MXPA99001115A - Phenyl-substituted cyclic ketoenol - Google Patents

Abstract

The invention relates to new phenyl-substituted cyclic ketoenol of formula (I) in which A, B, G, X, Y, Z and n are signified as indicated in the description, as well as several methods for the manufacture thereof and its use as a pesticide and herbicide.

Description

CYCLIC CETHENOLS FENIL-REPLACED DESCRIPTION OF THE INVENTION The invention relates to novel cyclic ketoenols phenyl-substituted, to various processes for their preparation and to their use as pesticides and herbicides. Derivatives of IH-arylpyrrolidinedione are known (EP-456 063, EP-521 334, EP-596 298, EP-613,884, EP-613 885, WO 94/01 997, WO 95/01358, WO 95/26954, WO 96/00382, WO 95 / 20572, EP 668 267) with herbicidal, acaricidal and insecticidal effect. However, the activity and spectrum of activity of these compounds are not always completely satisfactory, especially in the case of application quantities and low concentrations. In addition, compatibility with plants and their compounds is not always enough. According to this invention, new compounds of the formula (I) are provided REF. 29297 wherein X represents halogen, alkyl, alkenyl, alkynyl, alkoxy, alkenyloxy alkylthio, alkylsulfinyl, alkylsulfonyl, haloalkyl, haloalkenyl, -, haloalkoxy, haloalkenyloxy, nitro, cyano or represents phenyl, phenoxy, phenylthio, benzyloxy or benzylthio respectively substituted on given case, Y represents hydrogen halogen, alkyl, alkenyl, alkynyl, alkoxy, alkenyloxy alkylthio, alkylsulfinyl, alkylsulfonyl, haloalkyl, haloalkenyl, haloalkoxy, haloalkenyloxy, nitro or cyano, Z represents halogen, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, alkoxy alkenyloxy, haloalkoxy, haloalkenyloxy, nitro or cyano, n represents 0, 1, 2 or 3, A represents hydrogen, represents alkyl, alkenyl, alkynyl, alkoxyalkyl, polyalkoxyalkyl or alkylthioalkyl respectively substituted by halogen, represents saturated cycloalkyl or unsaturated, if necessary replaced, in the which at least one atom of the ring is, if necessary, replaced by a heteroatom, or represents aryl, arylalkyl or hetaryl substituted respectively by halogen, by alkyl, by haloalkyl, by alkoxy, by haloalkoxy, by cyano or by nitro, may optionally be substituted by phenoxy, by benzyloxy or by substituted hetaryloxy B represents hydrogen or represents alkyl, alkoxyalkyl respectively substituted by halogen, or A and B together with the carbon atom, to which they are linked represent a saturated or unsaturated .. which optionally contains a heteroatom, unsubstituted or substituted, G represents hydrogen (a) or represents one of the groups where E represents a metal ion equivalent or an ammonium ion, L represents oxygen or sulfur, M represents oxygen or sulfur, Rl represents alkyl, alkenyl, alkoxyalkyl, alkylthioalkyl or polyalkoxyalkyl respectively substituted, if appropriate, by halogen or represents cycloalkyl optionally substituted by halogen, by alkyl or by alkoxy, which may be interrupted by at least one heteroatom or represents phenyl, phenylalkyl, hetaryl, phenoxyalkyl or hetaryloxyalkyl respectively substituted, R "represents alkyl, alkenyl, alkoxyalkyl or polyalkoxyalkyl substituted respectively where appropriate by halogen or represents cycloalkyl, phenyl or benzyl respectively substituted, RJ, R4 and R ', independently of each other, represent alkyl, alkoxy, alkylamino, dialkylamino, alkylthio, alkenylthio or cycloalkylthio substituted respectively by halogen or represent phenyl, benzyl, phenoxy or phenylthio substituted respectively and RD and R1 , independently of one another, represent hydrogen, represent alkyl, cycloalkyl, alkenyl, alkoxy, alkoxyalkyl respectively substituted by halogen, represent substituted phenyl if appropriate, represent benzyl substituted if appropriate, or together with the N atom, with the which are linked, represent a cycle that is interrupted, if necessary, by oxygen or by sulfur. The compounds of the formula (I) can be presented, depending on the type of the substituents, such as geometric and / or optical isomers or as mixtures of isomers, in variable composition, which can be separated 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 are an object of the present invention. In the following, it will be discussed, to simplify, however, always compounds of the formula (I), even if they want to indicate both the pure compounds and, if necessary, also mixtures with variable proportions of isomeric compounds. It has further been found that the compounds of the formula (I) are obtained according to one of the methods described below: (A) The substituted 3-phenylpyrrolidin-2,4-diones or their enoles of the formula (I-a) are obtained. wherein A, B, X, Y, Z and n have those represented above when obtaining esters of N-acylamino-acids of the formula (II) in which A, B, X, Y, Z and n have those represented previously indicated YR "represents alkyl, (preferably alkyl having 1 to 6 carbon atoms), they are condensed intralecularly in the presence of a diluent and in the presence of a base In addition it has been found (B) a) that the compounds of the aforementioned formula (Ib), in which A, B, X, Y, Z, R1 and n have the above represented, if compounds of the formula (Ia) are reacted in which A, B, X, Y , Z and n have the above represented, with acyl halides of the formula (III) wherein R 1 has the above-indicated represented and Hal represents halogen (especially chlorine or bromine) or is reacted β) with anhydrides of carboxylic acids of the formula (IV) R ^ CO-O-CO-R1 IV) wherein R: has the abovementioned represented, optionally in the presence of a diluent and, if appropriate, in the presence of an acid-accepting agent; (C) that the compounds of the above-mentioned formula (Ic) are obtained, in which A, B, R2, M, X, Y, Z and n have the above represented and L represents oxygen, if compounds of the aforementioned formula (Ia) in which A, B, X, Y, Z, and n have the abovementioned representatives, respectively in each case with esters of chloroformic acid or thiol esters of chloroformic acid of the formula (V) R2-M-C0-C1 (V) wherein R "and M have the abovementioned representatives, if provided in the presence of a diluent and, if appropriate, in the presence of an acid-binding agent; Compounds of the formula indicated above (Ic) are obtained, in which A, B, R2, M, X, Y, Z and n have the above represented and L represents sulfur, if compounds of the formula indicated above (Ia) are reacted in which A, B, X, Y, Z, and n have the above represented, respectively in each case with esters of chloromethyothiophoric acid or with esters of chlorodithioformic acid of the formula (VI) wherein M and R "have the abovementioned representatives, if provided in the presence of a diluent and, if appropriate, in the presence of an acid-binding agent; (E) that the compounds of the formula indicated above are obtained ( Id), in which A, B, R3, X, Y, Z and n have the above represented, if the compounds of the formula indicated above (Ia) are reacted in which A, B, X, Y, Z , and n have the above represented, respectively in each case with sulfonyl chlorides of the formula (VII) R-S0; -C1 (VII) wherein R has the abovementioned represented, if giving in the presence of a diluent and, if appropriate, in the presence of an acid-accepting agent, (F) the compounds of the above-indicated formula (Ie) are obtained, in which A, B, L, R4, R5, X, Y, Z and n have the above represented, if compounds of the formula indicated above (Ia) are reacted in which A, B, X, Y, Z, and n have the above represented, respectively in each case with phosphorus compounds of the formula (VIIi wherein L, R4 and R15 have the above represented, and Hal represents halogen (especially chlorine or bromine), if appropriate in the presence of a diluent and, if appropriate, in the presence of an acid-binding agent, (G) that the compounds of the formula indicated above (If) are obtained, in which A, B, E, X, Y, Z and n have the above represented ones, if they are reacted compounds of the formula indicated above (I-a) in which A, B, X, Y, Z, and n have the abovementioned representatives, respectively in each case with metal or amines of the formulas (IX) or (X), R 10. R 11 Me (OR- J (i ?; (X) in which Me represents a mono or divalent metal (preferably an alkaline metal to an alkaline earth metal, such as lithium, sodium, potassium, magnesium or calcium) , t represents the number 1 or 2 and R1'1, R11, R1", independently represent each other hydrogen or alkyl (preferably alkyl of 1 to 8 carbon atoms), in case given in the presence of a diluent, (H ) that the compounds of the formula indicated above (Ig) are obtained, in which A, B, L, Rd, RJX, Y, Z and n have the abovementioned representatives, if compounds of the formula indicated above are reacted (Ia ) in which A, B, X, Y, Z, and n have the above represented, with carbamidyl chlorides or with thiocarbamidyl chlorides of the formula (XI) in which L, R ", R, have the abovementioned representatives, optionally 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 formula (Ia) are therefore important intermediates for obtaining the compounds according to the invention of the formula (I), in which G represents one of groups b), c), d), e), f) og ). Furthermore, it has been found that the novel compounds of the formula (I) have a very good activity as agents for controlling pests, preferably as insecticides, acaricides and herbicides. The compounds according to the invention are generally defined by the formula (I). The preferred substituents or the ranges of the residues indicated in the above formulas and in the formulas that follow are explained below: X Preferably, represents 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 the ß carbon atoms, haloalkyl with the ß carbon atoms, halogenalkenyl with 2 to ß carbon atoms, halogenalkoxy with the ß atoms carbon, halogenoalkenyloxy with 3 to 6 carbon atoms, nitro, cyano or represents phenyl, phenoxy, phenylthio, benzyloxy or benzylthio, substituted respectively by halogen, by alkyl with the ß carbon atoms, by alkoxy with the ß carbon atoms , with halogenalkyl having 1 to 4 carbon atoms, by halogenalkoxy with 1 to 4 carbon atoms, by nitro or by cyano.

Preferably, it represents halogen hydrogen, alkyl with the ß carbon atoms, alkenyl with 2 to 6 carbon atoms, alkynyl with 2 to 6 carbon atoms, alkoxy with l ß carbon atoms, alkenyloxy with 3 to 6 carbon atoms, alkylthio with 1 to 6 carbon atoms, alkylsulfinyla with 1 to 6 carbon atoms, alkylsulfonyl with the ß carbon atoms, haloalkyl with l ß carbon atoms, haloalkenyl with 2 to ß carbon atoms, haloalkoxy with the ß carbon atoms , halogenalkenyloxy with 3 to 6 carbon atoms, nitro or cyano, Z Preferably, represents halogen, alkyl having 1 to 6 carbon atoms, alkenyl with 2 to 6 carbon atoms, alkynyl with 2 to 6 carbon atoms, halogenoalkyl with the ß carbon atoms, haloalkenyl with 2 to 6 carbon atoms alkoxy with 1 to 6 carbon atoms, alkenyloxy with 3 to 6 carbon atoms, halogenoalkoxy with the ß carbon atoms, halogenoalkenyloxy with 3 to 6 carbon atoms, nitro or cyano, n preferably represents 0, 1, 2 or 3, A Preferably, represents hydrogen or represents alkyl with 1 to 12 carbon atoms, alkenyl with 2 to 8 carbon atoms, alkynyl with 2 to 8 carbon atoms, alkoxy with 1 to 10 carbon atoms-alkyl with 1 to 8 carbon atoms. carbon, poly-alkoxy with 1 to 8 carbon atoms-alkyl with 1 to 8 carbon atoms or alkylthio with 1 to 10 carbon atoms-alkyl with l ß carbon atoms substituted, if appropriate, by halogen, respectivelyrepresents cycloalkyl with 3 to 8 carbon atoms, optionally substituted by halogen, by alkyl with the ß carbon atoms or by alkoxy with the ß carbon atoms, in which a ring member is replaced, if appropriate, by an oxygen or by sulfur or represents phenyl or naphthyl, hetaryl containing 5 to 6 ring atoms, preferably alkyl with the β carbon atoms, or represents furanyl, pyridyl, imidazolyl, triazolyl, pyrazolyl, pyrimidyl, thiazolyl or thienyl or phenyl or naphthyl , if appropriate substituted by halogen, by alkyl with the ß carbon atoms, by halogen with the carbon atoms, by alkoxy with the carbon atoms, by haloalkoxy with the carbon atoms, by cyano 0 by nitro, optionally substituted by halogen, by alkyl with 1 to 4 carbon atoms, by allooxi with 1 to 4 carbon atoms, by haloalkyl with 1 to 2 carbon atoms, for halogenalkoxy with 1 to 2 carbon atoms, for cyano or for nitro, Preferably, it represents hydrogen or represents alkyl with 1 to 12 carbon atoms or alkoxy with 1 to 8 carbon atoms-alkyl with the β carbon atoms substituted, respectively, by halogen, or, preferably, A, B and the carbon atom with which they are linked represent cycloalkyl with 3 to 10 carbon atoms saturated or unsaturated, (in particular cycloalkyl with 5 to 8 carbon atoms), in which a ring member is optionally replaced by oxygen or by sulfur and which is optionally mono- or polysubstituted by alkyl with 1 to 8 carbon atoms, by cycloalkyl with 3 to 10 carbon atoms, by halogenalkyl with 1 to 8 carbon atoms, by alkoxy with 1 to 8 carbon atoms, alkylthio with 1 to 8 carbon atoms, by halogen or by phenyl or Preferably, A, B and the carbon atom to which they are attached represent cycloalkyl with 5 to 8 carbon atoms or cycloalkenyl with 5 to 8 carbon atoms, in which two substituents together with the carbon atoms, with which they are linked, represent alkanediyl with 5 to ß carbon atoms, alkenodiyl with 5 to 6 carbon atoms or alkanediyenyl with 6 carbon atoms substituted, where appropriate, by alkyl with the ß carbon atoms, by alkoxy with the ß carbon atoms or by halogen, a methylene group being optionally replaced by oxygen or by sulfur.

G preferably, represents hydrogen (a) or represents one of the groups in which E represents a metal ion equivalent or an ammonium ion, L represents oxygen or sulfur and M represents oxygen or sulfur.

R1 preferably represents 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 or represents cycloalkyl with 3 to 8 carbon atoms optionally substituted by halogen , by alkyl with the ß carbon atoms or by alkoxy with the ß carbon atoms, in which at least one methylene group is replaced by oxygen or sulfur, preferably represents phenyl optionally substituted by halogen, by cyano , by nitro, by alkyl with the ß carbon atoms, by alkoxy with the ß carbon atoms, haloalkyl with the ß carbon atoms, by haloalkoxy with the ß carbon atoms, by alkylthio with the ß carbon atoms or by l-alkylsulfonyl with the β-carbon atoms, preferably represents phenyl-C 1 -C 6 -alkyl optionally substituted by halogen, by nitro, by cyano, by C 1 -C 6 -alkyl, by alkoxy with the β-atom of carbon, by haloalkyl with the ß carbon atoms or by haloalkoxy with the ß carbon atoms, preferably represents hetaryl with 5 or 6 members, optionally substituted by halogen, or by alkyl with the ß carbon atoms (in particular pyrazolyl) , thiazolyl, pyridyl, pyrimidyl, furanyl or thienyl), preferably represents phenoxy-alkyl with the β carbon atoms optionally substituted by halogen or by alkyl with the β carbon atoms or preferably, represents hetaryloxy-alkyl with 1 to 6 carbon atoms, with 5 or 6 members, optionally substituted by halogen, by amino or by alkyl with the ß carbon atoms (in particular pyridyloxy-alkyl with the ß carbon atoms, pyrimidyloxy-alkyl with 6 carbon atoms or thiazolyloxy-alkyl with 1 to β carbon atoms). preferably, it represents alkyl with 1 to 20 carbon atoms, alkenyl with 2 to 20 carbon atoms, alkoxy with 1 to 8 carbon atoms-alkyl with 2 to 8 carbon atoms or poly-alkoxy with 1 to 8 carbon atoms-alkyl with 2 to 8 carbon atoms substituted respectively in case given by halogen Preferably, it represents cycloalkyl with 3 to 8 carbon atoms, optionally substituted by halogen, by alkyl with the ß carbon atoms or by alkoxy with the ß carbon atoms, or Preferably, represents phenyl or benzyl substituted respectively if appropriate by halogen, by cyano, by nitro, by alkyl with the ß carbon atoms, by alkoxy with the ß carbon atoms, by haloalkyl with the ß carbon atoms or by haloalkoxy with the ß carbon atoms.

R3 Preferably, it represents alkyl having from 1 to 8 carbon atoms substituted, if appropriate, by halogen or represents phenyl or benzyl substituted, where appropriate, by halogen, by alkyl with the β carbon atoms, by alkoxy with 1 to 6 carbon atoms, by halogenalkyl with 1 to 4 carbon atoms, by haloalkoxy with 1 to 4 carbon atoms, by cyano or by nitro. Preferably, R "and R 'represent, independently of each other, alkyl with 1 to 8 carbon atoms, alkoxy with 1 to 8 carbon atoms, alkylamino with 1 to 8 carbon atoms, di- (alkyl with 1 to 8 carbon atoms). carbon) 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 represent phenyl, phenoxy or phenylthio substituted respectively 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 halogenalkylthio with 1 to 4 carbon atoms, by alkyl with 1 to 4 carbon atoms or by halogenalkyl with 1 to 4 carbon atoms Preferably, and R 'represent, independently of one another, hydrogen, represent 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 1 to 8 carbon atoms substituted, if appropriate, by halogen, represent phenyl optionally substituted by halogen, by halogenalkyl with 1 to 8 carbon atoms, by alkyl with the ß carbon atoms or by alkoxy with 1 to 8 carbon atoms, benzyl optionally substituted by halogen, by alkyl with 1 to 8 carbon atoms, by haloalkyl with 1 to 8 carbon atoms or by alkoxy with 1 to 8 carbon atoms or together represent an alkylene radical having 3 to 6 carbon atoms, in which it is optionally replaced by a methylene group by oxygen or by sulfur.

Particularly preferably, X represents 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 , cyano or represents phenyl or benzyl substituted respectively by fluorine, chlorine, bromine, alkyl having 1 to 4 carbon atoms, alkoxy with 1 to 4 carbon atoms, halogenalkyl having 1 to 2 carbon atoms, halogenalkoxy with 1 to 2 carbon atoms, by nitro 0 for cyano. Particularly preferably, Y represents hydrogen, fluorine, chlorine, bromine, alkyl with 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 represents fluorine, chlorine, bromine, alkyl having 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.

Particularly preferably, n represents 0, 1, 2 or 3 (in particular represents 0, 1 or 2).

Particularly preferably, A represents hydrogen, represents alkyl having 1 to 10 carbon atoms or alkoxy with 1 to 8 carbon atoms-alkyl having the carbon atoms preferably substituted, respectively, by fluorine or chlorine, represents cycloalkyl with 3-carbon atoms. at 7 carbon atoms optionally substituted by fluorine, by chlorine, by alkyl with 1 to 4 carbon atoms or by alkoxy with 1 to 4 carbon atoms, or represents phenyl, furanyl, pyridyl, imidazolyl, triazolyl, pyrazolyl, pyrimidinyl , triazolyl, thienyl or phenyl-alkyl having from 1 to 4 carbon atoms each substituted, where appropriate, by fluorine, by chlorine, by bromine, by alkyl with 1 to 4 carbon atoms, by haloalkyl with 1 to 4 carbon atoms, alkoxy with 1 to 4 carbon atoms, by haloalkoxy with 1 to 4 carbon atoms, by cyano or by nitro. Particularly preferably, B represents hydrogen or represents alkyl having from 1 to 10 carbon atoms or alkoxy with the carbon atoms-alkyl having from 1 to 4 carbon atoms substituted, respectively, by fluorine or chlorine, or particularly preferably , A, B and the carbon atom to which they are linked represent cycloalkyl with 5 to 8 carbon atoms saturated or unsaturated, in which a ring member is replaced by oxygen or sulfur and which is optionally substituted by alkyl with the ß carbon atoms, by cycloalkyl with 3 to 8 carbon atoms, by halogenalkyl with 1 to 3 carbon atoms, by alkoxy with the ß carbon atoms, by alkylthio with 1 to 6 carbon atoms carbon, fluorine, chlorine or phenyl or particularly preferably A, B and the carbon atom to which they are attached represent cycloalkyl with 5 to ß carbon atoms or cycloalkenyl with 5 to 6 at. carbon atoms, in which two substituents together with the carbon atoms, with which they are bonded, represent alkanediyl having 5 to 6 carbon atoms, alkenodiyl having 5 to 10 carbon atoms or alkanediyenyl having 6 carbon atoms substituted respectively in the case given by alkyl having 1 to 5 carbon atoms, by alkoxy with 1 to 5 carbon atoms, by fluorine, by chlorine or by bromine, where a methylene group is replaced by oxygen or by sulfur. Particularly preferably, G represents hydrogen (a) or represents one of the groups in which i LO represents an equivalent of metal ion or an ammonium ion, L represents oxygen or sulfur and M represents oxygen or sulfur. Particularly preferably, R 1 represents alkyl with 1 to 16 carbon atoms, alkenyl with 2 to 16 carbon atoms, alkoxy with 1 to 6 carbon atoms-alkyl with the β carbon atoms, alkylthio with the β carbon atoms - alkyl with the ß carbon atoms, poly-alkoxy with the ß carbon atoms-alkyl with the β carbon atoms respectively substituted, if appropriate, by fluorine or chlorine or represents cycloalkyl with 3 to 7 carbon atoms, optionally substituted by fluorine, by chlorine, by alkyl with 1 to 5 carbon atoms or by alkoxy with 1 to 5 carbon atoms, in which one or two methylene groups, not directly adjacent, are replaced, by oxygen or by sulfur, It is particularly preferred to represent phenyl which is optionally substituted by fluorine, chlorine, bromine, cyano, nitro, alkyl with 1 to 4 carbon atoms, alkoxy with 1 to 4 carbon atoms, haloalkyl with 1 to 3 atoms d carbon / halogenalkoxy with 1 to 3 carbon atoms, for alkylthio with 1 to 4 carbon atoms or for alkylsulfonyl with 1 to 4 carbon atoms, Of especially preferred forroa, represents phenylalkyl with 1 to 4 carbon atoms substituted in case given by fluorine, by chlorine, by bromine, by alkyl with 1 to 4 carbon atoms, by alkoxy with 1 to 4 carbon atoms, by halogenalkyl with 1 to 3 carbon atoms, or by halogenalkoxy with 1 to 3 carbon atoms More preferably, it represents pyrazolyl, thiazolyl, pyridyl, pyrimidyl, furanyl, thienyl, respectively substituted by fluorine, chlorine, bromine or alkyl with 1 to 4 carbon atoms, and is particularly preferably phenoxy. alkyl with 1 to 5 carbon atoms optionally substituted by, by fluorine, chlorine, bromine or alkyl with 1 to 4 carbon atoms, or particularly preferably represents pyridyloxy-alkyl with 1 to 5 carbon atoms; carbon, pyrimidyloxy-C 1 -C 5 -alkyl or thiazolyloxy-C 1 -C 5 -alkyl optionally substituted, respectively, by fluorine, chlorine, bromine, amino or alkyl with 1 to 4 carbon atoms . Particularly preferably, it represents alkyl with 1 to 16 carbon atoms, alkenyl with 2 to 16 carbon atoms, alkoxy with 1 to ß carbon atoms-alkyl with 2 to ß carbon atoms or poly-alkoxy with the ß atoms of carbon-alkyl with 2 to 6 carbon atoms substituted, respectively, by fluorine, or chlorine, particularly preferably represents cycloalkyl with 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 Of especially preferred forroa, represents phenyl or benzyl respectively substituted, if appropriate, by fluorine, by chlorine, by bromine, by cyano, by nitro, by alkyl with 1 at 4 carbon atoms, by alkoxy with 1 to 3 carbon atoms, by halogenalkyl with 1 to 3 carbon atoms or by halogenalkoxy with 1 to 3 carbon atoms, particularly preferably, R "represents alkyl with the β-atoms of c arbono optionally substituted by fluorine or chlorine or represents phenyl or benzyl, optionally substituted, respectively, by fluorine, chlorine, bromine, alkyl with 1 to 5 carbon atoms, alkoxy with 1 to 5 carbon atoms, halogenalkyl with 1 to 3 carbon atoms, for halogenalkoxy with 1 to 3 carbon atoms, for cyano or for nitro, particularly preferably R ~ and RJ independently of each other, represent alkyl with the β carbon atoms, alkoxy with the ß carbon atoms, alkylamino with the ß carbon atoms, di- (alkyl with the ß carbon atoms) amino, alkylthio with the ß carbon atoms, alkenylthio with 3 to 4 carbon atoms, cycloalkylthio with 3 to 6 carbon atoms, respectively substituted, if appropriate, by fluorine or chlorine, or represent phenyl, phenoxy or phenylthio substituted, where appropriate, by fluorine, chlorine, bromine, nitro, cyano or alkoxy; to 3 carbon atoms, for halogenalkoxy with 1 to 3 carbon atoms, for alkylthio with 1 to 3 carbon atoms, for halogenalkylthio with 1 to 3 carbon atoms, for alkyl with 1 to 3 carbon atoms or for haloalkyl with 1 to 3 carbon atoms. Particularly preferably, and R 'represent, independently of one another, hydrogen, represent alkyl with the β carbon atoms, cycloalkyl with 3 to 6 carbon atoms, alkoxy with the β carbon atoms, alkenyl with 3 to 6 carbon atoms , alkoxy with the carbon atoms-alkyl having 1 to 6 carbon atoms substituted, where appropriate, by halogen, represent phenyl optionally substituted by halogen, by halogenalkyl with 1 to 5 carbon atoms, by alkyl with 1 to 5 carbon atoms; carbon atoms, or by alkoxy with 1 to 5 carbon atoms, represent benzyl optionally substituted by halogen, by alkyl with 1 to 5 carbon atoms, by halogenalkyl with 1 to 5 carbon atoms or by alkoxy with 1 to 5 carbon atoms; carbon atoms, or together they represent an alkylene radical having 3 to 10 carbon atoms, in which, if appropriate, a carbon atom is replaced by oxygen or by sulfur. Very particularly preferably, X represents fluorine, chlorine, bromine, methyl, ethyl, propyl, iso-propyl, methoxy, propoxy, iso-propoxy, trifluoromethyl, di-fluoromethoxy, trifluoromethoxy, nitro or cyano. Very particularly preferably, Y represents hydrogen, fluorine, chlorine, bromine, methyl, ethyl, n-propyl, i-propyl, n-butyl, isobutyl, tert-butyl, methoxy, ethoxy, propoxy-, iso-propoxy , allyloxy, methaloyloxy, trifluoromethyl, difluoromethoxy, trifluoromethoxy, nitro or cyano. Very particularly preferably, Z represents fluorine, chlorine, bromine, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, tert-butyl, methoxy, ethoxy, propoxy, iso-propoxy, difluoromethoxy, trifluoromethyl, trifluoromethoxy, nitro or cyano. Very particularly preferably, n represents 0, 1, 2 or 3 (in particular represents 0, 1 or 2, specifically represents 0 or 1).

Very particularly preferably, A represents hydrogen or represents alkyl having 1 to 8 carbon atoms or alkoxy with the β carbon atoms-alkyl having 1 to 4 carbon atoms substituted, respectively, respectively by fluorine or chlorine, represents cycloalkyl with 5 to 6 atoms optionally substituted by fluorine, chlorine, methyl, ethyl, isopropyl, tert-butyl, ethoxy or methoxy, or represent phenyl or benzyl each of which optionally substituted by fluorine, by chlorine, by methyl, by ethyl, by iso-propyl, by tert-butyl, by methoxy, by ethoxy, by trifluoromethyl, by difluoromethoxy, by trifluoromethoxy, cyano or nitro.

Very particularly preferably, B represents hydrogen or represents alkyl with 1 to 8 carbon atoms or alkoxy with 1 to 4 carbon atoms-alkyl having 1 to 2 carbon atoms, each of which is optionally substituted by fluorine, or very particularly preferably, A, B and the carbon atom, to which they are attached, represent cycloalkyl with 5 to 6 carbon atoms saturated or unsaturated, in which a methylene group is optionally replaced by oxygen or by sulfur and which is optionally substituted by methyl, ethyl, iopropyl, tert-butyl, trifluoromethyl, methoxy, ethoxy, fluorine, chlorine or phenyl or very particularly preferably, A, B and the carbon atom, to which they are attached, represent cycloalkyl with 5 to 6 carbon atoms or cycloalkenyl with 5 to 6 carbon atoms, in which two substituents together with the carbon atoms, with which they are bonded, represent alkanediyl with 5 to 10 carbon atoms arbono, alkenodiil with 5 to 6 carbon atoms or alkenodienediilo with 6 carbon atoms.

Very particularly preferably, G represents hydrogen (a) or represents one of the groups (in particular represents one of groups (a), (b) or (c)) in which E represents a metal ion equivalent or an ammonium ion, L represents oxygen or sulfur and M represents oxygen or sulfur. Very particularly preferably, R1 represents alkyl with 1 to 14 carbon atoms, • alkenyl with 2 to 4 carbon atoms, alkoxy with 1 to 6 carbon atoms-alkyl with the ß carbon atoms, alkylthio with 1 to 4 atoms carbon-alkyl with the ß carbon atoms or poly-alkoxy with 1 to 4 carbon atoms-alkyl having 1 to 4 carbon atoms substituted, where appropriate, respectively by fluorine or chlorine or optionally fluorine, chlorine, methyl, ethyl , propyl, i-propyl, butyl, i-butyl, tert-butyl, methoxy, ethoxy, propoxy, or iso-propoxy substituted with cycloalkyl having 3 to ß carbon atoms, in which one or two methylene groups are optionally substituted, not directly contiguous, by oxygen or by sulfur, very particularly preferably represents phenyl optionally substituted by fluorine, chloro-, bromo-, methyl-, ethyl-, propyl-, i-propyl-, methoxy-, ethoxy-, trifluoromethyl-, trifluoromethoxy-, methylthio-, ethylthio-, methylsulfonyl or ethylsulphonyl, very particularly preferably represents benzyl fluorine-, chloro-, bromo-, methyl-, ethyl-, propyl-, i-propyl-, methoxy-, ethoxy-, trifluoromethyl- or trifluoromethoxy-, very particularly preferably represents furanyl, thienyl, pyridyl, pyrimidyl, thiazolyl or pyrazolyl, each of which is optionally substituted by fluorine, chlorine, bromine, methyl or ethyl, very particularly preferably represents phenoxy-alkyl with 1 to 4 carbon atoms optionally substituted by fluorine, chloro-, methyl- or ethyl or very particularly preferably represents pyridoxy-alkyl with 1 to 4 carbon atoms, pyrimidyloxy-alkyl with 1 to 4 carbon atoms or triazolyloxy-alkyl with 1 to 4 carbon atoms, each of which is optionally substituted by fluorine, chlorine, ammonium, methyl or ethyl. Particularly preferably, R "represents alkyl with 1 to 14 carbon atoms, alkenyl with 2 to 14 carbon atoms, alkoxy with 1 to 4 carbon atoms-alkyl having 2 to 6 carbon atoms or poly-alkoxy with 1 to 4 carbon-alkyl atoms with 2 to 6 carbon atoms substituted, respectively, by fluorine or chlorineVery particularly preferably represents cycloalkyl with 3 to 10 carbon atoms optionally substituted by fluorine, chlorine, methyl, ethyl, iso-propyl or methoxy, very particularly preferably or represents phenyl or benzyl substituted respectively optionally fluorine, chlorine, cyano, nitro, methyl, ethyl, propyl, i-propyl, methoxy, ethoxy, trifluoromethyl or trifluoromethoxy. Particularly preferably, it represents methyl, ethyl, propyl, isopropyl, optionally substituted by fluorine or chlorine, or represents phenyl or benzyl, optionally substituted by fluorine, by chlorine, by bromine, by methyl, by ethyl, by propyl, by isopropyl, by tert-butyl, by methoxy, ethoxy, isopropoxy, tert-butoxy, trifluoromethyl, trifluoromethoxy, cyano or nitro, particularly preferably R4 and RJ independently of each other, represent 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 to 4 carbon atoms) amino, alkylthio with 1 to 4 carbon atoms, respectively substituted by fluorine or by chlorine or represent phenyl, phenoxy or phenylthio 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, respectively carbon, for rent ilthio with 1 to 2 carbon atoms, fluoroalkylthio with 1 to 2 carbon atoms or alkyl with 1 to 3 carbon atoms. Particularly preferably, R 'and R, independently of one another, represent hydrogen, represent alkyl with 1 to 4 carbon atoms, cycloalkyl with 3 to 6 carbon atoms, alkoxy with 1 to 4 carbon atoms, alkenyl with 3 to 4 carbon atoms or alkoxy with 1 to 4 carbon atoms-alkyl having 1 to 4 carbon atoms, respectively substituted, if appropriate, by fluorine or chlorine, optionally substituted phenyl represented by fluorine, chlorine, bromine, haloalkyl with 1 to 4 carbon atoms carbon, alkyl with 1 to 4 atoms of 58 carbon or alkoxy with 1 to 4 carbon atoms, represent benzyl optionally substituted by fluorine, chlorine, bromine, alkyl with 1 to 4 carbon atoms, halogenalkyl with 1 to 4 carbon atoms or alkoxy with 1 to 4 carbon atoms or together they represent an alkylene radical with 5 to 6 carbon atoms in which optionally a methylene group is replaced by oxygen or sulfur. The definitions of the radicals or the explanations indicated above in a general manner or in the preferred ranges can be combined arbitrarily with each other, ie even between the corresponding ranges and preferred ranges. These are valid for the final products as well as correspondingly for the starting products and for the intermediate products. The compounds of the formula (I) in which a combination of those represented above as preferred (preferably) will be present are preferred according to the invention. Especially preferred according to the invention are compounds of the formula (I), in which a combination of the abovementioned representatives is present, with particular preference.

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

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

The substituted radicals, if appropriate, can be mono- or polysubstituted, the substituents being the same or different in the case of multiple substitutions.

In particular, mention may be made, in addition to the compounds indicated in the preparation examples, of the following compounds of the formula (I-1-a): Table 2: A and B as indicated in table 1- X = Cl; Y = H; Z = H. Table 3: A and B as indicated in table 1 X = CH3; Y = CH3; Z = H. Table 4: A and B as indicated in table 1- X = CH3; Y = H; Z = 6-CH3. Table 5: A and B as indicated in table 1 X = CH; Y = CH5; Z = 5-CH3. Table 6: A and B as indicated in table 1 X = CH ^; Y = CH ,; Z = 6-CH3.

Table 7: A and B as indicated in table 1. X = Cl; Y = Cl; Z = H. Table 8: A and B as indicated in table 1. X = Cl; Y = CH3; Z = H. Table 9: A and B as indicated in table 1. X = CH3; Y = Cl; Z = H. Table 10: A and B as indicated in table 1. X = Cl; Y = Cl; Z = 6-CH3. Table 11: A and B as indicated in table 1. X = Cl; Y = CH3; Z = Cl. Table 12: A and B as indicated in table 1, X = CH3; Y = CH3; Z = 6-Cl. Table 13: A and B as indicated in table 1. X = CH3; Y = Cl; Z = 6-CH3. Table 14: A and B as indicated in table 1. X = CH¿; Y = CH3; Z = 6-Br. Table 15: A and B as indicated in table 1. Table 16: A and B as indicated in table 1 X = CH3; Y = Cl; Z = 5-CH3. Table 17: A and B as indicated in table 1 X = CH3; Y = Br; Z = 5-CH3. Table 18: A and B as indicated in table 1 X = Br; Y = CH3; Z = 5-CH3.

Table 19: A and B as indicated in table 1. X = Br; Y = Cl; Z = 6-CH3. Table 20: A and B as indicated in table 1. X = Br; Y = CH3; Z = 6-Cl. Table 21: A and B as indicated in table 1. X = Cl; Y = Br; Z = 6-CH3.

If, according to process (A), N- [(2,4,6-trimethylphenyl) -acetyl-2,2-dimethy1-5-amino-1, 3 -> 10 dioxan-5-carboxylate of methyl, the development of the process according to the invention can be represented by means of the scheme of the following formulas: If, according to procedure (Ba), 3- [(2,4-dichloro) -phenyl] -5,5- (2,4-dioxanpentamethylene) -2-pyrrolidin-2,4-dione and pivaloyl chloride are used As a starting product, the development of the process according to the invention can be represented by means of the following reaction scheme: If cis-3- [(2, 4-dimethyl) -phenyl] -5,5- [(3-methyl) -2,4-dioxapentamentylene] - [1-pyrrolidin-] is used according to the procedure (Bβ) 2,4-dione and acetic anhydride as starting compounds, the development of the process according to the invention can be represented by means of the following reaction scheme: Base If, according to process (C), cis-3- [(2,4,5-trimethyl) -phenyl] -5,5- [(3,3-tetramethylene) -2,4-dioxapentamentylene] -? "-pyrrolidin-2,4-dione and ethyl chloroformate as starting materials, the development of the process according to the invention can be represented by means of the following reaction scheme: If trans-3- [(2,6-dimethyl-4-bromo) -phenyl] -5,5- [(3-methyl) -2,4-dioxapentament ilen] - is used according to procedure (D) ? 3-pyrrolidin-2,4-dione and methyl chloromonothioformate as a starting material, the development of the reaction can be represented by means of the following scheme: If, according to the procedure (E), 3- [(2-chloro-4-methyl) -phenyl] -5,5- [(3, 3-pentamethylene) -2,4-dioxapentamentyl] -? J- is used pyrrolidin-2,4-dione and metasulfonyl chloride as starting material, the reaction can be represented as follows: If, according to process (F), 3- [(2,4,6-trimethyl) -phenyl] -5,5-f (2,4-dioxapentamentylene-β-pyrrolidin-2,4-dione and Methanoothio-phosphoryl chloride- (2, 2, 2-trifluoromethyl ester) as starting compounds, development may be represented by the following reaction scheme: If it is used, according to the procedure (G), 3 - [(2,4,6-trimethyl) -phenyl] -5,5- [(3, 3-diethynyloxy) -2,4-dioxapentamentylene] -? J- pyrrolidin-2,4-dione and NaOH as components, the development of the reaction of the process according to the invention can be represented by means of the following reaction scheme: If, according to the procedure (H), 3- [(2-methyl-1-4-chloro) -phenyl] -5,5- [(3, 3-dimethyl) -2,4-dioxapentamentylene] -? 3 is used -pyrrolidin-2,4-dione and dimethylcarbamidyl chloride as starting material, the development of the reaction can be represented by means of the following scheme: The compounds of the formula (II) require an initiation material in the process (A) according to the invention wherein A, B, D, X, Y, Z, R and n have the above represented, are new. The esters of the acylamino acids of the formula (II) are obtained, for example, if amino acid derivatives of the formula (XII) are acylated wherein A, B and Rb have the above represented, with substituted phenylacetyl halides of the formula (XIII) wherein X, Y Z and n have the above represented and Hal represents chlorine or bromine, (Chem. Reviews 52, 237-416 (1953); Bhattacharya, Indian J. Chem. 6, 341-5, 1968). The compounds of the formula (XII) are new. The esters of the aminiacids of the formula (XII) are obtained, for example by reacting esters of nitrocarboxylic acids of the formula (XIV) wherein A, B and R have the above-indicated, with hydrogen in the presence of a hydrogenation catalyst such as for example Raney cobalt or Raney nickel, palladium or platinum (for example on carbon as support material), if appropriate in the presence of a diluent such as for example methanol or ethanol, at temperatures between -20 ° C and + 200 ° C, preferably between 0 ° C and 150 ° C and at pressures comprised between 1 bar and 300 bar, preferably between 10 bar and 200 bars (see the production examples). The compounds of the formula (XIV) are particularly known or can be prepared according to known procedures (Piotrowska, Urbanski, olochowicz, Bulletin de L'Academie Polonaise des Science XIX, 591-94 1971). Furthermore, the acylaminoesters of the formula (II) are obtained, for example, if amino acid derivatives of the formula (XV) are oxidized. wherein A, B, X, Y Z and n have the above-indicated represented, in the presence of a cyanide source, an oxidizing reagent and an alcohol, if appropriate in the presence of a solvent. The compounds of the formula (XV) are new, however they can be prepared in analogy with known procedures (Polniaszek, Stevens, J. Org. Chem. 51, 3023-3027, 1986). The derivatives of the amino acids of the formula (XV for example if they are oxidized according to Swern, acylaminoalcohols of the formula (XVI) are obtained wherein A, B, X, Y Z and n have the above-indicated represented, (Polniaszek, Stevens, J. Org.Chem.-51, 3023-3027, 1986; Oura, Swern, Tetrahedron 34_, 1951; 1978). The compounds of formula (XVI) are new. The acylaminoalcohols of the formula (XVI) are obtained, for example, if 5-amino-5-hydroxymethyl-1,3-dioxanes of the formula (XVII) are acylated. wherein A and B have the above-indicated represented, with phenylacetyl halides of the formula (XIII) wherein X, Y, Z and n have the above-indicated and Hal represents chlorine or bromine, if appropriate in the presence of a solvent and, if appropriate, in the presence of a base. The compounds of the formula (XIII) are partially novel, however they can be prepared in principle in analogy with known processes (see the examples of obtaining the compounds of the formula XXXIII-b of the German patent application of the applicant with the file DE-19523850).

The compounds of the formula (XVII) are partially new. The aminoalcohols of the formula (XVII) are obtained, for example, if nitroalcohols of the formula (XVIII) are reacted (VIII) wherein A and B have the above-indicated, with hydrogen in the presence of a hydrogenation catalyst such as for example Raney cobalt or Raney nickel, palladium or platinum (for example on carbon as support material), if necessary in the presence of a diluent such as for example methanol or ethanol, at temperatures between -20 ° C and + 200 ° C, preferably between 0 ° C and 150 ° C. / at pressures comprised between 1 bar and 300 bar, preferably between 10 bar and 200 bars (see the production examples). Nitroalcohols required as starting materials, of the formula (XVIII) (XVIII) wherein A and B have the abovementioned one, are partially known and / or can be prepared according to known processes (see J.

Am. Chem. Soc. 63, 2635-2636 (1941); Synthesis 1993, 815-818, WO 95/00020). The compounds of the formula (XIII) are partially known and can be further prepared according to the patent applications cited at the outset or in the methods indicated therein. The acyl halides of the formula (III), the anhydrides of the carboxylic acids of the formula (IV), the esters of the chloroformic acid or the thioesters of the chloroformic acid of the formula (V), the esters of the chloro-onotioformic acid or the esters of the chlorodithioformic acid of the formula (VI), the sulfonyl chlorides of the formula (VII), the phosphorus compounds of the formula (VIII) and the metal hydroxides, metal alkoxides or amines of the formula (IX) and (X ) and the carbamidyl chlorides of the formula (XI), which are also necessary as starting materials for carrying out the processes (B), (C), (D), (E), (F), (G) and ( H), according to the invention, are generally known compounds of organic or inorganic chemistry. The process (A) is characterized in that compounds of the formula (II) are subjected to an intramolecular condensation, wherein A, B, X, Z, n and R8 have the abovementioned representatives, in the presence of a base. Suitable diluents in the process (A) according to the invention are all inert organic solvents. Preferably, hydrocarbons, such as toluene and xylene, esters, such as dibutyl ether, tetrahydrofuran, dioxane, glycoli ethyl ether and diglycidimethyl ether can be used, 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 tert-butanol. As bases (deprotonation agent), all customary proton acceptors can be used in carrying out the process (A) according to the invention. Preferably, alkali metal and alkaline earth metal oxides, hydroxides and carbonates, such as sodium hydroxide, hydroxide, can be used. of potassium, magnesium oxide, calcium oxide, sodium carbonate, potassium carbonate and calcium carbonate, which may also be employed in the presence of phase transfer catalysts such as, for example, tritylbenzylamine chloride, tetrabutylamino bromide, Adegon 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 widely. 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 the equimolar amount. However, it is also possible to use one or other of the components in a larger excess (up to 3 moles). The process (Ba) is characterized in that compounds of the formula (Ia) are reacted with carbonyl halides of the formula (III), if appropriate in the presence of a diluent and, if appropriate, in the presence of an acid-binding agent. . Suitable diluents in the process (Ba) according to the invention are all solvents which are inert towards acyl halides. Preferably they can face acyl halides. Preference is given to using hydrocarbons, such as benzine, benzene, toluene, xylene and tetralin, as well as halogenated hydrocarbons, such as methylene chloride, chloroform, carbon tetrachloride, chlorobenzene and o-dichlorobenzene, as well as ketones, such as acetone and methylisopropyl ketone. , nitriles, such as acetonitriles, further esters, 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 halogenide of The reaction can also be carried out in the presence of water, as acid-binding agents, all the customary acid acceptors can be used in the reaction according to process (Ba) according to the invention, it is preferable to use tertiary amines, such as triethylamine, pyridine, diazabicyclooctane (DABCO), diazabicyclodedec ene (DBU), diazabicyclononene (DBN), Hünig bases and N, N-dimethyl-aniline, in addition • alkaline earth metal oxides, 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 alkaline hydroxides such as sodium hydroxide and potassium hydroxide. The reaction temperatures in the process (Ba) 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 (Ba) according to the invention, the starting materials of the formula (I-a) and the carbonyl halide of the formula (III) are used, in general, respectively in approximately equivalent amounts. However, it is also possible to use the carbonyl halide in an excess of - greater (up to 5 moles). Working up is carried out by customary methods . The procedure (Bß) is characterized in that react compounds of the formula (I-a) with carboxylic acid anhydrides of the formula (IV), if appropriate in the presence of a diluent and, if appropriate, in the presence of an acid-binding agent. -k As diluents can be used in the Process (Bß) according to the invention preferably those diluents which are also preferably used when acyl halides are used. Otherwise, an excess of the carboxylic acid anhydride used simultaneously can act as diluent. As acid-binding agents added if appropriate, in the case of the process (Bß), preference is given to those acid acceptors which are preferably considered also when acyl halides are used. The reaction temperatures in the process (Bß) 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 (Bß) according to the invention, the starting materials of the formula (I-a) and the carboxylic acid anhydride of the formula (IV) are used in generally approximately equivalent amounts. However, it is also possible to use the carboxylic acid anhydride in a larger excess (up to 5 moles). Working up is carried out by customary methods. In general, it is produced in such a way that the solvent and anhydride of the carboxylic acid present in excess are removed as well as the carboxylic acid formed by distillation or by washing with an organic solvent or with water. Process (C) is characterized in that compounds of formula (Ia) are reacted, respectively, with esters of chloroformic acid or with thioesters of chloroformic acid of formula (V), if appropriate in the presence of a diluent and, if appropriate, in the presence of an acid-accepting agent. Suitable acid-binding agents are all the usual acid acceptors in the reaction according to process (C) according to the invention. Preferably, tertiary amides, such as triethylamine, pyridine, DABCO, DBÜ, DBA, Hünig and N, -dimethyl-aniline bases, as well as alkaline earth metal oxides such as magnesium and calcium oxide, further alkali metal carbonates and alkaline earth metals, such as sodium carbonate, potassium carbonate and calcium carbonate, as well as alkali hydroxides such as sodium hydroxide and potassium hydroxide. As a diluent, all solvents which are inert to the esters of chloroformic acid or to the thiol esters of chloroformic acid can be used in process (C) according to the invention. Preferably hydrocarbons, such as benzine, banzene, toluene, xylene and tetralin, in addition halogenated hydrocarbons, such as methylene chloride, chloroform, carbon tetrachloride, chlorobenzene and o-dichlorobenzene, in addition ketones, such as acetone and methylisopropyl ketone, nitriles such as acetonitrile, furthermore ethers, such as diethyl ester, tetrahydrofuran and dioxane, further esters of carboxylic acids, such as ethyl acetate and also strong polar solvents such as dimethyl sulfoxide and sulfolane. The reaction temperatures in the process (C) according to the invention can vary within wide limits. It is worked in the presence of a diluent and an acid-accepting agent, the reaction temperatures will generally be between -20 ° C and 100 ° C, preferably between 0 ° C and 50 ° C. > The process (C) according to the invention is generally carried out under normal pressure. When carrying out the process (C) according to the invention, the starting materials of the formula (I-a) and the corresponding chloroformic acid ester or chloroformic acid thiol ester of the formula (V) are used in general, respectively, in amounts > 10 approximately equivalent. However, it is also possible to use one or other of the components in a larger excess (up to 2 moles). The processing is carried out according to usual methods. In general we proceed in such a way that salts are eliminated The precipitate is concentrated and the mixture of the remaining reaction is concentrated by elimination of the diluent. The process (D) according to the invention is characterized in that compounds of the formula (I-a) are reacted with compounds of the formula (VI) in The presence of a diluent and, if appropriate, in the presence of an acid-binding agent. In the preparation process (D), about 1 mole of the acid ester is reacted per mole of the starting compound of the formula (I-a) Chloromonothiofstrimic acid or the chlorodithioformic acid ester of the formula (VI) at 0 to 120 ° C, preferably at 20 to 60 ° C. Suitable additives include all inert polar organic solvents, such as esters, 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 the enolate salt of the compounds of the formula (Ia) is prepared in a preferred embodiment by the addition of strong deprotonation agents, such as, for example, sodium hydride or tertiary butylate of post-step, the subsequent addition can be abandoned of acid-binding agents. If acid-binding agents are used, the usual inorganic and organic bases will be considered, for example, 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. Working up is carried out by customary methods. The process (E) according to the invention is characterized in that compounds of the formula (Ia) are reacted with sulfonyl chlorides of the formula (VII), if appropriate in the presence of a diluent and, if appropriate, in the presence of an agent Acid acceptor. In the preparation process (E), about 1 mole of sulfonyl chloride of the formula (VII) is reacted per mole of the starting compound of the formula (Ia) at -20 to 150 ° C, preferably at 20 to 70 ° C. ° C. Suitable diluents, if appropriate, are all inert polar organic solvents, such as esters, amines, ketones, esters of carboxylic acids, nitriles, sulphones, sulfoxides or halogenated hydrocarbons, such as methylene chloride. Preference is given to using dimethylsulfoxide, ethyl acetate, acetonitrile, tetrahydrofuran, dimethylformamide or methylene chloride. If the enolate salt of the compounds (Ia) is prepared in a preferred embodiment by the addition of strong deprotonation agents (such as, for example, sodium hydride or tertiary butylate of post-step), the subsequent addition can be abandoned of acid-binding agents. If acid-binding agents are used, the usual inorganic or organic bases will be used, for example, sodium hydroxide, sodium carbonate, potassium carbonate, pyridine, triethylamine can be exemplified. 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 process (F) according to the invention is characterized in that compounds of the formula (Ia) are reacted, respectively, with phosphorus compounds of the formula (VIII), if appropriate in the presence of a diluent and, if appropriate, in the presence of a Acid acceptor agent. In the preparation process (F), for the preparation of the compounds of the formula (Ie), one mole of the compounds (Ia) is reacted from 1 to 2, preferably from 1 to 1.3 moles of the phosphorus compound of the formula (VIII) at temperatures between -40 ° C and 150 ° C, preferably between -10 and 110 ° C. Suitable diluents, if appropriate, include all inert polar organic solvents, such as esters, amines, 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. Acid-binding agents added, if appropriate, include inorganic bases - Or organic compounds such as hydroxides, carbonates or amines. By way of example, sodium hydroxide, sodium carbonate, potassium carbonate, pyridine, triethylamine may be indicated. The reaction can be carried out at normal pressure or under higher pressure, preferably it will be operated 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 removal of the volatile components under vacuum. The process (G) is characterized in that compounds of the formula (Ia) are reacted with metal hydroxides or with metal alkoxides of the formula (IX) or with amines of the formula (X), optionally in the presence of a diluent . Diluents which can be employed in the process (G) according to the invention are preferably esters such as tetrahydrofuran, dioxane, diethyl ether or also alcohols such as methanol, ethanol, isopropanol, as well as water. The procedure (G) 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. In the preparation process (H), about 1 mole of carbamidyl chloride of the formula (XI) is reacted, per mole of the starting compound of the formula (Ia), at 0 to 150 ° C, preferably at 20 to 100 ° C. ° C. Suitable diluents, if any, come into consideration are all inert polar organic solvents, such as ethers, amides, ketones, esters of carboxylic acids, sulfones, sulfoxides or halogenated hydrocarbons. Preference is given to using dimethylsulphoxides, tetrahydrofuran, ethyl acetate, dimethylformamide or methyl chloride.

If the enolate salt of the compound (Ia) is prepared in a preferred embodiment by the addition of strong deprotonation agents (such as, for example, sodium hydride or potassium tertiary butylate), the further addition of acceptor agents can be abandoned. of acid. If acid-binding agents are used, the usual inorganic or organic bases will be used, examples being sodium hydroxide, sodium carbonate, potassium carbonate, triethylamine and pyridine. The reaction can be carried out at normal pressure or under higher pressure, preferably at normal pressure. Working up is carried out by customary methods. The active products are suitable for the fight against animal pests, preferably against atropods and nematodes, especially insects and arachnids, which occur in agriculture, in forestry, for the protection of stored products and materials as well as in the field 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 and Scutigera spec .. From the order of the syphilis, for example, Scutigerella immacualta. Of the order of the tisanes, for example. Lepisma saccharina. From the order of springtails, for example, Onychiurus armatus. From the order of the orthoptera, for example, Blatta orientalis, Periplaneta americana, Leucophaea maderae, Germanic Blattella; Acheta domesticus, Gryllotalpa spp., Locusta migratoria migratorioides, Melanoplus differentialis and Schistocerca gregaria. From the order of dermápteros, for example, Formatic auricularia. From the order of the Isoptera, for example, Reticulitermes spp ..

From the order of the anoplines, for example, Ph-yloxera vastatrix, Pemphigus spp., Pediculus humanus corporis, Hae atopinus spp., and Linognathus spp. From the order of the malogas, for example, Trichodectes spp. And Damalinea spp. From the order of the Thysanoptera, for example, Hercinothrips femoralis and Thrips tabaci. From the order of the heteroptera, for example, Eurygaster spp., Dysdercus intermedius, Piesma quedrata, Cimex lectularius, Rhodnius prolixus and Triatoma spp. From the order of the Homoptera, for example, Aleurodes brassicae, Bemisia tabaci, Trialeurodes vaporaiorum, Aphis possipii, Brevicoryne brassicae, Cruptomyzus ribis, Aphis fabae, Doralis po i, Erisoma lanigerum, Hyalopterus arundinis, Macrosip-hu-m avenae, Myzus spp. , Phorodon humili, Rhopalosiphum padi, Empoasca spp., Euscelis bilobatus, Nephotettix cincticeps, Lecanium corni, Saissetia oleae, Laodelphax striatellus, Nilaparvata lugens; Aonidiella aurantii, Aspidiotus hederae, Pseudococcus spp., Psylla spp. From the order of the lepidoptera, for example, pectinophora gossypiella, Bupalus piniarius, Cheimtobia brumata, Lithocolletis blancardella, Hyponomeuta padella, Plutella maciulipennis, Malacosorna neustria, Euproctis chrysorrhoea, Lymantria spp. , Bucculatrix thurberiella, Phyllocnistis citrella, Agrotis spp., Euxoa spp., Feltia spp., Earias insulana, Heliothis spp., Spodoptera exigua, Mamestra brassicae, Panolis flam-mea, Prodenia litura, Spodoptera spp., Trichoplusia 5 ni, Carpocapsa pomonella , Pieris spp., Chilo spp., Pyrausta nubilalis, Ephastia Kuehniella, Galleria mellonella, Tineola bisselliella, Tinea pellionella, Hofmannophila pseudospretella, Cacoecia podana, Capua - reticle, Choristoneura fumiferona, Clusia ambiguella, Homona magnánima and Tortrix viridana. The order of the Coleoptera, for example, Anobiu punctatum, Rhizopertha, Acanthoscelides obtectus, Acanthoscelides obtectus, Hylotrupes bajulus, Agelastica alni, Leptinotarsa decemlineata, Phaedon cochleariae, Diabrotica spp., Psylliodes chrysocephala, I Epilachna varivestis, Ato aria spp., Oryzaephilus surinamensis, Anthonomus spp., Sitophilus spp., Otirrhynchus sulcatus, Cosmopolites sordidus, Ceuthorrhynchus assimilis, Hypera postica, Dermestes spp., Trogoderma spp., Anrhrenus spp., Attagenus spp., Lyctus spp., Meligethes aeneus, Ptinus spp., Niptus hololecus, Gibbium psylloides, Tribolium spp., Tenebrio molitor, Agriotes spp., Conoderus spp. , Melolontha melolontha, A-mp-himallon solstitialis, Costelytra zealandica.

From the order of the Hymenoptera, for example, Diprion spp., Hoplocampa spp., Lasius spp., Monomorium pharaonis and Vespa spp., From the order of the dipterans, for example, Aedes spp., Anopheles spp., Culex spp., Drosophila melanogaster, Musca spp., Fannia spp., Calliphora erythrocephala, Lucilia spp., Chrysomya spp., Cuterebra spp., Gastrophilus spp., Hyppobosca spp., Stomoxys spp., Oestrus spp., Hypoderma spp., Tabanus spp., Tannia spp., • Bibio hortulanus, Ascinella frit, Ph-orbia spp., Pegomya hyoscyami, Ceratitis capitata, Dacus oleae and Tipula paludosa. From the order of the symphonoptera, for example, Xenopsylla cheopis, Ceratophyllus spp. From the order of the arachnids, for example Scorpio maurus, Lactrodectus mactans. From the order of mites, for example Acarus siró, Argas spp., Ornithodoro spp., Dermanyssus gallinae, Eriophyes ribis, Phyllocoptruta oleivora, Boophilus spp., Rhipicephalus spp., Amblyomma spp., Hyalomma spp., Ixodes spp., Psoroptes spp. ., Chorioptes spp., Sarcoptes spp., Tarsonemus spp., Bryobia praetiosa, Panoychus spp., Tetranychus spp.

The active compounds according to the invention are characterized in particular by high insecticidal and acaricidal activity. They can be employed particularly successfully for controlling harmful insects to plants, such as, for example, against the mustard beetle larvae leaf (Phaedon cochleariae) or against the larvae of the green rice leafhopper (Nephotettix cinticeps) and against the caterpillars of the cabbage moth (Plutella maculipennis). The active compounds according to the invention can also be used as defoliants, desiccants, agents for eliminating leafy-leaf plants and, especially, for destroying weeds. By weeds, in the broadest sense, we must understand the plants that grow in places where they are unwanted. The fact that the substances according to the invention act as total or selective herbicides depends essentially on the amount used. The active compounds according to the invention can be used, for example, in the following plants: Bad dicotyledonous herbs of the following types: Sinapis, Lepidium, Galiu, Stellaria, Matricaria, Anthemis, Galinsoga, Chenopodium, Urtica, Senecio, Amaranthus, Portulaca, Xanthium, Convolvulus, Ipomoea, Polygonum, Sesbania, Ambrosia, Cirsium, Carduus, Sonchus, Solanum , Rorippa, Rotala, Lindernia, Lamium, Veronica, Abutilon, Emex, Datura, Viola, Geleopsis, Papaver and Centeurea, Trifolium, Ranunculus, Taraxacum Dicotyledonous crops of the genera: Gossypium, Glycine, Beta, Daucus, Phaseolus, Pisum, Solanum, Linum, Ipomoea, Vicia, Nicotiana, Lycopersicon, Arachis, Brassica, Lactuca, Cucumis and Cucurbita.

Bad monocotyledonous herbs of the following kinds: Echinochloa, Setaria, Panicum, Digitaria, Phleum, Poa, Festuca, Eleusine, Brachiaria, Lolium, Bromus, Oats, Cyperus, Sorghum, Agropyron, Cycnodon, Fimbristylis, Sagittaria, Eleocharis, Scirpus, Paspalum, Ischaemum , Sphenoclea, Dactyloctenium, Agrostis, Alopecurus and Apera. Cultures of monocotyledonous classes: Oryza, Zea, Triticum, Hordeum, Oats, Sécale, Sorghum, Panicum, Saccharum, Ananas, Asparagus, Allium. The use of the active compounds according to the invention is, however, not limited in any way to these classes, but extends in the same way also to other plants.

The compounds are suitable, depending on the concentration, to completely combat the weeds, for example, in industrial and various facilities and on roads and squares, with and without tree growth. Likewise, compounds can be used to combat weeds in permanent crops, for example, in forest facilities, ornamental trees, fruit trees, vineyards, citrus trees, walnut trees, bananas, coffee, of tea, gum tree, oil palms, cocoa, berry fruits and hops in ornamental and sports paths and surfaces for meadows and to selectively control weeds in mono-annual crops. The active compounds according to the invention are very suitable for the selective control of mono-cotyledonous weeds in dicotyledonous cultures both in the pre-emergence procedure and in the post-emergence process. These can be used, for example, in cotton and sugar beet with a very good success for the fight against weeds. The active ingredients can be converted into customary formulations, such as solutions, emulsions, sticking powders, suspensions, powders, dusts, pastes, soluble powders, granules, suspension-emulsion concentrates, natural and synthetic materials impregnated with the product active, as well as microencapsulated in polymer materials. These formulations are prepared in known manner, for example, by mixing the active ingredients with extender materials, that is, with liquid solvents and / or solid diluents, if appropriate, using surfactants, that is, emulsifiers and / or dispersants and / o foam generating means. When using water as a filler, it is also possible, for example, to use organic solvents as auxiliary solvents. Particularly preferred liquid solvents are aromatic hydrocarbons, such as xylene, toluene or alkylnaphthalenes, chlorinated aromatic hydrocarbons and chlorinated aliphatic hydrocarbons, such as chlorobenzenes, chloroethylenes or methylene chlorides, aliphatic hydrocarbons, such as cyclohexane or paraffins, for example, fractions of crude oil, alcohols, such as butanol, or glycol, as well as their esters and ethers, ketones, such as acetone, methyl ethyl ketone, methyl isobutyl 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 mineral flours, such as kaolins, clays, talcum, certa, quartz, attapulgite, montmorillonite or diatomaceous earth and ground synthetic minerals, such as highly dispersed silicic acid, • aluminum and silicates, as solid excipients for granulates can be used natural broken 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, husks of walnut, coconut, corn ears and tobacco stalks; as emulsifiers and / or foam generators, non-inorganic and anionic emulsifiers, such as polyoxyethylenated fatty acid esters, polyoxyethylenated fatty alcohol esters, for example alkylaryl polyglycol esters, alkylsulfonates, alkyl sulfates, arylsulfonates, and the products of hydrolysis of albumin can be used; Suitable dispersants are, for example, lignin sulfite residual liquors and methylcellulose.

In the formulations can be used t adhesives such as carboxymethylcellulose, natural and synthetic powdered polymers, granules or in the form of latex, such as gum arabic, polyvinyl alcohol and polyvinyl acetate, as well as natural phospholipids, such as cephalin and lecithin and synthetic phospholipids. Other additives can be mineral and vegetable oils. Dyes, such as I • inorganic pigments, for example, iron oxide, titanium oxide, Prussian blue and organic dyes, such as alizarin dyes, azo dyes and metal phthalocyanine dyes and trace nutrients, such as iron, manganese, boron salts , copper, cobalt, molybdenum and zinc. The formulations generally contain between 0.1 to 95% by weight of active compound, preferably between 0.5 and 90% by weight. The active product according to the invention can They can be presented in their customary formulations in commerce as well as in the forms of application prepared from these formulations, in mixtures with other active products, such as insecticides, bait products, sterilizers, acaricides, nematicides, fungicides, growth regulators or herbicides. Insecticides include, for example, esters of phosphoric acid, carbamates, esters of carbonic acid, chlorinated hydrocarbons, phenylureas, products produced by micro-organisms, etc. Especially convenient blending components are, for example, the following products: Fungisides: 2-aminobutane; 2-anilino-4-methyl-1-6-cyclopropylpyrimidine; 2 ', 6' -dibromo-2-methyl-4 '-trifluromethoxy-4'-trifluoromethyl-1,3-triazole-5-carboxanilide; 2,6-dichloro-N- (4-trifluoromethylbenzyl) banzaide; (E) -2-methoimino-N-methy1-2- (2-phenoxyphenyl) acetamide; 8-hydroxyquinolinesulfate; methyl- (E) -2-2- [6- (2-cyanophenoxy) pyrimidin-4-yloxy] pheny1-3-methoxy-acrylate; methyl- (E) -methoxyimino [alpha- (o-tolyloxy) -o-tolyl] acetate; 2-Phenylphenol (OPP), Aldimorph, Ampropylfos, Anilazin, Azaconazole, Benalaxyl, Benodanil, Benomyl, Binapacryl, Biphenyl, Bitertanol, Blasticidin-S, Bro uconazole, Bupirimate, Buthiobate, Calciumpolysulfid, Captafol, Captan, Carbendazi, Carboxin, Chinomethionat ( Quinomethionat), Chloroneb, Chloropicrin, Chlorothalonil, Chlozolinat, Cufraneb, Cymoxanil, Cyproconazole, Cyprofuram, Dichlorophen, Diclobutrazol, Diclofluanid, Diclomezin, Dicloran, Diethofencarb, Difenoconazole, Dimethirimol, Di ethomorph, Diniconazole, Dinocap, Diphenyla in, Dipyrithion, Ditalimfos, Dithianon , Dodine, Drazoxolon, Edifenphos, Epoxyconazole, Ethirimol, Etridiazole, Fenarimol, Fenbuconazole, Fenfuram, Fenitropan, Fenpiclonil, Fenpropidin, Fenpropimorf, Fentinacetat, fentinhydroxyd, Ferbam, Ferimzone, Fluazinam, Fludioxonil, Fluoro ide, Fluquinconazole, Flusilazole, Flusulfamide, Flutolanil, Flutriafol, Folpet, Fosetyl-Aluminum, Fthalide, Fuberidazole, Furalaxil, Furmecyclox, Guazatine, Hexaclobenzene, Hexaconazole , Hymexazole, Imazalil, Imibenconazole, Iminoctadin, Iprobenfos (IBP), Iprodion, Isoprothiolan, Kasugamycin, copper compositions, such as; copper hydroxide, copper naphthenate, copper oxychloride, copper sulfate, copper oxime and mixtures of Bordeux, Mancopper, Mancozeb, Maneb Mepanipyrim, Mepronil, Metalaxyl, Metconazole, Methasulfocard, Methfuroxam, Metira, Metsulfuvax, Myclobutanil, NiqueldimetiIditiocarbamate, Nitrothal -isopropyl, Naurimol, Ofurace, Oxadixyl, Oxamocarb, Oxicarboxin, Perfurazoat, Penconazole, Pencycuron, Phosdiphen, Phthalid, Pimaricin, Piperalin, Polycarbamate, Polyoxin, Probenazole, Prochloraz, Procymidon, Propamocarb, Propiconazole, Propineb, Pyrazophos, Pyrifenox, 5 Pyrimethanil, Pyroquilon, Quintozen (PCNB), Sulfur and sulfur compositions, Tebuconazole, Tecloftalem, Tecnazen, Tetraconazole, Thiabendazole, Thicyofen, Thiophanat-ethyl, Thiram, 10 Tolclophos-methyl, Tolylfluanid, Triadi efon, Triadimenol, Triazoxid, Trichla id, Tricyclazole , Tridemorph, Triflu izol, Triforin, Triticonazole, Validamycin A, Vinclozolin, Zineb, Zira. 15) Bactericides: Bronopol, Dichlorophen, Nitrapyrin, nickel diethyldithiocarbamate, Kasugamycin, Octhilinon, furancarboxylic acid, Oxytetracyclin, 20 Probenazole, Streptomycin, Tecloftalam, copper sulfate and other copper preparations.

Insecticides / Asarisides / Nematicides: -Abamectin, Abamectin, AC 303 630, Acephat, Acrinat-hrin, Alanycarb, Aldicarb, Alphamethrin, Amitraz, Avermectin, AZ 60541, Azadirachtin, Azinphos, A, Azinphos M, Azocyclotin, Bacillus thuringiensis, Bendiocarb, Benfuracarb, Bensultap, Betacyluthrin, Bifenthrin, BPMC, Brofenprox, Bromophos A, Bufencarb, Buprofezin, Butocarboxin, Butylpiridaben, Cadusafos, Carbaryl, Carbofuran, Carbophenothion, Carbosulfan, Cartap, CGA 157 419, CGA 184699, Chloethocarb, Chlorethoxyphos, Chlorfenvinphos, Chlorfluazuron, Chlor ephos, Chlorpyrifos, Chlospyrifos M, Cis-Resmethrin, Clocythrin, Clofentezin, Cyanophos, Cycloprothrin, Cyfluthrin, Cyhalothrin, Cyhexatin, Cypermethrin, Cyro azin, Deltamethrin, Demeton M, Demeton S, Demeton-S -methyl, Diafenthiuron, Siazinon, Dichlofenthion, Dichlorvos, Dicliphos, Dicrothos, Diethion, Diflubenzuron, Dimethoat, Dymethylvinphos, Dioxathion, Disulfoton, Edifenphos, Emamectin, Esfenvalerat, Ethiophencarb, Ethion, Ethofenprox, Ethoprophos, Etofenprox, Etrimphos, Fenamiphos, Fenazaquin, Fenbutatinoxid , Fenitrothion, Fenobucarb, Fenothiocarb, Fenoxycarb, Fenpropathrin, Fenpyrad, Fenpyroximat, Fenthion, Fenvalerate, Fipronil, Fluazinam, Flucycloxuron, Flucythrinat, Flufenoxuron, Flufenprox, Fluvalinate, Fonophos, Formothion, Fasthiazat, Fubfenprox, Furathiocarb, HCH, Heptenophos, Hexaflumuron, Hexythiazox , Imidacloprid, Iprobenfos, Isazophos, Isofenphos, Isoprocarb, Isoxathion, Ive ectin, Lamda-cyhalothrin , Lufenuron, Malathion, Mecarbam, Mervinphos, Mesulfenphos, Metaldehyd, Methacrifos, Methamidophos, Methidathion, Methiocarb, Methomyl, Metolcarb, Milbemectin, Monocrotophos, Moxidectin, Naled, NC 184, NI 25, Nitenpyram Omethoat, Oxamyl, Oxydemethon M, Oxydeprofos, Parathion A, Parathion M, Permethrin, Phenthoat, Phorat, Phosalon, Phosmet, Phosphamdon, Phoxim, Pirimicarb, Pirimiphos M, Pirmiphos A, Profenofos, Promecarb, Propaphos, Propoxur, Prothiophos, Prothoat, Pymetrozin, Pyrachlophos, Pyradaphenthion, Pyresmethrin, Pyrethrum, Pyridaben , Pyrimidifen, pyriproxifen, Quinalphos. RH 5992. Saliyhion, Sebufos, Silafluofen, Sulfotep, Sulprofos, Tebufenozid, Tebufenpyrad, Tebupirimphos, Teflubenzuron, Tefluthrin, Te ephos, Terba, Terbufos, Tetrachlorvinphos, Thiafenox, Thiodicarb, Thiofanox, Thiomethon, Thionazin, Thuringiensin, Tralomethrin, Triarathen, Triazophos, Triazuron, Trichlorfon, Trifluuron, Trimethacarb, Vamidothio, XMC, Xylylcarb, Yl 5301/5302, Zetamethrin.

Herbides, for example, anuides, such as Diflufenican and Propanil; arylcarboxylic acid, such as dichloropicolinic acid, Dicamba and Picloram; aryloxyalkanoic acids, such as, for example, 2,4 D, 2,4 DB, 2,4 DP, Fluroxypyr, MCPA, MCPP and Triclopyr; esters of the aryloxy-phenoxy-alkanoic acids, such as • Diclofop-methyl, Fenoxaprop-ethyl, Fluazifop-butyl, Halaxyfop-methyl and Quizalofop-ethyl; azinones, such as for example Chloridazon and Norflurazon; carbamates, such as for example Chlorpropham; 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, Femesafen, Halosafen, Lactofen and Oxyfluorfen; ureas, such as for example Chlortoluron, Diuron, Fluometuron, Isoproturon, Linuron and Methabenzothiazuron; hydroxylamines, such as for example Alloxydim, Clethodim, Cycloxydim, Sethoxydim and Tralkoxydim; i idazolinones, such as, for example, Imazethapyr, Imazamethabenz, Imazapyr and Imazaquin; nitriles, such as for example Bromoxynil, Dichlobenil and Ioxynil; Oxyacetamides, such as for example Mefeneact; sulfonylureas, such as for example -Amidosulfuron, Bensulfuron-ethyl, chlorimuron-ethyl, Chlorsulfuron, Cinosulfuron, Metsulfuron-ethyl, Nicosulfuron, Primisulfuron, Pyrazosulfuron-ethyl, Thifensulfuron-methyl, Triasulfuron and Tribenuron-methyl; thiolcarbamate, such as for example butylates, cycloates, dialates, ETPC, Esprocab, Molinate, Prosulfocarb, Thiobancarb and Triallate; Triazines such as, for example, Atrazin, Simazin, Simetryna, Terbutryne and Terbutylazin; triazinones, such as for example hexazinon, Metamitron and Metribuzin; others, such as for example aminotriazole, Benfuresate, Bentazone, Cinmehylin, Clomazone, Clopyralid, Difenzoquat, Dithiopyr, Ethofumesate, Fluorchloridone, Glufosinate, Gliphosate, Isoxaben, Pyridate, Quinchlorac, Quinmerac, Sulphosate and Trhane. The active compound according to the invention can 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 through which the effect of the active products is increased, without the synergetic aggregate having to be active in it. The content in the active product of the forms of application 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% by weight. The application is carried out in a manner adapted to the forms of application. In the use against hygiene pests and stored products, active products are characterized by an excellent residual effect on wood and clay as well as good alkali stability on whitewashed supports. The active compounds according to the invention are not only active against plant pests, hygiene and stored products, but also in the field of veterinary medicine against animal parasites (ectoparasites) such as hard ticks, soft ticks , scabies mites, migratory mites, flies (suckers and mincers), fly parasitic larvae, lice, hair nits, nits of feathers and aphids, faith To these parasites belong: From the order of the anopluros, for example Hae atopinus spp., Linognathus spp., Pediculus spp., 5 Phtirus spp., Solenopotes spp. From the order of malofagids and amblycerine sub-orders as well as isoquinoline, for example Trimenopon spp., Menopon spp., Trinoton spp., - ~ Bovicola spp., Werneckiella spp., Lepikentron spp., Damalin 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., Atylotys ) spp., Tabanus spp., Haematopota spp., Philipomyia spp., Braula spp., Musca spp., Hydrotaea spp., Stomoxys spp., Haematobia spp., Morellia spp., Fannia spp., Glossina spp., Calliphora spp., Lucilia spp., Chrysomyia spp., ohlfahrtia spp., Sarcophaga spp., Oestrus spp., Hypoderma spp., Gasterophilus spp., Hippobosca spp., Lipoptena spp., Melophagus spp. From the order of the siphonapterids, for example Pulex spp., Ctenocephalides spp., Xenopsylla spp., 25 Ceratophyllus spp.

From the order of heteropterids, for example Cimex spp., Triatoma spp., Rhodnius spp., Panstrongylus spp. From the order of the blatarids, for example Blatta orientalis, Periplaneta americana, Germanic Blattella, Supella spp. From the order of mites (Acarida) and the order of the meta- as well as mesoestigmatos, for example Argas spp., Ornithodorus spp., Otabius spp., Ixodes spp., Amblyomma spp., Boophilus spp., Dermacentor spp.

Haemaphysalis spp., Hyalomma spp., Rhipicephalus spp., Dermanyssus spp., Raillietia spp., Pneumonyssus spp., Sternostoma spp., Varroa spp. From the order of actinedides (Prostigmata) and acars (Astigmata), for example Acarapis spp. ., Cheyletiella spp., Ornithocheyletia spp., Myobia spp., Psorergates spp., Demodex spp., Trombicula spp., Listrophorus spp., Acarus spp., Tyrophagus spp., Caloglyphus spp., Hypodectes spp., Petrolichus spp., Psoroptes spp., Chorioptes spp., Otodectes spp., Sarcoptes spp., Notoedres spp., Knemidocoptes spp., Cytodites spp., Laminosioptes spp. As an example it shows excellent activity against Boophilus microplus.

The active compounds according to the invention of the formula (I) are also suitable for the fight against anthropods., which attack useful animals in agriculture such as, for example, cows, lambs, goats, horses, pigs, donkeys, camels, buffalos, rabbits, chickens, turkeys, ducks, geese, bees, plus domestic animals such as, for example, dogs, cats, lounge birds, aquarium fish as well as so-called test animals, such as, for example, hamsters, guinea pigs, rats and mice. By fighting against these anthropods will avoid cases of death and reductions in performance (in the case of meat, milk, wool, skins, eggs, honey, etc.), in the way that, by using the active products according to the invention is possible a more economical and simple maintenance of the animals. The application of the active compounds according to the invention is carried out in the veterinary field in a known manner by enteral administration in the form of, for example, tablets, capsules, beverages, dragees, granules, pastes, bolis, by means of the process through the food "Feed-Through", of suppositories, by parenteral administration, such as, for example, by injection (intramuscular, subcutaneous, intravenous, intraperitoneal, etc.) implants, by nasal application, by dermal application in form, by example of immersion or bath (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, marks for the ears, marks for the tail, bands for the extremities, halters, marking devices, etc. When used for domestic livestock, birds, • pets, 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. It has also been found that the compounds according to the invention of the formula (I) show a high insecticidal effect against insects, which destroy industrial materials. By way of example and preference - however without limitation - the following insects may be mentioned: Beetles such as Hylotrupes bajulus, Chlorop orus pilosis, Anobium punctatum, Xestobium rufovillosum, Ptilinus pecticornis, Dendrobium pertinex, Ernobius mollis, Priobium carpini, Lyctus brunnes, Lyctus africanus, Lyctus planicollis, Lyctus linearis, Lyctus pubescens, Trogoxylon aequale, Minthes, rugicollis; Xyleborus spec., Trytodendron spec., Apate monacus, Bostrychus capucins, Heterobostrychus brunneus, Sinoxylon spec., Dinoderus minutus.

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

Termites, such as Kalotermes flavicollis, Cryptotermes brevis, Heterotermes indicated, Reticulitermes flavipes, Reticulitermes santonensis, Reticulitermes licifugus, Mastotermes give iniensis, Zootermopsis nevadensis, Coptetermes formosanus.

Tisanurus, such as Lepisma saccarina. By industrial materials, non-living materials will be understood in the present context, such as, preferably, synthetic materials, glues, glues, paper and cardboard, leather, wood and 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. For wood and wood processing products, which can be protected by means of the agents according to the invention or of the mixtures containing them, it should be understood, for example: construction wood, wooden beams, railway sleepers, parts for bridges, gullies for boats, wooden vehicles, boxes, pallets, containers, telephone poles, wooden coverings, wooden windows and doors, wooden plywood, plywood boards, carpentry works and wooden products, which find application, in a very general way, at 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 a diluent, emulsifier, dispersant and / or binder or binding agent, water repellent, optionally drying 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 test series prior to application. In general, however, it is sufficient to use 0.0001 to 20% by weight, preferably 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 organic-chemical solvents and / or a solvent or mixture of organo-chemical, oleaginous or oil-like solvents, which are not readily volatile and / or a solvent or mixture of polar organochemical solvents, is used. and / or water and, in case of faith, an emulsifier and / or humectant. As organochemical solvents, preference will be given to oleaginous or type solvents. oleaginous, with an evaporation index located above 35 and a flame point located above 30 ° C, preferably located above 45 ° C. By way of such solvents which are difficult to volate, insoluble in water, oleaginous or oil-like, > They will use corresponding mineral oils or their aromatic fractions or solvent mixtures containing mineral oils, preferably benzines for tests, petroleum and / or alkylbenzene. Advantageously, minerals with a boiling range from 170 to 220 ° C, benzene for f tests with a boiling range of 170 up to 220 ° C, spindle oil with a boiling range of 250 to 350 ° C, petroleum or aromatic hydrocarbons with a boiling range from 160 to 280 ° C, terpene oil and the like. In a preferred embodiment, liquid aliphatic hydrocarbons having a boiling range of 180 to 210 ° C or a high boiling point mixture of aromatic hydrocarbons will be used. and aliphatics with a boiling range of 180 to 220 ° C and / or spindle oil and / or onchloro-naphthalene, preferably a-mono-chloronaphthalene. Organic, sparingly soluble, oleaginous or oil-like solvents, with an evaporation value above 35 and with a flame point above 30 ° C, preferably above 45 ° C, can be partially replaced by solvents light or medium volatility organochemicals, provided that the solvent mixture has an evaporation index above 35 and a flame point above 30 ° C, preferably above 45 ° C, and that the insecticidal-fungicidal mixture is soluble or emulsifiable in this mixture of solvents. According to a preferred embodiment, a part of the solvent or of the organochemical solvent mixture or a solvent or mixture of aliphatic, polar organochemical solvents will be replaced. Preference is given to using aliphatic organochemical solvents containing hydroxyl and / or ester and / or ether groups, such as, for example, glycol ether, esters or the like. As organic-chemical binders, synthetic resins and / or setting drying oils, known per se, dilutable with water and / or soluble or dispersible or emulsifiable in the organic-chemical solvents used, will be used within the scope of the present invention. especially binders consisting of or containing acrylic resin, a vinyl resin, for example polyvinyl acetate, polyester resin, polycondensation or polyaddition resin, polyurethane resin, alkyd resin or modified alkyd resin, phenolic resin, hydrocarbon resin such as indeno-coumaron resin, silicone resin, vegetable drying and / or drying oils and / or physical drying binders based on a natural and / or synthetic resin. The synthetic resin, used as a binder, can be used in the form of an emulsion, dispersion or solution. Bitumen or bituminous substances up to 10% by weight can also be used as binders. In a complementary manner, dyes, pigments, water repellent agents, odor correctors and inhibitors or anticorrosive agents known per se, and the like, may be used. It is preferred to use at least one alkyd resin or a modified alkyd resin and / or a drying vegetable oil as the organochemical binder in the medium or concentrate 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 totally replaced by a fixing agent (mixture) or by a plasticizer (mixture). These additives must avoid a volatilization of the active products as well as a crystallization or a precipitation, preferably they replace 0.01 to 30% of the binder (referred to 100% of the binder used). The plasticizers are of the chemical grade of phthalic acid esters such as dibutyl, dioctyl or benzylbutyl phthalate, esters of phosphoric acid, such as tributyl phosphate, esters of adipic acid, such as di- adipate ( 2-ethylhexyl), stearates such as butyl stearate or amyl stearate, oleates such as butyl oleate, glycerin esters or high molecular weight glycol ethers, glycerin esters as well as esters of p-toluenesulfonic acid. Fixative agents are chemically based on polyvinylalkyl esters such as polyvinyl methyl ether or ketones such as benzophenone, ethylenebenzophenone.

As solvents or diluents, it enters especially considering water, if appropriate in a mixture with one or more of the solvents or diluents, emulsifiers and organo-chemical dispersants previously mentioned. Especially effective protection of the wood is achieved by impregnation processes on an industrial scale, for example, vacuum, double vacuum or pressure processes. 10 Agents ready for application may, if necessary, contain other insecticides and, if appropriate, one or more other fungicides. Additional components of the mixture are preferably insecticides and fungicides mentioned in WO 94/29 268. The compounds I cited in this document constitute, expressly, an integral part of the present application. Particularly preferred mixing components are insecticides such as Chlorpyriphos, Phoxi-m, Silafluofin, Alphamethrin, Cyfluthrin, Cypermethrin, Deltamethrin, Permethrin, Imidacloprid, NI-25, Flufenoxuron, Hexaflumuron and Triflumuron, as well as fungicides such as Epoxiconazole. , Hexaconazole, Azaconazole, Propiconazole, 25 Tebuconazole, Cyproconazole, Metconazole, Imazalil, Dichlorfluanid, Tolylfluanid, 3-iodo-2-propynyl-butylcarbamate, N-octyl-isothiazolin-3-one and 4,5-dichloro-N-octylisothiazolin- 3-one. The preparation and use of the active compounds according to the invention are apparent from the following examples.

Example of obtaining Example (I-a-1).

Add dropwise to 10 g (0.2 mol) of potassium tert-butylate in 50 ml of anhydrous tetrahydrofuran (THF), at reflux temperature, 12.5 g (0.0764 mol) of the compound according to the example (II-). l) in 100 ml of anhydrous toluene and stirring for 1.5 hours at reflux. For working up, pour over 100 ml of water, separate the aqueous phase, extract the toluene phase with 50 ml of water, combine the aqueous phases, wash with toluene and acidify, at 10 to 20 ° C, with concentrated HCl to pH 6. Extract three times with methylene chloride, dry, concentrate by evaporation and chromatograph the residue on silica gel with hexane / acetone 7: 3. Yield: 5.6 g (46% of theory), Melting point; 222-224 ° C. The following compounds of the formula (I-a) are prepared analogously or according to the general instructions for preparation: Table 22 Example (I-b-l) Combine 1.2 g (3.75 mol) of the compound according to example (Ia-1) and 1.1 ml (7.5 mmol) of triethylamine in 50 ml of anhydrous methylene chloride at 0 to 10 ° C, with 0.8 ml (7.5 mmole) - Isobutyryl chloride in 5 ml of anhydrous methylene chloride. It is stirred at room temperature until the reaction is complete according to the controls carried out by thin layer chromatography. For working up, it is washed twice with 50 ml of 0.5 N sodium hydroxide solution, water, dried over magnesium sulfate and concentrated by evaporation. The crude product is chromatographed with n-hexane / acetone 7: 3 on silica gel. Yield: 0.45 g (31% of theory), Melting point; 153-155 ° C. The following compounds of the formula (I-b-1) are prepared analogously or according to the general instructions for preparation: Table 23 Example (I-c-1) Add, dropwise, to 1.2 g (3.75 mmol) of the compound according to example (Ia-1) and 0.8 ml (5.5 mmol) of triethylamine in 50 ml of anhydrous CH2C12, at 0 to 10 ° C, 0.55 ml ( 5 mmole) of ethyl chloroformate in 5 ml of anhydrous methylene chloride and stirring at room temperature until the reaction is complete according to the controls carried out by thin layer chromatography. For the elaboration it is washed twice with 50 ml of sodium hydroxide lye 0. 5 N, dried over magnesium sulfate and concentrated by evaporation. The residue is chromatographed with hexane / acetone 7: 3 on silica gel. Yield: 0.55 g (38% of theory), Melting point; 138-140 ° C.

The following compounds of the formula (I-1-c) are prepared analogously or according to the general instructions for preparation: Table 24 Example (I-d-1) They were mixed with 0.8 ml of mesyl chloride in 5 ml of methylene chloride at 0 ° C, 3.6 g of the compound of example (Ia-7) in 50 ml of methylene chloride and 1.5 ml of triethylamine, and the mixture was stirred cold for 1 day. Chromatograph on silica gel to provide 2.50 g (58% of theory), m.p .: 212-214 ° C.

Example (I-f-1) At 20 ° C, 3.6 g of the compound of example (I-a-7) were mixed in 50 ml of methanol with 2 g of a sodium methoxide solution and stirred at this temperature for one day. The mixture is added in toluene and evaporated under reduced pressure. Yield: 4.50 g (99% of theory), m.p .: > 250 ° C.

Example (I-g-1) It is mixed with 1.4 g of morpholinecarbamyl chloride in 5 ml of ethyl acetate at reflux temperature, 3.6 g of the compound of example (Ia-7) in 50 ml of ethyl acetate and 1.5 ml of triethylamine, and the mixture is heated under reflux for a day. Chromatograph on silica gel to give 0.85 g (18% of theory), m.p .: 190-192 ° C.

Example (II-l) 102 g (0.63 mmol) of the compound according to example (XV-1), in 1,200 ml of methylene chloride, under argon, with 54 g of acetocyanhydrin and 10.5 ml of triethylamine were combined and stirred for 1 day at 20 °. C and concentrated by evaporation (reagent A). 46.5 g of oxalyl chloride were placed in 600 ml of methylene chloride. 81 g of dimethylsulfoxide in 210 ml of methylene chloride were added dropwise at -78 ° C. After 15 minutes, dropwise to reagent A (aldehydocyanhydrin), dissolved in 450 ml of methylene chloride, at -78 ° C, stirring continued for 30 minutes at -78 ° C and for 30 minutes at 30 ° C. -25 ° C. it is cooled again to -78 ° C and 230 ml of triethylamine are added dropwise. It is then stirred for 10 minutes at -78 ° C. After heating to -25 ° C it is combined with 1050 ml of methanol and stirred for 1 day at room temperature. The charge is poured into water, extracted with methylene chloride, dried and concentrated by evaporation. After chromatography on silica gel with n-hexane / acetone 7: 3 and crystallization with methylene chloride / n-hexane, 43 g are obtained. of the ester indicated above (19% of theory) with a melting point of 106 ° C. Analogously to the example (II-1) and according to the general indications for the preparation, the following compounds of the formula (II) are prepared: Table 25 (H) * 1) 400 MHz in d6-DMS0: d = 3.93 (d, 2H, 0-CH2), 4.08 (d, 2H, OCH2), 4.86 (c, 1H, CHMe). * 2) is cyclized (I-to-8) without further purification Example (XV-1) Add dropwise to 20 ml of oxalyl chloride in 1000 ml of anhydrous tetrahydrofuran at -70 ° C, 19 ml of DMSO, stir for another 3 minutes at -35 ° C, cool again to - 70 ° C and 65 g (0.25 mmol) of the compound according to Example XVI-1 are added dropwise in 300 ml of anhydrous tetrahydrofuran in the course of 1 hour. The mixture is stirred for a further 15 minutes at -35 ° C, 250 ml of triethylamine are added dropwise and the mixture is stirred for 1 day at room temperature. It is combined with n-hexane, the precipitate is filtered off, the filtrate is concentrated on a rotary evaporator and the residue is chromatographed on silica gel with methylene chloride / acetone 2: 1. Yield: 44.5 g (? 67% of theory) with a melting point of 110 ° C. Analogously to the example (XV-1) and according to the general indications, the following compounds of the formula (XV) are prepared: Table 26. • 1) is reacted as a crude product to provide (II-9) Example (XVI-1) 45 g (0.25 mole) of the compound according to Example XVII-1 were dissolved in 500 ml of anhydrous tetrahydrofuran, combined with 40 ml of triethylamine and 50 g of mesitylene-acetyl chloride were added dropwise at 0 ° C. stirred for 1 hour at room temperature. The precipitate was separated by filtration, the filtrate was concentrated by evaporation and the residue was chromatographed on silica gel with hexane / ethyl acetate 2: 1.

Yield: 66 g (? 82% of theoretical) with a melting point of 94 ° C.

In analogy with example XVI-1 and according to the general indications, the following compounds of formula XVI were prepared.

Table 27 (XV) * 1) is reacted as a crude product to provide (XV-10).

Example (XVII-1) 13.5 g (0.07 mole) of 5-amins- 2, 2-dimethyl-5-hydroxymethyl-l, 3-dioxane are hydrogenated in 100 ml of ethanol in the presence of 2 g of Raney nickel with hydrogen at 20 bar and 40 ° C. in the autoclave. The catalyst is filtered off, the filtrate is concentrated by evaporation, the residue is taken up in methylene chloride and the product is precipitated with n-hexane. Yield: 10.3 g (= 91% of theory). 1 H-NMR (200 MHz in d 6 -DMS0): d = 1.28 (s, 3 H, CH 3), 1.32 (s, 3 H, CH 3), 3.35 (s, 2 H, CH 2 OH), 3.4 (d, 2 H, 0 CH 2), 3.57 (d, 2H, OCH2).

Example XVIII-1 Dissolve 100 g of 2,2-dimethoxypropane in 1000 ml of acetone, add 5 g of p-toluenesulfonic acid, add 150 g of trishydroxymethylnitromethane and stir for 1 hour at room temperature. After the addition of another 100 g of 2, 2-dimethoxypropane is heated for 4 hours at 40 ° C, the filtrate is concentrated by evaporation and the residue is chromatographed on silica gel with hexane / acetone 7: 3. Yield: 75 g (= 39% of theory).

LH-NMR (200 MHz in d6-DMSO): d = 1.23 (s, 3H, CH3), 1.28 (s, 3H, CH3), 3.7 (d, 2H, CH2OH), 4.02 (d, 2H, OCH2), 4.32 (d, 2H, OCH2). The cis / trans isomer mixtures of the compounds of the formula XVIII, which are obtained when aldehydes are used, are separated into the isomers by crystallization, by chromatographic methods or by distillation.

Example of Use Example A Test with Tetranychus (OP-resistant / dip treatment) Solvent: 7.5 parts by weight of dimethylformamide 100 parts by weight of methanol Emulsifier: 2.5 parts by weight of alkylaryl polyglycol ether To obtain a convenient preparation of active compound mix 1 part by weight of the active product with the indicated amount of emulsifier and dilute the concentrate with water with water containing emulsifier to the desired concentration. Bean plants (Phaseolus vulgaris), which are strongly attacked by all stages of development of the common red spider mite Tetranychus urticae, are submerged in a preparation of the active compound at the desired concentration. After the desired time the destruction is determined in%. In this case 100% means that all red spider mites were removed; 0% means that no red spider mite has been removed. In this test, for example, the compounds according to the following preparation examples I-a-1, I-b-1 and I-c-1 at an exemplary concentration of the active compound of 0.1% show a destruction of > 98% after 13 days.

Example B 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 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 concentration desired.

Cabbage leaves (Brassica oleracea) are treated by being dipped into the preparation of the active compound of the desired concentration and covered with larvae of the green beetle of the leaves of the horseradish (Phaedon cochleariae), as long as the leaves are still moist. After the desired time the destruction is determined in%. In this case 100% means that all beetle larvae were destroyed; 0% means that no beetle larvae were destroyed. In this test, for example, the compounds according to the following preparation examples Ia-1, Ib-1,, Ib-2, Ib-3, Ib-4 and Ib-10 at an exemplary concentration of the active product of 0.1% are shown. 100% destruction after 7 days.

EXAMPLE C Assay with Plutella Solvent: 7 parts by weight of dimethylformamide. Emulsifier: 1 part by weight of alkyl polyglycol ether In order to obtain a convenient 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. Cabbage leaves (Brassica olerácea) are treated by being dipped into the preparation of the active compound of the desired concentration and covered with caterpillars of the cabbage moth (Plutella asculipennis) as long as the leaves are still moist. After the desired time the destruction is determined in%. In this case 100% means that all caterpillars were destroyed; 0% means that no caterpillar was destroyed. In this test, for example, the compounds according to the following preparation examples I-a-1, I-b-1 and I-c-1 are shown at an exemplary concentration of the active compound of 0.1%, a destruction of 100% after 7 days.

Example D Test with Nephotettix. Solvent: 7 parts by weight of dimethylformamide. Emulsifier: 1 part by weight of alkylaryl polyglycol ether To obtain a convenient 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 concentration desired. Rice seedlings (Oryza sativa) are treated by immersion in the preparation of the active product of the desired concentration and covered with larvae of green rice cicadas (Nephotettix cincticeps), as long as the leaves are still moist. After the desired time the destruction is determined in%. In this case 100% means that all the cicadas were destroyed; 0% means that no cicada was destroyed. In this test, for example, the compounds according to the following preparation examples Ia-1, Ib-1, Ic-1, Ib-2, Ic-2, Ia-4, Ib-8 and Ic-4 at a concentration Example of active product 0.1% destruction 100% after 6 days.

Example E Test are Spodoptera. Solvent: 7 parts by weight of dimethylformamide Emulsifier: 1 part by weight of alkylaryl polyglycol ether In order to obtain a suitable active product preparation, 1 part by weight of the active compound is mixed with the indicated amount of solvent and with the indicated amount of emulsifier and dilute the concentrate with water to the desired concentration. Cabbage leaves (Brassica olerácea) are treated by being dipped into the preparation of the active compound of the desired concentration and covered with caterpillars of the »10 nocturnal moth (Spodoptera frugiperda), as long as the leaves are still wet. After the desired time, the effect in% is determined. In this case 100% means that all the larvae were destroyed; 0% means that no larva was destroyed. ? In this test they show, for example, the compounds according to the following preparation examples I-b-2, I-a-4, I-b-8 and I-b-10 at an exemplary concentration of the active product of 0.1% one destruction of > 90% after 7 days.

Example F Test with Myzus 25 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 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.

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

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

In this test, for example, the compounds according to the following preparation examples Ia-1, Ia-3, Ib-2, Ic-2, Ia-4 and Ic-4 are shown at an exemplary concentration of the active product of 0.1%. destruction of > 90% after 6 days.

It is noted that in relation to this date, the best method known by the applicant to carry out the present invention, is the conventional one for the manufacture of the objects or products to which it refers. Having described the invention as above, the content of the following is claimed as property:

Claims (13)

1. Compounds of the formula (I- characterized in that: X means halogen, alkyl, alkenyl, alkynyl, alkoxy, alkenyloxy alkylthio, alkylsulfinyl, alkylsulfonyl, haloalkyl, haloalkenyl, haloalkoxy, haloalkenyloxy, nitro, cyano or means phenyl, phenoxy, phenylthio, benzyloxy or benzylthio respectively substituted, Y means halogen, alkyl, alkenyl, alkynyl, alkoxy, alkenyloxy alkylthio, alkylsulfinyl, alkylsulfonyl, haloalkyl, haloalkenyl, haloalkoxy, haloalkenyloxy, nitro or cyano, Z means halogen, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, alkoxy, alkenyloxy, haloalkoxy, haloalkenyloxy, nitro or cyano, n means 0, 1, 2 or 3, A means hydrogen, means alkyl, alkenyl, alkynyl, alkoxyalkyl, polyalkoxyalkyl or alkylthioalkyl respectively substituted, if appropriate by halogen, means saturated or unsaturated cycloalkyl, given substituted, in which at least one atom of the ring is replaced, if appropriate, by a heteroatom, or means aryl, arylalkyl or hetaryl substituted, where appropriate, by halogen, by alkyl, by haloalkyl, by alkoxy, by haloalkoxy, by cyano or by nitro, which may be substituted by phenoxy, by benzyloxy or by substituted hetaryloxy B means hydrogen or means alkyl, alkoxyalkyl respectively substituted, if appropriate, by halogen, or A and B together with the carbon atom, to which they are linked mean a saturated or unsaturated ring, which in case contains a heteroatom, unsubstituted or substituted, 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, M means oxygen or sulfur, R1 means alkyl, alkenyl, alkoxyalkyl, alkylthioalkyl or polyalkoxyalkyl respectively substituted, if appropriate, by halogen or means cycloalkyl optionally substituted by halogen, by alkyl or by alkoxy, which may be interrupted by at least one heteroatom or means phenyl, phenylalkyl, hetaryl, phenoxyalkyl or hetaryloxyalkyl respectively substituted, where appropriate, R2 means alkyl, alkenyl, alkoxyalkyl or polyalkoxyalkyl respectively substituted by halogen or means cycloalkyl, phenyl or benzyl respectively substituted, R3, R4 and R5, independently of each other, mean alkyl, alkoxy, alkylamino, dialkylamino, alkylthio, alkenylthio or cycloalkylthio substituted, where appropriate, by halogen or means phenyl, benzyl, phenoxy or phenylthio substituted, respectively, and R6 and R7, respectively independently of one another, they mean hydrogen, they mean alkyl, cycloalkyl, alkenyl, alkoxy, alkoxyalkyl respectively substituted, if appropriate, by halogen, phenyl is, if appropriate, substituted benzyl optionally substituted, or together with the N atom, with which they are linked, they mean a cycle that is interrupted if necessary by oxygen or by sulfur.

2. Compounds of the formula (I) according to claim 1, characterized in that: X represents halogen, alkyl with 1 to 6 carbon atoms, alkenyl with 2 to 6 carbon atoms, alkynyl with 2 to 6 carbon atoms, alkoxy with 1 to ß 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, halogenoalkenyloxy with 3 to 6 carbon atoms, nitro, cyano or represents phenyl, phenoxy, phenylthio, benzyloxy or benzylthio each substituted by halogen, if appropriate , by alkyl with 1 to 6 carbon atoms, by alkoxy with 1 to 6 carbon atoms, with haloalkyl with 1 to 4 carbon atoms, by halogenalkoxy with 1 to 4 carbon atoms, by nitro or by cyano. represents hydrogen halogen, alkyl with 1 to 6 carbon atoms, alkenyl with 2 to 6 carbon atoms, alkynyl with 2 to 6 carbon atoms, alkoxy with 1 to 6 carbon atoms, 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 atoms of carbon, halogenalkenyloxy with 3 to 6 carbon atoms, nitro or cyano, represents 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, halogenoalkenyloxy with 3 to 6 carbon atoms, nitro or cyano, n preferably represents 0, 1, 2 or 3, A represents hydrogen or represents alkyl with 1 to 12 carbon atoms, alkenyl with 2 to 8 carbon atoms, alkynyl with 2 to 8 carbon atoms, alkoxy with 1 to 10 carbon atoms-alkyl with 1 to 8 carbon atoms, C 1 -C 8 -alkoxy-C 1 -C 8 -alkyl or C 1 -C 10 -alkylthio-C 1 -C 6 -alkyl substituted, if appropriate, by halogen, represents cycloalkyl with 3 a 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 a ring member is replaced, if appropriate, by an oxygen or by sulfur or represents phenyl or naphthyl, hetaryl containing 5 to 6 ring atoms, preferably alkyl having 1 to 6 carbon atoms, or represents furanyl, pyridyl, imidazolyl, triazolyl, pyrazolyl, pyrimidyl, thiazolyl or thienyl or phenyl or naphthyl, respectively substituted in in the case given by halogen, by alkyl having 1 to 6 carbon atoms, by haloalkyl with 1 to 6 carbon atoms, by alkoxy with 1 to 6 carbon atoms, by haloalkoxy with 1 to 6 carbon atoms, by cyano or nitro, optionally substituted by halogen, by alkyl with 1 to 4 carbon atoms, by alkoxy with 1 to 4 carbon atoms, by halogenalkyl with 1 to 2 carbon atoms, by halogenalkoxy with 1 to 2 carbon atoms, cyano or by nitro, B represents hydrogen or represents alkyl with 1 to 12 carbon atoms or alkoxy with 1 to 8 carbon atoms-alkyl having 1 to 6 carbon atoms, respectively substituted, if appropriate, by halogen, or A, B and the carbon atom, with they are linked cycloalkyl with 3 to 10 carbon atoms saturated or unsaturated, (particularly cycloalkyl with 5 to 8 carbon atoms), which is replaced if necessary a ring member by oxygen or sulfur and which is optionally mono- or polysubstituted by alkyl with 1 to 8 carbon atoms, by cycloalkyl with 3 to 10 carbon atoms, by halogenalkyl with 1 to 8 carbon atoms, by alkoxy with 1 to 8 carbon atoms, by alkylthio with 1 to 8 carbon atoms, by halogen or by phenyl or A, B and the carbon atom with which they are linked represent cycloalkyl with 5 to 8 carbon atoms or cycloalkenyl with 5 to 8 carbon atoms, in which two substituents together with the carbon atoms, with which they are bound, they represent alkanediyl having 5 to 6 carbon atoms, alkenodiyl having 5 to 6 carbon atoms or alkanediyenyl with 6 carbon atoms substituted, where appropriate, by alkyl with 1 to 6 carbon atoms, alkoxy with 1 to 6 carbon atoms or by halogen, a methylene group being optionally replaced by oxygen or by sulfur. G represents hydrogen (a) or represents one of the groups R4 / R6 \ E (f) / R5 (?), - N (g). / L R7 in which E represents an equivalent of metal ion or an ammonium ion, L represents oxygen or sulfur, and klO M represents oxygen or sulfur. R1 represents 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 or represents cycloalkyl with 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 at least one methylene group is replaced by oxygen or sulfur, represents phenyl optionally substituted by halogen, by cyano , by nitro, by alkyl with 1 to 6 carbon atoms, by alkoxy with 1 to 6 carbon atoms, haloalkyl with 1 to 6 carbon atoms, by halogenalkoxy with 1 to 6 carbon atoms, by alkylthio with 1 to 6 atoms of carbon or by alkylsulfonyl with 1 to 6 carbon atoms carbon, represents phenyl-C 1 -C 6 -alkyl optionally substituted by halogen, by nitro, by cyano, by C 1 -C 6 -alkyl, by C 1 -C 6 -alkoxy, by haloalkyl with 1 to 6 carbon atoms or to halogenalkoxy with 1 to 6 carbon atoms, represents hetaryl with 5 or 6 members, optionally substituted by halogen, or by alkyl with 1 to 6 carbon atoms, represents f-xyloxy with 1 to 6. carbon atoms optionally substituted by halogen or by alkyl having 1 to 6 carbon atoms or represents 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, R2 represents 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- > The alkyl having 2 to 8 carbon atoms substituted, if appropriate, by halogen represents 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. 15 carbon atoms, or f represents phenyl or benzyl, respectively substituted, if appropriate, by halogen, by cyano, by nitro, by alkyl with 1 to 6 carbon atoms, by alkoxy with 1 to 6 carbon atoms, 20 haloalkyl with 1 to 6 carbon atoms or for halogenalkoxy with 1 to 6 carbon atoms, R represents alkyl with 1 to 8 carbon atoms substituted, if appropriate, by halogen or represents Phenyl or benzyl substituted, if appropriate, by halogen, by alkyl with 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; carbon, by cyano or by nitro. R 4 and R 5 represent, independently of each other, alkyl having 1 to 8 carbon atoms, alkoxy with 1 to 8 carbon atoms, alkylamino with 1 to 8 carbon atoms, di- (alkyl with 1 to 8 carbon atoms) amino, alkylthio with 1 to 8 carbon atoms, alkenylthio with 2 to 8 carbon atoms, cycloalkylthio with 3 to 7 carbon atoms substituted, where appropriate, by halogen or represent phenyl, phenoxy or phenylthio each substituted, if 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 halogenalkylthio with 1 to 4 carbon atoms, by alkyl with 1 to 4 carbon atoms or by halogen alkyl with 1 to 4 carbon atoms and R6 and R7 represent, independently of one another, hydrogen, represent 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 with 1 to 8 carbon atoms substituted, if appropriate, by halogenrepresent 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, 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 represent an alkylene radical having 3 to 6 carbon atoms, in which case it is replaced by a methylene group by oxygen or by sulfur.

3. Compounds of the formula (I) according to claim 1, characterized in that: represents fluorine, chlorine, bromine, alkyl with 1 to 4 carbon atoms, alkoxy with 1 to 4 carbon atoms, halogenalkyl with 1 to 4 carbon atoms, halogenalkoxy having 1 to 4 carbon atoms, nitro, cyano or represents phenyl or benzyl substituted respectively by fluorine, chlorine, bromine, alkyl with 1 to 4 carbon atoms, alkoxy with 1 to 4 carbon atoms, halogenalkyl with 1 to 2 carbon atoms, for halogenalkoxy with 1 to 2 carbon atoms, for nitro or for cyano, Y represents hydrogen, fluorine, chlorine, bromine, alkyl with 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, Z represents 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 represents 0, 1, 2 or 3, A represents hydrogen, represents alkyl with 1 to 10 carbon atoms or alkoxy with 1 to 8 carbon atoms-alkyl having 1 to 6 carbon atoms substituted, respectively, respectively by fluorine or chlorine, represents cycloalkyl with 3 to 7 carbon atoms carbon optionally substituted by fluorine, chlorine, alkyl with 1 to 4 carbon atoms or alkoxy with 1 to 4 carbon atoms, or represents phenyl, furanyl, pyridyl, imidazolyl, triazolyl, pyrazolyl, pyrimidinyl, triazolyl, thienyl or phenyl-C 1 -C 4 -alkyl substituted respectively by fluorine, by chlorine, by bromine, by C 1 -C 4 -alkyl, by haloalkyl with 1 to 4 C atoms, by alkoxy with 1 4 carbon atoms, by haloalkoxy with 1 to 4 carbon atoms, by cyano or by nitro. B represents hydrogen or represents alkyl having 1 to 10 carbon atoms or alkoxy having 1 to 6 carbon atoms-alkyl having 1 to 4 carbon atoms substituted, respectively, by fluorine or chlorine or A, B and the carbon atom to which they are attached represent cycloalkyl with 5 to 8 carbon atoms saturated or unsaturated, in which a ring member is optionally replaced by oxygen or by sulfur and which is substituted in case given by alkyl having 1 to 6 carbon atoms, by cycloalkyl with 3 to 8 carbon atoms, by halogenalkyl with 1 to 3 carbon atoms, by alkoxy with 1 to 6 carbon atoms, by alkylthio with 1 to 6 carbon atoms carbon, fluorine, chlorine or phenyl or A, B and the carbon atom, with which they are linked, represent cycloalkyl with 5 to 6 carbon atoms or cycloalkenyl with 5 to 6 carbon atoms, in which two substituents together with the carbon atoms, with which they are linked they represent alkanediyl having 5 to 6 carbon atoms, alkenodiyl having 5 to 6 carbon atoms or alkanedi-diyl with 6 carbon atoms substituted, where appropriate, by alkyl with 1 to 5 carbon atoms, by alkoxy with 1 to 5 carbon atoms , by fluorine, by chlorine or by bromine, where a methylene group is replaced by oxygen or sulfur. G represents hydrogen (a) represents one of the groups (d), in which E represents a metal ion equivalent or an ammonium ion, L represents oxygen or sulfur and M represents oxygen or sulfur. R1 represents alkyl with 1 to 16 carbon atoms, alkenyl with 2 to 16 carbon atoms, alkoxy with 1 to 6 carbon atoms-alkyl with 1 to 6 carbon atoms, alkylthio with 1 to 6 carbon atoms-alkyl with 1 with 6 carbon atoms, poly-alkoxy having 1 to 6 carbon atoms-alkyl having 1 to 6 carbon atoms substituted, respectively, by fluorine or chlorine or represents cycloalkyl having 3 to 7 carbon atoms, optionally substituted by fluorine, chlorine, alkyl with 1 to 5 carbon atoms or alkoxy with 1 to 5 carbon atomswhere one or two methylene groups, not directly adjacent, are replaced by oxygen or sulfur, represents 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 halogenalkyl with 1 to 3 carbon atoms, by halogenalkoxy with 1 to 3 carbon atoms, by alkylthio with 1 to 4 carbon atoms or by alkylsulfonyl with 1 at 4 carbon atoms, represents phenyl-C 1 -C 4 -alkyl 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, represents pyrazolyl, thiazolyl, pyridyl, pyrimidyl, furanyl, thienyl, respectively substituted, respectively, by fluorine, chlorine, bromine or alkyl with 1 to 4 carbon atoms, repre phenoxy-C1-C5alkyl optionally substituted by, by fluorine, by chlorine, by bromine or by alkyl with 1 to 4 carbon atoms, or represents pyridyloxy-alkyl with 1 to 5 carbon atoms, pyrimidyloxy -alkyl with 1 to 5 carbon atoms or thiazolyloxy-alkyl having 1 to 5 carbon atoms substituted, where appropriate, by fluorine, chlorine, bromine, amino or alkyl with 1 to 4 carbon atoms. 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 atoms-alkyl with 2 to 6 carbon atoms respectively substituted, if appropriate, by fluorine or chlorine, represents 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 represents phenyl or benzyl substituted respectively by fluorine, by chlorine, by bromine, by cyano, by nitro, by alkyl with 1 to 4 carbon atoms, by alkoxy with 1 to 3 carbon atoms, by halogenalkyl with 1 to 3 carbon atoms or by halogenalkoxy with 1 to 3 carbon atoms, R represents alkyl with the carbon atoms preferably substituted by fluorine or chlorine or represents phenyl or benzyl, optionally substituted, respectively, by fluorine, chlorine, bromine, alkyl with 1 to 5 carbon atoms, alkoxy with 1 to 5 carbon atoms, for halogen alkyl with 1 to 3 carbon atoms, for halogenalkoxy with 1 to 3 carbon atoms, for cyano or for nitro, R and R, independently of each other, represent 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) amino, alkylthio with 1 to 6 carbon atoms, alkenylthio with 3 to 4 carbon atoms, cycloalkylthio with 3 to 6 carbon atoms substituted, where appropriate, by fluorine or chlorine, or represent 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 haloalkylthio with 1 to 3 atoms of carbon, by alkyl with 1 to 3 carbon atoms or by haloalkyl with 1 to 3 carbon atoms. R6 and R7 represent, independently of one another, hydrogen, represent alkyl with 1 to 6 carbon atoms, cycloalkyl with 3 to 6 carbon atoms, alkoxy with 1 to 6 carbon atoms, alkenyl with 3 to 6 carbon atoms, alkoxy with 1 to 6 carbon atoms-alkyl having from 1 to 6 carbon atoms substituted, if appropriate, by halogen, represents phenyl optionally substituted by halogen, by halogenalkyl with 1 to 5 carbon atoms, by alkyl with 1 to 5 carbon atoms; carbon, or by alkoxy having 1 to 5 carbon atoms, represent benzyl optionally substituted by halogen, by alkyl with 1 to 5 carbon atoms, by halogenalkyl with 1 to 5 carbon atoms or by alkoxy with 1 to 5 carbon atoms; carbon, or together they represent an alkylene radical having 3 to 6 carbon atoms, in which, if appropriate, a carbon atom is replaced by oxygen or by sulfur.

4. Compounds of the formula (I) according to claim 1, characterized in that: X represents fluorine, chlorine, bromine, methyl, ethyl, propyl, iso-propyl, methoxy, propoxy, iso-propoxy, trifluoromethyl, difluoromethoxy, trifluoromethoxy, nitro or cyano, Y represents hydrogen, fluorine, chlorine, bromine, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, tert-butyl, methoxy, ethoxy, propoxy, iso-propoxy, allyloxy, methaloxy, trifluoromethyl , difluoromethoxy, trifluoromethoxy, nitro or cyano, Z represents fluorine, chlorine, bromine, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, tert-butyl, methoxy, ethoxy, propoxy, iso-propoxy, difluoromethoxy, trifluoromethyl, trifluoromethoxy, nitro or cyano, n represents 0, 1, 2 or 3,

A represents hydrogen or represents alkyl with 1 to 8 carbon atoms or alkoxy with 1 to 6 carbon atoms-alkyl having 1 to 4 carbon atoms substituted, respectively, respectively by fluorine or chlorine, represents cycloalkyl with 5 to 6 atoms substituted optionally by fluorine, chlorine, methyl, ethyl, isopropyl, tert-butyl, ethoxy or methoxy, or represent phenyl or benzyl each of which optionally substituted by fluorine, by chlorine, by methyl, by ethyl, by isopropyl, by tert-butyl, by methoxy, by ethoxy, by trifluoromethyl, by difluoromethoxy, by trifluoromethoxy, cyano or nitro. B represents hydrogen or represents alkyl with 1 to 8 carbon atoms or alkoxy with 1 to 4 carbon atoms-alkyl having 1 to 2 carbon atoms each of which is optionally substituted by • 5 fluorine, or A, B and the carbon atom, to which they are attached, represent cycloalkyl with 5 to 6 carbon atoms saturated or unsaturated, in which is optionally replaced a methylene group by oxygen or by sulfur and which is optionally substituted by methyl , ethyl, iopropyl, tert-butyl, trifluoromethyl, methoxy, ethoxy, fluorine, chlorine or phenyl or A, B and the carbon atom, to which they are attached, represent cycloalkyl with 5 to 6 carbon atoms or cycloalkenyl with 5 a 6 carbon atoms, in which two substituents together with the atoms of

The carbon atoms to which they are attached represent alkanediyl having 5 to 6 carbon atoms, alkenodiyl having 5 to 6 carbon atoms or alkenodienediyl having 6 carbon atoms. G represents hydrogen (a) represents one of the groups in which E represents an equivalent of metal ion or an ammonium ion, L represents oxygen or sulfur and M represents oxygen or sulfur, R1 represents alkyl with 1 to 14 carbon atoms, alkenyl with 2 to 4 carbon atoms, alkoxy with 1 to 6 carbon atoms-alkyl with 1 to * 6 carbon atoms, alkylthio with 1 to 4 carbon atoms - alkyl with 1 to 6 carbon atoms or poly-alkoxy with 1 to 4 carbon atoms-alkyl having 1 to 4 carbon atoms substituted, where appropriate, by fluorine or chlorine or optionally fluorine, chlorine, methyl, ethyl, propyl, -propyl, butyl, i-butyl, tert-butyl, methoxy, ethoxy, propoxy, or iso-propoxy substituted with cycloalkyl having 3 to 6 carbon atoms, in which one or two methylene groups, not directly adjacent, are optionally replaced, by oxygen or by sulfur, represents phenyl optionally substituted by fluorine, chloro-, bromo-, methyl-, ethyl-, propyl-, i-propyl-, methoxy-, ethoxy-, trifluoromethyl-, trifluoromethoxy-, methylthio-, ethylthio -, methylsulfonyl or ethylsulfonyl, represents benzyl fluorine-, chloro-, bromo-, methyl-, ethyl-, propyl-, i-propyl-, methoxy-, ethoxy-, trifluoromethyl- or trifluoromethoxy-, represents furanyl, thienyl, pyridyl, pyrimidyl, thiazolyl or pyrazolyl, each of which is optionally substituted by fluorine, chlorine, bromine, methyl or ethyl, represents phenoxy-C 1-4 alkyl optionally substituted by fluorine, chloro-, methyl- or ethyl or represents pyridoxy-alkyl having 1 to 4 carbon atoms, pyrimidyloxy-C 1-4 -alkyl or triazolyloxy-alkyl with 1 to 4 carbon atoms, each of which is optionally substituted by fluorine, chlorine, ammonium, methyl or ethyl, R2 represents alkyl with 1 to 14 carbon atoms, alkenyl with 2 to 14 carbon atoms, alkoxy with 1 C4-C4-alkyl having 2 to 6 carbon atoms or poly-alkoxy with 1 to 4 carbon atoms-alkyl having 2 to 6 carbon atoms, substituted respectively by fluorine or chlorine, represents cycloalkyl with 3 to 6 carbon atoms carbon atoms optionally substituted p or fluorine, by chlorine, by methyl, by ethyl, by isopropyl or by methoxy, or represents phenyl or benzyl optionally substituted respectively by fluorine, by chlorine, by cyano, by nitro, by methyl, by ethyl, by propyl, by i-propyl, by methoxy, by ethoxy, by trifluoromethyl or by trifluoromethoxy. R3 represents methyl, ethyl, propyl, isopropyl, optionally substituted by fluorine or chlorine, or represents phenyl or benzyl, optionally substituted by fluorine, by chlorine, by bromine, by methyl, by ethyl, by propyl, by iso-propyl, by tert-butyl, by methoxy, ethoxy, isopropoxy, tert-butoxy, trifluoromethyl, trifluoromethoxy, cyano or nitro, R4 and R5, independently of each other, represent 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 to 4 carbon atoms) amino, alkylthio having 1 to 4 carbon atoms, respectively substituted, if appropriate, by fluorine or chlorine, or representing phenyl, phenoxy or phenylthio substituted, where appropriate, by fluorine, chlorine, bromine, nitro, cyano, alkoxy, 1 to 2 carbon atoms, for fluoroalkoxy with 1 to 2 carbon atoms, for alkylthio with 1 to 2 carbon atoms, for fluoroalkylthio with 1 to 2 carbon atoms or alkyl with 1 to 3 carbon atoms. R6 and R7, independently of one another, represent hydrogen, represent alkyl with 1 to 4 carbon atoms, cycloalkyl with 3 to 6 carbon atoms, alkoxy with 1 to 4 carbon atoms, alkenyl with 3 to 4 carbon atoms or alkoxy with 1 to 4 carbon atoms-alkyl having 1 to 4 carbon atoms, optionally substituted by fluorine or chlorine, optionally substituted phenyl represented by fluorine, chlorine, bromine, halogen with 1 to 4 carbon atoms, alkyl with 1 to 4 carbon atoms or alkoxy with 1 to 4 carbon atoms, represent benzyl optionally substituted by fluorine, chlorine, bromine, alkyl with 1 to 4 carbon atoms, halogenalkyl with 1 to 4 carbon atoms or alkoxy with 1 to 4 carbon atoms carbon or together represent an alkylene radical with 5 to 6 carbon atoms in which optionally a methylene group is replaced by oxygen or sulfur. Process for the preparation of the formula (I) according to claim 1 / characterized in that (A) esters of N-acylamino acid of the formula (II) wherein A, B, D, X, Y, Z and n are each as defined above and R8 represents alkyl, they are condensed intramolecularly in the presence of a diluent and in the presence of a base and the resulting compounds of the formula (the) wherein A, B, X, Y, Z and n are each as defined in the foregoing, if any if subsequently reacted (B) a) with acyl halides of the formula (III) wherein R1 is as defined above in the claim 1 and Hal represents halogen or ß) is reacted with anhydrides of carboxylic acids of the formula (IV) R ^ CO-O-CO-R1 (IV) wherein R1 is as defined above, if appropriate in the presence of a diluent and, if appropriate, in the presence of an acid-accepting agent; or is reacted (C) with esters of chloroformic acid or thiol esters of chloroformic acid of the formula (V) R -M-CO-C1 (V) wherein R2 and M are each as defined in claim 1, if appropriate in the presence of a diluent and, if appropriate, in the presence of an acid-accepting agent; or they are reacted (D) with esters of chloromonothioformic acid or with esters of chlorodithioformic acid of the formula (VI) wherein M and R2 are each as defined in claim 1, if appropriate in the presence of a diluent and, if appropriate, in the presence of an acid-accepting agent; or are reacted (E) with sulfonyl chlorides of the formula (VII) R -S02-C1 (Vil) wherein R3 is as defined in claim 1, case giving in the presence of a diluent and, if appropriate, in the presence of an acid-accepting agent, or is reacted (F) with phosphorus compounds of the formula VIII), wherein L, R4 and R5 are each as defined in claim 1 and Hal represents halogen, if appropriate in the presence of a diluent and, if appropriate, in the presence of an acid-accepting agent, or reacted ( G) with metal compounds or with amines of the formulas (IX) or (X), in which Me represents a mono or divalent metal, t represents the number 1 or 2 and R10, R11, R12, independently represent each other hydrogen or alkyl, if given in the presence of a diluent, or are reacted (H ) with carbamidyl chlorides or with thiocarba idyl chlorides of the formula (XI) wherein L, R6, R7 are each as defined in claim 1, if appropriate in the presence of a diluent and, if appropriate, in the presence of an acid-binding agent. Compounds of the formula (XII characterized in that: A and B are each as defined in accordance with claim 1, and R9 represents alkyl,

7. Compounds of the formula (XV) characterized in that: A, B, X, Y Z and n are each as defined in accordance with claim 1.

8 Compounds of the formula (XVI) characterized because: A, B, 'X, Y, Z and n are each as Z defined in accordance with claim 1.

9. Pesticides and herbicides, characterized in that they have a content in at least one compound of the formula (I) according to claim 1.

10. Use of compounds of the formula (I) according to claim 1, for the control against pests and against the undesirable growth of plants.

11. Method for controlling pests, characterized in that compounds of the formula (I) according to claim 1 are allowed to act on the pests, on the undesirable growth of the plants and / or on their environment.

12. Process for the preparation of pesticides and herbicides, characterized in that compounds of the formula (I) according to claim 1 are mixed with extenders and / or with surfactants.

13. Use of compounds of the formula (I) according to claim 1, for the preparation of pesticides and herbicides.