EP2061319A1

EP2061319A1 - Insecticidal heterocyclic carboxylic acid derivatives

Info

Publication number: EP2061319A1
Application number: EP07726015A
Authority: EP
Inventors: Reiner Fischer; Herbert Gayer; Olaf Gebauer; Oliver Gaertzen; Ulrich Heinemann; Stefan Herrmann; Michael Müller; Thomas Schenke; Welf-Burkhard Wiese; Heinz-Juergen Wroblowsky; Eva-Maria Franken; Olga Malsam; Ulrich Görgens; Christian Arnold
Original assignee: Bayer CropScience AG
Current assignee: Bayer CropScience AG
Priority date: 2006-08-17
Filing date: 2007-06-14
Publication date: 2009-05-27
Also published as: DE102006039255A1; BRPI0715792A2; JP2010500979A; US20100222218A1; KR20090040468A; WO2008019723A1

Abstract

The invention relates to the use of heterocyclic carboxylic acid derivatives of the following formula (I), where the symbols have the meanings given in the description, or the agrochemically effective salts, or mixtures of said compounds and/or the agrochemically effective salts thereof with other active agents for preventing animal pests, method and means for preventing animal pests in and/or on plants or in and/or on plant seedstock, method for production of such agents and treated seedstock.

Description

Insecticidal heterocyclic carboxylic acid derivatives

The invention relates to the use of heterocyclic carboxylic acid derivatives of the following formula (I)

wherein the symbols have the meanings given in the description, or their agrochemically active salts or mixtures of these compounds and / or their agrochemically active salts with other active substances for controlling nematodes and animal pests, methods and agents for controlling nematodes and animal pests and / or on plants or in and / or on seeds of plants and / or in soil, processes for the preparation of such agents and treated seeds.

The present invention furthermore relates to heterocyclic carboxylic acid derivatives of the formula (I), processes for their preparation and their use for combating pests in agriculture, horticulture and forestry, in the protection of materials and in the household and hygiene sector.

The present invention also relates to the enhancement of the effect of pesticides containing insecticidal heterocyclic carboxylic acid derivatives of the formula (I) by the addition of ammonium or phosphonium salts and optionally penetration promoters, the corresponding agents, processes for their preparation and their use in crop protection, especially as insecticides and / or acaricides.

It is already known that certain pyrazolopyrimidine derivatives have fungicidal properties, see e.g. WO 04/000844, WO 05/082907 and WO 06/087120. Furthermore, it is already known that certain pyrazolopyrimidine derivatives possess insecticidal properties, see e.g. WO 04/000844.

However, as the ecological and economic requirements for modern pest control agents are constantly increasing, for example with regard to spectrum of action, toxicity, selectivity, amount of application, residue formation and favorable manufacturability, and, in addition, problems with resistance can occur, for example, the constant task is to develop new pesticides , which have advantages over the known at least in some areas. New heterocyclic carboxylic acid derivatives of the formula (I) have now been found

in which the symbols have the following meaning:

A is a nitrogen atom, in which case the bond in the pyrimidine ring is a single bond, or a carbon atom, in which case the bond in the pyridine ring is a double bond,

B ¹ stands for a nitrogen atom ^{O (} ^ ^er ^ ^r ^ ^as F ^ra S ^ment

B ² represents a nitrogen atom ^{0 (^} ^he ^ * ^r ^ ^ra ^as P S ^ment

Be represents a nitrogen atom ° ^ ^he ^ ^r ^ ^as fragment or a

Binding,

B ⁴ stands for the fragments where the dashed bonds may be single bonds, double bonds or aromatic bonds;

X is hydrogen, halogen, cyano, hydroxy, optionally substituted alkyl, optionally substituted alkoxy, optionally substituted phenyl, optionally substituted alkylthio, optionally substituted alkylsulfinyl or optionally substituted alkylsulfonyl;

Y is optionally substituted aryl, optionally substituted heterocyclyl, optionally substituted alkyl, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted cycloalkyl, optionally substituted cycloalkenyl, optionally substituted arylalkyl, halogen, an optionally substituted amino group, optionally substituted (C ₎ - Cg) alkoxy, optionally substituted (C _j -Cg) -alkylthio, optionally substituted (C 5 -C 10) -acyloxy, optionally substituted (Cg-C _j o) arylthio, optionally substituted hetero- cyclyloxy, optionally substituted (C6-C] _Q) aryl (Ci-C4) alkoxy, optionally substituted (C6-C o _j) aryl (C 1 -C 4) -alkylthio, optionally substituted heterocyclyl optionally substituted heterocyclyl (C ₁ -C 4) alkylthio, C (S) OR ⁸ , C (O) SR ⁸ or C (S) SR ⁸ ;

Z is hydroxy, halogen or in each case optionally substituted alkoxy, alkylthio,

R ¹

Alkylsulfonyl or the group - [s _{j ^}

^* FT

G ^1, G ² and G ⁵ independently of one another represent hydrogen, halogen, optionally substituted alkyl or optionally substituted cycloalkyl, O- (C _j-C4) alkyl or S (O) ₀ .2 (C ₁ -C ₄₎ alkyl;

L is oxygen or sulfur;

R! is hydrogen, optionally substituted alkyl, optionally substituted

Alkenyl, optionally substituted alkynyl, optionally substituted cycloalkyl or optionally substituted heterocyclyl, hydroxy, optionally substituted alkoxy, amine, optionally substituted alkylamine or optionally substituted

dialkylamine;

R2 is hydrogen or alkyl;

or

R 1 and R ² together with the nitrogen atom to which they are attached represent an optionally substituted heterocyclic ring;

R ³ is CO-N, CO-OR ⁶ , CO-SR ⁶ , CS-OR ⁶ or CS-SR ⁶ ; XR ⁵

R ^ is hydrogen, in each case optionally substituted alkyl, alkenyl or alkynyl, in each case optionally substituted saturated or unsaturated cycloalkyl, which may optionally be interrupted by heteroatoms, in each case optionally substituted phenyl, heteroaryl, arylalkyl, heteroarylalkyl or a cation such as mono- or bivalent Metal atoms or an ammonium ion optionally substituted by alkyl or arylalkyl; R ⁵ is hydrogen, in each case optionally substituted alkyl, alkoxy, alkenyl, alkenyloxy or alkynyl, for the groups COR ⁷ , S (O) i_ ₂ R ⁷ , cyano, COOR ⁷ ,

saturated, partially or fully unsaturated or aromatic, optionally substituted 5- or 6-membered heterocyclyl, which may optionally be one or up to three further

Heteroatoms selected from the group consisting of N, S and / or O atoms, wherein oxygen atoms may not be adjacent; or

R ⁴ and R- * together with the nitrogen atom to which they are attached represent an optionally substituted, saturated, unsaturated or aromatic ring which may optionally be interrupted by further heteroatoms;

R ⁶ is hydrogen, a cation, for example an optionally substituted by alkyl or

Arylalkyl substituted ammonium ion, in each case optionally substituted alkyl,

Alkenyl, alkynyl, in each case optionally substituted cycloalkyl or cycloalkenyl, which may optionally be interrupted by a heteroatom, optionally substituted cycloalkyl-alkyl or optionally substituted arylalkyl;

R ⁷ is hydrogen, in each case optionally substituted alkyl, alkenyl, alkynyl is in each case optionally substituted cycloalkyl-alkyl, cycloalkyl or cycloalkenyl, in each case optionally substituted aryl, heteroaryl, arylalkyl or heteroarylalkyl;

R 1 is hydrogen, in each case optionally substituted alkyl, alkenyl, alkynyl, alkoxy or NH-R ⁴ ;

or

R ⁴ and R ⁷ together with the N-CO or NS (O) _] .2 group to which they are attached form a 4- to 8-membered cycle containing one or more heteroatoms from the series sulfur, oxygen and / or or nitrogen, wherein oxygen atoms may not be adjacent;

or R ⁷ and R. 8, together with the nitrogen atom to which they are attached, represent an optionally substituted saturated or unsaturated ring which may optionally be interrupted by further heteroatoms;

R 1 and R ¹⁰ are each independently optionally substituted alkyl, alkenyl, alkoxy, alkenyloxy, alkynyloxy, cycloalkoxy, cycloalkenyloxy,

Cycloalkylalkoxy, alkylthio, alkenylthio, phenoxy, phenylthio, benzyloxy, benzylthio, heteroaryloxy, heteroarylthio, heteroarylalkoxy or heteroarylalkylthio;

or

R ⁹ and R ¹ 0 are together with the phosphorus atom to which they are attached form an optionally substituted 5- to 7-membered cyclic group, by one or two

Oxygen and / or sulfur atoms may be interrupted; and

R 1 and R 1 independently represent each optionally substituted alkyl, alkenyl, alkynyl, phenyl or phenylalkyl;

and agrochemically active salts thereof. The groups referred to above as optionally substituted, including groups and rings or cycles, may be unsubstituted or substituted, in particular with the same substituents as defined for the corresponding groups in the further embodiments of the present invention described below. Here, the substituents of one embodiment can be combined with those of another embodiment as desired.

Inventive heterocyclic carboxylic acid derivatives of the formula (I) and their agrochemically active salts are very suitable as pesticides, in particular for controlling animal pests such as insects, parasites of the subclass of Acari (Acarina) (such as mites, spider mites and / or ticks) and / or nematodes. Above all, the abovementioned compounds according to the invention exhibit a strong insecticidal and / or acaricidal and / or nematicidal activity and can be used both in crop protection, in the household and hygiene sector and in the protection of materials.

The compounds of the formula (I) can be used both in pure form and as mixtures of various possible isomeric forms, in particular of stereoisomers, such as E and Z, threo and erythro, and optical isomers, such as R and S isomers or Atropisomers, but optionally also of tautomers. The invention includes both the pure isomers and their mixtures. The compounds of formula (I) may optionally be present in different polymorphic forms or as a mixture of different polymorphic forms. Both the pure polymorphs and the polymorph mixtures are the subject of the invention and can be used according to the invention.

Depending on the nature of the substituents defined above, the compounds of formula (I) have acidic or basic properties and may form salts, optionally also internal salts. If the compounds of the formula (I) bear hydroxy, carboxy or other groups which induce acidic properties, these compounds can be reacted with bases to form salts. Suitable bases are, for example, hydroxides, carbonates, bicarbonates of the alkali and alkaline earth metals, in particular those of sodium, potassium, magnesium and calcium, furthermore ammonia, primary, secondary and tertiary amines having (QC ^ -alkyl radicals, mono-, di- and trialkanolamines of _(Q-C4) -alkanols, choline and chlorocholine. If the compounds of formula (I) amino, alkylamino or other groups inducing basic properties, these compounds can be reacted with acids to form salts. Suitable acids are for example mineral acids, such as Hydrochloric, sulfuric and phosphoric acid, organic acids such as acetic acid or oxalic acid, and acidic salts such as NaHSO ₄ and KHSO _4. The salts thus obtainable also have insecticidal properties.

The compounds according to the invention, namely the heterocyclic carboxylic acid derivatives are generally defined by the formula (I).

The present invention thus relates

(1) The use of chemical compounds, namely heterocyclic carboxylic acid derivatives of the following formula (I)

wherein

A represents a nitrogen atom, in which case the bond in the pyrimidine ring is a single bond, or represents a carbon atom, in which case the bond in the pyridine ring is a double bond,

- C-G ¹ B 1 for a nitrogen atom N = or for the fragment || .

B ^ represents a nitrogen ^{atom, 0 <^} ^he ^ ^"r ^ ^as fragment ° ^he d for a

Binding,

and

B ^ for the fragments where the dashed bonds may be single bonds, double bonds or aromatic bonds;

X is hydrogen, halogen, cyano, hydroxy, alkyl, alkoxy, phenyl, alkylthio, alkylsulfinyl or alkylsulfonyl;

Y is aryl, heterocyclyl, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl,

Arylalkyl, halogen, an amino group, (Cj-Cg) -alkoxy, (Cj-Cg) -alkylthio, (Cg-Cio) -aryloxy, (Cg-C10) -arylthio, heterocyclyloxy, (Cg-Cio) -aryl- (C ₁ -C ₄ ) -alkoxy, (C 9 -C 12) -aryl- (C ₁ -C ₄ ) -alkylthio, heterocyclyl (C ₁ -C ₄ ) -alkoxy, HeI-TOCyclicy- (C ₁ -C ₄ ) -alkylthio , C (S) OR ⁸ , C (O) SR ⁸ or C (S) SR ⁸ ;

Z is hydroxy, halogen or alkoxy, alkylthio, alkylsulfonyl or the group

G ^, G ^ and G ^ independently represent hydrogen, halogen, alkyl or

Cycloalkyl, O- (Cj-C4) alkyl or S (O) ₀ ^ (C i-C4>-alkyl;

L is oxygen or sulfur;

R! for hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl or heterocyclyl, hydroxy,

Alkoxy, amine, alkylamine or dialkylamine;

R ^ is hydrogen or alkyl;

or RI and R.2 together with the nitrogen atom to which they are attached represent a heterocyclic ring;

R3 is CO-N, CO-OR ^6, CO-SR ^6, OR ⁶ or CS-CS-SR ^6;

R ^ is hydrogen, alkyl, alkenyl or alkynyl, in each case saturated or unsaturated cycloalkyl, which may optionally be interrupted by heteroatoms,

Phenyl, heteroaryl, arylalkyl or heteroarylalkyl, or a cation such as monovalent or divalent metal atoms or an ammonium ion;

R ^ is hydrogen, alkyl, alkoxy, alkenyl, alkenyloxy or alkynyl, for the groups COR ⁷ , S (O) ₁ R ⁷ , cyano, COOR ⁷ ,

or saturated, partially or fully unsaturated or aromatic, 5- or 6-membered ring heterocyclyl optionally containing one or up to three further heteroatoms selected from the group consisting of N, S and O atoms, oxygen atoms not being adjacent , stands;

or

R ^ and R-> together with the nitrogen atom to which they are attached represent a saturated, unsaturated or aromatic ring which may optionally be interrupted by further heteroatoms;

R ^{6 is} hydrogen, a cation, for example an ammonium ion, alkyl, alkenyl, alkynyl, cycloalkyl or cycloalkenyl, which may be replaced by a

Hetero atom may be interrupted, cycloalkyl-alkyl or aryl, arylalkyl, heteroaryl or heteroaryl-alkyl;

R ^{7 is} hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl-alkyl, cycloalkyl or cycloalkenyl, aryl, heteroaryl, arylalkyl or heteroarylalkyl;

R ^{8 is} hydrogen, alkyl, alkenyl, alkynyl, alkoxy or NH-R ⁴ ;

or R ^ and R.7 together with the N-CO or NS (O)]. 2 group to which they are attached form an A to 8-membered cycle containing one or more heteroatoms from the group of sulfur, oxygen and / or or nitrogen, wherein oxygen atoms are not adjacent, form;

or

R 7 and R 8 together with the nitrogen atom to which they are attached represent an optionally substituted saturated or unsaturated ring which may optionally be interrupted by further heteroatoms;

R "and R 10 independently of one another are alkyl, alkenyl, alkoxy, alkenyloxy, alkynyloxy, cycloalkoxy, cycloalkenyloxy, cycloalkylalkoxy, alkylthio,

Alkenylthio, phenoxy, phenylthio, benzyloxy, benzylthio, heteroaryloxy, heteroarylthio, heteroarylalkoxy or heteroarylalkylthio;

or

R "and R 1" together with the phosphorus atom to which they are attached stand for an optionally substituted 5- to 7-membered cycle which may be interrupted by one or two oxygen and / or sulfur atoms;

and

R1 and R1 independently represent alkyl, alkenyl, alkynyl, phenyl or phenylalkyl;

or of agrochemically active salts thereof for controlling animal

pests;

(2) the use of a mixture comprising at least one of the compounds defined under (1) and / or at least one of their agrochemically active salts and a further active ingredient selected from the group consisting of insecticides, attractants, sterilants, bactericides, acaricides, nematicides, fungicides , growth-regulating substances, herbicides, safeners, fertilizers or semiochemicals for controlling animal pests;

(3) an agent for controlling animal pests in and / or on plants or in and / or on seeds of plants, said agent comprising at least one compound as defined under (1) and / or at least one of its agrochemically active compounds Salts or as under (2) mixture and agrochemically customary auxiliaries and / or additives;

(4) a method of controlling animal pests in and / or on plants or in and / or on seeds of plants comprising directly or indirectly contacting said pests with at least one as defined under (1)

Compound and / or at least one of their agrochemically active salts or a mixture as defined under (2) or an agent as defined under (3);

(5) a process for producing a defined agent as defined in (3) comprising mixing at least one compound as defined under (1) and / or at least one of their agrochemically active salts or a mixture as defined under (2) with agrochemically customary auxiliaries and / or additives; and

(6) Seed which has been treated with at least one compound as defined under (1) and / or at least one of its agrochemically active salts or a mixture as defined under (2) or an agent as defined under (3).

Preferred substituents, fragments or ranges of the radicals listed in the formulas mentioned above and below are explained below for a preferred embodiment of the present invention:

A preferably represents a nitrogen atom, in which case the bond in the pyrimidine ring is a single bond, or represents a carbon atom, in which case the bond in the pyridine ring is a double bond,

- CG ¹ B ¹ is preferably a nitrogen atom _* ■ __ or the fragment | | .

CG ² B ² is preferably a nitrogen atom *.-_ Or the fragment 11,

- CG ³ B ³ is preferably a nitrogen atom u_ or the fragment | | or for a bond,

- N - - C =

B ⁴ is preferably the fragments ό ³ or p3 where the dashed bonds may be single bonds, double bonds or aromatic bonds;

X is preferably hydrogen, fluorine, chlorine, bromine, cyano, hydroxy, alkoxy of 1 to 4

Carbon atoms or alkylthio of 1 to 4 carbon atoms, C _j -Cg alkyl or C 1 -C 4 haloalkyl;

Y is preferably C ₁ -C ₁ O-AIlCyI, C2-C j-Q alkenyl, C2-C \ _Q alkynyl, C3-C8-cycloalkyl, phenyl-Cj-Cio-alkyl, wherein Y is unsubstituted or partially or completely is halogenated and / or optionally carries one to three radicals R ^x , or Ci-Cio-H ^a l ° g ^ena alkyl, which optionally carries one to three radicals R ^x , wherein the R ^{x are the} same or different selected from the group from cyano, nitro, hydroxy, Cj-Cg-alkyl,

C _j -Cg -haloalkyl, C ₃ -C 6 -cycloalkyl, C ₁ -CO-alkoxy, C ₁ -Co-haloalkyl,

C ₁ -C ₆ -acrylic, C ₁ -C ₆ -haloalkylthio, C ₁ -C ₆ -acyloxyalkyl, C ₁ -C ₆ -haloalkylsulphinyl, C ₁ -C ₆ -alkylsulphonyl, C ₁ -C ₆ -halogenated alkylsulphonyl, C ₁ -C ₆ -alkylamino, di - C ^ Coe-alkylamino, C2-C ₆ -alkenyl, C ₂ -C ₆ alkenyloxy, C2-C6-alkynyl, C3-C ₆ oxy alkynyl and optionally halogenated alkenyl-C ₁ -C 4 -alkoxy and OXy-C ₁ -C 4 -alkyl-C ₁ -C 4 -alkyloxy; or

Y is preferably phenyl, which may optionally be monosubstituted, monosubstituted or differently monosubstituted by

Halogen, cyano, nitro, amino, hydroxy, formyl, carboxy, carboxyalkyl, carbamoyl, thiocarbamoyl;

in each case straight-chain or branched alkyl, alkoxy, alkylthio, alkylsulfinyl or alkylsulfonyl having in each case 1 to 6 carbon atoms;

in each case straight-chain or branched alkenyl, alkynyl, alkynyloxy or alkenyloxy having in each case 2 to 6 carbon atoms;

in each case straight-chain or branched haloalkyl, haloalkoxy, haloalkylthio,

Haloalkylsulfinyl or haloalkylsulfonyl each having 1 to 6 carbon atoms and 1 to 13 identical or different halogen atoms;

in each case straight-chain or branched haloalkenyl or haloalkenyloxy having in each case 2 to 6 carbon atoms and 1 to 11 identical or different halogen atoms; in each case straight-chain or branched alkylamino, dialkylamino, alkylcarbonyl, alkylcarbonyloxy, alkoxycarbonyl, alkylsulfonyloxy, hydroximinoalkyl or alkoximinoalkyl having in each case 1 to 6 carbon atoms in the individual alkyl moieties;

optionally mono- to disubstituted, by fluorine, chlorine, Cj ^ -alkyl or Ci-C3-alkoxy-substituted cycloalkyl having 3 to 8 carbon atoms;

2,3-propanediyl, 1,4-butanediyl, methylenedioxy (-O-CH ₂ -O-) or 1,2-ethylenedioxy (-O-CH ₂ -CH ₂ -O-), which radicals may be monosubstituted, polysubstituted, identically or differently substituted by halogen, alkyl having 1 to 4 carbon atoms and / or haloalkyl having 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms; or

Y is preferably saturated or wholly or partially unsaturated or aromatic heterocyclyl having 3 to 8 ring members and 1 to 3 heteroatoms from the group nitrogen, oxygen and sulfur, where the heterocyclyl may be monosubstituted or disubstituted by halogen, alkyl having 1 to 4 carbon atoms , Alkoxy of 1 to 4 carbon atoms, alkylthio of 1 to 4 carbon atoms, haloalkoxy of 1 to 4

Carbon atoms, haloalkylthio having 1 to 4 carbon atoms, hydroxy, mercapto, cyano, nitro and / or cycloalkyl having 3 to 6 carbon atoms or / and carboxyalkyl;

Z is preferably hydroxy, chlorine, bromine, in each case optionally 1 to 7

Halogen atoms substituted straight-chain or branched Cj -Cg-alkoxy, Cj -Cg-Al

/ kylthio, Q.-Cg-alkylsulfonyl or the group - ^;

G ^1, G ² and G * are preferably independently of one another represent hydrogen, halogen, optionally substituted by one or more halogen atoms substituted _C] -C4-alkyl, optionally substituted by one or more halogen atoms substituted C3-C6-cycloalkyl, SCH _3, SC ₂ H ₅ , SOCH ₃ , SOC ₂ H ₅ , SO ₂ CH ₃ , SO ₂ C ₂ H ₅ , OCH ₃ or OC ₂ H ₅ ;

L is oxygen or sulfur;

R! is preferably hydrogen, alkyl of 1 to 10 carbon atoms, which is unsubstituted or monosubstituted to five times, identically or differently substituted by halogen, cyano, hydroxy, alkoxy having 1 to 4 carbon atoms, cycloalkyl having 3 to 6 carbon atoms, mercapto, alkylthio with 1 to 4 carbon atoms, amino, mono- or dialkylamino each having 1 to 4 carbon atoms; or R 1 is preferably alkenyl of 3 to 10 carbon atoms which is unsubstituted or monosubstituted to trisubstituted, identically or differently substituted by halogen, cyano, hydroxy, alkoxy of 1 to 4 carbon atoms, cycloalkyl of 3 to 6 carbon atoms, mercapto, alkylthio of 1 to 4 carbon atoms, amino, mono- or dialkylamino each having 1 to 4 carbon atoms; or

R 1 is preferably alkynyl of 3 to 10 carbon atoms which is unsubstituted or monosubstituted to trisubstituted, identically or differently substituted by halogen, cyano, hydroxy, alkoxy of 1 to 4 carbon atoms, cycloalkyl of 3 to 6 carbon atoms, mercapto, alkylthio 1 to 4 carbon atoms, amino, mono- or dialkylamino each having 1 to 4 carbon atoms; or

R! preferably represents cycloalkyl having 3 to 10 carbon atoms which is unsubstituted or monosubstituted to trisubstituted, identically or differently substituted by halogen and / or alkyl, haloalkyl having in each case 1 to 4 carbon atoms; or

R! is preferably saturated or unsaturated heterocyclyl having 3 to 10 ring members and 1 to 3 heteroatoms, such as nitrogen, oxygen and / or sulfur, wherein the

Heterocyclyl is unsubstituted or mono- or polysubstituted by halogen, alkyl having 1 to 4 carbon atoms, alkoxy having 1 to 4 carbon atoms, cyano, nitro, cycloalkyl having 3 to 6 carbon atoms, hydroxy, alkoxy, alkenyloxy, alkynyloxy having 1 to 6 carbon atoms or mercapto ;

R 1 is preferably hydrogen or alkyl of 1 to 6 carbon atoms; or

R! and R ^ are preferably taken together with the nitrogen atom to which they are attached, for a saturated or unsaturated heterocyclic ring having 3 to 8 ring members, wherein the heterocycle optionally contains a further nitrogen, oxygen or sulfur atom as ring member and wherein the heterocycle is unsubstituted or may be substituted up to three times by fluorine, chlorine, bromine, alkyl having 1 to 4 carbon atoms,

Haloalkoxy having 1 to 4 carbon atoms and 1 to 9 fluorine and / or chlorine atoms, mercapto, thioalkyl having 1 to 4 carbon atoms and / or haloalkylthio having 1 to 4 carbon atoms and 1 to 9 fluorine and / or chlorine atoms;

R ³ is preferably CO-OR ⁶ , CO-SR ⁶ , CS-OR ⁶ or CS-SR ⁶ ; R ⁴ preferably represents hydrogen, cations from the series of the alkali or alkaline earth metals or ammonium ions NH4, mono-CC _j -C _j oVAlkylammoniurn, di- (C _j -C _j o) alkyl ammonium, tri- (Ci-Cio ) -Alkylammonium, tetra (Ci-Cio) -Alkylammonium, wherein the

Alkyl radicals of the ammonium ions may be substituted with aryl or hydroxy, or cholinium,

in each case optionally monosubstituted to polysubstituted by fluorine, chlorine, C _j -C ₄ alkoxy, C _j - C ₄ alkylthio, cyano, CO ₂ H or CO-OC _j -C ₄ alkyl-substituted C _j -C _jQ - alkyl, C ₃ - C _jQ alkenyl or _{C3-C] Q} alkynyl, in each case optionally monosubstituted to polysubstituted by fluorine, chlorine, C _r C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ - AIkOXy, CN, CO ₂ H or CO-O-C _j -C ₄ alkyl substituted Cβ-Cg-cycloalkyl or C5-Cg-cycloalkenyl, which may optionally be interrupted by an oxygen or sulfur atom,

in each case optionally mono- to trisubstituted by fluorine, chlorine, bromine, C _j -C ₄ alkyl, C _j - substituted C ₄ haloalkyl, C _j -C ₄ -alkoxy, C _j -C ₄ haloalkoxy, nitro or cyano, phenyl, Pyridyl, thiazolyl, pyrimidyl, benzyl, phenethyl, pyridinylmethyl or thiazolylmethyl;

R ⁵ is preferably hydrogen, each optionally mono- to _{polysubstituted} by fluorine and / or chlorine-substituted C _j -C _jQ alkyl, C _j -C _jQ alkoxy, C ₃ -C _jQ alkenyl, C ₃ -C _j o Alkenyloxy or C ₃ -C ₁₀ alkynyl; for the groups CO-R ⁷ , S (O) _j . ₂ R ^7, cyano,

or optionally in each case optionally once or twice by fluorine, chlorine, bromine, C 1 -C ₄ -

Alkyl, C 1 -C ₄ -alkoxy, cyano or nitro-substituted pyridine, pyrimidine, triazine, thiazole or pyrazole; or

R ⁴ and R ⁵ are preferably taken together with the nitrogen atom to which they are attached, for a mono- or polysubstituted by C 1 -C ₄ -alkyl-substituted saturated or unsaturated 5- or 6-ring, which may be interrupted by oxygen or sulfur can;

R6 preferably represents hydrogen, cations from the series of the alkali or alkaline earth metals or ammonium ions NH _4, mono- (C _j -C _j o) -Alkylamrnonium, di- (C _j -C _j o) alkyl ammonium, tri- (C _j -C _j o) -alkylammonium, tetra- (C _j -C _j o) -alkylammonium, wherein the alkyl radicals of the ammonium ions may be substituted by aryl or hydroxy, or

cholinium, in each case optionally monosubstituted to polysubstituted by fluorine, chlorine, C ₁ -C ₄ -alkoxy, C ₁ - C ₄ alkylthio, cyano, CO ₂ H or CO-OC _r C ₄ alkyl-substituted Ci-C ₁₀ alkyl, C ₃ - C-alkenyl or C ₃ -C ₁ O-AIkUIyI, in each case optionally mono- to polysubstituted by fluorine, chlorine, C _r C ₄ alkyl, C _j -C ₄ haloalkyl, C _r C ₄ alkoxy, CN , CO ₂ H or CO-O-C ₁ -C ₄ -alkyl-substituted C ₃ -C ₈ cycloalkyl, C ₃ -C ₆ cycloalkyl-Ci-C ₂ alkyl or C ₅ -C ₈ -

Cycloalkenyl, which may optionally be interrupted by an oxygen or sulfur atom,

in each case optionally mono- to trisubstituted by fluorine, chlorine, bromine, C _j -C ₄ alkyl, C ₁ - substituted C ₄ haloalkyl, C ₁ -C ₄ -alkoxy, CpC ^ haloalkoxy, nitro or cyano, phenyl, pyridyl, thiazolyl, Pyrimidyl, benzyl, phenethyl, pyridinylmethyl or

thiazolylmethyl;

R ⁷ is preferably hydrogen, in each case optionally mono- to polysubstituted by fluorine, chlorine, C _r C ₄ alkoxy, C _r C ₄ alkylthio, cyano, CO ₂ -H or CO-OC _j -C ₄ alkyl substituted C _1Q ₁ -C -alkyl, C ₃ -Ci0 alkenyl or C ₃ -C _j o-alkynyl, several times for each if necessary simply by fluorine, chlorine, C ₁ -C ₄ -alkyl, C _j -C ₄ - Haloalkyl, C ₁ -

C ₄ alkoxy, CN, CO ₂ H or CO-OC _r C ₄ -alkyl-substituted C ₃ -C ₈ -cycloalkyl, C ₃ -C ₆ -cycloalkyl-C ₁ -C ₂ -alkyl or C ₅ -C ₈ -cycloalkenyl, which may optionally be interrupted by an oxygen or sulfur atom,

in each case optionally mono- to trisubstituted by fluorine, chlorine, bromine, _C] -C ₄ alkyl, C _j -C ₄ haloalkyl, C _j -C ₄ alkoxy, C _j -C ₄ haloalkoxy, nitro or cyano phenyl , Pyridyl, thiazolyl, pyrimidyl, benzyl, phenethyl, pyridinylmethyl or thiazolylmethyl;

R.sup.8 is preferably hydrogen, in each case optionally mono- to polysubstituted by fluorine and / or chlorine-substituted CpCg-alkyl, C ₃ -C ₆ -alkenyl, C ₃ -C ₆ -alkynyl or C ₁ -C ₆ -alkoxy;

or

R ⁴ and R ⁷ preferably together with the N-CO or NS (O) i_ ₂ group to which they are attached form a 4- to 8-membered cycle which contains one or more heteroatoms from the series sulfur, oxygen and / or or nitrogen, wherein oxygen atoms may not be adjacent;

or R ⁷ and R ⁸ are preferably taken together with the nitrogen atom to which they are attached, for a mono- or polysubstituted by C 1 -C ₄ -alkyl-substituted saturated or unsaturated 5- or 6-ring, which may be interrupted by oxygen or sulfur can;

R ⁹ and R ¹⁰ are preferably independently of one another represent in each case optionally monosubstituted to polysubstituted by fluorine and / or chlorine-Ci-C ₈ alkyl, C ₃ -C ₈ alkenyl, C ₈ - alkoxy, C ₃ -C ₈ - alkenyloxy, C ₃ -C ₈ alkynyloxy, C] -C ₆ alkylthio, C ₃ -C ₆ alkenylthio, optionally mono- or disubstituted by fluorine, chlorine, _Ci-C4-alkyl, Ci-C ₄ haloalkyl, QC ₄ -alkoxy substituted C ₃ -C ₈ -cycloalkoxy, C ₄ -Cg -cycloalkenyloxy or C ₃ -C ₈ -cycloalkyl-C ₁ -C ₂ -alkoxy, in each case optionally mono- to trisubstituted by fluorine,

Chlorine, bromine, C ₁ -C ₄ -alkyl-C ₁ -C ₄ haloalkyl, C ₁ -C ₆ -alkoxy, C ₁ -C ₄ -haloalkoxy, C ₁ -C ₆ -alkylthio, cyano or nitro-substituted phenoxy, phenylthio, benzyloxy, benzylthio, Pyridinyloxy, pyrazolyloxy, pyridinylthio, pyrimidylthio, thiazolylthio, pyridyl-C _r C ₂ alkoxy, pyrimidyl C ₁ -C ₂ alkyloxy, thiazolyl C] C ₂ alkyloxy, pyridyl C _r C ₂ alkylthio, thiazolyl C _{r is} C ₂ -alkylthio or pyrimidyl-C ₁ -C ₂ -alkylthio;

or

R ⁹ and R ¹⁰ preferably together with the phosphorus atom to which they are bonded, represent an optionally mono- to trisubstituted by fluorine, chlorine, -C ₄ alkyl, _Ci-C4-alkoxy or Ci-C ₄ haloalkyl substituted five- to seven membered cycle which may be interrupted by one or two oxygen and / or sulfur atoms;

R ¹¹ and R ¹² are each, independently of one another, in each case optionally mono- to trisubstituted by fluorine or chlorine, C ₁ -C ₈ -alkyl, C ₃ -C ₈ -alkenyl or C ₃ -C ₈ -

Alkynyl, each optionally optionally once or twice by fluorine, chlorine, bromine, C] -C ₄ -

Alkyl, Ci-C ₄ haloalkyl, C] _-C4 alkoxy, CpC ₄ -haloalkoxy, cyano or nitro-substituted phenyl or benzyl.

The compounds of the invention are generally defined by the formula (I). Particularly preferred substituents, fragments or ranges of the radicals listed in the formulas mentioned above and below are explained below for a particularly preferred embodiment of the present invention:

A is particularly preferably a nitrogen atom, in which case the bond in the

Pyrimidine ring is a single bond, or for a carbon atom, in which case the bond in the pyridine ring is a double bond, B ¹ particularly preferably represents a nitrogen atom N = ^oc * ^er the fragment

-CG ¹

B ² particularly preferably represents a nitrogen atom M ^ = ^ ^he ^ ° ^for the fragment

- C-G ²

B ³ particularly preferably represents a nitrogen atom M ^ = d for the fragment ^he °

- CG ^J or for a bond,

- N- ^~ ? ⁼⁼

B ⁴ particularly preferably represents the fragments p3 or p3

where the dashed bonds, single bonds, double bonds or aromatic bonds can be;

X particularly preferably represents hydrogen, fluorine, chlorine, cyano, C _r C ₄ alkyl or C] -C ₂ -

Haloalkyl which may be substituted by one to five fluorine and / or chlorine atoms;

Y particularly preferably represents in each case optionally substituted by one to five fluorine and / or chlorine atoms substituted Cj-Cg-alkyl, C2-Cg-alkenyl, C2-Cg-alkynyl or C3-Cg-cycloalkyl;

or

Y is particularly preferably phenyl, which may optionally be monosubstituted to trisubstituted, identically or differently substituted by fluorine, chlorine, bromine, iodine, cyano, nitro, formyl, methyl, ethyl, n- or i-propyl, n-, i- , s- or t-butyl, vinyl, 1-propenyl, ethynyl, 1-propynyl, allyl, propargyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethylsulfinyl, Methylsulfonyl, ethylsulfonyl, allyloxy, propargyloxy, trifluoromethyl, trifluoroethyl, difluoromethoxy, trifluoromethoxy, difluorochloromethoxy, trifluoroethoxy, difluoromethylthio, difluorochloromethylthio, trifluoromethylthio, trifluoromethylsulfinyl, trifluoromethylsulfonyl, trichloroethinyloxy, trifluorethinyloxy, chloroallyloxy, iodopropargyloxy, methylamino, ethylamino, n- or i-propylamino, dimethylamino, diethylamino, acetyl, propionyl, acetyloxy, methoxycarbonyl, ethoxycarbonyl,

Hydroximinomethyl, hydroximinoethyl, methoximinomethyl, ethoximinomethyl, methoxy iminoethyl, ethoximinoethyl, cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl, or by

1,3-propanediyl, 1,4-butanediyl, methylenedioxy (-O-CH ₂ -O-), or 1,2-ethylenedioxy (-O-CH ₂ -CH ₂ ) linked in the 2,3-position or 3,4-position ₂ -O-), where these radicals may be mono- or polysubstituted by identical or different substituents by fluorine,

Chlorine, methyl, ethyl, n-propyl, i-propyl trifluoromethyl, carboxy and / or carboxymethyl; or

Y is particularly preferably pyridyl which is linked in the 2- or 4-position and may be monosubstituted, monosubstituted or differently substituted by fluorine, chlorine, bromine, cyano, hydroxyl, mercapto, nitro, methyl, ethyl, methoxy, methylthio , Hydroxyminomethyl, hydroximinoethyl, methoximinomethyl, methoximinoethyl, trifluoromethyl,

Carboxy and / or carboxymethyl or

Thiazolyl which is linked in the 2-, 4- or 5-position and may be mono- to disubstituted by identical or different substituents by fluorine, chlorine, bromine, cyano, nitro, hydroxy, mercapto, methyl, ethyl, methoxy, methylthio, hydroximinomethyl , Hydroximinoethyl,

Methoximinomethyl, methoximinoethyl, trifluoromethyl, carboxy and / or carboxymethyl or

Pyrimidyl which is linked in the 2- or 4-position and may be monosubstituted to trisubstituted, identically or differently, by fluorine, chlorine, bromine, cyano, nitro, hydroxyl, mercapto, methyl, ethyl, methoxy, methylthio, hydroximinomethyl, hydroximinoethyl,

Thienyl which is linked in the 2- or 4-position and may be monosubstituted to trisubstituted by identical or different substituents by fluorine, chlorine, bromine, cyano, nitro, hydroxy, mercapto, methyl, ethyl, methoxy, methylthio, hydroximinomethyl, hydroximinoethyl,

Methoximinomethyl, methoximinoethyl, trifluoromethyl, carboxy and / or carboxymethyl;

Z is particularly preferably chlorine, bromine, in each case optionally 1 to 3

Halogen atoms substituted straight-chain or branched QC ₄ -alkoxy, C ₁ -C ₄ -

Alkylthio or the group N.;

R ² G ¹ , G ² and G ³ are particularly preferably each independently hydrogen, halogen, optionally substituted by one or more halogen atoms (Ci-GO-alkyl optionally substituted by one or more halogen atoms cyclopropyl; SCH3, SC ₂ H ₅ , SOCH ₃ , SOC ₂ H ₅ , SO ₂ CH ₃ , SO ₂ C ₂ H ₅ , OCH ₃ or OC ₂ H ₅ ;

L is particularly preferably oxygen or sulfur;

R ¹ particularly preferably represents hydrogen, alkyl having 1 to 8 carbon atoms, which is unsubstituted or monosubstituted to trisubstituted, identically or differently, by fluorine, chlorine, cyano, alkoxy having 1 to 3 carbon atoms, cycloalkyl having 3 to 6 carbon atoms, alkylthio having 1 to 3 carbon atoms; or

R.1 particularly preferably represents alkenyl having 3 to 8 carbon atoms, which is unsubstituted or monosubstituted to trisubstituted, identically or differently substituted by fluorine, chlorine, cyano, alkoxy having 1 to 3 carbon atoms, cycloalkyl having 3 to 6 carbon atoms, alkylthio with 1 up to 3 carbon atoms; or

R! particularly preferably represents alkynyl having 3 to 8 carbon atoms, which is unsubstituted or monosubstituted to trisubstituted by identical or different substituents by fluorine, chlorine,

Cyano, alkoxy of 1 to 3 carbon atoms, cycloalkyl of 3 to 6 carbon atoms, alkylthio of 1 to 3 carbon atoms; or

R! particularly preferably represents cycloalkyl having 3 to 8 carbon atoms which is unsubstituted or monosubstituted to trisubstituted, identically or differently substituted by fluorine, chlorine and / or alkyl, haloalkyl, alkoxy having in each case 1 to 2 carbon atoms; or

R! particularly preferably represents saturated or unsaturated heterocyclyl of 3 to 8

Ring members and 1 to 2 heteroatoms, such as nitrogen, oxygen and / or sulfur, wherein the heterocyclyl is unsubstituted or monosubstituted or disubstituted by hydroxy, fluorine, chlorine, alkyl having 1 to 3 carbon atoms, alkoxy having 1 to 3 carbon atoms, cyano , Nitro or cycloalkyl having 3 to 6 carbon atoms;

R 1 particularly preferably represents hydrogen or alkyl having 1 to 6 carbon atoms; or

R! and R ^ are particularly preferably taken together with the nitrogen atom to which they are attached, for a saturated or unsaturated heterocyclic ring having 3 to 6

Ring members, wherein the heterocycle optionally contains a further nitrogen, oxygen or sulfur atom as ring member and wherein the heterocycle may be unsubstituted or substituted up to three times by fluorine, chlorine, bromine, alkyl having 1 to 3 carbon atoms lenstoffatomen, haloalkyl having 1 to 3 carbon atoms and 1 to 5 fluorine and / or chlorine atoms, alkoxy having 1 to 3 carbon atoms, haloalkoxy having 1 to 3 carbon atoms and 1 to 5 fluorine and / or chlorine atoms, thioalkyl having 1 to 3 carbon atoms and / or haloalkylthio having 1 to 3 carbon atoms and 1 to 5 fluorine and / or chlorine atoms;

R ³ is particularly preferably CON " ^R , CO-OR ⁶ , CO-SR ⁶ , CS-OR ⁶ or CS-SR ⁶ ;

V

R ⁴ particularly preferably represents hydrogen, Na ⁺ , K ⁺ , V ₂ Ca ²⁺ , V ₂ Mg ²⁺ , NH ₄ ⁺ , NH ₃ CH ₃ ⁺ , NH ₂ (CH ₃ ) ₂ ⁺ , NH (CH ₃ ) ₃ ⁺ , NH (C ₂ H ₅ ) /, NH ₂ (C ₂ Hj) ₂ ⁺ , NH ₃ C ₂ H ₅ ⁺ , NH ₃ IC ₃ H ₇ ⁺ ,

NH ₂ (iC ₃ H ₇ ) ₂ ⁺ , NH ₃ -CH ₂ -C ₆ H ₅ ⁺ , N (CH ₃ ) SH ₂ -C ₆ H ₅ ⁺ ,>

in each case optionally monosubstituted to trisubstituted by fluorine, chlorine, C ₁ -C ₃ -alkoxy, QC ₃ -

Alkylthio, cyano, CO ₂ H or CO-OC _r C ₃ alkyl substituted C _r C ₈ alkyl, C ₃ -C ₈ alkenyl or C ₃ -C ₈ alkynyl, each optionally optionally mono- to trisubstituted by fluorine, chlorine , C _r C ₃ alkyl, C _r C ₂ -haloalkyl, C _r C ₃ alkoxy, CN, CO ₂ H or CO-OC ₁ -C ₃ - alkyl-substituted C ₃ -C ₆ cycloalkyl, C ₃ -C ₆ -cycloalkyl-methyl or C ₅ -C ₆ -cycloalkenyl, which may optionally be interrupted by an oxygen or sulfur atom,

in each case optionally mono- to disubstituted by fluorine, chlorine, bromine, Ci-C ₃ alkyl, C _r C ₃ haloalkyl, C _r C ₃ alkoxy, C _r C ₃ haloalkoxy, nitro or cyano-substituted phenyl, pyridyl, thiazolyl , Pyrimidyl, benzyl, phenethyl, pyridinylmethyl or thiazolylmethyl;

R ⁵ particularly preferably represents hydrogen, in each case optionally monosubstituted to trisubstituted by fluorine and / or chlorine, C ₁ -C ₆ -alkyl, C ₁ -C ₆ -alkoxy, C ₃ -C ₈ -alkenyl, C ₃ -C ₈ -alkenyloxy or C C ₃ -C ₈ alkynyl; for the groups COR ⁷ , S (O) _1-2 R ⁷ , cyano, COOR ⁷ ,

or in each case optionally mono- to disubstituted by fluorine, chlorine, bromine, C _r C ₃ - alkyl, _Ci-C3 alkoxy, cyano, hydroxy or nitro-substituted pyridine, pyrimidine,

Triazine, thiazole, pyrazole, oxazole or triazole; or R ⁴ and R ⁵ are particularly preferably together with the nitrogen atom to which they are attached, for a saturated or unsaturated 5- or 6-membered ring optionally substituted once or twice by C ₁ -C ₂ -alkyl, which is optionally interrupted by oxygen or sulfur can be;

R ⁶ particularly preferably represents hydrogen, Na ⁺ , K ⁺ , 14 Ca ²⁺ , V ₂ Mg ²⁺ , NH ₄ ⁺ , NH ₃ CH ₃ ⁺ , NH ₂ (CH ₃ ) ₂ ⁺ , NH (CH ₃ ) ₃ ⁺ , NH (C ₂ H ₅ ) ₃ ⁺ , NH ₂ (C ₂ Hj) ₂ ⁺ , NH ₃ C ₂ H ₅ ⁺ , NH ₃ IC ₃ H ₇ ⁺ , NH ₂ (iC ₃ H ₇ ) ₂ ⁺ , NH ₃ -CH ₂ -C ₆ H ₅ ⁺ or N (CH ₃ ) ₃ -H ₂ -C ₆ H ₅ ⁺ ,

in each case optionally mono- to trisubstituted by fluorine, chlorine, Ci-C ₃ alkoxy, C ₁ -C ₃ - alkylthio, cyano, CO ₂ H or CO-OC _r C ₃ alkyl-substituted C _r C ₈ alkyl, C ₁ -C ₈ alkenyl or C] -C ₈ alkynyl, each optionally optionally mono- to trisubstituted by fluorine,

Chlorine, dC ₃ alkyl, C _r C ₃ haloalkyl, C _r C ₃ alkoxy, CN, CO ₂ H or CO-OC ₁ -C ₃ - alkyl-substituted C ₃ -C ₆ cycloalkyl, C ₃ -C ₆ Cycloalkylmethyl or C ₅ -C ₆ cycloalkenyl, which may optionally be interrupted by an oxygen or sulfur atom,

C ₄ haloalkyl, Ci-C ₄ alkoxy, C] -C ₄ haloalkoxy, nitro or cyano substituted in each case optionally mono- to disubstituted by fluorine, chlorine, bromine, Ci-C ₄ alkyl, C _r

Phenyl, pyridyl, thiazolyl, pyrimidyl, benzyl, phenethyl, pyridinylmethyl or thiazolylmethyl;

R ⁷ particularly preferably represents hydrogen, represents in each case optionally mono- to pentasubstituted by fluorine, chlorine, C _r C ₃ alkoxy, C _r C ₃ alkylthio, cyano, CO ₂ H or CO-OC ₁ -C ₃ -alkyl-substituted C -cg alkyl, C ₃ -C ₈ -alkenyl or C ₃ -C ₈ -alkynyl, in each case optionally mono- to trisubstituted by fluorine, chlorine, Ci-C ₄ alkyl, C _r C ₂ -haloalkyl, C ₂ Alkoxy, CN, CO ₂ H or CO-OC _r C ₂ -alkyl-substituted C ₃ -C ₆ -cycloalkyl, C ₃ -C ₆ -cycloalkyl-methyl or C ₅ -C ₆ -cycloalkenyl, which may be replaced by an oxygen or sulfur atom can be interrupted,

in each case optionally mono- to disubstituted by fluorine, chlorine, bromine, C ₁ -C ₃ -alkyl,

C _r C ₃ haloalkyl, _Ci-C3 alkoxy, _Ci-C3 haloalkoxy, nitro or cyano-substituted phenyl, pyridyl, thiazolyl, pyrimidyl, benzyl, phenethyl, pyridinylmethyl or thiazolyl methyl;

R ⁸ particularly preferably represents hydrogen, in each case optionally mono- to trisubstituted by fluorine and / or chlorine, C] -C ₄ alkyl, C ₃ -C ₄ - alkenyl, C ₃ -C ₄ alkynyl, or

C _r C ₄ alkoxy;

or R ⁴ and R ⁷ form particularly preferably with the N-CO or NS (O) i _-2 group to which they are attached, a 4- to 6-membered cycle containing one or more heteroatoms selected from sulfur, oxygen and or may contain nitrogen, wherein oxygen atoms may not be adjacent; or

R ⁷ and R ⁸ are particularly preferably taken together with the nitrogen atom to which they are attached, for a saturated or unsaturated 5- or 6-membered ring optionally substituted once to twice by C ₁ -C ₂ -alkyl, optionally substituted by oxygen or sulfur can be interrupted;

R ⁹ and R ¹⁰ are particularly preferably independently of one another in each case optionally monosubstituted to trisubstituted by fluorine and / or chlorine C _r C ₆ alkyl, C ₃ -C ₆ alkenyl, C ₁ -C ₆ -

Alkoxy, C ₃ -C ₆ alkenyloxy, C ₃ -C ₆ alkynyloxy, Ci-C ₄ alkylthio, C ₃ -C ₄ alkenylthio, each optionally mono- to disubstituted by fluorine, chlorine, C] -C ₂ alkyl , Ci-C ₂ haloalkyl, C] -C ₂ -alkoxy-substituted C ₃ -C ₆ cycloalkoxy, C ₄ -C ₆ -cycloalkenyloxy or C ₃ -C ₆ - alkyloxy cycloalkyl-C] -C _2, for each optionally mono- to disubstituted by fluorine, chlorine, bromine, C, -C ₄ alkyl-Ci-C ₂ haloalkyl, C, -C ₄ alkoxy, C, -C ₂ haloalkoxy, C ₁ -

C ₄ alkylthio, cyano or nitro substituted phenoxy, phenylthio, benzyloxy, benzylthio, pyridinyloxy, pyrazolyloxy, pyridinylthio, pyrimidylthio, thiazolylthio, pyridyl-methyloxy, pyrimidyl-methyloxy, thiazolyl-methyloxy, pyridyl-methylthio, thiazolyl-methylthio or pyrimidyl-methylthio ; or

R ⁹ and R ¹⁰ are particularly preferably taken together with the phosphorus atom to which they are attached, for an optionally mono- to disubstituted by fluorine, chlorine, Ci-C ₂ alkyl, Ci-C ₂ alkoxy or C _r C ₂ haloalkyl substituted five to six membered cycle which may be interrupted by one or two oxygen and / or sulfur atoms; and

R ¹¹ and R ¹² are particularly preferably independently of one another represent in each case optionally mono- to trisubstituted by fluorine or chlorine, Ci-C ₆ alkyl, C ₃ -C ₆ alkenyl or

C ₃ -C ₆ alkynyl.

The compounds of the invention are generally defined by the formula (I). Very particularly preferred substituents, fragments or ranges of the radicals listed in the formulas mentioned above and below are explained below for a very particularly preferred embodiment of the present invention; very particular preference is given here to the compounds of the formulas (I-1) to (I- ³ ) which correspond to formula (I), where the symbols A, B ¹ , B ² , B ³ and B ⁴ are very particularly preferred Meanings have: For the formula (1-1), A = C; B ¹ =; B ² = = Q-GG ² '; ? -; BB ^3J == == rCc-- G ³

and B ⁴ = = C -

for the formula (1-2), A = C; B ¹ = = C-G ¹ ; B ² = = N-; B ⁴ = N -

Il IR ³

and B ³ is a bond;

for the formula (1-3), A = N; B ¹ = ^{N ~} ; B ² = = C - G ² ; B ⁴ = = C

R ³ and B ³ is a bond.

The remaining symbols in the formulas (I-1) to (1-3) have the following very particularly preferred meanings:

X is very particularly preferably hydrogen, chlorine, methyl or trifluoromethyl;

Y very particularly preferably represents (C 1 -C 6) -alkyl, (C 3 -C 6) -alkenyl, (C 3 -C 6) -alkynyl,

(C3-C6) cycloalkyl wherein Y is unsubstituted or substituted by one to three fluorine or chlorine atoms; or

Y is very particularly preferably monosubstituted to trisubstituted phenyl having substituents selected from the group consisting of fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, tert-butyl, methoxy, ethoxy, trifluoromethyl, difluoromethoxy or trifluoromethoxy; or

Y very particularly preferably represents pyridyl which is linked in the 2- or 4-position and may be monosubstituted, disubstituted or differently substituted by fluorine, chlorine, bromine, cyano, methyl, ethyl, methoxy, methylthio or trifluoromethyl; or

Pyrimidyl which is linked in the 4-position and may be monosubstituted to trisubstituted, identically or differently substituted by fluorine, chlorine, bromine, cyano, methyl, ethyl, methoxy,

Methylthio or trifluoromethyl; or

Thienyl which is linked in the 2- or 3-position and may be monosubstituted, disubstituted or differently substituted by fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, methoxy or trifluoromethyl; Z is very particularly preferably chlorine, methoxy, ethoxy, methylthio, ethythio or the

Group N _;

R ²

G ¹ , G ² and G ³ are very particularly preferably each independently hydrogen, chlorine, bromine, methyl, ethyl, trifluoromethyl or cyclopropyl;

L is most preferably oxygen or sulfur;

R ¹ very particularly preferably represents hydrogen, alkyl having 1 to 6 carbon atoms, which is unsubstituted or monosubstituted to trisubstituted, identically or differently, by fluorine, chlorine, methoxy, ethoxy, cyclopropyl, cyclopentyl, cyclohexyl, methylthio or ethylthio; or

R * very particularly preferably represents alkenyl having 3 to 6 carbon atoms which is unsubstituted or monosubstituted to trisubstituted, identically or differently substituted by fluorine, chlorine, methoxy, ethoxy, methylthio or ethylthio; or

R! very particularly preferably represents alkynyl having 3 to 6 carbon atoms which is unsubstituted or monosubstituted to trisubstituted, identically or differently substituted by fluorine, chlorine, methoxy, ethoxy, methylthio or ethylthio; or

R! very particularly preferably represents cycloalkyl having 3 to 6 carbon atoms which is unsubstituted or monosubstituted to trisubstituted, identically or differently substituted by fluorine, chlorine, methyl, ethyl, methoxy or trifluoromethyl;

R ^ is most preferably hydrogen, methyl or ethyl; or

R 1 and R 3 together with the nitrogen atom to which they are attached are very particularly preferably a saturated or unsaturated heterocyclic ring having 3 to 6 ring members, where the heterocycle optionally contains a further nitrogen, oxygen or sulfur atom as ring member and wherein the heterocycle unsubstituted or substituted up to two times by fluorine, chlorine, methyl, ethyl, trifluoromethyl, methoxy or ethoxy;

R ³ is very particularly preferably CO-N ^ or CO-OR ⁶ ; R ⁴ very particularly preferably represents hydrogen, Na ⁺ , K ⁺ , V ₂ Ca ²⁺ , V ₂ Mg ²⁺ , NH ₄ ⁺ , NH ₃ CH ₃ ⁺ , NH ₂ (CH ₃ ) ₂ ⁺ , NH (CH ₃ ) ₃ ⁺ , NH (C ₂ Hs) ₃ ⁺ , NH ₂ (C ₂ Hj) ₂ ⁺ , NH ₃ C ₂ H ₅ ⁺ , NH ₃ IC ₃ H ₇ ⁺ , NH ₂ (iC ₃ H ₇ ) ₂ ⁺ , NH ₃ -CH ₂ -C ₆ H ₅ ⁺ or N (CH ₃ ) ₃ -H ₂ -C ₆ H ₅ ⁺ ,

in each case optionally mono- to trisubstituted by fluorine, chlorine, methoxy, ethoxy, methylthio, ethylthio, cyano, CO-O-methyl or ethyl-substituted CO-O-C _r C ₆ alkyl,

C ₃ -C ₆ alkenyl or C ₃ -C ₆ alkynyl, each optionally optionally mono- to trisubstituted by fluorine, chlorine, methyl, ethyl, trifluoromethyl, methoxy, ethoxy, cyano, CO-O-methyl or CO-O-ethyl substituted C ₃ -C ₆ cycloalkyl;

R.5 very particularly preferably represents hydrogen, represents in each case optionally mono- to trisubstituted by fluorine and / or chlorine-C] _-C6 alkyl, C _r C ₆ alkoxy, C ₃ -C ₆ -

Alkenyl, C ₃ -C ₆ -alkenyloxy or C ₃ -C ₆ -alkynyl, or for the groups COR ⁷ , S (O) ₁ R ⁷ , cyano, COOR ⁷ ,

or

R ⁴ and R ⁵ are most preferably taken together with the nitrogen atom to which they are attached, for saturated 5- or 6-membered ring, which may optionally be interrupted by oxygen or sulfur;

R ⁶ very particularly preferably represents hydrogen, Na ⁺ , K ⁺ , V ₂ Ca ²⁺ , V ₂ Mg ²⁺ , NH ₄ ⁺ , NH ₃ CH ₃ ⁺ , NH ₂ (CH ₃ ) ₂ ⁺ , NH (CH ₃ ) ₃ ⁺ , NH (C ₂ H ₅ ) ₃ ⁺ , NH ₂ (C ₂ H ₅ ) /, NH ₃ C ₂ H ₅ ⁺ , NH ₃ IC ₃ H ₇ ⁺ , NH ₂ (iC ₃ H ₇ ) ₂ ⁺ , NH ₃ -CH ₂ -C ₆ H ₅ ⁺ or N (CH ₃ ) ₃ -H ₂ -C ₆ H ₅ ⁺ ,

each optionally optionally mono- to trisubstituted by fluorine, chlorine, methoxy, ethoxy, methylthio, ethylthio, cyano, CO ₂ H, CO-O-methyl or CO-O-ethyl substituted CpC ₆ - alkyl, C ₃ -C ₆ alkenyl or C ₃ -C ₆ alkynyl;

R ⁷ very particularly preferably represents hydrogen, in each case optionally monosubstituted to trisubstituted by fluorine, chlorine, methoxy, ethoxy, methylthio, ethylthio, cyano, CO-O-

Methyl or ethyl-substituted CO-O-C _r C ₆ alkyl, C ₃ -C ₆ -alkenyl or C ₃ -C ₆ -alkynyl, represents in each case optionally monosubstituted by fluorine, chlorine, methyl, ethyl, methoxy, trifluoromethyl, cyano CO ₂ H, CO-O-methyl or CO-O-ethyl-substituted C ₃ -C ₆ - cycloalkyl, C ₃ -C ₆ -cycloalkyl-methyl, or _C5-C6 cycloalkenyl, which is optionally may be interrupted by an oxygen or sulfur atom, each optionally optionally mono- to disubstituted by fluorine, chlorine, bromine methyl, trifluoromethyl, methoxy-substituted phenyl, pyridyl, thiazolyl, pyrimidyl, benzyl, phenethyl, pyridinylmethyl or thiazolylmethyl;

R ⁸ most preferably represents hydrogen, methyl, ethyl, propyl, iso-propyl, AHyI, propargyl, C ₃ -C ₄ alkenyl, methoxy or ethoxy; or

R ⁷ and R ⁸ are most preferably taken together with the nitrogen atom to which they are attached, for a saturated 5- or 6-membered ring, which may optionally be interrupted by oxygen or sulfur; and

R ⁹ and R ¹⁰ are very particularly preferably each independently of the other preferably optionally mono- to trisubstituted by fluorine and / or chlorine methyl, ethyl, methoxy, ethoxy, propoxy, i-propoxy, butoxy, alkoxy, methylthio, ethylthio, propylthio, butylthio, i-Propylthio, sec-butylthio, allylthio.

The compounds of the invention are generally defined by the formula (I). Especially particularly preferred substituents, fragments or ranges of the radicals listed in the formulas mentioned above and below are explained below for a particularly particularly preferred embodiment of the present invention; especially particularly preferred are the compounds of the formulas (1-3) which correspond to the formula (I), where the symbols A, B ¹ , B ² , B ³ and B ^{4 have} the following particularly particularly particularly preferred meanings:

For the formula (1-3), A = N; B ¹ = ^{N ~} ; B ² = = C - G ² ; B ⁴ = = C

IIR ³

and B ^ is a bond.

The remaining symbols in the formula (1-3) have the following particularly particularly preferred meanings:

X is particularly particularly preferably hydrogen, chlorine, methyl or trifluoromethyl;

Y is particularly particularly preferably (C 1 -C 8) -alkyl, (C 3 -G) -alkenyl, (C 3 -C 6) -alkynyl, (C 3 -C 9) -cycloalkyl, where Y is unsubstituted or substituted by one to three fluoro or chlorine atoms is substituted; or Y is especially particularly preferably monosubstituted to trisubstituted phenyl having substituents selected from the group consisting of fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, tert-butyl, methoxy, ethoxy, trifluoromethyl, difluoromethoxy or trifluoromethoxy; or

Y is particularly particularly preferably pyridyl which is linked in the 2- or 4-position and may be monosubstituted, disubstituted or differently substituted by fluorine, chlorine, bromine, cyano, methyl, ethyl, methoxy, methylthio or trifluoromethyl; or

Pyrimidyl which is linked in the 4-position and may be monosubstituted to trisubstituted, identically or differently substituted by fluorine, chlorine, bromine, cyano, methyl, ethyl, methoxy, methylthio or trifluoromethyl; or

Thienyl which is linked in the 2- or 3-position and may be monosubstituted, disubstituted or differently substituted by fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, methoxy or trifluoromethyl;

Z is particularly particularly preferably chlorine, methoxy, ethoxy, methylthio,

_ ^{/ R1} Ethythio or the group N;

R ²

G ¹ , G ² and G ³ are very particularly preferably, independently of one another, hydrogen, chlorine, bromine, methyl, ethyl, trifluoromethyl or cyclopropyl;

In particular, L is very particularly preferably oxygen or sulfur;

In particular, R ¹ very particularly preferably represents hydrogen, alkyl having 1 to 6 carbon atoms, which is unsubstituted or monosubstituted to trisubstituted, identically or differently, by fluorine, chlorine, methoxy, ethoxy, cyclopropyl, cyclopentyl, cyclohexyl, methylthio or ethylthio; or

R.1 is particularly particularly preferably alkenyl having 3 to 6 carbon atoms, which is unsubstituted or monosubstituted to trisubstituted by identical or different substituents by fluorine, chlorine, methoxy, ethoxy, methylthio or ethylthio; or

R! is particularly particularly preferred for alkynyl having 3 to 6 carbon atoms, which is unsubstituted or monosubstituted to trisubstituted by identical or different substituents by fluorine, chlorine, methoxy, ethoxy, methylthio or ethylthio; or In particular, R 1 very particularly preferably represents cycloalkyl having 3 to 6 carbon atoms which is unsubstituted or monosubstituted to trisubstituted, identically or differently substituted by fluorine, chlorine, methyl, ethyl, methoxy or trifluoromethyl;

R.2 is particularly particularly preferably hydrogen, methyl or ethyl; or

More particularly, R1 and R2, together with the nitrogen atom to which they are attached, represent a saturated or unsaturated heterocyclic ring having from 3 to 6 ring members, where the heterocycle optionally represents another nitrogen, oxygen or sulfur atom as ring member and wherein the heterocycle may be unsubstituted or substituted up to twice by fluorine, chlorine, methyl,

Ethyl, trifluoromethyl, methoxy or ethoxy;

R 3

R is particularly particularly preferably hydrogen,

R-> is especially particularly preferably hydrogen, in each case optionally monosubstituted to trisubstituted by fluorine and / or chlorine, C ₁ -C ₆ -alkyl, C ₁ -C ₆ -alkoxy,

C ₃ -C ₆ alkenyl, C ₃ -C ₆ alkenyloxy or C ₃ -C ₆ alkynyl, or for the groups COR ⁷ , S (O) _j . 2R ⁷ , Cyano, COOR ⁷ ,

or R ⁴ and R ⁵ are particularly particularly preferred together with the nitrogen atom to which they are attached, for saturated 5- or 6-membered ring, which may optionally be interrupted by oxygen or sulfur;

R ⁶ is particularly particularly preferably hydrogen,

in each case optionally monosubstituted to trisubstituted by fluorine, chlorine, methoxy, ethoxy,

Methylthio, ethylthio, cyano, CO ₂ H, CO-O-methyl or CO-O-ethyl substituted CpC ₆ -alkyl, C ₃ -C ₆ -alkenyl or C ₃ -C ₆ -alkynyl;

R ⁷ particularly particularly preferably represents hydrogen, in each case optionally monosubstituted to trisubstituted by fluorine, chlorine, methoxy, ethoxy, methylthio, ethylthio, cyano, CO-O-methyl or CO-O-ethyl, C _r C ₆ -alkyl, C ₃ -C ₆ alkenyl or C ₃ -C ₆ -

Alkynyl, each optionally optionally substituted by fluorine, chlorine, methyl, ethyl, methoxy, trifluoromethyl, cyano, CO ₂ H, CO-O-methyl or CO-O-ethyl substituted C ₃ -C ₆ - cycloalkyl, C ₃ -C ₆ cycloalkyl-methyl, or _C5-C6 cycloalkenyl, which may be optionally interrupted by an oxygen or sulfur atom, in each case optionally mono- to disubstituted by fluorine, chlorine, bromine, methyl, trifluoromethyl,

Methoxy-substituted phenyl, pyridyl, thiazolyl, pyrimidyl, benzyl, phenethyl, pyridinylmethyl or thiazolylmethyl;

In particular, R ⁸ very particularly preferably represents hydrogen, methyl, ethyl, propyl, isopropyl, allyl, propargyl, C ₃ -C ₄ -alkenyl, methoxy or ethoxy; or

More particularly, R ⁷ and R ⁸ together with the nitrogen atom to which they are attached represent a saturated 5- or 6-membered ring which may optionally be interrupted by oxygen or sulfur; and

R ⁹ and R ¹⁰ are particularly particularly preferably each independently of one another in each case optionally mono- to trisubstituted by fluorine and / or chlorine, methyl, ethyl, methoxy, ethoxy, propoxy, isopropoxy, butoxy, alkyloxy, methylthio, ethylthio,

Propylthio, butylthio, i-propylthio, sec-butylthio, allylthio.

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. They apply accordingly to the end products as well as to the precursors and intermediates. Preference according to the invention is given to the compounds of the formula (1) which contain a combination of the meanings listed above as being preferred (preferred).

Particular preference according to the invention is given to the compounds of the formula (I) in which a combination of the meanings listed above as being particularly preferred is present.

Very particular preference according to the invention is given to the compounds of the formula (I) which contain a combination of the meanings given above as being very particularly preferred.

Particular preference is given in accordance with the invention to the compounds of the formula (I) which contain a combination of the meanings given above as being very particularly preferred.

Especially preferred compounds according to the invention are the compounds of the formula (I) which contain a combination of the meanings given above as being particularly particularly preferred.

Saturated or unsaturated hydrocarbon radicals, such as alkyl or alkenyl, may also be used in conjunction with heteroatoms, e.g. in alkoxy, as far as possible, in each case straight-chain or branched.

Unless otherwise specified, optionally substituted radicals may be monosubstituted or polysubstituted, with multiple substituents the substituents being the same or different.

It has already been described in the literature that the effect of various active substances can be increased by adding ammonium salts. However, they are salts acting as detergent (eg WO 95/017817) or salts with longer alkyl and / or aryl substituents which have a permeabilizing effect or increase the solubility of the active ingredient (eg EP-A 0 453 086, EP-A 0 664 081, FR-A 2 600 494, US 4 844 734, US 5 462 912, US 5 538 937, US-A 03/0224939, US-A 05/0009880, US-A 05/0096386). Furthermore, the prior art describes the effect only for certain active ingredients and / or certain applications of the corresponding agents. In still other cases are salts of sulfonic acids, in which the acids themselves paralyze acting on insects (US 2,842,476). An increase in activity, for example, by ammonium sulfate is described, for example, for the herbicides glyphosate and phosphinothricin (US Pat. No. 6,645,914, EP-A2 0 036 106). A corresponding effect on insecticides is neither disclosed nor suggested by this prior art. Also, the use of ammonium sulfate as a formulation aid is described for certain active ingredients and applications (WO 92/16108), but it is there to stabilize the formulation, not to increase the effect.

It has now been found, completely surprisingly, that the effect of insecticides and / or acaricides from the class of heterocyclic carboxylic acid derivatives (I) by the addition of ammonium or phosphonium salts to the application solution or by the incorporation of these salts into a formulation containing heterocyclic carboxylic acid derivatives (I. ) can be increased significantly. The present invention thus relates to the use of ammonium or phosphonium salts for increasing the efficacy of plant protection products containing insecticidally and / or acaricidally active heterocyclic carboxylic acid derivatives (I) as active ingredient. The invention also relates to compositions containing insecticidally and / or acaricidally active heterocyclic carboxylic acid derivatives (I) and the activity-enhancing ammonium or phosphonium salts, both formulated active ingredients and ready-to-use agents (spray liquors). Finally, the invention further relates to the use of these agents for controlling noxious insects and / or spider mites.

Ammonium and phosphonium salts which according to the invention increase the activity of crop protection agents containing heterocyclic carboxylic acid derivatives (I) are defined by formula (II)

in which

Q is nitrogen or phosphorus,

Q is preferably nitrogen,

R ²⁶ , R ²⁷ , R ²⁸ and R ²⁹ independently of one another represent hydrogen or in each case optionally substituted CpCg-alkyl or mono- or polyunsaturated, optionally substituted C 1 -C 8 -alkylene, where the substituents can be selected from halogen, nitro and cyano,

R ²⁶ , R ²⁷ ₅ R ²⁸ and R ²⁹ preferably independently of one another represent hydrogen or in each case optionally substituted C 1 -C ₄ -alkyl, where the substituents can be selected from halogen, nitro and cyano, R ²⁶ , R ²⁷ , R ²⁸ and R ^{29 more} preferably independently of one another are hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, s-butyl or t-butyl,

R ²⁶ , R ²⁷ , R ²⁸ and R ²⁹ most preferably represent hydrogen,

R ²⁶ , R ²⁷ , R ²⁸ and R ²⁹ furthermore very particularly preferably mean at the same time methyl or simultaneously ethyl,

n is 1, 2, 3 or 4,

n is preferably 1 or 2,

R ^{30 is} an inorganic or organic anion,

R ^{30 is} preferably hydrogen carbonate, tetraborate, fluoride, bromide, iodide, chloride, monohydrogen phosphate, dihydrogen phosphate, hydrogen sulfate, tartrate, sulfate, nitrate,

Thiosulphate, thiocyanate, formate, lactate, acetate, propionate, butyrate, pentanoate, citrate or oxalate,

R ³⁰ furthermore preferably represents carbonate, pentaborate, sulfite, benzoate, hydrogen oxalate, hydrogen citrate, methyl sulfate or tetrafluoroborate,

R ³⁰ particularly preferably represents lactate, sulfate, nitrate, thiosulphate, thiocyanate, citrate, oxalate, acetate or formate,

R ^{30 is} also particularly preferred for monohydrogen phosphate or dihydrogen phosphate, and

R ^{30 is} very particularly preferred for thiocyanate, dihydrogen phosphate, monohydrogen phosphate or sulfate.

The ammonium and phosphonium salts of the formula (II) can be used in a wide concentration range for increasing the effect of crop protection agents containing heterocyclic carboxylic acid derivatives (1). In general, the ammonium or phosphonium salts in the ready-to-use crop protection agent are used in a concentration of 0.5 to 80 mmol / l, preferably 0.75 to 37.5 mmol / l, particularly preferably 1.5 to 25 mmol / l. In the case of a formulated product, the concentration of ammonium and / or phosphonium salt in the formulation is chosen so that, after dilution of the formulation to the desired active ingredient concentration, it is expressed in this general, preferred or particularly preferred ranges. The concentration of the salt in the formulation is usually 1-50 wt .-%.

In a preferred embodiment of the invention, not only an ammonium and / or phosphonium salt, but additionally a penetration promoter is added to the crop protection agents to increase the effect. It can be described as completely surprising that even in these cases an even greater increase in activity can be observed. The present invention thus also relates to the use of a combination of penetration promoters and ammonium and / or phosphonium salts to increase the efficacy of crop protection agents containing insecticidally and / or acaricidally active heterocyclic carboxylic acid derivatives (I) as active ingredient. The invention also relates to compositions containing insecticidally and / or acaricidally active heterocyclic carboxylic acid derivatives (I), penetrants and ammonium and / or phosphonium salts, both formulated active ingredients and ready-to-use agents (spray liquors). Finally, the subject matter of the invention is the use of these agents for controlling harmful insects.

Suitable penetration promoters in the present context are all those substances which are usually used to improve the penetration of agrochemical active substances into plants. Penetration promoters are in this context defined by the fact that they can penetrate from the aqueous spray mixture and / or from the spray coating in the cuticle of the plant and thereby increase the material mobility (mobility) of active ingredients in the cuticle. The method described in the literature (Baur et al., 1997, Pesticide Science 51, 131-152) can be used to determine this property.

Suitable penetration promoters are, for example, alkanol alkoxylates. Penetration promoters according to the invention are alkanol alkoxylates of the formula

RO - (- AO) _v -R '(III)

in which

R is straight-chain or branched alkyl having 4 to 20 carbon atoms,

R ^{1 is} hydrogen, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, t-butyl, n-pentyl or n-hexyl,

AO stands for an ethylene oxide radical, a propylene oxide radical, a butylene oxide radical or mixtures of ethylene oxide and propylene oxide radicals or butylene oxide radicals and v stands for numbers from 2 to 30.

A preferred group of penetration enhancers are alkanol alkoxylates of the formula

RO - (- EO-) _n -R '(III-a) in which R has the meaning given above,

R 'has the meaning given above, EO is -CH ₂ -CH ₂ -O- and n is a number from 2 to 20.

Another preferred group of penetration promoters are alkanol alkoxylates of the formula RO - (- EO-) _p - (- PO-) _q -R '(III-b) in which

R has the abovementioned meaning, R 'has the abovementioned meaning, EO is -CH ₂ -CH ₂ -O-, PO is C ^o H ^π 2r-C y H p - Ou,

CH ₃

p stands for numbers from 1 to 10 and q stands for numbers from 1 to 10. Another preferred group of penetration promoters are alkanol alkoxylates of the formula

RO - (- PO-) _r - (EO-) _s -R '(iπ-c) in which

R has the meaning given above, R 'has the meaning given above, EO is -CH 2 -CH 2 -O-,

PO is CH-CH-0 _;

CH ₃

r is a number from 1 to 10 and s is a number from 1 to 10. Another preferred group of penetration enhancers are alkanol alkoxylates of the formula

RO - (- EO-) _p - (- BO-) _q -R '(md) in which

R and R 'have the meanings given above, EO is CH ₂ -CH ₂ -O-, BO is --CH _r CH _r CH-O,

CH ₃

p stands for numbers from 1 to 10 and q stands for numbers from 1 to 10. Another preferred group of penetration enhancers are alkanol alkoxylates of the formula

RO - (- BO-) _r - (- EO-) _s -R '(III-e) in which

R and R have the meanings given above,

BO represents - CH _r CH _r CH-O,

CH ₃

EO is CH ₂ -CH ₂ -O-, r is a number from 1 to 10 and s is a number from 1 to 10. Another preferred group of penetration promoters are alkanol alkoxylates of the formula

CH ₃ - (CH ₂ ) t -CH ₂ -O - (- CH ₂ -CH ₂ -O-) _u -R '(IH-O

in which

R 'has the meaning given above,

t stands for numbers from 8 to 13

u stands for numbers from 6 to 17.

In the formulas given above

R is preferably butyl, isobutyl, n-pentyl, i-pentyl, neopentyl, n-hexyl, i-hexyl, n-octyl, i-octyl, 2-ethylhexyl, nonyl, i-nonyl, decyl, n Dodecyl, i-dodecyl, lauryl, myristyl, i-tridecyl, trimethyl-nonyl, palmityl, stearyl or eicosyl.

As an example of an alkanol alkoxylate of the formula (III-c) is 2-ethyl-hexyl alkoxylate of the formula

in which

EO stands for -CH ₂ -CH ₂ -O-,

the numbers 8 and 6 represent average values called.

As an example of an alkanol alkoxylate of the formula (III-d) is the formula

CH ₃ - (CH ₂ ) ₁₀ -O - (- EO-) ₆ - (- BO-) ₂ -CH ₃ (III-d-1)

in which

EO is CH ₂ -CH ₂ -O-, BO stands for - CH ^ -CH _j -CH-O and

CH ₃

the numbers 10, 6 and 2 represent average values called.

Particularly preferred alkanol alkoxylates of the formula (ITI-f) are compounds of this formula in which

t for numbers from 9 to 12 and

u for numbers from 7 to 9

stands.

Very particular preference is given to alkanol alkoxylate of the formula (III-F-I)

CH ₃ - (CH2) t-CH2-O - (- CH ₂ -CH 2 -O-) _u -H (ffl-f- 1)

in which

t stands for the average 10.5 and

u stands for the average 8.4.

The alkanol alkoxylates are generally defined by the above formulas. These substances are mixtures of substances of the specified type with different chain lengths. For the indices, therefore, average values are calculated, which can also differ from whole numbers.

The alkanol alkoxylates of the formulas given are known and are partly available commercially or can be prepared by known methods (compare WO 98/35 553, WO 00/35 278 and EP-A 0 681 865).

Examples of suitable penetration promoters are substances which promote the availability of the compounds of the formula (I) in the spray coating. These include, for example, mineral or vegetable oils. Suitable oils are all mineral or vegetable, optionally modified, oils which can usually be used in agrochemical compositions. Examples include sunflower oil, rapeseed oil, olive oil, castor oil, rapeseed oil, corn kernel oil, cottonseed oil and soybean oil or the esters of said oils. Rape oil, sunflower oil and their methyl or ethyl esters are preferred. The concentration of penetration promoter can be varied within a wide range in the agents according to the invention. In the case of a formulated crop protection agent, it is generally from 1 to 95% by weight, preferably from 1 to 55% by weight, more preferably from 15 to 40% by weight. In the ready-to-use agents (spray liquors), the concentration is generally between 0.1 and 10 g / l, preferably between 0.5 and 5 g / l.

Plant protection agents according to the invention may also contain other components, for example surfactants or dispersing aids or emulsifiers.

Suitable nonionic surfactants or dispersing agents are all substances of this type which can usually be used in agrochemical compositions. Preference is given to polyethylene oxide-polypropylene oxide block copolymers, polyethylene glycol ethers of linear alcohols, reaction products of fatty acids with ethylene oxide and / or propylene oxide, furthermore polyvinyl alcohol, polyvinylpyrrolidone, copolymers of polyvinyl alcohol and polyvinylpyrrolidone and copolymers of (meth) acrylic acid and (meth) acrylic esters , furthermore alkyl ethoxylates and alkylaryl ethoxylates, which may optionally be phosphated and optionally neutralized with bases, wherein sorbitol ethoxylates may be mentioned by way of example, and polyoxyalkyleneamine derivatives.

Suitable anionic surfactants are all substances of this type conventionally usable in agrochemical compositions. Preference is given to alkali metal and alkaline earth metal salts of alkyl sulfonic acids or alkylaryl sulfonic acids.

Another preferred group of anionic surfactants or dispersing agents are salts of polystyrenesulfonic acids which are sparingly soluble in vegetable oil, salts of polyvinylsulfonic acids, salts of naphthalenesulfonic acid-formaldehyde condensation products, salts of condensation products of naphthalenesulfonic acid, phenolsulfonic acid and formaldehyde and salts of lignosulfonic acid.

Suitable additives which may be present in the formulations according to the invention are emulsifiers, foam-inhibiting agents, preservatives, antioxidants, dyes and inert fillers.

Preferred emulsifiers are ethoxylated nonylphenols, reaction products of alkylphenols with ethylene oxide and / or propylene oxide, ethoxylated arylalkylphenols, furthermore ethoxylated and propoxylated arylalkylphenols, and sulfated or phosphated arylalkyl ethoxylates or ethoxy-propoxylates, sorbitan derivatives such as polyethylene oxide sorbitan fatty acid esters and sorbitan Fatty acid esters, may be mentioned as examples. The active compounds according to the invention are suitable for plant tolerance, favorable warm-blood toxicity and good environmental compatibility for the protection of plants and plant organs, for increasing crop yields, improving the quality of the crop and for controlling animal pests, in particular insects, arachnids, helminths, nematodes and molluscs which are found in agriculture, horticulture, livestock, forests, gardens and recreational facilities, in the protection of materials and materials and in the hygiene sector. They can preferably be used as crop protection agents. They are effective against normally sensitive and resistant species as well as against all or individual stages of development. The above mentioned pests include:

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

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

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

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

From the order of Coleoptera e.g. Acanthoscelides obtectus, Adoretus spp., Agelastica alni,

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

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

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

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

From the order of the Heteroptera eg Anasa tristis, Antestiopsis spp., Blissus spp., Calocoris spp., Campylomma livida, Cavelerius spp., Cimex spp., Creontiades dilutus, Dasynus piperis, Dichelops furcatus, Diconocoris hewetti, Dysdercus spp., Euschistus spp , Eurygaster spp., Heliopeltis spp., Horcias nobilellus, Leptocorisa spp., Leptoglossus phyllopus, Lygus spp., Macropes excavatus, Miridae, Nezara spp., Oebalus spp., Pentomidae, Piesma quadrata, Piezodorus spp., Psallus seriatus, Pseudacysta persea, Rhodnius spp., Sahlbergella singularis, Scotinophora spp., Stephanitis nashi, Tibraca spp., Triatoma spp. From the order of Homoptera eg Acyrthosipon spp., Aeneolamia spp., Agonoscena spp., Aleurodes spp., Aleurolobus barodensis, Aleurothrixus spp., Amrasca spp., Anuraphis cardui, Aonidiella spp., Aphanostigma piri, Aphis spp., Arboridia apicalis, Aspidiella spp., Aspidiotus spp., Atanus spp., Aulacorthum solani, Bemisia spp., Brachycaudus helichrysii, Brachycolus spp., Brevicoryne brassicae, Calligypona marginata, Carneocephala fulgida, Ceratovacuna lanigera, Cercopidae, Ceroplastes spp., Chaetosiphon fragaefolii, Chionetis tegalensis, Chlorita onukii, Chromaphis juglandicola, Chrysomphalus ficus, Cicadulina mbila, Coccomytilus halli, Coccus spp., Cryptomyzus ribis, Dalbulus spp., Dialeurodes spp., Diaphorina spp., Diaspis spp., Doralis Sp., Drosicha spp., Dysaphis spp., Dysmicoccus spp., Empoasca spp., Eriosoma spp., Erythroneura spp., Euscelis bilobatus, Geococcus coffeae, Homalodisca coagulata, Hyalopterus arundinis, Icerya spp., Idiocerus spp., Idioscopus spp. , Laodelphax striatellus, Lecanium spp., Lepidosaphes spp., Lipaphis erysimi, Macrosiphum spp., Mahanarva fimbriolata, Melanaphis sacchari, Metcalfiella spp., Metopolophium dirhodum, Monellia costalis, Monelliopsis pecanis, Myzus spp., Nasonovia ribisnigri, Nephotettix spp., Nilaparvata lugens, Oncometopia spp., Orthezia praelonga, Parabemisia myricae, Paratrioza spp., Parlatoria spp., Pemphigus spp., Peregrinus maidis, Phenacoccus spp., Phloeomyzus passerinii, Phorodon humuli, Phylloxera spp., Pinnaspis aspidistrae, Planococcus spp. Protopulvinaria pyriformis, Pseudaulacaspis pentagona, Pseudococcus spp., Psylla spp., Pteromalus spp., Pyrilla spp., Quadraspidiotus spp., Quesada gigas, Rastrococcus spp., Rhopalosiphum spp., Saissetia spp., Scaphoides tita nus, Schizaphis graminum, Selenaspidus articulatus, Sogata spp., Sogatella furcifera, Sogatodes spp., Stictocephala festina, Tenalaphara malayensis, Tinocallis caryaefoliae, Tomaspis spp., Toxoptera spp., Tri- aleurodes vaporariorum, Trioza spp., Typhlocyba spp., Unaspis spp., Viteus vitifolii. From the order of Hymenoptera eg Diprion spp., Hoplocampa spp., Lasius spp., Monomorium pharaonis, Vespa spp.

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

From the order of Orthoptera, for example, Acheta domesticus, Blatta orientalis, Blattella germanica, Gryllotalpa spp., Leucophaea maderae, Locusta spp., Melanoplus spp., Periplaneta americana, Schistocerca gregaria. From the order of Siphonaptera eg Ceratophyllus spp., Xenopsylla cheopis. From the order of Symphyla eg Scutigerella immaculata. From the order of the Thysanoptera eg Baliothrips biformis, Enneothrips flavens, Frankliniella spp., Heliothrips spp., Hercinothrips femoralis, Kakothrips spp., Rhipiphorothrips cruentatus, Scirtothrips spp., Taeniothrips cardamoni, Thrips spp .. From the order of Thysanura eg Lepisma saccharina. The plant parasitic nematodes include, for example, Anguina spp., Aphelenchoides spp., Belonoaimus spp., Bursaphelenchus spp., Ditylenchus dipsaci, Globodera spp., Heliocotylenchus spp., Heterodera spp., Longidorus spp., Meloidogyne spp., Pratylenchus spp., Radopholus similis, Rotylenchus spp., Trichodorus spp., Tylenchorhynchus spp., Tylenchulus spp., Tylenchulus semipenetrans, Xiphinema spp. The compounds of the formula (I) according to the invention are distinguished, in particular, by potent activity against insects, parasites of the subclass of Acari (Acarina ) (such as mites, spider mites and / or ticks) and / or nematodes.

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

The active compounds can be converted into the customary formulations, such as solutions, emulsions, wettable powders, water- and oil-based suspensions, powders, dusts, pastes, soluble powders, soluble granules, scattering granules, suspension-emulsion concentrates, active substance-impregnated natural substances, active substance impregnated synthetic materials, fertilizers and micro-encapsulants in polymeric materials.

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

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

Suitable extenders are, for example, water, polar and non-polar organic chemical liquids, for example from the classes of aromatic and non-aromatic hydrocarbons (such as paraffins, Alkylbenzenes, alkylnaphthalenes, chlorobenzenes), alcohols and polyols (which may also be substituted, etherified and / or esterified), ketones (such as acetone, cyclohexanone), esters (including fats and oils) and (poly) ethers, the simple and substituted amines, amides, lactams (such as N-alkylpyrrolidones) and lactones, the sulfones and sulfoxides (such as dimethylsulfoxide).

In the case of using water as extender, for example, organic solvents can also be used as auxiliary solvents. Suitable liquid solvents are essentially: aromatics, such as xylene, toluene, or alkylnaphthalenes, chlorinated aromatics and chlorinated aliphatic hydrocarbons, such as chlorobenzenes, chloroethylenes or methylene chloride, aliphatic hydrocarbons, such as cyclohexane or paraffins, for example petroleum fractions, mineral and vegetable oils, alcohols such as butanol or glycol and their ethers and esters, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents such as dimethyl sulfoxide, and water. Suitable solid carriers are: for example, 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: eg broken and fractionated natural rocks such as calcite, marble, pumice, sepiolite, dolomite and synthetic granules of inorganic and organic flours and granules of organic material such as paper, sawdust, coconut shells, corn cobs and tobacco stalks; suitable emulsifiers and / or foam formers are: for example nonionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, for example alkylaryl polyglycol ethers, alkylsulfonates, alkyl sulfates, arylsulfonates and protein hydrolysates; suitable dispersants are nonionic and / or ionic substances, for example from the classes of alcohol POE and / or POP ethers, acid and / or POPPOE esters, alkylaryl and / or POP POE ethers, fatty and / or POP-POE adducts, POE and / or POP polyol derivatives, POE and / or POP sorbitan or sugar adducts, alkyl or aryl sulfates, sulfonates and phosphates or the corresponding PO-ether adducts. Further suitable oligo- or polymers, for example starting from vinylic monomers, from acrylic acid, from EO and / or PO alone or in combination with, for example, (poly) alcohols or (poly) amines. Furthermore, find use lignin and its sulfonic acid derivatives, simple and modified celluloses, aromatic and / or aliphatic sulfonic acids and their adducts with formaldehyde. Adhesives such as carboxymethylcellulose, natural and synthetic powdery, granular or latex-type polymers such as gum arabic, polyvinyl alcohol, polyvinyl acetate, and natural phospholipids such as cephalins and lecithins and synthetic phospholipids may be used in the formulations. Dyes such as inorganic pigments such as iron oxide, titanium oxide, ferrocyan blue and organic dyes such as alizarin, azo and metal phthalocyanine dyes and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc can be used. Other additives may be fragrances, mineral or vegetable optionally modified oils, waxes and nutrients (also trace nutrients), such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc.

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

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

The active ingredient according to the invention can be used in its commercial formulations as well as in the formulations prepared from these formulations in admixture with other active ingredients such as

Insecticides, attractants, sterilants, bactericides, acaricides, nematicides, fungicides, growth regulators, herbicides, safeners, fertilizers or semiochemicals.

Particularly favorable mixing partners are e.g. the following: Fungicides:

Inhibitors of nucleic acid synthesis

Benalaxyl, benalaxyl-M, bupirimate, chiralaxyl, clozylacon, dimethirimol, ethirimol, furalaxyl, hymexazole, mefenoxam, metalaxyl, metalaxyl-M, ofurace, oxadixyl, oxolinic acid

Inhibitors of mitosis and cell division

Benomyl, Carbendazim, Diethofencarb, Ethaboxam, Fuberidazole, Pencycuron, Thiabendazole, Thiophanate-methyl, Zoxamide

Inhibitors of the respiratory chain complex I

diflumetorim

Respiratory chain complex II inhibitors

Boscalid, Carboxin, Fenfuram, Flutolanil, Furametpyr, Furmecyclox, Mepronil, Oxycarboxin, Penthiopyrad, Thifluzamide Inhibitors of the respiratory chain complex IH

Azoxystrobin, Cyazofamide, Dimoxystrobin, Enestrobin, Famoxadone, Fenamidon, Fluoxastrobin, Kresoximmethyl, Metominostrobin, Orysastrobin, Pyraclostrobin, Picoxystrobin, Trifloxystrobin

decoupler

Dinocap, fluazinam

Inhibitors of ATP production

Fentin acetate, fentin chloride, fentin hydroxide, silthiofam

Inhibitors of amino acid and protein biosynthesis

Andoprim, blasticidin-S, cyprodinil, kasugamycin, kasugamycin hydrochloride hydrate,

Mepanipyrim, pyrimethanil

Inhibitors of signal transduction

Fenpiclonil, fludioxonil, quinoxyfen

Inhibitors of fat and membrane synthesis

Chlozolinate, iprodione, procymidone, vinclozolin

Ampropylfos, Potassium Ampropylfos, Edifenphos, Etridiazole, Iprobenfos (IBP), Isoprothiolane, Pyrazophos

Tolclofos-methyl, biphenyl

Iodocarb, propamocarb, propamocarb hydrochloride, propamocarb-fosetylate

Inhibitors of ergosterol biosynthesis

fenhexamid,

Azaconazole, bitertanol, bromuconazole, cyproconazole, diclobutrazole, difenoconazole, diniconazole, diniconazole-M, epoxiconazole, etaconazole, fenarimol, fenbuconazole, fluquinconazole, flurprimidol, flusilazole, flutriafol, furconazole, furconazole-cis, hexaconazole, imazalil, imazalil sulfate, imibenconazole, ipconazole, metconazole , Myclobutanil,

Nuarimol, Oxpoconazole, Paclobutrazol, Penconazole, Pefurazoate Prochloraz, Propiconazole, Prothioconazole, Pyrifenox, Simeconazole, Tebuconazole, Tetraconazole, Triadimefon, Triadimenol, Triflumizole Triforin, Triticonazole, Uniconazole, Voriconazole, Viniconazole, Aldimoφh, dodemorph, dodemoφhacetate, fenpropidin, fenpropimoφh, spiroxamine, tridemoφh,

Naftifine, pyributicarb, terbinafine

Inhibitors of cell wall synthesis

Benthiavalicarb, Bialaphos, Dimethomoφh, Flumoφh, Iprovalicarb, Mandipropamid,

Polyoxins, polyoxorim, validamycin A

Inhibitors of melanin biosynthesis

Caφropamid, diclocymet, fenoxanil, phthalide, pyroquilon, tricyclazole

induction of resistance

Acibenzolar-S-methyl, probenazole, tiadinil

Multisite

Captafol, captan, chlorothalonil, copper salts such as: copper hydroxide, copper naphthenate, copper oxychloride, copper sulfate, copper oxide, oxine-copper and bordeaux mixture, dichlofluanid, dithianon, dodine, dodine free base, ferbam, folpet, fluorofolpet, guazatine, guazatin acetate, iminoctadine, iminoctadinal besylate, Iminoctadine triacetate, mancopper,

Mancozeb, Maneb, Metiram, Metiram Zinc, propineb, sulfur and sulfur preparations containing calcium polysulphide, thiram, tolylfluanid, zineb, ziram

Other fungicides

Amibromdole, benthiazole, bethoxazine, capsimycin, carvone, quinomethionate, chloropicrin, cufraneb, cyflufenamid, cymoxanil, dazomet, debacarb, diclomezine, dichlorophen,

Diclorane, difenzoquat, difenzoquat methylsulphate, diphenylamine, ferimzone, flumetover, flusulfamide, fluopicolide, fluoroimide, fosetyl-aluminum, fosetyl-caclium, fosetyl-sodium, hexachlorobenzene, 8-hydroxyquinoline sulfate, irumamycin, methasulphocarb, metrafenone, methyl isothiocyanate, mildiomycin, natamycin, Nickel dimethyldithiocarbamate, nitrothal isopropyl, octhilinone, oxamocarb, oxyfenthiine,

Pentachlorophenol and salts, 2-phenylphenol and salts, piperine, propanosine sodium, proquinazide, pyribencarb, pyrrolnitrin, quintozene, tecloftalam, tecnazene, triazoxide, trichlamide, valiphenal, zarilamide,

2- (2 - {[6- (3-chloro-2-methylphenoxy) -5-fluoropyrimidin-4-yl] oxy} phenyl) -2- (methoxyimino) -N-methylacetamide, 2 - [[[[1- (3-fluoro-2-phenylethyl) oxy] phenyl] ethylidene] amino] oxy] methyl] -alpha (methoxyimino) -N-methyl-alpha-benzacetamide,

cis- 1 - (4-chlorophenyl) -2- (1H-1,2,4-triazol-1-yl) -cycloheptanol,

1 - [(4-methoxyphenoxy) methyl] -2,2-dimethylpropyl-1H-imidazole-1-carboxylic acid,

2,3,5,6-tetrachloro-4- (methylsulfonyl) -pyridine,

2-butoxy-6-iodo-3-propyl-benzopyranone-4-one,

2-chloro-N- (2,3-dihydro-1,1,3-trimethyl-1H-inden-4-yl) -3-pyridinecarboxamide,

3,4,5-trichloro-2,6-pyridinedicarbonitrile,

3,4-Dichloro-N- (2-cyanophenyl) isothiazole-5-carboxamide (Isotianil)

3- [5- (4-Chloφhenyl) -2,3-dimethylisoxazolidin-3-yl] pyridine,

5-Chloro-6- (2,4,6-trifluorophenyl) -N - [(1 R) -1,2,2-trimethylpropyl] [1,2,4] triazolo [1,5-a] pyrimidine-7 amine,

5-chloro-7- (4-methyl-1-piperidino) -6- (2,4,6-trifluorophenyl) [1,2,4] triazolo [1,5-a] pyrimidine,

5-Chloro-N - [(1R) -1,2-dimethylpropyl] -6- (2,4,6-trifluorophenyl) [1,2,4] triazolo [1,5-a] pyrimidin-7-amine .

Methyl 2 - [[[cyclopropyl [(4-methoxyphenyl) imino] methyl] thio] methyl] -. Alpha.- (methoxymethylene) benzoacetate,

Methyl 1 - (2,3-dihydro-2,2-dimethyl-1H-inden-1-yl) -1H-imidazole-5-carboxylate,

N- (3 ', 4'-dichloro-5-fluorobiphenyl-2-yl) -3- (difluoromethyl) -l-methyl-lH-pyrazole-4-carboxamide,

N- (3-ethyl-3,5,5-trimethyl-cyclohexyl) -3-formylamino-2-hydroxy-benzamide,

N- (4-chloro-2-nitrophenyl) -N-ethyl-4-methyl-benzenesulfonamid,

N- (4-chlorobenzyl) -3- [3-methoxy-4- (prop-2-yn-l-yloxy) phenyl] propanamide,

N - [(4-chloro-phenyl) (cyano) -methyl] -3- [3-methoxy-4- (prop-2-yn-1-yloxy) -phenyl] -propanamide,

N- (5-bromo-3-chloφyridin-2-yl) methyl-2,4-dichlornicotinamid,

N- [l- (5-bromo-3-chloropyridine-2-yl) ethyl] -2,4-dichloronicotinamid, (2S) -N- [2- [4 - [[3- (4-chlorophenyl) -2-propynyl] oxy] -3-methoxyphenyl] ethyl] -3-methyl-2- [(methylsulfonyl) amino] butanamide .

N - {(Z) - [(cyclopropylmethoxy) imino] [6- (difluoromethoxy) -2,3-difluorophenyl] methyl} -2-benzacetamide,

N- {2- [l, 1'-bi (cyclopropyl) -2-yl] phenyl 1} -3- (difluoromethyl) -1-methyl-1H-pyrazole-4-carboxamide,

N- {2- [3-chloro-5- (trifluoromethyl) pyridin-2-yl] ethyl} -2- (trifluoromethyl) benzamide,

N-ethyl-N-methyl-N '- {2-methyl-5- (trifluoromethyl) -4- [3- (trimethylsilyl) propoxy] phenyl} imidoformamide,

O- [1- (4-methoxyphenoxy) methyl] -2,2-dimethylpropyl] -1H-imidazole-1-carbothioic acid,

2-amino-4-methyl-N-phenyl-5-thiazolecarboxamide,

2,4-Dihydro-5-methoxy-2-methyl-4 - [[[[1- [3- (trifluoromethyl) phenyl] ethylidene] amino] oxy] methyl] phenyl] -3H-1 , 2,4-triazol-3-one (CAS No. 185336-79-2),

N- (6-methoxy-3-pyridinyl) -cyclopropane carboxamide,

bactericides:

Bronopol, dichlorophen, nitrapyrin, nickel dimethyldithiocarbamate, kasugamycin, octhilinone, furancarboxylic acid, oxytetracycline, probenazole, streptomycin, tecloftalam, copper sulfate and other copper preparations.

Insecticides / acaricides / nematicides: acetylcholinesterase (AChE) inhibitors carbamates, for example alanycarb, aldicarb, aldoxycarb, allyxycarb, aminocarb, bendiocarb, benfuracarb, bufencarb, butacarb, butocarboxime, butoxycarboxime, carbaryl, carbofuran,

Carbosulfan, Cloethocarb, Dimetilan, Ethiofencarb, Fenobucarb, Fenothiocarb, Formetanate, Furathiocarb, Isoprocarb, Metam-sodium, Methiocarb, Methomyl, Metolcarb, Oxamyl, Pirimicarb, Promecarb, Propoxur, Thiodicarb, Thiofanox, Trimethacarb, XMC, Xylylcarb, Triazamate Organophosphate, to Example Acephate, Azamethiphos, Azinphos (-methyl, -ethyl), Bromophos-ethyl, Bromfenvinfos (-methyl), Butathiofos, Cadusafos, Carbophenothione, Chloroethoxyfos, Chlorfenvinphos, Chlormephos, Chloφyrifos

(-methyl / -ethyl), coumaphos, cyanofenphos, cyanophos, chlorfenvinphos, demeton-S-methyl, demeton-S-methylsulphon, dialifos, diazinon, dichlofenthione, dichlorvos / DDVP, dicrotophos, dimethoates, dimethylvinphos, dioxabenzofos, disulfoton, EPN, Ethion, Ethoprophos, Etrimfos, Famphur, Fenamiphos, Fenitrothion,

Fensulfothion, Fenthion, Flupyrazofos, Fonofos, Formothion, Fosmethilane, Fosthiazate, Heptenophos, Iodofenphos, Iprobenfos, Isazofos, Isofenphos, Isopropyl O-salicylates, Isoxathion, Malathion, Mecarbam, Methacrifos, Methamidophos, Methidathion, Mevinphos, Monocrotophos, Naled, Omethoate, Oxydemeton -methyl, parathion (-methyl / -ethyl), phenthoates, phorates, phosalones, phosmet, phosphamidone, phosphocarb, phoxim,

Pirimiphos (-methylAethyl), Profenofos, Propaphos, Propetamphos, Prothiofos, Prothoates, Pyraclofos, Pyridaphenthion, Pyridathion, Quinalphos, Sebufos, Sulfotep, Sulprofos, Tebupirimfos, Temephos, Terbufos, Tetrachlorvinphos, Thiometone, Triazophos, Triclorfone, Vamidothion Sodium Channel Modulators / Voltage-Dependent Sodium Channel Blocker Pyrethroids, for example, acrinathrin, allethrin (d-cis-trans, d-trans), beta-cyfluthrin, bifenthrin, bioallethrin, bioallethrin-S-cyclopentyl isomer, bioethanomethrin, biopermethrin, bioresmethrin, chlovaporthrin, Cis-cypermethrin, cis-resmethrin, cis-permethrin, clocythrin, cycloprothrin, cyfluthrin, cyhalothrin, cypermethrin (alpha-, beta-, theta-, zeta-), cyphenothrin, deltamethrin, empenthrin (IR-isomer), esfenvalerate, etofenprox, Fenfluthrin, fenpropathrin, fenpyrithrin, fenvalerate, flubrocythrinates, flucythrinates, flufenprox, flumethrin, fluvalinates, fubfenprox, gamma-cyhalothrin, imiprothrin, kadethrin, lambda-cyhalothrin, metofluthrin, pe rmethrin (cis, trans), phenothrin (IR trans isomer), prallethrin, profuthrin, protrifenbute, pyresmethrin, resmethrin, RU 15525,

Silafluofen, tau-fluvalinate, tefluthrin, terallethrin, tetramethrin (-1R isomer), tralomethrin, transfluthrin, ZXI 8901, pyrethrin (pyrethrum) DDT oxadiazines, for example indoxacarb

Semicarbazone, for example metaflumizone (BAS3201) acetylcholine receptor agonists / antagonists chloronicotinyls, for example acetamipride, clothianidin, dinotefuran, imidacloprid, nitenpyram, nithiazines, thiacloprid, thiamethoxam nicotine, bensultap, cartap Acetylcholine receptor modulators Spinosyne, for example spinosad

GABA-controlled chloride channel antagonists Organochlorines, for example, Camphechlor, Chlordane, Endosulfan, Gamma-HCH, HCH, Heptachlor, Lindane, Methoxychlor Fiprole, for example, acetoprole, ethiprole, fipronil, pyrafluprole, pyriprole, vanilliprole chloride channel activators Mectins , for example, abamectin, emamectin, emamectin benzoate, ivermectin, lepimectin, milbemycin

Juvenile hormone mimetics, for example, diofenolan, epofenonans, fenoxycarb, hydroprene, kinoprenes,

Methoprene, Pyriproxifen, Triprene Ecdysonagonists / Disrupted Diacylhydrazines, for example Chromafenozide, Halofenozide, Methoxyfenozide, Tebufenozide inhibitors of chitin biosynthesis Benzoylharnstoffe, for example Bistrifluron, Chlofluazuron, Diflubenzuron, Fluazuron, Flucycloxuron, Flufenoxuron, Hexaflumuron, Lufenuron, Novaluron, Noviflumuron, Penfluron, Teflubenzuron, Triflumuron Buprofezin Cyromazine

Inhibitors of oxidative phosphorylation, ATP disruptors diafenthiuron

Organotin compounds, for example azocyclotin, cyhexatin, fenbutatin oxides

Decoupling of the oxidative phosphorylation by interruption of the H proton gradient pyrroles, for example chlorfenapyr dinitrophenols, for example binapacyrl, dinobutone, dinocap, DNOC, meptyldinocap

Site I electron transport inhibitors METI's, for example Fenazaquin, Fenpyroximate, Pyrimidifen, Pyridaben, Tebufenpyrad, Tolfenpyrad, Hydramethylnon Dicofol

Site II electron transport inhibitors

Cyenopyrafen, Cyflumetofen, Rotenone Site-Iü electron transport inhibitors

Acequinocyl, Fluacrypyrim Microbial disruptors of the insect intestinal membrane

Bacillus thuringiensis strains inhibitors of fatty synthesis tetronic acids, for example spirodiclofen, spiromesifen,

Tetramic acids, for example spirotetramat, cis-3- (2,5-dimethylphenyl) -4-hydroxy-8-methoxy-1-azaspiro [4.5] dec-3-en-2-one

Carboxamides, for example flonicamide

Octopaminergic agonists, for example, amitraz

Inhibitors of magnesium-stimulated ATPase, propargite

Nereistoxin analogs, for example thiocyclam hydrogen oxalate, thiosultap-sodium

Agonists of the ryanodine receptor, benzoic acid dicarboxamides, for example flubendiamide

anthranilamides, for example, rynaxypyr (3-bromo-N- {4-chloro-2-methyl-6- [(methylamino) arbonyl) -phenyl] -1-chloro-pyridine ^ -yO-1H-pyrazole-S-carboxamide)

Biologics, hormones or pheromones Azadirachtin, Bacillus spec, Beauveria spp., Codlemone, Metarrhizium spec.

Paecilomyces spec, thuringiensin, Verticillium spec. Active substances with unknown or nonspecific action mechanisms fumigants, for example aluminum phosphides, methyl bromides, sulfuryl fluoride feed inhibitors, for example cryolites, flonicamide, pymetrozine mite growth inhibitors, for example clofentezine, etoxazole, hexythiazox

Amidofiumet, benclothiaz, benzoximate, bifenazate, bromopropylate, buprofezin, quinomethionate, chlordimeform, chlorobenzilate, chloropicrin, clothiazoben, cycloprene,

Cyflumetofen, Dicyclanil, Fenoxacrim, Fentrifanil, Flubenzimine, Flufenerim, Flutenzine, Gossyplure, Hydramethylnone, Japonilure, Metoxadiazone, Petroleum, Piperonylbutoxide, Potassium oleate, Pyralidyl, Sulfluramid, Tetradifon, Tetrasul, Tri- arathene, Verbutin.

A mixture with other known active ingredients, such as herbicides, fertilizers, growth regulators, safeners, semiochemicals, or with agents for improving the plant properties is possible.

The active compounds according to the invention can furthermore be present when used as insecticides in their commercial formulations as well as in the formulations prepared from these formulations in admixture with synergists. Synergists are compounds which increase the effect of the active ingredients without the added synergist itself having to be active. The active compounds according to the invention may furthermore, when used as insecticides in their commercial formulations and in the forms of use prepared from these formulations, be present in mixtures with inhibitors which reduce degradation of the active ingredient after application in the environment of the plant, on the surface of plant parts or in plant tissues ,

The active substance content of the application forms prepared from the commercial formulations can vary within wide ranges. The active ingredient concentration of the use forms may be from 0.00000001 up to 95% by weight of active compound, preferably between 0.00001 and 1% by weight. The application is done in a custom forms adapted to the application. According to the invention, all plants and parts of plants can be treated. In this context, plants are understood as meaning all plants and plant populations, such as desired and undesired wild plants or crop plants (including naturally occurring crop plants). Crop plants can be plants which can be obtained by conventional breeding and optimization methods or by biotechnological and genetic engineering methods or combinations of these methods, including the transgenic plants and including the plant varieties which can or can not be protected by plant breeders' rights. Plant parts are to be understood as meaning all aboveground and underground parts and organs of the plants, such as shoot, leaf, flower and root, by way of example 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, such as cuttings, tubers, rhizomes, offshoots and seeds. The treatment according to the invention of the plants and plant parts with the active ingredients takes place directly or by acting on their environment, habitat or storage space according to the usual treatment methods, for example by dipping, pouring, spraying, evaporating, atomizing, spreading, brushing, injecting and in propagation material, in particular at Seeds, still by single or multi-layer coating.

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

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

Depending on the plant species or plant cultivars, their location and growth conditions (soils, climate, vegetation period, diet), the treatment according to the invention may also give rise to superadditive ("synergistic") effects. Thus, for example, reduced application rates and / or extensions of the activity spectrum and / or enhancement of the action 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 dryness or to bottoms, 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 Harvest products possible that go beyond the expected effects.

The preferred plants or plant varieties to be treated according to the invention to be treated include all plants which, as a result of the genetic engineering modification, obtained genetic material which gives these plants particularly advantageous valuable properties ("traits"). Examples of such properties are better plant growth, increased tolerance to high or low temperatures, increased tolerance to dryness or to bottoms salt, increased flowering, easier harvesting, acceleration of ripeness, higher crop yields, higher quality and / or higher nutritional value of the harvested products , higher shelf life and / or workability of the harvested products. Further and particularly emphasized examples of such properties are an increased defense of the plants against animal and microbial pests, as against insects, mites, phytopathogenic fungi, bacteria and / or viruses as well as an increased tolerance of the plants to certain herbicidal active substances. Examples of transgenic plants are the important crops such as cereals (wheat, rice), corn, soybeans, potatoes, sugar beets, tomatoes, peas and other vegetables, cotton, tobacco, oilseed rape and fruit plants (with the fruits apples, pears, citrus fruits and Grapes), with particular emphasis on maize, soya, potato, cotton, tobacco, rice, canola and oilseed rape. Traits that are particularly emphasized are the increased defense of the plants against insects, arachnids, nematodes and snails by toxins produced in the plants, in particular those which are produced by the genetic material from Bacillus thuringiensis (eg by the genes CryΙA (a) , CryΙA (b), CryΙA (c), CryllA, CrylllA, CryIIIB2, Cry9c Cry2Ab, Cry3Bb and CrylF and combinations thereof) in the plants (hereinafter "Bt plants"). Traits also highlight the increased resistance of plants to fungi, bacteria and viruses by systemic acquired resistance (SAR), systemin, phytoalexins, elicitors and resistance genes and correspondingly expressed proteins and toxins. Traits which are furthermore particularly emphasized are the increased tolerance of the plants to certain herbicidally active compounds, for example imidazolinones, sulfonylureas, glyphosate or phosphinotricin (eg "PAT" gene). The genes which confer the desired properties ("traits") can also occur in combinations with one another in the transgenic plants. Examples of "Bt plants" are maize varieties, cotton varieties, soybean varieties and potato varieties which are sold under the trade names YIELD GARD® (eg corn, cotton, soya), KnockOut® (eg maize), StarLink® (eg maize), Bollgard® ( Cotton), Nucotn® (cotton) and NewLeaf® (Potato) are sold. Examples of herbicide-tolerant plants are maize varieties, cotton varieties and soybean varieties, which are sold under the trade names Roundup Ready® (tolerance to glyphosate eg corn, cotton, soy), Liberty Link® (tolerance to phosphinotricin, eg rapeseed), IMI® (tolerance against imidazolinone) and STS® (tolerance to sulfonylureas eg corn). As herbicide-resistant (conventionally grown on herbicide tolerance) plants are also sold under the name Clearfϊeld® varieties (eg corn) mentioned. Of course, these statements also apply to future or future marketed plant varieties with these or future developed genetic traits. The listed plants can be treated particularly advantageously according to the invention with the compounds of the general formula I or the active substance mixtures according to the invention. The preferred ranges given above for the active compounds or mixtures also apply to the treatment of these plants. Particularly emphasized is the plant treatment with the compounds or mixtures specifically mentioned in the present text. The active compounds of the invention not only against plant, hygiene and storage pests, but also in the veterinary sector against animal parasites (ecto- and endoparasites) such as ticks, leather ticks, mange mites, running mites, flies (stinging and licking), parasitic fly larvae, lice , Hair pieces, featherlings and fleas. These parasites include: From the order of Anoplurida eg Haematopinus spp., Linognathus spp., Pediculus spp., Phtirus spp., Solenopotes spp.

From the order of Mallophagida and suborders Amblycerina and Ischnocerina, for example. Trimenopon spp., Menopon spp., Trinoton spp., Bovicola spp., Werneckiella spp., Lepikentron spp., Damalina spp., Trichodectes spp., Felicola spp. From 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. Wohlfahrtia spp., Sarcophaga spp., Oestrus spp., Hypoderma spp., Gasterophilus spp., Hippobosca spp., Lipoptena spp., Melophagus spp.

From the order of siphonapterida e.g. Pulex spp., Ctenocephalides spp., Xenopsylla spp., Ceratophyllus spp. From the order of Heteropterida, e.g. Cimex spp., Triatoma spp., Rhodnius spp., Panstrongylus spp.

From the order Blattarida eg Blatta orientalis, Periplaneta americana, Blattela germanica, Supella spp .. From the subclass of Acari (Acarina) and the orders of meta and mesostigmata eg Argas spp., Ornithodorus spp., Otobius spp., Ixodes spp., Amblyomma spp., Boophilus spp., Dermacentor spp., Haemophysalis spp., Hyalomma Spp., Rhipicephalus spp., Dermanyssus spp., Raillietia spp., Pneumonyssus spp., Sternostoma spp., Varroa spp. From the order of Actinedida (Prostigmata) and Acaridida (Astigmata) eg 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 compounds of the formula (I) are also suitable for controlling arthropods, the livestock, such as cattle, sheep , Goats, horses, pigs, donkeys, camels, buffalo, rabbits, chickens, put en, 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 infested. By controlling these arthropods deaths and reductions in performance (in meat, milk, wool, hides, eggs, honey, etc.) are reduced, so that a more economical and easier animal husbandry is possible by the use of the active compounds according to the invention.

The use of the active compounds according to the invention in the veterinary sector and animal husbandry in a known manner by enteral administration in the form of, for example, tablets, capsules, infusions, drenches, granules, pastes, BoIi, the feed-through process, suppositories, by parenteral Administration, for example 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, pouring (pour-on and spot -on), washing, powdering and with the aid of active substance-containing moldings, such as collars, ear tags, tail marks, limb bands, holsters, marking devices, etc.

In the application for livestock, poultry, pets, etc., the active compounds of the formula (I) can be used as formulations (for example powders, emulsions, flowable agents) which contain the active ingredients in an amount of from 1 to 80% by weight, directly or apply after 100 to 10,000 times dilution or use as a chemical bath.

In addition, it has been found that the compounds according to the invention show a high insecticidal activity against insects which destroy industrial materials.

By way of example, and preferably without limitation, the following insects may be mentioned: beetles such as Hylotrupes bajulus, Chlorophorus pilosis, Anobium punctatum, Xestobium rufovillosum, Ptilinus pecticornis, Dendrobium pertinex, Ernobius mollis, Priobium carpini, Lyctus brunneus, Lyctus africanus, Lyctus planicollis, Lyctus linearis, Lyctus pubescens, Trogoxylon aequale, Minthes rugicollis, Xyleborus spec. Tryptodendron spec. Apate monachus, Bostrychus capucins, Heterobostrychus brunneus, Sinoxylon spec. Dinoderus minutus; Hymenoptera such as Sirex juvencus, Urocerus gigas, Urocerus gigas taignus, Urocerus augur; Termites such as Kalotermes flavicollis, Cryptotermes brevis, Heterotermes indicola, Reticulitermes flavipes, Reticulitermes santonensis, Reticulitermes lucifugus, Mastotermes darwiniensis, Zootermopsis nevadensis, Coptotermes formosanus; Bristle tails like Lepisma saccharina.

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

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

With regard to possible additional admixing partners, reference is made to the above-mentioned insecticides and fungicides. At the same time, the compounds according to the invention can be used to protect against fouling of objects, in particular hulls, sieves, nets, structures, quay systems and signal systems, which come into contact with seawater or brackish water. Furthermore, the compounds according to the invention can be used alone or in combinations with other active substances as antifouling agents. The active compounds are also suitable for controlling animal pests in household, hygiene and storage protection, in particular of insects, arachnids and mites, which are used in closed rooms, such as apartments, factory buildings, offices, vehicle cabins u.a. occurrence. They can be used to control these pests, alone or in combination with other active ingredients and adjuvants in household insecticide products. They are effective against sensitive and resistant species and against all stages of development. These pests include:

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

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

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

From the order of Opiliones e.g. Pseudoscorpiones chelifer, Pseudoscorpiones cheiridium, Opiliones phalangium. From the order of isopods e.g. Oniscus asellus, Porcellio scaber.

From the order of Diplopoda eg Blaniulus guttulatus, Polydesmus spp .. From the order of Chilopoda eg Geophilus spp .. From the order of Zygentoma eg Ctenolepisma spp., Lepisma saccharina, Lepismodes inquilinus.

From the order of the Blattaria e.g. Blatta orientalis, Blattella germanica, Blattella asahinai,

Leucophaea maderae, Panchlora spp., Parcoblatta spp., Periplaneta australasiae, Periplaneta americana, Periplaneta brunnea, Periplaneta fuliginosa, Supella longipalpa.

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

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

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

From the order of Psocoptera e.g. Lepinatus spp., Liposcelis spp. From the order of Coleoptera e.g. Anthrenus spp., Attagenus spp., Dermestes spp., Latheticus oryzae, Necrobia spp., Ptinus spp., Rhizopertha dominica, Sitophilus granarius, Sitophilus oryzae,

Sitophilus zeamais, Stegobium paniceum.

From the order of Diptera e.g. Aedes aegypti, Aedes albopictus, Aedes taeniorhynchus,

Anopheles spp., Calliphora erythrocephala, Chrysozona pluvialis, Culex quinquefasciatus, Culex pipiens, Culex tarsalis, Drosophila spp., Fannia canicularis, Musca domestica, Phlebotomus spp.

Sarcophaga carnaria, Simulium spp., Stomoxys calcitrans, Tipula paludosa.

From the order of Lepidoptera e.g. Achroia grisella, Galleria mellonella, Plodia interpunctella,

Tinea cloacella, Tinea pellionella, Tineola bisselliella.

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

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

From the order of the Anoplura e.g. Pediculus humanus capitis, Pediculus humanus corporis,

Pemphigus spp., Phylloera vastatrix, Phthirus pubis. From the order of Heteroptera, e.g. Cimex hemipterus, Cimex lectularius, Rhodinus prolixus,

Triatoma infestans.

The application in the field of household insecticides is carried out alone or in combination with other suitable active ingredients such as phosphoric acid esters, carbamates, pyrethroids, neonicotinoids, growth regulators or active compounds from other known classes of insecticides. Application is in aerosols, non-pressurized sprays, e.g. Pump and atomizer sprays,

Fog machines, foggers, foams, gels, evaporator products with evaporator plates

Cellulose or plastic, liquid evaporators, gel and membrane evaporators, propeller-driven evaporators, energy-less or passive evaporation systems,

Moth papers, moth sacs and moth gels, as granules or dusts, in straw baits or bait stations. The compounds of the formula 1-3 mentioned in the table below are known from WO 05/056556, WO 05/082907 and the international patent application with the application number PCT / EP 2006/001064 or can be prepared by the processes described therein.

table

(1-3) * Ph = phenyl

O

67

68

70

74

example 1

Phaedon test (spray treatment)

Solvent: 78 parts by weight of acetone

1.5 parts by weight of dimethylformamide

Emulsifier: 0.5 part by weight of alkylaryl polyglycol ether

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

Chinese cabbage leaf discs (Brassica pekinensis) are sprayed with a preparation of active compound of the desired concentration and, after drying, are populated with larvae of the horseradish leaf beetle (Phaedon cochleariae).

After the desired time, the effect is determined in%. 100% means that all beetle larvae have been killed; 0% means that no beetle larvae have been killed.

In this test, for example, the following compounds of the preparation examples with an application rate of 500 g / ha have an efficacy of> 80%: 1-3-1, 1-3-3, 1-3-4, 1-3-5, 1 -3-6, 1-3-7, 1-3-9, 1-3-10, 1-3-11, 1-3-12, 1-3-13, 1-3-14, 1-3 -15, 1-3-16, 1-3-17, 1-3-19, 1-3-21, 1-3-22, 1-3-25, 1-3-26, 1-3-27 , 1-3-28, 1-3-29, 1-3-30, 1-3-31, 1-3-32, 1-3-35, 1-3-37, 1-3-38, 1 -3-39, 1-3-42, 1-3-47, 1-3-48, 1-3-49, 1-3-50, 1-3-52, 1-3-53, 1-3 -54, 1-3-55, 1-3-56, 1-3-57, 1-3-58, 1-3-59, 1-3-60, 1-3-61, 1-3-62 , 1-3-63, 1-3-64, 1-3-65, 1-3-66, 1-3-67, 1-3-68, 1-3-70, 1-3-71, 1 -3-72, 1-3-73, 1-3-74, 1-3-75, J-3-76, 1-3-77, 1-3-78, 1-3-79, 1-3 -80, 1-3-81, 1-3-82, 1-3-83, 1-3-84, 1-3-85, 1-3-86, 1-3-87, 1-3-88 , 1-3- 89, 1-3-90, 1-3-91, 1-3-92, 1-3-93, 1-3-94, 1-3-95, 1-3-96, 1 -3-98, 1-3-99, 1-3-101, 1-3-102, 1-3-104, I-3-109, 1-3-110, 1-3-111, 1-3 -112, 1-3-113, 1-3-114, 1-3-115, 1-3-116, 1-3-117, 1-3-118, 1-3-119, 1-3-120 , 1-3-121, 1-3-122, 1-3-123, 1-3-124, 1-3-125, 1-3-127, 1-3-128, 1-3-129, 1 -3-131, 1-3-132, 1-3-133, 1-3-135, 1-3-136, 1-3-137, 1-3-138, 1-3-139, 1-3 -140, 1-3-141, 1-3-142, 1-3-144, 1-3-145, 1-3-146, 1-3-147, 1-3-148, 1-3-149 , 1-3-150, 1-3-152, 1-3-154, 1-3-155, 1-3-156, 1-3-157, 1-3-158, 1-3-159, 1 -3-160, 1-3-161, 1-3-163, 1-3-164, 1-3-165, 1-3-166, 1-3-167, 1-3-168, 1-3 -169, 1-3-170, 1-3-172, 1-3-173, 1-3-174, 1-3-175, 1-3-176, 1-3-177, 1-3-179 , 1-3-180, 1-3-181, 1-3-182, 1-3-183, 1-3-184, 1-3-185, 1-3-186, 1-3-187, 1 -3-188, 1-3-189, 1-3-190, 1-3-191, 1-3-192, 1-3-193, 1-3-194, 1-3-195, 1-3 -196, 1-3-197, 1-3-198, 1-3-199, 1-3-200, 1-3-201, 1-3-202, 1-3-203, 1-3-204 , 1-3-205, 1-3-206, 1-3-207, 1-3-208, 1-3-209, 1-3-210, 1-3-211, 1-3-212, 1 -3-213, 1-3-214, 1-3-215, 1-3-216, 1-3-217, 1-3-218, 1-3-219, 1-3-220, 1-3 -221, 1-3-222, 1-3-223, 1-3-224, 1-3-225, 1-3-226, 1-3-227, 1-3-228, 1-3-229 , 1-3-230, 1-3-231, 1-3-232, 1-3-233, 1-3-234, 1-3-235, 1-3-236, 1-3-237, 1 -3-238, 1-3- 239, 1-3-240, 1-3-241, 1-3-242, 1-3-243, 1-3-244, 1-3-245, 1-3-246, 1-3-247, 1-3-248, 1-3-249, 1-3-251, 1-3-252, 1-3-253, 1-3-254, 1-3-255, 1-3-256, 1- 3-257, 1-3-258, 1-3-259, 1-3-260, 1-3-263, 1-3-264, 1-3-265, 1-3-266, 1-3- 267, 1-3-268, 1-3-269, 1-3-270, 1-3-272, 1-3-273, 1-3-274, 1-3-275, 1-3-276, 1-3-277, 1-3-278, 1-3-279, 1-3-280, 1-3-281, 1-3-282, 1-3-283, 1-3-284, 1- 3-285, 1-3-286, 1-3-287, 1-3-288, 1-3-289, 1-3-290, 1-3-291, 1-3-292, 1-3- 293, 1-3-294, 1-3-295, 1-3-296, 1-3-297, 1-3-298, 1-3-299, 1-3-300, 1-3-301, 1-3-302, 1-3-303, 1-3-304, 1-3-305, 1-3-307, 1-3-308, 1-3-309, 1-3-310, 1- 3-313, 1-3-314, 1-3-315, 1-3-316, 1-3-317, 1-3-318, 1-3-319, 1-3-320, 1-3- 321, 1-3-322, 1-3-323, 1-3-324, 1-3-325, 1-3-326, 1-3-327, 1-3-328, 1-3-329, 1-3-330, 1-3-331, 1-3-332, 1-3-333, 1-3-335, 1-3-336, 1-3-337, 1-3-338, 1- 3-339, 1-3-340, 1-3-342, 1-3-343, 1-3-344, 1-3-345, 1-3-346, 1-3-348, 1-3- 349, 1-3-359, 1-3-360, 1-3-361, 1-3-362, 1-3-363, 1-3-364, 1-3-365, 1-3-366, 1-3-367, 1-3- 368, 1-3-369, 1-3-370, 1-3-371, 1-3-372, 1-3-373, 1-3-374, 1-3-375, 1-3-376, 1-3-377, 1-3-378, 1-3-379, 1-3-380, 1-3-381, 1-3-382, 1-3-383, 1-3-384, 1- 3-385, 1-3-386, 1-3-387, 1-3-388, 1-3-389, 1-3- 390, 1-3-391, 1-3-392, 1-3- 393, 1-3-394, 1-3-395, 1-3-396, 1-3-397, 1-3-398, 1-3-399, 1-3-401, 1-3- 402, 1-3-403, 1-3-404, 1-3-406, 1-3-407, 1-3-408, 1-3-409-I-3-410.

Example 2

Myzus test (spray treatment)

Solvent: 78 parts by weight of acetone

1.5 parts by weight of dimethylformamide

Emulsifier: 0.5 part by weight of alkylaryl polyglycol ether

Chinese cabbage leaf discs (ßrassica pekinensis) infested with all stages of the green peach aphid (Myzus persicae) are sprayed with an active compound preparation of the desired concentration.

After the desired time, the effect is determined in%. 100% means that all aphids have been killed; 0% means that no aphids have been killed.

In this test, e.g. the following compounds of the preparation examples with a

Application rate of 500 g / ha an efficacy of> 80%: 1-3-5, 1-3-6, 1-3-7, 1-3-8, 1-3-9, 1-3-11, 1 -3-13, 1-3-16, 1-3-31, 1-3-32, 1-3-35, 1-3-43, 1-3-72, 1-3-84, 1-3 -87, 1-3-124, 1-3-184, 1-3-201, 1- 3-260, 1-3-268, 1-3-323, 1-3-349, 1-3-378, 1-3-379, 1-3-384, 1-3-385, 1-3- 386, 1-3-389, 1-3-390, 1-3-395, 1-3-408, 1-3-409, 1-3-410.

Example 3

Spodoptera fπigiperda test (spray treatment)

Solvent: 78 parts by weight of acetone

1.5 parts by weight of dimethylformamide

Emulsifier: 0.5 part by weight of alkylaryl polyglycol ether

Corn leaf discs {Zea mays) are sprayed with an active compound preparation of the desired concentration and, after drying, are infested with caterpillars of the armyworm (Spodoptera frugiperda).

After the desired time, the effect is determined in%. 100% means that all caterpillars have been killed; 0% means that no caterpillar has been killed.

In this test, for example, the following compounds of the preparation examples with an application rate of 500 g / ha have an efficacy of> 80%: 1-3-1, 1-3-5, 1-3-6, 1-3-8, 1 -3-9, 1-3- 10, 1-3-1 1, 1-3-12, 1-3-13, 1-3-14, 1-3-15, 1-3-16, 1- 3-17, 1-3-21, 1-3-23, 1-3-24, 1-3-25, 1-3-27, 1-3-28, 1-3-30, 1-3- 31, 1-3-32, 1-3-33, 1-3-35, 1-3-36, 1-3-37, 1-3-38, 1-3-45, 1-3-46, 1-3-47, 1-3-48, 1-3- 49, 1-3-50, 1-3-51, 1-3-58, 1-3-59, 1-3-60, 1- 3-61, 1-3-62, 1-3-64, 1-3-66, 1-3-67, 1-3-68, 1-3-71, 1-3-72, 1-3- 76, 1-3-79, 1-3-81, 1-3-84, 1-3-86, 1-3-87, 1-3-88, 1-3-89, 1-3-91, 1-3-92, 1-3-94, 1-3-96, 1-3-101, 1-3-102, 1-3-109, 1-3-112, 1-3-1, 13, 1 -3-1 14, 1-3-115, 1-3-116, 1-3-117, 1-3-118, 1-3-1 19, 1-3-121, 1-3-122, 1 -3-123, 1-3-124, 1-3-125, 1-3-127, 1-3-128, 1-3-129, 1-3-140, 1-3-141, 1-3 -142, 1-3-143, 1-3-144, 1-3-145, 1-3-146, 1-3-147, 1-3-149, 1-3-150, 1-3-152 , 1-3-154, 1-3-155, 1-3-156, 1-3-157, 1-3-158, 1-3-159, 1-3-160, 1-3-161, 1 -3-164, 1-3-165, 1-3-174, 1-3-176, 1-3-181, 1-3-18 2, 1-3- 183, 1-3-186, 1-3-187, 1-3-188, 1-3-191, 1-3-192, 1-3-193, 1-3-198, 1-3-202, 1-3-203, 1-3-205, 1-3-206, 1-3-207, 1-3-214, 1-3-215, 1-3-216, 1- 3-217, 1-3-218, 1-3-220, 1-3-221, 1-3-224, 1-3-225, 1-3-236, 1-3-242, 1-3- 245, 1-3-246, 1-3-247, 1-3-248, 1-3-249, 1-3-250, 1-3-251, 1-3-254, 1-3-255, 1-3- 256, 1-3-257, 1-3-259, 1-3-260, 1-3-262, 1-3-263, 1-3-280, 1-3-281, 1- 3-287, 1-3-298, 1-3-299, 1-3-300, 1-3-302, 1-3-304, 1-3-306, 1-3-308, 1-3- 309, 1-3-312, 1-3-317, 1-3-318, 1-3-319, 1-3-320, 1-3- 322, 1-3-325, 1-3-327, 1-3-328, 1-3-329, 1-3-330, 1-3-331, 1-3-334, 1-3-336, 1-3-337, 1-3-341, 1-3-342, 1-3-346, 1-3-347, 1-3-348, 1-3-349, 1-3-361, 1- 3-365, 1-3-370, 1-3-371, 1-3-372, 1-3-378, 1-3-381, 1-3-382, 1-3-397, 1-3- 400, 1-3-401, 1-3-402, 1-3-404, 1-3-408, 1-3-409.

Example 4

Tetranychus test, surgical-resistant (spray treatment)

Solvent: 78 parts by weight of acetone

1.5 parts by weight of dimethylformamide

Emulsifier: 0.5 part by weight of alkylaryl polyglycol ether

Bean leaf discs (Phaseolus vulgaris) infected by all stages of the common spider mite (Tetranychus urticae) are sprayed with an active compound preparation of the desired concentration.

After the desired time, the effect is determined in%. 100% means that all spider mites have been killed; 0% means that no spider mites have been killed.

In this test, e.g. the following compounds of the preparation examples have an activity of> 80% at an application rate of 100 g / ha: 1-3-58, 1-3-76, 1-3-315, 1-3-316, 1-3-318, 1-3-329, 1-3-330, 1-3-346, 1-3-348.

In this test, for example, the following compounds of the preparation examples show an activity of> 80% at an application rate of 500 g / ha: 1-3-6, 1-3-1 1, 1-3-14, 1-3-17 , 1-3-27, 1-3-38, 1-3-68, 1-3-79, 1-3-81, 1-3-92, 1-3-125, 1-3-246, 1 -3-248, 1-3-251, 1-3-260, 1-3-262, 1-3-283, 1-3-301, 1-3-302, 1-3-309, 1-3 -388, 1-3-389, 1-3-320, 1-3-334, 1-3-337, 1-3-340, 1-3-348, 1-3-359, 1-3-362 , 1-3-365, 1-3-382 "I-3-401, 1-3-407, 1-3-410.

Example 5

Lucilia cuprina test

Solvent: dimethyl sulfoxide To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amount of water and the concentrate is diluted with water to the desired concentration.

Vessels containing horsemeat treated with the preparation of active compound of the desired concentration are mated with (Lucilia cuprina) larvae.

After the desired time the kill is determined in%. 100% means that all larvae have been killed; 0% means that no larvae have been killed.

In this test, e.g. the following compounds of the preparation examples with a test concentration of 100 ppm have an efficacy of> 80%: 1-3-1, 1-3-6,, 1-3-7, 1-3-8, 1-3-9, I 3-10, 1-3-11, 1-3-12, 1-3-13, 1-3-14, 1-3-15, 1-3-16, 1-3-17, 1-3 -18, 1-3-19, 1-3-21, 1-3-22, 1-3-23, 1-3-24, 1-3-25, 1-3-26, 1-3-27 , 1-3-28, 1-3-30, 1-3-31, 1-3-32, 1-3-33, 1-3-35, 1-3-36, 1-3-37, 1 -3-38, 1-3- 63, 1-3-67, 1-3-76, 1-3-127, 1-3-129, 1-3-149, 1-3-188, 1-3 -205, 1-3-214, 1-3-225, 1-3-246, 1-3-248, 1-3251, 1-3-260, 1-3-323, 1-3-339 , 1-3-345, 1-3-346, 1-3-378, 1-3-379, 1-3-381, 1-3-382, 1-3-384, 1-3-385, 1 -3-386, 1-3-387, 1-3-389, 1-3-390, 1-3-392, 1-3-408, 1-3-409.

Example 6

Boophilus microplus test

Solvent: dimethyl sulfoxide

To prepare a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amount of solvent and the concentrate is diluted with solvent to the desired concentration.

The drug solution is injected into the abdomen {Boophilus mircoplus), the animals are transferred into trays and kept in an air-conditioned room.

After the desired time, the effect is determined in%. 100% means that no ticks have laid fertile eggs.

In this test, for example, the following compounds show an efficacy of> 80% for the test concentration of 20 μg / animal: 1-3-1, 1-3-4, 1-3-11, 1-3-12, 1-3- 17, 1-3-18, 1-3-27, 1-3-28, 1-3-31, I-3-33, 1-3-35, 1-3-36, 1-3-37, 1-3-38, 1-3-46, 1-3-58, 1-3-67, 1-3-74, 1-3-76, 1-3-88, 1-3-92, 1- 3-114, I-3-119, 1-3-122, 1-3-123, 1-3-127, 1-3-128, 1-3-129, 1-3-147, 1-3- 149, 1-3-159, 1-3-172, 1-3-176, 1-3-185, 1-3-187, 1-3-188, 1-3-202, 1-3-205, 1-3-214, 1-3-225, 1-3-227, 1-3-228, 1-3-229, 1-3-231, 1-3- 246, 1-3-248, 1-3-251, 1-3-259, 1-3-260, 1-3-302, 1-3-312, 1-3-326, 1-3-328, 1-3-337, 1-3-339, 1-3-346, 1-3-378, 1-3-381, 1-3-382, 1-3-389.

Example 7

Musca domestica test

Solvent: dimethyl sulfoxide

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

Vessels containing a sponge treated with the preparation of active compound of the desired concentration are occupied by (Musca domestic) adults.

After the desired time the kill is determined in%. 100% means that all flies have been killed; 0% means that no flies have been killed.

In this test, e.g. the following compound of the preparation example with a test concentration of 100 ppm has an effectiveness of> 80%: 1-3-16.

Example 8

Meloidogne test (MELGEV spray treatment)

Solvent: 80 parts by weight of acetone

To prepare a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amount of water and the concentrate is diluted with water to the desired concentration.

Vessels are filled with sand, drug solution Meloidogyne incognita egg larvae suspension and lettuce seeds. The lettuce seeds germinate and the plantlets develop. The galls develop at the roots.

After the desired time, the nematicidal activity is determined by means of bile formation in%. 100% means that no bile was found; 0% means that the number of bile on the treated plants corresponds to that of the untreated control. In this test, for example, the following compounds of the preparation examples show an activity of> 80% at an application rate of 20 ppm: 1-3-7, 1-3-41, 1-3-42, 1-3-46, 1-3 - 59, 1-3-61, 1-3-64, 1-3-65, 1-3-66, 1-3-70, 1-3-71, 1-3-78, 1-3-80 , 1-3-82, 1-3-96, 1-3-101, 1-3-1 15, I-3-1 16, 1-3-117, 1-3-118, 1-3-120 , 1-3-127, 1-3-131, 1-3-133, 1-3-135, 1-3-136, 1-3-137, 1-3-138, 1-3-163, 1 -3-164, 1-3-166, 1-3-198, 1-3-200, 1-3-262, 1-3-298, 1-3-311, 1-3-321, 1-3 -331, 1-3-334, 1-3-369, 1-3-407.

In this test, e.g. the following compounds of the preparation examples an effectiveness of> 80% at an application rate of 8 ppm: 1-3-10, 1-3-19, 1-3-21, 1-3-24.

In this test, e.g. the following compounds of the preparation examples have an activity of> 80% at an application rate of 4 ppm: 1-3-1, 1-3-29, 1-3-30, 1-3-99, 1-3-193, 1- 3-194, 1-3-227, 1-3-230, 1-3-275.

Example 9

Nilaparvata lugens test (NILALU hydroponic treatment)

Solvent: 78 parts by weight of acetone 1.5 parts by weight of dimethylformamide

Emulsifier: 0.5 part by weight of alkylaryl polyglycol ether

The preparation of the active compound is pipetted in water. The stated concentration refers to the amount of active substance per unit volume of water (mg / 1 = ppm), followed by the brown-backed rice leafhopper {Nilaparvata lugens).

After the desired time, the effect is determined in%. 100% means that all rice cicadas have been killed, 0% means that no rice cicadas have been killed.

In this test, e.g. the following compound of the preparation example with a test concentration of 500 ppm has an effectiveness of> 80%: 1-3-52.

Example 10 Heliotis virescens test (HELIVI spray treatment)

Solvent: 78 parts by weight of acetone

1.5 parts by weight of dimethylformamide

Emulsifier: 0.5 part by weight of alkylaryl polyglycol ether

Soybean leaves {Glycine max.) Are sprayed with an active compound preparation of the desired concentration and, after drying, are populated with eggs of the cotton bollworm {Heliotis virescens).

After the desired time, the effect is determined in%. 100% means that all eggs have been killed; 0% means that no eggs were killed.

In this test, e.g. the following compound of the preparation example with a test concentration of 500 ppm has an effectiveness of> 80%: 1-3-50.

Example 11: Increasing the Effectiveness of Ammonium / Phosphonium Salts in Combination with Penetration Promoters

Myzus persicae test

Solvent: 7 parts by weight of dimethylformamide

Emulsifier: 2 parts by weight of alkylaryl polyglycol ether

To prepare a suitable preparation of active compound, 1 part by weight of active compound is mixed with the indicated amounts of solvent and emulsifier, and the concentrate is diluted with emulsifier-containing water to the desired concentration. With the necessary addition of ammonium salts, penetration enhancers or ammonium salts and penetration promoters, these are pipetted in each case to the finished preparation solution in a concentration of 1000 ppm after dilution.

Paprika plants (Capsicum annuurή) which are heavily infested with the green peach aphid {Myzus persicae) are treated by drip-whisking with the preparation of active compound in the desired concentration. After the desired time the kill is determined in%. 100% means that all animals have been killed; O% means that no animals have been killed.

In this test, z. B. the following compound of the preparation examples good activity: see table

table

Example 12 Enhancement of Effectiveness by Ammonium / Phosphonium Salts in Combination with Penetration Promoters

Aphis gossypii test

Solvent: 7 parts by weight dimethylfibramide

Emulsifier: 2 parts by weight of alkylaryl polyglycol ether

Cotton plants (Gossypium hirsutum) heavily infested with the cotton aphid {Aphis gossypii) are treated by drip-wet spraying with the preparation of active compound 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.

In this test, z. B. the following compound of the preparation examples good activity: see table table

Claims

claims

1. Use of heterocyclic carboxylic acid derivatives of the following formula (1)

wherein

Binding,

and

X is hydrogen, halogen, cyano, hydroxy, alkyl, alkoxy, phenyl, alkylthio,

Alkylsulfinyl or alkylsulfonyl;

Y is aryl, heterocyclyl, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl,

Arylalkyl, halogen, an amino group, (Cj-Cg) -alkoxy, (C _] -Cg) -alkylthio, (C6-Cio) -aryloxy, (Cg-C0) -arylthio, heterocyclyloxy, (Co-CiO) - AIyI- (C ₁ - C4) -alkoxy, (Cg-C _j o) aryl (C \ -C4) alkylthio, heterocyclyl (C i -C ₄₎ alkoxy, heterocyclyl (C ₁ -C ₄₎ alkylthio, C ( S) OR ⁸ , C (O) SR ⁸ or C (S) SR ⁸ ;

Z is hydroxy, halogen or alkoxy, alkylthio, alkylsulfonyl or the group

G ^, G ^ and G ^{3 are} independently hydrogen, halogen, alkyl or

Cycloalkyl, 0- (C ₁ -C ₄ VAIlCyI or S (O) ₀ ^ (C iC ₄₎ -alkyl;

L is oxygen or sulfur;

R! is hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl or heterocyclyl, hydroxy, alkoxy, amine, alkylamine or dialkylamine;

R ^ is hydrogen or alkyl;

or

R! and R ^ together with the nitrogen atom to which they are attached represent a heterocyclic ring;

R 4 is hydrogen, alkyl, alkenyl or alkynyl, in each case saturated or unsaturated cycloalkyl which may optionally be interrupted by heteroatoms, phenyl, heteroaryl, arylalkyl or heteroarylalkyl or a cation such as monovalent or divalent metal atoms or an ammonium ion;

R ^ is hydrogen, alkyl, alkoxy, alkenyl, alkenyloxy or alkynyl, for the groups COR ⁷ , S (O)] R ⁷ , cyano, COOR ⁷ ,

or

R.4 and R.5 together with the nitrogen atom to which they are attached represent a saturated, unsaturated or aromatic ring which may optionally be interrupted by further heteroatoms;

R "is hydrogen, a cation, for example an ammonium ion, alkyl, alkenyl, alkynyl, cycloalkyl or cycloalkenyl, which is optionally substituted by a

R? is hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl-alkyl, cycloalkyl or cycloalkenyl, aryl, heteroaryl, arylalkyl or heteroarylalkyl;

R ^{8 is} hydrogen, alkyl, alkenyl, alkynyl, alkoxy or NH-R ⁴ ;

or

R ⁴ and R? together with the N-CO or NS (O) j.2 group to which they are attached, a 4- to 8-membered cycle which may contain one or more heteroatoms from the group consisting of sulfur, oxygen and / or nitrogen, wherein Oxygen atoms may not be adjacent form;

or

R? and R ⁸ together with the nitrogen atom to which they are attached represent an optionally substituted saturated or unsaturated ring which may optionally be interrupted by further heteroatoms;

R ^ and RIO independently of one another are alkyl, alkenyl, alkoxy, alkenyloxy,

Alkynyloxy, cycloalkoxy, cycloalkenyloxy, cycloalkylalkoxy, alkylthio, alkenylthio, phenoxy, phenylthio, benzyloxy, benzylthio,

Heteroaryloxy, heteroarylthio, heteroarylalkoxy or heteroarylalkylthio; or

R.9 and R * "together with the phosphorus atom to which they are attached stand for an optionally substituted 5- to 7-membered cycle which may be interrupted by one or two oxygen and / or sulfur atoms;

and

R 1 and R 2 independently represent alkyl, alkenyl, alkynyl, phenyl or phenylalkyl;

or

of agrochemically active salts thereof

for the control of animal pests.

2. Use according to claim 1, wherein in the event that independently

X is the radical alkyl, alkoxy, phenyl, alkylthio, alkylsulfinyl or alkylsulfonyl,

the aforementioned radicals are unsubstituted or substituted, preferably unsubstituted or substituted by one or more halogen atoms; and or

Y is aryl, heterocyclyl, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, arylalkyl, amino, (Cj-Cg) -alkoxy, (Ci-Cg) -alkylthio, (C6-Cio) -aryloxy, (C6-C _{1 ()} ) arylthio, heterocyclyloxy, (C6-Cjo) aryl- (Ci -)

C4) -alkoxy, (Cg-C0) -aryl (C 1 -C 4) -alkylthio, heterocyclyl- (C 1 -C 4) -alkoxy or heterocyclyl- (C 1 -C 4) -alkylthio,

the aforementioned radicals are unsubstituted or substituted; and or

Y is the radical alkyl, alkenyl, alkynyl, cycloalkyl or arylalkyl,

the abovementioned radicals are unsubstituted or partially or completely halogenated and / or optionally carry one to three radicals R ^x , where the R ^{x are} identically or differently selected from the group consisting of Cyano, nitro, hydroxy, C _j -CG-alkyl, Ci-COE-haloalkyl, C3-C6-cycloalkyl, Ci -CG-alkoxy, C _j -CG-haloalkoxy, Cj-Cg alkylthio, Ci-COE-haloalkylthio, Ci-Cg-alkylsulfinyl, Ci-Cg-haloalkylsulfinyl, Ci-Cg-alkylsulfonyl, Ci-Cβ-haloalkylsulfonyl, Ci-Cg-alkylamino, di-Cj-Cg-alkylamino, C2-C6-alkenyl, C2-C6-alkenyloxy, C 2 -C 6 -alkynyl, C 3 -C 6 -alkynyloxy and optionally halogenated oxy-C 1 -C 4 -alkyl-C 1 -C 4 -alkenoxy, oxy-C 1 -C 4 -alkenyl-C 1 -C 4 -alkoxy and oxy-C 1 -C 4 -alkoxy alkyl-C ^ -C4 alkyloxy; and or

stands for aryl,

the remainder is unsubstituted or

is monosubstituted, monosubstituted or differently substituted by halogen,

Cyano, nitro, amino, hydroxy, formyl, carboxy, carboxyalkyl, carbamoyl and / or thiocarbamoyl;

in each case straight-chain or branched alkenyl, alkynyl, alinyloxy or alkenyloxy having in each case 2 to 6 carbon atoms;

in each case straight-chain or branched haloalkyl, haloalkoxy, halogenoalkylthio, haloalkylsulfinyl or haloalkylsulfonyl having in each case 1 to 6 carbon atoms and 1 to 13 identical or different halogen atoms;

in each case straight-chain or branched haloalkenyl or haloalkenyloxy having in each case 2 to 6 carbon atoms and 1 to 11 identical or different halogen atoms;

in each case straight-chain or branched alkylamino, dialkylamino, alkylcarbonyl, alkylcarbonyloxy, alkoxycarbonyl, alkylsulfonyloxy, hydroximinoalkyl or alkoximinoalkyl having in each case 1 to 6 carbon atoms in the individual alkyl moieties;

optionally mono- to disubstituted, by fluorine, chlorine, C _j ^ alkyl or C _j -C3 alkoxy-substituted cycloalkyl having 3 to 8 carbon atoms; or

1,3-propanediyl, 1,4-butanediyl, methylenedioxy (-O-CH 2 -O-) or 1,2-ethylenedioxy (-O-C 1-6) - linked in the 2,3-position or 3,4-position, respectively ₂ -O-), where these radicals may be mono- or polysubstituted by identical or different substituents by halogen, alkyl having 1 to 4 carbon atoms and / or haloalkyl having 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms; and or

Y is heterocyclyl,

the abovementioned radical is unsubstituted or mono- or disubstituted by identical or different substituents by halogen, alkyl having 1 to 4 carbon atoms, alkoxy having 1 to 4 carbon atoms, alkylthio having 1 to 4 carbon atoms, haloalkoxy having 1 to 4 carbon atoms, haloalkylthio having 1 to 4 carbon atoms, hydroxy, mercapto, cyano, nitro and / or cycloalkyl having 3 to 6

Carbon atoms and / or carboxyalkyl; and or

Z is the radical alkoxy, alkylthio or alkylsulfonyl,

the aforementioned radicals are unsubstituted or substituted, preferably unsubstituted or substituted by one to seven halogen atoms; and or

G ^, G ^ and G ^ independently represent the radical alkyl, cycloalkyl O- (C ^ -

C ₄ ) -alkyl or S (O) o_2 (C 1 -C ₄ ) -alkyl,

the abovementioned radicals are unsubstituted or substituted independently of one another, are preferably unsubstituted independently of one another or are substituted by one or more halogen atoms; and or

R! the rest being alkyl, alkenyl, alkynyl, cycloalkyl, heterocyclyl, alkoxy, alkylamine or dialkylamine,

the aforementioned radicals are unsubstituted or substituted; and or

R ^{1 is} alkyl,

the abovementioned radical is unsubstituted or monosubstituted, monosubstituted or differently substituted by halogen, cyano, hydroxyl, alkoxy having 1 to 4 carbon atoms, cycloalkyl having 3 to 6 carbon atoms, mercapto, alkylthio having 1 to 4 carbon atoms, amino, mono- and / or or dialkylamino each having 1 to 4 carbon atoms; and or R ^{1 is} alkenyl,

the abovementioned radical is unsubstituted or monosubstituted to trisubstituted, identically or differently substituted by halogen, cyano, hydroxyl, alkoxy having 1 to 4 carbon atoms, cycloalkyl having 3 to 6 carbon atoms, mercapto, alkylthio having 1 to 4 carbon atoms, amino, mono- and / or or dialkylamino each having 1 to 4 carbon atoms; and or

R ^{1 is} alkynyl,

the abovementioned radical is unsubstituted or monosubstituted to trisubstituted, identically or differently substituted by halogen, cyano, hydroxyl, alkoxy having 1 to 4 carbon atoms, cycloalkyl having 3 to 6 carbon atoms, mercapto,

Alkylthio having 1 to 4 carbon atoms, amino, mono- and / or dialkylamino each having 1 to 4 carbon atoms; and or

R ^{1 is} cycloalkyl,

the aforesaid radical is unsubstituted or monosubstituted to trisubstituted, identically or differently substituted by halogen, alkyl and / or haloalkyl having in each case 1 to 4 carbon atoms; and or

R! represents heterocyclyl,

the abovementioned radical is unsubstituted or mono- or polysubstituted by identical or different substituents by halogen, alkyl having 1 to 4 carbon atoms, alkoxy having 1 to 4 carbon atoms, cyano, nitro, cycloalkyl having 3 to 6

Carbon atoms, hydroxy, alkoxy, alkenyloxy, alkynyloxy of 1 to 6 carbon atoms and / or mercapto; and or

R! and R 1 together with the nitrogen atom to which they are attached represent a heterocyclic ring,

the aforesaid heterocyclic ring is unsubstituted or substituted, preferably unsubstituted or substituted up to three times, identically or differently, by fluorine, chlorine, bromine, alkyl of 1 to 4 carbon atoms, haloalkyl of 1 to 4 carbon atoms and 1 to 9 fluorine and / or chlorine atoms , Hydroxy, alkoxy of 1 to 4 carbon atoms, haloalkoxy of 1 to 4 carbon atoms and 1 to 9 fluorine and / or chlorine atoms, mercapto, thioalkyl having 1 to 4 carbon atoms and / or haloalkylthio having 1 to 4 carbon atoms and 1 to 9 fluorine and / or chlorine atoms; and or

R 4 is the radical alkyl, alkenyl, alkynyl, saturated or unsaturated cycloalkyl, which may optionally be interrupted by heteroatoms, phenyl,

Heteroaryl, arylalkyl, heteroarylalkyl or an ammonium ion,

The abovementioned radicals is unsubstituted or substituted, preferably unsubstituted, or R ^ is selected from the group consisting of alkyl ammonium, especially mono- (C \ -C \ o) alkylammonium, di- (C \ -C \ _Q) alkylammonium, tri - (Ci-Cio) -alkylammonium and tetra (Ci-Cio) -alkylammonium, wherein the

Alkyl radicals of the ammonium ions can be substituted by aryl or hydroxyl, in each case mono- to polysubstituted, identically or differently, by fluorine, chlorine, C 1 -C 4 -alkoxy, C 1 -C 4 -alkylthio, cyano, CO 2 -H and / or CO-OC _j - C 1-6 alkyl-substituted alkyl, alkenyl and alkynyl, mono- to polysubstituted, identically or differently, by fluorine, chlorine, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkyl

Alkoxy, CN, CO2H and / or CO-OC j -C4-alkyl substituted C3-C8-cycloalkyl and C5-Cg-cycloalkenyl, which may optionally be interrupted by heteroatoms, mono- to trisubstituted identically or differently by fluorine, chlorine, bromine C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, nitro and / or cyano-substituted phenyl, heteroaryl,

Arylalkyl and heteroarylalkyl; and or

R ^ is the radical alkyl, alkoxy, alkenyl, alkenyloxy, alkynyl or saturated, partially or fully unsaturated or aromatic, 5- or 6-membered ring

Heterocyclyl, optionally containing one or up to three further heteroatoms selected from the group consisting of N, S and O atoms, wherein

Oxygen atoms are not allowed to be adjacent,

the abovementioned radicals are unsubstituted or substituted, are preferably unsubstituted or R 1 is selected from the group consisting of mono- to polysubstituted by identical or different fluorine and / or chlorine alkyl, alkoxy, alkenyl, alkenyloxy, alkynyl and mono- to disubstituted, identical or different manner by fluorine, chlorine, bromine, Ci-C ₄ alkyl, C] -C ₄ alkoxy, cyano and / or nitro-substituted heterocyclyl; and or R.4 and R.5 together with the nitrogen atom to which they are attached represent a saturated, unsaturated or aromatic ring which may optionally be interrupted by further heteroatoms,

the aforementioned ring is unsubstituted or substituted, preferably unsubstituted or monosubstituted or polysubstituted, identically or differently, by C 1 -C ₄ -alkyl; and or

R 6 is an ammonium ion, alkyl, alkenyl, alkynyl, cycloalkyl or cycloalkenyl, which may optionally be interrupted by a heteroatom, cycloalkyl-alkyl, aryl, arylalkyl, heteroaryl or heteroaryl-alkyl,

the abovementioned radicals are unsubstituted or substituted, preferably unsubstituted, or R "is selected from the group consisting of alkylammonium, in particular HiOnO- (C ₁ -C 4 -alkylammonium, di- (C ₁ -C 10) -alkylammonium, Ui- (C ₁ - C ₁ -C ₄ -alkylammonium and tetra-C ₁ -C ₄ -alkylammonium, where the alkyl radicals of the ammonium ions may be substituted identically or differently with aryl or hydroxy, in each case mono- to polysubstituted by identical or different substituents by fluorine, chlorine, C ₁ -C ₄ - AIkOXy, C ₁ -C ₄ -AHCyItIuO, cyano, CO2-H and / or CO-OC \ -C ₄ -alkyl substituted alkyl, alkenyl and alkynyl, in each case mono- to polysubstituted, identically or differently by fluorine, chlorine, C ₁ - C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy, CN, CO 2 H and / or CO-O-C ₁ -C ₄ -alkyl substituted cycloalkyl, cycloalkyl-alkyl and cycloalkenyl, which may be replaced by a Heteroatom may be interrupted, and in each case up to three times, identically or differently by fluorine, chlorine, bromine , C ₁ -C ₄ -alkyl, C iC ^ haloalkyl, C ₁ -C ₄ -alkoxy, C ₁ -C ₄ - haloalkoxy, nitro and / or cyano substituted aryl, arylalkyl, heteroaryl and heteroaryl-alkyl; and or

R? represents the radicals alkyl, alkenyl, alkynyl, cycloalkyl-alkyl, cycloalkyl, cycloalkenyl, aryl, heteroaryl, arylalkyl or heteroarylalkyl,

the abovementioned radicals are unsubstituted or substituted, are preferably unsubstituted or R 'is selected from the group consisting of in each case mono- to polysubstituted, identical or different by fluorine, chlorine, C ₁ -C ₄ -alkoxy, C ₁ -

C ₄ alkylthio, cyano, CO2 H and / or CO-OC ₁ -C ₄ -alkyl substituted alkyl, alkenyl and alkynyl, in each case monosubstituted to polysubstituted by identical or different fluorine, chlorine, C _j -C ₄ alkyl, C ₁ -C ₄ -haloalkyl, C ₁ -C ₄ -alkoxy, CN, CO2H and / or CO-OC ^ -C _j alkyl-substituted cycloalkyl, cycloalkyl-alkyl and cycloalkenyl ,. in each case monosubstituted to trisubstituted by identical or different fluorine, chlorine, bromine, C _j -C ^ alkyl, _C] -C4-haloalkyl, C \ -C 4 alkoxy, C _j -C ^ haloalkoxy, nitro and / or cyano-substituted aryl , Heteroaryl, arylalkyl and heteroarylalkyl; and or

R ^ represents the radicals alkyl, alkenyl, alkynyl or alkoxy,

the aforementioned radicals are unsubstituted or substituted, are preferably unsubstituted or R ° is selected from the group consisting of in each case mono- to polysubstituted by identical or different fluorine and / or chlorine alkyl, alkenyl, alkynyl and alkoxy; and or

R ^ and R °, together with the nitrogen atom to which they are bonded, represent a saturated or unsaturated ring, which may optionally be interrupted by further heteroatoms,

the aforementioned ring is unsubstituted or substituted, preferably unsubstituted or monosubstituted, monosubstituted or differently substituted by C 1 -C ₄ -alkyl; and or

R9 and R.10 are each independently alkyl, alkenyl, alkoxy, alkenyloxy, alkynyloxy, cycloalkoxy, cycloalkenyloxy, cycloalkylalkoxy, alkylthio, alkenylthio, phenoxy, phenylthio, benzyloxy, benzylthio, heteroaryloxy, heteroarylthio, heteroarylalkoxy or

Heteroarylalkylthio,

the abovementioned radicals are unsubstituted or substituted, are preferably unsubstituted or R 1 and R 3 "are independently selected from the group consisting of in each case mono- to polysubstituted by identical or different substituents by fluorine and / or chlorine

Alkyl, alkenyl, alkoxy, alkenyloxy, alkynyloxy, alkylthio, and alkenylthio, in each case mono- or disubstituted by identical or different fluorine, chlorine, C, -C ₄ alkyl, C _r C ₄ -haloalkyl and / or C ₁ -C ₄ - Alkoxy substituted cycloalkoxy, cycloalkenyloxy and cycloalkyl alkoxy, in each case mono- to trisubstituted, identical or different

Fluorine, chlorine, bromine, Ci-C ₆ alkyl-C _r C ₄ haloalkyl, C _r C ₆ alkoxy, C ₁ - C ₄ haloalkoxy, Cj-Cβ alkylthio, cyano and / or nitro-substituted Phenoxy, phenylthio, benzyloxy, benzylthio, heteroaryloxy, heteroarylthio, heteroarylalkoxy and heteroarylalkylthio; and or

R ^ and Rl "are together with the phosphorus atom to which they are attached, for a 5- to 7-membered cycle which may be interrupted by one or two oxygen and / or sulfur atoms,

the aforementioned cycle unsubstituted or substituted, preferably unsubstituted or monosubstituted to trisubstituted by identical or different fluorine, chlorine, C _r C ₄ alkyl, C _r C ₄ -alkoxy and / or C _r C ₄ - haloalkyl groups; and or

R 1 and R 2 independently of one another represent the radicals alkyl, alkenyl, alkynyl, phenyl or phenylalkyl,

the abovementioned radicals are unsubstituted or substituted, are preferably unsubstituted or R 1 and R 2 are independently selected from the group consisting of in each case monosubstituted to trisubstituted by identical or different fluorine and / or chlorine alkyl, alkenyl and alkynyl, and in each case simply disubstituted by identical or different fluorine, chlorine, bromine, Ci-C ₄ - alkyl, _{Ci-C4-haloalkyl,} Ci-C ₄ alkoxy, C] -C ₄ haloalkoxy, cyano and / or nitro substituted phenyl and phenylalkyl ,

3. Use according to claim 1 or 2, wherein

-CG ¹ B ^ for a nitrogen atom N ^ or for the fragment | | .

- C- G "

B ^ for a nitrogen atom N ^ ^oc * ^er ^ ^r ^ ^as fragment B ^ for a nitrogen atom ^oc * ^er * ^ ^r ^ ^as Frag ^1116111 or for a

Binding,

and

B ^{4 stands} for the fragments, where the dashed bonds may be single bonds, double bonds or aromatic bonds;

X is hydrogen, fluorine, chlorine, bromine, cyano, hydroxy, alkoxy of 1 to 4 carbon atoms or alkylthio of 1 to 4 carbon atoms, C ₁ -Cg -alkyl or C ₁ -C 4 -haloalkyl;

Y is C ₁ -C ₁₀ -alkyl, C ₂ -C ₁₀ -alkenyl, C ₂ -C ₁₀ -alkynyl, C ₃ -C ₈ -cycloalkyl,

Phenyl- ^ -C ^ alkyl, wherein Y is unsubstituted or partially or completely halogenated and / or optionally carries one to three radicals R ^x , stands, or for C ^ C ^ -haloalkyl which optionally carries one to three radicals R ^x , wherein the R ^{x are} identical or different selected from the group consisting of cyano, nitro, hydroxy, C ₁ -Co-AUCyI, C ^ Cg-haloalkyl, C ₃ -Cg-CyClOaIlCyI,

C ₁ -Cg-alkoxy, C ₁ -Cg-haloalkyl, C ₁ -C 6 -alkylthio, C ₁ -Cg -haloalkylthio, C ₁ -C -alkylsulphinyl, C ₁ -C 6 -halogenoalkylsulphinyl, C ₁ -Cg -alkylsulphonyl, C ₁ -Cg-haloalkylsulfonyl, C ^ Cg-alkylamino, di-C ^ Cg-alkylamino, C 2 -Cg -alkenyl, C 2 -Cg -alkenyloxy, C 2 -Cg -alkynyl, C 3 -Cg -alkinyloxy and optionally halogenated Oxy-C ₁ -C 4

3-alkyl-C ₁ -C 4 -alkoxy and OXy-C ₁ -C 4 -alkyl-C ₁ -C 4 -alkyloxy;

or

Y is phenyl which may optionally be monosubstituted, monosubstituted or differently substituted by halogen, cyano, nitro, amino, hydroxy, formyl, carboxy, carboxyalkyl, carbamoyl, thiocarbamoyl;

in each case straight-chain or branched alkyl, alkoxy, alkylthio, alkylsulfinyl or alkylsulfonyl having in each case 1 to 6 carbon atoms; in each case straight-chain or branched alkenyl, alkynyl, alinyloxy or alkenyloxy having in each case 2 to 6 carbon atoms;

in each case straight-chain or branched alkylamino, dialkylamino, alkylcarbonyl, alkylcarbonyloxy, alkoxycarbonyl, alkylsulfonyloxy, hydroximinoalkyl or

Alkoximinoalkyl having in each case 1 to 6 carbon atoms in the individual alkyl moieties;

optionally mono- to disubstituted, by fluorine, chlorine, C ^ -C3-alkyl or C _j ^ -alkoxy-substituted cycloalkyl having 3 to 8 carbon atoms; or

1,3-propanediyl, 1,4-butanediyl linked in the 2,3-position or 3,4-position,

Methylenedioxy (-O-CH ₂ -O-) or 1,2-ethylenedioxy (-O-CH ₂ -CH ₂ -O-), where these radicals may be mono- or polysubstituted by identical or different substituents by halogen, alkyl with 1 to 4 carbon atoms and / or haloalkyl having 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms;

or

Y is saturated or wholly or partially unsaturated or aromatic heterocyclyl having 3 to 8 ring members and 1 to 3 heteroatoms selected from nitrogen, oxygen and sulfur, where the heterocyclyl may be monosubstituted or disubstituted by halogen, alkyl having 1 to 4 carbon atoms, alkoxy having 1 to 4 carbon atoms, alkylthio having 1 to 4 carbon atoms, haloalkoxy having 1 to 4 carbon atoms, haloalkylthio having 1 to 4 carbon atoms, hydroxy, mercapto, cyano, nitro and / or cycloalkyl having 3 to 6 carbon atoms and / or carboxyalkyl; Z represents hydroxyl, chlorine, bromine, in each case optionally substituted by 1 to 7 halogen atoms, straight-chain or branched C 1 -C -alkoxy, C 1 -C 6 -alkylthio,

/

C _j -Cg-alkylsulfonyl or the group - _| s _j stands;

G ^, G ^ and G ^ independently represent hydrogen, halogen, Cj-C ^ alkyl optionally substituted by one or more halogen atoms, C3-Cg-cycloalkyl optionally substituted by one or more halogen atoms, SCH3, SC ₂ H ₅ , SOCH ₃ , SOC ₂ H ₅ , SO ₂ CH ₃ , SO ₂ C ₂ H ₅ , OCH ₃ or OC ₂ H ₅ ;

L is oxygen or sulfur;

R 1 is hydrogen or alkyl of 1 to 10 carbon atoms, which is unsubstituted or monosubstituted to five times, identically or differently substituted by halogen, cyano, hydroxy, alkoxy having 1 to 4 carbon atoms, cycloalkyl having 3 to 6 carbon atoms, mercapto, alkylthio with 1 to 4 carbon atoms, amino, mono- or dialkylamino each having 1 to 4

Carbon atoms;

or

R 1 is alkenyl of 3 to 10 carbon atoms which is unsubstituted or monosubstituted to trisubstituted, identically or differently substituted by halogen, cyano, hydroxy, alkoxy of 1 to 4 carbon atoms, cycloalkyl of 3 to 6

Carbon atoms, mercapto, alkylthio of 1 to 4 carbon atoms, amino,

Mono or dialkylamino each having 1 to 4 carbon atoms;

or

R 1 represents alkynyl having 3 to 10 carbon atoms which is unsubstituted or monosubstituted to trisubstituted by identical or different substituents by halogen, cyano,

Hydroxy, alkoxy of 1 to 4 carbon atoms, cycloalkyl of 3 to 6

Carbon atoms, mercapto, alkylthio of 1 to 4 carbon atoms, amino,

Mono or dialkylamino each having 1 to 4 carbon atoms;

or R1 is cycloalkyl of 3 to 10 carbon atoms which is unsubstituted or monosubstituted to trisubstituted, identically or differently substituted by halogen, alkyl and / or haloalkyl each having 1 to 4 carbon atoms;

or

RI for saturated or unsaturated heterocyclyl having 3 to 10 ring members and 1 to 3 heteroatoms such as nitrogen, oxygen and / or sulfur, wherein the heterocyclyl is unsubstituted or monosubstituted or polysubstituted by halogen, alkyl having 1 to 4 carbon atoms, alkoxy having 1 to 4 Carbon atoms, cyano, nitro, cycloalkyl having 3 to 6 carbon atoms, hydroxy, alkoxy, alkenyloxy, alkynyloxy having 1 to 6 carbon atoms or

Mercapto, stands;

R ^ is hydrogen or alkyl of 1 to 6 carbon atoms;

or

R! and R ^ together with the nitrogen atom to which they are attached represent a saturated or unsaturated heterocyclic ring having 3 to 8

Ring members, wherein the heterocycle optionally contains another nitrogen, oxygen or sulfur atom as ring member, and wherein the heterocycle may be unsubstituted or substituted up to three times by fluorine, chlorine, bromine, alkyl having 1 to 4 carbon atoms, haloalkyl with 1 to 4 carbon atoms and 1 to 9

Fluorine and / or chlorine atoms, hydroxy, alkoxy having 1 to 4 carbon atoms, haloalkoxy having 1 to 4 carbon atoms and 1 to 9 fluorine and / or chlorine atoms, mercapto, thioalkyl having 1 to 4 carbon atoms and / or haloalkylthio having 1 to 4 carbon atoms and 1 to 9 fluorine and / or chlorine atoms;

R ^{3 is} CO, CO-OR ⁶ , CO-SR ⁶ , CS-OR ⁶ or CS-SR ⁶ ;

R ^ is hydrogen, cations from the series of the alkali or alkaline earth metals or ammonium ions NH4, mono- (Ci-Cio) -alkylammonium, di- (C _j _-C] o) alkyl ammonium, tri- (C γ -C (o) -alkylammonium, tetra (C 1 -C 10) -alkylammonium, wherein the alkyl radicals of the ammonium ions may be substituted by aryl or hydroxy, or cholinium,

in each case optionally monosubstituted to polysubstituted by fluorine, chlorine, C1-C4 alkoxy, Ci-C4-alkylthio, cyano, CO2 H or CO-OC i-C4alkyl C _j _{-C] Q} alkyl, C3-C _j o-alkenyl or C3-C _j 0-alkynyl, in each case optionally monosubstituted to polysubstituted by fluorine, chlorine, Cj-C4 alkyl, _C] -C4-haloalkyl, C] - C4 alkoxy, CN, CO 2 H or CO OC _{j-C4-alkyl-substituted} C3-Cg-cycloalkyl or C5-Cg-cycloalkenyl, which may be optionally interrupted by an oxygen or sulfur atom,

in each case optionally mono- to trisubstituted by fluorine, chlorine, bromine C1-C4-

Alkyl, _C] -C4-haloalkyl, C \ -C 4 alkoxy, _C] -C4 haloalkoxy, nitro or cyano-substituted phenyl, pyridyl, thiazolyl, pyrimidyl, benzyl, phenethyl, pyridinylmethyl or thiazolylmethyl group;

R ⁵ is hydrogen, mono- or polysubstituted in each case optionally substituted by fluorine and / or _chlorine-C] _-C] o-alkyl, C _j -C _{j Q} alkoxy, _{C3-C] Q} alkenyl,

C3-C] o-alkenyloxy or C3-C] ( ₎ -alkynyl; for the groups CO-R ⁷ , S (O)] R ⁷ ,

or is in each case optionally mono- to disubstituted by fluorine, chlorine, bromine, C] -C ₄ alkyl, Ci-C ₄ alkoxy, cyano or nitro-substituted pyridine, pyrimidine, triazine, thiazole or pyrazole;

or

R ⁴ and R ⁵ together with the nitrogen atom to which they are bonded, represent an optionally mono- or polysubstituted by C _r C ₄ alkyl substituted saturated or unsaturated 5- or 6-membered ring, which may optionally be interrupted by oxygen or sulfur, stand;

R6 is hydrogen, cations from the series of the alkali or alkaline earth metals or ammonium ions NH4, mono- _(C] _-C] o) alkylammonium, di- _(C] _-C] o) alkyl ammonium, tri- _(C] -C \ o) alkylammonium, tetra _(C] -C o) alkylammonium, wherein the alkyl radicals of the ammonium ions may be substituted by aryl or hydroxy, or cholinium,

in each case optionally mono- to polysubstituted by fluorine, chlorine, C ₁ -C ₄ -alkoxy, C ₁ -C ₄ -alkylthio, cyano, CO ₂ -H or CO-C ₁ -C ₄ -alkyl-substituted C ₁ -C 10 -alkyl, C ₃ -C ₃ -cycloalkyl Alkenyl or C3-C j g alkynyl, each optionally mono- to polysubstituted by fluorine, chlorine, Cj-C / j-alkyl, Cj-C ^ haloalkyl, C] - C4-alkoxy, CN, CO2H or CO-OC C 1 -C 4 -alkyl-substituted C 3 -C 8 -cycloalkyl, C 3 -C 6 -cycloalkyl-C 1 -C ₂ -alkyl or C 5 -C 8 -cycloalkenyl, which may be interrupted by an oxygen or sulfur atom,

Alkyl, Ci-C4 haloalkyl, _C] -C4-alkoxy, C \ -C4 haloalkoxy, nitro or cyano-substituted phenyl, pyridyl, thiazolyl, pyrimidyl, benzyl, phenethyl, pyridinylmethyl or thiazolylmethyl group;

R ^{7 represents} hydrogen, in each case optionally mono- to polysubstituted by fluorine, chlorine, C 1 -C ₄ -alkoxy, C 1 -C ₄ -alkylthio, cyano, CO 2 -H or CO-OC j -C ₄ -alkyl-substituted C 1 -C 8 -oxo Alkyl, C 3 -C 12 -alkenyl or C 3 -C 10 -alkynyl, in each case optionally mono- to polysubstituted by fluorine, chlorine, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy

Haloalkyl, C ₁ ^ -AlkOXy, CN, CO2H or CO-OC iC ₄ alkyl substituted

C3-C8-cycloalkyl, C3-C6-cycloalkyl-C] _-C2 alkyl or Cs-Cg-cycloalkenyl, which may be optionally interrupted by an oxygen or sulfur atom,

in each case optionally monosubstituted to trisubstituted by fluorine, chlorine, bromine, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, nitro or cyano, phenyl, pyridyl, thiazolyl, pyrimidyl, Benzyl, phenethyl, pyridinylmethyl or thiazolylmethyl;

R ° is hydrogen, in each case optionally mono- to polysubstituted by fluorine and / or chlorine, substituted Cj-Cg-alkyl, C3-C6-alkenyl, C3-Cg-alkynyl or Ci-Cg-alkoxy;

or

R ⁴ and R ⁷ together with the N-CO or NS (O) i _-2 group to which they are attached form a 4- to 8-membered cycle containing one or more heteroatoms may contain from the series sulfur, oxygen and / or nitrogen, wherein oxygen atoms may not be adjacent form;

or

R ⁷ and R ^8, together with the nitrogen atom to which they are bonded, represent a saturated or unsaturated 5- or 6-member which may optionally be mono- to polysubstituted by CpC ₄ -alkyl and may optionally be interrupted by oxygen or sulfur;

R ⁹ and R ¹⁰ independently of one another in each case optionally mono- to polysubstituted by fluorine and / or chlorine substituted C _r C ₈ alkyl, C ₃ -C ₈ alkenyl, C ₁ -C ₈ alkoxy, C ₃ -C ₈ alkenyloxy , C ₃ -C ₈ alkynyloxy, C _r C ₆ alkylthio,

C ₃ -C ₆ alkenylthio, optionally mono- or disubstituted by fluorine, chlorine, Ci-C ₄ alkyl, dC ₄ haloalkyl, C _r C ₄ -alkoxy-substituted C ₃ -C ₈ cycloalkoxy, C ₄ -C ₈ -cycloalkenyloxy or C ₃ -C ₈ - cycloalkyl-Ci-C ₂ alkoxy, in each case optionally mono- to trisubstituted by fluorine, chlorine, bromine, Ci-Ce-alkyl-Ci-Q-haloalkyl, C _r C ₆ -

Alkoxy, C _r C ₄ haloalkoxy, Ci-C ₆ -alkylthio, cyano or nitro-substituted phenoxy, phenylthio, benzyloxy, benzylthio, pyridinyloxy, pyrazolyloxy, pyridinylthio, pyrimidylthio, thiazolylthio, pyridyl-Ci-C ₂ - alkoxy, pyrimidyl-C _{r is} C ₂ alkyloxy, thiazolyl C ₁ -C ₂ alkyloxy, pyridyl Cp C ₂ alkylthio, thiazolyl C _r C ₂ alkylthio or pyrimidyl C _r C ₂ alkylthio;

or

R ⁹ and R ¹⁰ to which they are bound together with the phosphorus atom, seven-membered an optionally mono- to C ₄ alkyl, Q-Q-alkoxy or Ci-C five- triple ₄ -haloalkyl substituted by fluorine, chlorine, C _r to Cyclus, which may be interrupted by one or two oxygen and / or sulfur atoms are;

and

R ¹¹ and R ¹² independently of one another in each case optionally monosubstituted to trisubstituted by fluorine or chlorine, C ₁ -C ₈ -alkyl, C ₃ -C ₈ -alkenyl or

C ₃ -C ₈ -alkynyl, in each case optionally mono- to disubstituted by fluorine, chlorine, bromine, C _r C ₄ alkyl, C _r C ₄ haloalkyl, C _r C ₄ alkoxy, C, - C ₄ haloalkoxy, cyano or nitro substituted phenyl or benzyl.

Use according to any one of claims 1 to 3, wherein

-CG ¹ B ^ for a nitrogen atom N = or for the fragment | | .

-CG ² B ^ for a nitrogen atom N = ° for the fragment | | .

- C-G ³ B-3 for a nitrogen atom N ^ or for the fragment | | or for one

Binding,

and

- N- ^~ ? ⁼

B ^{4 represents} the fragments p3 or p3,

where the dashed bonds, single bonds, double bonds or aromatic bonds can be;

X represents hydrogen, fluorine, chlorine, cyano, C _r C ₄ alkyl or C _r C ₂ haloalkyl, which may be substituted by one to five fluorine and / or chlorine atoms;

Y is in each case optionally substituted by one to five fluorine and / or chlorine atoms substituted Ci-Cg-alkyl, C2-Cg-alkenyl, C2-C6-alkynyl or C3-Cg-cycloalkyl;

or

Y is phenyl, which may optionally be monosubstituted to trisubstituted, identically or differently, by fluorine, chlorine, bromine, iodine, cyano, nitro, formyl, Methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, vinyl, 1-propenyl, ethynyl, 1-propynyl, allyl, propargyl, methoxy, ethoxy, n- or i-propoxy , Methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl, ethylsulfonyl, allyloxy, propargyloxy, trifluoromethyl, trifluoroethyl, difluoromethoxy, trifluoromethoxy, difluorochloromethoxy, trifluoroethoxy, difluoromethylthio, difluorochloromethylthio, trifluoromethylthio, trifluoromethylsulfinyl, trifluoromethylsulfonyl, Trichloroethinyloxy, trifluoroethinyloxy, chloroallyloxy, iodopropargyloxy, methylamino, ethylamino, n- or i-propylamino, dimethylamino, diethylamino, acetyl, propionyl, acetyloxy, methoxycarbonyl, ethoxycarbonyl, hydroximinomethyl, hydroximinoethyl, methoximinomethyl, ethoxyminomethyl, methoximinoethyl, ethoximinoethyl Cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl; or

is linked in the 2,3-position or 3,4-position of 1,3-propanediyl, 1, 4- butanediyl, methylenedioxy (-0-CH ₂ -O-) or 1, 2-ethylenedioxy (-0-CH ₂ - CH ₂ -O-), these radicals being monosubstituted, polysubstituted, identically or differently substituted by fluorine, chlorine, methyl, ethyl, n-propyl, i-propyl, trifluoromethyl, carboxy and / or carboxymethyl;

or

Y is pyridyl which is linked in the 2- or 4-position and may be monosubstituted to the quadruple, identical or different, by fluorine, chlorine, bromine,

Cyano, hydroxy, mercapto, nitro, methyl, ethyl, methoxy, methylthio, hydroximinomethyl, hydroximinoethyl, methoximinomethyl, methoximinoethyl, trifluoromethyl, carboxy and / or carboxymethyl; or

Thiazolyl which is linked in the 2-, 4- or 5-position and may be monosubstituted, disubstituted or differently substituted by fluorine, chlorine, bromine,

Cyano, nitro, hydroxy, mercapto, methyl, ethyl, methoxy, methylthio, hydroximinomethyl, hydroximinoethyl, methoximinomethyl, methoximinoethyl, trifluoromethyl, carboxy and / or carboxymethyl; or

Pyrimidyl which is linked in the 2- or 4-position and may be monosubstituted to trisubstituted, identically or differently, by fluorine, chlorine, bromine,

Cyano, nitro, hydroxy, mercapto, methyl, ethyl, methoxy, methylthio, hydroxycarbonyl iminomethyl, hydroximinoethyl, methoximinomethyl, methoximinoethyl, trifluoromethyl, carboxy and / or carboxymethyl; or

Thienyl which is linked in the 2- or 4-position and may be monosubstituted to trisubstituted, identically or differently, by fluorine, chlorine, bromine, cyano, nitro, hydroxyl, mercapto, methyl, ethyl, methoxy, methylthio, hydroximinomethyl, Hydroximinoethyl, methoximinomethyl, methoximinoethyl, trifluoromethyl, carboxy and / or carboxymethyl;

Z is chlorine, bromine, in each case optionally substituted by 1 to 3 halogen atoms, straight-chain or branched C _r C ₄ alkoxy, Ci-C ₄ alkylthio or

the group N is;

R ²

G ¹ , G ² and G ³ independently of one another represent hydrogen, halogen, (C 1 -C ₄ ) -alkyl optionally substituted by one or more halogen atoms, optionally substituted by one or more halogen atoms

cyclopropyl; SCH ₃ , SC ₂ H ₅ , SOCH ₃ , SOC ₂ H ₅ , SO ₂ CH ₃ , SO ₂ C ₂ H ₅ , OCH ₃ or OC ₂ H ₅ ;

L is oxygen or sulfur;

R ^{1 is} hydrogen, alkyl of 1 to 8 carbon atoms which is unsubstituted or monosubstituted to trisubstituted, identically or differently, by fluorine, chlorine, cyano, alkoxy of 1 to 3 carbon atoms, cycloalkyl of 3 to 6 carbon atoms, alkylthio of 1 to 8 carbon atoms 3 carbon atoms, stands;

or

R 1 represents alkenyl of 3 to 8 carbon atoms which is unsubstituted or monosubstituted to trisubstituted, identically or differently, by fluorine, chlorine, cyano, alkoxy of 1 to 3 carbon atoms, cycloalkyl of 3 to 6 carbon atoms, alkylthio of 1 to 3 carbon atoms , stands;

or

R! for alkynyl having 3 to 8 carbon atoms, which is unsubstituted or monosubstituted to trisubstituted by identical or different substituents by fluorine, chlorine, cyano, Alkoxy of 1 to 3 carbon atoms, cycloalkyl of 3 to 6 carbon atoms, alkylthio of 1 to 3 carbon atoms;

or

RI is cycloalkyl of 3 to 8 carbon atoms which is unsubstituted or monosubstituted to trisubstituted, identically or differently substituted by fluorine, chlorine and / or

Alkyl, haloalkyl, alkoxy each having 1 to 2 carbon atoms;

or

R.1 represents saturated or unsaturated heterocyclyl having 3 to 8 ring members and 1 to 2 heteroatoms, such as nitrogen, oxygen and / or sulfur, wherein the heterocyclyl is unsubstituted or monosubstituted or disubstituted by

Hydroxy, fluoro, chloro, alkyl of 1 to 3 carbon atoms, alkoxy of 1 to 3 carbon atoms, cyano, nitro or cycloalkyl of 3 to 6 carbon atoms;

R ^ is hydrogen or alkyl of 1 to 6 carbon atoms;

or

R! and R ^ together with the nitrogen atom to which they are attached represent a saturated or unsaturated heterocyclic ring having from 3 to 6 ring members, said heterocycle optionally containing another nitrogen, oxygen or sulfur atom as ring member and wherein said heterocycle is unsubstituted or may be substituted up to three times by fluorine, chlorine, bromine, alkyl having 1 to 3 carbon atoms, haloalkyl having 1 to 3 carbon atoms and 1 to 5 fluorine and / or chlorine atoms, alkoxy having 1 to 3 carbon atoms, haloalkoxy having 1 to 3 carbon atoms and 1 to 5 fluorine and / or chlorine atoms, thioalkyl having 1 to 3 carbon atoms and / or

Halogenalkylthio having 1 to 3 carbon atoms and 1 to 5 fluorine and / or chlorine atoms;

R ^{3 is} CON " ^R , CO-OR ⁶ , CO-SR ⁶ , CS-OR ⁶ or CS-SR ⁶ ; V R ^{4 is} hydrogen, Na ⁺ , K ⁺ , V ₂ Ca ²⁺ , '/ - Mg ²⁺ , NH ₄ ⁺ , NH ₃ CH ₃ ⁺ , NH ₂ (CH ₃ ) ₂ ⁺ , NH (CH ₃ ) ₃ ⁺ , NH (C ₂ Hs) ₃ ⁺ , NH ₂ (C ₂ Hs) ₂ ⁺ , NH ₃ C ₂ H ₅ ⁺ , NH ₃ IC ₃ H ₇ ⁺ , NH ₂ (JC ₃ Hy) ₂ ⁺ ,

NH ₃ -CH ₂ -C ₆ H ₅ ⁺ , N (CHj) ₃ -H ₂ -C ₆ H ₅ ⁺ , or,

in each case optionally mono- to trisubstituted by fluorine, chlorine, C _r C ₃ alkoxy, C _r C ₃ alkylthio, cyano, CO ₂ H or CO-OC, -C ₃ alkyl, substituted C ₁ -C ₈ -

Alkyl, C ₃ -C ₈ -alkenyl or C ₃ -C ₈ -alkynyl, in each case optionally mono- to trisubstituted by fluorine, chlorine, C _r C ₃ alkyl, Ci-C ₂ haloalkyl, C _r C ₃ alkoxy,

CN, CO ₂ H or CO-OC _r C ₃ -alkyl-substituted C ₃ -C ₆ -cycloalkyl, C ₃ -C ₆ -

Cycloalkylmethyl or C ₅ -C ₆ -cycloalkenyl, which may optionally be interrupted by an oxygen or sulfur atom,

each optionally optionally mono- to disubstituted by fluorine, chlorine, bromine, CpC ₃ - alkyl, C _r C ₃ haloalkyl, Ci-C ₃ alkoxy, Ci-C ₃ haloalkoxy, nitro or cyano-substituted phenyl, pyridyl, thiazolyl, pyrimidyl Benzyl, phenethyl, pyridinylmethyl or thiazolylmethyl;

R ^ represents hydrogen, represents in each case optionally mono- to trisubstituted by fluorine and / or chlorine, Ci-C ₈ alkyl, C _r C ₈ alkoxy, C ₃ -C ₈ alkenyl, C ₃ -C ₈ - alkenyloxy or C ₃ -C ₈ alkynyl; for the groups COR ⁷ , S (O) ₁ R ⁷ , cyano, COOR ⁷ ,

or optionally in each case optionally once or twice by fluorine, chlorine, bromine,

C ₁ -C ₃ -alkyl, C ₁ -C ₃ -alkoxy, cyano, hydroxy or nitro-substituted pyridine, pyrimidine, triazine, thiazole, pyrazole, oxazole or triazole;

or

R ⁴ and R ⁵ together with the nitrogen atom to which they are bonded, represent an optionally mono- or disubstituted by C _r C ₂ alkyl substituted saturated or unsaturated 5- or 6-membered ring, which may optionally be interrupted by oxygen or sulfur, stand; R ^{6 is} hydrogen, Na ⁺ , K ⁺ , V ₂ Ca ²⁺ , ¹ A Mg ²⁺ , NH ₄ ⁺ , NH ₃ CH ₃ ⁺ , NH ₂ (CH ₃ ) ₂ ⁺ , NH (CH ₃ ) ₃ ⁺ , NH (C ₂ H ₅ ) ₃ ⁴ , NH ₂ (C ₂ H ₅ ) /, NH ₃ C ₂ H ₅ ⁺ , NH ₃ IC ₃ H ₇ ⁺ , NH ₂ (iC ₃ H ₇ ) ₂ ⁺ , NH ₃ - CH ₂ -C ₆ H ₅ ⁺ or N (CH ₃ ) ₃ -H ₂ -C ₆ H ₅ ⁺ ,

in each case optionally mono- to trisubstituted by fluorine, chlorine, C _r C ₃ alkoxy, C _r C ₃ alkylthio, cyano, CO ₂ H or CO-OC, -C ₃ alkyl, substituted C ₈ -

Alkyl, CpCg-alkenyl or Ci-Cg-alkynyl, each optionally optionally mono- to trisubstituted by fluorine, chlorine, C _r C ₃ alkyl, C _r C ₃ haloalkyl, C _r C ₃ alkoxy,

in each case optionally mono- to disubstituted by fluorine, chlorine, bromine, Ci-C ₄ - alkyl, _{Ci-C4-haloalkyl,} Ci-C ₄ alkoxy, QQ-haloalkoxy, nitro or cyano-substituted phenyl, pyridyl, thiazolyl, pyrimidyl, Benzyl, phenethyl, pyridinylmethyl or thiazolylmethyl;

R ^{7 is} hydrogen, for each optionally simply to five times by fluorine,

Chlorine, C ₁ -C ₃ -alkoxy, C ₁ -C ₃ -alkylthio, cyano, CO ₂ H or CO-OC _r C ₃ -alkyl-substituted C ₁ -C ₈ -alkyl, C ₃ -C ₈ -alkenyl or C ₃ -C ₈ -alkynyl, each optionally optionally mono- to trisubstituted by fluorine, chlorine, QC ₄ alkyl, C _r C ₂ - haloalkyl, C _r C ₂ alkoxy, CN, CO ₂ H or CO-OC _r C ₂ alkyl substituted C C ₃ -C ₆ -cycloalkyl, C ₃ -C ₆ -cycloalkyl-methyl or C ₅ -C ₆ -cycloalkenyl, which may optionally be interrupted by an oxygen or sulfur atom,

in each case optionally mono- to disubstituted by fluorine, chlorine, bromine, Ci-C ₃ - alkyl, Ci-C ₃ haloalkyl, C _r C ₃ alkoxy, C] -C ₃ haloalkoxy, nitro or cyano-substituted phenyl, pyridyl, Thiazolyl, pyrimidyl, benzyl, phenethyl, pyridinylmethyl or thiazolylmethyl;

R ⁸ represents hydrogen, in each case optionally mono- to trisubstituted by fluorine and / or chlorine-substituted C] -C ₄ alkyl, C ₃ -C ₄ alkenyl, C ₃ -C ₄ alkynyl or C _r C ₄ alkoxy;

or

R ⁴ and R ⁷ together with the N-CO or NS (O) _{] -2} group to which they are attached form a 4- to 6-membered cycle containing one or more heteroatoms may contain from the series sulfur, oxygen and / or nitrogen, wherein oxygen atoms may not be adjacent form;

or

R ⁷ and R ^8, together with the nitrogen atom to which they are bonded, represent a saturated or unsaturated 5- or 6-member which is optionally mono- to disubstituted by C ₁ -C ₂ -alkyl and may be interrupted by oxygen or sulfur, stand;

R ⁹ and R ¹⁰ independently of one another in each case optionally mono- to trisubstituted by fluorine and / or chlorine, Ci-C ₆ alkyl, C ₃ -C ₆ alkenyl, C _r C ₆ alkoxy, C ₃ -C ₆ alkenyloxy, C ₃ -C ₆ alkynyloxy, C _r C ₄ alkylthio,

C ₃ -C ₄ -alkenylthio, each of which is optionally mono- to disubstituted by fluorine, chlorine, C ₁ -C ₂ -AIl ^ yI, C _r C ₂ -haloalkyl, C _r C ₂ -alkoxy-substituted C ₃ -C ₆ cycloalkoxy, C ₄ -C ₆ -cycloalkenyloxy or C ₃ -C ₆ - _{cycloalkyl-Ci-C2-alkyloxy,} in each case optionally mono- to disubstituted by fluorine, chlorine, bromine, C ₁ -C ₄ alkyl-C ₁ -C ₂ - Haloalkyl, C ₁ -

C ₄ alkoxy, C _r C ₂ -haloalkoxy, C ₁ -C ₄ alkylthio, methyloxy cyano or nitro-substituted phenoxy, phenylthio, benzyloxy, benzylthio, pyridinyloxy, pyrazolyloxy, pyridinylthio, pyrimidylthio, thiazolylthio, pyridyl, pyrimidyl methyloxy, Thiazolylmethyloxy, pyridylmethylthio, thiazolylmethylthio or pyrimidylmethylthio;

or

R ⁹ and R ¹⁰ to which they are together with the phosphorus atom bonded, represent an optionally mono- or disubstituted by fluorine, chlorine, C ₁ -C ₂ -AUCyI, C ₁ - C ₂ alkoxy or C _r C ₂ -haloalkyl substituted five - to six-membered cycle of by one or two oxygen and / or

Sulfur atoms can be interrupted, stand;

and

R ¹¹ and R ¹² independently of one another represent in each case optionally mono- to trisubstituted by fluorine or chlorine, Ci-C ₆ alkyl, C ₃ -C ₆ alkenyl or C ₃ -C ₆ alkynyl are.

Use according to any one of claims 1 to 4, wherein

for A, B ¹ , B ² , B ³ and B ⁴ either

a) A = - C -, B ¹ = ,, BB ^3J ==

and B ⁴ = C; or

R ³

b) A = C -, B ¹ = = C - G ¹ , B ² = = N -, B ⁴ = N and B ³ = one

Il IR ³

Binding is valid; or

c) A = N -, B ^J = ^{N -} , B ² = = C - G ² , B ⁴ = = C and B ³ =

IIR ^{3 is} a bond;

and

X is hydrogen, chlorine, methyl or trifluoromethyl;

Y is (C ₁ -Co) -AlRyI, (C ₃ - ₆₎ alkenyl, (C ₃ -C ₆₎ -alkynyl or (C ₃ -C ₆₎ -cycloalkyl, where Y is unsubstituted or substituted by one to three fluorine or chlorine atoms is substituted;

or

Y is monosubstituted to trisubstituted phenyl having substituents selected from the group consisting of fluoro, chloro, bromo, cyano, nitro, methyl, ethyl, tert -butyl, methoxy, ethoxy, trifluoromethyl, difluoromethoxy and trifluoromethoxy;

or

Y 'is pyridyl which is linked in the 2- or 4-position and may be mono- to disubstituted, identically or differently substituted by fluorine, chlorine, bromine, cyano, methyl, ethyl, methoxy, methylthio or trifluoromethyl; or Pyrimidyl which is linked in the 4-position and may be monosubstituted to trisubstituted, identically or differently substituted by fluorine, chlorine, bromine, cyano, methyl, ethyl, methoxy, methylthio or trifluoromethyl; or

Thienyl which is linked in the 2- or 3-position and may be monosubstituted, disubstituted, identical or differently substituted by fluorine, chlorine, bromine,

Cyano, nitro, methyl, ethyl, methoxy or trifluoromethyl;

Z is chlorine, methoxy, ethoxy, methylthio, ethythio or the group

- N stands; R ²

G ¹ , G ² and G ³ independently represent hydrogen, chlorine, bromine, methyl, ethyl, trifluoromethyl or cyclopropyl;

L is oxygen or sulfur;

R ¹ represents hydrogen, alkyl having 1 to 6 carbon atoms, which is unsubstituted or mono- to trisubstituted by identical or different substituents, by fluorine, chlorine, methoxy, ethoxy, cyclopropyl, cyclopentyl, cyclohexyl, methylthio or ethylthio group;

or

R 1 is alkenyl of 3 to 6 carbon atoms which is unsubstituted or monosubstituted to trisubstituted, identically or differently substituted by fluorine, chlorine, methoxy, ethoxy, methylthio or ethylthio;

or

R! alkynyl of 3 to 6 carbon atoms which is unsubstituted or monosubstituted to trisubstituted, identically or differently substituted by fluorine, chlorine, methoxy, ethoxy, methylthio or ethylthio;

or

R! for cycloalkyl of 3 to 6 carbon atoms which is unsubstituted or monosubstituted to trisubstituted, identically or differently substituted by fluorine, chlorine, methyl, ethyl, methoxy or trifluoromethyl; R ^{2 is} hydrogen, methyl or ethyl;

or

R ¹ and R ^2, together with the nitrogen atom to which they are attached, represent a saturated or unsaturated heterocyclic ring containing 3 to 6 ring members, the heterocycle optionally being another

Nitrogen, oxygen or sulfur atom as ring member and wherein the heterocycle may be unsubstituted or substituted up to two times by fluorine, chlorine, methyl, ethyl, trifluoromethyl, methoxy or ethoxy;

R ^{3 is} or CO-OR ⁶ ;

R ^{4 is} hydrogen, Na ⁺ , K ⁺ , V ₂ Ca ²⁺ , V ₂ Mg ²⁺ , NH ₄ ⁺ , NH ₃ CH ₃ ⁺ , NH ₂ (CH ₃ ) ₂ ⁺ , NH (CHa) ₃ ⁺ , NH (C ₂ Hs) ₃ ⁺ , NH ₂ (C ₂ H ₅ ) ₂ ⁺ , NH ₃ C ₂ H ₅ ⁺ , NH ₃ IC ₃ H ₇ ⁺ , NH ₂ (iC ₃ H ₇ ) ₂ ⁺ , NH ₃ -CH ₂ -C ₆ H ₅ ⁺ or N (CH ₃ ) ₃ -H ₂ -C ₆ H ₅ ⁺ ,

substituted in each case optionally mono- to trisubstituted by fluorine, chlorine, methoxy, ethoxy, methylthio, ethylthio, cyano, CO-O-methyl or CO-O-Ethyl C _r C ₆ alkyl, C ₃ -C ₆ -alkenyl or C ₃ C ₆ alkynyl, each optionally optionally mono- to trisubstituted by fluorine, chlorine, methyl, ethyl, trifluoromethyl, methoxy, ethoxy, cyano, CO-O-methyl or CO-O-ethyl substituted C ₃ -C ₆ cycloalkyl;

R ^ is hydrogen, for each optionally monosubstituted to trisubstituted by fluorine and / or chlorine C _r C ₆ alkyl, Ci-C ₆ alkoxy, C ₃ -C ₆ alkenyl, C ₃ -C ₆ alkenyloxy or C ₃ C ₆ alkynyl, or for the groups COR ⁷ , S (O) R ⁷ , cyano, COOR ⁷ ,

stands;

or R ⁴ and R ⁵ together with the nitrogen atom to which they are attached represent a saturated 5- or 6-membered ring which may optionally be interrupted by oxygen or sulfur;

R ^{6 is} hydrogen, Na ⁺ , K ⁺ , ¹ A Ca ²⁺ , Vi Mg ²⁺ , NH ₄ ⁺ , NH ₃ CH ₃ ⁺ , NH ₂ (CH ₃ ) ₂ ⁺ , NH (CH ₃ ) ₃ ⁺ , NH (C ₂ Hs) ₃ ⁺ , NH ₂ (C ₂ H ₅ ) ₂ ⁺ , NH ₃ C ₂ H ₅ ⁺ , NH ₃ IC ₃ H ₇ ⁺ , NH ₂ (iC ₃ H ₇ ) ₂ ⁺ ,

NH ₃ -CH ₂ -C ₆ H ₅ ⁺ or N (CH ₃ ) ₃ -H ₂ -C ₆ H ₅ ⁺ ,

in each case optionally mono- to trisubstituted by fluorine, chlorine, methoxy, ethoxy, methylthio, ethylthio, cyano, CO ₂ H, CO-O-methyl or CO-O-ethyl-substituted Ci-C ₆ alkyl, C ₃ -C ₆ - Alkenyl or C ₃ -C ₆ alkynyl;

R ^{7 is} hydrogen, in each case optionally once to three times by fluorine,

Chlorine, methoxy, ethoxy, methylthio, ethylthio, cyano, CO-O-methyl or CO-O-ethyl substituted C _r C ₆ alkyl, C ₃ -C ₆ alkenyl or C ₃ -C ₆ alkynyl, each optionally monosubstituted by fluorine, chlorine, methyl, ethyl, methoxy, trifluoromethyl, cyano, CO ₂ H, CO-O-methyl or CO-O-C ethyl ₃ - Cg cycloalkyl, C- _j -CG-cycloalkyl-methyl, or C5 C5-cycloalkenyl, which may optionally be interrupted by an oxygen or sulfur atom, each optionally optionally mono- to disubstituted by fluorine, chlorine, bromine methyl, trifluoromethyl, methoxy-substituted phenyl, pyridyl, thiazolyl, pyrimidyl, benzyl, phenethyl, pyridinylmethyl or thiazolylmethyl stands;

R ^{8 is} hydrogen, methyl, ethyl, propyl, isopropyl, allyl, propargyl, C ₃ -C ₄ -

Alkenyl, methoxy or ethoxy;

or

R ⁷ and R ⁸ together with the nitrogen atom to which they are attached stand for a saturated 5- or 6-membered ring, which may optionally be interrupted by oxygen or sulfur;

and

R ⁹ and R ¹⁰ independently of one another represent in each case optionally mono- to trisubstituted by fluorine and / or chlorine-substituted methyl, ethyl, methoxy, ethoxy, propoxy, i-propoxy, butoxy, alkyloxy, methylthio, ethylthio, propylthio, butylthio, i-propylthio, sec-butylthio, allylthio.

Use according to any one of claims 1 to 5, wherein

for A, B ¹ , B ² , B ³ and B ⁴

A = N, B ¹ = ^{N ~} , B ² = = C ^- G ² , B ⁴ = = C and B ³ = one

IIR ³ binding applies;

and

X is hydrogen, chloro, methyl or trifluoromethyl;

Y is (C ₁ -Co) -alkyl, (C ₃ - ₆₎ alkenyl, (C ₃ -C ₆₎ -alkynyl or (C ₃ -C ₆₎ -cycloalkyl, where Y is unsubstituted or substituted by one to three fluorine or chlorine atoms is substituted;

or

Y is pyridyl which is linked in the 2- or 4-position and may be monosubstituted, disubstituted or differently substituted by fluorine, chlorine, bromine, cyano, methyl, ethyl, methoxy, methylthio or trifluoromethyl; or

Thienyl which is linked in the 2- or 3-position and may be monosubstituted, disubstituted or differently substituted by fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, methoxy or trifluoromethyl; Z is chlorine, methoxy, ethoxy, methylthio, ethythio or the group

L is oxygen or sulfur;

R ^{1 is} hydrogen, alkyl of 1 to 6 carbon atoms which is unsubstituted or monosubstituted to trisubstituted, identically or differently, by fluorine, chlorine, methoxy, ethoxy, cyclopropyl, cyclopentyl, cyclohexyl, methylthio or ethylthio;

or

R! for cycloalkyl having 3 to 6 carbon atoms which is unsubstituted or monosubstituted to trisubstituted, identically or differently substituted by fluorine, chlorine, methyl,

Ethyl, methoxy or trifluoromethyl;

R ^ is hydrogen, methyl or ethyl;

or

R! and R ^ together with the nitrogen atom to which they are attached represent a saturated or unsaturated heterocyclic ring having 3 to 6

Ring members, wherein the heterocycle optionally contains a further nitrogen, oxygen or sulfur atom as a ring member, and wherein the heterocycle may be unsubstituted or substituted up to two times by fluorine, chlorine, methyl, ethyl, trifluoromethyl, methoxy or ethoxy;

R ^{4 is} hydrogen,

in each case optionally mono- to trisubstituted by fluorine, chlorine, methoxy, ethoxy, methylthio, ethylthio, cyano, CO-O-methyl or CO-O-ethyl-substituted C ₆ alkyl, C ₃ -C ₆ -alkenyl or C ₃ C ₆ alkynyl, each optionally optionally mono- to trisubstituted by fluorine, chlorine, methyl, ethyl, trifluoromethyl, methoxy, ethoxy, cyano, CO-O-methyl or CO-O-ethyl substituted C ₃ -C ₆ cycloalkyl;

R-> is hydrogen, for each optionally monosubstituted to trisubstituted by fluorine and / or chlorine C _r C ₆ alkyl, Ci-C ₆ alkoxy, C ₃ -C ₆ alkenyl, C ₃ -C ₆ alkenyloxy or C C ₃ -C ₆ -alkynyl, or for the groups COR ⁷ , S (O), J 2, cyano, COOR ⁷ ,

stands;

or

R ⁴ and R ⁵ together with the nitrogen atom to which they are attached represent a saturated 5- or 6-membered ring which may optionally be interrupted by oxygen or sulfur;

R ^{6 is} hydrogen,

in each case optionally monosubstituted to trisubstituted by fluorine, chlorine, methoxy, ethoxy, methylthio, ethylthio, cyano, CO ₂ H, CO-O-methyl or CO-O-ethyl C _r C ₆ -alkyl, C ₃ -C ₆ - alkenyl or C ₃ -C ₆ -alkynyl; R ^{7 is} hydrogen, in each case optionally once to three times by fluorine,

Chlorine, methoxy, ethoxy, methylthio, ethylthio, cyano, CO-O-methyl or CO-

O-ethyl-substituted C ₁ -C ₆ -alkyl, C ₃ -C ₆ -alkenyl or C ₃ -C ₆ -alkynyl, in each case optionally denoted simply by fluorine, chlorine, methyl, ethyl, methoxy, trifluoromethyl, cyano, CO ₂ H , CO-O-methyl or CO-O-ethyl substituted C ₃ -

C ₃ -C 6 -cycloalkyl, C ₃ -C 5 -cycloalkyl-methyl or C 5 -C 6 -cycloalkenyl, which may optionally be interrupted by an oxygen or sulfur atom, in each case optionally once to twice by fluorine, chlorine, bromine

Methyl, trifluoromethyl, methoxy substituted phenyl, pyridyl, thiazolyl, pyrimidyl, benzyl, phenethyl, pyridinylmethyl or thiazolylmethyl;

R ^{8 is} hydrogen, methyl, ethyl, propyl, iso-propyl, allyl, propargyl, C ₃ -C ₄ alkenyl, methoxy or ethoxy;

or

R ⁷ and R ⁸ together with the nitrogen atom to which they are attached represent a saturated 5- or 6-membered ring optionally substituted by oxygen or

Sulfur can be interrupted, stand;

and

R ⁹ and R ¹⁰ independently of one another are each optionally mono- to trisubstituted by fluorine and / or chlorine, methyl, ethyl, methoxy, ethoxy, propoxy, isopropoxy, butoxy, alkyloxy, methylthio, ethylthio,

Propylthio, butylthio, i-propylthio, sec-butylthio, allylthio.

7. Use of a mixture comprising at least one of the compounds defined in claims 1 to 6 and / or at least one of their agrochemically active salts and a further active ingredient selected from the group consisting of

Insecticides, attractants, sterilants, bactericides, acaricides, nematicides, fungicides, growth regulators, herbicides, safeners, fertilizers or semiochemicals for controlling animal pests.

Use according to any one of claims 1 to 7, wherein the animal pests are selected from the group consisting of insects, subclass parasites

Acari (Acarina), in particular mites, spider mites and ticks, and nematodes.

Use according to any one of claims 1 to 8 for the treatment of plants or for the treatment of seed of plants.

10. Use according to claim 9, wherein the plants are selected from the group of transgenic plants.

11. Means for controlling animal pests in and / or on plants or in and / or on seeds of plants, said means comprising at least one compound as defined in any one of claims 1 to 6 and / or at least one of their agrochemically active salts or a mixture as defined in claim 7 and agrochemically customary auxiliaries and / or additives.

12. Composition according to claim 11, wherein the auxiliaries and / or additives are selected from the group consisting of extenders and / or surface-active substances.

13. Means for controlling animal pests in and / or on plants or in and / or on seeds of plants, said means comprising at least one compound as defined in any one of claims 1 to 6 and / or at least one of their agrochemically active salts and at least one salt of the formula (II)

in which

Q is nitrogen or phosphorus,

R ²⁶ , R ²⁷ , R ²⁸ and R ²⁹ are each independently hydrogen or optionally substituted C _r C ₈ alkyl or mono- or polyunsaturated, optionally substituted C _r Cg-alkylene, wherein the substituents selected from halogen, nitro and cyano could be,

n is 1, 2, 3 or 4,

R ^{30 is} an inorganic or organic anion,

includes.

14. Composition according to claim 13, characterized in that the active ingredient content is between 0.5 and 50 wt .-%.

15. Composition according to claim 13 or 14, characterized in that the content of ammonium or phosphonium salt is between 0.5 and 80 mmol / 1.

16. Composition according to one or more of claims 13 to 15, characterized in that Q is nitrogen.

17. Composition according to claim 16, characterized in that R ^{30 represents} hydrogencarbonate, tetraborate, fluoride, bromide, iodide, chloride, monohydrogenphosphate, dihydrogenphosphate, hydrogensulphate, tartrate, sulphate, nitrate, thiosulphate, thiocyanate, formate, lactate, acetate, propionate, Butyrate, pentanoate, citrate or oxalate.

18. Composition according to claim 16, characterized in that R ^{30 represents} carbonate, pentaborate, sulfite, benzoate, hydrogen oxalate, hydrogen citrate, methyl sulfate or tetrafluoroborate.

19. A composition according to claim 16, characterized in that R ^{30 is} lactate, sulfate, nitrate, thiosulfate, thiocyanate, citrate, oxalate or formate.

20. A composition according to claim 16, characterized in that R ^{30 is} thiocyanate, dihydrogen phosphate, monohydrogen phosphate or sulfate.

21. Composition according to one of claims 13 to 20, characterized in that it contains at least one penetration promoter.

22. Composition according to claim 21, characterized in that the penetration promoter is a fatty alcohol alkoxylate of the formula (HI)

RO - (- AO) _v -R '(III)

in which

R is straight-chain or branched alkyl having 4 to 20 carbon atoms,

R 'is hydrogen, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, t-butyl, n-pentyl or n-hexyl,

AO stands for an ethylene oxide radical, a propylene oxide radical, a butylene oxide radical or mixtures of ethylene oxide and propylene oxide radicals or butylene oxide radicals and v is numbers from 2 to 30,

or a mineral or vegetable oil or the ester of a mineral or vegetable oil.

23. A composition according to claim 21, characterized in that the penetration promoter is the ester of a vegetable oil.

24. Composition according to claim 21, characterized in that the penetration promoter is rapeseed oil methyl ester.

25. Composition according to one of claims 21 to 24, characterized in that the content of penetration promoter is 1 to 95 wt .-%.

26. A method of controlling animal pests in and / or on plants or in and / or on seeds of plants comprising directly or indirectly contacting said pests with at least one compound as defined in claims 1 to 6 and / or at least one of their agrochemically active salts or a mixture as defined in claim 6 or an agent as defined in claims 11 to 25.

27. The method according to claim 26, wherein

(i) the animal pests are selected from the group consisting of insects, parasites of the subclass of Acari (Acarina), in particular mites, spider mites and ticks, and nematodes; and or

(ii) the plants are selected from the group consisting of transgenic plants.

A process for the preparation of an agent as defined in claims 11 to 25 comprising mixing at least one compound as defined in any one of claims 1 to 6 and / or at least one of their agrochemically active salts or a mixture as defined in claim 7 with agrochemical usual Auxiliaries and / or additives.

29. The method according to claim 28, wherein the auxiliaries and / or additives are selected from the group consisting of extenders and / or surface-active substances.

30. Seed comprising at least one compound as defined in any one of claims 1 to 6 and / or at least one of the agrochemically active thereof Salts or a mixture as defined in claim 7 or as defined in the claims 1 1 to 25 agent was treated.

31. Seed according to claim 30, wherein the seed is selected from seeds of transgenic plants.