MXPA99005063A

MXPA99005063A - Substituted phenylketoenols and their use as pesticides and herbicides

Info

Publication number: MXPA99005063A
Application number: MXPA/A/1999/005063A
Authority: MX
Inventors: Erdelen Christoph; Wachendorffneumann Ulrike; Fischer Reiner; Dollinger Markus; Bretschneider Thomas; Dahmen Peter; Hagemann Hermann; Graff Alan; Andersch Wolfram
Original assignee: Bayer Ag 51373 Leverkusen De
Priority date: 1996-12-12
Filing date: 1999-06-01
Publication date: 2000-04-24

Abstract

This invention concerns new phenyl-substituted cyclic ketoenols of formula (I) in which Het stand for one of the groups (1), (2) or (3), and G, V, W, Y, and Z have the meaning given in the description, processes and intermediate products for their production and their us as pesticides and herbicides.

Description

SUBSTITUTE PHENYLCETOENOLES AND THEIR EMPLOYMENT AS PESTICIDE AGENTS.

FIELD OF THE INVENTION.

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

DESCRIPTION OF THE PREVIOUS TECHNIQUE.

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

Derivatives of the IH-arylpyrrolidinedione are known (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, W0 95/26 954, WO 96/25395 and WO 96/35 664) with insecticidal, acaricidal effects and, if necessary herbicides.

Ref .: 30266 It is known that certain substituted derivatives of? 3-dihydrofuran-2-one have herbicidal properties (see DE-A-4 014 420). The synthesis of tetronic acid derivatives, used as starting materials (such as, for example, 3- (2-methyl-phenyl) -4-hydroxy-5- (4-fluorophenyl) -? 3-dihydrofuranone- (2) ) has also been described in De-A-4 014 420. Structurally similar compounds without indication of an insecticidal and / or acaricidal activity are known from the publication of Campbell et al., J. Chem. Soc. , Perkin Trans. 1, 1985, (8) 1567-76. In addition, derivatives of 3-aryl-α "* -dihydrofuranone with herbicidal, acaricidal and insecticidal properties are known from EP-A-528 156, EP-A-0 647 637, WO 96/25395, WO 96/20196 and by previously cited patent application not yet published .. Derivatives of 3-aryl-3-dihydrothiophenone are also known (WO 95/26 345, WO 96/25395 and WO 96/35664).

However, the acaricidal and insecticidal activity and / or the spectrum of activity and / or the compatibility with the plants of these compounds, especially against the crop plants, are not yet sufficient.

DETAILED DESCRIPTION OF THE INVENTION.

New compounds of the formula (I) have now been found x v (I) w z wherein V means hydrogen, halogen, alkyl or alkoxy, W means hydrogen, cyano, nitro, halogen, alkyl, alkenyl, alkynyl, alkoxy, halogenoalkyl, haloalkoxy or means phenyl, phenoxy, phenylthio, phenylalkoxy or phenylalkylthio substituted respectively X means halogen, alkyl, alkenyl, alkynyl, alkoxy, halogenoalkyl, halogenoalkoxy, cyano, nitro or means phenyl, phenoxy, phenylthio, phenylalkyloxy or phenylalkylthio respectively substituted, Y means hydrogen, halogen, alkyl, alkoxy, haloalkyl, haloalkoxy , cyano or nitro, Z means hydrogen, halogen, alkyl, alkoxy, haloalkyl, haloalkoxy, hydroxy, cyano, nitro or means phenoxy, phenylthio, hetaryloxy with 5 or 6 members, hetarylthio with 5 or 6 members, phenylalkyloxy or phenylalkylthio, respectively substituted if necessary, or Y and Z mean, together with the carbon atoms, with which they are linked, a subst where appropriate, and if appropriate interrupted by one or more heteroatoms, or W and Z signify, together with the carbon atoms, with which they are bound, a given substituted and optionally interrupted by a plurality of heteroatoms, Het means one of the groups where G means hydrogen (a) or means one of the groups R * - "R * (?) ' E means a metal ion equivalent or an ammonium ion L means oxygen or sulfur, M means oxygen or sulfur, R ~ means alkyl, alkenyl, alkoxyalkyl, alkylthioalkyl, or polyalkoxyalkyl respectively substituted, if appropriate, by halogen or cyan or means cycloalkyl or heterocyclyl substituted, where appropriate, by halogen, alkyl or alkoxy or phenyl, phenylalkyl, hetaryl, phenoxyalkyl or hetaryloxyalkyl respectively substituted, where appropriate, R "means alkyl, alkenyl, alkoxyalkyl or polyalkoxyalkyl, each optionally substituted by halogen or by cyano or means cycloalkyl, phenyl or benzyl substituted respectively where appropriate, R3, R4 and R5, independently of each other, mean alkyl, alkoxy, alkylamino, dialkylamino, alkylthio, alkenylthio or cycloalkylthio substituted respectively by halogen or by phenyl, benzyl, phenoxy or phenylthio Where appropriate, R 6 and R 7, independently of one another, signify hydrogen, are alkyl, cycloalkyl, alkenyl, alkoxy, alkoxyalkyl substituted, if appropriate, by halogen or by cyano or phenyl or benzyl, respectively, respectively, or together the atom of N, with which they are linked, form a cycle that contains, if necessary, oxygen or sulfur and, if necessary, substituted.

The compounds of the formula (I) can also be present, depending on the type of the substituents, as optical isomers or as mixtures of isomers, in a variable composition, which can, if appropriate, be separated in a customary manner. Both the pure isomers and also the mixtures of the isomers, their preparation and use as well as the agents containing them are an object of the present invention. In the following, the compounds of the formula (I) will always be discussed, even if both the pure compounds and, where appropriate, mixtures with variable proportions of the isomeric compounds are to be indicated.

Considering the meanings (I) to (3) of the Het groups the following fundamental structures (1-1) to (1-3) are produced where G, V, W, X, Y and Z have the meaning indicated above.

Taking into account the various meanings (a), (b), (c), (d), (e), (f) and (g) of group G, the following fundamental structures (Ila) are produced up to (Ilg), when Het means group (1), (l-l-d) where E, L, M, V, W, X, Y, Z, R1, R :, R3, R4, R5, R6 and R7 have the meanings indicated above.

Taking into account the various meanings (a), (b), (c), (d), (e), (f) and (g) of the G groups, the following fundamental structures are produced (I-2-a) to (I-2-g), when Het means group (2), (I-2-e) where E, L, M, V, W, X, Y, Z, R1, R2, R3, R4, R5, R6 and R7 have the meaning indicated above. Taking into consideration the various meanings (a), (b), (c), (d), (e), (f) and (g) of the G groups, the following fundamental structures are produced (I-3-a) to (I-3-g), when Het means group (3), (I-3-b) where # E, L, M, V, W, X, Y, Z, R1, R2, R3, R4, R5, R6 and R7 have the meanings indicated above.

It has also been found that new compounds of the formula (I) are obtained according to procedures described below: (A) The compounds of the formula (1-1-a) are obtained wherein V, W, X, Y and Z have the meanings indicated above, if compounds of the formula (II) are condensed intramolecularly wherein V, W, X, Y and Z have the meanings indicated above, and R8 means alkyl (preferably alkyl having 1 to 6 carbon atoms), in the presence of a diluent and in the presence of a base.

(B) It has further been found that the compounds of the formula (I-2-a) are obtained wherein V, W, X, Y and Z have the meanings indicated above, if compounds of the formula are condensed intramolecularly (III) wherein V, W, X, Y, Z and R8 have the meanings indicated above, in the presence of a diluent and in the presence of a base.

(C) It has also been found that the compounds of the formula (I-3-a) are obtained wherein V, W, X, Y and Z have the meanings indicated above, and compounds of the formula (IV) are intramolecularly cyclized wherein V, W, X, Y, Z and R8 have the meanings given above, and T means hydrogen, halogen, alkyl (preferably alkyl having 1 to 6 carbon atoms) or alkoxy (preferably alkoxy with 1 to 8 carbon atoms) carbon), if necessary in the presence of a diluent and in the presence of an acid.

It has further been found (D) that the compounds of the formulas indicated above (Ilb) are obtained (I-3-b), in which R1, V, W, X, Y and Z have the meanings indicated above, if compounds of the abovementioned formulas (Ila) are reacted to (I-3-a), in which V, W, X, Y and Z have the meanings indicated above, respectively a) with acyl halides of the formula ( V) Hal ^^ R1 T (V) wherein R "has the meaning indicated above and Hal means halogen (especially chlorine or bromine), or ß) with anhydrides of carboxylic acids of the formula (VI) R ^ CO-O-CO-R1 (VI) wherein R1 has the meaning indicated above, if appropriate in the presence of a diluent and, if appropriate, in the presence of an acid-accepting agent; (E) that the compounds of the formulas indicated above (Ilc) are obtained up to (I-3-c), in which R2, V, W, N, X, Y and Z have the meanings indicated above and L means oxygen , if compounds of the above-mentioned formulas (Ila) are reacted to (I-3-a), in which V, W, X, Y and Z have the meanings indicated above, respectively with esters of chloroformic acid or with thioesters of the chloroformic acid of the formula (VII) R-M-C0-C1 (VII) wherein R: and M have the meanings indicated above, if appropriate in the presence of a diluent and, if appropriate, in the presence of an acid-accepting agent; (F) that the compounds of the formulas indicated above (Ilc) to (I-3-c) are obtained, in which R2, V, W, M, X, Y and Z have the meanings indicated above and L means sulfur , if compounds of the formulas indicated above (Ila) are reacted to (I-3-a), in which V, W, X, Y and Z have the meanings indicated above, respectively with esters of chloromonothiophoric acid or with esters of the chlorodithioformic acid of the formula (VIII) and wherein M and R2 have the meanings indicated above, if appropriate in the presence of a diluent and, if appropriate, in the presence of an acid-binding agent, (G) that the compounds of the formulas indicated above (Ild) to (I-3-d) are obtained, in which R3, V, W, X, Y and Z have the meanings indicated above, if compounds are reacted of the formulas indicated above (Ila) to (I-3-a), in which V, W, X, Y and Z have the meanings indicated above, respectively with sulfonyl chlorides of the formula (IX), R3-S02-C1 (ix) wherein R 3 has the meaning indicated above, optionally in the presence of a diluent and, if appropriate, in the presence of an acid-accepting agent, (H) whereby the compounds of the abovementioned formulas (Ile) are obtained up to (1-3-e), in which L, R4, R5, V, W, X, Y and Z have the meanings indicated above, if compounds of the formulas indicated above (Ila) are reacted to (I-3) -a) in which V, W, X, Y and Z have the meanings indicated above, respectively with phosphorus compounds of the formula (X) Hal-P (X) L R in which L, R4 and R5 have the meanings indicated above and Hal means halogen (especially chlorine or bromine), if appropriate in the presence of a diluent and, if appropriate, in the presence of an acid-accepting agent, (I) to obtain compounds of the formulas indicated above (Ilf) up to (I-) 3-f), in which E, V, W, X, Y and Z have the meanings indicated above, if compounds of the formulas (Ila) to (I-3-a) are reacted, in which V, W, X, Y and Z have the meanings indicated above, respectively with metal compounds or with amines of the formulas (XI) or (XII) Me (OR10) t (XI) N (XH), 12 wherein Me means a mono or divalent metal (preferably an alkali metal or an alkaline earth metal such as lithium, sodium, potassium, magnesium or calcium), t means the numbers 1 or 2 and R10, R11, R12, independently. together, they mean halogen or alkyl (preferably alkyl having 1 to 8 carbon atoms), optionally in the presence of a diluent, (J) whereby the compounds of the formulas indicated above (Ilg) are obtained up to (I-3-) g), in which L, R6, R7, V, W, X, Y and Z have the meanings indicated above, if compounds of the formulas indicated above (Ila) are reacted to (I-3-a), in which V, W, X, Y and Z have the meanings indicated above, respectively a) with isocyanates or with isothiocyanates of the formula (XIID, Rb-N = C = L (XIII: wherein Rd and L have the meanings given above, optionally in the presence of a diluent and, if appropriate, in the presence of a catalyst, or ß) with carbamidyl chlorides or with thiocarbamidyl chlorides of the formula (XIV) wherein L, R6 and R7 have the meanings given above, if appropriate in the presence of a diluent and, if appropriate, in the presence of an acid-binding agent.

It has also been found that the novel compounds of the formula (I) have a very good activity as pesticide agents, preferably as insecticides, acaricides and herbicides and are also frequently , r compatible with plants in a very good way, especially in front of the crop plants.

The compounds according to the invention are generally defined by the formula (I). The substituents or the preferred ranges of the residues indicated in the formulas mentioned above and which will be cited below, are explained below: Preferably, 25 V means hydrogen, halogen, alkyl having 1 to 6 carbon atoms or alkoxy with 1 to 6 carbon atoms, Preferably, W means hydrogen, nitro, cyano, halogen, alkyl having 1 to 6 carbon atoms, alkenyl with 2 to 6 carbon atoms, alkynyl with 2 to 6 carbon atoms, alkoxy with 1 to 6 carbon atoms, haloalkyl with 1 to 4 carbon atoms, halogenalkoxy with 1 to 4 carbon atoms or means phenyl, phenoxy, phenylthio, phenyl-alkoxy with 1 to 4 carbon atoms or phenyl-alkylthio with 1 to 4 carbon atoms substituted, where appropriate, by halogen, by alkyl having 1 to 6 carbon atoms, by alkoxy with 1 to 6 carbon atoms, by halogen alkyl with 1 to 4 carbon atoms, by halogenalkoxy with 1 to 4 carbon atoms; carbon atoms, by nitro or by cyano.

Preferably, X means halogen, alkyl having 1 to 6 carbon atoms, alkenyl with 2 to 6 carbon atoms, alkynyl with 2 to 6 carbon atoms, alkoxy with 1 to 6 carbon atoms, halogen alkyl with 1 to 4 carbon atoms , halogenalkoxy with 1 to 4 carbon atoms, cyano, nitro or means phenyl, phenoxy, phenylthio, phenyl-alkoxy with 1 to 4 carbon atoms or phenyl-alkylthio with 1 to 4 carbon atoms, substituted, if appropriate, by halogen, by alkyl having 1 to 6 carbon atoms, by alkoxy with 1 to 6 carbon atoms, by haloalkyl with 1 to 4 carbon atoms, by haloalkoxy with 1 to 4 carbon atoms, by nitro or by cyano.

Preferably Y denotes hydrogen, halogen, alkyl having 1 to 6 carbon atoms, alkoxy with 1 to 6 carbon atoms, halogen with 1 to 4 carbon atoms, halogen with 1 to 4 carbon atoms, cyano or nitro.

Preferably, Z stands for hydrogen, halogen, alkyl having 1 to 6 carbon atoms, alkoxy with 1 to 6 carbon atoms, halogenalkyl with 1 to 4 carbon atoms, halogenalkoxy with 1 to 4 carbon atoms, hydroxy, cyano, nitro or means phenoxy, phenylthio, thiazolyloxy, pyridinyloxy, pyridinyloxy, pyrazolyloxy, phenyl-alkoxy with 1 to 4 atoms or phenyl-alkylthio with 1 to 4 carbon atoms substituted, where appropriate, by halogen, with alkyl having 1 to 4 carbon atoms , by alkoxy with 1 to 4 carbon atoms, by haloalkyl with 1 to 4 carbon atoms, by haloalkoxy with 1 to 4 carbon atoms, by nitro or by cyano, or Preferably, Y and Z mean, together with the carbon atoms, with which they are bonded, alkanediyl having 3 to 5 carbon atoms or alkenodiyl having 3 to 5 carbon atoms substituted respectively by halogen, by alkyl with 1 to 6 carbon atoms, by alkoxy with 1 to 6 carbon atoms or by haloalkyl with 1 to 4 carbon atoms, in which one or three members may be replaced by oxygen, sulfur, nitrogen or a group carbonyl, independently of one another, or W and Z mean together with the carbon atoms, to which they are bonded, alkanediyl having 3 to 5 carbon atoms or alkenodillo having 3 to 5 carbon atoms substituted, if appropriate, by halogen, alkyl with 1 to 6 carbon atoms, for alkoxy with 1 to 6 carbon atoms or for halogenalkyl with 1 to 4 carbon atoms, in which one to three members may be replaced by oxygen, by sulfur, by nitro geno or by a carbonyl group, independently of each other.

Preferably, Het means one of the groups Preferably G means hydrogen (a) or means one of the groups (especially means (a), (b) or (c)), in which E means a metal ion equivalent or an ammonium ion, L means oxygen or sulfur and M means oxygen or sulfur.

Preferably, R 1 means alkyl with 1 to 20 carbon atoms, alkenyl with 2 to 20 carbon atoms, alkoxy with 1 to 8 carbon atoms-alkyl with 1 to 8 carbon atoms, alkylthio with 1 to 8 carbon atoms-alkyl with 1 to 8 carbon atoms or poly-alkoxy with 1 to 8 carbon atoms-alkyl having 1 to 8 carbon atoms, respectively substituted, if appropriate, by halogen or cyano, or means cycloalkyl with 3 to 8 carbon atoms substituted if appropriate by halogen, by alkyl with 1 to 6 carbon atoms or by alkoxy with 1 to 6 carbon atoms, in which one or two methylene groups, not directly adjoining by oxygen and / or Sulfur means phenyl which is optionally substituted by halogen, cyano, nitro, alkyl with 1 to 6 carbon atoms, alkoxy with 1 to 6 carbon atoms, haloalkyl with 1 to 6 carbon atoms, halogenalkoxy with 1 to 6 carbon atoms, for alkylthio with 1 a 6 carbon atoms or by alkylsulfonyl with 1 to 6 carbon atoms, means phenyl-alkyl having 1 to 6 carbon atoms, optionally substituted by halogen, by nitro, by cyano, by alkyl with 1 to 6 carbon atoms, C 1 -C 6 -alkoxy, by halogenalkyl with 1 to 6 carbon atoms or by haloalkoxy with 1 to 6 carbon atoms, means hetaryl with 5 or 6 members, optionally substituted by halogen or by alkyl with 1 to 6 carbon atoms, with 1 or 2 heteroatoms of the series consisting of oxygen, sulfur and nitrogen (for example pyrazolyl, thiazoyl, pyridyl, pyrimidyl, furanyl or thienyl), means phenoxy-alkyl having 1 to 6 carbon atoms substituted by halogen or by alkyl having 1 to 6 carbon atoms, means hetaryloxy-alkyl having 1 to 6 carbon atoms, with 5 or 6 members, optionally substituted by halogen, by amino or by alkyl with 1 to 6 carbon atoms, with 1 or 2 heteroatoms of the series formed by oxygen, sulfur and nitrogen (for example pyridyloxy-C1-C6-alkyl, pyrimidyloxy-C1-C6-alkyl or thiazolyloxy-C1-C6-alkyl).

Preferably R2 means alkyl with 1 to 20 carbon atoms, alkenyl with 2 to 20 carbon atoms, alkoxy with 1 to 8 carbon atoms-alkyl with 2 to 8 carbon atoms or poly-alkoxy with 1 to 8 carbon atoms- alkyl with 2 to 8 carbon atoms substituted, if appropriate, by halogen or cyano, means cycloalkyl having 3 to 8 carbon atoms, optionally substituted by halogen, by alkyl having 1 to 6 carbon atoms or by alkoxy with 1 to 6 carbon atoms or means phenyl or benzyl substituted, where appropriate, by halogen, by cyano, by nitro, by alkyl with 1 to 6 carbon atoms, by alkoxy with 1 to 6 carbon atoms, by haloalkyl with 1 to 6 atoms carbon or halogenalkoxy with 1 to 6 carbon atoms.

Preferably R <3> represents alkyl having from 1 to 8 carbon atoms optionally substituted by halogen or means phenyl or benzyl, optionally substituted by halogen, by alkyl having 1 to 6 carbon atoms, by alkoxy with 1 to 6 carbon atoms , by halogenalkyl with 1 to 4 carbon atoms, by haloalkoxy with 1 to 4 carbon atoms, by cyano or by nitro.

Preferably, R4 and R5 mean, independently of each other, alkyl with 1 to 8 carbon atoms, alkoxy with 1 to 8 carbon atoms, alkylamino with 1 to 8 carbon atoms, di- (alkyl with 1 to 8 carbon atoms) amino, alkylthio with 1 to 8 carbon atoms or alkenylthio with 3 to 8 carbon atoms, respectively substituted, if appropriate, by halogen or by phenyl, phenoxy or phenylthio, respectively substituted, if appropriate, by halogen, by nitro, by cyano, by alkoxy with 1 to 4 carbon atoms, for halogenalkoxy with 1 to 4 carbon atoms, for alkylthio with 1 to 4 carbon atoms, for halogenalkylthio with 1 to 4 carbon atoms, for alkyl with 1 to 4 carbon atoms or for haloalkyl with 1 to 4 carbon atoms.

Preferably, R6 and R7 stand for, independently of one another, hydrogen, mean alkyl of 1 to 8 carbon atoms, cycloalkyl of 3 to 8 carbon atoms, alkoxy of 1 to 8 carbon atoms, alkenyl of 3 to 8 carbon atoms or C 1 -C 8 -alkoxy-C 2 -C 8 -alkoxy substituted, where appropriate, by halogen or cyano, means phenyl or benzyl substituted, if appropriate by halogen, by C 1 -C 8 -alkyl, by halogenalkyl with 1 to 8 carbon atoms or by alkoxy with 1 to 8 carbon atoms or together they mean an alkylene radical having 3 to 6 carbon atoms, optionally substituted by alkyl having 1 to 6 carbon atoms, in which If necessary, replace a methylene group by oxygen or by sulfur.

Particularly preferably V is hydrogen, fluorine, chlorine, bromine, alkyl having 1 to 4 carbon atoms or alkoxy with 1 to 4 carbon atoms.

Particularly preferably W denotes hydrogen, nitro, cyano, fluorine, chlorine, bromine, alkyl having 1 to 4 carbon atoms, alkoxy with 1 to 4 carbon atoms, halogen with 1 to 2 carbon atoms, halogenoalkoxy with 1 to 2 carbon atoms or means phenyl, phenoxy or benzyloxy substituted, where appropriate, by fluorine, chlorine, bromine, alkyl with 1 to 4 carbon atoms, alkoxy with 1 to 4 carbon atoms, halogenalkyl with 1 to 2 carbon atoms, by halogenalkoxy with 1 to 2 carbon atoms, by nitro or by cyano.

Particularly preferably, X means fluorine, chlorine, bromine, alkyl having 1 to 4 carbon atoms, alkoxy with 1 to 4 carbon atoms, halogenoalkyl with 1 to 2 carbon atoms, halogenalkoxy with 1 to 2 carbon atoms, cyano or "nitro" means phenyl, phenoxy or benzyloxy substituted, where appropriate, by fluorine, chlorine, bromine, alkyl with 1 to 4 carbon atoms, alkoxy with 1 to 4 carbon atoms, haloalkyl with 1 to 2 atoms of carbon, by halogenalkoxy with 1 to 2 carbon atoms, by nitro or by cyano.

Particularly preferably, Y denotes hydrogen, fluorine, chlorine, bromine, aikyl with 1 to 4 carbon atoms, alkoxy with 1 to 4 carbon atoms, halogenalkyl with 1 to 2 carbon atoms, halogenalkoxy with 1 to 2 carbon atoms , cyano or nitro.

Particularly preferably, Z means hydrogen, fluorine, chlorine, bromine, alkyl with 1 to 4 carbon atoms, alkoxy with 1 to 4 carbon atoms, halogenoalkyl with 1 to 2 carbon atoms, halogenalkoxy with 1 to 2 carbon atoms, hydroxy, cyano, nitro or means phenoxy or benzyloxy, respectively substituted, if appropriate, by fluorine, by chlorine, by bromine, by alkyl with 1 to 4 carbon atoms, by alkoxy with 1 to 4 carbon atoms, by halogenalkyl with 1 to 2 carbon atoms, by haloalkoxy with 1 to 2 carbon atoms, by nitro or by cyano, or Particularly preferably, Y and Z, together with the carbon atoms, to which they are bonded, are alkanediyl having 3 to 4 carbon atoms or alkenodiyl having 3 to 4 carbon atoms substituted, where appropriate, by fluorine or chlorine, by bromine-, by alkyl with 1 to 4 carbon atoms, by alkoxy with 1 to 4 carbon atoms or by halogenalkyl with 1 to 2 carbon atoms, in which 1 or 2 non-directly adjacent members can be replaced by oxygen, by sulfur or by nitrogen, independently of each other, or Particularly preferably, W and Z mean together with the carbon atoms, to which they are bonded, alkanediyl having 3 to 4 carbon atoms or alkenodiyl having 3 to 4 carbon atoms, respectively substituted, where appropriate, by fluorine, with chlorine , by bromine, by alkyl with 1 to 4 carbon atoms, by alkoxy with 1 to 4 carbon atoms or by haloalkyl with 1 to 2 carbon atoms, in which one or two members not directly adjacent to one another can be replaced by oxygen, by sulfur or by nitrogen.

Especially preferably, Het means one of the groups Particularly preferably, G means hydrogen (a) or means one of the groups < «> . (especially means (a), (b) or (c)) in which E means an equivalent metal ion or an ammonium ion, L means oxygen or sulfur and M means oxygen or sulfur.

Particularly preferably, R 1 represents alkyl with 1 to 16 carbon atoms, alkenyl with 2 to 16 carbon atoms, alkoxy with 1 to 6 carbon atoms-alkyl with 1 to 6 carbon atoms, alkylthio with 1 to 6 carbon atoms, carbon-C 1 -C 6 -alkyl or C 1 -C 6 -alkoxy-C 1 -C 6 -alkyl optionally substituted by fluorine or chlorine or by C 3 -C 7 -cycloalkyl , optionally substituted by fluorine, by chlorine, by alkyl with 1 to 5 carbon atoms or by alkoxy with 1 to 5 carbon atoms, in which one or two methylene groups not directly adjacent to one another are replaced by oxygen and or by sulfur, means phenyl substituted, if appropriate, by fluorine, by chlorine, by bromine, by cyano, by nitro, by alkyl with 1 to 4 carbon atoms, by alkoxy with 1 to 4 carbon atoms, by haloalkyl with 1 to 3 carbon atoms, by haloalkoxy with 1 to 3 át carbon atoms, by alkylthio having 1 to 4 carbon atoms or by alkylsulfonyl having 1 to 4 carbon atoms, means phenyl-alkyl having 1 to 4 carbon atoms, optionally substituted by fluorine, chlorine, bromine or alkyl with 1 to 4 carbon atoms, for alkoxy with 1 to 4 carbon atoms, for halogenalkyl with 1 to 3 carbon atoms or for halogenalkoxy with 1 to 3 carbon atoms, means pyrazolyl, thiazolyl, pyridyl, pyrimidyl, furanyl or thienyl each substituted by fluorine, chlorine, bromine or alkyl with 1 to 4 carbon atoms, respectively, means phenoxy-alkyl having 1 to 5 carbon atoms, optionally substituted by fluorine, chlorine, bromine or alkyl with 1 to 4 carbon atoms or means pyridyloxy-alkyl with 1 to 5 carbon atoms, pyrimidyloxy-alkyl with 1 to 5 carbon atoms or thiazolyloxy-alkyl with 1 to 5 carbon atoms substituted, respectively, by fluorine, chlorine, by bromine, by in or by alkyl with 1 to 4 carbon atoms.

Particularly preferably, R 2 represents alkyl with 1 to 16 carbon atoms, alkenyl with 2 to 16 carbon atoms, alkoxy with 1 to 6 carbon atoms-alkyl with 2 to 6 carbon atoms or poly-alkoxy with 1 to 6 Carbon-alkyl atoms having 2 to 6 carbon atoms, respectively substituted, if appropriate, by fluorine or chlorine, means cycloalkyl having 3 to 7 carbon atoms, optionally substituted by fluorine, chlorine, alkyl with 1 to 4 carbon atoms, carbon or by alkoxy having 1 to 4 carbon atoms, or means phenyl or benzyl, respectively substituted, if appropriate, by fluorine, by chlorine, by bromine, by cyano, by nitro, by alkyl with 1 to 4 carbon atoms, by alkoxy with 1 to 3 carbon atoms, by halogenalkyl with 1 to 3 carbon atoms or by halogenalkoxy with 1 to 3 carbon atoms.

Particularly preferably, R3 means alkyl having 1 to 6 carbon atoms, optionally substituted by fluorine or chlorine or means phenyl or benzyl, optionally substituted, respectively, by fluorine, chlorine, bromine or alkyl with 1 to 4 carbon atoms, by alkoxy with 1 to 4 carbon atoms, by halogenalkoxy with 1 to 2 carbon atoms, by haloalkyl with 1 to 2 carbon atoms, by cyano or by nitro.

Particularly preferably, R 4 and R 5 mean, independently of each other, alkyl having 1 to 6 carbon atoms, alkoxy with 1 to 6 carbon atoms, alkylamino having 1 to 6 carbon atoms, di- (alkyl having 1 to 6 atoms) carbon) amino, alkylthio having 1 to 6 carbon atoms or alkenylthio with 3 to 4 carbon atoms, optionally substituted respectively by fluorine or chlorine or by phenyl, phenoxy or phenylthio substituted, respectively, by fluorine, by chlorine , by bromine, by nitro, by cyano, by alkoxy with 1 to 3 carbon atoms, by halogenalkoxy with 1 to 3 carbon atoms, by alkylthio with 1 to 3 carbon atoms, by halogenalkylthio with 1 to 3 carbon atoms, by alkyl with 1 to 3 carbon atoms or by haloalkyl with 1 to 3 carbon atoms.

Particularly preferably, R6 and R7 stand for, independently of one another, hydrogen, mean alkyl with 1 to 6 carbon atoms, cycloalkyl with 3 to 6 carbon atoms, alkoxy with 1 to 6 carbon atoms, alkenyl with 3 to 6 atoms of carbon or C 1 -C 6 -alkoxy-C 2 -C 6 -alkyl substituted by fluorine or by chlorine, respectively, means phenyl or benzyl, respectively substituted, if appropriate, by fluorine, chlorine, bromine, halogenalkyl with 1 to 5 carbon atoms, for alkyl with 1 to 5 carbon atoms or for alkoxy with 1 to 5 carbon atoms, together mean an alkylene radical having 3 to 6 carbon atoms, optionally substituted by alkyl with 1 to 5 carbon atoms. to 4 carbon atoms, in which, if necessary, a methylene group is replaced by oxygen or by sulfur.

Very particularly preferably, V means hydrogen, fluorine, chlorine, bromine, methyl, ethyl, propyl, iso-propyl, tere-butyl, methoxy, ethoxy, propoxy or iso-propoxy.

Very particularly preferably W denotes hydrogen, nitro, cyano, fluorine, chlorine, bromine, methyl, ethyl, propyl, n-butyl, iso-propyl, isobutyl, methoxy, ethoxy, propoxy, iso-propoxy, trifluoromethyl, difluoromethoxy, trifluoromethoxy, phenyl or benzyloxy.

Very particularly preferably, X means fluorine, chlorine, bromine, methyl, ethyl, propyl, butyl, iso-butyl, iso-propyl, methoxy, ethoxy, propoxy, iso-propoxy, trifluoromethyl, trifluoromethoxy, difluoromethoxy, cyano, nitro, phenyl or benzyloxy.

Very particularly preferably, Y denotes hydrogen, fluorine, chlorine, bromine, methyl, ethyl, propyl, iso-propyl, n-butyl, iso-butyl, tere-butyl, methoxy, ethoxy, propoxy, iso-propoxy, trifluoromethyl, trifluoromethoxy, difluoromethoxy, cyano or nitro.

Very particularly preferably, Z means hydrogen, fluorine, chlorine, bromine, methyl, ethyl, propyl, butyl, iso-butyl, iso-propyl, tere-butyl, methoxy, ethoxy, propoxy, iso-propoxy, trifluoromethyl, trifluoromethoxy, difluoromethoxy, cyano or nitro, or very particularly preferably, Y and Z mean, together with the carbon atoms, to which they are bonded, alkanediyl having 3 to 4 carbon atoms, optionally substituted by fluorine, chlorine or methyl , by ethyl, by propyl, by isopropyl, by methoxy, by ethoxy, by propoxy, by iso-propoxy or by trifluoromethyl, in which two non-directly adjacent members are replaced by oxygen or Very particularly preferably, W and Z mean together with the carbon atoms, to which they are bonded, alkanediyl having 3 to 4 carbon atoms, optionally substituted by fluorine, chlorine, methyl, ethyl, propyl, by isopropyl, by methoxy, by ethoxy, by propoxy, by iso-propoxy or by trifluoromethyl, in which two members not directly contiguous by oxygen are replaced.

Very particularly preferably, Het means one of the groups Very particularly preferably, G means hydrogen (a) or means one of the groups (especially means (a), (b) or (c)) in which E means a metal ion equivalent or an ammonium ion, L means oxygen or sulfur and M means oxygen or sulfur.

Very particularly preferably, R 1 means alkyl with 1 to 14 carbon atoms, alkenyl with 2 to 14 carbon atoms, alkoxy with 1 to 4 carbon atoms-alkyl with 1 to 6 carbon atoms, alkylthio with 1 to 4 atoms carbon-alkyl with 1 to 6 carbon atoms, poly-alkoxy with 1 to 4 carbon atoms-alkyl having 1 to 4 carbon atoms substituted respectively by fluorine or chlorine or cycloalkyl with 3 to 6 carbon atoms carbon, optionally substituted by fluorine, by chlorine, by methyl, by ethyl, by n-propyl, by i-propyl, by n-butyl, by i-butyl, by tert-butyl, by methoxy, by ethoxy, by n -propoxy or iso-propoxy, in which one or two methylene groups not directly adjacent to one another are replaced by oxygen and / or sulfuris phenyl, optionally substituted by fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, n-propyl, i-propyl, methoxy, ethoxy, trifluoromethyl, trifluoromethoxy, by methylthio, ethylthio, methylsulfonyl or ethylsulphonyl, means benzyl optionally substituted by fluorine, chlorine, bromine, methyl, ethyl, n-propyl, i-propyl, methoxy, ethoxy, trifluoromethyl or trifluoromethoxy, means furanyl, thienyl or pyridyl respectively substituted, if appropriate, by fluorine, chlorine, bromine, methyl or ethyl, means phenoxy-alkyl having 1 to 4 carbon atoms, optionally substituted by fluorine, chlorine, methyl or ethyl or means pyridyloxy-alkyl with 1 to 4 carbon atoms, idyloxy-alkyl with 1 to 4 carbon atoms, or thiazolyloxy-alkyl with 1 to 4 carbon atoms substituted, respectively, by fluorine , by chlorine, by amino, by methyl or by ethyl.

Very particularly preferably R2 means alkyl having 1 to 14 carbon atoms, alkenyl having 2 to 14 carbon atoms, alkoxy with 1 to 4 carbon atoms-alkyl having 2 to 6 carbon atoms or poly-alkoxy with 1 to 4 carbon atoms - alkyl having 2 to 6 carbon atoms substituted, if appropriate, by fluorine or chlorine, means cycloalkyl having 3 to 6 carbon atoms, optionally substituted by fluorine, chlorine, methyl, ethyl, n-propyl, iso-propyl or methoxy, or phenyl or benzyl respectively substituted, where appropriate, by fluorine, chlorine, cyano, nitro, methyl, ethyl, n-propyl, i-propyl, by methoxy, by ethoxy, by trifluoromethyl or by trifluoromethoxy.

Very particularly preferably R.sup.3 is methyl, ethyl, propyl, iso-propyl, n-butyl, tert-butyl substituted, where appropriate, by fluorine or by chlorine or by phenyl or benzyl, respectively substituted, if appropriate, by fluorine, by chlorine , by bromine, by methyl, by ethyl, by isopropyl, by tert-butyl, by methoxy, by ethoxy, by iso-propoxy, by trifluoromethyl, by trifluoromethoxy, by cyano or by nitro.

Very particularly preferably, R 4 and R 5 mean, independently of each other, alkyl having 1 to 4 carbon atoms, alkoxy with 1 to 4 carbon atoms, alkylamino with 1 to 4 carbon atoms, di- (-alkyl with 1 to 4 carbon atoms) amino or alkylthio having 1 to 4 carbon atoms substituted, where appropriate, by fluorine or chlorine or by phenyl, phenoxy or phenylthio, respectively substituted, if appropriate, by fluorine, chlorine, bromine, nitro, cyano, by methyl, by methoxy, by trifluoromethyl or by trifluoromethoxy.

Very particularly preferably, R6 and R7 stand for, independently of one another, hydrogen, mean alkyl with 1 to 4 carbon atoms, cycloalkyl with 3 to 6 carbon atoms, alkoxy with 1 to 4 carbon atoms, alkenyl with 3 to 4 carbon atoms. C 1 -C 4 -alkyl or C 1 -C 4 -alkyl atoms with 2 to 4 carbon atoms, respectively substituted by fluorine or chlorine, respectively, mean phenyl or benzyl, respectively substituted, if appropriate, by fluorine, chlorine, bromine, by methyl, by methoxy or by trifluoromethyl or together they mean an alkylene radical having 5 or 6 carbon atoms, optionally substituted by methyl or ethyl, in which case a methylene group is replaced by oxygen or by sulfur.

The definitions of the remains or the explanations given above in a general manner or in the preferred ranges can be combined arbitrarily with each other, even between the corresponding intervals and the preferred ranges. These are valid for the final products as well as correspondingly for the starting products and for the intermediate products.

According to the invention, the compounds of the formula (I) are preferred, in which a combination of the meanings given above is particularly preferably present.

According to the invention, the compounds of the formula (I) are particularly preferred, in which a combination of the meanings given above is particularly preferably present.

According to the invention, the compounds of the formula (I) are very particularly preferred, in which a combination of the meanings indicated above is very particularly preferably present.

The saturated or unsaturated hydrocarbon radicals such as alkyl or alkenyl, even in combination with heteroatoms, such as for example in alkoxy, can be straight chain or branched chain, insofar as possible.

The substituted radicals can be mono- or polysubstituted, the substituents being the same or different than in the case of polysubstitutions.

In particular, in addition to the compounds indicated in the preparation examples, the following compounds of the formula (I-1-a) will be mentioned: W H Br H to H H Cl H Br H H Cl H Cl H H Cl H F H H F H Cl H H Cl * OCH3 H H Cl H CH3 H H OCH3 H Cl H H OCH3 H OCH3 H H CH3 H l H H CH3 H F H H CH3 H OCH3 H H CH3 H t-C4H9 H H CH3 H CH3 H H Cl Cl H H H Cl F H H H Cl OCH3 H H H Cl CH3 H H H Cl OC2H5 H H H OCH3 OCH3 H H H CH3 CH3 H H H Br CH3 Br H H Cl Cl CH3 H H CH3 Br CH3 H w H CH3 a CH3 H H CH3 OCHF2 CH3 H H CH3 OCH2CF3 CH3 H H CH3 OC2H3 CH3 H H CH3 OCH3 CH3 H H CH3 CH3 CH3 H H Br Br CH3 H H a Cl CH3 H H C2H3 C2H5 Br H H CH3 CH3 Br H H CH3 CH3 OCH3 H H Br Cl CH3 H H Br CH3 to H H Cl CH3 Br H H C2H5 Br CH3 H H CH3 0-C3H7 CH3 H H CH3 O-Bz * CH3 H H CH3 CH3 C! H H CH3 Ph »CH3 H H Cl H Cl a H CH3 H CH3 CH3 H CH3 H Cl CH3 H Br H Cl CH3 H Br H CH3 CH3 H. Cl H Br CH3 H Cl H Cl CH3 H CH3 H Br CH3 H Cl H Cl F Cl V X W Y _. «H CH3 HHHH HHHH Cl HHHH O H H H H H H H H H H H H H H 3 CH 3 CH 3 CH 3 CH 3 H 3 H 3 Br 3 CH 3 CH 3 CH 3 CH 3 CH 3 CH 3 CH 3 Cl 3 CH 3 H 3 CH 3 CH 3 CH 3 CH 3 CH 3 CH 3 CH 3 CH 3 CH 3 CH 3 CH 3 Cl H CH 3 CH3 CH3 Br H CH3 CH3 H Cl H CH3 CH3 H Br H Cl Cl H Br CH 3 CH 3 CH 3 CH 3 CH 3 * Bz = benzyl; Ph = phenyl.

In particular, in addition to the compounds indicated in the preparation examples, the following compounds of the formula (I-2-a) will be mentioned.

Table 2 where V, W, X, Y and Z have the meanings indicated in table 1.

In particular, in addition to the compounds indicated in the preparation examples, the following compounds of the formula (I-3-a) will be mentioned.

Table 3 in which Y, W, X, Y and Z have the meanings indicated in table 1.

If N- [(4-chloro-2,6-dimethyl-phenylacetyl) -3-amino-3-carboxyethyl-tetrahydropyran is used as starting material (A), according to process (A), it may be The development of the process according to the invention is represented by means of the following reaction scheme: If it is used, according to procedure (B), the O- [(2-chloro-6-methyl) -phenylacetyl] -2-hydroxy-3-carboxyethyl-tetrahydrofuran, the development of the process according to the invention can be represented by means of the following reaction scheme If, according to process (C), 2- [(2-chloro-4,6-dimethyl) -phenyl] -4- (4-methoxy) -benzylmercapto-4,4-methyleoxypropyl-3-oxo- ethyl valerianate, the development of the process according to the invention can be represented by means of the following reaction scheme: If 3- ((2-chloro-4-methyl) -phenyl] -5,5-methylene-oxypropyl-pyrrolidine-2,4-dione and the compound are used according to the procedure (Da). Pivaloyl chloride, as starting products, the development of the process according to the invention can be represented by means of the following reaction scheme: If they are used according to the procedure (D.) (variant ß) 3- [(2,4-dichloro) -phenyl] -4-hydroxy-5,5-methyleneoxypropyl-3-dihydrofuran-2-one and acetic anhydride as starting materials, development may be depicted of the process according to the invention by means of the following reaction scheme: If 8- [(2,4-dichloro) -phenyl] -5,5-methyleneoxy-propyl-pyrrolidin-2,4-dione and ethoxyethyl chloroformate are used as starting materials, they may be used according to process (E). The development of the process according to the invention is represented by means of the following reaction scheme: If 3- (2,5-dibromo-4-methyl) -phenyl] -4-hydroxy-5,5-methyleneoxy-propyl-3-dihydrofuran-2-one and the compound are used according to process (F), Methyl chloromonothioformate as starting materials, the development of the reaction may be represented as follows: If, according to process (G), 2- [(2,4,6-trimethyl) -phenyl] -5,5-methylene-oxypropyl-pyrrolidine-2,4-dione and methanesulfonyl chloride are used as the products of starting, the development of the reaction can be represented by means of the following reaction scheme: If 2- (4-bromo-2-chloro-6-methyl) -phenyl] -4-hydroxy-5,5-methyleneoxypropyl-3-dihydrophuran-2-one is used according to process (H), metantiofosfonilo- (2, 2, 2-trifluoroethyl ester) chloride as starting products, the development of the reaction can be represented by means of the following reaction scheme: If, according to process (I), 3- [(2, -dichloro) -6-methylphenyl] -5,5-methyleoxypropyl-pyrrolidin-2, -dione and NaOH are used as conipients, the procedure development may be illustrated. according to the invention by means of the following reaction scheme: Na (+) If 3- ((2-chloro-4-bromo-5-methyl) -phenyl] -4-hydroxy-5,5-methyleneoxypropyl-3-dihydro-furan-2 is used according to the procedure (variant a) -one and the ethylisocyanate as starting products, the development of the reaction can be represented by means of the following reaction scheme: If, according to process (J) (variant ß), 3- [(2-chloro-4,6-dimethyl-phenyl] -5,5-methyleneoxypropyl-pyrrolidin-2-dione and dimethylcarbamidyl chloride are used as starting products, the development of the reaction can be represented by means of the following reaction scheme: The compounds required as starting materials, in the process (A) according to the invention, of the formula (II), wherein V, W, X, Y, Z and R8 have the meanings indicated above, are new.

The esters of the acylacids of the formula (II) are obtained, for example, if amino acid derivatives of the formula (XV) are acylated r ~, 8? (XV) or -NN. wherein R has the meaning indicated above, with substituted phenylacetyl halides of the formula (XVI) wherein V, W, X, Y and Z have the above meanings and Hal means chlorine or bromine, (Chem. Reviews 52, 237-416 (1953); Bhattacharya, Indian J.

Chem. 6, 341-5, 1968) acylamino acids of the formula (XVII) are esterified. wherein V, W, X, Y and Z have the meanings indicated above, (Chem. Ind. (London) 1568 (1968)).

The compounds of the formula (XVII) where V, W, X, Y and Z have the meanings indicated above, are new.

The compounds of the formula (XVII) are obtained, for example, if the 3-aminotetrahydropyran-3-carboxylic acid of the formula (XVIII) is stacked. with substituted phenylacetyl halides of the formula (XVI) where V, W, X, Y and Z have the meanings indicated above and Hal means chlorine or bromine, according to Schotten-Baumann (Organikum, VES Deutscher Verlag der Wissenschaften, Berlin 1977, page 505).

The compounds of the formula (XVI) are partially novel and can be prepared according to known processes (see, for example, WO 97/02 243, WO 97/01 535 and DE-196 13 171).

The compounds of the formula (XVI) are obtained, for example, if substituted phenylacetic acids of the formula (XIX) are reacted (XIX) in which V, W, X, Y and Z have the meaning indicated above, with halogenating agents (for example thionyl chloride, thionyl bromide, oxalyl chloride, phosgene, phosphorus trichloride, phosphorus tribro uro , or phosphorus pentachloride), optionally in the presence of a diluent (for example chlorinated aliphatic or aromatic hydrocarbons, such as toluene or methylene chloride) at temperatures of -20 ° C to 150 ° C, preferably -10 ° C. ° C up to 100 ° C.

The compounds of the formula (XIX) are partially novel, can be obtained according to procedures known from the literature (Organikum 15th edition, page 533, VEB Deutscher Verlag der Wissenschaften, Berlin 1977, see for example WO 97/02 243, WO 07/01 535 and DE-196 13 171). The compounds of the formula (XIX) are obtained, for example, if substituted phenylacetic acid esters of the formula (XX) are hydrolyzed. ? - z rw - (XX) in which V, W, X, Y, Z and R8 have the meaning indicated above, in the presence of an acid, (for example an inorganic acid such as hydrochloric acid) or a base (for example of an alkaline hydroxide such as, for example, sodium or potassium hydroxide), and optionally a diluent (for example of an aqueous alcohol such as methanol or ethanol) at temperatures between 0 ° C and 150 ° C, preferably between 20 ° C and 100 ° C.

The compounds of the formula (XX) are partially novel, they can be prepared according to methods known in principle.

The compounds of the formula (XX) are obtained, for example, by reacting substituted 1, 1, 1-trichloro-2-phenylethanes of the formula (XXI) wherein V, W, X, Y and Z have the meaning indicated above, firstly with alcoholates (for example alkali metal alcoholates such as sodium methylate or sodium ethylate) in the presence of a diluent (for example alcohol) derivative of the alcoholate) at temperatures between 0 ° C and 150 ° C, preferably between 20 ° C and 120 ° C, and then with an acid (preferably an inorganic acid such as for example sulfuric acid), at temperatures ranging from -20 ° C and 150 ° C, preferably 0 ° C and 100 ° C (see DE-3 314 249).

The compounds of the formula (XXI) are partially new, they can be prepared according to processes known in principle.

The compounds of the formula (XXI) are obtained, for example, if they are reacted anilines of the formula (XXII) wherein V, W, X, Y and Z have the meaning indicated above, in the presence of an alkyl nitrite of the formula (XXIII) R13-ONO (XXIII) wherein R 13 means alkyl having 1 to 6 carbon atoms, in the presence of cupric chloride (II) and, if appropriate, in the presence of a diluent (for example of an aliphatic nitrile such as acetonitrile) at a temperature of -20 ° C up to 80 ° C, preferably from 0 ° C to 60 ° C, with vinylidene chloride (CH2 = CC12).

The compounds of the formula (XXII) are partially known compounds. However, these can be obtained according to processes known from the literature, for example by reduction of the corresponding nitro compounds or halides of anilines or acetanilides and subsequent retrodissociation.

The compounds of the formula (XXIII) are known compounds of organic chemistry. Cupric chloride (II) and vinylidene chloride have been known for a long time and can be acquired.

The compounds of the formula (XV) and (XVIII) are new. These can be obtained by methods known per se (see, for example, the publications Compagnon, Ann. Chim. (Paris) [14] 5, pages 11-23, 23-27 (1970), L. Munday, J. Chem. Soc. 4372 (1961); JT Eward, C. Jitrangeri, Can. J. Chem. 53, 3339 (1975).

In addition, the starting materials used in the above process (A) of the formula (II) can be prepared wherein V, W, X, Y, Z and R8 have the meanings indicated above, if the 3-amino-tetrahydropyran-3-carboxynitrile of the formula (XXIV) is reacted with substituted phenylacetic acid halides of the formula (XVI) wherein V, W, X, Y, Z and Hal have the meanings indicated above, to give compounds of the formula (XXV) wherein V, W, X, Y and Z have the meanings indicated above, and these are then subjected to an acid alcoholysis.

The compounds of the formula (XXV) are also new. The compounds of the formula (XXIV) are also new (see the preparation example).

The compounds, which are necessary as starting materials in the case of the process (B) according to the invention of the formula (III) wherein V, W, X, Y, Z and R8 have the meanings indicated above, are new.

These can be obtained according to methods known in principle in a simple manner.

The compounds of the formula (III) are obtained, for example, if 3-hydroxy-tetrahydropyran-3-carboxylic acid esters of the formula (XXVI) are acylated wherein R8 has the meaning indicated above, with substituted phenyl-acetic acid halides of the formula (XVI) wherein V, W, X, Y, Z and Hal have the meanings indicated above, (Chem. Reviews 52, 237-416 (1953)).

The esters of 3-hydroxy-tetrahydropyran-3-carboxylic acid of the formula (XXVI) are new. For example, the 3-hydroxy-tetrahydropyran-3-carboxy-nitrile of the formula (XXVI-a) is obtained in the presence of acids, for example according to Pinner (see the preparation example). The cyanohydrin is obtained, for example, by reaction of tetrahydropyran-3-one with cyanuric acid.

The compounds, necessary as starting materials in the case of the process (C) above, of the formula (IV) where T, V, W, X, Y, Z and R8 have the meanings indicated above, are new.

They can be obtained according to methods known in principle.

The compounds of the formula (IV) are obtained, for example, if the esters of the substituted phenylacetic acid of the formula (XX) are acylated wherein V, W, X, Y, R8 and Z have the meanings indicated above, with 2-benzylthiocarbonyl halides of the formula (XXVII) (XXVII) wherein T has the meaning indicated above, and Hal means halogen (especially chlorine or bromine), in the presence of strong bases (see, for example, MS Chambers, EJ Thomas, DJ illiams J. Chem. Soc. Chem. Commun. ., (1987), 1228).

The benzylthio carbonyl halides of the formula (XXVII) are new. These can be prepared according to known procedures (J. Antibiotics (1983), 2_6, 1589).

The acyl halides of the formula (V), the anhydrides of the carboxylic acids of the formula (VI), the esters of the chloroformic acid or the thioesters of the chloroformic acid of the formula (VII), the esters of the chloromonothioformic acid or the esters of the chlorodithioformic acid of the formula (VIII), the sulfonyl chlorides of the formula (IX), the phosphorus compounds of the formula (X) and the metal hydroxides, the metal oxides or the amines of the formulas (XI) and ( XII) and the isocyanates of the formula (XIII) and the carba idyl chlorides of the formula (XIV), which are also necessary as starting materials for carrying out the processes according to the invention (D), (E), (F ), (G), (H), (I) and (J) are generally known compounds of organic or inorganic chemistry.

The compounds of the formulas (XVI), (XIX), (XX), (XXI) and (XXII) are also known from the patent applications cited at the beginning and / or can be prepared according to the methods indicated therein (see also WO 96/35 664, WO 97/01 535, WO 97 / 02 243 and DE-196 13 171).

The process (A) is characterized in that the compounds of the formula (II) are subjected to an intramolecular condensation, in which V, W, X, Y, Z and R8 have the meanings indicated above, in the presence of a diluent and in presence of a base.

Suitable diluents in the process (A) according to the invention are all inert organic solvents with respect to the reaction partners. Preference is given to using hydrocarbons, such as toluene and xylene, in addition to ethers, such as dibutyl ether, tetrahydrofuran, dioxane, glycol dimethyl ether and diglycoldimethyl ether, in addition polar solvents such as dimethyl sulfoxide, sulfolane, dimethylformamide and N-methyl pyrrolidone, and alcohols such as methanol, ethanol, propanol, iso-propanol, butanol, iso-butanol and tert-butanol.

As bases (deprotonating agents), all customary proton acceptors can be used in the process (A) according to the invention. Preference is given to using oxides, hydroxides and carbonates of alkali metals and alkaline earth metals, such as sodium hydroxide, potassium hydroxide, magnesium oxide, calcium oxide, sodium carbonate, potassium carbonate and calcium carbonate, which can also be used in the presence of phase transfer catalysts such as for example triethylbenzylammonium chloride, tetrabutylammonium bromide, Adogen 464 (= etriltrialkyl chloride (with 8 to 10 carbon atoms) ammonium) or TDA 1 (= tris- (methoxyethoxyethyl) -amine) ). In addition, alkali metals such as sodium or potassium can be used. Furthermore, alkali metal and alkaline earth metal amides and hydrides such as sodium amide, sodium hydride and calcium hydride, and also alkali metal alcoholates such as sodium methylate, sodium ethylate and potassium tert-butylate can be used.

The temperature of the reaction in carrying out the process (A) according to the invention can vary within wide limits. In general, work is carried out at temperatures between -75 ° C and 200 ° C, preferably between -50 ° C and 150 ° C.

The process (A) according to the invention is generally carried out under normal pressure.

In carrying out the process (A) according to the invention, the reaction components of the formula (II) and the deprotonating bases are used in general in equimolar amounts or approximately twice the equimolar amounts. However, it is also possible to use one or other of the components in a larger excess (up to 3 moles).

The process (B) is characterized in that the compounds of the formula (III) are subjected to intramolecular condensation, in which V, W, X, Y, Z and Rft have the meanings indicated above, in the presence of a diluent and in the presence of a base.

Suitable diluents in the process (B) according to the invention are all organic solvents which are inert to the reaction partners. Preference is given to using hydrocarbons, such as toluene and xylene, and also ethers, such as dibutyl ether, tetramdrofuran, dioxane, glycol dimethyl ether and diglycoldimethyl ether, in addition polar solvents such as dimethyl sulfoxide, sulfolane, dimethylformamide and N-methyl-pyrrolidone. In addition, alcohols such as methanol, ethanol, propanol, iso-propanol, butanol, iso-butanol and tert-butanol can be used.

As bases (deprotonating agents), all customary proton acceptors can be used in the process (B) according to the invention. Preference is given to using oxides, hydroxides and carbonates of alkali metals and alkaline earth metals, such as sodium hydroxide, potassium hydroxide, magnesium oxide, calcium oxide, sodium carbonate, potassium carbonate and calcium carbonate, which can also be used in the presence of phase transfer catalysts such as for example triethylbenzylammonium chloride, tetrabutylammonium bromide, Adogen 464 (= methyltrialkyl chloride (with 8 to 10 carbon atoms) ammonium) or TDA 1 (= tris- (methoxyethoxyethyl) -amine) ). In addition, alkali metals such as sodium or potassium can be used. Furthermore, alkali metal and alkaline earth metal amides and hydrides, such as sodium amide, sodium hydride and calcium hydride, and also alkali metal alcoholates such as sodium methylate, sodium ethylate and potassium tert-butylate can also be used. .

The temperature of the reaction in the process (B) according to the invention can vary within wide limits. In general, work is carried out at temperatures between -75 ° C and 200 ° C, preferably between -50 ° C and 150 ° C.

In the process (B) according to the invention, it is generally carried out under normal pressure.

In carrying out the process (B) according to the invention, the reaction components of the formula (III) and the deprotonating bases are generally employed in approximately equimolar amounts. However, it is also possible to use one or other of the components in a larger excess (up to 3 moles).

Process (C) is characterized in that compounds of the formula (IV) in which T, V, W, X, Y, Z and R8 have the meanings given above, are intramolecularly cycled in the presence of an acid and, if appropriate , in the presence of a diluent. » Suitable diluents in the process (C) according to the invention are all inert organic solvents with respect to the reaction partners. Preferably hydrocarbons, such as toluene, xylene, in addition halogenated hydrocarbons such as dichloromethane, chloroform, ethylene chloride, chlorobenzene, dichlorobenzene, in addition polar solvents such as dimethyl sulfoxide, sulfolane, dimethylformamide and N-methyl-pyrrolidone can be employed. In addition, alcohols such as methanol, ethanol, propanol, iso-propanol, butanol, iso-butanol, tert-butanol can be used.

If necessary, the acid used can also serve as a diluent.

As acids can be used in the procedure (C) according to the invention all inorganic and organic acids, such as, for example, hydrohalic acids, sulfuric acid, alkyung, aryl and haloalkyl sulfonic acids, especially halogenated alkylcarboxylic acids such as trifluoroacetic acid.

The reaction temperature in carrying out the process (C) according to the invention can vary within wide limits. In general, the process is carried out at temperatures between 0 ° C and 250 ° C, preferably between 50 ° C and 150 ° C.

The process (C) according to the invention is generally carried out under normal pressure.

When carrying out the process (C) according to the invention, the reaction components of the formula (IV) and the acids are used, for example, in equimolar amounts. However, it is also possible, if appropriate, to use the acid in catalytic amounts.

The process (Da) is characterized in that the compounds of the formulas (Ila) to (I-3-a) are reacted, respectively, with carbonyl halides of the formula (V), if appropriate in the presence of a diluent and, if appropriate, given, in the presence of an acid-accepting agent.

All solvents which are inert to acyl halides can be used as diluents in the process (Da) according to the invention. Preferably, hydrocarbons such as benzine, benzene, toluene, xylene and tetralin can be used, in addition halogenated hydrocarbons, such as methylene chloride, chloroform, carbon tetrachloride, chlorobenzene and o-dichlorobenzene, further ketones, such as acetone and ethylisopropyl ketone, in addition ethers, such as diethyl ether, tetrahydrofuran and dioxane, further esters of carboxylic acids, such as ethyl acetate, and also strong polar solvents such as dimethylformamide, dimethylsulfoxide and sulfolane. When the stability to the hydrolysis of the acyl halide allows it, the reaction can also be carried out in the presence of water.

Suitable acid acceptors are all the usual acid acceptors in the reaction according to process (Da) of the invention. Preference is given to using tertiary amines, such as triethylamine, pyridine, diazabicyclooctane (DABCO), diazabicycloundecene (DBU), diazabicyclononene (DBN), Hünig and N, N-dimethyl-aniline bases, and also alkaline earth metal oxides, such as magnesium oxide and calcium oxide, further alkali metal and alkaline earth metal carbonates, such as sodium carbonate, potassium carbonate and calcium carbonate, as well as alkali metal hydroxides such as sodium hydroxide and potassium hydroxide.

The temperature of the reaction in the process (Da) according to the invention can vary within wide limits. In general, work is carried out at temperatures between -20 ° C and + 150 ° C, preferably between 0 ° C and 100 ° C.

When carrying out the process (Da) according to the invention, the starting materials of the formulas (Ila) to (I-3-a) and the carbonyl halide of the formula (V) are used in general, respectively, in approximately equivalents However, it is also possible to use the carbonyl halide in a larger excess (up to 5 moles). Working up is carried out by customary methods.

The process - (Dß) is characterized in that compounds of the formulas (Ila) to (I-3-a) respectively are reacted with carboxylic acid anhydrides of the formula (VI), if appropriate in the presence of a diluent and, given case, in the presence of an acid-accepting agent.

Diluents which can be employed in the process (Dβ) according to the invention are preferably those diluents which also come into consideration when acyl halides are used. An excess of the carboxylic acid anhydride employed simultaneously can also act as a diluent.

As acid-binding agents, which may be added if appropriate, preferably in the process (Dβ) are those acid-binding agents which are also preferably used when the acyl halides are used.

The temperature of the reaction in the process (Dβ) according to the invention can vary within wide limits. In general, work is carried out at temperatures between -20 ° C and + 150 ° C, preferably between 0 ° C and 100 ° C.

When carrying out the process (Dβ) according to the invention, the starting materials of the formulas (Ila) to (I-3-a) and the carboxylic acid anhydride of the formula (VI) are used in general in approximately equivalent amounts. . However, it is also possible to use the carboxylic acid anhydride in a larger excess (up to 5 moles). Working up is carried out by customary methods.

In general, the process is carried out in such a way that the diluent and anhydride of the carboxylic acid present in excess are removed as well as the carboxylic acid formed by distillation or by washing with an organic solvent.

The process (E) is characterized in that compounds of the formulas (I-1-a) are reacted to (I-3-a) respectively with esters of chloroformic acid or with thiol esters of chloroformic acid of the formula (VII) if appropriate in the presence of a diluent and, if appropriate, in the presence of an acid-binding agent.

As acid-binding agents, in the case of process (E) according to the invention, all customary acid acceptors are suitable. Preference is given to using tertiary amines such as triethylamine, pyridine, DABCO, DBU, DBN, Hünig and N, N-dimethyl-aniline bases, as well as alkali metal oxides such as magnesium and calcium oxide, as well as alkali metal carbonates and alkaline earth metals such as sodium carbonate, potassium carbonate and calcium carbonate, as well as alkali metal hydroxides such as sodium hydroxide and potassium hydroxide.

Suitable diluents in the process (E) according to the invention are all solvents which are inert to the esters of chloroformic acid or to the thiol esters of chloroformic acid. Preferably hydrocarbons such as benzine, benzene, toluene, xylene and tetralin can be used, in addition halogenated hydrocarbons such as methylene chloride, chloroform, carbon tetrachloride, chlorobenzene and o-dichlorobenzene, in addition ketones such as acetone and butylisopropyl ketone, in addition ethers, such as diethyl ether, tetrahydrofuran and dioxane, further esters of carboxylic acids such as ethyl acetate, in addition nitriles such as acetonitrile and also strong polar solvents such as dimethylformamide, dimethylsulfoxide and sulfolane.

The temperature of the reaction in carrying out the process (E) according to the invention can vary within wide limits. The reaction temperature is generally between -20 ° C and + 100 ° C, preferably between 0 ° C and 50 ° C.

The process (E) according to the invention is generally carried out under normal pressure.

When carrying out the process (E) according to the invention, the starting materials of the formulas (Ila) to (I-3-a) and the corresponding esters of chloroformic acid or the thiolesters of chloroformic acid of the formula (VII) are used. ), in general, respectively in approximately equivalent quantities. However, it is also possible to use one or other of the components in a larger excess (up to 2 moles). Working up is carried out by customary methods. In general, the process is carried out in such a manner that the precipitated salts are eliminated and the mixture of the remaining reaction is concentrated by evaporation by eliminating the diluent.

The process (F) according to the invention is characterized in that compounds of the formulas (Ila) to (I-3-a) are reacted respectively with compounds of the formula (VIII) in the presence of a diluent and, if appropriate, in presence of an acid accepting agent.

In the preparation process (F), it is reacted, per mole of the starting compound of the formulas (Ila) to (I-3-a) about 1 mole of chloromonothioformic acid ester or of the chlorodithioformic acid ester of the formula (VIII), ao up to 120 C, preferably at 20 to 60 ° C.

Suitable diluents, if appropriate, are all inert polar organic solvents such as ethers, amides, sulfones, sulfoxides, as well as haloalkanes.

Preference is given to using dimethylsulfoxide, tetrahydrofuran, dimethylformamide, ethyl acetate or methylene chloride.

If the enolate salt of the compounds is prepared (Ila) to (I-3-a) in a preferred embodiment, by the addition of strong deprotonation agents such as for example sodium hydride or tertiary potassium butylate, the further addition of acid-binding agents can be desisted .

As bases, all customary proton acceptors can be used in the process (F). Preference is given to using alkali metal hydrides, alkali metal alcoholates, carbonates or bicarbonates of alkali metals or alkaline earth metals, or nitrogenous bases. Sodium hydride, sodium methanolate, sodium hydroxide, calcium hydroxide, potassium carbonate, sodium bicarbonate, triethylamine, dibenzylamine, diisopropylamine, pyridine, quinoline, diazabicyclooctane (DABCO) diazabicyclononene (DBN) and diazabicycloundecene ( DBU).

The reaction can be carried out at normal pressure or under higher pressure, preferably at normal pressure. Working up is carried out by customary methods.

The process (G) according to the invention is characterized in that compounds of the formulas (Ila) to (I-3-a) are reacted, respectively, with sulfonyl chlorides of the formula (IX), optionally in the presence of a diluent and , if appropriate, in the presence of an acid-accepting agent.

In the preparation process (G), about 1 mole of sulfonyl chloride of the formula (IX) is reacted per mole of the starting compound of the formulas (Ila) to (I-3-a) to -20 to 150 ° C, preferably at 0 up to 70LC.

The process (G) is preferably carried out in the presence of a diluent.

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

Preference is given to using dimethylsulfoxide, tetrahydrofuran, dimethylformamide, ethyl acetate, methylene chloride.

If, in a preferred embodiment, the enolate salt of the compounds (Ila) to (I-3-a) is prepared by the addition of strong deprotonation agents (such as for example sodium hydride or tertiary butylate of potassium), the subsequent addition of acid-binding agents may be abandoned.

If acid-binding agents are used, the usual inorganic or organic bases will be used, for example sodium hydroxide, sodium carbonate, potassium carbonate, pyridine and triethylamine.

The process (H) according to the invention is characterized in that compounds of the formula (Ila) to (I-3-a) are reacted, respectively, with phosphorus compounds of the formula (X), if appropriate in the presence of a diluent, and if appropriate in the presence of an acid-binding agent.

In the preparation process (H), for the preparation of the compounds of the formulas (I-1-e) to (1-3-e) for 1 mol of the compounds are reacted (Ila) to (I-3-a), from 1 to 2, preferably from 1 to 1.3 moles of the phosphorus compound of the formula (X) at temperatures between -40 ° C and 150 ° C, preferably between -10 and 110 ° C.

The process (H) is preferably carried out in the presence of a diluent.

Suitable diluents are all inert polar organic solvents such as ethers, esters of carboxylic acids, halogenated hydrocarbons, ketones, amines, nitriles, sulphones, sulfoxides, etc.

Preference is given to using acetonitrile, di-ethyl sulfoxide, tetrahydrofuran, dimethylformamide, methylene chloride.

Suitable acid-binding agents, if appropriate, include all customary inorganic or organic bases such as hydroxides, carbonates, or amines. Examples which may be mentioned are sodium hydroxide, sodium carbonate, potassium carbonate, pyridine and triethylamine.

The reaction can be carried out at normal pressure or under higher pressure, preferably at normal pressure. The elaboration is carried out according to usual methods of organic chemistry. The final products are preferably purified by crystallization, purification by chromatography or by so-called "initial distillation" ie removal of the volatile components under vacuum.

Process (I) is characterized in that compounds of the formulas (Ila) to (I-3-a) are reacted respectively with metal hydroxides or with metal alkoxides of the formula (XI) or with amines of the formula (XII) , if necessary in the presence of a diluent.

Diluents which can be employed in the process (I) according to the invention are preferably ethers such as tetrahydrofuran, dioxane, diethyl ether or alcohols such as methanol, ethanol, isopropanol, as well as water. The process (I) according to the invention are generally carried out under normal pressure. The reaction temperature is generally between -20 ° C and 100 ° C, preferably between 0 ° C and 50 ° C.

The process (J) according to the invention is characterized in that compounds of the formulas (I-1-a) are reacted to (I-3-a), respectively with (Ja) compounds of the formula. (XIII) optionally in the presence of a diluent and, if appropriate, in the presence of a catalyst or (Jß) with compounds of the formula (XIV), if appropriate in the presence of a diluent and, if appropriate, in the presence of an acid-accepting agent.

In the preparation process (Ja), about 1 mole of isocyanate of the formula (XIII) is reacted at 0 to 100 ° C per mole of the starting compound of the formulas (Ila) to (I-3-a), preferably at 20 to 50 ° C.

The process (Ja) is preferably carried out in the presence of a diluent.

Suitable diluents are all inert organic solvents, such as aromatic hydrocarbons, halogenated hydrocarbons, ethers, amides, nitriles, sulphones or sulfoxides.

If necessary, catalysts can be added to accelerate the reaction. As organic catalysts, tin organic compounds, such as, for example, dibutyltin dilaurate, can be used very advantageously.

It will work preferably at normal pressure In the preparation process (Jß), about 1 mole of carbamidyl chloride of the formula (XIV) is reacted at 0 to 150 by mole of the starting compound of the formulas (Ila) to (I-3-a). ° C, preferably at 20 to 70 ° C.

Suitable diluents, if appropriate, are all inert polar organic solvents, such as ethers, esters of carboxylic acids, nitriles, ketones, amides, sulfones, sulfoxides or halogenated hydrocarbons.

Preference is given to using dimethylsulfoxide, tetrahydrofuran, dimethylformamide or methylene chloride.

If the enolate salt of the compounds is prepared (Ila) to (I-3-a) in a preferred embodiment, by the addition of strong deprotonation agents (such as for example sodium hydride or potassium tertiary butylate), the subsequent addition of accepting agents can be desisted of acid.

If acid-binding agents are used, the usual inorganic or organic bases will be used, for example, sodium hydroxide, sodium carbonate, potassium carbonate, triethylamine or pyridine can be exemplified.

The active compounds according to the invention are suitable for the control of animal pests, preferably arthropods and nematodes, especially insects and arachnids, which occur in agriculture, in forestry, in the protection of stored products and materials, as well as in the sector of hygiene. They are active against normally sensitive and resistant species as well as against all or some of the stages of development. The aforementioned pests include: From the order of the isopods, for example, Oniscus asellus, Armadillidium vulgare and Porcellio scaber.

From the order of the diplópodos, for example, Blaniulus guttulatus.

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

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

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

From the order of springtails, for example, Onychiurus armatus.

From the order of the orthoptera, for example, Blatta orientalis, Periplaneta americana, Leucophaea maderae, Germanic Blattella; Acheta domesticus, Gryllotalpa spp., Locusta migratoria migratorioides, Melanoplus differentialis and Schistocerca gregaria.

From the order of dermápteros, for example, Forfícula auricularia.

From the order of the Isoptera, for example, Reticulitermes spp ..

Of the order of the anópluros, for example, Phylloxera vastatrix, Pemphigus spp., Pediculus humanus corporis, Haematopinus spp., And Linognathus spp.

From the order of the malophagous, for example, Trichodectes spp. and Damalinea spp ..

From the order of the Thysanoptera, for example, Frankliniella occidentalis, Hercinothrips femoralis, Thrips palmi, Thrips tabaci.

-From the order of the heteroptera, for example, Eurygaster spp., Dysdercus intermedius, Piesma quadrata, Cimex Lectularius, Rhodnius prolixus and Triato a spp.

On the order of hoopters, for example, Aleurodes brassicae, Beisia tabaci, Trialeurodes vaporariorum, Aphis gossypii, Brevicoryne brassicae, Cryptomyzus ribis, Aphis fabae, Doralis pomi, Eriosoma lanigerum, Hyalopterus arundinis, Macrosiphum avenae, Myzus spp., Phorodon humuli, Rhopalosiphum padi, Empoasca spp., Euscelis bilobatus , Nephotettix cincticeps, Lecaniu corni, Saissetia oleae, Laodelphax striatellus, Nilaparvata lugens; Aonidiella aurantii, Aspidiotus hederae, Pseudococcus spp., Psylla spp.

From the order of the Lepidoptera, for example, Pectinophora gossypiella, Bupalus piniarius, Cheimatobia brumata, Lithocolletis blancardella, Hyponomeuta padella, Plutella maculipennis, Malacosoma neustria, Euproctis chrysorrhoea, Lymantria spp., Bucculatrix thurberiella, Phyllocnistis citrella, Agrotis spp., Euxoa spp. , Feltia spp., Earias insulana, Heliothis spp., Spodoptera exigua, Mamestra brassicae, Panolis flammea, Prodenia litura, Spodoptera spp., Trichoplusia ni, Carpocapsa pomonella, Pieris spp., Chilo spp. Pyrausta nubilalis, Ephestia kuehnieila, Galleria mellonella, Tineola bisselliella, Tinca pellionella, Hofmannophila pseudospretella, Cacoecia podana, Capua reticula, Choristoneura fumiferana, Clysia ambiguella, Homona magnánima and Tortrix viridana.

From the order of Coleoptera, for example, Anobium punctatum, Rhizopertha dominica, Acanthoscelides obtectus, Hylotrupes bajulus, Agelastica alni, Leptinotarsa decemimeata, Phaedon cochleariae, Diabrotica spp., Psylliodes chrysocephala, Epilachna varivestis, Atomaria spp., Oryzaephilus surinamensis, Anthonomus spp. , Sitophilus spp., Otiorrhynchus sulcatus, Cosmopolites sordidus, Ceuthorrhynchus assimilis, Hypera postica, Dermestes spp., Trogoderma spp., Anthrenus spp., Attagenus spp., Lyctus spp., Meligethes aeneus, Ptinus spp., Niptus hololeucus, Gibbium psylloides , Tribolium spp., Tenebrio molitor, Agriotes spp., Conoderus spp., Melolontha melolontha, Amphimallon solstitialis and Costelytra zealandica.

From the order of Hymenoptera, for example, Diprion spp., Hoplocampa spp., Lasius spp., Monomorium pharaonis and Vespa spp.

From the order of the dipterans, for example, Aedes spp. Anopheles spp., Culex spp., Drosophila melanogaster, Musca spp., Fannia spp., Calliphora erythrocephala, Lucilia spp., Chrysomia spp., Cuterebra spp., Gastrophilus spp. , Hyppobosca spp., Liriomyza spp., Stomoxys spp., Oestrus.spp. , Hypoderma spp., Tabanus spp., Tannia spp., Bibio hortulanus, Oscinella frit, Phorbia spp., Pegomyia hyoscyami, Ceratitis capitata, Dacus oleae and Typula paludosa.

From the order of siphonoptera, for example, Xenopsylla cheopis, Ceratophyllus spp ..

From the order of the arachnids, for example Scorpio maurus, Lactrodectus mactans.

From the order of mites, for example Acarus siró, Argas spp., Ornithodoros spp., Dermanyssus gallinae, Eriophyes ribis, Phyllocoptruta oleivora, Boophilus spp., Rhipicephalus spp., Amblyomma spp., Hyalomma spp., Ixodes spp., Psoroptes spp. ., Chorioptes spp., Sarcoptes spp., Tarsonemus spp., Bryobia praetiosa, Panonychus spp., Tetranychus spp.

The active compounds according to the invention are characterized by high insecticidal and acaricidal activity.

They can be used with an especially good success in the fight against insects harmful to plants such as, for example, the larvae of the leaf beetle of horseradish (Phaedon cochleariae) or against the larvae of the green rice cicada (Nephotettix cinticeps). ) and against the caterpillars of the cabbage beetle (Plutella maculipennis).

The compounds according to the invention also have a fungicidal effect, for example against Venturia inaequalis.

The active compounds according to the invention can also be used as defoliants, desiccants, herbicidal agents and especially as weed killers. By weeds, in the broadest sense, we must understand the plants that grow in places where they are unwanted. The fact that the substances according to the invention act as total or selective herbicides depends essentially on the amount used.

The doses of the active compounds according to the invention, necessary to combat weeds, are between 0.001 and 10 kg / ha, preferably between 0.005 and 5 kg / ha.

The active compounds according to the invention can be used, for example, in the following plants: Poor dicotyledonous herbs of the following classes: Sinapis Lepidium, Galiu, Stellaria, Matricaria, Anthemis, Galinsoga, Chenopodium, Urtica, Senecio, Anaranthus portulaca, Xanthium, Convolvulus, Ipomoea, Polygonum, Sesbania, Ambrosia, Cirsium, Carduus, Sonchus, Solanum, Rorippa , Rotóla, Lindernia, Lamium, Veronica, Abutilón, E ex, Datura, Viola, Galeopsis, Papaver, Centaurea, Tpfolium, Ranunculus, Taraxacum.

Dicotyledonous crops of the classes: Gossypium glycine, Beta, Daucus, Phaseolus, Pisun, Solanum, Linu, Ipomoea, Vicia, Nicotiana, Lycopersicon, Arachis, Brassica, Lactuca, Cucumis, Cucurbita.

Bad monocotyledonous herbs of the following kinds: Echinochloa, Setaria, Panicum, Digitaria, Phleum, Poa, Festuca, Eleusine, Brachiaria, Lolium, Brous, Oats, Cyperus, Sorghum, Agropyron, Cycnodon, Monochoria, Fimbristylis, Sagittaria, Eleocharis, Scirpus, Paspalum, Ischaemum, Sphenoclea, Dactyloctenium, Agrostis, Alopecurus, Apera.

Cultures of monocotyledonous classes: Oryza, Zea, Triticun, Hordeu, Avena, Sécale, Sorghum, Panicum, Saccharum, Ananas, Asparagus, Allium.

The use of the active compounds according to the invention is, however, not limited in any way to these classes, but extends in the same way also to other plants.

The compounds are suitable, depending on the concentration, to completely combat the weeds, for example, in industrial and road installations and in roads and squares, with and without tree growth.

Likewise, the compounds can be used to combat weeds in permanent crops, for example, in forest facilities, ornamental trees, fruit trees, vineyards, citrus trees, walnut trees, bananas, coffee, tea , of rubber, of palms of oil, of cocoa, of fruits of berries and of hops, on ornamental and sports paths and in surfaces for meadows and to fight the weeds selectively in the mono-annual crops.

The active compounds according to the invention are very suitable for the selective fight against monocotyledonous weeds in dicotyledonous crops, both in pre-emergence procedures and in post-emergence procedures. As an example, they can be used in cotton or sugar beet with very good success in the fight against harmful weeds.

The products according to the invention can be transformed into their customary formulations such as solutions, emulsions, sprayable powders, suspensions, powders, dusts, pastes, soluble powders, granules, suspension-emulsion concentrates, natural and synthetic products impregnated with the active compound as well as microencapsulated in polymer products.

These formulations are prepared in known manner, for example by mixing the active compounds with extenders, that is, with liquid solvents, liquefied gases under pressure and / or solid excipients, optionally with the use of surfactants, ie emulsifiers and / or dispersants and / or foam generating means.

When water is used as an extender, organic solvents can be used, for example, as auxiliary solvents. Preferred liquid solvents are: aromatic hydrocarbons, such as xylene, toluene or alkylnaphthalenes, the aromatic-doped hydrocarbons and the gold aliphatic hydrocarbons, such as chlorobenzenes, chloroethylenes or methylene chloride, the aliphatic hydrocarbons, such as cyclohexane or the paraffins, for example petroleum fractions, alcohols such as butanol or glycol, as well as their ethers and esters, ketones, such as acetone, ethylethylketone, ethyl isobutyl ketone or cyclohexanone, strongly polar solvents, such as dimethylformamide and dimethylsulfoxide as well as Water.

Suitable solid excipients are, for example, ammonium salts and ground natural minerals, such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth and synthetic molten minerals, such as highly dispersed silicic acid, the aluminum oxide and silicates; as solid excipients for granulates are considered: for example broken and fractionated natural minerals, such as calcite, marble, pumice, sepiolite and dolomite, as well as synthetic granules of inorganic and organic flours and granulates of organic material, such as sawdust , husks of coconut, corn ears and tobacco stalks; suitable emulsifiers and / or foamers are, for example, nonionic and anionic emulsifiers, such as polyoxyethylenated esters of fatty acids, polyoxyethylenated ethers of fatty alcohols, for example, alkylaryl polyglycol ether, alkylsulfonates, alkyl sulphates, arylsulfonates, as well as albumin hydrolysates; Dispersants are suitable as dispersants: for example, sulphite lignin liquors and methylcellulose.

In the formulations, adhesives such as carboxymethylcellulose, natural and synthetic polymers powdery, granulable or in the form of latex, such as gum arabic, polyvinyl alcohol, polyvinyl acetate, as well as natural phospholipids such as cefaliña and lecithin, and synthetic phtholipids can be used. Other additives can be mineral and vegetable oils.

Dyes, such as inorganic pigments, for example, iron oxide, titanium oxide, Prussian blue and organic dyes, such as metallic alizarin, azo and phthalocyanine dyes as well as trace nutrients, such as iron salts, manganese, may be employed. , boron, copper, cobalt, molybdenum and zinc.

The formulations contain, in general, between 0.1 and 95% by weight, preferably between 0.5 and 90% of active product.

The active compounds according to the invention can be present in their commercially available formulations as well as in the application forms prepared from these formulations, in admixture with other active ingredients, such as insecticides, baits, sterilizers, acaricides, nematicides, fungicides, growth regulating products or herbicides. Insecticides include, for example, esters of phosphoric acid, carbamates, esters of carbonic acid, chlorinated hydrocarbons, phenylureas, products prepared by means of microorganisms and the like.

Particularly convenient components of the mixture are, for example, the following: Fungicides: 2-Aminobutane; 2-anilino-4-methyl-6-cyclopropylpyrimidine; 2A 6 '-dibromo-2-methyl-4' -trifluoromethoxy-4'-trifluoromethyl-1,3-thiazole-5-carboxanilide; 2,6-dichloro-N- (4-trifluoromethylbenzyl) benzaide; (E) -2-methoxyimino-N-methyl-2- (2-phenoxyphenyl) acetamide; 8-hydroxyquinolinesulfate; methyl- (E) -2-2- [6- (2-cyanophenoxy) pyrimidin-4-yloxy] pheny1-3-methoxy-acrylate; methyl- (E) -methoxyimino [alpha- (o-tolyloxy) -o-tolyl] acetate; 2-Phenylphenol (OPP), Aldi orph, Ampropylfos, Anilazin, Azaconazole, Benalaxyl, Benodanil, Benomyl, Binapacryl, Biphenyl, Bitertanol, Blasticidin-S, Bromuconazole, Bupirimate, Buthiobate, Calciumpolysulfid, Captafol, Captan, Carbendazim, Carboxin, Chinomethionat ( Quino ethionat), Chloroneb, Chloropicrin, Chlorothalonil, Chlozolinat, Cufraneb, Cymoxanil, Cyproconazole, Cyprofuram, Dichlorophen, Diclobutrazol, Diclofluanid. , Diclomezin, Dicloran, Diethofencarb, Difenoconazole Di ethyrimol, Dimethomorph, Diniconazole, Dinocap, Diphenylamin, Dipyrithion, Ditali fos, Dithianon, Dodine, Drazoxolon, Edifenphos, Epoxyconazole, Ethirimol, Ettidiazole, Fenarimol, Fenbuconazole, Fenfuram, Fenitropan, Fenpiclonil, Fenpropidin, Fenpropimorf, Fentinacetat, Fentinhydroxyd, Ferban, Ferimzone, Fluazinam, Fludioxonil, Fluoromide, Fluquinconazole, Flusilazole, Flusulfamide, Flutolanil, Flutriafol, Folpet, Fosetyl-Aluminum, Fthalide, Fuberidazole, Furalaxil, Furmecyclox, Guazatine, Hexachlorobenzene, Hexaconazole, Hymexazole, Imazalil, Imibenconazole, Iminoctadin, Iprobenfos (IBP), Iprodion, Isoprothiolan, Kasugamycin, copper compositions, such as; copper hydroxide, copper naphthenate, copper oxychloride, copper sulfate, copper oxime and mixture of Bordeux, Mancopper, Mancozeb, Maneb, Mepanipyrim, Mepronil, Metalaxyl, Metconazole, Methasulfocarb, Methfuroxan, Metiram, Metsulfovax, Myclobutanil, Nickel dimethyldithiocarbamate , Nitrothal-isopropyl, Nuarimol, Ofurace, Oxadixyl, Oxamocarb, Oxycarboxin, Perfurazoat, Penconazole, Pencycuron, Phosdiphen, Phthalid, Pimaricin, Piperalin, Polycarbamate, Polyoxin, Probenazole, Prochloraz, Procymidon, Propa ocarb, Propiconazole, Propineb, Pyrazophos, Pyrifenox, Pyrimethanil, Pyroquilon, Quintozen (PCNB), Sulfur and Sulfur Compositions, Tebuconazole, Tecloftalam, Tecnazen, Tetraconazole, Thiabendazole, Thicyofen, Thiophanat-methyl, Thiram, Tolclophos-methyl, Tolylfluanid, Triadimefon, Triadimenol, Triazoxid, Trichlamid, Tricyclazole, Tridemorph , Triflumizol, Triforin, Triticonazole, Validamycin A, Vinclozolin, Zineb, Zira.

Bactericides: Bronopol, Dichlorophen, Nitrapyrin, nickel dimethyldithiocarbamate, Kasugamycin, Octhilinon, furancarboxylic acid, Oxytetracyclin, Probenazole, Streptomycin, Tecloftalam, copper sulfate and other copper preparations.

Insecticides / Acaricides / Nematicides: Abamectin, AC 303 630, Acephat, Acrinathrin, Alanycarb, Aldicarb, Alphamethrin, Amitraz, Avermectin, AZ 60541, Azadirachtin, Azinphos A, Azinphos M, Azocyclotin, Bacillus thuringiensis, Bendiocarb, Benfuracarb, Bensultap, Betacyflut rin , Bifenthrin, BPMC, Brofenprox, Bromophos A, Bufencarb, Buprofezin, Butocarboxin, Butylpiridaben, Cadusafos, Carbaryl, Carbofuran, Carbophenothion, Carbosulfan, Cartap, CGA 157 419, CGA 184699, Chloethocarb, Chlorethoxyphos, Chlorfenvinphos, Chlorfluazuron, Chlormephos, Chlorpyrifos, Chlorpyrifos M, Cis-Resmethrin, Clocythrin,. Clofentezin, Cyanophos, Cycloprothrin, Cyfluthrin, Cyhalothrin, Cyhexatin, Cyper ethrin, Cyromazin, Deltamethrin, Demeton M, Detonone S, Demeton-S-methyl, Diafenthiuron, Diazinon, Dichlofenthion, Dichlorvos, Dicliphos, Dicrotophos, Diethion, Diflubenzuron, Di ethoat , Dymethylvinphos, Dioxathion, Disulfoton, Edifenphos, Emamectin, Esfenvalerat, Ethiophencarb, Ethion, Ethofenprox, Ethoprophos, Etrimphos, Fenamiphos, Fenazaquin, Fenbutatinoxid, Fenitrothion, Fenobucarb, Fenothiocarb, Fenoxycarb, Fenpropathrin, Fenpyrad, Fenpyroximat, Fenthion, Fenvalerate, Fipronil, Fluazinam, Flucycloxuron, Flucythrinat, Flufenoxuron, Flufenprox, Fluvalinate, Fonophos, For othion, Fosthiazat, Fubfenprox, Furathiocarb, HCH, Heptenophos, Hexaflumuron, Hexythiazox, Imidacloprid, Iprobenfos, Isazophos, Isofenphos, Isoprocarb, Isoxathion, Ivermectin, Lamda- cyhalothrin, Lufenuron, Malathion, Mecarbam, Mervinphos, Mesulfenphos, Metaldehyd, Methacrifos, Methamidophos, Methidathion, Methiocarb, Methomyl, Metolcarb, Milbemectin, Monocrotophos, Moxidectin, Naled, NC 184, NI 25, Nitenpyram, Omethoat, Oxamyl, Oxydemethon M, Oxydeprofos , Parathion A, Parathion M, Permethrin, Phenthoat, Phorat, Phosalon, Phosmet, Phosphamidon, Phoxim, Pirimicarb, Piri iphos M. Pirimiphos A, Profenofos, Promecarb, Propaphos, Propoxur, Prothiophos, Prothoat, Py etrozin, Pyrachlophos, Pyridaphenthion, Pyres ethrin, Pyrethru, Pyridaben, Pyrimidifen, Pyriproxifen, Quinalphos. RH 5992. Salithion, Sebufos, Silafluofen, Sulfotep, Suiprofos, Tebufenozid, Tebufenpyrad, Tebupirimiphos, Teflubenzuron, Tefluthrin, Temephos, Terbam, Terbufos, Tetrachlorvinphos, Thiafenox, Thiodicarb, Thiofanox, Thiomethon, Thionazin, Thuringiensin, Tralo ethrin, Triarathen, Triazophos, Triazuron, Trichlorfon, Trifluuron, Trimethacarb, Vamidothion, XMC, Xylylcarb, YI 5301/5302, Zetamethrin.

Herbicides: for example, anuidas, such as Diflufenican and Propanil; arylcarboxylic acids, such as dichloropicolinic acid, Dicamba and Picloram; aryloxyalkanoic acids, such as, for example, 2.4 D, 2.4 DB, 2.4 DP, Fluroxypyr, MCPA, MCPP and Triclopyr; esters of the aryloxy-phenoxy-alkanoic acids, such as Diclofop-methyl, Fenoxaprop-ethyl, Fluazifop-butyl, Halaxyfop-methyl and Quizalofop-ethyl; azinones, such as for example Chloridazon and Norflurazon; carbamates, such as for example Chlorpropham; Des edipha, Phenmedipham and Propham; Chloroacetanilides, such as for example Alachlor, Acetochlor, Butachlor, Metazachlor, Metolachlor, Pretilachlor and Propachlor; dinitroanilines, such as for example Oryzalin, Pendimethalin and Trifluralin; diphenylethers, such as for example Acifluorfen, Bifenox, Fluoroglycofen, Fomesafen, Halosafen, Lactofen and Oxyfluorfen; ureas, such as for example Chlortoluron, Diuron, Fluometuron, Isoproturon, Linuron and Methabenzthiazuron; hydroxylamines, such as for example Alloxydim, Clethodim, Cycloxydim, Sethoxydim and Tralkoxydi; imidazolinones, such as, for example, I azethapyr, Imazamethabenz, Imazapyr and Imazaquin; nitriles, such as for example Bromoxynil, Dichlobenil and Ioxynil; Oxyaceta idas, such as for example Mefenacet; sulfonylureas, such as for example Amidosulfuron, Bensulfuronmethyl, Chlorimuron-ethyl, Chlorsulfuron, Cinosulfuron, Metsulfuron-methyl, Nicosulfuron, Primisulfuron, Pyrazosulfuron-ethyl, Thifensulfuron-methyl, Triasulfuron and Tribenuron-methyl; thiocarbamates, such as for example butylates, cycloates, dialates, EPTC, Esprocarb, Molinate, Prosulfocarb, Thiobencarb and Triallate; triazines, such as, for example, Atrazin, Cyanazin, Si azin, Simetryne, Terbutryne and Terbutylazin; triazinones, such as, for example, Hexazinon, Metamitron and Metribuzin; others, such as for example aminotriazole, Benfuresate, Bentazone, Cinmethylin, Clomazone, Clopyralid, Difenzoquat, Dithiopyr, Ethofumesate, Fluorchloridone, Glufosinate, Gliphosate, Isoxaben, Pyridate, Quinchlorac, Quinmerac, Sulphosate and Tridiphane.

The active compounds according to the invention can be present in their commercially available formulations as well as in the application forms prepared from these formulations in a mixture with synergists. The synergists are the compounds by which the effect of the active products is increased, without the synergetic aggregate having to be active in itself.

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

The application is carried out in a manner adapted to the forms of application.

In the use against hygiene pests and stored products, active products are characterized by an excellent residual effect on wood and clay as well as good alkali stability on whitewashed supports.

The active compounds according to the invention are not only active against plant pests, hygiene and stored products, but also in the field of veterinary medicine against animal parasites (ectoparasites) such as hard ticks, soft ticks , scabies mites, migratory mites, flies (suckers and mincers), fly parasitic larvae, lice, hair nits, feathered nits and fleas. To these parasites belong: From the order of the anopluros, for example Haematopinus spp., Linognathus spp., Pediculus spp., Phtirus spp., Solenopotes spp.

Of the order of the malofagidos and the sub-orders amblicerinos as well as isquinocerinos, for example Trimenopon spp., Menopon spp., Trinoton spp., Bovicola spp., Werneckieila spp., Lepikentron spp., Damalina spp., Trichodectes spp., Felicola spp.

From the order of the dipterans and the nematocerine sub-orders as well as brachycerins, for example Aedes spp., Anopheles spp., Culex spp., Simulium spp., Eusi ulium spp., Phlebotomus spp., Lutzomyia spp., Culicoides spp. , Chrysops spp., Hybomitra spp., Atylotus spp., Tabanus spp., Haematopota spp., Philipomyia spp., Braula spp., Musca spp., Hydrotaea spp., Stomoxys spp., Haematobia spp., Morellia spp., Fannia spp., Glossina spp., Calliphora spp., Lucilia spp., Chrysomyia spp., Wohlfahrtia spp., Sarcophaga spp., Oestrus spp., Hypoderma spp., Gasterophilus spp., Hippobosca spp., Lipoptena spp., Melophagus spp. .

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

Of the order of heteropterids, for example Cimex spp., Triatoma spp., Rhodnius spp., Panstrongylus spp.

From the order of the blataridos, for example Blatta orientalis, Periplaneta americana, Blattella germanica, Supella spp.

From the subclass of mites (Acarida) and the order of the meta- as well as mesoestigmatos, for example Argas spp., Ornithodorus spp., Otabius spp., Ixodes spp., Amblyomma spp., Boophilus spp., Dermacentor spp., Haemaphysalis spp., Hyalomma spp., Rhipicephalus spp., Dermanyssus spp., Raillietia spp., Pneumonyssus spp., Sternostoma spp., Varroa spp.

From the order of actinedides (Prostigmata) and acaridids (Astigmata), for example Acarapis spp., Cheyletiella spp., Ornithocheyletia spp., Myobia spp., Psorergates spp., Demodex spp., Trombicula spp., Listrophorus spp., Acarus spp. ., Tyrophagus spp., Caloglyphus spp., Hypodectes spp., Pterolichus spp., Psoroptes spp., Chorioptes spp., Otodectes spp., Sarcoptes spp., Notoedres spp., Knemidocoptes spp., Cytodites spp., Laminosioptes spp.

The active compounds according to the invention of formula (I) are also suitable for the control of arthropods, which attack animals useful in agriculture such as, for example, cows, lambs, goats, horses, pigs, donkeys, camels, buffaloes, rabbits, chickens, turkeys, ducks, geese, bees, other domestic animals such as, for example, dogs, cats, game birds, aquarium fish as well as so-called test animals, such as, for example, hamster , guinea pigs, rats and mice. By fighting against these arthropods death cases and yield reductions (in the case of meat, milk, wool, skins, eggs, honey, etc.) are avoided, so that, by using the active products according to the invention it is possible a more economical and simple maintenance of the animals.

The application of the active compounds according to the invention is carried out in the veterinary field in a known manner by enteral administration in the form of, for example, tablets, capsules, beverages, dragees, granules, pastes, bolis, by means of the process through the "feed-through" food, of suppositories, by parenteral administration, such as, for example, by injection (intramuscular, subcutaneous, intravenous, mtraperitoneal, etc.), and plantlets, by nasal application, by dermal application in the form of , for example dipping or bathing (Dippen), spray (Spray), surface watering (Pour-on and Spot-on), washing, dusting as well as with the aid of moldings containing the active product such as collars, ear tags, tail tags, limb bands, halters, tagging devices, etc.

When they are used for domestic livestock, birds, domestic animals etc. the active compounds (I) can be used as formulations (for example powders, emulsions, agents capable of spreading), containing the active compounds in amounts of 1 to 80% by weight, directly or after dilution of 100 to 10000 times or can be used as a chemical bath.

Furthermore, it has been found that the compounds according to the invention of the formula (I) show a high insecticidal effect against insects, which destroy industrial materials.

By way of example and preference - however without limitation - the following insects may be mentioned: Beetles, such as Hylotrupes ba ulus, Chlorophorus pilosis, Anobiu punctatum, Xestobium rufovillosum, Ptilinus pecticornis, Dendrobium pertinex, Ernobius mollis, Priobium carpini, Lyctus brunneus, Lyctus africanus, Lyctus planicollis, Lyctus linearis, Lyctus pubescens, Trogoxylon aequale, Minthes rugicollis; Xyleborus spec, Tryptodendron spec, Apate monachus, Bostrychus capucins, Heterobostrychus brunneus, Sinoxylon spec., Dinoderus minutus.

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

Termites, such as Kalotermes flavicollis, Cryptotermes brevis, Heterotermes indicala, Reticuliter es flavipes, Reticulitermes santonensis, Reticulitermes lucifugus, Mastotermes darwiniensis, Zootermopsis nevadensis, Coptotermes formosanus.

Thysanides, such as Lepisma saccarina.

By industrial materials, non-living materials will be understood in the present context, such as, preferably, synthetic materials, glues, glues, paper and cardboard, leather, wood and products of wood processing and paints.

In a very special way, the materials to be protected against attack by insects are made of wood and wood products.

For wood and wood processing products, which can be protected by means of the agents according to the invention or of the mixtures containing them, it should be understood, for example: wood for construction wooden beams, railway sleepers, parts for bridges, boat ribs, wooden vehicles, boxes, pallets, containers, telephone poles, wooden coverings, wooden windows and doors, wooden plywood, plywood boards, carpentry works or wood products, which find application, a very general way, in the home or in the construction industry.

The active compounds can be used as such, in the form of concentrates or customary formulations in general, such as powders, granules, solutions, suspensions, emulsions or pastes.

Said formulations can be prepared in a manner known per se, for example by mixing the active ingredients with at least one solvent or diluent, emulsifier, dispersants and / or binder or binding agent, water repellent, if appropriate driers and stabilizers. against UV and, if necessary, dyes and pigments as well as other processing aids.

The insecticidal agents or concentrates to be used for the protection of wood and wood materials contain the active compound according to the invention in a concentration of 0.0001 to 95% by weight, especially 0.001 to 60% by weight.

The amounts of the agents or concentrates used depend on the type and origin of the insects and the environment. The optimum application quantities can be determined respectively by means of series of tests prior to the application. In general, however, it is sufficient to employ from 0.0001 to 20% by weight, preferably from 0.001 to 10% by weight of the active product, based on the material to be protected.

A solvent or a mixture of organochemical solvents and / or a solvent or mixture of organo-chemical, oleaginous or oil-like solvents, which are difficult to volate and / or a solvent or mixture of polar organochemical solvents, is used as solvent and / or diluent. and / or water and, if appropriate, an emulsifier and / or humectant.

The organochemical solvents used are preferably oleaginous or oleaginous solvents, with an evaporation value above 35 and a flame point above 30 ° C, preferably above 45 ° C. By way of such water-insoluble, oil-soluble or oleaginous-type solvents which are difficult to volatile, corresponding mineral oils or their aromatic fractions or mixtures of solvents containing mineral oils, preferably benzine for tests, petroleum and / or alkylbenzene, will be used.

Advantageously mineral oils with a boiling range of 170 to 220 ° C, benzine for tests with a boiling range of 170 to 220CC, spindle oil with a boiling range of 250-350 ° C, petroleum or aromatic hydrocarbons will be used. with a boiling range of 160 to 280 ° C, terpentine oil and the like.

In a preferred embodiment, liquid aliphatic hydrocarbons having a boiling range of 180 to 210 ° C or a high-boiling mixture of aromatic and aliphatic hydrocarbons with a boiling range of 180 to 220 C and / or spindle oil will be used. and / or monochloronaphthalene, preferably a-mono-chloronaphthalene.

Organic, sparingly soluble, oleaginous or oil-like solvents, with an evaporation value above 35 and with a flame point above 30 ° C, preferably above 45 ° C, can be partially replaced by organic solvents. light or medium volatility chemicals, with the proviso that the solvent mixture has an evaporation index above 35 at a flame point above 30 ° C, preferably above 45 ° C, and that the The insecticide-fungicide mixture is soluble or emulsifiable in this mixture of solvents.

According to a preferred embodiment, a part of the solvent or of the mixture of argon-chemical solvents or a solvent or mixture of polar aliphatic organic-chemical solvents is replaced. Preference is given to using aliphatic organochemical solvents containing hydroxyl and / or ester and / or ether groups, such as, for example, glycol ether, esters or the like.

As organic-chemical binders, synthetic resins and / or setting drying oils, known per se, dilutable with water and / or soluble or dispersible or emulsifiable in the organic-chemical solvents used, will be used within the scope of the present invention. especially binders consisting of or containing acrylic resin, a vinyl resin, for example polyvinyl acetate, polyester ream, polycondensation or polyaddition resin, polyurethane ream, alkyd resin or modified alkyd resin, phenolic resin, hydrocarbon resin such as indeno-coumaron resin, silicone resin, vegetable drying and / or drying oils and / or physical drying binders based on a natural and / or synthetic resin.

The synthetic resin, used as a binder, can be used in the form of an emulsion, dispersion or solution. Bitumen or bituminous substances up to 10% by weight can also be used as binders. In a complementary manner, dyes, pigments, water-repelling agents, odor correctors and inhibitors or anticorrosive agents known per se and the like can be used.

It is preferred to use at least one alkyd resin or a modified alkyd resin and / or a drying vegetable oil in the medium or concentrate according to the invention as an organochemical binder. Preferably, alkyd resins having an oil content of greater than 45% by weight, preferably from 50 to 68% by weight, are preferably used according to the invention.

The aforementioned binder can be partially or totally replaced by a fixing agent (mixture) or by a plasticizer (mixture). These additives should avoid volatilization of active products as well as crystallization or precipitation. They preferably replace 0.01 to 30% of the binder (based on 100% of the binder used).

The plasticizers are of the chemical class of phthalic acid esters such as dibutyl, dioctyl or benzylbutyl phthalate, phosphoric acid esters, such as tributyl phosphate, esters of adipic acid, such as di- (D-adipate). 2-ethylhexyl), stearates such as butyl stearate or amyl stearate, oleates such as butyl oleate, glycemic ethers or high molecular weight glycol ethers, glycerin esters as well as esters of p-toluenesulfonic acid.

The binding agents are chemically based on polyvinylalkyl ethers such as polyvinyl methyl ether or on ketones such as benzophenone, ethylenebenzophenone.

Suitable as solvent or diluent is water, if appropriate mixed with one or more of the aforementioned solvents or diluents, emulsifier and organochemical dispersants.

Especially effective protection of the wood is achieved by impregnation processes on an industrial scale, for example vacuum, double vacuum or pressure processes.

The agents ready for application may, if necessary, contain other insecticides and, if appropriate, one or more fungicides.

The insecticides and fungicides mentioned in WO 94/29 268 are preferably used as additional components of the mixture. The compounds mentioned in this document are expressly an integral part of the present application.

Particularly preferred mixing components are insecticides, such as Chloxpyriphos, Phoxim, Silafluofin, Alphamethrin, Cyfluthrin, Cypermethrin, Deltamethrin, Permethrin, Imidacloprid, NI-25, Flufenoxuron, Hexaflumuron and Triflumuron, as well as fungicides such as Epoxiconazole, Hexaconazole. , Azaconazole, Propiconazole, Tebuconazole, Cyproconazole, Metconazole, Imazalil, Dichlorfluanid, Tolylfluanid, 3-iodo-2-propynyl-butylcarbamate, N-octyl-isothiazolin-3-one and 4,5-dichloro-N-octylisothiazolin-3-one .

The preparation and use of the active compounds according to the invention is apparent from the following examples.

Examples Example I-1-a-1.

Add dropwise to 14.05 g (0.125 mole) of potassium tertiarybutylate in 54 ml of absolute tetrahydrofuran (THF) at reflux temperature, 17.3 g of the compound according to example II-1, in 160 ml. of absolute toluene and stirred for another 1.5 hours at this temperature. After cooling, 160 ml of water are added, the phases are separated, the toluene phase is extracted with 80 ml of water and the combined aqueous phases are acidified at 0 to 20 ° C, with concentrated HCl. It is filtered by suction, washed, dried and the product is stirred for further purification with methyl tert -butyl (MTB) -hetero / n-hexane, separated by suction filtration and dried. Yield: 12.1 g (77% of theory), melting point: 200 ° C.

The following compounds of the formula (1-1-a) are prepared analogously or according to the general instructions for preparation: Table 4 Ex «na P.f. ° C I-l-a-2 H CH3 CH, CH, CH, 219 I-1-a-3 H CH 3 CH 3 Br H > 220 I-l-a-4 H H CH3 CH3 H 226 I-l-a-5 H Cl Cl Cl H > 220 I-l-a-6 H H CH3 CH3 CH3 130 I-l-a-7 H H CH3 H CH3 187 I-1-a-8 H Br Cl CH 3 H > 220 I-1-a-9 H H CH 3 Br CH 3 > 220 I-1-a-10 H Cl CH 3 Cl H > 220 I-l-a-11 H H Br CH3 CH3 145 I-l-a-12 H CH3 83 H Br 194 I-1-a-13 H CH, CH 3 CH, Br.

Example (I-l-b-1) 2.88 g (0.010 mole) of the compound according to example (Ila-1) and 2.1 ml (15 mmole) of triethylamine in 50 ml of anhydrous ethyl acetate are combined under reflux with 1.85 ml (0.15 mole) of pivaloyl chloride in 5 ml of anhydrous ethyl acetate. Stir at reflux until the reaction is complete according to the controls performed by thin layer chromatography. For working up, the filtrate is concentrated by evaporation, taken up in methylene chloride, washed twice with 50 ml of 0.5% sodium hydroxide solution, dried over magnesium sulfate and concentrated by evaporation. The crude product is recrystallized from MTB-ether / n-hexane. Performance: 2.0 g (53% of theory). Melting point: 193A. The following compounds of the formula (I-b-1) are prepared analogously or according to the general instructions for preparation: Table 5 E-i. n- V X y z R1 P.f. ° C I-l-b-2 H CH3 CH3 CH3 H i-C3H7 163 I-l-b-3 H CH3 CH3 CH3 CH3 i-C3H7 153 I-l-b-4 H CH 3 CH 3 CH 3 CH 3 2 -thienyl > 220 I-l-b-5 H CH3 CH3 Br H i-C3H7 190 I-1-b-6 H CH 3 CH 3 Br H 2 -thienyl > 220 I-1-b-7 H CH 3 CH 3 Br H 4-Cl-phenyl 209 I-l-b-8 H CH3 H H CH3 i-C3H7 178 I-l-b-9 H CH 3 H CH 3 CH 3 I-C 3 H 7 173 I-l-b-10 H CH3 H CH3 CH3 s-C4H9 193 I-l-b-11 H CH3 H CH3 H 1-C3H7 183 I-l-b-12 H Cl H Cl H i-C3H7 108 Example (I-1-c-1) 2.88 g (0.010 mol) of the compound according to example (Ila-1) and 1.4 ml (0.010 mol) of triethylamine are added dropwise in 50 ml of anhydrous CH2C12 at 0 to 10"C, 1.0 ml. (0.010 mole) of ethyl chloroformate in 5 ml of anhydrous methylene chloride and stirring at room temperature until the reaction is complete according to the controls carried out by thin layer chromatography For the preparation is washed twice with 50 ml of bleach. of 0.5 N sodium hydroxide, dried over magnesium sulfate and concentrated by evaporation Yield: 2.8 g (77% of theory), melting point: 157 ° C.

Analogously or according to the general indications for obtaining the following compounds of formula (I-1-c) are prepared: Table 6 __i__a_ R "P.f. ° C I-l-C-2 H CH. CH-, CH, CH. O 0 C2HS 163 I-l-c-3 H CH, CH, Br H O O C2H5 184 I-l-c-4 H H Cl Cl H O O C2H5 131 Example II-l 51.3 g (0.513 mol) of concentrated sulfuric acid are added dropwise at 30 to 40 ° C, carefully, 29.1 g (0.1016 mol) of the compound according to example (XXV-1) in 310 ml of methylene chloride Anhydrous and stirred for 2 hours at this temperature. Then, 69 ml of absolute methanol are added dropwise in such a way that an internal temperature of about 40 ° C is adjusted and stirred for another 6 hours at 40 to 70 ° C.

For working up, pour over 0.51 kg of ice, extract with methylene chloride, wash with aqueous sodium bicarbonate solution, dry and concentrate by evaporation. The residue is recrystallized from methyl tert-butyl ether / n-hexane. Yield: 17.3 g (53% of theory), melting point: 168 ° C.

The following compounds of the formula (II) are prepared analogously to the example (II-1) and according to the general indications for the preparation.

Table 7 II-2 H CH. CH3 CH3 CH3 CH, 78 II-3 H CH, CH3 Br H CH, 110 II-4 H H CH 3 CH 3 H CH, 68 II-5 H H Cl Cl H CH, 103 II-6 H H CH 3 CH 3 CH 3 CH, 92 II-7 H Br Cl CH3 H CH, 114 II-8 H Cl CH 3 Cl H CH, 204 II-9 H H CH3 H CH3 CH, 74 11-10 H H CH3 H H CH3 85 11-11 H H Br CH3 CH3 CH3 81 11-12 H H CH3 Br CH3 CH3 110 11-13 H CH3 CH3 H Br CH, 134 11-14 H H Cl -O-CF2-0- CH3 121 11-15 H CH, CH. CH, Br CH. 97 Example XXV-1 Add dropwise to 15.8 g of 3-aminotetrahydropyran-3-carbonitrile (according to Example XXIV) and 17.6 ml of triethylamine in 250 ml of absolute THF at 0 to 10 ° C, 25 g of mesityleneacetyl chloride. in 30 ml of absolute THF and stirring, until the reaction is complete. The mixture is introduced under stirring into a mixture of 500 ml of ice water and 200 ml of IN HCl. It is separated by filtration by suction, the residue is taken up in methylene chloride, dried and concentrated by evaporation. Yield 29.1 g (81% of theory), melting point 1531JC.

The following compounds of the formula (XXV) are prepared analogously to the example (XXV-1) or according to the general indications for preparation: Table 8 E1 «P« P.f. ° c XXV-2 H CH3 CH3 CH3 CH3 182 XXV-3 H CH3 CH3 Br H 187 XXV-4 H H CH3 CH3 H 137 XXV-5 H H Cl Cl H 162 XXV-6 H H CH3 CH3 CH3 159 XXV-7 H Br Cl CH3 H 158 XXV-8 H Cl CH3 Cl H 141 XXV-9 H H CH3 H CH3 148 XXV-10 H H CH3 H H 149 XXV-11 • H CH3 CH3 H Br 176 XXV-12 H H Br CH3 CH3 135 XXV-13 H H CH3 Br CH3 166 XXV-14 H H Cl -O-CF20- 115 XXV-15 H CH3 CH, CH, Br 212.

Example I-2-a-1. 18.1 g (0.057 mole) of the compound according to Example III-1 are added dropwise in 30 ml of anhydrous dimethylformamide (DMF) at 10 ° C slowly to 9.58 g (0.085 mole) of tert-butylate of potassium in 10 ml of anhydrous DMF and stirred overnight at room temperature. The DMF is distilled off, the residue is taken up in 1 liter of water and acidified slowly with concentrated HCl. It is separated by suction filtration, washed with water and dried under vacuum at 50 ° C. Melting point 261 C.

Analogously to the example (I-2-a-1) and according to the general routines, the following compounds of the formula (1-2-a) are obtained: Ei »nfi P.f. ° c? -2-a-2 H CH, CH, Cl H 266-269 I-2-a-3 H H CH, CH3 ^ 3 213-214 1-2 -a-4 CH, Br CH3 H 245 I-2-a-5 H CH, CH, Br H 270 I-2-a-6 H CH, Cl C 3 H 248-250 l-2-a-7 H CH, CH, CH, CH "218.

Example I-2-b-l.

Add dropwise to 2.88 g (0.01 mole) of the compound according to Example I-2-al and 1.2 g (0.012 mole) of triethylamine in 30 ml of anhydrous methylene chloride, 1.45 g (0.012 mole) of pivaloyl chloride and stir until the reaction is complete. It is elaborated in the usual way. Yield: 3.47 g, melting point: 108 ° C.

Analogously to the example (I-2-b-1) and according to the general routines, the following compounds of the formula (I-2-b) are prepared: Pj. pß V W X Y z R1 p.f. ° e I-2-b-2 H H CH 3 CH 3 CH 3 I-C 3 H 7 106-107 I-2-b-3 H CH3 CH3 CH3 H i-C3H7 115 I-2-b-4 H CH 3 CH 3 Cl H Í-C 3 H 7 109-110 Bi. na _. g.r. ° c I-2-b-5 H CH. Br CH, H i-C3H7 94 l-2-b-6 H CH, CH: Br H i-C3H7 118 I-2-b-7 H CH, Cl CH, H i-C3H7 96-98 I-2-b-8 H CH, CH, CH, CH 3 i-C 3 H 7 115.

Example I-2-c-l Add dropwise to 2.88 g (0.01 mol) of the compound according to Example I-2-al and 1.2 g (0.012 mol) of triethylamine in 30 ml of anhydrous methylene chloride, 1.64 g (0.012 mol) of isobutyl chloroformate and stir until the reaction is complete. It is elaborated in the usual way. Yield: 3.8 g, melting point: 107 ° C. Analogously to that of the example (I-2-cl) and according to the general indications for the preparation, the following compounds of the formula (I-2-c) are prepared : Pipe "P.f. ° C 1-2 -C-2 H H CH, CH, CH, O Í-C4H9 102-103 I-2-C-3 H CH 3 CH 3 CH, H S Y-C 3 H 7 105-106 I-2-C-4 H CH, CH, CH HO-C4H9 143 1-2 -c-5 H CH, Br CH3 HO-C4H9 89 I-2-C-6 H CH3 CH, Br HO- C4H9 138 I-2-C-7 H CH2 Cl CH3 HO Í-C4H9 90-92 I-2-C-8 H CH, CH, CH, CH, Y-C4H9 95.

Example (I-2-a-2). Analogously to that of example I-2-a-1, compound P.f. is obtained from the compound according to example (III-2). 266-269A.

Example (III-l) g (0.057 mol) of the compound according to example (XXVI) and 11.3 g of 2,4,6-tri-ethylphenyl-acetyl chloride are heated for 6 hours at 140 ° C and then degassed.

Yield 18.1 g of an oil, mass spectrum. (MS) (m / e): 334 (M \ 36%), 160 (38%), 133 (100%).

The following compounds of the formula (III) are obtained analogously to the example (III-1) or according to the general indications for the preparation: Ei - BB P. f. ° C. III-2 H CH3 CH, Cl H oil III-3 H H CH, CH3 CH3 oil III-4 H CH3 Br CH3 H oil III-5 • H CH3 CH3 Br H oil III-6 H CH3 Cl CH3 H oil 111-7 H CH, CH, CH, CH, oil.

Example XXIV.

(XXIV) To the mixture consisting of 222.4 g (3.27 mol) of 25% ammonia solution, 75 g (1.4 mol) of ammonium chloride, 68.7 g (1.4 mol) of sodium cyanide and 210 ml are added dropwise to the mixture. of water, at room temperature, 116.8 g (1.17 moles) of 3-oxa-cyclohexanone-1 (see Bull. Soc. Chim. Fr. (1970), (10), 3521-3) and stirred overnight 45 ° C. After extraction with methylene chloride, 95.2 g (64% of theory) of the above-mentioned compound were obtained, which was used without further purification in the preparation of the compounds of the formula XXV.

Example (XXVI).

The mixture of 89.3 g (0.7 mol) of the compound according to example (XXVIa) is saturated in 420 ml of ethanol, at 0 to -20 ° C, with HCl. It is stirred for a further 1 hour at 0 ° C and allowed to reach room temperature in the course of about 3 hours.

The excess HCl is removed in vacuo, then concentrated by evaporation. The residue is combined with 400 ml of cold water and stirred for 1 hour. It is extracted twice with methylene chloride, dried and concentrated by evaporation. Yield 90 g, P.e.0, 0666 ° C.

Example (XXVIa).

Add dropwise to 85.0 g (0.85 mol) of 3-oxa-cyclohexanone-1 (Bull. Soc. Chim. Fr. (1970) (10), 3521-3) and 0.72 ml of triethylamine, at room temperature. environment, 24.3 g (0.9 moles) of hydrocyanic acid and stirred for 1.5 hours more at room temperature. It is stabilized with 0.12 ml of o-phosphoric acid and is degassed in the vacuum of the water tube. Yield: 102 g (94% of theory).

Application examples: Example A Test with Mizus Solvent: 7 parts by weight of dimethylformamide. Emulsifier: 1 Part by weight of alkylaryl polyglycol ether.

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

Cabbage leaves (Brassica olaracea), which are strongly attacked by the louse of the peach leaf (Myzus persicae), are treated by immersion, with the preparation of active compound at the desired concentration.

After the desired time the destruction is determined in%. In this case 100% means that all the lice in the leaves were destroyed; 0% means that no leaf louse was destroyed.

In this test, they caused, for example, the compounds according to the preparation examples (Ila-2), (Ila-3), (Ilb-2) and (Ilc-1), at an exemplary concentration of the active product of 0.1%, after 6 days, a degree of destruction of 100%.

Example B Test with Nephotettix. Solvent: 20 parts by weight of dimethylformamide.

Emulsifier: 1 Part by weight of alkylaryl polyglycol ether.

Rice seedlings (Oryza sativa) are treated by immersion in the preparation of active compound of the desired concentration and are covered with larvae of green rice cicadas (Nephotettix cincticeps), as long as the seedlings are still moist.

After the desired time the destruction is determined in%. In this case 100% means that all the cicadas were destroyed; 0% means that no cicada was destroyed.

In this test, they caused, for example, the compounds according to the preparation examples (Ila-1), (Ila-2), (Ila-3), (Ilb-1), (Ilb-2), (Ilb-3) , (Ilb-4), (Ilb-5) and (Ilc-3) at an exemplary concentration of the active product of 0.1%, after 6 days, a degree of destruction of 100%.

Example C Phaedon larvae test Solvent: 7 parts by weight of dimethylformamide Estrusant: 1 part by weight of alkylaryl polyglycol ether To obtain a suitable preparation of active compound, 1 part by weight of active compound is mixed with the indicated amount of solvent and with the indicated amount of emulsifier and the concentrate is diluted with water to the desired concentration.

Cabbage leaves (Brassica olaracea) are treated by immersion in the preparation of the active compound at the desired concentration and are covered with larvae of the green horseradish beetle (Phaedon cochleariae), as long as the leaves are still moist.

After the desired time the destruction is determined in%. In this case 100% means that all larvae of the beetles were destroyed; 0% means that no larvae of the beetles were destroyed.

In this test, for example, compounds were produced according to the preparation examples (Ila-1), (1-1-a-2), (Ila-3), (Ilb-1), (Ilb-2), ( Ilb-3), (Ilb-4), (Ilb-5) and (Ilc-1), at an exemplary concentration of the active product of 0.1%, after 7 days, a degree of destruction of 100%.

Example D Test with Spodoptera frugiperda Solvent: 7 parts by weight of dimethylformamide Emulsifier: 1 part by weight of alkylaryl polyglycol ether To obtain a suitable preparation of active compound, 1 part by weight of active compound is mixed with the indicated amount of solvent and with the indicated amount of emulsifier and the concentrate is diluted with water to the desired concentration.

Cabbage leaves (Brassica olaracea) are treated by immersion in the preparation of the active compound at the desired concentration and are covered with larvae of the nocturnal moth (Spodoptera frugiperda), as long as the leaves are still moist.

After the desired time the destruction is determined in%. In this case 100% means that all caterpillars were destroyed; 0% means that no caterpillar was destroyed.

In this test, they caused, for example, the compounds according to the preparation examples (I-1-b-4) and (I-l-c-1), at an exemplary concentration of the active product of 0.1%, after 7 days, a degree of destruction of 100%.

Example E Test with Tetranychus (resistant OP / immersion treatment) Solvent: 3 parts by weight of dimethylformamide Emulsifier: 1 Part by weight of alkylaryl polyglycol ether To obtain a suitable active product preparation, 1 part by weight of the active compound is mixed with the indicated amount of solvent and with the indicated amount of emulsifier and the concentrate is diluted with water to the desired concentration. _p? Bean plants (Phaseolus vulgaris), which are strongly attacked by all stages of development of the common red spider mite or the common red spider mite Tetranychus urticae, are submerged in a preparation of the active compound at the desired concentration.

After the desired time the elimination is determined in%. In this case 100% means that all red spider mites were removed; 0% means that no red spider mite has been removed.

In this test, for example, they elicited the compounds of the preparation examples (I-1-a-1), (I-1-b-1), (I-1-b-2) and (I-1-c-1), at an exemplary concentration of the active product of 0.1%, after 13 days, a degree of destruction of 100%.

It is noted that in relation to this date, the best method known to the applicant, to carry out the aforementioned invention, is that which is clear from the present description of the invention.

Having described the invention as above, property is claimed as contained in the following:

Claims

1. Compound of the formula (I) characterized in that V means hydrogen, halogen, alkyl or alkoxy, W means hydrogen, cyano, nitro, halogen, alkyl, alkenyl, alkynyl, alkoxy, halogenoalkyl, halogenalkoxy or means phenyl, phenoxy, phenylthio, phenylalkoxy or phenylalkylthio respectively substituted, X means halogen, alkyl, alkenyl, alkynyl, alkoxy, halogenoalkyl, halogenoalkoxy, cyano, nitro or means phenyl, phenoxy, phenylthio, phenylalkyloxy or phenylalkylthio respectively substituted, Y means hydrogen, halogen, alkyl, alkoxy, haloalkyl, haloalkoxy, cyano or nitro, Z means hydrogen, halogen, alkyl, alkoxy, haloalkyl, haloalkoxy, hydroxy, cyano, nitro or means phenoxy, phenylthio, hetaryloxy with 5 or 6 members, hetarylthio with 5 or 6 members, phenylalkyloxy or phenylalkylthio, respectively substituted if any, or Y and Z mean, together with the carbon atoms, with which they are linked, a replaced cycle in case 10 and, if necessary, interrupted by one or more heteroatoms, or W and Z signify, together with the carbon atoms, with which they are linked, a substituted cycle if necessary and, if necessary, interrupted by a plurality of 15 heteroatoms, Het means one of the groups Cl where G means hydrogen (a) or means one of the groups RR5 < ß > where E means a metal ion equivalent or an ammonium ion L means oxygen or sulfur, M means oxygen or sulfur, R1 means alkyl, alkenyl, alkoxyalkyl, alkylthioalkyl, or polyalkoxyalkyl respectively substituted, if appropriate, by halogen or by cyano or means cycloalkyl or heterocyclyl substituted, where appropriate, by halogen, alkyl or alkoxy or phenyl, phenylalkyl, hetaryl, phenoxyalkyl or hetaryloxyalkyl respectively substituted, if appropriate, R- means alkyl, alkenyl, alkoxyalkyl or polyalkoxyalkyl, each optionally substituted by halogen or per cyano or means cycloalkyl, phenyl or benzyl substituted respectively where appropriate, R3, R4 and R5, independently of each other, mean alkyl, alkoxy, alkylamino, dialkylamino, alkylthio, alkenylthio or cycloalkylthio respectively substituted, if appropriate, by halogen or phenyl, benzyl, phenoxy or phenylthio sub Where appropriate, R6 and R7, independently of one another, mean hydrogen, meaning alkyl, cycloalkyl, alkenyl, alkoxy, alkoxyalkyl substituted, where appropriate, by halogen or by cyano or phenyl or benzyl, respectively, respectively, or together with the N atom, with which they are bound, they form a cycle containing, if necessary, oxygen or sulfur and, if necessary, substituted.

2. Compounds of the formula (I) according to claim 1, characterized in that V means hydrogen, halogen, alkyl having 1 to 6 carbon atoms or alkoxy with 1 to 6 carbon atoms, W stands for hydrogen, nitro, cyano, halogen, alkyl with 1 to 6 carbon atoms, alkenyl with 2 to 6 carbon atoms, alkynyl with 2 to 6 carbon atoms, alkoxy with 1 to 6 carbon atoms, haloalkyl with 1 a 4 carbon atoms, halogenalkoxy with 1 to 4 carbon atoms or means phenyl, phenoxy, phenylthio, phenyl-alkoxy with 1 to 4 carbon atoms or phenyl-alkylthio with 1 to 4 carbon atoms, substituted, if appropriate, by halogen , by alkyl having 1 to 6 carbon atoms, by alkoxy with 1 to 6 carbon atoms, by halogenalkyl with 1 to 4 carbon atoms, by halogenalkoxy with 1 to 4 carbon atoms, by nitro or by cyano. X means halogen, alkyl with 1 to 6 carbon atoms, alkenyl with 2 to 6 carbon atoms, alkynyl with 2 to 6 carbon atoms, alkoxy with 1 to 6 carbon atoms, haloalkyl with 1 to 4 carbon atoms, halogenalkoxy with 1 to 4 carbon atoms, cyano, nitro or means phenyl, phenoxy, phenylthio, phenyl-alkoxy with 1 atoms of carbon or phenyl-alkylthio having 1 to 4 carbon atoms substituted, where appropriate, by halogen, by alkyl having 1 to 6 carbon atoms, by alkoxy with 1 to 6 carbon atoms, by halogen with 1 to 4 carbon atoms , by haloalkoxy with 1 to 4 carbon atoms, by nitro or by cyano. Y means hydrogen, halogen, alkyl having 1 to 6 carbon atoms, alkoxy with 1 to 6 carbon atoms, halogen with 1 to 4 carbon atoms, halogenalkoxy with 1 to 4 carbon atoms, cyano or nitro. Z means hydrogen, halogen, alkyl having 1 to 6 carbon atoms, alkoxy with 1 to 6 carbon atoms, halagenalkyl with 1 to 4 carbon atoms, halogenalkoxy with 1 to 4 carbon atoms, hydroxy, cyano, nitro or phenoxy phenylthio, thiazolyloxy, pyridinyloxy, pyrimidyloxy, pyrazolyloxy, phenyl-alkoxy with 1 to 4 atoms or phenyl-alkylthio with 1 to 4 carbon atoms substituted, where appropriate, by halogen, with alkyl having 1 to 4 carbon atoms, by alkoxy with 1 to 4 carbon atoms, by haloalkyl with 1 to 4 carbon atoms, by haloalkoxy with 1 to 4 carbon atoms, by nitro or by cyano, or Y and Z signify, together with the carbon atoms, with which they are bonded, alkanediyl having 3 to 5 carbon atoms or alkenodiyl having 3 to 5 carbon atoms substituted, if appropriate, by halogen, with alkyl having 1 to 6 atoms of carbon, by alkoxy with 1 to 6 carbon atoms or by haloalkyl with 1 to 4 carbon atoms, in which, if desired, one to three members may be replaced by oxygen, sulfur, nitrogen or a carbonyl group, independently of each other, or W and Z mean together with the carbon atoms, with which they are bonded, alkanediyl with 3 to 5 carbon atoms or alkenodillo with 3 to 5 carbon atoms substituted, if appropriate by halogen, by alkyl with 1 to 6 carbon atoms, by alkoxy with 1 to 6 carbon atoms or by haloalkyl with 1 to 4 carbon atoms, in which one to three members may be replaced by oxygen, sulfur, nitrogen or a graph upo carbonyl, independently of each other, Het means one of the groups Preferably G means hydrogen (a) or means one of the groups in which E means a metal ion equivalent or an ammonium ion, L means oxygen or sulfur and M means oxygen or sulfur. R * means alkyl with 1 to 20 carbon atoms, alkenyl with 2 to 20 carbon atoms, alkoxy with 1 to 8 carbon atoms-alkyl with 1 to 8 carbon atoms, alkylthio with 1 to 8 carbon atoms-alkyl with 1 to 8 carbon atoms or poly-alkoxy with 1 to 8 carbon atoms-alkyl having 1 to 8 carbon atoms, respectively substituted, if appropriate, by halogen or cyano, or means cycloalkyl having 3 to 8 carbon atoms substituted case given by halogen, by alkyl having 1 to 6 carbon atoms or by alkoxy with 1 to 6 carbon atoms, in which one or two methylene groups, not directly adjacent by oxygen and / or by sulfur, are optionally replaced, means phenyl which is optionally substituted by halogen, by cyano, by nitro, by alkyl with 1 to 6 carbon atoms, by alkoxy with 1 to 6 carbon atoms, by halogenalkyl with 1 to 6 carbon atoms, by haloalkoxy with 1 to 6 carbon atoms, for alkylthio with 1 to 6 carbon atoms or by alkylsulfonyl having 1 to 6 carbon atoms, means phenyl-alkyl having 1 to 6 carbon atoms, optionally substituted by halogen, by nitro, by cyano, by alkyl with 1 to 6 carbon atoms, by alkoxy with 1 to 6 carbon atoms, by halogenalkyl with 1 to 6 carbon atoms or by halogenalkoxy with 1 to 6 carbon atoms, means hetaryl with 5 or 6 members, optionally substituted by halogen or by alkyl with 1 to 6 carbon atoms, with 1 or 2 heteroatoms of the series consisting of oxygen, sulfur and nitrogen means phenoxy-alkyl having 1 to 6 carbon atoms substituted by halogen or by alkyl having 1 to 6 carbon atoms, means hetaryloxy-alkyl with 1 to 6 carbon atoms. carbon, with 5 or 6 members substituted if appropriate by halogen, by amino or by alkyl with 1 to 6 carbon atoms, with 1 or 2 heteroatoms of the series consisting of oxygen, sulfur and nitrogen R means alkyl with 1 to 20 atoms carbon, alkenyl with 2 to 20 carbon volumes, alkoxy having 1 to 8 carbon atoms-alkyl having 2 to 8 carbon atoms or poly-C 1 8 carbon atoms with alkyl 2 8 carbon atoms substituted respectively by halogen or by cyano, means cycloalkyl having 3 to 8 carbon atoms, optionally substituted by halogen, by alkyl with 1 to 6 carbon atoms or by alkoxy with 1 to 6 carbon atoms or means phenyl or benzyl substituted, if appropriate, by halogen, by cyano, by nitro, by alkyl having 1 to 6 carbon atoms, by alkoxy with 1 to 6 carbon atoms, by halogenalkyl with 1 to 6 carbon atoms or by halogenalkoxy with 1 to 6 carbon atoms, R- represents alkyl having from 1 to 8 carbon atoms substituted, if appropriate, by halogen or means phenyl or benzyl substituted, where appropriate, by halogen, by alkyl having 1 to 6 carbon atoms, by alkoxy with 1 to 6 carbon atoms, by halogenalkyl with 1 to 4 carbon atoms, by halogenalkoxy with 1 to 4 carbon atoms, by cyano or by nitro, R4 and R5 mean, independently of each other, alkyl with 1 to 8 carbon atoms, alkoxy with 1 to 8 carbon atoms, alkylamino with 1 to 8 carbon atoms, di- (alkyl with 1 to 8 carbon atoms) amino, alkylthio with 1 to 8 carbon atoms or alkenylthio with 3 to 8 carbon atoms, respectively substituted, if appropriate, by halogen or by phenyl, phenoxy or phenylthio each substituted, where appropriate, by halogen, by nitro, by cyano, by alkoxy with 1 to 8 carbon atoms; to 4 carbon atoms, for halogenalkoxy with 1 to 4 carbon atoms, for alkylthio with 1 to 4 carbon atoms, for halogenalkylthio with 1 to 4 carbon atoms, for alkyl with 1 to 4 carbon atoms or for haloalkyl with 1 to 4 carbon atoms, Rh and R 1, independently of one another, hydrogen, mean alkyl having 1 to 8 carbon atoms, cycloalkyl with 3 to 8 carbon atoms, alkoxy with 1 to 8 carbon atoms, alkenyl with 3 to 8 carbon atoms or alkoxy with 1 to 8 carbon atoms-alkyl having 2 to 8 carbon atoms substituted, where appropriate, by halogen or cyano, means phenyl or benzyl substituted, where appropriate, by halogen, by alkyl having 1 to 8 carbon atoms, by haloalkyl with 1 to 8 carbon atoms or by alkoxy with 1 to 8 carbon atoms or together they mean an alkylene radical having 3 to 6 carbon atoms, optionally substituted by alkyl having 1 to 6 carbon atoms, in which it is replaced in case given a methylene group by oxygen or by sulfur,

3. Compound of the formula (I) according to claim 1, characterized in that V means hydrogen, fluorine, chlorine, bromine, alkyl with 1 to 4 carbon atoms or alkoxy with 1 to 4 carbon atoms, W stands for hydrogen, nitro, cyano, fluorine, chlorine, bromine, alkyl with 1 to 4 carbon atoms, alkoxy with 1 to 4 carbon atoms, halogenalkyl with 1 to 2 carbon atoms, halogenalkoxy with 1 to 2 carbon atoms or means phenyl, phenoxy or benzyloxy substituted, where appropriate, by fluorine, chlorine, bromine, alkyl with 1 to 4 carbon atoms, alkoxy with 1 to 4 carbon atoms, halogenalkyl with 1 to 2 carbon atoms, by halogenalkoxy with 1 to 2 carbon atoms, by nitro or by cyano, X means fluorine, chlorine, bromine, alkyl having 1 to 4 carbon atoms, alkoxy with 1 to 4 carbon atoms, halogenalkyl with 1 to 2 carbon atoms, halogenalkoxy with 1 to 2 carbon atoms, cyano, nitro or means phenyl , phenoxy or benzyloxy substituted, where appropriate, by fluorine, chlorine, bromine, alkyl with 1 to 4 carbon atoms, alkoxy with 1 to 4 carbon atoms, haloalkyl with 1 to 2 carbon atoms, halogenalkoxy with 1 to 2 carbon atoms, by nitro or by cyano, Y means hydrogen, fluorine, chlorine, bromine, aikyl with 1 to 4 carbon atoms, alkoxy with 1 to 4 carbon atoms, halogenalkyl with 1 to 2 carbon atoms, halogenalkoxy with 1 to 2 carbon atoms, cyano or nitro, Z means hydrogen, fluorine, chlorine, brominealkyl with 1 to 4 carbon atoms, alkoxy with 1 to 4 carbon atoms, haloalkyl with 1 to 2 carbon atoms, haloalkoxy with 1 to 2 carbon atoms, hydroxy, cyano, nitro or means phenoxy or benzyloxy substituted respectively in case given by fluorine, chlorine, bromine, alkyl with 1 to 4 carbon atoms, alkoxy with 1 to 4 carbon atoms, halogenalkyl with 1 to 2 carbon atoms, halogenalkoxy with 1 to 2 carbon atoms , by nitro or by cyano, or Y and Z signify, together with the carbon atoms, with which they are bonded, alkanediyl having 3 to 4 carbon atoms or alkenodiyl having 3 to 4 carbon atoms, respectively substituted, if appropriate, by fluorine, chlorine, bromine, alkyl with 1 to 4 carbon atoms, for alkoxy with 1 to 4 carbon atoms or for halogenalkyl with 1 to 2 carbon atoms, in which 1 or 2 non-directly adjacent members can be replaced by oxygen, sulfur or by nitrogen, independently of each other, or W and Z mean together with the carbon atoms, with which they are bonded, alkanediyl having 3 to 4 carbon atoms or alkenodiyl having 3 to 4 carbon atoms, respectively substituted, if appropriate, by fluorine, chlorine, bromine, alkyl with 1 to 4 carbon atoms, for alkoxy with 1 to 4 carbon atoms or for halogenoalkyl with 1 to 2, carbon atoms, in which one or two non-directly adjacent members can be replaced by oxygen, sulfur or nitrogen, Het means one of the groups G means hydrogen (a) or means one of the groups wherein E means an equivalent of metal ion or an ammonium ion, L means oxygen or sulfur and M means oxygen or sulfur, R1 means alkyl with 1 to 16 carbon atoms, alkenyl with 2 to 16 carbon atoms, alkoxy with 1 C 6 -alkyl-C 1-6 -alkyl, C 1-6 -alkylthio-C 1-6 -alkyl, or C 1-6 -alkoxy-C 1-6 -alkyl with 1 to 6 C atoms of carbon substituted respectively by fluorine or by chlorine or by cycloalkyl with 3 to 7 carbon atoms, optionally substituted by fluorine, by chlorine, by alkyl with 1 to 5 carbon atoms or by alkoxy with 1 to 5 carbon atoms of carbon, in which one or two methylene groups directly adjacent to one another are replaced by oxygen and / or sulfur, means phenyl substituted, if appropriate, by fluorine, by chlorine, by bromine, by cyano, by nitro, by alkyl with 1 to 4 carbon atoms, by alkoxy with 1 to 4 atoms carbon atoms, by halogenalkyl with 1 to 3 carbon atoms, by halogenalkoxy with 1 to 3 carbon atoms, by alkylthio with 1 to 4 carbon atoms or by alkylsulfonyl with 1 to 4 carbon atoms, means phenyl-alkyl with 1 to 4 carbon atoms. at 4 carbon atoms optionally substituted by fluorine, chlorine, bromine, alkyl with 1 to 4 carbon atoms, alkoxy with 1 to 4 carbon atoms, halogenalkyl with 1 to 3 carbon atoms or halogenalkoxy with 1 a 3 carbon atoms, means pyrazolyl, thiazolyl, pyridyl, pyrimidyl, furanyl or thienyl, respectively substituted, if appropriate, by fluorine, chlorine, bromine or alkyl with 1 to 4 carbon atoms, means phenoxy-alkyl with 1 to 5 atoms of carbon, optionally substituted by fluorine, by chlorine, by bromine 0 by alkyl with 1 to 4 carbon atoms or means pyridyloxy-alkyl with 1 to 5 carbon atoms, pyrimidyloxy-alkyl with 1 to 5 carbon atoms or thiazolyloxy-alkyl with 1 to 5 carbon atoms, respectively substituted by fluorine, chlorine, bromine, amino or alkyl with 1 to 4 carbon atoms, means alkyl with 1 to 16 carbon atoms, alkenyl with 2 to 16 carbon atoms, alkoxy with 1 to 6 carbon atoms-alkyl having 2 to 6 carbon atoms or poly-alkoxy with 1 to 6 carbon atoms-alkyl with 2 to 6 carbon atoms substituted, respectively, by fluorine or chlorine, means cycloalkyl having 3 to 7 carbon atoms, optionally substituted by fluorine, chlorine, alkyl with 1 to 4 carbon atoms or alkoxy with 1 to 4 carbon atoms; to 4 carbon atoms, or means phenyl or benzyl substituted respectively by fluorine, by chlorine, by bromine, by cyano, by nitro, by alkyl with 1 to 4 carbon atoms, by alkoxy with 1 to 3 carbon atoms , by halogenalkyl with 1 to 3 carbon atoms or by halogenalkoxy with 1 to 3 carbon atoms, RJ means alkyl having 1 to 6 carbon atoms, optionally substituted by fluorine or by chlorine or means phenyl or benzyl, respectively substituted, if appropriate, by fluorine, chlorine, bromine, alkyl with 1 to 4 carbon atoms, alkoxy with 1 to 4 carbon atoms, for halogenalkoxy with 1 to 2 carbon atoms, for halogenalkyl with 1 to 2 carbon atoms, for cyano or for nitro, P ^ and R5 mean, independently of each other, alkyl having 1 to 6 carbon atoms, alkoxy with 1 to 6 carbon atoms, C 1 -C 6 -alkylamino, di- (C 1 -C 6 -alkyl) amino, C 1 -C 6 -alkylthio or alkenylthio with 3 to 4 carbon atoms substituted, respectively, by fluorine or chlorine or phenyl, phenoxy, or phenylthio substituted respectively by fluorine, by chlorine, by bromine, by nitro, by cyano, by alkoxy with 1 to 3 carbon atoms, by halogenalkoxy with 1 to 3 carbon atoms, alkylthio with 1 to 3 carbon atoms, for halogenalkylthio with 1 to 3 carbon atoms, for alkyl with 1 to 3 carbon atoms or for halogenalkyl with 1 to 3 carbon atoms, they mean, independently of each other, hydrogen, they mean alkyl with 1 to 6 carbon atoms, cycloalkyl with 3 to 6 carbon atoms, alkoxy with 1 to 6 carbon atoms, alkenyl with 3 to 6 carbon atoms or alkoxy with 1 to 6 Carbon-alkyl atoms having 2 to 6 carbon atoms, respectively substituted, if appropriate, by fluorine or chlorine, means phenyl or benzyl substituted, where appropriate, by fluorine, chlorine, bromine, halogen with 1 to 5 carbon atoms , by alkyl with 1 to 5 carbon atoms or by alkoxy with 1 to 5 carbon atoms, together they mean an alkylene radical having 3 to 6 carbon atoms, optionally substituted by alkyl with 1 to 4 carbon atoms, which is optionally replaced by a methylene group by oxygen or by sulfur.

4. Compound of the formula (I) according to claim 1, characterized in that V means hydrogen, fluorine, chlorine, bromine, methyl, ethyl, propyl, iso-propyl, tert-butyl, methoxy, ethoxy, propoxy or iso-propoxy, W stands for hydrogen, nitro, cyano, fluorine, chlorine, bromine, methyl, ethyl, propyl, n-butyl, iso-propyl, isobutyl, methoxy, ethoxy, propoxy, iso-propoxy, trifluoromethyl, difluoromethoxy, trifluoromethoxy, phenyl or benzyloxy, X means fluorine, chlorine, bromine, methyl, ethyl, propyl, butyl, iso-butyl, iso-propyl, methoxy, ethoxy, propoxy, iso-propoxy, trifluoromethyl, trifluoromethoxy, difluoromethoxy, cyano, nitro, phenyl or benzyloxy, Y means hydrogen, fluorine, chlorine, bromine, methyl, ethyl, propyl, iso-propyl, n-butyl, iso-butyl, tert-butyl, methoxy, ethoxy, propoxy, iso-propoxy, trifluoromethyl, trifluoromethoxy, difluoromethoxy, cyano or nitro, Z means hydrogen, fluorine, chlorine, bromine, methyl, ethyl, propyl, butyl, iso-butyl, iso-propyl, tert-butyl, methoxy, ethoxy, propoxy, iso-propoxy, trifluoromethyl, trifluoromethoxy, difluoromethoxy, cyano or nitro, or Y and Z signify together with the carbon atoms, to which they are bonded, alkanediyl having 3 to 4 carbon atoms, optionally substituted by fluorine, chlorine, methyl, ethyl, propyl, isopropyl, methoxy, by ethoxy, by propoxy, by iso-propoxy or by trifluoromethyl, in which two not directly adjacent members are replaced by oxygen or W and Z mean together with the carbon atoms, to which they are bonded, alkanediyl having 3 to 4 carbon atoms, optionally substituted by fluorine, chlorine, methyl, ethyl, propyl, isopropyl, methoxy, by ethoxy, by propoxy, by iso-propoxy or by trifluoromethyl, in which two members not directly adjacent to one another are replaced by oxygen, Het means one of the groups G means hydrogen (a) or means one of the groups < and). wherein E means an equivalent metal ion or an ammonium ion, L means oxygen or sulfur and M means oxygen or sulfur, R "means alkyl with 1 to 14 carbon atoms, alkenyl with 2 to 14 carbon atoms, alkoxy with 1 to 4 carbon atoms-alkyl having 1 to 6 carbon atoms, alkylthio having 1 to 4 carbon atoms-alkyl having 1 to 6 carbon atoms, poly-alkoxy with 1 to 4 carbon atoms-alkyl having 1 to 4 carbon atoms carbon atoms substituted, where appropriate, by fluorine or by chlorine or means cycloalkyl having 3 to 6 carbon atoms, optionally substituted by fluorine, chlorine, methyl, ethyl, n-propyl, i-propyl, n-butyl, by i-butyl, by tert-butyl, by methoxy, by ethoxy, by n-propoxy or by iso-propoxy, in which one or two methylene groups directly adjacent to one another are replaced by oxygen and / or or by sulfur, means phenyl substituted, if appropriate, by fluorine, by chlorine, by bromine, by cyano, by nitr or, by methyl, ethyl, n-propyl, i-propyl, methoxy, ethoxy, trifluoromethyl, trifluoromethoxy, methylthio, ethylthio, methylsulfonyl or ethylsulfonyl, means benzyl optionally substituted by fluorine, by chlorine, by bromine, by methyl, by ethyl, by n-propyl, by i-propyl, by methoxy, by ethoxy, by trifluoromethyl or by trifluoromethoxy, means furanyl, thienyl or pyridyl respectively substituted, if appropriate by fluorine, by chlorine, bromine, methyl or ethyl, means phenoxy-alkyl having 1 to 4 carbon atoms, optionally substituted by fluorine, chlorine, methyl or ethyl or pyridyloxy-alkyl having 1 to 4 carbon atoms, pyrimidyloxy-C 1 -C 4 -alkyl, or thiazolyloxy-C 1 -C 4 -alkyl optionally substituted by fluorine, chlorine, amino, methyl or ethyl, means alkyl having 1 to 14 carbon atoms, alkenyl having 2 to 14 carbon atoms, alkoxy having 1 to 4 carbon atoms-alkyl having 2 to 6 carbon atoms or poly-alkoxy having 1 to 4 carbon atoms - alkyl having 2 to 6 carbon atoms substituted respectively by fluorine or chlorine, means cycloalkyl having 3 to 6 carbon atoms, optionally substituted by fluorine, chlorine, methyl, ethyl, n-propyl, iso- propyl or methoxy, or phenyl or benzyl respectively substituted, if appropriate, by fluorine, by chlorine, by cyano, by nitro, by methyl, by ethyl, by n-propyl, by i-propyl, by methoxy, by ethoxy, by trifluoromethyl or trifluoromethoxy, R3 means methyl, ethyl, propyl, iso-propyl, n-butyl, tert-butyl, respectively substituted, if appropriate, by fluorine or by chlorine or means phenyl or benzyl substituted, if appropriate by fluorine, by chlorine, respectively , by bromine, by methyl, by ethyl, by isopropyl, by tert-butyl, methoxy, ethoxy, iso-propoxy, trifluoromethyl, trifluoromethoxy, cyano or nitro, R4 and R5 mean, independently of each other, alkyl having 1 to 4 carbon atoms, alkoxy with 1 to 4 carbon atoms, alkylamino having 1 to 4 carbon atoms, di- (C1 to 4 carbon alkyl) amino or alkylthio having from 1 to 4 carbon atoms, respectively substituted by fluorine or by chlorine, or by phenyl, phenoxy or phenylthio substituted, where appropriate, by fluorine, chlorine, bromine, nitro, cyano, methyl, methoxy , by trifluoromethyl or by trifluoromethoxy, R6 and R stand for, independently of one another, hydrogen, meaning alkyl with 1 to 4 carbon atoms, cycloalkyl with 3 to 6 carbon atoms, alkoxy with 1 to 4 carbon atoms, alkenyl with 3 to 4 carbon atoms or alkoxy with 1 to 4 carbon atoms-alkyl having 2 to 4 carbon atoms substituted, if appropriate, by fluorine or chlorine, means phenyl or benzyl, optionally substituted, respectively, by fluorine, chlorine, bromine, methyl, methoxy or by trifluoromethyl or together they mean an alkylene radical having 5 or 6 carbon atoms, optionally substituted by methyl or ethyl, in which, if appropriate, a methylene group is replaced by oxygen or by sulfur.

5. Process for obtaining compounds of the formula (I) according to claim 1, characterized in that (A) the compounds of the formula (I-1-a) are obtained (I-1-a) in which V, W, X, Y and Z have the meanings in the claim 1, if compounds of the formula are condensed intramolecularly (II) wherein V, W, X, Y and Z have the above meanings, and R "means alkyl in the presence of a diluent and in the presence of a base, (B) the compounds of the formula (I-2-) are obtained to) wherein V, W, X, Y and Z have the meanings indicated above, if compounds of the formula (III) are condensed intramolecularly wherein V, W, X, Y, Z and R8 have the meanings indicated above, in the presence of a diluent and in the presence of a base, X) the compounds of the formula (I-3-a) are obtained wherein V, W, X, Y and Z have the meanings indicated above, if compounds of the formula (IV) are intramolecularly cyclized wherein V, W, X, Y, Z and R * have the meanings indicated above, and T means hydrogen, halogen, alkyl or alkoxy, if appropriate in the presence of a diluent and in the presence of an acid, and then in given the compounds thus obtained from the formulas indicated above (Ila) to (I-3-a) in which V, W, X, Y and Z have the meanings indicated above, respectively (D) a) are reacted with acyl halides of the formula (V) wherein R1 has the meaning indicated in claim 1 and Hal means halogen, or ß) with anhydrides of carboxylic acids of the formula (VI) R ^ CO-O-CO-R1 (VI) wherein R "has the meaning indicated above, if appropriate in the presence of a diluent and, if appropriate, in the presence of an acid-binding agent; (E) are reacted with esters of chloroformic acid or with thioesters of chloroformic acid of the formula (VII) R2-M-C0-C1 (VII) wherein R: and M have the meanings indicated above, if appropriate in the presence of a diluent and, if appropriate, in the presence of an acid-accepting agent; (F) are reacted with esters of chloromonothioformic acid or with esters of chlorodithioformic acid of formula (VIII) C wherein M and R: have the meanings indicated in claim 1, optionally in the presence of a diluent and, if appropriate, in the presence of an acid-binding agent, or (G) are reacted with sulfonyl chlorides of the formula (IX) R¿-S0-C1 (IX) wherein RJ has the meaning indicated in claim 1, if appropriate in the presence of a diluent and, if appropriate, in the presence of an acid-accepting agent; or (H) are reacted with phosphorus compounds of the formula (X) R4 / Hal-P (X) L Rs wherein L, R4 and R "have the meanings indicated in claim 1 and Hal means halogen, if appropriate in the presence of a diluent and, if appropriate, in the presence of an acid-binding agent or (I) are reacted with metal compounds or with amines of the formulas (XI) or (XII) Me (ORX IX: 10 in which Me means a mono or divalent metal, t means the numbers 1 or 2 and R ", R", R ", independently of one another, signify hydrogen or alkyl, if appropriate in the presence of a diluent, (J) a) are reacted with isocyanates or with isothiocyanates of the formula (XIII), R'-N = C = L (XIII wherein RÉ and L have the meanings indicated in claim 1, if appropriate in the presence of a diluent and, if appropriate, in the presence of a catalyst, or ß) are reacted with carbamidyl chlorides or with thiocarbamidyl chlorides of the formula (XIV) wherein L, R6 and R7 have the meanings indicated in claim 1, if appropriate in the presence of a diluent and, if appropriate, in the presence of an acid-accepting agent.

6. Compound of the formula (II) (i ") characterized in that V, W, X, Y and Z have the meanings indicated in claim 1, and R8 means alkyl

7. Compound of the formula (XVII) characterized in that V, W, X, Y and Z have the meanings indicated in claim 1.

8. Compound of the formula (XXV) characterized in that V, W, X, Y and Z have the meanings indicated in claim 1.

9. Compound of the formula (III) characterized in that V, W, X, Y, and Z have the above indicated meanings and Rs means alkyl.

10. Compounds of the formula (XXVI) characterized in that R "means alkyl

11. Compound of the formula (IV) characterized in that T, V, W, X, Y, and Z have the meanings indicated above and Rd means alkyl.

12. Compounds of the formula (XXVII. ' (XXVII) characterized in that T means hydrogen, halogen, alkyl or alkoxy, Hal means halogen.

13. The compound of the formula (XXIV)

14. Composite of the formula characterized in that R "means alkyl.

15. The compound of the formula CO-H (XVIII) NH,

16. Pesticide agents or agents. herbicides, characterized in that they have a content in a compound of the formula (I) according to claim 1.

17. Use of the compounds of the formula (I) according to claim 1, characterized in that they fight against pests and against weeds.

18. Procedure for the control of the Q pests and against weeds, characterized in that the compounds of the formula (I), according to claim 1, are allowed to act on the pests or on the weeds and / or on their environment.

19. Process for obtaining pesticides and herbicidal agents, characterized in that compounds of the formula (I) according to claim 1 are mixed with extenders and / or surfactants. 0 5