MXPA00000538A - 2-[pyrazolyl and triazolyl-3'-oxymethylene]-phenyl-isoxazolones, triazolones and tetrazolones as pesticides and fungicides - Google Patents

Abstract

The invention relates to 2-[pyrazolyl and triazolyl-3'-oxymethylene]-phenyl-isoxazolones, triazolones and tetrazolones of formula (I), wherein the indices and the substituents have the following meaning:X represents a group A, B or C,#indicating the bond with the phenyl ring, Ra being hydrogen, halogen, alkyl or alkoxy and Rb being alkyl;Y represents N or CRc, Rc being hydrogen, halogen or alkyl;n represents 0, 1, 2, 3 or 4 and the substituents R1 can be different when n is greater than 1;R1represents nitro, cyano or halogen, optionally substituted alkyl or optionally substituted alkoxy or if n is 2, additionally an optionally substituted bridge which is bound to two adjacent ring atoms, said bridge containing three to four members from the group of 3 or 4 carbon atoms, 2 to 3 carbon atoms and 1 or 2 nitrogen, oxygen and/or sulphur atoms, and together with the ring to which it is bound may form a partially unsaturated or aromatic radical;R2 represents hydrogen, nitro, cyano, halogen, alkyl, halogenalkyl, alkoxy, alkylthio or alkoxycarbonyl and R3 represents optionally substituted alkyl, optionally substituted cycloalkyl, optionally substituted aryl or optionally substituted hetaryl.

Description

2- [PIRAZ0LIL- AND TRIAZOLIL-3 '-OXIMETILEN] PHENYLISOXAZOLONES, - TRIAZOLONAS AND -TETRAZOLONAS, ITS PREPARATION AND ITS USE The present invention relates to 2- [pyrazolyl- and triazolyl-3'-oxymethylene] phenylisoxazolones, -triazolones and -tetrazolones of the formula I where: X is a group A, B or C, where # refers to the bond with the phenyl ring and Ra is hydrogen, halogen, C?-C4 alkyl or C alco-C4 alkoxy and R b is C 1 -C 4 alkyl; Y is N or CRC, where Rc is hydrogen, halogen or C alquilo-C4 alkyl; n is 0, 1, 2, 3 or 4, where the substituents R1 may be different if n is greater than 1; R 1 is nitro, cyano, halogen, Ci-Cβ alkyl with or without substitution or alkoxy with or without substitution or is also, if n is 2, a bridge with or without substitution containing from 3 to 4 members of group 3 or 4 carbon atoms, 2 to 3 carbon atoms and 1 or 2 nitrogen atoms, oxygen and / or sulfur fixed on two adjacent ring atoms, it being possible for this bridge to form together with the ring on which a radical is partially fixed unsaturated or aromatic; R 2 is hydrogen, nitro, cyano, halogen, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl C 1 -C 4 alkyloxy C 1 -C 4 alkyl or C 4 -C 4 alkoxycarbonyl; R3 is Ci-Cß alkyl with or without substitution, C3-C6 cycloalkyl with or without substitution, aryl with or without substitution or hetaryl with or without substitution. In addition, the present invention relates to processes for the preparation of these compounds, to compositions comprising these compounds and to their use for controlling animal pests or harmful fungi. WO-A 93/15046, WO-A 96/01256 and WO-A 96/01258 present 2- [pyrazolyl-4-oxymethylene] anuides and 2- [triazolyl-4-oxymethylene] anuides to control animal pests and fungi harmful. WO-A 95/14009, WO-A 96/36229, WO-A 96/38425, WO-A 97/05120 and WO-A 97/02255 present 4-phenyl-2,3-dihydroisoxazolones, 4-phenyl -2,4-dihydrotriazolones and 2-phenyl-2,5-dihydrotetrazolones having substituents on the ortho position of the phenyl radical. It is an object of the present invention to offer compounds that have improved activity. We have found that this object is achieved through the compounds defined at the beginning. In addition, the invention offers processes for preparing them, compositions comprising said compounds and methods for controlling animal pests and harmful fungi by the use of the compounds I. The compounds of the formula I differ from those presented in the aforementioned publications WO-A 93 / 15046, WO-A 96/01256 and WO-A 96/01258 in the radical isoxazolone, triazolone or tetrazolone in the phenyl ring, and differ from the compounds presented in WO-A 95/14009, WO-A 96/36229, WO-A 96/38425, WO-A 97/05120 and WO-A 97/02255 in the oxymethylene pyrazolyl group or oxymethylenetriazolyl in the phenyl ring. In comparison with the compounds of the prior art, the compounds of the formula I have an increased activity against harmful fungi and animal pests. The compounds of the formula I can be obtained per se by a method similar to the methods described in WO-A 95/14009, WO-A 96/01256, WO-A 96/01258, WO-A 96/36229 , WO-A 96/38425, WO-A 97/05120, or WO-A 97/02255. The compounds I can be obtained by several routes, it being immaterial for the synthesis that the group X or the pyrazolyl or triazolyl group is constituted first. For greater clarity, the term X is therefore used for the radical X * or a suitable precursor of this radical and the term E # is used for the pyrazolyl or triazolyl group or a suitable precursor thereof in the descriptions of the reactions then. The compounds I are obtained, for example, by the conversion of a benzyl derivative of the formula II * in the presence of a base with a 3-hydroxypyrazole or 3-hydroxytriazole of the formula III into the corresponding phenyl derivative of the formula V *.

(R1 II 'III If the radical X in the formula V is a group A, B or C, the phenyl compounds of the formula V # correspond to those of the formula I. In the formula II, L is a nucleophilically displaceable group, for example halogen (for example, chlorine, bromine and iodine), or an alkyl or aryl sulfonate (for example methylsulfonate, trifluoromethylsulfonate, phenylsulfonate and 4-methylphenylsulfonate). The etherification of the compounds II * and III is usually carried out at a temperature comprised within a range from 0 ° C to 80 ° C, preferably from 20 ° C to 60 ° C. Suitable solvents are aromatic hydrocarbons such as for example toluene, o-, m- and p-xylene, halogenated hydroxycarbons such as for example methylene chloride, chloroform and chlorobenzene, ethers such as diethyl ether, diisopropyl ether, methyl tert-butyl ether, dioxane , anisole and tetrahydrofuran, nitriles such as acetonitrile and propionitrile, alcohols such as for example methanol, ethanol, n-propanol, i-propanol, n-butanol and tert-butanol, ketones such as ketones and methyl ethyl ketone and dimethyl sulfoxide, dimethylformamide, dimethylacetamide , 1,3-dimethylimidazolidin-2-one and 1,2-dimethyltetahydro-2 (1H) -pyrimidine, preferably methylene chloride, acetone, toluene, methyl tert-butyl ether and dimethylformamide. Mixtures of the aforementioned solvents can also be used. In general, suitable bases are inorganic compounds such as, for example, alkali metal hydroxides and iron alkali metal hydroxides (for example, lithium hydroxide, sodium hydroxide, potassium hydroxide and calcium hydroxide), alkali metal oxides and metal oxides ferrous alkalines (for example, lithium oxide, sodium oxide, calcium oxide and magnesium oxide), alkali metal hydrides and ferrous alkali metal hydrides (for example, lithium hydride, sodium hydride, potassium hydride and calcium hydride), alkali metal amides (for example lithium amide, sodium amide and potassium amide), alkali metal carbonates and alkali metal carbonates ferrous (for example, lithium carbonate and calcium carbonate), and alkali metal bicarbonates (for example sodium bicarbonate), organometallic compounds, particularly alkali metal alkyls (for example methyllithium, butyllithium, and phenyllithium), alkylmagnesium halides (for example methylmagnesium chloride) and alkali metal alkoxides and ferrous alkali metal alkoxides (by example sodium methoxide, sodium ethoxide, potassium ethoxide, potassium tert-butoxide and dimethoxymagnesium), in addition organic bases, for example tertiary amines such as trimethylamine, triethylamine, triisopropylethylamine and n-methylpiperidine, pyridine, substituted pyridines such as for example collidine , lutidine and 4-dimethylaminopyridine, as well as bi-cyclic amines. Sodium hydroxide, potassium carbonate and potassium tert-butoxide are especially preferred. In general terms, the bases are used in equimolar quantities, either in excess or, if appropriate, as solvent. It may be helpful for the reaction to add a catalytic amount of a crown ether (for example, 18-crown-6 or 15-crown-5). It is also possible to carry out the reaction in a two-phase system comprising a solution of hydroxides or carbonates of alkali metals or ferrous alkali metals in water and an organic phase (for example aromatic and / or halogenated hydrocarbons). Suitable phase transfer catalysts for this purpose are, for example, ammonium halides and ammonium tetrafluoroborates (for example benzyltriethylammonium chloride, benzyltributylammonium bromide, tetrabutylammonium chloride, hexadecyltrimethylammonium bromide or tetrabutylammonium tetrafluoroborate) and phosphonium (for example tetrabutylphosphonium chloride and tetrabutylphosphonium bromide). It may be helpful for the reaction to initially convert the 3-hydroxypyrazole with the base to the corresponding hydroxylate which then reacts with the benzyl derivative. The compounds of benzyl II * required for the preparation of compounds I are presented in literature (see WO-A 95/14009, WO-A 96/36229, WO-A 97/02255). They can be obtained through the following synthetic route: (Ra-alkoxy or halogen) Compounds of the formula IIA * wherein Ra is alkyl are obtained from the corresponding phenylacetic esters Ilh * by the routes known from US 4,952,573 and WO-A 96/36229.

Compounds of formula IIB can be obtained by the following synthesis route [see WO-A 95/14009; WO-A 96/36229; WO-A 97/02255]: The nitro group of lia can be reduced under generally customary conditions, preferably by catalytic hydrogenation, by reduction with iron, tin or zinc in the presence of an acid, by reduction with alkali metals in the presence of a base or by reduction catalyzed by an enzyme. [see Houben-Weyl, vol. IV / lc, 4th. Edition, page 506 et seq., Thieme Verlag Stuttgart and New York (1980); ibid. vol. IV / ld, 4th. Edition, page 473 et seq. (1981); heterocycles, vol. 31, page 2201 (1990)]. Some nitrobenzene derivatives of the formula Ia '* are known in the literature [see WO-A 93/15046; WO-A 95/14009], or they can be prepared in accordance with the literature mentioned.

The reaction of lia with phosgene or a phosgene equivalent, such as for example phenyl chloroformate or diphosgene or triphosgene, is usually carried out at a temperature comprised within a range of -10 ° C to 250 ° C, preferably from 10 ° C to 110 ° C, in an inert organic solvent, in the presence of a base or a catalyst [see Chem. Ber., vol. 72, page 457 (1972); Chem. Soc. Rev., vol. 3, page 209 (1974); 7? Ngew. Chem., Vol. 107, page 2746 (1995)].

In the formula lid * "Hal" is a halogen atom, such as chlorine or bromine. The benzyl compounds IIB * required for the preparation of compounds IB wherein Ra is alkyl or alkoxy are also known from the literature [see WO-A 96/36229], or can be obtained through the methods indicated in the literature [see J. Org. Chem., Vol. 43 (1978) page 936]. They can be obtained by reaction of the carbamates of the formula lie * with amidines IVb or orthoesters IVc: Compounds of the formula IIC can be obtained through the following synthesis route [see WO-A 95/14009; WO-A 96/36229; WO-A 97/02255]: The reaction of the isocyanates Ilb * with Ivd azides is usually carried out at a temperature comprised within a range of -10 ° C to 200 ° C, preferably 20 ° C to 140 ° C, in an inert inert solvent, if appropriate in the presence of a base or an acid [see J. Org. Chem., Vol. 45, page 5130 (1980); J. Am. Chem. Soc, vol. 81, page 3076 (1959); Tetrahedron, vol. 31, page 765 (1975); J. Org. Chem., Vol. 38, page 675 (1973)]. In the formula IVd, M is a cation of the group of the alkali metals or ferrous alkali metals, trialkylsilyl or alkyl. Preferably, trimethylsilyl azide is used. The alkylation of the tetrazolinones líe * to provide IIC * is usually carried out at a temperature between -20 ° C and 180 ° C, preferably from 20 ° C to 120 ° C, in an inert organic solvent in the presence of a base [see Synth. Common., Vol. 18, page 2011 (1988); J. Chem. Soc. Chem. Commun., Page 735 (1987)]. Suitable alkylating agents are, for example, alkyl halides, alkylsulfonates, alkyl-p-toluenesulfonates, alkyltrifluoromethanesulfonates, alcohols, dialkyl ethers or alkyl-p-bromophenylsulfonates, particularly methyl iodide or dimethyl sulfate. If E * in the formulas IIA *, Ilb * and IIC * is the pyrazole group or the triazole group, the compounds IIA *, IIB * and IIC * correspond to the compounds IA, IB and IC, respectively. These syntheses are not only suitable for the preparation of benzyl II * compounds, but can be used in principle at each stage of the synthesis of the pyrazole or triazole group for the formation of groups A, B or C. The synthesis of the group X is particularly preferably carried out in the stage of the compounds Ia '* or IIb' wherein E * is hydrogen or the pyrazole or triazole group. Illa 3-hydroxypyrazoles are also presented in the literature, or they can be prepared by the methods described there [J. Heterocycl. Chem. 30, (1993), 49, Chem. Ber. 107, (1974), 1318, Chem. Pharm. Bull. 19, (1971), 1389, Tetrahedron Lett. 11, (1970), 875, Chem. Heterocycl. Comp. 5, (1969), 527, Chem. Ber. 102, (1969), 3260, Chem. Ber. 109, (1976), 261, J. Org. Chem. 31, (1966), 1538, Tetrahedron 43, (1987), 607]. The 3-hydroxypyrazoles Illa are especially advantageous when obtained by the processes described in WO-A 97/03969 and in DE Application No. 19 652 516.0. 2-Hydroxytriazoles Illb are also presented in the literature or can be prepared by the methods described there [Chem. Ber. 56, (1923), 1794; DE-A 21 50 169; DE-A 22 00 436; US-A 4,433,148; J. Med. Chem. 33, (1990), 2772; Synthesis 1987, 986; DE-A 22 60 015; DE-A 24 17 970]. The reaction mixtures are treated in a customary manner, for example by mixing them with water, separating the phases and, if appropriate, chromatographically purifying the crude products. Some of the intermediate products and final products are obtained in the form of viscous, colorless or slightly brown oils, free of volatile components or purified under reduced pressure and at a moderately high temperature. If the intermediate products and the final products are obtained as solids, the purification can also be carried out by recrystallization or by digestion. The compounds I can contain acid or basic centers and can therefore form acid addition products or base addition products or salts. The acids for the acid addition products are, inter alia, mineral acids (for example hydrohalic acids such as hydrochloric acid and hydrobromic acid, phosphoric acid, sulfuric acid, nitric acid), organic acids (for example, formic acid, acetic acid) , oxalic acid, malonic acid, lactic acid, malic acid, succinic acid, tartaric acid, citric acid, salicylic acid, p-toluenesulfonic acid, dodecylbenzenesulfonic acid) or other protonic acid compounds (eg, saccharin). Bases for the base addition products are, among others, oxides, hydroxides, carbonates or bicarbonates of alkali metals or ferrous alkali metals (for example potassium hydroxide, sodium hydroxide, potassium carbonate or sodium carbonate), or ammonium compounds (for example ammonium hydroxide). In some of the definitions of symbols provided in the formulas above, collective terms were used which generally represent the following substituents: Halogen: fluorine, chlorine, bromine and iodine; Alkyl: straight or branched chain saturated hydrocarbon radicals having 1 to 4 or 6 carbon atoms, for example, methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl and 1, 1 -dimethylethyl; Haloalkyl: straight chain or branched alkyl groups having 1 4 carbon atoms (in accordance with the above), it being possible for the hydrogen atoms in these groups to be partially or totally replaced by halogen atoms in accordance with mentioned above, for example C 1 -C 2 haloalkyl such as for example chloromethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 1-fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2- trifluoroethyl, 2-chloro-2-fluoroethyl, 2,2,2-trichloroethyl and pentafluoroethyl; Alkylcarbonyl: straight or branched chain alkyl groups, in particular those having 1 to 10 carbon atoms (according to the above), bonded to the backbone through a carbonyl group (-CO-); Alkoxy; straight or branched chain alkyl groups having from 1 to 4 carbon atoms (according to the above) attached to the backbone through an oxygen atom (-0-); Alkoxycarbonyl: straight or branched chain alkoxy groups having from 1 to 4 carbon atoms (as mentioned above), attached on the backbone through a carbonyl group (-C0-); Alkylthio: straight chain or branched alkyl groups having from 1 to 4 carbon atoms (as mentioned above), attached on the backbone through a sulfur atom (-S-); Cycloalkyl: monocyclic saturated hydrocarbon groups having from 3 to 6 carbon ring members, for example cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl; Aryl: a mononuclear to trinuclear aromatic ring system containing from 6 to 14 carbon ring members, for example, phenyl, naphthyl, and anthracenyl; Hetaryl: 5- or 6-membered heteroaromatic, for example: 5-membered heteroaryl containing one to four nitrogen atoms or one to three nitrogen atoms and one sulfur atom or one oxygen atom; 5-ring hetaryl groups which can, in addition to carbon atoms, contain one to four nitrogen atoms or one to three nitrogen atoms and one sulfur atom or one oxygen atom as ring members, for example 2 -furyl, 3-furyl, 2-thienyl, 3-thienyl, 2-pyrrolyl, 3-pyrrolyl, 3-isoxazolyl, 4-isoxazolyl, 5-isoxazolyl, 3-isothiazolyl, 4-isothiazolyl, 5-isothiazolyl, 3-pyrazolyl , 4-pyrazolyl, 5-pyrazolyl, 2-oxazolyl, 4-oxazolyl, 5-oxazolyl, 2-thiazolyl, 4-thiazolyl, 5-thiazolyl, 2-imidazolyl, 4-imidazolyl, 1, 2, 4-oxadiazol-3 -yl, 1,2,4-oxadiazol-5-yl, 1, 2,4-thiadiazol-3-yl, 1, 2,4-thiadiazol-5-yl, 1, 2,4-triazol-3-yl , 1, 3, 4-oxadiazol-2-yl, 1,3,4-thiadiazol-2-yl and 1, 3, 4-triazol-2-yl; benzofused 5-membered hetaryl containing from one to three nitrogen atoms either a nitrogen atom and an oxygen atom or a sulfur atom: 5-membered ring hetaryl groups which may, in addition to carbon atoms, contain one four nitrogen atoms either one to three nitrogen atoms and one sulfur atom or one oxygen atom as ring members, and wherein two neighboring carbon ring members or a nitrogen and a neighboring carbon ring member can be bridged by a buta-1, 3-dien-l, 4-diyl group; 5-membered hetaryl fixed through nitrogen and containing one to four nitrogen atoms, or benzofused 5-membered hetaryl bonded through nitrogen and containing one to three nitrogen atoms: 5-membered ring hetaryl groups they can, in addition to carbon atoms, contain one to four nitrogen atoms or one to three nitrogen atoms as ring members, and wherein two neighboring carbon ring members or a nitrogen or a neighboring carbon ring member they may be bordered by a buta-1,3-dien-l, 4-diyl group, these rings are attached to the backbone through one of the nitrogen ring members; 6-membered hetaryl containing one to three or one to four nitrogen atoms: hetaryl ring groups of 6 members which can, in addition to carbon atoms, contain from one to three or from one to four nitrogen atoms as ring members, for example, 2-pyridinyl, 3-pyridinyl, 4-pyridinyl, 3-pyridazinyl, 4-pyridazinyl, 2-pyrimidinyl, 4-pyrimidinyl, 5-pyrimidinyl, 2-pyrazinyl, 1, 3, 5 triazin-2-yl and 1, 2,4-triazin-3-yl; As for the alkyl, alkenyl and alkynyl groups, the term "with or without substitution" is intended to mean that these groups may be partially or fully halogenated (ie, the hydrogen atoms of those groups may be partially or totally replaced). by halogen atoms identical or different as mentioned above (preferably fluorine, chlorine and bromine, particularly fluorine and chlorine) and / or carry from one to three, particularly one, of the following radicals: alkoxy? -C.sup.-haloalkoxy Ci-C? / alkylthio Ci-C?. haloalkylthio Ci-Cβ alkylamino C? -C6, dialkylamino Ci-C? alkenyloxy C2-C6 haloalkenyloxy C2-C6, alkynyloxy C2-C6, haloalkynyloxy C2-C6 cycloalkyl C3-C6. C3-C6 cycloalkyloxy, C3-Cd cycloalkenyl, C3-C6 cycloalkenyloxy / or mononuclear or dinuclear aromatic ring system with or without substitution which can, in addition to carbon atoms, contain from one to four nitrogen atoms or one or two nitrogen atoms and one oxygen atom or one sulfur atom or one oxygen or it can be a sulfur atom as ring members (in accordance with that mentioned above) fixed directly on the substituent an oxygen atom (-0 -), a sulfur atom - (S-) or through an amino group (-NRa-), ie aryl radicals such as phenyl and naphthyl, preferably phenyl or 1-naphthyl or 2-naphthyl , and hetaryl radicals, such as, for example, 5-membered ring heteroaromatics containing from one to three nitrogen atoms and / or an oxygen atom or a sulfur atom such as, for example, 2-furyl, 3-furyl, 2-thienyl, 3-thienyl, 1-pyrrolyl, 2-pyrrolyl, 3-pyrrolyl, 3-isoxazolyl, 4 -isoxazolyl, 5-isoxazolyl, 3-isothiazolyl, 4-isothiazolyl, 5-isothiazolyl, 1-pyrazolyl, 3-pyrazolyl, 4-pyrazolyl, 5-pyrazolyl, 2-oxazolyl, 4-oxazolyl, 5-oxazolyl, 2-thiazolyl , 4-thiazolyl, 5-thiazolyl, 1-imidazolyl, 2-imidazolyl, 4-imidazolyl, 1, 2, 4-oxadiazol-3-yl, 1, 2,4-oxadiazol-5-yl, 1,2,4 -thiadiazol-3-yl, 1, 2,4-thiadiazol-5-yl, 1, 2, 5-triazol-3-yl, 1, 2, 3-triazol-4-yl, 1, 2, 3-triazole -5-yl, 1, 2, 3-triazol-4-yl, 5-tetrazolyl, 1, 2, 3, 4-thiatriazol-5-yl and 1,2,3,4-oxatriazol-5-yl, particularly 3-isoxazolyl, 5-isoxazolyl, 4-oxazolyl, 4-thiazolyl, 1,3-oxadiazol-2-yl and 1, 3, 4-thiadiazol-2-yl; heteroaromatic six-membered ring containing one to four nitrogen atoms as heteroatoms such as 2-pyridinyl, 3-pyridinyl, 4-pyridinyl, 3-pyridazinyl, 4-pyridazinyl, 2-pyrimidinyl, 4-pyrimidinyl, 5- pyrimidinyl, 2-pyrazinyl, 1, 3, 5-triazin-2-yl, 1,2,4-triazin-3-yl and 1, 2, 4, 5-tetrazin-3-yl, particularly 2-pyridinyl, 3 pyridinyl, 4-pyridinyl, 2-pyrimidinyl, 4-pyrimidinyl, 2-pyrazinyl and 4-pyridazinyl. As for the cyclic groups (saturated, unsaturated or aromatic), the term "with or without substitution" has the purpose of expressing that these groups may be partially or totally halogenated [ie, the hydrogen atoms of these groups may be partially or completely replaced by identical or different halogen atoms according to the above mentioned (preferably fluorine, chlorine or bromine, particularly fluorine or chlorine)] and / or carrying from one to four (particularly from one to three) of the following radicals: cyano, nitro, hydroxy, amino, carboxyl, aminocarbonyl, alkyl, haloalkyl, alkenyl, haloalkenyl, alkenyloxy, haloalkenyloxy, alkynyl, haloalkynyl, alkynyloxy, haloalkynyloxy, alkoxy, haloalkoxy, alkylthio, haloalkylthio, alkylamino, dialkylamino, alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy, alkylaminocarbonyl, dialkylaminocarbonyl, alkylacarbonylamino, alkoxycarbonylamino, alkylcarbonyl-N-alkylamino and alkylcarbonyl-N-alkylamino [sic], wherein the alkyl groups in these radicals preferably contain from 1 to 6 carbon atoms, particularly from 1 to 4 carbon atoms and where the alkenyl or alkynyl groups mentioned in these radicals contain from 2 to 8, preferably from 2 to 6, particularly from 2 to 4 carbon atoms; and / or one to three (in particular one) of the following radicals: cycloalkyl, cycloalkoxy, cycloalkylthio, cycloalkylamino, cycloalkyl-N-alkylamino, heterocyclyl, heterocyclyloxy, heterocyclylthio, heterocyclylamino or heterocyclyl-N-alkylamino, without substitution or with substitution by customary groups, wherein the cyclic systems contain from 3 to 12 ring members, preferably from 2 to 8 ring members, particularly from 3 to 6 ring members, and the alkyl groups in these radicals preferably contain from 1 to 6. carbon atoms, particularly from 1 to 4 carbon atoms; aryl, aryloxy, arylthio, arylamino, aryl-N-alkylamino, arylalkoxy, arylalkylthio, arylalkylamino, arylalkyl-N-alkylamino, hetaryl, hetaryloxy, hetarylthio, hetarilamino, hetaryl-N-alkylamino, hetarilalcoxi, hetarilalquiltio, hetarilalquilamino and hetarilalquil-N- alkylamino, without substitution or with substitution by customary groups, where the aryl radicals preferably contain from 6 to 10 ring members, particularly 6 ring members (phenyl), the hetaryl radicals contain in particular 5 or 6 ring members and the Alkyl groups in these radicals preferably contain from 1 to 6 carbon atoms, particularly from 1 to 4 carbon atoms and / or one or two (particularly one) of the following radicals: formyl, Cr111 = NORIV [where R111 is hydrogen, alkyl, cycloalkyl and aryl and R 1 V is alkyl, alkenyl, haloalkenyl, alkynyl and arylalkyl (where the above-mentioned alkyl groups preferably contain from 1 to 6 carbon atoms, in particular C.sub.1 to 4 carbon atoms, the cycloalkyl groups, alkenyl groups and alkynyl groups mentioned preferably contain from 3 to 8, particularly from 3 to 6 carbon atoms) and aryl is in particular phenyl without substitution or with substitution by groups usual] or NRv-CO-D-Rvi [where Rv is hydrogen, hydroxy, C2-C6 alkenyl, C2-C6 alkenyl, C2-C6 alkynyl, C6-C6 alkoxy, C2-C6 alkenyloxy. C 2 -C 6 alkynyloxy, C 1 -C 6 alkoxy C 1 -C 6 alkyl, C 1 -C 6 alkoxy C 1 -C 6 alkoxy and C 6 -C 6 alkoxycarbonyl. Rvi is hydrogen, C6-C6 alkyl / C2-C6 alkenyl. C2-C6 alkynyl C-C6 cycloalkyl. C3-C6 cycloalkenyl, aryl, arylalkyl C? -C6, hetaryl and hetarylalkyl Ci-Ce and D is a direct bond, oxygen or nitrogen, where nitrogen can carry one of the groups mentioned in RV1], and / or where two carbon atoms neighboring the cyclic systems can carry a C3-C5 alkylene, C3-C5 alkenylene, C2-C4 oxyalkylene, C1-C3 oxyalkyleneoxy, C2-C oxyalkenylene, C2-C4 oxyalkenyleneoxy, or butadiene-diol group, where these bridges in turn can be partially or fully halogenated and / or can carry from one to three, particularly one or two, of the following radicals: C? -C alkyl, C? -C haloalkyl, C? -C4 alkoxy C1-C4 haloalkoxy and C? -C4 alkylthio . Regarding its biological activity, preference is given to compounds I A.

In addition, compounds of the formula IB are also preferred. < R Preference is also given to IC compounds, ^ O N W W N-N R * > In addition, preference is given to compounds I wherein Ra is methoxy. In addition, preference is also given to compounds I in which Ra is methyl. In addition, preference is also given to the compounds I wherein R is methyl. In the same way, preference is given to the compounds I where n is 0 or 1, particularly 0. In addition, preference is given to compounds I wherein R1 is in the 6-position. In addition, preference is given to compounds I in where R1 is halogen or methyl. In the same way, preference is given to compounds I in which R "'is hydrogen, In addition, preference is given to compounds I in which R3 is C6-C6 alkyl, with or without substitution. compounds I wherein R3 is phenyl or benzyl, it being possible for the phenyl radical to be partially or fully halogenated and / or [lacuna] from one to three of the following radicals: cyano, nitro, Ci-Cß alkyl, haloalkyl C? -C4 , C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy, C 1 -C 4 alkoxy C 1 -C 4 alkyl, C 3 -C 6 cycloalkyl, C 1 -C 4 alkylcarbonyl, C 1 -C 4 alkoxycarbonyl phenyl, phenoxy and C 1 -C 4 phenylalkoxy the phenyl rings in turn may be partially or totally halogenated and / or carry from one to three of the following radicals: cyano, nitro, alkyl CL-C4, haloalkyl C? ~ C2 / alkoxy C? -C haloalkoxy C? C2, C3-C6 cycloalkyl C5-C4 alkylcarbonyl or C1-C4 alkoxycarbonyl, and / or a group CR '= N0R "wherein R' is hydrogen or C alquilo-C4 alkyl and R" is Ci-Cß alkyl I two carbon atoms adjacent to the phenyl ring may be attached by a C1-C3 oxyalkoxy bridge or a C1-C3 oxyhaloalkoxy bridge. In addition, compounds I in which R3 is pyridyl are particularly preferred, wherein the pyridyl ring may be partially or fully halogenated and / or carry from one to three of the following radicals: cyano, nitro, alkyl C? -C4, haloalkyl C1-C2 alkoxy C1-C4, haloalkoxy C? -C2 cycloalkyl C3-C6, alkylcarbonyl C? -C4 or alkoxycarbonyl C? _C. In addition, compounds I in which Rb is hydrogen are preferred. In addition, compounds IA.l, IA.2, LA.3 and IA.4 wherein (R1 ^ is hydrogen, 6-chloro or 6- ethyl, R2 is hydrogen or methyl and R3 is cyclohexyl, benzyl, phenyl, pyridyl or pyrazinyl with or without substitution by halogen or C 1 -C 4 haloalkyl.

IA.l CH, In addition, compounds IA.5, IA.6, IA.7, IA.8, IA.9, IA.10, IA.ll and IA.12 where (R1) - is hydrogen, 6-chloro or either 6-methyl, Rd is halogen, nitro, cyano, C1-C9 alkyl. Ci-C2 haloalkyl, cyclohexyl, C? -C6 alkoxy, C? -C2 haloalkoxy, C? -C3 phenylalkoxy or phenyl wherein the phenyl ring may be unsubstituted or substituted by halogen, methyl or methoxy, is pyridyl, C1-alkoxycarbonyl -C4, methoxymethyl or a group C (CH3) = N-alkoxy C1.-C4, and the index m is 1-5, particularly 1 or CH, Particularly preferred are compounds IB.l, IB.2, IB.3 and IB.4 wherein (R1 ^ is hydrogen, 6-chloro or 6-methyl, R "is hydrogen or methyl and R3 is cyclohexyl, benzyl, phenyl , pyridyl or pyrazinyl without substitution or with substitution by halogen or C1-C4 haloalkyl.

CH, CH, In addition, particular preference is given to compounds IB.5, IB.6, IB.7, IB.8, IB.9, IB.10, IB.11 and IB.12 wherein (R1) -, is hydrogen, -clor or either 6-methyl, Rd is halogen, nitro, cyano, C1-C9 alkyl, haloalkyl C? -C2, cyclohexyl, Ci-C? alkoxy, C? -C2 haloalkoxy, C1-C3 phenylalkoxy or phenyl where the phenyl may be unsubstituted or substituted by halogen, methyl or methoxy, is pyridyl, C1-C4 alkoxycarbonyl, methoxymethyl, or a group C (CH3) = N-C1-C4 alkoxy and the m-index is 1-5, particularly 1 or 2.

CH, CH, .2 N - N CH, N - CH, CH, CH, Likewise, IC compounds are preferred. l and IC .2 where (R1) -. is hydrogen, 6-chloro or 6-methyl, R2 is hydrogen or methyl and R3 is cyclohexyl, benzyl, phenyl, pyridyl or pyrazinyl without substitution either with halogen substitution or with haloalkyl C? ~ C.

CH, CH, In addition, compounds IC.3, IC.4, IC.5 and IC.6 are preferred in which (R1) n is hydrogen, 6-chloro or 6-methyl, Rd is halogen, nitro, cyano, Ci- Co, C halo-C2 haloalkyl, cyclohexyl, C?-C6 alkoxy / C halo-C2 haloalkoxy. C 1 -C 3 phenylalkoxy or phenyl wherein the phenyl ring may be unsubstituted or substituted by halogen, methyl or methoxy, is pyridyl, C 1 -C 4 alkoxymethylmethyl or a group C (CH 3) = N-C 1 -C 4 alkoxy and index m is 1-5, particularly 1 or 2.

CH, CH, As for the variables, the particularly preferred embodiments of the intermediate products correspond to the variables of the groups and / or radicals A, B, C, Y, Ra, Rb, (R1) n, R2 and R3 of the formula I. As for its use, particular preference is given to compounds I compiled in the following tables. In addition, the groups mentioned for a substituent in the tables are, in themselves and independently of the combination in which they are mentioned, a particularly preferred embodiment of the substituent in question. Table 1 Compounds of the formula IA.l wherein for each compound R2 and R3 correspond to a row of Table A Table 2 Compounds of the formula IA.2 where for each compound R2 and R3 correspond to a row of Table A Table 3 Compounds of formula IA.3 where for each compound (R1) r? / R2 and R3 correspond to a row of Table A Table 4 Compounds of formula IA.4 where for each compound R2 and R3 correspond to a row of Table A Table 5 Compounds of formula IA. 5 where (R1) r. is hydrogen and for each compound (Rd) m corresponds to a row of Table B Table 6 Compounds of formula IA.5 wherein (R1) n is 6-chloro and for each compound (R) m correspond to a row of Table B Table 7 Compounds of formula IA.5 wherein (R1) n is 6-methyl and for each compound (Rc) m corresponds to a row of Table B Table 8 Compounds of formula IA.6 wherein (R1), -! is hydrogen and for each compound (R ") rr correspond to a row of the Table B Table 9 Compounds of formula IA.6 where (Rx) n is 6-chloro and for each compound (Rd) m corresponds to a row of Table B Table 10 Compounds of formula IA.6 where (R1) ,. is 6-methyl and for each compound (R =) m corresponds to a row of the Table B Table 11 Compounds of formula IA.7 where (R ^ n is hydrogen and for each compound (R ~) rr correspond to a row of Table B Table 12 Compounds of formula IA.8 where (R1) ,! is hydrogen and for each compound (R) rr. correspond to a row of the Table B Table 13 Compounds of formula IA.9 wherein (R1) n is hydrogen and for each compound (Rd) m corresponds to a row of the Table B Table 14 Compounds of formula IA.9 wherein (R1) n is 6-chloro and for each compound (Rd) m corresponds to a row of Table B Table 15 Compounds of formula IA.9 wherein (R1) n is 6-methyl and for each compound (Rd) m correspond to one. row of Table B Table 16 Compounds of the formula IA.10 wherein (R1) n is hydrogen and for each compound (Rd) m corresponds to a row of the Table B Table 17 Compounds of the formula IA.10 wherein (R1) n is 6-chloro and for each compound (R) rr correspond to a row of the Table B Table 18 Compounds of the formula IA.10 wherein (R1) n is 6-methyl and for each compound (Rd) m corresponds to a row of the Table B Table 19 Compounds of formula IA.ll where (R1 ^ is hydrogen and for each compound (Rd) m correspond to a row of Table B Table 20 Compounds of formula IA.12 where [R1) n is hydrogen and for each compound (Rd) m correspond to a row of the Table B Table 21 Compounds of the formula IB.l where for each compound (R1) n, R2 and R3 correspond to a row of Table A Table 22 Compounds of the formula IB.2 where for each compound (R1) n / 2 and R3 correspond to a row of Table A Table 23 Compounds of formula IB.3 where for each compound (R ^ n, R2 and R3 correspond to a row of Table A Table 24 Compounds of the formula IB.4 where for each compound (R1) n R2 and 3 correspond to a row of Table A Table 25 Compounds of formula IB.5 wherein (R1) n is hydrogen and for compound (Rd) m correspond to a row of Table B Table 26 Compounds of formula IB.5 wherein (R1) n is 6-chloro and for compound (Rd) m correspond to a row of Table B Table 27 Compounds of formula IB.5 wherein (R1) n is 6-methyl and for compound (R) m correspond to a row of Table B Table 28 Compounds of the formula IB.6 wherein (R1) n is hydrogen and for compound (Rd) m correspond to a row of Table B Table 29 Compounds of the formula IB.6 wherein (R1) n is 6-chloro and for compound (Rd) m corresponds to a row of Table B Table 30 Compounds of the formula IB.6 wherein (R1) n is 6-methyl and for compound (Rd) m correspond to a row of Table B Table 31 Compounds of the formula IB.7 wherein (R1) n is hydrogen and for compound (Rd) m correspond to a row of Table B Table 32 Compounds of the formula IB.8 wherein (R1) n is hydrogen and for compound (Rd) m correspond to a row of Table B Table 33 Compounds of formula IB.9 where. { R1) n is hydrogen and for compound (Rd) m correspond to a row of Table B Table 34 Compounds of formula IB.9 wherein (R1) n is 6-chloro and for compound (Rd) ra correspond to a row of Table B Table 35 Compounds of formula IB.9 wherein (R1) n is 6-methyl and for compound (Rd) ra correspond to a row of Table B Table 36 Compounds of formula IB.10 wherein (R1) n is hydrogen and for compound (Rd) m correspond to a row of Table B Table 37 Compounds of the formula IB.10 wherein (R1) n is 6-chloro and for compound (Rd) m corresponds to a row of Table B Table 38 Compounds of the formula IB.10 wherein (R1) n is 6-methyl and for compound (Rd) m corresponds to a row of Table B Table 39 Compounds of the formula IB.11 wherein (R1) n is hydrogen and for compound (Rd) m correspond to a row of Table B Table 40 Compounds of the formula IB.12 wherein (R ^ n is hydrogen and for compound (Rd) m corresponds to a row of Table B Table 41 Compounds of formula IC.l where for each compound (R1) n / R ~ and R3 correspond to a row of Table A Table 42 Compounds of formula IC.2 where each compound (R1) nf R2 and R3 correspond to a row of Table A Table 43 Compounds of formula IC.3 where (R1) n is hydrogen and for compound (Rd) m correspond to a row of Table B Table 44 Compounds of formula IC .3 wherein (R1) ,, is 6-chloro and for compound (Rd) m corresponds to a row of Table B Table 45 Compounds of the formula IC. 3 wherein (Ra) n is 6-methyl and for compound (Rd) m correspond to a row of Table B Table 46 Compounds of formula IC.4 where (R1 ^ is hydrogen and for compound (Rd) m correspond to a row of Table B Table 47 Compounds of the formula IC.4 where (R1) ,. is 6-chloro and for compound (Rd) m corresponds to a row of Table B Table 48 Compounds of the formula IC.4 wherein (R1) n is 6-methyl and for compound (Rd) m correspond to a row of Table B Table 49 Compounds of the formula IC.5 wherein (Ra) n is hydrogen and for compound (Rd) m correspond to a row of Table B Table 50 Compounds of the formula IC.6 wherein (R1 ^ is hydrogen and for compound (Rd) m correspond to a row of Table B Table A No. (R?) N R? A-l H H ciciohexyl A-2 H H benzyl A-3 H H phenyl A- H H 2 -pyridyl A- 5 H H 5-Cl-pyridyl-2 A- 6 H H 5-CF 3 -pyridyl-2 A- 7 H H 2 -pyrazinyl A- 8 H CH3 cyclohexyl A- 9 H CH3 benzyl A-10 H CH3 phenyl A-ll H CH3 2-pyridyl A- 12 H CH3 5-Cl-pyridyl-2 A-13 H CH3 5-CF3-pyridyl-2 A-14 H CH3 2-pyracinyl A-15 6-C1 H cyclohexyl A-16 6-C1 H benzyl A-17 6-C1 H phenyl A-18 6-C1 H 2 -pyridyl A-19 6-C1 H 5-Cl-pyridyl-2 A-20 6-C1 H 5-CF 3 -pyridyl-2 A-21 6-C1 H 2 -pyrazinyl A-22 6-C1 CH3 cyclohexyl A-23 6-C1 CH3 benzyl A-24 6-C1 CH3 phenyl A-25 6-C1 CH3 2-pyridyl A-26 6-C1 CH3 5-Cl-pyridyl-2 A-27 6-C1 CH3 5-CF3-pyridyl-2 A-28 6-C1 CH3 2-pyrazinyl A-29 6-CH3 H cyclohexyl A-30 6-CH3 H benzyl A-31 6-CH3 H phenyl A- 32 6-CH3 H 2 -pyridyl A-33 6-CH3 H 5-Cl-pyridyl-2 A-34 6-CH3 H 5-CF3-pyridyl-2 A-35 6-CH5 H 2-pyracinil A-36 6-CH3 CH3 cyclohexyl A- 37 6-CH3 CH3 benzyl A-38 6-CH3 CH3 phenyl A-39 6-CH3 CH3 2-pyridyl A-40 6-CH3 CH3 5-Cl-pyridyl-2 A-41 6-CH3 CH3 5-CF3-pyridyl-2 A-42 6-CH3 CH3 2-pyracinyl Table B Bl H B-2 2-F B-3 3-F B-4 4-F B-5 2, 4-F2 B-6 2,4,6-F3 B-7 2,3,4,5 , 6- -F5 B-8 2,3-F2 B-9 2-Cl B-10 3-Cl B-ll 4-C1 B-12 2,3-Cl 2 B-13 2,4-Cl 2 B-14 2,5-Cl 2 B-15 2, 6-Cl 2 B-16 3,4-Cl 2 B-17 3,5-Cl B-18 2,3,4-Cl 3 B-19 2,3,5-Cl3 B-20 2,3,6-Cl3 B-21 2,4,5-Cl3 B-22 2.4, 6-Cl3 B-23 3,4,5-Cl3 B-24 2,3,4,6-Cl4 B-26 2,3,4,5,6-Cl5 B-27 2-Br B-28 3-Br B-29 4-Br B-30 2, 4-Br 2 B-31 2,5-Br 2 B-32 2,6-Br 2 B-33 2,4,6 -Br3 B-34 2,3,4,5, 6-Br5 B-35 2-J B-36 2-J B-37 4-J B-38 2,4-J 2 B-39 2-Cl, 3-F B-40 2-Cl, 4-F B-41 2-Cl, 5-F 'B-42 2-Cl, 6-F B-43 2-Cl, 3-Br B-44 2-Cl, 4-Br B-45 2-Cl, 5-Br B-46 2-Cl, 6-Br B-47 2-Br, 3-Cl B-48 2-Br, 4-Cl B-49 2-Br, 5-Cl B-50 2-Br, 3-F B-51 2-Br, 4-F B-52 2-Br, 5-F B-53 2-Br, 6-F B-54 2-F,; 3-Cl B-55 2-F, - 4-Cl B-56 2-F,! 5-Cl B-57 3-Cl, 4-F B-58 3-Cl, 5-F B-59 3-Cl, 4-Br B-60 3-Cl, 5-Br B-61 3-F, 4-Cl B-62 3-F, 4-Br B-63 3-Br, 4-Cl B-64 3-Br, 4-F B-65 2,6-Cl 2, 4-Br B-66 2-CH3 B-67 3-CH 3 B-68 4-CH 3 B-69 2,3- (CH 3) 2 B-70 2,4- (CH 3) 2 B-71 2.5- (CH3) 2 B-72 2.6- (CH3) 2 B-73 3.4- (CH3) 2 B-74 3.5- (CH3) 2 B-75 2,3,5- (CH 3) 3 B-76 2,3,4- (CH 3) 3 B-77 2.3, 6- (CH3) 3 B-78 2,4,5- (CH 3) 3 B-80 3,4,5- (CH 3) 3 B-81 2,3,4,6- (CH 3) 4 B-82 2,3,5 / 6- (CH 3) 4 B-84 2-C 2 H 5 B-85 3-C 2 H 5 B-86 4-C 2 H 5 B-87 2,4- (C 2 H 5) 5 B-88 2.6- (C2H5) 2 B-89 3.5- (C2H5) 2 B-90 2,4,6- (C 2 H 5) 3 B-91 2-n-C3H7 B-92 3-n-C3H7 B-93 4-n-C3H7 B-97 2.4- (i-C3H7) 2 B-98 2.6- (i-C3H7) 2 B-99 3.5- (i-C3H7) 2 B-101 3-s_ C4H9 B-102 4-S-C4H9 B-103 2-t-C4H9 B-104 3-t- C4H9 B-105 4-t -C4H9 B-106 4-n-C9H19 B-109 2-CH3, 4-i-C3H7 B-110 2-CH3, 5-i-C3H7 B-112 2-cyclo? -C6H ?? B-113 -3-Cyclo-C6Hn B-114 4-Cyclo-C6Hn B-115 2-Cl, 4-C6H5 B-116 2-Br, 4-C6H5 B-117 2-OCH3 B-120 2-OC2H5 B-121 3-O-C2H5 B-122 4-O-C2H5 B-123 2-0-n-C3H7 B-124 3-0-n-C3H7 B-125 4-0-n -C3H B-126 3-O-Í-C3H-? B-128 4-0-i-C3H7 B-132 2-0-CH2C6H5 B-133 3-0-CH2C6H5 B-134 4-0-CH2C6H5 B-135 2-0- (CH2) 3C6H5 B-136 4-0- (CH:) 3C6H5 B-137 2,3- (OCH 3) 2 B-138 2,4- (0CH 3) 2 B-139 2,5- (OCH 3) 2 B-140 2,6- (OCH 3) 2 B-141 3,4- (0CH 3 ) 2 B-142 3.5- (0CH3) 2 B-143 2-0-t-C4H9 B-144 3-0-t-C4H9 B-145 4-0-t-C4H9 B-146 3- (3 '-Cl-C6H4) B-147 4- (4'-CH3-C6H4) B-148 2-0-C6H5 B-149 3-0-C6H5 B-150 4-0-C6H5 B-151 2-0- (2'-F-C6H4) B-152 3-0- (3'-Cl-C6H4) B-153 4-0- (4'-CH3-C6H4) B-154 2.3, 6- (CH3) 3. 4-F B-155 2.3, 6- (CH3) 3. 4-Cl B-156 2.3, 6- (CH3) 3/4-Br B-157 2,4- (CH 3) 2. 6-F B-158 2.4- (CH3) 2, 6-C1 B-159 2.4- (CH3) 2, 6-Br B-160 2-i-C3H7, 4-Cl, 5-CH3 B-161 2-Cl, 4-NO2 B-162 2-NO;, 4 -Cl B-163 2-OCH 3, 5-N0 2 B-165 2,4-Cl 2. 6-N02 B-166 2,6-Cl 2. 4-N02 B-167 2,6-Br2, 4-N02 B-168 2,6-J2, 4-NO2 B-169 2-CH3, 5-i-C3H7, 4-Cl B-170 2-CO2CH3 B -171 3-CO2CH3 B-173 2-CH2OCH3 B-174 3-CH2OCH3 B-176 2-Me-4-CH5-CH (CH3) -CO B-177 2-CH3-4- (CH3-C = NOCH3) B-179 2-CH3-4- (CH3-C = NO-n-C3H7) B-180 2-CH3-4- (CH3-C = NO-n-C3H7) B-181 2.5- (CH3) 2-4- (CH3-C = NOCH3) B-182 2, 5- (CH3) 2-4- (CH3-C = NOC2H3) B-183 2.5- (CH3-4- (CH3-C = NO -n-C3H7) (sic) B-184 2, 5- (CH3) 2-4- (CH3-C = NO-Y-C3H7) B-185 2-C6H5 B-186 3-C6H5 B-187 4-C6H5 B-188 2- (2 '-F-C6H4) B-189 2-CH3, 5-Br B-190 2-CH3, 6-Br B-191 2-Cl, 3-CH3 B-195 2-F, 4-CH3 B-196 2-F, 5-CH3 B-197 2-Br, 3-CH3 B-198 2-Br, 4-CH3 B-199 2-Br, 5-CH3 B-200 3-CH3, 4-Cl B-201 3-CH3, 5-Cl B-202 3-CH3, 4-F B-203 3-CH3, 5-F B-205 3-CH3, 5-Br B-206 3-F, 4-CH3 B-207 3-Cl, 4-CH3 B-208 3-Br, 4-CH3 B-209 2-CL, 4,5- (CH 3) 2 B-210 2-Br, 4,5- (CH 3) 2 B-211 2-Cl, 3,5- (CH 3)? B-212 2-Br, 3,5- (CH 3) 2 B-213 2,6-C12, 4, -CH3 B-215 2,6-Br2, 4-CH3 B-216 2,4-Br2, 6-CH3 B-217 2,4-F2, 6-CH3 B-218 2,4-Br2, 6-CH3 B-219 2.6- (CH3) 2, 4-F B-220 2.6- (CH3) 2, 4-Cl B-221 2.6- (CH3) 2. 4-Br B-222 3.5- (CH3) 2, 4-F B-223 3.5- (CH3) 2. 4-Cl B-224 3.5- (CH3) 2, 4-Br B-226 3-CF3 B-228 2-OCF3 B-229 3-OCF3 B-230 4-OCF3 B-231 3-OCH2CHF2 B-232 2- NO2 B-233 3-NO2 B-234 4-N02 B-235 2-CN B-236 3-CN B-237 4-CN B-238 2-CH 3, 3-Cl B-239 2-CH 3 4-Cl B-241 2-CH3, 6-C1 B-243 2-CH3 / 4-F B-248 2-pyridyl-2'-B-249 3-pyridyl-3'-B-250 4-pyridyl-4 'Compounds I are suitable as fungicides. They have an excellent activity against a broad spectrum of phytopathogenic fungi, particularly of the Ascomycetes class, Deuteromycetes, Phycomycetes and Basidiomycetes. Some of them act systemically and can be used to protect crops as fungicides that have an action on the foliage and on the ground. They are especially important to control a large number of fungi in several crops such as wheat, rye, barley, oats, rice, corn, grass, banana, cotton, soybeans, coffee, sugar cane, grapes, fruit species, ornamental species and vegetables such as cucumbers, tomatoes, green beans, potatoes, and cucurbits, as well as the seeds of these plants. Specifically, they are suitable for controlling the following plant diseases: Alternaria species in vegetables and fruits, Botrytis cinerea (gray mold) in strawberries, vegetables, ornamental plants and grapes, Cercospora arachidicola in peanuts, Erysiphe cichoracearum and Sphaerotheca fuliginea in cucurbits. , Erysiphe graminis (powdery mildew) in cereals, Fusarium and Verticillium species in several plants, Species of Helminthosporium in cereals, Species of Mycosphaerella in bananas and peanuts, Phytophthora infestans in potatoes and tomatoes, Plasmopara viticulture in grapes, Podosphaera leucotricha in apples, Pseudocercosporella herpotrichoides in wheat and barley, Species of Pseudoperonospora in hops and cucumbers, Puccinia species in cereals, Pyricularia oryzae in rice, Species of Rhizoctonia in cotton, rice and turf, Septoria nodorum in wheat, • Uncinula necator in grapes, • Species of ustilago in cereals and sugarcane , and • Venturia species (crust) in apples and pears. In addition, the compounds I are suitable for controlling harmful fungi such as, for example, Paecilomyces variotti in the protection of materials (for example, wood, paper, paint dispersions, fibers or woven) and in the protection of stored products. The compounds I are used for the treatment of fungi or of the plants, seeds, materials or soils to be protected against attacks by fungi with a fungicidally effective amount of the active compounds. The application can be carried out before or after the infection of the materials, plants or seeds by the fungi. The fungicidal compositions generally comprise from 0.1 to 95% by weight of active compound, preferably from 0.5 to 90% by weight of active compound. For use in crop protection, the application regimes, depending in each case on the type of effect desired, vary from 0.01 to 2.0 kg of active compound per hectare. Seed treatment generally requires amounts of active compounds from 0.001 to 0.1 g, preferably from 0.001 to 0.05 g, per kilogram of seeds.

For use in the protection of stored materials or products, the rate of active compound application depends on the type of application area and the desired effect. Typical application regimes for the protection of materials are, for example, 0.001 g to 2 kg, preferably 0.005 g to 1 kg of active compound per cubic meter of treated material. The compounds of the formula I are also suitable for the efficient control of animal pests of the insect class, arachnids and nematodes. They can be used in the protection of crops and in the hygiene sector, for the protection of materials and in the veterinary sector to control al pests. They are especially suitable for controlling the following al pests: • insects of the order of Lepidoptera such as Agrotis ypsilon, Agrotis segetum, Alabama argillacea, Anticarsia gemmatalis, Argyresthia conjugella, Autographa gamma, Bupalus piniarius, Cacoecia murinana, Capua reticulana, Cheimatobia brumata, Choristoneura fumiferana, Choristoneura occidentalis, Cirphis unipuncta, Cydia pomonella, Dendrolimus pini, Diaph nitidalis, Diatraea grandiosella, Elands insulana, Elasmopalpus lignosellus, Eupoecilia ambiguella, Evetria bouliana, Feltia subterránea, Galleria mellonella, Grapholitha funebrana, Grapholitha molesta, Heliothis armigera, Heliothis virescens , Heliothis zea, Hellula undalis, Hibernia defoliaria, Hyphantria cunea, Hyponomeuta malinellus, Keiferia lycopersicella, Lambdina fiscellaria, Laphygma exigua, Leucoptera coffeella, Leucoptera scitella, Lithocolletis blancardella, Lobesia botrana, Loxostege sticticalis, Lymantria dispar, Ly antria monac ha, Lyonetia clerkella, Malacosoma neustria, Mamestra brassicae, Orgy pseudotsugata, Ostrinia nubilalis, Panolis flammea, Pectinophora gossypiella, Peridroma saucia, Phalera bucephala, Phthorimaea operculella, Phyllocnistis citrella, Pieris brassicae, Plathypena scabra, Plutella xylostella, Pseudoplusia includens, Rhyacionia frustrana, Scrobipalpula absoluta, Sitotroga cerealella, Sparganothis pilleriana, Spodoptera frugiperda, Spodoptera littoralis, Spodoptera litura, Thaumatopoea pityocampa, Tortrix viridana, Trichoplusia ni and Zeiraphera canadensis, • beetles (coleoptera), for example Agrilus sinuatus, Agriotes lineatus, Agriotes obscurus, Amphimallus solstitialis, andrus dispar, Anthonomus grandis, Anthonomus pomorum, Atomaria linearis, Blastophagus piniperda, Blitophaga undata, Bruchus rufimanus, Bruchus pisorum, Bruchus lentis, Byctiscus betulae, Cassida nebulosa, Cerotoma trifurcata, Ceuthorrhynchus assimilis, Ceuthorrhynchus napi, Chaetocnema tibialis, Conoderus v espertinus, Crioceris asparagi, Diabrotica longicornis, Diabrotica 12-punctata, Diabrotica virgifera, Epilachna varivestis, Epitrix hirtipennis, Eutinobothrus brasiliensis, Hylobius abietis, Hypera brunneipennis, Hypera postica, Ips typographus, Lema bilineata, Lema melanopus, Leptinotarsa decemlineata, Limonius californicus, Lissorhoptrus oryzophilus, Melanotus communis, Meligethes aeneus, Melolontha hippocast Melolontha melolontha, Oulema oryzae, Ortiorrhynchus sulcatus, Otiorrhynchus ovatus, Phaedon cochleariae, Phyllotreta chrysocephala, Phyllophaga sp., Phyllopertha horticulturally, Phyllotreta nemorum, Phyllotreta striolata, Popillia japonica, Sitona lineatus and Sitophilus granaria , • Diptera, for example Aedes aegypti, Aedes vexans, Anastrepha ludens, Anopheles maculipennis, Ceratitis capitata, Chrysomya bezziana, Chrysomya hominivoraz, Chrysomya macellaria, Contarinia sorghicola, Cordylobia anthropophaga, Culex pipiens, Dacus cucurbitae, Dacus oleae, Dasineura brassicae, Fannia cularis, Gasterophilus intestinalis, Glossina morsitans, Haematobia irritans, Haplodiplosis equestris, Hylemyia platura, Hypoderma lineata, Liriomyza sativae, Liriomyza trifolii, Lucilia caprina, Lucilia cuprina, Lucilia sericata, Lycoria pectoralis, Mayetiola destructor, Musca domestica, Muscina stabulans, Oestrus ovis , Oscinella frit, Pegomya hysocyami, Phorbia antiqua, Phorbia brassicae, Phorbia coarctata, Rhagoletis cerasi, Rhagoletis pomonella, Tabanus bovinus, Typula oleracea and Typula paludosa, Thips (Thysanoptera), such as Frankliniella fusca, Frankliniella occidentalis, Frankliniella tritici, Scirtothrips citris, Thrips oryzae, Thrips palmi and Thrips tabaci, • hymenoptera, for example Athalia rosae, Atta cephalotes, Atta sexdens, Atta texana, Hoplocampa minuta, Hoploca pa testudínea, Monomorium pharaonis, Solenopsis geminata and Solenopsis invicta, • Heteroptera, for example Acrosternum hilare, Blissus leucopterus, Cyrtopeltis notatus, Dysdercus cingulatus, Dysdercus intermedius, Eurygaster integriceps, Euschistus impictiventris, Leptoglossus phyllopus, Lygus lineolaris, Lygus pratensis, Nezara viridula, Piesma quadrata , Solubea insularis and Thyanta perditor, • Homoptera, eg Acyrthosiphon onobrychis, Adelges laricis, Aphidula nasturtii, Aphis fabae, Aphis pomi, Aphis sambuci, Brachycaudus cardui, Brevicoryne brassicae, Cerosipha gossypii, Dreyfusia nord annianae, Dreyfus piceae, Dysaphis radicóla, Dysaulacorthum pseudosolani, Empoasca fabae, Macrosiphum avenae, Macrosiphum euphorbiae, Macrosiphon rosae, Megoura viciae, Metopolophium dirhodum, Myzodes persicae, Myzus cerasi, Nilaparvata lugens, Pemphigus bursarius, Perkinsiella saccharicida, Phorodon humuli, Psylla mali, Psylla piri, Rhopalomyzus ascalonicus, Rhopalosiphum maidis, Sappaphis mala, Sappaphis mali, Schizaphis graminum, Schizoneura lanuginosa, Trialeurodes vaporariorum and Viteus vitifolii, • Termites (Isoptera), for example Acheta domestica, Blatta orientalis, Blattella germanica, Forfícula auricularia, Gryllotalpa gryllotalpa, Locusta migratoria, Melanoplus bivittatus, Melanoplus femur-rubrum, Melanoplus mexicanus, Melanoplus sanguinipes, Melanoplus spretus, Nomadacris septemfasciata, Periplantea americana, Schistocerca americana, Schistocerca peregrina, Stauronotus maroccanus and Tachycines asynamorus, • arachnoids such as arachnids (Acariña), for example, Amblyomma americanum, Amblyomma variegatum, Argas persicus, Boophilus annulatus , Boophilus decoloratus, Boophilus microplus, Brevipalpus phoenicis, Bryobia praetiosa, Dermacentor silvarum, Eotetranychus carpini, Eriophyes sheldoni, Hyalomma truncatum, Ixodes ricinus, Ixodes rubicundus, Ornithodorus moubata, Otobius megnini, Paratetranychus pilosus, Dermanyssus gallinae, Phyllocoptruta oleiv ora, Polyphagotarsoneums latus, Psoroptes ovis, Rhipicephalus appendiculatus, Rhipicephalus evertsi, Sarcoptes scabiei, Tetranychus cinnabarinus, Tetranychus kanza ai, Tetranychus pacificus, Tetranychus telarius and Tetranychus urticae, • nematodes such as root-gall nematodes, eg Meloidogyne hapla, Meloidogyne incognito, Meloidogyne javanica, cyst formation nematodes, eg Globodera rostochiensis, Heterodera avenae, Heterodera glycines, Heterodera schachtii, Heterodera trifolli, stem and leaf nematodes, eg, Belonilaimus longicaudatus, Ditylenchus destructor, Ditylenchus dipsaci, Heliocotylenchus multicinctus, Longidorus elongatus, Radopholus similis, Rotylenchus robustus, Trichodorus primitivus, Tylenchorhynchus claytoni, Tylenchorhynchus dubius, Pratylenchus neglectus, Pratylenchus penetrans, Pratylenchus curvitatus and Pratylenchus goodeyi. To control animal pests under free conditions, the active compound application rate is from 0.1 to 2.0, preferably from 0.2 to 1.0, kg / hectare. The compounds I can be converted into the customary formulations, for example, solutions, emulsions, suspensions, powders, pastes and granules. The form of application depends on the particular use foreseen; in each case, it must guarantee a fine and regular distribution of the compound according to the invention. The formulations are prepared in known manner, for example, by extending the active compound with solvents and / or vehicles, if desired using emulsifiers and dispersants, where, if water is used as a diluent, other organic solvents can also be used as auxiliary solvents. . Auxiliary suitable for this purpose are essentially: solvents such as aromatics (for example xylene), chlorinated aromatics (for example chlorobenzenes), paraffins (for example petroleum fractions), alcohols (for example methanol, butanol), ketones (for example cyclohexanone), amines (for example ethanolamine, dimethylformamide) and water; vehicles such as ground natural minerals (for example kaolins, clayey soils, talc, chalk) as well as ground synthetic minerals (for example finely divided silica, silicates); emulsifiers such as nonionic and anionic emulsifiers (for example polyoxyethylene, fatty alcohol ethers, alkylsulfonates and arylsulfonates) as well as dispersants such as lignosulfite and methylcellulose waste liquors. Suitable surfactants are the ammonium and alkali metal and ferrous alkali metal salts of lignosulfonic acid, naphthalenesulfonic acid, phenolsulfonic acid, dibutylnaphthalenesulfonic acid, alkylarylsulfonates, alkyl sulfates, alkyl sulfonates, fatty alcohol sulfates, as well as fatty acids and metal salts alkalines and ferrous alkali metal salts thereof, salts of glycol ethers of sulfated fatty alcohols, condensation products of sulfonated naphthalene and derivatives of naphthalene with formaldehyde, condensation products of naphthalene or of naphthalenesulfonic acid with phenol and formaldehyde, octylphenol ethers of polyoxyethylene, isooctylphenol, octylphenol and nonylphenol ethoxylates, alkylphenol polyglycol ethers, tributylphenyl polyglycol ethers, alkylaryl polyether alcohols, isotridecyl alcohol, fatty alcohol ethylene oxide condensates, ethoxylated castor oil, alkyl ethers polyoxyethylene, ethoxylated polyoxyethylene, acetal of polyglycol ether of lauryl alcohol, sorbitol esters, liquors of lignosulfite residue and methylcellulose. Suitable for the preparation of directly sprayable solutions, emulsions, pastes or dispersions in oil are petroleum fractions that have medium to high boiling points, such as kerosene or diesel fuel, coal tar oils and oils of origin vegetable or animal, aliphatic, cyclic and aromatic hydrocarbons, for example benzene, toluene, xylene, paraffin, tetrahydronaphthalene, alkylated naphthalenes or derivatives thereof, methanol, ethanol, propanol, butanol, chloroform, carbon tetrachloride, cyclohexanol, cyclohexanone, chlorobenzene , isophorone, strongly polar solvents, for example dimethylformamide, dimethyl sulfoxide, N-methylpyrrolidone and water. Powders, spraying compositions can be prepared by mixing or co-grinding the active substances with a solid carrier. Granules, for example coated granules, impregnated granules and homogeneous granules, can be prepared by binding the active ingredients to the solid carriers. Solid carriers are, for example, mineral earths, such as silica gel, silicas, silica gels, silicates, talc, kaolin, clay, limestone, chalk, chalk, clay earth, loess, dolomite, diatomaceous earth, sulphate. calcium, magnesium sulfate, magnesium oxide, ground synthetic materials, fertilizers, such as, for example, ammonium sulfate, ammonium phosphate, ammonium nitrate, ureas and products of vegetable origin, such as, for example, cereal particles, bark particles, tree, wood particles and nutshell particles, cellulose powders and other solid vehicles. The formulations generally comprise from 0.01 to 95% by weight, preferably from 0.1 to 90% by weight, of the active compound. The active compounds are used in a purity of 90% to 100%, preferably 95% to 100%) according to the NMR spectrum. Examples of formulations are: I.5 parts by weight of a compound according to the present invention are completely mixed with 95 parts by weight of finely divided kaolin. This provides a composition for sprinkling comprising 5% by weight of the active compound. II. 30 parts by weight of a compound according to the invention are completely mixed with a mixture of 92 parts by weight of silica gel powder and 8 parts by weight of paraffin oil which had been sprayed on the surface of this silica gel . This provides an active compound preparation having good adhesive properties (content of active compound: 23% by weight). III. 10 parts by weight of a compound according to the present invention is dissolved in a mixture comprising 90 parts by weight of xylene, 6 parts by weight of the addition product of 8 to 10 moles of ethylene oxide with 1 mole of oleic acid N-monoethanolamide, 2 parts by weight of the calcium salt of dodecylbenzenesulfonic acid and 2 parts by weight of the addition product of 40 moles of ethylene oxide with 1 mole of castor oil (content of active compound: 9% by weight). IV. 20 parts by weight of a compound according to the present invention is dissolved in a mixture comprising 60 parts by weight of cyclohexanone, 30 parts by weight of isobutanol, 5 parts by weight of an addition product of 7 moles of ethylene oxide with 1 mole of isooctylphenol and 5 parts by weight of the addition product of 40 moles of ethylene oxide with 1 mole of castor oil (content of active compound: 16% by weight). V.80 parts by weight of a compound according to the present invention are completely mixed with 3 parts by weight of the sodium salt of diisobutylnaphthalene-alpha-sulfonic acid, 10 parts by weight of the sodium salt of a lignosulfonic acid from a sulphite residue liquor and 7 parts by weight of silica gel powder, and ground in a hammer mill (content of active compound: 80% by weight). SAW . 90 parts by weight of a compound according to the present invention are mixed with 10 parts by weight of N-methyl-alpha-pyrrolidone, providing a solution which is suitable for use in the form of very small drops (content of active compound: 90% by weight). VII. 20 parts by weight of a compound according to the present invention are dissolved in a mixture comprising 40 parts by weight of cyclohexanone, 30 parts by weight of isobutanol, 20 parts by weight of the addition product of 7 moles of ethylene oxide with 1 mole of isooctylphenol and 10 parts by weight of the addition product of 40 moles of ethylene oxide with 1 mole of castor oil. The solution is poured into 100,000 parts by weight of water and finely dispersed therein, yielding an aqueous dispersion comprising 0.02% by weight of the active compound. VIII. 20 parts by weight of a compound according to the present invention are mixed well with 3 parts by weight of the sodium salt of diisobutylnaphthalene-alpha-sulphonic acid, 17 parts by weight of the sodium salt of a lignosulfonic acid from a sodium liqueur. sulfite residue and 60 parts by weight of a silica gel powder, and ground in a hammer mill. The mixture is finely dispersed in 20,000 parts by weight of water, providing a spray liquor comprising 0.1% by weight of active compound. The active compounds can be applied as such, in the form of their formulations or in the forms of application prepared therefrom, for example, in the form of directly sprayable solutions, powders, suspensions or dispersions, emulsions, dispersions in oil, pastes. , powders, compositions to be applied to the bole or granules, by means of spraying, atomization, spraying, application to the bole or irrigation. The forms of application are totally dependent on the intended uses; in each case they should insofar as possible ensure the finest possible distribution of the active compounds according to the invention. The aqueous forms of use can be prepared from emulsion concentrates, pastes, or wettable powders (spray powders, dispersions in oil) by the addition of water. To prepare the emulsions, pastes or dispersions in oil, the substances can be homogenized in water as such or dissolved in an oil or solvent, by means of wetting agents, binders, dispersants or emulsifiers. However, concentrates comprising active compound, wetting agent, binder, dispersant or emulsifier and possibly solvent and oil which are suitable for dilution with water can also be prepared. The concentration of active compound in ready-to-use preparations can vary over a relatively wide range. In general, they comprise from 0.0001 to 10%, preferably from 0.01 to 1%. It is also possible to employ the active compounds with good success in the ultra low volume process (ULV), it being possible to apply formulations comprising more than 95% by weight of active compound or else to the active compound without additives. It is possible to mix oils of various types, herbicides, fungicides, other pesticides, or bactericides with the active compounds, even, if appropriate, immediately before application (mixed in the tank). These agents can be mixed with the compositions according to the present invention in a weight ratio of 1:10 to 10: 1. The compounds according to the present invention in the form of use as fungicides can also be present with other active compounds, for example, with herbicides, insecticides, growth regulators, fungicides, or with fertilizers. In many cases, a mixture of the compounds I or the compositions comprising them in the form of use as fungicides with other fungicides results in a broader spectrum of fungicidal activity. The following list of fungicides, together with which the compounds according to the present invention can be used, is intended to illustrate the possible combinations, but not to impose any limitations: • sulfur, dithiocarbamates and their derivatives, such as, for example, dimethyldithiocarbamate iron (III), zinc dimethyldithiocarbamate, zinc ethylene bisdithiocarbamate, manganese ethylene bisdithiocarbamate, manganese zinc ethylene diamine bisdithiocarbamate, tetramethylthiuram disulfides, zinc ammonia complex (N, N-ethylene bisdithiocarbamate), zinc ammonia complex (N, N ') propylenebisdithiocarbamate), zinc (N, N'-propylenebisdithiocarbamate), N, N'-polypropylenebis (thiocarbamoyl) disulfide; • nitro derivatives, such as, for example, dinitro (1-methylheptyl) phenyl crotonate, 2-sec-butyl-4,6-dinitrophenyl-3,3-dimethyl acrylate, 2-sec-butyl-4,6-carbonate. dinitrophenylisopropyl, diisopropyl 5-nitroisophthalate; • heterocyclic substances, such as, for example, 2-heptadecyl-2-imidazoline acetate, 2,4-dichloro-6- (o-chloroanilino) -s-triazine, O-diethyl, 5-amino-1-phthalimidophosphothioate bis (dimethylamino) phosphinyl] -3-phenyl-1,2,4-triazole, 2,3-dicyano-1,4-dithioanthraquinone, 2-thio-l, 3-dithiolo [4,5-b] quinoxaline, 1 - (methyl butylcarbamoyl) -2-benzimidazolcarbamate, 2-methoxycarbonylaminobenzimidazole, 2- (furyl- (2)) benzimidazole, 2- (thiazolyl) - (4)) benzimidazole, N- (1,1, 2,2-tetrachloroethylthio) ) tetrahydrophthalimide, N-trichloromethylthiotetrahydroftalimide, N-trichloromethylthiophthalimide, • N-dichlorofluoromethylthio-N ', N'-dimethyl-N-phenyl sulfuric diamide, 5-ethoxy-3-trichloromethyl-1,2,3-thiadiazole, 2-thiocyanatomethylthiobenzothiazole, 1,4-dichloro-2,5-dimethoxy-benzene, 4- (2-chlorophenylhydrazono) -3-methyl-5-isoxazolone, 2-thio-l-pyridine oxide, 8-hydroxyquinoline or its copper salt, , 3-dihydro-5-carboxanilido-6-methyl-l, 4-oxathiane, 2,3-dihydro-5-carboxanilido-6-methyl-l, 4-oxatiina- 4, 4-dioxide, 2-methyl-5,6-dihydro-4H-pyran-3-carboxanilide, 2-methyl-furan-3-carboxanilide, 2,5-dimethyl-furan-3-carboxanilide, 2,, 5-trimethyl-furan-3 -carboxanilide, N-cyclohexyl-2, 5-dimethyl-furan-3-carboxamide, N-cyclohexyl-N-methoxy-2,5-dimethyl-furan-3-carboxamide, 2-methylbenzanilide, 2-iodobenzanilide, N-formyl-N-acetal -morpholine 2,2,2, -triichloroethyl, piperazin-1,4-diyl-bis- (1- (2, 2, 2-trichloroethyl) -formamide, 1- (3,4-dichloroanilino) -1-formylamino- 2, 2, 2-trichloroethane, 2,6-dimethyl-N-tridecylmorpholine or its salts, 2,6-dimethyl-N-cyclododecylmorpholine or its salts, N- [3- (p-tert-butylphenyl) -2-methylpropyl ] -cis-2, 6-dimethylmorpholine, N- [3- (p-tert-butylphenyl) -2-methylpropyl] piperidine, 1- [2- (2,4-dichlorophenyl) -4-ethyl-1, 3- dioxolan-2-ylethyl] -1H-1, 2,4-triazole, 1- [2- (2, -dichlorophenyl) -4-n-propyl-l, 3-dioxolan-2-ylethyl] -1H-1, 2,4-triazole, N- (n-propyl) -N- (2,4,6-trichlorophenoxyethyl) -N'-imidazolylurea, 1- (4-chlorophenoxy) -3,3-dimethyl-1- (1H- 1, 2, -triazol-1-yl) - 2-butanone, 1- (4-chlorophenoxy) -3,3-dimethyl-1- (1 H-1,2,4-triazol-1-yl) -2-butanol, (2RS, 3RS) -1- [3 - (2-chlorophenyl) -2- (4-fluorophenyl) oxiran-2-ylmethyl] -1H-1, 2,4-triazole, alpha- (2-chlorophenyl) -alpha- (4-chlorophenyl) -5-pyrimidinemethanol , 5-buty1-2-dimethylamino-4-hydroxy-6-methyl-pyrimidine, bis (p-chlorophenyl) -3-pyridinemethanol, 1,2-bis (3-ethoxycarbonyl-2-thioureido) benzene, 1-2 bis (3-methoxycarbonyl-2-thioureido) benzene, • strobilurines such as, for example, methyl E-methoxyimino- [alpha- (o-tolyloxy) -o-tolyl] acetate, E-2-. { 2- [6- (2-cyano-phenoxy) pyrimidin-4-yloxy] phenyl} Methyl-3-methoxyacrylate, N-methyl-E-methoxyimino- [alpha- (2-phenoxyphenyl)] -acetamide, N-methyl-E-methoxyimino- [alpha- (2,5-dimethylphenoxy) -o-tolyl] acetamide, • anilinopyrimidines, such as for example N- (4,6-dimethylpyrimidin-2-yl) aniline, N- [4-methyl-6- (1-propynyl) pyrimidin-2-yl] aniline, N- [4- methyl-6-cyclopropyl-pyrimidin-2-yl] aniline, • phenylpyrroles such as 4- (2, 2-difluoro-1,3-benzodioxol-4-yl) pyrrole-3-carbonitrile, • cinnamides, such as for example 3- (4-chlorophenyl) -3- (3, 4-dimethoxyphenyl) acryloylmorpholine, and various fungicides, such as, for example, dodecylguanidine acetate, 3- [3- (3,5-dimethyl-2-oxycyclohexyl) -2-hydroxyethyl] glutarimide, hexachlorobenzene, methyl-N- (2,6-di-ethylphenyl) -N- (2-furoyl) -DL-alaninate, methyl ester of DL-N- (2,6-dimethylphenyl) -N- (2 '- methoxyacetyl) alanine, (N- (2,6-dimethylphenyl) -N-chloroacetyl-D, L-2-aminobutyrolactone, methyl ester of DL-N- (2,6-dimethylphenyl) -N- (phenylacetyl) alanine, -methyl-5-vinyl-3- (3, 5-dichloride) rophenyl) -2,4-dioxo-l, 3-oxazolidine, 3- (3,5-dichlorophenyl) -5-methyl-5-methoxymethyl-l, 3-oxazolidon-2,4-dione, 3- (3, 5-dichlorophenyl) -1-isopropylcarbamoylhydantoin, N- (3,5-dichlorophenyl) -1,2-dimethylcyclopropane-1,2-dicarboximide, 2-cyano- [N- (ethylaminocarbonyl) -2-methoximino] acetamide, 1- [2- (2,4-dichlorophenyl) pentyl] -1H-1,2, -triazole, 2,4-dubluoro-alpha- (1H-1,2,4-triazolyl-1-methyl) -benzhydryl alcohol, N - (3-chloro-2, 6-dinitro-4-trifluoromethylphenyl) -5-trifluoromethyl-3-chloro-2-aminopyridine, 1- ((bis (4-fluorophenyl) methylsilyl) -methyl) -1H-1,2,4-triazole. Synthesis Examples The procedures offered in the synthesis examples below were employed to prepare additional I compounds by means of an appropriate modification of the starting materials. The compounds obtained in this way appear in the list in the following tables, together with physical data. Example 1: 2,4-dihydro-5-methoxy-2-methyl-4-. { 2- [1- (4-fluorophenyl) -1,2, -triazolyl-3] oxymethylphenyl} -3H-1, 2,4-triazol-3-one [J-1] CH, A mixture of 0.6 g (3 ramol) of (4-fluorophenyl) -3-hydroxytriazole in 15 ml of dimethylformamide was mixed with 0.1 g (3.6 mmol) of sodium hydride and stirred at a temperature of 20 to 25 ° C for approximately 5 minutes. Subsequently 1 g (3.3 mmol) of 4- (2-bromomethylphenyl) -2,4-dihydro-5-methoxy-2-methyl-3H-1, 2,4-triazol-3-one was added [WO-A 95 / 14,009] subsequently and the mixture was stirred at a temperature of 20 to 25 ° C for about 14 hours. Water was added, and the aqueous phase was extracted with methyl tert-butyl ether. The combined organic phases were extracted with water, dried and concentrated. Silica gel chromatography of the residue using a cyclohexane / ethyl acetate mixture afforded 0.55 g of the title compound as a light yellow solid with a melting point of 137-139 ° C. 1 H-NMR (CDC13): 3.45 (s, 3H); 3.95 (s, 3H); 5.4 (s, 2H); 7.1 -7.3 (m, 3H); 7.45 (m, 2H); 7.55 (m, 2H); 7.75 (d, br, 1H); 8.15 ppm (s, 1H). Example 2: 2,5-dihydro-2-methyl-5-. { 2- [1- (4-fluorophenyl) -pyrazol-3-yl] oxymethylphenyl} tetrazolone [1-3] CH.

A solution of 1.36 (7 mmol) of 1- (4-fluorophenyl) -3-hydroxy-pyrazole in 25 ml of anhydrous dimethylformamide (DMF) was mixed with 0.18 g of sodium hydride. The mixture was stirred at a temperature of 20-25 ° C for about one hour, a solution of 1.88 g (7 mmol) of 2,5-dihydro-2-methyl-5- (2-bromomethylphenyl) tetrazolone was added [WO. -A 96/36229] in 15 ml of anhydrous DMF and the solution was stirred at a temperature of 20-25 ° C for an additional 14 hours. The solution was diluted with 300 ml of a diluted NaCl solution extracted with methyl tert-butyl ether (MTBE) and the combined organic phases were then washed with water and dried. The solvent was removed by distillation and the residue was chromatographed on silica gel (cyclohexane / MTBE 1: 1) to give 1.8 g of the title compound as clear yellow crystals of melting point 89-93 ° C. Example 3: 2,4-dihydro-2,5-dimethyl-4-. { 2- [1- (4-chlorophenyl) -pyrazol-3-yl] oxymethylphenyl} -3H-1, 2,4-triazol-3-one [1-46] Example 3a: 2- [1- (4-chlorophenyl) pyrazol-3-yl] oxymethylaniline At a temperature of 20-25 ° C and under a hydrogen pressure of 20 bar, a mixture of hydrogenated with stirring was stirred for about 20 hours. 30 g (90 mmol) of 2- [1- (4-chlorophenyl) pyrazol-3-yl] oxymethylnitrobenzene and 2 g of platinum in activated carbon (5%) in 200 ml of ethyl acetate. The mixture was filtered through A1203 and the solvent was removed from the filtrate by distillation, yielding 23.3 g of the aniline in the form of yellow crystals of melting point 81-83 ° C. 2H NMR (CDC15; d in ppm): 7.65 (d, 1H); 7.5 (d, 2H); 7.35 (d, 2H); 7.25 (d, 1H); 7.15 (t, br, 1H); 6.7 (m, 2H); 5.9 (d, 1H); 5.25 (s, 2H); 4.15 (s, br, 2H) Example 3b: phenyl 2- [1- (4-chlorophenyl) pyrazol-3-yl] oxymethylcarbamate A mixture of the aniline of Example 3a and 12 g (0.15 mol) of pyridine in 200 ml of methylene chloride was mixed with 16 g (0.1 mol) of phenyl chloroformate at a temperature of 0 ° C, and the mixture was then stirred at a temperature of 20-25 ° C for about 1.5 hours. The mixture was washed with dilute hydrochloric acid and water and dried, and the solvent was removed by distillation. Digestion of the residue in diisopropyl ether gave 41 g of the title compound as light yellow crystals with a melting point of 143-144 ° C. 2H NMR (CDC13; d in ppm): 8.95 (s, br, 1H); 7.95 (d, br, 2H); 7.65 (d, 1H); 7.55 (d, 2H); 7.45 (d, 1H); 7.05-7.45 (m, 9H); 5.9 (d, 1H); 5.4 (s, 2H). Example 3c: N-. { 2- [1- (4-chlorophenyl) pyrazol-3-yl] oxymethylphenyl} -N'-methylsemicarbazide A mixture of the ester from example 3b and 3.5 g (75 mmol) of methylhydrazine in 100 ml of methylene chloride was stirred at a temperature of 20-25 ° C for about 15 hours. The solvent was removed by distillation and the residue was digested in methyl tert-butyl ether (MTBE), affording 6.5 g of the title compound as bright yellow crystals of melting point 152-154 ° C. U NMR (CDC13; d in ppm): 9.3 (s, br, 1H); 8.1 (d, 1H); 7.7 (d, 1H); 7.65 (d, 2H); 7.35 (m, 4H); 7.0 (t, 1H); 5.9 (d, 1H); 5.3 (s, 2H); 3.7 (s, 2H); 3.2 (s, 3H). Example 3d 2, -dihydro-2, 5-dimethyl-4-. { 2- [1- (4-chlorophenyl) -pyrazol-3-yl] oxymethylphenyl} -3H-1, 2,4-triazol-3-one [1-46] A mixture of 6 g (16 mmol) of semicarbazide from example 3c and a spatula tip of p-toluenesulfonic acid in 50 ml of triethyl orthoacetate was refluxed for about 5 hours. The solvent was removed by distillation and the residue was chromatographed on silica gel (cyclohexane / ethyl acetate mixture), affording 1.9 g of the title compound as yellow crystals with a melting point of 107-108 ° C. . * H NMR (CDC13; d in ppm): 7.7 (m, 2H); 7.5 (m, 4H); 7.35 (d, 2H); 7.2 (d, 1H); 5.85 (d, 1H); 5.25 (dd, 2H); 3.45 (s, 3H); 2.0 (s, 3H). Table 1 No. Formula (R1 ^ Ra and RJ p.f. [° C] IR [cm "1] 1-1 IB H OCH3 CH3 N H 4-F-C6H4 137-139 1723, 1615, 1546, 1502, 1-2 IB H OCH3 CH3 CH H 4-Cl-C6H4 1480, 1458, 1414, 1390, 1360, 744 1-3 IC H - CH3 CH H 4 - Cl - C6H4 89-93 1-4 IB H OCH3 CH3 CH H 3.4 - Cl2 - 120-123 C6H 1-5 IB H Cl CH3 CH H 4 - CH3 - 146 -149 C6H 1-6 IB H OCH3 CH3 CH H 4-CH3- 106-108 C6H 1-7 IB H Cl CH3 CH H 2 -CH3- 115-118 pyridyl-6 1725, 1615, I-IB H OCH3 CH; CH H pyridyl- 1505, 1480, 6 1466, 1414, 1390, 1360 1-9 IB H Cl CH 3 CH H 4-OC 2 H 5 - 128-135 CeH 1-10 IB H OCH 3 CH 3 CH H 4-OC 2 H 5 - 1723, 1615, C 6 H 4 1543, 1516, 1481, 1457, 1414, 1392, 1247, 1050 1-11 IB H Cl CH3 CH H 3- Cl- CßH 104-109 1-12 IB H OCH3 CH3 CH H 3- Cl - CßH.4 116-118 1-13 IB H Cl CH 3 CH H 2 - Cl- C 6 H 1728, 1545, 1495, 1476, 1452, 1396, 1360, 761, 737, 621 1-14 IB H OCH3 CH3 CH H 2 - Cl- C6H4 1725, 1615, 1546, 1495, 1477, 1452, 1414, 1361, 761, 743 -15 IB H Cl CH3 CH H 2,4-F2- 100-103 C6H4 1725, 1615, 1550, 1517, 1-16 IB H OCH3 CH3 CH H 2.4-F2- 1482, 1457, CeH4 1446, 1415, 1270, 970 1-17 IB H Cl CH 3 CH H 3-Cl- 85-94 pyridyl-6 I-ll IB H OCH 3 CH 3 CH H 3 -Cl- 121-129 pyridyl-6 1-19 IB H Cl CH, CH H 3- CF3- 111-117 C6H 1717, 1613, 1556, 1507, 1-20. IB H OCH3 CH3 CH H 3-CF3-1477, 1455, C6H4 1357, 1332, 1170, 1115 1726, 1546, 1499, 1480, 1-21 IB H Cl CH 3 CH H 4-Br-C 6 H 4 1458, 1421, 1392, 1358, 1076, 935 1724, 1615, 1547 r 1499, -22 IB H OCH 3 CH, CH H 4-Br-C 6 H 4 1480, 1457 , 1414, 1389, 1360 1077 1728, 1546, 1496, 1475, -23 IB H Cl CH3 CH H 2,4-Cl2- 1458 r 1417, C6H4 1397 1358, 1059, 763 1725, 1615, 1547 r 1496, -24 IB H OCH3 CH3 CH H 2.4-Cl2-1477 r 1414, CeH4 1389 1359, 1321 744 1727 1538, 1490 1459, -25 IB H Cl CH3 CH H C2H5 1397, 1380, 1365 765, 737, 621 1724, 1615 , 1536, 1505, -26 IB H OCH3 CH3 CH H C2H5 1489, 1458, 1414; 1388, 1321, 743 1-27 IB H Cl CH 3 C (CH 3) H 4-CH 3 - 119-130 1725, 1615, 1519, 1506, I-2Í IB H OCH3 CH3 C (CH3) H 4-CH3- 1480, 1457, CdH4 1414, 1361, 1199, 941 1-29 IB H Cl CH 3 C (CH 3) H 2,4-Cl 2 -81-85 CeH 1-30 IB H OCH 3 CH 3 C (CH 3) H 2,4-Cl 2- 141-145 C 6 H 4 1729, 1599, 1540, 1500, 1-31 IB H Cl CH3 C (CH3) H C5H5 1466, 1398, 1363, 1197, 763, 756 1-32 IB H OCH3 CH3 C (CH3) H C6H5 134-137 1-33 IB H Cl CH 3 CC 1 H 4-CH 3 -130-133 C 6 H 4 1723, 1615, 1554, 1510, 1-34 IB H OCH3 CH3 CC1 H 4-CH3- 1479, 1457, C6H4 1414, 1390, 1361, 1118 1726 r 1544, 1500, 1480, - 35 IB H Cl CH3 NH 4-Cl-C6H4 1458 r 1397, 1330 , 1242, 1093, 974 1706 r 1619, 1603 r 1547, 1 - . 1 - . 1 -36 IB H OCH3 CH3 N H 4-Cl-C6H4 1486 r 1477, 1336, 1326, 1083, 980 1726 r 1544, 1494, 1477, 1-37 IB H Cl CH 3 N H 2,4-Cl 2 - 1457, 1396, CeH 4 1331 t 1274, 1065, 994 1723 1616, 1545 1479, I-3 Í IB H OCH3 CH3 N H 2,4-Cl2- 1457 1414, CeH4 1388 1330, 1066 974 1728, 1542, 3.4-1505 1481, 1 -39 IB H Cl CH3 N H (CH3) 2- 1458 1397, 1065, 994 3.4- 127-131 1-40 IB H OCH3 CH3 NH (CH3) 2- C6H3 1-41 IB H Cl CH3 NH 4-CF3- 134-145 1-42 IB H OCH3 CH3 NH 4-CF3- 145-149 C6H4 1728 1540, 1488 1457 , 1-43 IB H Cl CH5 N CH3 2,4-Cl2- 1419 1396, C6H4 1349 1274, 1018 994 1724 1616, 1541 1502, 1-44 IB H OCH3 CH3 N CH3 2,4-Cl2- 1480 1457 C6H4 1415 1389, 1350 1068 1641 1603, 1546 1502, 1-45 IA H OCH3 CH5 CH N 4-Cl-C6H4 1481 1400, 1383 1359, 1028 936 1722 1613, 1546 1502, 1-46 IB 6- OCH3 CH3 CH H 4-Cl-C6H4 1488 1502, CH3 1425, 1413, 1390, 1358, 1070 1-47 IB H CH3 CH3 CH H 4-Cl-C6H4 107-109 1-48 IB 6- H CH3 CH H 4-Cl-C6H4 126-128 CH3 1-49 IB HH CH3 CH H 4-Cl-C6H4 130- 132 1-50 IB 6- CH3 CH3 CH H 4-Cl-C6H4 120-124 CH3 Examples of action against harmful fungi The fungicidal action of the compounds of the formula I was demonstrated through the following experiments: The active compounds, separately or together, were formulated as a 10% emulsion in a mixture of 63% by weight of cyclohexanone and 27% by weight of emulsifier and diluted with water to obtain the desired concentration. Example of use 1 - Activity against Plasmopara vitícola Leaves of grape in pots of the variety "Müller-Thurgau" were sprayed with an aqueous preparation of the active compound prepared from a stock solution of 10% of active compound, 63% of ciciohexanone and 27% emulsifier until runoff. In order to be able to evaluate the long-term activity of the substances, the plants were kept for 7 days in the greenhouse after drying the sprayed coating. Only then the leaves were inoculated with a suspension of aqueous zoospores of Plasmopara viticola. The vines were then held first in a chamber saturated with steam at a temperature of 24 ° C for 48 hours, and then in a greenhouse at a temperature of 20-30 ° C for 5 days. The plants were then kept for an additional 16 hours in a chamber with high atmospheric humidity to stimulate spore formation. The magnitude of the infection on the lower sides was evaluated visually afterwards. In this test, plants that had been treated with 16 ppm of compounds No. 1-2, 1-4, 1-6, 1-8, 1-10, 1-12, I-16, 1-18, 1-20, 1-22, 1-24, 1-28, 1-32, 1-38 and 1-44 had a maximum infection of 15%, while infection levels in the case of untreated plants were 75% Example of use 2 - Activity against Puccinia recondite in wheat (rust from the wheat leaf) Leaves from wheat plantlets in pots of the variety "Frühgold" were sprinkled with spores of wheat leaf rust (Puccinia recóndita). Afterwards, the pots were kept in a chamber with high atmospheric humidity (from 90 to 95%) and a temperature of 20 to 22 ° C for 24 hours. During this period, the spores germinated and the germinal tubules penetrated the tissue of the leaf. The next day, the infected plants were sprayed with an aqueous active compound formulation to the point of runoff. After drying the sprayed coating, the test plants were grown for 7 days in a greenhouse at a temperature of 20-22 ° C and under a relative atmospheric humidity of 65-70%. Afterwards, the magnitude of the development of the rust fungus in the leaves was determined. In this test, plants that had been treated with 16 ppm of compounds No. 1-2, 1-4, 1-6, 1-16, 1-22, 1-24, I-28, 1-32 and 1-38 had an infection or greater than 15% while the infection levels of the untreated plants were 80%. Example of use 3 - Activity against Pyricularia oryzae (protective) Leaves of small rice plants in pots of the variety "Tai-Nong 67" were sprayed with an aqueous active compound formulation to the point of runoff. The next day, the plants were inoculated with an aqueous suspension of spores of Pyricularia oryzae. The test plants were subsequently maintained for 6 days in conditioning chambers at a temperature of 22-24 ° C and under a relative atmospheric humidity of 95-99%. Afterwards, the magnitude of the development of the disease in the leaves was visually determined.

In this test, plants that had been treated with 16 ppm of compounds No. 1-2, 1-6, 1-12, 1-16, 1-18, 1-20, 1-21, 1-22, 1-23, 1-24, 1-28, 1-30, 1-32 and 1-40 presented an infection of 0 to 15% while the levels of infection of the untreated plants were 90%. EXAMPLES OF ACTION AGAINST ANIMAL PESTS The action of the compounds of the formula I against animal pests was demonstrated through the following experiments: The active compounds were formulated a. as a 0.1% solution in acetone or b. as a 10% emulsion in a mixture of 70% by weight of ciciohexanone, 20% by weight of Nekanil® LN (Lutensol® AP6, wetting agent based on ethoxylated alkyl phenols having an emulsifying and dispersing action) and % by weight of Wettol_MS (nonionic emulsifier based on ethoxylated castor oil) and were diluted in the case of a. with acetone and in the case of b. with water in order to provide the desired concentration. After the completion of the experiments, in each case, the lowest concentration was determined with which the compounds continued to cause an inhibition or mortality of 80 to 100% in comparison with the control experiments without treatment (critical or minimum concentration).

Claims (3)

CLAIMS 2- [pyrazolyl- and triazolyl-3'-oxymethylene] phenylisoxazolones, -triazolones and -tetrazolones of the formula I where: X is a group A, B or C, where # refers to the bond with the phenyl ring and Ra is hydrogen, halogen, C1-C4 alkyl or C: -C4 alkoxy and Rb is C? -C alkyl; Y is N or CRC, where Rc is hydrogen, halogen or C alquilo-C4 alkyl; n is 0, 1, 2, 3 or 4, where the substituents R1 may be different if n is greater than 1; R 1 is nitro, cyano, halogen, Ci-Cβ alkyl with or without substitution or alkoxy with or without substitution or is also, if n is 2, a bridge with or without substitution containing from 3 to 4 members of group 3 or 4 carbon atoms, 2 to 3 carbon atoms and 1 or 2 nitrogen atoms, oxygen and / or sulfur fixed on two adjacent ring atoms, it being possible for this bridge to form together with the ring on which a radical is partially fixed unsaturated or aromatic; R 2 is hydrogen, nitro, cyano, halogen, C 1 -C 4 alkyl, C 1 -C haloalkyl, C 1 -C 4 alkoxy, C 1 -C alkylthio or C 1 -C 4 alkoxycarbonyl; R3 is Ci-Cß alkyl with or without substitution, C3-Cß cycloalkyl with or without substitution, aryl with or without substitution or hetaryl with or without substitution. A process for the preparation of the compounds of the formula I according to claim 1, which comprises the reaction of a benzyl derivative of the formula II wherein L is a nucleophilically displaceable group, in the presence of a base with a 3-hydroxypyrazole or 3-hydroxytriazole of the formula III A process for the preparation of compounds of the formula IB, wherein Ra is C? -C4 alkyl or C? -C4 alkoxy, and Y, Rb, Rc, R1, n, R2 and R3 are each in accordance with that defined in claim 1, comprising reactive anilines of the formula lia with phosgene or an equivalent of phosgene to provide isocyanates of the formula IIb and reacting Ilb with alkylhydrazines C? ~ C4 to provide carbamates of the formula lie cyclizing lie with phosgene or an equivalent of phosgene to provide triazolones of the formula and converting lid either by reaction with alcohols of the formula IVa, Re-0H IVa where Re is C? -C4 alkyl, in triazolones of the formula IB wherein Ra is C1-C4 alkoxy, or by reaction with amidines of the formula IVb, wherein Ra is C 1 -C 4 alkyl or C 4 -C 4 alkoxy, or with orthoesters of the formula IVc, Ra-C (0CH 3) 3 IVe wherein Ra is C 1 -C 4 alkyl or C 1 -C 4 alkoxy in triazolones of the formula IB wherein Ra is C 1 -C 4 alkyl or C

1 -C 4 alkoxy. A process for the preparation of compounds of the formula IC wherein Y, Rb, Rc, R1, n, R2 and R3 are each in accordance with that defined in claim 1, which comprises the reaction of anilines of the formula with phosgene or an equivalent of phosgene to provide isocyanates of the formula Ilb and reacting Ilb with azides of the formula IVd, M-N3 IVd where M is a cation selected from the group consisting of alkali metals or ferrous alkali metals, trialkylsilyl or alkyl to provide tetrazolones of the formula and converting it by alkylation into compounds of the formula IC. A composition suitable for controlling animal pests or harmful fungi, comprising a solid or liquid carrier and a compound of formula I in accordance with claim 1. The use of compounds I according to claim 1 for preparing a composition suitable for controlling animal pests or harmful fungi. A method for controlling harmful fungi, comprising treating the fungi or the materials, plants, soil or seeds to be protected against fungal attack with an effective amount of a compound of the formula I in accordance with that claimed in claim 1 . A method for controlling animal pests comprising the treatment of the animal pests or the materials, plants, soil or seeds to be protected against them with an effective amount of a compound of the formula I in accordance with that claimed in claim 1. SUMMARY OF THE INVENTION 2 [pyrazolyl- and triazolyl-3'-oxymethylene] phenylisoxazolones, triazolones and -tetrazolones of the formula I (' where: X is a group A, B or C, where # denotes the bond with the phenyl ring and Ra is hydrogen, halogen, alkyl or alkoxy and Rb is alkyl; Y is N or CRC, where Rc is hydrogen, halogen or alkyl; N is 0, 1, 2, 3 or 4, where the substituents R1 may be different if n is greater than 1; R1 is nitro, cyano, halogen, alkyl with or without substitution or alkoxy with or without substitution or is additionally, if n is 2, a bridge with or without substitution containing from 3 to 4 members of group 3 or 4 atoms of carbon, 2 to 3 carbon atoms and 1 or 2 nitrogen atoms, oxygen and / or sulfur joined on two adjacent ring atoms, it being possible for this bridge to form, together with the ring on which a partially unsaturated or aromatic radical is attached; R 2 is hydrogen, nitro, cyano, halogen, alkyl, haloalkyl, alkoxy, alkylthio or alkoxycarbonyl; R3 is alkyl with or without substitution, cycloalkyl with or without substitution, aryl with or without substitution or hetaryl with or without substitution.