MXPA00002937A - Utilizing spirocyclic phenyl keto-enols as pesticides and herbicides - Google Patents

Abstract

The invention relates to novel spirocyclic phenyl keto-enols of general formula (I) in which Het represents one of the groups (1), (2) or (3), Q represents (A);(B);(C);(D);(E) or (F), and X, Y, Z, m, n, R6, R9, R10, R11 have meanings given in the description. The invention also relates to further methods and intermediate products for the production of said spirocyclic phenyl keto-enols and the utilization thereof as pesticides and herbicides.

Description

PHYCYCLETHENOLS ESPIROCYCLIC AS PESTICIDES AND HERBICIDES. Field of the invention. The invention relates to new spirocyclic ilketoenols, to various processes and to intermediates for their preparation and their use as pesticides and herbicides. Description of the prior art. It has already been disclosed that certain cyclic ketoenols, phenylsubstiruides, are active as insecticides, acaricides or herbicides, for example the derivatives of lH-aryl pyrrolidine (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 95/26 954, WO 95/20 572, EP -A-0 668 267, WO 96/25 395, WO 96/35 664, WO 97/01 535 and WO 97/02 243). It is also known that certain substituted? '-dihydrofuran-2-one derivatives have herbicidal properties (cf. DE-A-4 014 420). It has also been described in DE-A-4 014 420 the synthesis of the tetronic acid derivatives, used as starting compounds (such as, for example, 3- (2-methyl-phenyl) -4-hydroxide. -5- (4-Fluorophenyl) -?, - dihydrofuranone- (2)). It is known from the publication Campbell ct al .. J. Chem. Soc, Perkin Trans, 1. 1985, (8) 1567-76 structured compounds in a similar manner without indication of an insecticidal and / or acaricidal activity. Furthermore, 3-aryl-3-dihydrofuranone derivatives with herbicidal, acaricidal and insecticidal properties are known from EP-A-528 156, EP-A-0 647 637. WO 95/26345, WO 96/20 196, WO 96/25 395, WO 96/35 664, WO 97/01 535. WO 97/02 243 and WO 97/36 868. However, the activity and spectrum of activity of these compounds are not always completely satisfactory especially in the case of amounts of REF. 32984 application and low concentrations. Furthermore, the compatibility with plants of these compounds is not always sufficient. DETAILED DESCRIPTION OF THE INVENTION New compounds of the formula (I) have been found wherein X means halogen, alkyl, alkenyl, alkynyl, alkoxy. alkenyloxy, alkylthio, alkylsulfonyl. alkylsulfonyl. haloalkyl, haloalkenyl, haloalkoxy. haloalkenyloxy, nitro, cyano or means phenyl. phenoxy, phenylthio. benzyloxy or benzylthio substituted respectively, if appropriate. Y means hydrogen, halogen, alkyl, alkenyl. alkynyl. alkoxy alkenyloxy. alkyone. alkylsulfinyl, alkylsulfonyl. haloalkyl. haloalkenyl. halogenoalcoxy. haloalkeniioxy. nitro or cyano. Z means halogen, alkyl, alkenyl. alkynyl. haloalkyl. haloalkenyl. alkoxy alkenyloxy. halogenoalcoxy. haloalkenyloxy. nitro or cyano, n means 0. 1, 2 or 3, Het means one of the groups (2) or where G means hydrogen (a) or means one of the groups (and). 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. optionally substituted alkylthioalkyl or polyalkoxyalkyl means cycloalkyl optionally substituted by halogen, by alkyl or by alkoxy, which may be interrupted by one or more heteroatoms or means phenyl. phenylalkyl. hetaryl, phenoxyalkyl or hetaryloxyalkyl respectively substituted, R: means alkyl, alkenyl. alkoxyalkyl or polyhaloalkyl substituted respectively by halogen or cycloalkyl. phenyl or benzyl substituted respectively, if appropriate. R RJ > R ?, independently of each other. they mean alkyl, alkoxy. alkylamine, dialkylamino, alkylthio, alkenylthio or cycloalkylthio substituted, where appropriate by halogen or by phenyl, benzyl, phenoxy or phenylthio respectively substituted, if appropriate, R6 and R7, independently of one another, mean hydrogen, meaning alkyl, cycloalkyl, alkenyl, alkoxy or alkoxyalkyl substituted, where appropriate, by halogen, can mean substituted phenyl, optionally substituted benzyl, or, together with the N atom, to which they are attached, they mean a ring containing, if appropriate, oxygen or sulfur, What does it mean 11 OR \ / \ / C- N-N \ 11 10 / R OR Ru means hydrogen, means alkyl, cycloalkyl, phenyl, benzyl or hetaryl substituted respectively if appropriate, or means CO-R1: CO: -R :: SO -R '; 1 ! R / CONH. , CONHRn or CO- \ 12 R R "'means hydrogen or alkyl, R" means alkyl or alkenyl, R ?: means alkyl or alkenyl, m means 0, l or 2, R independently of R' nene the meanings given above for R R: independently of R has the meanings indicated above for R :.

The compounds of the formula (I) can also be present, depending on the type of substituents, in the form of geometrical and / or optical isomers or mixtures of isomers, with a variable composition. Which can be separated, if necessary, in the usual manner and manner. Both the pure isomers and also the mixtures of the isomers, their preparation and use, as well as the agents containing them, constitute an object of the present invention. However, the compounds of the formula (I) will always be discussed below in order to simplify even when both the pure compounds and, where appropriate, also mixtures with variable proportions of the isomeric compounds are indicated. • Taking into account the meanings (1) to (3) of the Het group, the following main structures (1-1) to (1-3) are produced: where Q. G. X, Y, Z, n and m have the meanings indicated above Taking into consideration the various meanings (a), ib), (c). (from). (f) > (g) of group G the following main structures (I-1 -a) are produced (I-1-g), when Het means group (1).

(I-l-c): (-): (i- i -g) where E. L. M. Q, X. Y. Z. n. m. R1 R \ R ?, R, R RL 'and R ~ have the meanings indicated above. T taking into consideration the different meanings (a), (b). (c), (d). (e), (f) and (g) of group G are produced structures (I-2-a) through (I-2-g), next major, when Het means group (2), (i-i-s) where E. L, M, Q, X, Y, Z, n, m, R \ R \ R \ R4, R5, R ° and R7 have the meanings 0 previously indicated. Taking into account the various meanings (a), (b), (c), (d), (e), (f) and (g) of group G, the structures (I-2-a) are produced up to (I) -2-g), next major, when Het means group (2), (I -2-a) (I-2-b) C (I-2-c) (I-2-d) (I-2-e): (I-2-f): (I-2-g): where E, L, M, Q. X, Y, Z, n. m, R :, R :. R \ R \ R \ R "and RP have the meanings indicated above, taking into consideration the various meanings (a), (b), < c), (d), (e), (0 and (g) of the group G the following structures are produced (i-3-a) through (I-3-g), when Het means group (3). (I-3-a) (I-3-b) (I-3-c) (I-3-d) (I-3-e) (I-3-f) (I-3-g) where E, L. M, Q, X, Y, Z. n. m. R. R :. R. R "R \ R '\ R ~ have the meanings indicated above. It has also been found that the new compounds of the formula" (I) are obtained according to one of the procedures described below (A). 3-Phenylpyrrolidone is obtained? d? n-2.4-d? onas replaced or else their enols of the formula (I- l -a) wherein Q, X, Y, Z, m and n have the meanings indicated above, if N-acylamino acid esters of the formula (II) are condensed intromolecularly where Q, X, Y, Z, m and n have the meanings indicated above. and R1, means alkyl (preferably alkyl having 1 to 6 carbon atoms in the presence of a diluent in the presence of a base) (B) In addition, it has been found that the 3-phenol-4- derivatives are obtained. substituted hydroxyl-? '- dihydrofuranone of the formula (I-2-a) wherein Q. X, Y, Z, m and n have the meanings indicated above, if carboxylic acid esters of the formula (III) are condensed intramolecularly, where Q. X, Y. Z, m. n and R 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 substituted 3-phenyl-4-hydroxy-3-dihydrotyl-ofenone derivatives of the formula (I-3-a) are obtained. wherein Q, X, Y, Z, m and n have the meanings indicated above, if ß-ketocarboxylic acid esters of the formula are intramolecularly cyclized (IV) where Q. X. (D), Z, m. n and R 'have the meanings indicated above and W means hydrogen, halogen, alkyl, preferably alkyl having 1 to 6 carbon atoms or alkoxy (preferably alkoxy with 1 to 8 carbon atoms), in the presence of a diluent and in the presence of a acid. It has further been found that the compounds of the above-indicated formulas (I-1-b) to (I-3-b) are obtained. cn which (E) Q. X, Y, Z. m, n and R; they have the meanings indicated above, if compounds of the previously indicated formulas (I-1-a) are converted to (I-3-a). in which Q, XYZ m and n have the meanings indicated above, respectively x) with acyl chlorides of the formula (V) in which R has the meanings 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-R 1 (VI) in which R 1 has the meanings given above, optionally 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 (I-1-c) are obtained up to (I-3-c), in which Q. R :. MXY 2. m \ n have the meanings indicated above and L means oxygen, if compounds of the formulas indicated above (I-l -a) are reacted to (I-3-a), in which QX Y, Z. m \ n have the meanings indicated above, respectively with esters of chloroformic acid or thiol esters of chloroformic acid of the formula (VII) R: -M-CO-CI (VII) in which 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: (G) that the compounds of the formulas indicated above (Ilc) are obtained up to (1-3-c), which Q, R2, M, X, Y, Z, m and n have the meanings indicated above and L means sulfur, if compounds of the formulas indicated above (I-la) are reacted to (I-3-a), in which Q, X, Y, Z, m and n have the meanings indicated above, respectively with esters of chloromonothioformic acid or with esters of chlorodithioformic acid of the formula (VIII) wherein M and R2 have the meanings given 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 above-mentioned formulas are obtained (I - l -d) to (I-3-d), in which Q, R '. XYZ myn have the meanings indicated above, if compounds of the formulas indicated above (Il -a) to (I-3-a) are reacted, in which Q, X. Y, Z. and m have the meanings indicated above, respectively with sulfonyl chlorides of the formula (IX) R'-SO.-Cl (IX) in which R has the meaning indicated above, optionally in the presence of a diluent and, if appropriate, in the presence of an agent Acid acceptor.

(I) that the compounds of the formulas indicated above (Ile) are obtained up to (I-3-e), in which Q, L, R \ R5, X, Y, Z, and m have the meanings indicated above, if compounds of the above-mentioned formulas (I-la) are reacted to (I-3-a), in which Q, X, Y, Z, m and n have the meanings indicated above, respectively with phosphorus compounds of the formula ( X) wherein L, R 4 and R 5 have the meanings given 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-binding agent, (J) that the compounds of the formulas indicated above are obtained (I-1 -0 to (1-3-0) in which Q, E, X, Y, Z, m and n have the meanings indicated above, if compounds of the formulas indicated above (Il -a) to (I-3-a), in which Q. X, Y, Z, m and n have the meanings indicated above, respectively with metal compounds or with amines of the formulas (XI) or (XII).

R 'Me (OR13 (XI) N (XII) R' in which Me means a mono or divalent metal (preferably an alkaline or alkaline earth metal, such as lithium, sodium, potassium, magnesium or calcium), t means 1 or 2 and R13, R14, R15, independently of one another, mean hydrogen or alkyl, (preferably alkyl having 1 to 8 carbon atoms), optionally in the presence of a diluent, (K) whereby the compounds of the abovementioned formulas are obtained (Ilg) to (I-3-g), in which Q, L, R °, R7, X, Y, Z, m and n have the meanings indicated above if they are reacted compounds of the formulas indicated above (I- the ) to (I-3-a), in which Q, X, Y, Z. and m have the meanings indicated above, respectively a) with isocyanates or with isothiocyanates of the formula (XIII) R6-N = C = L ( XIII) in which R "and L have the meanings indicated above, if necessary in the presence of a diluent and, if necessary, in the presence of a catalyst or β) with carbamidyl chlorides or with thiocarbamidyl chlorides of the formula (XIV) wherein L.R'1 and R7 have the meanings indicated above, if appropriate in the presence of a diluent and, if appropriate, in the presence of an acid-accepting agent. The compounds according to the invention of the formulas (I-la), (I-2-a) and (I-3-a) are therefore important intermediates for the preparation of the compounds according to the invention of the formulas (1 -1), (1-2) and (1-3), in which G means respectively one of groups b), c), d), e), og). It has also been found that the novel compounds of the formula (I) have a very good activity as pesticide agents, preferably as insecticides or acaricides and as herbicides. The compounds according to the invention are generally defined by the formula (I). The substituents or preferred ranges of the radicals indicated in the abovementioned formulas and which will be cited below are explained as follows: Preferably, X means halogen, alkyl having 1 to 6 carbon atoms, alkenyl having 2 to 6 carbon atoms, carbon, alkynyl with 2 to 6 carbon atoms, alkoxy with 1 to 6 carbon atoms, alkenyloxy with 3 to 6 carbon atoms, alkylthio with 1 to 6 carbon atoms, alkylsulfinyl with 1 to 6 carbon atoms, alkylsulfonyl with 1 to 6 carbon atoms, haloalkyl with 1 to 6 carbon atoms, haloalkenyl with 2 to 6 'carbon atom, haloalkoxy with 1 to 6 carbon atoms, haloalkenyloxy with 3 to 6 carbon atoms, nitro, cyano or means phenyl, phenoxy phenylthio, benzyloxy or benzylthio substituted, if appropriate, by halogen, by alkyl with 1 to 6 carbon atoms, by alkoxy with 1 to 6 carbon atoms, by haloalkyl with 1 to 6 carbon atoms, by haloalkoxy with 1 to 4 atoms of carbon, by nitro or by cyano.

Preferably, 'Y means hydrogen, 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, alkenyloxy with 3 to 6 carbon atoms, alkylthio with 1 to 6 carbon atoms, alkylsulfinyl with 1 to 6 carbon atoms, alkylsulfonyl with 1 to 6 carbon atoms, halogenalkyl with 1 to 6 carbon atoms, halogenalkenyl with 2 to 6 carbon atoms, halogenalkoxy with 1 to 6 carbon atoms, haloalkenyloxy with 3 to 6 carbon atoms, nitro or cyano. Preferably, Z means halogen, alkyl having 1 to 6 carbon atoms, alkenyl with 2 to 6 carbon atoms, alkynyl with 2 to 6 carbon atoms, halogenalkyl with 1 to 6 carbon atoms, halogenalkenyl with 2 to 6 carbon atoms alkoxy with 1 to 6 carbon atoms, alkenyloxy with 3 to 6 carbon atoms, halogenalkoxy with 1 to 6 carbon atoms, haloalkenyloxy with 3 to 6 carbon atoms, nitro or cyano. Preferably, n means 0, 1, 2 or 3. Preferably, Het means one of the groups Preferably, G means hydrogen (a) or means one of the groups OR R? . SC ^ - R "R R1 (b). And M- '(c), (d), // R (e). where 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 substituted, where appropriate, by halogen, 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, in which, if appropriate, one or more, non-directly adjacent methylene groups (especially not more than two) are replaced 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, by alkylthio with 1 to 6 carbon atoms or by alkylsulfonyl with 1 to 6 carbon atoms, means phenyl-alkyl with 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 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 (for example pyrazolyl, thiazolyl, pyridyl, pyrimidyl, furanyl or thienyl), means phenoxy-alkyl having 1 to 6 carbon atoms, optionally substituted by halogen or by alkyl with 1 to 6 carbon atoms or means hetaryloxy-alkyl having from 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 (for example pyridyloxy-alkyl having 1 to 6 carbon atoms, pyrimidyloxy-alkyl with 1 to 6 ato carbon or thiazolyloxy-alkyl with 1 to 6 carbon atoms). Preferably, it 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 having 2 to 8 carbon atoms substituted, if appropriate, by halogen, means cycloalkyl having 3 to 8 carbon atoms, optionally substituted by halogen, by alkyl having 1 to 6 carbon atoms or by alkoxy having from 1 to 6 carbon atoms; carbon, 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 halogenalkyl with 1 to 6 carbon atoms or by haloalkoxy with 1 to 6 carbon atoms. means alkyl having from 1 to 8 carbon atoms, optionally substituted by halogen or by phenyl or benzyl, optionally substituted by halogen, by alkyl with 1 to 6 carbon atoms, by alkoxy with 1 to 6 carbon atoms, by haloalkyl with 1 to 4 carbon atoms, by halogenalkoxy with 1 to 4 carbon atoms < by cyano or by nitro. Preferably, and R ^ stand for, independently of one another, alkyl with 1 to 8 carbon atoms, alkoxy with 1 to 8 carbon atoms, alkylamino with 1 to 8 carbon atoms. di- (C 1 -C 8 -alkyl) amino, C 1 -C 8 -alkylthio, C 2 -C 8 -alkenylthio, C 3 -C 7 -alkylthio substituted, where appropriate, by halogen or phenyl , phenoxy or phenylthio substituted, where appropriate, by halogen, by nitro, by cyano, by alkoxy with 1 to 4 carbon atoms, by halogenalkoxy with 1 to 4 carbon atoms, by alkylthio with 1 to 4 carbon atoms, by haloalkylthio with 1 to 4 carbon atoms, for alkyl with 1 to 4 carbon atoms or by haloalkyl with 1 to 4 carbon atoms.

Preferably, R6 and R7 stand for, 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 C 1 -C 8 -alkoxy-alkyl having from 1 to 8 carbon atoms substituted, if appropriate, by halogen, means phenyl optionally substituted by halogen, by halogenalkyl with 1 to 8 carbon atoms, by alkyl with 1 to 8 carbon atoms or by alkoxy with 1 to 8 carbon atoms, means benzyl optionally substituted by halogen, by alkyl with 1 to 8 carbon atoms, by halogenalkyl with 1 to 8 carbon atoms or by alkoxy with 1 to 8 carbon atoms of carbon or together represent an alkylene radical having 3 to 6 carbon atoms, in which, if appropriate, it is replaced by oxygen or by sulfur, a methylene group not directly adjacent to the nitrogen atom. Preferably, Q means Rs OR '\ • / \ / C = N-N or C \ 10 / N OR' Preferably R "means hydrogen, means alkyl with 8 carbon atoms, optionally substituted by halogen, means cycloalkyl with 3 to 8 carbon atoms, optionally substituted by halogen, by alkyl with 4 carbon atoms or by alkoxy with 1 to 4 carbon atoms or means phenyl, benzyl or ethanyl substituted, where appropriate, by halogen, by alkyl with 1 to 6 carbon atoms, by alkoxy with 1 to 4 carbon atoms, by halogenalkyl with 1 to 4 carbon atoms, halogenalkoxy with 1 to 4 carbon atoms, by nitro or by cyano (for example pyridyl, pyrimidyl or thiazolyl), or means CO-R1, CO2R2 ', SO2R1', CONH2, CONHR11 or 11 R / CON, 12 * R Preferably, R10 means hydrogen or alkyl with 1 to 8 carbon atoms. Preferably, R "and R ?: are the same or different and mean alkyl with 1 to 6 carbon atoms or alkenyl with 3 to 6 carbon atoms Preferably, m means 0 or 1. Preferably R 'independently of R1 has the meanings previously indicated as being preferred for R. Preferably, R.sup.2 independently of R.sub.1 has the meanings indicated above for R, particularly preferably X denotes fluorine, chlorine, bromine, alkyl having 1 to 4 carbon atoms, alkoxy with 1 to 4 carbon atoms, halogenalkyl with 1 to 4 carbon atoms, halogenalkoxy with 1 to 4 carbon atoms, nitro or cyano.

Particularly preferably, Y denotes hydrogen, fluorine, chlorine, bromine, alkyl having 1 to 4 carbon atoms, alkoxy with 1 to 4 carbon atoms, halogenalkyl with 1 to 4 carbon atoms, halogenalkoxy with 1 to 4 carbon atoms , nitro or cyano. Particularly preferably, Z means fluorine, chlorine, bromine, alkyl having 1 to 4 carbon atoms, halogen with 1 to 4 carbon atoms, alkoxy with 1 to 4 carbon atoms, halogen with 1 to 4 carbon atoms, nitro or cyano. Particularly preferably, n means 0, 1 or 2. More preferably, Het means one of the groups Particularly preferably, G means hydrogen (a) or means one of the groups E «, - '(9). (especially means a) b) or c)), where E means a metal ion equivalent or an ammonium ion, L means oxygen or sulfur and M means oxygen or sulfur. Particularly preferably, R 1 means alkyl having 1 to 16 carbon atoms, alkenyl having 2 to 16 carbon atoms, alkoxy with 1 to 6 carbon atoms-alkyl having 1 to 6 carbon atoms or alkylthio having 1 to 6 carbon atoms. carbon-alkyl having from 1 to 6 carbon atoms substituted, if appropriate, by fluorine or by chlorine or means cycloalkyl having 3 to 7 carbon atoms optionally substituted by fluorine, chlorine, alkyl with 1 to 5 carbon atoms or by alkoxy with 1 to 5 carbon atomsis phenyl, optionally substituted 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; carbon or halogenalkoxy with 1 to 3 carbon atoms means phenyl-alkyl with 1 to 4 carbon atoms optionally substituted by fluorine, chlorine, bromine, alkyl with 1 to 4 carbon atoms, alkoxy with 1 to 4 carbon atoms, by halogenalkyl with 1 to 3 carbon atoms or by halogenalkoxy with 1 to 3 carbon atoms or means pyrazolyl, thiazolyl, pyridyl, pyrimidyl, furanyl or thienyl respectively substituted, if appropriate, by fluorine, by chlorine, by bromine 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, means cycloalkyl having 3 to 7 carbon atoms optionally substituted by fluorine, chlorine, alkyl having 1 to 4 carbon atoms or alkoxy with 1 to 4 carbon atoms or means phenyl or benzyl substituted, where 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 atoms of carbon, by halogenalkyl with 1 to 3 carbon atoms or by halogenalkoxy with 1 to 3 carbon atoms. R 'is particularly preferably alkyl having from 1 to 6 carbon atoms, optionally substituted by fluorine or chlorine or by phenyl or benzyl substituted, where appropriate, by fluorine, chlorine, bromine or alkyl with 1 to 5 carbon atoms, by alkoxy with 1 to 5 carbon atoms, by halogenalkyl with 1 to 3 carbon atoms, by haloalkoxy with 1 to 3 carbon atoms, by cyano or by nitro. Particularly preferably, R 4 and R "~ mean, independently of one another, alkyl having 1 to 6 carbon atoms, alkoxy with 1 to 6 carbon atoms, alkylamino with 1 to 6 carbon atoms, di- (alkyl with 1 to 6 carbon atoms) amino, alkylthio with 1 to 6 carbon atoms, alkenylthio with 3 to 4 carbon atoms or cycloalkylthio with 3 to 6 carbon atoms substituted respectively by fluorine or chlorine or means 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 halogenalkyl with 1 to 3 carbon atoms, particularly preferably R6 and R ^ mean, independently of one another, hydrogen, mean alkyl with 1 to 6 atoms of carbon, 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 atoms-alkyl with 1 to 6 carbon atoms substituted respectively given by halogen (especially fluorine or chlorine) means phenyl optionally substituted by halogen, by halogenalkyl with 1 to 5 carbon atoms, by alkyl with 1 to 5 carbon atoms or by alkoxy with 1 to 5 carbon atoms, means benzyl optionally substituted by halogen, by alkyl having 1 to 5 carbon atoms, by haloalkyl with 1 to carbon atoms or by alkoxy with 1 to 5 carbon atoms, or together they mean an alkylene radical having 3 to 6 carbon atoms, in which, in the case of oxygen or sulfur, it is replaced by a methylene group not directly adjacent to the carbon atom. the nitrogen atom. Particularly preferably, Q means 11 Ra OR \ / \ / C = N-N C 11/10 / V R OR Particularly preferably, R ° means hydrogen, means alkyl having 1 to 6 carbon atoms, optionally substituted by fluorine or chlorine, means cycloalkyl having 3 to 7 carbon atoms.

The term "carbon" means phenyl or benzyl, pyrimidyl or thiazolyl optionally substituted, respectively, by fluorine, chlorine, bromine, alkyl with 1 to 5 carbon atoms, alkoxy with 1 to 4 carbon atoms, haloalkyl with 1 a 2 carbon atoms, by halogenalkoxy with 1 to 2 carbon atoms, by nitro or by cyano. or means CO-R1 I D CO2R2 ', SO2Rr, CONH2, CONHR1 1 or 0 Especially preferably. R 10 denotes hydrogen or alkyl having 1 to 6 carbon atoms R "and R 12 are preferably identical or different and represent alkyl having 1 to 4 carbon atoms. m means 1. Especially preferably. R 'independently of R1 has the meanings indicated above with particular preference for R1. Particularly preferably R2, independently of R2, has the meanings indicated above, particularly preferably R2. Very particularly preferably, X means fluorine, chlorine, bromine, methyl, ethyl, n-propyl, isopropyl, methoxy, ethoxy, n-propoxy, iso-propoxy, trifluoromethyl, difluoromethoxy, trifluoromethoxy, nitro or cyano. Very particularly preferably Y denotes hydrogen, fluorine, chlorine, bromine, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, tere. -butyl, methoxy, ethoxy, n-propoxy, iso-propoxy, trifluoromethyl, difluoromethoxy, trifluoromethoxy, nitro or cyano. Very particularly preferably, Z means fluorine, chlorine, bromine, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, tere-butyl, methoxy, ethoxy, n-propoxy. iso-propoxy, difluoromethoxy, trifluoromethoxy, nitro or cyano. Very particularly preferably, n means 0, 1 or 2, mainly means 0 or 1. Very particularly preferably. Het means one of the groups Very particularly preferably, G means hydrogen (a) or means one of the groups O L R-, SO ^ - R ". R¿ R 0». M (c). (D)., // ^ < especially means (b) or (c). where 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: 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 or alkylthio with 1 to 4 carbon atoms-alkyl with 1 to 6 carbon atoms substituted respectively by fluorine or by chlorine or means cycloalkyl with 5 to 6 carbon atoms optionally substituted by methyl, ethyl, per tere. -butyl or methoxy, means phenyl optionally substituted by fluorine, chlorine, bromine, cyano, nitro, methyl, methoxy, trifluoromethyl or trifluoromethoxy, benzyl optionally substituted by fluorine, by chlorine , by bromine, by methyl, by methoxy, by trifluoromethyl or by trifluoromethoxy or means furanyl, thienyl or pyridyl respectively substituted, if appropriate by fluorine, by chlorine, by bromine or by methyl. Very particularly preferably R2 means alkyl having 1 to 14 carbon atoms, alkenyl having 2 to 14 carbon atoms or alkoxy having 1 to 4 carbon atoms-alkyl having 2 to 6 carbon atoms, cycloalkyl with 3 to 6 carbon atoms carbon atoms optionally substituted by methyl or by methoxy or means phenyl or benzyl substituted, where appropriate, by fluorine, chlorine, bromine, cyano, nitro, methyl, methoxy, trifluoromethyl or trifluoromethoxy. Very particularly preferably, R 'means methyl, ethyl, n-propyl, iso-propyl, optionally substituted by fluorine or by chlorine or means phenyl or benzyl substituted respectively given by fluorine, by chlorine, by bromine, by methyl, by ethyl, by n-propyl, by isopropyl, by tere. -butyl, by methoxy, by ethoxy, by isopropoxy, by tert-butoxy, by trifluoromethyl, by trifluoromethoxy, by cyano or by nitro. Very particularly preferably, R4 and R * independently of one another, mean alkyl with 1 to 4 carbon atoms.

T carbon, 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 with 1 to 4 carbon atoms respectively substitued by fluorine or by chlorine or by phenyl, phenoxy or phenylthio, respectively substituted by fluorine, by chlorine, by bromine, by nitro, by cyano, by alkoxy with 1 to 2 carbon atoms, by fluoroalkoxy with 1 to 2 carbon atoms, by alkylthio with 1 to 2 carbon atoms, by fluoroalkylthio with 1 to 2 carbon atoms or by alkyl with 1 to 3 carbon atoms. Very particularly preferably R6 and R7 stand for hydrogen independently, 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. carbon or alkoxy atoms with 1 to 4 carbon atoms-alkyl having 1 to 4 carbon atoms substituted, if appropriate, by fluorine or chlorine, mean phenyl optionally substituted by fluorine, chlorine, bromine, trifluoromethyl, by methyl or by methoxy, they mean benzyl optionally substituted by fluorine, by chlorine, by bromine, by alkyl with 1 to 4 carbon atoms, by halogenalkyl with 1 to 4 carbon atoms or by alkoxy with 1 to 4 carbon atoms or together they mean an alkylene radical having 5 to 6 carbon atoms, in which, if appropriate, it is replaced by oxygen or by sulfur, a methylene group not directly adjacent to the nitrogen atom. Very particularly preferably, Q means \ \ \ \ CHOH C- OR C = N-R C = N-O-R "/ / / / 11 Rs OR \ / C- -N C 11/10 R OR Very particularly preferably R9 is hydrogen, is alkyl having 1 to 4 carbon atoms, is cycloalkyl having 3 to 6 carbon atoms or is phenyl or benzyl optionally substituted, respectively, by fluorine, chlorine, bromine or methyl , by ethyl, by n-propyl, by iso-propyl, by tere. -butyl, by methoxy, by trifluoromethyl, by trifluoromethoxy, by nitro or by cyano or means CO-R1, COiR2 ', SO2R1', CONH2, CONHR11, 11 / CON. 12"R Very particularly preferably, R '"means hydrogen or methyl, R" and R ?: are very particularly preferably different and represent methyl or ethyl. Very particularly preferably, m means 1. Very particularly preferably, R 1 independently of R 'has the abovementioned meanings, very particularly preferably for R 1. Very particularly preferably. R2 independently of R2 has the abovementioned meanings very particularly preferably for R :.

The definitions of the remains or the explanations given above in a general manner or indicated in the preferred ranges can be combined arbitrarily with each other, that is to say 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 indicated above is preferably (preferably) present. According to the invention, the compounds of the formula (I), in which a combination of the abovementioned meanings is particularly preferably present, are particularly preferred. According to the invention, the compounds of the formula (I), in which a combination of the abovementioned meanings is very particularly preferably present, are very particularly preferred. The saturated or unsaturated hydrocarbon moieties such as alkyl or alkenyl can be, even in combination with heteroatoms, such as for example in alkoxy, insofar as possible, respectively straight-chain or branched chain. The substituted radicals can be mono- or polysubstituted, the substituents being the same or different 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) can be mentioned.

Table 1: m = 1 \ CH-OH / Tables 2 to 8. Compounds of the formula (I-l-a) Table 2: X, Y and Zn as indicated in table 1. m = 1 \ Q = / C = 0 Table 3: X, Y and Zn as indicated in table 1. m = 1 \ Q = C- N-OCH, / Table 4: X, Y v Zn as indicated in table 1. m Table 5. X, Y and Zn as indicated in table 1. m = 1 \ Q = = - NHCOC, / Table 6: X. Y v Zn as indicated in table 1. m = 1 \ Q = C = N- NHCO2C2Hs Table 7: X, Y v Zn as indicated in table 1. m = 1 \ C = N - NHSO2CH3 Table 8: X, Y and Zn as indicated in table 1. m = 1 In particular, in addition to the compounds indicated in the preparation examples, mention may be made of the following compounds of the formula (I -2-a): Table 9: = l \ Q = CH-OH Tables 10 to 16. Compounds of the formula (I-2-a). Table 10: X, Y and Zn as indicated in table 9 m = l \ Q = / C = O Table 11: X, Y and Zn as indicated in table 9 m = l \ Q v = C = N-OCH 3, Table 12: X, Y and Zn as indicated in table 9 m = 1 \ Q = c = N - OC2 2H '' 5 / Table 13: X, Y and Zn as indicated in table 9 m = 1 \ Q v = C = N- NHCOCH 3, Table 14: X, Y and Zn as indicated in table 9 m = 1 \ Q = C = - NHC02C2Hs Table 15: X, Y and Zn as indicated in table 9 m = 1 Q = ^ C = N - NHSO2CH.

Table 16: X, Y and Zn as indicated in table 9 m = 1 In particular, in addition to the compounds indicated in the preparation examples, mention may be made of the following compounds of the formula (I-3-a): Table 17: m = l \ Q = c CH-OH / Tables 18 to 24. Compounds of the formula (I-3-a) Table 18: X, Y and Zp as indicated in table 17 m = 1 \ Table 19: X, Y and Zn as indicated in table 17 m = 1 Table 20: X, Y and Zn as indicated in table 17 m = 1 Table 21: X, Y and Zn as indicated in table 17 m = 1 \ Q = C = N- -NHCOCH, / Table 22: X, Y and Zn as indicated in table 17 m = 1 \ Q = C = - NHSO H, / Table 23: X, Y and Zn as indicated in table 17 m = l Table 24: X, Y and Zn [as indicated in table 17] m = 1 If N-f (2,4,6-trimethyl-phenyl) -acetyl] -l-amino-4-methoxyimino-cyclohexane-carboxylic acid methyl ester is used as starting material, the development may be depicted of the process according to the invention by means of the following reaction scheme.

If the ethyl O - [(2,4-dichloro-phenyl) -acetyl] -l-hydroxy-4-oxo-cyclohexanecarboxylate is used according to process (B), the development of the process according to the invention can be represented. by means of the following reaction scheme: If 2- (2,4-dimethyl-phenyl) -4- (4-methoxy) -benzylmercapto-4,4- (3-oxo-pentamethylene) -3-oxo-butyrate is used according to process (C) ethyl may be represented the development of the process according to the invention by means of the following reaction scheme: If 3- ((2-chloro-4-methyl) -phenyl] -5,5 - [(3-phenylimino) -pentamethylene] -pyrrolidine-2,4-dione is used as starting material according to the procedure (Da) ) the T =, 3-f (2-chloro-4-methyl) -phenyl] -5.5 - [(3-phenylimino) -pentamethylene] -pyrrolidine-2,4-dione and pivaloyl chloride, the development of the process may be represented. the invention by means of the following reaction scheme.

If 3- ((4-chloro-2-methyl-2-phenyl) -4-hydroxy-5,5-I (3-benzyloxyimino) -pentamethylene] - is used as the starting material in the process (Dβ)? - 5-dihydrofuran-2-one acetic anhydride, the development of the process according to the invention can be represented by means of the following reaction scheme: If 3- ((2,4-dichloro-6-meetyl) -phenyl] -5,5 - [(3-oxo-pentamethylene) J-pyrrolidin-2 is used as the starting compound according to process (E), 4-dione according to the procedure (E) 3 - [(2,4-dichloro-6-meetil) -phenyl] -5,5 - [(3-oxo-pentamethylene) j- pyrrolidin-2,4-dione chloroformate of ethoxyethyl, the development may be of the process according to the invention by means of the following reaction scheme: If they are used as starting materials according to process (F), variant to 3 - [(2-chloro) -phenyl] -4-hydroxy-5,5-f3- (2-acetyl-hydrazino) -pentamethylene] - or 3-Dihydrofuran-2-opa and methyl chloromonothioformate, the development of the process according to the invention can be represented by means of the following reaction scheme: If 3- (2,6-dichloro-4-methyl) -phenyl] -4-hydroxy-4,4 - [(3-methoxyimino) -pentamethylene] - is used as the starting material according to process (G); 3- dihydrofuran-2-one and chloride, the development of the reaction can be represented by means of the following reaction scheme: If 3- (2,5-dichloro) -phenyl] -5,5 - [(3-oxa) -pentamethylene] -pyridinidine-2,4-dione and methanothium chloride are used as starting materials according to process (H) -phosphonyl- (2,2,2-trifluoroethyl ester), the development of the reaction can be represented by means of the following reaction scheme: If 3 - [(2,4-dichloro) -phenylJ-5,5 - [(3-ethoxy? M? No? -? Entamet? Len] -p is used as starting material according to process (I)? rrol? din-2,4-d? ona and NaOH, the development of the process according to the invention can be represented by means of the following reaction scheme If 3- ((2,4,5-trimethoxy) -phenyl] -4-hydroxy-5,5 - [(2-oxo) -tetramethylene] -? 3-dihydrofuran is used as starting material according to the procedure (Ja) -2-one and the ethyl isocyanate can be represented the development of the reaction by means of the following reaction scheme: If 3- (2,3,4,6-tetramethylene-phenyl] -5,5 - [(4-methoxamino) -pentamethylene) -pyrrolid is used as starting material according to the procedure (Jβ)? n-2,4-d? ona > dimethylcarbamidyl chloride the development of the reaction can be represented by means of the following scheme The compounds of the formula (II), necessary as starting materials in the process (A) according to the invention where Q, X, Y, Z, m. n and R8 have the meanings indicated above, they are new. The esters of the acylamino acids of the formula (II) are obtained, for example, by acylating amino acid derivatives of the formula (XV) in which Q, m and R8 have the meanings indicated above, with substituted phenylacetyl halides of the formula (XVI) wherein X.Y.Z.sub.v n have the above-indicated meanings v Hal means chlorine or bromine, (Chem. Reviews 52, 237-416 (1953); Bhattacharya, Indian, J. Chem. 6, 341-5, 1968) or if acylamino acids of the formula (XVII) are esterified where Q. m. X. Y, Z and n have the meanings indicated above, (Chem. Ind. (London) 1568 (1968)). The compounds of the formula (XVII) where Q, m. X. Y. Z and n have the meanings indicated above. they are new. The compounds of the formula (XVII) are obtained if they are acylated according to Schotten-Baumann amino acids of the formula (XVIII) a- < c and. (XVIII) wherein Q and m have the meanings indicated above, with substituted phenylacetyl halides of the formula (XVI) wherein X, Y. Z and n have the above meanings and Hal means chlorine or bromine, (Organikum, VEB Deutscher Verlag der Wissenschaften, Berlin 1977, page 505).

The compounds of the formula (XVI) are partially known. These can be obtained according to known processes (see for example Henecka, Houben-Weyl, Methoden der Organischen Chemie, volume 8. pages 467-469 (1952)) or are known from the patent applications cited at the beginning or WO 98/05638 and WO 976868.

In addition, the starting materials of the formula (II) used in process (A) above can be obtained wherein Q, X, Y, Z, m, n and R8 have the meanings indicated above, if aminonitriles of the formula (XIX) are reacted where Q and m have the meanings indicated above. with substituted phenylacetyl halides of the formula (xvi) in which X, Y, Z, n and Hal have the meanings indicated above, to give compounds of the formula (XX) wherein Q, X, Y, Z, m and n have the meanings indicated above, and these are then subjected to acid hydrolysis. The compounds of the formula (XX) are also new. i c, The following reaction schemes show, by way of example, synthetic routes for the starting materials of the formula (II). The uppercase letters located behind some numbers of the formulas serve to differentiate different meanings of Q. In part, 0 will also be used in the procurement examples. In the following reaction schemes reference will be made to the compounds of the formulas (XXVIII), where Q and m have the meanings indicated above. Exemplary compounds for various meanings of Q and for m = 1 have been indicated in the formulations, however, they are covered by the formulas indicated above.

^ OR11 The radicals R 'in Q = can also mean together an alkanediyl group with 2 to 3 carbon atoms, optionally substituted by methyl or ethyl Outline Reaction 1 Reaction Scheme la. XV II-E Reaction Scheme 2.

The compounds of the formula (III) necessary as starting materials in the case of the process (B) according to the invention where Q ', X, Y, Z, m, n and R8 have the meanings indicated above, are new. These can be obtained in a simple manner according to methods known in principle. In this way, the compounds of the formula (III) are obtained, for example, if 2-hydroxycarboxylic acid esters of the formula (XXI) are acylated.

OH wherein Q, m and Rs have the meanings indicated above, with substituted phenylacetyl halides of the formula (XVI) wherein X, Y, Z, n and Hal have the meanings indicated above, (Chem. Reviews 52, 237-416 (1953)). The following reaction scheme shows, by way of example, synthetic routes for the starting materials of the formula (III) and for the final products of the formula (I). The uppercase letters located behind some numbers of the formulas serve to differentiate different meanings of Q. In part, they will also be used in the procurement examples. In the reaction scheme reference will be made to the compounds of the formula where Q and m have the meaning indicated above. In the formula schema exemplary compounds have been indicated for various meanings of Q and for m = 1. however, they are covered by the previously indicated formulas.

The radicals R in Q = can also mean together an alkanediyl group with 2 to 3 carbon atoms, optionally substituted by methyl or ethyl.

Reaction Scheme 3. HO- \ = o Reaction Scheme 3a. m-c The compounds of the formula (IV), necessary as starting products in the case of the process (C) above 10 in which Q, W, X, Y, Z, m, n and Rs have the meanings indicated above, are new. These can be obtained according to methods known in principle. The compounds of the formula (IV) are obtained, for example, if substituted fatty acid esters of the formula (XXII) are acylated wherein X.Y, Z, n and R8 have the meaning indicated above, with 2-benzyl-carbonyl halides of the formula (XXIII) ^ wherein Q and W have the meanings indicated above and Hal means halogen (especially chlorine or bromine), in the presence of bases fuepes (see for example M.S. Chambers, E.J. Thomas, D.J. Williams, J. Chem. Soc. Chem. Commun., (1987), 1228). The compounds of the formula (XXII) are partially known from the patent applications cited at the beginning. The compounds of the formula (XXII) are obtained, for example, if compounds of the formula (XXIV) are esterified. wherein X, Y. Z and n have the meaning indicated above, 0 in the presence of alcohols and water-removing agents (for example concentrated sulfuric acid), or alcohols with compounds of the formula (XVI), wherein X, Y, Z, n and Hal have the meanings indicated above, (Chem. Reviews 52, 237-416 (1953)). The benzylthio carbonyl halides of the formula (XXIII) are new.

These can be obtained according to known procedures (J. Antibiotics (1983), 26, 1589, WO 95/26 345). The acyl halides of the formula (V), the anhydrides of 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, metal oxides or amines of the formula (XI) \ (XII), the isocyanates of the formula (XIII) and the carbamidyl chlorides of the formula (XIV). Further 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 chemistry or inorganic chemistry. The compounds of formulas (V) to (XIV) are also known from the patent applications mentioned at the beginning or can be obtained according to the methods indicated therein. The process (A) is characterized in that compounds of the formula (II) are subjected to intramolecular condensation, wherein Q, X, Y, Z, m, n and R8 have the meanings indicated above, in the presence of a base. In the process according to (A) in formula (II) Q the group can also mean wherein X, Y, Z and n have the meanings indicated above. This also applies to the meaning of Q in formula (III) in the process according to (B). Suitable diluents in the process (A) according to the invention are all inert organic solvents. Preferably, hydrocarbons, such as toluene and xylene, can be used. further 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, as well as alcohols such as methanol, ethanol, propanol, iso-propanol, butanol. iso-butanol and tere. -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 (= 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 tert-butylate potassium. The reaction temperatures in the process (A) 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 (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 generally employed in approximately equimolar amounts up to twice molar. 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 compounds of the formula (III) are subjected to an intramolecular condensation., wherein Q, X, Y, Z, m, n and R8 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 inert organic solvents. Preferably, hydrocarbons such as toluene and xylene can be used. Also ethers, such as dibutyl ether, tetrahydrofuran, dioxane, ghcoldimethyl ether and digiicoldimethyl ether, in addition polar solvents, such as dimethylsulfoxide, sulfolane. dimethylformamide and N-methyl-pyrrolidone. Furthermore, alcohols such as methanol, ethanol, propanol, iso-propanol, butanol, iso-butanol and tere can be used. -butanol. 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 tert-butylate potassium. The reaction temperatures in the process (B) 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 (B) according to the invention 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 Q, W, X are intramolecularly cyclized. , Y, Z, m, n and R8 have the meaning indicated above in the presence of an acid and, if appropriate, in the presence of a diluent.All inert organic solvents can be used as diluents in process (C) according to the invention. hydrocarbons such as toluene and xylene, in addition halogenated hydrocarbons such as dichloromethane, chloroform, ethylene chloride, chlorobenzene, dichlorobenzene, in addition polar solvents, such as dimethylsulfoxide, sulfolane, dimethylformamide and N-methyl-pyrrolidone can be employed. methanol, ethanol, propanol, iso-propanol, butanol, isobutanol, tere. -butanol, If appropriate, the acid used can also be used as a diluent. In the process (C) according to the invention, all customary inorganic and organic acids such as, for example, hydrohalic acids, sulfuric acid, alkyl-, aryl- and halogenoalkylsulfonic acids, especially halogenated alkylcarboxylic acids such as, for example, trifluoroacetic acid, can be used . The reaction temperatures in 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. In carrying out the process (C) according to the invention, the reaction components of the formulas (IV) and the acids are used in equimolar amounts. However, it is also possible, if appropriate, to use the acid as a solvent or as a catalyst. The process (Da) is characterized in that compounds of the formulas (I-la) to (I-3-a) are reacted respectively with carbonyl halides of the formula (V), if appropriate in the presence of a diluent, and given case, 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 can be used, benzene, toluene, xylene and tetralin, in addition halogenated hydrocarbons such as methylene chloride, chloroform, carbon tetrachloride, chlorobenzene and o-dichlorobenzene, further ketones, such as acetone, and methylisopropyl ketone, nitriles such as acetonitrile, further ethers, such as diethyl ether, tetrahydrofuran and dioxane, further esters of carboxylic acids such as ethyl acetate and also strong polar solvents, such as dimethyl sulfoxide 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 the process (Da) according to the invention. Preference is given to tertiary amines, such as triethylamine, pyridine, diazabicyclooctane (DABCO), diazabicycloundecene (DBU), diazabicyclononene (DBN). bases of Hunig and N, N-dimethylaniline, plus oxides of alkaline earth metals. such as magnesium and calcium oxide, further alkali metal and alkaline earth metal carbonates, such as sodium carbonate, potassium carbonate and calcium carbonate as well as alkali hydroxides such as sodium hydroxide and potassium hydroxide. The reaction temperatures 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 -l- 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 (I-la) 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 (I-la) to (I-3-a) are reacted with carboxylic acid anhydrides of the formula (VI), if appropriate, in the presence of a diluent and, if appropriate, in the presence of an acid-accepting agent. Diluents which can preferably be used in the process (Dβ) according to the invention are those diluents which also preferably fall into consideration in the case where acyl halides are used. In addition, an excess of the carboxylic acid anhydride used at the same time can also act as a diluent. As acid-binding agents added if appropriate, in the case of the process (Dβ), preference is given to those acid-binding agents which also enter preferably in consideration in the case of the use of the acyl halides The reaction temperatures 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 (I-la) to (I-3-a) and the carboxylic acid anhydride of the formula (VI) are used in general in amounts respectively approximately equivalent. 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 carboxylic acid anhydride present in excess as well as the carboxylic acid formed are distilled off or washed out with an organic solvent or with water. The process (E) is characterized in that compounds of the formulas (I-la) to (I-3-a) respectively are reacted with esters of chloroformic acid or with thiol esters of the chloroformic acid of the formula (VII), if appropriate. presence of a diluent and, if appropriate, in the presence of an acid-accepting agent. Suitable acid-binding agents are, in the case of the reaction according to process (E) according to the invention, all customary acid acceptors. Preferably, tertiary amines such as triethylamine can be used., pyridine, DABCO, DBU, DBA, bases of Hunig and N, N-d? methyl-aniline, besides oxides of alkaline earth metals. such as magnesium 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. Suitable diluents in the process (E) according to the invention are all solvents which are inert to the esters of chloroformic acid or to thiolesters 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, and also ketones, such as acetone, dimethyl isopropyl ketone, nitriles such as acetonitrile. , in addition ethers such as diethyl ether, tetrahydrofuran and dioxane, further esters of carboxylic acids such as ethyl acetate and in addition also strong polar solvents such as dimethyl sulfoxide and sulfolane. The reaction temperatures in the process (E) according to the invention can vary within wide limits. If working in the presence of a diluent and an acid-binding agent, the reaction temperatures will generally be 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 (I-la) to (I-3-a) and the corresponding esters of the chloroformic acid or the thiolesters of the chloroformic acid of the formula are used (VII) in general, respectively, in approximately equivalent amounts. 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 (I-la) to (I-3-a) are reacted, respectively, with compounds of the formula (VIII) in the presence of a diluent and, if appropriate , in the presence of an acid-accepting agent. In the case of the preparation process (F), about 1 mole of chlorornonothiophoric acid ester or chlorodithioformic acid ester of formula (I-la) up to (I-3-a) is used per mole of the starting compound of the formulas (I-la). the formula (VIII) at 0 to 120 ° C, preferably 20 to 60 ° C. Suitable diluents, if appropriate, include all inert polar organic solvents, such as ethers, nitriles, ketones, esters of carboxylic acids, amides, sulfones, sulfoxides, as well as haloalkanes. Preference is given to using dimethylsulfoxide, tetrahydrofuran, ethyl acetate, dimethylformamide or methylene chloride. If, in a preferred embodiment, the enolate salt is formed by the addition of strong deprotonation agents such as, for example, sodium hydride or tertiary potassium butylate, of the compounds (Ila) to (I-3-a), desist to the complementary addition of acid-binding agents. If acid-binding agents are used, the usual inorganic or organic bases will be used, examples being sodium hydroxide, sodium carbonate, potassium carbonate, pyridine, triethylamine. The reaction can be carried out at normal pressure or also 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 (I-la) to (I-3-a) are reacted, respectively, with sulfonyl chlorides of the formula (IX), if appropriate in the presence of a diluent. and if applicable, in the presence of an acid-accepting agent.

In the preparation process (G), per mol of the starting compound of the formula (Ila) up to (I-3-a) about 1 mol of sulfonyl chloride of the formula (IX) is used at -20 to 150 °. C, preferably at 20 to 70 ° C. Suitable diluents, if appropriate, include all inert polar organic solvents such as ethers, amides, ketones, esters of carboxylic acids, nitriles, sulphones, sulfoxides or halogenated hydrocarbons, such as methylene chloride. Preference is given to using dimethylsulfoxide, ethyl acetate, nitrile acetate, tetrahydrofuran, dimethylformamide, methylene chloride. If the enolate salt of the compounds (I-la) is formed up to (I-3-a) in a preferred embodiment by the addition of strong deprotonating agents, (such as for example sodium hydride or potassium tertiary butylate) ), the complementary addition of acid-binding agents may be abandoned. If acid-binding agents are used, the usual inorganic or organic bases will be used, examples being sodium hydroxide, sodium carbonate, potassium carbonate, pyridine, triethylamine.

The reaction can be carried out at normal pressure or under higher pressure, preferably at normal pressure. The preparation is carried out according to customary methods The process (H) according to the invention is characterized in that compounds of the formulas (I-1 -a) to (I-3-a) are reacted respectively with phosphorus compounds of the formula (X) if necessary in the presence of a diluent \ if appropriate, in the presence of an acid-accepting agent. In the preparation process (H), for the preparation of the compounds of the formulas (I-le) to (I-3-e), on 1 mole of the compounds (I-1 -a) 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. Suitable diluents, optionally added, are all inert organic polar solvents such as ethers, amides, ketones, esters of carboxylic acids, nitriles, alcohols, sulphides, sulfones, sulfoxides, etc. Preference is given to using acetonitrile, dimethyl sulfoxide, ethyl acetate, tetrahydrofuran, dimethylformamide or methylene chloride. Suitable acid-binding agents, optionally added, are customary inorganic or organic bases such as hydroxides, carbonates or amides. Examples which may be mentioned are sodium hydroxide, sodium carbonate, potassium carbonate, pyridine, 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 purification of the final products obtained is preferably carried out by crystallization, purification by chromatography or by so-called "initial distillation", ie elimination of the volatile components in vacuum. Process (I) is characterized in that compounds of the formulas (I-la) to (I-3-a) are reacted with metal hydroxides either with metal oxides of the formula (XI) or with amines of the formula (XII) ), if appropriate in the presence of a diluent Diluents such as tetrahydrofuran, dioxane, diethyl ether as well as alcohols such as methanol, ethanol, isopropanol, as well as water can be used as diluents in the process (I) according to the invention. The process (I) according to the invention is generally carried out under normal pressure. The reaction temperatures are 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-la) to (I-3-a) are reacted, respectively, with (Ja) compounds of the formula (XIII), if appropriate in the presence of a diluent andif 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-binding 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 (I-la) to (I-3-a), preferably at 20 to 50 ° C. Suitable diluents, if appropriate, are all inert organic solvents such as ethers, amides, nitriles, ketones, carboxylic acid esters, sulphones, sulfoxides. If necessary, catalysts can be added to accelerate the reaction. The organic compounds of tin, such as, for example, dibutyltin dilaurate, can be used as catalysts in a very advantageous manner. Preferably work at normal pressure. In the preparation process (Jß), about 1 mole of carbamidyl chloride of the formula (XIV) is reacted per mole of the starting compound of the formulas (I-la) to (I-3-a) to 0 to 150 ° C, preferably at 20 to 70 ° C: Suitable diluents, if any, include all inert polar organic solvents, such as ethers, amides, ketones. esters of carboxylic acids, sulfones, sulfoxides or halogenated hydrocarbons. Preference is given to using dimethylsulfoxide, tetrahydrofuran, ethyl acetate, dimethylformamide or methylene chloride.

If the enolate salt of the compounds (I-la) is formed up to (I-3-a) in a preferred embodiment, by the addition of strong deprotonating agents, (such as for example sodium hydride or tertiary butylate of potassium), the complementary addition of acid-binding agents may be abandoned. If acid-binding agents are used, the usual inorganic or organic bases are suitable, examples being sodium hydroxide, sodium carbonate, potassium carbonate, triethylamine or pyridine. The reaction can be carried out under normal pressure or under higher pressure, preferably at normal pressure. Working up is carried out by customary methods. The active products are suitable for the control of animal pests, preferably against arthropods and nematodes, especially against insects and arachnids, which occur in agriculture in forestry, for the protection of stored products and materials and 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 pests mentioned above belong to: 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, Scutigera spec. From the order of the symphyla, 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, Blattella germanica, Acheta domesticus, Gryllotalpa spp., Locusta migratory migratory ides, Melanoplus differentialis, Schistocerca gregaria. From the order of dermotteos, for example, Auricular paraphysis. From the order of the Isoptera, for example, Reticul kermes spp. From the order of the anopplura, for example, Phylloxera vastatrix, Pemphigus spp., Pediculus humanus corporis, Haematopinus spp., Linognathus spp. From the order of the malophagus, for example , Trichodectes spp., Damalinea spp. From the order of the Thysanoptera, for example, Hercinothrips femoralis, Thrips tabaci. From the order of the heteroptera, for example, Eurygaster spp., Dysdercus intermedius, Piesma quadrata, Cimex lectularius, Rhodnius prolixus, Triatoma spp.

From the order of the Homoptera, for example, Aleurodes brassicae, Bemisia 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, Lecanium corni, Saissetia oleae. Laodelphax stpatellus, 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 .. Bucculatpx 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 kuehniella, Galleria mellonella, Tineola bisselliella, Tinea pellionella, Hof annophila pseudospretella, Cacoecia podana, Capua reticulana, Choristoneura fumíferana, Clysia ambiguella, Homona magnánima, Tortix viridana From the order of Coleoptera, for example Anobium punctatum, Rhizopertha dominica, Acanthoscelides obtectus, Acanthoscelides obtectus, Hylotrupes bajulus, Agelastica alni, Leptinotarsa decemlineata, 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, Costelytra zealandica; From the order of hymenoptera. for example. Diprion spp. , Hoplocampa spp., Lasius spp. , Monomorium pharaonis, 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. , Chrysomyia spp. , Cuterebra spp., Gastrophilus spp. , Hyppobosca spp., Stomoxys spp. , Oestrus spp. Hypoderma spp. , Tabanus spp. , Tannia spp., Bibio hortulanus, Oscinella fpt. Phorbia spp. , Pegomyia hyoscyami, Ceratitis capitata, Dacus oleae. Typical paludosa From the order of siphonoptera. for example, Xenopsylla cheopis, Ceratophyllus spp. From the order of arachnids, for example Scorpio maurus, Latrodectus mactans.

From the order of mites, for example, Acarus siró, Argas spp., Ornithodoros spp., TJermanyssus gallinae, Eriophyes ribis, Phyllocoptruta oleivor-t, 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, against larvae of the horseradish leaf beetle (Phaedon cochleariae), against the larvae of the green rice cicada (Nephotettix cincticeps). , against the louse of the leaf of the peach tree (Myzus persicae) and also against the mite of the spider mite of the fruit trees (Panonychus ulmi). The active compounds according to the invention can also be used as defoliants, desiccants, agents for killing weeds, and especially, as weed killers. Weeds, in the broadest sense, will be understood as plants growing in places where they grow. 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 active compounds according to the invention can be used, for example, in the following plants: Bad dicotyledonous herbs of the classes Sinapis, Lepidium, Galium. Stellaria, Matricaria, Anthemis. Galinsoga, Chenopodium, Urtica, Senecio, Amaranthus, Portulaca, Xanthium, Convolvulus. Ipomoea. Polygonum, Sesbania, Ambrosia, Cirsium, Carduus, Soncchus. Solanum Rorippa Royala, Lindernia, Lamium, Veronica. Abutilon, Emex, Datura, Viola, Galeopsis, Papaver, Centaurea, Trifolium, Ranunculus, Teraxacum.

Dicotyledonous crops of the classes: Gossypium, Glycine, Beta, Daucus, Phaseolus, Pisum, Solanum, Linum, Ipomea, Vicia, Nicotiana, Lycopersicon, Arachis, Brassica, Lactuca, Gucumis, Cucurbita. Bad monocotyledonous herbs of the following kinds: Echinochloa, Setaria, Panicum, Digitaria, Phleum, Poa, Fesmca, Eleusine, Brachiaria, Lolium, Bromus, Oats, Cyperus, Sorghum,, Agropyron, Cycnodon, Monocharia, Fimbristylis, Sagittaria, Eleocharis, Scirpus, Paspalum, Ischaemum, Sphenoclea, Dactyloctenium, Agrostis, Alopecurus, Apera. Cultures of monocotyledonous classes: Oryza, Zea, Triticum, Hordeum, Avena, Sécale, Sorghum, Panicum, Saccharum, Ananas, Asparagus, Allium. The use of the active compounds according to the invention is not, however, limited in any way to these classes, but is also understood on other plants as well. 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. Also, compounds can be used to control 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, in ornamental and sport routes and 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 control of monocotyledonous weeds with dicotyledonous crops in the pre-emergence and post-emergence process. They can be used for example in cotton or in sugar beet with a very good success to combat harmful herbs. The active products can be transformed into the usual formulations, such as solutions, emulsions, sprayable powders, suspensions, powders, dusts, pastes, soluble powders, granules, suspension-emulsion concentrates, natural and synthetic materials impregnated with the active substance as well as microencapsulated in polymer materials. These formulations are prepared in known manner, for example, by mixing the active substances with extender materials, that is, with liquid solvents and / or solid excipients, where appropriate, using surfactants, that is emulsifiers and / or dispersants and / or foam generating means. In the case of using water as a filler, organic solvents can also be used as auxiliary solvents, for example. Suitable liquid solvents are essentially aromatic hydrocarbons, such as xylene, toluene or alkylnaphthalenes, chlorinated aromatic hydrocarbons and chlorinated aliphatic hydrocarbons, such as chlorobenzenes. chloroethylenes or methylene chloride, aliphatic hydrocarbons, such as cyclohexane or paraffins, for example, fractions of crude petroleum, mineral and vegetable oils, alcohols, such as butanol, or glycol, as well as their esters and ethers, ketones, such as acetone, methyl ethyl ketone, mctylisobutyl ketone or cyclohexanone, strongly polar solvents, such as dimethylformamide and dimethyl sulfoxide, as well as water. Suitable solid excipients are, for example, ammonium salts and natural ground minerals, such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth and ground synthetic minerals, such as highly dispersed silicic acid, aluminum oxide and silicates, as solid excipients for granulates are considered: for example, broken and fractionated natural minerals, such as calcite, marble, pumice, sepiolite, dolomite, as well as synthetic granules of inorganic and organic flours, as well as granulates of organic materials, such as sawdust, coconut-nut shells, corn ears and tobacco stems, as emulsifiers and / or foam generators are considered: for example, non-ionogenic, and anionic emulsifiers, such as polyoxyethylenated esters of fatty acids, polyoxyethylenated ethers of fatty alcohols, for example, alkylaryl-poly licolyester, alkylsulfonates, alkyl sulfates, arylsulfonates, as well as albumin hydrolysates; Suitable dispersants are: for example sulphite leaching of lignin and methylcellulose. Adhesives such as carboxymethylcellulose, natural and synthetic polymers powdery, granulated or in the form of latex, such as gum arabic, polyvinyl alcohol, polyvinyl acetate, can be used in the formulations. as well as natural phospholipids, such as cephalins and lecithins, and synthetic phospholipids. Other additives can be mineral and vegetable oils. Dyes, such as inorganic pigments, for example, iron oxide, titanium oxide, ferrocyanic blue and organic dyes, such as alizarin dyes, metallic azo and phthalocyanine dyes and trace nutrients, such as iron salts, can be employed. manganese, boron, copper, cobalt, molybdenum and zinc The formulations generally contain between 0.1 to 95% by weight of active substance, preferably between 0.5 and 90%. The active compound according to the invention can be present in its commercially available formulations as well as in the forms of application, prepared from these formulations, in admixture with other active ingredients, such as insecticides, baits, sterilants, acaricides, nematicides, fungicides. , growth regulating products or herbicides. Insecticides include, for example, esters of phosphoric acid, carbamates, esters of carboxylic acids, chlorinated hydrocarbons, phenylureas, products generated by micro-organisms, etc. Particularly convenient mixing components are, for example, the following fungicides: 2-Aminobutane; 2-anilino-4-methyl-6-cyclopropylpyrimidine; 2 ', 6'-dibromo-2-methyl-4'-trifluoromethoxy-4'-trifluoromethyl-l, 3-thiazole-5-carboxanilide; 2,6-dichloro-N- (4-trifluoromethylbenzyl) benzaide, (E) -2-methoxyimino-N-methyl-2- (2-phenoxyphenyl) acetamide; 8-hydroxyquinolinesulfate; methyI- (E) -2- 2- [6- (2-cyanophenoxy) pipmidin-4-yloxy] phenyl-3-methoxy-acrylate; methyl- (E) -methoxyim? fafa- (o-tolyl-oxy) -o-toIyl] acetate; 2-Phenylphenol (OPP), Aldimorph, Ampropylfos, Anilazin, Azaconazole, Benalaxyl, Benodanil, Benomyl. Binapacryl. BiphenvI. Bitertanol, Blasticidin-S, Bromuconazole, Bupirimate. Buthiobate, Calciumpolysulfid, Captafol, Captan, Carbendazim, Carboxin, Chinomethionat (Chomethionat), Chloroneb, Chioropicrm, Chlorothalonil, Chlozolinat, Cufraneb, Cymoxanil, Cyproconazole, Cyprofuram, Dichlorophen, Diclobutrazol, Diclofuanid, Diclomezin, Dicloran, Diethofencarb, Difenoconazole, Dimethipmol, Dimethomorph , Diniconazole, Dinocap, Diphenylamin, Dipyrithion, Ditali fos, Dithianon, Dodin, Drazoxolon, Edifenphos, Epoxyconazole, Ethypoly, Etpdiazole, Fenarimol, Fenbuconazole, Fenfuram, Fenitropan, Feniciclo-nil, Fenpropidin, Fenpropimorf, Fentinacetate, Fentinhy-droxyd, Ferbam, Ferimzone, Fluazinam, Fludioxonil, Fluor-omide, Fluquinconazole, Flusilazole, Flusulfamide, Fluto-lanil, Flutriafol, Folpet, Fosetyl-Aluminum, Füíalide, Fuberidazole, Furalaxil, Furmecyclox, Guazatine, Hexachlorobenzene, Hexaconazole, Hymexazole, Imazalil, Imibenconazole, Iminoctadin, Iprobenfos (PPI), 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, Metiram, Metsulfovax, Myclobutanil, Nickel Dimethyldithiocarbamate, Nitrothal-isopropyl, Nuarimol, Ofurace, Oxadixyf, Oxamocarb, Oxycarboxin, Perfurazoat, Penconazole, Pencycuron, Phosdiphen, Pimaricin, Piperalin, Polyoxin, Probenazole, Prochloraz, Procymidon, Propamocarb, Propiconazole, Propineb, Pyrazophos, Pyrefenox, Pyrimethanil, Pyroquilon, Quintozen (PCNB), Sulfur and sulfur compositions, Tebuconazole, Tecloftalam, Tecnazen, Tetraconazole, Thiabendazole. Thicyofen. Thiophanatmethyl, Thiram, Tolcloph? S-methyl ?, Tolylfluanid, Triadimefon, Triadimenol, Triazoxid, Trichlamid, Tpcyclazole, Tridemorph, Triflumizole, Triforin, Triticonazole, Validamycin A, Vínclozolin, Zineb, Ziram. Bactericides: Bronopol, Dichlorophen, Nitrapyrin, nickel dimethyldithiocarbamate, 'Kasugamycin, Octhilinon, furanocarboxylic acid, Oxytetracyclin, Probenazole, Streptomycin, Tecloftalam, copper sulfate and other copper preparations. Insecticides / Acaricides / Nematicides: Abamectin, Acephat, Acetamiprid, Acrinathrin, Alanycarb, Aldicarb, Aldoxycarb, Alpha-cypermethrin, Alphamethrin, Amitraz, Avermectin, AZ 60541, Azadirachtin, Azamethiphos, Azinphos A, Azinphos M, Azocyclotin, Bacillus popilliae, Bacillus sphaericus , Bacillus subtilis, Bacillus thuringiensis, Baculovirus, Beauveria bassiana, Beauveria tenella, Bendiocarb, Benfuracarb, Bensultap, Benzoximate, Betacyluthrin, Bifenazate, Bifenthrin, Bioethanomethrin, Biopermethrin, BPMC, Bromophos A, Bufencarb, Buprofezin, Butathiophos, Butocarboxin, Butylpiridaben, Cadusafos, Carbaryl, Carbofuran, Carbophenothion, Carbosulfan, Cartap, Chloethocarb, Chlorethoxyphos, Chlorfenapyr, Chlorfenvinphos, Chlorfluazuron, Chlormephos, Chlorpyrifos, Chlorpyrifos M, Chlovaporthrin, Cis-Resmethrin, Cispermethrin, Clocythrin, cloethocarb, Clofentezine, Cyanophos, Cycloprene, Cycloprothrin, Cyfluthrin, Cyhalothrin , Cyhexatin, Cypermethrin, Cyromazine, Deltamethrin, Demeton M, Demeton S, Demeton-S-methyl, Diaclkoden, Diafenthiuron, Diazinon, Dichlorvos, Diflubenzuron, Dimethoat, Dimethylvinphos, Diofenolan, Disulfoton, Docusat-sodium, Dofenapyn, Eflusilanate, Emamectin. Empenthpn, Endosulfan, Eniomopfthora spp. , Esfenvalerate, Ethiophencarb, Ethion, Ethoprophos, Ethofenprox. Etoxazole, Etrimphos, Fenamiphos, Fenazaquin. Fenbutatin oxide. Fenitrothion, Fenothiocarb, Fenoxacrim, Fenoxycarb, Fenpropathrin, Fenpyrad, Fenpyrithrin, Fenpyroximate, Fenvalerate, Fenthion, Fenvalerate, Fipronil, Fluazinam, Fluazuron, Flubrocythrinate, Flucycloxuron, Flucythrinate, Flufenoxuron. Flutenzine, Fluvalinate, Fonophos, Fosmethilan, Fosthiazate, Fubfenprox, Furathiocarb, Granulosevirus, Halofenozide, HCH, Heptepophos, Hexaflumuron, Hexythiazox, Hydroprene, Imidacloprid, Isazophos, Isofenphos, Isoxathion, Ivemectin, Nuclear polyhedrovirus, Lamda-cyhalothrin, Lufenuron, Malathion, Mecarbam, Metaldehyd, Methamidophos, Metharhizium anisopliae, Metharhizium flavoviride, Methidathion, Methiocarb, Methomyl, Methoxyfenizide, Metolcarb, Metoxadiazone, Mevinphos, Milbemectin, Monocrotophos, Naled. Nitenpyram, Nithiazine, Novaluron, Omethoat, Oxamyl, Oxydemethon M, Paecilomyces fumosoroseus, Parathion A, Parathion M, Permethrin, Phenthoat, Phorat, Phosalon, Phosmet, Phosphamidon. Phoxim, Pirimicarb, Pirimiphos A, Pirimiphos M, Profenofos, Promecarb, Propaphos, Propoxur, Prothiophos, Prothoat, Pymetrozine. Pyrachlophos. Pyresmethrin, Pyrethrum, Pyridaben, Pyridathion, Pyrimidifen, Pyriproxifen, Quinalphos. Ribavirin, Salithion. Sebufos, Silafluofen, Spinosad, Sulfotep, Sulprofos, Taufluvalinate, Tebufenozide, Tebufeppyrad. Tebupirimphos, Teflubenzuron, Tefluthrin, Temephos, Temivinphos. Terbufos, Tetrachlorvinphos, Theta-cypermetrin. Thiapronil, Thiatriphos, Thiocyclam hydrogen oxalate, Thiodicarb, Thiophox, Thuringiensin, Tralocythrin, Tralomethrin, Triarathene, Triazamate, Triazophos, Triazuron, Trichlophenidine, Trichlorfon, Triflumuron, Trimethacarb, Vamidothion, Vaniliprole, Verticillium lecanii, YI 5302, Zeta-cypermethrin, Zolaprofos, (lR-cis) - [5- (phenylmethyl) -3-furanyl] -methyl-3- [(dihydro-2-oxo-3 (2H) -furaniIiden) -methyl] -2,2-dimethylcyclopropanecarboxylate (3-phenoxyphenyl) -methyl-2,2,3,3-tetramethylcyclopropanecarboxylate 1 - [(2-chloro-5 -thiazolyl) methyl] tetrahydro-3,5-dimethyl-N-nitro-1,3,5-triazin-2 (1 H) -imine 2- (2-Chloro-6-fluorophenyl) -4- [4- (1, 1-dimethylethyl) phenyl] -4,5-dihydro-oxazole 2- (acetyloxy) -3-dodecyl-1,4-naphthalenedione 2 -chloro-N - [[[4- (1-phenylethoxy) -pheny] -amino] -carbonyl] -benzamide 2-chloro-N - [[[4- (2,2-dichloro-l, l-difluorethoxy) -phenyl] ] -amino] -carbonyl] -benzamide 3-Methylphenyl-propylcarbamate 4- [4- (4-ethoxyphenyl) -4-methylpentyl] -l-fluoro-2-phenoxy-benzene 4-chloro-2- (1, 1-dimethylethyl) -5 - [[2- (2,6-dimethyl-4-phenoxyphenoxy) ethyl] thio] -3 (2H) -pyridazinone 4-chloro-2- (2-chloro-2-methylpropyl) -5 - [(6-iodo-3-pyridinyl) methoxy] -3 (2H) -pyridazinone 4-chloro-5-f (6-chloro-3-pyridinyl) methoxy] -2- (3,4-dichlorophenyl) -3 (2H) -pyridazinone Bacillus thuringiensis strain EG-2348 [2-benzoyl-l- (l, l -dimethyl) -hydrazide of benzoic acid benzoate of 2,2-dimethyl-3- (2,4-dichlorophenyl) -2-oxo-l-oxaspiro [4.5Jdec-3-en-4-yl f3 - [(6-chloro-3-pyridinyl) methylJ-2-thiazolidinylidene) -cianamide dihydro-2- (nitromethylene) -2H-l, 3-thiazine-3 (4H ) -carboxaldehyde ethyl- [2 - [[1,6-dihydro-6-oxo-l- (phenylmethyl) -4-pyridazinyl] oxy] etiI] -carbamate N- (3,4,4-trifluor-l -oxo-3-butenyl) ) -glycine N- (4-chlorophenyl) -3- [4- (difluoromethoxy) phenyI] -4,5-dihydro-4-phenylimide-1H-pyrazole-1-carboxamide N - [(2-chloro-5 -thiazolyl) methyl] -N'-methyl-N "-nitro-guanide N-methyl-N '- (1-methyl-2-propenyl) -1,2-hydrazindicarbotioamide N-methyl-N'-2-propenyl- 1, 2-hydrazindicarbothioamide O, O-diethyl- [2- (dipropylamino) -2-oxoethyl] -ethylphosphoramidothioate Herbicides: for example, anuides, such as for example diflufenican and propanil, arylcarboxylic acids, such as for example dichloropicolinic acid, Dicamba and Picloram, aryloxyalkanoic acids, such as, for example, 2,4 D, 2,4 DB, 2,4 DP, Flu roxypyr, MCPA, MCPP and Triclopyr; esters of the aryloxyphenoxyalkane 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; Desmedipham, 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 Methabenzothiazuron; hydroxylamipals, such as for example Alloxydim, Cletodim, Cycloxydim, Sethoxydim and Tralkoxydim; imidazolinones, such as, for example, Imazethapyr, Imazemethabenz, Imazapyr and Imazaquin; nitriles, such as for example Bromoxynil. Dichlobenil and Ioxynil; Oxyacetamides, such as for example Mefenacet; sulfonylureas, such as for example Amidosulfuron, Bensulfuron-methylo, Chlorimuron-ethyl, Chlorsulfuron,. Cinosulfuron, Metsulfuron-methyl, Nicosulfuron, Primisulfuron, Pyrazosulfuron-ethyl, Thifensulfuron-methyl, Triasulfuron and Tribenuron-methyl; thiocarbamates, such as for example Butylates, Cycloates, Diallates, EPTC, Esprocarb, Molinate, Prosulfocarb, Thiobencarb and Triallate; triazines such as, for example, Atrazin, Cyanazin, Simazin, Simetryna, Terbutryne and Terbutylazin; triazinones, such as for example Hexazinon, Metamitron and Mmetribuzin; others, such as for example Aminotriazole, Benfuresate, Bentazone, Cinmethilin, Clomazone, Clopyralid, Difenzoquat, Dithiopyr, Ethofumesate, Fluorchloridone, Glufosinate, Gliphosate, Isoxaben, Pyridate, Quinchlorac, Quinmerac, Sulphosate and Tridiphane. The active compound according to the invention can also be present in its 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 ingredient content of the application forms prepared from the commercially available formulations can vary within wide limits. The active compound concentration of the application forms can be between 0.0000001 to 95 by weight of active compound, preferably between 0.0001 and 1 c 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 stability to alkalis on limed substrates. 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. From the order of malofagids and amblycerine sub-orders as well as ischinocerines, for example Trimenopon spp., Menopon spp., Trinoton spp., Bovicola spp., Werneckiella 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., Eusimulium spp. , Phlebotomus spp., Lutzomyia spp. , Culicoides spp., Chrysops spp. , Hybomitra spp., Atylotus spp., Tabanus spp. , Haematopota spp. , Philipomya spp. , Braula spp. , Musca spp. , Hydrotaea spp. , Stomoxys spp. , Haematobia spp., Morellia spp., Fannia spp., Glossina spp., Calliphora spp., Lucilia spp. , Chrysomya spp. , Wohlfahrtia spp. , Sarcophaga spp. , Oestrus spp., Hypodema 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. From the order of heteropterids, for example Ci ex spp. , Triatoma spp. , Rhodnius spp., Panstrongylus spp. From the order of the blataridos. for example Blatta orientalis. American Periplaneta. Germanic Blattella. Supella spp. Of the sub-class of mites (Acarida) and of the order of the meta- as well as mesoestigmatos, for example Argas spp., Ornithodorus spp., Otabius spp. , Ixodés spp., Amblyomma spp., Boophilus spp., Dermacentor spp., Haemaphysalis spp., Hyalomma spp., Rhipicephalus spp., Dermanyssus spp., Raillietia spp., Pneumonyssus spp., Sternostoma spp., Varroa spp. order of the actinedides (Prostigmata) and acaridids (Astigmata), for example Acarapis spp., Cheyletiella spp., Ornithocheyletia spp., Myobia spp., Psoresgates 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. As an example, they show excellent activity against Boophilus microplus and Lucilia cuprina. 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 is possible a more economical and simple animal maintenance. 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, intraperitoneal and the like), implants, by nasal application, by dermal application in form, for example immersion or bathing (Dippen), spray (Spray), surface watering (Pour-on and Spot-on), washing, dusting as well as with the aid of molded bodies containing the active product such as collars, ear tags, tail tags, limb bands, halters, marking 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 10,000 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. In an exemplary and preferred way - however without limitation - the following insects may be mentioned: Beetles, such as Hylotrupes bajulus, Chlorophorus pilosis, Anobium punctatum, Xestobium rufovillosum, Ptilinus pecticornis. Dendrobium pertinex, Ernobius mollis, Ppobium carpine, Lyctus brunneus. Lyctus africanus, Lyctus planicollis, Lyctus linearis. Lyctus pubescens. Trogoxylon aequale, Minthes rugicollis; Xyleborus spec. Tryptodepdron spec. Apate monachus, Bostrychus capucins, Heterobostrychus brunneus. Sinoxylon spec. , Dinoderus minutes. Hymenoptera, such as Sirex juvencus, Urocerus gigas, Urocerus gigas taignus, Urocerus augur. Termites Reticulitermes, such as Kalotermes flavicollis, Cryptotermes brevis, Heterotermes indicala, Reticulitermes flavipes, Reticulitermes santonensis, Reticulitermes lucifügus, Mastotermes darwiniensis, Zootermopsis nevadensis, Coptotermes formosanus. Thysanides, such as Lepisma saccarina. Industrial materials will be understood in the present context as non-living materials, such as, preferably, synthetic materials, glues, glues, paper and cardboard, leather, wood and wood processing products and paints.

In a very special way, the materials to be protected against attack by insects are made of wood and wood products. By wood and wood processing products, which can be protected by means of the agents according to the. invention or mixtures containing them, shall be understood, for example: construction timber, wooden beams, railway sleepers, parts for bridges, ribs for boats, wooden vehicles, boxes, pallets, containers, telephone poles, coatings of wood, wooden windows and doors, wooden plywood, plywood plates, carpentry works or wood products, which find application, in 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, optionally drying agents 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. As solvent and / or diluent, 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 volatilize and / or a solvent or mixture of organo-chemical solvents. polar and / or water and, if appropriate, an emulsifier and / or humectant. As organochemical solvents, preference will be given to 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 220 ° C, spindle oil with a boiling range of 250 to 350 ° C, petroleum or aromatic hydrocarbons 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 having a boiling range of 180 to 220 ° C and / or oil for use are used. spindles and / or monochloronaphthalene, preferably a-monochloronaphthalene. Organic solvents, which are difficult to volatile, oleaginous or oleaginous, with an evaporation index above 35 and with a flame point above 30 ° C., preferably above 45 ° C., can be partially replaced by organic solvents. light chemicals or medium volatility, with the proviso that the solvent mixture has an evaporation index above 35 and a flame point above 30 ° C, preferably above 45 ° C, and that the insecticide-fungicide mixture is soluble or emulsifiable in this solvent mixture According to a preferred embodiment, a part of the solvent or mixture of organochemical solvents or a solvent or mixture of aliphatic, polar, organic chemical solvents is preferably used. aliphatics containing hydroxyl and / or ester and / or ether groups, such as, for example, ghol ether, esters or the like Synthetic resin and / or drying oils will be used as organochemical binders within the scope of the present invention of curing, in themselves known, dilutable with water and / or soluble or dispersible or emulsifiable in the organo-chemical solvents used, especially agglutinates formed by or containing acrylic resin, a vinyl resin, for example polyvinyl acetate, polyester resin, polycondensation or polyaddition resin, polyurethane resin, alkyd resin or modified alkyd resin, phenolic resin, hydrocarbon resin such as resin of indeno-coumaron, 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 employ at least one alkyd resin or a modified alkyd resin and / or a drying vegetable oil as the organochemical binder according to the invention. 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 completely replaced by a fixing agent (mixture) or by a plasticizer (mixture). These additives must prevent volatilization of the active compounds, as well as crystallization or precipitation. Preferably, they 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, adipic acid esters, such as di- (D-adipate). 2-ethylhexyl), stearates such as butyl stearate or amyl stearate, oleates such as butyl oleate, glycerin ethers or high molecular weight glycol ethers, glycerin esters as well as esters of p-toluenesulfonic acid. Fixative agents are chemically based on polyvinylalkyl ethers such as polyvinyl methyl ether or 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. Agents ready for application may, if necessary, contain other insecticides and. if necessary, one or several 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 constitute, expressly, integral part of the present application. Particularly preferred mixing components are insecticides, such as Chlorpyriphos, Phoxim, Silafluofin, Alphamethrin. Cyfluthpn, Cypermethrin, Deltamethrin, Permethrin, Imidacloprid, NI-25. Flufenoxuron. Hexaflumuron and Trifiumuron, 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-di-chloro-N-octylisothiazolin- 3 -one The preparation and use of the active compounds according to the invention are apparent from the following examples. The capital letters located behind some of the numbers in the examples will serve to find these structures more easily in the formulas schemas. These designate different meanings of Q. Examples. Example I-1-a-1 7.8 g of potassium tert-butylate in 20 ml of anhydrous DMF (dimethylformamide), at 60 ° C, 7.2 g of the compound according to example IIC-1 in 10 ml of anhydrous DMF are added. Stir at this temperature until the reaction is complete (controls by means of thin layer chromatography (DC), eluent methylene chloride: ethyl acetate 5: 3), concentrate by evaporation in vacuo, collect the residue in 100 ml. of water and acidified at approximately 0 ° C with 20% hydrochloric acid. The precipitate is separated by suction filtration and dried. Performance 4.0 g (61 9 of the theory), P.f. 250 ° C.

Example I-1-a-2 Il-E In 50 ml of DMF, 12 g of potassium tert-butylate and 5.3 g of compound II-E are stirred for 2 hours at 80 ° C. It is combined with toluene and concentrated by evaporation in vacuo. The residue is taken up in 30 ml of ice water and combined at approximately 0 ° C. with 20% hydrochloric acid until the pH value is between 5 and 6. It is then filtered off by suction and purified. by column chromatography (silica gel, methylene chloride 'ethyl acetate' 3). Yield 1.15 g (36% of theory), P.f. 163 ° C. Example I-1-a-3.

II-B-2 Analogously, starting with the compounds according to example II-B-2, the above-mentioned compound with a melting point > 250 ° C.

Example I-1-a-4.

P.f. 186-188 ° C According to the above-mentioned methods, the products of the formula (I-1-a) indicated in Table 25 below are also prepared. Table 25 Example I-1-b-1. 2 g of the compound according to Example I-1-a-1 were refluxed with 1.1 ml of triethylamine and 0.75 g of isobutyryl chloride for 4 hours in 50 ml of ethyl acetate (ethyl acetate). It is concentrated by evaporation and the residue is chromatographed on silica gel (eluent hexane: acetone 7: 3). Yield 1.15 g (48 9 of the theory), P.f. 247 ° C. Example I-1-b-2. The following compound having a melting point of 189 ° C is obtained analogously to that of Example I-1-b-1.

Example I-1-c-1.

Add dropwise to 1.3 g of the compound according to example (Ila-1) and 0.6 ml of triethylamine in 50 ml of anhydrous methylene chloride at 0 ° C, 0.4 ml of chloroformate. of ethyl in 5 ml of anhydrous methylene chloride and stirred for a more days without refrigeration. It is then washed twice with 50 ml of 0.5 N NaOH, dried and concentrated by evaporation. Yield 0.70 g (45% of theory). P.f. 196 ° C. Example I-2-a-1.

It is added, drop by drop, to 1 1 .22 g of tere-potassium butylate, in 100 ml of DMF anhydrous, a solution of 34.6 g of the compound according to Example III-A-1 and stir overnight at room temperature For working up, 1 liter of HCl is added dropwise in the reaction mixture. extract with methylene chloride. it is dried and concentrated by evaporation. The residue is chromatographed with ethyl acetate on silica gel. D Yield 5.5 g (18 9 of the theory) P. f 190-195 ° C.

Example I-2-a-2.

They are added, drop by drop, to 6.72 g of tere. potassium buniate, in 5 ml of DMF, at 0 to 10 ° C, 15 g of the compound according to example III-2, dissolved in 15 ml of DMF. It is stirred overnight at room temperature, concentrated by evaporation, the residue is taken up in water and acidified under ice cooling with HCl. The precipitate is separated by suction filtration and dried. Yield 10.9 g (62 9 of the theory), P.f. 74-80 ° C. Analogous to that of the examples I-2-a-1 and I-2-a-2 or according to the general indications for the preparation, the compounds of the formula I-2-a are prepared.

Table 26.

Example I-2-a-ll Add dropwise to 6.5 g of potassium tert-butylate in 40 ml of DMF (dimethylformamide), at room temperature, 9.3 g of the compound according to example (III-C-1), heating to room temperature. this case the reaction mixture. It is stirred for a further day at room temperature, combined with water and extracted with methylene chloride. The aqueous phase is acidified with HCl (pH 2-3) and extracted with methylene chloride. The organic phase is concentrated by evaporation. Yield 3.40 g (68% of theory). P.f. 272 ° C. According to the methods indicated above, the products of the formula (I-2-a) indicated in Table 27 below Table 27 are also prepared. i 0 Example I-2-b-l.

Add dropwise to 3.00 g of the compound according to example 1-2 -a-1 and 1.52 ml of triethylamine in 40 ml of methylene chloride, at 0 to 10 ° C, 1.24 g of chloride of pivaloyl, dissolved in 10 ml of methylene chloride and stirred overnight at room temperature. The reaction mixture is washed successively with 10 5c solution of citric acid, NaHCO3 solution of NaCl solution, dried and concentrated by evaporation. The residue is chromatographed on silica gel with the eluent 3: 1 cyclohexane: ethyl acetate. Yield 1.79 g (theory 47), P.f. 133-136 ° C. Example I-2-b-2. 0.96 g of compound gel according to example I-2-b-l, 0.25 g of O-methylhydroxylamipa hydrochloride and 1 g of molecular sieve 3 A are added in 15 ml of methanol for 12 hours at room temperature. The molecular sieve is separated by filtration, concentrated by evaporation, the residue is partitioned between water and methylene chloride, the organic phase is dried and concentrated by evaporation in a vacuum. The residue is chromatographed on silica gel with ethyl cyclohexane acetate 5: 1. Yield 0.39 g (39% of theory), P.f. 115-127 ° C. The following compounds of the formula (I-2-b) are prepared analogously to Examples I-2-b-1 and I-2-b-2 or according to the general instructions for preparation. Table 28 (I-2-b) -HO- Example I-2-c-1.

In a manner analogous to that of Example I-2-b-1, the above-mentioned compound is obtained when isopropyl chloroformate is used instead of pivaloyl chloride, with a yield of 46% of theory. P.f. 140-141 ° C Example I-2-C-2.

In a manner analogous to that of example I-2-b-1, the above-mentioned compound is obtained when isopropylthio chlorotormate is used instead of pivaloyl chloride, with a yield of 1.3 g in the form of an oil. Analogously to the examples I-2-c-1 and I-2-C-2 or in accordance with the general instructions for preparation, the following compounds of the formula 1-2-c are prepared.

Table 29.

Example II-B-1.

It is added, drop by drop, to 75 g of concentrated sulfuric acid, at an internal temperature of 30 to 40 ° C, a suspension of 50 g of the compound according to example XX-C-1 and stirred for another 2 hours to this temperature. Then, dropwise, 110 ml of methanol are added in such a way that an internal temperature of 40 ° C is established. It is then stirred for another 6 hours at 40 to 70 ° C. Coming on 600 g of ice, it is combined with aqueous NaHCO solution; and extracted with methylene chloride. Yield 40 g (74 9 of the theory), P.f. 136-137 ° C. Example II-B-2.

In a manner analogous to that of! Example II-B-1 1, 7 g (15 9. of the theory) of the above-indicated compound are obtained from 69 g of the compound according to example XX-B-1. P.f. 1 18-120 ° C.

Example H-C-1 Combine 20 g of the compound according to example II-B-1 in 50 ml of pyridine at room temperature with 4.2 g of O-methylhydroxylamine hydrochloride. and stirred for 4 hours at 50 ° C. Concentrate by evaporation in vacuo, combine the residue with about 50 ml of water and extract three times with methylene chloride. The combined organic phases are dried and concentrated by evaporation. The residue is chromatographed on silica gel with methylene chloride: ethyl acetate 5: 3. i c Yield 19.9 g (99 9 of the theory). P.f. 158-160 ° C. Example II-E-1. 32 g of the compound of the formula (XV) are combined and 57 ml of triethylamine in 200 ml of tetrahydrofuran at -10 to 0 ° C, with 34 g of 2,4-dimethylphenylacetyl chloride and stirring for a further day at room temperature. It is separated by suction filtration and the filtrate is concentrated by evaporation. The residue is chromatographed on silica gel. Yield 5.3 g. 'H-NMR (400 MHz, d6-DMSO): d = 2.19-2.25 (4s, 12H, Ar CH3), 4.63-4.69, 4.82-4.86 (m, 1H , CO-O-CH), 6.9-7.06 (m, 6H, Ar-H). Example III-l.

To 27.90 g of ethyl l-hydroxyl-4-oxo-c-clohexanecarboxylate in 150 ml of toluene, 29.55 g of 2,4,6-phenylphenylacetyl chloride is added and heated overnight. under reflux. It is then concentrated by evaporation in vacuo and the crude product is used without further purification in the cyclocondensation reaction Yield 42.9 g (theory 82), oil Example III-2.

Add dropwise to 10 g of the compound of Example XXI-3 and 5.6 g of triethylamine, in 100 ml of methylene chloride, at 0 to 10 ° C, 9, 14 g of chloride of 2,4 , 6-trimethylphenylacetyl and stir overnight at room temperature. It is then washed with water, the organic phase is dried and concentrated by evaporation. Yield 15.14 g. oil. In a manner analogous to that of Examples III-1 and III-2 or in accordance with the general indications for preparation, the following compounds of formula III are prepared.

Table 30 Example III-C-1.

Combine 1 1 g of the compound according to example (XXI-2) with 200 ml of toluene at room temperature with 40 g of 2,4-d-chlorophenylacetyl chloride (3.5 equivalents) and heat for 1 day under reflux. It is concentrated by evaporation and the residue is chromatographed on silica gel with hexane / ethyl acetate 2/1. P.f. 57 ° C. Example XIX- 1.

To the mixture consisting of 414.2 g of 25% solution of ammonia, 139.6 g of ammonium chloride, 127.9 g of sodium cyanide and 392 ml of water, at room temperature, are added dropwise to the mixture. , 3 g of 4-hydroxycyclohexanone and stir overnight at 45 ° C. The precipitate is separated by filtration by suction and dries. Yield 197 g (64% of theory), P.f. 130 ° C. Example XIX-2.

To the mixture formed by 48.5 g of 25 ml solution of ammonia, 16.4 g of ammonium chloride, 15.0 g of sodium cyanide in 46 ml of water are added dropwise at room temperature. 36.0 g of the compound according to Example XXV-1 and stirred overnight at 38 ° C. After extraction with methylene chloride and working up in the usual manner, 33.8 g (79.5t of theory) of the above-mentioned compound are obtained in the form of an oil. -.o Example XX- A-l. 49 g of l-cyano-4-hydroxycyclohexylamine, according to example XIX-1 and 49 ml of triethylamine, are added in 500 ml of THF at -20 ° C, 79 g of 2,4-dichlorophenylacetyl chloride in 50 g. ml of THF. It is stirred for 1 hour at room temperature, extracted with 1 liter of 0.5 N HCl, the organic phase is dried and concentrated by evaporation. Yield 70 g (61% of theory), P.f. 148-150 ° C. Example XX-B-1. 70 g of the compound according to example XX-A-1 are oxidized analogously to that of example XXV-1. Yield 69.0 g (99 9 of the theory), P. f 76-78 ° C.

Example XX-C-1. 33 g of the compound according to example XIX-1 and 32 ml of triethylamine are added to 100 ml of THF (tetrahydrofuran) at approximately 0 ° C, 40 g of 2,4,6-trimethylphenylacetyl chloride in 50 ml. of THF and stirred for 2 hours at room temperature. For the preparation, the reaction mixture is shaken with 1 liter of NaOH IN, the organic phase is separated, dried and concentrated by evaporation. Yield 52 g (79% of theory). P.f. 22 ° C. Example XXI-1. I D Add, dropwise, to 102.0 g of cyclohexanedione-1, 4- 0 monoethylene glycol (commercially available) and 0.6 ml of triethylamine in 102 ml of ethanol, at room temperature. 2S.7 ml of cyanuric acid and stir for 1 hour at room temperature. It is combined with 229 ml of ethanol, shaken at 0 to 5 ° C with gaseous HCl and stirred overnight at room temperature. It is then concentrated by evaporation in vacuo and the residue is stirred in 980 ml of water overnight at room temperature. It is extracted with methylene chloride, the organic phase is washed with saturated KJCOJ solution, dried and concentrated by evaporation. Yield 68.3 g (50% theory), oil. Example XXI-2.

Saturated with gaseous HCl about 1 kg of the compound according to example XXX-1 in 5 liters of n-butanol at -20 to 0 ° C. It is stirred for approximately 3 hours at 0 ° C, then overnight without cooling. Concentrate by evaporation in vacuo, combine the residue with about 5 liters of water and stir for 1 hour at room temperature. It is extracted with 2.5 liters of methylene chloride, dried and concentrated by evaporation-c, yield 1.376 g (81 5c of the theory), yellow oil. Example XXI-3.

The following are stirred overnight at 50 ° C 1.86 g of the compound according to Example XXI-1 and 0.88 g of O-methylhydroxylamine hydrochloride in 20 ml of pyridine. Concentrate by evaporation in vacuo, collect the residue in water and methylene chloride, wash with 10 citric acid. the organic phase is dried and concentrated by evaporation. Yield 1.7 g, oil Example XXV-1. 300 ml of methylene chloride are added at -70 ° C to 11 ml of oxalyl chloride. Add 10 ml of DMSO (dimethyl sulfoxide) and stir for 3 minutes at -35 ° C. Cool to -70 ° C again and add 150 g of the compound according to Example XXVI-1 as a 10% solution in methylene chloride over the course of 1 hour. Stir for another 15 minutes at -35 ° C, then add 130 ml of triethylamine and stir for 1 hour at room temperature. It is then carefully combined with water, extracted with methylene chloride and filtered through silica gel. Yield 7.9 g (56 9 of theory), oil. Example XXVI-1.

Combine, at room temperature, 5.7 g of 4-hydroxy-cyclohexanone in 50 ml of pyridine, with 4.2 g of O-methylhydroxyamine hydrochloride and stir for 4 hours at 50 ° C. It is concentrated by evaporation in a vacuum, the residue is taken up in approximately 50 ml of water and extracted three times with methylene chloride. The combined organic phases are dried and concentrated by evaporation. Yield 6.9 g (96 5c of theory), oil.

Example XXVII-1.

To 446.4 g of ammonium carbonate and 98.0 g of sodium cyanide in 1600 ml of water, a solution of 70.5 g of the compound according to example XXV-1 in 1600 ml of ethanol is added and stirred for 120 hours. hours at 60 ° C. It is then cooled to 5 ° C and the precipitate is separated by suction filtration. Yield 156.7 g (74% of theory), P.f. > 250 ° C. Example XXX- 1.

AAZ To 1,004.4 g of 4-hydroxycyclohexanone and 3.70 ml of triethylamine are added dropwise at room temperature over the course of about 45 minutes, 249.5 g of cyanuric acid and stirred for about 1 hour. hour to 65 ° C. It is stabilized with 0.6 ml of o-phosphoric acid at 85 ° C and dried under a water pump vacuum. The crude product cn is transformed, without further elaboration, into the compounds of the formula (XXI). Application examples: Example A Ensa or with Myzus. 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 oleracea), which are strongly attacked by the louse of the peach leaf (Myzus persicae), are treated by immersion in the preparation of the active compound of the desired concentration. At the end of the desired time the destruction is determined in percentage. In this case, 100% means that all the lice in the leaf were destroyed; 0% means that no leaf louse was destroyed. In this test, for example, the compounds were produced according to the preparation examples I-2-b-2, I-2-C-2, I-2-b-3, I-2-b-4, I-2 -a-8, I-2-a-9, i-2-b-8, I-2-C-5, I-2-b-9, 1-2-c-or, I-2-b -10, I-2-bl l, I-2-b-12, I-2-C-7, Ila-1 and Ilb-1 at an exemplary concentration of active product of 0.1 9 c caused a destruction respectively of the 100 5c after 6 days. Example B Test with Nephotettix. Solvent: 7 parts by weight of dimethylformamide. Emulsifier: 1 Part by weight of alkylaryl glycol ether. To obtain a suitable preparation of active compound, 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. Rice seedlings (Oryza sativa) they are treated by immersion in the preparation of active product of the desired concentration and are covered with larvae of green rice cicadas (Nephotettix cincticeps), while the seedlings are still wet. 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, for example, the compounds were produced according to the preparation examples I-2-a-2, I-2-b-3, I-2-D-4, I-2-b-5, I-2 -C-2, I-2-a-5, I-2-a-6, I-2-C-3, I-2-b-7, I-2-C-4, I-2-a -7, I-2-a-9, I-2-b-9, I-2-C-6, Ila-1 and Ilb-1 at an exemplifying concentration of active product of 0.1% caused destruction respectively of 100% after 6 days. EXAMPLE C Assay with Panonychus Solvent: 3 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 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 containing emulsifier to the desired concentration. Plum saplings are sprayed, with an approximate height of 30 cm (Prunus domestica), which are strongly attacked by all development stages of the spider mite of the fruit trees (Panonychus ulmi), with an active product preparation of the desired concentration. After the desired time, the effect on the fruit is determined. . In this case 100 c means that all the mites of the spider mite were destroyed. 0 5c means that no spider mite was destroyed. In this test, for example, the compound according to the preparation example I-2-b-2 at an exemplary concentration of the active compound of 0.02% had a 100% effect after 7 days. Example D Test with Phaedon larvae Solvent: 7 parts by weight of dimethylformamide. Emulsifier: 1 Part by weight of alkylaryl polyglycol ether. To obtain a convenient preparation of suitable 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 olerácea) are treated by immersion in the preparation of active product of the desired concentration and are covered with larvae of the horseradish leaf beetle (Phaedon cochleariae), while the leaves are still moist. After the desired time, the destruction is determined at 5. In this case 100 5c means that all the larvae of the beetle were destroyed, 0 9 means that no beetle larvae were destroyed. In this test, for example, they elicited the compounds according to the preparation examples I-2-b-2, I -2-b-3, I-2-C-2, 1-2-c-or, Ila-1 and Ilb-1 at an exemplary concentration of active product of 0.1 1 a destruction respectively of 100 5c after 7 days Example E Test with Spodoptera Frugiperda Solvent: 7 parts by weight of dimethylforma ida. Emulsifier: 1 Part by weight of alkylarylglycol 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 olerácea) are treated by immersion in the preparation of the active compound of the desired concentration and are covered with caterpillars of the moth nocmela (Spodoptera frugiperda), while the leaves are still moist. After the desired time, the degree of destruction in% is determined. In this case 100% means that all caterpillars were destroyed; 0 5th means that no caterpillar was destroyed. In this test, for example, the compounds according to the preparation examples I-2-b-2, I-2-b-3, I-2-C-2, I-2-C-5, Ila-1 were produced , and Ilb-1 at an exemplary concentration of the active product of 0.1% a degree of destruction respectively of 100% after 7 days. Example F Test with Tetranychus (OP-resistant / dip treatment) Solvent: 3 parts by weight of dimethylformamide Emulsifier: 1 Part by weight of alkylaryl polyglycol ether. To obtain a convenient preparation of suitable active compound, part I by weight of the active compound is mixed with the indicated amount of solvent and the indicated amount of emulsifier and the concentrate is diluted with water to the desired concentration. Bean plants (Phaseolus vulgaris), which are strongly attacked by all the stages of the development of the common spider mite (Tetranychus urticae), are treated by immersion in a preparation of the active compound of the desired concentration. After the desired time, the effect on is determined. In this case they mean 100% that all spider mites were killed; 0% means that no spider mite was killed. • In this test, for example, compounds were produced according to the preparation examples I-2-b-2, I-2-a-2, I-2-b-3, I-2-b-4, I- 2-b-5, I-2-C-2, I-2-C-3, I-2-C-5, I-2-b-9, I-2-C-6, I-2- b-10, I-2-bl and Ilb-1 at an exemplary concentration of the active product of 0.01% an effect respectively of 100% after 7 days. Example G Test with resistant Boophilus microplus / strain Parkhurst SP-resistepte. Test animals: Adult females raised. Solvent: Dimethylsulfoxide. 20 mg of active compound are dissolved in 1 ml of dimethyl sulfoxide, the lower concentrations are prepared by dilutions in the same solvent.

The test is carried out with quintuple determinations. 1 μl of the solution is injected into the abdomen, the animals are transferred to capsules and stored in an air-conditioned room. The effect controls are carried out after 7 days with respect to the inhibition of egg laying. An effect of 100 5c means that none of the ticks has laid eggs. In this test, for example, the compounds according to the preparation examples I-1-a-1 and I-1-b-1 were available at an exemplary concentration of active compound of 20 μg / animal, respectively, an effect of 100 μl. Example H Blowfly larvae / developmental inhibitor effect. Test animals: Lucilia cuprina larvae Solvent: Dimethylsulfoxide. 20 mg of active compound are dissolved in 1 ml of dimethylsulphoxide, the lower concentrations are prepared by dilutions with distilled H.O.

Approximately 20 Lucilia cuprina larvae are placed in test tubes, containing approximately 1 cm3 of horse meat and 0.5 ml of the preparation of active product to be tested. After 24 and 48 hours the activity of the preparation of the active product is determined. The test tubes are transferred to cups with the bottom covered with sand. After another 2 days, the test tubes are removed and the number of pupae is counted. The effect of the preparation of the active product is evaluated according to the number of flies that have hatched after 1.5 times the development time of an untreated control. In this case 100% means that no fly hatched; 0% means that all flies normally hatched. In this test, for example, the compounds according to the preparation examples I-2-b-2 and I-1-a-1 were prepared at an exemplary concentration of the active compound of 1000 ppm respectively, a 100% effect. 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.

Claims (6)

REmR r AqoNES Having described the invention as above, the content-in-the following claims are claimed as property:

1. - Compounds of the formula (I) characterized because; X means halogen, alkyl, alkenyl, alkynyl, alkoxy, alkenyloxy, alkylthio, alkylsulfinyl, alkylsulfonyl, haloalkyl, haloalkenyl, haloalkoxy, haloalkenyloxy, nitro, cyano or means phenoyl, phenoxy, phenylthio, benzyloxy or benzylthio respectively substituted, Y means hydrogen, halogen, alkyl, alkenyl, alkynyl, alkoxy, alkenyloxy, alkylthio, alkylsulfinyl, alkylsulfonyl, haloalkyl, haloalkenyl, haloalkoxy, haloalkenyloxy, nitro or cyano, Z stands for halogen, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, alkoxy, alkenyloxy, haloalkoxy, haloalkenyloxy, nitro or cyano, n means 0, 1, 2 or 3, Het means one of the groups (2) or where G means hydrogen (a) or means one of the groups R ° E (0 / N (g) "R7 where 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, means cycloalkyl optionally substituted by halogen, by alkyl or by alkoxy, which may be interrupted by one or more heteroatoms or means phenyl, phenylalkyl, hetaryl, phenoxyalkyl or hetaryloxyalkyl respectively substituted, where R <2> is alkyl, alkenyl, alkoxyalkyl or polyalkoxyalkyl, optionally substituted by halogen, or means cycloalkyl. phenyl or benzyl substituted, if appropriate, R <R> and R <5>, 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, R6 and R \ each independently denote hydrogen, are alkyl, cycloalkyl, alkenyl, alkoxy or alkoxyalkyl substituted by halogen, optionally substituted phenyl, optionally substituted benzyl, or together with the N atom, to which they are bonded, they mean a ring containing, if necessary, oxygen or sulfur, What does it mean R "means hydrogen, means alkyl, cycloalkyl, phenyl, benzyl or hetaryl respectively substituted, or means CO-R1; CO.-R:; SO.-R1; 11 R / CONH- ,; CONHRn or CO- - N, 1- R means hydrogen or alkyl, R "means alkyl or alkenyl. R ?: means alkyl or alkenyl, m means 0, 1 or 2, R 'independently of R' has the meanings indicated above for R1 and R2 independently of R2 has the meanings indicated above for R2.

2. - Compounds of the formula (I) according to claim 1, car-Eteiza? -s p rqué; 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, alkenyloxy with 3 to 6 carbon atoms, alkylthio with 1 to 6 carbon atoms, alkylsulfinyl with 1 to 6 carbon atoms, alkylsulfonyl with 1 to 6 carbon atoms, halogenalkyl with 1 to 6 carbon atoms, halogenalkenyl with 2 to 6 carbon bonds, haloalkoxy with 1 to 6 atoms of carbon, halogenalkenyloxy having 3 to 6 carbon atoms, nitro, cyano or means phenyl, phenoxy, phenylthio, benzyloxy or benzylthio substituted, where appropriate, by halogen, 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 halogenalkoxy with 1 to 4 carbon atoms, by nitro or by cyano, Y means hydrogen, halogen, alkyl with 1 to 6 carbon atoms, alkenyl with 2 to 6 carbon atoms, alky nyl with 2 to 6 carbon atoms, alkoxy with 1 to 6 carbon atoms, alkenyloxy with 3 to 6 carbon atoms, alkylthio with 1 to 6 carbon atoms, alkylsulfinyl with 1 to 6 carbon atoms, alkylsulfonyl with 1 to 6 carbon atoms, haloalkyl with 1 to 6 carbon atoms carbon, halogenalkenyl with 2 to 6 carbon atoms, halogenalkoxy with 1 to 6 carbon atoms, haloalkenyloxy with 3 to 6 carbon atoms, nitro or cyano, Z means halogen, alkyl with 1 to 6 carbon atoms, alkenyl with 2 a 6 carbon atoms, alkynyl with 2 to 6 carbon atoms, haloalkyl with 1 to 6 carbon atoms, halogenalkenyl with 2 to 6 carbon atoms, alkoxy with 1 to 6 carbon atoms, alkenyloxy with 3 to 6 carbon atoms, halogenalkoxy with 1 to 6 carbon atoms, haloalkenyloxy with 3 to 6 carbon atoms carbon, nitro or cyano, n means 0, 1, 2 or 3, Het means one of the groups G means hydrogen (a) or means one of the groups O SO ^ - R R "^ R1 (b), J M e (c), v r-, 5 W 'L // ^ R = (e). R ° E (0 / N. (9) T ' where 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 with 1 to 8 carbon atoms carbon, substituted, if appropriate, by halogen, 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, in which If necessary, one or more methylene groups directly adjacent to each other (especially not more than two) are replaced by oxygen and / or sulfur, phenyl which is optionally substituted by halogen, by cyano, by nitro, by alkyl having from 1 to 6 carbon atoms , by alkoxy with 1 to 6 atoms carbon atoms, by halogenalkyl with 1 to 6 carbon atoms, by haloalkoxy with 1 to 6 carbon atoms, by alkylthio with 1 to 6 carbon atoms or by alkylsulfonyl with 1 to 6 carbon atoms, means phenyl-alkyl with 1 to 6 carbon atoms. at 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 haloalkoxy with 1 to 6 carbon atoms means hetaryl with 5 or 6 members, optionally substituted by halogen or by alkyl having 1 to 6 carbon atoms (for example pyrazolyl, thiazolyl, pyridyl, pipmidyl, furanyl or thienyl), means phenoxy alkyl having 1 to 6 carbon atoms optionally substituted by halogen or by alkyl having 1 to 6 carbon atoms or 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 (for example pyridyloxy-alkyl with 1 to 6 carbon atoms, pyrimidyloxy-alkyl with 1 to 6 carbon atoms or thiazolyloxy-alkyl with 1 to 6 carbon atoms), R2 means alkyl with 1 to 20 carbon atoms carbon, 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 respectively if appropriate by halogen, 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 respectively in in the case given 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 or by halogenalkoxy with 1 to 6 carbon atoms . means alkyl having from 1 to 8 carbon atoms optionally substituted by halogen or means phenyl or benzyl, respectively 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 haloalkoxy with 1 to 4 carbon atoms, by cyano or by nitro, R4 and R - independently, mean alkyl with 1 to 8 carbon atoms, alkoxy with 1 to 8 carbon atoms, alkylamino with I to 8 carbon atoms, di- (a-alkyl with 1 to 8 carbon atoms) amino, alkylthio with 1 to 8 carbon atoms, alkenylthio with 2 to 8 carbon atoms, cycloalkylthio with 3 to 7 carbon atoms substituted, where appropriate, by halogen or phenyl, phenoxy or phenylthio, respectively substituted, if appropriate, by halogen, by nitro, cyano, by alkoxy with 1 to 4 carbon atoms, by halogenalkoxy with 1 to 4 carbon atoms, by alkylthio with 1 to 4 carbon atoms, by halogenalkylthio with 1 to 4 carbon atoms, by alkyl with 1 to 4 atoms of carbon or by halogen alkyl with 1 to 4 carbon atoms arbono R6 and R7 stand for hydrogen independently, meaning alkyl with 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 from 1 to 8 carbon atoms substituted, if appropriate, by halogen, means phenyl optionally substituted by halogen, by halogenalkyl with 1 to 8 carbon atoms, by alkyl with 1 to 8 carbon atoms; carbon or alkoxy with 1 to 8 carbon atoms, meaning benzyl optionally substituted by halogen, by alkyl with 1 to 8 carbon atoms, 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, in which it is replaced, if necessary by oxygen or sulfur, with a methylene group not directly adjacent to the nitrogen atom, Q means Rs OR '\ / \ / C = N-N C / \ 10 / OR' R9 is hydrogen, is alkyl having from 1 to 8 carbon atoms, optionally substituted by halogen, means cycloalkyl having from 3 to 8 carbon atoms, optionally substituted by halogen, by alkyl having 1 to 4 carbon atoms or by alkoxy with 1 to 4 carbon atoms; to 4 carbon atoms or means phenyl, benzyl or ethanyl substituted respectively by halogen, by alkyl with 1 to 6 carbon atoms, by alkoxy with 1 to 4 carbon atoms, by halogenalkyl with 1 to 4 carbon atoms, by halogenalkoxy with 1 to 4 carbon atoms, by nitro or by cyano (for example pyridyl, pyrimidyl or thiazolyl), or means CO-R1, CO2R2 ', SO2R1', CONH2, CONHR "or 11 R / CON, 12" R R10 means hydrogen or alkyl having 1 to 8 carbon atoms, Rn and R12 are the same or different and mean alkyl having 1 to 6 carbon atoms or alkenyl having 3 to 6 carbon atoms, m means 0 or 1, Rr independently of R1 has the meanings indicated above as being preferred for R 1, R 2 independently of R 2 has the meanings indicated above preferably for R 2.

3. Compounds of the formula (I) according to claim 1, characterized in that X means fluorine, chlorine, bromine, alkyl having 1 to 4 carbon atoms, alkoxy with 1 to 4 carbon atoms, haloalkyl with 1 to 4 carbon atoms, halogenalkoxy with 1 to 4 carbon atoms, nitro or cyano, Y means hydrogen, fluorine, chlorine, bromine, alkyl with 1 to 4 carbon atoms, alkoxy with 1 to 4 carbon atoms, haloalkyl with 1 to 4 carbon atoms, halogenalkoxy with 1 to 4 carbon atoms, nitro or cyano, Z means fluorine, chlorine, bromine, alkyl with 1 to 4 carbon atoms, halogenalkyl with 1 to 4 carbon atoms, alkoxy with 1 to 4 carbon atoms, halogenalkoxy with 1 to 4 carbon atoms, nitro or cyano, n means 0, 1 or 2, Het means one of the groups G means hydrogen (a) or means one of the groups where E means a metal ion equivalent or an ammonium ion, L means oxygen or sulfur and M means oxygen or sulfur, 1 means alkyl with 1 to 16 carbon atoms, alkenyl with 2 to 16 carbon atoms, alkoxy with 1 to 6 carbon atoms-C 1 -C 6 -alkyl or C 1 -C 6 -alkylthio-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, means phenyl optionally substituted by fluorine, chlorine, bromine, cyano, 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 or by halogenalkoxy with 1 to 3 carbon atoms, means phenyl-alkyl with 1 to 4 atoms carbon replaced, if applicable, by fl or, chlorine, bromine, alkyl having 1 to 4 carbon atoms, alkoxy having 1 to 4 carbon atoms, by halogenalkyl with 1 to 3 carbon atoms or by halogenalkoxy with 1 to 3 carbon atoms or means pyrazolyl, thiazolyl, pyridyl, pyrimidyl, furanyl or thienyl respectively substituted, if appropriate, by fluorine, chlorine, bromine or alkyl with 1 to 4 carbon atoms, R2 means 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 with 6 carbon atoms-alkyl having 2 to 6 carbon atoms, respectively substituted, if appropriate, by fluorine, means cycloalkyl having 3 to 7 carbon atoms optionally substituted by fluorine, chlorine, alkyl with 1 to 4 carbon atoms or by alkoxy with 1 to 4 carbon atoms or means phenyl or benzyl substituted, respectively, by fluorine, by chlorine, by bromine, by cyano, by nitro, by alkyl by 1 to 4 carbon atoms, by alkoxy by 1 to 3 carbon atoms, by halogenalkyl with 1 to 3 carbon atoms or by halogenalkoxy with 1 to 3 carbon atoms, R 'means alkyl with 1 to 6 carbon atoms optionally substituted by fluorine or by chlorine or means phenyl or benzyl respectively substituted by fluorine, chlorine, bromine, alkyl with 1 to 5 carbon atoms, alkoxy with 1 to 5 carbon atoms, halogenalkyl with I to 3 carbon atoms, halogenalkoxy with 1 to 3 carbon atoms, cyano or by nitro, R4 and R5 mean, independently of each other, alkyl with 1 to 6 carbon atoms, alkoxy with 1 to 6 carbon atoms, alkylamino with 1 to 6 carbon atoms, di- (alkyl with 1 to 6 carbon atoms), carbon) amino, alkylthio with 1 to 6 carbon atoms, alkenylthio with 3 to 4 carbon atoms or cycloalkylthio with 3 to 6 carbon atoms respectively substituted, if appropriate, by fluorine or by chlorine or means phenyl, phenoxy or phenylthio substituted, where appropriate, by fluorine, chlorine, bromine, nitro, cyano, alkoxy with 1 to 3 atoms carbon, 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, R6 and R7 signify, 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 carbon or alkoxy having 1 to 6 carbon atoms-alkyl having 1 to 6 carbon atoms substituted, if appropriate, by halogen (especially fluorine or chlorine) means phenyl optionally substituted by halogen, by halogen alkyl with 1 to 5 carbon atoms, carbon, by alkyl with 1 to 5 carbon atoms or by alkoxy with 1 to 5 carbon atoms, means benzyl optionally substituted by halogen, by alkyl with 1 to 5 carbon atoms, by haloalkyl with 1 to 5 carbon atoms or by alkoxy with 1 to 5 carbon atoms, or together they mean an alkylene radical having 3 to 6 carbon atoms, in which, if necessary, it is replaced by oxygen or by sulfur, a methylene group not directly adjacent to the atom. nitrogen mo, Q means n 11 OR \ / \ / C = N-N C / 10 / X 11 R OR R9 means hydrogen, means alkyl having 1 to 6 carbon atoms optionally substituted by fluorine or chlorine, means cycloalkyl having 3 to 7 carbon atoms or means phenyl or benzyl, pyrimidyl or thiazolyl respectively substituted, if appropriate, by fluorine, chlorine, by bromine, by alkyl with 1 to 5 carbon atoms, by alkoxy with 1 to 4 carbon atoms, by halogen with 1 to 2 carbon atoms, by halogenalkoxy with 1 to 2 carbon atoms, by nitro or by cyano , or means CO-R ' CO2R2 ', SO2R1', CONH2 > CONHR1 1 or 11 R TO WITH. 12"R R10 means hydrogen or alkyl having 1 to 6 carbon atoms, RI! and R12 are the same or different and mean alkyl having 1 to 4 carbon atoms, m means 1, R 'independently of R' has the meanings indicated above, with particular preference for R 1. R2 independently of R2 has the meanings indicated above of especially preferred for R :.

4. Compounds of the formula (I) according to claim 1, ca -.c -.t-rxz-- ± s caxjue X means fluorine, chlorine, bromine, methyl, ethyl, n-propyl. isopropyl, methoxy, ethoxy. n-propoxy, iso-propoxy, trifluoromethyl, difluoromethoxy, trifluoromethoxy, nitro or cyano, Y means hydrogen, fluorine, chlorine, bromine, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, tere. -butyl, methoxy, ethoxy, n-propoxy, iso-propoxy, trifluoromethyl, difluoromethoxy, trifluoromethoxy, nitro or cyano, Z means fluorine, chlorine, bromine, methyl, ethyl, n-propyl, i-propyl, n-butyl, - Butyl, tere. -butyl, methoxy, ethoxy, n-propoxy, iso-propoxy, difluoromethoxy, trifluoromethoxy, nitro or cyano. n means 0, 1 or 2, Het means one of the groups G means hydrogen (a) or means one of the groups R * E with N (9). L R especially means (b) or (c), where E means a metal ion equivalent or an ammonium ion. L means oxygen or sulfur and M means oxygen or sulfur, R1 means alkyl with 1 to 14 carbon atoms, alkenyl with 2 to 14 carbon atoms, akoxy with 1 to 4 carbon atoms-alkyl with 1 to 6 carbon atoms or alkylthio having from 1 to 4 carbon atoms-alkyl having from 1 to 6 carbon atoms substituted, if appropriate, by fluorine or chlorine or by cycloalkyl having 3 to 6 carbon atoms, optionally substituted by methyl, by ethyl, per tere. -butyl or methoxy, means phenyl substituted, if appropriate, by fluorine, by chlorineby bromine, by cyano, by nitro, by methyl, by methoxy, by trifluoromethyl or by trifluoromethoxy, means benzyl optionally substituted by fluorine, by chlorine, by bromine, by methyl, by methoxy, by trifluoromethyl or by trifluoromethoxy or furanyl, thienyl or pyridyl respectively substituted, if appropriate, by fluorine, chlorine, bromine or methyl, R2 means alkyl having 1 to 14 carbon atoms, alkenyl with 2 to 14 carbon atoms or alkoxy with 1 to 4 carbon atoms -alkyl with 2 to 6 carbon atoms, means cycloalkyl with 3 to 6 carbon atoms, optionally substituted by methyl or methoxy or means phenyl or benzyl, respectively substituted, if appropriate, by fluorine, chlorine, bromine, cyano, by nitro, by methyl, by methoxy, by trifluorontium or by trifluoromethoxy, R1 means methyl, ethyl, n-propyl, iso-propyl, optionally substituted by fluorine or by chlorine or means phenyl or benzyl substituted respectively where appropriate fluorine, chlorine, bromine, methyl, ethyl, n-propyl, iso-propyl, tere-butyl, methoxy, ethoxy, isopropoxy, tert-butoxy, trifluoromethyl, by trifluoromethoxy, by cyano or by nitro, R4 and R5 independently of each other, mean alkyl with 1 to 4 carbon atoms, alkoxy with 1 to 4 carbon atoms, alkylamino with 1 to 4 carbon atoms, di- (alkyl with 1 at 4 carbon atoms) amino or alkylthio having 1 to 4 carbon atoms, respectively substituted, if appropriate, by fluorine or chlorine or by phenyl, phenoxy or phenylthio, respectively substituted, if appropriate, by fluorine, chlorine, bromine, nitro, by cyano, by alkoxy with 1 to 2 carbon atoms, by fluoroalkoxy with 1 to 2 carbon atoms, by alkylthio with 1 to 2 carbon atoms, by fluoroalkylthio with 1 to 2 carbon atoms or by alkyl with 1 to 3 atoms of carbon, R6 and R7 mean, independently of each other, hydrogen, mean alk uilo with 1 to 4 carbon atoms, cycloalkyl with 3 to 6 carbon atoms, alkoxy with 1 to 4 carbon atoms, alkenyl having 3 to 4 carbon atoms or alkoxy having 1 to 4 carbon atoms-alkyl having 1 to 4 carbon atoms substituted, where appropriate, by fluorine or chlorine, mean phenyl substituted by fluorine , by chlorine, by bromine, by trifluoromethyl, by methyl or by methoxy, means benzyl optionally substituted by fluorine, by chlorine, by bromine, by alkyl with 1 to 4 carbon atoms, by halogenalkyl with 1 to 4 carbon atoms or by alkoxy with 1 to 4 carbon atoms or together they mean an alkylene radical having 5 to 6 carbon atoms, in which, if necessary, it is replaced by oxygen or by sulfur, a methylene group not directly adjacent to the nitrogen atom, Q means \ \ \ \ CHOH • C = OC = N-Rβ C = NO ~ R / '/ / R9 means hydrogen, means alkyl having 1 to 4 carbon atoms, means cycloalkyl having 3 to 6 carbon atoms or means phenyl or benzyl substituted, where appropriate, by fluorine, by chlorine, by bromine, by methyl, by ethyl, by n -propyl, by iso-propyl, by tere. -butyl, by methoxy, by trifluoromethyl, by trifluopnetoxy, by nitro or by cyano or means CO-R1, CO2R2, SO2R1 ', CONH2, CONHR "11 R / CON, 12" R R '° means hydrogen or methyl, R "and R' ~ are the same or different \ mean methyl or ethyl, m means I, R 'independently of R' has the meanings given above, very particularly preferably for R1, R2 independently of R: has the meanings indicated above for very particular preference for R:

5. Process for obtaining compounds of the formula (I) according to claim 1, characterized in that, for obtaining the compounds (A) of the formula (I- 1 -a) wherein Q, X, Y, Z, m and n have the meanings indicated in claim 1, compounds of the formula (II) are condensed intramolecularly where Q, X, Y, Z, m and n have the meanings indicated above, R8 means alkyl, in the presence of a diluent and in the presence of a base, (B) for the preparation of the compounds of the formula 0-2-a) t H2) m Where Q, X, Y, Z, m and n have the meanings indicated above, compounds of the formula (III) are condensed intramolecularly wherein i - Q, X, Y, Z, m, n and Rs have the meanings indicated above. in the presence of a diluent and in the presence of a base. (C) for obtaining the compounds of the formula (I-3-a) where Q, X, Y. Z, m and n have the meanings indicated above. compounds of the formula (IV) are iptramolecularly cyclized wherein Q, X, Y, Z, m, n and R8 have the meanings given above and means hydrogen, halogen, alkyl, in the presence of a diluent and in the presence of an acid and, if appropriate, then the compounds, obtainable from this way, of the formulas (I-la), (I-2-a) and (I-3-a) are reacted respectively (Da) with acyl chlorides of the formula (V) wherein R1 has the meanings indicated in claim 1, and Hal means halogen. (p) with anhydrides of carboxylic acids of the formula (VI) R 1 -CO-O-CO-R 1 (VI) in which R 'has the meanings given above, optionally in the presence of a diluent and, if appropriate , in the presence of an acid accepting agent; or (E) with esters of chloroformic acid or with thiol esters of chloroformic acid of the formula (VII) .R2-M-CO-Cl (VII) in which R2 and M have the meanings indicated in claim 1, where appropriate in the presence of a diluyeme and, if appropriate, in the presence of an acid-accepting agent; or (F) with esters of chloromonothioformic acid or with esters of chlorodithioformic acid of the formula (VIII) wherein M and R2 have the meanings indicated above. if necessary in the presence of a diluent \. if appropriate, in the presence of an acid-accepting agent; or (G) with sulfonyl chlorides of the formula (IX) R'-SO.-CI (IX) in which R 3 has the meaning indicated in claim 1. if necessary in the presence of a diluent and, if appropriate , in the presence of an acid-binding agent, or (H) with phosphorus compounds of the formula (X) wherein L, R4 and R5 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-accepting agent; or (I) with metal compounds or amines of the formulas (XI) or (XII) 10, 13 14 -R "N 'Me (ORI3) t (XI) (XII) 15 R i -; in which Me means a mono or divalent metal, t means 1 or 2 and Rp, Ru, R15 independently of one another, mean hydrogen or alkyl, if appropriate in the presence of a diluent; or 0 (Ja) with isocyanates or isothiocyanates of the formula (XIII) R "-N = C = L (XIII) in which R6 and L have the meanings indicated in claim 1, if appropriate in the presence of a diluent. if appropriate, in the presence of a catalyst, or (ß) with c-chloridyl chlorides or with thiocarbamidyl chlorides of the formula (XIV) wherein L, R ° 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.- Compounds of the formula (II) caracter-.za ± -s poroqL-s; Q, X, Y, Z, m and n have the meanings indicated above, \ RE means alkyl. 1.- Compounds of the formula (XVII) paxjje; Q, m, X, Y, Z and n have the meanings indicated in claim 1, 8. Compounds of the formula (III) c - rar - ± - riza ± e perqué; Q, X, Y, Z, m and n have the meanings indicated above and Rf means alkyl. 20 9.- Compounds of the formula (IV) « -.0 pxque; Q, W, X, Y, Z, m and n have the meanings indicated above and R8 means alkyl. 10. Pesticidal agents or herbicidal agents, characterized in that they have a content of a compound of the formula (I) according to claim 1. 11. Use of the compounds of the formula (I) according to claim 1, for the fight against pests and against weeds. 12. Procedure for the fight against pests and against weeds, characterized in that compounds of the formula (I) according to claim 1 are allowed to accumulate on the pests and / or on the weeds and / or on their environment . 13. Process for obtaining pesticidal agents and acaricidal agents characterized in that compounds of the formula (I) according to claim 1 are mixed with extenders and / or surfactants. SUMMARY OF THE INVENTION The invention relates to novel spirocyclic phenylkethoenols of the general formula (I) where Het represents one of groups (1), (2) or (3) Q represents (A); (B); (C); (D); (E) or (F) \ \ / OR C = N- / OR "(E) (F) and X, Y, Z, m, n, R ", R9, RI. R" have the meanings indicated in the description. The invention also relates to processes and intermediates for the preparation of said spirocyclic phenylkethoenols and to the use thereof as pesticides and herbicides.