MXPA00012631A - 1,3-oxazoline and 1,3-thiazoline derivatives, method for producing the same and their use as pesticides - Google Patents

Abstract

The invention relates to 1,3-oxazoline and 1,3-thiazoline derivatives having formula (I), wherein the symbols have the following meanings:A represents phenyl, pyridyl, pyrimidinyl, pyrazinyl, pyrazolyl or thienyl;E represents a single bond, (C1-C4)-alkylene, -O-CH2- or CH2-O-;G represents a radical of group (a), (b), (c) and (d) and Z represents oxygen or sulfur. Compounds of formula (I) exhibit very good acaricidal and insecticidal effect especially as regards spectrum of activity and effectiveness.

Description

DERIVATIVES OF 1, 3-OXAZOLINA AND 1.3-TIAZOLINA, ITS PREPARATION AND ITS USE AS PESTICIDES DESCRIPTIVE MEMORY The invention relates to diaryl-1,3-oxazolines and diaryl-1,3-thiazolines, to processes for their preparation, to compositions comprising them, and to their use for controlling animal pests, in particular insects, mites, ectoparasites and helminths. . Due to their biological activity, some 1,3-oxazolines and 1,3-thiazolines are suitable for controlling animal pests (see, for example, EP-A-0 345 775 and EP-A-0 432 661; A-97/06153; WO-A-93/24470 and WO-A-95/04726). However, the level of action and / or duration of action of these prior art compounds is not completely satisfactory in all fields of application, in particular against certain organisms or when applied at low concentrations. Because modern pesticides must meet a wide range of demands, for example regarding level, duration and spectrum of action, spectrum of use, toxicity, combination with other active substances, combination with formulation or synthesis aids, and because the existence of resistance is possible, the development of such substances can not be considered as finished, and there is continuously a high demand ______________ A ^ MáMÜB. ^^^ ÜliÉÉ? of novel compounds that are advantageous over the known compounds, at least insofar as some aspects are concerned. It is an object of the present invention to provide compounds that broaden the spectrum of pesticides in various aspects. This objective, and other objectives that are not explicitly mentioned and that can be deduced or concluded from the ideas discussed in the present invention, are solved with 1,3-oxazoline and 1,3-thiazoline derivatives of the formula (I) wherein the symbols have the following meanings: A is phenyl, pyridyl, pyrimidinyl, pyrazinyl, pyrazolyl or thienyl, each of the aforementioned groups being optionally substituted with one or more, preferably one, two or three, X radicals; X is the same as or different from a) halogen, cyano, nitro; b) C 1 -C 4 alkyl, C 2 -C 4 alkenyl, C 2 -C 4 alkynyl, C 1 -C 4 alkoxy, C 1 -C 4 alkylthio, C 1 -C 4 alkylsulfinyl, C 3 -C 8 cycloalkyl, C 4 -C 8 cycloalkenyl, phenyl, the radicals of group b being optionally substituted with one or more, preferably one, two or three, radicals which are selected from the group consisting of halogen, cyano, _ ^^^ _ U «IMI C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy and C1-C4 haloalkoxy; E is a single bond, C1-C4 alkylene, -O-CH2- or -CH2-O-; G is a radical selected from the group consisting of: Z is oxygen or sulfur; R1, R2 and R3 are identical or different, hydrogen, halogen, C1-C4 haloalkyl, C1-C4 alkyl, C? -C4 alkoxy, C1-C4 haloalkoxy or cyano; R4 is hydrogen or C? -C8 alkyl group, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, C3-C8 cycloalkenyl, C4-C10 cycloalkylalkyl or C-C2 phenylalkyl? , each of the aforementioned groups being optionally substituted with one or more substituents which are selected from the group consisting of halogen, C 1 -C 4 alkyl, C 1 -C 3 haloalkyl, C 1 -C 4 alkoxy, C 1 -C 3 halogenoalkoxy , x - j - * - •? - • - • - - - 1 - 1 - C 1 -C 3 alkylthio, C 3 -C 8 cycloalkyl, C 7 -C 2 phenylalkoxy, C 2 -C 4 alkylcarbonyl, alkoxycarbonyl, C 2 -C 6 monoalkylcarbonyl and dialkylamino- carbonyl of C3-C9, cyano and tri-alkylsilyl of C1-C4; R5 and R6 are the same as or different from a) hydrogen, halogen, cyano, C2-C5 alkylcarbonyl formyl, C2-C8 alkoxycarbonyl, C3-C9 monoalkylcarbonyl and dialkylaminocarbonyl, b) CrC8 alkyl, C3-C8 cycloalkyl, cycloalkenyl C4-C8, C 1 -C 8 alkoxyalkyl, CrC 8 alkylthio, Cs alkylsulfinyl, CrC 8 alkylsulfonyl, NR 7 R 8, phenyl, phenoxy, phenylalkyl C 12, C7-C2-phenylalkoxy, heterocyclyl, preferably C4-C7-oxacycloalkyl, C4-C7-oxacycloalkenyl, C4-C-cycloalkyl, C4-C-cycloalkenyl, pyridyl, pyrimidinyl, pyrazinyl, furanyl, thienyl, pyrrolyl, imidazolyl , pyrazolyl, triazolyl, thiazolyl, oxadiazolyl, heterocyclyloxy derivatives, heterocyclyl-C1-C4 alkoxy, heterocyclylalkyl of C3-C2, each of the groups b being optionally substituted with one or more, preferably one to three radicals that are selected from the group consisting of halogen, C 1 -C 4 alkyl, C 1 -C 3 haloalkyl, C 1 -C 3 alkoxy, C 1 -C 3 halogenoalkoxy, C 1 -C 3 alkylthio, NR 7 R 8, C 2 -C 5 alkylcarbonyl, alkoxycarbonyl C2-C8, C3-C9 monoalkylcarbonyl and dialkylaminocarbonyl, cyano and trialkylsilyl C1-C4; c) C 1 -C 8 alkoxy, each of the groups c being optionally substituted with one or more, preferably one to three, radicals which are selected from the group consisting of halogen, C 1 -C 3 alkylthio, NR 7 R 8, alkylcarbonyl C2-C5, C2-C8 alkoxycarbonyl, C3-C9 monoalkylcarbonyl and dialkylaminocarbonyl, cyano and trialkylsilyl of C1-C4; od) R5 and R6 together preferably form a monicyclic ring which originates by linking two of the groups mentioned in b), preferably C3-C5 alkylene, C2-C4 alkyleneoxy, C1-C3 alkylenedioxy, alkylene C2-C4 or alkylenethio of C2-C4; R7 and R8 are identical or different a) hydrogen; b) CrC8 alkyl, C3-C8 cycloalkyl, C7-C12 phenylalkyl, C6-C6 alkylcarbonyl, CrC6 alkylsulfonyl which are optionally substituted with one or more, preferably one to three radicals which are selected from the group consists of halogen, C 1 -C 4 alkyl, C 1 -C 3 haloalkyl, C 1 -C 4 alkoxy, C 1 -C 3 halogenoalkoxy, C 1 -C 3 alkylthio, C 1 -C 3 alkylamino, C 1 -C 3 dialkylamino, C 3 cycloalkyl -C8, cyano and trialkyl (CrC4); or c) R7 and R8 together are C3-C7 alkylene, oxa-alkylene, aza-alkylene or C3-C7 thia-alkylene, C3-C-alkylenecarbonyl, or C3-C7alkylene sulfonyl; their pure isomers (optical and geometric isomers) and mixtures of these isomers, their N-oxides and their salts which are suitable for use as pesticides. "* < ~ * '-.» »« &> • -> - •>' Surprisingly the compounds of the formula (I) have a better acaricidal and insecticidal activity with respect to the spectrum of action and the potency of the known 1,3-oxazoline derivatives and 1,3-thiazoline The symbols in the formula (I) preferably have the following meanings: A is preferably phenyl or pyridyl, especially preferred phenyl. preferably a) halogen, cyano, nitro or 10 b) C 1 -C 4 alkyl, C 1 -C 4 alkenyl, C 1 -C 4 alkynyl, C 1 -C 4 alkoxy, C 1 -C 4 alkylthio, C 1 -C 4 alkylsulfinyl, cycloalkyl of C3-C7, C4-C8 cycloalkenyl, the radicals of group b being optionally substituted with one or more, preferably one, two or three radicals which are selected from the group consisting of halogen, cyano, C1-C4 alkoxy and C 1 -C 4 halogenoalkoxy; X is especially preferred halogen, C 1 -C 4 alkyl, C 1 -C 3 haloalkyl, C 1 -C alkoxy 4 or C-1-C3 halogenoalkoxy. E is preferably a single bond or -CH2-, especially preferably a single bond. 20 G is preferably - "-" - - '• *' • • J '"- * - * - - -' - '' • * '"' - '- * "- a ^^ - ^ - especially preferred 3-pyridyl. Z is preferably oxygen R 1, R 2, R 3 are preferably H, halogen, C 4 haloalkyl, C 1 -C 4 alkyl, C 1 -C 4 alkoxy, C 1 -C 4 halogenoalkoxy or cyano, especially preferred H, halogen, C1-C4 haloalkyl, d-C4 alkyl, C1-C4 alkoxy, C1-C4 haloalkoxy, R4 is preferably H or C-?-C8 alkyl which is optionally substituted with one or more, preferably 1 to 3 radicals which are selected from the group consisting of halogen, C1-C4 alkyl, C1-C3 halogenoalkyl, C1-C4 alkoxy, C-1-C3 haloalkoxy, C1-C3 alkylthio, C3- cycloalkyl C8, cyano or trialkylsilyl of C 1 -C 4, R 5, R 6 are preferably a) H, halogen, cyano, b) CrC 8 alkyl, C 3 -C 8 cycloalkyl, C 4 -C 8 cycloalkenyl, C 12 alkylthio C8, C?-C8 alkylsulfinyl, C--C8 alkylsulfonyl, C fen-phenyl phenylalkyl, phenylalkoxy of C -C ?2, C4-C oxycycloalkyl or C4-C-oxacycloalkenyl, the groups b being optionally substituted with one or more, preferably 1 to 3, radicals which are selected from the group consisting of halogen, C1-6alkyl C4, C1-C3 halogenoalkyl, C.-C3 alkoxy, C.sub.1 -C3 halogenoalkoxy, C-1-C3 alkylthio and cyano, c) C.-C8 alkoxy which may be optionally substituted with one or more, preferably 1 to 3 radicals which are selected from the group consisting of halogen, C1-C3 alkylthio and cyano. __iw_a_i_i_á _ »_ i_t_i_t_t_i_. ^^^^ t ^^^? ^ a ?? R5, R6 are preferably especially a) H, halogen, cyano, b) Ci-Cs alkyl, C---C8 alkoxy, C3-C8 cycloalkyl, C4-C8 cycloalkenyl, CrC8 alkylthio, alkylsulfinyl of CrC8, C -? - C8 alkylsulfonyl, C -? 2 phenylalkyl or C - C2 phenylalkoxy, the b groups being substituted with one or more, preferably 1 to 3 radicals which are selected from the group consisting of halogen , C 1 -C 4 alkyl, C 1 -C 3 halogenoalkyl and cyano. In the above formula, it should be understood that "halogen" means a fluorine, chlorine, bromine or iodine atom; the term "C 1 -C 4 alkyl" means an unbranched or branched hydrocarbon radical having from 1 to 4 carbon atoms such as, for example, methyl, ethyl, propyl, isopropyl, 1-butyl, 2-butyl radicals , 2-methylpropyl or tert-butyl: the term "C -? - C8 alkyl" means the aforementioned alkyl radicals and, for example, the pentyl, 2-methylbutyl, 1, 1-dimethylbutyl, hexyl, heptyl, octyl radicals or 1, 1, 3,3-tetramethylbutyl; the term "C 1 -C 4 halogenoalkyl" means an alkyl group mentioned under the term "C 1 -C 4 alkyl" in which one or more hydrogen atoms are replaced with the aforementioned halogen atoms, preferably chlorine or fluorine, such as, for example, the trifluoromethyl group, the 1-fluoroethyl group, the group, 2,2,2-trifluoroethyl, the group tfMMMiaMA-. ... d. ».. mw * ^ - chloromethyl, fluoromethyl, the difluromethyl group or the 1,2-tetrafluoroethyl group; the term "C3-C8 cycloalkyl" means, for example, the cyclopropyl, cyclobutyl or cyclopentyl group; and the cyclohexyl, cycloheptyl or cyclooctyl radical; the term "C3-C8 halogenocycloalkyl" means one of the aforementioned C3-C5 cycloalkyl radicals in which one or more, in the case of fluoro optionally also all, the hydrogen atoms are replaced with halogen, preferably fluorine or chlorine, such as, for example, the 2,2-difluoro or 2,2-dichlorocyclopropane group or the fluorocyclopentane radical; the term "C2-C alkenyl" means, for example, the vinyl, allyl, 2-methyl-2-propenyl or 2-butenyl group: the term "C2-C4 halogenoalkenyl" means an alkenyl group of C2-C4 in the which some or, in the case of fluorine also all the hydrogen atoms are replaced with halogen, preferably fluorine or chlorine; the term "C2-C4 alkynyl" means, for example, the ethynyl, propargyl, 2-methyl-2-propynyl or 2-butynyl groups; the term "C2-C8 alkynyl" means, for example, the aforementioned radicals and, for example, the 1-pentynyl, 2-pentynyl, 3-pentynyl, 4-pentynyl or 1-octynyl groups, the term "haloalkynyl of C2" -C4"means a C2-C4 alkynyl group in which some, in the case of fluorine also all, the hydrogen atoms are replaced with halogen atoms, preferably fluorine or chlorine; the term "C1-C4 hydroxyalkyl" means, for example, hydroxymethyl, 1-hydroxyethyl, 2-hydroxyethyl, 1-hydroxy-1-methylethyl or 1-hydroxypropyl groups; the term "(C r C 4) alkanoyl-C 1 -C 4 alkyl" means, for example, an acetylmethyl, propionylmethyl, 2-acetylethyl group or a butyrylmethyl group; the term "C 1 -C 4 alkanoyl" means, for example, the formyl, acetyl, propionyl, 2-methylpropionyl or butyryl group; the term "C 8 -C 8 alkanoyl" means the aforementioned radicals and for example, the valeroyl, pivaloyl, hexanoyl, heptanoyl or octanoyl groups; the term "C 1 -C 12 alkanoyl" means, for example, the aforementioned radicals and, for example, the nonanoyl, decanoyl or dodecanoyl groups; the term "C2-C4 halogenoalkanoyl" means a C 1 -C 4 alkanoyl group in which some, and in the case of fluorine also all, the hydrogen atoms are replaced with halogen atoms, preferably fluorine or chlorine; the term "C2-C12 halogenoalkanoyl" means a C1-C20 alkanoyl group in which some, and also in the case of fluorine all, the hydrogen atoms are replaced with halogen atoms, preferably fluorine or chlorine; the term "cyano-C1-C4 alkyl" means a cyanoalkyl group whose hydrocarbon radical has the meanings given by the term "C1-C4 alkyl"; the terms "C1-C4 nitroalkyl" or "C1-C4 thiocyanoalkyl" mean one of the aforementioned C1-C4 alkyl groups which are substituted with a nitro group or a thiocyano group; the term "C1-C4 alkoxycarbonyl" means, for example, the methoxycarbonyl, ethoxycarbonyl, propoxycarbonyl, butoxycarbonyl or tert-butoxycarbonyl groups; the term "C 8 -alkoxycarbonyl" means, for example, the aforementioned radicals and, for example, pentyloxycarbonyl, hexyloxycarbonyl or octyloxycarbonyl groups; the term "d-C 2 alkoxycarbonyl" means the aforementioned radicals and, for example, the nonyloxycarbonyl, 2-methyloxycarbonyl, decyloxycarbonyl or docecyloxycarbonyl groups; the term "C 1 -C 4 alkoxycarbonyl (dC 4)" means, for example, a methoxycarbonylmethyl, ethoxycarbonylmethyl or methoxycarbonylethyl group; the term "C 1 -C 4 halogenoalkoxycarbonyl" means a C 1 -C 4 alkoxycarbonyl group in which one or more, in the case of fluorine , -, * ..,. -. *** .. , ". , -.,. ,. .. .. i. s ¡i **** «* - optionally all, the hydrogen atoms are replaced with halogen, preferably fluorine or chlorine; the term "C 1 -C alkylthio" means an alkylthio group whose hydrocarbon radical has the meanings given for the term "C 1 -C 4 alkyl"; the term "C 1 -C 8 alkylthio" means an alkylthio group whose alkyl radical has the meaning given by the term "CrC 8 alkyl"; the term "C 1 -C 4 halogenoalkylthio" means a C 1 -C 4 alkylthio group in which one or more, in the case of fluorine optionally all, the hydrogen atoms of the hydrocarbon portion are replaced with halogen, in particular chlorine or fluorine; the term "C 1 -C 4 alkylsulfinyl" means, for example, the methyl-, ethyl-, propyl-, isopropyl-, butyl-, isobutyl-, sec-butyl- or tert-butyl-sulfinyl groups; the term "C 1 -C 8 alkylsulfinyl" means one of the aforementioned alkylsulfinyl groups and, for example, the pentylsulfinyl, 2-methylbutylsulfinyl, hexylsulfinyl or octylsulfinyl groups; the term "C 1 -C 4 alkylsulfonyl" means, for example, the methyl-, ethyl-, propyl-, isopropyl-, butyl-, isobutyl-, sec-butyl- or tert-butyl-sulfonyl groups; the terms "C 1 -C 4 halogenoalkylsulfinyl" and "C 1 -C 4 halogenoalkylsulfonyl" mean C 1 -C 4 alkylsulfinyl and C 1 -C 4 alkylsulfonyl radicals having the abovementioned meanings in which one or more, in the case of fluorine optionally all, the hydrogen atoms of the hydrocarbon portion are replaced with halogen, in particular chlorine or fluoro; the terms "fluoromethyl sulfinyl" and "fluoromethylsulfonyl" mean the mono-, di- and trifluoromethylsulfinyl and -sulfonyl groups; the term "C 1 -C 4 alkoxy" means an alkoxy group whose hydrocarbon radical has the meaning given for the term "C 1 -C 4 alkyl"; the term "C 1 - C 8 alkoxy" means an alkoxy group whose hydrocarbon radical has the meaning given for the term "C 1 -C 2 alkyl"; the term "C 1 -C 8 alkylsulfonyl" means one of the aforementioned alkylsulfonyl groups and for example, the pentyl-, 2-methylbutyl-, hexyl-, heptyl-, or octylsulfonyl groups; the term "C 1 -C 4 alkylamino" means, for example, the methylamino, ethylamino, propylamino, isopropylamino, butylamino, isobutylamino, sec-butylamino, or tert-butylamino groups; the term "C 1 -C 8 alkylamino" means one of the aforementioned C 1 -C 4 alkylamino groups and for example, the pentylamino, hexylamino, heptylamino or octylamino groups; the term "C1-C4 dialkylamino" means, for example, the dimethylamino, methylethylamino, diethylamino, dipropylamino or dibutylamino groups, and also cyclic systems such as, for example, the pyrrolidino or piperidino group; the term "dialkylamino of C -? - C8" means one of the aforementioned dialkylamino groups of C-1-C4 and for example, the dipentylamino, diexylamino or dioctylamino groups, the term "C1-C4 halogenoalkoxy" means a halogenoalkoxy group whose halohydrocarbon radical has the meaning given for the term "C 1 -C 4 halogenoalkyl"; the term "(C 1 -C) alkoxy-C 1 -C 4 alkyl" means, for example, a 1-methoxyethyl group, a 2-methoxyethyl group, a 2-ethoxyethyl group, a methoxymethyl group or an ethoxymethyl group, a group 3 -methoxypropyl or a 4-butoxybutyl group; the terms "halogenoalkoxy (CrC4) -alkyl of C1-C4" "alkoxy (Ct-C4) -halogenoalkyl of C1-C4" and "halogenoalkoxy (C.-C4) -halogenoalkyl of C1-C4", means alkoxy radicals (C -? - C4) - C1-C4 alkyl having the meanings mentioned above in which one or more, in the case of fluorine optionally also all hydrogen atoms of the hydrocarbon portions of interest are replaced with halogen, preferably chlorine or fluorine; the term "(C 1 -C 4) -alkyl-C 1 -C 4 alkyl" means, for example, methylthiomethyl, ethylthiomethyl, propylthiomethyl, 2-methylthioethyl, 2-ethylthioethyl or 3-methylthiopropyl; the term "heterocyclyl" means a system of heteroaromatic or heteroaliphatic rings in which "heteroaromatic ring system" is to be understood as meaning an aryl radical in which at least one CH group is replaced by N and / or at least two adjacent CH groups are replaced with S, NH, or O, for example a radical of thiophene, furan, pyrrole, thiazole, oxazole, imidazole isothiazole, isoxasol, pyrazole, 1,3,4-oxadiazole, 1, 3,4- thiadiazole, 1,4-triazole, 1,4-oxadiazole, 1,4-thiadiazole, 1,4-triazole, 1,3-triazole, 1, 2,3,4- tetrazole, benzo [b] thiophene, benzo [b] furan, indole, benzo [c] thiophene, benzo [b] furan, isoindol, benzoxazole, benzothiazole, benzimidazole, benzisoxazole, benzisothiazole, benzopyrazole, benzothiadiazole, benzotriazole, dibenzofuran, dibenzothiophene , carbazole, pyridine, pyrazine, pyrimidine pyridazine, 1, 3,5-triazine, 1, 2,4-triazine, 1, 2,4,5-triazine, quinoline, isoquinoline, quinoxaline, quinazoline, cinoline, 1, 8- naphthyridine, 1 , 5-naphthyridine, 1, 6-naphthyridine, 1,7-naphthyridine, phthalazine, pyridopyrimidine, purine, pteridine or 4H-quinolizine; the term "heteroaliphatic ring system" means a C3-C8 cycloalkyl radical in which at least one carbon unit is replaced with O, S or a group NR11 and R11 is hydrogen, C1-C4 alkyl, C1 alkoxy -C4 or aryl; the term "heterocyclyloxy" or "heterocyclylthio" means one of the aforementioned heterocyclic radicals which are linked by an oxygen or sulfur atom; the term "C3-C8 cycloalkoxy" or "C3-C8 cycloalkylthio" means one of the aforementioned C3-C8 cycloalkyl radicals which are linked by an oxygen or sulfur atom; the term "C 1 -C 4 aryl alkanoyl" means, for example, the phenylacetyl, 3-phenylpropionyl, 2-phenylpropionyl, 2-methyl-2-phenylpropionyl, 4-phenylbutyryl or naphthylacetyl group; the term "(C3-C8) cycloalkyl-C1-C4alkanoyl" means, for example, the group cyclopropylcarbonyl, cyclobutylcarbonyl, cyclopentylcarbonyl, cyclohexylcarbonyl, cyclohexylacetyl cyclohexylbutyryl; the term "C 1 -C 4 heterocycloalkyl-alkanoyl" means, for example, the tenoyl, furoyl, nicotinoyl, thienylacetyl or pyridinpropionyl group; the term "(C3-C8) cycloalkoxycarbonyl" means, for example, the cyclobutyloxycarbonyl, cyclopentyloxycarbonyl, cyclohexyloxycarbonyl or cycloheptyloxycarbonyl group; The term "(C3-C8) cycloalkyl-C1-C4 alkoxycarbonyl" means, for example, the group cyclopropylmethoxycarbonyl, cyclobutylmethoxycarbonyl, cyclopentyloxymethoxycarbonyl, cyclohexyloxymethoxycarbonyl, 1- (cyclohexyl) ethoxycarbonyl or 2- (cyclohexyl) ethoxycarbonyl; The explanation given above is applied analogously to the homologs or radicals obtained therefrom. The present invention relates to the compounds of the formula (I) in the form of the free base or of an acid addition salt. The acids that can be used for the formation of the salt are inorganic acids such as hydrochloric acid, hydrobromic acid, nitric acid, sulfuric acid, phosphoric acid, or organic acids such as formic acid, acetic acid, propionic acid, malonic acid, oxalic acid, fumaric acid, adipic acid, stearic acid, oleic acid, methanesulfonic acid, benzenesulfonic acid or toluenesulfonic acid. Some of the compounds of the formula (I) have one or more asymmetric carbon atoms or stereoisomers in the double bonds. Therefore, enantiomers or diastereomers may be present. The invention encompasses not only the pure isomers, but also their mixtures. The diastereomeric mixtures can be resolved into the individual components by customary methods, for example by selective crystallization from appropriate solvents or by chromatography. The racemates can be resolved into the enantiomers by customary methods, for example by salt formation with an enantiomerically pure, chiral acid, separation of the diastereomeric salts and release of the pure enantiomers by means of a base. Preferred in a very special way are the following groups of compounds of the formula (la) up to the formula (le): J a ^ 'a * AjJ - -. m n ^^ n * MJ ^^^^^ H | MÉg | In these formulas X1, X2, Z, R4, R5 and R6 each have the meanings given in the formula (I) (X1, X2? .. X). Particularly preferred are the compounds of the formula (Ia1) up to the formula (Ia4): in this case Z, R5 and R6 each have the meanings given in the formula (I) The compounds according to the invention are prepared by methods known per se from the literature, since these are described in normal works in organic synthesis, for example Houben-Weyl, Methoden der Organischen Chemie [Methods in Organic Chemistry], Georg- Thieme-Verlag, Stuttgart.

The preparation is carried out under reaction conditions which are known and appropriate for the reactions mentioned above. Other variants which are known per se, but which are not illustrated in the present invention in greater detail, may also be used. If desired, the starting materials can also be formed in situ, such that they are not isolated from the reaction mixture but are reacted immediately to give the compounds of the formula The general chemistry of 1,3-oxazolines is described, for example, in Tetrahedron, 1994, 50, 2297-2360 and in Nachr. Chem. Tech. Lab. 1996, 44, 744-750. The invention also relates to a process for preparing compounds of the formula (I) by reacting known 1,3-oxazolines and 1,3-thiazolines of the formula (II) (see, for example, EP-A-0 345 775). ) (appropriately substituted with R1, R2, R3) with metalated pyridine compounds of the formula (III) (appropriately substituted with R4, R5, R6), which comprises reacting a halogen and a perfluoroalkylsulfonate compound of the formula (II) ) wherein Y is Cl, Br, I or perfluoroalkylsulfonate and A, Z and E have the meanings given in the formula (I) With an organometallic compound of the formula (III) GM (III) in which 5 M is a group projection containing B-, Sn- or Zn- and G has the meaning given in formula (I), with palladium catalysis. The methods of A to H for the synthesis of a variety of subgroups of compounds of the formula (I) can be mentioned by way of example: Method A (II) (III) (I) G = 3-pyridyl, 4-pyridyl, 2-pyridon-5-yl, 2-pyridon-3-yl (see formula (I)). The connection of the phenyl ring with a pyridine ring is carried out, for example by palladium catalysis using Suzuki coupling, Stille coupling or Negishi coupling (see for example, P. Knochel, Chem. Review 1993, 93, 2117-2188 or Jiro Tsuji, Palladium Reagents and Catalysts, John Wiley &Sons, 1996). _u_ ________________ _____________ É ____ It is also possible to exchange the functional linking groups between (II) and (III): Method B (SAW) It is also possible to first construct a pyridyl-phenyl structural unit and convert these precursors to 1,3-oxazolines and 1,3-thiazolines of the formula (I).

Method C The oxazoline precursors of the formula (II) are prepared, for example, by the following routes, some of which are known (EP-A-0 432 661, G. Helmchen, Tetrahedron 1996, 52, 7547-7583)) The activated carboxylic acid derivatives are reacted with aminoalcohols (VI) (appropriately substituted with R1, R2, R3) (synthesis K. Drauz, J. Org. Chem. 1993, 58, 3568-3571) to give the amidoalcohols ( Vile).

METHOD D (Ex. VP3) Y = CI, Br, CrtBsio,? DSio The chlorides (VIII) (Y = CI) are obtained from the amidoalcohols (Vil) for example using thionyl chloride; where sulfone halides are used, sulfonates (Vil) are formed (Y = for example mesylate, tosylate). The oxazolines (II) are formed from (VIII) by the action of the bases. Method E (Ex. VP4) Y = Cl, Br, Omesilo, Otosilo Bases which are suitable are, for example, basic salts such as alkali metal hydroxide, alkali metal carbonate, hydrides, alkoxides and amines. Starting from the 4-hydroxyphenyl derivatives of (II), the triflates can be obtaiby sulfonation with, for example, trifluoromethanesulfonyl chloride. The oxazoline precursors of the formula (IV) containing a tin group are accessible by Stille coupling with distanano: Method F (Ex. VP5) The pyridine precursors of the formula (III) are formed, for example by generating metalated pyridine derivatives with the appropriate substituents R4, R5, R6 as in the formula (I) and their reaction with, for example, boric esters, tin halides. or zinc halides.

Method G (Ex. VP7, VP8) M = B (OR) 2, SnR3, ZnHal R = alkyl, alkylene Amino alcohol (VI) precursors can be prepared by reducing known 2-hydroxyacetophenone oximes by hydride.

Method H (Ex. Vp2) The collections of compounds of the formula (I) which can be synthesized by the aforementioscheme can also be prepared in parallel, and this can be done manually or in semi-automated or fully automated form. In this case, it is possible, for example, to automate the reaction, treatment or purification process of the products or of the intermediaries. In total, this should be understood as meaning the procedure as described, S.H. DeWitt in a_idi_ ia? ¡_ £ u¡i ^^ dí ___ > "Annual Reports in Combinatorial Chemistry and Molecular Diversity: Automated synthesis", volume 1, Verlag Escom 1997, pages 69 to 77. A series of commercially available apparatuses as offered by, for example, Stem Corporation, Woodrolfe Road, Tollesbury, Essex , CM9 (SE, England or H + P Labortechnik, Bruckmannring 28, 85764 OderschleiBheim, Germany, can be used for the parallel process of the reaction and treatment.) For the parallel purification of compounds of the formula (I), or of the intermediates obtaiduring the preparation, use can be made, inter alia, of chromatography apparatuses, for example those by ISCO, Inc., 4700 Superior Street, Lincoln, NE 68504, USA The mentioapparatuses lead to a modular process in which They automate the individual steps of the procedure, however, manual operations can be performed between the steps of the procedure.This can be avoided using semi-automated automation systems -integrated or fully integrated where the automation modules in question are operated, for example by robots. Such automation systems can be obtai for example from Zymark Corporation, Zymark Center, Hopkinton, MA 01748, USA. In addition to what has been described herein, the compounds of the formula (I) can be prepared partially or completely with solid-phase supported methods. For this purpose, the individual intermediary steps or all the intermediate steps of the synthesis or of a synthesis adapted to be adapted to the procedure in question are directed to a synthetic resin. The synthesis methods with solid phase support are described extensively in the specialized literature, for example Barry A. Bunin in "The Combinational Index", Academic Press, 1998. The use of synthesis methods with solid phase support allows a series of protocols that are known from the literature, and that in turn, can be developed manually or in an automated way. For example, the "tea bag" method (Houghten, US 4,631, 211; Houghten et al., Proc. Nati, Acad. Sci, 1985, 82, 5131-5135), where IRORI products are used, 11149 North Torrey Pines Road, La Jolla, CA 92037, USA, can be semi-automated. Parallel synthesis automation with solid phase support is successfully developed, for example, by Argonaut Technologies devices, Inc., 887 Industrial Road, San Carlos, CA 94070, USA or MultiSynTech GmbH, Wullener Feld 4, 58454 Witten, Germany. The preparation of the processes described herein yields compounds of the formula (I) in the form of collections of substance which are referred to as banks. The present invention also relates to libraries comprising at least two compounds of the formula (I). The compounds of the formula (I) are suitable for controlling animal pests, in particular insects, arachnids, helminths and molluscs, very especially preferably for controlling insects and arachnids found in agriculture, in cattle breeding, in forests, in the protection of stored goods and materials, and in the hygiene sector, and have a good tolerance in plants and favorable toxicity for the species _a _ ^ _ 4 _ ^ _ ^ _ ^ __ aíÁ_ila_1 _? _ a_ of warm blood. They are active against normally sensitive and resistant species and against all stages of development or individual stages. The aforementioned pests include: on the order of Acariña, for example, Acarus siró, Argas spp., Ornithodoros spp., Dermanyssus gallinea, 5 Eriophyes ribis, Phyllocoptruta oleivora, Boophilus spp., Rhipicephalus spp., Ambiyomma spp., Hyalomma spp. , Ixodes spp., Psoroptes spp., Chorioptes spp., Sarcoptes spp., Tarsonemus spp., Bryobia praetiosa, Panonychus spp., Tetranychus spp., Eotetranychus spp., Oligonychus spp., Eutetranychus spp. From the order of Isopoda, for example, Oniscus aselus, Armadium 10 vulgare, Porcellio scaber. From the order of Diplopoda, for example, Blaniulus guttulatus. From the order of Chilopoda, for example, Geophilus carpophagus, Scutigera spp. From the order of Symphyla, for example, cutigerella immaculata. 15 From the order of Thysanura, for example, Lepisma saccharina. From the order of Collembola, for example, Onychiurus armatus. From the order of Orthoptera, for example, Blatta orientalis, Periplaneta americana, Leucophaea maderae, Blattella germanica, Acheta domesticus, Gryllotalpa spp., Locusta migratoria migratorioides, Melanoplus 20 differentialis, Schistocerca gregaria. From the order of Isoptera, for example, Reticulitermes spp. «ÜÉÜMÉMUH aaá? Ui áriwÉ From the order of: Anoplura, for example, Phylloera vastatrix, Pemphigus spp., Pediculus humanus corporis, Haematopinus spp., Linognathus ssp. From the order of Mallophaga, for example, Trichodectes spp., Damalinea spp. From the order of Thysanoptera, for example, Hercinothrips femoralis, Thrips tabaci. From the order of Heteroptera, for example, Eurygaster spp., Dysdercus intermedius, Piesma quadrata, Cimex lectularius, Rhodnius prolixus, Triatoma spp. From the order of Homoptera, for example, Aleurodes brassicae, Bemisia tabaci, Trialeurodes vaporariorum, Aphis gossypii, Brevicoryne brassicae, Cryptomyzus ribis, Doralis fabae, Doralis pomi, Eriosoma lanigerum, Hyalopterus arundinis, Macrosiphum avenae, Myzus spp., Phorodon humuli, Rhopalosiphum padi , Empoasca spp., Euscelus bilobatus, Nephotettix cincticeps, Lecanium corni, Saissetia oleae, Laodelphax striatellus, Nilaparvata lugens, Aonidiella aurantii, Aspidiotus hederae, Pseudococcus spp., Psylla spp. From the order of Lepidopter, for example, Pectinophora gossypiella, Bupalus piniarius, Cheimatobia brumata, Lithocolletis blancardella, Hyponomeuta padella, Plutella maculipennis, Malacosoma neustria, Euproctis chrysorrhoea, Lymantria spp., Bucculatrix thurberiella, Phyllocnistis citrella, Agrotis spp., Euxoa spp., Feltia spp., Earias insulana, Heliothis spp., Laphygma exigua, Mamestra brassicae, Panolis flammea, Prodenia litura, Spodoptera spp., Trichoplusia ni, Carpocapsa pomonella, Pieris spp., Chilo spp., Pyrausta nubilalis, Ephestia kuehniella, Galleria mellonella, Cacoecia podana, Capua reticulana, Choristoneura fumiferana, Clysia ambiguella, Homona magnanimous, Tortrix viridana. From the order of Coleoptera, for example, Anobium punctatum, Rhizopertha dominica, Bruchidius obtectus, Acanthoscelides obtectus, Hylotrupes bajulus, Agelastica alni, Leptinotarsa decemlineata, Phaedon cochleariae, Diabrotica spp., Psylloides chrysocephala, Epilachna varivestis, Atomaria ssp., Oryzaephilus surinamensis, Anthonomus spp., Sitophilus spp., Otiorrhynchus sulcatus, Cosmopolites sordidus, Centhorrynchus assimilis, Hypera postica, Dermestes spp., Trogoderma, Anthrenus spp., Attagenus spp., Lyctus spp., Meligethes aeneus, Ptinus spp., Niptus hololeucus, Gibbium psylloides, Tribolium spp., Tenebrio molitor, Agriotes spp., Conoderus spp., Melolontha melolontha, Amphimallon solstitialis, Costelytra zealyica. From the order of Hymenoptera, for example, Diprion spp., Hoplocampa spp., Lasius spp., Monomorium pharaonis, Vespa spp. From the order of Diptera, for example, Aedes spp., Anopheles spp., Culex spp., Drosophila melanogaster, Musca spp., Fannia spp., Calliphora erythcephala, Lucilia spp., Chrysomyia spp., Cuterebra spp., Gastrophilus spp., Hypobosca spp., Stomoxys spp., Oestrus spp., Hypoderma spp., Tabanus spp., Tannia spp., Bibio hortulanus, Oscinella frit, Phorbia spp., Pegomyia hyoscyami, Ceratitis capitata, Dacus oleae, Typula paludosa.

¡G ^ g ^ ^ From the order of Siphonaptera, for example, Xenopsylla cheopsis, Ceratophyllus spp. From the order of Arachnida for example, Scorpio maurus, Latrodectus mactans. 5 From the helminth class, for example, Haemonchus, Trichostongulus, Ostertagia, Cooperia, Chabertia, Strongyloides, Oesophagostomum, Hyostrongulus, Ancylostoma, Ascaris and Heterakis and also Fasciola. From the Gastropoda class, for example, Deroceras spp., Arion 10 spp., Lymnaea spp., Galba spp., Succinea spp., Biomphalaria spp., Bulinus spp., Oncomelania spp. From the Bivalve class, for example, Dreissena spp. Plant parasitic nematodes that can be controlled according to the invention include, for example, root parasitic and land-swelling nematodes, such as, for example, those of the general Meloidogyne class (loop nematodes). of root, such as Melodogyne incognita, Meloidogyne hapla and Meloidogyne javanica), Heterodera and Globodera (spore-forming nematodes, such as Globodera rostochiensis, Globodera paluda, Heterodera trifolii) and of the 20 genera Rodopholus, such as Radapholus similis, Pratylenchus such as Pratylenchus neglectus, Pratylenchus penetrans and Pratylenchus curvitatus; Tylenchulus such as Tylenchulus semipenetrans, Tylenchorhynchus, such as Tylenchorhynchus dubius and Tylenchorhynchus _1-U-_Í l * U? AU. claytoni, Rotylenchus such as Rotylenchus robustus, Heliocotylenchus such as Haliocotylenchus multicinctus, Belonoaimus such as Belonoaimus longicaudatus, Longidorus such as Longidorus elongatus, Trichodorus such as Trichodorus primitivus and Xiphinema such as Xiphinerna index. Other genera of nematodes that can be controlled using the compounds according to the invention are Ditylenchus (stem parasites, such as Ditylenchus dipsaci and Ditylenchus destructor), Aphelenchoides (leaf nematodes, such as Aphelenchoides ritzemabosi) and Anguina (seed nematodes, such as Anguina tritici). The invention also relates to compositions, for example crop protection compositions, preferably insecticide, acaricides, ixodicils, nematicides, moluscomicides or fungicides, especially and preferably insecticidal and acaricidal compositions comprising one or more compounds of the formula (I) in addition to suitable formulation aids. In general, the compositions according to the invention comprise from 1 to 95% by weight of the active substances of the formula (I). To prepare the compositions according to the invention, the active substance and the other additives are combined and brought into a suitable use form. They can be formulated in several ways, depending on the biological and / or chemical / physical parameters that prevail. The following are examples of possible formulations: - ^^ lttMikfMa Wettable powders (WP), emulsifying concentrates (EC), aqueous solutions (SL), emulsions, sprayable solutions, dispersions based on water or oil (SC), emulsions in suspension (SE), powders (SE), seed conditioning products, granules in the form of 5 microgranules, sprinkling granules, coated granules and absorption granules, water dispersible granules (WG), ULV microcapsule formulations, waxes or baits. These individual types of formulations are known in principle, and are described, for example in Winnacker-Küchler, "Chemical Technology ", volume 7, C. Hauser Verlag Munich, 4th edition 1986, van Falkenberg," Pesticides Formulations ", Marcel Dekker NY, 2nd Edition 1972-73, K. Martens," Spray Drying Hybook ", 3rd Edition 1979, G Goodwin Ltd. London The necessary formulation aids such as materials inerts, surfactants, solvents and other additives are also known and described, for example, in Watkins, "Handbook of Insecticide Dust Diluents and Garriers", 2nd Edition., Darly Books, Caldwell N.J .; H. v. Olphen, "Introduction to Clay Colloid Chemistry", 2nd Edition., J. Wiley & Sons, N.Y .; Marsden, "Solvents Guide", 2nd Edition., Interscience, N.Y. 1950; McCutcheon's, "Detergents and Emulsifiers Annual", MC Publ. Corp., Ridgewood N.J .; Sisley and Wood, "Encyclopedia of Active Surface Agents", Chem. Publ. Co. Inc., N.Y. 1964; Schonfedt, "Grenzfláchenaktive Áthylenoxidaddukte", [Surface-active ethylene oxide adducts] Wiss. Verlagsgesell., Stuttgart 1967; _ ___-_? L_i_tf_a _ * _ ^ _ t_M -__ _áal_a._taA ^ a_ ^ É_Mk_M > _fc1_ak_t_ A É ^ HiiiÉi Winnacker-Küchler, "Chemische Technologie", Volume 7, C. Hauser Verlag Munich, 4th Edition 1986. Based on these formulations, it is also possible to prepare combinations with other effective active materials to kill pests, 5 fertilizers and / or growth regulators, for example in the form of an instant mix formulation or tank mix. Wettable powders are preparations which are uniformly dispersible in water, which in addition to the active substance also comprises humectants, for example polyoxyethylated alkylphenols, polyoxyethylated fatty alcohols, alkyl sulfonates and alkylphenolsulfonates and dispersants, for example sodium lignosulfonate or 2,2'- sodium dinaphthylmethane-6,6'-d-sulphonate, in addition to a diluent or inert material. The emulsifying concentrates are prepared by dissolving the active substance in an organic solvent, for example butanol, cyclohexanone, dimethylformamide, xylene or other high-boiling aromatics or hydrocarbons, with the addition of one or more emulsifiers. As emulsifiers, the following may be used, for example calcium alkylarylsulfonate such as calcium dodecylbenzenesulfonate, or nonionic emulsifiers such as polyglycol fatty acid esters, polyglycol fatty acid esters, polyglycolyl alkylaryl ethers, fatty alcohol polyglycol ethers, propylene oxide / ethylene oxide condensates, alkyl polyethers, sorbitan fatty acid esters, polyoxyethylene sorbitan fatty acid esters or polyoxyethylene sorbitol esters.

MÉi ^ JßÜkáátfMk M ^ M ^ AhM ^^? ÜMMbii * For example, powders are obtained by grinding the active substance with finely divided solid materials, for example talcs or natural clays, such as kaolin, bentonite, pyrophyllite or diatomaceous earth. Granules can be prepared either by atomizing the active substance on granulated adsorbable inert material or by applying the concentrates of active substance on the surface of carrier materials such as sand or kaolinites, or of granulated inert material, by means of adhesives, for example polyvinyl alcohol or polyacrylate sodium, or other mineral oils. Suitable active substances can also be granulated in the manner that is customary for the preparation of fertilizer granules if desired as a mixture with fertilizers. The concentration of active substance in wettable powders is, for example, approximately 10 to 90% by weight, the rest at 100% by weight is composed of customary formulation auxiliaries. In the case of the emulsifying concentrates, the concentration of active substance may be approximately 5 to 80% by weight. The formulations in the form of powders generally comprise from 5 to 20% by weight of active substance, solutions sprinkled by approximately 2 to 20% by weight. In the case of granules, the content of active substance depends partially if the active compound is in liquid or solid form and which are the filler granulation aids and the like which are being used. In addition, the aforementioned active substance formulations comprise, if appropriate, the adherents, humectants, ? dispersants, emulsifiers, penetrants, solvents, fillers or vehicles that are conventional in each case. For use, the concentrates, which are present in commercially available form, if desired, are diluted in the usual manner, for example in the case of wettable powders, emulsifying concentrates, dispersions and in some cases some microgranules using water. Preparations in the form of powders and granules and sprayable solutions are generally not diluted in any way with another inert substance prior to use. The speed of application required varies with external conditions such as inter alia, temperature and humidity. It can vary within wide limits, for example between 0.0005 and 10.0 kg / ha or more of the active substance, but it is preferable between 0.001 and 5 kg / ha. The active substances according to the invention, in their commercially available formulations and in the forms of use prepared from these formulations (see the compositions mentioned above) can be present in mixtures with other active substances such as insecticides, attractants, sterilants, acaricides, nematocides, fungicides, mollusc annihilators, growth regulating substances or herbicides. Pesticides include, for example, phosphoric esters, carbamates, carboxylic esters, formamidines, tin compounds and materials produced by microorganisms.

The preferred compounds in mixtures are: 1.- From the group of phosphorus compounds: acephate, azamethiphos, azinphos-ethyl, azinphos-methyl, bromophos, bromophos-ethyl, cadusafos (F-67825), chloretoxyphos, chlorfenvinphos, chlorormephos, chlorpyrifos , chlorpyrifos-methyl-demeton, demeton-S-methyl, demeton-S-methyl sulfone, dialiphos, diazinon, dichlorvos, dicrotophos, dimethoate, disulfoton, EPN, etion, ethoprofos, etrimfos, famfur, fenamiphos, fenitriotion, fensulfotion, fention, fonofos, formothion, fosthiazato (ASC-66824), heptenofos, isazofos, isotioato, isoxation, malathion, metacrofos, methamidophos, metidation, salition, mevinfos, monocrotofos, naled ometoato, oxidemeton-methyl, paration, paration-methyl, fentoato, phorate, phosalone, phospholane, phosphocarb (BAS-301), phosmet, phosphamidon, phoxim, pyramiphos, pyrimiphos-ethyl, pyrimiphos-methyl, profenofos, propafos, proetamfos, protiofos, pyraclofos, piridapention, quinalfos, sulprofos, temefos, terbufos, tebupirimfos, tetrachlorinated , thiometon, triazophos, trichlorfon, vamidotion; 2.- Of the group of carbamates: alanycarb (OK-135), aldicarb, 2-sec-butylphenyl methylcarbamate (BPMC), carbaryl, carbofuran, carbosulfan, cloetocarb, benfuracarb, etiofencarb, furathiocarb, HCN-801, isoprocarb, methomyl., 5-methyl-m-cumenylbutyryl (methyl) carbamate, oxamyl, pyrimicarb, propoxur, thiodicarb, thiofanox, 1-methylthio (ethyldepeamino) -N-methyl-N- (morpholinothio) carbamate (UC 51717), triazamate; 3.- From the group of carboxylic esters: acrinatin, allethrin, alphamethrin, 5-benzyl-3-furylmethyl (E) - (1 R) -cis-2,2-dimethyl-3- (2-oxothiolan-3-ylidenemethyl) Cyclopropanecarboxylate, beta-Cyfluthrin, beta-cypermethrin, ^ Ü ^^ UHÉ ilMI bioallethrin, bioallethrin ((s) -cyclopentyl), bioresmethrin, bifenthrin, (RS) - 1-cyano-1- (6-phenoxy-2-pyridyl) methyl (1 RS) -trans- 3 (-4-tert-butylphenyl) -2,2-dimethylcyclopropanecarboxylate (NCI 85193), cycloprotin, cyfluthrin, cyhalothrin, citritrin, cypermethrin, cyphenothrin, deltamethrin, empenthrin, esfenvalerate, 5-fenfluthrin, fenpropathrin, fenvalerate, flucythrinate, flumethrin, fluvalinate (D isomer), imiprothrin (S-41311), lambda-cyhalothrin, permethrin, phenothrin ((R) simero), prallethrin, pyrethrins (natural products), resmethrin, tefluthrin, tetramethrin, teta-cypermethrin (TD-2344), tralometrine , transfluthrin, zetacypermethrin (F-56701); 10 4.- Of the group of amidines: amitraz, clordimeform; 5.- From the group of compounds tin cyhexatin, fenbutatin oxide; 6.- Others: abamectin, ABG-9008, acetamiprid, falcitera anagrafa, AKD-1022, AKD-3059, ANS-118, bacillus thuringiensis, beauveria bassianea, bensultap, bidenazate (D-2341), binapacril, BJL-932, bromopropilate, BTG-504, BTG-505, buprofezin, camphechlor, cartap, chlorobenzilate, chlorfenapyr, chlorfluazuron, 2- (4-chlorophenyl) -4, 5-diphenylthiophene (UBI-T 930), chlorpentezine, chromafenozide (ANS-118), CG-216, CG-217, CG-234, A-184699, 2-naphthylmethylcyclopropanecarboxylate (Role 2-0470), ciromazin, diacloden (thiamethoxam), diafentiuron, ethyl 2-chloro-N- (3,5-dichloro-4- (1, 1, 2, 3,3,3-hexafluoro-1 -proploxy) phenyl) carbamoyl) -2- carboximidate, DDT, dicofol, diflubenzuron, N- (2,3-dihydro-3-methyl-1,3-thiazol-2-ylidene) -2,4-xylidine, dinobuton, dinocap, diofenolan, DPX-062, emamectin benzoate (MK-244), - T-lllllimi? | -r? Il__ __i ______ i ____ ??. Ml n - I l 1É11 ti «? ___ N__ _. nn ttn * ¿a ^ ?????????????????????? endosulphan, ethiprole (sulfetiprol), etofenprox, ethoxazole (YI-5301), fenazaquin, fenoxicarb, fipronil, fluazuron, flumite (flufenzine, SZI-121), 2-fluoro-5- (4- (4-ethoxyphenyl) -4-methyl-1-pentyl) diphenyl ester (MTI 800), franulosis and nuclear polyhedrosis virus, fenpyroximate, fentiocarb, flubenzimine, flucycloxuron, flufenoxuron, flufenprox (ICI-A5683), fluproxifen, gamma-HCH, halofenozide (RH-0345), halofenprox (MTI-732), hexaflumuron (DE_473), hexitiazox, HOI-9004, hydramethylnon ( AC 217300), lufenuron, imidacloprid, indoxacarb (DPX-M062), kanemite (AKD-2023), M-020, MTI-446, ivermectin, M-020, methoxyfenozide (intrepid, RH-2485), milbemectin, NC-196, neemgard, nitenpyram (TI-304), 2-nitromethyl-4,5-dihydro-6H-thiazine (DS 52618), 2-nitromethyl-3,4-dihydrothiazole (SD 35651), 2- Nitromethylene-1,2-thiazinan-3-ylcarcarbamaldehyde (WL 108477), Pyriproxyfen (S-71639), NC-196, NC-1111, NNI-9768, Novaluron (MCW-275), OK-9701, OK-9601, OK-9602, propargite, pymetrozine, pyridaben, pyrimidifen (SU-8801), RH-0.45, RH-2485, RH-2485, RYI-210, S-1283, S-1833, SB7242, SI-8601, silafluofen, silomadine (CG-177), spinosad, SU-9118, tebufenozide, tebufenpyrad (MK-239), teflubenzuron, tetradifon, tetrasul, thiacloprid, thiocyclam, TI-435, tolfenpirad (OMI-88), triazamate (RH-7988), triflumuron , verbutin, vertalac (mikotal), YI-5301. The content of active substance of the use form prepared from the commercially available formulations can vary from 0.00000001 to 95% by weight of active substance, preferably between 0.00001 and 1% by weight. The application is carried out in a customary way adapted to suit the forms of use.

The invention also relates to a method for controlling harmful insects, Acariña, molluscs and / or nematodes which, in an effective amount of a compound according to the invention or a composition according to the invention, are applied to these or to the plants, areas or substrates infected with them. The use of a compound according to the invention or of a composition according to the invention for controlling harmful insects, Acarina, molluscs and / or nematodes are also the material of the invention. The active substances according to the invention are also suitable for use in the field of veterinary medicine, preferably for controlling endoparasites and ectoparasites, and in the field of animal husbandry. The active substances according to the invention can be applied in a known manner, such as by oral administration in the form of, for example, tablets, capsules, beverages or granules, by thermal application in the form of, for example, dipping, sprinkling, pouring in and local application in and sprinkling, or by parenteral administration in the form of, for example, an injection. In addition, the compounds according to the invention are also suitable for use in technology, for example as wood preservatives, as preservatives for paints, in cooling lubricants for metal works, or as a preservative for drilling and cutting oils. Accordingly, the compounds of the formula (I) according to the invention can also be used particularly and conveniently in the raising of cattle (for example cattle, sheep, pigs, and birds such as chickens, geese and Similar). In a preferred embodiment of the invention, novel compounds, if suitable in associated formulations (see above), are administered orally to the animals, and if appropriate together with the drinking water or food. As the excretion in the stool is extremely efficient, the development of insects in the feces of animals can be very easily avoided in this way. The doses and formulations that are appropriate in each case, depend in particular on the species and stage of development of productive livestock and also on the risk of infestation and can be easily determined and established by usual methods. For example, the compounds can be used in cattle at doses of 0.01 to 1 mg / kg of body weight. The compounds of the formula (1) according to the invention are also distinguished by an outstanding fungicidal action. Fungal pathogens that have already penetrated the plant tissue can be controlled successful way in healing way. This is especially important and convenient in the case of those fungal diseases that can no longer be effectively controlled with fungicides that are otherwise usual once the infection has started. The spectrum of action of ? li_ £ l _________________________________________ ^ 4 the claimed compounds encompass a variety of economically important phytopathogenic fungi, such as, for example, Plasmopara vitivola, Phytophtora infestans, erysiphe graminis, Pyricularia oryzae, Pyrenophora teres, Leptosphaerea nodorum and Pellicularia sasakii, as well as Puccinia recondita. These compounds of the formula (I) which are predominantly effective for killing insects, mites, molluscs or nematodes, can be applied, in their commercially available formulations, either alone or in combination with other fungicides known from the literature. Fungicides which are known from the literature and which can be combined according to the invention with the compounds of the formula (I) are, for example, the following products: aldimorf, andaprim, anilazine, BAS 480F, BAS 450F, benalaxyl , benodanil, benomyl, binapacril, bitertanol, bromuconazole buthiobate, captafol, captan, carbendazim, carboxin, CGA 173506, ciproduram, diclofluanid, diclomezine, diclobutrazol, diethofencarb, difenconazole (CGA 169374), difluconazole, dimethirimol, dimetomorph, diniconazole, dicnocap, dithianon, dodemorf, dodine, edifenfos, etirimol, etridiazol, fenarimol, fenfuram, fenpiclonil, fenpropidin, fenpropimorf, fentin acetate, fentin, hydroxide, ferimzone (TF164), fluazinam, fluobenzimine, fluquinconazole, fluorimide, flusilazole, flutolanil, flpet, fosetyl aluminum, fuberidazole, fulsulfamide (MT-F 651), furalaxyl, furconazole, furmeciclox, guazatine, hexaconazole, ICI A5504 imazalil, imibenconazole, iprobenfos, prodion, isoprothiolane, KNF 317, copper compounds such as copper oxychloride, oxina-copper, copper oxide, mancozeb, maneb, mepanipyrim (KIF 3535), metoconazole, mepronil, metalaxyl, metasulfocarb, metfuroxam MON 24000, myclobutanil , nabam, nitrotalidopropyl, nuarimol, ofurace, oxadixilo, oxycarboxin, penconazole, pencicuron, PP 969, probenazole, propineb, prochloraz, procimidon, propamocarb, propiconazole, protiocarb, piracarb olid, pyrazophos, pirifenox, piroquilon, babenzazol, RH7592, sulfur, tebuconazole, TF 167, thiabendazole, ticiofen, thiophanate-methyl, thiram, tolclofos-methyl, tolylfluanid, triadimefon, triadimenol, tricor- lazole tridemorph, triflumizole, triforine, validamicin, vinclozolin, XRD 563, zineb, sodium dodecyl sulphonate, sodium dodecyl sulfate, ether C13 / C15-sodium azole sulfonate, sodium cetostearyl phosphate ether, dioctylsodium sulfosuccinate, sodium propylene naphthalenesulfonate, sodium methylenebisnaphthalenesulfonate, cetyltrimethylammonium chloride, salts of amines primary, secondary and tertiary long chain, alkylpropylene amines, laurylpyrimidinium bromide, ethoxylated quaternized fatty amines, alkyldimethylbenzylammonium chloride and 1-hydroxyethyl-2-alkyl-imidazoline. The aforementioned compounds for the combinations are known active substances, many of them are described in C.D.S., Tomlin, S.B. Walker, The pesticide manual, 11th Edition, British Crop Protection Council, Farnham, 1997. The content of the active substance of the ready-to-use forms of commercially available formulations may vary within the broad ranges from 0.0001 to 95% in substance weight d.Maiu? iii.iÉ? _ß_Hl _ ^ __ ^ _ _i_ii_ active, preferably 0.0001 to 1% by weight. They are applied in a customary way adapted so that they adapt to the forms of use. They are customarily used to suit the forms of use, for example, by applying them to control pathogenic fungi, an amount effective to kill fungi of a compound according to the invention to these fungi or to plants, to areas infested with them, or the seed. The invention also relates to the seed, treated or coated with an effective amount of a compound according to the invention or of a composition according to the invention. The compounds of the formula (I) can also be used to control harmful organisms in known genetically engineered plant crops, or plants genetically engineered for development. As a rule, transgenic plants are distinguished by particularly advantageous properties, for example by resistance to particular crop protection agents, resistance to plant diseases or pathogens of plant diseases, such as particular insects or microorganisms such as fungi, bacteria or viruses. . Other particular properties involve, for example, the harvested material with respect to quantity, quality, storage properties, composition and specific constituents. Thus, it is known that transgenic plants in which the starch content is increased, or the quality of the starch is altered, or where the harvested material has a different fatty acid composition. Its use is preferred in economically important transgenic crops, of useful and ornamental plants, for example of cereals such as wheat, barley, rye, oats, millet, rice, cassava and maize or other crops of sugar beet, cotton, soybean, oilseed rape. , potatoes, tomatoes, peas and other types of vegetables. When used in transgenic crops, particularly those that have insect resistance, effects are often observed, in addition to the effects against harmful organisms that are observed in other crops, which are specific for application in the transgenic crop in question, for example an altered or specifically extended spectrum of pest that can be controlled, or altered application rates which can be used for application. Therefore, the invention also relates to the use of compounds of the formula (I) to control harmful organisms in transgenic crop plants. The use according to the invention of compounds of the formula (I) or of compositions containing them, for example insecticide, acaricide, molluscicide, nematicide or fungicide, also includes the case in which the compound of the formula (I) or its salt, is formed from a precursor only after the application, for example in the insect, in a plant or in the ground.

The content of the German patent application 198 15 026.1, whose priority is claimed by the present application, and the content of the attached abstract, are therefore expressly incorporated by reference; these are part of the present description in the form of an appointment. The following examples are intended to illustrate the invention, without restricting it.

A. EXAMPLES OF PREPARATIONS VP1 Precursor of O-Methyloxime of 4'-bromo-2-hydroxyacetophenone Sodium formate (244.6 g, 3597 mmol) in ethanol / water 7: 3 (1 l), 2,4'-dibromoacetophenone (200 g, 719) was introduced. mmoles) was added in portions at about 60 ° C, and then the mixture was refluxed for 7 hours. Then it was mixed with water (1 I). Upon cooling, the hydroxyketone was crystallized and isolated by suction filtration. This gave the hydroxyketone intermediate (143.6 g, 93% yield) in its pure form; This was mixed with O-methylhydroxylamine hydrochloride (59.0 g, 706 mmol) and sodium acetate (57.9 g, 706 mmol) in dioxane / water 9: 1 (700 mL), and the mixture was refluxed for 3 hours. After stirring with water (1.3 L) and extraction with heptane / ethyl acetate 1: 1, o-methyl oxime of 4'-bromo-2-hydroxyacetophenone 174.3 g, an oil was obtained, purity approximately 90%, 2 isomers .

VP2 precursor: 2-amino-2- (4-bromophenyl) ethanol (amino alcohol of formula VI) O-methyl oxime of 4'-bromo-2-hydroxyacetophenone (54.8 g, 224 mmol), was added dropwise to 20 ° C under nitrogen as a solution in 5 THF to a mixture of lithium hydride-aluminum (20 g, 505 mmol) and aluminum chloride (15.3 g, 112 mmol) in THF (350 mL). After 4 hours, the mixture was hydrolyzed (40 ml of methanol, 200 ml of 2N NaOH), and extracted with heptane / ethyl acetate. The crude product (42 g) was recrystallized from heptane / ethyl acetate 2: 1. This gave 2-amino-2- (4-bromophenyl) ethanol, 29.3 g, 10 colorless crystals, m.p. 95 ° C.

VP3 precursor: N-ri- (4'-bromophenyl-2-hydroxyethyl) -2,6-difluorobenzamide (formula VID 2,6-difluorobenzoyl chloride (13.8 ml, 110 mmol) was added dropwise at 20 ° C, to 2-amino-2- (4-bromophenyl) ethanol (25.0 g, 116 mmol) and triethylamine (19.5 ml, 139 mmol) in THF (150 ml). After 15 hours, the mixture was stirred with water and extracted with heptane / ethyl acetate. This gave the product amido alcohol, 38.6 g, pale yellow solid, m.p. 141 ° C. ^^^ j ^ jjg? ^? jX VP4 Precursor: 2-.2,6-d? -fluorophenyl) -4- (4-bromophenyl) oxazole (Formula III) Synthesis using the thionyl chloride / alkali metal hydroxide method The amido alcohol VP3 (38.5 g, 108 mmol) was mixed in dichloromethane with thionyl chloride (9.7 ml, 130 mmol) and heated for 5 hours at 40 ° C. The mixture was concentrated and the residue (= amidochloride, 36.5 g) was refluxed with 6N NaOH (32.5 ml) in dioxane (180 ml) (6 hours). The mixture was stirred with water and extracted with ethyl acetate. The crude product (oil 31.8 g) was recrystallized from heptane / ethyl acetate 9: 1. This gave 2- (2,6-difluorophenyl) -4- (4-bromophenyl) oxazoline, 17.8 g, colorless crystals, m.p. 98 ° C; e.g. 365 ° C (GC).

Synthesis using the tosyl chloride / amine method The VP3 amido alcohol (5.0 g, 14.0 mmol) was mixed in dichloromethane (40 ml) with triethylamine (5.67 g, 56 mmol) and tosyl chloride (2.94 g, 15.5 mmol), and refluxed for 5 hours. The mixture was concentrated, and the residue was stirred with water and extracted with ethyl acetate. The crude product (4.6 g) was recrystallized with ethanol / water 8: 2. This gave 2- (2,6-difluorophenyl) -4- (4-bromophenyl) oxazoin, 3.4 g, colorless crystals, m.p. 97 ° C; 1 H NMR (CDCl 3, ppm): 4.24, 4.81, 5.43, oxazoline; 7.00, 7.43, F2C6H3; 7.23, 7.51, BrC6H4.

VP5 precursor: 2- (2,6-dichlorophenyl) -4- (4-trimethylastanophenyl) -oxazoline (formula IX) VP3 2- (2,6-difluorophenyl) -4- (4-bromophenyl) oxazoline (16.4 g , 48.8 mmole) was introduced into dioxane under nitrogen, hexamethyldistan (20 g, 61.2 mmol), Pd (PPh3) 4 (1.4 g, 1.2 mmol) and lithium chloride (0.38 g, 4.4 mmol) were added, and the mixture was added. He refluxed for 7 hours. The reaction mixture was stirred with water and extracted with heptane / ethyl acetate. The crude product (19.6 g, oil) contained approximately 70% of the Sn product. Separation by chromatography (eluent: heptane / ethyl acetate 2: 1) yielded 2- (2,6-dichlorophenyl) -4- (4-trimethylstanylphenyl) oxazoline, 13.4 g, oil, which became crystalline, DC Rf 0.59 (VP4 Rf 0.49).

VP6 precursor: 5-bromo-2-trifluoro-methoxy-pyridine Sodium hydride (18.6 g, 60%, 464 mmol) was added in DMF (500 ml) under nitrogen. Trifluoroethanol (32.2 ml 443 mmoles) was added in portions at 10 ° C. After 1 hour, 2,5-dibromopyridine (100 g, 422 mmol) was added portionwise, and the mixture was stirred in a water bath for 24 hours at 20 ° C. It was then stirred with water and extracted with ethane / ethyl acetate 9: 1. Distillation of the crude product (105 g) yielded 5-bromo-1-trifluoroethoxypyridine, 82.1 g (93% purity) colorless fluid, e.g. 97-104 ° C at 18 mbar. Other alkoxypyridines and alkylthiopyridines were prepared analogously.

VP7 precursor: 5,5-dimethyl-2- (2-trifluoroethoxy-pyridin-5-yl) -1, 3.2-dioxaborin-5-bromo-2-trichloroethoxypyridine (30.0 g, 117 mmol) was introduced into THF / diethyl ether 2: 1 (250 ml) under nitrogen, and cooled. A solution of 5 n-butyllithium (2.5 M, 53.9 ml, 135 mmol) was added at about -85 ° C using a syringe. After 10 minutes, isopropyl borate (33.1 ml, 141 mmol) was added dropwise at about -80 ° C. The temperature of the mixture was allowed to rise to -10 ° C and acetic acid (10.1 ml, 176 mmole) and 2,2-dimethylpropanediol (15.9 g, 152 mmole) were added. After After 10 hours at 20 ° C, the mixture was stirred with water and extracted with heptane / ethyl acetate. The crude product (31.5 g) was recrystallized using heptane / ethyl acetate 95: 5. This gave 5,5-dimethyl-2- (2-trifluoroethoxypyridin-5-yl) -1, 3,2-dioxaborin, 20.3 g, white solid; H NMR (CDCl 3, ppm): 1.02, Me; 3.75, OCH2; 4.77, PyOCH2; 6.82, 7.97, 8.50, PyH. Other 2-pyridyl-1, 3,2-dioxaborinones were prepared analogously.

VP8 precursor: 2-Ethoxy-5-trimethylstanilpyridine 5-Bromo-2-ethoxypyridine (14.9 g, 68 mmol) was introduced into THF / diethyl ether 2: 1 (120 ml) under nitrogen. N-Butyllithium / hexane solution (2.5 M, 33 mL, 82 mmol) was added at -80 ° C. After 15 minutes, chlorotrimethyltin (16.4 g, 82 mmol), dissolved in THF, was added dropwise. The temperature of the mixture was allowed to rise to 0 ° C, and the mixture was ^^^^ ___ g ^ ^ ^^^ ^ i =? m was stirred with water and extracted with heptane / ethyl acetate. The crude product (15.7 g) was distilled in vacuo. This gave 2-ethoxy-5-trimethylstanylpyridine, 1.2 g, e.g. 66-75 ° C at 1.2 mbar. Other stanilpyridines were separated analogously.

VP9 precursor: 5- [4-1-amino-2-hydroxyethyl-2-trifluoroethoxypyridine 2-amino-2- (4-bromophenyl) ethanol VP2 (3.8 g, 17.1 mmol) and 5.5- dimethyl-2- (2-trifluoroethoxypyridin-5-yl) -1,2,2-dioxaborinam VP7 (6.55 g, 20.4 mmol) were refluxed together with tetrakis (triphenylphosphine) palladium (0.63 g, 3 mol%) , sodium carbonate (3.7 g, 35.4 mmol) in toluene / ethanol / water (8: 2: 1, 50 ml) for 7 hours. After the extraction and purification treatment by column chromatography, 5- [4- (1-amino-2-hydroxyethyl) phenyl] -2-trifluoroethoxypyridine, 2.2 g, m.p. 129 ° C.

Oxazoline products 2- (2,6-D-fluoro-phenyl) -4-r4- (2-ethoxypyridin-5-yl) -phenyl-oxazoline (Example No. 2) 2- (2,6-difluorophenyl) -4- (4-bromophenyl) Oxazoline (VP4) (5.00 g, 14.8 mmol) was mixed with 2-ethoxy-5-trimethylestanilpyridine (VP8) (5.06 g, 17.8 mmol), Pd (PPh3) (0.68 g, 0.59 mmol) and lithium chloride ( 0.12 g, 2.9 mmol) in dioxane (40 ml) and the mixture was refluxed under nitrogen (7 hours). After extraction and chromatography, 2- (2,6-diflurorphenyl) - . . . . . . ... -. »,. . . . «... . < . . . . < 8hfe ^ .A «~ -. 4- [4- (2-ethoxypyridin-5-yl) pheny] oxazoline, 3.86 g, m.p. 119 ° C; 1 H NMR (CDCl 3, ppm): 1.42, 4.35, OCH 2 CH 3; 4.40, 4.84, 5.51, oxazoline; 6.79, 7.77, 8.36, pyridine; 7.00, 7.41, 7.54, phenyl. 2- (2,6-d.fluorophenyl) -4- [4- (2-trifluoroethoxypyridin-5-yl) phenol] oxazoline (Example No. 3) 2- (2,6-difluorophenyl) -4- (4-bromophenyl) oxazoline (VP4) (2.0 g, 5.9 mmol) was mixed with 2-trifluoroethoxy-5-trimethylstannyl pyridine (2.61 g, 7.7 mmole), tetrakis (triphenylphosphine) palladium (0.22 g, 0.18 mmole), and lithium chloride (0.38 g, 8.9 mmole) in dioxane (30 ml) and refluxed for 9 hours. After the extraction treatment and column chromatography, 2- (2,6-difluorophenyl) -4- [4- (2-trifluoroethoxypyridin-5-yl) phenyl] oxazoline, 1.37 g, colorless crystals was obtained. 19 F NMR (CDCl 3): -75.05 (CF 3), -110.45 (ArF). 2- (2,6-D-fluorophenyl) -4-r4- (2-n-propyloxypyridin-5-yl) phenoxazole (Example No. 4) 2- (2,6-difluorophenyl) -4- (4-bromophenyl) oxazoline (VP4) (2.0 g, 2.9 mmol) was mixed with 2-n-propyloxy-5-trimethylstan-pyridine (4.6 g, 50%, 7.7 mmol), Pd (PPh3) 4 (0.35 g). , 0.3 mmoles) and lithium chloride (50 mg) in dioxane and the mixture was refluxed under nitrogen (7 hours). After chromatography and recrystallization from heptane / ethyl acetate 95: 5, 2- (2,6-d-fluoro-phenyl) -4- [4- (2-propyloxypyridin-5-yl) phenyl] oxazoline, 1.21 was obtained. g, colorless crystals; 1 H NMR (CDCl 3, ppm): 1.05, 1.82, 4.29, OC3H7; 4.32, 4.86, 5.51, oxazoline; 6.80, 7.78, 8.37, pyridine; 7.02, 7.42, 7.54, phenyl. 2- (2,6-difluorophenyl) -4-f4- (2-isobutyloxypyridin-5-yl) phenoxazole (Example No. 8) 2- (2,6-difluorophenyl) -4- (4-bromophenyl) ) oxazoline (1.00 g, 2.96 mmol) was mixed with 5,5-dimethyl-2- (2-isobutyloxy-pyridin-5-yl) -1, 3,2, -10 dioxaborin (1.4 g, purity) 80%, 4.3 mmol), Pd (PPh3) 4 (0.17 g, 0.15 mmol) and sodium carbonate (0.62 g, 5.9 mmol) in toluene / ethanol / water 8: 2: 1 (15 ml) and the mixture was refluxed for 8 hours under nitrogen. After extraction and chromatography, 2- (2,6-difluorophenyl) -4- [4- (2-isobutyloxypyridin-5-yl) phenyl] oxazoline, 1.14 g, colorless oil was obtained. 1 H NMR (CDCl 3, ppm): 1.04, 2.11, 4.10, o-isobutyl; 4.33, 4.84, . 51, oxazoline; 7.00, 7.42, 7.55, phenyl; 6.81, 7.77, 8.37, pyridine. 2- (2,6-difluorophenyl) -4- [4- (2-trifluoroethoxypyridin-5-yl) phenntanezoline (Example No. 19) 2- (2,6-difluorophenyl) -4- ( 4-bromophenyl) thiazoline (0.90 g, 2.5 mmol, obtained from VP3 precursor and Lawesson's reagent in toluene), was mixed with 2-trifluoroethoxy-5-trimethylstanylpyridine (1.21 g, 3.6 mmol), Pd (PPh3) 4 ( 0.15 g) and lithium chloride (0.16 g) in dioxane (10 ml), and the mixture was refluxed.

MMMÉ? WÉÍ - I • É Aá ái for 8 hours. After extraction and chromatography, 2- (2,6-difluorophenyl) -4- [4- (2-trifluoroethoxy-pyridin-5-yl) phenyl] thiazoline, 0.46 g, beige solid; MS: M + 450. 1 H NMR (CDCl 3, ppm): 3.45, 3.94, 5.83, thiazoline; 4.82, OCH2CF3; 6.95, 7.87, 8.36, pyridine, 7.00, 7.40, 7.53, phenyl. 2- (2,6-d.fluorophenyl) -4- [4- (2-n-propylpyridn-5-yl) phenylazoline (Example No. 34) 2- ( 2,6-difluorophenyl) -4- (4-bromophenyl) oxazoline (0.8 g, 2.4 mmol) was refluxed for 8 hours with dimethyl-2- (2-n-propylpyridin-5-yl) -1, 3 , 2-dioxaborin (0.72 g, 3.1 mmol), Pd (PPh3) 4 (0.14 g, 0.12 mmol) and sodium carbonate (0.5 g) in toluene / ethanol / water 8: 2: 1 (11 ml). After extraction and chromatography, 2- (2,6-difluorophenyl) -4- [4- (2-n-propylpyridin-5-yl) phenyl] oxazoline, 0.20 g, pale-colored solid was obtained. 1 H NMR (CDCl 3, ppm): 1.01, 1.80, 2.81, n-propyl; 4.34, 4.85, . 53 oxazoline; 7.00, 7.44, 7.59, phenyl; 7.21, 7.79, 8.76, pyridyl. 2- (2,6-difluorophenyl) -4-r4- (2-ethylsulfonyl-pyridin-5-yl) phenoxazoline (Example No. 40) 2- (2,6-difluorophenyl) -4 - [4- (2-ethylthio-pyridin-5-yl) phenyl] oxazoline (Example No. 39; 0.60 g, 1.5 mmol) was stirred for 5 hours at 20 ° C with 3-chloroperbenzoic acid (0.41 g, 1.7 mmol) in dichloroethane (10 ml).

After extraction and chromatography, 2- (2,6-difluorophenyl) -4- [4- (2-ethylsulfonylpyridin-5-yl) phenyl] oxazoline, 0.21, colorless oil was obtained. 1 H NMR (CDCl 3, ppm): 1.24, 2.98, 3.21, SO-CH 2 CH 3; 4.33, 4.87, 5.56, oxazoline; 7.01, 7.48, 7.64, phenyl 8.03, 8.11, 8.84, pyridine. 2- (2,6-difluorophenyl) -4-r4- (2 (N-acetylethylamine) pyridin-5-iPphenylexazoline (Example No. 51) 2- (2,6-difluorophenyl) -4- (4- Trimethylglycanoyl) oxazole (0.84 g, 2.0 mmol) was mixed with 2- (N-acetylamino) -5-iodopyridine (0.93 g, 3.2 mmol), Pd (PPh3) 4 (0.12 g) and lithium (0.15 g) in dioxane (10 ml), and the mixture was refluxed for 8 hours After separation by chromatography (eluent: ethyl acetate), 2- (2,6-difluorophenyl) -4- [ 4- (2- (N-acetylamino) pyridin-5-yl) phenyl] oxazoline, 0.31 g, pale oil, 1 H NMR (CDCl 3, ppm): 1.19, 3.94, NC2H5, 2.08, COCH3, 4.33, 4.87, 5.54, oxazoline, 7.00, 7.43, 7.48, 7.61, phenyl, 7.32, 7.96, 8.75, pyridine. 2- (2,6-d-fluoro-phenyl) -4-f4- (1-n-propyl-2-pyridon-5-yl) phenyl-oxazolyl (Example No. 152) 2- (2,6-d.fluorophenyl) -4- (4-trimethylstanylphenyl) oxazoline (0.5 g, 1.2 mmol) was mixed with 1-n-propyl-5-bromo-2-pyridine (0.51 g, 2.4 mmol), Pd (PPh3) 4 (70 mg) and lithium chloride (0.20 g) in dioxane (10 ml), and refluxed 8 hours under nitrogen. After the extraction treatment and chromatography (eluent: ethyl acetate), 2- (2,6-difluorophenyl) -4- [4- (1-n-propyl-2-pyridon-5-yl) phenyl] was obtained] oxazole, 0.20 g, oil. 1 H NMR (CDCl 3, ppm): 1.00, 1.81, 3.96, NC3H7; 4.30, 4.83, 5.49, oxazoline; 6.64, pyridone; 7.00, 7.4-7.7, phenyl and pyridone. 2- (2-chlorophenol) -4-r4- (2-trifluoroethoxy-pyridin-5-yl) phenyxazole (Example No. 25) 2- (2-chlorophenyl) -4- (4 -bromophenyl) oxazoline (prepared in analogy to VP4) (0.80 g, 2.4 mmol) and 5,5-dimethyl-2- (2-trifluoroethoxypyridin-5-yl) -1, 3,2-dioxaborinone VP7 (1.03 g , 3.6 mmoles) was refluxed with Pd (PPh3) 4 (0.1 g) and sodium carbonate (0.5 g) in toluene / ethanol / water 8: 2: 1, 11 ml) (8 hours). After extraction and column chromatography, 2- (2-chlorophenyl) -4- [4- (2-trifluoroethoxypyridin-5-yl) phenyl] oxazoline was obtained as a pale-colored oil, 0.86 g; 1 H NMR (CDCl 3): 4.31, 4.80, 5.50, oxazoline; 4.80 OCH2CF3; 6.93, 7.3-7.5, 7.84, 8.35, pyridine and phenyl. 2- (2,6-difluorophenyl) -4-f2-ethoxy-4- (2-trifluoroethoxypyridin-5-D-phenylexazoline (Example No. 106) Example 106 was prepared in analogy to example 25. 1 H NMR (CDCl 3) : 1.45, 4.15 OEt; 4.45, 4.92, 5.73, oxazoline; 4. 81 OCH2CF3; 6.94, 7.84, 8.35, pyridine; 6.98, 7.12, 7.41, 7.53, phenyl. 2- (2-fluorophenyl) -4-f4- (2-trifluoroethoxypyridin-5-yl-phenoxazoline (Example No. 402) Example 402 was prepared in analogy to example no.25.1H NMR (CDCl3): 4.31, 4.82, 5.48, oxazoline, 4.80, OCH2CF3, 6.92, 7.84, 8.35, pyridine, 7.20, 7.40, 7.50, 8.00, phenyl. 1 -, .... »...... i ^ ..-. .... ..... ,, ... . --.- .. * _ A. CHEMICAL EXAMPLES (TABLES 1-8) TABLE 1 Oxazolines and thiazolines of the formula (I), G = 3-pyridyl No of Ar Z R5 R ° Physical data (p.f., 20 ° c 18 ° C, NMR fifteen 50, NMR 22 Ar2 O OCH2CF3 H dTÉHMÍliiHItttlaiiii HMiiMairiüiÉ ^ fgi ^ dgiáM _________ 23 Ar2 O OnC3H7 24 Ar3 O OC2H5 H 25 Ar3 O OCH2CF3 H 26 Ar3 O OnC3H7 H 27 Ar4 O OC2H5 H 28 Ar4 O OCH2CF3 H pf: 136-137 ° C 1H - NMR (CDCl 3, TMS: d = 2.46 (s, 6H, CH 3); 4.33, 4.88, 5.57 (each dd, 1 H, oxazoline); 4.85 8q, 2H, CH 2 CF 3); 6.97 7.90, 8.39 (each dd, 1 H, PyH); 7.59, 7.51 (each m, 2H, C6H4), 7.08-7.28 (m, 3H, C6H3). 19F-NMR (CDCI3, CFCI3). d = -74.3 29 Ar4 O OnC3H7 H 30 Ar1 O OCH (CF3) CH2O H CH3 31 Ar1 O CH3 H 32 Ar1 O CF3 H 33 Ar1 O C2H5 H 34 Ar1 O nC3H7 H 35 Ar1 O nC4H9 H p.f. 1 17 ° C 36 Ar1 O nCsHii H 15 37 Ar1 O nCeH-13 H 38 Ar1 O SCF3 H 39 Ar1 O SC2Hd H p.f. 100 ° C 40 Ar1 O SO-C2H5 H 41 Ar1 O SO2-C2H5 H 42 Ar1 O SCH2CF3 H 43 Ar1 O S-nC3H7 H p.f. 90 ° C 44 Ar1 O SO-nC3H7 H 45 Ar1 O SO2-nC3H7 H 46 Ar1 O S-nC4H9 H 20 47 Ar1 O Br H EM 414, 416 48 Ar1 O Cl Cl 49 Ar1 O NH-COCH3 H t_Ék (Ui__ia __ ^ __ _i 50 Ar1 O NH-COC2H5 51 Ar1 ON (C2H5) COCH3 H NMR 52 Ar1 O 1 -Morpholinyl H pf 170 ° C 53 Ar1 O CH2OCH3 H 54 Ar1 O CH2OC2p5 H 55 Ar1 O C2H4OCp3 H 56 Ar1 O OCH2C6p5 H pf 120 ° C 57 Ar1 O OCH2CON (CH3) 2 H 58 Ar1 O OC2H4CH (CH3) 2 H 59 Ar1 O OCH2CH (C2H5) CH H 60 Ar1 O OCH2-COOCH3 H 61 Ar1 O OCHF2 H 1 ßf NMR: - 90.1, d; -110.5, ArF H3 - '* - "• f - * - ~ -... a.» «-«.

TABLE 2 Oxazolines of the formula (I), G = 3-pyridyl No. of X1 X¿ Z E R1 RD Data eg. physical 100 F F O CH2 H OC? H5 p.f. 105 ° C 101 F F O CH2 H OCH2CF3 102 F F O CH2 H OnC3H7 103 F F O - 2-F OC? H5 104 F F O - 2-CI OC? CF3 10 105 F F O - 2-OCH3 OC? H5 NMR ddi ílÉMfii &ampilii TABLE 3 Oxazolines of the formula (I). G = 2-pyridon-5-yl No. of X X2 R4 R5 Physical data eg 150 F F H H p.f. 197 ° C 151 FF C2Hd H 152 FF nC3H7 H NMR 153 FF CH -CH = CH2 H 154 FF CH2-CH = CH-CH3 H 155 FF CH2CON (CH3) 2 H 156 FF CHF2 H 157 FF CH2CF3 H 158 FF CH2C6H5 H 159 FF CH2CH (CH3) 2 H 160 FF CH2-CCH H 161 FF CH2-CC-CH3 H 162 FF cC6H.? H 162 F F cC5H9 H 163 F F CH2cCßH ?? H 164 F F C2H4? C2H5 H 165 F F CH2OCH2C8H5 H 166 F F C2Hd 3-Cl 167 F F nC3H7 3-Cl 168 F F C2H5 3-CH3 169 F F nC3H7 3-CH3 dáUád? iÉ. He > ^ M > ? d ^ Í ^ > TABLE 4 Oxazolines of the formula fl). G = 4-pyridyl No. of X x R Physical data eg. 170 F F O H p.f. 137 ° C 171 FFO OC2H5 172 FFO Cl 10 173 F Cl O OC2H5 174 FFO C2H5 175 FFO nC H9 176 FFO OCH2CF3 177 FFO CF3 178 FFO OnC3H7 179 FFO SC2H5 180 FFO SO-C2H5 181 FFO SO2-C2H5 182 FFS OC2H5 15 183 FFS OnC3H7 184 FFO OCH2-3-pyridyl 185 FFO 1 -pyrrolyl u ^ g ^ MiüilMtti _ ^^^ _ a | kdMaajMÉ || tt¡ TABLE 5 Oxazolines of the formula f). G = 2-pyridon-3-yl No. of ex. X1 X2 R4 R5 Physical data 200 FFOC C22HH5 H 201 FFOC C22HH5 6-OC2H5 202 FFOC C22HH5 6-OCH2CF 203 FFOC C22HH5 6-OnC3H7 204 FFOC CHH33 H 205 FFOC CHH33 6-OC2H5 206 FFO CH3 6-OCH2CF 207 FFO CH3 6-OnC3H7 208 FFO CH3 5-CI 209 FFO CH3 5-Br 210 FFOC CHH2? CF3 H 211 FFO CH2CF3 6-OC2H5 TABLE 6 Oxazolines of the formula fl). G = 2-pyridone-4-yl No. of ex. X1 X2 R4 R5 Physical data 250 FF CH3 H 251 FF C2H5 H 10 252 FF CH2CF3 H 253 FF nC2H7 H 254 FF iC3H7 H 255 FF nC4H9 H 256 FF CH2CH (CH3) 2 H 257 FF CH2C6H5 H 258 FF CH2CC6H11 H 259 FF CH2H4OCH3 H 260 FF C2H4? C H5 H 261 FF C2H5 5-CI 15 > .. -pull. Jmtz TABLE 7 Oxazolines of the formula fl). G = 3-pyridinyl. Ar = heteroaryl. of ej. Ar R5 R6 Physical data »» - ,. -. * .. «• -. ^^^ Éüaa ^ Bdiiii MÉRIÜMMIliÉWHM ^^^ A Ed ^^^ ita.MMiM. aMaHi? aaiiUHaw? l? áÉaBaab_l? _b_k_u _ ^ _ ^ talba ......,. . to**..-... .,,-,-.

TABLE 8 Oxazolines of the formula I, G = 3-pyridyl R5 = heterocyclyl heterocyclyloxy, heterocyclylalkyl, heterocyclylalkoxy X1 X2 Rfc R5 Data No. of ex. physical 350 F F H 351 F F H O 354 H. ..H, 355 H -O 357 F F H 358 F F H ^, CH,? II 359 H • o-N Ukl? L > i &^ U ^ ni > 361 F F H Y. 362 F F H Y 364 H ^ - N -o. 365 F F H 367 F F H 369 F F H O-CI 370 F F H * ~. // 371 F F H 372 F F H JJ F H -0. 15 373 F s- 374 F o. F H 0C.-H4-C OCH O-Ch OCrtr 382 F F H TABLE 9 Oxazolines of the formula fl). G = 3-pyridinyl No. of ex. X1 RB R5 Physical data 400 2-F 4-F H OCH2CF3 1 F NMR: -75.1, tr, CF3, -105.4, m, ArF 401 2-F 5-F OCH2CF3 9F NMR fifteen - . 15 -74.3, CF3; -115.1, -118.7, ArF 402 2-F OCH2CF3 NMR, m.p. 101 ° C GJüiMMiidY 7 412 2-OCH3 H H OCH2CF3 B. EXAMPLES OF FORMULATIONS a) A powder is obtained by mixing 10 parts by weight of active substance and 90 parts by weight of talc as an inert material, and grinding the mixture in a hammer mill. b) A wettable powder which is easily dispersible in water, is obtained by mixing 25 parts by weight of active substance, 65 parts by weight of quartz containing kaolin as inert material, 10 parts by weight of potassium lignosulfate and 1 part by weight of sodium oleoylmethyltaurinate as a humectant and dispersant, and grinding the mixture in a spinning disc mill. c) A dispersion concentrate which is readily dispersible in water, is prepared by mixing 40 parts by weight of active substance with 7 parts by weight of a monoester sulfosuccinic, 2 parts by weight of a sodium lignosulfonate and 51 parts by weight of water , and grinding the mixture in a ball mill to a fineness below 5 microns.

M ^? Tmt *? Ma? Td) An emulsifiable concentrate can be prepared from 15 parts by weight of active substance, 75 parts by weight of cyclohexanone as a solvent, and 10 parts by weight of oxyethylated nonylphenol (10 EO) as an emulsifier . E) Granules can be prepared from 2 to 15 parts by weight of active substance and a carrier material for inert granule such as attapulguite, pumice granules and / or sand of cuerzo. It is convenient to use a suspension of a wettable powder of example b) with a solids content of 30%, which is sprinkled on the surface of 10 attapulgite granules, and these are dried and mixed tightly. The wettable powder reaches an amount of about 5% by weight, and the inert carrier material of about 95% by weight of the finished granules.

C. BIOLOGICAL EXAMPLES EXAMPLE 1 Effect on Tetranychus urticae mites Bean plants (Phaseolus vulgaris), which were severely infected with a full population of mites (Tetranvchus urticae), were sprayed to the point of exhaustion with an aqueous solution of the formulated preparation to be tested. Mortality of all stages MteHMM ^ ÍHi | M? _É _______? of acarus was determined after 7 days. At a concentration of 300 ppm (based on the content of active substance), the preparations of examples 1, 2,3,4,7,8,9,14,18,21, 31, 40,41, 43,44 , 47,51, 106,152 and 153, showed a mortality of 90-100%.

EXAMPLE 2 Effect on the aphid Aphis fabae Beans (Vicia faba) which were densely populated with the black bean aphid (Aphis fabae) were sprayed to the point of exhaustion, with an aqueous solution of the formulated preparation to be tested. The mortality of the acids was determined after three days. At a concentration of 300 ppm (based on the content of active substance), the preparations of Examples 1, 2,3,4,7,8,152, showed a mortality of 90-100%.

EXAMPLE 3 Effect on the butterfly larva Spodoptera litoralis larvae L4 of the Egyptian cotton leaves worm (Spodoptera litoralis), were introduced in a petri dish whose bottom had been covered with filter paper and contained approximately 5 ml of nutrient medium. Then, the filter paper, the nutrient paper and the lavas that had been introduced were sprinkled with an aqueous solution of the formulated preparation to be tested. Then, the petri dish was sealed with a lid. After storage for 4 days at approximately 23 ° C, the effect of the preparation on the larvae was determined. At a concentration of 5 300 ppm (based on the content of active substance), the preparations of examples 3,4,22,105, 106, showed a larval mortality of 90-100%.

EXAMPLE 4 10 Effect on the larval stage of Heliothis virescens eggs A petri dish was prepared whose bottom was covered with filter paper, and which contained approximately 5 ml of nutrient medium. Sections of filter paper containing approximately 30 eggs of 24 hours old of the tobacco budworm, were immersed for 5 seconds in an aqueous solution of the formulated preparation to be tested, and then placed in the petri dish. Another 200 μl of the aqueous solution was distributed over the nutrient medium. After the petri dish was sealed, it was stored in a controlled environment cabinet about 25 ° C. after storage for 6 days, the mortality of the preparation was determined on the eggs and larvae hatched therefrom. At a concentration of 300 ppm (based on the content of active substance), the preparations of the Examples 1, 2,3,4,5,6,7,8,14,17,21, 22,23,34,35,39,40,43,44,106, caused a mortality of 90-100%.

EXAMPLE 5 Effect on the worm of the corn buds Diabrotica undecimpunctata Corn seed was previously germinated for 6 hours while submerged in water, then placed in 10-ml glass tubes and covered with 2 ml of soil in each case. After 1 ml of water was added, the plants remained in the glass tubes at 21 ° C until the height of the plant was about 3 cm. Then, 10 L2 worm larvae of the corn buds (Diabrotica undecimpunctata) were introduced into each tube on the ground. Two hours later, 1 ml of an aqueous solution of the formulated preparation to be tested was pipetted onto the surface of the soil inside the tubes. After storage for 5 days under laboratory conditions at 21 ° C, The existence of life on earth and root sections was examined, and mortality was determined. At a concentration of 300 ppm (based on the content of active substance), the preparations of Examples 2,3,5,9,19,39 showed a mortality of 100% of the test animals employed.

EXAMPLE 6 Effect on Lucilia cupren larvae In a test container, 20 freshly hatched 5 larvae of Luciiia cuprina were placed on a nutrient medium for ground sheep larvae, which contained the test substance in a concentration of 100 ppm. The growth of the larvae on the nutrient medium was monitored for 72 hours until the larva 3. At a concentration of 100 ppm (based on the content of active substance), the preparations 10 of the examples 2,3,4,5,105, 106 , showed a 100% mortality in the fly larvae used.

EXAMPLE 7 Effect on the stages of development of the cat flea 15 Ctenocephalides felis The nutrient medium of the cat flea larvae, composed of equal parts of blood meal and quartz sand, was mixed with the test substance at a concentration of 1000 ppm. Approximately 30 20 flea eggs recently obtained from a breeding colony were transferred to the medium. To evaluate the effect of the preparation, we observed the hatching of the flea larvae and their development in adult pupae and fleas. The test substances of Examples 2, 3 and 4 caused a 100% mortality.

Claims (19)

NOVELTY OF THE INVENTION CLAIMS

1. A 1,3-oxazoline derivative and a 1,3-thiazoline derivative of the formula (I) Wherein the symbols have the following meanings: A is phenyl, pyridyl, pyrimidinyl, pyrazinyl, pyrazolyl or thienyl, each of the aforementioned groups being optionally substituted with one or more radicals X; X is the same as or different from) halogen, cyano, nitro; b) C 1 -C 4 alkyl, C 2 -C 4 alkenyl, C 2 -C 4 alkynyl, C 4 alkoxy, C 1 -C 4 alkylthio, d-C 4 alkylsulfinyl, C 3 -C 8 cycloalkyl, C 4 -C 8 cycloalkenyl, phenyl, the radicals of group b being optionally substituted with one or more radicals selected from the group consisting of halogen, cyano, C1-C4 alkyl, halogenalkyl of C.-C4, alkoxy of C1-C4 and halogenoalkoxy of C. -C4; E is a Simple bond, C1-C4 alkylene, -O-CH2- or -CH2-O-; G is a radical selected from the group consisting of: MMfcaatfÉÜMÉ Z is oxygen or sulfur; R1, R2 and R3 are identical or different, hydrogen, halogen, C1-C4 haloalkyl, C1-C4 alkyl, C1-C4 alkoxy, C-io-C4 haloalkoxy or cyano; R4 is hydrogen or alkyl group of CrC8, alkenyl of C2-C8, alkynyl of C2-C8, cycloalkyl of C3-C8, cycloalkenyl of C3-C8, cycloalkylalkyl of C4-C10 or phenylalkyl of C7-C-? 2, each one of the aforementioned groups optionally substituted with one or more substituents which are selected from the group consisting of halogen, C1-C4 alkyl, C1-C3 haloalkyl, C1-C4 alkoxy, C1-C3 halogenoalkoxy, C1 alkylthio -C3, C3-C8 cycloalkyl, C7-C12 phenylalkoxy, C2-C4 alkylcarbonyl, alkoxycarbonyl, C2-C6 monoalkylcarbonyl and C3-C9 dialkylaminocarbonyl, cyano and tri-alkylsilyl C1-C4; R5 and R6 are the same as or different from a) hydrogen, halogen, cyano, C2-C5 alkylcarbonyl formyl, C2-C8 alkoxycarbonyl, C3-C9 monoalkylcarbonyl and dialkylaminocarbonyl; b) C?-C8 alkyl, C3-C8 cycloalkyl, C-C8 cycloalkenyl, C -?-C8 alkoxyalkyl, C?-C8 alkylthio, C 8 -alkylsulfinyl, C?-C8 alkylsulfonyl, NR 7 R 8, phenyl, phenoxy, phenylalkyl of C7-C-i2, phenylalkoxy of C7-Ci2, heterocyclyl, heterocyclyl derivatives, heterocyclyl-alkoxy of C.-C4, heterocyclylalkyl of C3-C12, each of groups b being optionally substituted with one or more, preferably one to three radicals which are selected from the group consisting of halogen, C1-C4 alkyl, C1-C3 haloalkyl, C1-C3 alkoxy, C1-C3 halogenoalkoxy, C1-C3 alkylthio, NR7R8 , C2-C5 alkylcarbonyl, C2-C8 alkoxycarbonyl, C3-C9 monoalkylcarbonyl and dialkylaminocarbonyl, cyano and trialkylsilyl of C-1-C4; c) C 1 -C 8 alkoxy, each of the groups c being optionally substituted with one or more radicals which are selected from the group consisting of halogen, C 1 -C 3 alkylthio, NR 7 R 8, C 2 -C 5 alkylcarbonyl, alkoxycarbonyl C2-C8, C3-C9 monoalkylcarbonyl and dialkylaminocarbonyl, cyano and trialkylsilyl of C1-C4; d) R5 and R6 together form a ring which is originated by linking two of the groups mentioned in b), preferably C3-C5 alkylene, C2-C4 alkyleneoxy, C1-C3 alkylenedioxy, C2-C4 alkyleneamino or alkylenethio of C2-C4; R7 and R8 are the same or different a) hydrogen; b) C8 alkyl, C3-C8 cycloalkyl, C7-Ci2 phenylalkyl, Ci-C3 alkylcarbonyl, Ci-Cß alkylsulfonyl which are optionally substituted with one or more radicals which are selected from the group consisting of halogen, C 1 -C 4 alkyl, C 1 -C 3 haloalkyl, C 1 -C 4 alkoxy, C 1 -C 3 halogenoalkoxy, C 1 -C 3 alkylthio, C 1 -C 3 alkylamino, C 1 -C 3 dialkylamino, C 3 -C 8 cycloalkyl, cyano and trialkylsilyl of C 1 -C 4; or c) R7 and R8 together are C3-C alkylene, oxa-alkylene, aza-alkylene or thia-alkylene of C3-C, alkylenecarbonyl of C3-C, or alkylenesulfonyl of C3-C.

2. - A compound of the formula (I) according to claim 1, further characterized in that the symbols have the following meanings: A is phenyl or pyridyl; X is a) halogen, cyano, nitro or b) C 1 -C 4 alkyl, C 1 -C 4 alkenyl, C 1 -C 4 alkynyl, C 1 -C 4 alkoxy, C 1 -C 4 alkylthio, C 1 -C 4 alkylsulfinyl, cycloalkyl of C3-C, C-C8 cycloalkenyl, the radicals of group b being optionally substituted with one or more radicals which are selected from the group consisting of halogen, cyano, C1-C4 alkoxy and C1-C4 halogenoalkoxy; E is a simple link or is -CH2-; G is

Z is oxygen; R1, R2, R3 are H, halogen, C1-C4 haloalkyl, CrC alkyl, C1-C4 alkoxy, C-1-C4 haloalkoxy or cyano; R4 is H or alkyl of 15 CrC8 which is optionally substituted with one or more radicals which are selected from the group consisting of halogen, C4 alkyl, C1-C3 haloalkyl, C1-C4 alkoxy, C1-C3 haloalkoxy, C1-C3 alkylthio , C3-C8 cycloalkyl, cyano or trialkylsilyl of C -? - C4; R5, R6 are a) H, halogen, cyano; b) CrC8 alkyl, C3-C8 cycloalkyl, cycloalkenyl

C4-C8, C-C8-alkylthio, C-C8-alkylsulfinyl, CrC8-alkylsulfonyl, C7-C2-phenylalkyl, C7-C2-phenylalkoxy, C4-C7-oxycycloalkyl or C4-oxacycloalkenyl C7, the groups b being optionally substituted with one or more radicals that are selected from the group consisting of • -j > -üfa-: 8 halogen, C1-C4 alkyl, C1-C3 haloalkyl, C.-C3 alkoxy, C1-C3 haloalkoxy, C1-C3 alkylthio and cyano; or c) C -? - C8 alkoxy which may be optionally substituted with one or more radicals which are selected from the group consisting of halogen, C1-C3 alkylthio and cyano. 3. A compound of the formula (I) according to claim 1 or 2, further characterized in that the symbols have the following meanings: A is phenyl; X is halogen, C1-C4 alkyl, C1-C3 haloalkyl, C1-C4 alkoxy or C-β-C3 haloalkoxy; E is a simple link; G is 3-pyridyl; Z is oxygen; R1, R2, R3 are H, halogen, C1-C4 haloalkyl, C1-C4 alkyl, C4 alkoxy, C1-C4 haloalkoxy; R4 is H or CrC8 alkyl which is optionally substituted with one or more radicals which are selected from the group consisting of halogen, C1-C4 alkyl, C1-C3 haloalkyl, C1-C4 alkoxy, C1-C3 halogenoalkoxy , C1-C3 alkylthio, C3-C8 cycloalkyl, cyano or trialkylsilyl of CrC4; R5, R6 are a) H, halogen, cyano, b) C -? - C8 alkyl, C -? - C8 alkoxy; C3-C8 cycloalkyl, C4-C8 cycloalkenyl, C? -C8 alkylthio, Ci-Cs alkylsulfinyl, C-pC alkylsulfonyl, C7-Ci2 phenylalkyl, or C7-C12 phenylalkoxy, the groups b being optionally substituted with one or more radicals that are selected from the group consisting of halogen, C1-C4 alkyl, C1-C3 halogenoalkyl, and cyano. 4. A compound of the formula (I) according to one or more of claims 1 to 3, which is selected from the groups consisting of (la) to (le): -, ^ a ^^ ri ^ tlÍit fc «MMh ^^^^^ *« * - ^ fc * ^ - ^^ JMa ^^ - ^ M »-a -» »» »» M ^ M ^ ** « i.MJfc ^^ MMtli. ^^ 1 t? __ t__? ? GÍ ?? 1 1tfc l ^^ fc-¿Atiaüa__a_¡__ in which the symbols have the meanings given in the formula (I) in claims 1 to 3.

5. A compound of the formula (I) according to claim 4, which is selected from the group consisting of (Ia1) to 5 (Ia4): • mn üiál * - * - '"-" - * "- - -'- ** - • - .- _y - ^^^ -_-_-_-___ ^ _ ^ _ A_J_ _j _-_ t_i _ ^ _ tiM_á en which symbols have the meanings given in formula (I) in claims 1 to 3.

6. A process for preparing compounds of formula (I) according to one or more of claims 1 to 5, which comprises reacting a halogen and a perfluoroalkylsulfonate compound of the formula (II) wherein Y is Cl, Br, I or perfluoroalkylsulfonate and A, Z and E have the meanings given in formula (I), with an organometallic compound of formula (III) GM (III), in which M is a leaving group containing B-, Sn- or Zn- and G has the meanings given in formula (I) in claim 1, with palladium catalysis.

7. A composition for crop protection comprising at least one compound according to any of claims 1 to 5 and at least one formulation aid.

8. A fungicidal composition according to claim 7, further characterized in that it comprises an amount effective to kill fungi, of at least one compound according to any of claims 1 to 7 together with the additives or auxiliaries conventionally used for this. application.

9. An insecticidal, acaricidal or nematicidal composition according to claim 7, further characterized in that it comprises an effective amount of at least one compound according to any of claims 1 to 5, together with the additives or auxiliaries conventionally used for this application .

10. A composition for crop protection comprising an effective amount to kill fungi, insects, mites or nematodes, of at least one compound according to any of claims 1 to 5 and at least one additional active substance together with the auxiliaries and additives conventionally used for this application.

11. A composition to be used in the protection of wood or as a preservative in sealants, in paints, in coolants lubricants for metal work or in oils for drilling and cutting, comprising an effective amount of at least one compound in accordance with any of claims 1 to 5 together with auxiliaries and additives conventionally used for these applications.

12. A compound according to any of claims 1 to 5 or a composition according to claim 7, 9 or 10, to be used as a veterinary drug.

13. A process for preparing a composition according to any of claims 7 to 11, further characterized in that it comprises combining the active substance and the other additives and bringing the mixture to an appropriate use form.

14. The use of a compound according to any of claims 1 to 5, or of a composition according to any of claims 7, 8, 10 and 11 as a fungicide.

15. The use of a compound according to any of claims 1 to 5 or of a composition according to any of claims 7, 8 and 11 as a wood preservative or as a preservative in sealants, in paints, in lubricants coolants for metal work or in oils for drilling and cutting.

16. The use of a compound according to any of claims 1 to 5 or of a composition according to any of claims 7, 9 or 10 to control insects, mites, molluscs and harmful nematodes.

17. A method for controlling phytopathogenic fungi, comprising applying an effective amount to kill fungi, a compound according to any of claims 1 to 5 or a composition according to any of claims 7, 8, 10 and 11 to these fungi or to the plants, areas or substrates infected with them, or to the seeds.

18. A method for controlling insects, mites, molluscs and harmful nematodes, in which an effective amount of a compound according to any of claims 1 to 5 or of a composition according to any of claims 7 is applied, 9 or 10 to these or to the plants, areas or substrates infected with them.

19. - Seeds, treated or coated with an effective amount of a compound according to any of claims 1 to 5 or of a composition according to any of claims 7, 9 or 10. _ * ______ ^? __ i_____ SUMMARY OF THE INVENTION The invention relates to 1, 3-oxazoline and 1,3-thiazoline derivatives having the formula (I), wherein the symbols have the following meanings: A represents phenyl, pyridyl, pyrimidinyl, pyrazinyl, pyrazolyl or thienyl; E represents a single bond, C 1 -C 4 alkylene, -O-CH 2 - or CH 2 -O-; G represents a radical of group (a), (b), (c) and (d) (d) and Z represents oxygen or sulfur; The compounds of the formula (I) exhibit an excellent acaricidal and insecticidal effect, especially as regards the spectrum of activity and effectiveness. P00 / 1684F 4 -- . 4 -•*- *