SK283343B6 - Imino oxyphenyl acetic acid derivatives, methods and intermediates for their preparation and use thereof - Google Patents

Abstract

The invention relates to 2-imino oxyphenyl acetic acid derivatives of formula (I), to the salts of said derivatives, methods and intermediates for their preparation and use thereof.

Description

Technical field

The present invention relates to 2-iminooxyphenylacetic acid derivatives, processes and intermediates for the preparation of compounds of formula (I), as well as compositions containing them and their use for controlling animal pests and harmful fungi.

BACKGROUND OF THE INVENTION

Phenylacetic acid derivatives are known from the literature for use against animal pests and harmful fungi (EP-A 370 629, EP-A 463 488, EP-A 460 575, WO-A 95/21 154, WO-A 95/21 153, WO-A 95/18789).

SUMMARY OF THE INVENTION

In contrast, the main object of the present invention are compounds that more strongly inhibit mitochondrial respiration and thereby provide improved action against animal pests and harmful fungi.

The invention relates to 2-iminooxyphenylacetic acid derivatives of the general formula (I)

(I), in which the substituents and indices have the following meanings: R ¹ C (CO ₂ CH ₃ ) = NOCH ₃ (Ia), C (CONHCH ₃ ) = NOCH ₃ (1b), C (CONH ₂ ) = NOCH ₃ ( Ic), C (CO ₂ CH ₃ ) = CHOCH ₃ (1d) or C (CO ₂ CH ₃ ) = CHCH ₃ (1e);

R ^{2 is} cyano, nitro, halogen, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl or C 1 -C 4 alkoxy;

m 0, 1 or 2, wherein the radicals R ² may be different when m is 2;

R ³ is hydrogen, cyano, hydroxy, halogen, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 6 alkoxyalkyl, C 1 -C 6 alkoxy C 1 -C 6 haloalkoxy, C 1 -C 6 alkylthio, cyclopropyl, C 1 -C 6 alkenyl, C 1 -C 6 aryloxyalkyl, benzyl or benzyloxy, the aromatic rings of this radical may bear: one to three of the following: cyano, nitro, halogen, C1-C6alkyl, C1-C6haloalkyl, C1-C6alkoxy, C1-C6haloalkoxy or C1-C6alkyl; C (CH ₃ ) = NYR ^α , where is

^And R is alkyl having 1 to 6 carbon atoms and

Y is oxygen or nitrogen, wherein the nitrogen atom carries a hydrogen atom or an alkyl group having 1 to 6 carbon atoms;

R ( ⁴⁾ is hydrogen or cyano.

substituted or unsubstituted alkyl, alkenyl, alkynyl, cycloalkyl, heterocyclyl, aryl and hetaryl groups;

substituted or unsubstituted alkoxy, alkenyloxy, alkynyloxy, cycloalkoxy, heterocyclyloxy, aryloxy and hetaryloxy groups;

substituted or unsubstituted arylthio and hetarylthio;

-Q _p -C- (R ⁵ ) = N-Y'-R ⁶ or -QON = CR ⁷ R ⁸ , wherein

Q represents a direct bond, CH ₂ , CH (CH ₃ ), CH (CH ₂ CH ₃ ) or 1,1-cyclopropyl group;

p is 0 or 1;

Y represents an oxygen or nitrogen atom, wherein the nitrogen atom carries a hydrogen atom or an alkyl group having 1 to 4 carbon atoms;

R ^{5 is} one of the groups listed for R ³ or substituted or unsubstituted cycloalkoxy, heterocyclyloxy, aryloxy, hetaryloxy, arylthio and heteroarylthio;

R ^{6 is} substituted or unsubstituted (C 1 -C 10) alkyl, (C 3 -C 6) cycloalkyl, (C 2 -C 10) alkenyl, (C 2 -C 10) alkynyl, (C 1 -C 10) alkylcarbonyl, C 2 -C 10 alkenylcarbonyl, C 2 -C 10 alkynylcarbonyl or C 1 -C 10 alkylsulfonyl;

substituted or unsubstituted aryl, hetaryl, arylcarbonyl, hetarylcarbonyl, arylsulfonyl or hetarylsulfonyl groups;

R ⁷ , R ^{8 are} methyl, ethyl, phenyl and benzyl, the aromatic rings of which may bear one to three of the following substituents: cyano, nitro, halogen, C 1-6 alkyl, C 1-6 haloalkyl carbon atoms, (C1-C6) alkoxy or (C1-C6) haloalkoxy;

R ³ and R ⁴ is, together with the carbon atom to which it is attached, a four or eight-membered ring which besides carbon atoms, can contain one or two oxygen and / or sulfur and / or Níl- and / or N (C _r C 4 -alkyl) -groups in which the carbon atoms may bear one of the following substituents: a halogen atom, an alkyl group having 1 to 6 carbon atoms or an alkoxyimino group having 1 to 4 carbon atoms; while

R ³ and R ⁴ are not simultaneously attached to the carbon atom through the heteroatom; as well as their salts.

Accordingly, the compounds of formula (I) defined above were first found. In addition, processes and intermediates have been found for the production of these compounds, as well as suitable compositions containing them for controlling animal pests and harmful fungi.

Compounds of formula (I) may be prepared by a variety of methods, and it is generally irrelevant whether the group -ON = CR ³ R ⁴ (hereinafter also referred to as "side chain") or the radical R ¹ (hereinafter referred to below) is first formed. also as "pharmacophore"), respectively, in which stage of preparation of "pharmacophore" the "side chain" is attached to the structure.

1. In the preparation of the compounds of formula (I), wherein R ¹ is C (CO ₂ CH ₃₎ = NOCH ₃ (Ia),

C (CO ₂ CH ₃ ) = CHOCH ₃ (1d) or C (CO ₂ CH ₃ ) = CHCH ₃ (1e), for example, is carried out by converting a benzoic acid ester of formula (II) in the presence of a base with an oxime of formula (III) to the corresponding derivative of formula (IV), compound (IV) is saponified to the corresponding carboxylic acid (IVa) and compound (IVa) is subsequently converted first to chloride (Va) and then to cyanide (Vb). The cyanide (Vb) is converted by the Pinner reaction to the corresponding α-ketoester (VI) and (VI) is subsequently converted or

(a) with O-methylhydroxylamine or its salt (VIIa) to the corresponding compound (Ia) [C (CO ₂ CH ₃ ) = NOCH ₃ ], or

b) with a Wittig or Wittig-Homer reagent of formula (VIIIb) to the corresponding compound (Id) [R = C (CO ₃ CH ₃ ) = CHOCH ₃ ], or

b) with a Wittig or Wittig-Homer reagent of formula (Vile) to the corresponding compound (Ie) [R = C (CO ₂ CH ₃ ) = CHCH ₃ ].

(Ie) O

L in formula (II) is a leaving group common to nucleophilic aromatic substitution, such as a halogen atom (e.g., fluorine, chlorine, bromine), nitro or sulfo.

R in formula (II) represents an alkyl group having 1 to 4 carbon atoms, in particular methyl.

ΐ in formula (VIIa) means an anion of an inorganic acid, in particular a halide anion.

P * in formulas (VIIb) and (VIIe) means a phosphonate or phosphonium halide residue suitable for the Wittig or Wittig-Homer reaction.

1A. The reaction of the benzoic acid ester (II) with the oxime (III) is usually carried out at temperatures from -20 ° C to 170 ° C, preferably from 0 ° C to 100 ° C in an inert organic solvent in the presence of a base [J. Heterocycl. Chem. 4,441 (1967); J. Org. Chem. 49, 180 (1984); Synthesis 1975, 782; J. Heterocycl. Chem. 26, 1293 (1989)].

(II) (IV) such as methylene chloride, chloroform and chlorobenzene, an ether such as diethyl ether, diisopropyl ether, tert-butyl methyl ether, dioxane, anisole and tetrahydrofuran, nitriles such as acetonitrile and propionitrile, ketones such as acetone, methyl ethyl ketone, diethyl ketone and tert. as well as dimethylsulfoxide and dimethylformamide, dimethylacetamide, 1,3-dimethylimidazolidin-2-one, 1,3-dimethyltetrahydro-2 (1H) -pyrimidinone and hexamethylphosphoric triamide, particularly preferably tetrahydrofuran, dimethylsulfoxide, dimethylacetamide and dimethylformamide, dimethylformamide -2 (lH) -pyrimidinone. Mixtures of the solvents mentioned may also be used.

Suitable bases are, in general, inorganic compounds, such as alkali metal and alkaline earth metal hydrides such as lithium hydride, sodium hydride, potassium hydride and calcium hydride, alkali metal and alkaline earth metal carbonates such as lithium carbonate and calcium carbonate, and silver carbonate. , alkali metal hydrogencarbonates such as sodium bicarbonate, organometallic compounds, especially alkali metal alkyls such as methyl lithium, butyl lithium and phenyl lithium, alkylmagnesium halides such as methylmagnesium chloride, and alkali metal and alkaline earth metal alcoholates such as sodium methoxide, sodium ethoxide, sodium ethoxide potassium, tert-butanoate and dimethoxymagnesium; in addition, organic bases such as tertiary amines such as trimethylamine, triethylamine, triisopropylethylamine and N-methylpiperidine, pyridine, substituted pyridine such as colidine, latidine and 4-dimethylaminopyridine as well as bicyclic amines. Particularly preferred are sodium hydride, potassium carbonate, potassium methoxide, potassium ethoxide, potassium tert-butoxide and sodium methylate. The bases can generally be used in equimolar amounts, in excess or, optionally, as solvent.

Given the completeness of the reaction, it may be advantageous to carry out the reaction in the presence of catalytic amounts of a crown ether such as 18-Krone-6 or 15-Krone-5 or in the presence of another conventional phase transfer catalyst. Suitable phase-transfer catalysts are ammonium halides and tetrafluoroborates, such as benzyltriethylammonium chloride, benzyltributylammonium chloride, tetrabutylammonium chloride, hexadecyltrimethylammonium bromide and tetrabutylammonium phosphonium phosphate, and also tetrabutylammonium boronate, such as tetrabutylammonium phosphonium boronate.

The starting compounds are generally reacted in equimolar amounts. To achieve yield, it may be advantageous to use an excess of compound (III) relative to compound (II).

Given the rate of reaction and its completeness, it may be advantageous if compound (III) is first treated with a base and the resulting salt is reacted with compound (II).

The starting materials of formula (II) required for the preparation of the compounds of formula (I) are known from the literature. The starting materials (III) are known from the literature described or can be obtained by the processes described therein (cf. WO-A 95/21 153).

IB. The conversion of the ester (IV) to the corresponding acid (IVa) is carried out in a known manner and by acidic or alkaline saponification at temperatures from 0 ° C to 100 ° C, preferably from 0 ° C to 50 ° C, in an inert organic solvent or aqueous / organic solvents in the presence of a base or an acid [basic saponification cf. J. Org. Chem. 30, 3676 (1965); acid saponification compare: Chem. Ind. (London) 1964,193].

Suitable solvents are aromatic hydrocarbons such as toluene, o-, m- and p-xylene, halogenated hydrocarbons,

The carboxylic acid of formula (IVa) thus obtained is subsequently converted into the corresponding chloride of formula (Va) in a known manner using conventional chlorinating agents, at temperatures from 0 ° C to 150 ° C, preferably from 0 ° C to 100 ° C, optionally in the presence of an inert organic solvent [Houben-Weyl, Ergänzugsband 5, p. 59ff, 225ff and 664ff].

The chlorinating agents are any, for this purpose the commonly used reagents, in particular, SOC1 _2, (COC1) _{2 3} .POC1, AlClj PC1 and _fifth The chlorinating agent is generally used in excess or optionally as a solvent.

Suitable solvents are aliphatic hydrocarbons such as pentane, hexane, cyclohexane and petroleum ether, aromatic hydrocarbons such as toluene, o-, m- and p-xylene, as well as halogenated hydrocarbons such as methylene chloride, chloroform and chlorobenzene. Mixtures of the solvents mentioned may also be used.

The starting materials are generally reacted in at least equimolar amounts. To achieve yield, it may be advantageous to use an excess chlorinating agent relative to compound (IVa).

IC. The conversion of the benzoic acid chloride of formula (Va) to the corresponding cyanide (Vb) is carried out in a known manner [DE Pat. prihl. no. 19,603,990.8; Bull. Chem. Soc. Jpn. 60,1085 (1987); Synthesis 1983, 636; J. Org. Chem. 43, 2280 (1978); Tetrahedron Lett. 1974 2275] at temperatures from 0 ° C to 150 ° C, preferably from 10 ° C to 100 ° C using an inorganic cyanide, in an inert organic solvent, optionally in the presence of a catalyst.

(Vb)

Suitable inorganic cyanides are the metal cyanides of the first major group or subgroup of the periodic table, for example lithium, sodium, potassium, copper and silver, in particular copper, as well as organic cyanides such as trimethylsilyl cyanide.

Suitable solvents are aliphatic hydrocarbons such as pentane, hexane, cyclohexane and petroleum ether, aromatic hydrocarbons such as toluene, o-, m- and p-xylene, halogenated hydrocarbons such as methylene chloride, chloroform and chlorobenzene, ether such as diethyl ether, diisopropyl ether, tert-propyl ether. butyl methyl ether, dioxane, anisole and tetrahydrofuran, nitriles such as acetonitrile and propionitrile, ketones such as acetone, methyl ethyl ketone, diethyl ketone and tert-butyl methyl ketone, alcohols such as methanol, ethanol, n-propanol, isopropanol, n-butanol and tert-butanol, as well as dimethylsulfoxide and dimethylformamide, particularly preferably toluene, methylene chloride and tetrahydrofuran. Mixtures of the solvents mentioned may also be used.

The use of a catalyst is recommended for reaction with the above cyanide compounds except CuCN. Suitable catalysts are conventional phase transfer catalysts, in particular ammonium salts such as tetraammonium bromide.

The starting compounds are generally used in equimolar amounts. To achieve yield, it may be advantageous to use an excess of cyanide relative to the compound of formula (Va).

ID. Conversion of cyanide (Vb) to α-ketoester (VI) is carried out in a known manner in the sense of a Pinner reaction at temperatures from 0 ° C to 150 ° C, preferably from 30 ° C to 100 ° C, in alcohol (R-OH) in the presence acid and catalyst [Tetrahedron Lett. 21, 3539 (1980); J. Org. Chem. 47, 2342 (1982)].

As acids or acid catalysts there are used inorganic acids such as hydrofluoric acid, hydrochloric acid, hydrobromic acid, sulfuric acid and perchlorosulphuric acid, Lewis acids such as boron trifluoride, aluminum chloride, ferric chloride, tin tetrachloride, titanium tetrachloride and zinc chloride, as well as organic acids such as formic acid, acetic acid, propionic acid, oxalic acid, citric acid and trifluoroacetic acid.

The acids are generally used in at least equimolar amounts, preferably in excess.

1E. Reaction of α-ketoester (VI) with O-methylhydroxylamine, respectively. its salt (VIIa) to compound (Ia) is carried out in a known manner at temperatures from 0 ° C to 100 ° C, preferably from 20 ° C to 70 ° C in an inert organic solvent, optionally in the presence of a base [US-A 5 221 762 ].

Suitable solvents are aliphatic hydrocarbons such as pentane, hexane, cyclohexane and petroleum ether, aromatic hydrocarbons such as toluene, o-, m- and p-xylene, halogenated hydrocarbons such as methylene chloride, chloroform and chlorobenzene, ether such as diethyl ether, diisopropyl ether, tert-propyl ether. butyl methyl ether, dioxane, anisole and tetrahydrofuran, nitriles such as acetonitrile and propionitrile, ketones such as acetone, methyl ethyl ketone, diethyl ketone and tert-butyl methyl ketone, alcohols such as methanol, ethanol, n-propanol, isopropanol, n-butanol and tert-butanol, as well as dimethylsulfoxide and dimethylformamide, particularly preferably dimethylformamide or alcohols. Mixtures of the solvents mentioned may also be used.

Suitable bases are, in general, inorganic compounds, such as alkali metal and alkaline earth metal hydroxides, such as lithium hydroxide, sodium hydroxide, potassium hydroxide and calcium hydroxide, alkali metal and alkaline earth metal oxides, such as lithium oxide, sodium oxide, calcium oxide and the like. magnesium oxide, alkali metal and alkaline earth metal hydrides such as lithium hydride, sodium hydride, potassium hydride and calcium hydride, alkali metal amides, such as lithium amide, sodium amide and potassium amide, alkali metal and alkaline earth metal carbonates, such as lithium carbonate and calcium carbonate as well as alkali metal bicarbonates such as sodium bicarbonate, organometallic compounds, in particular alkali metal alkyls such as methyl lithium, butyllithium and phenyl lithium, alkylmagnesium halides such as methylmagnesium chloride, and alkali metal and alkaline earth metal alcoholates such as methoxide potassium ethanolate, potassium tert-butoxide and dimethoxymagnesium; in addition, organic bases such as tertiary amines such as trimethylamine, triethylamine, triisopropylethylamine and N-methylpiperidine, pyridine, substituted pyridine such as colidine, latidine and 4-dimethylaminopyridines, as well as bicyclic amines. Particularly preferred are tertiary amines.

The bases are generally used in catalytic amounts, but can also be used in equimolar amounts, in excess or optionally as a solvent.

The starting materials are generally reacted in equimolar amounts. To achieve yield, it may be advantageous to use the compound of formula (VIIa) in excess of (IV).

1F. The conversion of the α-ketoester (VI) with compound (VIIb) to compound (Id) is carried out in a known manner in the sense of Wittig and Wittig, respectively. Wittig-Homer reaction at temperatures from 0 ° C to 100 ° C, preferably from 0 ° C to 50 ° C in an inert organic solvent in the presence of a base and a catalyst [Tetrahedron 44, 3727 (1988)].

Suitable solvents are aliphatic hydrocarbons such as pentane, hexane, cyclohexane and petroleum ether, aromatic hydrocarbons such as toluene, o-, m- and p-xylene, halogenated hydrocarbons such as methylene chloride, chloroform and chlorobenzene, ether such as diethyl ether, diisopropyl ether, tert-propyl ether. butyl methyl ether, dioxane, anisole and tetrahydrofuran, nitriles such as acetonitrile and propionitrile, ketones such as acetone, methyl ethyl ketone, diethyl ketone and tert.-butyl methyl ketone, alcohols such as methanol, ethanol, n-propanol, isopropanol, n-butanol and tert-butanol, as well as dimethylsulfoxide and dimethylformamide, particularly preferably dimethylformamide. Mixtures of the solvents mentioned may also be used.

Suitable bases are, in general, inorganic compounds, such as alkali metal and alkaline earth metal hydroxides, such as lithium hydroxide, sodium hydroxide, potassium hydroxide and calcium hydroxide, alkali metal and alkaline earth metal oxides, such as lithium oxide, sodium oxide, calcium oxide and the like. magnesium oxide, alkali metal and alkaline earth metal hydrides such as lithium hydride, sodium hydride, potassium hydride and calcium hydride, alkali metal amides such as lithium amide, sodium amide and potassium amide, alkali metal and alkaline earth metal carbonates such as lithium carbonate; calcium carbonate as well as alkali metal bicarbonates such as sodium bicarbonate, organometallic compounds, in particular alkali metal alkyls such as methyl lithium, butyllithium and phenyl lithium, alkylmagnesium halides such as methylmagnesium chloride and alkali metal and alkaline earth metal alcoholates such as sodium methoxide, sodium methoxide . potassium ethanolate, potassium tert-butanolate and dimethoxymagnesium; in addition, organic bases such as tertiary amines such as trimethylamine, triethylamine, triisopropylethylamine and N-methylpiperidine, pyridine, substituted pyridine such as colidine, latidine and 4-dimethylaminopyridines, as well as bicyclic amines. Alcoholates are particularly preferred.

The bases are generally used in catalytic amounts, but can also be used in equimolar amounts, in excess or optionally as a solvent.

The starting compounds are generally used in equimolar amounts. To achieve a yield, it may be advantageous to use compound (VIIIb) in excess of compound (VI).

IG. The conversion of the α-ketoester (VI) with the compound (VIIa) to the compound (Id) is carried out in a manner known per se in the sense of Wittig, respectively. Wittig-Homer reaction at temperatures from 0 ° C to 100 ° C, preferably from 0 ° C to 50 ° C in an inert organic solvent in the presence of a base and a catalyst [Austr. J. Chem. 34, 2363 (1981); Can. J. Chem. 49, 2143 (1971)].

Suitable solvents are aliphatic hydrocarbons such as pentane, hexane, cyclohexane and petroleum ether, aromatic hydrocarbons such as toluene, o-, m- and p-xylene, halogenated hydrocarbons such as methylene chloride, chloroform and chlorobenzene, ether such as diethyl ether, diisopropyl ether, tert-propyl ether. butyl methyl ether, dioxane, anisole and tetrahydrofuran, nitriles such as acetonitrile and propionitrile, ketones such as acetone, methyl ethyl ketone, diethyl ketone and tert.-butyl methyl ketone, alcohols such as methanol, ethanol, n-propanol, isopropanol, n-butanol and tert-butanol, as well as dimethylsulfoxide and dimethylformamide, particularly preferably dimethylformamide. Mixtures of the solvents mentioned may also be used.

Suitable bases are, in general, inorganic compounds, such as alkali metal and alkaline earth metal hydroxides, such as lithium hydroxide, sodium hydroxide, potassium hydroxide and calcium hydroxide, alkali metal and alkaline earth metal oxides, such as lithium oxide, sodium oxide, calcium oxide and the like. magnesium oxide, alkali metal and alkaline earth metal hydrides such as lithium hydride, sodium hydride, potassium hydride and calcium hydride, alkali metal amides such as lithium amide, sodium amide and potassium amide, alkali metal and alkaline earth metal carbonates such as lithium carbonate; calcium carbonate as well as alkali metal bicarbonates such as sodium bicarbonate, organometallic compounds, in particular alkali metal alkyls such as methyl lithium, butyllithium and phenyl lithium, alkylmagnesium halides such as methylmagnesium chloride, and alkali metal and alkaline earth metal alcoholates such as sodium methoxide,potassium ethanolate, potassium tert-butoxide and dimethoxymagnesium; in addition, organic bases such as tertiary amines such as trimethylamine, triethylamine, triisopropylethylamine and N-methylpiperidine, pyridine, substituted pyridine such as colidine, latidine and 4-dimethylaminopyridines, as well as bicyclic amines. Alcoholates are particularly preferred.

The bases are generally used in catalytic amounts, but can also be used in equimolar amounts, in excess or optionally as a solvent.

The starting compounds are generally used in equimolar amounts. To achieve yield can

It is preferred to use Compound (VIIe) in excess of Compound (VI).

2. Particularly preferably compounds (Vb) are also prepared by reacting a cyanide of formula (Vc) with an oxime of formula (III) as described in point IA.

(Vo)

-TE-

3. Compounds of formula (VI) are preferably also obtained by converting the α-keto ester of formula (VIa) to compound (VIb) and reacting (VIb) in situ with a ketone and a compound of formula (VIb). with an aldehyde (IX) to a compound of formula (VI).

The groups R 'and R in formula (VIa) independently represent an alkyl group having 1 to 6 carbon atoms or an aryl group.

The liberation of the hydroxylamine (VIb) from the oxime (VIa) and further reaction of the thus obtained reaction mixture with the ketone of formula (IX) is carried out in a known manner at temperatures from 0 ° C to 150 ° C, preferably 0 ° C to 50 ° C in inert organic solvent in the presence of an acid or catalyst.

Suitable solvents are aliphatic hydrocarbons such as pentane, hexane, cyclohexane and petroleum ether, aromatic hydrocarbons such as toluene, o-, m- and p-xylene, halogenated hydrocarbons such as methylene chloride, chloroform and chlorobenzene, ether such as diethyl ether, diisopropyl ether, tert-propyl ether. butyl methyl ether, dioxane, anisole and tetrahydrofuran, nitriles such as acetonitrile and propionitrile, ketones such as acetone, methyl ethyl ketone, diethyl ketone and tert-butyl methyl ketone, alcohols such as methanol, ethanol, n-propanol, isopropanol, n-butanol and tert-butanol, as well as dimethylsulfoxide and dimethylformamide, particularly preferably alcohol. Mixtures of the solvents mentioned may also be used.

As acids and acid catalysts there are used inorganic acids such as hydrofluoric acid, hydrochloric acid, hydrobromic acid, sulfuric acid and perchlorosulphuric acid, Lewis acids such as boron trifluoride, aluminum chloride, ferric chloride, tin tetrachloride, titanium tetrachloride and zinc chloride, as well as organic acids such as formic acid, acetic acid, propionic acid, oxalic acid, citric acid and trifluoroacetic acid.

The acids are generally used in catalytic amounts, but can also be used in equimolar amounts, in excess or optionally as a solvent.

The starting compounds are generally used in equimolar amounts to one another. To achieve yield, it may be advantageous to use compound (IX) in excess of compound (VIIIb).

4. Compounds (I) wherein R ¹ is C (CONHCH ₃ ) = NOCH ₃ (Ib) or C (CONH ₂ ) = NOCH ₃ (1c) can be obtained, for example, by leaving the compound of formula (lia) known react with methylamine or a salt thereof (XIII) or with ammonia or an ammonium salt, for example

Z 'in formula (XIII) is an anion of an inorganic acid, in particular a halogen anion such as chlorine and bromine.

This reaction is usually carried out at temperatures from 0 ° C to 150 ° C, preferably from 0 ° C to 70 ° C, in an inert organic solvent, optionally in the presence of a base.

Suitable solvents are aliphatic hydrocarbons such as pentane, hexane, cyclohexane and petroleum ether, aromatic hydrocarbons such as toluene, o-, m- and p-xylene, halogenated hydrocarbons such as methylene chloride, chloroform and chlorobenzene, ether such as diethyl ether, diisopropyl ether, tert-propyl ether. butyl methyl ether, dioxane, anisole and tetrahydrofuran, nitriles such as acetonitrile and propionitrile, ketones such as acetone, methyl ethyl ketone, diethyl ketone and tert-butyl methyl ketone, alcohols such as methanol, ethanol, n-propanol, isopropanol, n-butanol and tert-butanol, as well as dimethylsulfoxide and dimethylformamide, particularly preferably tetrahydrofuran. Mixtures of the solvents mentioned may also be used.

When ammonium salts are used as starting materials, the reaction is preferably carried out in the presence of a base. Suitable bases are, in general, inorganic compounds, such as alkali metal and alkaline earth metal hydroxides, such as lithium hydroxide, sodium hydroxide, potassium hydroxide and calcium hydroxide, alkali metal and alkaline earth metal oxides, such as lithium oxide, sodium oxide, calcium oxide and the like. magnesium oxide, alkali metal and alkaline earth metal hydrides such as lithium hydride, sodium hydride, potassium hydride and calcium hydride, alkali metal amides such as lithium amide, sodium amide and potassium amide, alkali metal and alkaline earth metal carbonates such as lithium carbonate and calcium carbonate, as well as alkali metal bicarbonates such as sodium bicarbonate, organometallic compounds, in particular alkali metal alkyls such as methyl lithium, butyllithium and phenyl lithium, alkylmagnesium halides such as methylmagnesium chloride, and alkali metal and alkaline earth metal alcoholates such as methoxide . potassium ethanolate, potassium tert-butoxide and dimethoxymagnesium; in addition, organic bases such as tertiary amines such as trimethylamine, triethylamine, triisopropylethylamine and N-methylpiperidine, pyridine, substituted pyridine such as colidine, latidine and 4-dimethylaminopyridines, as well as bicyclic amines. Particularly preferred are tertiary amines, respectively. potassium carbonate.

The bases are used at least in equimolar amounts, in excess or optionally as a solvent.

The starting compounds are generally used in equimolar amounts. To achieve the yield, it may be advantageous to use compound (XIII), optionally ammonia, in excess of compound (Ia).

5. According to a particularly preferred embodiment, the compound of formula (Ib) is preferably obtained by first converting the α-ketoamide of formula (VIc) with the oxime of formula (III) to the corresponding amide of formula (VId) under the conditions described under IA. and (VId) is then reacted with O-methylhydroxylamine or a salt thereof (VIIa) under the conditions described under 4. above.

(V! C) O

6. According to another method, compound (I) is also obtained by converting the α-keto ester of formula (Vie) with N-hydroxyphthalimide (XI) to the corresponding protected oxime of formula (VIf). The α-ketoester function of the oxime (Vlf) can then be converted into various R ¹ groups in a manner known per se according to the above procedure (compare formulas (XIIa) and (XIIb)). The phthalimide protecting group is then cleaved in a known manner using hydrazine in ethanol [Synthesis 23, 682 (1979)] or hydrogen bromide in acetic acid [J. Org. Chem. 28, 1604 (1963)] and the obtained O-substituted hydroxylamine (compare formulas (XIIIa) and (XIIIb)) is reacted in situ with a ketone of formula (IX) to a compound of formula (I).

The progress of the reactions is shown in the following reaction scheme.

The individual reactions are carried out generally and in particular under the conditions described in the introduction.

Compounds (VI1) which are required as starting materials for the above-mentioned reactions can be obtained, for example, according to the following reaction scheme:

The corresponding reaction procedures provide the α-keto ester of formula (VI), optionally the corresponding α-ketoamide, when the group L is substituted under the conditions described in the introduction by the group -ON = CR ³ R ⁴ , by reaction with an oxime of formula (III) (XIVa), (XIVV), (XVb) or (VII)).

The procedure is carried out in accordance with the method described in Coli. Czech. Chem. Commun. 29, 97/119 (1964).

According to another method, compound (I) is also obtained from phenyl ketones of formula (XVI) according to the methods described in EP-A 178 826, EP-A 256 667 and EP-A 468 775 according to the following reaction scheme:

The individual reactions are carried out generally and in particular under the conditions described in the introduction.

7. According to another particularly preferred process, the compound of formula (I) is also obtained by first converting the α-ketoester of formula (Vie) to the corresponding α-ketoester (VI) by reaction with oxime (III). The .alpha.-ketoester function of oxime (VI) can then be converted to various R ^{@ 1} groups in a manner known per se.

(xvi) (xvi °> <xvi?

The group L can be replaced by the radical -ON = CR ³ R as described in this reaction procedure to give the steps of compounds (XVIa), (XVIb) and (XVII).

The reaction mixtures are worked up in a manner known per se, for example by mixing with water, phase separation and optionally chromatographic purification of the crude products. The intermediates and end products are obtained in part in the form of colorless or light brown viscous oils and are freed from volatile constituents under reduced pressure and slightly elevated temperatures or purified. If the intermediates and end products are obtained in the form of solids, purification can also be carried out by recrystallization or digestion.

Salts of the compounds of formula (I) may be obtained by a conventional method in which the compound of formula (I) is reacted in water or an inert organic solvent at temperatures from -80 ° C to 120 ° C, preferably from 0 ° C to 60 ° C, with an acid suitable for salt formation.

Suitable acids are, for example, mineral acids such as sulfuric acid and phosphoric acid or Lewis acids such as zinc chloride.

In general, the type of salt is non-critical to the use of the compounds of the formula against animal pests and harmful fungi. For the purposes of the invention, preference is given to those salts which are not limiting to plants, areas, materials, seeds and premises to be removed from plant pests and harmful fungi.

Compounds of formula (I) may, in view of their double bonds, be -C = N-, respectively. -C = C- occur as E- and Z-isomers, with respect to the double bond of the radical R ¹ , the E-isomers are, in principle, more biologically active and thus also more advantageous.

Due to the double bond of the ON = CR ³ R ^{4 group} and the other double bonds occurring in the R ³ and R ⁴ residues, E- and Z-isomers may also occur. In general, compounds (I) in which these double bonds represent the E-configuration are preferred.

Usually, these double bonds will be formed predominantly in the E-configuration during synthesis. Mixtures of isomers may be or are conveniently separated into the individual isomers, for example by fractional crystallization or chromatography, or may be converted to other isomers by treatment with protonic acids or Lewis acids, or by treatment with light. If an isomeric mixture is obtained in the synthesis, in general, resolution is not necessary since the isomers of the invention can be partially interchanged with each other under the influence of light, agents used in the formulations or also in vivo.

In the above definitions, the terms used in the formulas described herein include collective terms, which may generally be represented by the following substituents:

Halogen: fluorine, chlorine, bromine, iodine;

Alkyl: saturated, linear or branched hydrocarbon groups having 1 to 4, 6 or 10 carbon atoms, for example alkyl having 1 to 6 carbon atoms such as methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl .

1,1-dimethylethyl, pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl, hexyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, 1-methylpentyl, 2- methylpentyl, 3-methylpentyl, 4-methylpentyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1,1,2-trimethylpropyl, 1,2,2-trimethylpropyl, 1-ethyl-1-methylpropyl and 1-ethyl-2-methylpropyl;

Haloalkyl: linear or branched alkyl groups having 1 to 4, 6 or 10 carbon atoms (as mentioned above), in which groups, all or part of the hydrogen atoms may be replaced by halogen atoms as mentioned above, e.g. 2 carbon atoms such as chloromethyl, bromomethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 1-chloroethyl, 1-bromomethyl, 1-fluoroethyl, 2-fluoroethyl, 2-fluoroethyl , 2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl, 2-chloro-2,2-difluoroethyl,

2,2-dichloro-2-fluoroethyl, 2,2,2-trichloroethyl and pentafluoroethyl;

Alkylcarbonyl: an alkyl group having 1 to 6 or 10 carbon atoms (as described above) which is bonded to the structure via a carbonyl group (-CO-);

Alkylsulfonyl: a straight or branched alkyl group having 1 to 6 or 10 carbon atoms (as mentioned above) which is bonded to the structure via a sulfonyl group (-SO _R);

Alkylsulfoxyl: a linear or branched alkyl group having 1 to 6 carbon atoms (as described above) which is bound to the structure via a sulfoxyl group (-SO ₃ -);

Alkoxy: linear or branched alkyl groups having 1 to 4 or 6 carbon atoms (as mentioned above) which are bonded to the structure via an oxygen atom (-O-);

Haloalkoxy: linear or branched haloalkyl groups having 1 to 4, 6 or 10 carbon atoms (as mentioned above) which are bonded to the structure via an oxygen atom (-O-);

Alkoxycarbonyl: (C 1 -C 6) alkoxy (as described above) attached to a structure bonded via a carbonyl group (-CO-);

Alkoxyimino: linear or branched (C 1 -C 4) alkyl groups (as described above) which are bonded to the structure via an oxyimino group (-ON =);

Alkylthio: linear or branched alkyl groups having 1 to 6 carbon atoms (as mentioned above) which are bonded to the structure via a sulfur atom (-S-);

Alkylamino: a linear or branched alkyl group having 1 to 6 carbon atoms (as described above) which is attached to the structure by a C 2-6 amino group (-NH-);

Dialkylamino: two independent, linear or branched alkyl groups having from 1 to 6 carbon atoms (as mentioned above), which are bonded to the structure via a nitrogen atom;

Alkylaminocarbonyl: a (C 1 -C 6) alkylamino group (as described above) which is bound to the structure via a carbonyl group (-CO-);

Dialkylaminocarbonyl: a dialkylamino group with two independent C 1 -C 6 -alkyl groups (as mentioned above) which are bonded to the structure via a carbonyl group (-CO-);

Alkylaminothiocarbonyl: a (C 1 -C 6) alkylamino group (as described above) attached to the structure via a thiocarbonyl (-CS-) group;

SK 283343 Β6

Dialkylaminothiocarbonyl: a dialkylamino group having two independent alkyl groups having 1 to 6 carbon atoms (as described above) which is bound to the structure via a thiocarbonyl (-CS-) group;

Alkenyl: unsaturated, linear or branched hydrocarbon groups of 2 to 6 or 10 carbon atoms and a double bond at any position, for example alkenyl of 2 to 6 carbon atoms such as ethenyl, 1-propenyl, 2-propenyl, 1-methylctenyl, 1 -butenyl, 2-butenyl, 3-butenyl, 1-methyl-1-propenyl, 2-methyl-1-propenyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl, 1-pentenyl, 2-pentenyl 3-pentenyl, 4-pentenyl, 1-methyl-1-butenyl, 2-methyl-1-butenyl, 3-methyl-1-butenyl, 1-methyl-2-butenyl, 2-methyl-2-butenyl, 3 -methyl-2-butenyl, 1-methyl-3-butenyl, 2-methyl-3-butenyl, 3-methyl-3-butenyl, 1,1-dimethyl-2-propenyl, 1,2-dimethyl-1-propenyl 1,2-dimethyl-2-propenyl, 1-ethyl-1-propenyl, 1-ethyl-2-propenyl, 1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, 5-hexenyl, 1-methyl 1-pentenyl, 2-methyl-1-pentenyl, 3-methyl-1-pentenyl, 4-methyl-1-pentenyl, 1-methyl-2-pentenyl, 2-methyl-2-pentenyl, 3-methyl-2 -pentenyl, 4-methyl-2-pentenyl, 1-methyl-3-pentenyl, 2-methyl-3-pentenyl, 3-methyl-3-pentenyl, 4-methyl-3-pentenyl, 1-methyl-4-pentenyl, 2-methyl-4-pentenyl, 3-methyl-4-pentenyl, 4-methyl-4-pentenyl, 1,1-dimethyl-2-butenyl, 1,1-dimethyl-3- butenyl, 1,2-dimethyl-1-butenyl, 1,2-dimethyl-2-butenyl, 1,2-dimethyl-3-butenyl,

1,3-dimethyl-1-butenyl, 1,3-dimethyl-2-butenyl, 1,3-dimethyl-3-butenyl, 2,2-dimethyl-3-butenyl, 2,3-dimethyl-1-butenyl,

2,3-dimethyl-2-butenyl, 2,3-dimethyl-3-butenyl, 3,3-dimethyl-1-butenyl, 3,3-dimethyl-2-butenyl, 1-ethyl-1-butenyl, 1- ethyl-2-butenyl, 1-ethyl-3-butenyl, 2-ethyl-1-butenyl, 2-ethyl-2-butenyl, 2-ethyl-3-butenyl, 1,1,2-trimethyl-2-propenyl, 1-ethyl-1-methyl-2-propenyl, 1-ethyl-2-methyl-1-propenyl and 1-ethyl-2-methyl-2-propenyl;

Alkenyloxy: unsaturated, linear or branched hydrocarbon groups having 3 to 6 or 10 carbon atoms and a double bond at any position, not adjacent to the heteroatom (as mentioned above), which are bonded to the structure via an oxygen atom (-O-);

Alkenylcarbonyl: unsaturated, linear or branched hydrocarbon groups having 2 to 10 carbon atoms and a double bond at any position (as described above) which are bonded to the structure via a carbonyl group (-CO-);

Alkynyl: unsaturated, linear or branched hydrocarbon groups of 2 to 4, 6, 8 or 10 carbon atoms and a triple bond at any position, for example alkynyl of 2 to 6 carbon atoms such as ethynyl, 1-propynyl, 2-propynyl, 1 -butinyl, 2-butynyl, 3-butynyl, 1-methyl-2-propynyl, 1-pentynyl, 2-pentynyl, 3-pentynyl, 4-pentynyl, 1-methyl-2-butynyl, 1-methyl-3-butynyl , 2-methyl-3-butynyl, 3-methyl-1-butynyl, 1,1-dimethyl-2-propynyl, 1-ethyl-2-propynyl, 2-hexynyl, 3-hexynyl, 4-hexynyl, 5-hexynyl , 1-methyl-2-pentynyl, 1-methyl-3-pentynyl, 1-methyl-4-pentynyl, 2-methyl-3-pentynyl, 2-methyl-4-pentynyl, 3-methyl-1-pentynyl, 3 -methyl-4-pentynyl, 4-methyl-1-pentynyl, 4-methyl-2-pentynyl, 1,1-dimethyl-2-butynyl, 1,1-dimethyl-3-butynyl, 1,2-dimethyl-3 butynyl, 2,2-dimethyl-3-butynyl, 3,3-dimethyl-1-butynyl, 1-ethyl-2-butynyl, 1-ethyl-3-butynyl, 2-ethyl-3-butynyl and 1-ethyl -l-methyl-2-propynyl;

Alkinyloxy: unsaturated, linear or branched hydrocarbon groups having 3 to 10 carbon atoms and a triple bond at any position (as described above) which are bonded to the structure via an oxygen atom (-O-);

Alkynylcarbonyl: unsaturated, linear or branched hydrocarbon groups having 2 to 10 carbon atoms and a triple bond at any position (as described above) which are bonded to the structure via a carbonyl group (-CO-);

Cycloalkyl: monocyclic, saturated hydrocarbon groups having 3 to 6 or 10 carbon cyclic members, for example, a cycloalkyl group having 3 to 8 carbon atoms, such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl or cyclooctyl;

Cycloalkoxy: monocyclic, saturated hydrocarbon groups having 3 to 6 or 10 carbon cyclic members (as mentioned above) which are attached to the structure via an oxygen atom (-O-);

Cycloalkenyl: monocyclic, unsaturated hydrocarbon groups having 3 to 6 or 10 carbon cyclic carbon members and a double bond at any position in the ring, for example a 5 to 8 carbon cycloalkenyl group such as cyclopentenyl, cyclohexenyl, cycloheptenyl and cyclooctenyl;

Heterocyclyl: 5- to 6-membered heterocycles containing, besides carbon, one to three nitrogen and / or oxygen and / or sulfur atoms in the ring, for example 2-tetrahydrofuranyl, 3-tetrahydrofuranyl, 2-tetrahydrothienyl, 3-tetrahydrothienyl, 2-pyrrolidinyl 3-pyrrolidinyl, 3-isoxazolidinyl, 4-isoxazolidinyl, 5-isoxazolidinyl, 3-isothiazolidinyl, 4-isothiazolidinyl, 5-isothiazolidinyl, 3-pyrazolidinyl, 4-pyrazolidinyl, 5-pyrazolidinyl, 2-oxazolidinyl, 4-oxazolidinyl, 5 -oxazolidinyl, 2-thiazolidinyl, 4-thiazolidinyl, 5-thiazolidinyl, 2-imidazolidinyl, 4-imidazolidinyl, 1,2,4-oxadiazolidin-3-yl, 1,2,4-oxadiazolidin-5-yl, 1,2 1,4-thiadiazolidin-3-yl, 1,2,4-thiadiazolidin-5-yl, 1,2,4-thiazolidin-3-yl, 1,3,4-oxadiazolidin-2-yl, 1,3,4 -thiadiazolidin-2-yl, 1,3,4-triazolidin-2-yl, 2,3-dihydrofur-2-yl, 2,3-dihydrofur-3-yl, 2,4-dihydrofur-2-yl, 2 4-Dihydrofur-3-yl, 2,3-dihydrothien-2-yl, 2,3-dihydrothien-3-yl, 2,4-dihydrothien-2-yl, 2,4-dihydrothien-3-yl, 2 3-pyrolin-2-yl, 2,3-pyrolin-3-yl, 2,4-pyrolin-2-yl, 2,4-pyr olin-3-yl, 2,3-isoxazolin-3-yl, 3,4-isoxazolin-3-yl, 4,5-isoxazolin-3-yl, 2,3-isoxazolin-4-yl, 3,4- isoxazolin-4-yl, 4,5-isoxazolin-4-yl,

2,3-isoxazolin-5-yl, 3,4-isoxazolin-5-yl, 4,5-isoxazolin-5-yl, 2,3-isothiazolin-3-yl, 3,4-isothiazolin-3-yl, 4, 5-isothiazolin-3-yl, 3,2-isothiazolin-4-yl, 3,4-isothiazolin-4-yl, 4,5-isothiazolin-4-yl, 2,3-isothiazolin-5-yl, 3, 4-isothiazolin-5-yl, 4,5-isothiazolin-5-yl, 2,3-dihydropyrazol-1-yl, 2,3-dihydropyrazol-5-yl, 3,4-dihydropyrazol-1-yl, 3, 4-dihydropyrazol-3-yl, 3,4-dihydropyrazol-4-yl, 3,4-dihydropyrazol-5-yl, 4,5-dihydropyrazol-1-yl, 4,5-dihydropyrazol-3-yl, 4, 5-dihydropyrazol-4-yl, 4,5-dihydropyrazol-5-yl, 2,3-dihydrooxazol-2-yl, 2,3-dihydrooxazol-3-yl, 2,3-dihydrooxazol-4-yl,

2,3-dihydroisoxazol-5-yl, 3,4-dihydrooxazol-2-yl, 3,4-dihydrooxazol-3-yl, 3,4-dihydrooxazol-4-yl, 3,4-dihydrooxazol-5-yl, 2- piperidinyl, 3-piperidinyl, 4-piperidinyl, 1,3-dioxan-5-yl, 2-tetrahydropyranyl, 4-tetrahydropyranyl, 2-tetrahydrothienyl, 3-tetrahydropyridazinyl, 4-tetrahydropyridazinyl, 5-tetrahydropyrimidinyl, 2-tetrahydropyrazinyl, 1, 3,5-tetrahydrotriazin-2-yl and 1,2,4-tetrahydrotriazin-3-yl;

Heterocyclyloxy: 5- or 6-membered heterocycles (as mentioned above), which are attached to the structure via an oxygen atom (-O-);

Aryl: an aromatic ring system of one to three nuclei containing 6 to 14 carbon ring members, for example phenyl, naphthyl and anthracenyl;

Aryloxy: an aromatic ring system with one to three nuclei (as mentioned above), which is attached to the structure via an oxygen atom (-O-);

Arylthio: an aromatic ring system with one to three nuclei (as mentioned above), which is attached to the structure via a sulfur atom (-S-);

Arylcarbonyl: an aromatic ring system with one to three nuclei (as mentioned above), which is attached to the structure via a carbonyl group (-CO-);

Arylsulfonyl: an aromatic ring system with one to three nuclei (as mentioned above), which is attached to the structure via a sulfonyl group (-SO ₂ -);

Hetaryl: an aromatic ring system with one or two nuclei containing in the ring 5-, 6-, 9- or 10 atoms, which, in addition to carbon atoms, may contain heteroatoms selected from the group consisting of oxygen, sulfur and nitrogen: 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: a 5-membered heterocycle which, in addition to carbon atoms, may contain one to four nitrogen atoms or one to three nitrogen atoms and one sulfur or oxygen atom such as ring members such as 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- triazole -3-yl, 1,3,4-oxadiazol-2-yl, 1,3,4-thiadiazol-2-yl and 1,3,4-triazol-2-yl;

- benzocondensed 5-membered heteroaryl containing one to three nitrogen atoms or one nitrogen atom and one oxygen or one sulfur atom: a 5-membered heterocycle which, in addition to carbon atoms, may contain one to four nitrogen atoms or one to three nitrogen atoms and one a sulfur atom or one oxygen atom as ring members, and in which two adjacent cyclic carbon members or one cyclic nitrogen member and one adjacent cyclic carbon member may be linked by a buta-1,3-diene-1,4-diyl group;

- a nitrogen-bonded 5-membered heteroaryl containing one to four nitrogen atoms or a nitrogen-bonded benzocondensed 5-membered heteroaryl containing one to three nitrogen atoms: a 5-membered heterocycle which, in addition to carbon atoms, may contain one to four nitrogen atoms or one up to three nitrogen atoms as ring members, in which two adjacent cyclic carbon members or one cyclic nitrogen member and one adjacent cyclic carbon member may be bridged by buta-1,3-dien-1,4-diyl, which cycles may be bonded to a structure through any of the cyclic nitrogen members;

6-membered heteroaryl containing one to three or one to four nitrogen atoms: a 6-membered heterocycle which, in addition to the carbon atoms, may contain one to three or 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, 1,2,4-triazine- 3-yl and 1,2,4,5-triazin-3-yl;

Iletaryloxy: an aromatic ring system with one or two nuclei (as mentioned above), which is attached to the structure via an oxygen atom (-O-);

Hetaryltio: an aromatic ring system with one or two nuclei (as mentioned above), which is attached to the structure via a sulfur atom (-S-);

Hetarylcarbonyl: an aromatic ring system with one or two nuclei (as mentioned above), which is attached to the structure via a carbonyl group (-CO-);

Heterarylsulfonyl: an aromatic ring system with one or two nuclei (as mentioned above), which is bound to the structure via a sulfonyl group (-SO ₂ -).

The term "optionally substituted" in relation to an alkyl, alkenyl and alkynyl group indicates that these groups may be partially or fully halogenated (i.e., the hydrogen atoms in these groups may be partially or fully replaced by the same or different halogen atoms as mentioned above) , (preferably fluorine, chlorine or bromine)] and / or may carry one to three (preferably one) of the following groups:

- cyano, nitro, hydroxy, amino, formyl, carboxy, aminocarbonyl, alkoxy, haloalkoxy, alkylthio, haloalkylthio, alkylamino, dialkylamino, alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy, alkylaminocarbonyl, dialkylaminocarbonyl, alkylcarbonylamino, alkoxycarbonylamino, alkylcarbonyl-N-alkylamino and alkylcarbonyl-N-alkyl-amino, wherein the alkyl groups in these radicals preferably contain 1 to 6 carbon atoms, especially 1 to 4 carbon atoms;

- unsubstituted or customarily substituted cycloalkyl, cycloalkoxy, cycloalkylthio, cycloalkylamino, cycloalkyl-N-alkylamino, heterocyclyl, heterocyclyloxy, heterocyclylthio, heterocyclylamino, preferably up to 12 ring members of the ring system, preferably 3 to 3 ring alkyl, ring members, in particular 3 to 6 ring members, and the alkyl groups in these radicals preferably contain 1 to 6 carbon atoms, in particular 1 to 4 carbon atoms;

- unsubstituted or customary substituted aryl, aryloxy, arylthio, arylamino, aryl-N-alkylamino, arylalkoxy, arylalkylthio, arylalkylamino, arylalkyl-N-alkylamino, hetaryl, hetaryl, hetaryl, hetaryl, hetaryl, hetaryl, hetarylalkylthio, hetarylalkylamino and hetarylalkyl-N-alkylamino, wherein the aryl radicals preferably contain 6 to 10 ring members, in particular 6 ring members (phenyl), the hetaryl radicals preferably contain 5 or 6 ring members and the alkyl groups in these radicals preferably contain 1 to 6 carbon atoms, in particular 1 to 4 carbon atoms.

The term "optionally substituted" in relation to cyclic (saturated, unsaturated or aromatic) groups indicates that these groups may be partially or fully halogenated (that is, the hydrogen atoms in these groups may be partially or fully replaced by the same or different halogen atoms, as mentioned (preferably fluorine, chlorine or bromine, in particular fluorine or chlorine)] and / or may carry one to four (especially one to three) of the following groups:

- cyano, nitro, hydroxy, amino, carboxy, aminocarbonyl, alkyl, haloalkyl, alkenyl, haloalkenyl, alkenyloxy, halogénalkenyloxylová, alkynyl, haloalkynyl, Al kinyloxylová, halogénalkinyloxylová, alkoxy, haloalkoxy, alkylthio, haloalkylthio, alkylamino, dialkylamino, alkylcarbonyl, alkoxycarbonyl , alkylcarbonyloxy, alkylaminocarbonyl, dialkylaminocarbonyl, alkylcarbonylamino, alkoxycarbonylamino, alkylcarbonyl-N-alkylamino and alkylcarbonyl-N-alkylamino, wherein the alkyl groups in these radicals preferably contain from 1 to 6 carbon atoms, in particular from 1 to 4 carbon atoms contain 2 to 8, preferably 2 to 6, especially 2 to 4, carbon atoms in these radicals;

and / or one to three (in particular one) of the following groups:

- unsubstituted or customarily substituted cycloalkyl, cycloalkoxy, cycloalkylthio, cycloalkylamino, cycloalkyl-N-alkylamino, heterocyclyl, heterocyclyloxy, heterocyclylthio, heterocyclylamino, preferably up to 12 ring members of the ring system, preferably 3 to 3 ring alkyl, ring members, in particular 3 to 6 ring members, and the alkyl groups in these radicals preferably contain 1 to 6 carbon atoms, in particular 1 to 4 carbon atoms;

- unsubstituted or customary substituted aryl, aryloxy, arylthio, arylamino, aryl-N-alkylamino, arylalkoxy, arylalkylthio, arylalkylamino, arylalkyl-N-alkylamino, hetaryl, hetaryl, hetaryl, hetaryl, hetaryl, hetaryl, hetaryl, hetaryl, hetaryl, hetaryl, hetaryl, a group, hetarylalkylthio, hetarylalkylamino and hetarylalkyl-N-alkylamino, wherein the aryl radicals preferably contain 6 to 10 ring members, in particular 6 ring members (phenyl), the hetaryl radicals preferably contain 5 or 6 ring members and the alkyl groups in these radicals preferably contain 1 up to 6 carbon atoms, in particular 1 to 4 carbon atoms, and / or may contain one or two (preferably one) of the following groups:

- formyl group,

- CR ^V = NOR ^VI [wherein R ^v is hydrogen, alkyl, cycloalkyl and aryl and R ^v1 is alkyl, alkenyl, haloalkyl, alkynyl and arylalkyl (wherein said alkyl groups preferably contain 1 to 6 carbon atoms, in particular 1 to 6 carbon atoms) (4 carbon atoms, said cycloalkyl, alkenyl and alkynyl groups preferably contain 3 to 8, in particular 3 to 6 carbon atoms) and aryl means in particular phenyl, which may be unsubstituted or substituted by conventional groups] or

- NR ^{V 1} '-CO-DR ^{V 1} [wherein R ^v is hydrogen, hydroxy, C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 1 -C 6 alkoxy C 6 -C 6 alkenyloxy, C 2 -C 6 alkynyloxy, C 1 -C 6 alkoxyalkyl and C 1 -C 6 alkyl, C 1 -C 6 alkoxyalkoxy each alkoxy moiety, C 1 -C 6 alkoxycarbonyl, R ¹ is hydrogen, C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 3 cycloalkyl C 1 -C 6 cycloalkenyl, C 1 -C 6 aryl, C 1 -C 6 arylalkyl, hetaryl and haryl alkyl And D represents a direct bond, an oxygen atom or a nitrogen atom, wherein the nitrogen atom may carry one of the groups given for R ¹ and / or wherein two adjacent carbon atoms of the cyclic system may carry an alkylene group (C až-C alk) alkenyl, (C až-C alk) alkenylene, (C až-C oxy) oxyalkylene, (C až-C oxy) oxyalkyleneoxy, (C až-C oxy) oxyalkenylene, (C až-C oxy) oxyalkenylene (C až-C 4) the bridges may be partially or fully halogenated and / or contain one to three, in particular one or two of the following substituents:

- (C1-C4) -alkyl, (C1-C4) -haloalkyl, (C1-C4) -alkoxy, (C1-C4) -haloalkoxy, (C1-C4) -alkylthio.

The usual substituents are, in particular, the following substituents: cyano, nitro, halogen, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy, (C 1 -C 4) alkylamino, (C 1 -C 4) dialkylamino and (C 1 -C 4) alkylthio.

In view of their biological activity, compounds of formula (1) in which R ^{4 has the} following meanings are preferred: alkyl, alkenyl, alkynyl, alkoxy, alkenyloxy or alkynyloxy, wherein the hydrocarbon groups may be partially or fully halogenated and / or carry one to three of the following substituents:

- cyano, nitro, hydroxy, mercapto, amino, carboxyl, aminocarbonyl, aminothiocarbonyl,

- alkylsulfonyl of 1 to 6 carbon atoms, alkylsulfoxyl of 1 to 6 carbon atoms, alkylcarbonyl of 1 to 6 carbon atoms, cycloalkyl of 1 to 6 carbon atoms, alkoxy of 1 to 6 carbon atoms, haloalkoxy of 1 to 6 carbon atoms, (C 1 -C 6) alkoxycarbonyl, (C 1 -C 6) alkylthio, (C 1 -C 6) alkylamino, (C 1 -C 6) dialkylamino, (C 1 -C 6) alkylaminocarbonyl, (C 1 -C 6) dialkylaminocarbonyl, (C 1 -C 6) alkylaminothiocarbonyl, (C 1 -C 6) dialkylaminothiocarbonyl, (C 2 -C 6) alkenyloxy group,

benzyloxy, aryl, aryloxy, hetaryl and hetaryloxy, wherein the aromatic rings may be substituted with the usual groups; a cycloalkyl, cycloalkoxy, heterocyclyl or heterocyclyloxy group, wherein the cyclic groups may be partially or fully halogenated and / or carry one to three of the following substituents:

- cyano, nitro, hydroxy, mercapto, amino, carboxyl, aminocarbonyl, aminothiocarbonyl,

- (C1-C6) -alkyl, (C1-C6) -haloalkyl, (C1-C6) -alkylsulfonyl, (C1-C6) -alkylsulfoxyl, (C1-C6) -carbonyl, (C3-C6) cycloalkyl, (C 1 -C 6) alkoxy, (C 1 -C 6) haloalkoxy, (C 1 -C 6) alkoxycarbonyl, (C 1 -C 6) alkylthio, (C 1 -C 6) alkylamino, (C 1 -C 6) alkylamino C 1 -C 6 alkylaminocarbonyl, C 1 -C 6 dialkylaminocarbonyl, C 1 -C 6 alkylaminothiocarbonyl, C 1 -C 6 dialkylaminothiocarbonyl, C 2 -C 6 alkenyl, C 2 -C 6 alkenyloxy, C 2 -C 6 alkenyloxy

a benzyl, benzyloxy, aryl, aryloxy, hetaryl and hetaryloxy group, wherein the aromatic rings may be substituted with the usual groups;

an aryl, hetaryl, aryloxy or hetaryloxy group, wherein the cyclic groups may be partially or fully halogenated and / or carry one to three of the following substituents:

- cyano, nitro, hydroxy, mercapto, amino, carboxyl, aminocarbonyl, aminothiocarbonyl,

- (C 1 -C 6) alkyl, (C 1 -C 6) haloalkyl, (C 1 -C 6) alkylsulfonyl, (C 1 -C 6) alkylsulfoxyl, (C 1 -C 6) alkylcarbonyl, (C 3 -C 6) cycloalkyl, (C 1 -C 6) alkoxy, (C 1 -C 6) haloalkoxy, (C 1 -C 6) alkoxycarbonyl, (C 1 -C 6) alkylthio, (C 1 -C 6) alkylamino, (C 1 -C 6) dialkylamino (C 1 -C 6) alkylaminocarbonyl, (C 1 -C 6) dialkylaminocarbonyl, (C 1 -C 6) alkylaminothiocarbonyl, (C 1 -C 6) dialkylaminothiocarbonyl, (C 2 -C 6) alkenyl, (C 2 -C 6) alkenyloxy,

benzyl, benzyloxy, aryl, aryloxy, hetaryl and hetaryloxy, wherein the aromatic rings may be substituted with the usual groups;

- C (= NOR ¹ ) -A _n -R or NR'-CO-DR ^1V , wherein represents; A is an oxygen, sulfur or nitrogen atom, wherein the nitrogen atom may carry a hydrogen atom or an alkyl group having 1 to 6 carbon atoms;

n is 0 or 1;

R ( ¹⁾ is hydrogen, alkyl of 1 to 6 carbon atoms, alkenyl of 3 to 6 carbon atoms or alkynyl of 3 to 6 carbon atoms;

R is hydrogen or alkyl of 1 to 6 carbon atoms;

D is a direct bond, oxygen or NR ^b (R ^b = hydrogen, alkyl of 1 to 6 carbon atoms, alkenyl of 2 to 6 carbon atoms, alkynyl of 2 to 6 carbon atoms, cycloalkyl of 3 to 6 carbon atoms, cycloalkenyl of 3 to 6 carbon atoms 6 carbon atoms, aryl, arylalkyl of 1 to 6 carbon atoms in the alkyl moiety, hetaryl and hetarylalkyl of 1 to 6 carbon atoms in the alkyl moiety);

R ^{1 is} hydrogen, hydroxy, C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 1 -C 6 alkoxy, C 2 -C 6 alkenyloxy, C 2 alkynyloxy up to 6 carbon atoms, alkoxyalkyl having 1 to 6 carbon atoms in the alkoxy and alkyl moieties, alkoxyalkoxy having 1 to 6 carbon atoms in each alkoxy moiety, and alkoxycarbonyl having 1 to 6 carbon atoms;

R ^{1 is} hydrogen, (C 1 -C 6) alkyl, (C 2 -C 6) alkenyl, (C 2 -C 6) alkynyl, (C 3 -C 6) cycloalkyl, (C 3 -C 6) cycloalkenyl, aryl, (C 1 -C 6) arylalkyl up to 6 carbon atoms in the alkyl moiety, hetaryl and hetarylalkyl having 1 to 6 carbon atoms in the alkyl moiety;

Particularly preferred are phenyl derivatives of formula (I) in which the substituents have the following meanings:

R ³ is H, CN, alkyl of 1 to 6 carbon atoms, halogénalkyiová of 1 to 6 carbon atoms, cycloalkyl having 3 to 6 carbon atoms, cycloalkylalkyl having 3 to 6 carbon atoms in the cycloalkyl part and 1 to 4 carbon atoms in the alkyl aryl, arylalkyl of 1 to 4 carbon atoms and aryloxyalkyl of 1 to 4 carbon atoms, wherein the aromatic rings may be partially or fully halogenated and / or contain one to three of the following substituents: cyano, nitro, alkyl of 1 to 4 carbon atoms; 6 carbon atoms, halogénalkyiová of 1 to 6 carbon atoms, alkoxy of 1 to 6 carbon atoms, haloalkoxy of 1 to 6 carbon atoms, and C (= NOR ') - and R _I1;

R ⁴ optionally substituted aryl, hetaryl, aryloxy, hetaryloxy, arylthio and hetarylthio;

-Q _P -C (R ⁵ ) = N-Y'-R ⁶ or -QON = CR ⁷ R ⁸ ,

R ³ and R ⁴ together with the hydrogen atom to which they are attached form a four- or eight-membered ring which, in addition to the carbon atoms, may contain one or two oxygen and / or sulfur atoms and / or NH- and / or N (C) - C ₄ alkyl) -, and wherein the carbon atoms may carry the following substituents: halogen, alkyl of 1 to 6 carbon atoms or an alkoxyimino group having 1 to 4 carbon atoms; while

R ³ and R ⁴ are not simultaneously bonded via a heteroatom to a carbon atom.

Further preferred are phenyl derivatives of formula (1) in which the substituents have the following meanings: R ³ is hydrogen, cyano, halogen, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 6 alkoxy C 1 -C 6 haloalkoxy, C 1 -C 6 alkylthio, C 3 -C 6 cycloalkyl, C 3 -C 6 cycloalkylalkyl and C 1 -C 4 alkyl, aryl, (C 1 -C 4) arylalkyl, (C 1 -C 4) aryloxyalkyl and (C 1 -C 4) aryloxyalkoxy, wherein the aromatic rings may be partially or fully halogenated and / or contain one to three of the following substituents: cyano, nitro, alkyl (C 1 -C 6) group, (C 1 -C 6) haloalkyl, (C 1 -C 6) alkoxy up to 6 carbon atoms, haloalkoxy of 1 to 6 carbon atoms and C (= NOR ') - A _n -R;

R ⁴ optionally substituted aryl and hetaryl;

-Q _p -C (R ⁵ ) = N-Y'-R ⁶ or -QON = CR ⁷ R ⁸ ,

R ³ and R ⁴ are not simultaneously bonded via a heteroatom to a carbon atom.

Further preferred are compounds of formula (I) wherein:

- m O,

- R ¹ group (Ia), (Ib), (Ic) and (Id),

- a group R ¹ (Ib),

- R ¹ group (Id),

- R ³ is alkyl having 1 to 4 carbon atoms (especially methyl)

- R ⁴ optionally substituted alkyl of 1 to 6 carbon atoms,

- R ⁴ optionally substituted alkenyl of 2 to 6 carbon atoms,

- R ⁴ optionally substituted aryl (especially 3-substituted phenyl),

- R ³ methyl and R ⁴ optionally substituted alkyl of 1 to 6 carbon atoms,

- R ³ methyl and R ⁴ optionally substituted aryl (especially 3-substituted phenyl),

- R ⁴ C (R ⁵ ) = N-Y'-R ⁶ , wherein Y ¹ represents in particular an oxygen atom and R ⁵ represents in particular methyl, ethyl, allyl or propargyl.

Also preferred are compounds of formula (I) in which is

- R ^{3 is} C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, cyclopropyl or C (CH ₃ ) = NO-C _r C ₆ -alkyl a

- R ^{4 is} aryl, hetaryl or benzyl, wherein the aromatic rings may be partially or fully halogenated and / or carry one to three of the following substituents: cyano, nitro, C 1 -C 6 alkyl, haloalkyl 1 (C 1 -C 6) alkoxy, (C 1 -C 6) alkoxy, (C 1 -C 6) haloalkoxy and C (= NOR'A _n- R); or

-R ⁴ C (R ⁵ ) = N-Y'-R ⁵

Also preferred are compounds of formula (I) in which is

- R ^{3 is} C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, cyclopropyl or C (CH ₃ ) = NO-C | -C ₆ -alkyl a

- R ^{4 is an} alkyl group having 1 to 6 carbon atoms, an alkenyl group having 2 to 6 carbon atoms, an alkenyl group having 2 to 6 carbon atoms, or a cyclopropyl group, these radicals being partially or fully halogenated and / or carrying one to three aryl and hetaryl, wherein the aromatic rings may carry one to three of the following substituents: cyano, halogen, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 6 alkoxy C 1 -C 6 halogen and C 1 -C 6 haloalkoxy.

Also preferred are compounds of formula (I) in which is

- R ³ is alkyl having 1 to 6 carbon atoms, haloalkyl of 1 to 6 carbon atoms, cyclopropyl or C _(CH3) = NO-C ₁ -C ₆ alkyl and

- R ^{4 is} C 1 -C 6 alkoxy, which radical may be partially or fully halogenated and / or carry one to three of the following aryl and hetaryl groups, the aromatic rings of which may carry one to three of the following substituents: cyano, halogen, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 6 alkoxy and C 1 -C 6 haloalkoxy.

Also preferred are compounds of formula (I) in which is

- R ^{3 is} C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, cyclopropyl or C (CH ₃ ) = NO-C _C6 alkyl, and

- R ^{4 is} C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkenyl or cyclopropyl, these radicals may be partially or fully halogenated and / or carry one to three of the radicals; the following groups: aryl and hetaryl, wherein the aromatic groups may carry one to three of the following substituents: cyano, halogen, alkyl of 1 to 6 carbon atoms, haloalkyl of 1 to 6 carbon atoms, alkoxy of 1 to 6 C 1 -C 6 haloalkoxy or C 1 -C 6 haloalkoxy;

- R ⁴ an aryl, hetaryl or benzyl, where the aromatic rings in these radicals to be partially or fully halogenated and / or carry one to three of the following substituents: cyano, nitro, alkyl of 1 to 6 carbon atoms, haloalkyl of (C 1 -C 6), (C 1 -C 6) alkoxy, (C 1 -C 6) haloalkoxy and (2 (= Ν0Κ) -Α "-Κ; or

-R ⁴ C (R ⁵ ) = N-Y'-R ⁶ .

Also preferred are compounds of formula (I) in which is

- R ³ alkyl of 1 to 6 carbon atoms, haloalkoxy of 1 to 6 carbon atoms, cyclopropyl or C _(CH3) = NO-C ₁ -C ₆ alkyl and

- R ^{4 is} alkoxy having 1 to 6 carbon atoms, the radical of which may be partially or fully halogenated and / or carry one to three of the following groups: aryl and hetaryl, wherein the aromatic groups may carry one to three of the following substituents: cyano, halogen, alkyl of 1 to 6 carbon atoms, haloalkyl of 1 to 6 carbon atoms, alkoxy of 1 to 6 carbon atoms and haloalkoxy of 1 to 6 carbon atoms, or

R ^{4 is} aryloxy, hetaryloxy or N-aryl-N-methylamino, wherein the aromatic rings in these radicals may be partially or fully halogenated and / or carry one to three of the following substituents: cyano, nitro, alkyl of 1 to 6 C 1 -C 6 haloalkyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy and C (= NOR ') - A _n -R'', or

-R ⁴ C (R ⁵ ) = N-Y'-R ⁶ .

Compounds of formula (1.1) are particularly preferred for use against animal pests and harmful fungi.

in which the substituents and indices have the following meanings: R ¹ C (CO ₂ CH ₃ ) = CHCH ₃ , C (CO ₂ CH ₃ ) = CHOCH ₃ , C (CO ₂ CH ₃ ) = NOCH ₃ or C (CONHCH ₃ > NOCH ₃ ;

R ^{2 is} cyano, halogen, C 1 -C 4 alkyl, C 1 -C 2 haloalkyl, C 1 -C 4 alkoxy, C 1 -C 2 haloalkoxy and C 3 -C 6 cycloalkyl;

m 0 or 1;

R ³ is hydrogen, hydroxy, cyano, (C 1 -C 4) alkyl, (C 1 -C 2) haloalkyl, (C 1 -C 4) alkoxy, (C 1 -C 2) haloalkyloxy, (C 3 -C 6) cycloalkyl carbon atoms, cycloalkylalkyl having 3 to 6 carbon atoms in cycloalkyl and 1 to 4 carbon atoms in the alkyl moiety, or benzyl groups which are substituted by conventional groups,

R ⁴ is hydrogen or C 3 -C 6 cycloalkyl, C 1 -C 6 alkyl, C 1 -C 6 alkoxy which may be partially or fully halogenated and / or may carry one to three (in particular one) from the following groups: cyano, (C 1 -C 4) alkoxy, (C 3 -C 6) cycloalkyl, unsubstituted or substituted phenyl, naphthyl, pyridyl, pyrazinyl, thienyl, pyrazolyl or isoxazolyl;

unsubstituted or substituted phenyl, naphthyl, pyridyl, pyrazinyl, thienyl, pyrazolyl or isoxazolyl groups;

unsubstituted or substituted by phenoxy, naphthyloxy, pyridyloxy, pyrazinyloxy, thienyloxy, pyrazolyloxy or isoxazolyloxy; or

R ³ and R ⁴ together with the carbon atom to which they are attached, a saturated or partially unsaturated four- to eight-membered ring which, in addition to the carbon atoms as ring members, may contain one heteroatom selected from oxygen, sulfur and nitrogen, and which may may be partially halogenated and / or may carry one to three of the following groups: (C1-C4) alkyl, (C1-C4) haloalkyl, (C1-C4) alkoxy, (C1-C4) haloalkoxy, oxo (= O) and alkoxyimino having 1 to 4 carbon atoms (= N-alkoxy) wherein

R ³ and R ⁴ are not simultaneously attached to the carbon atom through the heteroatom.

7. In addition, compounds of formula (1.3) are particularly preferred for use against animal pests and harmful fungi.

in which the substituents and indices have the following meanings: R ¹ C (CO ₂ CH ₃ ) = CHCH ₃ , C (CO ₂ CH ₃ ) = CHOCH ₃ , C (CO ₂ CH ₃ ) = NOCH ₃ or C (CONHCH ₃ ) = NOČH ₃ ;

R-cyano, halogen, C 1 -C 4 alkyl, C 1 -C 2 haloalkyl, C 1 -C 4 alkoxy, C 1 -C 2 haloalkoxy, and C 3 -C 6 cycloalkyl ;

m 0 or 1;

R ³ is hydrogen, cyano, halogen, C 1 -C 4 alkyl, C 1 -C 2 haloalkyl, C 1 -C 4 alkoxy, C 1 -C 2 haloalkoxy, and C 3 -C 3 cycloalkyl 6 carbon atoms;

R ⁵ is hydrogen, cyano, halogen, C 1 -C 4 alkyl, C 1 -C 2 haloalkyl, C 1 -C 4 alkoxy, C 1 -C 2 haloalkoxy, and C 3 -C 3 cycloalkyl 6 carbon atoms;

Y ¹ O, NH or N (CH _3);

R ( ⁶⁾ is hydrogen, (C1-C6) alkyl, which may bear the following groups: (C1-C4) alkoxy, unsubstituted or conventional, C3-C6-cycloalkyl, unsubstituted or phenyl-substituted group;

(C 3 -C 6) alkenyl, (C 3 -C 6) haloalkenyl, (C 3 -C 6) alkynyl, (C 3 -C 6) haloalkynyl, or unsubstituted or C 3 -C 6 -cycloalkyl substituted by conventional groups.

In addition, other compounds of formula (1.5) are preferred for use against animal pests and harmful fungi.

(1.5) in which the substituents and indices have the following meanings: R ¹ C (CO ₂ CH ₃ ) = CHCH ₃ , C (CO ₂ CH ₃ ) = CHOCH ₃ , C (CO ₂ CH ₃ ) = NOCH ₃ or

C (CONHCH ₃₎ = NOCH _3;

R ^{2 is} cyano, halogen, C 1 -C 4 alkyl, C 1 -C 2 haloalkyl, C 1 -C 4 alkoxy, C 1 -C 2 haloalkoxy and C 3 -C 6 cycloalkyl;

m 0 or 1;

R ³ is hydrogen, cyano, halogen, C 1 -C 4 alkyl, C 1 -C 2 haloalkyl, C 1 -C 4 alkoxy, C 1 -C 2 haloalkoxy and C 3 -C 6 cycloalkyl carbon atoms;

R ^x is hydrogen, halogen, C 1 -C 4 alkyl, C 1 -C 2 haloalkyl, C 1 -C 4 alkoxy, C 1 -C 2 haloalkoxy, and C 3 -C 6 cycloalkyl alkyl;

R ¹ is hydrogen, C 1 -C 6 alkyl, which may be partially or fully halogenated and / or may carry one to three (in particular one) of the following groups: C 1 -C 4 alkoxy, unsubstituted or substituted by conventional groups (C 3 -C 6) cycloalkyl or unsubstituted or substituted phenyl; (C 1 -C 6) alkoxy, (C 1 -C 6) haloalkoxy, unsubstituted or substituted by C 3 -C 6 cycloalkyl, unsubstituted or substituted by phenyl, unsubstituted or substituted by pyridyl or unsubstituted by conventional groups substituted pyrimidyl;

R ⁷ is hydrogen, cyano, halogen, C 1 -C 4 alkyl, C 1 -C 2 haloalkyl and C 3 -C 6 cycloalkyl, or

R ^y and R 'together with the double bond to which they are attached form a cycloalkenyl group having 4 to 6 carbon atoms.

Preferred for use are the compounds of formula (I) which are listed in the following tables. In addition, independently of the combination in which they are mentioned, the groups listed as substituents in the tables represent a particularly preferred substituent.

Table 1

Compounds of formula (Ia) in which R @ ² _m is hydrogen and the combination of R @ ³ and R @ ⁴ for the compound each corresponds to one row in Table A.

Table 2

Compounds of general formula (Ib.1) in which R ² _m is hydrogen and the combination of R ³ and R ⁴ for the compound corresponds in each case to one row in Table A.

Table 6

Compounds of formula (Ia.2) wherein R ² _m is hydrogen and the combination of R ³ and R ⁴ for the compound each corresponds to one row in Table A.

(La.2)

Table 7

Compounds of general formula (Ib.2) in which R ² _m is hydrogen and the combination of R ³ and R ⁴ for the compound each corresponds to one row in Table A.

Table 3

Compounds of formula (1c.1) in which R ² _m is hydrogen and the combination of R ³ and R ⁴ for the compound corresponds in each case to one row in Table A.

The compounds of formula (Ic.2), wherein R ² is hydrogen, and _{R A} combination of the radicals R ³ and R ⁴ for each compound corresponds to one line of table A.

(Ic.l)

Table 4

Compounds of formula (Id.1) in which R @ ² _m is hydrogen and the combination of R @ ³ and R @ ⁴ for the compound each corresponds to one row in Table A.

(Ic.2)

Compounds of formula (Id.2) in which R ² _m is hydrogen and the combination of R ³ and R ⁴ for the compound each corresponds to one row in Table A.

(Id.l)

Table 5

Compounds of formula (Ie.l) wherein R ² _m is hydrogen and the combination of R ³ and R ⁴ for the compound each corresponds to one row in Table A.

Table 10

Compounds of formula (Ie.2) in which R ² _m is hydrogen and the combination of R ³ and R ⁴ for the compound each corresponds to one row in Table A.

SK 283343 Β6

Table A:

Nr. R ^J R ⁴ A.L. H CH A.2 H CHjCHj A. 3 H CHjCHjCHj A. 4 The TA (CH) j A.5 H CHjCHjCHjCHj A.6 H C (CK i) j A.7 The CH (CH3) CWjCKi A.8 M CeH _s A.9 H 2-F-CIH * A.10 H 3-FC ₄ H ₄ A.11 H 4-F-CIH * A.12 H 3-CH3-C _with H < ₊ > A.13 H 3-OCXj-CsH ₄ A. 14 H 3-CFj-CIH < A.15 H 3-Cl-CGX < A.16 The 2-CH-CGH * A.27 H 4-CK i-CIHIE a. ia H cyclopropyl A.19 H cyclohexyl A. 20 H CHjCHjCl A, 21 M CHaCHjCRjCN A.22 H CH ₃ -C _{Th 5} A. 23 H CHjCMjCHjCHa-OCH A.24 The CHjCHj-OCHiCHj A.25 H CH ₂ C (CH ₃ ) = NOCH ₃ A. 26 H CH 3 -U-F'C ₆ H ₄ ] A. 27 H CH 3 - [3-CH-C ₆ H ₄ ] A.28 H 3-CN-C5H4

ar; R ³ · A.29 M 3, S- (CH3) ₂ -C1H3 A.30 H 3-COCH-CIHIE A.31 H 3 [C (CH) "NOCHj) -CíH4 A.32 H lrnaphthyl A.33 H CHíCRj-O-CcHj A. 34 The CH ₂ - (3-Cl-pyridin-5-yl) A.35 H 4-OCH-pyridin-2-yl A.35 H CH ₂ - (5-Cl-pyrasin-2-yl) A.37 N 2-thienyl A. 39 H 3-CH (CH) J-isoxazol-5'yl A.39 H 3-CíHj-pyrazol-yl A. 40 H OCH (CH) j A. 41 H OCHjCHjCHjCKjCHj A. 42 H H-U-F-CíHd A.43 H OCH 3 - (4-F-CgH ₄ ) A.44 H O- [CH ₃ € ~ -pyridln-2-yl] A.45 H C-CO- _(4-Cl-4 CEH) A.45 H NH- (4-Cl-C 8 H 11) A.47 CH CH, A.48 CH CHjCHj A.49 CH CHjCHjCKj A.50 CH CH (CH3) ₂ A.51 CH CHjCJfjCHjCHj A.52 CH C (CH3) 3 A.53 CH CHICHjÍCHjCRj A.54 CH CIH, A.55 CH 2-F-CgHg A.5S CH 3-F-CíHj A.57 CK i 4-FC «H _t A. 59 CH 3-CH-CgHg A. 59 CH 3-OCH-CJH * A.60 CH 3-CFj-C _TH ( A.61 CK i 3-Cl-CgM ₄ .62 CK i 2-CH-CjHj .63 CH 4-CH-cghj A.64 CH cyclopropyl A.6 $ CH cycLahexyl A.66 CH CHjCHjCl

Hr. R ³ R A.67 CH ch ₂ ck ₂ ck ₂ cn A.6B CH CH-cghj A.69 CH CK ₂ CH ₃ CH ₂ CH ₂ -OCH 3 A.70 CH CHjCHj-OCHjCHj A.71 CH CH3C (CH3) sNOCH3 A.72 CH CH ₂ - [4-FC ₆ H ₄ ] A.73 CH CH ₂ - (3-CN-C 8 H ₄₎ A, 74 CH 3-CN-C6H4 A.75 CH S.A-ÍCHjlj-cghj Λ.76 CH 3-COCMj-CgHg A.77 CH 3- (c (CH 3) -NOCB 3] -C 8 H 8 A.7B CH 1-naphthyl A.79 CH CK ₂ CH ₂ -O-Cl ₅ A.eo CH CH ₂ - (3-Cl-pyridin-5-yl) x.ei ch ₃ 4-OCH-pyridin-2-yl . .62 CH CH ₂ - [S-Cl-pyrazin-2-yl] A.83 ch ₃ 2-thienyl A.84 CH 3-CH (CH 2) ₂ -oxaaol-5-yl A.85 CH 3-CjHs-pyrazol-l-yl A.86 CH OCH (CH3) a A.87 CH OCHjCHjCHjCHjCHj A.88 CH O- (4-F-CgRj A.89 CH OCH ₂ - (4-F-C ₄ H ₄ ) A.90. CH O- [6-CH 3 -pyridin-2-yl] A.91 CH C-CO- [4-Cl-C4H4] A.92 CK i NH- (4-Cl-CgHg] A.93 OH CH A.94 OH CHjCHjCHjCHj A.95 OH CH (CH3) 2 A.9 « OH 3-CH 3 -C ₅ H 4 A.97 OH CH 3 -Cl ₅ A.98 OH 3,5-Clj-CíHj A.99 OCH CH A. 100 OCH CHjCHjCHíCRj A. 101 OCH CHCH ₃ ) ₂ A.102 OCH CHaCHjCHjCHjCHjCHj A.103 OCH 3-CH-CgHg A. 104 OCH CH ₂ -CH ₅ A.105 OCH 3,5-Cl-C 1 H 3

ΝΓ. R ³ R < A. 105 OCHjCHj CH A. 107 OCHjCHj CK2CH2CHJ A. 103 OCHjCHj CH (CH3) j A. 109 OCHjCHj CHjCHjCKjCHjCHj A. 110 OCHjCHj J-CH-cghj A. 111 OCK ₂ CHj CKj '| 4'F ~ C | H <) A. 112 OCH2CH3 2,4-Fj-C ₍ Hj A. 113 cyclopropyl CH A.114 cyclopropyl CHjCHjCKj A. 115 cyclopropyl OCH2CH3 A. 115 cyclopropyl CgH _s A. 117 Cl CgH _s A.118 Cl CH A.119 Cl CH (CH) j A.120 Cl 3-CH-C H _t < A.121 Cl 3-CN-Cl ₄ A.122 Cl CK CH ₂ -OC ₆ IF5 λ.123 Cl CHjCHj-OCHjCHj A.124 Cl CH) - (4-C ₆ F'C _4] A.125 SCKJA CH A.126 SCHj CjHs A.127 SCHj CH (CH) j A.128 CHĺCHjh CH A.129 CHICHjlj CHjCHj A.130 CH (CH) j C _S H _S A.131 CH <CH 31 ₂ OCH A.132 CH (CH3) f OCH (CH3) ₂ A.133 CH (CH3) j 3-CH-C <H ' A.134 CN CH A.135 CN 3-CH 3 -C ₆ H ₄ A. 136 CN CH ₂ - (2,4-Cl ₂ -CeH 3) A. 137 CN CKjCKjCHjCHj A.139 CN CW (CKj> ₂ A. 139 CHjCHj CIIj R. 140 CHjCHj CHjCHj A. 141 CH ₂ CKj CH ₂ CH ₂ CH 3 A. 142 CF. ₂ CHj CH (CH3) 2 A.143 CH ₂ CXj CH ₂ CH ₂ CH ₂ CH 3 A. 14 * CH2CH3 C (CH3) j

Hr. R ³ and ⁴ A.145 CHjCHj CH (CH3) CH3CH3 A. 146 CHjCHj CíK _S A.147 CHjCHj 2-F-Cl ₄ A. 148 CH2CH3 3-F-CjKg A. 149 CHjCHj F-i-CgHg A. 150 CHjCHj 3-CR ₃ -C ₁ H 4 A.151 CHjCHj 3-OCH 3 -C 8 H ₄ A.152 CHjCHj 3-CFj-Ceiq A. 153 CHjCHj 3-Cl-C ₄ H ₄ A.154 CHjC.Tj 2-CH3-C5H4 A.155 CH ₂ C 8j 4-CH 3 -C ₆ H ₄ A. 156 CK2CH3 cyelopropyl A.157 CK2CH3 cyclohexyl A.158 CHjCHj CHjCHjCl A.159 CHjCHj CHjCHjCKjCN A.160 CH2CH3 CH-cghj A.161 CH3CH3 CHjCHjCHjCHj-OCRj A. 162 CH3CH3 CHjCHj-OCHjCHj A.163 CH ₂ CH ₃ CKjC (CH3) -NCH3 A.164 CHjCHj CXA-U-F-CeiM A.165 Chick Ca ₂ - [3-CN-ClH] A.166 CHjCHj 3-CN-C ₆ H ₄ A.167 CH2CH3 3.5- _(CH3) 2-CcHj A.168 CHjCHj 3-COCH 3 -C 6 H ₄ A. 169 CHjCHj 3- [C (CH 3) = NOCH ₃ ] - C 8 H ₈ A.170 CH ₃ CH ₃ 1-naphthyl A.171 CHjCHj CHjCKj-O-CSKS A.172 chjCH ₃ CHj- [3-C pyriäin-5-yl] A.173 CHjCHj 4-OCM3 "pyridin-2-yl A.174 CHjCHj CHj- | 5-C pyratin-2-yl] A.175 CHjCHj 2-thienyl A. 176 CHjCHj 3-CH (CH3) -1-oxazol-5-yl A.177 CHjCHj 3-C ₄ H 5 -pyrrolol-1-yl A. 178 CHjCHj OCH (CH3) j A. 179 CHjCHj OCHjCHjCHjCHjCH) A.190 CHjCHj O- [4-FC _e R] A. 191 CHjCHj OCH-U-F-CgHg] A.182 CHjCHj O- [6-CH) -pyridin-2-yl] A. 183 CHjCHj 0-C0- [4-C H ₄ C <i

Nr. R ³ R A.223 CH2CH3 CH-F-CtCHjHM CíKd A.224 CHjCHj CK-CC1-14-P-CgHg] A.225 CHjCHj CCI-CH-tri-F-Cglq] A.226 CHjCHj C (CH3) -CH- 14-FC ₄ H ₄ ] A.227 CH-CH-CjHj A.228 CK _i-ct Hj CH-C (CH3> C «H $ A.229 CH-cghj CH = CC1-NAV ₅ A.230 C 6 -C ₆ H ₅ C (CH 3) -CH-C 8 H 3 A.231 CH-CgXg CCL-CH-cghj A.232 CK i-CjHs CH-CH- [4-F-C 8 H 8] A.233 CK i-CsH5 CH-C (CH3) - [4-F-CGH | J A.234 CH-C _e H _p CH-CC1-14-F-C A.235 -CB-CgMg CCL-CH- [4-F-CgE] A.236 CHj'CsHs C (CH 3) -CK- (4-F-C 8 H 8) A.237 H CH (CH3) CH {C) -N0CHj A.239 H CH (CH 3) -C (CH 3) -NCCH 3 CH 3 A.239 H CH (CH) -C _t H ₅ A.240 H CHlCHjl-II-F-C.HU A.241 H 1-CgH8-cyclo-propyl A.242 The 1- (4-Cl-C4H4) -cyclopropyl A.243 H CHjC (CH) -NOCH) A.244 H CRjCťCHjl-MXHjCH) A.245 H 1- [C1CH3] -NOCH3] cyclopropyl A.246 CH CH [CH3] -C (CH3) -HOCH3 A.247 CH, CH [CH]} - C (Ct H) = NOCH ₃ CR ₃ A.248 CH) CHICHjl-C ^ A. 249 CK ₃ CHKHjHU-P-CgKg) A.250 CH) l-cyclopropyl-CjHj A.251 CH) 1- (4-Cl-C (H ₄ ) -cyclopropyl) A.252 CH) CH3C (CH3) sNOCH3 A.253 CH) _The CH C (CH)) -NOCHjCHj A.254 CH, 1- [C (CH 3 -NOCR 3 -cyclopropyl) A.2 = 5 CHjCHj CK (CH3) - C (CH3J-KOCHi) A.256 CHjCHj CH (CH 3) -C (CH 3) = NOCH 3 CH 3 A.257 CHjCHj CH (CH) - C 8 H 8 _s A.258 CHjCHj CHĺCHjJ-K-F-CgHg] A.259 CKjCH ₃ l-cyclopropyl-cghj A. 260 CHiCHj 1- (4-Cl-C 8 H 11 -cyclopropyl) A.261 CHjCHj CH 3 C (CH 3) -NOCH 3

Hr. R ³ R A.184 CHjCHj NH- (4-Cl-CeKd A.195 CH Chjo? = C (CH) j A.186 CH3 CHjON = C (CH 3) -CHjCH3 A.187 -CB CKjON-C (CH) C _D H _S A.188 CH CKjOM-C (CH) - [4-C1 _4-CIM) A.189 CHjCHj CHjON-C (CH) j A.190 CHjCHj CH 3 ON = C (CH 3) -CH 3 CH 3 A.191 CHjCHj CHjON'C (CH) -CíHs A.192 · CHjCHj CKjON -C (CH>) - (4-Cl-CGH _4] A.193 CH-CIHS CH 3 ON = C (CH 3) 3 A.194 CH-cghj CH 3 -CH 2 CH 3 -CH 3 CH 3 A. 195 CMJ-CjHj CHjON-C (CHj) 'GjHj A. 196 CH-CGH; CH3ON-C (CH3) - (4-CI-C4H4) A.197 H CH 'CH-CjHg A.198 H CH-C (CH 3) -C ₄ H 8 A. 199 H CH-CC1-CIHS A.200 H C (CH 3) 3 CH-C 3 H 8 A. 201 H CCKH-CsHj A.202 H CH-CH- (4-F-C 5 H 4 J) A.203 H CH-C (CH) - (4-P-C 8 H *) A. 204 H CH-CC1-14 - C ₆ E _4] A.205 H CC1-CH-14-F (CgH ₄ ) A.206 H C (CH 3 = CH- [4-FC ₄ H ₄ ] A.207 CH CH-CH-Ph A.20B CH CH-C (CH) C ₄ H S A.209 CH CH = CCI-cghj A.210 CH C (CK) 1 = CH-C ₄ H 5 A.211 CH CCi.-CH-C ₄ H S A.212 CH CH 2 CH- [4-FC _with H ₄ l K.213 CH) CH 2 C (CKj) - (4-FC ₅ H ₄ 1) A. 214 CH CK-CC1 * HF-Cl ₄ ] A.215 CH CC1-CH- [4-F-Cl ₄ ] A.216 CH) C (CH3) ^and CH4-14-F-C4H4;] , A.217 CHjCHj CH 2 CH-C ₄ K5 A.218 CH, OJ, CH-C (CH ₃ ) -C «H _$ A.219 CHjCK) CH-CC1-C18 ₅ A. 220 CHjCHj C (CH3 = CH-CgM5) A.221 CHjCHj CC1 »CH-C _S H _S A.222 CH ₂ CH) CH-CH * [4-F-C 1 H ₄ ]

Nr. Ä ³ R ⁴ A.262 CHjCHj CH3C (CH3) -NOCR3CB3 A.263 CHjCHj 1- | C (C H) -MOCHj) -cyclopropyl A.264 CNJ-cghj CHČCMjJ-CfChjl-NOC. A.265 CH-CTH) CRÍCHjHCICHjÍ-NOCRjCH) X.266 CNJ-cghj CH (CH) -CgHs A.267 CH-CíHj CHĺCHjJ-H-F-CíHgJ A.268 CH-CGHS IC ₄ W 3 -cyclopropyl A.269 CH-cghj 1-H-Cl-CsHg] -tyclopiopyi A.270 CH-cghj CH 3 C (CH 3) -NOCH 3 A.271 CH-cghj Oi _with c (CH3) -JWCH3CH) A. 272 CK »-CgHj 1- (C (CH) 1 'NOCHjJ-cyclopropyl- A. 273 - ICH ₄ - A.274 - (CH) s A.275 - (O-CHjJj JCHjIj- A.275 - ICH ₃ - 3- (CH ₃ ) ₃ - A.277 - (CH 3) j -CH (CH ₃ ) - [CH ₂ ] j - A.278 - (CH3) j-C (-0) - (0¾) j- A.279 ~ (CH 3) j -C (= NOCH 3) - CH 3 j - A.280 - (CH 3) j -C (OCH 3) j - (CH 3) - A.2B1 -CH ₂ -CH ₁ CH ₂ -CH ₁ -CH (CH 3) -CH ₂ - A.282 - (CH ₂ 1 j-CK (CH 3) -CH 3 -) A.283 -CH-CH-C (-HOCH 3) -CH'CH- A.284 -CH 3 -C 1 -NOCH. ) - (CH 3> j -

Table 11

The compounds of formula (Ia. 3) in which R ² _m is hydrogen, Y is oxygen and the combination of the radicals R ^3, R ^4, R ⁵ and R ⁶ for each compound corresponds to one line of Table B.

Table 12

The compounds of formula (IA.3) wherein R _{^2, R} a is H, Y is NH and the combination of the radicals R ^3, R ^4, R ⁵ and R ⁶ for each compound corresponds to one line of Table B.

Table 13

Compounds of formula (Ia.3) in which R ₁ is hydrogen, Y is N (CH ₃ ) and the combination of R ³ , R ⁴ , R ⁵ and R ⁶ for the compound each corresponds to one row in Table B.

Table 14

Compounds of formula (Ib.3) wherein R ² _m is hydrogen, Y is oxygen and the combination of R ³ , R ⁴ , R ⁵ and R ⁶ for the compound each corresponds to one row in Table B.

° (Ib.3)

Table 15

Compounds of formula (Ib.3) wherein R ² _m is hydrogen, Y is NH and the combination of R ³ , R ⁴ , R ⁵ and R ⁶ for the compound each corresponds to one row in Table B.

Table 16

Compounds of formula (Ia.3) wherein R ² _m is hydrogen, Y is N (CH ₃ ) and the combination of R ³ , R ⁴ , R ⁵ and R ⁶ for the compound each corresponds to one row in Table B.

Table 17

Compounds of formula (Ic.3) wherein R ² _m is hydrogen, Y is oxygen and the combination of R ³ , R ⁴ , R ⁵ and R ⁶ for the compound each corresponds to one row in Table B.

Table 18

Compounds of formula (Ic.3) wherein R ² _m is hydrogen, Y is NH and the combination of R ³ , R ⁴ , R ⁵ and R ⁶ for the compound each corresponds to one row in Table B.

Table 19

Compounds of formula (Ic.3) wherein R ² _m is hydrogen, Y is N (CH ₃ ) and the combination of R ³ , R ⁴ , R ⁵ and R ⁶ for the compound each corresponds to one row in Table B.

Table 20

Compounds of formula (Id.3) in which R ² _m is hydrogen, Y is oxygen and the combination of R ³ , R ⁴ , R ⁵ and R ⁶ for the compound each corresponds to one row in Table B.

Table 21

Compounds of formula (Id.3) wherein R ² _m is hydrogen, Y is NH and the combination of R ³ , R ⁴ , R ⁵ and R ⁶ for the compound each corresponds to one row in Table B.

Table 22

The compounds of formula (Id.3) wherein R _{^2, R} a is H, Y represents N (CH ₃₎ a combination of the radicals R ^3, R ^4, R ⁵ and R ⁶ for each compound corresponds to one line of Table B.

Table 23

The compounds of formula (Ie.3) in which R ² _m is hydrogen, Y is oxygen and the combination of the radicals R ^3, R ^4, R ⁵ and R ⁶ for each compound corresponds to one line of Table B.

Table 24

Compounds of formula (Ie.3) wherein R ² _m is hydrogen, Y is NH and the combination of R ³ , R ⁴ , R ⁵ and R ⁶ for the compound each corresponds to one row in Table B.

Table 25

The compounds of formula (Ie.3) in which R ² _m is hydrogen, Y is N (CH ₃₎ a combination of the radicals R ^3, R ^4, R ⁵ and R ⁶ for each compound corresponds to one line of Table B.

Table 26

The compounds of formula (la.4), wherein R ² is hydrogen, Y is oxygen and the combination of the radicals R ^3, R ^4, R ⁵ and R ⁶ for each compound corresponds to one line of Table B.

(Ic.4)

Table 33

Compounds of formula (Ic.4) wherein R ² _m is hydrogen, Y is NH and the combination of R ³ , R ⁴ , R ⁵ and R ⁶ for the compound each corresponds to one row in Table B.

Table 27

The compounds of formula (la.4), wherein R ² is hydrogen, Y is NH and the combination of the radicals R ^3, R ^4, R ⁵ and R ⁶ for each compound corresponds to one line of Table B.

Table 28

The compounds of formula (la.4) wherein R _{^2, R} a is H, Y represents N (CH ₃₎ a combination of the radicals R ^3, R ^4, R ⁵ and R ⁶ for each compound corresponds to one line of Table B.

Table 29

Compounds of formula (Ib.4) wherein R ² _m is hydrogen, Y is oxygen and the combination of R ³ , R ⁴ , R ⁵ and R ⁶ for the compound each corresponds to one row in Table B.

Table 30

Compounds of formula (Ib.4) wherein R ² _m is hydrogen, Y is NH and the combination of R ³ , R ⁴ , R ⁵ and R ⁶ for the compound each corresponds to one row in Table B.

Table 31

Compounds of formula (Ib.4) wherein R ² _m is hydrogen, Y is N (CH ₃ ) and the combination of R ³ , R ⁴ , R ⁵ and R ⁶ for the compound each corresponds to one row in Table B.

Table 32

Compounds of formula (Ic.4) wherein R ² _m is hydrogen, Y is oxygen and the combination of R ³ , R ⁴ , R ⁵ and R ⁶ for the compound each corresponds to one row in Table B.

Table 34

The compounds of formula (Ic.4) wherein R _{^2, R} a is H, Y represents N (CH ₃₎ a combination of the radicals R ^3, R ^4, R ⁵ and R ⁶ for each compound corresponds to one line of Table B.

Table 35

Compounds of formula (Id.4) wherein R ² is hydrogen, Y is oxygen and the combination of R ³ , R ⁴ , R ⁵ and R ⁶ for the compound each corresponds to one row in Table B.

Compounds of formula (Id.4) wherein R ² _m is hydrogen, Y is NH and the combination of R ³ , R ⁴ , R ⁵ and R ⁶ for the compound each corresponds to one row in Table B.

Table 37

Compounds of formula (Id.4) wherein R ² _m is hydrogen, Y is N (CH ₃ ) and the combination of R ³ , R ⁴ , R ⁵ and R ⁶ for the compound each corresponds to one row in Table B.

Table 38

The compounds of formula (Ie.4) in which R ² _m is hydrogen, Y is oxygen and the combination of the radicals R ^3, R ^4, R ⁵ and R ⁶ for each compound corresponds to one line of Table B.

Table 39

The compounds of formula (le.4) in which R ² _m is hydrogen, Y is NH and the combination of the radicals R, R ^4, R ⁵ and R ⁶ for each compound corresponds to one line of Table B.

Table 40

Compounds of formula (Ie.4) in which R ² _m is hydrogen, Y is N (CH ₃ ) and the combination of R ³ , R ⁴ , R ⁵ and R ⁶ for the compound each corresponds to one row in Table B.

Table B:

Hr. R ^J r5 R® 3.1 Cl H H B.2 Cl CH H B.3 Cl CRjCHj The 3.4 Cl CFj H B.5 Cl CHP ₂ B B. 6 Cl CHjF R B.7 Cl Cl H B.8 Cl OCH ₃ H 2.9 Cl OCH2CH3 H 10.08 Cl CN H B.11 CH H H D. 12 CH CH H 3.13 I cWJ CHjCHj H

Nr. R ³ R ³ R ^s B.53 CFj CHjCHj CH B.S4 CFj CFj CH B.55 CFj CHFj CH) B. 56 CFj CHjP CH, B.57 CFj Cl CH B. 58 CFj OCH CH B.59 CFj OCH ₂ CK3 CK i B.60 CFj CN CH B.61 Cl H CHjCHj B.62 CL CH CHjCHj B.63 Cl CHjCHj CHjCHj B. 54 Cl CF) CHjCHj B.65 Cl CHFj CHjCH. B.66 Cl CHjF CHjCH. B.67 Cl Cl CH ₂ CH 3 B.6B Cl OCH] CHjCHj B.69 Cl OCHjCHj CH ₂ CH 3 B.70 Cl CN ch ₂ ckj B.71 CH The CH ₂ CK ₃ B.72 CH CH CHjCHj B. 73 CH CHjCHj ch ₂ ch ₃ B.74 CH CFj CHjCHj B. 75 CH CHFj CHjCHj B.76 CH CHjF CHjCHj B.77 CH) Cl CHjCHj B. 78 CH OCH) CHjCH) B.79 CH OCKjCKj CHjCHj B.80 CH) CN CHjCHj B. 81 CFj H CHjCHj B.82 CFj CK i CHjCHj B. 83 CFj CHjCHj CHjCHj B.84 CFj CFj CHjCHj B.85 CFj CHFj CKjCH ₃ B.66 cf ₃ CHjF CHjCHj B.87 CFj Cl CH ₂ CH 3 B. 88 CFj OCH CHjCHj B.89 CFj OCHjCHj CHjCHj B.90 CFj CN CHjCHj B.91 Cl H CHjCHjCH.

Nr. R ³ R ^s R ^ť B. 14 CH CFj H B.1S CH) chf ₂ The 3.16 CH CHjF H B.17 CK) Cl H B.18 CH OCH The B.19 CH OCHaCHj H B.20 CH CN H B.21 CFj H The B.22 CF) CH H B.23 CFj CHjCHj H B.24 CFj CF) H B.25 CFj CKfj H B.26 CFj CHjF H B.27 CFj Cl H B.28 CFj OCH H D. 29 CFj OCH ₂ TA ₃ H B. 30 CFj CN H B.31 Cl H CH) B.32 Cl CH) CH) 3:33 CL CHjCHj CH) B.34 Cl CF) CH) B.35 CL chf ₂ CH 3:36 Cl CHjF CH B.37 Cl Cl CH B.38 CL OCH) CH, B.39 Cl OCHjCHj CH B.40 Cl CN CH B.41 CH H CH) B.42 CH CH CH B.43 CH CHjCHj CH B. 44 CH CFj CH B.45 CH CHFj CH B. 45 CH cb ₂ f CH B.47 CH Cl CH B.48 CH OCH) CH B. 49 CH OCHjCHj CH B.SO CH) CN CH B.51 CFj H CH B.S2 CFj CH) CH

Nr. Ä ² R® R ^s B.92 Cl CH CHjCHjCHí B.93 Cl CHjCHj CH ₂ CH ₂ CH 3 B.94 Cl CFj CH ₂ CB ₂ CHj B.95 Cl CHFj CHjCHjCHj B. 96 Cl ch ₂ f CH ₂ CK ₂ CH ₃ B.97 Cl Cl CH ₂ CH ₂ CH) B.98 Cl OCH CH ₂ CH ₂ CH 3 B.99 Cl OCHjCH ₃ CH ₂ CH ₂ CH 3 B.100 Cl CN CHjCHjCHj B.101 CH 3 CH ₂ CK ₂ CH ₃ B. 102 CH) CH ch ₂ ch ₂ ch ₃ B.103 CH CHjCKj CHjCHjCHj B.104 CH CF, CH ₂ CH ₂ CH _p - B.105 CH chf ₂ CHjCHjCHj 8106 CH CHjF CHjCHjCHj B. 107 CH Cl CHjCHjCHj B.108 CH, OCH CH ₂ CH ₂ CH ₃ B, 109 ch ₃ OCHjCHj CHjCHjCHj B. 110 CH) CN CH ₂ CH ₂ CH ₃ B. 111 CFj The ch ₂ ck ₂ ch ₃ B.112 CFj CH) CH ₂ CH ₂ CH 3 3.113 CFj CHjCHí CH 3 CH ₂ CH 3 3.114 CPJ CFj CH ₂ CH ₂ CH) B. 115 CFj CHFj ch ₂ ch ₂ ch ₃ B.116 CPJ cr ₂ f 1 H ₂ CH ₂ CH 3 B.117 CFj Cl CHjCHjCHj B. 118 CPJ OCH CHjCHjCHj B.119 CFj OCHjCHj CH ₂ CH ₂ CH ₃ B.120 CFj CH CH ₂ CH ₂ CH ₃ 8.121 cl H CH (CH) j B.122 Cl ch ₃ CH (CH) 1 B. 123 Cl CH ₂ CH) CH _(CH3) j B. 124 Cl CFj CH _(CH3) j 3.125 Cl CHFj ch (ch ₃ ) ₃ B.126 Cl CHjF CH (CH3) ₂ B. 127 CL Cl CH (CH3) 1 3128 Cl OCH CH (CH)) j B. 129 Cl OCH2CH3 CH _(CH3) j B.130 Cl CN CH (CH3) j

Nr. R ^J R ^s R B. 131 CH H CH (CK i) j B. 133 CH CH CH (CH) j B. 133 CH CHjCHj CH (CH) j B. 134 CH CFj CJ (CH) j B. 133 CH CHFj CHĺCHjža B. 13 « CH CHjP CH (CH) j B.137 CH Cl CH (CH) j B.138 CH OCH CH (CH3) j B.139 CH OCHjCHj CH (CH3) j B.140 CH CN CH (CH3) j B. 141 CFj H CH (CH) j B.143 CFj CH CH (CH3) a B. 143 CFj CHjCHj CH (CH) and B. 144 CFj CFj CHlCHjJa B.145 CFj CHFj CH (CH3) a 8.14 ' CFj CHjF CHICH) B. 147 CFj Cl CH (CH3) a B. 145 CRJ OCH caiatjH B.149 CFj OCHjCHj CH (CH3) j B.150 CFj CN CH (CH) and B. 151 Cl H CK ₃ CH = CH 3 9.152 Cl CH CH ₃ CH = CH ₂ B.153 Cl CHjCHj CHjCH-CH B. 154 Cl CFj CHjCHCHj 3155 Cl CHFj CHjCH'CHj B.15 « Cl CHjF CHjCH-CH B.157 Cl Cl C8jCH »CH B.158 Cl. OCH CHjCH-CH B.159 Cl OCHjCHj CK ₃ CK = CKj B.160 Cl CN CHjCH-CH B.161 CH H CHjCH-CH B. 162 CH CH CHjCH-CH B.163 CH CHjCHj CK ₃ CK-CH B.164 CH CFj CHjCH-CH B.165 CH CHFj CH ₃ CH-CH ₃ B.166 CH] CHjF ch ₃ ch = ch ₃ B.167 CH Cl en ₃ ch «ch ₂ B.168 CH OCH CHjCH-CH B.169 CH OCHjCHj CHjCH = CH

Nr. R3 R 5 R ^ť B.2D9 CFj OCKiCHj CH ₂ CH-CH-C1 B.310 CFj CN CH3CH = CH-Cl (trans) B.211 Cl H CHjCCI-CH B.212 Cl CH CHjCCl-CH B.213 Cl CHjCHj CHjCCl «CK i B.214 Cl CFj CHjCCI-CH B.215 Cl CHFj CRjCCl '= CH B.216 Cl CHj P CHjCCICHj B.217 cl Cl CHjCCI ^ Hj B.218 Cl OCH CHjCC1 = CH B.219 CL OCHjCHj CH _and CCl = CH3 B.220 CL CN CHjCCl'CHj B.221 CH H CHjCCl'CHj B.222 CH CH CHjCC1 "CH B.223 ch ₃ CH ₃ CH ₃ CHjCCI-CH B.224 ch ₃ CFj CHjCCl-CH B.225 CH CHFj CHjCCl-CH B.226 CH CHjF CHjCCI-CH B. 227 ch ₃ Cl CHjCC1 = CH B. 229 CH OCH CHjCCI-CH B.229 CH ₃ OCHjCHj CHjCOCHj B. 230 ch ₃ CN CHjCCl'CHj B.231 CFj M CHjCCl'CHj B.232 • CP ₃ CH CHjCC1 = CH B.233 CFj CHjCHj CHjCCl'CHj B.234 cf ₃ cf ₃ CHjCCI-CH B.23S CFj CHFj CHjCCl'CHj B.236 CFj CHjF CHjCCl'CHj B.237 CFj Cl CHjCCl CH _i B.238 cf ₃ OCH CXjCC1 -CH ₂ B.239 cf ₃ OCHjCHj CH ₂ CC 1 "CHj B.240 CFj CN CHjCCICHj 3241 CL The CHjCaCH 3242 CI CH CH _and CCH 3243 Cl CH ₃ CH ₃ CH ₂ C * CH 3,244 CL CFj CHjCeCH B.245 CL CHFj CHjCBCH 3.246 CL CHjF CH2CBCH B.247 CL Cl CHjCbCK

Nr. Rí Rí R ^ť B.170 CH CN CH ₂ CH = CH ₂ B.271 CFj H ch ₂ ch «ch ₂ B.172 C?) CH CHjCH «CH B.173 CPJ CHjCHj CHjCH "CH B.174 CFj CFj CHjCH-CH B.175 CFj CHFj CHjCH-CH B.176 CFj CH ₃ f CHjCH-CH B.177 CFj Cl ch ₂ ch = ch ₃ B.178 CFj OCH CHjCH = CH B.179 CFj OCHjCHj CHjCíf-CMa B.180 CFj CN CHjCK = CH B.181 Cl H CH3CH «CH-C1 (trans) B. 182 Cl CH CH-CH = ct-ci (trans) B.183 Cl CHjCHj CH3CH = CH-C1 (trans) B.194 Cl CFj CH3CH »CH-Cl [trans] B.185 Cl CHFj CH3C = CH-Cl (trans) B.186 Cl CHjF CH3CH = CH-cl (trans) B.187 Cl Cl CH3CH = CH-C1 (trans) B.138 Cl OCH CH3CK-CH-Cl (trans) B. 189 Cl OCHjCHj CH3CH-CH-ci (trans) B.190 Cl CN CH3CH = CH-Cl (trans) B.191 CH H CH ₃ CH CH-C1 (trans) B.192 CH CH CH-CH «CH-Cl (trans) B.193 CH CHaCHj CHjCK CH-Cl (trans) B.194 CH CFj CH3CH = CH-C1 (trans) B.195 CH CHFj CH3CHCH-C1 (trans) B.196 CH CHjF CH 3 CH-CH-Cl (trans) B.197 CH Cl CH3CH-CH-C1 (trans) B.198 CH OCH CHaCH-CH-Cl B.199 CH OCHjCHj CHCHCHCH-Cl (trans) B.200 CH CN CH _and CH = CH-CL (trans) B.201 CFj The CH3CH = CH-Cl (trans) B.203 CFj CH CH 3 CH-CH-Cl (trans) B. 203 CFj CHjCHj CH 3 CH-CH-Cl (trans) B.204 CFj CFj CH 3 CH-CH-Cl (trans) B. 205 CFj CHFj CH _and CH = CH-CL (trans) B.2C6 CFj CHjF CH ₃ CH = CH-Cl (trans) B.207 CFj Cl 2H ₂ = CH-C 1 (trans) B.208 CFj OCH CHiCH »CH-ci (trans)

Nr. R ' R ^s R ⁶ B.248 Cl OCH CHjCeCH B.249 Cl OCHjCHj CHjCBCH B. 250 Cl CN CHjC «CH B.251 ch ₃ H CHjCeCH B.252 CH CH CHjCSCH B.253 CH CHjCHj CHjCaCH B.254 CH CFj CHjC »CH B.255 CH CHFj CHjC »CH B. 256 CH CH1F CHjCäCH B.257 CH Cl CHjCHCH 3258 ch ₃ OCH CHjCSCH B.259 CH OCHjCH ₃ CHjC «CK B.260 CH CN CHjChCM- B.261 CPJ H CHjCbCH B.262 C? J CH ₃ CHjCsCH B.263 CFj CH ₃ CH ₃ CHjCWCH B.264 CFj CFj CHjCBCH B.265 CPJ CHFj CHjCaCH B. 266 CFj CHjF CH ₂ CaCH B.267 CPJ Cl CHjCbCH B. 268 cf ₃ OCH CHjCbCK B.269 CFj OCHjCHj CHjC'CK 3.270 CFj CN CHjCbCK B.271 Cl H CHjCbCCHj B.272 Cl CH CHjCbCCHj B. 273 Cl CHjCHj CHjCbCCHj B.274 Cl CFj CHjCbCCHj B.275 Cl CHFj CHjCbCCHj 3.276 Cl CHjF CHjCbCCHj B.277 Cl Cl CHjCbCCHj B.378 cl OCH CHjCbCCHj B.279 Cl och ₂ ch ₃ CHjCbCCHj B.280 Cl CN CHjCbCCHj 8.281 CH H CHjCbCCHj B.282 ch ₃ CH CHjCbCCHj B.283 CH CHjCHj CHjChCCHs B.284 CH CFj CHjCbCCHj B. 285 CH CHFj CMjC »CCH ₃ B. 286 CH CHjF CHjCbCCHj

Nr. R ³ J- ^RS R 6.28 * 7 CK) Cl CH ₂ CbCCH ₃ B. 288 CH) OCH CKjCbCCHj 5 B. 289 CH, OCHjCHj CHjCeCCH. B.290 CH CN ck ₂ cch. B.291 CFj H CKiCaCCH) B.292 CFj CH CH ₂ CSCCH ₃ 10 6,293 CF, CHjCHj CHjC «CCHj B.294 CF, CFj CHjCeCCHj B.295 CF) CHFj CHjCwCCK) B. 296 CF) CH ₂ F CHjCeCCH) B.297 CF) Cl CH ₂ C · CCH 3 15 B.298 C? ₃ OCH CH ₂ C (CCH) B.299 . CFj OCHjCH. CHjCaCCH. B.300 CF) CN CH ₂ C (CCH) B.301 Cl H CHjCeC-I 20 B. 302 Cl CH ch ₂ c »ci B.303 Cl CHjCHj CHjCSC-I B.304 Cl CFj CHjCeC-I B.305 Cl CHFj CH2CBC-I 25 8,306 Cl CHjF CB ₂ CMC-1 B.307 Cl Cl CH _? CEC I B.308 Cl OCH CHjC «C-I 3309 Cl OCHjCHj CHĺCaC-I B.310 CL CN CHjCRC-I JU B. 311 CH H CHjC «C-I B.312 CH CH cH ₂ CBC-r B.313 CH CHjCHj CH) I-CBC 3,314 CH CFj cH ₃ CBC-r 35 B.315 CK i CHFj CHiCeC-I B.316 CH CH? CHjCac-r B. 317 CH) Cl CHjC »C-I B. 313 CK i OCH CHjCac-I 40 B. 319 CH OCHjCH. cK) C 'c-r B.320 CH CN CH) C 'C-X B.321 CFj H CH) C = C-I ' 8322 CFj CH CK ₂ C · CI 45 B.323 CF) CH ₂ CH 3 : m ₃ ci B.324 CFj CFj : h ₃ csc B.325 CFj CHF) OHjCeC-I

Nr. R ³ R ⁵ Ä ⁶ B.365 Cl CHFj CHjCHj-O-CHjCHj B.366 Cl CHjF CMjCMj-O-CHjCHj B.367 CL Cl CK ₂ CH-O-CH-CH) B.369 Cl OCH) CHjCHj-O-CHjCHj B.369 CL OCHjCHj CHjCHj-O-CHjCH. B.370 Cl CN CHjCHj-O-CHjCHj B.371 CH H CHjCHj-Ο-CHjCHj B.372 CH CH) CH ₂ CH 3 -O-CH 2 CH 3 B.373 CH CHjCHj CH ₂ CH ₃ -O-CH ₃ CH) a.374 CH CFj CHjCHj-O-CHjCHj B.375 CH CHFj CHjCHs-O-CHjCMj B.376 CM) CHjF CH ₂ CH ₂ -O-CH ₃ CH ₃ B.377 CH Cl CH ₂ CH ₂ -O-CH ₃ CH) 0.378 CH OCH) CH ₂ CH 3 -O-CH ₂ CH 3 B.379 CH OCHjCHj CHjCHj-O-CHjCHj B. 380 CH CH CH ₂ CH ₂ -O-CH ₂ CH) B.381 CF) & CHaCHj-O-CHjCH) B. 382 CFj CH CHjCHj-O-CHjCHj B.383 CFj • CHjCHj CHjCKj-O-CKjCK) B.384 C? J CFj CHjCHj-O-CHjCHj 6.385 CFj CHFj CHjCHj-O-CHjCK) B. 386 CFj CHjF CHjCHj-O-CHjCW) B.387 cf ₃ Cl CH ₂ CH ₂ -O-CH ₃ CH ₃ B.388 CF) OCH) CHjCHj-O-CHjCHj B.389 CF) och ₃ ch ₃ CHjCHj-O-CHjCHj 6.390 CFj CN CHjCMj-O-CHjCH. 8.391 Cl H CH-CIHS 6.392 Cl CK i CH-CjHs B.393 Cl CHjCHj CH-CJH. 6394 Cl CFj CK i-CIHS 8.396 Cl CHFj CH-CjHs 6.396 Cl CHjF ch ₂ -c _s h _s 6397 Cl Cl CH 3 -C 11 H _p B.398 Cl OCK) CH-CTHS 3,399 Cl och ₂ ch ₃ CKj-C _€ E ₅ B.400 Cl CN CH-CjHj B.401 CH) H CH 3 -C ₄ H _s B.402 CH) CH CK i-C «H5 B.403 CH) CH ₃ CH ₃ JCH ₂ -c ₆ h _p

Nr. R ¹ RS R B.326 CPJ CHjF CHjCaC-I B.327 CFj Cl CH ₂ C ₈ C-X Β.32Θ CFj OCH) CHjCbC-I B. 329 CFj OCHjCHj CH 3 C S C-I B.330 CFj CN Chico »C-I B.331 Cl H CKÍCHjlCeCH B.332 Cl CH CH (-CB) FEATURES 8333 Cl CHíCHj CH _(CH3) C »CH B.334 Cl CFj CH (CH,) ČSCH B.335 Cl CHFj CH (CH] C 'CH B.336 Cl CKjP TA (CH) j-CH B.337 Cl Cl CH (CH} C 'CH B. 330 Cl OCH CH (CH3) C, CH B.339 CL. OCHjCHj CH (CK i) C * CH B.340 CL CN CH (CH) C 'CH D.341 CH H CH _(CH3) C »CR 6.342 CH CK) CH (CH)) C * TA 0343 CH3 CHjCHj CHICH ₃ ) CBCH B.344 CH CFj CHtCHj) C «CH B.345 CK i CHFj CH _{CH3) CBCB B.346 CH) CHjF CHlCHjJCBCH ».367 CH Cl CH (CH)) C 'TA B.348 CH OCH CH _(CH3) CwCH B.349 CH OCHjCHj CHtCHjJCBCH B. 350 CH CN CH _<CH3) CBCH B.351 CFj H CH {CH} C 'CH B.352 CF, CH) Chicha,) C «CH B.353 CF) CHjCHj CH (CH) C »CH B.354 CF ₃ CFj CH {CH) CbCK B.355 CFj CHFj CMlCHjJCBCH B.356 CFj CHjF CH (CH) CbCK 6.357 CFj Cl CH (CH) C »CK B. 358 CF) OCH) CKÍCHjJCaCH 3.359 CF) och ₂ cK) CH (CH) CBCH B.360 CFj CN CHtCHpCBOJ 6.361 Cl H CHjCHj-O-CTtjCXj B.362 ci CH CH ₂ CH-C-CH ₂ CK B.363 CL CHjCHj CHjCHj-O-CHjClíj B. 364 Cl CF, CH _and CH ₅ -O-CH ₃ CH ₃

Nr. R ¹ RS R B.404 CH CF, CH-CGHS B.405 ch ₃ CHFj cWa-CgH ₅ B.406 CH CHjF CH 1 -C ₆ H _s B.407 CK i Cl CH 3 -C ₆ N _S B.408 CH OCH CH-CfiHs B. 409 CH OCHjCHj CH-CGHS B.410 CK i CN CHU-C5H5 B.411 CFj H CHU-C5H5 B.412 CFj CH CH-CeHj B. 413 CFj CHjCHj CH-CGHS B.414 CFj CFj ch ₂ -c _s h ₅ B.415 CFj CHFj CH 3 -C ₅ H ₅ B. 416 CFj CHjF ch ₂ -c _s h _s - B.417 CFj Cl ch, -c ₆ h ₅ B. 418 CFj OCH CH-CgRj B-419 cf, OCHjCWj CH-CGHS B. 420 CFj CN C «) - C ₅ K _N B.421 .it H cydopropyl B.422 Cl CH cydopropyl B.423 CL CHjCHj cyclopropyl B. 424 Cl CFj qyclopropyl B.425 Cl CHF, cydopropyl B. 426 Cl CHjF cydopropyl B.427 Cl Cl cydopropyl B. 428 Cl OCH cydopropyl B.429 Cl OCHjCHj cydopropyl B.430 Cl CN cydopropyl B.43X CK i H cyclopropyl B.432 CH CH, cyclopropyl B.433 CH, CH ₂ CH 3 cyclopropyl B.434 CH) CFj cydopropyl B.435 CH CHFj cyclopropyl B. 436 CK i CHjF cydopropyl B.437 CH Cl cyclopcopyl B. 438 CH, OCH cyclopropyl B.439 CH OCHjCHj cyclopropyl B.440 CH CN cyclopropyl B.441 CFj N. cyclopropyl B. 442 CFj CH cyclopropyl

Nr. R ³ R 5 R B.443 CFj CHjCHj cyclopropyl B.444 CFj CFj cyclopropyl B.445 CFj chf ₂ cyclopropyl 9446 CFj CHjF cyclopropyl B. 44? CFj Cl cyclopropyl 3.440 CFj OCH cyclopropyl B.449 CFj OCHjCHj cyclopropyl B.450 CFj CN cyclcprcpyl 9.451 CL H CH - (2,2-Cl-cyclopropyl) 9452 CL CH CH 3 - (2,2 -C 1 -cyclopropyl) 9453 Cl CHjCHj CH 2 - <2,2-C 1 -cyclopropyl} 3.4S4 Cl CFj CH 3 - (2,2-C 1 -cyclopropyl) 3.455 CL CHFj CHj- (2,2-Clj-cyclopropyl) B.456 Cl CH? CHj- (2.2-Clj-cyclopropylJ 3457 Cl Cl CHj- (2,2-CIJ-cyclopropyl) B.458 Cl OCH CH 3 - (2,2-C 1 -cyclopropyl) B.459 Cl OCHjCHj CHS (2,2-Clj-cyclopropyl) B.460 Cl CN CH 3 - (2,2-Cl 3 -cyclopropyl) B.461 CH H CH 3 - (2,2-Cl 3 -cyclopropyl) S.462 CH CH, CH3- (2,2-Cl3-cyclopropyl) 9.463 CH CHjCHj CHj- (2,2-Clj-cyclopropyl) 3464 CH CFj CH 2 - (2,2-C 1 -cyclopropyl) B.465 CH CHF; CH3- (2,2-Cl3-cyclopropyl) B. 466 CH CHjF CH 3 - (2,2-C 1 -cyclopropyl) B.467 CH Cl CH 2 - (2,2-C 1 -cyclopropyl) 1 B.468 CH OCH CH 3 - (2,2-C 1 -cyclopropyl) B.469 CH OCHjCHj CH 3 - (2,2-C 1 -cyclopropylpropyl) B.470 CH CN CH3- (2,2-Cl3-cyclopropyl) B.471 CFj H CH 2 - (2,2-C 1 -cyclopropyl) B.472 CFj CH CH3- (2,2-Cl3-cyclopropyl) B.473 CFj CHjCHj CHj- (2,2-Clj-cyclopropyl) B.474 CFj CFj CKj- (2,2-Clj-cycloprcpy 1) B.475 CFj CHFj CH 3 - (2,2-Cl 3 -cyclopropyl) a. 476 CFj CHjF CH 3 - (2,2-Cl 3 -cyclopropyl) B.477 C? J Cl CH 3 - (2,2-C 1 -cyclopropyl) B.478 CFj · OCH CKj- (2,2-Clj-cyclopropyl) B.479 CFj OCHjCHj CH3- (2,2-Cl3-cyclopropyl) B. 480 CFj CN CH 3 - (2,2 -Cl 3 -cyclopropyl) B. 461 X CH H

Nr. R ¹ RS R B.521 CHjCHj CH CH B.522 CHjCHj CHjCHj CH B.523 CH ₃ CH ₃ CFj CH B. 524 CHjCHj Cl CH B.525 CHjCHj OCH CH B.526 CHFj CH CH B.527 chf ₂ CHjCHj CH B.528 CHFj CFj CH B.529 CHFj Cl CH B.530 CHFj OCH CH 8.531 CHjF CH CH B. 532 CHjF CHjCHj CH B. 533 CHjF CFj CH B. 534 CHjF Cl CH B.535 CHjP OCH CH B.536 OCH CH CH B.537 OCH ch ₂ ch ₃ CH B.538 OCH CFj CH B.539 OCH CL CH B.540 OCH CCHj CH B.541 OCHjCHj CH CH 9542 OCHjCHj CHjCHj CH B.543 OCHjCHj CFj CH 3544 OCHjCHj CL CH 3.545 OCHjCHj 'OCHj CH B.546 CN CH CH B.547 CN CHjCHj CH B.548 CN CFj CH B.549 CN Cl CH B.550 CN OCH CH B.551 H CH ch ₂ ch ₃ B.552 H CHjCHj CH _and CH 3 B.553 H CFj CEaCHj B.554 The Cl CHjCHj B.555 H OCH CHjCHj B.556 CHjCHj CH CHjCHj B.557 CHjCHj CHjCHj CH ₃ CH ₃ B. 558 CH ₂ CH 3 CFj CHjCHj B, 559 CHjCHj Cl CHjCHj

Nr. R ^J R ^s R6 B.482 H CHjCHj H B.483 H CFj H S.484 H Cl The 3.48S H OCH H B. 486 CHjCHj CH H B.487 CH2CH3 CHjCHj H B-488 CH ₃ CH ₃ CFj H B.489 CHjCHj CL H B.490 CHjCHj OCH H B.491 CHFj CH The B.432 CHFj CKJCK ₃ H B.493 CHFj CFj The B.494 CHFj Cl H B.495 CHFj OCH H B.496 CH ₂ F CH H B.497 CHjF CHjCHj H B.498 CHjP CFj H B.499 CHjF Cl H B.500 ck ₂ f OCH3 H B.501 OCH CH H B. 502 OCH3 CHjCHj H B.503 OCH CFj H B.504 OCH Cl H B.505 OCH OCH H B.506 OCHjCHj CH, H B.507 OCHjCHj CHjCHj H B.SOB OCHjCHj CFj H B.509 OCH, CH ₃ Cl H B.510 OCHjCHj OCH H B.511 CN CH H B.512 CN CHjCHj H B.513 CN CFj H B.514 CN Cl H B.515 CN OCH H B.516 H CH CH B.517 H CHjCHj CH B.518 H CFj CH B.519 H Cl ch ₃ B.520 H OCH CHj.

Nr. R ³ R ³ r « B.560 CHjCHj OCH CH ₃ CH ₃ B.561 CHFj CH CHjCHj B.562 CHFj CHjCHj CHjCHj B.563 CHFj CFj CHjCHj B.554 CHFj . Cl CHjCHj B.565 CHFj OCH CHjCHj B.566 CHjF CH CHjCHj B. 567 CHjP CHjCHj CH ₃ CH ₃ B.568 CHjF CFj CHjCHj B. 569 CHjF Cl CHjCHj B.570 CHjF OCH CHjCHj B.571 OCH ch ₃ CHjCHj B.572 OCH CHjCHj CHjCHj .. B.573 OCH CFj CHjCHj B.574 OCH Cl CHjCHj B.575 OCH OCH CHjCHj B.576 OCHjCHj CH CHjCHj B.577 OCHjCH ₃ CHjCHj CH ₃ CH ₃ B.578 OCHjCHj CFj CHjCHj B.579 OCHjCHj Cl CHjCHj B. 580 OCHjCHj OCH CHjCHj B.581 CN ch ₃ ch ₂ ch ₃ B. 582 CN CHjCHj CHjCHj B.583 CN cf ₃ CHjCHj B.584 CN Cl CHjCHj B.5B5 CN OCH CKjCK ₃ B.536 H ch ₃ CHjCHjCHj B.587 H CH ₃ CH ₃ CH ₃ CH ₃ CH ₃ B.598 H cf ₃ CHjCHjCHj B.589 H Cl CHjCHjCHj B.590 H OCH CHjCKjCNj B.591 CHjCHj CH CHjCHjCHj B.592 CHjCHj CHjCHj CH ₃ CH ₃ CH ₃ B.593 CHjCHj CPJ CHjCHjCHj B. 594 CHjCHj Cl CHjCHjCHj B. 595 CHjCHj OCH CH ₃ CH ₃ CH ₃ B. 596 CHFj CH CHjCHjCHj B.597 CHFj CHjCHj CHjCHjCHj B. 598 CrJFj CFj CHjCHjCHj

Nr. X » R ⁵ R ^e B.599 CHFj Cl CKjCHjCKj B. 600 CHFj OCH ₃ CHjCKjCHj B. 601 CH ₂ F CH CH ₂ CH ₂ CH 3 B.602 CHjF CH ₂ CK} CHjCK ₂ CHj B.603 CHj F CF, CHjCHjCHj B. 604 Chifa Cl CH ₂ CH ₃ CH ₃ B.605 CHjF OCH} CHjCHjCHj B.606 OCH CH CHjCHjCHj B. 607 OCH CH ₂ CH 3 CHjCHjCHj B.608 OCH CFj CHjCHjCHj B.609 OCH) Cl CHjCHjCHj B.610 OCH} OCH CHjCHjCHj B.611 ocwjcwj CH CHjCHjCHj B.612 OCHjCHj CHjCHj CHjCHjCHj B. 613 OCHjCHj CP, CHjCHjCHj B. 614 OCHjCHj Cl CHjCHjCHj B.615 OCHjCHj OCH) CHjCHjCHj B.516 CN CH CHjCHjCHj B. 617 CN CHjCHj CHjCK ₂ CHj B.618 CN CFj CHjCKiCHj B. 619 CN Cl CHjCHjCHj B.620 CN OCH) CHjCHjCHj B.621 H CH CH (CHj jj B.622 The CHjCHj CH (CH3) j B. 523 The CFj CH (CH 2 i j B.624 H ci CH _(CH3) j B. 625 H OCKj CH (CH3) j B.626 CN ₂ CHj CH CH (CH3) j B. 627 CKjCHj CHjCHj CH (CH3) j B.628 CHjCHj CFj CH (CH3) j B. 629 CKjCBj Cl CH (CH3) i B.630 CHjCHj OCH CH (CH3) i B. 631 CHFj CH) CS (CH3) ₂ B.632 chf ₂ CHjCHj CH (CH ₂ ) ₂ B.633 CHFj CFj CBlCHjjj H.6M CHFj Cl CH (CH3) ₂ 3,635 CHFj OCH) CH (CH3) 1 B.636 CH _and F CH CH (CK ₃ ) j 6637 CH ₂ F CH ₂ CH 3 CH (CH) j

Nr. R ³ RS R ^ť B.677 OCH) CHjCHj CHjCH-CH B.678 OCH CP) CHjCH = CH B. 679 OCH) Cl CH ₂ CH = CH 3 B. 680 OCH OCH CH ₂ CH = CH 3 B.681 OCHjCHj CRJ CH ₂ CH = CH 3 6682 OCHjCHj CHjCHj CHjCH'CHj B. 683 OCHjCHj CPJ CHjCH-CH B. 684 OCHjCHj Cl CHjCH'CHj B. 685 OCHjCH) OCH CHjCH = CH B.686 CN CH CHjCH-CH B.687 CN ch ₂ ch ₃ CH ₃ CH = CH ₂ 6688 CN CF) CH ₂ CH CH 2 8689 CN Cl CHjCH-CH, 6.690 CN OCH) CHjCH <Hj B.691 H CH CH3CH = CH-ci (trans) B.692 H CHjCHj CH 3 CH-CH-Cl (trans) 6.693 H CFj CH 3 -C 1 -CK-d (trans) 6.694 H Cl CH3CH = CH-Cl (trans) 6.695 H OCH CH3CH «CH-C1 (trans) 6.696 CHsCNj CH CHjCH’CHi (trans) 8.697 CHjCHj CHjCHj CHjCH’CH-cl (trans) 6698 CHjCHj CFj CH3CH = CH-ci (trans) 6.699 CHjCHj Cl CH 3 CH-CH-Cl (trans) B.700 CHjCHj OCH) CH 3 CH-CH-Cl (trans) B.701 CHFj CH CKiCH = CKi (trans) 6702 CHF) CHjCHj CH3CH = CH-Cl (trans) S.703 CHF) CPJ CH3CH = CH-C1 (trans) B.704 CHFj Cl CH3CH = CH-Cl (trans) B.705 CHFj OCH CH 3 CH 2 CH-Cl (trans) B.706 CHjF CH CH3CH = CH-Cl (trans) B.707 ch ₂ f CHjCHj CH3CH = CH-Cl (trans) B. 708 CHjF CFj CH3CH = CH.C1 (trans) B 709 CHjF Cl CH 3 CH-CH-Cl (trans) B.71D CHjF OCR) CH3CH »CH-Cl (trans) B.711 OCH CH CH ₃ CH * CH-C 1 (trans) B.712 OCH CH ₂ CH 3 CH) CH * CH-C (trans) B.713 OCH CFj 1K _with CH = CK-Cl (trans) 6714 OCH Cl CH 3 CH-CH-Cl (trans) B.715 OCH) OCH ÍKjCK’CH-Cl (trans)

Nr. R ³ rs R ^e B. 638 CHjF CF) CH (CH3) j B.639 CH ₂ F Cl CH ₃ H ₃ B.640 CHjF OCKj ch (cH) ₁₂ B.541 OCH CH CHtCHjíj B.642 OCH CHjCH) CH (CH) j 3643 DCJíj C? J CH (CH)) j B.644 OCH Cl CH (CH3) i 3645 OCH OCH CH (CH) j B.646 OCHjCHj CH CR (CH) j 3.64? OCHjCHj CHjCH) CH (CH)) j 3648 OCX ₂ CHj CFj CH (CH3) j B.649 OCH ₂ CHj Cl CH _(CH3) j B.650 OCHjCHj OCH CH (CH)) ». B. 651 CN CH CH (CH) j B.652 CN CHjCHj CH (CH) j B.653 CN C?) CH (CH3) ₂ B. 654 CN ci CH (CH3) j B.655 CN OCH) CH (CH) j B.656 H CH) CHjCH = CH B.657 H CHjCHj CH) CH ₂ CH ₂ B.658 H CFj CHjCReCHa B. 659 H Cl CHjCH-CH B.660 The OCH CH) ₂ CH-CH B.661 CHjCHj CH CHjCHjCHj B.662 CHjCH) CHjCHj C ₅ H ₂ CH ₂ CH 2 B. 663 CHjCHj CFJ CHjCH = CH B.664 CH ₂ CH 3 ci CH ₂ CH-CH ₂ B.665 CHjCHj OCH CHjCH = CH B.666 CHFj CH CHjCM-CH B. 661 CHFj CHjCHj CHjCH-CH B.668 CHFj CFj CHjCK CK i = B.669 CHFj Cl CHjCH-CH 0.Í7O CHFj OCH CHJCHJCHJ B.671 CHjF CH ch ₂ ch = cw ₂ 3672 CH) F CWjCHj ch ₂ ch-ch ₂ B.673 CHjF CF} CHjCH-CH B. 671 ch ₂ f Cl CHjCHjCHj B.675 CHjF OCH) CH3CH-CH2 | B. 676 OCH CH CH ₂ CH = CK i

Nr. R ³ RS R ^£ 8715 OCHjCHj CH CH ₂ CH = CH-C 1 (trans) B.717 OCHjCHj CHjCHj CH3CH = CH-Cl (trans) B.718 OCHjCHj CF) CH 3 CH-CK-ci (trans) B.719 OCHjCHj Cl CKjCH = CH-Cl (trans) B.720 OCHjCHj OCK) CHjCH’CK-C2 (trans) B, 721 CN CH CN ₂ CH = CH-C (trans) B.722 CN CHjCHj CH3CW = CK-Cl (trans) B.723 CN CFj CHiCH ”CH-ci (trans) B.724 CN cl CH3CH = CH-Cl (trans) B.725 CN OCH CH _and CH = CH-Cl (trans) B.726 H CH CHjCCl-CH B.727 The CHjCHj CHjCCl-CH B.728 H CFj CHjCCl-CH B.729 H Cl CHjCC1 »CH B.730 H OCKj CH ₅ CC 1 -CH ₂ B, 731 CHjCH) CH CHjCC1 = CH B.732 CHjCH] CHjCHj CH ₃ Cl ₂ = CH ₂ B. 733 CHjCHj CFj CH ₃ CCL = CH ₂ B.734 CHjCHj Cl CHjCCl = CH B.735 CHjCHj OCH CHjCCL-Chi B.736 chf ₂ CH CHjCCl = CH B.737 CHFj CHjCHj CH ₃ Cl ₂ = CH ₂ B.738 CHFj CFj CHjCCI'CHj B.739 CHFj Cl CHjCC1 = CH B.740 CHFj OCH) CH ₂ CC 1 CB ₂ B.741 CHjF CH CHjCďCHj B.742 CHjF CH ₂ CKj ch ₂ cci-ch ₂ B.743 CHjF CF) CHjCCL = CH B. 744 CHjF Cl CHjCďCHj B.745 ch ₂ f OCH) CHjCC1 = CH B.746 OCH CH CHjCCľCHj B.747 OCH CHjCHj CH ₂ CC 1 CB ₂ B.748 OCH CFj CHjCCl'CHj H.749 OCH Cl CH ₂ CC 1 CH ₂ B.750 OCH OCH CH ₂ CC1 »€ H ₂ E.751 OCHjCHj CH CHjCC1 = CH B.752 OCHjCHj CHjCHj CH ₂ CC 1 "CHj B.753 OCHjCH} CPJ CHjCC1 CK i = B.754 OCHjCHj Cl CHjCC1 = CH

Nr. R ³ R ⁵ R B.755 OCHjCHj OCH CMjCCl-CK i 3,756 CN CH CHjCC1 = CH 3757 feeling CHjCHj CHjCC1 = CH 3758 CN CFj CH ₂ CC 1 = CH 3 B.759 CN Cl CHjCC1 «CH B. 760 CN OCH CH _t CCl'Ctti B.761 H CH CHjCaCH B. 762 H CHjCHj CHjCsCH B.763 The CFj CHjC®CK B.764 The Cl CHjC «CH B.765 B OCH CHjC «CH B.766 CHjCHj CH CKjCeCK B.767 CHjCHj CHjCHj CHjCBCH B.768 CHjCHj CFj CHjCaCH B.769 CHjCHj Cl CKjCaCK B.770 CHjCHj OCH CH _and C «CH B.771 CHFj CH CHjC »CH B.772 CHFj CHjCHj CHjCsCH B.773 CHFj CFj CKjCCH B.774 CKF2 Cl Cejc B.775 CHFj OCH CKjCBCK B.77 « CHjF CH CHjCsCH B.777 CHjF CHjCHj CHjCaCH B.778 CHjF CFj CHjCECK B.779 CRjP Cl CHjCaCH B.780 CKjF OCH CHjCCH B.781 OCH CH CKjC «CK B. 783 OCHj · CHjCHj CHjC «CH B.783 och ₃ CFj CH _S C CH B.784 OCH Cl CHjCsCH B.78S □ CH OCH CR 3 C = CH B.786 OCHjCHj CH CR3C> CR B.787 OCHjCHj CHjCHj CHjCaCH B.788 OCHjCHj CFj CHjCbCK B.789 OCHjCHj Cl CKjCBCH B.790 OCHjCHj OCH CRjCeCH B.791 CN CH CHjCaCH B.792 CN CHjCHj CHjCeCH B.793 CN CFj CHjCaCH

Nr. R ³ R ⁵ R ^ť B.832 H CHjCHj ch ₂ cbc-i B.833 H CFj CHjCaC-I B.834 H Cl _CH2 C "C B.835 OCH CHjCmC-I B. 636 CH ₂ CK ₃ CH CH ₂ CaCl ₂ B.837 CHjCHj CHjCHj CHjC »C-I B.838 CHjCHj CFj ch ₂ cbc-i B. 839 CX ₂ CHj Cl CHjCaC-I B.840 CHjCHj OCKj CHsCaC-I B.841 CHFj CH CRjCaC-r B. 842 CHFj CKjCHj CHjCaC-I B.843 CHFj CFj CHjCaC-I B.844 CHFj Cl CRjCaC-I B.845 CHFj OCH CHjCeC-I B.846 CHjF CH CKjCC-I B.847 CHjF CHjCHj cb ₂ c «ci B.846 CHjF CFj CKjCbC-T 9849 CHjF Cl CRjC «C-I B.850 CHjF OCH CHjCaC-I B.851 OCH CH CHjCBC-I B.852 OCH CHjCHj CHjCeC-l 3,853 OCH CFj CHjCeC-J B.854 OCH cl CHjC «C-I B.855 OCH OCH CHjCeC-I B.856 OCHjCHj CH CHjCC-I B. 857 OCHjCHj CHjCHj CMjC «C-I B.858 OCHjCHj CFj CHjC «C-I B. 859 OCHjCHj Cl CHjCwC-I B.860 OCHjCHj OCH CRjCC-I B.861 CN CH CRjCaC-I 8.862 CK CHjCHj CHjCBC-I B.663 CN CFj CHjCaC-I 3. 864 and Cl CHjCaC-I B. 865 CN OCKj CHjCaC-X B. 866 H CH CH (CH) CaCl B.867 H CHjCHj TA (CH) ČKCH B.868 H CFj CHlCHjlCaCH B. 869 H Cl CHťCHjJCeCH B. 870 H OCH CHÍCHjICsCH

Nr. B ¹ RS R ^s B. 794 CN Cl CH ₂ C «H 5 B.795 CN OCH CH ₂ CMCH B.796 H CH CHjCWCCHj B.797 H CHjCHj CHjC »CCHj B.798 H CFj CKjCaCCHj 10 B.799 H Cl CHjCaCCKj B.800 H OCH CHjC »CCHj B.801 CHjCHj CH CHjCMCCSj B.802 CHjCHj CHjCHj CHjC »CCHj B. 803 CHjCHj CFj CHjCwCCHj 15 B.604 OJjCHj Cl CHjCaCCHj B.805 CHjCHj OCH CHjCacCHj B.806 CHFj CH CHjCSCCHj 3837 CHFj CHjCHj CHjCaCCHj 20 B.808 CHFj CFj CR ₂ CaCCH 3 B.839 chf ₂ Cl CHjC «CCHj B.320 aid laik OCH CHjCSCCHj B.811. CH ₂ F CH CHjCaCCHj 25 B. 612 CHjF CHjCHj CHjC «CCKj B.813 CHjF CFj CHjCSCCHj B.814 CHjF Cl CHjCacCHj B.815 CHjF OCH CHjCacCHj 30 B. 81 « OCH CH CHjCBCCHj B.817 OCH CH2CH3 CHjC «CCHj B.818 OCH CFj CH ₂ C = CCH 3 B.81 $ OCH Cl CHjCacCHj B.820 OCH OCH CHjCacCHj 35 B. 821 OCKjCKj CH CCK-CHjC] B.822 OCHjCHj CHjCHj CHjCaCCKj 3,823 OCHjCHj CFj CHjCacCHj B. 824 OCHjCHj Cl CHjCaCOfj 40 B. 825 OCHjCHj OCH CHjCaCCHj B. 826 CN CH CHjCSCCHj B. 827 CN CH ₂ CH 3 CH ₂ C ₅ CH ₃ B. 928 CN CFj CHjCSCCHj B.829 CN Cl ZHjCiCCHj B. 830 CN OCH CHjC »CCHj B.831 H CH 3 is CH 3 C-I

Nr. R ³ R R ' B.671 CHjCHj CH CH [CH) CISCH B.872 CHjCHj CHjCHj CH (CHi) CaC i B.873 CHjCHj CFj CHĺCHjJCaCH B.874 CHjCHj Cl CH (CH) C »CH 3,875 CHjCHj OCKj CH (CH) C-CH B.876 CHFj CH CHCCMjiCaCH B.877 CHFj CHjCHj CH (CWJ) CaCl 3878 CHFj CFj CH (CRJ) CaCl B. 879 CHFj Cl CH (CH) CaCl B. 880 chf ₂ OCH CH (CH) CSCH B.881 CHjF CH CH (CH) CBCH B.882 CHjF CHjCHj CHĺCKjICaCH B. 893 CHjF CFj CKlCHjíQaCH B.8B4 CHjF Cl CH (CH) CwCH B.885 CHjF OCH CH (CH]) C-CH B. 886 OCH CH CH (CK i) CaCl B.887 Ooops! CHjCHj CH (CMj) CsCH B.888 OCH CFj CH | C3J) CHCH 3.989 OCH Cl CH (CH3) CaCH B.390 OCH OCH CKÍCHjJCwCH B. 891 OCHjCHj CH CHÍCHjlCaCH 3,992 OCHjCHj CHjCHj CatCHjJCwCH 3893 OCHjCHj CFj CHICKjICbCK B.6Í4 OCHjCHj Cl CHlCHjlCaCH B.895 OCHjCHj OCH CB [CH3CaCH B.896 CN CH CH (CH) CaCl B.897 CN CHjCHj CHlCHjíCeCH B.899 CN CFj CHlCHjlCwCH B. 899 CN Cl CHtCHjíCaCK B. 900 CM OCH CHlCHjICaCH B, 901 H CH CKjCHj-O'CHjCHj B.902 H CHjCHj CHjCHj-O-CHjCHj 3.903 H CFj CHjCHj-Ο- · CHjCHj B.904 H CL CH3CH3-Q ~ CH3CH3 B.905 H OCH CHjCHjO-CHjCHj B.9Q6 CHjCHj CH CHjCHj-Q-CKjCHj 3907 CHjCHj CHjCHj CHjCHj-C-CKíCHj 3.908 CHjCHj CFj CHjCHj-O-CHjCHj B.909 CHjCHj Cl CBjCHj-O-CHjCHj

Nr. R ' R ^s R B. 910 CHjCHj OCH CH ₂ CH ₂ -O-CH ₂ CH 3 B.911 CHFj CH? CH ₂ CH ₃ -O-CH ₂ CH ₃ B.912 CHF2 CH ₃ CH ₃ CH2CH2-O-CH2CH3 B.913 CHFj CPJ CH ₂ CH ₂ -O-CH ₂ CH 3 B, 914 CHFj Cl CHjCHj-O-CKjCHj B.915 CHFj ockj CHjCHj-O-CHjCHj B.916 CHjF CH CHjCKj-O-CHjCHj B, 917 CHjF CHjCHj CHjCHj-Q-CHjCííj B.918 CHjF CFj CHjCHj-O-CHjCHj B.919 CHjF Cl chjchj-o-chjcH) B.920 CHjF OCH) CH2CH2-O-CHJCH3 B. 921 OCH ch ₃ CHJCHJ-O-CHJCH) B.922 CCH ₃ ch ₂ ch ₃ CH ₃ CH ₂ -O-CH ₂ CH ₃ B.923 OCH CFj CHjCHj-Q-QHjCKj B.924 OCH Cl CH ₂ CH ₂ -O-CH ₃ CH ₃ B.925 OCH OCH CH ₃ CH ₃ -O-CN ₃ CH ₃ B.925 OCHjCHj CH CHjCHj-O-CHjCHj B. 321 OCHjCHj CHjCHj CH ₂ CH 3 -O-CH 2 CH 3 B.92S OCHjCHj CFj CHjCHj-O-CHaCHj B.929 OCH2CH3 Cl CH ₂ CH ₂ -O-CH ₃ CH ₃ B.930 □ CHjCHj OCK3 CH2CH2-O-CH2CH3 B. 931 CN CH CHJCHJ-O-CH2CH3 B.932 CN CHjCHj CH ₂ CH ₃ -O-CH ₂ CH ₃ B.933 CN CFj CHjCHj-O-CHICHE) B.934 CN Cl CH ₂ CH ₃ -O-CH ₃ CH ₃ B.935 CN OCH) CHjCHj-Q-CHjCHj B. 93 « H CH3 CH-cghj B.917 H CHjCHj CH ₂ -C ₅ Hj B.938 H CFj CKI-Ph B.939 H Cl CH-CGHS B.940 H OCH CHL-CGHS B.941 CHjCHj CH CH-cghj B.942 CHjCHj CH2CH3 CH2-C _with H5 B.943 CHjCHj CFj CH-Ph B. 944 CHjCHj Cl CH ₂ -C _{5 TH} B. 945 CKjCH) OCH CH ₂ -C ₈ H ₅ B.946 CHFj CH ch ₃ -c «h _p B. 947 chf ₂ CH2CH3 CH-CjHj B.548 chf ₂ CFj ch ₂ -c _s k _s

Nr. R ³ R ^s R ' B.988 CHjF CFj cyclopropyl B. 989 CH ₂ F Cl cyclopropyl B.990 ch ₂ ? OCH cyclopropyl B.991 OCH CH cyclopropyl B.992 OCH CHjCHj cyclopropyl B.993 OCH CPJ cyclopropyl B.994 OCH; Cl cyclopropyl B.99S OCH OCH cyclopropyl B. .99 6 OCKjCHj CH cyclopropyl B.997 OCHjCHj CHjCH) cyclopropyl B.998 OCHjCHj CFj cyclopropyl B.989 OCHjCHj Cl cyclopropyl a.1003 OCHjCHj OCH cyclopropyl 3.1001 CN CH cyclopropyl 3.1002 CN CHjCHj cyclopropyl 3.1003 CN CFj cyclopropyl B.1004 CN Cl cyclopropyl B.1005 CN OCH cyclopropyl 9.1006 11 CH CHj- (2,2-LJ-cyclopropyi) 3.1007 H CHjCHj CH3- (2,2-Cl3-cyolopropyl) 3,100 H CFj CHj- (2,2-Clj-cyclopropyl) 3.1069 M Cl CHj- (2,2-Cl ₂ -cycloprDpyl) 3.1010 H OCH CH 3 - (2/2-Cl 3 -cyclopropyl) 3.1011 CHjCHj CH CH3- (2,2-di-cyclopropyl) 3.1012 CHjCHj CHjCHj CH ₂ - (2,2-CLJ-cyclopropyl) 9.1013 CHjCHj CFj CH3- [2,2-Cl3-cyclopropyl] B.1014 CHjCHj Cl CHj- (2,2-Clj-cyelopropyl) 8.1015 CMjCH ₃ OCH CH ₃ - (2,2-cl ₃ -cyclopropyl) í.1016 CHF) CH) CH3- (2,2-Cl3-cyclopropyl) B.1017 CHFj CHjCHj CH 2 - (2,2-C 1 -cyclopropyl) B.1018 CHFj CFj CH 3 - (2,2-Cl 3 -cyclopropyl) 8.1019 CHFj cl CH 3 - (2,2-Cl 3 -cyclopropyl) 3.1020 CHFj OCH CH ₂ - (2,2-Cl 1 -cyclopropyl) B.1021 CHjF CH CH ₂ - (2,2-Clj-cyclopropyl) B.1022 CHjF CHjCHj CH3- (2,2-C1-cyelopropyl) 3.1023 CHjF CFj CH 2 - (2,2-C 1 -cycloptapyl) B.1024 CHjF Cl CH3- (2,2-di-cyclopropyl) 3.1025 CHjF OCH CH3- (2,2-Cl3-cyclopropyl) 8.1026 QCft3 CH CH 3 -12,2-C 1 -cyclopropyl)

Nr. R ' R ⁵ R B.949 CHFj Cl CH-cghj B.950 CHF) OCH ch ₂ -c «h $ 5 B.951 CHjF CH CH-CjHj B.952 CH? CHjCHj CH 3 -C 11 H _p B.953 CHjF CFj CMJ-cghj B.954 CHjF Cl CH ₂ -CiWi 10 B.955 CHjF OCH Chi-CgJJs B.956 OCH CK i CIÍj-CjHj B.957 OCH CHjCHj CH-CGH. B.958 OCH CFj _CH3 * $ CGH B.959 OCH Cl CH-cghj 15 B. 960 OCH OCH CH-CgBg B.961 OCHjCHj CK ₃ CH-CgHj- B. »62 OCHjCHj CH ₂ CH 3 CH-CGHS B.963 OCHjCHj CFj CH-cghj 20 B.964 OCHjCHj Cl CH 3 -C ₁₁ H _s B.965 OCHjCHj OCH CH2-CGH ₅ B.966 CH CH CH-CgHg B.967 CN ch ₂ ch ₃ CH-cghj 25 B.968 CN CFj CH-cghj B.969 CN Cl CH-CíHj B.970 CN OCH CH-CIHS B.971 H CH cyclopropyl 30 B.972 H ch ₂ ch ₃ cyclopropyl B.973 The CFj cyclopropyl B.974 H Cl cyclopropyl B.975 H OCH cyclopropyl B.976 CHjCHj CH cyclopropyl 35 B.977 CHjCHj CHjCHj cyclopropyl B.978 CHjCHj CFj cyclopropyl B.979 CHjCHj Cl cyclopropyl B. 980 CHjCHj OCH cyclopropyl 40 B.981 CHF) CH eyclopropyl B.982 CHF) CHjCHj cyclopropyl B.983 CHFj CFj cyclopropyl B. 984 CHFj Cl cyclopropyl 45 B. 983 CHFj OCH cyclopropyl B.98 « CHjF CH cyclopropyl B.9Í7 CHj F ch ₂ ch ₃ cyclopropyl

Nr. R ³ R ^s R ^s B.102 OCH CHjCHj CH3- (2,2-clj-cyclopropyl) 9.102 OCH CF) CH3- (2,2-Cl3-eycloprepyl) 5 8.1029 OCH Cl CH 3 - (2,2-Cl 3 -cyclopropyl) 8.1O3C OCH) OCH) CH3- (2,2-C1-cyelopropyl) 8.1031 OCHjCHj CH CH 2 - (2,2-C 1 -cyclopropyl) 3.1032 OCHjCHj CHjCHj CH 3 - (2,2 -Cl 3 -cyclopropyl) 10 8.1033 OCH ₂ CHj CFj CH3- (2,2-Cl3-cyclopropyl) 3.1034 OCHjCHj Cl CH 3 - (2,2-C 1 -cyclopropyl) 8.1035 OCHjCHj OCH) CH3- (2,2-C1-cyelopropyl) 3.1036 CN CH CH3- (2,2-Clg-cyclopropyl) 15 3.1037 CN CHjCHj CH 3 - (2,2-C 1 -cyclopropyl) B.1038 CH CPJ CH2 - (2,2-C1-cyclopropyl) | B.1039 CN Cl CHj- (2,8-Clj-cyclopropyl) B.1040 CN OCH CH3- (2,2-CL-cyclopropyl) 3.1041 Cl CHjCec-Cl 20 9.1042 Cl CH CH _and C »C-Cl B.1C43 Cl CHjCHj CHjCeC-Cl 9.1044 .it CFj CHjCeC-Cl 3.1045 Cl CHFj CHjľ 'C-Cl 25 B. 104 « Cl CH? CHjC 'C-Cl B.1047 Cl Cl CRjCeC-Cl B.1046 Cl OCH CHjCBC-Cl B.1049 Cl OCHjCHj CHjCeC-Cl 9.1050 Cl CN CHjCWC-Cl 30 B.1051 CH, H CHjC 'C-Cl B.1052 CH CH CH 3 C = C-Cl 3.1053 CH) CHjCHj CHjC »C-Cl .1054 CH CFj CHjCeC-Cl 35 .1055 CH) CHFj CHjCWC-Cl .1056 CH CH? CH ₂ C «C-C1 .1057 CH Cl CHjC 'C-Cl .1058 CH OCH) CHjCeC-Cl 40 .1059 CH OCHjCHj CHjCeC-Cl -10S0 CH CS CHjC 'C-Cl .1061 C F) H CHjCaC-Cl .1062 CFj CH) CHjCBC-Cl 45 .1063 CFj CHjCHj CfíjCBC-Cl .1064 CFj CFJ CHjC »C ~ CL .1065 CFj CHFj ZHjC'C-Cl

Nr. »1 RS R ' B.1066 CFj CHjF CHjCaC-Cl B.1067 CFj Cl CHjC 'C-Cl B.1068 CFj OCH cji ₃ cec-ci B.1069 CFj OCHjCHj CHjCaC-Cl B, 1070 CFj CN CHjCC-Cl B.1071 The CHU CBjCeC-Cl 9.1072 H CHjCHj CHjCaC-Cl B.1073 The CFi CHjCaC-Cl B.1074 H Cl CHjCaC-Cl B.1075 The OCH3 _CBC-CH3 C1 B.1076 CHjCHj CH CHjC 'C-C1 B.1077 CHjCKj CHjCHj CMjC 'C-C1 B.1078 CHjCHj CPJ ch ₃ c = c-c_ B.1079 CHjCHj Cl CHjCaC-Cl 3.1080 CHjCHj OCH CH _q CaC-Cl 3.1091 CHFj CH, CB-C 1 -C ₃ CHC 3.1032 CHFj CHjCHj CH _S C «C-C1 3.1083 CHFj CFj CHjCaC-Cl 3.1084 CHFj Cl CHjC 'C-Cl 3.1095 CHFj OCH CHjCaC-Cl 3.1086 CH _and P CH CHjCBC-Cl 9.1037 CH ₂ F CHjCHj _CH2 C.tbd.C-C1 B.10BB ch ₂ f CFj CHjCaC-Cl 9.1089 CHjF Cl CMjCbC-Cl 9.1090 CHjF OCH CHjCaC-Cl B.1091 OCH ₃ CH, Chace »C-Cl B.1092 OCH CHjCHj CHjCaC-Cl B.1093 OCH CFj CHacec Chi B.1094 OCH Cl CHjC 'C-Cl B.1095 OCH OCH CHjCaC-Cl B.1096 OCHjCHj CH CK ₂ C «C-C1 B.1097 OCHjCHj CHjCHj CH 2 'C-C1 B.1098 OCHjCHj CFj CHjCaC-Cl B.1099 OCHjCHj Cl CH ₂ C «C-C1 B.1100 OCHjCHj OCH CHjCBC-Cl B.1101 CN CH, CH 2 'C-C1 B.1102 CN CHjCHj CHjCaC-Cl B.1103 CN CFj CHjCeC-Cl B.1104 CN Cl CHjCsC-Cl

Nr. R3 R ⁵ R < B.1144 CHjCHj Cl _CHjCaC-3 CKjCH B.1145 CHjCHj OCH; CHjCaC-CHjCHj B. 1146 CHFj CH CHjCaC-CHjCHj B.1147 CHFj CHjCHj CHjC 'C-CH ₂ Ca B.1148 CHFj CFj CHjCaC-CHjCHj B.1149 CHFj Cl CHíChc-CHjCH) B.1150 CHFj OCH CH ₂ Cec-CH ₃ CH ₃ B.1151 CHjF CH CHjCaC-CHjCHj 8.1152 CH? CHjCHj CHjCaC-CHjCHj 8.1153 ch ₂ f CFj CH ₂ C «-CHjCHCH B.1154 CHjF Cl CH ₂ Cl ₂ -CH ₃ CH ₃ B.1155 ch ₂ ? OCH) CHjCeC-CHaCXj B.1156 OCH CH CKjCaC-CKjCHj 3.1157 OCH CHjCHj CK ₂ C «CH -CHj 3.1158 OCH CFj CHjC «C-CHjCHj 3.1159 OCH Cl CHjC «C-CHjCHj 3.1160 OCH OCH CWiCeC-CHjCNj 3.1161 OCHjCHj CK i CHjCaC-CHiClíj 9.1162 OCHjCHj CHjCHj CHjCaC-CHjCHj 9.1163 OCHjCHj CFj CHjCaC-CHjCHj 9.1164 OCHjCHj Cl CH3C8C-CXjCK ₃ 9.1165 OCHjCHj OCH) CHjCBC-CHjCHj 3.1166 CM CH CKjCeC-CífaCKj B.1167 CN CHjCHj CXjCaC-CKyCHj 9.1168 CN CFj CHjCaC-CHjCHj B.1169 CN Cl CHjC-C-CHjCHj 3.1170 CN OCH CHjCaC-CHjCHj B.1171 Cl H CHjCC-CFj B.1172 Cl CH CHjC »C-CFj B.1173 Cl CHjCHj CHíCsC-CFj B.1174 Cl CFj CHjCSC-CFj 3.1175 Cl CHFj CHjC «C-CFj 3.1176 cl CHjF CHjCbc-CFj S.1177 Cl Cl CH ₂ Cbc-CF 3 3.1178 Cl OCH) CHjCaC-CFj B. 1179 Cl CCHjCHj CHjCaC-CFj B. 1180 Cl CH CHjC «C-CFj B.1181 CK, H CHjCaC-CPJ B.1182 CH CH CH _and CC-CF 3

Nr. £ 3 R ⁵ R B.110 CN OCH CHjCeC-Cl B.110 Cl H CH 3 C-CH 3 CH 3 B.1101 Cl CH CHjCbC-CHjCHj B.1106 Cl CHjCHj CHjC «C-CHjCKj B.1109 Cl CFj CH ₃ C ₃ CH ₃ cm ₃ B.1110 Cl CHFj CH ₃ C «-CHjCHCH B.1111 Cl CHjF CHjCaC-CHjCHj 3.1.112 Cl Cl CHjCeC-CHjCHj B.1113 Cl OCH CHjCaC-CHjCHj B.1114 Cl OCHjCHj CHjCaC-CHjCHj B.1115 Cl CN CHjCec-CTjCHj B.1116 CH H CKjC äSC-CH 3 CH 3 8.1117 CH, CH CH C _S C-GHjCHj B.1118 CH CHjCHj CHjCsC-CHjCHj B.111 » CH CFj CHjCaC-CHjCKj 3.1120 CH CHFj CH ₂ Ce-CK ₃ CH ₃ B.1121 CH CHjF CHjC «C-CHjCHj B.1122 CH Cl CH ₂ CC-CH ₃ CN B.1123 CH OCH CHjCbC-CHjCHj B.1124 CH OCHjCHj CH 3 C - CH 3 CH 3 9.1129 CH CN CHjCbC-CNjCKj 3.1126 CFj H CHjCaC-CHjCHj B.1127 CFj CH, CHjC-C-CKjCHj B.1128 CFj CHjCBj CHjCbC-CHjCHj 3.1129 CFj CFj CHjCeC-CHjCHj 3.1130 CFj chf ₂ CH ₂ C «C-CH ₂ C ij 3.1131 CFj CHjF CHjCeC-CHjCHj 3.1112 CFj Cl CSjCeC-CHjCHj 3.1133 CFj OCH CHiCeC-CHjCHj 3.1114 CFj OCHjCHj CHjCBC-CHjCKj 3.1135 CFj CN CHjC «C-CHjCHj 3.1136 H CH CH ₂ Cl ₂ -CH ₂ CH ₃ B.1137 H CHjCHj CH ₂ Cl ₂ -CH ₂ CH 3 3.1138 H CFj CH ₅ CmC-CH ₂ CH 3 3.1139 H Cl CHjCaC-CHjCHj 3.1140 H OCH ₃ CHjCsC-CHjCHj B.1141 CHjCHj CH CH ₂ CwC-CH ₂ CH 3 B.1142 CHjCHj CH2CH3 : k _with C «C-CH3CH _} 3.1143 CHjCHj CFj : hjC3C-ch ₂ che

Hr. R ' R ' ä.1163 CK » CHjCKj CHjCaC-CF) B. 1184 CE) CF) CK ₂ C · C-CF 3 B.118? CH) CHF, CH ₂ C «C-CF 3 B.1186 CK) CHjF CHjCBC-CFj 3.1187 CK i .it Cejc «C-CF) 3.1188 CT OCH) CH ₂ C «C-CF 3 B.1189 CH OCHjCHj CK ₂ CaC-CF 3 B.1190 CH CH CH ₂ C »C-CF 3 1.1191 CF) N CHjCHC-CFj 3.1192 CFj CH) CHjCwC-CFj 3.1193 CFj CHjCHj CHjCBC-CFj 8.1194 CFj CFj CHjCSC-CFj B.1195 CFj ch? ₂ CM ₂ CeC- £ F ₃ J.1196 cf ₃ CHjF CH _and C * C-Cfj 3.1197 CFj Cl CHjC »C-CFj B.1198 CFj OCH CHjCaC-CF) B. 1199 CFj OCHjCHj CHjC »C-CF, 9.1200 CFj CN CHjCeC-CFj 3.1201 E CH CHjCeC-CFj 3.1202 H CHjCHj CHjC «C-CFj 3.1203 H CFj CH ₂ C »C-CF 3 3.1204 H Cl CH ₂ C «C-CF 3 3.1205 H OCH CH 3 C-CF 3 3.1206 CHjCKj CH OHjChC-CFj 3.1207 CHjCHj CHjCHj CK ₂ C «C-CF ₃ .12 08 CHjCHj CFj Chico »C-CFi 3.1209 CHjCHj Cl CK ₂ CeC-CF _} 9.1210 CHjCJJj OCH CHjCBC-CFj 3.1211 CHFj CK i CKjCsC-CFj 3.1212 CHFj CKjCHj CHjCaCO. 3.1213 CHF-. CFj CKjC · C-CFj 3.1214 CHFj Cl CKjC »C-CFj 3.1215 CHFj OCH CHjC DEG-CFj ) .1216 CH, F CH CíjCaC-CF, 3.1217 ch ₂ f CHjCHj CKjC »C-CFj 9.1216 CHjF CFj CHjCeC-CFj 3.1219 CHjF Cl CHjC 'C' CFj 3.1210 ch ₂ f OCH) CB CAC-CFj 3.1221 OCH) CH CHjOC-CFj

Nr. R ³ R ^s R ' B.1222 OCH CHjCHj CH ₂ C »C-CF 3 B.1223 OCH CF) CHjC 'C' CFj B.1224 OCH Cl CHjC «C-CFj 8.122S OCH OCH CH ₂ C »C-CF 3 B.1226 OCH _and CH) CM, CRjCeC-CF) B.1227 OCKjCH) CHjCHj CH ₂ CeC-CF) B.1228 OCKjCH) CFj CHjChC-CFj 0.1229 OCH ₂ CHj Cl CH ₂ CeC-CF 3 B.1230 OCHjCHj OCH) CHjCbC-CFj B.1231 CN CH3 CH _and CC-CF 3 B.1232 CN CHjCHj CH) C »C-CF ₃ B.1233 CN CF) CH) CHC-CFj B.1234 CN Cl CHjCeC-CFj B.1235 CN OCH) CH ₂ C «C-CF ₃ 3.1236 Cl H CH 3 C = C-C (CH 3) j B.1237 Cl CH CH2Cl2-C (CH2) 3 B.1238 Cl CHjCHj CH3CaC-C (CH3)) B.1239 Cl CF) CH2Cl2-C (CH2) 3 B.1240 Cl CHF) CH3CmC-C (CH3) j B.1241 Cl CH) F CH 3 C-C (CH 3) B.1242 Cl Cl CH _and C1-CC (CH3) B.1243 Cl OCH) CH ₃ CClCH ₃ ) ₃ 3.1244 Cl OCHjCHj CX ₂ C 'CC (CH) 3 B.1245 Cl CN CH ₂ C = CC (CH ₃ ) 3 3.1246 CH) The CeO ₂ CH-C (CH ₃ l 3 B.1247 CH CH) CK _S C CC (CH) | ) 3.1246 CK ₃ CHaCHj CH) CaC-C (CH))) 3.1249 CH) CFj CH ₂ C 3 -C-CH (CH) 1 3 B.1250 CH) CHFj CHjCbC-CÍCHjJj 3.1251 CH CHj F CH ₃ Ca CC (CK ₃ ) ₃ 0.1252 CH Cl CH ₂ CHC-C (CH 3) 3 3.1253 CH) OCH) CH ₂ C = CC (CH 3) 3 0.1254 CH, OCHjCH) CH ₂ C · CC (CH ₃ ) ₃ 3.1255 CK) CN CH ₂ CwC-C (CH ₃ j) B.1256 CFj H CH ₂ C · CC (CH ₃ ) 3 B.1257 CFj CH, CH ₂ Cl ₂ (CH 3) 3 B.1258 CF) CH2CH3 CH ₂ C * CC (CH 3) 3 B.1259 c) CFj CHaC = CC (CH3) ₃ B.1260 CF _} CHFj CH ₂ C * C-CH3)

Nr. R ³ R ^s R 0.1300 CN OCH CH ₂ CsC-C ₍ CH 3) 3 8.1301 Cl H CHiCsC -C _{Th 5} 3.1302 Cl CH Chaco «C-CeH5 B.1303 Cl Chacha) CEjC »CC _£ K ₅ B.1304 Cl CFj CH 3 C = CC _with K _s B. 1305 Cl chf ₂ CEjC = CC ₆ H _p B.1306 Cl ch ₂ f CH ₂ C = CC ₅ K ₅ B.1307 Cl Cl Chacaca-CjEj B.1308 Cl OCH CHjCaC-cihi B.1309 Cl CCNjCH] CeO ₂ CH-C ₅ H _g B.1310 Cl CN CH _and C = CC _with H _s B.1311 CH) CH ₂ C ^and CC _S H _p B.1312 ch ₃ CH CH ₂ CSC-C _S 5s 8.1313 CH CH ₂ CH ₃ CH ₂ CC-CsH 5 8.1314 ch ₃ CFj CHjCsC-CIH; B.1315 CH) CHFj CH ₂ CC-Cl ₅ B.1316 CH) CHjF CH ₂ C = CC (Hs 8.1317 CH) Cl CH ₂ CHC-C (W ₅ B.1318 CH) OCH) CHjCssC-CIHS B.1319 CH OCNjCHj CH ₂ C «C-CHH ₅ 8.1320 CH CH CeO ₂ CH-C _T hs B.1321 CFj H CHjCSC C _D H _p B.1322 CFj ch ₃ CH ₂ CaC-C ₆ H ₅ B.1323 CFj ch ₂ ch ₃ CH 3 CHC-CeH ₅ B.1324 C Fj CFj CH ₂ C · CC ₄ H _p B. 1325 cf ₃ CHFA CHjCeC-CIHS B.1326 CF) CH ₂ F CHiCeC-Ph 3.1327 CFj Cl CHjCWC-CíHj 3.1328 CF] OCH CH 3 (CC _e H) B. 1329 CF] OCHjCHj CHjC »C-C $ K) B.1330 CF] CN CH 3 Ca-C CH _s a.1331 H CH CH 3 C ₆ CC ₆ H _p 0.1332 H CHjCH) CHjCwC-CEH » 0.1333 H CF] CH 3 C = CC _and H _s B.1334 H Cl CH ₂ C «C-C 8 H 8 0.1335 H OCH CH) CaC-C _e H _p B.1336 CHjCHj ch ₃ CH _and C ₆ -C ₆ H 5 B.1337 CHjCHj CHjCK) CHjC-C-CIHS B.1338 CHjCH) CF, CH _with CsC-Cl ₅

Nr. k ³ R R ⁵ B.1261 CF) CHjF CH ₃ CSC-C (CH ₃ ) j B. 1262 CF) Cl CKjCaC-C (CH3) 3 B.1263 C F) OCH CH1CBC-C _(CH3) 3 3.1264 cf ₃ OCHjCHj CH ₂ C * CC (CH ₃ ) ₃ B.1265 cf ₃ CN CX ₂ C * CC (CH 3) j B.1266 H CH) CH ₂ Cl ₂ (CH ₃ ) j B.1267 H CKjCMj CH ₂ Cl ₂ (CH 3) j 3.1268 H CFj CM) C * C-C (CH ·)}) B.1269 H Cl CHaCeC-C (CH3)) B.1270 H OCH) CH ₂ Cl ₂ (CH ₃ ) ₃ B.1271 CHjCHj CH CH ₂ C · C-C 1 H 3 3.1272 CHjCHj CHjCHj CH) CBC-C (CH3) j B.1273 CHjCHj cr ₃ CHíCbC-CÍCMjIj 3.1274 CHjCHj Cl CH 3 C-C (CH 3) 3.1275 CB ₂ CH) OCH CH ₂ Cl ₂ (CH ₂ Cl 2) 3.1276 CHP) CH) CH _and CHCl 3 (CH 3) 3.1277 chf ₂ ch ₂ ch ₃ CH ₂ C · CC (CH ₃ ) ₃ B.1278 • CHFj cf ₃ CH ₂ CSC-C (CH ₃ )) B.1279 Cilfit Cl CH) CaC-C (CH3)) B.1280 C8P) OCH CH) C »C-C (CHj) j 3.1281 CHjF CH CHjC 'C-C (CH31) 3.1282 CHjF CHjCHj CH3CaC-C (CH3) j B.1263 ch ₂ f C Fj CH ₂ C = CC (CH ₃ J) B.1284 ch ₂ f Cl C, C-C (CH3) j B. 1285 CHjF OCH CH3CaC-C (CH3)) 3.1266 OCH CH CHiCBC-C _(CH3) j 3.1287 OCH) CHjCK) CH) C 'CC (CH _{3) 3} B.1288 OCH3 C Fj CH 3 Cl 2 (CH ₃ ) ₃ B.1289 OCH) Cl CH ₂ CSC-CH ₃ )) B.1290 OCH OCH) CH3CeC-C (CK)) B.1291 OCHjCH) CH CH) C »C-C (CH)) j 8.1292 OCHjCHj CKjCXj CH3COCOC (IC3) 3 B.1293 OCK ₂ CHj CFj CH3CaC-C (CH3)) B.1294 OCHjCHj Cl CMíCac-C _{(CH3) 3} B.1295 OCKjCH) OCH) CH2Cl2-C (CH3) 3 B. 1296 CN CH ₃ CH _and CaC-C (CH _a ) j B.1297 CH CHjCHj CKjC £ CC (CB _{3) 3} B.129B CN CF) CH3CaC-C (CH3) ₃ 3.1299 CN Cl CH ₂ C (CC (CK3))

Nr. R ³ rs R B.133 CH ₂ CH 3 Cl CH ₂ CaC-Cl ₅ 3134 CHjCKj OCH) CH ₂ CsC-C ₃ H _s 3134 CHF) CH) CH _with ChC-C <H _s 3.1344 CHFj CHjCHj CH ₂ C «C-CHH _p 3.1343 chf ₂ CFj CH ₂ CaC-C _e H _p 3.1344 CHFj Cl CHjCaC-CjHs B.1345 CHFj OCH) CH _with C _»no-ct Hj B.1346 CHjF CH CHjCeC-CíHj 3.1347 CHj F CHjCHj CK] C “CC _with H ₅ 3.1348 CHjF CFj CH 3 Cl ₂ H ₄ B. 1349 ch ₂ f Cl CHjCaC-CIHS B.1350 CHjF OCH CH ₂ C · CC ₆ X _p B.1331 OCH CH CH ₂ CsC-e _with H ₅ B.1352 OCH3 CH ₂ CH 3 CH ₃ Cl 2 C ₆ H $ B.1353 OC83 CFj CHjCssC-cihi B.1354 OCH) Cl CHjCeC -C _e H _p 8.1355 OCH OCH) c: c = _a í _£ Hs cc B.1356 OCH ₂ CK3 CH ₃ CH _and CeC-C _€ H _p B.1357 och ₂ ch ₃ CHjCHj CH ₂ CbC-C _with K _s B.1358 OCH ₂ CHj CF) CH ₂ CaC-C ₆ K _p B.1359 OCHjCHj Cl CH ₂ CeC-C _with H _s B.1360 OCHjCH) OCH) CK ₂ CeC-C _e n ₃ B.1361 CN CH) CKaCeC-C _with W ₅ B.1362 CN CHjCHj CH ₂ C = CC ₅ H _S B.1363 CN CFj CH ₂ CaC-C _with K _s Θ.1364 CN Cl CH ₂ CaC-C _S K $ 3.1365 CN OCH Chace 'CC _t H _p B. 1366 Cl H CH _and C 'C- (2-Cl-C RI _{C 4)} B.1367 Cl CR) CM ₂ CaC- (2-Cl-C _with H ₄ ) 3.1368 Cl CHjCHj CH _and C = C- (2-Cl-C _c Hi) B.1369 Cl CFj CH 2 Cl 2 - (2-Cl-C ₆ H ₄ ) B.1370 Cl CHPj CH ₂ CsC- (2-CL-C ₆ H ₄ ) B 1371 Cl CHjF CH ₂ CaC- (2-Cl-C _e H ₄ ) 3.1372 Cl Cl CH _and C «C- (2-Cl-C ₆ M ₄ ) B.1373 Cl OCH CH _and C »C- (2-Cl-C ₆ H ₄ ) 3.1374 Cl OCHaCH) CH3C SC- (2-Cl-C ₄ H ₄ ) 8.1375 Cl CM H _and CAC- (2-Cl-C ₆ H ₄₎ 3.1376 CH) H : hjcbc- (2-ci-c ₆ hrs ₄ ) 3.1377 CH) CH -HiC «C- (2-c1-C ₆ H ₄ )

nr. R ³ R ^s R B.1378 CH CHaCKj CH ₂ C = C- (2-CL-C ₄ H ₄ ) B.1379 CH CFj CH _and CC- (S-CL-Cicl · B.1380 CH οηγ ₂ CH 3 Ca-C- (2-Cl-C ₄ H ₄ ) B.1381 CH CHjF CHjCsC- (2-Cl-C ₆ H ₄₎ B.1382 ch ₃ Cl CHjC 'C- (2-C1 _4-CIH) B.1383 CH OCH CH ₂ C = C- (2-C 1 -C ₄ H ₄ ) B.1384 'CHj OCHjCHj CitaCaC-ts-C CfXi) B.1385 CH CH CH ₂ C · C- (2-Cl-C ₅ H ₄ ) B, 1386 CFj H CH _{2 (} CbCl 2 -C 1 -C ₄ H ₄ ) B.1387 CFj CH CH ₂ C → C- (2-C 1 -C ₄ H ₄ ) B.1388 CFj CHjCHj CH3C »C- | 2-C1-C ₄ H ₄ ) B.1389 CFj CFj CH ₂ Chc- (2-C1-C _with E ₄ ) B.1390 CFj CKFj CHjC 'C (itcl-C ₆ H ₄₎ B.1391 CFj CHjF CHaCec-o-C CííQ) B.1392 CFj Cl CH ₂ CBC- (2-Cl-C ₄ H ₄ ) B.1393 CFj OCH CH ₂ C = C- (2-Cl-C ₄ H ₄ ) B.1394 CFj OCHjCHj CH ₂ C → C- (2-Cl-C ₄ H ₄ ) B.1395 CFj CN CHĺCeC-U-C ^ CJH B.1396 H CH CH 3 C = C- (2-C 1 -C ₄ H ₄ ) B.1397 H CHjCHj CH ₂ C = C- (2-C 1 -C ₄ H ₄ ) 3.1398 H CFj CH ₂ C · C- (2-Cl-C ₄ H ₄ ) 3.1399 H Cl CH ₂ C-C- (2-Cl-CeH ₄ ) B.1400 H OCH CH ₂ C = C- (2-Cl-ClH) 3.1401 CHjCHj CH CH ₂ C · C- (1-C 1 -C ₄ H ₄ ) 3.1402 ch ₂ ch ₃ CHjCHj ch ₂ c-c- (2-Cl-CeH ₄ ) 3.1403 CHjCHj CFj CH ₂ C »C- (2-C1 _4-CIH> 3.1404 CHjCHj Cl CHjC®C- (2-C 1-C ₆ H ₄₎ 3.1405 CHjCHj OCH CHjCaC-U-C ^ Focus) 3.14Q6 CHFj CK i CH ₂ C «C- (2-Cl-C ₆ H 4) 3.1407 chf ₂ ch ₂ ch ₃ CH ₂ CeC- (2-Cl-CfMd B.1408 CHF _a CFj CH ₂ C «C- (2-C 1 -C 4 H 4 J) 3.1409 CK? And Cl _A CEC-CH _(2-Cl-4 NAV) 3.1410 CHFj OCH CH ₂ C · C- (2-Cl-C6H ₄ ) B.1411 CKjF CH CH ₂ C = C- (2-Cl-C ₄ H, _S) J.1412 ch ₂ p CHjCHj CHjCMC- u-cl-c h h ₄ ) B.1413 CH _and F CFj CH _and CsC- (2-Cl-C _e H ₄ ) B.1414 CR ₂ F Cl CH ₂ CeC-1a-Cl-ClHi) B.1415 CHj F OCH CE ₂ ChC- (2-c: -C _£ H4) B.1416 OCH CH CH ₂ CHC- (2-Cl-C 8 H 4)

Nr. R ³ R ⁵ R ⁵ 3.1417 OCH CH ₂ CH 3 CH ₂ C · C- (2-Cl-C ₆ H ₄ ) B.1418 OCH CFj CH ₂ C® C- (2-C 1 -C ₄ H ₄ ) B.1419 OCH Cl CK ₂ C · C- (2 “Cl-CgH ₄ ) B.1420 OCH OCH CK ₂ C C C- (2-CX-C ₄ H ₄ ) 3.1421 OCHjCHj CH CHjCsc- (2-Cl ~ C _s H ₄₎ 3.1422 OCHj CH j CHjCHj CH ₂ C • C- | 2-CL-C ₄ H ₄ ) B.1423 OCHjCHj CFj CH3C * C-12-Cl-C6H *) 3.1424 OCHjCHj Cl CH _and CAC- [2-Cl-C 6 H ₄₎ 3.1425 OCHjCHj OCH CHjCsC- _(2-Cl-4 CTH) S.1426 CN CH CH ₂ C * C- (2-Cl-C ₆ H _4> B.1427 CN CHjCHj CH ₂ CsC-12-Cl-C _with H ₄ } B.1428 CN CFj CH ₂ CeC- (2-Cl-C ₄ H ₄ ) B.1429 CN Cl CH ₂ CsC- (2-CL-C ₄ H ₄ L) B.1430 CN OCH CH ₂ CsC- (2-Cl-C ₆ H ₄ )

Table 41

Compounds of formula (Ia) in which R @ ² _m is hydrogen and the combination of the radicals R @ ³ , R @ ^x , R @ ^y and R @ ^z for the compound corresponds in each case to one row in Table C.

O (Ia.5)

Table 42

Compounds of general formula (Ib.5) in which R ² _m is hydrogen and the combination of R ³ , R ^x , R ^y and R ^z for the compound each corresponds to one row in Table C.

Compounds of formula (Ic.5) wherein R ² _m is hydrogen and the combination of R ³ , R ^x , R ^y and R ^z for the compound each corresponds to one row in Table C.

Compounds of formula (Id.5) in which R ² _m is hydrogen and the combination of R ³ , R ^x , R ^y and R ^z for the compound always corresponds to one row in Table C.

(Id.5)

Table 45

Compounds of formula (Ie.5) in which R ² _m is hydrogen and the combination of R ³ , R ^x , R ^y and R ^z for the compound each corresponds to one row in Table C.

R ^and ur -C _M ľ CRjQ. The XI about (Ie.5) Table 46

Compounds of formula (Ia.6) in which R ² _m represents hydrogen and the combination of the radicals R ³ , R ^x , R ^y and R ^z for the compound always corresponds to one row in Table C.

Compounds of formula (Ib.6) in which R ² _m is hydrogen and the combination of R ³ , R ^x , R ^y and R ^z for the compound each corresponds to one row in Table C.

Table 48

The compounds of formula (Ic.6), wherein R ² is hydrogen, and _{R A} combination of the radicals R ^3, R ^x, R ^y and R @ ^z for each compound corresponds to one line of Table C.

Cr. «5 H ¹ The 8 » C .12 13 CH, H CH 2 CH 2) C ₍ N, H CH, H C <C, H 14 CW, H 4-R-c.H, H 15 CH, H i-Cl-l-pyridyl H 16 CH, H r H Π CH, H CN H 18 CH, CH, H H 13 CH, CH, CM, The 20 CH, CH, C, C, The 21 CH, CH, C, H, H 23 CH, CM, << », The 23 CH, CH, Chicha,) H 24 CH, CH, cyclopropyl H with CH, CTI, CF, U 6 CH, CH, OCH H F CH, CH, CC, H, X C « CH, CH, CH, -C, H, H C 9 CH, CH, H {CH) --H, H C U CH, CH, ίΛ H C 1 CH, CH, 4-rC.H ₅ H C 2 CH, CH, 4-Cl-i-pyridinyl H C 3 CH, CH, r and C * CH, CH, CN H C 5 CH, C, H, H H C 6 CH, C} H CH, rt C 7 CH, C, B, C, H, H C B C $ 8 C, H, H C I ' CH, C «B» H C 0 CH, C, B, CHICKj) A C 1 CH, C, H) cyclopropyl s C 2 CH, CJM, cr. tt. C 3 CK, C, Ks OCH WITH C 4 CH, C, H, OC, H _$ H C WITH CH, C, H, ΟΗ, -ΟΛ The C C 6 CH, C, clay CHICB, C ₄ Bj H > CH, C, H, C _S H, H C CH, C, H _S 4-R-NAV. WITH 9 CH, C, K ₅ 4-11-2-Pyridyl 3 CH, C, C, ^F *

Table 49

Compounds of formula (Id.6) in which R ² _m is hydrogen and the combination of R ³ , R ^x , R ^y and R ^z for the compound each corresponds to one row in Table C.

Table 50 (Id.6)

Compounds of formula (Ie.6) in which R ² _m is hydrogen and the combination of the radicals R ³ , R ^x , R ^y and R ^z for the compound each corresponds to one row in Table C.

Hr. R ' R ' C.51 CH, C, H _S CN H C.52 CH, cyclopropyl H C.53 CH, cyclopropyl CH, H C.54 CH, cyclopropyl C, C, H No.55 «J cyclopropyl C) H » H C $ 6 ch. cyclopropyl C ₍ H, H. C.57 CH, cyclopropyl CHiCKíh . H No.58 CH, cyclopropyl cyclopropyl H C.59 CH, cyclopropyl CF, H C. 60 CH, Cyclopropyt OCH H c.íl CH, cyclopropyl OC f> j H No.62 CH, cyclopropyl CKI-CFN, H C.53 CJT, cyclopropyl CH (CH 3 J C 5 H, H C. 54 CH, cyclopropyl C ₍ H, H C.5S CH) cyclopropyl 4-FC _TH, H No.66 CH, Cycloyrcpyl 4-Cl-2-pyridyl « C. 61 CH, cyclopropyl F H ς, 6ί CH, cyclopropyl CN H C.59 CH, LF> H H C. 20 CH, CF, CH, H No.71 CH, CF, C. To, The No.72 CZ, CF, C ij H No.73 CP, CF, C, H, H No.74 CN, CF, ch (o :,) H No.75 CN, CP, cyclopropyl The No.76 CN, CP, CF, H No. 77 CH, CF) OCH The No.71 CH, CP) OC, H _S H No.79 CH, cr. CH-CIHS H C. M CH, CF, CHlCHjiCjW. H c.ei CN, CP) e «H ₅ The C.B3 CH, CF, 4-F-C, H, H No.83 CH, cr, 4-Cl-2-Fyri.dyl H , C.B4 CH, CF, F H C.B5 CH, cr. CN H C.84 CH, Cl H H :. "7 CH, Cl CH, H C.BB CK, Cl C, H, The No.89 CK, Cl C, H, H

Table C

Hr. R ³ R ¹ Rí R ' C.I. CH H H H C.2 CH, H CH, H C.3 CH, H C ₃ H _S H C.4 CH, H CJH. H C.5 CH, H c ₄ h, H C.6 CH, H CH (CH), H C.7 CH, H cyclopropyl H C.3 CH, H CF, H C.9 CH, H OCH H C.10 CH, H OC ₂ H, H c. 11 CH, H CH-cihi H

Hr. X » »* R> R · 90 CH, Cl C, H, H H ch. Cl CTOjh H 92 CH, Cl cyclopropyl The 93 CH) Cl CP, The 94 CH, Cl OCH H 95 CH, Cl OC, H, H 95 '' J Cl H 97 CH, Cl CH (eK, iC, H) H 9 B CH, ci C <H | M »9 CH, Cl 4-R-Cji, H C 100 CH, Cl 4-Cl-3-pyridyl x C 101 CH, Cl The C 102 CK> Cl CT n C 103 CK, The C 10 « CH, e "i, H C 105 CH, C, H, The C 05 CK, C, C, The C 107 CK) c «« 4 H C 101 CK, CHTCH,,, H C 09 CK, cyclopropyl » C 1 » CK, CP, H C 11 CH, OCH H e 11 CH, OCjH. H C 13 CH, r CHrCjH. The C 1 ' CH, r CHICHitCtH. The C 1S CN, r t <3 < The "No." 17 CH, T 4--cut, The CH, r 4-Cl-i-Pyrl <Ty The C 11 CH, r T x C 19 CH, r CN H C 20 CH, steel, « C 31 CH, OCH CH, H C 22 CH, OCH C * X C 23 CH, OCH C, C, H C 24 CK, OCH C, C, H C 25 CH, OCH CHICH ,,, The C 26 CH, OCH cyclopropyl H C 29 CH, OCH cr, x C 2S CH, OCH OCH X

Nr. R ³ R No R ¹ no.129 CH, OCH OC, H _S H No.330 CH, OCH CK i-CjKs H No.131 CH OCH (CHICH) C ₍ Hs H No.132 CH, OCH C _t H ₅ H No.133 CH OCH 4-F-CjHj B č.134 CH OCH 4-Cl-2-Pyiidyl H C. 135 CH OCH F H No.136 CH OCH CH H no.137 ČKJ H The CH No.138 CH H CH CH No.139 CH H CjHs CH No.140 CH H C ₃ K ₇ CH No.141 CH) H CjHj CH No.142 CH H CH _(R) j CH no.143 CH H cyclopropyl CH No.144 'CH) H ch CH č.145 CH H oh, CH, č.146 CH H OCjHj CH No.147 CH, H CKL-CíHj CH C. 148 CH, H CHťCHjJCíKj CH č.349 CH) H CíH _S CH No.150 CH H 4-FC <M _} CH C. 151 CH H 4-Cl-2-pyridyl CK i č.152 CH) H F CH, č.153 CH H CN CH No.154 CH, CH H CH C. 155 CH CH CH CH C. 156 CK) CH CjH ₅ CH C. 157 CH) CH j CJH? CH C. 158 CH, CH C) H CH č.159 CH CK, CH (CHjl? CH No.160 CH CH cyclopropyl CH C. 161 CH CK i CFj Π CH č.162 CH, CH OCH CH No.163 CH, CH OCjHs CH C. 164 CH CH CH-CjHj CH No.165 CH ck ₃ CHÍCHjICcHs CH C. 166 CH, CH c ₄ h _p CH No.167 CH CH 4-PC _t H _p CH

Nr. R ³ R » in R » č.207 CH, CF, CjHs CH č.208 CH, CF, CJH. CH, č.209 CH CP) C <H, CH, č.210 CH CFj CH (CH3) ₂ CH, č.211 CH CF, cyclopropyl CH, No. 212 . CH CFj CF, CH, No.213 CH CF) OCH CH, No.214 CH) CFj OCjMs CH, No.215 CH, CFj CH-CIK & CH, No.216 CH CF, CH (CH) C <Hj CH, No.217 CH, CFj ’ C ₍ H, CH, č.218 CK i CPJ 4-r-Cl ₅ CH, C-219 CH _} CFj 4-Cl-2-Fyridyl CH, n.220 CH, CFj F CH, No.221 CH, CF, CN CH, C. 222 CH, Cl H CH, C. 223 CH, Cl CH, CH, No.224 CH, Cl CjH _s CH, č.225 CH Cl CjHj CH, C. 226 CH, Cl C <Hj CH No. 227 CH Cl CH (CH3) j CH č.228 CH Cl cyclopropyl CK, č.229 CH Cl • Ch CH, No.230 CH, Cl OCH CH, No.231 CH, Cl OCjH. CH No.232 CH Cl CH 3 -C ₅ H ₅ CH No.233 CH, Cl CH (CH 2 Cl _{2 5)} CH č.234 ch ₃ Cl C _D H _p CH, č.235 CH Cl 4-P-CsHj CH, No.236 CH) Cl 4-C1-2- · Pyridyl CH No.237 CH, Cl P CH, č.238 CH Cl CN CH č.239 CK, P The CK i • No.240 CH, F CH, CH č.241 CH, F CjHj CH, č.242 CH, F CJH. CH, č.243 CH P c ₄ h, CH, č.244 CH F CHfCH.) CH _} No 245 CH F cyclopropyl CH

Nr. R ³ R RX R · No.168 CH CH 4-Cl-2-pyridyl CH No.169 CH CH F CH No.170 CH CH CN CH 171 event CH C) H ₅ H CH No.172 CH C) H _S CH CH No.173 CH C) H ₅ CjHs CH number 174 CH CjHs CjHj CH C. 175 CH CjHs C) H CH No.176 CH CjH ₅ CH (CH3) j CH No.177 CH CjHs cyclopropyl CH č.178 CH CjHs CFj CH No.179 CH CjHs OCH ch ₃ C.180 CH CjH _s OC, H _S. CH č.181 CH CjHs CH-Ph CH No.182 CH C) H _S CH (CH) ₅ CIH CH No.183 CH CjHj C <Hs CH No.184 CH CjHs 4-F 'C _f H ₅ CH No.185 CH C ₂ Hs 4-Cl-2-Fyridyl ch. No.186 CH CJT-s CH č.187 CH CjHs CN CH No. 188 CH cyclopropyl H ch. C.1B9 CH cyclopropyl CH CH) No.190 CH cyclopropyl CjHj CH) No.191 · CH cyclopropyl CJH. CH C.192 CH cyclopropyl C <H, CH, No.193 CH cyclopropyl CH (CH3) i CH č.194 CH cyclopropyl cyclopropyl CH No.195 CH cyclopropyl ch CH No. 196 CH cyclopropyl OCH) CH, č.197 CH cyclopropyl CCjHs CH) No. 198 CH cyclopropyl CK i-CIHS CH C.199 CH cyclopropyl CH (CH) C H _{S p} CH, C.200 CH cyclopropyl C _{Th 5} CH no.201 CH cyclopropyl 4-F-CJH. CH C.202 CH cyclopropyl 4-Cl-2-pyridyl CH no.203 CH cyclopropyl CH) no.204 CH cyclopropyl CN CH, C.205 CH CF) H CH č.206 CH CFj CH CH

Nr. X ³ R ' W R ' č.246 CH, CF, CH, C. 247 CH, OCH CH, č.248 CH, OCjHj CH, č.249 CH, CH-CIH) CH, No.250 CH) CH (CH) ₅ CIH CH, No. 251 CH) F CH ₅ CH, No.252 CH, 4-F-Ph CH) č.253 CH, F 4-Cl-2-Fyridyl CH, No.254 CH, F F CH, No.355 CH CN CH, C. 256 CK) □ CH, H CH, No.257 CH OCH CH CH, C. 258 CH) OCH CjH _s . CH, C. 259 CH, OCH CJH? CH, č.260 CH OCH C «H CH, No.261 CH OCH TA (CHjl) CH No.262 CH, OCH cyclopropyl CH) č.263 CH, OCH C ?, CH) No.264 CII3 OCH OCH) CH, č.265 CH, OCH OCsHs CH) C-266 CH OCH CH-CjHs CH č.267 CH OCH CHCCHjJCíHs CH) C.268 CH OCH C «H $ CH č.269 CH, OCH 4-F-CjHs CH) č.270 CH, OCH 4-Cl-2-pyridyl CH č.271 CH OCH F CH, No.272 CH, OCH CN CH č.273 H CH) H The # 274 H CH, CE, H # 275 H CH C, H _S H # 276 H CH, CJH. H č.277 H CH, C <H> H č.278 H CH CH _(S> T H No. 279 The CH, cyclopropyl H č.280 H CH CF, R no.281 H CH, OCH H č.282 H CH OCjHj H č.283 H CH, CH 3 -Cl ₅ H No.284 H CH, TA (CH)) C * H H

Hr. R ³ R RF R » No.285 The CH C ₅ H ₅ H No.286 H CH 4-F-CIHS H No.287 H CH 4-Cl-2-pyridyl H C.288 H CH H č.289 The CK i CN H C. 290 H CH H CH č.291 H CH CH CH C, 292 H CH CjHj CH č.293 The CK i CjHj CH č.294 H CH c <h ₉ CH č.295 H CH CH _(CH3) j CH no.296 H CH cyclopropyl CH č.297 H CH CFj CH C. 298 H CH OCH CH No.299 H CH OCjHj CH No.300 H CH CHj-C _with K, CH no.301 H CH CH (CH) C ₆ H S CH no.302 H CH C _D H _p CH No.303 H CH 4-F-CIHS CH č.304 H CK i 4-Cl-2-pyridyl . CH C.305 H CH F CH C. 306 H CH CN CH No.307 M CFj H The c.308 H CFj CH H No.309 H CFj CjHj H č.310 ' H CFj c, h ₇ H č.311 H CFj c ₄ h, H č.312 H CFj CH (CH3) _S H C.313 H CFj cyclopropyl H C.324 and CFj CFj H č.315 H CFj OCH H č.316 B CFj OCjKs H C.317 H CFj CH-CtRj H No. 318 H CFj CH (CHjlC <Ks H č.319 H CFj C «Hs H No.320 H CFj 4-FC «H _ä H č.321 H CFj 4-Cl-2-pyridyl H C. 322 H CFj F H C.323 H CFj CN H

Nr. R ^J R ^x R R ¹ č.363 CFj CH, CH (CH3) j CH C.364 CFj CH cyclopropyl CH, C.365 CFj CH, CF » CH, č.366 CFj CH, OCH CH č.367 CFj CH, oc ₂ h ₅ CH C.368 C? J CH CKI-CIHS CH no.369 CFj CH, CH (CH ₃ ) C _S H _S CH C.370 CFj CH, CjHs CH C.371 CFj CH 4-FC «H ₄ CH C.372 CFj CK i 4-Cl-2-pyridyl CH, C.373 CFj CH F CH, C. 374 CFj CH, CN CH, C.375 CFj CFj H H C.376 CFj CFj CH, H C.377 CFj CF, C, H, H C, 378 CFj CFj CJH. H No.379 CFj CF] C <H, H C.380 CFj C F, CH (CH), H No.381 CFj CFj cyclopropyl H No. 382 CFj CF, CFj H No.383 CFj CFj OCH H C. 384 CFj CFj OC _and H _p H C.385 CFj CF, CH-CjHs The č.386 CFj CFj CH (CH) C _t H _p H č.387 CFj CFj CIH, H C. 388 CFj CFj 4-F-C 'H S The C.389 CFj C F, 4-Cl-2-pyridyl H č.390 CFj CFj F H č.391 CFj cf ₃ CN H No.392 CFj CFj H CH C.393 CFj CFj CH CH, C.394 CFj CFj C ₂ H _p CH, C.395 CFj CF, CJH. CH č.396 CF) CFj CJH. CH, Nr.397 CFj CFj CH (CH 2) 2 CH, No.398 CF) CF, cyclopropyl CH C.399 CFj CFj C F, CH, C.400 CF, CFj OCH CH, no.401 CFj CFj -oc ₂ h _p CH

Nr. R ³ R RF R ' C.324 H CFj H CH No.325 H CFj CH CH C. 326 H CFj c ₂ h ₅ CH C.32? H CFj CJH. CHj. No.328 H CF, C <H, CH č.329 H CFj TA (CH) j CH No.330 H CFj cyclopropyl CH No.331 H CFj CFj CK i č.332 H CFj OCHj. CH No.333 H CFj OCjHs CH, č.334 H CFj Cfíj-CjHj CH, No.335 H CFj CH (CH) C _t Hi CH C. 335 H CFj C «H _S CH, č.337 H CFj 4-FC _t H _p CH č.338 H CFj 4-Cl-2-pyridyl CH č.339 H CFj F CH, č.340 H CFj CN CH, č.341 CF) CH H H č.342 CFj CH CH H č.343 CFj CH C, M _S H C. 344 CFj CH CJH. H No.345 CFj CH C <H, X No.345 CFj CH CH ICH ₁₂ H No. 347 · CFj CH cyclopropyl H č.348 CF, CH CFj H č.349 CFj CK i OCH H No. 350 CFj CH OCjHj H č.351 CFj CH CH-CIHS B C.352 CFj CH CHtCHjJCjHí « č.353 CFj CH CíHj H č.354 CFj CH 4-R-CjHs H No.355 CFj CH 4-Cl-2-pyridyl H C.356 CFj CH F H C.357 CFj CH CN H No.358 CFj CH H CH č.359 CFj CH CH CH C.360 CFj CH CjK ₅ CH No.361 CFj CH CJH. CH C. 362 CFj CH C <H, CH

Nr. R ³ R ^x RF R ' C.402 CFj CFj CH ₂ -C ₆ H ₅ CH C.403 CFj CFj CKtCHjJCíH. CH No.404 CFj CF, C _S H _S ch ₃ No.405 CF, CFj 4-FC ₆ H _p CH č.406 CF, CFj 4-Cl-2-pyridyl CH, No. 407 CFj CFj F CH, No.408 CFj CF, CN CH, C.40? Cl CH H H C.410 Cl CH CH H C.411 Cl CH CJH. H č.412 Cl CH CJH. H C.413 Cl CH CJH. H č.414 Cl CH CH (CH) j H No.415 cl CH cyclopropyl H C.416 Cl CH, CF, H C.417 Cl CH och ₃ H C.418 Cl CH, OCjHj H C.419 Cl CH, CH-CIHS H C.420 Cl CH, CH _(CH3) CsHí H C.421 Cl CH, C, H _S H C. 422 Cl CH 4-F-$ CSH H C.423 Cl CH 4-Cl-2-pyridyl H No. 424 Cl CH, F H č.425 Cl CH CN H no.426 Cl CH H CH, C.427 Cl CH, CH CH No.428 Cl CH CjH _S CH, č.429 Cl CH CjHj CH, C.430 Cl CH, C, H, CH, č.431 Cl CH, CH (CH 3), CH, č.432 Cl CH cyclopropyl CH, č.433 Cl CH CF, CH, C.434 Cl CH OCH CH, No.435 Cl CH OC ₂ H _p CH, č.436 Cl CH CH 1 -C ₆ H ₅ CH, C.437 Cl ch ₃ CH (CH) ₅ CIH ch ₃ 438. Cl CH E _N H ₅ CH, no.439 Cl CH, 4-F-CfHs CH C.440 Cl CH 4-Cl-2-pyridyl CH

SK 283343 Β6

Hr. R ' R R R ' C. 441 Cl CH, F CH č.442 Cl CH, CN CH C. 443 Cl CF, H H č.444 Cl CF, CH H č.445 Cl CFj CjHj H č.446 Cl CF, C, H ₇ H C.447 Cl CFj C.H) H ' č.446 Cl CFj CH (CRF, H C.449 Cl CFj cyclopropyl H c.450 Cl CF, CFj H č.451 CL CF, OCH The č.452 Cl cr ₃ OCjHj H No 453 Cl CFj Chi-CIKS H C.4S4 Cl C F, CH (CH3) CsH _s H č.455 Cl CF, C _S H _S H C. 456 • Cl CFj 4-FC _f H ₄ H č.457 Cl CFj 4-Cl-2-pyridyl H C.458 Cl CFj H C.459 Cl CFj CH H C.460 Cl CF, H CH C. 461 Cl CFj crtj CH č.462 ci CF, C ₂ H _S CH č.463 Cl CFj CjHt CH C.464 Cl CF, C.H. CH C.465 Cl CF, CH (CH 3), CH č.466 Cl CFj cyclopropyl CH, C.467 Cl CF, CFj CH, No. 468 Cl CFj OCH CH, C.469 Cl CFj OCjEs CH C.470 Cl CFj CH ₂ -C ₁ H ₅ CH C.471 Cl CFj CH (CH) C _e H _S CH C.472 Cl CFj C _{ H $ CH C.473 Cl CF, 4-F-Ph CH č.474 Cl CFj 4-Cl-2-pyridyl CH, C.475 Cl CFj F CH, C. 476 C CFj CN CH C.477 H CH H F C.478 The CH CH F C.479 H CH, c ₂ h ₅ ^F

Nr. R ³ R RF R ' C.519 H CH C ₂ H _S Cl No.520 H CH, CJH. Cl č.521 H CH, CB (CH), Cl C.522 H CH cyclopropyl Cl C. 523 H CH CFj CL č.524 H CH OCH Cl C.525 H CH CRS Cl No. 526 H CH 4-F-CíHj Cl C.527 H CFj R F C.528 H CFj CH, F C.529 H CFj CjH _S P C.530 H CFj C, H ₇ F C.531 H CFj CH (CH) j F C.532 H CFj cyclopropyl F C.S33 H CFj CF, P C.534 H CFj OCH F C.S35 H CFj CÄ P C.536 H CFj 4-P-CíHj F Ľ.537 H CFj H CjHj C.538 n CFj CH C ₂ Ms C. 539 H CFj CjHj c ₂ h. C. 540 H CFj CjHj CJH. C. 541 H CF, CH (CH), c ₂ h _p C.542 H CFj cyclopropyl CjHj C.543 H CFj CFj C _and H _p c.544 The CFj OCH C ₂ «N C.545 H CFj C <H _S CjHj C.546 H cf ₃ 4-F-CíHj C ₂ Hs No.547 H CFj H CFj C.548 H CF ₃ CH CFj C.549 H cf ₃ CjHs CFj C.550 H CFj · CJH. CFj C.SS1 H CF, CH (CH3) j cf ₃ C.5S2 H CF, cyclopropyl CFj C.553 H CFj CFj CF, C.554 H CFj OCH CFj C.555 H CFj C _f H _p CFj C.556 H CFj 4-FC <H _$ CFj C.557 H CFj H CN

Nr. R ³ R ^x RY R ' C.460 H CH c ₃ s? F č.461 H CH CH (CH3) ₂ F C.482 H CH Cycloprcpyl F C.483 H CH CFj F C.484 CH OCH F C.485 H CH C »H _S F C.486 H CH, 4-F ~ C «H _p r C.487 CH H c * C.486 H CH CH, CjH ₅ C.489 H CH CjHj C ₂ Hj C.490 H CH CJH. CJH. c.491 H CH CH (CH,) J c ₂ h ₅ C.492 H CH ₃ cyclopropyl CJH. C.493 H CH CFj CjHj C.494 H CH OCH3 CjH ₅ C.495 H CH, c ₈ h ₅ CJH. C.496 H CH 4-F-CjHs c ₂ h ₅ č.457 H CH H CFj C.498 H CH CH CFj No.499 H CH C3H5 CFj C.500 H CH CJH? CFj č.501 H CH CH (CH3) j CFj č.502 H CH cyclopropyl CFj C. 503> H CH CFj cr ₃ C. 504 H CH OCH CFj C.SOS H CH, c ₆ h ₅ CFj C.506 H CH 4-F-C5H5 CFj C. 507 H CH H CN č.508 H CH CH CN C.509 H CH C ₂ Hj CN č.510 H CH CJH. CN č.511 H CH CH (CH3) 3 CN č.512 H CH cyclopropyl CN No.513 H CH cf ₃ CN C.514 H CH, OCH CN C.515 H CH • CH _p CN č.516 H CH 4-F-CIHS CN C.517 H CH H Cl No.518 H CH CH Cl

Nr. R ³ R ^x RF R ' C.558 H CFj CH CN C.559 H CFj c ₂ h ₅ CN C.550 H CFj CJH. CN C. 561 H CFj CH (CH3) ₂ CN C.562 H CFj cyclopropyl CN No.563 H CFj cf ₃ CM C.564 The CFj OCH CN # 565 The CFj C, B, CN C.566 H CF, 4-P-Ph CN č.567 H cf ₃ H Cl # 568 H CFj CH Cl C.569 H CFj C ₂ Hs Cl C. 570 H CFj CjHj Cl No.571 H CFj CH (CH3) 1 cl C.572 H CFj cyclopropyl Cl C.573 CFj CFj Cl C.574 H CFj OCH Cl C.575 H CFj c ₅ h _p Cl C.576 H CFj 4-F-CIHS Cl C.577 CFj CH H ť C.578 CFj CH CH F C.579 CFj CH, CjHj F C.560 C F, CH CJH. P C.S61 CFj CH, CH (CH3) ₂ F C. 562 CFj CH cyclopropyl F C. 583 CFj CH CF ₃ F No.584 CFj CH OCH P C.585 CFj CH CíHj F C.586 CFj CH 4-F-CjHs F C.587 CF, CH H c ₂ h ₅ C.580 CFj CH CH CjH ₅ No.589 CF, CH, C2H5 C ₂ H _S C.590 CF, CH, c ₃ h ₇ CjH ₅ C.591 CF, CH CH (CH,) J c ₂ h _p C.592 CFj CH cyclopropyl C ₃ Hs C.593 CFj CH cf ₃ C ₂ H _S C.594 CFj CH och ₃ c ₃ h ₅ C.595 CFj CH, C, H, c ₂ h. C.S96 CFj CH 4-F-CIHS C3H5

SK 283343 Β6

Nr. R ³ R ' ry R C.597 CFj CH H CFj C.593 CFj CH CH CFj C.59 » cr, CH c ₂ h _p CF) C.600 CFj CH, CjHj CP _} C.60L C? J CH, CH (CH,) J CF) C.602 CFj CH cyclopropyl CFj no.603 CFj CH CFj CFj C.604 CFj CH OCH CFj No 605 CFj CH CjHj CPJ C.606 CFj CH 4-FC ₄ H _p CFj č.607 CFj CH _} R CN no.60 CFj CH> CH CN C. 603 CFj CH CjHs CN J C.610 CFj CH CjHj CN number 611 CFj CH CH (CH3) j CN C.612 CFj CH cyclopropyl CN C. 613 CFj CH CFj CN C.614 CPJ CH OCH CN C.61 $ CFj CH CIHS CN C.616 CFj CH 4-F-Cjiís CN No.617 CFj CH H Cl č.618 CFj CH CH Cl # 619 CFj CH c _} h ₅ Cl C.620 CFj CH CjHj Cl C.621 CFj CH CH (CH 3), Cl # 622 CFj CH cyclopropyl CL # 623 CPJ CH CFj Cl No. 624 CFj CH OCH Cl C.625 CFj CH CjHs Cl C.626 CFj CH 4-P---H, Cl C.627 CFj CFj H F č.628 CFj CFj CH F C.629 CP, CFj CjH _s F .C.63Q CFj CFj CjH ₇ F C.631 CFj CFj CH (CH3) ₂ F C.632 CFj CFj cyclopropyl ť C.633 CF, CFj C F, F C.634 CFj CFj OCH F C.635 CFj CFj C «H $ F

Nr. R ³ R RY R ^z C.636 CFj CFj 4-F-Cl ₅ F C.637 CFj CFj H C ₂ H ₅ C.638 CF] CF] CH CjHs C.639 CFj CFj CjHs c ₂ h ₅ C.640 cf ₃ CFj CjK ₇ CjHs C.641 CFj CF) CH (CH 2> 2) c ₂ h _p C.642 CPJ CFj cyclopropyl c ₂ Hs C.643 CF] CFj CFj CjH ₅ C.644 CFj CFj OCH) C2H5 C.64S CFj CFj C4H5 CjH _s C. 646 CPJ CFj 4-F-C4H5 CjHj No 647 CFj CF) H CFj C. 648 CFj CFj CHj- CFj C. 649 CFj CF) C) H ₅ CFj C.650 CFj CF) CjH ₇ CFj C.651 CFj CFj CH (CH3) j CFj C. 652 CFj CFj cyclopropyl CFj C.653 CFj CFj CFj CFj C.654 CFj CF) OCH CFj c.655 CFj CFj C _with Hs CFj C.656 CFj CFj 4-FC «H _p CFj No. 657 CFj CFj H CN C.658 CF) CF) CH CN C.659 CFj CFj CjH ₅ CN C.660 CPJ CFj CjH ₇ CN No. 661 CFj CFj CH (CtíjJ j CN č.662 CFj C F) cyclopropyl CN C. 663 CFj CFj CFj CN C.664 CFj CFj OCH CN C. 665 CFj CFj Ph CN C.666 CFj CFj 4-FC ₄ H _p CN C.667 CFj CFj The Cl C.668 CFj CFj CH Cl C.669 CFj CFj C2H5 Cl C.670 CFj CFj CjHj Cl č.671 CFj CFj CH (CH) j Cl č.672 CFj CFj cyclopropyl Cl C.673 CFj CFj CFj Cl C.674 C F, CFj OCH Cl

Nr. R ³ R ' Rf R C.675 C? J CFj c ₄ h ₅ Cl No 676 CPJ CF) 4-FC _» H _p Cl 5 C.677 Cl CH H F C.S7S Cl CH CH F C.679 Cl CH C ₅ H ₅ F C.580 Cl CH) CjH ₇ F 10 C.681 Cl CH CH (CH3) d F · C.682 ci CH Cyelopropyl F C.683 Cl CH) CF) P c.684 ci CH OCH F 15 C.685 Cl CH C _£ Hs F C.686 Cl CH 4-FC «H ₄ F C.687 Cl CH H CjH ₅ C.688 CL CH) CH C3H5 C.689 Cl CH C2E5 CjHs 20 C.690  Cl CH C) H ₇ CjHs C.691 Cl CH) CH (CH3) j c ₂ h $ C.692 Cl CH cyclopropyl C _and H ₅ C.693 Cl CH CFj c ₂ h _p 25 C.694 CL CH OCH C ₂ H _S C.695 Cl CH C _S H _S C ₂ Hj C.695 Cl CH 4-F ~ C ₆ H ₅ CIHS C.697 Cl CH H cf ₃ # 698 Cl CH CH CF) jb C.699 Cl CH C2H5 CFj c.700 ' Cl CH CJH. CFj C. 701 Cl CH) CH (CH ₃ I j CFj C.702 Cl CH cyclopropyl CFj 35 C.703 Cl CH CFj CFj C.704 Cl CH OCH CFj C. 705 Cl CH C _S H _S CFj C.706 Cl CH 4-F-C5H5 CFj 40 No.707 Cl CH H CN C.708 Cl CH CH CN C.709 Cl CH C ₂ K ₅ CN C.710 Cl CH CJH. CN 45 C, 711 Cl CH CH (CH ₂ Cl ₂₎ CN C.712 Cl CH Cyclopropyl j CN C.713 Cl CH CFj j CN

Nr. R ' R ry R ¹ C.714 CL CH OCH CN C. 715 Cl CH c _s h ₅ CN C.716 CL CH 4-F-C4H5 CN C.717 Cl CH H Cl No.718 CL CH CH Cl C.719 Cl CK i CjHs Cl C.720 Cl CH CjH ₇ Cl C.721 Cl CH CH (CH3) 1 Cl C.722 Cl CH cyclopropyl Cl C.723 CL CH CFj Cl C.724 CL CH OCH Cl C.725 CL CK i C <H ₅ Cl C. 726 Cl CH 4-F C ~ $ H $ Cl C.727 CL CFj H F. C.728 Cl CFj CH) F C.729 Cl CFj CjHs F C.730 Cl CFj C) H ₇ F C.731 Cl CFj CH (CH)} j F C.732 CL CFj cyclopropyl F C.733 C CFj CF) F C.734 Cl CFj OCH F C.735 Cl CFj C _f Hs F C.736 Cl CFj 4-F-CIHS F C. 737 · Cl CFj H C ₂ H ₅ C.738 CL CFj CH c ₂ h _p C.739 Cl CFj CjHs CjHs C.740 Cl CFj CjH ₇ CjHs C. 741 CL CFj CH (CH3) ₂ c ₂ h ₅ C.742 Cl CFj cyclopropyl C ₂ Hs C.743 Cl CFj CFj CjH _s C.744 CL CFj OCH CjHs C.745 ci CFj C _t H _p c ₂ Pcs C.746 Cl CPJ 4-F-Ph CjHs C.747 Cl CFj H CFj C.748 CL CFj CH, CFj C.749 Cl CFj C) H _S CFj C.750 Cl CFj C) H ₇ CFj C.751 CL CFj CH (CH3) j CFj C.752 Cl CFJ cyclopropyl C F,

Hr. R ³ R RY R C.753 Cl CFj CFj CFj C.754 Cl CFj OCH CFj C.755 Cl CFj C ₆ h _p CFj C.756 Cl CFj 4-F-CJH5 CFj C.757 Cl CFj H CN C.758 Cl CFj CH CN C.753 Cl CFj CjHs CN C.760 Cl CFj CjH ₇ CN C.761 Cl CFj CH (CH 3 H CN C.762 Cl CPJ Cyciopropyl CN C.763 Cl CFj CFj CN C.764 cl CFj OCH CN C.765 Cl CFj C _S H _S CN C.766 Cl CFj 4-F-CjHs CN C.767 Cl CFj H Cl C.768 Cl CFj CH Cl C.769 Cl CFj c ₂ h ₅ Cl No.770 Cl CFj CJH? Cl C.771 Cl CFj CH (CH3) j Cl C.772 Cl CFj Cyciopropyl Cl C. 773 Cl CFj CFj Cl C.774 Cl CFj OCH Cl C.775 Cl CFj c ₆ h _p Cl C.776 Cl CFj 4-FC _» H _p Cl C. 777 CH H H F C.778 CH H CH F C.779 CH H C _and H _S F C.780 CH H CjHt F C.781 CH H CH (CH3) j F C.702 CH H Cyciopropyl F C.783 CH The CFj F C.784 CH H OCH F C.785 CH H C _D H _p F C.786 CH H 4-F-C4H5 F C. 737 CH CH H F C.788 CH CK i CK i F C.789 CH CH C2H5 F No. 790 CH CH CjHj F C.791 CH CK i CH (CH3) 2 F

Nr. R ³ R RY R č.792 CH CH Cyciopropyl F C.793 CH CK i CFj F C.794 CK i CH OCH F C.795 CH CH C «H _S F C.796 CH CH 4-F-CIHS F C.797 CK i CjH ₅ H F C.799 CH c ₃ h ₅ CH F C.799 CK i CjH ₅ CjHs F C. 800 CH CjHs CjH ₇ F C. 801 CH CjHj CH (CH3) 2 F C. 802 CH CjHj Cyciopropyl F C. 803 CH CjHj CFj F C. 804 CH CjH _$ OCH) - F C.805 CH, CjHj CeKs F C.806 CH CjHj 4-F-CgKj F C.807 CH Cyciopropyl The F C.808 CH Cyciopropyl CH P C.809 CH Cyciopropyl CjKs F C.810 CH Cyciopropyl CJH? F C.811 CH Cyciopropyl CH (CH3) ₂ F C. 612 CH Cyciopropyl Cyciopropyl F C.813 CH Cyciopropyl CFj F C.814 CH Cyciopropyl OCH F C.815 CH Cyciopropyl C _D H _p F C.816 CH Cyciopropyl 4-F-CGHS F C.817 CHU CFj H F C.818 CH CFj CH F C. 819 CK i CFj CjHj F C. 820 CH CFj CJH? F C.821 CH CFj CH (CH3) 2 F C. 822 CH CFj Cyciopropyl F. C. 823 CH CPJ CFj F C. 824 CH CFj OCH F C. 825 CH) CFj c »h ₅ F C. 826 CH) CF) 4-PC ₆ H _p F C. 627 CH Cl H F C. 828 CH, Cl CK i F C. 829 CH, Cl CjHg F C. 630 CH, Cl CJH. F

Nr. R ¹ R ^x RF R ' C.831 CH Cl CHICHjlj F C.832 CH cl Cyciopropyl F C.833 -CB Cl CFj F C.834 CEJ Cl OCH F C. 835 CH Cl CjHj F C.836 CH Cl 4-F-C4Hs Γ C.837 CH F H . F C.836 CH F CH F C.839 CK i F CjHj F C.840 CH F CJH. F C.841 -CB F ' CH (CH) 2 F C. 842 CK i F Cyciopropyl F C. 843 CH F CFj F C.844 CH F OCH F C.845 CK i F C _t H _p F C.046 CH F 4-F-CTHS F C. 847 CH OCH H F C.848 CH OCH CH F C.849 CH OCH CjH _s F C.850 CH OCH CJH. F C. 851 CK i OCKj CKťCKjh F C.852 CH OCH Cyolopropyl F C. 853 CH OCH CFj F C.854 CH OCH OCH F C.855 CK i OCH . _Ct Hj F C. 85í CK i CCHj 4'F-CgKs F C.857 CH H H CjHj C.853 CH H CH) CjHj C.859 CK i H CjHs CjH ₅ C. 660 CH H CjHj CjHs C.861 CK i H CH (CH3) j CJH $ C.862 CH H Cyciopropyl CjHj C.863 CH H CFj C ₃ H $ , C.864 CH The OCH CjH _s C.865 CH H CíH _S CjH _s C, 866 CH H 4-F-CfHj CjHj C.867 CH CK i H CjHs C.86B CH CH CH CjHj C.869 CH) CH c, h ₅ CjHs

Nr. R ³ 9 * RY R C.870 CH CH C3K7 CjH _S C.871 CH, CH CH (CHjlj CjHj C.872 CH CH Cyciopropyl CjHs C.873 CH CH CFj CjHs C.874 CH CH OCH CjHj C.875 • CHj CH C <H _S c ₂ h ₅ C.876 CH CH 4-Fc _with H _s C _and H ₅ C.877 CH CjHj H CjHs No.878 • CNJ CjHj CH CaH _s C.879 CH, CjHj CjHs CjH ₅ C.880 CH CjHj CJH. cahs C.881 CK, CjHj CH (CH3) j cahs C.892 CH CjHj Cyciopropyl cahs C.8B3 CH CjHs CFj cahs C.884 CH CJH $ OCH CJH. C.885 CH CjHs C »H _S CjHj C.886 CH CjHs 4-F-CgHg CjHs C.087 CH Cyciopropyl H CjHj C.888 CH, Cyciopropyl CK i CjHs C.889 CH, Cyciopropyl CjHj CjH _s C. 890 CK i Cyciopropyl CjH ₇ CjH ₅ C.891 CH Cyciopropyl CHĺCHjl. CjHs C.892 CH Cyciopropyl Cyciopropyl CjH ₅ C.893 CH Cyciopropyl CFj CjHs C. 894 CH) Cyelcpropyl OCH CjH _s C.89S CH, Cyciopropyl C _t Hs CjH _s C.896 -CB Cycloprepyl 4-P-cghj CjHs C.897 CH) CF) H CjHg C. 898 CH CFj CH) CjHs C. 899 CH CFj CjHs CjH _S # 900 CH CFj CjHj CjHs C.901 CH CF) CH (CH3) j CjHs C.902 ' CH CFj Cyciopropyl CjHs No.903 CH CFj CFj CjHs C.904 CH CFj CCHj CjHs C.905 CH, CFj CgKs CjHs C.906 CH CFj 4-FC _t K _p CjHs C.907 CH Cl H CjHs

Nr. R kf R C.9Q8 CH, Cl CH CjHj C.909 CH Cl CjHj CjKj # 910 CH Cl CJH. CjHj C.911 CK i Cl FC _{(CH}) 2} C _S H _S # 912 CH Cl cyclopropyl CjHs C.913 CH Cl CFj CjHj C.914 CK i Cl OCH CjHs C.915 CK i Cl C _c H _p CjH _s C.916 CH) Cl 4-FC <H ₅ C, H _S C.917 CH r H CjHs C.918 CH F CH CjHs C.919 CH F CjHj CjHj C. 920 CH r C) K _? CjHj c.921 CH F CHfCKjh CJH. No. 322 CH r cyclopropyl CjHs C.923 • CHj F CFj CjH _S C. 924 CH P OCH CJH. C.92S CH F CILS CjMj C.926 CH F 4-F-CGHS C ₃ Hj C.927 CH OCH H CjHs C.928 CH OCH) CH) CjHj C.929 CK i OCH CjHj C ₂ H ₅ C.930 CH OCH CJH. CjHj C.931 CH OCH CH (CH3) j CjHj C.932 CH OCH cyclopropyl CjHs C.933 CH OCH CFj CJH. C.934 CH OCH OCH CjHj C.935 CH OCH C _S HS CjHj C.936 CH OCH 4-F-CIHS CjHj C.937 CH H H CF, C.938 CH) H CH CFj C.919 CH H CjHj CFj C.940 CH H CjK _T CFj C. 941 CK i H CH (CH3 h CFj C.942 CH H cyclopropyl CFj C.943 CH H CF, CFj C.944 CH H OCH CFj C.945 CH H C _S H $ CFj C. 946 CH H 4-F-C 'Hj CFj

Nr. R ³ R RX C.986 CH CF) 4-F-CIH) CFj C.987 CH Cl H CFj C.988 CH) Cl CH C F) C. 999 CK i CL CjHj CF) C.990 CH, Cl CjHj CFj C.991 CH, Cl CH (CH3) j CFj C.992 CH) CL cyclopropyl CF) C.993 CH Cl CF) CFj C.994 CH Cl OCH CFj C.995 CH Cl CSKS CF) C. 996 CH Cl 4-FC * H ₄ CF, C.997 CH F H CFj C.998 CH) F CH CFj C.999 CH F CjH ₅ CFj C.lOOO CH F CjHj CFj C.1001 CH F CH (CH3) j CFj C.1Ď02 CH F cyclopropyl CFj C.1003 CH) F CFj CFj C.1004 CH) F OCH) CF) C.10C5 CH F CjHj C Fj C.1006 CH F 4-F-CIKS cf ₃ C.1007 CH OCH) H cf ₃ C.1008 CH OCH CK, C?) C.1009 CH OCH) CjHj CFj No.1010 CH) OCH CjHj CFj C.1011 CH OCH CR _(CH3) j CF) C.1C12 CH) OCH cyclopropyl CF, C.1013 • CK) OCH CFj CF) C.1014 CK i OCH) OCH) CF) C.1015 CH OCH C4K5 CFj C.1016 CK i OCH 4-FC _t Hj CF) C.1017 CK) H H CN C.1018 CH _} H CH, CN No.1019 CH H CJM, CN No. 1020 CH H CjHj CN C.1021 CH H CH (CH) j CN No.1022 CH II cyclopropyl CN C. 1023 CH) H CFj CN C.1024 CH3H • OCH, CN

Nr. R ³ R ^x W R ^x No.94? CH CH H CFj C.948 CH CH CH ₃ CF) C.949 CH CH CjHs CFj C.950 CH CH CjHj CF) C.951 CH) CH CH (CH)) j CFj C.952 CH CK i cyclopropyl CFj C.953 CK i CH) CFj CF) C.954 CH CK i OCH) CF) C.955 CH CH) C «Ks CF) C.956 CK i CH 4-F-ČSKI CFj C.9S7 CH CjHj The CFj C.958 CH CjHs CH CF) C.959 CH) C, H, CjKj. CFj C.960 CH CJH. CjHj CFj C.961 CH) CjH ₅ CH (CH j} CFj C.962 CH C: K ₅ cyclopropyl CF) C.963 CH C ₂ K ₅ CFj CF) C.964 CH C ₂ H _S OCH CFj C.965 CH) CjHj CjHs CFj C. 966 CH, CjH _s 4-FC _with H ₅ CFj C.967 CH cyclopropyl H CFj 0.968 CH cyclopropyl CH CFj C.969 CH cyclopropyl CjHs CFj C.970. CH cyclopropyl CjHj CFj C.971 CH cyclopropyl CH (CH3) j . ^CF J C.972 CH cyclopropyl cyclopropyl CF) C.973 CH cyclopropyl CFj CFj C.974 CH cyclopropyl OCH3 CFj C.975 CH cyclopropyl C «H _S CFj C.976 ck, cyclopropyl 4-F-CjHs CF) C.977 CK i CF) H CFj C.978 CH C Fj CH CFj C-979 CH CFj CjK _s CFj C.980 CH CFj C3H7 CFj C.981 CH CFj CH (CH3) j CF) C 3S2 CH CFj cyclopropyl CFj C.993 CK i CFj CFj CFj C.984 CK i CFj OCKj CFj C.985 CH CFj CjHs c F)

Nr. R ³ R RF R No.1025 CH H c _s h ₅ CN C.1026 CH H 4-F-CjHj CN C.1027 CH CK i H CN C.1028 CH) CH CH, CN C.1029 CH CH) CjH _s CN No.1030 CH, CH CJH. CN C.1031 CH CH CH (CXJ »j CN No.1032 CH, CH cyclopropyl CN No 1033 CK] CH CFj CN č.1034 CH CH OCH CN C.1035 CH CH) C (H $ CN C.1036 CH CK i 4 -? - C _e H ₅ CN C.1037 CH c ₂ h $ H _ CN C.1038 CH C ₂ H ₅ CH CN C. 1039 CH) CjHj CjH ₅ CN # 1040 CK i CjHs CJH. CN C.1041 CK) CjHs CH (CH3) j CN C. 1042 CH) C »with cyclopropyl CN C.1043 CH CjHj CFj CN C.1044 CH CjHs OCH CK C.1045 CH CjHs c ₆ h ₅ CN C.1046 CH CjHs 4-F-CeIIj CN C.1047 CH cyclopropyl H CN # 1040 CH) cyclopropyl CH CN C.1049 CH cyclopropyl CJH. CN C.10S0 CH, cyclopropyl CJH. CN C.1051 CH cyclopropyl CK (CH ₃ hr CN C.1052 CH cyclopropyl cyclopropyl CN C.1053 CH cyclopropyl CFj CN C.1054 CH cyclopropyl OCH CN 0.1055 CH) cyclopropyl cghj CN C.1056 CH) cyclopropyl 4-FC _» H _S CN C. 1057 CH) CFj H CN C.1058 CH CFj CH, CN C.1059 CH, CFj cahs CN C. 1060 CH C F) CJH. CN C.1061 CH CF, CH (CH3) j CN C.1062 CH CF) cyclopropyl CN C.1063 CH CF, CF) CH

SK 283343 Β6

Nr. R ¹ R ' BX R ' # 1064 ch ₃ CF, OCH CN ' C.1065 CK i CFj Crffc CN C.1066 CH CFj 4-F-CIKS CN C.1067 CH Cl H CN C 1068 CH  Cl CH CN C.1069 . CH Cl CjHs CN C.1070 CH Cl CJK CN C.1071 CH Cl CH (CH3) ₂ CN C.1072 CH Cl Cyclcpropyl CN C.1073 CH Cl CFj CN C. 1074 CH Cl OCH CN C.1075 ch ₃ Cl C ₅ Hs CN C.1076 ch ₃ Cl 4-PC ₆ H ₅ CN C.1077 CK i F H CN C.1078 CH F CH CN C.1079 CK i C ₅ H ₅ CN č.1080 CH P CjK ₇ CN c.1081 CH F ch (ck ₃ ) ₂ CN C.1082 ch ₃ F cyclopropyl CN 1083 CH F CFj CN C. 1094 ch ₃ F OCH CN No.1085 ch ₃ F C _with H ₅ CN C.1086 CH F 4-F-cghj CN C.1087 CH OCH H CN C.1088 CH OCH . CHi CN C.1089 CH OCH C2H5 CN C.1090 CH OCH ₃ CjHj CN C.1091 CH OCH CH <CK i) j CN C.1092 CH OCH cyclopropyl CN C.1093 CH OCH CFj CN no.1094 CH OCH □ CH CN C.1095 CH OCH c _s h ₈ CN C.1096 CH OCH 4-F-cghj CN č.1097 CH H II Cl C.1098 CH H CH Cl C.1099 CH H c ₂ h _p Cl c.1100 ch ₃ H CJH. Cl C.1101 ch ₃ H CH (CH3) j cl C.1102 ch ₃ H cyclopropyl cl

Hr. R ³ R R R ¹ C.1142 CH CF) cyclopropyl Cl C.1143 CH CF) CFj Cl C.1144 CH CFj OCH Cl C.114C CH CF, C «H _S Cl C.1146 CH) CF,. 4-F-CIH, CL no.1147 CH) Cl H Cl C.1148 CH, Cl CH Cl C. 1149 CH Cl CjRj Cl c.1150 CH Cl CJK Cl 'C.1151 CH Cl CH _{(CH3) 2} Cl C.1152 CH Cl cyclopropyl Cl C.1153 CH ci CFj Cl C.1154 CH Cl OCH Cl C.1155 CH Cl C * H _S Cl C.1155 CH Cl 4-F-CjHs Cl C.1157 ’CHj F H OR C.1158 CH F CH Cl C.1159 CK i F CjHs Cl C.1160 CH F CjHj Cl C.1161 ch ₃ F CH _{(CH3) 2} Cl C. 1162 CH F cyclopropyl Cl C.1163 CH F CFj Cl C.1164 CH F OCH CL C.1165 CH F CíH _s CL No. 1166 CH, F 4-F-CgWj Cl C.11S7 CH OCH H Cl C.1168 CH OCH CH) Cl route No. 1169 CH OCH CjHj Cl C.1170 CH OCH CjHi Cl No.117 . CH OCH CH (CH3) ₂ Cl C.1172 CH OCH cyclopropyl CL C.1173 CH och ₃ CFj Cl C.1174 CH OCH OCH Cl C.1175 CH, OCH C «H C C.1176 CH OCH 4-FC <H _p Cl C.1177 CH CH ch ₂ ch ₂ C.1178 CK i CF) ch ₂ ch ₂ C.1179 CFj CH CHjCHj c.1180 CH C) H _S CHjCHj

Nr. R ³ R ' RX R ' C.1103 CH H CFj Cl C.1104 CH H OCH Cl C.1105 CH H CsHj Cl C.1106 CH H 4-F-CjHs Cl C.1107 CH CH H Cl C.1108 CH CH CH cl C-1109 CH CH c ₃ h _p Cl C.1110 ch ₃ CH C ₃ Hi Cl C.1111 CK i CH) CH (CH3) j Cl C. 1112 . CH CH cyclopropyl Cl C.1113 CH CH) CFj CL C.1114 CH CH OCH Cl C.1115 CH CH C _S Hs. Cl C.1116 CH CK i 4-FC ₆ H ₄ Cl C.1117 CH CjHs H ci C.1119 CH CjH _s CH Cl c.1119 ch ₃ CjHs C _Z H _S Cl C.1120 CH CjK ₅ CJH. Cl C.1121 CH CjHj CH (CH) j Cl C.1122 CH CjH ₅ cyclopropyl Cl C.1123 CH CjHs CFj Cl No.1124 CH C ₂ K ₅ OCH Cl C.1125 CH C _Z H _S c ₆ h » Cl C.1126 CH C ₂ H _p 4-F-CsH _p Cl C.1127 CH cyclopropyl The Cl C.1128 CH cyclopropyl CH Cl C.1129 CH cyclopropyl C _S H _S Cl c.1130 CK i cyclopropyl c ₃ h, Cl C.1131 CH cyclopropyl CH (CH3) 1 Cl C.1132 CH cyclopropyl cyclopropyl cl No. 1133 CH cyclopropyl CFj Cl C.1134 CH Cyclcpropyl och ₃ Cl C.1135 CH cyclopropyl CeH _s Cl C.1136 CH cyclopropyl 4-F-Cl ₅ L1 C.1137 CH CF, H Cl C.1138 CH CFj CH Cl C.1139 CH CFj C ₂ H _p Cl C.1140 CH CFj CjH ₇ Cl C.1141 CH CF) CH (CIIj) ₂ Cl

Nr. R ³ R Ry | r * C.1181 C ₂ Hj CH CHjCHa C.1182 Cl CH CHjCHj C.1103 CH Cl CHjCHj C.1184 CH CH CH ₂ CW _and CH _a C.1185 C8j CFj CH ₂ CH ₃ Cl ₂ C.1186 Cl) CH CH ₂ CH ₂ CH ₂ C.1187 ch ₃ CaHj CHjCHjCHj C.1188 c ₂ h _p CH CH ₂ CH ₂ CK ₂ c.1189 Cl CH CH ₂ CB ₂ CHj C.1190 CH Cl ch ₂ ch ₂ ch ₂ C. 1191 CH CH CH ₂ CH ₂ CH ₂ CH ₂ C.1192 CH) CFj CHjCHjCHjCEj C.1193 CF ₃ CH CHjCHjCHjCHj C.1194 CH CjHs CH ₂ CH ₂ CH ₂ C.1195 CjH ₅ CH CHjCHjCHjCHj C.1196 Cl CH CKjCKjCHjCHa C.1197 CH Cl CH ₂ CH ₂ CH ₃ CH ₂ C.1198 CH ₃ CH ₃ CH H H C.1199 CHjCHj CH CH H C.1200 CHjCHj CH) CjHj H C.1201 CHjCHj CH) CJH) H C. 1202 CHjCHj CH C «H H C.1203 CHiCHj CH TA (CH) j H C.1204. CHjCHj CH cyclopropyl H C.1205 CrfjGHj CH) CFj M C.1206 CHjCHj CH OCH H C.1207 CHjCHj CH OCjHj H C.1208 CHjCKj CH CH-cghj H No 1209 CHjCHj CH CH (CH) C _S Hj H C.1210 CHjCHj CK i C «H _S H C.1211 CHjCHj CH 4-F-CIHS H C.1212 CHjCHj CK i 4-Cl-2-pyridyl H C.1213 CHjCHj CH F H C.1214 CHjCHj CH CH H C.1215 CHjCHj CjHj H H C.1216 CHjCHj CjHj CH H C.1217 CHjCHj CjH ₅ CjHj The C. 1218 CHjCHj CJH $ CJH) H C.1219 CHjCHj CjHs C, H, H

Nr. R ³ R RF R C.1220 CHjCHj CjHs CH (CH) j H C.1221 CHjCHj CjH _s cyclopropyl H C.1222 CHjCHj CjH _s cf ₃ H C.1223 CHjCHj CjH _s och ₃ H C.1224 CHjCHj CjH ₅ OCjHj H C.1225 CHjCHj CjH _S CH-Ph H C. 1226 CHjCHj CjH ₅ CHICHjJCíHs H N.122? CHjCHj CjHs C <Hj H C-1228 CHjCHj CjH _S 4 _PC-TH $ H 1229 CHjCHj CjHs 4-Cl-2-pyridyl H C.1230 CHjCHj CjH _s H C.1231 CHjCHj CJH. CN H C.1232 CHjCHj cf ₃ n H C.1233 CH ₂ CH 3 CFj ch ₃ H C.1234 CHjCHj CFj CjH ₅ H No1235 CHjCHj CFj CjHj H C.1236 CHjCHj CFj C < »s H C.1237 CHjCHj cf ₃ CH (CH> j H C.1238 CHjCHj cf ₃ cyclopropyl H C.1239 CHjCHj cf ₃ CFj The # 1240 CHjCHj cf ₃ OCH H No 1241 CHjCHj cf ₃ OCjH _s R C.1242 CHjCX ₃ CFj CH-CIKS H C.1243 CHjCHj CFj CK (CH ₃ ) C ₄ H $ H 1244 CHjCHj CFj CjHs H C. 1245 CHjCHj CFj L-F-CjHj H C.1246 CH ₃ CH ₃ CFj 4-Cl-2-pyridyl H C.1247 CHjCHj CFj F H C.1248 CHjCHj CFj CU The C.1249 CHjCHj Cl H H C.1250 CH ₂ CH 3 Cl CH H č.1251 CHjCHj Cl CjHj H C.1252 CHjCHj Cl CjH ₇ H C.1253 CHjCHj Cl C _t H _p H C.1254 CHjCHj Cl CH (CH3) j H C.1255 CHjCHj Cl cyclopropyl H C.1256 CH ₂ CH ₃ Cl CFj H C.1237 CHjCM ₃ Cl OCH H C.1258 CHjCHj Cl OCjH _; H

Nr. R ³ R RF R ^r C.1298 CHiCHj CH) r CH C.1299 CH ₃ CH ₃ CH CN CH c.1300 ch ₂ ch ₃ CjHs H CH C. 1301 CHjCHj CjHs ch ₃ CH C.1302 CHjCHj CjH ₅ CjHs CH C.1303 CHjCHj CjHj CjHj CH C.1304 ch ₂ ch ₃ CjHs C «Hj CH c.1305 CHjCHj CjHs CH (CH) j CH C.1306 CHjCHj CjHs cyclopropyl CH C.1307 ch ₂ ch ₃ CjHs CFj CH C.1308 ch ₂ ch ₃ CjH _S ocm ₃ CH C.1309 ch ₂ ch ₃ CjH ₅ OCjHs CK i C.1310 CHjCHj CjH ₅ ch ₂ -c ₆ h _p CK i C.1311 CH ₂ CH 3 CjHs CH (CH 3 CH 3 CH 3) CH C.1312 CHjCHj CjH _S C _T hs CH C.1313 CHjCHj CjHs 4-F-CIKS CH C.1314 ch ₃ ch ₃ CILS 4-Cl-2-Pyrldyl CH C.1315 ch ₂ ch ₃ c ₂ h ₅ F CK i C.1316 CHjCHj C ₂ Hs CN CH C.1317 CHjCHj CFj H CK i C.1318 ch ₂ ck3 CFj CH CH C.1319 CH ₂ CH 3 CFj c ₂ h ₅ CH C.1320 ch ₂ ch ₃ cf ₃ c ₃ h, CH C.1321 ch ₂ ch ₃ CFj CjHs CH) C.1322 CH ₃ CH ₃ CFj .CHĺCHjh CH C.1323 CK ₃ CK ₃ CFj cyclopropyl CK i C.1324 ch ₂ ch ₃ CFj CFj CH 1325 CK ₂ CHj CFj OCH CH C.1326 ch ₂ ch ₃ CFj OCjHs CH C.1327 ck ₂ ch ₃ CFj CH-CjKj CH C.1323 CH ₃ CH ₃ CFj CM (CH 3) C ₄ H ₅ CH C. 1329 CH ₂ CH 3 CFj C «H _S CK i c.1330 Chicha) CFj 4-F-CSKS CH C.1331 CHjCHj CFj 4-Cl-2-pyridyl CH C.1332 ch ₂ ch ₃ CFj P CH c.1333 CHjCHj CFj CN CH 1334. ch ₂ ch ₃ Cl H CH C.1335 CH ₂ CH 3 Cl ch ₃ ch ₃ C.1336 CHjCHj Cl CjH _s CH

Nr. R ' R RF R ^x C.1259 CH ₂ CK ₃ Cl CH ₂ -C ₅ H ₅ H no.1260 CHjCHj Cl CH _(CH3) C _e H ₅ H C.1261 CHjCHj Cl C «H _S H C. 1262 ch ₂ ch ₃ Cl 4 -? - CIHS H C.1263 CHjCHj Cl 4-Cl-2-pyridyl H C.1264 ch ₂ ch ₃ Cl F H C.1265 CH ₂ CH 3 Cl CN H C. 1266 CH _and CH 3 OCH H H C.1267 CHjCHj OCH ch ₃ H C.1268 CHjCHj OCH CjHs H C.1269 CHjCHj OCH) CjHj H C. 1270 CHjCHj OCH) CIH) Π # 1271 CK ₂ C »j OCH CH (CH) j The No1272 CHjCHj OCH) cyclopropyl H C.1273 CHjCHj OCH cf ₃ H C.1274 CH ₃ CH ₃ OCH) och ₃ H 1275 CHaCHj OCH) OCjHs H 1275 CH ₂ CH 3 OCH) CK i-CfiHs H C.1277 CHjCHj OCH CH (CH ₃ ) Cl 5 H C.1279 CHjCHj OCH C «H _p H C.1279 ch ₂ ch ₃ OCH 4-FC ₆ Hs H c.1280 CHjCHj OCH) 4-Cl-2-Fyridyl H C.1281 CH ₃ CH ₃ OCH F H C.1282 CHjCHj OCH) CN H C.1283 CHjCHj CH H CH C.1284 CHjCHj CH CK i CH C.1285 CHjCHj CH CjH ₅ CH) C.1286 ch ₂ ch ₃ CH CJH. CH No.1287 CHjCHj CH C «Hj CH C.1288 CHjCHj ch ₃ CH (CH3) ch ₃ C.1289 CHaCHj CH cyclopropyl CH) C.1290 ch ₂ ch ₃ CH CFj ch ₃ C.1291 CHaCHj CH OCH CH) C.1292 CHjCHj CH OCjHs CH C. 1293 CHjCHj CH CH-C _e H _p CH C.1294 CHjCHj CH CH (CH 3) C ₄ H ₅ CH C.129S CH ₃ CH ₃ CH C _D H _p CH C.1296 CHjCHj ch ₃ 4-FC ₄ Hs CH C.1297 CHjCHj ch ₃ 4-Cl-2-pyridyl CH

Nr. R ³ R ^x RF R C.1337 CH ₂ CH 3 Cl CjH _T ch ₃ C.1338 CK ₂ CHj CL c ₄ h, CH C.1339 CHjCHj Cl CH (CH3) ₃ CH C.1340 C'1 ₂ CHj Cl cyclopropyl CH C.1341 ch ₂ ch ₃ Cl CFj ch ₃ C.1342 CHjCHj Cl OCH CH C.1343 CH ₂ CH 3 CL OCjHs CH C.1344 CHaCHj CL CH-Ph CH C.1345 CH ₂ CH _} Cl CH (CH ₃ ) C ₄ H 5 CH C.1346 CHjCHj Cl C ₍ H _S ch ₃ C.1347 CH ₂ CH 3 Cl 4-FC ₆ H ₄ CH C.1348 CHjCHj Cl 4-Cl-2-pyridyl CH C.1349 ch ₂ ch ₃ Cl F CH c.1350 CHjCHj Cl CN CH C.1351 ch ₂ ch ₃ OCH H CH C.1352 ch ₂ ch ₃ OCH CH CH C.1353 CHjCHj OCH CjHs CH C.1354 CH ₂ CH 3 OCH CjH ₇ CH C.1355 CH ₂ CH 3 OCH CjHs CH C.1356 ch ₂ ch ₃ OCH CH (CH3) 5 CH C.1357 ch ₂ ch ₃ OCH cyclopropyl CH C.1358 ck ₂ ch ₃ och ₃ CFj CH C.1359 CHaCHj OCH OCH CH C.1360 CH ₂ CH 3 OCH oc ₂ h _p CH C.1361 CH ₂ CH 3 OCH CH ₂ -C ₆ H 5 CH C.1362 CH ₂ CH 3 OCKj CH (CH3) Cl2 _s CH C.1363 CHaCHj OCH C ₄ Hs CH C.1364 CHjCHj OCH 4-FC ₆ H _p CH c.1365 ch ₂ ch ₃ OCH 4-Cl-2-pyridyl CH C.1366 ch ₂ ch ₃ OCH F CH C.1367 CHjCHj OCH CN CH

It is known that inhibitors of mitochondrial respiration of fungi can be used as fungicides such as antimycin (cf. "Inhibitors to Mitochondrial Functions", Hrsg .: Rieske et al .; Pergamon Press, Oxfrod 1981, p. 110). However, there are various disadvantages to the practical use of antimycin, such as heavy and costly production and insufficient stability under the conditions of use, for example in plant protection.

Mitochondrial respiration is the basis of metabolism. Energy in the form of adenosine triphosphate (ATP) is collected in the mitochondria by respiration. Finally, inhibition of mitochondrial respiration results in inhibition of ATP production.

For example, the compounds of formula (I) of the invention inhibit mitochondrial respiration of noxious fungi. In fungi that have been treated with the compounds of the invention, the attenuation of the ATP metabolism or the formation of the ATP compound is reduced. an energy-dependent process of metabolism, thus eliminating fungal growth and dying fungi.

Accordingly, mitochondrial respiration is inhibited in animal pests.

The compounds of formula (I) are therefore suitable for protection against animal pests, in particular from the class of insects, arachnids and nematodes, and against harmful fungi.

The compounds of formula (I) exhibit excellent activity against a broad spectrum of phytopathogenic fungi, in particular from the class of Ascomycetes, Deuteromycetes, Phycomycetes and Basidiomycetes. They are partially systemically effective and can be used as foliar and soil fungicides in plant protection.

They are of particular importance in the protection against numerous fungi in various crop plants, such as wheat, rye, barley, oats, rice, corn, grass, bananas, cotton, soybeans, coffee, sugar cane, vine, fruit and ornamental plants and vegetables such as are cucumbers, beans, tomatoes, potatoes and pumpkin plants, as well as the seeds of these plants.

Especially suitable for protection against the following plant diseases: Ervsiphe graminis (powdery mildew) for cereals, Erisiphe cichoracearum and Sphaerotheca fuliginae on pumpkin plants, Podosphera leucotricha on apples, Unicula necator on vines, Puccinia on rye, Rhinoceros on rye, Rhinoceros on grain lawn, Ustilago species on grain and sugar cane, Venturia inaequalis on apples, Helminthosporium grain, Septoria nodorum on wheat, Botrytis cinerea (gray mold) on strawberries, vegetables, ornamental plants and vines, Cercospora arachidicola on peanuts, Pseudoceridesides on wheat, barley, Pyricularia oryzae on rice, Phytophthora infestans on potatoes and tomatoes, Fusarium and Verticilium on various plants, Plasmopara viticola on vine, Pseudocercosporella on hops and cucumbers, Altemaria on vegetables and fruits, as well as Mycospheres .

The compounds of formula (I) are further suitable for controlling harmful fungi and fungi in the protection of material (e.g., wood, paper, paint dispersions, fibers and possibly fabrics) and in the protection of stocks.

The compounds of formula (I) are used by treating the plants, seeds, materials or soil to be protected from fungal attack with a fungicidally effective amount of the active compounds. The use is carried out before or after attack of the materials, plants or seeds by the fungi.

They can be used in the form of customary formulations such as solutions, emulsions, suspensions, dust, powder, pastes or granules. The form of use depends on the intended use, and in any case is intended to ensure a fine and uniform distribution of the compound of the invention. The formulations are prepared in a known manner, for example by mixing the active ingredient with a solvent and / or carriers, as desired, using emulsifying and dispersing agents, and in the case of water as a diluent, other organic solvents such as co-solvents may be used. Basically suitable excipients are: diluents such as aromatic compounds (e.g. xylene), chlorinated aromatic compounds (e.g. chlorophenols), paraffins (e.g. petroleum fractions), alcohols (e.g. methanol, butanol), ketones (e.g. cyclohexanone), amines ( such as ethanolamine, dimethylformamide) and water; carriers such as natural stone meal (e.g. kaolin, clay, talc, chalk) and synthetic stone meal (e.g. high disperse silicic acid, silicates); emulsifying agents such as non-ionic and anionic emulsifiers (e.g. polyoxyethylene fatty alcohol ether, alkylsulfonates and arylsulfonates) and dispersing agents such as lignosulfite lyes and methylcellulose.

The fungicidal compositions generally contain between 0.1 and 95, preferably between 0.5 and 90% by weight of active ingredient.

Depending on the type of effect desired, the amounts used for plant protection vary between 0.01 and 2.0 kg of active substance per ha.

In the treatment of seed, generally 0.001 to 0.1 g, preferably 0.01 to 0.05 g, of active ingredient per kilogram of seed is required.

When used in the protection of material or stocks, the amount of active substance applied depends on the type of application and the desired effect. The usual amounts for protecting the material are, for example, 0.001 g to 2 kg, preferably 0.005 g to 1 kg, of active ingredient per meter of cubic material to be treated.

The compositions according to the invention can be used as fungicides together with other active substances, for example with herbicides, insecticides, growth regulators, fungicides or even fertilizers.

When mixed with fungicides, in many cases the fungicidal efficacy spectrum is increased.

The following list of fungicides with which the compounds of the invention may be used together illustrates but does not limit the possibilities of combination:

sulfur, dithiocarbamates and derivatives thereof, such as iron dimethyldithiocarbamate, zinc dimethyldithiocarbamate, zinc ethylenebisdithiocarbamate, magnesium ethylenebisdithiocarbamate, magnesium zinc ethylenediamine-bis-dithiocarbamate, tetramethylthiurpuramate complex, tetramethylthiurpuramate complex, Zinc N, N'-propylene-bis-dithiocarbamate, zinc Ν, Ν'-propylene-bis-dithiocarbamate, N, N'-polypropylene-bis (thiocarbamoyl) disulfide;

nitro derivatives, such as dinitro (1-methylheptyl) phenyl crotonate, 2-sec-butyl-4,6-dinitrophenyl-3,3-dimethyl acrylate, 2-sec-butyl-4,6-dinitrophenylisopropyl carbonate, 5-nitroisophthalic acid diisopropyl ester;

heterocyclic compounds such as 2-heptadecyl-2-imidazoline acetate, 2,4-dichloro-6- (o-chloroanilino) -s-triazine, O, O-diethylphthalimidophosphonothioate, 5-amino-1- [bis- (dimethylamino)) phosphonyl] -3-phenyl-1,2,4-triazole, 2,3-dicyano-1,4-dithioanthraquinone, 2-thio-1,3-dithiolo [4,5-b] quinoxaline, 1- (methyl ester) (butylcarbamoyl) -2-benzimidazolecarbamine, 2-methoxycarbonylaminobenzimidazole, 2- (furyl- (2)) -benzimidazole, 2- (thiazolyl- (4)) -benzimidazole, N- (1,1,2,3-tetrachloroethylthio) tetrahydrophthalimide , N-trichloromethylthiothetrahydrophthalimide, N-trichloromethylthiophthalimide, N-dichlorofluoromethylthio-N ', N'-dimethyl-N-phenyldiamide sulfuric acid, 5-ethoxy-3-trichloromethyl-1,2,3-thiadiazole, 2-rodanomethylthiobenzyl -dichloro-2,5-dimethoxybenzole, 4- (2-chlorophenylhydrazono) -3-methyl-5-isoxazolone, pyridine-2-thio-1-oxide, 8-hydroxyquinoline, or its copper salt, 2,3-dihydro- 5-carboxanilido-6-methyl-1,4-oxathiin, salt, 2,3-dihydro-5-carboxanilido-6-methyl-1,4-oxathiin-4,4-dioxide, 2-methyl- anilide 5,6-Dihydro-4H-pyran-3-carboxylic acid anilide39

2,5-dimethylfuran-3-carboxylic acid anilide, 2,4,5-trimethylfuran-3-carboxylic acid anilide, 2,5-dimethylfuran-3-carboxylic acid cyclohexylamide, N-cyclohexyl-N-methoxy- 2,5-dimethylfuran-3-carboxylic acid, 2-methylbenzoic acid anilide, 2-iodobenzoic acid anilide, N-formyl-N-morpholino-2,2,2-trichloroacetal piperazine-1,4-dimethylbenzoic acid - (2,2,2-trichloroethyl) formamide, 1- (3,4-dichloroanilino) -1-formylamino-2,2,2-trichloroethane, 2,6-dimethyl-N-tridecylmorpholine, or salts thereof, 2, 6-dimethyl-N-cyclododecylmorpholine or its salts, N- [3- (p-tert-butylphenyl) -2-methylpropyl] -cis-2,6-dimethylmorpholine, N- (p-tert-butylphenyl) - 2-methylpropyl] piperidine, 1- (2- (2,4-dichlorophenyl) -4-ethyl-1,3-dioxol-2-y] -ethyl) -1H-1,2,4-triazole 1- [2- (2,4-dichlorophenyl) -4-n-propyl-1,3-dioxolan-2-yl-ethyl] -1H-1,2,4-triazole, N- (n-propyl) -N- (2,4,6-trichlorophenoxyethyl) -N-imidazolylurea, 1- (4-chlorophenoxy) -3,3-dimethyl-1- (1H-1,2,4-triazol-1-yl) -2-butanone, l - (4-chlorophenoxy) -3,3-dimethyl-1- (1H-1,2,4-triazol-1-yl) -2-butanol, (2RS, 3RS) -1- [3- (2-chlorophenyl) -2- (4-Fluorophenyl-oxan-2-ylmethyl) -1H-1,2,4-triazole, α- (2-chlorophenyl) -α- (4-chlorophenyl) -5-pyrimidinemethanol, 5-butyl- 2-dimethylamino-4-hydroxy-6-methylpyrimidine, bis- (p-chlorophenyl) -3-pyridinemethanol, 1,2-bis (3-ethoxycarbonyl-2-thioureudo) benzole, 1,2-bis- (3-methoxycarbonyl) -2-thioureudo) benzole, strobilurines such as methyl E-methoxyimino- [α- (o-tolyloxy) -o-tolyl] acetate, methyl E-2- [2- [6- (2-cyanophenoxy) pyrimidine-4- yl-oxy] phenyl] -3-methoxyacrylate, methyl E-methoxyimino [α- (2-phenoxyphenyl)] acetamide, methyl E-methoxyimino- [α- (2,5-dimethylphenoxy) -o-tolyl] acetamide anilinopyridines such as 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, phenylpyrrole such as 4- (2,2-difluoro-1,3-benzodioxol-4-yl) -pyrrole-3-carbonitrile, cinnamic acid amides such as 3- (4- chlorophenyl) -3- (3,4-dimethoxyphenyl) morpholide of acrylic acid, as well as miscellaneous e fungicides such as dodecylguanidine acetate, 3- [3- (3,5-dimethyl-2-oxycyclohexyl) -2-hydroxyethyl] glutarimide, hexachlorobenzene, DL-methyl-N- (2,6-diraethylpheynl) -N-furoyl (2 ) -alaninate, DL-N- (2,6-dimethylphenyl) -N- (2-methoxyacetyl) alanine methyl ester,

N- (2,6-dimethylphenyl) -N-chloroacetyl-DL-2-aminobutyrolactone, DL-N- (2,6-dimethylphenyl) -N- (phenylacetyl) -alanine methyl ester, 5-methyl-5-vinyl-3- (3,5-Dichlorophenyl) -2,4-dioxo-1,3-oxazolidine, 3- [3,5-dichlorophenyl- (5-methyl-5-methoxymethyl) -1,3-oxazolidine-2,4-dione 3- (3,5-dichlorophenyl) -1-isopropylcarbamoylhydantoin, N- (3,5-dichlorophenyl) -1,2-dimethylcyclopropane-1,2-diimide carboxylic acid, 2-cyano- [N- (ethylaminocarbonyl) - 2-Methoxyimino] acetamide, 1- [2- (2,4-Dichlorophenyl) pentyl] -1H-1,2,4-triazole, 2,4-difluoro-α- (1H-1,2,4- N- (3-chloro-2,6-dinitro-4-trifluoromethylphenyl) -5-trifluoromethyl-3-chloro-2-aminopyridine, 1 - ((bis- (4-fluorophenyl) methylsilyl) trioazoline) -1-methylbenzhydryl alcohol methyl) -1H-1,2,4-triazole.

The compounds of formula (I) are furthermore suitable as effective protection against pests of the insect, arachnid and nematode class. They can be used in plant protection as well as in the field of hygiene, stock protection and in the veterinary field as pesticides.

The harmful insects include, for example, Lepidoptera, such as Agrotis ypsilon, Agrotis segetum, Alabama argillacea, Anticarsia gemmatalis, Argyresthia conjugella, Autographa gamma, Bupalus piniarius, Cacoecia murinana, Cheucobistura brumata, Cheimatobistura brumata, Cheimatobia brumata, Cheimatobia brumata, Cyndia pomonella, Dendrolimus pini, Diaphania nitidalis

Diatraea grandiosella, Earias insulana, Elasmopalpus lignosellus, Eupoecilia ambiquella, Evetia bouliana, Feltia subterranea, Galleria mellonella, Graphilitha molebella, Heliothis armigera, Helithis virescens, Heliothis zea, Heliothis zea, , Lambdina fiscellaria, Laphygma exigua, Leucoptera coffeella, Leucoptera scitella, Lithocolletis blancardella, Lobesia botrana, Loxistege sticticalis, Lymantria monacha, Lygiatria clerkella, Malacosoma neustria, Perennial moss, Orestia brassicain, Orgyia brassicain, Orgyia brassicain, saucia, Phalera bucephala, Phthorimaea operculella, Phyllocnistis citrella, Pieris brassicae, Plathypena scabra, Plutella xylostella, Pseudoplusia inclusens, Rhyacionia frustrana, Scrobipalpula absolututa, Spitropodia spiller, Spargodontis piller, Spiperopodoptera and litura, Traumatopoea pityocampa, Tortrix viridana, Trichopulsia ni, Zeiraphera canadensis.

Among the beetles (Coleoptera), for example, Agrilus sinuatus, Agriotes lineatus, Agriotes obscurus, Amphimallus solstitialis, Anisandrus dispar, Anthonomus grandis, Anthonomus pomorum, Atomaria linearis, Blastophagus piniperda, Blitophaga undata, Bruchus rufusanisis, Bruchus rufusanisus, Nebulosa, Cerotoma trifurcata, Ceuthorrhynchus assimilis, Ceutrhorrhynchus napi, Chactocnema tibialis, Conoderus vespertinus, Crioceris asparagi, Diabrotica longicomis, Diabrotica 12-punctat, Hybrobius viris, Epinotis viris , Ips typographus, Lema bilineata, Lema malonopus, Leptinotarsa decemlineata, Limonius califomicus, Lissorhoptrus oryzophilus, Melanotus communis, Meligontes hippocastani, Melolontha melolontha, Oulema oryzaeusioriorus, Ortiorhynususioriorus, Ortiorhyrosus, oriorza aga sp., Phyllopertha horticola, Phyllotreta nemorum, Phyllotreta striolata, Popillia japica, Sitona lineatus, Sitophilus granaria.

Of the Diptera family, for example, Aedes aegypti, Aedes vexans, Anastrepha ludens, Anopheles maculipennis, Ceratitis capitata, Crysomya bezziana, Chrysomya hominivorax, Crysomya macellaria, Daisy, Cordylobia anus, Cordylobia anusrope, Cordylobia anus, canicularis, Gasterophilus intestinalis, Glossina morsitans, Hematodia irritans, Haplodiplosis equestris, Hylemyia platura, Hypoderma lineata, Liriomyza sativae, Liriomyza trifolii, Lucilia caprina, Lucilia cuprina, Lycoria pectoralis, Muscis stestica, Muscina stestica Oscinella frit, Pegomya hysocyami, Phorbia antiqua, Phorbia brassicae, Phorbia coarctata, Rhagoletis cerasi, Rhagoletis pomonella, Tabanus bovinus, Tipula oleracea, Tipula paludosa.

From the order of the tufts (Thysanoptera), for example, Frankliniella fusca, Frankliniella occidentalis, Frankliniella tritici, Scirtothrips citri, Thrips oryzae, Thrips palmi, Thrips tabaci.

Among the Hymenoptera, for example, Athalia rosae, Atta cephalotes, Atta sexdens, Atta texana, Hoplocampa minuta, Hoplocampa testudinea, Monomorium pharaonis, Solenopsis geminata, Solenopsis invicta.

From the range of Heteroptera, for example, Acrostcmum hilare, Blissus leucopterus, Cyrtopeltis notarus, Dysdercus cingulatus, Dysdercus intermedius, Eurygaster intergriceps, Leptoglossus phyl lopus, Lygus lineolaratis, Lygus lineolarisis, Lygus lineolaratis, Lygus lineolaratis, Lygus lineolarisis, Lygus.

Among the family of homoptera (Homoptera), for example, Acyrthosiphon onobrychis, Adelges laricis, Aphidula nasturtii, Aphis fabae, Aphis pomi, Aphis sambuci, Brachycaudus cardui, Brevicoryne brassicae, Cerosipha gossypii, Dreyfusia nismaneolae, Avenae, Macrosiphum euphorbiae, Macrosiphon rosae, Megoura viciae, Metopolophium lugens, Pemphigus bursarius, Perkinsiella saccharidica, Phorodon humuli, Psylla Mali, Psylla piri, Rhopalomyzus ascalonicus, Rhopalosiphum malamis, Sappinis sapis, Sappaphis malais, Sappaphis malais, Sappaphis mala Viteus vitifolii.

From the series of termites (Isoptera), for example, Calotermes flavicollis, Leucotermes flavipes, Reticulitermes lucifugus, Termes natalensis.

In the range of Orthoptera, for example, Acheta domestica, Blatta orientalis, Blattella germanica, Forticula auricularia, Gryllotalpa gryllotalpa, Locusta migratoria, Melanoplus femurrubrum, Melanoplus mexicanus, Melanoplus spp. Peregrina, Stauronotus maroccanus, Tachycines asynamorus.

From the class of Arachnoides, for example, arachnids (Acarina) such as Amblyomma americanum, Amblyomma variegatum, Argas persicus, Boophilus annulatus, Boophilus decoloratus, Boophilus microplus, Brevipalpus phoenicis, Rbyobia praetiosa, Dermacentor silvarum, Iotetusriatodes, Eotetranrichus, Eotetranychus Omithodorus moubata, Otobius megnini, Paratetranychus pilosus, Dermanyssus gallinae, Phyllocoptruta oleivora, Polyphagotarsonemus latus, Psoroptes ovis, Rhipicephalus appendiculatus, Tetraweed, Tetranususus, Tetranyususus, Tetranyususus, Tetranyususus, Tetranyususus, Tetranyususus, Tetranyususus

From the class of nematodes, for example root nematodes, for example Meloidogyne hapla, Meloidogyne incognita, Meloidogyne javanica, cyst-forming nematodes, e.g. Dipsaci, Heliocotylenchus multicinctus, Longidorus elongatus, Radopholus similis, Rotylenchus robustus, Trichodorus primitivus, Tylenchorhynchus claytoni, Tylenchorhynchus dubius, Pratylenchus neglectus, Pratylenchus penetrans, Pratylenilenusus curvitatus.

The active compounds may be administered alone, in the form of their formulations or in dosage forms prepared therefrom, for example in the form of directly sprayable solutions, powders, suspensions or dispersions, emulsions, oil dispersions, pastes, dusting agents, spreading agents, granules by spraying, fogging, dusting, sprinkling or watering. The dosage forms depend on the intended use; in any case, the finest possible distribution of the active compounds according to the invention should be ensured.

The concentrations of the active compounds in the ready-to-use preparations can vary considerably.

They are generally between 0.0001 and 10%, preferably between 0.01 and 1%.

The active compounds can also be applied with a good result by the Ultra Low Volume (ULV) method, whereby formulations with more than 95% by weight can be used. or even an active substance without additives.

The application rates of the active ingredients for pest control are 0.1 to 2.0 kg, preferably 0.2 to 1.0 kg ha, under outdoor conditions.

For the production of directly sprayable solutions, emulsions, pastes or oil dispersions, suitable fractions of medium or high boiling mineral oils, such as kerosene or diesel fuel, coal tar oils such as vegetable or animal oils, aliphatic, cyclic or aromatic hydrocarbons, for example benzene, toluene, xylene, paraffin, tetrahydronaphthalene, alkylated naphthalenes and derivatives thereof, methanol, ethanol, propanol, butanol, chloroform, carbon tetrachloride, cyclohexanol, cyclohexanone, chlorobenzene, isophorone, strong polar solvents such as dimethylformamide, dimethylsulfoxide, N-methylsulfoxide, N-methylsulfoxide, Water.

Aqueous use forms can be prepared from emulsion concentrates, pastes or wettable powders (dusting agents, oil dispersions) by adding water. For the production of emulsions, pastes or oil dispersions, substances alone or dissolved in an oil or solvent, homogenized with wetting agents, adhesives, dispersing or emulsifying agents in water may be used. However, concentrates consisting of the active ingredient, wetting agents, adhesives, dispersing or emulsifying agents and, optionally, solvent or oil, which are suitable for dilution with water, may also be prepared.

Suitable surfactants are alkali metal salts, alkaline earth metal salts, ammonium salts of lignminesulfonic acid, naphthalenesulfonic acid, phenolsulfonic acid, dibutylnaphthalenesulfonic acid, alkylarylsulfonates, alkylsulfates, alkylsulfonates, sulfonates of the fatty alcohol and their fatty acids, and their fatty acids, alkaline earth metal salts, salts of sulfated fatty alcohol glycol ether, condensates of sulfonated naphthalene and naphthalene derivatives with formaldehyde, condensates of naphthalene or of naphthalenesulfonic acid with phenol and formaldehyde, polyoxyethylene octylphenol ether, ethoxylated isooctylphenol, octylphenol, nonylphenol, alkylphenyl polyglycol ethers, tributylphenyl polyglycol ether, alkylaryl polyether alcohols, condensates of ethylene oxide fatty alcohol, ethoxylated castor oil, polyoxyethylene alkyl ether, ethoxylated polyoxypropylene, lauryl alcohol polyglycol eracetal, sorbitester, lignin sulphite waste liquor and methylcellulose.

Powder, dusting and spreading agents are prepared by mixing or grinding the active ingredients with a solid carrier.

The formulations generally comprise between 0.01 and 95% by weight, preferably between 0.1 and 90% by weight. of the active substance. The active compounds are employed in a purity of from 90% to 100%, preferably 95% to 100% (according to NMR spectrum).

DETAILED DESCRIPTION OF THE INVENTION

I. 5 parts by weight of a compound of the invention are intimately mixed with 95 parts by weight of fine kaolin. In this way, a dusting composition is obtained which contains 5% by weight of active ingredient.

II. 30 parts by weight of the compound of the invention are intimately mixed with a mixture of 92 parts by weight of a powdered silica gel and 8 parts by weight of paraffin oil sprayed onto the surface of the silica gel. In this way a modified active substance with a good adhesion (23% by weight of active substance) is obtained.

III. 10 parts by weight of a compound of the invention are dissolved in a mixture consisting of 90 parts by weight of xylene, 6 parts by weight of a composite product consisting of 8 to 10 moles of ethylene oxide per mole of oleic acid N-monoethanolamide, 2 parts by weight of calcium dodecylbenzenesulfonic acid. consisting of 40 moles of ethylene oxide per mole of castor oil (9% active ingredient content).

IV. 20 parts by weight of a compound of the invention are dissolved in a mixture of 60 parts by weight of cyclohexanone, 30 parts by weight of isobutanol, 5 parts by weight of a composite product consisting of 7 moles of ethylene oxide per mole of isooctylphenol, 5 parts by weight of a composite product consisting of 40 moles of ethylene oxide per mole. castor oil (16% active ingredient content).

V. 80 parts by weight of a compound of the invention are intimately mixed with 3 parts by weight of diisobutylnaphthalene-α-sulfonic acid sodium salt, 10 parts by weight of lignin sulphonic acid sodium salt from sulphite waste liquors and 7 parts by weight of a silica gel powder and ground in a hammer mill. content of 80% by weight of active substance).

VI. 90 parts by weight of the compound of the invention are mixed with 10 parts by weight of N-methyl-α-pyrrolidone to form a solution suitable for application in small drops (content 90% by weight of active substance).

VII. 20 parts by weight of a compound of the invention are dissolved in a mixture consisting of 40 parts by weight of cyclohexanone, 30 parts by weight of isobutanol, 20 parts by weight of a product composed of 7 moles ethylene oxide per mole isooctylphenol and 10 parts by weight of a product composed of 40 moles ethylene oxide per mole castor. oil. Pouring and carefully mixing the solution in 100,000 parts by weight of water produces an aqueous dispersion containing 0.02% by weight of the active ingredient.

VIII. 20 parts by weight of the compound of the invention are intimately mixed with 3 parts by weight of diisobutylnaphthalene-α-sulfonic acid sodium salt, 17 parts by weight of lignin sulphonic acid sodium salt from sulphite waste liquors and 60 parts by weight of silica gel powder and ground in a hammer mill. Mixing the mixture in 20,000 parts by weight of water produces a spray solution containing 0.1% by weight of the active ingredient.

Granules, for example coated, impregnating or homogeneous granules, may be prepared by binding the active ingredients to solid carriers. Solid carriers are, for example, mineral soils such as silica gel, silicic acid, silica gel, silicates, talc, kaolin, aluminous, limestone, lime, chalk, bolus, loess, clay, dolomite, diatomaceous earth, calcium sulfate, magnesium sulfate, magnesium oxide , ground plastics, fertilizers such as ammonium sulfate, ammonium phosphate, ammonium nitrate, urea and plant products such as cereal flour, tree bark flour, wood and nut shells, cellulose powder and other solid carriers.

Alternatively, the active compounds may be added immediately prior to the application of oils of various types, herbicides, fungicides, other pests, bactericides. These compositions may be admixed with the compositions of the invention in a weight ratio of 1: 10 to 10: 1.

Synthesis examples

The procedures outlined in the following Synthesis Examples were used to appropriately modify the starting compounds to provide additional compounds of Formula (I). The compounds thus prepared are listed in the following tables together with physical data.

The chemical shift (in ppm) of the 1 H-NMR spectrum was measured against tetramethylsilane (br = broad signal, s = singlet, d = doublet, m = multiplet).

1. Preparation of intermediates

1. a Synthesis of 2-fluorobenzaldehyde cyanohydrin

To a suspension of 179 g of potassium cyanide in 500 ml of diethyl ether, 171 g of 2-fluorobenzaldehyde was added dropwise with stirring at room temperature, followed by a solution of 148 g of ammonium chloride in 600 ml of water over 5 minutes under ice-cooling. After stirring for 2 hours at room temperature (about 25 ° C), the phases are separated, the ether phase is washed once with dilute NaCl solution, three times with water, dried and concentrated. This afforded 191 g (91%) of the title compound as an oil.

1 H-NMR (CDCl 3): 4.20 (s, br, 1H, OH), 5.75 (s, 1H, CHOH), 7.05-7.75 (m, 4H, phenyl-H).

1. b Synthesis of 2-fluoromethanedioic acid methyl esterimide hydrochloride

235 g of cyanohydrin from 1a are dissolved in 1000 ml of diethyl ether and 100 g of methanol. To this mixture, 126 g of a 55% HCl solution in ether (69 g HCl) was added dropwise over 15 minutes under ice-cooling. After standing for 20 hours at room temperature (about 25 ° C), the precipitate is filtered off and allowed to dry under a stream of nitrogen. Yield: 108 g of the title compound.

1 H-NMR [D ₆ -dimethylsulfoxide (D ₆ -DMSO)]: 3.05 (s, 3H, OCH 3), 5.12 (s, 1H, CHOH), 6.25 (s, br, 1H, CHOH) 7.10-7.60 (m, 4H, phenyl-H).

1. c Synthesis of 2-fluoro-butyric acid methyl ester

The product of 1.b (108 g) was heated with stirring in 450 ml of water under reflux for half an hour. After cooling, it is extracted three times with ether, the ether phase is dried and concentrated. 77 g of the title compound are obtained.

1 H-NMR (D ₆ -DMSO): 3.62 (s, 3H, OCH ₃ ), 5.40 (s, 1H, CHOH), 6.30 (s, br, 1H, CHOH), 7.10 - 7.40 (m, 4H, phenyl-H).

1. d Synthesis of 2-fluorophenylglyoxylic acid methyl ester

To 77.1 g of the product from 1. c in 700 ml of CH ₂ Cl ₂ is added 3.2 g of KBr, 8.7 g of Na ₂ HPO ₄ , 7.6 g of NaH ₂ PO ₄ , 2.8 g of 2.2, 6,6-tetramethylpiperidine-N-oxide as well as 600 ml of water. With stirring at 20 ° C, 343 g of a 12.5% NaOCl solution were added dropwise over half an hour. The reaction mixture was allowed to stir for 1 hour. The organic phase was separated, the aqueous phase was extracted once with CH ₂ C1 _2nd The combined organic phases are washed three times with water, dried and concentrated. 72.3 g of the title compound are obtained.

1 H-NMR (CDCl 3): 3.97 (s, 3H, OCH ₃ ), 7.08 (dd, 1H, phenyl-H), 7.16 (dd, 1H, phenyl-H), 7.33 ( dd, 1H, phenyl-H), 7.93 ppm (dd, 1H, phenyl-H).

1. e Synthesis of 2-fluorophenylglyoxylic acid methylamide

To a solution of 36 g (0.2 mol) of the product from 1. in 150 ml of tetrahydrofuran at 25 ° C was added 17.1 g (0.22 mol = 1.1 equivalents) of a solution of methylamine (40% solution in methylene chloride). water). After stirring for 3 hours, the solvent was removed under reduced pressure. The residue thus obtained is crystallized. 30.0 g of the title compound is obtained (m.p. 98-100 ° C).

1 H-NMR (CDCl 3): 3.01 (d, 3H, NCH 3), 6.98 (d, 1H, NH), 7.05-7.18 (m, 2H, phenyl-H), 7.60 (dd, 1H, phenyl-H), 7.94 (t, 1H, phenyl-H).

1. f Synthesis of butane-2,3-dione-O-methyloxime

CH ₃

To 18.7 g of (E) -diacetylmonoxime in 100 ml of methanol was added 43.8 g of pyridine, followed by dropwise dropwise stirring with 17 g of o-methylhydroxylamine hydrochloride dissolved in 50 ml of methanol. After three hours, the reaction mixture is concentrated to dryness, the residue is taken up in ether and washed with dilute hydrochloric acid, then the ether layer is dried and concentrated. 24 g of the title compound are obtained. 1 H-NMR (CDCl ₃ ): 2.01 + 2.09 (2xs, 6H, CH 3), 3.98 (s, 3H, OCH 3), 8.59 (s, 1H, OH).

1. g Synthesis of 3-methylpent-3-en-2-one oxime

CH ₃

To a solution consisting of 50 g (0.5 mol) of 3-methylpent-3-en-2-one in 500 ml of methanol is added 80 g (1 mol) of pyridine and 35 g (0.5 mol) of hydroxylamine hydrochloride. After stirring at room temperature (about 25 ° C) for 12 hours, the reaction mixture was freed from the solvent under reduced pressure. The residue is taken up in tert-butyl methyl ether. The organic phase is washed with water and dilute hydrochloric acid, dried and concentrated under reduced pressure. 48.0 g of the title compound are obtained as white crystals (m.p. 70-72 ° C).

1 H-NMR (CDCl 3): 1.78 (d, 3H, CH 3), 1.85 (s, 3H, CH 3), 2.04 (s, 3H, CH 3), 6.01 (g, 3 H, = CH), 9.98 (s, 1H, OH).

1. h Synthesis of 2-oxo- [2- (1-metatolylethylideneamininooxy) phenyl] acetic acid methyl ester

To a mixture of 4 g of 3-methylacetophenooxime in 20 ml of dimethylacetamide (DMA) is added 3.0 g of potassium tert-butanolate at 20 ° C, stirred for half an hour and then a mixture of 5 is added dropwise at 15 ° C. 9 g of fluorophenylglyoxylic acid methyl ester in 20 ml of DMA. After three hours at 20 ° C, a sufficient amount of methyl t-butyl ether and aqueous NH ₄ Cl solution are added, the phases are separated and the organic phase is washed three times with NH ₄ Cl solution, then dried and concentrated. Column chromatography gave silica gel 4.1 g of the title compound.

1 H-NMR (CDCl 3): 2.40 + 2.41 (2 xs, 6H, CH 3), 3.85 (s, 3H, OCH ₃ ), 7.14 (m, 1H, phenyl-H), 7 22-7.63 (m, 6H, phenyl-H); 7.80 (dd, 1H, phenyl-H).

1. i Synthesis of [2- (2-methoxyimino-1-methylpropylideneamininooxy) phenyl] oxoacetic acid methyl ester

To 2.3 g of the product from 1.f was added 2.0 g of potassium tert-butanolate, the mixture was stirred for half an hour, and then 3 g of 2-fluorophenylglyoxalic acid methyl ester from 1. d, dissolved in 6 ml of DMA (dimethylformamide), maintaining the temperature at 20 ° C by ice cooling. The reaction mixture was then further stirred for 2 hours. For work-up, a solution of NH ₄ Cl was added to the reaction mixture and the aqueous phase was extracted several times with ether. The combined organic phases were washed with ammonium chloride solution, dried and concentrated. 3.9 g of the title compound were obtained.

1 H-NMR (CDCl 3): 2.09 + 2.22 (2 xs, 6H, CH 3), 3.88 + + 4.01 (2 xs, 6H, OCH ₃ ), 7.50 (dd, 2H, phenyl-H), 7.82 (d, 1H, phenyl-H).

1. j Synthesis of 2-oxo- [2- (2-methoxyimino-1-methylpropylideneamininooxy) phenyl] acetic acid N-methylamide

A mixture consisting of 1.4 g (10.5 mmol) of the product of 1.f, 1.2 g (11 mmol) of potassium tert-butoxide and 1.8 g (10 mmol) of the product of 1.e and 30 ml of dimethylacetamide is stirred for 1 hour at 60 ° C. The reaction mixture thus obtained is poured into ice water. The aqueous mixture was extracted twice with CH ₂ Cl ₂ . The combined organic phases are dried with Na ₂ SO ₄ and then concentrated under reduced pressure. 1.3 g of the title compound was obtained as a brown oil.

1 H-NMR (CDCl ₃ ): 2.02 + 2.20 (2 xs, 6H, CH ₃ ), 2.91 (d, 3H, NCH ₃ ), 3.98 (s, 3H, OCH 3), 6 , 89 (d, 1H, NCH), 7.09 (d, 1H, phenyl-H), 7.31 (t, 1H, phenyl-H), 7.49 (t, 1H, phenyl-H), 7 65 (d, 1H, phenyl-H).

1. k Synthesis of 2-oxo- [2- (1-ethoxyethylidenaminooxy) phenyl] acetic acid methyl ester

1H, phenyl-H), 7.38 (d, 1H, phenyl-H), 7.54 (t, 1H, phenyl-H),

7.76 (d, 1H, phenyl-H).

1. 1 Synthesis of 2-oxo- [2- (3-methylpent-3-en-2-ylideneminooxy) phenyl] acetic acid methyl ester

A mixture consisting of 3.0 g (20 mmol) of the product of 1. g,

2.2 g (20 mmol) of potassium tert-butoxide and 20 ml of methanol were evaporated to dryness after stirring at approximately 25 ° C.

The residue was taken up in 20 ml of dimethylformamide, a solution of 3.5 g (20 mmol) of the product of 1 d and 10 ml of dimethylformamide was added, and the resulting mixture was stirred at 50 ° C for 2 hours. The reaction mixture was diluted with water and extracted with tert-butyl methyl ether. The combined organic phases were dried and concentrated under reduced pressure. The residue (4.0 g oil) was purified by column chromatography [silica gel, cyclohexane / ethyl acetate (10 → 5/1)]. 2.0 g of the title compound was obtained as an oil.

1 H-NMR (CDCl 3): 1.82 (d, 3H, CH ₃ ), 1.90 + 2.04 (2 xs, 6H, CH 3), 3.85 (s, 3H, OCH 3), 6.14 (q, 2H, -CH), 7.10 (t, 1H, phenyl-H), 7.52 (m, 2H, phenyl-H), 7.80 (d, 1H, phenyl-H).

2. Preparation of compounds I

2.a Synthesis of methoxyimino- [2- (1-metatolylethylideneamininooxy) phenyl] acetic acid methyl ester

J 2 CH ₂ CH 3

CH ₃

To a solution of 22.7 g of 1-ethoxyethylaminoxime in 300 mL of toluene was added 24.7 g (0.22 mol) of potassium tert-butanolate, followed by stirring for 2 hours. The reaction mixture thus obtained was concentrated at 40 ° C under reduced pressure and the residue was taken up in dimethylformamide.

A solution of 40.1 g (0.22 mol) in 250 ml of dimethylformamide was added dropwise at 15 ° C. After 3 hours, water was added to the reaction mixture, and the mixture was extracted three times with tert-butyl methyl ether. The combined organic phases were dried over Na ₂ SO ₄ and concentrated under reduced pressure. The remaining oil was purified by column chromatography [silica gel, cyclohexane / ethyl acetate (10: 1)]. 30 g of the title compound were obtained as an oil.

1 H-NMR (CDCl 3): 1.28 (t, 3H, CH ₃ ), 2.08 (s, 3H, CH ₃ ), 3.83 + 3.88 (2 xs, 6H, OCH ₃ ), 4 18 (g, 2H, OCH ₂ ), 7.05 (t,

0.8 g of the ketoester from 1.h was stirred in 7 ml of methanol with 0.24 g of o-methylhydroxylamine hydrochloride and 0.23 g of pyridine at 50 ° C for one hour. Then the methanol was removed in vacuo and the residue was taken up in ethyl acetate, washed with dilute hydrochloric acid and then with water, dried and concentrated. A crude yield of 6.3 g was obtained, which crystallized slowly. After purification by column chromatography, it was isolated in two fractions

2.2 g of the title compound, m.p. 90 ° C. 1 H-NMR (CDCl 3): 2.32 + 2.34 (2 xs, 6H, CH ₃ ), 3.82 + + 4.09 (2 xs, 6H, OCH ₃ ), 7.10 (t, 1H) , phenyl-H), 7.21-7.61 (m, 7H, phenyl-H).

2. b Synthesis of 2-methoxyimino-N-methyl-2- [2- (1-metatolylethylideneamininooxy) phenyl] acetic acid methylamide

about

It was dried over Na ₂ SO ₄ and concentrated under reduced pressure. 1.1 g of the title compound was obtained as a yellow oil.

2. e Synthesis of 3-methoxy- [2- (2-methoxyimino-1-methylpropylideneamininooxy) phenyl] acrylic acid methyl ester

To 0.5 g of the oxime ether from 2 and 4 ml of tetrahydrofuran was added portionwise at reflux temperature 2.9 ml of a 40% aqueous solution of methylamine. The reaction mixture was further stirred overnight, then concentrated under reduced pressure, taken up in acetic acid ester, washed with NaCl solution, dried and concentrated. 0.4 g of the title compound was obtained as pale yellow crystals, m.p. 109-111 ° C.

1 H-NMR (CDCl 3): 2.35 + 2.40 (2xs, 6H, CH 3), 2.92 (d, 3H, NCH ₃ ), 4.00 (s, 3H, OCH 3), 6.68 (d, 1H, NH), 7.10 (t, 1H, phenyl-H), 7.22-7.62 (m, 7H, phenyl-H).

2. c Synthesis of methoxyimino- [2- (2-methoxyimino-1-methyl-propylidenaminooxy) phenyl] acetic acid methyl ester

ABOUT

0.83 g of o-methylhydroxylamine was added to 3 g of the crude product from 1 and 20 ml of methanol at room temperature (about 25 ° C). After 3 hours the solvent was removed in vacuo and the residue was subjected to silica gel column chromatography eluting with cyclohexane / ethyl acetate 15: 1. 1.3 g of the title compound was isolated as a second fraction, m.p. 93-94 ° C. 1 H-NMR (DMSO ₆ ): 2.01 + 2.04 (2xs, 6H, CH ₃ ), 3.71 (s, 3H, NCH ₃ ), 3.95 (s, 6H, OCH ₃ ), 7.12 (m, 1H, phenyl-H), 7.31 (d, 1H, phenyl-H), 7.43 (d, 2H, phenyl-H).

2. d Synthesis of methoxyimino- [2- (2-methoxyimino-1-methylpropylidenaminooxy) phenyl] acetic acid methylamide

The crude product of Preparation Example 1, i.e. 2.4 g of this product dissolved in 10 ml of DMF, was added dropwise to a mixture of 5.6 g of methoxymethyltriphenylphosphonium chloride and 2.5 g of a 30% solution of sodium methylate (in methanol). in 20 ml DMF. After three hours, 30 ml of water was added dropwise with cooling and the precipitate formed was filtered off with suction. Chromatography over silica with cyclohexane / ethyl acetate as eluent yielded 1.8 g of the title compound as a pale yellow solid (m.p. 101 ° C).

1 H-NMR (CDCl 3): 2.09 + 2.11 (2 xs, 6H, CH ₃ ), 3.65 + + 3.82 (2 xs, 6H, OCH ₃ ), 7.01 (t, 1H) , phenyl-H), 7.22 (m, 2H, phenyl-H), 7.45 (d, 1H, phenyl-H), 7.49 (s, 1H, phenyl-H).

2. f Synthesis of 3-methoxy- [2- (1-ethoxyethylidenaminooxy) phenyl] acrylic acid methyl ester

Method A

The product of 2. c (0.6 g) in 10 ml of tetrahydrofuran was allowed to stir overnight with 3.6 g of a 40% aqueous methylamine solution at room temperature (about 25 ° C). To remove the solvent under reduced pressure and add water, isolate and dry the resulting crystalline precipitate, 0.3 g of the title compound was obtained (mp 122-123 ° C).

1 H-NMR (CDCl 3): 2.05 + 2.12 (2 xs, 6H, CH 3), 2.90 (d, 3H, NCH ₃ ), 3.92 + 3.98 (2 xs, 6H, OCH) ₃ ), 6.70 (m, 1H, NH), 7.07 (t, 1H, phenyl-H), 7.22 (d, 1H, phenyl-H), 7.38 (t, 1H, phenyl- H, 7.49 (d, 1H, phenyl-H).

Method B

To a solution of 1.1 g (4 mmol) of the product of 1.j in 30 ml of methanol was added 0.4 g (4.2 mmol) of o-methylhydroxylamine hydrochloride and 0.5 g (6 mmol) of pyridine. After 2 hours at 50 ° C, the solvent and the base were removed under reduced pressure. The residue was taken up in ethyl acetate and washed twice with water and dilute hydrochloric acid. The organic phase was

To a solution consisting of 6.9 g (0.02 mol) of methoxymethyltriphenylphosphonium chloride, 3.1 g (0.017 mol) of sodium methanolate (30% in methanol) and 30 ml of dimethylformamide was added dropwise a solution of 2.7 g (0.01 mol) of the product from 1 to 10 ml of dimethylformamide. After three hours, the reaction mixture was poured into ice water and extracted with tert-butyl methyl ether. The combined organic phases were dried over Na _; SO ₄ and concentrated under reduced pressure. The residue thus obtained was purified by column chromatography [Kieselgel, toluene / ethyl acetate (10/1)]. 1.9 g of the title compound was obtained as an oil.

1 H-NMR (CDCl 3): 1.26 (t, 3H, CH 3), 2.00 (s, 3H, CH ₃ ), 3.65 (s, 3H, OCH ₃ ), 3.80 (s, 3H) , OCH), 4.18 (q, 2H, _OCH2), 6.95 (t, IH, phenyl-H), 7.20 (d, IH, phenyl-H), 7.30 (t, IH, phenyl-H), 7.43 (d, 1H, phenyl-H), 7.50 (s, 1H, = CH).

2. g Synthesis of 2-methoxyimino- [2- (1-ethoxyethylidenaminooxy) phenyl] acetic acid methyl ester

ABOUT

To a mixture consisting of 1.0 g (4.0 mmol) of the product from

1. To 5 ml of methanol was added 0.25 g of o-methylhydroxylamine and the mixture was stirred for about 24 hours at a temperature of about 25 ° C. The reaction mixture was concentrated under reduced pressure and the remaining residue was taken up in CH ₂ C1 _2nd The organic phase was washed with water, dried and concentrated under reduced pressure. 1.0 g of the title compound [2: 1 isomer mixture] was obtained. 1 H-NMR (CDCl 3): 1.26 (t, 3H, CH ₃ ), 2.01 + 2.05 (2 xs, 6H) , CH ₃ ), 3.86 + 4.04 (2 xs, 6H, OCH ₃ ), 4.10 (q, 2H, OCH ₂ ), 6.94 - 7.50 (m, 4H, phenyl-H) .

2. h Synthesis of 2-methoxyimino- [2- (phenylmethylidenaminooxy) phenyl] acetic acid methyl ester

To a solution of 1.0 g (3.4 mmol) of the product from 1 to 5 ml of methanol was added 1.8 g (17 mmol) of benzaldehyde and 0.33 g of methanesulfonic acid, and the mixture thus obtained was stirred for 1 hour. The solution was concentrated under reduced pressure and the remaining residue was taken up in CH ₂ C1 _2nd The organic phase was washed with water, dried and concentrated. The resulting residue was purified by column chromatography [toluene / ethyl acetate (10/1)]. 400 mg of the title compound was obtained as an oil.

1 H-NMR (CDCl 3): 3.95 (s, 3H, OCH ₃ ), 4.02 (s, 3H, OCH ₃ ), 7.30-7.68 (m, 9H, phenyl-H), 8 , 05 (s, 1H, = CH).

2. i Synthesis of 2- [2- (3-methylpent-3-en-2-ylideniminooxy) phenyl] but-2-enoic acid methyl ester

To a mixture of 4.7 g (14.5 mmol) of ethyltriphenylphosphonium chloride in 20 ml of dimethylformamide was added at 25 ° C.

2.2 g (12 mmol) of sodium methanolate solution (30% in methanol). A solution of 2.0 g of the product from 1.1 in 10 ml of dimethylformamide was then added dropwise to the mixture thus obtained, and the mixture was stirred for a further two hours. Water was then added to the reaction mixture, and the mixture was extracted with tert-butyl methyl ether. The combined organic phases were dried and concentrated under reduced pressure. The remaining residue was purified by column chromatography [cyclohexanoluene / ethyl acetate (10/1)]. 700 mg of the title compound was obtained as a solid [m.p. 90-93 ° C].

1 H-NMR (CDCl 3): 1.72 (d, 3H, CH 3), 1.80 (d, 3H, CH 3), 1.89 (s, 3H, CH 3), 2.03 (s, 3H, CH 3) ), 3.68 (s, 3H, _OCH3), 6.03 (pseudo q, IH, CH), 6.98 to 7.35 (m, 5H, phenyl-H, CH), 7, 50 (d, 1H, = CH).

Table I (1)

R 'R ³

I ©

Nr. R ¹ R ' R physical data KD .1 the CH 3-C ₃ -C ₆ H ₄ 90 ° C 1 (1) .2 lb CH 3-CH 3 -C ₄ H ₄ 109-111C 1 (1), 3 la CH 4-CH-Cítq 99 ° C 1 (1), 4 lb CH 4-CH-CM 109'C 1 (1) .5 14 -CH ₂ - (CH ₂ ) j -CH ₂ - O1 1 (1) .6 la @ ³ H: 1.32 (t, 3H); 2.05 (s, 3H); 3.92 (a, 3H); 4.05 (s, 3H); 4.09 (q, 2H). 5.95-7.42 t, 4H)

Nr. R ¹ R ³ R ⁴ physical data KD .7 id CH OC ₂ H _p MS: 1.28 (t, 3H); 2.03 (s, 3H)? 3.76 (s, 3H); 3.34 4.08 (ie, 2H); 6.98 (t, 1H); 7.8 (d, 1H); 7.21 (t, 1H); 7.42 7.50 (s, 1H). 1 (1) .9 la 128 ° C 1 (1) .9 lb rV ^! 135-137 ° C

Nr. rl R ^} R ⁵ R ⁶ physical data 1 (2) .1 la CH 4-F-CIHS CHU 112 ° C 1 (2) .2 la CH CK ₃ CH 93'C t (2) .3 lb CH CH CH 122 - 123'C 1 (2) .4 Id CH 4-FC _€ H _p CK i 141'C 1 (2) .5 ib CH 4-FC _with H _} CH 139'C 1 (2) .6 id CH CH CH (CH3) j 103'c 1 (2) .7 Id CH CK i CH ÍDI'C 1 (2) .8 Id CK i CH TA (CH) 2 97'C I (2> .9 la CH CH CjH ₅ 106 - 109'C 1 (2) .10 lb CH CH CjHs 119 - 123'C t (2) .11 la CjHj ch ₃ CH 92 - 97'C C (21 lb CjHj CH CH 97 - ÍOO’C 1 (2) .13 la CH CK i TA (CH) j 74®C 1 (21:14 Id c ₂ h _p CK i ch ₃ 1711, 1647, 1542, 1288, 1266. 1132 1 (2) .15 Id CH CH CjHj 78 - 00’C 1 (2) .16 for CK ₃ CH CSjOCH 51 - 53’C K2J.L7 Id ch ₃ CK i CHjCCK 59 - 63 ° C 1 (21:18 lb ch ₃ CK i CHjC -CH 146 - 149'C 1 (21:19 lb CH C2H5 CH 113 ° C 1 (2) .20 Id CH CjH ₅ CH 1713, 1630, 1541, 1258, 1128, 1051.

Nr. Rf R ^J R ⁵ R ' physical data - 1 (2) .21 la CH C ₂ Hj ch ₃ 1732, 1453, 1224, 1207, 1073, 1050. 1 (2), 22 lb CsHj ch ₃ CjHs 101 - 103'C 1 (2) .23 Id c ₂ Hs CH C ₂ H ₅ Mp = 92 ° C 1 (2) .24 la C ₂ w ₅ CHj ' CjHj 102 0 * 1 (2), 25 lb C ₂ Hs CH CH (CH3) j 92 - 94'C 1 (2) .26 Id c ₂ h ₅ CH CH (CH3) ₂ 74 - 78'C 1 (2) .27 la C2H5 CH CH (CH3) ₂ 93 - 96'C 1 (2) .28 lb c ₂ Hs CH CHjCeCH 95 -100’C Γ (2J.29 rd Cjíís CK i ch ₂ c «ch 1712, 2637, 1542, 1252, 1218, 1129. 1 (2) .30 la c ₂ h _p CK i CH ₂ CbCH 1731, 1480, 1453, 1227, 1207, 1072. 1 (2) .31 lb CJH $ CH ch ₃ 122-125 ^e C 1 (2) .32 Id C ₄ H ₅ ch ₃ CH 116-120'C 1 (2) .33 ia CsHj CH CH 107 - 113'C 1 (2) .34 la CH OCH (CH3) ₂ CH 7 ° C r (2) .35 lb ch ₃ CHjCHj CHjOČH 100-1030c 1 (2) .36 la ch ₃ CHjCHj CHjOCH 94-97 ^e C 1 (2) .37 Id CH CHjCHj CH ₂ OCH O1 6 (2) .38 la CH CHjCHj CHjCHj Mp 91-95 ° C 1 (2) .39 lb ch ₃ CH ₂ CH 3 CHjCHj Mp 91-93 ° C 1 (2) .40 Id CH CHjCHj CH ₂ CH 3 01 1 (2) .41 le CH CHjCHj CHjCHj O1 1 (3) .42 la ch ₃ CHjOCHj CH O1 t (2) .43 lb CH CHjOCHj ch ₃ 95-100 ° C

Table I | 3>:

Nr. R ¹ R ^} R ry R ¹ physical iíAede I (3) .1 ia ch ₃ H CIH, H 102'C K3) .2 lb CH H c «h ₅ H 155 ° C 1 (3) .3 la CHi H 4-FC _t H $ H 109 ^c C 1 (3) .4 ib CK i H 4-F-CjHs H 72 - 75'C 1 (3) .5 ra CH H 4-Cl-CIHIE H 141'C 1 (31 .6 ib ΓČHj H 4-Cl-CjKä M 147 ^c C 1 (3) .7 la CH, The CH, cm ₃ 56-60 ° C

M sorbitol + 0.01 M KH ₂ PO ₄ + 0.0004 M disodium ethylenediaminetetraacetic acid + 0.3% bovine serum albumin + 0.0007 M KCN + 6 x 10 ^-6 Ubichinone-50 + + 0.01 M Sodium succinate + 0.15% cytochrome C (pH 7.5) added a solution of the test compound in dimethylsulfoxide and the reduction rate of cytochrome C was determined photometrically by increasing the extinction at 546 nm. A sample with the corresponding amount of pure DMSO served as a control. The inhibition value for the indicated concentrations of the active substance is then calculated as follows.

Nr. R ¹ R ' R ^x RY physical data 1 (3) .8 ib ch ₃ H CH, CH 85 - 88'C 1 (3) .9 ib ch ₃ CH CH H 53-54 ^B C 1 (3) .10 ib CH CH CH (CH3) j The 69-71 ^e C 1 (3), 11 la ch ₃ CH3 CK ₃ H 81-53 ^e C 1 (3) .12 Xa CH CH CH (CH3) 2 H 90-92 ^e C 1 (3) .13 Id CH3 CH CH, H 90 - 93’c 1 (3), 14 .M CH ch ₃ CK (CK ₃ ) 3 H 78 - 80'C 1 (3) .15 Xa CH CH CH H 69-72C 1 (3) .1 ' Ie CH CH CH (CH _{3) 3} H 56 - 59'C 1 (3) .17 la CH H H C4H5 88 ^and C 1 (3) .16 la CH CH, CjH ₅ H 83 - 86'C 1 (3) .19 ib CK i CK, CjH ₅ H 81 - 86'C 1 (3) .20 Id CH CH C2H5 H 77-79 * C 1 (3) .21 Ie CH CH, C _and H ₅ H O1 1 (3) .22 la CH, CH CjH ₇ H 80 - 82'C 1 (3) .23 ib CH CH C3H7 H 99-100 ° C 1 (3) .24 Id CH, CH, C3H7 H Mp 74-75 ° C 1 (3), 25 Ie CH CH, C ₃ H ₇ H Mp 54-56 ° C 1 (3) .26 ib CH CH 4-FC ₆ H ₃ H Mp 140-142 ° C 1 (3) .27 la CH CH C ₆ K ₅ H Mp 115-117 ° C 1 (3) .2b la CH CH F-i-CjHi H Mp 103-105 ° C 1 (3) .29 Id CH, CH C ₆ Hs H 108 ^with C 1 (3) .30 Id CH CH 4-FC _with H ₄ H LoFlo ^ C 1 (3) .31 s CH CH CeH _S The Mp 81-83 ° C 1 (3) .32 Xe CH CH 4-FC _$ K ₃ The Mp 82-84 ° C

Nr. R ^J R < 1 H-NMR (CDCl 3, ppm) * VI.1 H ch ₃ 3'CH ₃ -C ₄ K ₄ 2.42 (3H, s), 2.44 (3H, s), 3.85 (3H, n ', 7.1'7.9 (8H, vier Multiplatts)) WITH VI. 2 H CH C (CH) »KOCHj 2.1 (3H, s); 2.2 (3K, col. 3.75 (3H, .delta.), 4.0 (3H, s), 7.1-7.9 (4K, vulture) E, E

Double Inhibitory Configuration% Inhibition = 100 &amp;

where Δ E means extinction change, Δ t time change,

control conversion rate and (± £) '* sample conversion rate.

The following table shows the effect of the compounds of the invention on the inhibition of breathing of the yeast mitochondria by Saccharomyces cerevisiae, the phytopathogenic fungi of Drechsler sorokiniana, as well as the house flies, Musca domestica.

Inhibition of mitochondrial respiration is always given as the value of ₁₅ o (which is the concentration of the test compound at which 50% inhibition is observed) and as the F-value, which is the relative value defined as follows:

I ₅₀ (test compound) p = ---------------------------- (Standard compound)

Examples of action against harmful fungi and fungi

The action of compounds as inhibitors of mitochondrial respiration

In order to determine the effect of the compounds of the invention on mitochondrial respiration, it was first necessary to isolate mitochondria from the plant material examined. For this purpose, in the case of yeast Saccharomyces cerevisiae, a 30% to 40% suspension of fungal cells in an aqueous solution of 0.6 M mannitol, + 0.01 M Tris [hydroxymethyl] aminomethane + 0.002 M disodium ethylenediaminetetraacetic acid (pH 6.8) ) was placed in a glass ball mill and the extract was fractionated by differentiated centrifugation at 1000 x g and 12,000 x g. Mitochondria were found in a 12,000 x g precipitate of centrifugation.

By analogy, mitochondria can be isolated from other fungi, for example from the phytopathogenic fungi Drechslera sorokiniana (synonym of Helminhosporium sativum), from the human pathogenic dermatophyte Trichophyton mentagrophytes, as well as from other organisms, such as the house flies (Musca domesticus).

The action of the compounds on the respiratory chain was determined to give a suspension of mitochondria in an aqueous solution of 0.01 M Tris- [hydroxymethyl] aminomethane + 0.65

The so-called enol etherstilbene of the following formula serves as a standard compound:

Table II

Inhibition of mitochondrial respiration by compounds of formula (I) of Tables I (1) to I (3)

no. Sacaharcm. cerevisiae 3 SO (Mol / 1} F 1 (1) .1 2.7 . 10 '' 0.96 KD.2 3.2 . 10 ⁷ 11 1 (2) .7 3.3 . 10 ' 0.14 1 (2) .2 1.2 . 10 " 0.43 1 (2) -3 2.7 . 10 ' 9.6

The fungicidal activity of the compounds of formula (I) against harmful fungi can be demonstrated by the following greenhouse experiments.

The active ingredients were prepared as a 20% emulsion in a mixture consisting of 70% by weight. % cyclohexanone, 20 wt. % By weight of Nekanil ^R LN (Lutens® AP6, an emulsifying and dispersing crosslinker based on ethoxylated alkylphenols) and 10 wt. Emulphor ^R EL (Emulan ^R EL, an ethoxylated fatty alcohol emulsifier) and diluted as necessary with water to the desired concentration.

The leaves of wheat seedlings ('Kanzler' variety) were first treated with an aqueous preparation of the active substance (containing 250 ppm). After about 24 hours, the plants were dusted with spores of wheat powdery mildew (Erysiphe graminis var. Tritici).

The plants so treated were then incubated for 7 days at 20-22 ° C and 75-80% relative humidity. The extent of fungal development was then determined.

In this test, the plants treated with the compounds of the invention showed an attack of 15% or less, the plants treated with the known active compound (Compound No. 195, Table 3, EP-A 463 488) showed an attack of 40% and untreated plants showed an attack of 70%.

In another corresponding test (Kanzler wheat seedlings, amount of 63 ppm used), in which the plants were first infected and incubated and subsequently treated with the active substances, the plants treated with the compounds according to the invention showed an attack of 5% or less, the plants treated the known active compound (Compound No. 195, Table 3, EP-A 463 488) attacked 25% and untreated plants attacked 60%.

In the corresponding test (wheat seedlings of the "Frühgold" variety, 250 ppm used), in which the plants were first treated with the active substances and subsequently infected and incubated, the plants treated with the compounds according to the invention showed an infestation of 15% or less and untreated plants 75%.

Effect against Plasmopara viticola (peronospora)

Potted grapevine ('Múller Thurgau' variety) was sprayed with the preparation of active ingredient until dripping (amount used: 63 ppm). After 8 days, the plants were sprayed with zoospores of Plasmopara viticola and kept for five days at a temperature of 20-30 ° C under high air humidity. The plants were then kept under high humidity for 16 hours prior to assessment. Evaluation was performed visually.

In this test, the plants treated with the active compounds according to the invention showed an attack of 15% or less, whereas the untreated (control) plants showed an attack of 70%.

Examples of action against animal pests

The effect of the compounds of formula (I) against insecticides, arachnids and nematodes was demonstrated by the following greenhouse experiments:

The active ingredients were prepared

(a) as a 0,1% solution in acetone; or

b) as a 10% emulsion in a mixture consisting of 70 wt. % cyclohexanol, 20 wt. % By weight of Nekanil ^R LN (Lutensol ^R AP6, an emulsifying and dispersing crosslinker based on ethoxylated alkylphenols) and 10 wt. Emulphor ^R EL (emulsifier based on ethoxylated fatty alcohol) and diluted as necessary to the desired concentration, in case of (a) acetone and in case (b) water.

At the end of the experiments, the lowest concentration was always determined at which the compounds still exhibited an 80-100% inhibition (efficiency threshold or minimum concentration) as compared to the untreated controls.

Aphis fabae (contact aphid), contact effect

Heavily infested broad beans (Vicia faba) were sprayed with an aqueous preparation of the active ingredient. After 24 hours, the degree of mortality was determined.

In this experiment, compound 1 (2) .9 exhibited an activity threshold of 200 ppm.

Heliothis virescens contact / feeding effect

Approximately 10 cm high tobacco plants were treated with an aqueous active ingredient preparation. After drying, 10 larvae of larval stage 3 were placed on the plant. After 48 hours, mortality was determined and inhibition devoured.

In this experiment, compound 1 (2) .17 exhibited an activity threshold of 40 ppm.

Nephotettix cinncticeps (Grasshopper), contact effect

The ring filter was treated with an aqueous preparation of the active ingredient and subsequently 5 adult grasshoppers were placed on it. Mortality was evaluated after 24 hours.

In this experiment, compounds 1. (1) .4, 1. (2) .7, 1. (2) .19, 1. (2) .20, 1. (2) .21, 1. (2) .22, 1. (2) .25, 1. (2) .26, 1. (2) .27.1. (2) .28 and 1. (2) .29 efficiency threshold of 0.2 mg or less .

Prodenia litura (Egyptian cottonseed), contact / fire effect

Five L3 developmental stages (10 to 12 mm) that did not suffer any damage in the contact trial were maintained on standard nutrition (3.1 L water, 80 g agar, 137 g beer yeast, 515 g corn flour, 130 g wheat germ as well as the usual ingredients and vitamins (20 g Wesson salt, 5 g Nipagine, 5 g sorbine, 10 g cellulose, 18 g ascorbic acid, 1 g Lutavit ^R (vitamin), 5 ml alcoholic biotin solution) The observation was carried out until the hatching of the butterflies in the control experiment without the active substance.

In this experiment, compounds 1. (2) .2.1. (2) .16 and 1. (2) .27 had an activity threshold of 0.2 mg or less.

Tetranychus telarius, contact effect

Heavily infested bean pot plants containing two germinate leaves were treated with an aqueous active ingredient preparation. After 5 days in the greenhouse, the success rate of destruction was determined using a microscope.

In this experiment, compounds 1. (2) .2, 1. (2) .6, 1. (2) .7, 1. (2) .8, 1. (2) .9, 1. (2) .13, 1. (2) .14, 1. (2) .15, 1. (2) .16, 1. (2) .17.1 (2) .19, 1. (2) .20 and 1. (2) .21 efficiency threshold of 200 ppm or less.

Claims (11)

PATENT CLAIMS Compounds of general formula (I) in which the substituents and indices have the following meanings: R ¹ C (CO ₂ CH ₃ ) = NOCH ₃ (Ia), C (CONHCH ₃ ) = NOCH ₃ (1b), C (CONH ₂ ) = NOCH ₃ (Ic), C (CO ₂ CH ₃ ) = CHOCH ₃ (1d) or C (CO ₂ CH ₃ ) = CHCH ₃ (Ie); R ^{2 is} cyano, nitro, halogen, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl or C 1 -C 4 alkoxy; m 0, 1 or 2, wherein the radical R ² may be different when m is 2; R ³ is H, cyano, hydroxy, halo, alkyl of 1 to 6 carbon atoms, haloalkyl of 1 to 6 carbon atoms, alkoxyalkyl of C 1 -C 6 alkoxy and C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, C 1 -C 6 alkylthio, cyclopropyl, alkenyl C 2 -C 6 aryloxyalkyl, C 1 -C 6 aryloxyalkyl, benzyl or benzyloxy, the aromatic rings of which may bear one to three of the following groups: cyano, nitro, halogen, C 1-6 alkyl C 1 -C 6 haloalkyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy or C (CH ₃ ) = N-YR ^a , where: ^And R is alkyl having 1 to 6 carbon atoms and Y is an oxygen or nitrogen atom, the nitrogen atom bearing one hydrogen atom or an alkyl group having 1 to 6 carbon atoms; R ( ⁴⁾ is hydrogen or cyano, substituted or unsubstituted alkyl, alkenyl, alkynyl, cycloalkyl, heterocyclyl, aryl and hetaryl; substituted or unsubstituted alkoxy, alkenyloxy, alkynyloxy, cycloalkoxy, heterocyclyloxy, aryloxy and hetaryloxy groups; substituted or unsubstituted arylthio and hetarylthio; -Q _P -C- (R ^S ) = N-Y'-R ⁶ or -QON = CR ⁷ R ⁸ , wherein Q represents a direct bond, CH ₂ , CH (CH ₃ ), CH (CH ₂ CH ₃ ) or 1,1-cyclopropyl group; p is 0 or 1; Y represents an oxygen or nitrogen atom, wherein the nitrogen atom carries one hydrogen atom or an alkyl group having 1 to 4 carbon atoms; R ^{5 is} one of R ³ or substituted or unsubstituted cycloalkoxy, heterocyclyloxy, aryloxy, hetaryloxy, arylthio and hetarylthio; R ⁶ substituted or unsubstituted C 1 -C 10 alkyl, C 3 -C 6 cycloalkyl, C 2 -C 10 alkenyl, C 2 -C 10 alkynyl, C 1 -C 10 alkylcarbonyl a (C 2 -C 10) alkenylcarbonyl, (C 2 -C 10) alkynylcarbonyl or (C 1 -C 10) alkylsulfonyl group; substituted or unsubstituted aryl, hetaryl, arylcarbonyl, hetarylcarbonyl, arylsulfonyl or hetarylsulfonyl groups; R ⁷ , R ^{8 are} methyl, ethyl, phenyl and benzyl, the aromatic rings of which may bear one to three of the following substituents: cyano, nitro, halogen, C 1-6 alkyl, C 1-6 haloalkyl carbon atoms, (C1-C6) alkoxy or (C1-C6) haloalkoxy; R ³ and R ⁴ together with the carbon atom to which they are attached means a four- or eight-membered ring which, in addition to the carbon atoms, may contain one or two oxygen and / or sulfur atoms and / or NH- and / or N (C _r C) _4- alkyl), and these carbon atoms may bear one of the following substituents: a halogen atom, a (C1-C6) alkyl group or a (C1-C4) alkoxyimino group; while R ³ and R ⁴ are not simultaneously attached to the carbon atom through the heteroatom; as well as their salts. Compounds of formula (I) according to claim 1, in which R ^{4 has the} following meaning: alkyl, alkenyl, alkynyl, alkoxy, alkenyloxy or alkynyloxy, wherein the hydrocarbon groups may be partially or fully halogenated and / or carry one to three of the following substituents: - cyano, nitro, hydroxy, mercapto, amino, carboxyl, aminocarbonyl, aminothiocarbonyl, - alkylsulfonyl of 1 to 6 carbon atoms, alkylsulfoxyl of 1 to 6 carbon atoms, alkylcarbonyl of 1 to 6 carbon atoms, cycloalkyl of 1 to 6 carbon atoms, alkoxy of 1 to 6 carbon atoms, haloalkoxy of 1 to 6 carbon atoms, C 1 -C 6 alkoxycarbonyl, C 1 -C 6 alkylthio, C 1 -C 6 alkylamino, C 1 -C 6 dialkylamino, C 1 -C 6 alkylaminocarbonyl, C 1 -C 6 dialkylaminocarbonyl, alkylaminothiothiocarbonyl (C 1 -C 6), (C 1 -C 6) dialkylaminothiocarbonyl, (C 2 -C 6) alkenyloxy, a benzyloxy, aryl, aryloxy, hetaryl and hetaryloxy group, wherein the aromatic rings may be substituted with the usual groups; a cycloalkyl, cycloalkoxy, heterocyclyl or heterocyclyloxy group, wherein the cyclic groups may be partially or fully halogenated and / or carry one to three of the following substituents: - cyano, nitro, hydroxy, mercapto, amino, carboxyl, anionocarbonyl, aminothiocarbonyl, - (C 1 -C 6) alkyl, (C 1 -C 6) haloalkyl, (C 1 -C 6) alkylsulfonyl, (C 1 -C 6) alkylsulfoxyl, (C 1 -C 6) alkylcarbonyl, (C 3 -C 6) cycloalkyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, C 1 -C 6 alkoxycarbonyl, C 1 -C 6 alkylthio, C 1 -C 6 alkylamino, C 1 -C 6 dialkylamino, alkylamino carbonyl (C 1 -C 6) dialkyl, (C 1 -C 6) dialkylaminocarbonyl, (C 1 -C 6) alkylaminothiocarbonyl, (C 1 -C 6) dialkylaminothiocarbonyl, (C 2 -C 6) alkenyl, (C 2 -C 6) alkenyloxy group, a benzyl, benzyloxy, aryl, aryloxy, hetaryl and hetaryloxy group, wherein the aromatic rings may be substituted with the usual groups; an aryl, hetaryl, aryloxy or hetaryloxy group, wherein the cyclic groups may be partially or fully halogenated and / or carry one to three of the following substituents: - cyano, nitro, hydroxy, mercapto, amino, carboxyl, aminocarbonyl, aminothiocarbonyl, - (C 1 -C 6) alkyl, (C 1 -C 6) haloalkyl, (C 1 -C 6) alkylsulfonyl, (C 1 -C 6) alkylsulfoxyl, (C 1 -C 6) alkylcarbonyl, (C 3 -C 6) cycloalkyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, C 1 -C 6 alkoxycarbonyl, C 1 -C 6 alkylthio, C 1 -C 6 alkylamino, C 1 -C 6 dialkylamino, alkylaminocarbonyl (C 1 -C 6), (C 1 -C 6) dialkylaminocarbonyl, (C 1 -C 6) alkylaminothiocarbonyl, (C 1 -C 6) dialkylaminothiocarbonyl, (C 2 -C 6) alkenyl, (C 2 -C 6) alkenyloxy group, a benzyl, benzyloxy, aryl, aryloxy, hetaryl, hetaryloxy group, wherein the aromatic rings may be substituted with the usual groups; - C (= NOR ') - A _n -R or NR'-CO-DR ^iv , wherein represents; A is an oxygen, sulfur or nitrogen atom, wherein the nitrogen atom may carry a hydrogen atom or an alkyl group having 1 to 6 carbon atoms; n is 0 or 1; R ( ¹⁾ is hydrogen, alkyl of 1 to 6 carbon atoms, alkenyl of 3 to 6 carbon atoms or alkynyl of 3 to 6 carbon atoms; R &lt; 1 &gt; is hydrogen or alkyl of 1 to 6 carbon atoms; D is a direct bond, oxygen or NR ^b (R ^b = hydrogen, C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 3 -C 6 cycloalkyl, cycloalkenyl (C až-C,) aryl, (C až-Cryry) aryl, (C až-C hry) aryl, hetaryl and C aetary-Cetary h hetarylalkyl); R 'is hydrogen, hydroxy, (C 1 -C 6) alkyl, (C 2 -C 6) alkenyl, (C 2 -C 6) alkynyl, (C 1 -C 6) alkoxy, (C 2 -C 6) alkenyloxy, (C 1 -C 6) alkynyloxy C 2 -C 6, C 1 -C 6 alkoxyalkyl and C 1 -C 6 alkoxyalkoxy, C 1 -C 6 alkoxyalkoxy and C 1 -C 6 alkoxycarbonyl; R ^'in hydrogen atom, alkyl group having 1 to 6 carbon atoms, alkenyl of 2 to 6 carbon atoms, alkynyl of 2 to 6 carbon atoms, cycloalkyl having 3 to 6 carbon atoms, cycloalkenyl of 3-6 carbon atoms, aryl, aralkyl, C 1 -C 6, hetaryl and C 1 -C 6 hetarylalkyl. Animal pest control agents or harmful fungi, characterized in that they contain a solid or liquid carrier and a compound of formula (I) according to claim 1. A method of controlling harmful fungi, characterized in that the fungi or materials, plants, soil or seed to be protected from fungal attack are treated with an effective amount of a compound of formula (I) according to claim 1. A method of controlling animal pests, characterized in that the pests or materials, plants, soil or seed to be protected from attack by the pests are treated with an effective amount of a compound of formula (I) according to claim 1. Use of compounds of formula (I) according to claim 1 for the manufacture of a composition for controlling animal pests or harmful fungi. Use of compounds of formula (I) according to claim 1, for controlling animal pests or harmful fungi by means of a suitable agent. A process for the preparation of compounds of formula (I) according to claim 1, wherein R ¹ is C (CO ₂ CH ₃ ) = NOCH ₃ (Ia), C (CO ₂ CH ₃ ) = CHOCH ₃ (Id) or C (CO) ₂ CH ₃ ) = CHCH ₃ (Ie), characterized in that the benzoic acid ester of formula (II) (H) wherein 1 is a nucleophilic exchangeable leaving group and R is a C 1 -C 4 alkyl group is converted into presence of a base with an oxime of formula (III) R ³ (III) to the corresponding carboxylic acid ester of formula (IV) (IV) (IV) is saponified to the corresponding carboxylic acid, and (IV), and is then converted into the chloride (Va) (Va), and then converted to cyanide (Vb (Vb) and (Vb) are converted by the Pinner reaction to the corresponding α-ketoester of formula (VI) wherein R ² and m are as defined in claim 1, and T represents an oxygen or nitrogen atom, wherein the nitrogen atom may carry a hydrogen atom or an alkyl group having 1 to 6 carbon atoms; R is C 1 -C 4 alkyl, and L is -ON = CR ³ R ⁴ , wherein R ³ and R ⁴ are as defined in claim 1. and (VI) is subsequently carried out; or (a) with O-methylhydroxylamine or its salt (VIIa) CH ₃ -O-NH ₂ CH ₃ -O-NH ₃ ⁺ Z '(VIIa), where Z is a halide anion, to the corresponding compound (Ia) [R = C (CO ₂ CH ₃ ) = NOCH ₃ ], b) with a Wittig or Wittig-Horner reagent of formula (VIIIb) CH ₃ -O-CH ₂ -P * (VIIIb), wherein P * represents a phosphonate or phosphonium halide, to the corresponding compound (1d) [R = C (CO ₂ CH ₃ ) -CHOCH ₃ ], or c) with Wittig or Wittig-Horner reagent of formula (Vile) CH ₃ -CH ₂ -P * (Villa) to the corresponding compound (Ie) [R = C (CO ₂ CH ₃ ) = CHCH ₃ J. A process for the preparation of compounds (I) according to claim 1, wherein R ¹ is C (CONHCH ₃ ) = NOCH ₃ (1b) or C (CONH ₂ ) = NOCH ₃ (Ic), characterized in that the compound of formula (la) according to claim 8, is converted with methylamine or a salt thereof (XIII) CH ₃ -NH ₂ CH, -NHfZ '(XIII), where Z is a halide anion, to the corresponding compound of formula (1b) [R = C (CONHCH ₃ ) = NOCH ₃ ] (1b) or with ammonia or ammonium salt to the corresponding Compound (Ic) [R = C (CONH ₂ ) = NOCH ₃ ] Intermediates of formula (Vb) according to claim 8. Document Boilers (Vb) 11. Intermediates of formula (X)