenylalkyloxy, hetaryl or hetarylalkyl, where hetaryl with 5 to 6 ring atoms (for example furanyl, pyridyl, Imidazolyl, triazolyl, pyrazolyl, pyrimidyl, thiazolyl or thienyl),

Re ^ preferably for hydrogen, for each Ci-Cg-alkylcarbonyl, C1-Cg-alkoxycarbonyl optionally substituted by fluorine and / or chlorine, for each optionally one to four times by halogen, Ci-Cg-alkyl, C ^ -Cg- Alkoxy, Cj-C ^ haloalkyl, C ^ - C4-haloalkoxy, nitro or cyano substituted phenyl-carbonyl or phenyl-Cι-C.4-alkyloxycarbonyl,

k preferably represents the numbers 1 to 3,

m preferably represents the numbers 0 to 2, Re and Re ² preferably form a five- to six-membered ring which can optionally be interrupted by an oxygen or sulfur atom,

Ll and 1? preferably independently of one another for hydrogen, cyano, fluorine, chlorine, bromine, iodine, Ci-Cg-alkyl, Ci-Cφ-haloalkyl, Cj-Cg-alkoxy, Ci-Qj-haloalkoxy, Cι-C4-alkyl-S (0) _m -, -C-C4-haloalkyl-S (0) _m -, for each optionally single to triple by fluorine, chlorine, bromine, Cj-Cg-alkyl, C ^ -Cg-alkoxy, C1-C4- haloalkyl, Cι - C-4-haloalkoxy, cyano or nitro substituted phenyl, phenoxy, pyridinyloxy, thiazolyloxy or pyrimidyloxy,

L ² preferably for hydrogen, fluorine, chlorine, bromine, iodine, cyano, for each Ci-Ci _Q- alkyl optionally substituted by fluorine and / or chlorine, C2-C1 _Q -alkenyl, C2-Cg-alkynyl, for each optionally substituted by fluorine, chlorine, C3-Cg-cycloalkyl, for each optionally optionally up to three times by fluorine, chlorine, bromine, Ci-Cg-alkyl, Cj-Cg-alkoxy, Cι-C4-haloalkyl, C1-C4-haloalkoxy, cyano or nitro substituted phenyl, pyridyl, thienyl, pyrimidyl or thiazolyl,

or for a group

M ² -Re ⁶

is in which

M ² preferably represents - - or -S (0) _m - and

Re ^ preferred for C _j -Cg-alkyl, C2-Cg-alkenyl, C3 ~ Cg-alkynyl or C3-Cg-cycloalkyl, each optionally substituted by fluorine and / or chlorine, for each optionally up to three times by fluorine, chlorine, bromine , Cj-Cg-alkyl, Cj-Cg-alkoxy, C1-C4-haloalkyl, Cι-C -haloalkoxy, cyano or nitro substituted phenyl, pyridyl, pyrimidyl or thiazolyl,

Li and L ³

or

L ² and ß preferably together each form a five- to six-membered ring optionally substituted by fluorine and / or CJ-C J-alkyl, which may optionally be interrupted by one or two oxygen atoms. It is particularly preferred to use compounds of the formula II in which

K particularly preferably represents chlorine, bromine and iodine,

Re, Re ² and Re ^{3 are} particularly preferably each independently of one another for hydrogen or for a group of the formula

stand in which

M particularly preferably represents C i-Cg-alkylene, C3-Cg-alkenylene or C3-Cg-alkynylene,

Q particularly preferably represents hydrogen, fluorine, chlorine, cyano, trifluoromethyl, C3-Cg-cycloalkyl or a group T-Re ⁴ ,

in which

T particularly preferably represents -O- or -S (0) _m -,

Re ⁴ particularly preferably represents hydrogen, in each case optionally mono- to trisubstituted by fluorine and / or chlorine-substituted C 1 -C 6 -alkyl, C3-Cg-alkenyl, C3-Cg-alkynyl or C3-Cg-cycloalkyl,

k particularly preferably represents the numbers 1 to 3,

m particularly preferably represents the numbers 0 to 2,

L and 1? independently of one another particularly preferably for hydrogen, fluorine, chlorine, bromine, iodine, cyano, C _j -C ^ alkyl, Cι-C2-haloalkyl, Cι-C4 alkoxy, C _j -C ^ haloalkoxy, for each optionally phenyl or phenoxy which is monosubstituted or disubstituted by fluorine, chlorine, bromine, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, C 1 -C 2 -haloalkyl, C 1 -C 4 -haloalkoxy, cyano or nitro,

L ² particularly preferably represents hydrogen, fluorine, chlorine, bromine, iodine, cyano, represents in each case optionally substituted once to thirteen times by fluorine and / or chlorine-substituted C _j -Cg- alkyl, C2-Cg alkenyl, C2-Cg alkynyl, C3 -Cg-cycloalkyl or for a group

M ² -Re ⁶ is in which

M ² particularly preferably represents -O- or -S (0) _m -,

and

Re "is particularly preferred for C 1 -C 6 -alkyl, C 1 -C 6 -alkenyl, C 2 -C 6 -alkynyl or C 3 -C 6 -cycloalkyl, each of which is monosubstituted to thirteen times substituted by fluorine and / or chlorine, for each optionally monosubstituted or disubstituted by fluorine , Chlorine, bromine, C ₁ -C 4 alkyl, -C 4 -C alkoxy, trifluoromethyl, difluoromethoxy, trifluoromethoxy, cyano or nitro substituted phenyl or pyridyl.

It is very particularly preferred to use compounds of the formula D) in which

K very particularly preferably represents iodine,

Re * and Re ² very particularly preferably represent hydrogen,

Re ³ very particularly preferably for a group of the formula

M * -Q

is in which

M ¹ very particularly preferably for -CHCH ₃ -CH -, -C (CH3) ₂ -CH ₂ -, -CHC ₂ H ₅ -CH ₂ -, - - CC - CH; -C (C ₂ H ₅ ) 2-CH ₂ -, / \ ^H 3 ^C C ₂ H ₅

Q very particularly preferably for hydrogen, fluorine, chlorine, cyano, trifluoromethyl, C3-C - cycloalkyl or for a group

T-Re ⁴ stands,

in which

T very particularly preferably represents -S-, -SO- or -SO2-,

Re ⁴ very particularly preferably for methyl, ethyl, n-propyl, isopropyl, n-butyl, iso-butyl, sec-butyl or tert-butyl, allyl which is optionally mono- to trisubstituted by fluorine and / or chlorine, Butenyl or isoprenyl, L and ß independently of one another very particularly preferably represent hydrogen, fluorine, chlorine, bromine, iodine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, methoxy, ethoxy, trifluoromethyl, difluoromethoxy or trifluoromethoxy,

L ² very particularly preferably for hydrogen, fluorine, chlorine, bromine, iodine, cyano, for each methyl, ethyl, n-propyl, iso-propyl, n-butyl, iso-butyl which is optionally monosubstituted to nine times by fluorine and / or chlorine , sec-butyl, tert-butyl, allyl, butenyl or isoprenyl or for a group

M ² -Re ⁶

stands,

M ² very particularly preferably represents oxygen or sulfur,

and

Re> very particularly preferably for methyl, ethyl, n-propyl, iso-propyl, n-butyl, iso-butyl, sec.-butyl, tert.-butyl, allyl, each of which is monosubstituted or disubstituted by fluorine and / or chlorine. Butenyl or isoprenyl, represents phenyl which is optionally mono- to disubstituted by fluorine, chlorine, bromine, methyl, ethyl, methoxy, trifluoromethyl, difluoromethoxy, trifluoromethoxy, cyano or nitro.

It is particularly preferably the compound of the formula II-1

Surprisingly, the insecticidal and / or acaricidal action of the active compound combinations according to the invention is substantially higher than the sum of the actions of the individual active compounds. So there is an unforeseeable, real synergistic effect and not just an addition.

In addition to at least one active ingredient of the formula (I), the active compound combinations according to the invention contain at least one active ingredient of the formula (II). Active substance combinations containing compounds of the formula (I) are preferred,

in which

X represents Ci -Qj-alkyl, bromine, Ci -Gψ-alkoxy or Ci -C3-haloalkyl,

Y represents hydrogen, Ci-Gψ-alkyl, fluorine, chlorine, bromine, Ci-Q / j-alkoxy, C1-C3 -haloalkyl,

Z represents C 1 -C ₄ -alkyl, chlorine, bromine, C 1 -C ₄ -alkoxy,

n stands for a number from 0-2,

A for hydrogen or in each case optionally up to three times substituted by fluorine, straight-chain or branched C 1 -C 6 -alkyl, C 1 -C 6 -alkenyl, C 1 -C 4 -alkoxy-C 1 -C 2 -alkyl, cycloalkyl having 3-8 ring atoms, which may be by Oxygen and / or sulfur can be interrupted or for phenyl which is optionally monosubstituted or disubstituted by fluorine, chlorine, bromine, C 1 -C 2 -alk l, C 1 -C 2 -haloalkyl, C 1 -C 2 -alkoxy, C 1 -C 4 -haloalkoxy, nitro or benzyl,

B represents hydrogen, C 1 -C ₂ alkyl or C j -C ₂ alkoxy-C j -C ₂ alkyl

or in what

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 mono- or disubstituted by fluorine, chlorine, C1-C4-alkyl, Cι-C4-alkoxy, Cι- C2-haloalkyl, -C-C2-haloalkoxy or C1-C2- alkylthio substituted 3- to 7-membered ring form,

G for hydrogen (a) or for the groups

CO-R ¹ (b) (c) -SOr-R ^J (d)

/ .R ° -fi O- ^{<e) or} c R. ^■ »

in which R represents in each case optionally mono- to pentasubstituted by fluorine or chlorine, C _j - C ₁₆ alkyl, C ₂ -C ₁₆ alkenyl, C -C4-alkoxy-C -C ₄ alkyl, C ₁ -C ₄ -alkylthio-Cι -C ₄ alkyl or cycloalkyl with 3-6 ring atoms, which can be interrupted by oxygen and / or sulfur atoms, is optionally monosubstituted or disubstituted by fluorine, chlorine, bromine, nitro, C -C4-al yl, Cι- C4-Alko y, -C-C4-haloalkyl, C -C4-haloalkoxy-substituted phenyl stands for optionally mono- to disubstituted by fluorine, chlorine, bromine, -C-C4 ~ alkyl, C -C4 alkoxy, Ci-Qψ-haloalkyl -, -C-C4-haloalkoxy-substituted benzyl stands for pyridyl, pyrimidyl, thiazolyl or pyrazolyl which is optionally mono- to disubstituted by chlorine, bromine and / or C-C4-alk l,

R ² for each optionally single to fivefold fluorine or chlorine by substituted C1-C ₂ o-alkyl, C ₂ -C ₂ o-alkenyl, C ₁ -Cg-alkoxy-C ₂ -Cg-alkyl, -C-Cg-polyalkoxy- C ₂ -Cg-al_kyl represents phenyl or benzyl, in each case optionally one to two times by fluorine, chlorine, bromine, nitro, C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, C1-C4-haloalkyl-substituent,

R3 for C1-C4-AH VI which is optionally monosubstituted to pentasubstituted by fluorine or chlorine, for in each case optionally monosubstituted to twice by Cι -Al-yl, fluorine, chlorine, bromine, C -C4-haloalkyl, C -C4-alkoxy, C -C4-haloalkoxy, nitro or cyano substituted phenyl or benzyl,

R ⁴ and R-> independently of one another for C 1 -C ₄ -Al 1, C -C ₄ -alko, C -C ₄ -l ylamino, di- (C -C ₄ ) -alkylamino, each optionally mono- to trisubstituted by fluorine or chlorine, -CC alkylthio, C2-C-alkenylthio, C3-Cg-cycloalkyl-thio, for each optionally one to two times by fluorine, chlorine, bromine, nitro, cyano, C -C 2 -alko y, -C-C2-haloalkoxy, -C-C2-alkylthio, C -C2-haloalkylthio, C -C2-alkyl, C ~ C2-haloalkyl substituted phenyl, phenoxy or phenylthio,

R "and R ^ independently of one another, each optionally monosubstituted to trisubstituted by fluorine or chlorine, Ci-Cg-alkyl, C -Cg-alkoxy, C3-Cg-alkenyl, Ci-C4-alkoxy-Cι-C2-alkyl, for optionally benzyl which is monosubstituted or disubstituted by fluorine, chlorine, bromine, C.sub.2 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 alkyl or C.sub.4 -C.sub.4 alkoxy or together represents an optionally by oxygen or Sulfur-interrupted 5- to 6-membered ring, which may optionally be substituted by C 1 -C 2 -Al 1,

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

For the radicals designated with halogen in the preferred ranges, halogen preferably represents chlorine and fluorine.

Active ingredient combinations containing compounds of the formula (ϊ) are particularly preferred,

in which

X represents C 1 -C 4 -alkyl, C 1 -C 4 -alko y or trifluoromethyl,

Y represents hydrogen, C -C4-alkyl, chlorine, bromine, -C-C4-alkoxy, C -C2-haloalkyl,

Z represents C -C ₄ alkyl, chlorine, bromine, C -C ^ alkoxy,

n represents 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 monosubstituted or substituted by C -C4-Alk l or Cι ~ C4-alkoxy,

G for hydrogen (a) or for the groups

- CO-R ¹ (b) (c) stands

in which

R represents in each case optionally mono- to trisubstituted by fluorine or chlorine, C _j - Ci2 alkyl, C ₂ -Cι ₂ -alkenyl, C ₁ -C 4 -alkoxy-C ₁ -C 2 alkyl, or cycloalkyl having 3-6 ring atoms, which may be interrupted by 1 to 2 oxygen atoms, is, optionally monosubstituted by fluorine, chlorine, bromine, nitro, C -C 4 alkyl, C _j -C ^ alkoxy, trifluoromethyl or trifluoromethoxy-substituted phenyl;

R ^{2 represents} C _j -C ^ alyl, C ₂ -C ₁₂ alkenyl, C ₁ -C alkoxy-C ₂ -C 4 alkyl, represents phenyl or benzyl which is in each case simply substituted by fluorine, chlorine, bromine, nitro, C -C4-Al1, C -C4alkoxy or trifluoromethyl, and at least one active compound of the formula (II).

Active ingredient combinations containing compounds of the formula (T) are very particularly preferred,

in which

X represents methyl, ethyl, methoxy, ethoxy or trifluoromethyl,

Y represents hydrogen, methyl, ethyl, chlorine, bromine, methoxy or trifluoromethyl,

Z represents methyl, ethyl, chlorine, bromine or methoxy,

n represents 0 or 1,

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

G for hydrogen (a) or for the groups

in which

Rl for each optionally monosubstituted to trisubstituted by fluorine or chlorine-Cg-alkyl, C ₂ -Cg-alkenyl, C -C ₃ -alkoxy-Cι-C2-alkyl, or cycloalkyl with 3-6 ring atoms, which by 1 to 2 oxygen atoms can be interrupted, represents phenyl optionally substituted by fluorine, chlorine, bromine, methyl, methoxy, trifluoromethyl or trifluoromethoxy;

R ^{2 represents} C 1 -Cg alkyl, C ₂ -Cg alkenyl, Ci -C ₄ alkoxy-C ₂ -C ₃ alkyl, each optionally simply by fluorine, chlorine, bromine, nitro, methyl, methoxy or trifluoromethyl-substituted phenyl or benzyl,

and at least one active ingredient of the formula (IQ. Active substance combinations containing the compound of the formula (Ib-1) are particularly preferred

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

Active compound combinations containing the compound of the formula (I-b-1) and the active compound of the formula (II-l) are emphasized.

The general definitions or explanations of residues or explanations listed above or in preferred areas can be combined with one another, that is to say also between the respective areas and preferred areas. They apply accordingly to the end products as well as to the preliminary and intermediate products.

According to the invention, preference is given to the compounds of the formulas (I) and (II) in which there is a combination of the meanings listed above as preferred (preferred).

According to the invention, particular preference is given to the compounds of the formulas (I) and (II) in which there is a combination of the meanings listed above as being particularly preferred.

According to the invention, very particular preference is given to the compounds of the formulas (I) and (II) in which there is a combination of the meanings listed above as being very particularly preferred.

Saturated or unsaturated hydrocarbon radicals such as alkyl or alkenyl, also in combination with heteroatoms, such as e.g. in alkoxy, where possible, be straight-chain or branched.

Unless otherwise stated, optionally substituted radicals can be mono- or polysubstituted, and in the case of multiple substitutions the substituents can be the same or different. The active ingredient combinations can also contain other fungicidal, acaricidal or insecticidal active mixing partners.

If the active substances are present in the active substance combinations according to the invention in certain weight ratios, the synergistic effect is particularly evident. However, the weight ratios of the active ingredients in the active ingredient combinations can be varied within a relatively wide range. In general, the combinations according to the invention contain active ingredients of the formula (I) and the mixing partner of the formula () in the stated preferred and particularly preferred mixing ratios:

The preferred mixing ratio is 500.T to 1:50.

The particularly preferred mixing ratio is 25: 1 to 1:10.

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

The active compound combinations according to the invention are suitable, with good plant tolerance, favorable warm-blood toxicity and good environmental compatibility, for combating animal damage, preferably arthropods and nematodes, in particular insects and arachnids, which are used in agriculture, animal health, in forests, in gardens and leisure facilities, in Storage and material protection as well as in the hygiene sector. They are effective against normally sensitive and resistant species as well as against all or individual stages of development. The pests mentioned above include:

From the order of the Isopoda e.g. Oniscus asellus, Armadillidium vulgare, Porcellio scaber.

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

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

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

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

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

From the order of the Orthoptera, for example Acheta domesticus, Gryllotalpa spp., Locusta migratoria migratorioides, Melanoplus spp., Schistocerca gregaria. From the order of the Blattariä, for example Blatta orientalis, Periplaneta americana, Leucophaea maderae, Blattella germanica.

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

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

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

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

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

From the order of the 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., Macroiphusumum padi, Empoasca spp., Euscelis bilobatus, Nephotettix cincticeps, Lecanium corni, Saissetia oleae, Laodelphax striatellus, Nilaparvata lugens, Aonidiella aurantii, Aspidiotus hederae, Pseudococcus spp., Psylla spp.

From the order of the Lepidoptera e.g. Pectinophora gossypiella, Bupalus piniarius, Cheimatobia brumata, Lithocolletis blancardella, Hyponomeuta padella, Plutella xylostella, Malacosoma neustria, Euproctis chrysorrhoea, Lymantria spp., Bucculatrix thurberiisisppppi, Fpp., Phyllocnist spp., Mamestra brassicae, Panolis flammea, Spodoptera spp., Trichoplusia ni, Carpocapsa pomonella, Pieris spp., Chilo spp., Pyrausta nubilalis, Ephestia kuehniella, Galleria mellonella, Tineola bisselliella, Tinea pellionellaanaellaanaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaella pellaella , Choristoneura fumiferana, Clysia ambiguella, Homona magnanima, Tortrix viridana, Cnaphalocerus spp., Oulema oryzae.

From the order of the Coleoptera, for example, Anobium punctatum, Rhizopertha dominica, Bruchidius obtectus, Acanthoscelides obtectus, Hylotrupes bajulus, Agelastica alni, Leptinotarsa decemlineata, Phaedon cochleariae, Diabrotica spp., Psylliodive chrysoisisamnaisppas, Atomium spp spp., Sitophilus spp., Otiorrhynchus sulcatus, Cosmopolites sordidus, Ceuthorrhynchus assimilis, Hypera postica, Dermestes spp., Trogoderma spp., Anthrenus spp., Attagenus spp., Lyctus spp., Meligethus aeneuc., Ptin., Ptin psylloides, Tribolium spp., Tenebrio molitor, Agriotes spp., Cono- derus spp., Melolontha melolόntha, Amphimallon solstitialis, Costelytra zealandica, Lissorhoptrus oryzophilus.

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

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

From the class of the Arachnida e.g. Scorpio maurus, Latrodectus mactans, Acarus siro, Argas spp., Ornithodoros spp., Dermanyssus gallinae, Eriophyes ribis, Phyllocoptruta oleivora, Boophilus spp., Rhipicephalus spp., Amblyomma spp., Hyalo ma spp., Ixodes , Chorioptes spp., Sarcoptes spp., Tarsonemus spp., Bryobia praetiosa, Panonychus spp., Tetranychus spp., Hemitarsonemus spp., Brevipalpus spp ..

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., Bursaph.

The active compound combinations of compounds of the formula (I) and at least one compound of the formula (II) according to the invention are particularly suitable for controlling “biting” pests. These include in particular the following pests:

From the order of the Lepidoptera, for example Pectinophora gossypiella, Bupalus piniarius, Cheimatobia brumata, Lithocolletis blancardella, Hyponomeuta .padella, Plutella xylostella, Malacosoma neustria, Euproctis chrysorrhoea, Lymantria spp., Agristella syll spp., Earias insulana, Heliothis spp., Mamestra brassicae, Panolis flammea, Spodoptera spp., Trichoplusia ni, Carpocapsa pomonella, Pieris spp., Chilo spp., Pyrausta nubilalis, Ephestia kuehniella, Galleria mellonelliella, Hofella tinellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaella tellaolaellaella tellaolaellaella tellaolaellaella pseudospretella, Cacoecia podana, Capua reticulana, Choristoneura fumiferana, Clysia ambiguella, Homona magnanima, Tortrix viridana, Cnaphalocerus spp., Oulema oryzae. From the order of the Coleoptera, for example, Anobium punctatum, Rhizopertha dominica, Bruchidius obtectus, Acanthoscelides obtectus, Hylotrupes bajulus, Agelastica alni, Leptinotarsa decemlineata, Phaedon cochleariae, Diabrotica spp., Psylliodive chrysoisisamnaisppas, Atomium spp spp., Sitophilus spp., Otiorrhynchus sulcatus, Cosmopolites sordidus, Ceuthorrhynchus assimilis, Hypera postica, Dermestes spp., Trogoderma spp., Anthrenus spp., Attagenus spp., Lyctus spp., Meligethus aeneuc., Ptin., Ptin psylloides, Tribolium spp., Tenebrio molitor, Agriotes spp., Conoderus spp., Melolontha melolontha, Amphimallon solstitialis, Costelytra zealandica, Lissorhoptrus oryzophilus.

The active compound combinations according to the invention of compounds of the formula (I) and at least one compound of the formula (H) are also particularly suitable for controlling “sucking” pests. These include in particular the following pests:

From the order of the 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., Maculiiphumumpp padi, Empoasca spp., Euscelis bilobatus, Nephotettix cincticeps, Lecanium corni, Saissetia oleae, Laodelphax striatellus, Nilaparvata lugens, Aonidiella aurantii, Aspidiotus hederae, Pseudococcus spp., Psylla spp.

The active substance combinations according to the invention are notable in particular for an excellent action against caterpillars, beetle larvae, spider mites, aphids and leaf fly.

The active substance combinations according to the invention 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 and very fine encapsulations in polymeric substances ,

These formulations are made in a known manner, e.g. by mixing the active ingredients with extenders, that is to say liquid solvents and / or solid carriers, optionally using surface-active agents, that is to say emulsifiers and / or dispersants and / or foam-generating agents.

If water is used as an extender, e.g. organic solvents can also be used as auxiliary solvents. The liquid solvents essentially come in

Question: Aromatics, such as xylene, toluene, or alkylnaphthalenes, chlorinated aromatics and chlorinated aliphatic hydrocarbons, such as chlorobenzenes, chlorethylenes or methylene chloride, aliphatic table 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.

The following are suitable as solid carriers:

e.g. Ammonium salts and natural rock powders such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth and synthetic rock powders such as highly disperse silica, aluminum oxide and silicates are suitable as solid carriers for granules: e.g. broken and fractionated natural rocks such as calcite, marble, pumice, sepiolite, dolomite and synthetic granules from inorganic and organic flours as well as granules from organic material such as sawdust, coconut shells, corn cobs and tobacco stems; as emulsifying and / or foaming agents are possible: e.g. nonionic and anionic emulsifiers such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, e.g. Alkylaryl polyglycol ethers, alkyl sulfonates, alkyl sulfates, aryl sulfonates and protein hydrolyzates; Possible dispersants are: e.g. Lignin sulfite liquor and methyl cellulose.

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

Dyes such as inorganic pigments, e.g. 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.

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 and in the use forms prepared from these formulations in a mixture with other active compounds, such as insecticides, attractants, sterilants, bactericides, acaricides, nematicides, fungicides, growth-regulating substances or herbicides. Insecticides include, for example, phosphoric acid esters, carbamates, carboxylic acid esters, chlorinated hydrocarbons, phenylureas, substances produced by microorganisms and others A mixture with other known active ingredients, such as herbicides or with fertilizers and growth regulators, is also possible.

When used as insecticides, the active compound combinations according to the invention can furthermore be present in their commercially available formulations and in the use forms prepared from these formulations in a mixture with synergists. Synergists are compounds that increase the effectiveness of the active ingredients without the added synergist itself having to be active.

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

The application takes place in a customary manner adapted to the application forms.

When used against hygiene pests and pests of stored products, the active substance combinations are notable for an excellent residual action on wood and clay and for good stability to alkali on limed substrates.

The active compound combinations according to the invention act not only against plant, hygiene and stored-product pests, but also in the veterinary sector against animal parasites (ectoparasites) such as shield ticks, leather ticks, space mites, running mites, flies (stinging and licking), parasitic fly larvae, lice, hair lice, Featherlings and fleas. These parasites include:

From the order of the Anoplurida e.g. Haematopinus spp., Linognathus spp., Pediculus spp., Phtirus spp., Solenopotes spp ..

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

From the order of the Heteropterida e.g. Ci ex spp., Triatoma spp., Rhodnius spp., Panstrongylus spp ..

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

From the subclass of Acaria (Acarida) and the orders of the 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., Der anyssus spp., Raillietia spp., Pneumony spp., Sternostoma spp., Varroa spp ..

From the order of the 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., Hypodterol spp ., Psoroptes spp., Chorioptes spp., Otodectes spp., Sarcoptes spp., Notoedres spp., Knemidocoptes spp., Cytodites spp., Laminosioptes spp ..

The combinations of active substances according to the invention are also suitable for combating arthropods which are used in agricultural animals, such as e.g. Cattle, sheep, goats, horses, pigs, donkeys, camels, buffalo, rabbits, chickens, turkeys, ducks, geese, bees, other pets such as e.g. Dogs, cats, house birds, aquarium fish and so-called experimental animals, such as Infest hamsters, guinea pigs, rats and mice. By combating these arthropods, deaths and reduced performance (in the case of meat, milk, wool, skins, eggs, honey, etc.) are to be reduced, so that the use of the active compound combinations according to the invention enables more economical and simple animal husbandry.

The active compound combinations according to the invention are used in the veterinary sector in a known manner by enteral administration in the form of, for example, tablets, capsules, drinkers, drenches, granules, pastes, boluses, the feed-through method, suppositories, by parenteral administration, for example by Injections (intramuscular, subcutaneous, intravenous, intraperitonal, etc.), implants, by nasal application, by dermal application in the form of, for example, diving or bathing (dipping), spraying (spray), pouring on (pour-on and spot-on), washing , the powder and with the help of shaped articles containing active ingredients, such as collars, ear tags, tail tags, limb tapes, holsters, marking devices, etc. When used for cattle ^", poultry, pets and the like, the active compound used as formulations (for example powders, emulsions, flowables) which comprise the active compounds in an amount of 1 to 80 wt .-%, directly or after 100 to 10 Apply a thousandfold dilution or use it as a chemical bath.

It was also found that the active compound combinations according to the invention show a high insecticidal action against insects which destroy industrial materials.

The following insects may be mentioned by way of example and preferably, but without limitation:

Beetle like

Hylotrupes bajulus, Chlorophorus pilosis, Anobium punctatum, Xestobium rufovillosum, Ptilinus pecticomis, Dendrobium pertinex, Emobius mollis, Priobium carpini, Lyctus brunneus, Lyctus afπcanus, Lyctus planicollis, Lyctus linearescese, Lyctus pubescuses, speculum, Lyctus linearesces, spec. Tryptodendron spec. Apate monachus, Bostrychus capucins, Heterobostrychus brunneus, Sinoxylon spec. Dinoderus minutus.

Skin wing like

Sirex juvencus, Urocerus gigas, Urocerus gigas taignus, Uroceras augur.

Termites like

Kalotermes flavicollis, Cryptotermes brevis, Heterotermes indicola, Reticulitermes flavipes, Reticulitermes santonensis, Reticulitermes lucifugus, Mastotermes darwi iensis, Zootermopsis nevadensis, Coptotermes formosanus.

Bristle tails such as Lepisma saccharina.

In the present context, technical materials are to be understood as non-living materials, such as preferably plastics, adhesives, glues, papers and cartons, leather, wood, wood processing products and paints.

The material to be protected from insect infestation is very particularly preferably wood and wood processing products.

Wood and wood processing products which can be protected by the agent according to the invention or mixtures containing it are to be understood as examples: Lumber, wooden beams, railway sleepers, bridge parts, jetties, wooden vehicles, boxes, pallets, containers, telephone poles, wooden cladding, wooden windows and doors, plywood, chipboard, carpentry or wooden products that are generally used in house construction or in the. Find carpentry use.

The active substance 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 ingredients with at least one solvent or diluent, emulsifier, dispersant and / or binder or fixative, water repellent, optionally siccatives and UV stabilizers and optionally dyes and pigments and further processing aids.

The insecticidal compositions or concentrates used to protect wood and wood-based materials contain the active ingredient according to the invention in a concentration of 0.0001 to 95% by weight, in particular 0.001 to 60% by weight.

The amount of the agents or concentrates used depends on the type and occurrence of the insects and on the medium. The optimum amount of use can be determined in each case by test series. In general, however, it is sufficient to use 0.0001 to 20% by weight, preferably 0.001 to 10% by weight, of the active compound, based on the material to be protected.

An organic chemical solvent or solvent mixture and / or an oily or oily or low-volatile organic chemical solvent or solvent mixture and / or a polar organic chemical solvent or solvent mixture and / or water and optionally an emulsifier and / or wetting agents.

The organic chemical solvents used are preferably oily or oily solvents with an evaporation number above 35 and a flash point above 30 ° C., preferably above 45 ° C. Corresponding mineral oils or their aromatic fractions or mineral oil-containing solvent mixtures, preferably white spirit, petroleum and / or alkylbenzene, are used as such low-volatility, water-insoluble, oily and oily solvents. Mineral oils with a boiling range of 170 to 220 ° C, white spirit with a boiling range of 170 to 220 ° C, spindle oil with a boiling range of 250 to 350 ° C, petroleum or aromatics with a boiling range of 160 to 280 ° C, turpentine oil and Like. Used.

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

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

According to a preferred embodiment, part of the organic chemical solvent or solvent mixture or an aliphatic polar organic chemical solvent or solvent mixture is replaced. Aliphatic organic chemical solvents containing hydroxyl and / or ester and / or ether groups, such as, for example, glycol ethers, esters or the like, are preferably used.

In the context of the present invention, the organic chemical binders used are the water-digestible synthetic resins which are known per se and / or which are soluble or dispersible or emulsifiable in the organic chemical solvents used and / or binding drying oils, in particular binders consisting of or containing an acrylate resin, a vinyl resin, e.g. 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 based on a natural and / / or synthetic resin used.

The synthetic resin used as a binder can 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-repellants, odor correctors and inhibitors or anticorrosive agents and the like can be used. According to the invention, at least one alkyd resin or modified alkyd resin and / or a drying vegetable oil is preferably contained in the agent or in the concentrate as the organic chemical binder. 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.

All or part of the binder mentioned can be replaced by a fixing agent (mixture) or a plasticizer (mixture). These additives are intended to prevent volatilization of the active ingredients and crystallization or precipitation. They preferably replace 0.01 to 30% of the binder (based on 100% of the binder used).

The plasticizers come from the chemical classes of phthalic acid esters such as dibutyl, dioctyl or benzyl butyl phthalate, phosphoric acid 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, higher glycerol glycol or glycerol ether and p-toluenesulfonic acid ester.

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

Water is also particularly suitable as a solvent or diluent, optionally in a mixture with one or more of the above-mentioned organic chemical solvents or diluents, emulsifiers and dispersants.

A particularly effective wood protection is achieved through industrial impregnation processes, e.g. Vacuum, double vacuum or pressure process.

At the same time, the active substance combinations according to the invention can be used to protect objects, in particular hulls, sieves, nets, structures, quay systems and signaling systems which come into contact with sea or brackish water.

Overgrowth by sessile oligochaetes, such as lime tube worms, and by mussels and species of G ppe Ledamorpha (barnacles), such as various types of Lepas and Scalpellum, or by species from the group Balanomorpha (barnacles), such as Baianus or Pollicipes species, increases the frictional resistance of ships and subsequently leads to a significant increase in operating costs due to increased energy consumption and, moreover, frequent dry dock stays.

In addition to the growth by algae, for example Ectocarpus sp. and Ceramium sp., vegetation by sessile entraster groups, which are grouped under the name Cirripedia (barnacles), is of particular importance. It has now surprisingly been found that the active ingredient combinations according to the invention have an excellent antifouling effect.

By using the active ingredient combinations according to the invention, heavy metals such as e.g. in bis (trialkyltin) sulfϊden, tri-n-butylziimlaurat, tri - «- butylzi_ιnchlorid, copper (I) oxide, triethyltin chloride, tri-n-butyl (2-phenyl-4-chlorophenoxy) tin, tributyltin oxide, molybdenum disulfide, Antimony oxide, polymeric butyl titanate, phenyl (bispyridine) bismuth chloride, tri-butyltin fluoride, manganese ethylene bisthiocarbamate, zinc dimethyldithiocarbamate, zinc ethylene bisthiocarbamate, zinc and copper salts of 2-pyridinethiol-l-oxydi-oxydiamethyldiharbamoyl (iodide) oxydimethylamide, bisdimethyl imide, -ethylene-bisdithiocarbamate, copper thiocyanate, copper phthalate and tributyltin halides or the concentration of these compounds can be significantly reduced.

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

The following are preferably suitable as combination partners for the antifouling agents according to the invention:

Algicides like

2-tert-Bu1ylamino-4-cyclopropylamino-6-methylthio-l, 3,5-triazine, dichlorophene, diuron, endothal, fentin acetate, isoproturon, methabenzthiazuron, oxyfluorfen, quinoclamine and terbutryn;

Fungicides like

Benzo [b] thiophenecarboxylic acid cyclohexylamide-S, S-dioxide, dichlofluanid, fluorfolpet, 3-iodo-2-propynyl-butylcarbamate, tolylfluanid and azoles such as

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

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,. Tefrabutyldistannoxane, 2,3,5,6-tettac or-4- (methylsulfonyl) pyridine, 2,4,5,6-tetrachloroisophthalonitrile, tetramethylthiuram disulfide and 2,4,6-trichlorophenylmaleimide.

The anti-fouling agents used contain the active compound combinations according to the invention in a concentration of 0.001 to 50% by weight, in particular of 0.01 to 20% by weight.

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

In addition to the algicidal, fungicidal, molluscicidal and insecticidal active substances according to the invention, antifoulm 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, in particular in an aqueous system, vinyl chloride / vinyl acetate copolymer systems in the form of aqueous dispersions or in the form of organic solvent systems, butadiene / - styrene / acrylonitrile rubbers, drying agents Oils such as linseed oil, resin esters or modified hard resins in combination with tar or bitumen, asphalt and epoxy compounds, small amounts of chlorinated rubber, chlorinated polypropylene and vinyl resins.

Paints may also contain inorganic pigments, organic pigments or dyes, which are preferably insoluble in seawater. Paints may also contain materials such as rosin to enable controlled release of the active ingredients. The paints may also contain plasticizers, modifiers affecting theological properties, and other conventional ingredients. The compounds according to the invention or the abovementioned mixtures can also be incorporated into self-polishing antifouling systems.

The active ingredient combinations are also suitable for combating animal pests, in particular insects, arachnids and mites, which live in closed rooms, such as apartments, factory halls, offices, vehicle cabins, etc. 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 the Scorpionidea, for example Buthus occitanus. From the order of the Acariria, for example Argas persicus, Argas reflexus, Bryobia ssp., Dermanyssus gallinae, Glyciphagus domesticus, Omithodoms moubat, Rhipicephalus sanguineus, Trombicula alfreddugesi, Neutrombicula autumnalis, Dermatophagoides pteronissimus, Dermatophagoides pteronissimus.

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

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

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

From the order of the Diplopoda e.g. Blaniulus guttulatus, Polydesmus spp ..

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

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

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

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

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

From the order of the 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 the Diptera e.g. Aedes aegypti, Aedes albopictus, Aedes taeniorhynchus, Anopheles spp., Calliphora erythrocephala, Chrysozona pluvialis, Culex quinquefasciatus, Culex pipiens, Culex tarsalis, Phrosophila spp., Fannia canicularis calcitrans, Tipula paludosa.

From the order of the Lepidoptera, for example Achroia grisella, Galleria mellonella, Plodia interpunctella, Tinea cloacella, Tinea pellionella, Tineola bisselliella. From the order of the Siphonaptera, for example Ctenocephalides canis, Ctenocephalides felis, Pulex irritans, Tunga penetrans, Xenopsylla cheopis.

From the order of the Hymenoptera 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, Phthims pubis.

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

They are used in aerosols, non-pressurized sprays, e.g. Pump and atomizer sprays, fog machines, foggels, foams, gels, vaporizer products with vaporizer platelets made of cellulose or plastic, liquid vaporizers, gel and membrane vaporizers, propeller-driven vaporizers, energy-free or passive evaporation systems, moth papers, moth bags and moth gels, as granules or dust, in scattered dust or bait stations.

According to the invention, all plants and parts of plants can be treated. Plants are understood here to mean all plants and plant populations, such as desired and undesired wild plants or crop plants (including naturally occurring crop plants). Crop plants can be plants which can be obtained by conventional breeding and optimization methods or by biotechnological and genetic engineering methods or combinations of these methods, including the transgenic plants and including the plant cultivars which can or cannot be protected by plant breeders' rights. Plant parts are to be understood to mean all above-ground and underground parts and organs of plants, such as shoots, leaves, flowers and roots, examples being leaves, needles, stems, stems, flowers, fruiting bodies, fruits and seeds, and roots, tubers and rhizomes , The plant parts also include crops and vegetative and generative propagation material, for example cuttings, tubers, rhizomes, offshoots and seeds.

The treatment of the plants and parts of plants with the active compounds according to the invention is carried out directly or by acting on their surroundings, living space or storage space according to the customary treatment methods, for example by dipping, spraying, evaporating, atomizing, scattering, spreading and in the case of propagation material, in particular seeds single or multi-layer wrapping. As already mentioned above, according to the invention, all plants and their parts can be treated. In a preferred embodiment, wild plant species or plant species and their parts obtained by conventional biological breeding methods, such as crossing or protoplast fusion, are treated. In a further preferred embodiment, 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 “parts of plants” was explained above.

Plants of the plant varieties which are in each case commercially available or in use are particularly preferably treated according to the invention.

Depending on the plant species or plant cultivars, their location and growth conditions (soils, climate, vegetation period, nutrition), the treatment according to the invention can also cause superadditive (“synergistic”) effects. For example, reduced application rates and / or extensions of the activity spectrum and / or one Enhancing the effect of the substances and agents which can be used according to the invention, better plant growth, increased tolerance to high or low temperatures, increased tolerance to drought or to water or soil salt content, increased flowering performance, easier harvesting, acceleration of ripening, higher crop yields, higher quality and / or higher nutritional value of the harvested products, higher shelf life and / or workability of the harvested products possible, which go beyond the effects that are actually to be expected.

The preferred transgenic plants or plant cultivars to be treated according to the invention include all plants which have received genetic material through the genetic engineering modification, 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 drought or to water or soil salt content, increased flowering performance, easier harvesting, acceleration of ripening, higher harvest yields, higher quality and / or higher nutritional value of the harvested products, higher storability and / or workability of the Further and particularly highlighted 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 vir and an increased tolerance of the plants to certain herbicidal active ingredients. Examples of transgenic plants are the important crop plants, such as cereals (wheat, rice), corn, soybeans, potatoes, cotton, tobacco, rapeseed and fruit plants (with the fruits apples, pears, citrus fruits and grapes), where Corn, soybeans, potatoes, cotton, tobacco and rapeseed are particularly highlighted. The properties (“traits”) which are particularly emphasized are the plants' increased defense against insects, arachnids, nematodes and snails due to toxins which arise in the plants, in particular those which are caused by the genetic material from Bacillus thuringiensis (for example by the genes CryIA (a) , CryIA (b), CryIA (c), CryllA, CrylllA, CrymB2, Cry9c Cry2Ab, Cry3Bb and CrylF as well as their combinations) are produced in the plants (hereinafter “Bt plants”). The increased defense of plants against fungi, bacteria and viruses by systemic acquired resistance (SAR), systemin, phytoalexins, elicitors and resistance genes and correspondingly expressed proteins and toxins are also particularly emphasized as properties (“traits”). As properties (“traits”) ) are also particularly emphasized the increased tolerance of the plants to certain herbicidal active ingredients, for example imidazolinones, sulfonylureas, glyphosate or phosphinotricin (for example "PAT" gene). The genes conferring the desired properties ("traits") can in each case also occur in combinations with one another in the transgenic plants. Examples of “Bt plants” are maize, cotton, soy and potato, which are sold under the trade names YIELD GARD® (eg maize, cotton, soy), KnockOut® (eg maize), StarLink® (eg maize), Bollgard ® (cotton), Nucotn® (cotton) and NewLeaf® (potato). Examples of herbicide-tolerant plants are corn varieties, cotton varieties and soy varieties which are sold under the trade names Roundup Ready® (tolerance to glyphosates, for example corn, cotton, soybeans) ), Liberty Link® (tolerance against phosphinotricin, eg rapeseed), EVO® (tolerance against imidazolinones) and STS® (tolerance against sulfonylureas eg maize). The herbicide-resistant plants (conventionally bred to herbicide tolerance) are also among the with the name Clearfield® (eg maize), and of course these statements also apply to plant varieties developed in the future or to the market in the future s with these or future-developed genetic traits.

The plants listed can be treated particularly advantageously according to the invention with the active compound mixtures according to the invention. The preferred ranges given for the mixtures above also apply to the treatment of these plants. Plant treatment with the mixtures specifically listed in this text should be particularly emphasized.

The good insecticidal and acaricidal activity of the active compound combinations according to the invention can be seen from the examples below. While the individual active ingredients have weaknesses in their effects, the combinations show an effect that goes beyond a simple summation of effects. Insecticides and acaricides always have a synergistic effect if 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 active ingredients can be calculated as follows according to the so-called "Colby formula" (see S.R. Colby, "Calculating Synergistic and Antagonistic Responses of Herbicide Combinations", Weeds 1967.15, 20-22):

If

X means the degree of destruction, expressed in% of the untreated control, when the active compound A is used in an application rate of m g / ha or in a concentration of m ppm,

Y means the degree of destruction, expressed in% of the untreated control, when the active compound B is used in an application rate of n g ha or in a concentration of n ppm and

E means the degree of destruction, expressed in% of the untreated control, when active ingredients A and B are used in application rates of and n g / ha or in a concentration of m and n ppm,

X • Y then E = X + Y 100

If the actual degree of insecticidal killing is greater than calculated, the combination is superadditive in its killing, ie there is a synergistic effect. In this case, the degree of mortality actually observed must be greater than the value for the expected degree of mortality (E) calculated from the above formula.

Examples

Example A

Phaedon larvae test

Solvent: 7 parts by weight of dimethylformamide

Emulsifier: 2 parts by weight of alkylaryl polyglycol ether

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

Cabbage leaves (Brassica oleracea) are treated by being dipped into the preparation of active compound of the desired concentration and 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 none of the beetle larvae have been killed. The determined kill rates are calculated using the Colby formula (see page 33).

In this test, the following combination of active substances according to the present application showed a synergistically enhanced activity compared to the individually used active substances:

Table A Plant Harmful Insect Phaedon Larva Test

* found = Effect found ** calc. = Effect calculated using Colby's formula

Example B

Spodoptera frugiperda test

Solvent: 7 parts by weight of dimethylformamide

Emulsifier: 2 parts by weight of alkylaryl polyglycol ether

Cabbage leaves (Brassica oleracea) are treated by being dipped into the preparation of active compound of the desired concentration and populated with caterpillars of the army worm (Spodoptera frugiperda) while the leaves are still moist.

After the desired time, the kill is determined in%. 100% means that all caterpillars have been killed; 0% means that no caterpillars have been killed. The determined kill rates are calculated using the Colby formula (see page 33).

Table B plant-damaging insect Spodoptera frugiperda test

* found = Effect found ** calc. = Effect calculated using Colby's formula

Claims

claims

Agent containing compounds of the formula (I)

in which

X represents Ci-Cg-alkyl, bromine, Ci-Cg-alkoxy or C -C3-haloalkyl,

Y represents hydrogen, Ci-Cg-alkyl, halogen, Ci-Cg-alkoxy, C -C3 -haloalkyl,

Z represents C -Cg-alkyl, halogen, C -Cg-alkoxy, n represents a number from 0-3,

A for hydrogen or in each case optionally substituted by halogen, straight-chain or branched C -C 2 -alkyl, C2-Cg-alkenyl, C2-Cg-alkynyl, CJ-CI _Q - alkoxy-C -Cg-alkyl, C -Cg-polyalkoxy- C ₂ -Cg-alkyl, C -C ₀ -alkylthio-C ₂ -Cg-alkyl, cycloalkyl with 3-8 ring atoms, which can be interrupted by oxygen and / or sulfur or in each case optionally by halogen, C -Cg-alkyl, C -Cg-haloalkyl-, C -Cg-alkoxy-, C -Cg-haloalkoxy, nitro-substituted phenyl or phenyl-C -Cg-alkyl,

B represents 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 a saturated or unsaturated, optionally interrupted by oxygen and / or sulfur and optionally by halogen, C -Cg-alkyl, C -Cg-alkoxy, C -C4-haloalkyl, C. -C ^ -haloalkoxy, Ci-C ^ alkylthio or optionally substituted phenyl substituted or optionally benzo-fused 3- to 8-membered ring, For hydrogen (a) or for the groups

CO-R ¹ (b) (°) - SOj-R ³ (d)

in which

Rl for each optionally substituted by halogen C -C-20-alkyl, C2-C20-alkenyl, -C-Cg-alkoxy-C -Cg-alkyl, -C-Cg-alkylthio-C -Cg-alkyl, Ci-Cg-polyalkoxy -C2-Cg-alkyl or cycloalkyl having 3-8 ring atoms, which can be interrupted by oxygen and / or sulfur atoms, is optionally halogen, nitro, Ci-Cg-alkyl, C -Cg-alkoxy, C -Cg - Haloalkyl, C -Cg-haloalkoxy-substituted phenyl, optionally for halogen, C -Cg-alkyl, C-Cg-alkoxy-, Cι ~ Cg-haloalkyl, Ci-Cg-haloalkoxy-substituted phenyl-Ci- Cg-alkyl is pyridyl, pyrimidyl, thiazolyl or pyrazolyl which is optionally substituted by halogen and / or C-Cg-alkyl, is phenoxy-C-Cg-alkyl which is optionally substituted by halogen and / or C -Cg-alkyl .

R ^{2 represents} in each case optionally substituted by halogen C -C20 -Al yl, C2-C20-alkenyl, C -Cg-alkoxy-C2-Cg-alkyl or C -Cg-polyalkoxy-C2-Cg-alkyl, each in each case by Halogen, nitro, Ci-Cg-alkyl, Ci-Cg-alkoxy, C -Cg-haloalkyl-substituted phenyl or benzyl,

R3 for C -Cg-alkyl optionally substituted by halogen, for phenyl or benzyl substituted in each case optionally by C -C4-Al 1, halogen, C -C4-haloalkyl, C -C4-alkoxy, C - C4-haloalkoxy, nitro or cyano stands,

R ⁴ and R independently of one another each represent Ci-Cg-alkyl, Ci-Cg-alkoxy, C-Cg-alkylamino, di- (C-Cg) -alkylamino, optionally substituted by halogen, -C-Cg-alkylthio, C2-C5-alkenylthio, C ₂ -C ₅ -alkynylthio, C ₃ -C7-cycloalkylthio, for each optionally by halogen, nitro, cyano, -C-C-4-alkoxy, C1-C4-haloalkoxy , C -C4-alkylthio, C -C4-haloalkylthio, C -C4-alk l, C -C4-haloalkyl substituted phenyl, phenoxy or phenylthio,

R "and R 'independently of one another for C 1 -C 8 -alk l, C 1 -C 8 -alkoxy, C 3 -C 8 -alkenyl, C 1 -C 6 -alkoxy-C 1 -C 8 -alkyl, optionally substituted by halogen, for optionally by halogen, Ci-Cg-haloalkyl, C -Cg-alkyl or Ci-Cg-alkoxy substituted phenyl, for benzyl optionally substituted by halogen, C-Cg-alkyl, Ci-Cg-haloalkyl or Ci-Cg-alkoxy or together for an optionally 5 to 6-membered ring interrupted by oxygen or sulfur, which may optionally be substituted by C 1 -C 6 -alkyl,

and at least one phthalic acid diamide of the formula (II)

in which

K represents halogen, cyano, alkyl, haloalkyl, alkoxy or haloalkoxy,

Rel, Re ² , Re ^ each independently of one another for hydrogen, cyano, for C3-Cg-cycloalkyl optionally substituted by halogen or for a group of the formula M ² -Q

stand in which

M * represents optionally substituted alkylene, alkenylene or alkynylene,

Q for hydrogen, halogen, cyano, nitro, haloalkyl, in each case optionally substituted C3-Cg-cycloalkyl, alkylcarbonyl or alkoxycarbonyl, in each case optionally substituted phenyl, hetaryl or for a group T-Re ⁴ stands,

in which

T stands for -0-, -S (0) _m - or - N -, Re ⁵

Re ^ represents hydrogen, in each case optionally substituted alkylcarbonyl, alkoxycarbonyl, phenylcarbonyl or phenylalkoxycarbonyl,

k represents the numbers 1 to 4, represents the numbers 0 to 2,

Re ^ and Re ² together form an optionally substituted four- to seven-membered ring which can optionally be interrupted by heteroatoms,

Ll and ß independently of one another represent hydrogen, halogen, cyano or in each case optionally substituted alkyl, alkoxy, alk-S (0) _m -, phenyl, phenoxy or hetaryloxy,

L ² for hydrogen, halogen, cyano, in each case optionally substituted alkyl, alkenyl, alkynyl, haloalkyl, cycloalkyl, phenyl, hetaryl or for the group

M ² -Re ⁶ stands,

in which

M ² represents -O- or -S (0) _m -,

and

Re ^ represents in each case optionally substituted alkyl, alkenyl, alkynyl, cycloalkyl, phenyl or hetaryl,

Ll and L ^ or L and L ² together form an optionally substituted five- to six-membered ring which may optionally be interrupted by heteroatoms.

2. Composition according spoke 1, containing compounds of formula (II) in which

K represents fluorine, chlorine, bromine, iodine, cyano, Ci-Cg-alkyl, Ci-Cg-haloalkyl, Ci-Cg-alkoxy or Ci-Cg-haloalkoxy,

Rel, Re ² and Re3 each independently of one another for hydrogen, cyano, for C3-Cg-cycloalkyl optionally substituted by halogen or for a group of the formula

Ml-Q _k are in which

Ml represents Ci-Cg-alkylene, C3-Cg-alkenylene or C3-Cg-alkinylene,

Q for hydrogen, halogen, cyano, nitro, haloalkyl or for C3-Cg-cycloalkyl optionally substituted by fluorine, chlorine, Ci-Cg-alkyl or Ci-Cg-alkoxy, in which one or two ring members not directly adjacent by oxygen and / or sulfur are replaced or for each optionally substituted by halogen substituted Ci-Cg-alkylcarbonyl or Ci-Cg-alkoxycarbonyl or for each optionally replaced by halogen, Ci-Cg-alkyl, Ci-Cg-haloalkyl, Ci-Cg-alkoxy, Ci Cg-haloalkoxy, cyano or nitro substituted phenyl or hetaryl with 5 to 6 ring atoms (for example furanyl, pyridyl, imidazolyl, triazolyl, pyrazolyl, pyrimidyl, thiazolyl or thienyl) or for a group

T-Re ⁴ stands in which

T stands for -0-, -S (0) _m - or —N—, Re ⁵

Re ⁴ for hydrogen, for in each case optionally substituted by fluorine and / or chlorine, Ci-Cg-alkyl, C3-Cg-alkenyl, C3-Cg-alkynyl, C3-Cg-cycloalkyl, C3-Cg-Cycloälkyl-C -C2-alkyl, Ci-Cg-alkylcarbonyl, Ci-Cg-alkoxycarbonyl, each optionally optionally up to four times by halogen, Ci-Cg-alkyl, Ci-Cg-alkoxy, Ci-Qψ-haloalkyl , C -C4 haloalkoxy, nitro or cyano substituted phenyl, C1-C.4-phenylal.kyl, Ci-Q _j -phenylalkyloxy, hetaryl or hetarylalkyl, where hetaryl has 5 to 6 ring atoms, e ^ is hydrogen, for each Ci-Cg-alkylcarbonyl, Ci-Cg-alkoxycarbonyl, optionally substituted by fluorine and / or chlorine, for each optionally optionally up to four times by halogen, Ci-Cg-alkyl, Ci-Cg-alkoxy, C1-C4-haloalkyl, Cι-C4 Haloalkoxy, nitro or cyano substituted phenylcarbonyl or phenyl-C 1 -C 4 -alkyloxycarbonyl,

k represents the numbers 1 to 3,

m represents the numbers 0 to 2,

Rel and Re ^{2 form} a five- to six-membered ring which can optionally be interrupted by an oxygen or sulfur atom,

L and ß independently of one another for hydrogen, cyano, fluorine, chlorine, bromine, iodine, C -Cg-alkyl, Cι-C4-haloalkyl, Ci-Cg-alkoxy, Ci-C ^ -haloalkoxy, Ci-C4-alkyl-S (0) _m -, -Cι-G4-haloalkyl-S (0) _m -, for each optionally single to triple by fluorine, chlorine, bromine, C -Cg-alkyl, Ci-Cg-alkoxy, C1-C4- haloalkyl, -C-C4-haloalkoxy, cyano or nitro substituted phenyl, phenoxy, pyridinyloxy, thiazolyloxy or pyrimidyloxy,

L ² for hydrogen, fluorine, chlorine, bromine, iodine, cyano, for each Ci-CiQ-alkyl optionally substituted by fluorine and / or chlorine, C ^ -CiQ-alkenyl, C2-C - alkynyl, for each optionally by fluorine, Chlorine-substituted C3-C - cycloalkyl, each optionally optionally up to three times by fluorine, chlorine, bromine, Ci-Cg-alkyl, C -Cg-alkoxy, Cι-C4-haloalkyl, C -C-4-haloalkoxy, cyano or nitro substituted phenyl, pyridyl, thienyl, pyrimidyl or thiazolyl,

or for a group

M ² -Re ⁶

is in which M ^{2 represents} -O- or -S (0) _m - and

Re "for each Ci-Cg-alkyl, C-2-Cg-alkenyl, C3-Cg-alkynyl or C3-Cg-cycloalkyl which is optionally substituted by fluorine and / or chlorine, for each optionally up to three times by fluorine, chlorine, bromine Ci-Cg-alkyl, C-Cg-alkoxy, Ci-C halo-alkyl, Ci-C ^ -haloalkoxy, cyano or nitro substituted phenyl, pyridyl, pyrimidyl or thiazolyl,

L ¹ and L ³ or

L ^{2 and} L ³ together in each case form a five- to six-membered ring which is optionally substituted by fluorine and / or C ² -C ² -alkyl and which can optionally be interrupted by one or two oxygen atoms.

3. Composition according spoke 1, containing compounds of formula (II) in which

K represents chlorine, bromine and iodine,

Re% Re ² and Re ³ each independently for hydrogen or for a group of the formula

Ml-Q stand in which

M represents C -Cg-alkylene, C3-Cg-alkenylene or C3-Cg-alkynylene,

Q for hydrogen, fluorine, chlorine, cyano, trifluoromethyl, C3-Cg-cycloalkyl or for a group

T-Re ⁴ stands in which

T stands for -O- or -S (0) _m -,

Re ⁴ represents hydrogen, in each case optionally Ci to Cg-alkyl, C3-Cg-alkenyl, C-Cg-alkynyl or C3-C-cycloalkyl which is monosubstituted to trisubstituted by fluorine and or chlorine, k represents the numbers ^" 1 to 3,

m represents the numbers 0 to 2,

L * and L ³ independently of one another for hydrogen, fluorine, chlorine, bromine, iodine, cyano, C 1 -C 4 -alk l, C 1 -C 2 -haloalkyl, C 1 -C 4 -alkoxy, C -C 2 -haloalkoxy, each optionally simple phenyl or phenoxy substituted twice by fluorine, chlorine, bromine, C1-C4-alkyl, -CC-C4-alkoxy, -C-C2-haloalkyl, C-C2-haloalkoxy, cyano or nitro,

L ² for hydrogen, fluorine, chlorine, bromine, iodine, cyano, for each Ci-Cg-alkyl which is optionally monosubstituted to thirteen times substituted by fluorine and / or chlorine, C-2-C-alkenyl, C2-Cg-alkynyl, C3- Cg-cycloalkyl or for a group

M ² -Re ⁶

is in which

M ^{2 represents} -O- or -S (0) _m -,

and

Re "for C 1 -C 6 -alkyl, C 1 -C 6 -alkenyl, C 2 -C 6 -alkynyl or C 3 -C 6 -cycloalkyl which are optionally monosubstituted to thirteen times substituted by fluorine and / or chlorine, for each optionally monosubstituted to double by fluorine, chlorine , Bromine, C 1 -C 4 alk 1, C 1 -C 4 alkoxy, trifluoromethyl, difluoromethoxy, trifluoromethoxy, cyano or nitro substituted phenyl or pyridyl.

Agent according to claim 1, containing compounds of formula (II) in which

K stands for iodine,

Re and Re ^{2 represent} hydrogen,

Re ³ for a group of the formula

M -Q!

is in which Ml for -CHCH3-CH2-, -C (CH ₃ ) ₂ -CH ₂ -, -CHC ₂ H ₅ -CH ₂ -,, -C (C ₂ H ₅ ) 2-CH2-,

Q represents hydrogen, fluorine, chlorine, cyano, trifluoromethyl, C3-Cg-cycloalkyl or a group T-Re ⁴ in which

T stands for -S-, -SO- or -S0 ₂ -,

Re ^{4 represents} in each case monosubstituted to trisubstituted by fluorine and / or chlorine, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl or tert-butyl, allyl, butenyl or isoprenyl , iß and L ³ independently of one another represent hydrogen, fluorine, chlorine, bromine, iodine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, methoxy, ethoxy, trifluoromethyl, difluoromethoxy or trifluoromethoxy,

L ² for hydrogen, fluorine, chlorine, bromine, iodine, cyano, for each methyl, ethyl, n-propyl, iso-propyl, n-butyl, iso-butyl, optionally substituted up to nine times by fluorine and / or chlorine. -Butyl, tert-butyl, allyl, butenyl or isoprenyl or for a group

M ² -Re ⁶ is M ^{2 is} oxygen or sulfur, and

Re "for each methyl, ethyl, n-propyl, iso-propyl, n-butyl, iso-butyl, sec.-butyl, tert-butyl, tert-butyl, allyl, butenyl or isoprenyl, optionally substituted up to nine times by fluorine and or chlorine, for phenyl which is optionally mono- to disubstituted by fluorine, chlorine, bromine, methyl, ethyl, methoxy, trifluoromethyl, difluoromethoxy, trifluoromethoxy, cyano or nitro.

5. Agent according spoke 1, containing the compound of formula (II-1)

6. Composition according spoke 1, containing compounds of formula (I) in which

X represents C i -C4 alkyl, bromine, C i -C4 alkoxy or C i -C3 haloalkyl,

Y represents hydrogen, C 1 -C 4 -Al 1, fluorine, chlorine, bromine, C 1 -C 4 -alko, C 1 -C 3 -haloalkyl,

Z stands for C 1 -C 4 -alkyl, chlorine, bromine, C 1 -C 4 -alkoxy, n stands for a number from 0-2,

A for hydrogen or in each case optionally up to three times substituted by fluorine, straight-chain or branched Ci-Cg-alkyl, C ^ -Cg-alkenyl, Ci-C4-alkoxy-C -C2-alkyl, cycloalkyl with 3-8 ring atoms, optionally by Oxygen and / or sulfur can be interrupted or phenyl or optionally substituted by fluorine, chlorine, bromine, C 1 -C 2 -alk l, C 1 -C 2 -haloalkyl, C 1 -C 2 -alkoxy, C 1 -C 2 -alkalkoxy, nitro Benzyl is, B is hydrogen, -CC ₂ -alkyl or -C-C ₂ alkoxy -CC-C ₂ alkyl or in which

A and B together with the carbon atom to which they are attached a saturated or unsaturated, optionally interrupted by oxygen and / or sulfur and optionally simply to twice by fluorine, chlorine, Ci-C4-alkyl, Ci-C ^ alkoxy, Cι -C2-haloalkyl, -CC-2-haloalkoxy or C ~ C2-alkylthio substituted 3- to 7-membered ring form,

G for hydrogen (a) or for the groups

stands,

in which

Rl for C ₁ -C 6 -alkyl, C ₂ -C 6 -alkenyl, C 1 -C 4 -alkoxy-C -C -alkyl, C1-C4-alkylthio-C -C4-alkyl or optionally substituted up to five times by fluorine or chlorine Cycloalkyl with 3-6 ring atoms, which can be interrupted by oxygen and or sulfur atoms, stands for optionally single to double by fluorine, chlorine, bromine, nitro, C1-C4- alkyl, -C-C4-alkoxy, Cι-C4- Halogenoalkyl, -C-C4-haloalkoxy-substituted phenyl stands for optionally mono- to disubstituted by fluorine, chlorine, bromine, -C-C4-alkyl, Ci-C alkoxy, -C-C-4-haloalkyl-, C1-C4-haloalkoxy- substituted benzyl is pyridyl, pyrimidyl, thiazolyl or pyrazolyl which is optionally mono- to disubstituted by chlorine, bromine and / or Ci-C alkyl,

R ^{2 is} in each case optionally up to five times fluorine or chlorine by substituted C1-C20-alkyl, C2-C20 "al enyl, -C-Cg-alkoxy-C2-Cg-alkyl, Ci-Cg-polyalkoxy-C2-Cg-alkyl represents phenyl or benzyl, in each case optionally one to two times by fluorine, chlorine, bromine, nitro, Ci-Cg-alkyl, C-Cg-alkoxy, C1-C4-haloalkyl-substituent.

R ³ for C 1 -C 4 -alkyl which is optionally monosubstituted to pentasubstituted by fluorine or chlorine, for each optionally monosubstituted to twice by C 1 -C 4 -alkyl, fluorine, chlorine, bromine, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy, -C-C4-haloalkoxy, nitro or cyano substituted phenyl or benzyl, R ⁴ and R ^ independently of one another, each optionally monosubstituted to trisubstituted by fluorine or chlorine, C 1 -C 4 -alk l, C 1 -C 4 -alkoxy, C 1 -C 4 -alkylamino, di- (C 1 -C 4) -alkylamino, Cι -C4-alkylthio, C2-C4-alkenylthio, C ^ -Cg- cycloalkylthio, for each optionally one to two times by fluorine, chlorine, bromine, nitro, cyano, -C-C2-alkoxy, Ci-C ^ -haloalkoxy, Ci C ^ -alkyl thio, -C-C2-haloalkylthio, -C-C2-alkyl, -C-C2-haloalkyl substituted phenyl, phenoxy or phenylthio,

R 6 and R ⁷ independently of one another fiir each case optionally mono- to trisubstituted by fluorine or chlorine-substituted Ci-Cg-alkyl, Ci-Cg-alkoxy, C3-Cg alkenyl, Cι-C4-alkoxy-Cι-C2-alkyl, optionally monosubstituted benzyl which is substituted twice by fluorine, chlorine, bromine, C 1 -C 2 -haloalkyl, C 1 -C 4 alkyl or C 1 -C 4 alkoxy or together represent a 5- to 6-membered ring which may be interrupted by oxygen or sulfur and which, if appropriate can be substituted by C-C2-Alk l.

7. Composition according spoke ϊ containing compounds of formula (I) in which

X is C 1 -C 4 -alk l, C 1 -C 4 -alkoxy or trifluoromethyl,

Y represents hydrogen, C 1 -C 4 -Al 1, chlorine, bromine, C 1 -C 4 -alkoxy, C -C 2 -haloalkyl,

Z represents -CC alkyl, chlorine, bromine, -C -alkoxy, n represents 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 monosubstituted by C -C4-Alk l or Ci-Qφ-alkoxy,

G for hydrogen (a) or for the groups

- CO-R ¹ (b) (c) stands in which R ^l for each optionally mono- to trisubstituted by fluorine or chlorine -CC2-alkyl, C2-Ci2-alkenyl, -C-C4-alkoxy-CC-C2-alkyl, or cycloalkyl with 3-6 ring atoms, which by 1 to 2 Oxygen atoms can be interrupted, stands for phenyl optionally substituted by fluorine, chlorine, bromine, nitro, Ci-C alkyl, C1-C4-alkoxy, trifluoromethyl or trifluoromethoxy;

^R2 is Cι-Cι ₂ alkyl, C ₂ -Cι ₂ alkenyl, Cι-C ₄ -alkoxy-C ₂ -C ₄ -alkyl, represents in each case optionally emfach by fluorine, chlorine, bromine, nitro, Cι- C4-Alk l, Ci-C alkoxy or trifluoromethyl substituted phenyl or benzyl.

Agent according spoke 1, containing compounds of formula (I)

in which

X represents methyl, ethyl, methoxy, ethoxy or trifluoromethyl,

Z represents methyl, ethyl, chlorine, bromine or methoxy,

n represents 0 or 1,

G for hydrogen (a) or for the groups

in which

R * for each optionally mono- to trisubstituted by fluorine or chlorine substituted Ci-Cg-alkyl, C ^ -Cg-alkenyl, -C-C3-alkoxy-Cι-C2-alkyl, or cycloalkyl with 3-6 ring atoms, which by 1 to 2 oxygen atoms can be interrupted, represents phenyl optionally substituted by fluorine, chlorine, bromine, methyl, methoxy, trifluoromethyl or trifluoromethoxy;

R ^{2 represents} Ci-Cg-alkyl, C ₂ -Cg-alkenyl, -CC-C4-alkoxy-C ₂ -C ₃ -alkyl, for each optionally simply by fluorine, chlorine, bromine, nitro, methyl, methoxy or trifluoromethyl substituted phenyl or benzyl.

9. Composition according spoke 1, containing the compound of formula (I-b-1)

10. Composition according to claim 1 containing the compounds of the formulas (I-b-1) and (H-l).

11. Use of mixtures, as defined in spoke 1, for controlling animal pests.

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

13. A process for the preparation of insecticidal and acaricidal agents, characterized in that mixtures, as defined in claim 1, are mixed with extenders and / or surface-active substances.