KR100518372B1 - Substituted phenylketoenols as pesticides and herbicides - Google Patents

Abstract

The present invention relates to novel compounds of general formula (I), their preparation, intermediates for their preparation, and their use as pesticides and herbicides:

Where

Het is a group

Represents one of

A, B, D, G, V, W, X, Y and Z are as mentioned in the specification.

Description

Substituted phenylketoenols as pesticides and herbicides

The present invention relates to novel phenyl-substituted cyclic ketoenols, many methods for their preparation, intermediates for their preparation, and their use as pesticides and herbicides.

It is already known that certain phenyl-substituted cyclic ketoenols are active as insecticides, acaricides and / or herbicides.

The pharmaceutical properties of 3-acyl-pyrrolidine-2,4-dione are already known (S. Suzuki et al. Chem. Pharm. Bull. 15 1120 (1967)). In addition, N-phenylpyrrolidine-2,4-dione is known. R. Schmierer and H. It was synthesized by H. Mildenberger (Liebigs Ann. Chem. 1985, 1095). However, the biological activity for these compounds is not yet known.

EP-A-0 262 399 and GB-A-2 266 888 describe 3-aryl-pyrrolidine-2,4-dione compounds of similar structure but do not mention herbicidal, pesticidal or acaricide activity. Did. Unsubstituted bicyclic 3-aryl-pyrrolidine-2,4-dione derivatives (EP-A-355 599 and EP-A-415 211) having herbicidal, pesticidal or acaricide activity and substituted mono Click 3-aryl-pyrrolidine-2,4-dione derivatives (EP-A-377 893 and EP-A-442 077) are known.

Polycyclic 3-aryl-pyrrolidine-2,4-dione derivatives (EP-A-442 073) and 1H-aryl-pyrrolidine-dione derivatives (EP-A-456 063, EP-A-521 334 , EP-A-596 298, EP-A-613 884, EP-A-613 885, DE 44 40 594, WO 94/01 997, WO 95/01 358, WO 95/20 572, EP-A-668 267 and WO 95/26 954 are also known.

It is known that certain substituted Δ ³ -dihydrofuran-2-one derivatives have herbicidal activity (DE-A-4 014 420). Synthesis of Tetronic Acid Derivatives (eg 3- (2-methyl-phenyl) -4-hydroxy-5- (4-fluorophenyl) -Δ ³ -dihydrofuran-2-one) used as starting material This is also described in DE-A-4 014 420. Compounds of similar structure are described by Campbell et al., J. Chem. Soc., Perkin Trnas. 1, 1985, (8) 1567-76, but no description of pesticidal and / or acaricide activity. In addition, 3-aryl-Δ ³ -dihydrofuranone derivatives having herbicidal, acaricide and pesticidal activity are described in EP-A-528 156 and EP-A-0 647 637. 3-aryl-Δ ³ -dihydrothiophenone derivatives are known (WO 95/26 345).

Certain phenyl-pyrone derivatives unsubstituted in the phenyl ring are already known (see AM Chirazi, T. Kappe and E. Ziegler, Arch. Pharm. Chem. Ber. 91, 2849), the use of these compounds which can be used as pesticides is not mentioned. Phenyl-pyrone derivatives having herbicidal, acaricide and pesticidal activity and substituted in the phenyl ring are described in EP-A-588 137.

Certain 5-phenyl-1,3-thiazine derivatives unsubstituted in the phenyl ring are already known (see E. Ziegler and E. Stiner, Monatsh. 95, 147 (1964), R. Ketcham, T. Kappe). And E. Ziegler, J. Heterocycl. Chem. 10, 223 (1973)), the use of these compounds which can be used as pesticides is not mentioned. 5-phenyl-1,3-thiazine derivatives having herbicidal, acaricide and pesticidal activity and substituted in phenyl rings are described in WO 94/14 785.

However, acaricide and pesticidal activity and / or range of action and / or tolerance of these compounds to plants, especially crops, are not always satisfactory.

According to the invention novel compounds of the general formula (I) have been found:

Where

V represents hydrogen, halogen, alkyl or alkoxy,

W represents cyano, nitro, halogen, alkyl, alkenyl, alkynyl, alkoxy, halogenoalkyl, halogenoalkoxy, or optionally substituted phenyl, phenoxy, phenylthio, phenylalkoxy or phenylalkylthio,

X is hydrogen, halogen, alkyl, alkenyl, alkynyl, alkoxy, halogenoalkyl, halogenoalkoxy, cyano, nitro, or each optionally substituted phenyl, phenoxy, phenylthio, phenylalkyloxy or phenylalkylthio Indicates,

Y represents hydrogen, halogen, alkyl, alkoxy, halogenoalkyl, halogenoalkoxy, cyano or nitro,

Z is halogen, alkyl, alkoxy, halogenoalkyl, halogenoalkoxy, hydroxyl, cyano, nitro, or optionally substituted phenoxy, phenylthio, 5- to 6-membered hetaryloxy, 5- to 6- Original hetarylthio, phenylalkyloxy or phenylalkylthio;

Y and Z together with the carbon atoms to which they are attached represent an optionally substituted cycle which is optionally interrupted by one or more heteroatoms, V, X and W represent one of the abovementioned meanings,

W and Z together with the carbon atoms to which they are attached represent an optionally substituted cycle which is optionally interrupted by one or more heteroatoms, V, X and Y represent one of the abovementioned meanings,

Het is a group

Represents one of

From here,

A is hydrogen, each optionally halogen-substituted alkyl, alkenyl, alkoxyalkyl, polyalkoxyalkyl or alkylthioalkyl, each saturated or unsaturated, optionally substituted cycloalkyl or heterocyclyl, or each optionally halogen-, alkyl-, Halogenoalkyl-, alkoxy-, halogenoalkoxy-, cyano- or nitro-substituted aryl, arylalkyl or hetaryl;

B represents hydrogen, alkyl or alkoxyalkyl, or

A and B together with the carbon atoms to which they are attached represent saturated or unsaturated, optionally substituted carbocycles or heterocycles,

D is hydrogen or alkyl, alkenyl, alkynyl, alkoxyalkyl, polyalkoxyalkyl, alkylthioalkyl, saturated or unsaturated cycloalkyl, saturated or unsaturated heterocyclyl, arylalkyl, aryl, hetarylalkyl and hetaryl Represents an optionally substituted radical selected from the group consisting of

A and D together with the atoms to which they are attached, each represent an optionally substituted carbocycle or heterocycle,

G is hydrogen (a) or

Represents one of

From here,

E represents a metal ion equivalent or ammonium ion,

L represents oxygen or sulfur,

M represents oxygen or sulfur,

Each R ¹ is optionally halogen-substituted alkyl, alkenyl, alkoxyalkyl, alkylthioalkyl or polyalkoxyalkyl, or each optionally halogen-, alkyl- or alkoxy-substituted cycloalkyl or heterocyclyl, or each optionally substituted Phenyl, phenylalkyl, hetaryl, phenoxyalkyl or hetaryloxyalkyl,

Each R ² represents optionally halogen-substituted alkyl, alkenyl, alkoxyalkyl or polyalkoxyalkyl, or each optionally substituted cycloalkyl, phenyl or benzyl,

R ³ , R ⁴ and R ⁵ are each independently of one another each independently halogen-substituted alkyl, alkoxy, alkylamino, dialkylamino, alkylthio, alkenylthio or cycloalkylthio, or each optionally substituted phenyl, benzyl, Phenoxy or phenylthio,

R ⁶ and R ⁷ each independently represent hydrogen, each optionally halogen-substituted alkyl, cycloalkyl, alkenyl, alkoxy or alkoxyalkyl, or each optionally substituted phenyl or benzyl, or an N-atom to which they are attached Together, optionally represents a cycle containing oxygen or sulfur and optionally substituted,

Of these compounds

The compound of is excluded.

The compounds of formula (I) may exist as geometric and / or optical isomers or as mixtures of isomers of different compositions, depending on the nature of the substituents, which may be separated by conventional means, if appropriate. Pure isomers and isomer mixtures, methods for their preparation and use, and compositions containing them are the object of the present invention. However, the compounds of the general formula (I) hereafter are intended for the sake of convenience to denote mixtures having always pure compounds and, if appropriate, different proportions of isomeric compounds.

Taking into account the meanings (1) to (5) of the group Het, the following main structures (I-1) to (I-5) are formed:

In the above formula,

A, B, D, G, V, W, X, Y and Z are as mentioned above, respectively.

Considering the various meanings (a), (b), (c), (d), (e), (f) and (g) of group (G), when Het represents group (1), The following main structures (I-1-a) to (I-1-g) are formed:

In the above formula,

A, B, E, L, M, V, W, X, Y, Z, R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ and R ⁷ are each as mentioned above.

Considering the various meanings (a), (b), (c), (d), (e), (f) and (g) of group (G), when Het represents group (2), The following main structures (I-2-a) to (I-2-g) are formed:

In the above formula,

A, B, E, L, M, V, W, X, Y, Z, R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ and R ⁷ are each as mentioned above.

Considering the various meanings (a), (b), (c), (d), (e), (f) and (g) of group (G), when Het represents group (3), The following main structures (I-3-a) to (I-3-g) are formed:

In the above formula,

A, B, E, L, M, V, W, X, Y, Z, R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ and R ⁷ are each as mentioned above.

Depending on the position of substituent G, the compound of general formula (I-4) is in the form of two isomers of general formula (I-4) _a and (I-4) _{b which} are intended to be represented by the dotted lines in general formula (I-4). Can exist:

The compounds of the general formulas (I-4) _a and (I-4) _b may exist in mixtures and in the form of pure isomers. The mixture of the compounds of the general formulas (I-4) _a and (I-4) _b can be separated, if desired, by a physical method, for example by a chromatography method, in a manner known per se.

For clarity, only one of the possible isomers in each case is presented hereafter. This does not exclude the possibility that the compound may optionally exist in the isomer mixture or in the form of each isomer.

Considering the various meanings (a), (b), (c), (d), (e), (f) and (g) of the group (G), when Het represents the group (4), The following main structures (I-4-a) to (I-4-g) are formed:

In the above formula,

A, D, E, L, M, V, W, X, Y, Z, R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ and R ⁷ are each as mentioned above.

Considering the various meanings (a), (b), (c), (d), (e), (f) and (g) of group (G), when Het represents group (5), The following main structures (I-5-a) to (I-5-g) are formed:

In the above formula,

A, E, L, M, V, W, X, Y, Z, R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ and R ⁷ are each as mentioned above.

It has also been found that the compounds of the general formula (I) according to the invention can be obtained by one of the following methods:

(A) It has been found that the compound of formula (I-1-a) is obtained by intramolecular condensation of a compound of formula (II) in the presence of a diluent and in the presence of a base:

In the above formula,

A, B, V, W, X, Y and Z Are each as mentioned above,

R ⁸ represents alkyl, preferably C ₁ -C ₆ -alkyl.

(B) It has been found that the compound of the general formula (I-2-a) is obtained by intramolecular condensation of the compound of the general formula (III) in the presence of a diluent and in the presence of a base:

In the above formula,

A, B, V, W, X, Y, Z and R ⁸ are each as mentioned above.

(C) It has been found that the compounds of the general formula (I-3-a) are obtained by intramolecular ring closure of the compounds of the general formula (IV), optionally in the presence of a diluent and in the presence of an acid:

In the above formula,

A, B, V, W, X, Y, Z and R ⁸ are each as mentioned above,

T represents hydrogen, halogen, alkyl, preferably C ₁ -C ₆ -alkyl or alkoxy, preferably C ₁ -C ₈ -alkoxy.

(D) The compound of formula (I-4-a) is a compound of formula (V) or a silyl enol ether thereof, wherein the compound of formula (Va) is optionally in the presence and in the case of a diluent It was thus found to be obtained by reacting with a compound of formula (VI) in the presence of an acid acceptor:

In the above formula,

A, D, V, W, X, Y and Z are as mentioned above, respectively.

R ^{8 '} represents alkyl, preferably methyl,

Hal represents halogen, preferably chlorine or bromine.

(E) The compound of the following general formula (I-5-a) is a compound of the following general formula (VI), in the presence of a diluent and optionally in the presence of an acid acceptor It was found to be obtained by reacting with:

In the above formula,

A, V, W, X, Y, Z and Hal are as mentioned above, respectively.

Also,

(F) The compounds of the general formulas (I-1-b) to (I-5-b) wherein A, B, D, R ¹ , V, W, X, Y and Z are each as mentioned above are A, B, D, V, W, X, Y and Z respectively represent compounds of the general formulas (I-1-a) to (I-5-a) as mentioned above, in the presence and in the case of a diluent In the presence of an acid-binder,

(α) react with an acid halide of the general formula (VIII)

(β) was found to be obtained by reacting with a carboxylic anhydride of the general formula (IX):

R ¹ -CO-O-CO-R ¹ (IX)

In the above formula,

R ¹ is as defined above,

Hal represents halogen, in particular chlorine or bromine.

(G) compounds of the general formulas (I-1-c) to (I-5-c) wherein A, B, D, R ² , V, W, M, X, Y and Z are each as mentioned above, In each case A, B, D, V, W, X, Y and Z respectively represent compounds of the general formulas (I-1-a) to (I-5-a) as mentioned above, if desired It was found to be obtained by reacting with a chloroformic ester or chloroformic thioester of the general formula (X) in the presence of and optionally in the presence of an acid-binder:

R ² -M-CO-Cl (X)

In the above formula,

R ² and M are as defined above, respectively.

(H) A, B, D, R ² , V, W, M, X, Y and Z are the same as mentioned above, and L represents sulfur (I-1-c) to (I-5) The compounds of -c) are in each case compounds of the general formulas (I-1-a) to (I-5-a) wherein A, B, D, V, W, X, Y and Z are each as mentioned above. of,

(α) optionally reacting with a chloromonothioformic ester or chlorodithioformic ester of the general formula (XI) in the presence of a diluent and optionally in the presence of an acid-binding agent, or

(β) it has been found to be obtained by reacting with carbon disulfide optionally in the presence of a diluent and optionally in the presence of a base, followed by reaction with a compound of the general formula (XII):

R ² -Hal (XII)

In the above formula,

R ² is as defined above,

Hal represents chlorine, bromine or iodine.

(I) compounds of the general formulas (I-1-d) to (I-5-d) in which A, B, D, R ³ , V, W, X, Y and Z are each mentioned above, In which A, B, D, V, W, X, Y and Z are each of the compounds of the general formulas (I-1-a) to (I-5-a) as mentioned above, optionally in the presence of a diluent It has been found to be obtained by reacting with sulfonyl chloride of the general formula (XIII) under and optionally in the presence of an acid-binder:

R ³ -SO ₂ -Cl (XIII)

In the above formula,

R ³ is as defined above.

(J) A, B, D, L, R ⁴ , R ⁵ , V, W, X, Y and Z are each of the general formulas (I-1-e) to (I-5-e) as mentioned above In each case A, B, D, V, W, X, Y and Z are each of the compounds of the general formulas (I-1-a) to (I-5-a) It was found to be obtained by reacting with a phosphorus compound of the general formula (XIV) in the presence of a diluent and optionally in the presence of an acid-binding agent:

In the above formula,

L, R ⁴ and R ⁵ are each as defined above,

Hal represents halogen, in particular chlorine or bromine.

(K) The compounds of the general formulas (I-1-f) to (I-5-f) in which A, B, D, E, V, W, X, Y and Z are each mentioned above, A, B, D, V, W, X, Y and Z respectively represent compounds of the general formulas (I-1-a) to (I-5-a) as mentioned above, in the presence of a diluent, if desired It was found to be obtained by reacting with a metal compound or amine of the general formula (XV) or (XVI):

Me (OR ¹⁰ ) _t (XV)

In the above formula,

Me represents a mono- or divalent metal, preferably an alkali or alkaline earth metal such as lithium, sodium, potassium, magnesium or calcium,

t represents a number of 1 or 2,

R ¹⁰ , R ¹¹ and R ¹² each independently represent hydrogen or alkyl, preferably C ₁ -C ₈ -alkyl.

(L) A, B, D, L, R ⁶ , R ⁷ , V, W, X, Y and Z are the general formulas (I-1-g) to (I-5-g), as mentioned above, respectively. In each case A, B, D, V, W, X, Y and Z are the compounds of the general formulas (I-1-a) to (I-5-a) If the

(α) optionally reacting with an isocyanate or isothiocyanate of the general formula (XVII) in the presence of a diluent and optionally in the presence of a catalyst, or

(β) It has been found to be obtained by reacting carbamoyl chloride or thiocarbamoyl chloride of the general formula (XVIII) in the presence of a diluent, and optionally in the presence of an acid-binding agent:

R ⁶ -N = C = L (XVII)

In the above formula,

R ⁶ , R ⁷ and L are as defined above, respectively.

It has also been surprisingly found that the compounds of the general formula (I) according to the invention have very good activity as pesticides, preferably insecticides, acaricides and herbicides, with which plants, in particular crops, are very well tolerated. lost.

Formula (I) provides a general definition of a compound according to the invention. Preferred ranges of substituents or radicals in the formulas mentioned above and hereinafter are described below:

V preferably represents hydrogen, halogen, C _1-6 -alkyl or C _1-6 -alkoxy,

W is preferably cyano, nitro, halogen, C _1-6 -alkyl, C _2-6 -alkenyl, C _2-6 -alkynyl, C _1-6 -alkoxy, C _1-4 -halogenoalkyl , C _1-4 - halogenoalkyl alkoxy, or respectively optionally halogen -, C _1-6 - alkyl -, C _1-6 - alkoxy -, C _1-4 - halogenoalkyl -, C _1-4 - halogenoalkyl alkoxy -Nitro- or cyano-substituted phenyl, phenoxy, phenylthio, phenyl-C _1-4 -alkoxy or phenyl-C _1-4 -alkylthio,

X is preferably hydrogen, halogen, C _1-6 -alkyl, C _2-6 -alkenyl, C _2-6 -alkynyl, C _1-6 -alkoxy, C _1-4 -halogenoalkyl, C _{1 4} - halogeno, cyano, nitro or respectively optionally halogen -, C _1-6 - alkyl -, C _1-6 - alkoxy -, C _1-4 - halogenoalkyl -, C _1-4 -haloalkyl Genoalkoxy-, nitro- or cyano-substituted phenyl, phenoxy, phenylthio, phenyl-C _1-4 -alkoxy or phenyl-C _1-4 -alkylthio;

Y preferably represents hydrogen, halogen, C _1-6 -alkyl, C _1-6 -alkoxy, C _1-4 -halogenoalkyl, C _1-4 -halogenoalkoxy, cyano or nitro,

Z is preferably halogen, C _1-6 -alkyl, C _1-6 -alkoxy, C _1-4 -halogenoalkyl, C _1-4 -halogenoalkoxy, hydroxyl, cyano, nitro, or optionally each halogen -, C _1-4 - alkyl -, C _1-4 - alkoxy -, C _1-4 - halogenoalkyl -, C _1-4 - halogenoalkyl alkoxy-, nitro- or cyano-substituted phenoxy City, Phenylthio, thiazolyloxy, pyridinyloxy, pyrimidyloxy, pyrazolyloxy, phenyl-C _1-4 -alkoxy or phenyl-C _1-4 -alkylthio;

Y and Z are together, preferably each independently halogen-, C _{1-6 -alkyl-} , C _1-6 -alkoxy- or C _1-4 -halogenoalkyl-substituted and one to three members independently of one another C _3-5 -alkanediyl or C _3-5 -alkenediyl which may be optionally substituted by oxygen, sulfur, nitrogen or carbonyl groups, or

W and Z together are preferably each optionally halogen-, C _{1-6 -alkyl-} , C _1-6 -alkoxy- or C _1-4 -halogenoalkyl-substituted and one to three members are independent of each other C _3-5 -alkanediyl or C _3-5 -alkenediyl which may be optionally substituted by oxygen, sulfur, nitrogen or carbonyl groups,

Het is preferably a group

Represents one of

From here,

A is preferably hydrogen, each optionally halogen-substituted C _1-12 -alkyl, C _2-8 -alkenyl, C _1-10 -alkoxy-C _1-8 -alkyl, poly-C _1-8 -alkoxy -C _1-8 -alkyl or C _1-10 -alkylthio-C _1-6 -alkyl, or optionally one or two directly non-methylene groups are replaced by oxygen and / or sulfur and optionally halogen-, C _{1-6 -alkyl-} or C _1-6 -alkoxy-substituted C _3-8 -cycloalkyl, or preferably each independently halogen, C _1-6 -alkyl-, C _1-6 -halogeno alkyl -, C _1-6 - alkoxy -, C _1-6 - halogenoalkyl alkoxy-, cyano- or nitro-substituted phenyl, naphthyl, phenyl -C _1-6 - alkyl, naphthyl, -C _1-6 -Alkyl or hetaryl having one or three heteroatoms selected from the group consisting of 5 or 6 reducers and oxygen, sulfur and nitrogen,

B preferably represents hydrogen, C _1-12 -alkyl or C _1-8 -alkoxy-C _1-6 -alkyl, or

A and B together with the carbon atoms to which they are attached, preferably in each case one methylene group are optionally replaced by oxygen or sulfur and are C _1-8 -alkyl, C _3-10 -cycloalkyl, C _1-8 -Represents C _3-10 -cycloalkyl or C _5-10 -cycloalkenyl optionally substituted with halogenoalkyl, C _1-8 -alkoxy, C _1-8 -alkylthio, halogen or phenyl,

A and B are further 5- to 8-membered together with the carbon atoms to which they are attached, preferably by alkylenediyl groups optionally containing one or two oxygen and / or sulfur atoms, or together with the carbon atoms to which they are attached C _5-6 -cycloalkyl substituted by an alkylenedioxy group or an alkylenedithioyl group forming a ring, or

A and B together with the carbon atoms to which they are attached, preferably each of the two carbon atoms is optionally C _{1-6 -alkyl-} , C _{1-6 -alkoxy-} or halogen-substituted C _3-6 -alkanediyl, C _3-8 -cycloalkyl or C ₅ -linked by C _3-6 -alkenediyl or C _4-6 -alkanediendiyl, in which case one methylene group is optionally replaced by oxygen or sulfur ₈ -cycloalkenyl,

D is preferably hydrogen, respectively optionally halogen-substituted C _1-12 - alkyl -, C _3-8 - alkenyl, C _3-8 - alkynyl, C _1-10 - alkoxy -C _2-8 - alkyl , Poly-C _1-8 -alkoxy-C _2-8 -alkyl or C _1-10 -alkylthio-C _2-8 -alkyl, or optionally one or two directly non-methylene groups are oxygen and / or sulfur Represents C _3-8 -cycloalkyl which is substituted by and optionally halogen-, C _{1-4 -alkyl-} , C _1-4 -alkoxy- or C _1-4 -halogenoalkyl-substituted, preferably each optionally halogen -, C _1-6 - alkyl -, C _1-6 - halogenoalkyl -, C _1-6 - alkoxy -, C _1-6 - halogenoalkyl alkoxy-, cyano- or nitro-substituted phenyl, With hetaryl, phenyl-C _1-6 -alkyl or 5 or 6 reducers and oxygen, sulfur and nitrogen having one or two heteroatoms selected from the group consisting of 5 or 6 reducers and oxygen, sulfur and nitrogen One of the configured groups, or Het having heteroatoms aryl -C _1-6 - or represent alkyl,

A and D together are preferably C _1-10 -alkyl, C _1-6 -alkoxy, in which one methylene group in each case is optionally replaced by oxygen or sulfur and each is optionally halogen-substituted by halogen, By C _1-6 -alkylthio, C _3-7 -cycloalkyl, phenyl or benzyloxy, or in each case one methylene group is optionally substituted by oxygen or sulfur and optionally substituted by C _1-6 -alkyl _3-6 C to form a fused ring-alkanediyl, C _3-6-al canned yl or C _4-6 - an alkane by diendi one optionally substituted C _3-6 - alkanediyl, C _3-6 -Alkenediyl or C _4-6 -alkanedenediyl group;

A and D are each optionally

C _3-6 -alkanediyl or C _3-6 -alkenediyl group containing one of

G is preferably hydrogen (a) or

Represents one of

From here,

E represents a metal ion equivalent or ammonium ion,

L represents oxygen or sulfur,

M represents oxygen or sulfur,

R ¹ is preferably each halogen-substituted C _1-20 -alkyl, C _2-20 -alkenyl, C _1-8 -alkoxy-C _1-8 -alkyl, C _1-8 -alkylthio-C _1-8 -alkyl or poly-C _1-8 -alkoxy-C _1-8 -alkyl; C _3-8 -cycloalkyl which is halogen-, C _{1-6 -alkyl-} or C _1-6 -alkoxy-substituted and one or two directly non-contiguous methylene groups are optionally replaced by oxygen and / or sulfur; Optionally halogen-, cyano-, nitro -, C _1-6 - alkyl -, C _1-6 - alkoxy -, C _1-6 - halogenoalkyl -, C _{1-6-halogeno-alkoxy} -, C _{1- 6} -alkylthio- or C _1-6 -alkylsulfonyl-substituted phenyl; Optionally halogen-, nitro-, cyano-, C _1-6 - alkyl -, C _1-6 - alkoxy -, C _1-6 - halogenoalkyl - or C _{1-6-halogeno-alkoxy-substituted} phenyl- C _1-6 -alkyl; 5- or 6-membered hetaryl having one or two heteroatoms selected from the group consisting of oxygen, sulfur and nitrogen and optionally halogen- or C _1-6 -alkyl-substituted; Optionally halogen- or C _1-6 -alkyl-substituted phenoxy-C _1-6 -alkyl; Or a halogen-, amino- or C _1-6 -alkyl-substituted 5- or 6-membered hetaryloxy-C _1-6 -having one or two heteroatoms selected from the group consisting of oxygen, sulfur and nitrogen; Alkyl,

R ² is preferably each halogen-substituted C _1-20 -alkyl, C _2-20 -alkenyl, C _1-8 -alkoxy-C _2-8 -alkyl or poly-C _{1-8 -alkoxy-} C _2-8 -alkyl; Optionally halogen-, C _{1-6 -alkyl-} or C _1-6 -alkoxy-substituted C _3-8 -cycloalkyl; Or respectively optionally halogen-, cyano-, nitro -, C _1-6 - alkyl -, C _1-6 - alkoxy -, C _1-6 - halogenoalkyl - or C _{1-6-halogeno-alkoxy-substituted} Phenyl or benzyl,

R ³ is preferably halogen-substituted C _1-8 -alkyl, or each optionally halogen-, C _{1-6 -alkyl-} , C _1-6 -alkoxy-, C _1-4 -halogenoalkyl- or C _1-4 -halogenoalkoxy-, cyano- or nitro-substituted phenyl or benzyl,

R ⁴ and R ⁵ are each independently of each other preferably halogen-substituted C _1-8 -alkyl, C _1-8 -alkoxy, C _1-8 -alkylamino, di (C _1-8 -alkyl) amino, C _1-8 - alkylthio or C _3-8 - alkenyl, thio, or respectively optionally halogen-, nitro-, cyano-, C _1-4 - alkoxy -, C _1-4 - halogenoalkyl alkoxy-, C _1-4 - alkylthio -, C _1-4 - halogenoalkyl thio -, C _1-4-alkyl-or C _1-4 - halogenoalkyl - represents a substituted phenyl, phenoxy or phenylthio,

R ⁶ and R ⁷ are preferably independently of each other hydrogen, each optionally halogen-substituted C _1-8 -alkyl, C _3-8 -cycloalkyl, C _1-8 -alkoxy, C _3-8 -alkenyl or C _1-8 -alkoxy-C _2-8 -alkyl, or optionally halogen-, C _1-8 -alkyl-, C _1-8 -halogenoalkyl- or C _1-8 -alkoxy-substituted phenyl or benzyl Or together, one methylene group represents C _3-6 -alkylene radicals which are optionally substituted by oxygen or sulfur and optionally C _1-6 -alkyl-substituted,

R ¹³ is preferably hydrogen, or each optionally halogen-substituted C _1-8 -alkyl or C _1-8 -alkoxy, one methylene group is optionally replaced by oxygen or sulfur and optionally halogen-, C _{1-4 -Alkyl-} or C _1-4 -alkoxy-substituted C _3-8 -cycloalkyl, or optionally each halogen-, C _{1-6 -alkyl-} , C _1-6 -alkoxy-, C _1-4 -halogeno Alkyl-, C _1-4 -halogenoalkoxy-, nitro- or cyano-substituted phenyl, phenyl-C _1-4 -alkyl or phenyl-C _1-4 -alkoxy,

R ¹⁴ preferably represents hydrogen or C _1-8 -alkyl, or

R ¹³ and R ¹⁴ together represent preferably C _4-6 -alkanediyl,

R ¹⁵ and R ¹⁶ are the same or different and preferably represent C _1-6 -alkyl,

R ¹⁵ and R ¹⁶ together, preferably C _1-6 - by alkyl, or an optionally halogen -, C _1-4 - alkyl -, C _1-4 - halogenoalkyl -, C _1-4 - alkoxy - , C _2-4 -alkanediyl radical optionally substituted by C _1-4 -halogenoalkoxy-, nitro- or cyano-substituted phenyl,

R ¹⁷ and R ¹⁸ are each independently of each other hydrogen, optionally halogen-substituted C _1-8 -alkyl, or optionally halogen-, C _{1-6 -alkyl-} , C _{1-6 -alkoxy-} , C _{1 -4} -halogenoalkyl-, C _1-4 -halogenoalkoxy-, nitro- or cyano-substituted phenyl, or

R ¹⁷ and R ¹⁸ preferably together with the carbon atom to which they are attached represent C _5-7 -cycloalkyl in which one methylene group is optionally replaced by oxygen or sulfur and optionally C _1-4 -alkyl-substituted,

R ¹⁹ and R ²⁰ are each independently of each other preferably C _1-10 -alkyl, C _2-10 -alkenyl, C _1-10 -alkoxy, C _1-10 -alkylamino, C _3-10 -alkenyl Amino, di (C _1-10 -alkyl) amino or di (C _3-10 -alkenyl) amino.

V particularly preferably represents hydrogen, fluorine, chlorine, bromine, C _1-4 -alkyl or C _1-4 -alkoxy,

W is particularly preferably cyano, nitro, fluorine, chlorine, bromine, C _1-4 -alkyl, C _1-4 -alkoxy, C _1-2 -halogenoalkyl, C _1-2 -halogenoalkoxy, or respectively optionally fluorine-, chlorine -, bromine -, C _1-4 - alkyl -, C _1-4 - alkoxy -, C _1-2 - halogenoalkyl -, C _1-2 - halogenoalkyl alkoxy-, nitro-, or Cyano-substituted phenyl, phenoxy, benzyl or benzyloxy,

X is particularly preferably hydrogen, fluorine, chlorine, bromine, C _1-4 -alkyl, C _1-4 -alkoxy, C _1-2 -halogenoalkyl, C _1-2 -halogenoalkoxy, cyano, nitro , or respectively optionally fluorine -, chlorine -, bromine -, C _1-4 - alkyl -, C _1-4 - alkoxy -, C _1-2 - halogenoalkyl -, C _1-2 - halogenoalkyl alkoxy-, nitro Or cyano-substituted phenyl, phenoxy, benzyl or benzyloxy,

Y is particularly preferably hydrogen, fluorine, chlorine, bromine, C _1-4 -alkyl, C _1-4 -alkoxy, C _1-2 -halogenoalkyl, C _1-2 -halogenoalkoxy, cyano or nitro Indicates

Z is particularly preferably fluorine, chlorine, bromine, C _1-4 -alkyl, C _1-4 -alkoxy, C _1-2 -halogenoalkyl, C _1-2 -halogenoalkoxy, hydroxyl, cyano, nitro or respectively optionally fluorine-, chlorine -, bromine -, C _1-4 - alkyl -, C _1-4 - alkoxy -, C _1-2 - halogenoalkyl -, C _1-2 - halogenoalkyl alkoxy-, Nitro- or cyano-substituted phenoxy or benzyloxy, or

Y and Z together are particularly preferably each independently fluorine-, chlorine-, bromine-, C _{1-4 -alkyl-} , C _1-4 -alkoxy- or C _1-2 -halogenoalkyl-substituted one or two direct source that are not adjacent each independently oxygen, sulfur or nitrogen by a C _3-4 optionally replaced - or C _3-4 alkanediyl-known or shown to be canned,

W and Z together are particularly preferably each independently fluorine-, chlorine-, bromine-, C _{1-4 -alkyl-} , C _1-4 -alkoxy- or C _1-2 -halogenoalkyl-substituted one or Al represents the canned one, - two direct source that are not adjacent to each other independently optionally replaced by oxygen, sulfur or nitrogen, C _3-4 - alkanediyl or C _3-4

Het is particularly preferably the following group

Represents one of

From here,

A is particularly preferably hydrogen, each optionally fluorine- or chlorine-substituted C _{1-10 -alkyl-} , C _2-6 -alkenyl, C _1-8 -alkoxy-C _1-6 -alkyl, poly-C _1-6 -alkoxy-C _1-6 -alkyl or C _1-8 -alkylthio-C _1-6 -alkyl, or one or two directly non-adjacent methylene groups, are optionally replaced by oxygen and / or sulfur Optionally fluorine, chlorine-, C _{1-4 -alkyl-} or C _1-4 -alkoxy-substituted C _3-7 -cycloalkyl, or optionally fluorine-, chlorine-, bromine-, C _1-4 -alkyl, respectively -, C _1-4 - halogenoalkyl -, C _1-4 - alkoxy -, C _1-4 - halogenoalkyl alkoxy-, cyano- or nitro-substituted phenyl, furanyl, pyridyl, imidazolyl, Triazolyl, pyrazolyl, indolyl, thiazolyl, thienyl or phenyl-Ci_ ₄ -alkyl,

B particularly preferably represents hydrogen, C _1-10 -alkyl or C _1-6 -alkoxy-C _1-4 -alkyl,

A and B, together with the carbon atoms to which they are attached, are particularly preferably each one methylene group optionally substituted by oxygen or sulfur and are C _1-6 -alkyl, C _3-8 -cycloalkyl, C _1-3- C _3-8 -cycloalkyl or C _5-8 -cycloalkenyl optionally substituted with halogenoalkyl, C _1-6 -alkoxy, C _1-6 -alkylthio, fluorine, chlorine or phenyl, or

A and B are further 5- to 7-membered rings together with the carbon atoms to which they are attached, particularly preferably by alkylenediyl groups optionally containing one or two oxygen or sulfur atoms, or together with the carbon atoms to which they are attached; C _5-6 -cycloalkyl substituted by an alkylenedioxy or alkylenedithiol group which forms

A and B together with the carbon atom to which they are attached particularly preferably C _1-4 each optionally two carbon atoms - alkyl -, C _1-4 - alkoxy -, fluorine-, chlorine-or bromine-substituted C ₃ C _3-6 -cycloalkyl or C _5-6 linked by _-5 -alkanediyl, C _3-5 -alkenediyl or butadienediyl, each optionally with one methylene group replaced by oxygen or sulfur -Represents cycloalkenyl,

D is particularly preferably hydrogen, each optionally fluorine- or chlorine-substituted C _1-10 -alkyl, C _3-6 -alkenyl, C _3-6 -alkynyl, C _1-8 -alkoxy-C _{2- 6} -alkyl, poly-C _1-6 -alkoxy-C _2-6 -alkyl or C _1-8 -alkylthio-C _2-6 -alkyl, or one or two directly non-methylene groups are oxygen and / Or optionally substituted by sulfur and optionally fluorine-, chlorine-, C _{1-4 -alkyl-} , C _1-4 -alkoxy- or C _1-2 -halogenoalkyl-substituted C _3-7 -cycloalkyl or, most preferably, each optionally fluorine -, chlorine -, bromine -, C _1-4 - alkyl -, C _1-4 - halogenoalkyl -, C _1-4 - alkoxy -, C _1-4 - halogenoalkyl Alkoxy-, cyano- or nitro-substituted phenyl, furanyl, imidazolyl, pyridyl, thiazolyl, pyrazolyl, pyrimidyl, pyrrolyl, thienyl, triazolyl or phenyl-C _1-4 -alkyl Or

A and D are together, particularly preferably C _1-6 -alkyl, C _1-4 -alkoxy, each of which one carbon atom is optionally substituted by oxygen or sulfur and each is optionally fluorine- or chlorine-substituted , Optionally substituted by C _1-4 -alkylthio, C _3-6 -cycloalkyl, phenyl or benzyloxy, or each optionally

C _3-5 -alkanediyl or C _3-5 -alkenediyl group containing either

G is particularly preferably hydrogen (a) or a group

Represents one of

From here,

E represents a metal ion equivalent or ammonium ion,

L represents oxygen or sulfur,

M represents oxygen or sulfur,

R ¹ is particularly preferably each fluorine- or chlorine-substituted C _1-16 -alkyl, C _2-16 -alkenyl, C _1-6 -alkoxy-C _1-6 -alkyl, C _1-6- Alkylthio-C _1-6 -alkyl or poly-C _1-6 -alkoxy-C _1-6 -alkyl; C _3-7 -optionally substituted with fluorine-, chlorine-, C _{1-5 -alkyl-} or C _1-5 -alkoxy-substituted and one or two non-contiguous methylene groups optionally substituted by oxygen and / or sulfur. Cycloalkyl; Optionally fluorine -, chlorine -, bromine -, cyano-, nitro -, C _1-4 - alkyl -, C _1-4 - alkoxy -, C _1-3 - halogenoalkyl -, C _1-3 - halogenoalkyl Alkoxy-, C _1-4 -alkylthio- or C _1-4 -alkylsulfonyl-substituted phenyl; Optionally fluorine-, chlorine-, bromine-, C _{1-4 -alkyl-} , C _1-4 -alkoxy-, C _1-3 -halogenoalkyl- or C _1-3 -halogenoalkoxy-substituted phenyl-C _1-4 -alkyl; Optionally fluorine-, chlorine-, bromine- or C _1-4 -alkyl-substituted pyrazolyl, thiazolyl, pyridyl, pyrimidyl, furanyl or thienyl; Optionally fluorine-, chlorine-, bromine- or C _1-4 -alkyl-substituted phenoxy-C _1-5 -alkyl; Or optionally fluorine, chlorine-, bromine-, amino- or C _1-4 -alkyl-substituted pyridyloxy-Ci_ ₅ -alkyl, pyrimidyloxy-Ci_ ₅ -alkyl or thiazolyloxy- C _1-5 -alkyl,

R ² is particularly preferably each fluorine- or chlorine-substituted C _1-16 -alkyl, C _2-16 -alkenyl, C _1-6 -alkoxy-C _2-6 -alkyl or poly-C _{1- 6} -alkoxy-C _2-6 -alkyl; Optionally fluorine-, chlorine-, C _{1-4 -alkyl-} or C _1-4 -alkoxy-substituted C _3-7 -cycloalkyl; Or respectively optionally fluorine-, chlorine -, bromine -, cyano-, nitro -, C _1-4 - alkyl -, C _1-3 - alkoxy -, C _1-3 - halogenoalkyl - or C _1-3 - Halogenoalkoxy-substituted phenyl or benzyl,

R ³ is particularly preferably fluorine- or chlorine-substituted C _1-6 -alkyl, or each optionally fluorine-, chlorine-, bromine-, C _{1-4 -alkyl-} , C _1-4 -alkoxy-, C _1-2 -halogenoalkoxy-, C _1-2 -halogenoalkyl-, cyano- or nitro-substituted phenyl or benzyl,

R ⁴ and R ⁵ are each particularly preferably independently of one another each independently fluorine- or chlorine-substituted C _1-6 -alkyl, C _1-6 -alkoxy, C _1-6 -alkylamino, di (C _{1- 6} -alkyl) amino, C _1-6 -alkylthio or C _3-4 -alkenylthio, or optionally fluorine-, chlorine-, bromine-, nitro-, cyano-, C _1-3 -alkoxy-, C _{1-3-halogeno-alkoxy} -, C _1-3 - alkylthio -, C _1-3 - halogenoalkyl thio -, C _1-3-alkyl-or C _1-3 - halogenoalkyl-substituted phenyl , Phenoxy or phenylthio,

R ⁶ and R ⁷ are each particularly preferably independently of one another hydrogen, each optionally fluorine- or chlorine-substituted C _1-6 -alkyl, C _3-6 -cycloalkyl, C _1-6 -alkoxy, C _{3- 6} -alkenyl or C _1-6 - alkoxy -C _2-6 - alkyl, or respectively optionally fluorine -, chlorine -, bromine -, C _1-5 - halogenoalkyl -, C _1-5-alkyl-or C _1-5 -alkoxy-substituted phenyl or benzyl, or together, one methylene group, optionally substituted by oxygen or sulfur and optionally C _1-4 -alkyl-substituted C _3-6 -alkylene radicals ,

R ¹³ is particularly preferably hydrogen or each optionally fluorine- or chlorine-substituted C _1-6 -alkyl or C _1-6 -alkoxy, or one methylene group is optionally replaced by oxygen or sulfur and optionally fluorine- , C _{1-2 -alkyl-} or C _1-2 -alkoxy-substituted C _3-7 -cycloalkyl, or particularly preferably each independently fluorine-, chlorine-, bromine-, C _1-5 -alkyl -, C _1-5 - alkoxy -, C _1-2 - halogenoalkyl -, C _1-2 - halogenoalkyl alkoxy-, nitro- or cyano-substituted phenyl, phenyl -C _1-3 - alkyl or phenyl -C _1-2 -alkyloxy,

R ¹⁴ particularly preferably represents hydrogen or C _1-6 -alkyl, or

R ¹³ and R ¹⁴ together, particularly preferably represent C _4-6 -alkanediyl,

R ¹⁵ and R ¹⁶ are the same or different and particularly preferably represent C _1-4 -alkyl,

R ¹⁵ and R ¹⁶ together, particularly preferably by C _1-4 -alkyl, or optionally fluorine-, chlorine-, bromine-, C _1-2 -alkyl-, C _1-2 -halogenoalkyl-, C _1-2 - alkoxy -, C _1-2 - halogenoalkyl alkoxy-, nitro- or cyano-represents the alkanediyl radical - optionally substituted C _2-3 substituted by phenyl.

V very particularly preferably represents hydrogen, fluorine, chlorine, bromine, methyl, ethyl, propyl, isopropyl, t-butyl, methoxy, ethoxy, propoxy or isopropoxy,

W is very particularly preferably cyano, nitro, fluorine, chlorine, bromine, methyl, ethyl, propyl, butyl, isopropyl, isobutyl, t-butyl, methoxy, ethoxy, propoxy, isopropoxy, tri Fluoromethyl, difluoromethoxy, trifluoromethoxy, phenyl or benzyloxy,

X is very particularly preferably hydrogen, fluorine, chlorine, bromine, methyl, ethyl, propyl, butyl, isobutyl, isopropyl, t-butyl, methoxy, ethoxy, propoxy, isopropoxy, trifluoromethyl Trifluoromethoxy, difluoromethoxy, cyano, nitro, phenyl or benzyloxy,

Y is very particularly preferably hydrogen, fluorine, chlorine, bromine, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, t-butyl, methoxy, ethoxy, propoxy, isopropoxy, trifluoromethyl , Trifluoromethoxy, difluoromethoxy, cyano or nitro,

Z is very particularly preferably fluorine, chlorine, bromine, methyl, ethyl, propyl, butyl, isobutyl, isopropyl, t-butyl, methoxy, ethoxy, propoxy, isopropoxy, trifluoromethyl, tri Fluoromethoxy, difluoromethoxy, cyano or nitro, or

Y and Z together, very particularly preferably, two directly non-adjacent circles are optionally replaced by oxygen and optionally fluorine-, chlorine-, methyl-, ethyl-, propyl-, isopropyl-, methoxy-, Oxy-, propoxy-, isopropoxy- or trifluoromethyl-substituted C _3-4 -alkanediyl, or

W and Z together, very particularly preferably, two directly non-adjacent circles are optionally replaced by oxygen and optionally fluorine-, chlorine-, methyl-, ethyl-, propyl-, isopropyl-, methoxy-, Oxy-, propoxy-, isopropoxy- or trifluoromethyl-substituted C _3-4 -alkanediyl;

Het is very particularly preferably the following group

Represents one of

From here,

A is very particularly preferably hydrogen, each optionally fluorine- or chlorine-substituted C _1-8 -alkyl, C _2-4 -alkenyl, C _1-6 -alkoxy-C _1-4 -alkyl, poly-C _1-4 -alkoxy-C _1-4 -alkyl or C _1-6 -alkylthio-C _1-4 -alkyl, or one or two directly non-adjacent methylene groups, are optionally replaced by oxygen and / or sulfur Optionally fluorine-, chlorine-, methyl- or methoxy-substituted C _3-6 -cycloalkyl, or each optionally fluorine-, chlorine-, bromine-, methyl-, ethyl-, n-propyl-, isopropyl-, Methoxy-, ethoxy-, trifluoromethyl-, trifluoromethoxy-, cyano- or nitro-substituted phenyl, pyridyl or benzyl,

B very particularly preferably represents hydrogen, C _1-8 -alkyl or C _1-4 -alkoxy-C _1-2 -alkyl,

A and B together with the carbon atoms to which they are bound, very particularly preferably in each case one methylene group are optionally replaced by oxygen or sulfur and methyl, ethyl, n-propyl, isopropyl, butyl, isobutyl, sec -Butyl, t-butyl, cyclohexyl, trifluoromethyl, methoxy, ethoxy, n-propoxy, isopropoxy, butoxy, isobutoxy, sec-butoxy, t-butoxy, methylthio, ethyl C _3-8 -cycloalkyl or C _5-8 -cycloalkenyl optionally substituted with thio, fluorine, chlorine or phenyl, or

A and B together with the carbon atoms to which they are attached, very particularly preferably form an additional 5- or 6-membered ring by an alkylenediyl group optionally containing an oxygen or sulfur atom, or together with a bonded carbon atom C _5-6 -cycloalkyl substituted by alkylenedioxy group, or

A and B together with the carbon atoms to which they are attached are very particularly preferably C _3-6 -cyclo linked by two carbon atoms connected by C _3-4 -alkanediyl, C _3-4 -alkenediyl or butadienediyl Alkyl or C _5-6 -cycloalkenyl,

D is very particularly preferably hydrogen or C _1-8 -alkyl, C ₃ -optionally substituted with one or two directly non-methylene groups, each optionally substituted by oxygen and / or sulfur, each fluorine- or chlorine-substituted ₄ -alkenyl, C _3-4 -alkynyl, C _1-6 -alkoxy-C _2-4 -alkyl, poly-C _1-4 -alkoxy-C _2-4 -alkyl, C _1-4 -alkylthio -C _2-4 -alkyl or C _3-6 -cycloalkyl, or optionally fluorine-, chlorine-, bromine-, methyl-, ethyl-, n-propyl-, isopropyl-, methoxy-, ethoxy- , Trifluoromethyl-, trifluoromethoxy-, cyano- or nitro-substituted phenyl, furanyl, pyridyl, thienyl or benzyl, or

A and D together are very particularly preferably C _1-6 -alkyl or C ₁ , in which case one methylene group is optionally replaced by oxygen or sulfur and each is optionally fluorine- or chlorine-substituted ₄ - an alkoxy optionally substituted by C _3-5 - denotes the Al canned yl group, - or C _3-5 alkanediyl

G is very particularly preferably hydrogen (a) or

Represents one of

From here,

E represents a metal ion equivalent or ammonium ion,

L represents oxygen or sulfur,

M represents oxygen or sulfur,

R ¹ is very particularly preferably each optionally fluorine- or chlorine-substituted C _1-14 -alkyl, C _2-14 -alkenyl, C _1-4 -alkoxy-C _1-6 -alkyl, C _{1-4 -Alkylthio} -Ci_ ₆ -alkyl or poly-Ci_ ₄ -alkoxy-Ci_ ₄ -alkyl; One or two non-contiguous methylene groups are optionally replaced by oxygen and / or sulfur and optionally fluorine-, chlorine-, methyl-, ethyl-, n-propyl-, i-propyl-, n-butyl-, i -Butyl-, t-butyl-, methoxy-, ethoxy-, n-propoxy- or isopropoxy-substituted C _3-6 -cycloalkyl; Optionally fluorine-, chlorine-, bromine-, cyano-, nitro-, methyl-, ethyl-, n-propyl-, i-propyl-, methoxy-, ethoxy-, trifluoromethyl-, trifluorome Oxy-, methylthio-, ethylthio-, methylsulfonyl- or ethylsulfonyl-substituted phenyl; Optionally fluorine-, chlorine-, bromine-, methyl-, ethyl-, n-propyl-, i-propyl-, methoxy-, ethoxy-, trifluoromethyl- or trifluoromethoxy-substituted benzyl; Each optionally optionally fluorine-, chlorine-, bromine-, methyl- or ethyl-substituted furanyl, thienyl or pyridyl; Optionally fluorine-, chlorine-, methyl- or ethyl-substituted phenoxy-C _1-4 -alkyl; Or respectively optionally fluorine-, chlorine-, amino-, methyl- or ethyl-substituted pyridyloxy -C _1-4 - alkyl, pyrimidyl-oxy -C _1-4 - alkyl or thiazolyl oxy -C _1-4 - Alkyl,

R ² is very particularly preferably each optionally fluorine- or chlorine-substituted C _1-14 -alkyl, C _2-14 -alkenyl, C _1-4 -alkoxy-C _2-6 -alkyl or poly-C _{1 -4} -alkoxy-C _2-6 -alkyl; Optionally fluorine-, chlorine-, methyl-, ethyl-, n-propyl-, isopropyl- or methoxy-substituted C _3-6 -cycloalkyl; Or optionally fluorine-, chlorine-, cyano-, nitro-, methyl-, ethyl-, n-propyl-, i-propyl-, methoxy-, ethoxy-, trifluoromethyl- or trifluoromethoxy -Substituted phenyl or benzyl,

R ³ is very particularly preferably optionally fluorine- or chlorine-substituted methyl, ethyl, propyl, isopropyl, butyl or t-butyl, or each optionally fluorine-, chlorine-, bromine-, methyl-, ethyl-, iso Propyl-, t-butyl, methoxy-, ethoxy-, isopropoxy-, trifluoromethyl-, trifluoromethoxy-, cyano- or nitro-substituted phenyl or benzyl,

R ⁴ and R ⁵ are each very particularly preferably independently of one another each independently fluorine- or chlorine-substituted C _1-4 -alkyl, C _1-4 -alkoxy, C _1-4 -alkylamino, di (C _{1 -4} -alkyl) amino or C _1-4 -alkylthio, or optionally fluorine-, chlorine-, bromine-, nitro-, cyano-, methyl-, methoxy-, trifluoromethyl- or trifluorome Oxy-substituted phenyl, phenoxy or phenylthio,

R ⁶ and R ⁷ are each very particularly preferably independently of one another hydrogen, each optionally fluorine- or chlorine-substituted C _1-4 -alkyl, C _3-6 -cycloalkyl, C _1-4 -alkoxy, C _{3 -4} -alkenyl or C _1-4 -alkoxy-C _2-4 -alkyl, or optionally fluorine, chlorine-, bromine-, methyl-, methoxy- or trifluoromethyl-substituted phenyl or benzyl, respectively Or together, one methylene group represents a C _5-6 -alkylene radical optionally substituted by oxygen or sulfur and optionally methyl- or ethyl-substituted.

In each case the following compounds are excluded (described in EP-O 528 156):

In the compound of formula (I-2), only substituent V among substituents X, V, Y, Z and W represents hydrogen, and when X, Y, Z and W have a meaning other than hydrogen, Z does not represent halogen. Preference is given to compounds of the general formula (I-2).

The definitions or explanations of the radicals mentioned above as general or preferred can be combined with one another as desired, ie can be combined between each range and a preferred range. This applies correspondingly to the final product, precursors and intermediates.

For the purposes of the present invention, preference is given to compounds of the formula (I) in which the meanings mentioned as preferred above are combined.

For the purposes of the present invention, particular preference is given to compounds of the formula (I) in which the meanings mentioned as particularly preferred above are combined.

For the purposes of the present invention, very particular preference is given to compounds of the formula (I) in which the meanings mentioned as very particularly preferred above are combined.

Saturated or unsaturated hydrocarbon radicals such as alkyl or alkenyl are in each case straight or branched chain, including those linked with hetero atoms, such as in alkoxy.

The optionally substituted radical may be mono- or polysubstituted, and when polysubstituted, the substituents may be the same or different.

a) A, B and the carbon atom to which they are attached have the meaning mentioned above as being particularly particularly preferred and V represents hydrogen,

b) A, B and the carbon atoms to which they are attached have the meaning mentioned above as being particularly particularly preferred and V and Y represent hydrogen

Particular preference is given to compounds of the general formulas (I-1) to (I-3).

In addition to the compounds mentioned in the preparation examples, compounds of the general formula (I-1-a) may be specifically mentioned:

TABLE 1 V = H; W = CH ₃ ; X = CH ₃ ; Y = CH ₃ ; Z = CH ₃

TABLE 2

A and B are as defined in Table 1,

V = H; W = CH ₃ ; X = CH ₃ ; Y = H; Z = Cl.

TABLE 3

A and B are as defined in Table 1,

V = H; W = CH ₃ ; X = CH ₃ ; Y = CH ₃ ; Z = F.

TABLE 4

A and B are as defined in Table 1,

V = H; W = CH ₃ ; X = CH ₃ ; Y = CH ₃ ; Z = Cl.

TABLE 5

A and B are as defined in Table 1,

V = H; W = CH ₃ ; X = CH ₃ ; Y = CH ₃ ; Z = Br.

TABLE 6

A and B are as defined in Table 1,

V = CH ₃ ; W = CH ₃ ; X = CH ₃ ; Y = H; Z = CH ₃ .

TABLE 7

A and B are as defined in Table 1,

V = CH ₃ ; W = CH ₃ ; X = H; Y = CH ₃ ; Z = CH ₃ .

TABLE 8

A and B are as defined in Table 1,

V = H; W = CH ₃ ; X = CH ₃ ; Y = H; Z = Br.

TABLE 9

A and B are as defined in Table 1,

V = H; W = Cl; X = Cl; Y = H; Z = Br.

TABLE 10

A and B are as defined in Table 1,

V = H; W = Br; X = Br; Y, Z =-(CH ₂ ) _3- .

TABLE 11

A and B are as defined in Table 1,

V = H; W = CH ₃ ; X = OCH ₃ ; Y = H; Z = Br.

TABLE 12

A and B are as defined in Table 1,

V = CH ₃ ; W = CH ₃ ; X = CH ₃ ; Y = CH ₃ ; Z = CH ₃ .

TABLE 13

A and B are as defined in Table 1,

V = H; W = Cl; X = Cl; Y = Cl; Z = CH ₃ .

TABLE 14

A and B are as defined in Table 1,

V = H; W = Br; X = Br; Y = Br; Z = CH ₃ .

In addition to the compounds mentioned in the preparation examples, compounds of the general formula (I-2-a) may be specifically mentioned:

TABLE 15 V = H; W = CH ₃ ; X = CH ₃ ; Y = CH ₃ ; Z = CH ₃ .

TABLE 16

A and B are as defined in Table 15,

V = H; W = CH ₃ ; X = CH ₃ ; Y = H; Z = Cl.

TABLE 17

A and B are as defined in Table 15,

V = CH ₃ ; W = CH ₃ ; X = CH ₃ ; Y = H; Z = CH ₃ .

TABLE 18

A and B are as defined in Table 15,

V = CH ₃ ; W = CH ₃ ; X = H; Y = CH ₃ ; Z = CH ₃ .

TABLE 19

A and B are as defined in Table 15,

V = H; W = CH ₃ ; X = CH ₃ ; Y = H; Z = Br.

TABLE 20

A and B are as defined in Table 15,

V = H; W = Cl; X = Cl; Y = H; Z = Br.

TABLE 21

A and B are as defined in Table 15,

V = H; W = Br; X = Br; Y, Z =-(CH ₃ ) _2- .

Table 22

A and B are as defined in Table 15,

V = H; W = CH ₃ ; X = OCH ₃ ; Y = H; Z = Br.

TABLE 23

A and B are as defined in Table 15,

V = CH ₃ ; W = CH ₃ ; X = CH ₃ ; Y = CH ₃ ; Z = CH ₃ .

TABLE 24

A and B are as defined in Table 15,

V = H; W = Cl; X = Cl; Y = Cl; Z = CH ₃ .

TABLE 25

A and B are as defined in Table 15,

V = H; W = Br; X = Br; Y = Br, Z = CH ₃ .

In addition to the compounds mentioned in the preparation examples, compounds of the general formula (I-3-a) may be specifically mentioned:

TABLE 26

V = H; W = CH ₃ ; X = CH ₃ ; Y = CH ₃ ; Z = CH ₃ .

TABLE 27

A and B are as defined in Table 26,

V = H; W = CH ₃ ; X = CH ₃ ; Y = H; Z = Cl.

TABLE 28

A and B are as defined in Table 26,

V = H; W = CH ₃ ; X = CH ₃ ; Y = CH ₃ ; Z = Cl.

TABLE 29

A and B are as defined in Table 26,

V = H; W = CH ₃ ; X = CH ₃ ; Y = CH ₃ ; Z = F.

TABLE 30

A and B are as defined in Table 26,

V = H; W = CH ₃ ; X = CH ₃ ; Y = CH ₃ ; Z = Br.

Table 31

A and B are as defined in Table 26,

V = CH ₃ ; W = CH ₃ ; X = CH ₃ ; Y = H; Z = CH ₃ .

Table 32

A and B are as defined in Table 26,

V = CH ₃ ; W = CH ₃ ; X = H; Y = CH ₃ ; Z = CH ₃ .

Table 33

A and B are as defined in Table 26,

V = H; W = CH ₃ ; X = CH ₃ ; Y = H; Z = Br.

Table 34

A and B are as defined in Table 26,

V = H; W = Cl; X = Cl; Y = H; Z = Br.

Table 35

A and B are as defined in Table 26,

V = H; W = Br; X = Br; Y, Z =-(CH ₂ ) _3- .

TABLE 36

A and B are as defined in Table 26,

V = H; W = CH ₃ ; X = OCH ₃ ; Y = H, Z = Br.

TABLE 37

A and B are as defined in Table 26,

V = CH ₃ ; W = CH ₃ ; X = CH ₃ ; Y = CH ₃ , Z = CH ₃ .

Table 38

A and B are as defined in Table 26,

V = H; W = Cl; X = Cl; Y = Cl, Z = CH ₃ .

TABLE 39

A and B are as defined in Table 26,

V = H; W = Br; X = Br; Y = Br, Z = CH ₃ .

In addition to the compounds mentioned in the preparation examples, compounds of the general formula (I-4-a) may be specifically mentioned:

TABLE 40

V = H; W = CH ₃ ; X = CH ₃ ; Y = CH ₃ ; Z = CH ₃ .

Table 41

A and D are as defined in Table 40,

V = H; W = CH ₃ ; X = CH ₃ ; Y = H; Z = Cl.

Table 42

A and D are as defined in Table 40,

V = H; W = CH ₃ ; X = CH ₃ ; Y = CH ₃ ; Z = Cl.

Table 43

A and D are as defined in Table 40,

V = H; W = CH ₃ ; X = CH ₃ ; Y = CH ₃ ; Z = F.

Table 44

A and D are as defined in Table 40,

V = H; W = CH ₃ ; X = CH ₃ ; Y = CH ₃ ; Z = Br.

TABLE 45

A and D are as defined in Table 40,

V = CH ₃ ; W = CH ₃ ; X = CH ₃ ; Y = H; Z = CH ₃ .

TABLE 46

A and D are as defined in Table 40,

V = CH ₃ ; W = CH ₃ ; X = H; Y = CH ₃ ; Z = CH ₃ .

TABLE 47

A and D are as defined in Table 40,

V = H; W = CH ₃ ; X = CH ₃ ; Y = H; Z = Br.

TABLE 48

A and D are as defined in Table 40,

V = H; W = Cl; X = Cl; Y = H; Z = Br.

Table 49

A and D are as defined in Table 40,

V = H; W = Br; X = Br; Y, Z =-(CH ₂ ) _3- .

TABLE 50

A and D are as defined in Table 40,

V = H; W = CH ₃ ; X = OCH ₃ ; Y = H, Z = Br.

Table 51

A and D are as defined in Table 40,

V = CH ₃ ; W = CH ₃ ; X = CH ₃ ; Y = CH ₃ , Z = CH ₃ .

Table 52

A and D are as defined in Table 40,

V = H; W = Cl; X = Cl; Y = Cl, Z = CH ₃ .

In addition to the compounds mentioned in the preparation examples, compounds of the general formula (I-5-a) may be specifically mentioned:

TABLE 54

V = H; W = CH ₃ ; X = CH ₃ ; Y = CH ₃ ; Z = CH ₃ .

TABLE 55

A is as defined in Table 54,

V = H; W = CH ₃ ; X = CH ₃ ; Y = H; Z = Cl.

TABLE 56

A is as defined in Table 54,

V = H; W = CH ₃ ; X = CH ₃ ; Y = CH ₃ ; Z = Cl.

When ethyl N-[(3,4-dichloro-2,6-dimethyl) -phenylacetyl] -1-amino-4-ethyl-cyclohexanecarboxylate is used as starting material according to method (A), The process of the process according to the invention can be represented by the following scheme:

When using ethyl O-[(2,5-dichloro-6-methyl) -phenylacetyl] hydroxyacetate according to method (B), the process of the process according to the invention can be represented by the following scheme:

Ethyl 2-[(2-chloro-4,5,6-trimethyl) -phenyl] -4- (4-methoxy) -benzylmercapto-4-methyl-3-oxo-valerate according to method (C) When using, the process of the process according to the invention can be represented by the following scheme:

When chlorocarbonyl 2-[(3,4-dichloro-2,6-dimethyl) -phenyl] ketene and acetone are used as starting materials according to method (D), the process of the process according to the invention is Can be represented as:

In the case of using chlorocarbonyl 2-[(2,3,4,6-tetramethyl) -phenyl] ketene and thiobenzamide as starting materials according to process (E), the process of the process according to the invention is It can be represented by the scheme:

3-[(2,5-dichloro-4,6-dimethyl) -phenyl] -5,5-dimethylpyrrolidine-2,4-dione and pivaloyl chloride as starting materials according to method (Fα) If so, the process of the process according to the invention can be represented by the following scheme:

When using 3-[(2,3-dichloro) -phenyl] -4-hydroxy-5-phenyl-Δ ³ -dihydrofuran-2-one and acetic anhydride as starting materials according to method (Fβ) The process of the process according to the invention can be represented by the following scheme:

8-[(2,4-dichloro-3-methyl) -phenyl] -5,5-pentamethylenepyrrolidine-2,4-dione and ethoxyethyl chloroformate as starting materials according to method (G) When used, the process of the process according to the invention can be represented by the following scheme:

3-[(2,6-dibromo-3,4-dimethyl) -phenyl] -4-hydroxy-6- (3-pyridyl) -pyrone and methyl chloromonothioformate according to method (Hα) When using as starting material, the process of the process according to the invention can be represented by the following scheme:

5-[(3-chloro-2,6-dimethyl) -phenyl] -6-hydroxy-2- (4-chlorophenyl) -thiazin-4-one, carbon disulfide and methyl urine according to method (Hβ) In the case of using an amide as a starting material, the process of the process according to the invention can be represented by the following scheme:

2-[(2,3,4,6-tetramethyl) -phenyl] -5,5-[(3-methyl) pentamethylene] -pyrrolidine-2,4-dione and methane according to method (I) When using sulfonyl chloride as starting material, the process of the process according to the invention can be represented by the following scheme:

2-[(2-chloro-5,6-dimethyl) -phenyl] -4-hydroxy-5-methyl-6- (2-pyridyl) -pyrone and 2,2,2- according to method (J) When trifluoroethyl chloromethanethio-phosphonate is used as starting material, the process of the process according to the invention can be represented by the following scheme:

3-[(2,4,5-trichloro) -6-methylphenyl] -5-cyclopropyl-5-methyl-pyrrolidine-2,4-dione and NaOH as starting materials according to method (K) If so, the process of the process according to the invention can be represented by the following scheme:

3-[(2,6-dichloro-4-bromo-3-methyl) -phenyl] -4-hydroxy-5,5-tetramethylene-Δ ³ -dihydro-furan-2 according to Method (Lα) In the case of using -one and ethyl isocyanate as starting materials, the process of the process according to the invention can be represented by the following scheme:

When 3-[(2-chloro-5,6-dimethyl) -phenyl] -5-methyl-pyrrolidine-2,4-dione and dimethylcarbamoyl chloride are used as starting materials according to the method (Lβ) The process of the process according to the invention can be represented by the following scheme:

The compounds of the general formula (II) below which are required as starting materials in the process (A) according to the invention are novel:

In the above formula,

A, B, V, W, X, Y, Z and R ⁸ have the meanings mentioned above.

Acylamino acid esters of formula (II) are for example acylated with amino acid derivatives of formula (XIX) with substituted phenylacetyl halides of formula (XX) (see Chem. Reviews 52, 237). -416 (1953); Bhattacharya, Indian J. Chem. 6, 341-5, 1968), esterifying acylamino acids of the general formula (XXI) (see Chem. Ind. (London) 1568 (1968)) Obtained by:

In the above formula,

A, B, V, W, X, Y, Z and R ⁸ each have the meanings mentioned above,

Hal represents chlorine or bromine.

Compounds of formula (XXI) are novel:

In the above formula,

A, B, V, W, X, Y and Z have the meanings mentioned above, respectively.

Compounds of the general formula (XXI) are prepared according to Schott-Baumann (Orgikinum, VEB Deutscher Verlag der Wissenschaften, Berlin 1977, p. 505) to the amino acids of the general formula (XXII) Obtained by acylation with substituted phenylacetyl halide of

In the above formula,

A, B, V, W, X, Y and Z have the meanings mentioned above,

Hal represents chlorine or bromine.

Some of the compounds of formula (XX) are novel and can be prepared by known methods.

Compounds of formula (XX) are for example substituted phenylacetic acid of formula (XXIII) in the presence of a diluent (optionally chlorinated aliphatic or aromatic hydrocarbons such as for example toluene or methylene chloride) By reaction with a halogenating agent (e.g. thionyl chloride, thionyl bromide, oxalyl chloride, phosgene, phosphorus trichloride, phosphorus tribromide or phosphorus pentachloride) at a temperature of -20 to 150 ° C, preferably -10 to 100 ° C Is obtained:

In the above formula,

V, W, X, Y and Z have the meanings mentioned above, respectively.

Some of the general formula (XXIII) compounds are novel and can be prepared by methods known from Organickum 15th edition, p.533, VEB Deutscher Verlag der Wissenschaften, Berlin 1977. Compounds of the general formula (XXIII) are, for example, substituted phenylacetic acid esters of the general formula (XXIV) with acids (e.g. hydrochloric acid such as hydrochloric acid) at a temperature of 0 to 150 < RTI ID = 0.0 > ) Or in the presence of a base (for example an alkali metal hydroxide such as sodium or potassium hydroxide) and optionally in the presence of a diluent (for example an aqueous alcohol such as methanol or ethanol). Is obtained:

In the above formula,

V, W, X, Y, Z and R ⁸ each have the meanings mentioned above.

Some of the compounds of formula (XXIV) are novel and can in principle be prepared by known methods.

Compounds of the general formula (XXIV) are, for example, first substituted with 1,1,1-trichloro-2-phenylethane of the general formula (XXV) at a temperature of 0 to 150 캜, preferably 20 to 120 캜. In the presence of a diluent (eg an alcohol derived from an alkoxide) in the presence of an alkoxide (for example an alkali metal alkoxide such as sodium methoxide or sodium ethoxide), followed by -20 to 150 ° C., preferably 0 Obtained by reaction with an acid (preferably inorganic acid, for example sulfuric acid) at a temperature of from 100 ° C. (see DE-33 14 249):

In the above formula,

V, W, X, Y and Z have the meanings mentioned above, respectively.

Some of the compounds of formula (XXV) are novel and can in principle be prepared by known methods.

Compounds of general formula (XXV) can be prepared by, for example, aniline of general formula (XXVI) in the presence of alkyl nitrite of general formula (XXVII), in the presence of copper (II) chloride, and optionally diluents ( Obtained by reaction with vinylidene chloride (CH ₂ = CCl ₂ ) at a temperature of -20 to 80 ° C., preferably 0 to 60 ° C., in the presence of an aliphatic nitrile such as acetonitrile):

R ²¹ -ONO (XXVII)

In the above formula,

V, W, X, Y and Z each have the meanings mentioned above,

R ²¹ represents alkyl, preferably C _1-6 -alkyl.

Some of the compounds of the general formula (XXVI) are known compounds or can in principle be prepared by known methods. Compounds of formula (XXVII) are known compounds of organic chemistry. Copper (II) chloride and vinylidene chloride have been known for a long time and are commercially available.

Compounds of formulas (XIX) and (XXII) are known in some cases and / or may be prepared by known methods (see, eg, Compagnon, Miocque, Ann. Chim. (Paris) [14] 5, p 11-22, 23-27 (1970).

Substituted cyclic aminocarboxylic acids of formula (XXIIa) in which A and B form a ring can generally be obtained by Bucherer-Bergs synthesis or by Strecker synthesis, each of In the case of different isomeric forms. Thus, isomers (denoted as β for convenience) where the radicals R and the carboxyl groups are located in the horizontal plane are mainly obtained according to the conditions of the Bucher-Bugs synthesis, whereas the amino groups and the radicals R are subject to the conditions of the strecker synthesis. Isomers located in the horizontal plane (referred to below for convenience) are mainly obtained (L. Munday, J. Chem. Soc. 4372 (1961); JT Eward, C. Jitrangeri, Can. J. Chem. 53, 3339). (1975)):

Boucher-Bugs Synthetic Tracker Synthesis

(β-isomer) (α-isomer)

In addition, the starting material of formula (II) used in the method (A) is reacted with a substituted phenylacetyl halide of formula (XX) by reacting an aminonitrile of formula (XXVIII) with a compound of formula (XXIX) After being obtained, it is obtained by acid alcoholysis:

In the above formula,

A, B, V, W, X, Y, Z, R ⁸ and Hal each have the meanings mentioned above.

Compounds of formula (XXIX) are also novel.

The compounds of the general formula (III) which are required as starting materials in the process (B) according to the invention are novel:

In the above formula,

A, B, V, W, X, Y, Z and R ⁸ each have the meanings mentioned above.

These can in principle be produced simply by known methods.

Compounds of formula (III) are obtained, for example, by acylating the 2-hydroxycarboxylic acid esters of formula (XXX) with substituted phenylacetyl halides of formula (XX) (see Chem. Reviews 52, 237-416 (1953):

In the above formula,

A, B, V, W, X, Y, Z, R ⁸ and Hal each have the meanings mentioned above.

In addition, compounds of formula (III) are obtained by alkylating substituted phenylacetic acid of formula (XXIII) with an α-halogenocarboxylic acid ester of formula (XXXI):

In the above formula,

A, B, V, W, X, Y, Z and R ⁸ have the meanings mentioned above,

Hal represents chlorine or bromine.

Compounds of formula (XXXI) are commercially available.

The compounds of formula (IV) which are required as starting materials for process (C) are novel:

In the above formula,

A, B, T, V, W, X, Y, Z and R ⁸ have the meanings mentioned above, respectively.

These can in principle be produced by known methods.

Compounds of formula (IV) are obtained by acylating, for example, substituted phenylacetic esters of formula (XXIV) with 2-benzylthio-carbonyl halides of formula (XXXII) in the presence of a strong base (see E.g. MS Chambers, EJ Thomas, DJ Williams, J. Chem. Soc.Chem.Commun., (1987), 1228):

In the above formula,

A, B, T, V, W, X, Y, Z and R ⁸ each have the aforementioned meanings,

Hal represents halogen, in particular chlorine or bromine.

Benzylthio-carbonyl halides of formula (XXXII) are known in some cases and / or can be prepared by known methods (J. Antibiotics (1983), 26, 1589).

The halogenocarbonylketene of formula (VI) required as starting material for process (D) is novel. These can in principle be prepared simply by known methods (see eg Org. Prep. Proced. Int., 7, (4), 155-158, 1975 and DE 1 945 703). Compounds of formula (VI) may be substituted with substituted phenylmalonic acid of formula (XXXIII), optionally in the presence of a catalyst such as diethylformamide, methylsterylformamide or triphenylphosphine, and If desired an acid halide such as thionyl chloride, phosphorus (V), phosphorus chloride at a temperature of -20 to 200 ° C, preferably 0 to 150 ° C, in the presence of a base such as pyridine or triethylamine (III), obtained by reacting with oxalyl chloride, phosgene or thionyl bromide:

In the above formula,

V, W, X, Y and Z each have the meanings mentioned above,

Hal represents chlorine or bromine.

Substituted phenylmalonic acid of formula (XXXIII) is novel. However, they can be prepared simply by known methods, for example by saponifying substituted phenylmalonic acid esters of the general formula (XXXIV) (see, for example, Organikum, VEB Deutscher Verlag der Wissenschaften, Berlin 1977, p. 517 ff):

In the above formula,

V, W, X, Y, Z and R ⁸ each have the meanings mentioned above.

Carbonyl compounds of formula (V) or compounds of formula (Va) which are silyl enol ethers thereof which are needed as starting materials for the process (E) according to the invention are commercially available, generally known or known It can be obtained by the method.

In the above formula,

A, D and R ^{8 '} each have the meaning mentioned above.

The preparation of the ketenoic acid chlorides of the general formula (VI) which are necessary as starting materials for carrying out the process (E) according to the invention has already been mentioned in the process (D) according to the invention. Thioamides of the general formula (VII) necessary to carry out process (E) according to the invention are compounds generally known in organic chemistry.

Wherein A has the meanings mentioned above.

The malonic esters of formula (XXXIV) are novel and can be prepared by methods generally known in organic chemistry (see, eg, Tetrahedron Lett. 27, 2763 (1986) and Organikum, VEB Deutscher Verlag der Wissenschaften, Berlin). 1977, p. 587 ff):

Acid halides of general formula (VIII), general formula (IX), which are additionally required as starting materials for carrying out the processes (F), (G), (H), (J), (K) and (L) according to the invention. Carboxylic anhydride of), chloroformic acid ester or chloroformic acid thioester of general formula (X), chloromonothioformic acid ester or chlorodithioformic acid ester of general formula (XI), alkyl halide of general formula (XII), general formula ( XIII) sulfonyl chloride, phosphorus compound of formula (XIV), metal hydroxide of formulas (XV) and (XVI), metal alkoxide or amine, isocyanate of formula (XVII) and of formula (XVIII) Carbamoyl chloride is a generally known compound of organic or inorganic chemistry.

Formulas (V), (VII) to (XVIII), (XIX), (XXII), (XXVIII), (XXX), (XXXI), (XXXII), (XXXIII) and (XXXIV) are cited at the outset. It may be prepared by the method described in the patent application and / or described herein.

Method (A) shows that A, B, V, W, X, Y, Z and R ⁸ respectively condensate intramolecularly condensed compounds of formula (II) as defined above in the presence of a diluent and in the presence of a base. It features.

Diluents used in process (A) according to the invention are all organic solvents which are inert to the reactants. These are preferably hydrocarbons such as toluene and xylene, ethers such as dibutyl ether, tetrahydrofuran, dioxane, glycol dimethyl ether and diglycol dimethyl ether, dimethyl sulfoxide, sulfolane, dimethylformamide and N-methyl Polar solvents such as pyrrolidone and alcohols such as methanol, ethanol, propanol, isopropanol, butanol, isobutanol and t-butanol can be used.

Suitable bases (deprotonating agents) used in process (A) according to the invention can be all conventional proton acceptors. As these, alkali and alkaline earth metal oxides, hydroxides and carbonates, such as sodium hydroxide, potassium hydroxide, magnesium oxide, calcium oxide, sodium carbonate, potassium carbonate and calcium carbonate, can also be used, which are also respectively phase transfer catalysts, for example For example triethylbenzylammonium chloride, tetrabutylammonium bromide, adogen 464 (= methyltrialkyl (C _8-10 ) ammonium chloride) or TDA 1 (= tris- (methoxyethoxyethyl) amine) . Alkali metals such as sodium or potassium can further be used. Alkali and alkaline earth metal amides and hydrides such as sodium amide, sodium hydride and calcium hydride, and alkali metal alkoxides such as sodium methoxide, sodium ethoxide and potassium t-butoxide may also be used.

When carrying out process (A) according to the invention, the reaction temperature can be varied within a relatively wide range. In general, the reaction is carried out at a temperature of -50 ° C to 250 ° C, preferably -30 ° C to 150 ° C.

Process (A) according to the invention is generally carried out under atmospheric pressure.

In the case of carrying out the method (A) according to the present invention, the reactive moiety and the deprotonation base of the general formula (II) are generally used in equimolar amounts to about 2 times equimolar amounts. However, it is also possible to use one component or another component in large amounts (up to 3 moles).

Method (B) shows that A, B, V, W, X, Y, Z and R ⁸ respectively condensate intramolecularly condensed compounds of formula (III) as defined above in the presence of a diluent and in the presence of a base. It features.

Diluents used in process (B) according to the invention are all organic solvents which are inert to the reactants. These are preferably hydrocarbons such as toluene and xylene, ethers such as dibutyl ether, tetrahydrofuran, dioxane, glycol dimethyl ether and diglycol dimethyl ether, dimethyl sulfoxide, sulfolane, dimethylformamide and N-methyl Polar solvents such as pyrrolidone can be used. Alcohols such as methanol, ethanol, propanol, isopropanol, butanol, isobutanol and t-butanol may also be used.

Suitable bases (deprotonating agents) used in process (B) according to the invention can be all conventional proton acceptors. As these, alkali and alkaline earth metal oxides, hydroxides and carbonates, such as sodium hydroxide, potassium hydroxide, magnesium oxide, calcium oxide, sodium carbonate, potassium carbonate and calcium carbonate, can also be used, which are also respectively phase transfer catalysts, for example For example triethylbenzylammonium chloride, tetrabutylammonium bromide, adogen 464 (= methyltrialkyl (C _8-10 ) ammonium chloride) or TDA 1 (= tris- (methoxyethoxyethyl) amine) . Alkali metals such as sodium or potassium can further be used. Alkali and alkaline earth metal amides and hydrides such as sodium amide, sodium hydride and calcium hydride, and alkali metal alkoxides such as sodium methoxide, sodium ethoxide and potassium t-butoxide may also be used.

In carrying out process (B) according to the invention, the reaction temperature can be varied within a relatively wide range. In general, the reaction is carried out at a temperature of -50 ° C to 250 ° C, preferably -30 ° C to 150 ° C.

Process (B) according to the invention is generally carried out under atmospheric pressure.

In carrying out the process (B) according to the invention, the reactive component and the deprotonated base of the general formula (III) are generally used in about equimolar amounts. However, it is also possible to use one component or another component in large amounts (up to 3 moles).

Method (C) is a method in which A, B, T, V, W, X, Y, Z and R ⁸ are each intramolecular ring closure in the presence of an acid and in the presence of a diluent It is characterized by.

Diluents used in process (C) according to the invention are all organic solvents which are inert to the reactants. These are preferably hydrocarbons such as toluene and xylene, halogenated hydrocarbons such as dichloromethane, chloroform, ethylene chloride, chlorobenzene and dichlorobenzene, dimethyl sulfoxide, sulfolane, dimethylformamide and N-methylpyrrolidone Polar solvents can be used. Alcohols such as methanol, ethanol, propanol, isopropanol, butanol, isobutanol and t-butanol can be used.

The acid used may also optionally be used as a diluent.

Acids which can be used in the process (C) according to the invention are all customary inorganic and organic acids, for example hydrohalic acid, sulfuric acid, alkyl-, aryl- and haloalkylsulfonic acids; Halogenated alkylcarboxylic acids, for example trifluoroacetic acid, are especially used.

In carrying out process (C) according to the invention, the reaction temperature can be varied within a relatively wide range. In general, the reaction is carried out at a temperature of -30 ° C to 250 ° C, preferably 0 ° C to 150 ° C.

Process (C) according to the invention is generally carried out under atmospheric pressure.

In the case of carrying out the method (C) according to the present invention, the reactive component and the acid of the general formula (IV) are used, for example, in equimolar amounts. However, it is also possible to optionally use an acid in catalytic amounts.

Process (D) according to the invention comprises a compound of formula (Va) wherein A and B are each a carbonyl compound of formula (V) or a silyl enol ether thereof, as defined above, optionally in the presence of a diluent And, optionally, in the presence of an acid acceptor, V, W, X, Y and Z, respectively, react with the ketenoic acid halides of general formula (VI) as defined above.

Diluents used in process (D) according to the invention are all organic solvents which are inert to the reactants. These are preferably hydrocarbons such as o-dichlorobenzene, tetralin, toluene and xylene, ethers such as dibutylether, glycoldimethylether and diglycoldimethylether, and dimethyl sulfoxide, sulfolane, dimethylformamide or Polar solvents such as N-methylpyrrolidone can be used.

Acid acceptors that can be used to perform the method (D) according to the invention are all conventional acid acceptors.

These are preferably triethylamine, pyridine, diazabicyclooctane (DABCO), diazabicycloundecene (DBU), diazabicyclononene (DBN), Huenig base or N, N-dimethylaniline Tertiary amines such as can be used.

In carrying out process (D) according to the invention, the reaction temperature can be varied within a relatively wide range. In general, the reaction is carried out at a temperature of 0 ° C to 250 ° C, preferably 50 ° C to 220 ° C.

Process (D) according to the invention is preferably carried out at atmospheric pressure.

In carrying out the method (D) according to the invention, the reactive components of the general formulas (V) and (VI), and optionally the acid acceptor, are generally used in approximately equimolar amounts. However, it is also possible to use one component or another component in large amounts (up to 5 moles).

The process (E) according to the invention is a process in which A is substituted with thioamides of the general formula (VII) as defined above in the presence of a diluent, and optionally in the presence of an acid acceptor, V, W, X, Y And Z are each reacted with a ketenoic acid halide of formula (VI) as defined above.

Diluents used in process (E) according to the invention are all organic solvents which are inert to the reactants. These are preferably hydrocarbons such as o-dichlorobenzene, tetralin, toluene and xylene, ethers such as dibutylether, glycoldimethylether and diglycoldimethylether, and dimethyl sulfoxide, sulfolane, dimethylformamide and Polar solvents such as N-methylpyrrolidone can be used.

Acid acceptors that can be used to carry out the method (E) according to the invention are all conventional acid acceptors.

These are preferably 3 such as triethylamine, pyridine, diazabicyclooctane (DABCO), diazabicycloundecene (DBU), diazabicyclononene (DBN), Hunig base and N, N-dimethylaniline Tertiary amines may be used.

When carrying out process (E) according to the invention, the reaction temperature can be varied within a relatively wide range. In general, the reaction is carried out at a temperature of 0 ° C to 250 ° C, preferably 20 ° C to 220 ° C.

Process (E) according to the invention is conveniently carried out at atmospheric pressure.

In carrying out the method (E) according to the invention, the reactive components of the general formulas (VII) and (VI), and optionally the acid acceptor, are generally used in approximately equimolar amounts. However, it is also possible to use one component or another component in large amounts (up to 5 moles).

Process (Fα) is a process in which the compounds of the general formulas (I-1-a) to (I-5-a) are in each case, optionally in the presence of a diluent, and optionally in the presence of an acid-binder, Reaction with the carboxylic acid halide of VIII).

Diluents which can be used in the process (Fα) according to the invention are all solvents which are inert to the acid halide. These are preferably ketones such as hydrocarbons such as benzine, benzene, toluene, xylene and tetralin, halogenated hydrocarbons such as methylene chloride, chloroform, carbon tetrachloride, chlorobenzene and o-dichlorobenzene, acetone and methyl isopropyl ketone , Ethers such as diethylether, tetrahydrofuran and dioxane, carboxylic acid esters such as ethyl acetate, and also polar solvents such as dimethylformamide, dimethyl sulfoxide and sulfolane can be used. The reaction can also be carried out in the presence of water if the acid halide is stable to hydrolysis.

In the reaction by the method (Fα) according to the invention, suitable acid-binding agents are all customary acid acceptors. These are preferably 3 such as triethylamine, pyridine, diazabicyclooctane (DABCO), diazabicycloundecene (DBU), diazabicyclononene (DBN), Hunig base and N, N-dimethylaniline Alkaline earth metal oxides such as tertiary amines, magnesium oxide and calcium oxide, alkali metal and alkaline earth metal carbonates such as sodium carbonate, potassium carbonate and calcium carbonate and also alkali metals such as sodium hydroxide and potassium hydroxide can be used.

In the case of carrying out the method (Fα) according to the invention, the reaction temperature can be varied within a relatively wide range. In general, the reaction is carried out at a temperature of -20 ° C to + 150 ° C, preferably 0 ° C to 100 ° C.

When carrying out the process (Fα) according to the invention, the starting materials of the general formulas (I-1-a) to (I-5-a) and the carboxylic acid halides of the general formula (VIII) are generally in approximately equivalent amounts Used. However, it is also possible to use carboxylic acid halides in large amounts (up to 5 moles). Post-treatment is carried out according to conventional methods.

Method (Fβ) is a compound of formula (I-1-a) to (I-5-a), respectively, in the presence of a diluent, and optionally in the presence of an acid-binder, It is characterized by reacting with carboxylic anhydride.

Diluents which can be used in the process (Fβ) according to the invention are preferably suitable diluents when using acid halides. On the other hand, carboxylic acid anhydrides used in excess may also act as diluents at the same time.

Acid-binding agents optionally added to process (Fβ) are preferably suitable acid-binding agents when using acid halides.

When carrying out the process (Fβ) according to the invention, the reaction temperature can be varied within a relatively wide range. In general, the reaction is carried out at a temperature of -20 ° C to + 150 ° C, preferably 0 ° C to 100 ° C.

In carrying out the process (Fβ) according to the invention, the starting materials of the general formulas (I-1-a) to (I-5-a) and the carboxylic acid anhydrides of the general formula (XI) are generally in each case approximately Used in equivalent amounts. However, it is also possible to use carboxylic anhydride in large excess (5 mol or less). Post-treatment is carried out according to conventional methods.

In general, the workup is carried out by removing the carboxylic anhydrides and diluents present in excess and also the resulting carboxylic acids by distillation or by washing with organic solvents or water.

Process (G) comprises compounds of formulas (I-1-a) to (I-5-a), respectively, in the presence of a diluent, and optionally in the presence of an acid-binder, in which It is characterized by reacting with chloroform acid ester or chloroform acid thioester.

Acid-binding agents which can be used in process (G) according to the invention are all customary acid acceptors. These preferably include triethylamine, pyridine, DABCO, DBU, DBN, Hunig base and tertiary amines such as N, N-dimethylaniline, alkaline earth metal oxides such as magnesium oxide and calcium oxide, sodium carbonate, potassium carbonate and Alkali and alkaline earth metal carbonates such as calcium carbonate and also alkali metals such as sodium hydroxide and potassium hydroxide can be used.

Diluents which can be used in process (G) according to the invention are all solvents which are inert to chloroformic acid esters or chloroformic acid thioesters. These are preferably ketones such as hydrocarbons such as benzine, benzene, toluene, xylene and tetralin, halogenated hydrocarbons such as methylene chloride, chloroform, carbon tetrachloride, chlorobenzene and o-dichlorobenzene, acetone and methyl isopropyl ketone Ethers such as diethyl ether, tetrahydrofuran and dioxane, carboxylic acid esters such as ethyl acetate, nitriles such as acetonitrile, and also polar solvents such as dimethylformamide, dimethyl sulfoxide and sulfolane can be used.

In carrying out process (G) according to the invention, the reaction temperature can be varied within a relatively wide range. The reaction temperature is generally -20 ° C to + 100 ° C, preferably 0 ° C to 50 ° C.

Process (G) according to the invention is generally carried out under atmospheric pressure.

When carrying out process (G) according to the invention, suitable starting materials of general formulas (I-1-a) to (I-5-a) and suitable chloroformic acid esters or chloroformic acid thioesters of general formula (X) Is generally used in equivalent amounts. However, it is also possible to use one component or another component in large amounts (up to 2 moles). Post-treatment is carried out according to conventional methods. In general, the workup is carried out by removing the precipitated salts, removing the diluent and concentrating the remaining reaction mixture.

Method (H) according to the present invention respectively comprises compounds of general formulas (I-1-a) to (I-5-a),

Reacting with a compound of formula (XI) in the presence of a (Hα) diluent, and optionally in the presence of an acid-binding agent, or

(Hβ) is characterized by reacting with carbon disulfide, optionally in the presence of a diluent, and optionally in the presence of a base, followed by reaction with an alkyl halide of the general formula (XII).

In process (Hα) according to the invention, about 1 mole of chloromonothioformic acid ester or chloroditi of general formula (XI) per mole of starting compound of general formulas (I-1-a) to (I-5-a) The formic acid ester is reacted at a temperature of 0 ° C to 120 ° C, preferably 20 ° C to 60 ° C.

Diluents which may optionally be added are all inert polar organic solvents such as ethers, amides, sulfones, sulfoxides and halogenoalkanes.

Dimethyl sulfoxide, tetrahydrofuran, dimethylformamide or methylene chloride are preferably used.

In a preferred embodiment, further addition is provided when a strong deprotonating agent, for example sodium hydride or potassium tert-butoxide, is added to prepare the enolate salts of compounds (I-1-a) to (I-5-a) There is no need to add an acid-binder.

Where acid-binding agents are used, customary inorganic or organic bases are suitable, for example sodium hydroxide, sodium carbonate, potassium carbonate, pyridine and triethylamine.

The reaction can be carried out at atmospheric or elevated pressure, but preferably at atmospheric pressure. Post-treatment is carried out according to conventional methods.

In the process (Hβ) according to the invention, equimolar amounts or excess carbon disulfide are added in each case per mole of starting compound of general formulas (I-1-a) to (I-5-a). In this case the reaction is preferably reacted at a temperature of 0 ° C to 50 ° C and in particular at 20 ° C to 30 ° C.

Sometimes it is convenient to prepare the corresponding salts from the compounds of the general formulas (I-1-a) to (I-5-a) by first adding a base (for example potassium tert-butoxide or sodium hydride). Compounds (I-1-a) to (I-5-a) are each stirred for several hours until completion of the formation of the intermediate compound, for example at room temperature, followed by reaction with carbon disulfide.

Bases that can be used in the method (Hβ) are all conventional proton receptors. As these, preferably alkali metal hydrides, alkali metal alkoxides, alkali metal or alkaline earth metal carbonates or bicarbonates, or nitrogen bases can be used. These include, for example, sodium hydride, sodium methoxide, sodium hydroxide, calcium hydroxide, potassium carbonate, sodium bicarbonate, triethylamine, dibenzylamine, diisopropylamine, pyridine, quinoline, diazabicyclooctane (DABCO), dias Xabicyclononene (DBN) and diazabicycloundecene (DBU) may be mentioned.

Diluents which can be used in the process are all conventional solvents.

These preferably include aromatic hydrocarbons such as benzene or toluene, alcohols such as methanol, ethanol, isopropanol or ethylene glycol, nitriles such as acetonitrile, ethers such as tetrahydrofuran or dioxane, amides such as dimethylformamide, or Polar solvents such as dimethyl sulfoxide or sulfolane can be used.

The reaction of general loading (XII) with alkyl halides is preferably carried out at 0 ° C to 70 ° C and in particular at 20 ° C to 50 ° C. In this case, at least equimolar amounts of alkyl halides are used.

The reaction is carried out at atmospheric or elevated pressure, preferably at atmospheric pressure.

Post-treatment is carried out according to conventional methods.

Process (I) according to the invention is carried out in general in the presence of compounds of the general formulas (I-1-a) to (I-5-a), respectively in the presence of a diluent and optionally in the presence of an acid-binder Reaction with sulfonylchloride of formula (XIII).

In the preparation method (I), about 1 mole of sulfonyl chloride of the general formula (XIII) is added at -20 ° C to 150 ° C per mole of the starting compounds of the general formulas (I-1-a) to (I-5-a) In particular, it reacts at 0 to 70 degreeC.

Method (I) is preferably carried out in the presence of a diluent.

Possible diluents are all inert polar organic solvents such as ethers, amides, ketones, carboxylic esters, nitriles, sulfones, sulfoxides or halogenated hydrocarbons, for example methylene chloride.

Dimethyl sulfoxide, tetrahydrofuran, dimethylformamide and methylene chloride are preferably used.

In a preferred embodiment, further addition is provided when a strong deprotonating agent, for example sodium hydride or potassium tert-butoxide, is added to prepare the enolate salts of compounds (I-1-a) to (I-5-a) There is no need to add an acid-binder.

Where acid-binding agents are used, customary inorganic or organic bases are suitable, for example sodium hydroxide, sodium carbonate, potassium carbonate, pyridine and triethylamine.

The reaction can be carried out at atmospheric or elevated pressure, but preferably at atmospheric pressure. Post-treatment is carried out according to conventional methods.

Process (J) according to the invention is carried out in general in the presence of compounds of the general formulas (I-1-a) to (I-5-a), respectively in the presence of a diluent and optionally in the presence of an acid-binder Reacted with a phosphorus compound of formula (XIV).

In the preparation method (J), in order to obtain a compound of the general formulas (I-1-e) to (I-5-e), start of general formulas (I-1-a) to (I-5-a) 1 to 2 moles, preferably 1 to 1.3 moles, of the phosphorus compound of the general formula (XIV) are reacted at -40 ° C to 150 ° C, preferably -10 ° C to 110 ° C per mole of the compound.

Method (J) is preferably carried out in the presence of a diluent.

Possible diluents are all inert polar organic solvents such as ethers, carboxylic acid esters, halogenated hydrocarbons, ketones, amides, nitriles, sulfones, sulfoxides and the like.

Acetonitrile, dimethylsulfoxide, tetrahydrofuran, dimethylformamide and methylene chloride are preferably used.

Acid-binding agents which may optionally be added are conventional inorganic or organic bases such as hydroxides, carbonates or amines. These may be mentioned sodium hydroxide, sodium carbonate, potassium carbonate, pyridine and triethylamine.

The reaction can be carried out at atmospheric or elevated pressure, but preferably at atmospheric pressure. Post-treatment is carried out according to conventional methods of organic chemistry. The final product is preferably purified by crystallization, chromatography purification or so-called "incipient distillation" (ie removal of volatiles in vacuo).

Method (K) is a compound of formulas (I-1-a) to (I-5-a), each of which is optionally a metal hydroxide or metal alkoxide or a general formula of formula (XV) in the presence of a diluent And reacts with an amine of (XVI).

Diluents which can be used in the process (K) according to the invention are ethers such as tetrahydrofuran, dioxane, diethyl ether, alcohols such as methanol, ethanol isopropanol and water. Process (K) according to the invention is generally carried out at atmospheric pressure. The reaction temperature is generally -20 ° C to 100 ° C, preferably 0 ° C to 50 ° C.

Process (L) according to the present invention respectively comprises compounds of general formulas (I-1-a) to (I-5-a),

(Lα) optionally react with a compound of formula (XVII) in the presence of a diluent and optionally in the presence of a catalyst, or

(Lβ) is characterized in that it reacts with a compound of the general formula (XVIII), optionally in the presence of a diluent, and optionally in the presence of an acid-binding agent.

In the preparation method (Lα), about 1 mole of isocyanate of the general formula (XVII) per mole of starting compound of the general formulas (I-1-a) to (I-5-a) is 0 ° C to 100 ° C, preferably The reaction is carried out at 20 ° C to 50 ° C.

Method (Lα) is preferably carried out in the presence of a diluent.

Diluents that can be used are all inert organic solvents such as aromatic hydrocarbons, halogenated hydrocarbons, ethers, amides, nitriles, sulfones or sulfoxides.

A catalyst may optionally be added to promote the reaction rate. The catalyst used is very advantageously an organotin compound, for example dibutyltin dilaurate.

The reaction is preferably carried out at atmospheric pressure.

In the preparation method (Lβ), about 1 mole of carbamoyl chloride of the general formula (XVIII) per mole of starting compound of the general formulas (I-1-a) to (I-5-a) is 0 ° C to 150 ° C, preferably Preferably at 20 ° C to 70 ° C.

Diluents which may optionally be added are all inert organic solvents such as ethers, carboxylic acid esters, nitriles, ketones, amides, sulfones, sulfoxides or halogenated hydrocarbons.

Dimethyl sulfoxide, tetrahydrofuran, dimethylformamide or methylene chloride are preferably used.

In a preferred embodiment, further addition is provided when a strong deprotonating agent, for example sodium hydride or potassium tert-butoxide, is added to prepare the enolate salts of compounds (I-1-a) to (I-5-a) There is no need to add an acid-binder.

Where acid-binding agents are used, customary inorganic or organic bases are suitable, for example sodium hydroxide, sodium carbonate, potassium carbonate, triethylamine or pyridine.

The reaction is carried out at atmospheric or elevated pressure, preferably at atmospheric pressure. Post-treatment is carried out according to conventional methods.

The active compounds according to the invention are suitable for controlling animal pests, preferably arthropods and nematodes, especially insects and arachnids, encountered in the fields of agriculture, forestry, storage products and materials, and hygiene. They are active for all or some stages of species and development that are moderately sensitive or resistant. The pests mentioned above include:

The order of Isopoda, for example Oniscus asellus, Armadillidium vulgare and Porcellio scaber.

From the order of Diloplopoda, for example Blaniulus guttulatus.

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

From the order of the symphyla, for example Scutigerella immaculata.

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

The order of Collembola, for example Onychiurus armatus.

From the order of Orthoptera, for example, Blata orientalis, Periplaneta americana, Leucophaea maderae, Blatella germanica, Ah Keta Domestikus, Gryllotalpa spp., Locusta migratoria migratorioides, Melanoplus differentialis and Systoser Schistocerca gregaria.

From the order of the dermaptera, for example Porficula auricularia.

Termite Isoptera, for example Reticulitermes spp.

Anoplura, for example, Phylloxera vastatrix, Pemphigus spp., Pediculus humanus corporis, Haematopinus spp. And Linognathus spp.

Allophaga, for example Trichodectes spp. And Damalinea spp.

From the order of the Thysanoptera, for example, Hercinothrips femoralis and Tripps tabaci.

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

The cicada (Homoptera), for example Aleurodes brassicae, Bemisia tabaci, Trialeurodes vaporariorum, Apis gossypii, Brevicoryne brassicae, Cryptomyzus ribis, Apis fabae, Doralis pomi, Eriosoma lanigerum, hyaloptherus Arundinis (Hyalopterus arundinis), Macrosisph avenae, Myzus spp., Phorodon humuli, Rhopalosiphum padi, Empoasca species spp.), Eucelis bilobatus, Nephotettix cincticeps, Lecanium corni, Saissetia oleae, Lao delfax str Laodelphax striatellus, Nilapa Bata Lou Regensburg (Nilaparvata lugens), Oh sludge de Ella Augusta is T (Aonidiella aurantii), ah Speedy ohtuseu Hedera (Aspidiotus hederae), pseudo nose Syracuse species (Pseudococcus spp.) And programs Silas species (Psylla spp.).

Lepidoptera, for example Pectinophora gossypiella, Bupalus piniarius, Cheimatobia brumata, Lithocolletis blancardella, Hyponomeuta padella, Flutella maculipennis, Malacosoma neustria, Euprotis chrysorrhoea, Lymantria spp. ), Buculatrix thurberiella, Phyloknistis citrella, Agrotis spp., Euxoa spp., Feltia spp., Earias insulana, Heliothis spp., Spodoptera exigua, Mamestra brassicae, Panolis flammea, Prodenia Ritu Prodenia litura, Spodoptera spp., Trichoplusia ni, Carpocapsa pomonella, Pieris spp., Chilo spp. .), Pyrausta nubilalis, Ephestia kuehniella, Galleria mellonella, Tineola bisselliella, Tinnea pellionella ), Hofmannophila pseudospretella, Cacaocia podana, Capua reticulana, Choristoneura fumiferana, Clichy ambugella (Clysia ambiguella), Homona magnanima, and Tortrix viridana.

Trees of the Coleoptera, for example, Anobium punctatum, Rhizopertha dominica, Acanthoscelides obtectus, Hilotrupes bajulus, Agelastica alni, Leptinotarsa decemlineata, Phaedon cochleariae, Diabrotica spp., Psylliodes chrysocephala, Epilachna varivestis, Atomaria spp., Oryzaephilus surinamensis, Antonomus spp., Cytophilus spp. Sitophilus spp.), Otiorrhynchus sulcatus, Cosmopolites sordidus, Cethorthornchnch assimilis, Hypera postica, Derme Dermestes spp., Trogoderma spp., Anthrenus spp., Attagenus spp., Lyctus spp., Mellige Meligethes aeneus, Ptinus spp., Niptus hololeucus, Gibbium psylloides, Tribolium spp., Teneblio Molytoro molitor, Agriotes spp., Conoderus spp., Melolontha melolontha, Amphimallon solstitialis and Kostelitraze Alandica (Costelytra zealandica).

Hymenopera, for example Diprion spp., Hoplocampa spp., Lasius spp., Monomorium pharaonis and Vespa species ( Vespa spp.).

Diptera, for example Aedes spp., Anopheles spp., Culex spp., Drosophila melanogaster, Musca species ( Musca spp.), Pannia spp., Califora erythrocephala, Lucilia spp., Chrysomyia spp., Cuterebra spp. ), Gastrophilus spp., Hippobosca spp., Stomoxys spp., Oestrus spp., Hypoderma spp. , Tabanus spp., Tannia spp., Bibio hortulanus, Oscinella frit, Phorbia spp., Pegomina hyosquiami (Pegomyia hyoscyami), Ceratitis capitata, Dacus oleae and Tipula paludosa.

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

Arachnida, for example Scorpio maurus and Latrodectus mactans.

The order of the ticks Acarina, for example, Acarus siro, Argas spp., Ornithodoros spp., Dermanyssus gallinae, Eriopies libis (Eriophyes ribis), Phyllocoptruta oleivora, Bophillus spp., Rhipicephalus spp., Amblyomma spp., Hyalomma spp. ., Ixodes spp., Psoroptes spp., Chorioptes spp., Sarcoptes spp., Tarsonemus spp. ), Bryobia praetiosa, Panonychus spp. And Tetranychus spp.

The active compounds according to the invention exhibit high pesticidal and acaricide activity.

The active compounds according to the invention are plant harmful insects, for example mustard larvae (Phaedon cochleariae), cicada larvae (Nephotettix cincticeps) and Chinese cabbage It is used particularly successfully to control moth caterpillars (Plutella maculipennis).

The active compounds according to the invention can also be used as deciduous, drying, broadleaf plant killing agents and in particular weed-removing agents. The term "weeds" broadly means all plants that grow in unwanted places. Whether the compounds according to the invention act as total or selective herbicides depends essentially on the amount used.

The amount of active compound according to the invention necessary for controlling weeds is from 0.001 to 10 kg / dl, preferably 0.005 to 5 kg / dl.

The active compounds according to the invention can be used, for example, in connection with the following plants:

Dicotyledonous weeds of the following genus: Sinapis, Lepidium, Gallium, Stellaria, Matricaria, Anthemis, Galinsoga, Ke Nopodium, Urtica, Senesio, Amaranthus, Portulaca, Xanthium, Convolvulus, Ipomoea, Polygonum, Sesbania, Ambrosia, Cirsium, Carduus, Sonchus, Solanum, Rorippa, Rotala ), Lindernia, Lamium, Veronica, Abutilon, Emex, Datura, Viola, Galeopsis, Papaver, Centaurea, Trifolium, Ranunculus and Taraxacum.

Dicotyledonous crops of the following genus: Gossypium, Glycine, Beta, Doucus, Phaseolus, Pisum, Solanum, Linum ), Ipomoea, Vicia, Nicotiana, Lycopersicon, Arachis, Brassica, Lactuca, Cucumis ) And Cucurbita.

Monocot weeds in the genus: Echinochloa, Setaria, Panicum, Digitaria, Phleum, Poa, Festusca, Festuca, Eleusin, Brachiaria, Lolium, Bromus, Avena, Cyperus, Sorghum, Agropyron, Sino Cynodon, Monochoria, Fimbristylis, Sagittaria, Eleocharis, Scirpus, Paspalum, Iscamum ), Sphenoclea, Dactyloctenium, Agrostis, Alopecurus and Apera.

Monocot crops of the following genus: Oryza, Zea, Triticum, Hordeum, Avena, Secale, Sorghum, Panicum Panicum), Saccharum, Ananas, Asparagus and Allium.

However, the use of the active compounds according to the invention is not limited at all in the above and extends to other plants in the same way.

The compounds of the invention are suitable for the overall control of weeds, depending on concentration, for example on industrial areas and railways, and on sidewalks and plazas with or without trees. Similarly, the compounds of the present invention include, for example, plantation, ornamental water, orchard, vineyard, citrus field, nut orchard, banana plantation, coffee plantation, tea plantation, rubber plantation, palm plantation, cocoa plantation, soft fruit plantation and hop field, decoration It can be used to control weeds in perennial crops growing on grass, sports lawns and pastures, and to selectively control weeds in annual crops.

The active compounds according to the invention are very suitable for the selective control of annual weeds in biennial crops before and after germination. They can be very useful for controlling grass weeds, for example in cotton or beet.

The active compounds according to the invention are in solution, emulsions, hydrating powders, suspensions, powders, powders, pastes, soluble powders, granules, suspension-emulsion concentrates, natural and synthetic substances impregnated with the active compounds, and polymeric materials. It can be converted into a conventional formulation such as an ultrafine capsule.

These formulations are prepared by known methods, for example by mixing the active compounds with extenders, ie liquid solvents and / or solid carriers, optionally using surfactants, ie emulsifiers and / or dispersants and / or foam formers.

When water is used as the extender, organic solvents can also be used, for example, as auxiliary solvents. As a liquid solvent, Aromatic compounds, such as xylene, toluene, or alkylnaphthalene mainly; Chlorinated aromatic or chlorinated aliphatic hydrocarbons such as chlorobenzene, chloroethylene or methylene chloride; Aliphatic hydrocarbons such as cyclohexane or paraffins such as petroleum fractions, mineral oils and vegetable oils; Alcohols such as butanol or glycols and their ethers and esters; Ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone; Strong polar solvents such as dimethylformamide and dimethylsulfoxide, and water are suitable.

Suitable solid carriers are ammonium salts and ground natural minerals such as kaolin, clay, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth, and ground synthetic minerals such as highly dispersed silica, alumina and silicate. Do. Solid carriers for granulation include, for example, pulverized and classified natural rocks such as calcite, marble, pumice, calcite and dolomite, and synthetic granules of inorganic and organic powders, and organic such as sawdust, coconut husk, corncobs and tobacco stems. Granules of material are suitable. Emulsifiers and / or foam formers include, for example, nonionic and anionic emulsifiers, for example polyoxyethylene fatty alcohol ethers such as polyoxyethylene fatty acid esters, alkylaryl polyglycol ethers, alkylsulfonates, alkylsulfates, arylsulfos Nate and albumen hydrolysis products are suitable. Suitable dispersants are, for example, lignin-sulfite waste liquors and methylcellulose.

Adhesives such as carboxymethylcellulose and natural and synthetic polymers in the form of powders, granules or latex, such as gum arabic, polyvinyl alcohol and polyvinyl acetate, or natural and synthetic phospholipids such as cephalin and lecithin, may be used in the formulation. Can be. As other additives, mineral oil and vegetable oil may be used.

Colorants such as inorganic pigments such as iron oxide, titanium oxide and prussian blue, and organic pigments such as alizarin dyes, azo dyes and metal phthalocyanine dyes, and salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc; You can also use the same micronutrients.

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

The active compounds according to the present invention may be used in combination with other active compounds such as insecticides, attractants, sterilizers, acaricides, nematicides, fungicides, growth regulators or herbicides in commercially available formulations and use forms prepared from these preparations. May be present as a mixture of. Pesticides include, for example, phosphates, carbamates, carboxylates, chlorinated hydrocarbons, phenylurea and materials produced by microorganisms.

Examples of particularly advantageous mixture components are the following compounds:

Fungicides:

2-aminobutane; 2-anilino-4-methyl-6-cyclopropyl-pyrimidine; 2 ', 6'-dibromo-2-methyl-4'-trifluoromethoxy-4'-trifluoro-methyl-1,3-thiazole-5-carboxanilide; 2,6-dichloro-N- (4-trifluoromethylbenzyl) benzamide; (E) -2-methoxyimino-N-methyl-2- (2-phenoxyphenyl) -acetamide; 8-hydroxyquinoline sulfate; Methyl (E) -2- {2- [6- (2-cyanophenoxy) -pyrimidin-4-yloxy] -phenyl} -3-methoxyacrylate; Methyl- (E) -methoximino [alpha- (o-tolyloxy) -o-tolyl] acetate; 2-phenylphenol (OPP), Aldimorph, Ampropyl Force, Anilazine, Azaconazole, Benalacyl, Benodanil, Benomil, Binapacryl, Biphenyl, Vitertanol, Blastisidin-S, Bromuconazole, burimate, butiobate, calcium polysulfide, captapol, captan, carbendazim, carboxycin, quinomethionate, chloroneb, chloropicrine, chlorothalonil, clozolinate, cupraneb, Cymoxanyl, cyproconazole, cyprofuram, dichlorophene, diclobutrazole, diclofloanide, diclomezin, dichloran, dietofencarb, difenokazole, dimethymolol, dimethomorph , Diconazole, dinocap, diphenylamine, dipyrithione, ditalimfoss, dithianon, dodine, drazoxolone, edifene force, epoxyconazole, etirimole, ethriazole, phenarimol, fenbuco Nazol, fenfuram, phenytropane, fenpiclonyl, fenpropidine, fenpropormoff, fentin a Tate, fentin hydroxide, ferbam, perimzone, fluazinam, fludioxonil, fluoromid, fluquinconazole, flusilazole, flusulfamid, flutoranyl, flutriafol, polpet, pocetyl- Aluminum, phthalide, fuberidazole, furlaxyl, purmecyclox, guazin, hexachlorobenzene, hexaconazole, hymexazole, imazaryl, imibenconazole, iminottadine, iprobenfos (IBP), Iprodione, isoprothiolane, kasugamycin, copper preparations such as copper hydroxide, copper naphthenate, copper oxychloride, copper sulfate, copper oxide, auxin-copper and Bordeaux mixtures, mancopers, mancozebs, Manev, Mepanipyrim, Mepronyl, Metallaccil, Metconazole, Metasulfocarb, Metfuroxam, Methiram, Metsulfobox, Michaelrobutanyl, Nickel Dimethyldithiocarbamate, Nitrotal-iso Profile, Noir Mall, Opuras, Oxadisyl, Oxamocarb, oxycarboxine, pepurazoate, fenconazole, penicuron, phosphodiphene, phthalide, fimaricin, piperaline, polycarbamate, polyoxine, probenazole, prochloraz, procmidone , Propamocarb, propiconazole, propineb, pyrazophos, pyrifenox, pyrimethanyl, pyroquilon, quintogen (PCNB), sulfur and sulfur preparations, tebuconazole, teclophthalam, technazen , Tetraconazole, thibendazole, thithiophene, thiophanate-methyl, thiram, tollclofos-methyl, tolylufluoride, triadimefon, triadimenol, triazoside, triclamid, trici Clazol, tridemorph, triflumizol, tripolin, triticazole, validamycin A, vinclozoline, geneb, zelam.

        Fungicides:

Bronopol, dichlorophene, nitrapyrin, nickel dimethyldithiocarbamate, kasugamycin, octylinone, furancarboxylic acid, oxytetracycline, probenazole, streptomycin, teclophthalam, copper sulfate and other copper agents.

        Pesticides / Acaricides / Nematicides:

Abamectin, AC 303,630, Acetate, Acrinatrin, Alanicab, Aldicarb, Alphamethrin, Amitraz, Avermectin, AZ 60541, Azadirachtin, Ajinfoss A, Ajinfoss M, Azocyclo Tin, Bacillus thuringiensis, bendiocarb, benfuracarb, benzaltope, betacyfluthrin, bifenthrin, BPMC, brofenprox, bromophos A, bufencarb, buprofezin, butokacsin, butyl Pyidaben, kadusafos, cabaril, cabofuran, cabofennotion, cabosulphan, katop, CGA 157 419, CGA 184 699, cloetocarb, chlorethoxyphosphate, chlorfenbinfos, chlorfluazuron, chlorme Force, Chlorpyriphos, Chlorpyriphos M, Cis-Resmethrin, Closightin, Clofentezin, Cyanophosph, Cycloprotrin, Cyfluthrin, Cyhalothrin, Cyhexatin, Cypermethrin, Cylo Margin, Deltamethrin, Demetone-M, Demetone-S, Demetone-S-methyl, Di Pentiuron, diazinon, diclopention, dichlorboth, diclifoss, dicrotophos, diethione, diflubenzuron, dimethatoate, dimethylbinfoss, dioxation, disulfotone, ediffenfoss, emma Mectin, Espenvalate, Ethiophenecarb, Ethion, Etofenprox, Etoprophos, Etrifoam, Phenamifoss, Penazaquine, Penbutatin, Phenytrothion, Phenobucarb, Phenothiocarb , Phenoxycarb, phenpropartin, fenpyrad, fenpyroximate, pention, fenvalrate, fipronil, fluazinam, flucycloxanthone, flucitalinate, flufenoxuron, flufenprox , Fluvalinate, phonophos, formitol, phosphthiazate, fufenfenx, furathiocarb, HCH, heptenophos, hexaflumuron, hexiax, imidacloprid, isprobenfos, isazofoss , Isopenfoss, isoprocarb, isoxation, iver Tin, lambda-cyhalothrin, lufenuron, malathion, mecarbam, mebinfos, mesulfenfos, metaldehyde, metacryphos, metamidophos, methidathione, methiocarb, methamyl, methol Carb, Milvemectin, Monoclotophos, Moxidecin, Naled, NC 184, NI 25, Nitenpyram, Ometoate, Oxamyl, Oxidemetone M, Oxidepropos, Parathion A, Parathion M, Permethrin, Pento Eight, Forate, Posalone, Posmet, Phosphomidone, Bombide, Pyrimicarb, Pyrimiphos M, Pyrimiphos A, Propenophos, Promecarb, Propaphos, Propoxur, Prothiophos , Protoate, pymetrozine, pyraclophos, pyridapention, pyresmethrin, pyrethrum, pyridaben, pyrimidipene, pyriproxyfen, quinalforce, RH 5992, salityon, cebufoss, silafluorophene , Sulfothep, Sulprophos, Tebufenozide, Tebufenpyrad, Tebupyrimphos, Tepple Benjuron, Tefluthrin, Temephos, Terbham, Terbuphos, Tetrachlorbinfos, Thiaphenox, Thiodicarb, Thiophanox, Thiomethone, Thionazin, Turingiencin, Tralomethrin, Triara Ten, triazofoss, triazuron, trichlorphone, triflumuron, trimetacarb, tamidothion, XMC, xylylcarb, YI 5301/5302, zetamethrin.

       Herbicides:

Anilides such as, for example, diflufenican and propanyl; Arylcarboxylic acids such as, for example, dichloropicolinic acid, dicamba and picloram; Aryloxyalkanoic acids such as, for example, 2,4-D, 2,4-DB, 2,4-DP, fluoxypyr, MCPA, MCPP and triclopyr; Aryloxy-phenoxy-alkanoic acid esters such as, for example, diclopov-methyl, phenoxaprop-ethyl, fluazifop-butyl, halooxypop-methyl, and quinacofop-ethyl; Azinones such as, for example, chloridazone and norflurazon; Carbamate, such as chlorprofam, desmedapem, penmedipam, and profam; Chloroacetanilides such as, for example, alachlor, acetochlor, butachlor, metazachlor, metolachlor, pretilachlor, and propachlor; Dinitroanilines such as, for example, oryzaline, pendimethalin and trituralin; Diphenyl ethers such as, for example, asifluorophene, biphenox, fluoroglycopene, pomesafen, halosafen, lactofen and oxyfluorfen; Ureas such as, for example, chlorotoluron, diuron, fluoromethuron, isoproturon, linuron and metabenzthiazuron; Hydroxylamines such as, for example, alkoxydim, cletodim, cycloxydim, cetoxydim and trakoxydim; Imidazolinones such as for example imazetapyr, imazamethabenz, imazapyr and imazaquin; Nitriles such as, for example, bromoxynil, diclobenyl and oxynyl; Oxyacetamides such as for example mefenacet; For example amidosulfuron, bensulfuron-methyl, chlorimuron-ethyl, chlorsulfuron, cynosulfuron, metsulfuron-methyl, nicosulfuron, primisulfuron, pyrazosulfuron-ethyl, thifensulfuron- Sulfonylureas such as methyl, triasulfuron and tribenuron-methyl; Thiol carbamates such as, for example, butyrate, cycloate, dialate, EPTC, esprocarb, molinate, prosulfocarb, thiobenecarb and trialate; Triazines such as, for example, atrazine, cyanazine, simazine, cymetrin, terbutryn and terbutylazine; Triazinones such as, for example, hexazinone, metamitrone, and metrizine; For example aminotriazole, benfuresate, bentazone, synmethylin, clomazone, clopyralide, dipfencuart, dithiopyr, etofumesate, fluorochloridone, glufosinate, glyphosate Others such as isoxaben, pyridate, quinclolac, quinmerak, sulfosate and tridiphane.

The active compounds according to the invention may also be present in their commercially available formulations and in the use forms prepared from these formulations in admixture with synergists. Synergists are compounds that do not have to be active on their own but increase the action of the active compound.

The active compound concentration in the use form can vary within a significant range. The active compound concentration of the use forms can be 0.0000001 to 95% by weight, preferably 0.0001 to 1% by weight.

The compound is used in a conventional manner suitable for the use form.

When used against pests of sanitary pests and stored products, the active compounds not only have excellent residual activity on wood and clay, but also have good stability against alkalis on limed substrates.

The active compounds according to the invention are also useful in the field of veterinary medicine, as well as in pests of plants, hygiene and stored products, for example true mites, princess mites, scab mites, trombiculids. ) Mites, flies (spit or vampire), parasitic fly larvae, teeth, hairy teeth, algae teeth and fleas. These parasites include:

Anoplurida, for example Haematopinus spp., Linognathus spp., Pediculus spp., Phetirus spp. And Solenopo Solenopotes spp.

Molophagida and Amoklycerina and Ischnocerina, for example, Trimenopon spp., Menopon spp., Trinoton species spp.), Bovicola spp., Weneckiella spp., Lepikentron spp., Damalina spp., Trichodextes spp. ) And Felicola spp.

Pseudomonas and Amok nematocerina and Brachyycerina, for example Aedes spp., Anopheles spp., Culex spp., Simulium species ( Simulium spp.), Eusimulium spp., Phlebotomus spp., Lutzomyia spp., Culicoides spp., Chrysops species spp.), Hibomitra spp., Atylotus spp., Tabanus spp., Haematopota spp., Philippimia spp. , Braula spp., Musca spp., Hydrotaea spp., Stomoxys spp., Haematobia spp., Morelia Morellia spp., Pannia spp., Glossina spp., Calliphora spp., Lucilia spp., Chrysomyia spp. ), Allpatia species (Wo hlfahrtia spp.), Sarcophaga spp., Oestrus spp., Hypoderma spp., Gasosterophilus spp., Hippobosca species (Hyppobosca) spp.), Lipoptena spp. and Melophagus spp.

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

From the order Heteroopterida, for example Cimex spp., Triatoma spp., Rhodnius spp. And Panstrongylus spp.

Neck of the Battarida, for example Blata orientalis, Periplaneta americana, Blatela germanica, and Supella spp.

Acarida subclass and the tree of Meta- and Mesostigmata, for example, Argas spp., Ornithodorus spp., Otabius spp. ), Ixodes spp., Amblyomma spp., Bophillus spp., Dermacentor spp., Haemaphysalis spp., Hyalomma spp., Ripicephalus spp., Dermanyssus spp., Rileytia spp., Pneumonyssus spp., Sturk Sternostoma spp. And Varroa spp.

Actinedida (Prostigmata) and Acaridida (Astigmata), such as, for example, Acarapis spp., Cheiletiella spp. 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., And Laminosioptes spp.

The active compounds according to the present invention show excellent activity against Boophilus microplus and Lucilia cuprina.

The active compounds according to the invention can also be used for agricultural livestock such as cattle, sheep, goats, horses, pigs, donkeys, camels, buffaloes, rabbits, chickens, turkeys, ducks, geese and bees, and other domesticated animals, eg For example, it is suitable for controlling arthropods that invade dogs, cats, cage birds and fish tanks, and also so-called laboratory animals such as hamsters, guinea pigs, rats and mice. Rescuing these arthropods reduces death and yield reduction (for example in the production of meat, milk, wool, hides, eggs, honey, etc.), making use of the active compounds according to the invention more economical and convenient. Animal breeding becomes possible.

The active compounds which can be used according to the invention can be used in the veterinary field, for example, by enteral administration in the form of tablets, capsules, drinks, potions, granules, pastes, antacids, by methods of mixing drugs into feeds and suppositories, Parenteral administration, for example by injection (intramuscular, subcutaneous, intravenous and intraperitoneal, etc.), by the form of insertion, by intranasal administration, for example dipping or soaking, spraying, swelling and drip, Use in known manner by transdermal administration in the form of washes and mists and in the form of shaped articles containing the active compounds, for example in the form of necklaces, ear tags, tail marks, leg bands, bridles or indicators. do.

When administered to livestock, poultry, domestic animals and the like, the active compound of formula (I) is directly administered as a preparation containing 1 to 80% by weight of the active compound (e.g. powders, emulsions, flowables). Or it may be diluted to 100 to 10,000 times, or may be used in the form of a chemical bath.

The compounds of formula (I) according to the invention have also been found to exhibit effective pesticidal activity against insects which destroy industrial substances.

The following pests may be mentioned as preferred examples, but are not limited to these:

Beetles, for example, Hylotrupes bajulus, Chlorophorus pilosis, Anobium punctatum, Xestobium rufovillosum, Plinis pecticornis, Dendrobium pertinex, Ernobius mollis, Priobium carpini, Lyctus brunneus, Rick Lyctus africanus, Lyctus planicollis, Lyctus linearis, Lyctus pubescens, Trogoxylon aequale, Mintes Minthes rugicollis, Xyleborus spp., Tryptodendron spp., Apate monachus, Bostrychus capucins, Heterobostricus brunuus robostrychus brunnes), Synoxylon species, Dinoderus minutus.

Dermapterans, for example, Sirex jubencus, Urocerus gigas, Urocerus gigas taignus, Urocerus augurs augur).

Termites such as Kalotermes flavicollis, Cryptotermes brevis, Heterotermes indicola, Reticulitermes flavipes , Reticulitermes santonensis, Reticulitermes lucifugus, Mastotermes darwiniensis, Zotermopsis nevadensis, Coff Coptotermes formosanus.

Bristletails, for example Lepisma saccharina.

In this regard, industrial materials should be understood in the sense of non-living materials, for example synthetics, glues, glue, paper and board, leather, wood and processed wood products, and paints.

Materials that must be very particularly protected against infestation of pests are wood and processed wood products.

Wood and processed wood products which can be protected by the composition according to the invention are for example construction wood, wooden beams, railway sleepers, bridge components, breakwaters, wooden vehicles, boxes, pallets, containers, It should be understood to include telephone poles, wooden signs, windows and doors made of wood, plywood, chip boards, connectors, or woodwork generally used in house construction or furniture.

The active compounds can be used on their own in the form of concentrates or in the form of common customary formulations, for example in the form of powders, granules, solutions, suspensions, emulsions or pastes.

The abovementioned preparations are prepared by methods known per se, for example, the active compound may be prepared by at least one solvent or diluent, emulsifier, dispersant and / or binder or fixative, waterproofing agent, desiccant and UV stabilizer, and If desired, it may be prepared by mixing with colorants and pigments and other processing aids.

Insecticidal compositions or concentrates used to protect wood or wood materials contain active compounds according to the invention in concentrations of from 0.0001 to 95% by weight, in particular from 0.001 to 60% by weight.

The amount of composition or concentrate used depends on the type and frequency of the insects and the medium. The optimum application amount can be determined by a series of tests in each case of use. In general, however, it is sufficient to use 0.0001 to 20% by weight, preferably 0.001 to 10% by weight, based on the material to be protected.

The solvents and / or diluents used are organic chemical solvents or solvent mixtures and / or low volatility oily or oily organic chemical solvents or solvent mixtures and / or polar organic chemical solvents or solvent mixtures and / or water, and emulsifiers and / or if appropriate Or humectant.

Organic chemical solvents which are preferably used are oily or oily solvents having an evaporation number of at least 35 and a flashpoint of at least 30 ° C, preferably at least 45 ° C. Materials used as low volatility and water-insoluble oily and oily solvents are suitable mineral oils or their aromatic fractions, or mineral oil-containing solvent mixtures, preferably White spirit, petroleum and / or alkylbenzenes,

Advantageously used materials are mineral oils having a boiling range of 170 to 220 ° C., white oils having a boiling range of 170 to 220 ° C., spindle oils having a boiling range of 250 to 350 ° C., petroleum having a boiling range of 160 to 280 ° C. Or aromatic compounds, terpentine essences, and the like.

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

Low volatility organic oily or oily solvents having an evaporation index of at least 35 and a flash point of at least 30 ° C., preferably at least 45 ° C., wherein the solvent mixture also has a flash point of at least 35 and a flash point of at least 30 ° C., preferably at least 45 ° C. If the pesticide / fungicide mixture can be dissolved or emulsified in this solvent mixture, it may be partially replaced by an intermediate or high volatility organic chemical solvent.

In a preferred embodiment, a portion of the organic chemical solvent or solvent mixture is replaced with an aliphatic polar organic chemical solvent or solvent mixture. Preferably used materials are aliphatic organic chemical solvents having hydroxyl and / or ester and / or ether groups, for example glycol ethers, esters and the like.

The organic chemical binders used within the scope of the invention are known per se and can be diluted with water and / or dissolved, dispersed or emulsified in the organic solvents used, and in particular dry oils, in particular acrylics. Rate resins, vinyl resins such as polyvinyl acetate, polyester resins, polycondensation or polyaddition resins, polyurethane resins, alkyd resins or modified alkyd resins, phenolic resins, hydrocarbon resins such as indene / coumar A binder consisting of or comprising a coumarone resin, a silicone resin, a dry vegetable oil and / or a dry oil and / or a physical dry binder based on natural and / or synthetic resins.

Synthetic resins used as binders can be used in the form of emulsions, dispersions or solutions. Up to 10% by weight bitumen or bituminous material may also be used as the binder. In addition, colorants, pigments, waterproofing agents, odor masking materials and inhibitors or corrosion inhibitors known per se can be used.

The composition or concentrate according to the invention preferably contains at least one alkyd resin or modified alkyd resin and / or dry vegetable oil as organic chemical binder. Preferably used materials according to the invention are alkyd resins having an oil content of at least 45% by weight, preferably 50 to 68% by weight.

All or part of the above mentioned binders may be replaced with fixatives (mixtures) or plasticizers (mixtures). These additives are used to prevent volatilization and crystallization or precipitation of the active compounds. They preferably replace 0.01 to 30% of the binder (based on 100% of the binder used).

Plasticizers are phthalic acid esters such as dibutyl phthalate, dioctyl phthalate or benzylbutyl phthalate, phosphoric acid esters such as tributyl phosphate, adipic acid esters such as di- (2-ethylhexyl) adi Chemical groups of pates, stearates such as butyl stearate or amyl stearate, oleates such as butyl oleate, glycerol ethers or relatively high molecular weight glycol ethers, glycerol esters and p-toluenesulfonic acid esters Is selected from.

The fixative is chemically based on polyvinyl alkyl ethers such as polyvinyl methyl ether, or ketones such as benzophenone and ethylenebenzophenone.

Particularly suitable as solvents or diluents is also water which, if appropriate, is present in a mixture with one or more of the aforementioned organic chemical solvents or diluents, emulsifiers and dispersants.

Wood is particularly effectively protected by large scale industrial injection methods, for example vacuum, double vacuum or pressurized treatment.

If appropriate, the ready-to-use composition may further contain other pesticides and, if appropriate, also one or more fungicides.

Further suitable components which can be mixed are preferably the insecticides and fungicides mentioned in WO 94/29 268. The compounds mentioned in this document are clearly part of the present application.

Very particularly preferred components that can be mixed are insecticides, for example chlorpyriphos, bombardment, silafluorine, alphamethrin, cyflutrin, cipermethrin, deltamethrin, permethrin, imidacloprid, NI-25, flu Phenoxalone, hexaflumuron and triflumuron, and fungicides, for example epoxyconazole, hexaconazole, azaconazole, propiconazole, tebuconazole, cyproconazole, metconazole, forehead Zaryl, diclofluanide, tolyluanide, 3-iodo-2-propynylbutylcarbamate, N-octyl-isothiazolin-3-one and 4,5-dichloro-N-octylisothiazoline -3-one.

Examples of preparation and use of the active compounds according to the invention are illustrated by the following examples.

Manufacturing Example

Example (I-1-a-1)

β-isomer

Under reflux, 29.6 g (0.0764 mol) of the compound prepared by the method of Example (II-1) in 160 ml of anhydrous toluene was added to 22.7 g (0.2 mol) of potassium t-butoxide in 60 ml of anhydrous tetrahydrofuran (THF). Was added dropwise and the mixture was stirred at reflux for 1.5 h. After workup, 230 ml of water was added, the aqueous phase was separated and the toluene phase was extracted with 110 ml of water, the aqueous phases were combined and washed with toluene and then concentrated to pH 1 with concentrated HCl at 10-20 ° C. Acidified. The product was suction filtered, washed to dryness and washed by stirring in methyl t-butyl ether (MTB) ether / n-hexane.

Yield: 13.7 g (56% of theory), Melting point:> 220 ° C.

The compounds of the following examples (I-1-a) were prepared analogously or according to the general preparation methods:

Table 57

Table 57 Continued

Example (I-1-b-1)

β-isomer

2.5 ml (18 mmol) of triethylamine in 70 ml of anhydrous methylene chloride and 3.84 g (0.012 mol) of the compound prepared by the method of Example (I-1-a-1) were dried at 0-10 DEG C. 5 Treated with 2.2 ml (0.18 mol) of isovaleryl chloride in ml and the mixture was stirred at RT until the reaction was complete (check by TLC). As a workup, the mixture was washed twice with 50 ml of 0.5N aqueous sodium hydroxide solution, dried over magnesium sulfate and evaporated. The crude product was recrystallized from MTB ether / n-hexane.

Yield: 1.6 g (33% of theory), Melting point: 218 ° C.

The compounds of the following examples (I-b-1) were prepared analogously or according to the general preparation methods:

TABLE 58

Table 58 Continued

Example (I-1-c-1)

β-isomer

1.2 ml (0.012 mol) of ethyl chloroformate in 5 ml of anhydrous methylene chloride at 0-10 DEG C. 1.7 ml (0.012 mol) of triethylamine in 70 ml of anhydrous CH ₂ Cl ₂ and Example (I-1-a- To 3.84 g (0.012 mol) of the compound prepared by the method of 1) was added dropwise, and the mixture was stirred at room temperature until completion of the reaction (confirmed by TLC). As a workup, the mixture was washed twice with 50 ml of 0.5N aqueous sodium hydroxide solution, dried over magnesium sulfate and evaporated.

Yield: 3.6 g (76% of theory), Melting point:> 220 ° C.

The compounds of the following examples (I-1-c) were prepared similarly or according to the general preparation methods:

Table 59

Example (II-1)

At 30 to 40 ° C., 16.7 g (0.0544 mol) of the compound prepared by the method of Example (XXIX-1) in 160 ml of anhydrous methylene chloride was added dropwise to 26.6 g (0.257 mol) of concentrated sulfuric acid, and the mixture was stirred at this temperature. Stir for hours. Thereafter, 37 mL of anhydrous methanol was added so that the internal temperature was about 40 ° C, and stirring was continued for an additional 6 hours at 40 to 70 ° C.

After workup, the mixture was poured into 0.28 kg of ice, extracted with methylene chloride, washed with aqueous sodium bicarbonate solution, dried and evaporated. The residue was recrystallized from methyl t-butyl ether / n-hexane.

Yield: 16.5 g (89% of theory), Melting point: 168 ° C.

Example (II-2)

β-isomer

15.9 g (0.08 mol) of 3-chloro-2,6-dimethylphenylacetic acid and 17.7 ml (0.24 mol) of thionyl chloride were stirred for 30 minutes at room temperature and then at 80 ° C. until gas evolution ceased. Excess thionylchloride was removed at 50 ° C. under reduced pressure. 50 ml of anhydrous toluene were added and the solution was once again evaporated. The residue was dissolved in 100 mL of dry THF (solution 1).

At 0 to 10 ° C., solution 1 is added dropwise to 24.6 ml (0.176 mol) of triethylamine and 16.8 g of methyl cis-4-methylcyclohexylamine-1-carboxylate in 160 ml of anhydrous THF, and the solution is then kept at room temperature. Stirred for 1 hour. The mixture was suction filtered, washed with anhydrous THF and then evaporated. The residue was dissolved in methylene chloride, washed with 0.5N HCl, dried and evaporated. The crude product was recrystallized from methyl t-butyl ether / n-hexane.

Yield: 26.9 g (74% of theory), Melting point: 163 占 폚.

The following compounds of formula (II) were prepared similarly to Examples (II-1) and (II-2) and according to the general preparation methods:

TABLE 60

Compound of formula (II)

Table 60 Continued

Example (XXIX-1)

Solution 1 was prepared as described in Example (II-2) starting from 12.6 g of 3-chloro-2,6-dimethylphenylacetic acid.

At 0-10 ° C., solution 1 was added dropwise to 9.2 ml (0.066 mol) of triethylamine and 15.1 g of 4-amino-4-cyano-tetrahydropyran (70% strength) in 120 ml of dry THF, and then the mixture was The mixture was further stirred for 1 hour at room temperature. The mixture was then evaporated to dissolve the residue in methylene chloride, washed with 0.5N HCl, dried and evaporated. The crude product was recrystallized from MTB ether / n-hexane.

Yield: 16.7 g (90% of theory), Melting point: 176 ° C.

The following compounds of formula (XXIX) were prepared similarly to examples (XXIX-1) and according to the general preparation methods:

TABLE 61

Example (I-2-a-1)

8.42 g (75 mmol) of potassium t-butoxide were first introduced into 50 mL of anhydrous tetrahydrofuran (THF) and prepared by the method of Example (III-1) in 50 mL of anhydrous THF at 0-10 ° C. 17.62 g (50 mmol) of 1-ethyloxycarbonyl-cyclohexyl 3-chloro-2,6-dimethylphenylacetate was added dropwise and the solution was stirred overnight at room temperature.

After workup, the reaction mixture was poured into 600 mL of water, acidified with 10% strength hydrochloric acid, the product was filtered off with suction, dissolved in methylene chloride, concentrated and the crystals were triturated with petroleum ether.

Yield: 9.7 g (63% of theory), Melting point: 193 ° C.

The following compound (I-2-a) was prepared similarly to Example (I-2-a-1) and according to the general preparation method:

Table 62

Compound of formula (I-2-a)

Example (I-2-b-1)

3.06 g (10 mmol) of the compound prepared by the method of Example (I-2-a-1) were first introduced into 40 mL of anhydrous THF, and 1.1 g (11 mmol) of triethylamine was added, followed by pivalo. A solution of 1.2 g (10 mmol) of monochloride was added dropwise while cooling with ice and stirred overnight at room temperature. After workup, the solution was concentrated and stirred with water, then suction filtered, dried and the residue was dissolved in ether, washed with 1N NaOH, dried over MgSO ₄ and evaporated. For purification, the crude product was mixed with a small amount of petroleum ether.

Yield: 3.1 g (79% of theory), Melting point: 126 ° C.

Compounds of the following general formula (I-2-b) were prepared analogously or according to general methods of preparation:

TABLE 63

Compound Of Formula (I-2-b)

Example (I-2-c-1)

0.68 g (5 mmol) of isobutyl chloroformate was mixed with 0.55 g (5.5 mmol) of triethylamine in 20 mL of dichloromethane at room temperature and 1.50 g of the compound prepared by the method of Example (I-2-a-4) 5 mmol) dropwise. Stirring was continued for 2 hours. The mixture was then washed with 10% strength aqueous citric acid and 1N aqueous sodium hydroxide solution and concentrated to dryness over dichloromethane. The residue obtained as an oil was stirred with petroleum ether and the solid formed was suction filtered.

Yield: 0.76 g, Melting point: 118 to 119 ° C.

Compounds of the following general formula (I-2-c) were prepared analogously or according to general methods of preparation:

TABLE 63a

1) ¹ H NMR, δ = 1.10, 1.10-2.30, 2.11, 2.22, 3.25 / 3.60, 3.35 / 3.39, 6.87

1) ¹ H NMR, δ = 1.0, 1.5-2.3, 2.10, 2.23, 3.25 / 3.60, 3.35 / 3.38, 6.90

Example (III-1)

After 10.85 g (50 mmol) of 3-chloro-2,6-dimethyl-phenylacetyl chloride and 8.6 g (50 mmol) of ethyl 1-hydroxycyclohexanecarboxylate were boiled in 100 ml of toluene for 1 hour, the solution was Evaporated.

Yield: 17.5 g (quantitative) of 1-ethoxycarbonyl-cyclohexyl 3-chloro-2,6-dimethylphenylacetate as a colorless oil.

^{GC / MS m / e - =} M + 352 (6%), 155 (100%), 109 (48%), 81 (76%), 29 (76%).

Table 64

Compound of formula (III)

The compound of formula (III) was obtained as a viscous oil and in most cases was converted to a compound of formula (I-2-a) without further purification and characterization.

Example (I-3-a-1)

16.2 g (35 mmol) of the compound obtained by the method of Example (IV-1) were first introduced into 70 ml of toluene and 35 ml of trifluoroacetic acid and heated at reflux for 5 hours. Trifluoroacetic acid was evaporated under reduced pressure and the residue was treated twice with toluene and then evaporated under reduced pressure. The residue was dissolved in 400 mL of water and 120 mL of methyl t-butyl ether (MTB) ether, made alkaline with NaOH and then extracted twice with MTB ether to acidify the aqueous phase with hydrochloric acid. The aqueous phase was extracted three times with MTB ether and then the organic phase was concentrated to dryness.

Yield: 8.5 g (78% of theory); Melting point 226-231 ° C.

Example (I-3-b-1)

1.5 g (4.7 mmol) of the compound prepared by the method of Example (I-3-a-1) in 20 mL of anhydrous methylene chloride were treated with 0.98 mL (1.5 eq) of triethylamine. 0.86 g (1.5 eq) of ethoxyacetyl chloride dissolved in 3 ml of anhydrous methylene chloride was added dropwise with ice cooling. The solution was stirred at room temperature for 1-2 hours, washed twice with 10% strength citric acid, and the combined aqueous acidic acids were extracted with methylene chloride. The combined organic phases were washed twice with 1N NaOH and the aqueous alkaline phase was then extracted with methylene chloride. The combined organic phases were dried and concentrated.

Yield: 1.70 g (86% of theory); oil.

¹ H-NMR (400 MHz, CDCl ₃ ): 1.08 (t, 3H); 1.1-2.1 (m, 10 H); 2.1-2.2 (4 s, 12 H); 3.1 (q, 2H); 3.9 (m, 2 H); 6.83 (s, 1 H).

Example (I-3-b-2)

Similarly to Example (I-3-b-1), pivaloylchloride was used to give the following compound as an oil

Yield: 2.00 g (100% of theory).

Example (I-3-c-1)

1.5 g (4.7 mmol) of the compound prepared by the method of Example (I-3-a-1) were added to 0.91 mL of isobutyl chloroformate under the reaction conditions described in Example (I-3-b-1). 1.5 eq) to give 1.85 g (94% of theory) of the compound.

Melting point: 83-89 ° C.

Example (IV-1)

1 drop of dimethylformamide (DMF) followed by 11.4 g (96 mmol) of thionyl chloride was added to the following compound in 70 ml of anhydrous toluene.

18 g (64 mmol) was added. The solution was stirred at room temperature for 5 minutes and then at 100 ° C. until gas evolution ceased. The mixture was concentrated under reduced pressure and treated twice with toluene, distilled in each case again, and then the mixture was stirred under high vacuum for 1 hour. The obtained acid chloride was dissolved in 40 ml of anhydrous tetrahydrofuran (THF) (solution A).

At 0 ° C., 57 ml (177 mmol) of a lithium diisopropylamide (LDA) solution were first introduced into 100 ml of dry THF. At this temperature, 22.1 g (107 mmol) of methyl 2,3,4,6-tetramethylphenylacetate dissolved in 40 ml of dry THF was added dropwise and stirring was continued for 30 minutes.

Subsequently, again at 0 ° C., solution A was added dropwise and the mixture was stirred for 1 hour without cooling.

The mixture was mixed with 350 ml MTB ether and a few drops of water, washed twice with 10% strength ammonium chloride aqueous solution, and the organic phase was concentrated to dryness. The crude product was stirred with petroleum ether. The product was suction filtered and dried.

Yield: 16.20 g (54% of theory); Melting point: 114-116 ° C.

Example (I-4-a-1)

2.4 g (10 mmol) of 2,3,5,6-tetramethylphenylchlorocarbonylketene were first introduced into 20 ml of toluene (p.a.). At room temperature, 1.35 g (10 mmol) of 2-pyridylethylketone were added and the solution was stirred at reflux for 8 hours. The product precipitated upon cooling. The precipitate was suction filtered and washed twice with cyclohexane.

Yield: 1.4 g (41% of theory); Melting point: 202-205 ° C.

The compounds of formula (I-4-a) described in the tables below were prepared similarly to examples (I-4-a-1) or according to the general preparation methods:

TABLE 65

       Example (I-4-b-1)

1.7 g (5 mmol) of the compound prepared by the method of Example (I-4-a-6) were first introduced into 20 ml of ethyl acetate (pa). At 20 ° C., 0.5 g (5 mmol) of triethylamine were added, and 0.39 g (5 mmol) of ClCOCH ₃ in 5 mL of ethyl acetate at 0 ° C. was added dropwise. The reaction was carried out under water exclusion. The mixture was stirred at 20 ° C for 20 h. The precipitate was separated and washed with ethyl acetate. The organic phase was washed twice with 25 ml of semi-concentrated NaCl solution, dried over sodium sulfate and then neutralized.

Yield: 1 g (53% of theory); Melting point: 170-172 ° C.

Compounds of the following general formula (I-4-b) were obtained analogously or according to general methods of preparation:

Table 65-a

Example (I-4-c-1)

1.7 g (5 mmol) of the compound prepared by the method of Example (I-4-a-6) were first introduced into 20 ml of ethyl acetate (pa). At 20 ° C., 0.5 g (5 mmol) of triethylamine were added, and 0.47 g (5 mmol) of ClCO ₂ CH ₃ in 5 mL of ethyl acetate was added dropwise at 0 ° C. The reaction was carried out under water exclusion. The mixture was stirred at 20 ° C for 20 h. After workup, the precipitate was separated and washed with ethyl acetate. The organic phase was washed twice with 25 ml of semi-concentrated NaCl solution, dried over sodium sulfate and then neutralized.

Yield: 1.6 g (81% of theory); Melting point: 136-139 ° C.

Example (VI-1)

At room temperature, 31 ml of thionyl chloride was added dropwise to 15 g (63.5 mmol) of the compound prepared by the method of Example (XXXIII-1) in 20 ml of toluene, and the solution was first stirred at room temperature for 1 hour, and then about 95 Stir overnight at ° C. After cooling, HCl and SO ₂ were blown through argon through the solution at about 45 ° C. and residual volatile compounds were removed under high vacuum.

Yield: 7.4 g (52% of theory); Boiling Point: 110-111 ° C./0.08 mbar.

Example (VI-2)

Similar to Example (VI-1) or according to the general preparation, the following compounds were obtained:

¹ H-NMR (400 MHz, CDCl ₃ ): δ = 2.13 (s, 3H, Ar-CH ₃ ), 2.22 (s, 3H, Ar-CH ₃ ), 2.28 (s, 6H, 2 x Ar-CH ₃ ), 6.49 (s, 1 H, Ar-H).

Example (XXXIII-1)

At room temperature, 40 g (0.155 mmol) of the compound prepared by the method of Example (XXXIV-1) were added to 28.2 g of potassium hydroxide in 75.6 ml of methanol and 37.8 g of water, and the mixture was heated at reflux for 10 hours.

After cooling, the mixture was concentrated under reduced pressure, and the residue was dissolved in about 100 mL of ice water and then acidified with semi-concentrated hydrochloric acid while cooling. The phases were separated and extracted with toluene. The solid was separated, suction filtered, stirred with a small amount of toluene, and then suction filtered once more.

Yield: 35.20 g (70.3% of theory); Melting point: 193-198 ° C.

Example (XXXIII-2)

Similar compounds as in Example (XXXIII-1) or according to the general preparation, the following compounds having a melting point of 181 ° C. (decomposition) were obtained:

Example (XXXIV-1)

At room temperature, 350 g (3.5 mol) of dimethyl carbonate were added to 7.9 g (0.264 mol) of 80% strength sodium hydride, followed by 42.0 g (0.203 mol) of methyl 2,3,5,6-tetramethylphenylacetate at 85 to 90 ° C. ) Was slowly added dropwise and the mixture was stirred overnight. After cooling, a small amount of methanol was added to the mixture, poured into about 1 L of ice water and acidified with semi-concentrated hydrochloric acid. The organic phase was separated and the aqueous phase was extracted with toluene, then the combined organic phases were concentrated to dryness. The residue was distilled off under high vacuum.

Yield: 41.9 g (82% of theory); Melting point: 125-129 ° C.

Similar to Example (XXXIV-1) and according to the general preparation methods, the following compounds having melting points of 132 to 134 ° C. were obtained:

Example (XXIII-1)

At room temperature, 171.9 g of the compound prepared by the method of Example (XXVI-1) was added dropwise to a mixture of 85.8 g (1.532 mol) of KOH in 224 ml of methanol and 110.2 ml of water, and the mixture was heated at reflux for 5 hours. . After cooling, the mixture was diluted with 300 mL of water and washed with methyl t-butyl ether. The aqueous phase was acidified with semiconcentrated hydrochloric acid, filtered off with suction, dried and the residue was recrystallized from toluene.

Yield: 111.4 g (about 69% of theory); Melting point: 128-130 ° C.

The following compounds of formula (XXIII) were obtained similarly to examples (XXIII-1) and according to the general preparation:

TABLE 66

Example (XXIV-1)

At room temperature, 992 ml of a 30% strength sodium methoxide solution in methanol was added dropwise to a solution of 353.7 g (1.3 mol) of the compound prepared by the method of Example (XXV-1) in 560 ml of methanol, and the mixture was stirred for 5 hours. Boiling under reflux. After cooling to room temperature, 148 ml of concentrated sulfuric acid was added dropwise, and the mixture was then heated under reflux for 1 hour, cooled to concentrate, mixed with water, extracted with methylene chloride, dried and concentrated. 179.1 g of the desired product (XXIV-1) (about 51% according to GC), acid XXIII-1 and 1,3-dichloro-2,6-dimethylbenzene were obtained. This mixture was used for the reaction of Example (XXIII-1).

Compounds of the following general formula (XXIV) were obtained similarly to examples (XXIV-1) and according to the general preparation methods:

TABLE 67

These compounds were used directly as crude products in the synthesis to prepare compounds of general formula (XXIII).

Example (XXV-1)

2205 g (22.8 moles) of 1,1-dichloroethylene (vinylidene chloride) were cooled in 255 g (1.776 moles) of anhydrous copper (II) chloride and 229.7 g (2.27 moles) of t-butyl nitrite in 990 ml of anhydrous acetonitrile. To the mixture was added dropwise and the mixture was kept at room temperature. Thereafter, a mixture of 232 g (1.49 mol) of 3-chloro-2,6-dimethylaniline in 1500 ml of anhydrous acetonitrile was added dropwise at a temperature of 30 DEG C or lower. At room temperature, the mixture was stirred until gas evolution ceased, then the mixture was carefully poured into 6 L of 20% strength hydrochloric acid and extracted with methylene chloride. The combined organic phases were washed once more with 20% strength hydrochloric acid, dried and concentrated. The residual oil was used in the reaction of Example (XXIV-1) without further workup.

Compounds of the following general formula (XXV) were obtained similarly to examples (XXV-1) and according to the general preparation methods:

TABLE 68

The compounds described in Table 68 were used as crude products in the saponification reaction to prepare compounds of general formula (XXIV) and therefore no longer specified.

       Example of use:

       Example 1

Phaedon Larva Test

Solvent: Dimethylformamide 7 parts by weight

Emulsifier: 1 part by weight of alkylaryl polyglycol ether

1 part by weight of the active compound is mixed with the specified amount of solvent and the specified amount of emulsifier and the concentrate is diluted with water to the desired concentration to prepare a suitable formulation of the active compound.

Cabbage leaves (Brasica oleracea) are treated by immersion in the active compound formulation of the desired concentration, and infected with mustard worm larvae (Phaedon cocleariae) while the leaves are moist.

After a certain period of time, the percent rescued was determined. 100% means that all mustard larvae have been killed; 0% means that no mustard larvae have been killed.

In this test, for example, Production Examples (I-1-a-2), (I-1-a-3), (I-1-b-1), (I-1-b-2) and The compound of (I-1-c-1) showed a rescue rate of 100% after 7 days at an exemplary active compound concentration of 1000 ppm.

Example 2

Tetranicus test (OP tolerance / spray treatment)

Solvent: 3 parts by weight of dimethylformamide

Emulsifier: 1 part by weight of alkylaryl polyglycol ether

1 part by weight of the active compound is mixed with the specified amount of solvent and the specified amount of emulsifier and the concentrate is diluted with water to the desired concentration to prepare a suitable formulation of the active compound.

Soybean plants (Phaseolus vulgaris) heavily infected with spotted mites at all stages (Tetranychus urticae) are sprayed with the active compound preparation at the desired concentration.

After a certain period of time, the percentage of relief is determined. 100% means that all spot mites have been killed; 0% means that the spotted mites were not killed at all.

In this test, for example, the compound of Preparation Example (I-1-a-2) showed 100% activity after 7 days at an exemplary active compound concentration of 1000 ppm.

       Example 3

Flutella test

Solvent: Dimethylformamide 7 parts by weight

Emulsifier: 1 part by weight of alkylaryl polyglycol ether

1 part by weight of the active compound is mixed with the specified amount of solvent and the specified amount of emulsifier and the concentrate is diluted with water to the desired concentration to prepare a suitable formulation of the active compound.

Cabbage leaves (Brassica oleracea) are treated by immersion in the active compound preparation at the desired concentration and infected with cabbage moth (flutella maculenpenis) caterpillars while the leaves are moist.

After a certain period of time, the percent rescued was determined. 100% means that all caterpillars have been killed; 0% means that none of the caterpillars have been killed.

In this test, for example, Production Examples (I-1-a-3), (I-1-b-1), (I-1-b-2), (I-1-b-6) and Compound of (I-1-c-1) showed a rescue rate of 100% after 7 days at an exemplary active compound concentration of 0.1%

Example 4

Spodovterra Exam

Solvent: Dimethylformamide 7 parts by weight

Emulsifier: 1 part by weight of alkylaryl polyglycol ether

1 part by weight of the active compound is mixed with the specified amount of solvent and the specified amount of emulsifier and the concentrate is diluted with water to the desired concentration to prepare a suitable formulation of the active compound.

Cabbage leaves (Brassica oleracea) are treated by immersion in the active compound formulation at the desired concentration and infected with owl moth (Spodoptera frugiperda) caterpillars while the leaves are moist.

After a certain period of time, the percentage of relief is determined. 100% means that all caterpillars have been killed; 0% means that none of the caterpillars have been killed.

In this test, for example, the compounds of Preparation Examples (I-1-a-2), (I-1-a-3) and (I-1-b-4) give exemplary active compound concentrations of 0.1% At 7 days after at least 80%.

Example 5

Nepotetics test

Solvent: Dimethylformamide 7 parts by weight

Emulsifier: 1 part by weight of alkylaryl polyglycol ether

1 part by weight of the active compound is mixed with the specified amount of solvent and the specified amount of emulsifier and the concentrate is diluted with water to the desired concentration to prepare a suitable formulation of the active compound.

Rice (Oryza sativa) is treated by dipping into active compound formulations of the desired concentration and infected with larvae (Nephotettix cincticeps) larvae while the rice is moist.

After a certain period of time, the percentage of relief is determined. 100% means that all the cicadas have been killed; 0% means that no single cicada larvae have been killed.

In this test, for example, Production Examples (I-1-a-1), (I-1-a-2), (I-1-a-3), (I-1-b-1), (I-1-b-2), (I-1-b-3), (I-1-b-4), (I-1-b-5), (I-1-b-6) and The compound of (I-1-c-2) showed a rescue rate of 100% after 6 days at an exemplary active compound concentration of 0.1%.

Example 6

Miss Juice Test

Solvent: Dimethylformamide 7 parts by weight

Emulsifier: 1 part by weight of alkylaryl polyglycol ether

1 part by weight of the active compound is mixed with the specified amount of solvent and the specified amount of emulsifier and the concentrate is diluted with water to the desired concentration to prepare a suitable formulation of the active compound.

Cabbage leaves (Brassica oleracea) heavily infected with peach aphid (Myzus persicae) are treated by immersion in the active compound preparation at the desired concentration.

After a certain period of time, the percentage of relief is determined. 100% means that all aphids have been killed; 0% means that the aphid has not been killed at all.

In this test, for example, Production Examples (I-1-a-1), (I-1-a-2), (I-1-a-3), (I-1-b-2), Compounds of (I-1-b-3) and (I-2-a-1) exhibited a rescue rate of at least 80% after 6 days at an exemplary active compound concentration of 0.1%.

Example 7

Tetranicus test (OP tolerance / immersion treatment)

Solvent: 3 parts by weight of dimethylformamide

Emulsifier: 1 part by weight of alkylaryl polyglycol ether

1 part by weight of the active compound is mixed with the specified amount of solvent and the specified amount of emulsifier and the concentrate is diluted with water to the desired concentration to prepare a suitable formulation of the active compound.

Soybean plants (Phaseolus vulgaris) heavily infected with spotted mites (Tetranicus urticae) at all stages are immersed in the active compound preparation at the desired concentration.

After a certain period of time, the percentage of relief is determined. 100% means that all spot mites have been killed; 0% means that the spotted mites were not killed at all.

In this test, for example, Production Examples (I-1-a-1), (I-1-a-2), (I-1-a-3), (I-1-b-2) and The compound of (I-2-b-1) showed a 100% rescue after 5 days at an exemplary active compound concentration of 0.1%.

Claims (15)

Compound of Formula (I): Where V represents hydrogen, halogen, C _1-6 -alkyl or C _1-6 -alkoxy, W is cyano, nitro, halogen, C _1-6 -alkyl, C _2-6 -alkenyl, C _2-6 -alkynyl, C _1-6 -alkoxy, C _1-4 -halogenoalkyl, C _{1 -4-halogeno-alkoxy,} or each, halogen -, C _1-6 - alkyl -, C _1-6 - alkyl cock when -, C _1-4 - halogenoalkyl -, C _1-4 - halogenoalkyl alkoxy-, Nitro- or cyano-substituted or unsubstituted phenyl, phenoxy, phenylthio, phenyl-C _1-4 -alkoxy or phenyl-C _1-4 -alkylthio; X is hydrogen, halogen, C _1-6 -alkyl, C _2-6 -alkenyl, C _2-6 -alkynyl, C _1-6 -alkoxy, C _1-4 -halogenoalkyl, C _1-4- halogeno, cyano, nitro, or each halogen -, C _1-6 - alkyl -, C _1-6 - alkoxy -, C _1-4 - halogenoalkyl -, C _1-4 - halogenoalkyl alkoxy-, Nitro- or cyano-substituted or unsubstituted phenyl, phenoxy, phenylthio, phenyl-C _1-4 -alkoxy or phenyl-C _1-4 -alkylthio; Y represents hydrogen, halogen, C _1-6 -alkyl, C _1-6 -alkoxy, C _1-4 -halogenoalkyl, C _1-4 -halogenoalkoxy, cyano or nitro, Z is halogen, C _1-6 -alkyl, C _1-6 -alkoxy, C _1-4 -halogenoalkyl, C _1-4 -halogenoalkoxy, hydroxyl, cyano, nitro, or halogen, respectively, C _1-4 - alkyl -, C _1-4 - alkoxy -, C _1-4 - halogenoalkyl -, C _1-4 - halogenoalkyl alkoxy-, nitro- or cyano-substituted, or a phenoxy, phenyl unsubstituted Thio, thiazolyloxy, pyridinyloxy, pyrimidyloxy, pyrazolyloxy, phenyl-C _1-4 -alkoxy or phenyl-C _1-4 -alkylthio; Y and Z together are each halogen-, C _{1-6 -alkyl-} , C _1-6 -alkoxy- or C _1-4 -halogenoalkyl-substituted or unsubstituted and one to three members are independently oxygen , C _3-5 -alkanediyl or C _3-5 -alkenediyl, which may be replaced by sulfur, nitrogen or carbonyl groups, or W and Z together are each halogen-, C _{1-6 -alkyl-} , C _1-6 -alkoxy- or C _1-4 -halogenoalkyl-substituted or unsubstituted and one to three members are independently oxygen , C _3-5 -alkanediyl or C _3-5 -alkenediyl which may be replaced by sulfur, nitrogen or carbonyl groups, Het is a group Represents one of From here, A is hydrogen, halogen-substituted or unsubstituted C _1-12 -alkyl, C _2-8 -alkenyl, C _1-10 -alkoxy-C _1-8 -alkyl, poly-C _{1-8 -alkoxy-} C _1-8 -alkyl or C _1-10 -alkylthio-C _1-6 -alkyl, or one or two directly non-methylene groups can be replaced by oxygen, sulfur or oxygen and sulfur and halogen-, C _{1-6 -alkyl-} , or C _1-6 -alkoxy-substituted or unsubstituted C _3-8 -cycloalkyl, or each halogen-, C _{1-6 -alkyl-} , C _1-6 -halo Genoalkyl-, C _1-6 -alkoxy-, C _1-6 -halogenoalkoxy-, cyano- or nitro-substituted or unsubstituted phenyl, naphthyl, phenyl-C _1-6 -alkyl, naphthyl- Hetaryl having 1 to 3 heteroatoms selected from the group consisting of C _1-6 -alkyl or 5 or 6 reducers and oxygen, sulfur and nitrogen, B represents hydrogen, C _1-12 -alkyl or C _1-8 -alkoxy-C _1-6 -alkyl, or A and B together with the carbon atoms to which they are attached, in each case one methylene group can be replaced by oxygen or sulfur and C _1-8 -alkyl, C _3-10 -cycloalkyl, C _1-8 -halo Or represent C _3-10 -cycloalkyl or C _5-10 -cycloalkenyl unsubstituted or substituted with genoalkyl, C _1-8 -alkoxy, C _1-8 -alkylthio, halogen or phenyl, A and B are further 5- to 8 together with the carbon atoms to which they are attached, by alkylenediyl groups which may contain one or two atoms selected from the group consisting of oxygen and sulfur, or together with the carbon atoms to which they are attached; C _5-6 -cycloalkyl substituted by an alkylenedioxy group or an alkylenedithioyl group forming a membered ring, or A and B, together with the carbon atoms to which they are attached, are each C _{1-6 -alkyl-} , C _{1-6 -alkoxy-} or halogen-substituted or unsubstituted C _3-6 -alkanediyl, C C _3-8 -cycloalkyl or C _5-8 -linked by _3-6 -alkenediyl or C _4-6 -alkanediendiyl, in which case one methylene group is replaced by oxygen or sulfur Cycloalkenyl, G is hydrogen (a) or Represents one of From here, E represents a mono- or divalent metal or ammonium ion, L represents oxygen or sulfur, M represents oxygen or sulfur, R ¹ is halogen-substituted or unsubstituted C _1-20 -alkyl, C _2-20 -alkenyl, C _1-8 -alkoxy-C _1-8 -alkyl, C _1-8 -alkylthio-C _{1 -8} -alkyl or poly-C _1-8 -alkoxy-C _1-8 -alkyl; Halogen -, C _1-6-alkyl-or C _1-6 - alkoxy-substituted and with one or two not directly adjacent methylene groups are replaced by oxygen, sulfur, or oxygen and sulfur, C _3-8 - Cycloalkyl; Halogen-, cyano-, nitro -, C _1-6 - alkyl -, C _1-6 - alkoxy -, C _1-6 - halogenoalkyl -, C _{1-6-halogeno-alkoxy} -, C _1-6 -Alkylthio- or C _1-6 -alkylsulfonyl-substituted or unsubstituted phenyl; Halogen-, nitro-, cyano-. C _1-6- - alkyl -, C _1-6 - alkoxy -, C _1-6 - halogenoalkyl -, C _{1-6-halogeno-alkoxy-substituted} or unsubstituted phenyl -C _1-6 - alkyl; Halogen- or C _1-6 -alkyl-substituted or unsubstituted 5- or 6-membered hetaryl having one or two heteroatoms selected from the group consisting of oxygen, sulfur and nitrogen; Halogen- or C _1-6 -alkyl-substituted or unsubstituted phenoxy-C _1-6 -alkyl; Or halogen-, amino- or C _1-6 -alkyl-substituted or unsubstituted 5- or 6-membered hetaryloxy-C _1- having one or two heteroatoms selected from the group consisting of oxygen, sulfur and nitrogen ₆ -alkyl, R ² is halogen-substituted or unsubstituted C _1-20 -alkyl, C _2-20 -alkenyl, C _1-8 -alkoxy-C _2-8 -alkyl or poly-C _1-8 -alkoxy-C _2-8 -alkyl; Halogen-, C _{1-6 -alkyl-} or C _1-6 -alkoxy-substituted or unsubstituted C _3-8 -cycloalkyl; Or respectively halogen-, cyano-, nitro -, C _1-6 - alkyl -, C _1-6 - alkoxy -, C _1-6 - halogenoalkyl - or C _{1-6-halogeno-alkoxy-substituted} or unsubstituted Substituted phenyl or benzyl, R ³ is halogen-substituted or unsubstituted C _1-8 -alkyl, or halogen-, C _{1-6 -alkyl-} , C _1-6 -alkoxy-, C _1-4 -halogenoalkyl- or C _{1, respectively -4} -halogenoalkoxy-, cyano- or nitro-substituted or unsubstituted phenyl or benzyl, R ⁴ and R ⁵ are each independently of each other halogen-substituted or unsubstituted C _1-8 -alkyl, C _1-8 -alkoxy, C _1-8 -alkylamino, di (C _1-8 -alkyl) amino , C _1-8 - alkylthio or C _3-8 - alkenyl, thio, or respectively halogen-, nitro-, cyano-, C _1-4 - alkoxy -, C _{1-4-halogeno-alkoxy} -, C _{1 4} - alkylthio -, C _1-4 - halogenoalkyl thio -, C _1-4 -alkyl-or C _1-4 - halogenoalkyl-substituted, or represents an unsubstituted phenyl, phenoxy or phenylthio, R ⁶ and R ⁷ independently of one another are hydrogen, each halogen-substituted or unsubstituted C _1-8 -alkyl, C _3-8 -cycloalkyl, C _1-8 -alkoxy, C _3-8 -alkenyl or C _1-8 -alkoxy-C _2-8 -alkyl, or halogen-, C _1-8 -alkyl-, C _1-8 -halogenoalkyl- or C _1-8 -alkoxy-substituted or unsubstituted phenyl or Benzyl, or together, one methylene group, may be replaced by oxygen or sulfur and represent C _1-6 -alkyl-substituted or unsubstituted C _3-6 -alkylene radicals, Of these compounds The compound of is excluded. (A) intramolecular condensation of the compound of formula (II) in the presence of a diluent and in the presence of a base to obtain a compound of formula (I-1-a), or (B) intramolecular condensation of the compound of formula (III) in the presence of a diluent and in the presence of a base to obtain a compound of formula (I-2-a), or (C) intramolecular ring closure of the compound of formula (IV) in the presence of an acid to give a compound of formula (I-3-a), or Compounds of the general formulas (I-1-a) and (I-2-a) obtained above, (F) in the presence of an acid-binder,    (α) react with an acid halide of formula (VIII), or    (β) react with carboxylic anhydride of general formula (IX), or (G) react with chloroformic acid ester or chloroformic acid thioester of general formula (X), or (Hα) react with a chloromonothioformic ester or chlorodithioformic ester of general formula (XI), After reacting with (Hβ) carbon disulfide, and subsequently with a compound of formula (XII), (I) react with sulfonyl chloride of formula (XIII), or (J) react with a phosphorus compound of general formula (XIV), or (K) reacts with a metal compound or amine of the general formula (XV) or (XVI), or (Lα) reacted with an isocyanate or isothiocyanate of formula (XVII), or (Lβ) A process for preparing a compound of formula (I) according to claim 1 characterized by reacting with carbamoyl chloride or thiocarbamoyl chloride of formula (XVIII): R ¹ -CO-O-CO-R ¹ (IX) R ² -M-CO-Cl (X) R ² -Hal (XII) R ³ -SO ₂ -Cl (XIII) Me (OR ¹⁰ ) _t (XV) R ⁶ -N = C = L (XVII) In the above formula, Het is a group Represents one of Where G is as mentioned in claim 1, A, B, V, W, X, Y, L, M, Z, R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ are each as mentioned in claim 1, R ⁸ represents C _1-6 -alkyl, T represents hydrogen, halogen, C _1-6 -alkyl or C _1-8 -alkoxy, Hal in formulas (VIII) and (XIV) represents halogen, Hal in formula (XII) represents chlorine, bromine or iodine, Me represents a monovalent or divalent metal, t represents a number of 1 or 2, R ¹⁰ , R ¹¹ and R ¹² each independently represent hydrogen or C _1-8 -alkyl. The method of claim 1, V represents hydrogen, fluorine, chlorine, bromine, C _1-4 -alkyl or C _1-4 -alkoxy, W is cyano, nitro, fluorine, chlorine, bromine, C _1-4 -alkyl, C _1-4 -alkoxy, C _1-2 -halogenoalkyl, C _1-2 -halogenoalkoxy, or fluorine, respectively, chlorine -, bromine -, C _1-4 - alkyl -, C _1-4 - alkoxy -, C _1-2 - halogenoalkyl -, C _1-2 - halogenoalkyl alkoxy-, nitro- or cyano-substituted or Unsubstituted phenyl, phenoxy, benzyl or benzyloxy, X is hydrogen, fluorine, chlorine, bromine, C _1-4 -alkyl, C _1-4 -alkoxy, C _1-2 -halogenoalkyl, C _1-2 -halogenoalkoxy, cyano, nitro, or fluorine, respectively -, chlorine -, bromine -, C _1-4 - alkyl -, C _1-4 - alkoxy -, C _1-2 - halogenoalkyl -, C _1-2 - halogenoalkyl alkoxy-, nitro- or cyano- Substituted or unsubstituted phenyl, phenoxy, benzyl or benzyloxy, Y represents hydrogen, fluorine, chlorine, bromine, C _1-4 -alkyl, C _1-4 -alkoxy, C _1-2 -halogenoalkyl, C _1-2 -halogenoalkoxy, cyano or nitro, Z is fluorine, chlorine, bromine, C _1-4 -alkyl, C _1-4 -alkoxy, C _1-2 -halogenoalkyl, C _1-2 -halogenoalkoxy, hydroxyl, cyano, nitro, or each fluorine -, chlorine -, bromine -, C _1-4 - alkyl -, C _1-4 - alkoxy -, C _1-2 - halogenoalkyl -, C _1-2 - halogenoalkyl alkoxy-, nitro-, or cyano -Represent substituted or unsubstituted phenoxy or benzyloxy, or Y and Z together are fluorine-, chlorine-, bromine-, C _{1-4 -alkyl-} , C _1-4 -alkoxy- or C _1-2 -halogenoalkyl-substituted or unsubstituted and one or two two won are not directly adjacent to one another independently represent oxygen, sulfur or nitrogen, which may be replaced by C _3-4 - alkanediyl or C _3-4 - know or indicate the canned one, W and Z together are fluorine-, chlorine-, bromine-, C _{1-4 -alkyl-} , C _1-4 -alkoxy- or C _1-2 -halogenoalkyl-substituted or unsubstituted and one or two Al represents the canned one, - the won are not directly adjacent each independently replaced by an oxygen, sulfur or nitrogen by C _3-4 - alkanediyl or C _3-4 Het is a group Represents one of From here, A is hydrogen, fluorine- or chlorine-substituted or unsubstituted C _{1-10 -alkyl-} , C _2-6 -alkenyl, C _1-8 -alkoxy-C _1-6 -alkyl, poly-C _{1- 6} -alkoxy-C _1-6 -alkyl or C _1-8 -alkylthio-C _1-6 -alkyl, or one or two non-contiguous methylene groups may be replaced by oxygen, sulfur, or oxygen and sulfur Fluorine-, chlorine-, C _{1-4 -alkyl-} or C _1-4 -alkoxy-substituted or unsubstituted C _3-7 -cycloalkyl, or fluorine-, chlorine-, bromine-, C _{1- 4} - alkyl -, C _1-4 - halogenoalkyl -, C _1-4 - alkoxy -, C _1-4 - halogenoalkyl alkoxy-, cyano- or nitro-substituted or unsubstituted phenyl, furanyl, pyridinyl Dill, imidazolyl, triazolyl, pyrazolyl, indolyl, thiazolyl, thienyl or phenyl-Ci_ ₄ -alkyl, B represents hydrogen, C _1-10 -alkyl or C _1-6 -alkoxy-C _1-4 -alkyl, or A and B together with the carbon atoms to which they are attached, each methylene group may be replaced by oxygen or sulfur and may be C _1-6 -alkyl, C _3-8 -cycloalkyl, C _1-3 -halogenoalkyl , C _1-6 - alkoxy, C _{1-6-substituted} at the alkylthio, fluorine, chlorine or phenyl or unsubstituted C _3-8 - or indicate a cycloalkenyl, - cycloalkyl or C _5-8 A and B together with the carbon atoms to which they are attached form an additional 5- to 7-membered ring by an alkylenediyl group which may contain one or two oxygen or sulfur atoms, or with the carbon atoms to which they are attached C _5-6 -cycloalkyl unsubstituted or substituted by alkylenedioxy or alkylenedithiol groups, or A and B together with the carbon atoms to which they are attached, C _3-5 each having two carbon atoms C _{1-4 -alkyl-} , C _1-4 -alkoxy-, fluorine-, chlorine- or bromine-substituted or unsubstituted C _3-6 -cycloalkyl or C _5-6 linked by alkanediyl, C _3-5 -alkenediyl or butadienediyl, each of which may be replaced by one methylene group by oxygen or sulfur Cycloalkenyl, G is hydrogen (a) or Represents one of From here, E represents a mono- or divalent metal or ammonium ion, L represents oxygen or sulfur, M represents oxygen or sulfur, R ¹ is fluorine- or chlorine-substituted or unsubstituted C _1-16 -alkyl, C _2-16 -alkenyl, C _1-6 -alkoxy-C _1-6 -alkyl, C _1-6 -alkylthio -C _1-6 -alkyl or poly-C _1-6 -alkoxy-C _1-6 -alkyl; Fluorine-, chlorine-, C _{1-5 -alkyl-} or C _1-5 -alkoxy-substituted or unsubstituted and one or two directly non-contiguous methylene groups may be replaced by oxygen, sulfur or oxygen and sulfur C _3-7 -cycloalkyl; Fluorine -, chlorine -, bromine -, cyano-, nitro -, C _1-4 - alkyl -, C _1-4 - alkoxy -, C _1-3 - halogenoalkyl -, C _1-3-halogeno alkoxy -, C _1-4 -alkylthio- or C _1-4 -alkylsulfonyl-substituted or unsubstituted phenyl; Fluorine-, chlorine-, bromine-, C _{1-4 -alkyl-} , C _1-4 -alkoxy-, C _1-3 -halogenoalkyl- or C _1-3 -halogenoalkoxy-substituted or unsubstituted phenyl -C _1-4 -alkyl; Fluorine-, chlorine-, bromine- or C _1-4 -alkyl-substituted or unsubstituted pyrazolyl, thiazolyl, pyridyl, pyrimidyl, furanyl or thienyl; Fluorine-, chlorine-, bromine- or C _1-4 -alkyl-substituted or unsubstituted phenoxy-C _1-5 -alkyl; Or fluorine, chlorine, bromine, amino- or C _1-4 -alkyl-substituted or unsubstituted pyridyloxy-C _1-5 -alkyl, pyrimidyloxy-C _1-5 -alkyl or thiazolyl Oxy-Ci_ ₅ -alkyl, R ² is fluorine- or chlorine-substituted or unsubstituted C _1-16 -alkyl, C _2-16 -alkenyl, C _1-6 -alkoxy-C _2-6 -alkyl or poly-C _1-6- Alkoxy-C _2-6 -alkyl; Fluorine-, chlorine-, C _{1-4 -alkyl-} or C _1-4 -alkoxy-substituted or unsubstituted C _3-7 -cycloalkyl; Or respectively fluorine-, chlorine -, bromine -, cyano-, nitro -, C _1-4 - alkyl -, C _1-3 - alkoxy -, C _1-3 - halogenoalkyl - or C _1-3 - haloalkyl Genoalkoxy-substituted or unsubstituted phenyl or benzyl, R ³ is fluorine- or chlorine-substituted or unsubstituted C _1-6 -alkyl, or fluorine-, chlorine-, bromine-, C _{1-4 -alkyl-} , C _1-4 -alkoxy-, C _{1- 2} -halogenoalkoxy-, C _1-2 -halogenoalkyl-, cyano- or nitro-substituted or unsubstituted phenyl or benzyl, R ⁴ and R ⁵ are each independently of each other fluorine- or chlorine-substituted or unsubstituted C _1-6 -alkyl, C _1-6 -alkoxy, C _1-6 -alkylamino, di (C _1-6- Alkyl) amino, C _1-6 -alkylthio or C _3-4 -alkenylthio, or fluorine-, chlorine-, bromine-, nitro-, cyano-, C _1-3 -alkoxy-, C _{1- 3-halogeno-alkoxy} -, C _1-3 - alkylthio -, C _1-3 - halogenoalkyl thio -, C _1-3-alkyl-or C _1-3 - halogenoalkyl-substituted or unsubstituted phenyl , Phenoxy or phenylthio, R ⁶ and R ⁷ are each independently hydrogen, fluorine- or chlorine-substituted or unsubstituted C _1-6 -alkyl, C _3-6 -cycloalkyl, C _1-6 -alkoxy, C _3-6- alkenyl, or C _1-6 - alkoxy -C _2-6 - alkyl, or respectively fluorine-, chlorine -, bromine -, C _1-5 - halogenoalkyl -, C _1-5 - alkyl-C or _1-5 C _3-6 -alkylene which represents -alkoxy-substituted or unsubstituted phenyl or benzyl, or together, one methylene group can be replaced by oxygen or sulfur and C _1-4 -alkyl-substituted or unsubstituted Indicates radicals, Of these compounds The compound of formula (I) is excluded. The method of claim 1, V represents hydrogen, fluorine, chlorine, bromine, methyl, ethyl, propyl, isopropyl, t-butyl, methoxy, ethoxy, propoxy or isopropoxy, W is cyano, nitro, fluorine, chlorine, bromine, methyl, ethyl, propyl, butyl, isopropyl, isobutyl, t-butyl, methoxy, ethoxy, propoxy, isopropoxy, trifluoromethyl, di Fluoromethoxy, trifluoromethoxy, phenyl or benzyloxy, X is hydrogen, fluorine, chlorine, bromine, methyl, ethyl, propyl, butyl, isobutyl, isopropyl, t-butyl, methoxy, ethoxy, propoxy, isopropoxy, trifluoromethyl, trifluoromethoxy , Difluoromethoxy, cyano, nitro, phenyl or benzyloxy, Y is hydrogen, fluorine, chlorine, bromine, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, t-butyl, methoxy, ethoxy, propoxy, isopropoxy, trifluoromethyl, trifluoromethoxy , Difluoromethoxy, cyano or nitro, Z is fluorine, chlorine, bromine, methyl, ethyl, propyl, butyl, isobutyl, isopropyl, t-butyl, methoxy, ethoxy, propoxy, isopropoxy, trifluoromethyl, trifluoromethoxy, di Fluoromethoxy, cyano or nitro, or Y and Z together, two directly non-adjacent circles can be replaced by oxygen and fluorine-, chlorine-, methyl-, ethyl-, propyl-, isopropyl-, methoxy-, ethoxy-, propoxy -Represents isopropoxy- or trifluoromethyl-substituted or unsubstituted C _3-4 -alkanediyl, or W and Z together, two directly non-adjacent circles can be replaced by oxygen and fluorine-, chlorine-, methyl-, ethyl-, propyl-, isopropyl-, methoxy-, ethoxy-, propoxy -Represents isopropoxy- or trifluoromethyl-substituted or unsubstituted C _3-4 -alkanediyl, Het is a group Represents one of From here, A is hydrogen, fluorine- or chlorine-substituted or unsubstituted C _1-8 -alkyl, C _2-4 -alkenyl, C _1-6 -alkoxy-C _1-4 -alkyl, poly-C _{1-4 -Alkoxy} -C _1-4 -alkyl or C _1-6 -alkylthio-C _1-4 -alkyl, or one or two directly non-methylene groups can be replaced by oxygen, sulfur, or oxygen and sulfur Fluorine-, chlorine-, methyl- or methoxy-substituted or unsubstituted C _3-6 -cycloalkyl, or fluorine-, chlorine-, bromine-, methyl-, ethyl-, n-propyl-, isopropyl, respectively -Methoxy-, ethoxy-, trifluoromethyl-, trifluoromethoxy-, cyano- or nitro-substituted or unsubstituted phenyl, pyridyl or benzyl, B represents hydrogen, C _1-8 -alkyl or C _1-4 -alkoxy-C _1-2 -alkyl, or A and B together with the carbon atoms to which they are attached, in each case one methylene group may be replaced by oxygen or sulfur and methyl, ethyl, n-propyl, isopropyl, butyl, isobutyl, sec-butyl, t -Butyl, cyclohexyl, trifluoromethyl, methoxy, ethoxy, n-propoxy, isopropoxy, butoxy, isobutoxy, sec-butoxy, t-butoxy, methylthio, ethylthio, fluorine, C _3-8 -cycloalkyl or C _5-8 -cycloalkenyl unsubstituted or substituted with chlorine or phenyl; A and B are alkylenedioxy groups which, together with the carbon atoms to which they are attached, form an additional 5- or 6-membered ring by alkylenediyl groups which may contain oxygen or sulfur atoms, or together with the carbon atoms to which they are attached; C _5-6 -cycloalkyl substituted by A and B together with the carbon atom to which they are attached are C _3-6 -cycloalkyl or C _5-wherein two carbon atoms are linked by C _3-4 -alkanediyl, C _3-4 -alkenediyl or butadienediyl ₆ -cycloalkenyl, G is hydrogen (a) or Represents one of From here, E represents a mono- or divalent metal or ammonium ion, L represents oxygen or sulfur, M represents oxygen or sulfur, R ¹ is fluorine- or chlorine-substituted or unsubstituted C _1-14 -alkyl, C _2-14 -alkenyl, C _1-4 -alkoxy-C _1-6 -alkyl, C _1-4 -alkylthio -C _1-6 -alkyl or poly-C _1-4 -alkoxy-C _1-4 -alkyl; One or two non-contiguous methylene groups can be replaced by oxygen, sulfur, or oxygen and sulfur and can be replaced by fluorine-, chlorine-, methyl-, ethyl-, n-propyl-, i-propyl-, n-butyl i-butyl-, t-butyl-, methoxy-, ethoxy-, n-propoxy- or isopropoxy-substituted or unsubstituted C _3-6 -cycloalkyl; Fluorine-, chlorine-, bromine-, cyano-, nitro-, methyl-, ethyl-, n-propyl-, i-propyl-, methoxy-, ethoxy-, trifluoromethyl-, trifluoromethoxy -Methylthio-, ethylthio-, methylsulfonyl- or ethylsulfonyl-substituted or unsubstituted phenyl; Fluorine-, chlorine-, bromine-, methyl-, ethyl-, n-propyl-, i-propyl-, methoxy-, ethoxy-, trifluoromethyl- or trifluoromethoxy-substituted or unsubstituted benzyl ; Fluorine-, chlorine-, bromine-, methyl- or ethyl-substituted or unsubstituted furanyl, thienyl or pyridyl, respectively; Fluorine-, chlorine-, methyl- or ethyl-substituted or unsubstituted phenoxy-C _1-4 -alkyl; Or respectively fluorine-, chlorine-, amino-, methyl- or ethyl-substituted or unsubstituted pyridyloxy -C _1-4 - alkyl, pyrimidyl-oxy -C _1-4 - alkyl or thiazolyl oxy -C _{1- 4} -alkyl, R ² is fluorine- or chlorine-substituted or unsubstituted C _1-14 -alkyl, C _2-14 -alkenyl, C _1-4 -alkoxy-C _2-6 -alkyl or poly-C _1-4- Alkoxy-C _2-6 -alkyl; Fluorine-, chlorine-, methyl-, ethyl-, n-propyl-, isopropyl- or methoxy-substituted or unsubstituted C _3-6 -cycloalkyl; Or fluorine, chlorine, cyano-, nitro-, methyl-, ethyl-, n-propyl-, i-propyl-, methoxy-, ethoxy-, trifluoromethyl- or trifluoromethoxy- Substituted or unsubstituted phenyl or benzyl, R ³ is fluorine- or chlorine-substituted or unsubstituted methyl, ethyl, propyl, isopropyl, butyl or t-butyl, or fluorine-, chlorine-, bromine-, methyl-, ethyl-, isopropyl-, t -Butyl, methoxy-, ethoxy-, isopropoxy-, trifluoromethyl-, trifluoromethoxy-, cyano- or nitro-substituted or unsubstituted phenyl or benzyl, R ⁴ and R ⁵ are each independently of each other fluorine- or chlorine-substituted or unsubstituted C _1-4 -alkyl, C _1-4 -alkoxy, C _1-4 -alkylamino, di (C _1-4- Alkyl) amino or C _1-4 -alkylthio, or fluorine-, chlorine-, bromine-, nitro-, cyano-, methyl-, methoxy-, trifluoromethyl- or trifluoromethoxy-substituted, respectively Unsubstituted phenyl, phenoxy or phenylthio, R ⁶ and R ⁷ are each independently of each other hydrogen, fluorine- or chlorine-substituted or unsubstituted C _1-4 -alkyl, C _3-6 -cycloalkyl, C _1-4 -alkoxy, C _3-4- Alkenyl or C _1-4 -alkoxy-C _2-4 -alkyl, or fluorine-, chlorine-, bromine-, methyl-, methoxy- or trifluoromethyl-substituted or unsubstituted phenyl or benzyl, respectively Or together, one methylene group may be replaced by oxygen or sulfur and represents methyl- or ethyl-substituted or unsubstituted C _5-6 -alkylene radicals, Of these compounds The compound of formula (I) is excluded. Compound of formula (II): In the above formula, A, B, V, W, X, Y and Z each have the meanings mentioned in claim 1, R ⁸ represents C _1-6 -alkyl. Compound of Formula (XXI): In the above formula, A, B, V, W, X, Y and Z each have the meaning mentioned in claim 1. Compound of formula (XXIX): In the above formula, A, B, V, W, X, Y and Z each have the meaning mentioned in claim 1. Compound of formula (III): In the above formula, A, B, V, W, X, Y and Z each have the meanings mentioned in claim 1, R ⁸ represents C _1-6 -alkyl. Compound of formula (IV): In the above formula, A, B, V, W, X, Y and Z each have the meanings mentioned in claim 1, R ⁸ represents C _1-6 -alkyl, T represents hydrogen, halogen, C _1-6 -alkyl or C _1-8 -alkoxy. Compound of general formula (XXIII): In the above formula, V, W, X, Y and Z each have the meaning mentioned in claim 1. Compound of general formula (XXIV): In the above formula, V, W, X, Y and Z each have the meaning mentioned in claim 1, R ⁸ represents C _1-6 -alkyl. Compound of general formula (XXV): In the above formula, V, W, X, Y and Z each have the meaning mentioned in claim 1. A pesticide or herbicide for exterminating insect pests, comprising the compound of formula (I) according to claim 1. A method of controlling pests and weeds, characterized in that the compounds of formula (I) according to claim 1 are acted on pests and weeds, or their habitats. A process for preparing pesticide pesticides and herbicides, characterized in that the compound of formula (I) according to claim 1 is mixed with an extender, a surfactant, or an extender and a surfactant.