AU709902B2 - Iminooxyphenyl acetic acid derivatives, their preparation, intermediates for their preparation, and their use - Google Patents

Description

0050/46490 3 Moreover, the invention relates to processes and intermediates for the preparation of the compounds I, to compositions comprising them, and to their use for controlling animal pests and harmful fungi.

Phenylacetic acid derivatives for controlling animal pests and harmful fungi have been disclosed in the literature (EP-A 370 629, EP-A 463 488, EP-A 460 575, WO-A 95/21,154, WO-A 95/21,153, WO-A 95/18,789).

It is an object of the present invention to provide compounds which are more powerful inhibitors of mitochondrial respiration and thus have an improved activity against animal pests and harmful fungi.

We have found that this object is achieved by the compounds I defined at the outset. We have furthermore found processes and intermediates for the preparation of these compounds, and compositions which are suitable for controlling animal pests and harmful fungi.

The compounds I can be prepared by various routes, it generally being irrelevant whether the group -O-N=CR 3

R

4 (also termed "side chain" hereinbelow) or the radical R 1 (also termed "pharmacophore" hereinbelow) is synthesized first, or in which precursor of the "pharmacophore" the "side chain" is coupled with the skeleton.

1. For example, in the preparation of the compounds I where R 1 is C(C0 2

CH

3

)=NOCH

3

C(CO

2

CH

3

)=CHOCH

3 (Id) or C(C0 2

CH

3

)=CHCH

3 a procedure is followed in which a benzoic ester of the formula II is converted with an oxime of the formula III in the presence of a base to give the corresponding derivative of the formula IV, IV is hydrolyzed to give the corresponding carboxylic acid IVa, and IVa is subsequently first reacted to give the chloride Va and then the cyanide Vb, Vb is converted into the corresponding a-ketoester VI via a Pinner reaction, and VI is subsequently converted either a) with O-methylhydroxylamine or a salt thereof (VIIa) to give the corresponding compound Ia [R C(CO 2

CH

3

)=NOCH

3 or b) with a Wittig or Wittig-Horner reagent of the formula VIIb to give the corresponding compound Id [R C(C0 2

CH

3

)=CHOCH

3 or 0050/46490 4 b) [sic] with a Wittig or Wittig-Horner reagent of the formula VIIc to give the corresponding compound Ie [R C(CO 2

CH

3

)=CHCH

3

(R

2 0-OR (B.1) N-ON- 0

R

3

O~O

>=N-O

R

3 P(0)

R

3 (Vb)

(D)

0H 3 -0-NH 2

CH

3

-O-NH

3

DZ

(VIla)

CH

3 -0-CH 2 (VIlb)_

(F)

CH

3

-CH

2

-P*

(VIIc)

(G)

00H 3

R

3

CH

3 0N Ir N 1a 0 N-O'Ja

OCH

3

R

3

CH

3 0C0

Y

(Id)0 N-Ofa

OH

R

3

CH

3

-O

1W~ 0 L in formula II is a leaving group conventionally used in nucleophilic aromatic substitution, such as halogen (eg.

fluorine, chlorine, bromine), nitro or sulfonate.

R in formula II is a Cl-C 4 -alkyl group, in particular methyl.

0050/46490 Z- in formula Vila is the anion of an inorganic acid, in particular a halide anion.

P* in formulae VIIb and VIIc is a phosphonate suitable for a Wittig or Wittig-Horner reaction or a phosphonium halide radical.

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

(R N-OH R 4 R2 R RM L R(11) N-O

(A)

020 OR R 3 0 OR (II) (IV) Suitable solvents are aromatic hydrocarbons such as toluene, m- and p-xylene, halogenated hydrocarbons such as methylene chloride, chloroform and chlorobenzene, ethers 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-butyl methyl ketone, and also dimethyl sulfoxide and dimethylformamide, dimethylacetamide, 1,3-dimethylimidazolidin-2-one, 1,3-dimethyltetrahydro-2(1H)-pyrimidinone and hexamethylphosphoric triamide, especially preferably tetrahydrofuran, dimethyl sulfoxide, dimethylacetamide, dimethylformamide and 1,3-dimethyltetrahydro-2(1H)-pyrimidinone. Mixtures of these may also be used.

Bases which are suitable are, generally, inorganic compounds such as alkali metal hydrides and alkaline earth metal hydrides, such as lithium hydride, sodium hydride, potassium hydride and calcium hydride, alkali metal carbonates and alkaline earth metal carbonates such as lithium carbonate and calcium carbonate, furthermore silver carbonate, alkali metal hydrogen carbonates such as sodium hydrogen carbonate, organometallic compounds, in particular alkali metal alkyls such as methyllithium, butyllithium and phenyllithium, alkylmagnesium halides such as methylmagnesium chloride, and also alkali metal alkoxides and alkaline earth metal 0050/46490 6 alkoxides such as sodium methoxide, sodium ethoxide, potassium methoxide, potassium ethoxide, potassium tert-butoxide and dimethoxymagnesium, furthermore organic bases, eg. tertiary amines such as trimethylamine, triethylamine, triisopropylethylamine and N-methylpiperidine, pyridine, substituted pyridines such as collidine, lutidine and 4-dimethylaminopyridine, and also bicyclic amines.

Substances which are especially preferred are sodium hydride, potassium carbonate, potasium methoxide, potassium ethoxide, potassium tert-butoxide and sodium methoxide. In general, the bases are employed in equimolar amounts, in excess or, if appropriate, as the solvent.

With a view to 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-crown-6 or 15-crown-5, or of another customary phase-transfer catalyst.

Suitable phase-transfer catalysts are ammonium halides and ammonium tetrafluoroborates such as benzyltriethylammonium chloride, benzyltributylammonium chloride, tetrabutylammonium chloride, hexadecyltrimethylammonium bromide and tetrabutylammonium tetrafluoroborate, and also phosphonium halides such as tetrabutylphosphonium chloride and tetraphenylphosphonium bromide.

In general, the starting materials are reacted with each other in equimolar amounts. It may be advantageous for the yield to employ III in an excess based on II.

With a view to the reaction rate and to the completeness of the reaction, it may be advantageous first to treat the compounds III with base and to react the resulting salt with the compound II.

The starting materials II required for the preparation of the compounds I have been disclosed in the literature. Those starting materials III which are not already known from the literature cited at the outset can be obtained by the methods described therein (cf. WO-A 95/21,153).

lB. The reaction of the ester IV to the corresponding acid IVa is carried out in a manner known per se by means of acidic or alkaline hydrolysis at from 0°C to 100oC, preferably from 0 C to 50 0 C, in an inert organic solvent or aqueous/organic solvents in the presence of a base or of an acid [alkaline

~II_

0050/46490 7 hydrolysis, cf.: J.Org.Chem. 30, (1965) 3676; acidic hydrolysis, cf.: Chem.Ind. (London) 1964, 193].

R4 R2m R4 N-O l N-Om

R

3 O OR

R

3 O OH (IV) (IVa) The resulting carboxylic acid IVa is subsequently [lacuna] in a manner known per se using customary chlorinating agents at from 0°C to 150°C, preferably 0°C to 100 0 C, in the presence or absence of an inert organic solvent [Houben-Weyl, Supplementary Volume 5, p. 59 et seq., 225 et seq. and 664 et seq.].

R4 R2m R4 R2m N-O 0 (B.2) R3 OH

R

3 O- CI (IVa) (Va) Suitable chlorinating reagents are all reagents conventionally used for this purpose, in particular SOC12, (COC1) 2 POC13, AlC1 3 and PC15. In general, the chlorinating agents are used in an excess or, if desired, as the solvent.

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

In general, the starting materials are reacted with each other in at least equimolar amounts. It may be advantageous for the yield to employ the chlorinating agent in an excess based on IVa.

IC. The reaction of benzoyl chloride Va to give the corresponding cyanide Vb is carried out in a manner known per se [DE Appl.

No. 19 603 990.8; Bull.Chem.Soc.Jpn. 60, (1987) 1085; Synthesis 1983, 636; J.Org.Chem. 43, (1978) 2280; Tetrahedron.Lett.

1974, 2275] at from OOC to 1500C, preferably 100C to 1000C, using an inorganic cyanide in an inert organic solvent in the presence or absence of a catalyst.

KA/

3 7, 0050/46490 8 R4 R2m R4 R2m N-O N-O

R

3 O CI R 3 O C-N (Va) (Vb) Suitable inorganic cyanides are cyanides of metals of the first main group or the subgroups of the Periodic Table, for example lithium, sodium, potassium, copper and silver, in particular copper, and organic cyanides such as trimethylsilyl cyanide.

Suitable solvents are aliphatic hydrocarbons such as pentane, hexane, cyclohexane and petroleum ether, aromatic hydrocarbons such as toluene, m- and p-xylene, halogenated hydrocarbons such as methylene chloride, chloroform and chlorobenzene, ethers such as diethyl ether, diisopropyl ether, tertbutyl 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 and also dimethyl sulfoxide and dimethylformamide, especially preferably toluene, methylene chloride and tetrahydrofuran.

Mixtures of these may also be used.

The use of a catalyst is recommended when carrying out the reaction with the abovementioned cyanide compounds, with the exception of CuCN. Catalysts which are used are customary phase-transfer catalysts, in particular ammonium salts such as tetrabutylammonium bromide.

In general, the starting materials are reacted with each other in equimolar amounts. It may be advantageous for the yield to employ the cyanide in an excess based on Va.

iD. The reaction of the cyanide Vb to give the a-ketoester VI is carried out in a manner known per se by way of a Pinner reaction at from OOC to 1500C, preferably 30 0 C to 1000C, in an alcohol (R-OH) in the presence of an acid and of a catalyst [Tetrahedron Lett. 21, (1980) 3539; J.Org.Chem. 47, (1982) 2342].

0050/46490 9 R4 R2m R 4 R2m N-O 1 N-0

OR

R3 O CN R 3

O

(Vb) (VI) 0 Acids and acidic catalysts which are used are inorganic acids such as hydrofluoric acid, hydrochloric acid, hydrobromic acid, sulfuric acid and perchloric acid, Lewis acids such as boron trifluoride, aluminum trichloride, iron(III) chloride, tin(IV) chloride, titanium(IV) chloride and zinc(II) chloride, and organic acids such as formic acid, acetic acid, propionic acid, oxalic acid, citric acid and trifluoroacetic acid.

In general, the acids are used in at least equimolar amounts, but preferably in excess.

1E. The reaction of the a-ketoester VI with O-methylhydroxylamine or a salt thereof (VIIa) to give the compound Ia is carried out in a manner known per se at from 0OC to 100 0 C, preferably 200C to 700C, in an inert organic solvent in the presence or absence of a base [US-A 5,221,762].

CH

3

-O-NH

2

R

4 R2m CH3-O-NH 3 ZG R 4 R2 (VIla) N-0 N-0 OR OCH 3

R

3

R

3

CH

3

ON

(VI) 0 (la) 0 Suitable solvents are aliphatic hydrocarbons such as pentane, hexane, cyclohexane and petroleum ether, aromatic hydrocarbons such as toluene, m- and p-xylene, halogenated hydrocarbons such as methylene chloride, chloroform and chlorobenzene, ethers such as diethyl ether, diisopropyi ether, tertbutyl methyl ether, dioxane, anisole and tetrahydrofuran, nitriles such as acetonitrile and propionitrile, ketones such as acetone, methyl ethyl ketone, diethyl ketone and tertbutyl methyl ketone, alcohols such as methanol, ethanol, n-propanol, isopropanol, n-butanol and tert-butanol and also dimethyl sulfoxide and dimethylformamide, especially 0050/46490 preferably dimethylformamide or alcohols. Mixtures of these may also be used.

Bases which are suitable are, generally, inorganic compounds such as alkali metal hydroxides and alkaline earth metal hydroxides such as lithium hydroxide, sodium hydroxide, potassium hydroxide and calcium hydroxide, alkali metal oxides and alkaline earth metal oxides such as lithium oxide, sodium oxide, calcium oxide and magnesium oxide, alkali metal hydrides 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 carbonates and alkaline earth metal carbonates such as lithium carbonate and calcium carbonate, and also alkali metal hydrogen carbonates such as sodium hydrogen carbonate, organometallic compounds, in particular alkali metal alkyls such as methyllithium, butyllithium and phenyllithium, alkylmagnesium halides such as methylmagnesium chloride and alkali metal alkoxides and alkaline earth metal alkoxides such as sodium methoxide, sodium ethoxide, potassium ethoxide, potassium tert-butoxide and dimethoxymagnesium, furthermore organic bases, eg.

tertiary amines such as trimethylamine, triethylamine, triisopropylethylamine and N-methylpiperidine, pyridine, substituted pyridines such as collidine, lutidine and 4-dimethylaminopyridine, and also bicyclic amines. Tertiary amines are especially preferred.

In general, the bases are employed in catalytic amounts, but they may also be used in equimolar amounts, in an excess or, if desired, as the solvent.

In general, the starting materials are reacted with each other in equimolar amounts. It may be advantageous for the yield to employ VIIa in an excess based on VI.

1F. The reaction of the a-ketoester VI with [lacuna] to give the compound Id is carried out in a manner known per se by way of a Wittig or Wittig-Horner reaction at from 0°C to 100°C, preferably 0°C to 50°C, in an inert organic solvent in the presence of a base and of a catalyst [Tetrahedron 44, (1988) 3727].

0050/46490 11 R R2 CH 3

CH

2 R4 R2m OR

OCH

3 R O

R

3

CH

3

OC

(VI) 0 (Id) 0 Suitable solvents are aliphatic hydrocarbons such as pentane, hexane, cyclohexane and petroleum ether, aromatic hydrocarbons such as toluene, m- and p-xylene, halogenated hydrocarbons such as methylene chloride, chloroform and chlorobenzene, ethers such as diethyl ether, diisopropyl ether, tertbutyl methyl ether, dioxane, anisole and tetrahydrofuran, nitriles such as acetonitrile and propionitrile, ketones such as acetone, methyl ethyl ketone, diethyl ketone and tertbutyl methyl ketone, alcohols such as methanol, ethanol, n-propanol, isopropanol, n-butanol and tert-butanol and also dimethyl sulfoxide and dimethylformamide, especially preferably dimethylformamide. Mixtures of these may also be used.

Bases which are suitable are, generally, inorganic compounds such as alkali metal hydroxides and alkaline earth metal hydroxides such as lithium hydroxide, sodium hydroxide, potassium hydroxide and calcium hydroxide, alkali metal oxides and alkaline earth metal oxides such as lithium oxide, sodium oxide, calcium oxide and magnesium oxide, alkali metal hydrides 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 carbonates and alkaline earth metal carbonates such as lithium carbonate and calcium carbonate, and also alkali metal hydrogen carbonates such as sodium hydrogen carbonate, organometallic compounds, in particular alkali metal alkyls such as methyllithium, butyllithium and phenyllithium, alkylmagnesium halides such as methylmagnesium chloride and alkali metal alkoxides and alkaline earth metal alkoxides such as sodium methoxide, sodium ethoxide, potassium ethoxide, potassium tert-butoxide and dimethoxymagnesium, furthermore organic bases, eg.

tertiary amines such as trimethylamine, triethylamine, triisopropylethylamine and N-methylpiperidine, pyridine, substituted pyridines such as collidine, lutidine and 4-dimethylaminopyridine, and also bicyclic amines. Alkoxides are especially preferred.

In general, the bases are employed in catalytic amounts, but they may also be used in equimolar amounts, in an excess or, if desired, as the solvent.

In general, the starting materials are reacted with each other in equimolar amounts. It may be advantageous for the yield to employ VIIb in an excess based on VI.

1G. The reaction of the a-ketoester VI with VIIc to give the compound Ie is carried out in a manner known per se by way of a Wittig or Wittig-Horner reaction at from O0C to 100'C, preferably O'C to 50C, in an inert organic solvent in the presence of a base and of a catalyst (Austr.J.Chem. 34, (1981) 2363; Can.J.Chem. A4, (1971) 2143].

R*

-R

2

CH

3

-CH

2 -P P* Rl 4 R2 M

(V

ll c) R3 OR N

OR

3

R

3

H-COCH

3 I) 0 (le) 0 Suitable solvents are aliphatic hydrocarbons such as pentane, hexane, cyclohexane and petroleum ether, aromatic hydrocarbons such as toluene, m- and p-xylene, halogenated hydrocarbons such as methylene chloride, chloroform and chlorobenzene, ethers such as diethyl ether, diisopropyl ether, tertbutyl methyl ether, dioxane, anisole and tetrahydrofuran, nitriles such as acetonitrile and propionitrile, ketones such as acetone, methyl ethyl ketone, diethyl ketone and tertbutyl methyl ketone, alcohols such as methanol, ethanol, n-propanol, opanol i rpanol, n-butanol and tert-butanol and also dimethyl sulfoxide and dimethylformamide, especially preferably dimethylformamide. Mixtures of these may also be used.

Bases which are suitable are, generally, inorganic compounds such as alkali metal hydroxides and alkaline earth metal hydroxides such as lithium hydroxide, sodium hydroxide, potasslum hydroxide and calcium hydroxide, alkali metal oxides and alkaline earth metal oxides such as lithium oxide, sodium oxide, calcium oxide and magnesium oxide, alkali metal hydrides 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 carbonates and alkaline earth metal carbonates such as lithium carbonate and calcium

I

0050/46490 13 carbonate, and also alkali metal hydrogen carbonates such as sodium hydrogen carbonate, organometallic compounds, in particular alkali metal alkyls such as methyllithium, butyllithium and phenyllithium, alkylmagnesium halides such as methylmagnesium chloride and alkali metal alkoxides and alkaline earth metal alkoxides such as sodium methoxide, sodium ethoxide, potassium ethoxide, potassium tert-butoxide and dimethoxymagnesium, furthermore organic bases, eg.

tertiary amines such as trimethylamine, triethylamine, triisopropylethylamine and N-methylpiperidine, pyridine, substituted pyridines such as collidine, lutidine and 4 -dimethylaminopyridine, and also bicyclic amines. Alkoxides are especially preferred.

In general, the bases are employed in catalytic amounts, but they may also be used in equimolar amounts, in an excess or, if desired, as the solvent.

In general, the starting materials are reacted with each other in equimolar amounts. It may be advantageous for the yield to employ VIIc in an excess based on VI.

2. The compounds Vb are also especially preferably obtained by reacting a cyanide of the formula Vc with an oxime of the formula III as described under item 1A.

R4R 2 m R 4

R

2 m 30 N-OH L N-O

R

3 C=N R3 C N O C-N R3 C=N (III) (Vc) (Vb) 3. The compounds of the formula VI are advantageously also obtained by converting an a-ketoester of the formula VIa into the compound VIb and reacting VIb in situ with a ketone or aldehyde IX to give VI.

0050/46490 14 R'-O Rm R2 -0 H2NO N O OR

OR

R" O) R O R (Vla) 0 (VIb) O R4Ro

R

3 R4

R

2 m (IX) Y OR

R

3

O

(VI) o In formula VIa, the groups R' and R" independently of one another are Ci-C 6 -alkyl or aryl.

The hydroxylamine VIb is liberated from the oxime VIa, and the resulting reaction mixture is further reacted with the ketone IX in a manner known per se at from 0 C to 150°C, preferably 0°C to 50 0 C, in an inert organic solvent in the presence of an acid or of a catalyst.

Suitable solvents are aliphatic hydrocarbons such as pentane, hexane, cyclohexane and petroleum ether, aromatic hydrocarbons such as toluene, m- and p-xylene, halogenated hydrocarbons such as methylene chloride, chloroform and chlorobenzene, ethers such as diethyl ether, diisopropyl ether, tertbutyl methyl ether, dioxane, anisole and tetrahydrofuran, nitriles such as acetonitrile and propionitrile, ketones such as acetone, methyl ethyl ketone, diethyl ketone and tertbutyl methyl ketone, alcohols such as methanol, ethanol, n-propanol, isopropanol, n-butanol and tert-butanol and also dimethyl sulfoxide and dimethylformamide, especially preferably alcohols. Mixtures of these may also be used.

Acids and acidic catalysts which are used are inorganic acids such as hydrofluoric acid, hydrochloric acid, hydrobromic acid, sulfuric acid and perchloric acid, Lewis acids such as boron trifluoride, aluminum trichloride, iron(III) chloride, tin(IV) chloride, titanium(IV) chloride and zinc(II) chloride, and organic acids such as formic acid, acetic acid, propionic acid, oxalic acid, citric acid and trifluoroacetic acid.

0050/46490 In general, the acids are employed in catalytic amounts, but they may also be used in equimolar amounts, in an excess or, if appropriate, as the solvent.

In general, the starting materials are reacted with each other in equimolar amounts. It may be advantageous for the yield to employ IX in an excess based on VIIb.

4. Compounds I where R 1 is C(CONHCH 3

)=NOCH

3 (Ib) or

C(CONH

2

)=NOCH

3 (Ic) are obtained, for example, by reacting a compound of the formula Ia in a manner known per se with methylamine or a salt thereof (XIII) or with ammonia or an ammonium salt, eg.

R4 N

R

2 m CH 3

-NH

2 R 4 R2 m aCH 3 -NH Ze S CH 3 N OCH 3 (XIII) HN NHCH 3 R 3 CH30NJ-^ I R3 CH3ON iT^ (la) 0 (Ib) 0 Z- in formula XIII is the anion of an inorganic acid, in particular a halide anion such as chlorine and bromine.

This reaction is normally carried out at from 0°C to 150 0

C,

preferably 0°C to 70 0 C, in an inert organic solvent in the presence or absence of a base. Suitable solvents are aliphatic hydrocarbons such as pentane, hexane, cyclohexane and petroleum ether, aromatic hydrocarbons such as toluene, mand p-xylene, halogenated hydrocarbons such as methylene chloride, chloroform and chlorobenzene, ethers 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-butyl methyl ketone, alcohols such as methanol, ethanol, n-propanol, isopropanol, n-butanol and tert-butanol and also dimethyl sulfoxide and dimethylformamide, especially preferably tetrahydrofuran.

Mixtures of these may also be used.

In the event that the ammonium salts are employed as the starting materials, the reaction is advantageously carried out in the presence of a base. Bases which are suitable are, generally, inorganic compounds such as alkali metal hydroxides and alkaline earth metal hydroxides such as lithium hydroxide, sodium hydroxide, potassium hydroxide and calcium hydroxide, alkali metal oxides and alkaline earth metal oxides such as lithium oxide, sodium oxide, calcium oxide and 16 magnesium oxide, alkali metal hydrides 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 carbonates and alkaline earth metal carbonates such as lithium carbonate and calcium carbonate, and also alkali metal hydrogen carbonates such as sodium hydrogen carbonate, organometallic compounds, in particular alkali metal alkyls such as methyllithium, butyllithium and phenyllithium, alkylmagnesium halides such as methylmagnesium chloride and alkali metal alkoxides and alkaline earth metal alkoxides such as sodium methoxide, sodium ethoxide, potassium ethoxide, potassium tert-butoxide and dimethoxymagnesium, furthermore organic bases, eg. tertiary amines such as trimethylamine, triethylamine, triisopropylethylamine and N-methylpiperidine, pyridine, substituted pyridines such as collidine, lutidine and 4 -dimethylaminopyridine, and also bicyclic amines. Tertiary amines and potassium carbonate are especially preferred.

The bases are used in at least equimolar amounts, in an excess or, if desired, as the solvent.

In general, the starting materials are reacted with each other in equimolar amounts. It may be advantageous for the yield to employ XIII or ammonia in an excess based on Ia.

In an especially preferred process, the compounds Ib are .advantageously obtained by first converting an a-ketoamide of the formula VIc with an oxime of the formula III under the conditions described for 1A. to give the corresponding amide of the formula VId and subsequently reacting VId with O-methylhydroxylamine or a salt thereof (VIIa) under the conditions described for 4.

R

4 L-O iN- S'

R

3 (III) -o SNHR

NHR

40

I

(VIc) 0 (VId) o CH3-O-NK

CH

3 -O-NH'Z2Pla) R4 R2m N/

NHR

R

3

CH

3 0-N

N

(Ib) 0

I

0050/46490 17 6. In a further process, the compounds I are also obtained by converting an a-ketoester VIe with N-hydroxyphthalimide

(XI)

to give the corresponding protected oxime of the formula VIf.

The a-ketoester function of the oxime VIf can subsequently be converted into the various groups R 1 in a manner known per se as specified for the above-described processes (cf. formulae XIIa and XIIb). The phthalimide protective group is subsequently eliminated in a manner known per se using hydrazine in ethanol [Synthesis 23, (1979) 682] or with hydrogen bromide in acetic acid [J.Org.Chem. 28, (1963) 1604], and the resulting O-substituted hydroxylamine (cf.

formulae XIIIa and XIIIb) is reacted in situ with the ketone of the formula IX to give I.

The reaction sequence is outlined in the below.

reaction scheme 0 N-OH (XI) 0 (Vie) 0 (VIf) I I (Xlla) (Xllb) 0 X R 2 m

H

2 NO O (Xllla) 0

R

2 m

H

2

N

0 NHR (Xlllb) 0 _____1_11_1111111M 0050/46490

R

2 m

H

2

NO

(Xll)

OR

U

(XIIIa) O

R

2 m

H

2

NO

UY

NHR

(Xlllb) 0 The individual reactions are carried out in general and in particular under the process conditions described at the outset.

7. In a further especially preferred process, the compounds I are also obtained by first converting the a-ketoester VIe into the corresponding a-ketoester VI by means of reaction with the oxime III. The a-ketoester function of the oxime VI can subsequently be converted in a manner known per se into the various groups R 1 as specified in the above-described processes.

R

4 N-OH

R

3 R4 R2-O

SOR

R3 O O OR J0 R4N- R 2 R O

NHR

(Vlh)

O

C~--I

R4 N- R2 SU

OR

R

3

U

o

I

R4 N-0 R3 U NHR

R

3

U

0 0050/46490 19 The individual reactions are carried out in general and in particular under the process conditions described at the outset.

The compounds VIe which are required as starting material for the above reactions are obtained, for example, as shown in the reaction scheme which follows: 1 0 L mL R2-- R2m 0 H HO C=N HO (XIVa) (XIVb) (XVa) ONH 2

C

R 2 m R2m OR

OR

HO O R O(XVb) OVe)o O

O

The corresponding reaction sequence gives the a-ketoester of the formula VI or the corresponding a-ketoamide when group L is substituted by group -ON=CR 3

R

4 as specified in the conditions described at the outset by means of a reaction with the oxime III (at the level of the compounds XIVa, XIVb, XVb or VIe).

The process is carried out as specified in the methods described in Coll. Czech. Chem. Commun. 29, (1964) 97/119.

In a further process, the compounds I are also obtained as specified in the methods described in EP-A 178 826, EP-A 256 667 and EP-A 468 775 as shown in the reaction scheme which follows, starting from phenyl ketones of the formula XVI: 0050/46490 R2M

R

2 m

R

2 m L

LCH

LL

OR

U

O

O

(XVia) (XVIb)

(XVII)

In this reaction sequence, group L can be replaced by the radical

-ON=CR

3

R

4 at the levels of the compounds XVIa, XVIb and XVII in the manner described above.

The reaction mixtures are worked up in the customary manner, for example by mixing with water, phase separation and, if desired, chromatographic purification of the crude products. In some cases, the intermediates and end products are obtained in the form of colorless or pale brown viscous oils which are freed or purified from volatile components under reduced pressure at moderately elevated temperature. If the intermediates and end products are obtained as solids, they may also be purified by recrystallization or digestion.

The salts of the compounds I may be obtained in a manner known per se by treating a compound I with an acid suitable for salt formation at from -80°C to 12000, preferably OOC to 600C, in water or an inert organic solvent.

Examples of suitable acids are mineral acids such as sulfuric acid and phosphoric acid, or Lewis acids such as zinc chloride.

In general, the type of salt is not critical with a view to the use of the compounds I against animal pests and harmful fungi.

Preferred for the purposes of the invention are those salts which do not adversely affect the plants, areas, materials, seeds and spaces to be kept free from animal pests or harmful fungi.

In relation to their C=N or C=C double bonds, the compounds I can be in the form of E and Z isomers; with a view to the double bond of the radical R 1 the E isomers are generally biologically more acive and actve and thus preferred.

With a view to the double bond of the O-N=CR 3

R

4 group and other double bonds found in the radicals R 3 and R 4 E and Z isomers are also possible. In general, preferred compounds I are those where these double bonds are in the E configuration.

These double bonds are normally formed upon synthesis predominantly in the E configuration. The isomer mixtures can 0050/46490 21 either be separated into the individual isomers in the customary manner, for example by fractional crystallization or chromatography, or they may be converted into other isomers when exposed to protonic acids or Lewis acids or light. If isomer mixtures are obtained upon synthesis, separation is generally not necessary since in some cases the isomers may be converted into each other during application according to the invention due to exposure to light, formulation medium or else in vivo.

In the definitions of the symbols in the formulae above, collective terms were used which generally represent the following substituents: Halogen: fluorine, chlorine, bromine and iodine; Alkyl: saturated straight-chain or branched hydrocarbon radicals having 1 to 4, 6 or 10 carbon atoms, eg. C 1

-C

6 -alkyl 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-l-methylpropyl and l-ethyl-2-methylpropyl; Haloalkyl: straight-chain or branched alkyl groups having 1 to 4, 6 or 10 carbon atoms (as mentioned above), it being possible for some or all of the hydrogen atoms in these groups to be replaced by halogen atoms as mentioned above, eg. C 1

-C

2 -haloalkyl such as chloromethyl, bromomethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, l-chloroethyl, 1-bromoethyl, 1-fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 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 mentioned above), which is bonded to the skeleton via a carbonyl group Alkylsulfonyl: a straight-chain or branched alkyl group having 1 to 6 or 10 carbon atoms (as mentioned above) which is bonded to the skeleton via a sulfonyl group (-SO 2 0050/46490 22 Alkylsulfoxyl: a straight-chain or branched alkyl group having 1 to 6 carbon atoms (as mentioned above) which is bonded to the skeleton via a sulfoxyl group (-S0 3 Alkoxy: straight-chain or branched alkyl groups having 1 to 4 or 6 carbon atoms (as mentioned above) which are bonded to the skeleton via an oxygen atom Haloalkoxy: straight-chain or branched haloalkyl groups having 1 to 4, 6 or 10 carbon atoms (as mentioned above) which are bonded to the skeleton via an oxygen atom Alkoxycarbonyl: an alkoxy group having 1 to 6 carbon atoms (as mentioned above) which is bonded to the skeleton via a carbonyl group Alkoxyimino: straight-chain or branched alkyl groups having 1 to 4 carbon atoms (as mentioned above) which are bonded to the skeleton via an oxyimino group Alkylthio: straight-chain or branched alkyl groups having 1 to 6 carbon atoms (as mentioned above) which are bonded to the skeleton via a sulfur atom Alkylamino: a straight-chain or branched alkyl group having 1 to 6 carbon atoms (as mentioned above) which is bonded to the skeleton via an amino group Dialkylamino: two independent straight-chain or branched alkyl groups having in each case 1 to 6 carbon atoms (as mentioned above) which are bonded to the skeleton via a nitrogen atom; Alkylaminocarbonyl: an alkylamino group having 1 to 6 carbon atoms (as mentioned above) which is bonded to the skeleton via a carbonyl group Dialkylaminocarbonyl: a dialkylamino group having two independent Ci-C 6 -alkyl groups (as mentioned above) which is bonded to the skeleton via a carbonyl group Alkylaminothiocarbonyl: an alkylamino group having 1 to 6 carbon atoms (as mentioned above) which is bonded to the skeleton via a thiocarbonyl group 0050/46490 23 Dialkylaminothiocarbonyl: a dialkylamino group having two independent

CI-C

6 -alkyl group (as mentioned above) which is bonded to the skeleton via a thiocarbonyl group Alkenyl: unsaturated straight-chain or branched hydrocarbon radicals having 2 to 6 or 10 carbon atoms and a double bond in any position, eg. C 2

-C

6 -alkenyl such as ethenyl, 1-propenyl, 2-propenyl, 1-methylethenyl, 1-butenyl, 2-butenyl, 3-butenyl, l-methyl-1-propenyl, 2-methyl-1-propenyl, 1-methyl-2-propenyi, 2-methyl-2-propenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-methyl-l-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, l, 2 -dimethyl-2-propenyl, 1-ethyl-1-propenyl, 1-ethyl-2propenyl, 1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, l-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-1butenyl, 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, l-ethyl-1-methyl-2-propenyl, l-ethyl-2-methyl-1-propenyl and l-ethyl-2-methyl-2-propenyl; Alkenyloxy: unsaturated straight-chain or branched hydrocarbon radicals having 3 to 6 or 10 carbon atoms and a double bond in any position which is not adjacent to the hetero atom (as mentioned above) which are bonded to the skeleton via an oxygen atom Alkenylcarbonyl: unsaturated straight-chain or branched hydrocarbon radicals having 2 to 10 carbon atoms and a double bond in any position (as mentioned above) which are bonded to the skeleton via a carbonyl group Alkynyl: straight-chain or branched hydrocarbon groups having 2 to 4, 6, 8 or 10 carbon atoms and a triple bond in any position, eg. C2-C 6 -alkynyl such as ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methyl-2-propynyl, 1-pentynyl, 0050/46490 24 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, 1-hexynyl, 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 l-ethyl-1-methyl-2-propynyl; Alkynyloxy: unsaturated straight-chain or branched hydrocarbon radicals having 3 to 10 carbon atoms and a triple bond in any position which is not adjacent to the hetero atom (as mentioned above) which are bonded to the skeleton via an oxygen atom Alkynylcarbonyl: unsaturated straight-chain or branched hydrocarbon radicals having 2 to 10 carbon atoms and a triple bond in any position (as mentioned above) which are bonded to the skeleton via a carbonyl group Cycloalkyl: monocyclic saturated hydrocarbon groups having 3 to 6 or 10 carbon ring members, eg. C3-C 8 -cycloalkyl such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl and cyclooctyl; Cycloalkoxy: monocyclic saturated hydrocarbon groups having 3 to 6 or 10 carbon ring members (as mentioned above) which are bonded to the skeleton via an oxygen group Cycloalkenyl: monocyclic monounsaturated hydrocarbon groups having 3 to 6 or 10 carbon ring members and a double bond in any position of the ring, eg. C 5

-C

8 -cycloalkyl such as cyclopentenyl, cyclohexenyl, cycloheptenyl and cyclooctenyl; Heterocyclyl: 5- or 6-membered heterocycles containing, besides carbon ring members, one to three nitrogen atoms and/or an oxygen or sulfur atom or one or two oxygen and/or sulfur atoms, eg.

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, idinyl, 2-imidazolidinyl, 4-imidazolidinyl, 1,2,4-oxadiazolidin-3-yl, 1,2,4-oxadiazolidin-5-yl, 1,2,4-thiadiazolidin-3-yl, 0050/46490 1,2, 4-thiadiazolidin-5-yl, 1,2, 4-triazolidin-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-pyrrolin-2-yl, 2, 3-pyrrolin-3-yl, 2, 4-pyrrolin-2-yl, 2, 4-pyrrolin-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, 3,4-isoxazolin-5-yl, 4,5-isoxazolin-5-yl, 2,3-isothiazolin-3-yl, 3,4-isothiazolin-3-yl, 4,5-isothiazolin-3-yl, 2, 3-isothiazolin-4-yl, 3, 4-isothiazolin-4-yl, 4, 5-isothiazolin-4-yl, 2, 3, 4-isothiazolin-5-yl, 4 2, 3-dihydropyrazol-1-yl, 2, 3-dihydropyrazol-2-yl, 2, 3-dihydropyrazol-3-yl, 2, 3-dihydropyrazol-4-yl, 2, 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, pyrazol-5-yl, 2, 3-dihydrooxazol-2-yl, 2, 3-dihydrooxazol-3-yl, 2, 3-dihydrooxazol-4-yl, 2, 3-dihydrooxazol-5-yl, 3, 4-dihydrooxazol-2-yl, 3, 4-dihydrooxazol-3-yl, 3, 4-dihydrooxazol-4-yl, 3 ,4-dihydrooxazol-5-yl, 3, 4-dihydrooxazol-2-yl, 3, 4-dihydrooxazol-3-yl, 3, 4-dihydrooxazol-4-yl, 2-piperidinyl, 3-piperidinyl, 4-piperidinyl, 1,3-dioxan-5-yl, 2-tetrahydropyranyl, 4-tetrahydropyranyl, 2-tetrahydrothienyl, 3-tetrahydropyridazinyl, 4-tetrahydropyridazinyl, 2-tetrahydropyrimidinyl, 4-tetrahydropyrimidinyl, 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 bonded to the skeleton via an oxygen atom Aryl: a mono- to trinuclear aromatic ring system containing 6 to 14 ring members, eg. phenyl, naphthyl and anthracenyl; Aryloxy: a mono- to trinuclear aromatic ring system (as mentioned above)l which is bonded to the skeleton via an oxygen atom Arylthio: a mono- to trinuclear aromatic ring system (as mentioned above) which is bonded to the skeleton via a sulfur atom 0050/46490 26 Arylcarbonyl: a mono- to trinuclear aromatic ring system (as mentioned above) which is bonded to the skeleton via a carbonyl group Arylsulfonyl: a mono- to trinuclear aromatic ring system (as mentioned above) which is bonded to the skeleton via a sulfonyl group Hetaryl: a mono- or binuclear, 9- or 10-membered aromatic ring system which, besides carbon ring members, contains hetero atoms from the group consisting of oxygen, sulfur and nitrogen, eg.

5-membered hetaryl containing one to four nitrogen atoms or one to three nitrogen atoms and a sulfur or oxygen atom: hetaryl ring group which, besides carbon atoms, may contain one to four nitrogen atoms or one to three nitrogen atoms and a sulfur or oxygen atom as ring members, eg. 2-furyl, 3-furyl, 2-thienyl, 3-thienyl, 2-pyrrolyl, 3-pyrrolyl, 3-isoxazolyl, 4-isoxazolyl, 5-isoxazolyl, 3-isothiazolyl, 4-isothiazolyl, 3-pyrazolyl, 4-pyrazolyl, 2-oxazolyl, 4-oxazolyl, 5-oxazolyl, 2-thiazolyl, 4-thiazolyl, 2-imidazolyl, 4-imidazolyl, 1,2,4-oxadiazol-3-yl, 1,2,4-oxadiazol-5-yl, 1,2,4-thiadiazol-3-yl, 1,2,4-thiadiazol-5-yl, 1,2,4-triazol-3-yl, 1,3,4-oxadiazol-2-yl, 1,3,4-thiadiazol-2-yl and 1,3,4-triazol-2-yl; benzo-fused 5-membered hetaryl. containing one to three nitrogen atoms or a nitrogen atom and an oxygen or sulfur atom: hetaryl ring groups which, besides carbon atoms, may contain one to four nitrogen atoms or one to three nitrogen atoms and a sulfur or oxygen atom as ring members, and in which two adjacent carbon ring members or a nitrogen and an adjacent carbon ring member may be bridged by a buta-1,3-diene-1,4-diyl group; 5-membered hetaryl, bonded via nitrogen and containing one to four nitrogen atoms, or benzo-fused 5-membered hetaryl. bonded via nitrogen and containing one to three nitrogen atoms: hetaryl ring groups which, besides carbon atoms, may contain one to four nitrogen atoms, or one to three nitrogen atoms, as ring members and in which two adjacent carbon ring members or a nitrogen and an adjacent carbon ring member may be bridged by a buta-1,3-diene-1,4-diyl group, these rings being bonded to the skeleton via one of the nitrogen ring members; 6-membered hetaryl, containing one to three, or one to four, nitrogen atoms: 6-membered hetaryl ring groups which, besides carbon atoms, may contain one to three, or one to four, nitrogen atoms as ring members, eg. 2-pyridinyl, 3-pyridinyl, 0050/46490 27 4-pyridinyl, 3-pyridazinyl, 4-pyridazinyl, 2-pyrimidinyl, 4-pyrimidinyl, 5-pyrimidinyl, 2-pyrazinyl, 1,3,5-triazin-2-yl and 1,2,4-triazin-3-yl; Hetaryloxy: a mono- or binuclear heteroaromatic ring system (as mentioned above) which is bonded to the skeleton via an oxygen atom Hetarylthio: a mono- or binuclear heteroaromatic ring system (as mentioned above) which is bonded to the skeleton via a sulfur atom Hetarylcarbonyl: a mono- or binuclear heteroaromatic ring system (as mentioned above) which is bonded to the skeleton via a carbonyl group Hetarylsulfonyl: a mono- or binuclear heteroaromatic ring system (as mentioned above) which is bonded to the skeleton via a sulfonyl group (-SO 2 The addition "unsubstituted or substituted" when relating to alkyl, alkenyl and alkynyl groups is intended to express that these groups may be partially or fully halogenated [ie. some or all of the hydrogen atoms of these groups may be replaced by identical or different halogen atoms as mentioned above (preferably fluorine, chlorine or bromine)] and/or may have attached to them one to three (preferably one) of the following radicals: cyano, nitro, hydroxyl, amino, formyl, carboxyl, aminocarbonyl, alkoxy, haloalkoxy, alkylthio, haloalkylthio, alkylamino, dialkylamino, alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy, alkylaminocarbonyl, dialkylaminocarbonyl, alkylcarbonylamino, alkoxycarbonylamino, alkylcarbonyl-N-alkylamino and alkylcarbonyl-N-alkylamino, the alkyl groups in these radicals preferably containing 1 to 6 carbon atoms, in particular 1 to 4 carbon atoms; cycloalkyl, cycloalkoxy, cycloalkylthio, cycloalkylamino, cycloalkyl-N-alkylamino, heterocyclyl, heterocyclyloxy, heterocyclylthio, heterocyclylamino or heterocyclyl- N-alkylamino, unsubstituted or substituted by customary groups, the cyclic systems containing 3 to 12 ring members, preferably 2 to 8 ring members, in particular 3 to 6 ring members and the alkyl groups in these radicals preferably containing 1 to 6 carbon atoms, in particular 1 to 4 carbon atoms; aryl, aryloxy, arylthio, arylamino, aryl-N-alkylamino, arylalkoxy, arylalkylthio, arylalkylamino, arylalkyl- N-alkylamino, hetaryl, hetaryloxy, hetarylthio, hetarylamino, hetaryl-N-alkylamino, hetarylalkoxy, hetarylalkylthio, 0050/46490 28 hetarylalkylamino and hetarylalkyl-N-alkylamino, unsubstituted or substituted by customary groups, the aryl radicals preferably containing 6 to 10 ring members, in particular 6 ring members (phenyl), the hetaryl radicals containing in particular 5 or 6 ring members and the alkyl groups in these radicals preferably containing 1 to 6 carbon atoms, in particular 1 to 4 carbon atoms.

The addition "unsubstituted or substituted" when relating to the cyclic (saturated, unsaturated or aromatic) groups is intended to express that these groups may be partially or fully halogenated [ie. some or all of the hydrogen atoms in these groups may be replaced by identical or different halogen atoms as mentioned above (preferably fluorine, chlorine or bromine, in particular fluorine or chlorine)] and/or may have attached to them 1 to 4 (in particular 1 to 3) of the following radicals: cyano, nitro, hydroxyl, amino, carboxyl, aminocarbonyl, alkyl, haloalkyl, alkenyl, haloalkenyl, alkenyloxy, haloalkenyloxy, alkynyl, haloalkynyl, alkynyloxy, haloalkynyloxy, alkoxy, haloalkoxy, alkylthio, haloalkylthio, alkylamino, dialkylamino, alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy, alkylaminocarbonyl, dialkylaminocarbonyl, alkylcarbonylamino, alkoxycarbonylamino, alkylcarbonyl-N-alkylamino and alkylcarbonyl-N-alkylamino, the alkyl groups in these radicals preferably containing 1 to 6 carbon atoms, in particular 1 to 4 carbon atoms, and the alkenyl or alkynyl groups mentioned in these radicals containing 2 to 8, preferably 2 to 6, in particular 2 to 4 carbon atoms; and/or one to three (in particular one) of the following radicals: cycloalkyl, cycloalkoxy, cycloalkylthio, cycloalkylamino, cycloalkyl-N-alkylamino, heterocyclyl, heterocyclyloxy, heterocyclylthio, heterocyclylamino or heterocyclyl-N-alkylamino, unsubstituted or substituted by customary groups, the cyclic systems containing 3 to 12 ring members, preferably 2 to 8 ring members, in particular 3 to 6 ring members and the alkyl groups in these radicals preferably containing 1 to 6 carbon atoms, in particular 1 to 4 carbon atoms; aryl, aryloxy, arylthio, arylamino, aryl-N-alkylamino, arylalkoxy, arylalkylthio, arylalkylamino, arylalkyl-N-alkylamino, hetaryl, hetaryloxy, hetarylthio, hetarylamino, hetaryl- N-alkylamino, hetarylalkoxy, hetarylalkylthio, hetarylalkylamino and hetarylalkyl-N-alkylamino, unsubstituted or substituted by customary groups, the aryl radicals preferably containing 6 to 10 ring members, in particular 6 ring members (phenyl), the hetaryl radicals containing, in particular, 5 or 0050/46490 29 6 ring members and the alkyl groups in these radicals preferably containing 1 to 6 carbon atoms, in particular 1 to 4 carbon atoms and/or can have attached to them one or two (in particular one) of the following radicals: formyl, CRV=NORVi [where R v is hydrogen, alkyl, cycloalkyl and aryl and Rvi is alkyl, alkenyl, haloalkenyl, alkynyl and arylalkyl (the abovementioned alkyl groups preferably containing 1 to 6 carbon atoms, in particular 1 to 4 carbon atoms, the abovementioned cycloalkyl groups, alkenyl groups and alkynyl groups preferably containing 3 to 8, in particular 3 to 6, carbon atoms) and aryl is, in particular, phenyl which is unsubstituted or may be substituted by customary groups] or NRvii-CO-D-Rviii [where Rvii is hydrogen, hydroxyl, Cl-C 6 -alkyl,

C

2

-C

6 -alkenyl, C2-C 6 -alkynyl, Cl-C 6 -alkoxy, C2-C 6 -alkenyloxy,

C

2

-C

6 -alkynyloxy, Ci-C 6 -alkoxy-Cl-C 6 -alkyl, Cl-C 6 -alkoxy- Ci-C 6 -alkoxy and Ci-C 6 -alkoxycarbonyl, R viii is hydrogen, Ci-C 6 -alkyl, C 2

-C

6 -alkenyl, C 2

-C

6 -alkynyl, C 3

-C

6 -cycloalkyl,

C

3

-C

6 -cycloalkenyl, aryl, aryl-Cl-C 6 -alkyl, hetaryl and hetaryl-Cl-C 6 -alkyl and D is a direct bond, oxygen or nitrogen, it being possible for the nitrogen to have attached to it one of the groups mentioned under R vi and/or where two adjacent C atoms of the cyclic systems may have attached to them a C 3 -Cs-alkylene, C 3

-C

5 -alkenylene, oxy-C 2

-C

4 alkylene, oxy-C 1

-C

3 -alkyleneoxy, oxy-C 2

-C

4 -alkenylene, oxy-C 2

-C

4 alkenyleneoxy or butadienediyl group, it being possible for these bridges, in turn, to be partially or fully halogenated and/or to have attached to them one to three, in particular one or two, of the following radicals:

C

1

-C

4 -alkyl, CI-C 4 -haloalkyl, CI-C 4 -alkoxy, Cl-C 4 -haloalkoxy and C1-C 4 -alkylthio.

Customary groups are to be understood as meaning, in particular, the following substituents: cyano, nitro, halogen, C 1

-C

4 -alkyl, C1-C 4 -haloalkyl, Cl-C 4 -alkoxy, Cl-C 4 -haloalkoxy, C 1

-C

4 -alkylamino, di-Ci-C 4 -alkylamino and C 1

-C

4 -alkylthio.

Preferred compounds with a view to their biological activities are those where R 4 has the following meanings: alkyl, alkenyl, alkynyl, alkoxy, alkenyloxy or alkynyloxy, it being possible for the hydrocarbon groups, in turn, to be partially or fully halogenated and/or to have attached to them one to three of the following radicals: cyano, nitro, hydroxyl, mercapto, amino, carboxyl, aminocarbonyl, aminothiocarbonyl, 0050/46490

-CI-C

6 -alkylsulfonyl, CI-C6-alkylsulfoxyl

CI-C

6 -alkyl.carbonyl, C 3

-C

6 -cycloalkyl, Cl-C 6 -alkoxy, Cl-C 6 -haloalkoxy, C1-C6-alkoxycarbonyl, Cl-C 6 -alkylthio, Cl-C 6 -alkylamino, di-Cl-C 6 -alkylamino, Cl-C6-alkylaminocarbonyl, di-Cl-C 6 alkylaminocarbonyl, Ci-C6-alkylaminothiocarbonyl, di-Cl-C 6 alkylaininothiocarbonyl, C2-C 6 -alkenyloxy, -benzyloxy, aryl, aryloxy, hetaryl and hetaryloxy, it being possible for the aromatic rings to be substituted by customary groups; cycloalkyl, cycloalkoxy, heterocyclyl or heterocyclyloxy, it being possible for the cyclic groups, in turn, to be partially or fully halogenated and/or to have attached to them one to three of the following radicals: cyano, nitro, hydroxyl, mercapto, amino, carboxyl, aminocarbonyl, aminothiocarbonyl,

CI-C

6 -alkyl, Cj-C 6 -haloalkyl, Cl-C6-alkylsulfonyl, Ci-C6-alkylsulfoxyl, Cl-C6-alkylcarbonyl, C3-C6-cycloalkyl,

CI-C

6 -alkoxy, Cl-C 6 -haloalkoxy, Cl-C6-alkoxycarbonyl,

CI-C

6 -alkylthio, Cl-C 6 -alkylamino, di-Cl-C 6 -alkylamino, C1-C6-alkylaminocarbonyl, di-C1l-C6-alkylaminocarbonyl, Cl-C6-alkylaminothiocarbonyl, di-Cl-C6-alkylaminothiocarbo.

nyl, C2-C6-alkenyl, C2-C 6 -alkenyloxy, benzyl, benzyloxy, aryl, aryloxy, hetaryl and hetaryloxy, it being possible for the aromatic rings to be substituted by customary groups; aryl, hetaryl, aryloxy or hetaryloxy, it being possible for the cyclic groups, in turn, to be partially or fully halogenated and/or to have attached to them one to three of the following radicals: cyano, nitro, hydroxyl, mercapto, amino, carboxyl, aminocarbonyl, aminothiocarbonyl, Ci-C 6 -alkyl, Cl-C 6 -haloalkyl, Cl-C 6 -alkylsulfonyl, C1-C6-alkylsulfoxyl, Cl-C 6 -alkylcarbonyl,

C

3

-C

6 -cycloalkyl,

CI-C

6 -alkoxy, Ci-0 6 haloalkoxy, Cl-C6-alkoxycarbonyl, Cl-C6-alkylthio, Ci-C 6 -alkylamino, di-C 1

C

6 -alkylamino, C1-C6-alkylaminocarbonyl, di-Ci-C6-alkylaminocarbonyl, C1-C6-alkylaminothiocarbonyl, di-Ci-C 6 -alkylaminothiocarbonyl, C2-C 6 -alkenyl, C2-C 6 -alkenyloxy, benzyl, benzyloxy, aryl, aryloxy, hetaryl, hetaryloxy, it being possible for the aromatic rings to be substituted by customary groups, C (=NORi) -An-Rii or IRii-CO-D-Riv; 0050/46490 31 A is oxygen, sulfur or nitrogen, the nitrogen having attached to it hydrogen or Cl-C 6 -alkyl; n is 0ori1; Ri is hydrogen, Cl-C 6 -alkyl, C3-C 6 -alkenyl or

C

3

-C

6 -alkynyl; Rii is hydrogen or Cl-C 6 -alkyl; D is a direct bond, oxygen or N~Rb (Rb hydrogen,

CI-C

6 -alkyl, C2-C 6 -alkenyl, C2-C 6 -alkynyl, C3-C6-cycloalkyl, C3-C6-cycloalkenyl, aryl, aryl- Cl-C 6 -alkyl, hetaryl and hetaryl-Cl-C 6 -alkyl); Riii is hydrogen, hydroxyl, Cl-C 6 -alkyl, C2-C6-alkenyl, C2-C 6 -alkynyl, Cl-C 6 -alkoxy, C2-C6-alkenyloxy, C2-C6-alkynyloxy, C1-C6-alkoxy-Cl-C 6 -alkyl, C1-C6-alkoxy-Cl-C 6 -alkoxy and Cl-C6-alkoxycarbonyl; Riv is hydrogen, Cl"C 6 -alkyl, C2-C 6 -alkenyl, C2-C 6 -alkynyl, C3-C6-cycloalkyl, C3-C 6 -cycloalkenyl, aryl, aryl-Cl-C 6 -alkyl, hetaryl and hetaryl-Cl-C 6 -alkyl.

Especially preferred phenyl derivatives of the formula I are those where the substituents have the following meanings:

R

3 is hydrogen or cyano, Ci-C 6 -alkyl, Ci-C 6 -haloalkyl, C3-C6-CYCloalkyl, C3-C6-cycloalkyl-C 1

_C

4 -alkyl, aryl, aryl-Cl-C 4 -alkyl and aryloxy-Cl-C 4 -alkyl, it being possible for the aromatic rings to be partially or fully halogenated and/or to have attached to them one to three of the following radicals: cyano, nitro, Cl-C 6 -alkyl, Cl-C 6 -haloalkyl, Cl-C 6 -alkoxy, Cl-C6-haloalkoxy, and

R

4 is unsubstituted or substituted aryl, hetaryl, aryloxy, hetaryloxy, arylthio and hetarylthio; -Qp-C (R 5 )=N-Yl-R 6 or -Q-O-N=CR 7

R

8

R

3 and R 4 together with the carbon atom to which they are bonded are a four- to eight-membered ring which, besides carbon atoms, may contain one or two oxygen and/or sulfur 0050/46490 32 atoms and/or NH and/or N(C 1

-C

4 -alkyl) groups and whose carbon atoms may have attached to them one of the following substituents: halogen, Cl-C 6 -alkyl or C1-C 4 -alkoxyimino;

R

3 and R 4 not simultaneously being bonded to the carbon atom via hetero atoms.

Moreover, preferred phenyl derivatives of the formula I are those where the substituents have the following meanings:

R

3 is hydrogen, cyano, halogen,

C

1

-C

6 -alkyl, Cl-C 6 -haloalkyl, Cl-C 6 -alkoxy, C 1 -C6haloalkoxy, Ci-C 6 -alkylthio, C 3

-C

6 -cycloalkyl, C3-C6-cycloalkyl- 1

-C

4 -alkyl, aryl, aryl-C 1

-C

4 -alkyl, aryloxy-Cl-C 4 -alkyl and aryl-C 1

-C

4 -alkoxy, it being possible for the aromatic rings to be partially or fully halogenated and/or to have attached to them one to three of the following radicals: cyano, nitro, Ci-C 6 -alkyl, Cl-C 6 -haloalkyl, C 1

-C

6 -alkoxy,

C

1

-C

6 -haloalkoxy, and C(=NORi)-An-Rii;

R

4 is unsubstituted or substituted aryl and hetaryl; -Qp-C(R 5

)=N-Y

1

-R

6 or -Q-O-N=CR 7

R

8

R

3 and R 4 not simultaneously being bonded to the carbon atom via hetero atoms.

Furthermore, preferred compounds of the formula I are those where m is 0,

R

1 is the groups (Ic) and (Id),

R

1 is the group (Ib),

R

1 is the group (Id),

R

3 is C 1

-C

4 -alkyl (in particular methyl),

R

4 is unsubstituted or substituted Ci-C 6 -alkyl,

R

4 is unsubstituted or substituted C 2

-C

6 -alkenyl,

R

4 is unsubstituted or substituted aryl (in particular 3-substituted phenyl),

R

3 is methyl and R 4 is unsubstituted or substituted C 1

-C

6 -alkyl,

R

3 is methyl and R 4 is unsubstituted or substituted aryl (in particular 3-substituted phenyl),

R

4 is C(R 5

)=N-Y

1

-R

6 where yl is, in particular, oxygen and R is, in particular, methyl, ethyl, allyl or propargyl.

0050/46490 33 Furthermore, preferred compounds of the formula I are those where

R

3 is C1-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

1

-C

6 -alkyl, and

R

4 is aryl, hetaryl or benzyl, it being possible for the aromatic rings in these radicals to be partially or fully halogenated and/or to have attached to them one to three of the following radicals: cyano, nitro, C 1

-C

6 -alkyl, C 1

-C

6 -haloalkyl, Ci-C 6 -alkoxy, Cl-C 6 -haloalkoxy and C(=NORi)-An-Rii, or

R

4 is CR 5

=N-Y

1

-R

6 Furthermore, preferred compounds of the formula I are those where

R

3 is C 1

-C

6 -alkyl, Cl-C 6 -haloalkyl, CI-C 6 -alkoxy, C 1

-C

6 -haloalkoxy, cyclopropyl or C(CH 3

)=NO-C

1

-C

6 -alkyl, and

R

4 is C 1

-C

6 -alkyl, C 2

-C

6 -alkenyl, C2-C 6 -alkenyl or cyclopropyl, it being possible for these radicals to be partially or fully halogenated and/or to have attached to them one to three of the following groups: aryl and hetaryl, it being possible for the aromatic groups, in turn, to have attached to them one to three of the following substituents: cyano, halogen, C-C-alkyl, C-C-haloalkyl, C 1

-C

6 -alkoxy and C 1

-C

6 -haloalkoxy.

Furthermore, preferred compounds of the formula I are those where

R

3 is C 1

-C

6 -alkyl, C 1 -C-haloalkyl, cyclopropyl or

C(CH

3

)=NO-C

1 -C-alkyl, and

R

4 is C 1

-C

6 -alkoxy, it being possible for this radical to be partially or fully halogenated and/or to have attached to it one to three of the following groups: aryl and hetaryl, it being possible for the aromatic groups, in turn, to have attached to them 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 C1-C 6 -haloalkoxy.

Furthermore, preferred compounds of the formula I are those where

R

3 is C 1

-C

6 -alkyl, C 1

-C

6 -haloalkyl, C1-C 6 -alkoxy,

C

1

-C

6 -haloalkoxy, cyclopropyl or C(CH 3

)=NO-C

1

-C

6 -alkyl, and

R

4 is C 1 -C-alkyl, C 2

-C

6 -alkenyl, C 2

-C

6 -alkenyl [sic] or cyclopropyl, it being possible for these radicals to be partially or fully halogenated and/or to have attached to them one to three of the following groups: aryl and hetaryl, it being possible for the aromatic groups, in turn, to have attached to them 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, or 0050/46490 34

R

4 is aryl, hetaryl or benzyl, it being possible for the aromatic rings in these radicals to be partially or fully halogenated and/or to have attached to them one to three of the following radicals: cyano, nitro, Cl-C 6 -alkyl, Cl-C 6 -haloalkyl, Cl-C 6 -alkoxy, C 1

-C

6 -haloalkoxy and C(=NORi)-An-Rii, or

R

4 is CR 5

=N-Y

1

-R

6 Furthermore, preferred compounds of the formula I are those where

R

3 is Ci-C 6 -alkyl, Cl-C 6 -haloalkoxy, cyclopropyl or

C(CH

3

)=NO-C

1

-C

6 -alkyl steht, and

R

4 is C 1

-C

6 -alkyloxy, it being possible for this radical to be partially or fully halogenated and/or to have attached to it one to three of the following groups: aryl and hetaryl, it being possible for the aromatic groups, in turn, to have attached to them one to three of the following substituents: cyano, halogen, C 1

-C

6 -alkyl, Cl-C 6 -haloalkyl, Cl-C 6 -alkoxy and Ci-C 6 -haloalkoxy, or

R

4 is aryloxy, hetaryloxy or N-aryl-N-methylamino, it being possible for the aromatic rings in these radicals to be partially or fully halogenated and/or to have attached to them one to three of the following radicals: cyano, nitro,

C

1

-C

6 -alkyl, Cl-C 6 -haloalkyl, Cl-C 6 -alkoxy, C 1

-C

6 -haloalkoxy and C(=NORi)-An-R i i or

R

4 is CR 5

=N-Y

1

-R

6 Especially preferred compounds with a view to the use against animal pests and harmful fungi are those of the formula I.1 3 0 2O N2 R 4 30(1.1)

R

1 R3 where the substituents and the index have the following meanings:

R

1 is C(C0 2

CH

3

)=CHCH

3 C(C0 2

CH

3

)=CHOCH

3

C(CO

2

CH

3

)=NOCH

3 or

C(CONHCH

3

)=NOCH

3

R

2 is cyano, halogen, Ci-C 4 -alkyl, Cl-C 2 -haloalkyl, C 1

-C

4 -alkoxy,

C

1

-C

2 -haloalkoxy and C 3

-C

6 -cycloalkyl; m is 0 or 1;

R

3 is hydrogen, hydroxyl, cyano, 0050/46490

C

1

-C

4 -alkyl, C 1

-C

2 -haloalkyl, Ci-C 4 -alkoxy, Ci-C 2 -haloalkoxy,

C

3

-C

6 -cycloalkyl, C3-C 6 -cycloalkyl-Cl-C 4 -alkyl, or benzyl which may be substituted by customary groups;

R

4 is hydrogen, C 3

-C

6 -cycloalkyl, Ci-C 6 -alkyl or Ci-C 6 -alkoxy which may be partially or fully halogenated and/or may have attached to it one to three (in particular one) of the following groups: cyano, Ci-C 4 -alkoxy,

C

3

-C

6 -cycloalkyl, or phenyl, naphthyl, pyridinyl, pyrazinyl, thienyl, pyrazolyl or isoxazolyl, each of which is unsubstituted or substituted by customary groups; phenyl, naphthyl, pyridinyl, pyrazinyl, thienyl, pyrazolyl or isoxazolyl, each of which is unsubstituted or substituted by customary groups; phenoxy, naphthyloxy, pyridinyloxy, pyrazinyloxy, thienyloxy, pyrazolyloxy or isoxazolyloxy, each of which is unsubstituted or substituted by customary groups; or

R

3 and R 4 together with the carbon atom to which they are bonded are a saturated or partially unsaturated, four- to eight-membered ring which, besides hydrocarbon [sic] ring members, may contain a hetero atom from the group consisting of oxygen, sulfur and nitrogen and which may be partially halogenated and/or may have attached to it one to three of the following groups: C 1

-C

4 -alkyl, Ci-C 4 -haloalkyl, C1-C 4 -alkoxy, Cl-C 4 -haloalkoxy, oxo and C1-C4-alkoxyimino (=N-alkoxy)

R

3 and R 4 not simultaneously being bonded to the carbon atom via hetero atoms.

Compounds which are furthermore especially preferred with a view to the use against animal pests and harmful fungi are those of the formula 1.3

R

2 mN

R

6 W'al (1.3) where the substituents and the index have the following meanings: 0050/46490 36

R

1 is 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, Cl-C 4 -alkyl, Ci-C 2 -haloalkyl, Ci-C 4 -alkoxy, Cl-C 2 -haloalkoxy and C 3

-C

6 -cycloalkyl; m is 0ori1;

R

3 is hydrogen, cyano, halogen, Cl-C 4 -alkyl, Cl-C 2 haloalkyl, Cl-C 4 -alkoxy, Cl-C 2 -haloalkoxy and C3-C 6 -cycloalkyl;

R

5 is hydrogen, cyano, halogen, Ci-C 4 -alkyl, Cl-C 2 -haloalkyl, Cl-C 4 -alkoxy, Ci-C 2 -haloalkoxy and C 3

-C

6 -cycloalkyl; Y' is 0, NH or N(CH 3

R

6 is hydrogen,

CI-C

6 -alkyl which may have attached to it one of the following groups: Cl-C 4 -alkoxy, C3-C6-CYCloalkyl which is unsubstituted or substituted by customary groups, or phenyl which is unsubstituted or substituted by customary groups;

C

3

-C

6 -alkenyl, C 3

-C

6 haloalkenyl, C3-C 6 -alkynyl, C 3

-C

6 -haloalkynyl, or C 3

-C

6 -cycloalkyl which is unsubstituted or substituted by customary groups.

Furthermore, especially preferred compounds with a view to the use against animal pests and harmful fungi are those of the formula 2 Rx Ri R 3

RZ

where the substituents and the index have the following meanings: RI is C(CO 2

CH

3

)=CHCH

3

C(CO

2

CH

3

)=CHOCH

3 C(C0 2

CH

3

)=NOCH

3 or C (CONHCH 3

)=NOCH

3

R

2 is cyano, halogen, Cl-C 4 -alkyl, Cl-C 2 -haloalkyl, Cl-C 4 -alkoxy, C1-C2-haloalkoxy and C3-C 6 -CYCloalkyl; m is 0or 1; 0050/46490 37

R

3 is hydrogen, cyano, halogen, Cl-C 4 -alkyl, Ci-C 2 -haloalkyl,

C

1

-C

4 -alkoxy, Ci-C 2 -haloalkoxy and C3-C 6 -cycloalkyl; Rx is hydrogen, halogen, Ci-C 4 -alkyl, Cl-C 2 -haloalkyl, Ci-C 4 -alkoxy, C 1

-C

2 -haloalkoxy and C3-C 6 -cycloalkyl; RY is hydrogen,

C

1

-C

6 -alkyl, which may be partially or fully halogenated and/ or may have attached to it one to three (in particular one) of the following groups: C 1

-C

4 -alkoxy, C3-C 6 -cycloalkyl which is unsubstituted or substituted by customary groups, or phenyl which is unsubstituted or substituted by customary groups; Ci-C 6 -alkoxy, C 1

-C

6 -haloalkoxy,

C

3

-C

6 -cycloalkyl which is unsubstituted or substituted by customary groups; phenyl which is unsubstituted or substituted by customary groups, pyridyl which is unsubstituted or substituted by customary groups, or pyrimidyl which is unsubstituted or substituted by customary groups; Rz is hydrogen, cyano, halogen, C 1

-C

4 -alkyl, Ci-C 2 -haloalkyl and C3-C 6 -cycloalkyl, or RY and R x together with the double bond to which they are bonded are C4-C 6 -cycloalkenyl.

Especially preferred compounds I with a view to their use are those compiled in the tables which follow. Moreover, the groups mentioned in the tables for one substituent are, on their own, an especially preferred embodiment of the substituent in question, independently of the combination in which they are mentioned.

Table 1 Compounds of the general formula Ia.l where R 2 m is hydrogen and the combination of the radicals R 3 and R 4 for each compound corresponds to one line of Table A

R

2 m N R 4 5 ,OCH a4

N

OCHR3 0050/46490 38 Table 2 Compounds of the general formula Ib.1 where R 2 m is hydrogen and the combination of the radicals R 3 and R 4 for each compound corresponds to one line of Table A

R

2 m

R

0 Table 3 Compounds of the general formula Ic.l where R 2 m is hydrogen and the combination of the radicals R 3 and R 4 for each compound corresponds to one line of Table A

R

2 m

R

4

H

2 N CH 3 (Ic.1) NOCH R 3 0 Table 4 Compounds of the general formula Id.l where R 2 m is hydrogen and the combination of the radicals R 3 and R 4 for each compound corresponds to one line of Table A

R

2 m R4 0 O N

SCH

3 Q OCH3 (Id.1)

R

3 o Table Compounds of the general formula Ie.l where R 2 m is hydrogen and the combination of the radicals R 3 and R 4 for each compound corresponds to one line of Table A

R

2 mN

CH

3

OCH

3 (le.) 0 Table 6 Compounds of the general formula Ia.2 where R 2 m is hydrogen and the combination of the radicals R 3 and R 4 for each compound cor- 0050/46490 39 responds to one line of Table A

R

2 m -N R 3 0

CH

3

N/OCH

3 01 1Table 7 Compounds of the general formula Ib.2 where R2m is hydrogen and the combination of the radicals R 3 and R 4 for each compound corresponds to one line of Table A

R

2 m OR

CH

3 NH Nl OCH 3

R

4 b2) 0 Table 8 Compounds of the general formula Ic.2 where R 2 m is hydrogen and the combination of the radicals R 3 and R 4 for each compound corresponds to one line of Table A

R

2 m N R 3

H

2 N ,OCH (Ic.2) 0 Table 9 Compounds of the general formula Id.2 where R 2 m is hydrogen and the combination of the radicals R 3 and R 4 for each compound corresponds to one line of Table A R' Im- R 3 -ON R CH OCHs (Id.2) 0 STable Compounds of the general formula Ie.2 where R 2 m is hydrogen and the combination of the radicals R 3 and R 4 for each compound -Ut\ 0050/46490 corresponds to one line of Table A 2 mN

R

3

CH

3 O H 3

R

0 Table A: (Ie.2) No. R 3

R

A. 1 H CH 3 A. 2 H CH 2

CH

3 A. 3 H MHCH, 2

CH-A

A. 4 H CH(CH 3 2 A. 5 H CH 2

CH

2

CH

2

CH

3 A.6 H C(CH 3 3 A.7 H CH(CH 3

)CH

2

CH

3 A.8 H C 6

H

A.9 H 2-F-C 6

H

4 H 3-F-C 6

H

4 A.11 H 4-F-C 6

H

4 A.12 H 3-CH 3

-C

6

H

4 A.13 H 3-OCH 3

-C

6

H

4 A.14 H 3-CF 3

-C

6

H

4 H 3-Cl-C 6

H

4 A.16 H 2-CH 3

-C

6

H

4 A.17 H 4-CH 3

-C

6

H

4 A.18 H cyclopropyl A.19 H cyclohexyl H CH 2

CH

2 Cl A.21 H CH 2 CHgCHgCN A.22 H CH 2

-C

6

H

A.23 H CH 2

CH

2

CH

2

CH

2

-OCH

3 A.24 H CH 2

CH

2

-OCH

2

CH

3 H CH 2

C(CH

3

)=NOCH

3 A.26 H CH 2 -[4-F-C 6

H

4 A.27 H CH 2 -[3-CN-C 6

H

4 A.28 H 13-CN-C 6

H

4 0050/46490 No. R 3

R

4 A.29 H 3, 5- (CHA) 2

-C

6

H

3 A.30 H 3-COCH 3

-C

6

H

4 A.31 H 3- C(CH 3

=NOCH

3 I -C 6

H

4 A.32 H 1-naphthyl A.33 H CH 2

CH

2

-O-C

6

H

A.34 H CH 2 -[3-C1-pyridin-5-yl] A.35 H 4-OCH 3 -pyridin-2-yl A.36 H CH2-[5-Cl-pyrazin-2-yl] A.37 H 2-thienyl A.38 H 3-CH(CH 3 2 A.39 H 3-C 6

H

5 -pyrazol-1-yl H OCH(CH 3 2 A.41 H OCH 2

CH

2

CH

2

CH

2

CH

3 A.42 H 0-[4-F-C 6

H

4 A.43 H OCH 2 -[4-F-C 6

H

4 A.44 H O-[6-CH 3 -pyridin-2-yl] H O-CO-[4-C1-C 6

H

4 A.46 H NH-[4-C1-C 6

H

4 A.47

CH

3

CH

3 258CH H2H A.49

CH

3

CH

2 CH2 3

CH

3

CH(CH

3 2 A .51

CH

3

CH

2

CH

2

CH

2

CH

3 A.52

CH

3 C(CH 3 3 A.53

CH

3

CH(CH

3

)CH

2

CH

3 A.54

CH

3

C

6

H

CH

3 2-F-C 6

H

4 A.56 CH 3 3-F-C 6

H

4 A.57

CH

3 4-F-C 6

H

4 A.58

CH

3 3-CH 3

-C

6

H

4 A.59

CH

3 3-OCH 3

-C

6

H

4 A.60 OH 3 3-CF 3

-C

6

H

4 A.61

CH

3 3-C1-C 6

H

4 A.62

OH

3 2-CH 3

-C

6

H

4 A.63

OH

3 4-CH 3

-C

6

H

4 A.64 OH 3 cyclopropyl A.65

OH

3 cyclohexyl A.66

OH

3

CH

2

CH

2 Cl 0050/46490 No. R 3

R

A.67 CH 3

CH

2

CH

2

CH

2

CN

A .68 CH 3

CH

2

-C

6

H

A.69 CH 3

CH

2

CH

2

CH

2

CH

2

-OCH

3

CH

3

CH

2

CH

2

-OCH

2

CH

3 A .71 CH 3

CH

2 C (CH 3

='OCH

3 A.72 CH 3

CH

2 -[4-F-C 6

H

4 A.73

CH

3

CH

2 -fj3-CN-C 6

H

4 *A.74 CH 3 3-CN-0 6

H

4

CH

3 3,5-(CH 3 2

-C

6

H

3 A.76 CH 3 3-COCH 3

-C

6

H

4 A.77 CH 3 3- [C (CH 3

=NOCH

3

]I-C

6

H

4 A.78 CH 3 1-naphthyl A.79 CH 3

CH

2

CH

2

-O-C

6

H

CH

3

CH

2 A .81 CH 3 4-OCH 3 -pyridin-2--yl A.82 CH 3

CH

2 -jj5-C1--pyrazin-2-yl] A.83 CH 3 2-thienyl A .84 CH 3 3-CH(CH 3 2 A .85 CH 3 3-C 6

H

5 -pyrazol-1-yl A .86 CH 3

OCH(CH

3 2 *.87 CH 3

OCH

2

CH

2

CH

2

CH

2

CH

3 A.88 CH 3 O-[4-F-C 6

H

4 A.89 CH 3

OCH

2 -[4-F-C 6

H

4 A.90

CH

3 O-[6-CH 3 -pyridin-2-yl] A.91 CH 3 0-CO-[4-Cl-C 6

H

4 A.92 CH 3 NH-[4-Cl-C 6

H

4 A.93 OH CH 3 A.94 OH CH 2

CH

2

CH

2

CH

3 A.95 OH CH(CH 3 2 A.96 OH 3-CH 3

-C

6

H

4 A.97 OH CH 2

-C

6

H

A.98 OH 3,5-1 2

-C

6

H

3 A.99 OCH 3

CH

3 A. 100 OCH 3

CH

2

CH

2

CH

2

CH

3 A.101 OCH 3

CH(CH

3 2 A. 102 OCH 3

CH

2

CH

2

CH

2

CH

2

CH

2

CH

3 A.103 OCH 3 3-CH 3

-C

6

H

4 A.104 OCH 3

CH

2

-C

6

H

A.105 OCH 3 3, 5-Cl 2

-C

6

H

3 0050/46490 No.R34 A.106

OCH

2

CH

3

CH

3 A. 107 OCH 2

CH

3

CH

2

CH

2

CH

3 A.108

OCH

2

CH

3

CH(CH

3 2 A.109 OCH 2

CH

3

CH

2

CH

2

CH

2

CH

2

CH

3 A.110 OCH 2

CH

3 3-CH 3

-C

6

H

4 A.111 OCH 2

CH

3

CH

2 -[4-F-C 6

H

4 A.112

OCH

2

CH

3 2,4-F 2

-C

6

H

3 A.113 cyclopropyl

CH

3 A.114 cyclopropyl CH 2 CHqCH 3

A

A.115 cyclopropyl

OCH

2

CH

3 A.116 cyclopropyl C 6

H

A.117 cl C 6

H

A.118 Cl CH 3 A.119 Cl CH(CH 3 2 A.120 Cl 3-CH 3

-C

6

H

4 A.121 Cl 3-CN-C 6

H

4 A. 122 Cl CH 2

CH

2

-O-C

6

H

A.123 Cl CH 2 CHq-OCHqCH 3

A

A.124 Cl CH 2 -[4-F-C 6

H

4 A.125 SCH 3

CH

3 A.126 SCH 3

C

6

H

A.127

SCH

3

CH(CH

3 2 A.128

CH(CH

3 2

CH

3 A.129

CH(CH

3 2

CH

2

CH

3 A.130

CH(CH

3 2

C

6

H

A.131

CH(CH

3 2

OCH

3 A.132 CH(CH 3 2

OCH(CH

3 2 A.133 CH(CH 3 2 3-CH 3

-C

6

H

4 A.134 CN CH 3 A.135 CN 3-CH 3

-C

6

H

4 A.136 CN CH 2 -[2,4-C1 2

-C

6

H

3 A, 137 CN CH 2

CH

2

CH

2

CH

3 A.138 CN CH(CH 3 2 A.139

CH

2

CH

3

CH

3 A. 140 CH 2

CH

3

CH

2

CH

3 A.141 CH 2

CH

3

CH-)CH-

2

CH

3

A

A.142 CH 2

CH

3

CH(CH

3 2 A. 143 CH 2

CH

3

CH

2

CH

2

CH

2

CH

3 A.144

CH

2

CH

3

IC(CH

3 3 0050/46490 No. R 3

R

A.145 CH 2

CH

3

CH(CH

3

)CH

2

CH

3 A.146 CH 2

CH

3

C

6

H

A. 147 CH 2

CH

3 2-F-C 6

H

4 A. 148 CH 2

CH

3 3-F-C 6

H

4 A.149 CH 2

CH

3 4-F-C 6

H

4 A.150 CH 2

CH

3 3-CH 3

-C

6

H

4 A.151 CH 2

CH

3 3-OCH 3

-C

6

H

4 A.152 CH 2

CH

3 3-CF 3

-C

6

H

4 A.153 CH 2

CH

3 3-Cl-C 6

H

4 A. 154 CH 2

CH

3 2-CH 3

-C

6

H

4 A. 155 CH 2

CH

3 4-CH 3

-C

6

H

4 A.156 CH 2

CH

3 cyclopropyl A.157 CH 2

CH

3 cyclohexyl A. 158 CH 2

CH

3

CH

2

CH

2

C.

A. 159 CH 2

CH

3

CH

2 CH-gCH- 2

CN

A. 160 CH 2

CH

3

CH

2

-C

6

H

A. 161 CH 2

CH

3

CH

2

CH

2

CH

2

CH

2

-OCH

3 A. 162 CH 2

CH

3

CH

2

CH

2

-OCH

2

CH

3 A.163 CH 2

CH

3

CH

2

C(CH

3

)=NOCH

3 A.164 CH 2

CH

3

CH

2 -(4-F-C 6

H

4 A.165 CH 2

CH

3

CH

2 -[3-CN-C 6

H

4 1 A.166 CH 2

CH

3 3-CN-C 6

H

4 A.167 CH 2

CH

3 3, 5- (CH 3 2

-C

6

H

3 A.168 CH 2

CH

3 3-COCH 3

-C

6

H

4 A.169 CH 2

CH

3 3-[C(CH 3

)=NQCH

3

]-C

6

H

4 A.170 CH 2

CH

3 1-naphthyl A. 171 CH 2

CH

3

CH

2

CH

2

-O-C

6

H

A. 172 CH 2

CH

3

CH

2 A.173 CH 2

CH

3 4-OCH 3 -pyridin-2-yl A. 174 CH 2

CH

3

CH

2 -[5-Cl-pyrazin-2-yl] A.175 CH 2

CH

3 2-thienyl A. 176 CH 2

CH

3 3-CH(CH 3 2 A.177 CH 2

CH

3 3-C 6

H

5 -pyrazol-1-yl A.178 CH 2

CH

3

OCH(CH

3 2 A. 179 CH 2

CH

3

OCH

2

CH

2

CH

2

CH

2

CH

3 A.180 CH 2

CH

3 O-[4-F-C 6

H

4 A.181 CH 2

CH

3

QCH

2 6

H

4 1 A. 182 CH 2

CH

3 0- [6-CH 3 -pyridin-2--yl] A.183 CH 2

CH

3 0-CO-[4-Cl-C 6

H

4

J

0050/46490 No.R34 A.184

CH

2

CH

3 NH-[4-Cl-C 6

H

4 A..185

OH

3

CH

2 ON=C (CHA) 2 A.186 OH 3

CH

2

ON=C(CH

3

)-CH

2

CH

3 A.187

CH

3

CH

2

ON=C(CH

3

)-C

6

H

A .188

CH

3

CH

2

ON=C(CH

3 )-[4-Cl-C 6

H

4 A.189

CH

2

CH

3

CH

2 ObI=C(CH 3 2 A.190 CH 2

CH

3

CH

2

ON=C(CH

3

)-CH

2

CH

3 A.191

CH

2

CH

3

CH

2

OI'=C(CH

3

)-C

6

H

A. 192

CH

2

CH

3

CH

2

ON=C(CH

3 )-[4-Cl-C 6

H

4 A.193

CH

2

-C

6

H

5

CH

2

ON=C(CH

3 2 A. 194 CH 2

-C

6

H

5

CH

2 ON=C (CHA)-CH 2

CH

3 A.195

CH

2

-C

6

H,

5

CH

2

O-N=C(CH

3

-C

6

H

A.196

CH

2

-C

6

H

5

CH

2

N=(CH

3 )-[4-Cl-C 6

H

4 A.197 H CH=CH-C 6

H

A.198 H CH=C(CH 3

)-C

6

H

A.199 H CH=CCl-C 6

H

A.200 H C(CH 3

)=CH-C

6

H

A.201 H CC1=CH-C 6

H

A.202 H CH=CH-[4-F-C 6

H

4 A.203 H CH=C(CH 3 6

H

4 A.204 H CH=CC1-[4-F-C 6

H

4 A.205 H CC1=CH-[4-F-C 6

H

4 A.206 H C(CH 3 )=CH-[4-F-C 6

H

4 A.207

OH

3

CH=CH-C

6

H

A.208

OH

3 CH=C(CH 3

)-C

6

H

A..209

OH

3 OH=OC1-C 6

H

A.210

OH

3

C(CH

3

)=CH-C

6

H

A.211

OH

3 CC1=CH-C 6

H

A..212

OH

3 CH=CH- [4-F-C 6

H

4 A.213

CH

3

CH=C(CH

3 6

H

4 A.214

OH

3 CH=CC1-[4-F-C 6

H

4 A .215

OH

3 CC1=CH-[4-F-C 6

H

4 A.216 CH 3

C(CH

3 6 1 4 A.217 CH2CH3

CH=OH-C

6

H

A.218 012013 CH=C(CH 3

)-C

6

H

A.219

CH

2

CH

3 CH=CO1-C 6

H

A.220 CH 2

CH

3

C(CH

3

)=CH-C

6

H

A.221 CH 2

CH

3 CC1=CH-CgHq A. 222

CH

2

CH

3 CH=CH- [4-F-C 6

H

4 1 0050/46490 No.R34 A.223

CH

2

CH

3 CH-=C (CH 3 [4-F-C 6

H

4 1 A.224

CH

2

CH

3 CH=CC1- [4-F-C 6

H

4 1 A.225 CH 2

CH

3 CC1=*-CH- [4-F-C 6

H

4 1 A.226

CH

2

CH

3

C(CH

3 )=CH-[4-F-C 6

H

4 A.227

CH

2

-C

6

H

5

CH=CH-C

6

H

A.228

CH

2

-C

6

H

5

CH=C(CH

3

)-C

6

H

A.229 CH 2

-C

6

H

5 CH=CCl-C 6

H

A.230

CH

2

-C

6

H

5

C(CH

3

)=CH-C

6

H

A.231 CH 2

-C

6

H

5 CC1=CH-CrH, A.232

CH

2

-C

6

H

5 CH=CH- [4-F-C 6

H

4 1 A.233

CH

2

-C

6

H

5

CH=C(CH

3 6

H

4 A.234

CH

2

-C

6

H

5 CH=CC1-[4-F-C 6

H

4 A.235

CH

2

-C

6

H

5 CC1=CH- [4-F-C 6

H

4 1 A.236

CH

2

-C

6

H

5

C(CH

3 )=CH-[4-F-C 6

H

4

J

A.237 H CH(CH 3

)-C(CH

3

)=NOCH

3 A.238 H CH(CH 3

)-C(CH

3

)=NOCH

2

CH

3 A.239 H CH(CH 3

)-C

6

H

A.240 H CH(CH 3 6

H

4 A.241 H 1-C6H 5 -CYClopropy.

A.242 H l-[4-Cl-C 6

H

4 ]-cyclopropyl A.243 H CH 2 C (CH 3

=NOCH

3 A.244 H CH 2

C(CH

3

)=NOCH

2

CH

3 A.245 H l-[C(CH 3

)=NOCH

3 ]-cyclopropyl A .246

CH

3

CH(CH

3

)-C(CH

3

)=NOCH

3 A.247

CH

3 CH (CH 3 -C (CH 3

=NOCH

2

CH

3 A.248

CH

3 CH(0H 3

)-C

6

H

A.249

CH

3

CH(CH

3 6

H

4 A..250

CH

3 1-C6H 5 -cyclopropyl A.251

CH

3 l-[4-Cl-C 6

H

4 ]-cyclopropyl A.252

CH

3

CH

2

C(CH

3

)=NOCH

3 A.253

CH

3 CH2C(CH 3

)=NOCH

2

CH

3 A.254

CH

3 lJIC(CH 3

)=NOCH

3 ]-cyclopropyl A.255 CH 2

CH

3

CH(CH

3

)-C(CH

3

)=NOCH

3 A.256

CH

2

CH

3

CH(CH

3

)-C(CH

3

)=NOCH

2

CH

3 A.257

CH

2

CH

3

CH(CH

3

)-C

6

H

A.258

CH

2

CH

3

CH(CH

3 6

H

4 A.259 CH 2

CH

3 1-C 6

H

5 -CYClopropyl A. 260 CH 2

CH

3 1- [4-C1-C 6

H

4 1]-cyclopropyl A.261

CH

2

CH

3

CH

2

C(CH

3

)=NOCH

3 0050/46490 No. R3R 4 A.262

CH

2

CH

3

CH

2 C (CH 3

=NOCH

2

CH

3 A.263

CH

2

CH

3 1-(C(CH 3

)=NOCH

3 1-cyclopropyl A.264

CH

2

-C

6

H

5 CH(CH3)-C(CH 3

)=NOCH

3 A.265

CH

2

-C

6

H

5

CH(CH

3

)-C(CH

3

)=NOCH

2

CH

3 A.266

CH

2

-C

6

H

5

CH(CH

3

)-C

6

H

A.267

CH

2

-C

6

H

5

CH(CH

3 6

H

4 A.268

CH

2

-C

6

H

5 1-C6H5--cyclopropyl A.269

CH

2

-C

6

H

5 l-[ 4 -Cl-C6H4]-cyclopropyl A.270

CH

2

-C

6

H

5

CH

2

C(CH

3

)=NOCH

3 A.271

CH

2

-C

6

H

5

CH

2

C(CH

3 )=NOCHgCH 3 4 A.272

CH

2

-C

6

H

5 1-[C(CH 3

)=NOCH

3 ]-cyclopropyl A.273

-(CH

2 )4- A.274 A.275 (H)0-C2- A.276 A.277 (H)2C CA-(H)2 A.278- C22- 2 A.279

-(CH

2 2 -C (=NOCH 3

(H

2 2 A.280 -(H)2C(C3 -(H)2 A.281

-CH

2

-CH(CH

3

)-CH

2

-CH(CH

3

)-CH

2 A.282

-(CH

2 3

CH(CH

3

)-CH

2 A.283

-CH=CH-C(=NOCH

3

)-CH=CH-

A.84-CH 2 -C (=NOCH 3

(H

2 3 Table 11 Compounds of the general formula Ia.3 where 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 Q-

N

0 (1a.3) Table 12 Compounds of the general formula Ia.3 where R 2 m is hydrogen, Y 4is 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 0050/46490 Table 13 Compounds of the general formula Ia.3 where R 2 m is hydrogen, Y is N(CH 3 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 14 Compounds of the general formula Ib.3 where 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

R

2 m m N RN

R

CH

3 N N OCH3 R3 0 (lb.3) Table Compounds of the general formula Ib.3 where R 2 m 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 16 Compounds of the general formula Ib.3 where R 2 m is hydrogen, Y is N(CH 3 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 17 Compounds of the general formula Ic.3 where 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

R

2 m O N NI R H N .CH I (lc.3) Table 18 Compounds of the general formula Ic.3 where R 2 m 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 0050/46490 Table 19 Compounds of the general formula Ic.3 where R 2 m is hy is N(CH 3 and the combination of the radicals R 3

R

4 for each compound corresponds to one line of Table B Table Compounds of the general formula Id.3 where R 2 is hy is oxygen, and the combination of the radicals R 3

R

4 for each compound corresponds to one line of Table B 6 hy R5 rdrogen, Y

R

5 and R 6 drogen, Y

R

5 and R 6 (Id.3) drogen, Y and R 6 for Table 21 Compounds of the general formula Id.3 where R 2 m is is NH, and the combination of the radicals R 3

R

4 each compound corresponds to one line of Table B Table 22 Compounds of the general formula Id.3 where R 2 m is hy is N(CH 3 and the combination of the radicals R 3

R

4 for each compound corresponds to one line of Table B Table 23 Compounds of the general formula Ie.3 where R 2 m is hy is oxygen, and the combination of the radicals R 3

R

4 for each compound corresponds to one line of Table B drogen, Y

R

5 and R 6 'drogen, Y

R

5 and R 6 (le.3)

R

2 m 5

N

H

3 CH 3 R3 0 Table 24 Compounds of the general formula Ie.3 where R 2 m 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 0050/46490 Table Compounds of the general formula Ie.3 where R 2 m is hydrogen, Y is N(CH 3 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 26 Compounds of the general formula Ia.4 where R 2 m is is oxygen, and the combination of the radicals R 3 for each compound corresponds to one line of Table hydrogen, Y

R

4

R

5 and R 6

B

(la.4) -R6 Table 27 Compounds of the general formula Ia.4 where R 2 m is is NH, and the combination of the radicals R 3

R

4 each compound corresponds to one line of Table B hydrogen, Y

R

5 and R 6 for Table 28 Compounds of the general formula Ia.4 where R2m is hy is N(CH 3 and the combination of the radicals R 3

R

4 for each compound corresponds to one line of Table B Table 29 Compounds of the general formula Ib.4 where R 2 m is hy is oxygen, and the combination of the radicals R 3

R

4 for each compound corresponds to one line of Table B drogen, Y

R

5 and R 6 drogen, Y

R

5 and R 6 (lb.4) R 2 m N N R 0N

CH

3 NHT N 0CH 3

R

3

Y

1 0

-R

6 Table Compounds of the general formula Ib.4 where R 2 m 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 1~1_ 0050/46490 Table 31 Compounds of the general formula Ib.4 where R 2 m is hydrogen, Y is N(CH 3 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 32 Compounds of the general formula Ic.4 where 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 (lc.4)

-R

6 Table 33 Compounds of the general formula Ic.4 where R 2 m 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 34 Compounds of the general formula Ic.4 where R 2 m is hydrogen, Y is N(CH 3 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 Compounds of the general formula Id.4 where R2m 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 (ld.4) Table 36 Compounds of the general formula Id.4 where R2m 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 0050/46490 Table 37 Compounds of the general formula Id.4 where R 2 m is hydrogen, Y is N(CH 3 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 38 Compounds of the general formula Ie.4 where 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 (le.4)

R

6 Table 39 Compounds of the general formula Ie.4 where R 2 m 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 Compounds of the general formula Ie.4 where R 2 m is hydrogen, Y is N(CH 3 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 B: No. R 3 R5 R6 B.1 Cl H H B.2 Cl CH 3

H

B.3 Cl CH 2

CH

3

H

B.4 Cl CF 3

H

Cl CHF 2

H

B.6 Cl CH 2 F H B.7 Cl Cl H B.8 Cl OCH 3

H

B.9 Cl OCH 2

CH

3

H

Cl CN H B.11 CH 3 H H B.12 CH 3

CH

3

H

B.13 CH 3

CH

2

CH

3

H

0050/46490 No. R 3

RSR

6 B. 14 OH 3 OF 3

H

B. 15 CH 3 CHF 2

H

B. 16 OH 3

CH

2 F H B. 17 CH 3 Cl H B. 18 CH 3 00H 3

H

B. 19 CH 3 OCH 2

CH

3

H

B.20 CH 3 ON H B.21.

OF

3 H H B.22

OF

3 OH 3

H

B.23

CF

3 CH 2

CH

3

H

B.24

CF

3 CF 3

H

B.25

OF

3 CHF 2

H

B.26

OF

3 CH 2 F H B.27

CF

3 Cl H B.28

CF

3 00H 3

H

B.29 OF 3 00H 2

CH

3

H

OF

3 ON H B.31 Cl H

OH

3 B.32 01

OH

3

OH

3 B.33 01 OH 2

CH

3

OH

3 B.34 Cl

CF

3

OH

3 Cl

CHF

2

OH

3 B.36 01

CH

2 F OH 3 B.37 Cl Cl OH 3 B.38 Cl 00H 3

OH

3 B.39 01

OCH

2

CH

3

OH

3 Cl ON

OH

3 B.41

OH

3 H OH 3 B.42

OH

3 OH 3

OH

3 B.43

OH

3 CH 2

CH

3

CH

3 B.44

OH

3 OF 3 OH 3

OH

3 CHF 2

OH

3 B-46 OH 3 CH 2 F OH 3 B.47

OH

3 Cl

OH

3 B.4

OH

3 OCH 3

OH

3 B.49

OH

3 00H 2

CH

3

OH

3

OH

3 ON

OH

3 B.51

CF

3 H

OH

3 B.2

F

3 O H 3

OH

3 0050/46490 No. R 3

R

5

R

B. 53 CF 3 CH 2

CH

3

CH

3 B.54

CF

3 CF 3

CH

3 5B.55 CF 3

CHF

2

CH

3 B.56

CF

3 CH 2 F CH 3 B.57

CF

3 Cl CH 3 B.58

CF

3 OCH 3

CH

3 10B.59 CF 3

OCH

2

CH

3

CH

3

CF

3 CN

CH

3 B.61 Cl H CHqCHq B.62 Cl

CH

3

CH

2

CH

3 B.63 Cl

CH

2

CH

3

CH

2

CH

3 15B.64 Cl

CF

3 CH 2

C-

3 B.6-r Cl

CHF

2

CH

2

CH

3 B.66 Cl

CH

2 F CH 2

CH

3 B.67 Cl Cl CH 2

CH

3 B.68 Cl

OCH

3

CH

2

CH

3 B.69 Cl

OCH

2

CH

3

CH

2

CH

3 Cl CN CH 2

CH

3 B.71 CH 3 H CH 2

CH

3 B.72 CH 3

CH

3

CH

2

CH

3 B.73 CH 3

CH

2

CH

3

CH

2

,CH

3 B.74

CH

3 CF 3

CH

2

CH

3

CH

3 CHF 2

CH

2

CH

3 B.76~ CH HF C 2

H

B.77 CH 3 C2 CH 2 CH2 3 B.77

CH

3 OCH CH 2

CH

3 B.79

CH

3 OHCH 3

CH

2

CH

3 13.80

CH

3 OCN2H

CH

2

CH

3 35B.80

CF

3 HN CH 2

CH

3 .82

CF

3 CH

CH

2 C H 3 B3.83

CF

3 CHCH 3

CH

2

CH

3 B.84

CF

3 CHC 3

CH

2

CH

3 40R.85

CF

3 CHF3

CH

2

CH

3 40B.86 CF 3

CH

2 F CH 2

CH

3 13.87

CF

3 Cl2

CH

2

CH

3 1.88

CF

3 OcH

CH

2

CH

3 1.89

CF

3 OHCH 3

CH

2

CH

3 B.89_ 1.90

CF

3 CN CH 2

CH

3 1.91 Cl H CH 2

CH

2

CH

3 0050/46490 No. R3R 5

R

B. 92 Cl

CH

3

CH

2

CH

2

CH

3 B.93 Cl CH 2

CH

3

CH

2

CH

2

CH

3 B.94 Cl CF 3 CHqCHqCH 3 i Cl CHF 2

CH

2

CH

2

CH

3 B.96 Cl CH 2 F CHqCH 2

)CH

3 B.97 Cl Cl CH 2

)CH

2

CH

3

A

B.98 Cl

OCH

3

CH

2

CH

2

CH

3 B.99 Cl OCH 2

CH

3

CH

2

CH

2

CH

3 B.100 Cl CN CH7CH 2 ?CH-i B.101 CH 3 H CH 2

CH

2

CH

3 B.102 OH 3 CH 3

CH

2

CH

2

CH

3 B.103 CH 3

CH

2

CH

3

CH

2

CH

2

CH

3 B.104 OH 3 CF 3

CH

2

CH

2

CH

3 B.105 CH 3 CHF 2

CH

2

CH

2

CH

3 B. 106 OH 3

CH

2 F CHqCHqCH 3

A

B.107 CH 3 Cl CH 2

CH

2

?CH

3 i B. 108 CH 3

OCH

3

CH

2

CH

2

CH

3 B.109 OH 3

OCH

2

CH

3

CH

2

CH

2

CH

3 B.110 OH 3 CN CH 2

CH

2 CH-i B.111 CF 3 H CH 2

CH

2

CH

3 B.112 CF 3 OH 3

CH

2

CH

2

CH

3 B.113 CF 3

CH

2

CH

3

CH

2

CH

2

CH-

B.114 OF 3 OF 3

CH

2

CH

2

CH

3 B. 115 OF 3

CHF

2

CH

2

CH

2

CH

3 B. 116 CF 3

CH

2 F CH 2 CHqCH 3

A

B.117 OF 3 01 CH 2

CH

2

CH

3 B. 118 OF 3 00H 3

CH

2

CH

2

CH

3 B. 119 CF 3

OCH

2

CH

3

CH

2

CH

2

CH

3 B. 120 OF 3 ON CH 2

CH

2

CH

3 B.121 Cl H CH(CH 3 2 B.122 Cl

OH

3

CH(CH

3 2 B.123 Cl

CH

2

CH

3

ICH(CH

3 2 B.124 Cl

CF

3

CH(CH

3 2 B.125 Cl

CHF

2

CH(CH

3 2 B.126 Cl

OH

2 F CH(CH 3 2 B.127 Cl Cl CH(CH 3 2 B.128 Cl

OCH

3

CH(CH

3 2 B.129 Cl

OCH

2

CH

3

OH(CH

3 2 B.130 Cl ON ICH(CH 3 2 0050/46490 No. R 3 RS6 B. 131 CH 3 H CH(CH 3 2 B. 132 CH 3

CH

3

CH(CH

3 2 B. 133 CH 3

CH

2

CH

3

CH(CH

3 2 B. 134 CH 3

CF

3

CH(CH

3 2 B. 135 CH 3

CHF

2

CH(CH

3 2 B. 136 CH 3

CH

2 F CH(CH 3 2 B. 137 CH 3 Cl CH(CH 3 2 B. 138 CH 3

OCH

3

CH(CH

3 2 B. 139 CH 3

OCH

2

CH

3

CH(CH

3 2 B.140 CH 3 CN CH(CH 3 2 B.141 CF 3 H CH(CH 3 2 B.142 CF 3

CH

3

CH(CH

3 2 B.143 CF 3

CH

2

CH

3

CH(CH

3 2 B.144 CF 3

CF

3

CH(CH

3 2 B.145 CF 3

CHF

2

CH(CH

3 2 B.146 CF 3

CH

2 F CH(CH 3 2 B.147 CF 3 Cl CH(CH 3 2 B.148 CF 3

OCH

3

CH(CH

3 2 B.149 CF 3

OCH

2

CH

3

CH(CH

3 2 B.150 CF 3 CN CH(CH 3 2 B.151 Cl H CH 2

CH=CH

2 B.152 Cl CH 3

CH

2

CH=CH

2 B.153 Cl

CH

2

CH

3

CH

2

CH=CH

2 B.154 Cl

CF

3

CH

2

CH=CH

2 B.155 Cl

CHF

2

CH

2

CH=CH

2 B.156 Cl

CH

2 F CH 2

CH=CH

2 B.157 Cl Cl CH 2

CH=CH

2 B.158 Cl

OCH

3

CH

2

CH=CH

2 B.159 Cl OCH 2

CH

3

CH

2

CH=CH

2 B.160 Cl CU CH 2

CH=CH

2 B.161 CH 3 H CH 2

CH=CH

2 B.162 CH 3

CH

3

CH

2

CH=CH

2 B. 163 CH 3

CH

2

CH

3

CH

2

CH=CH

2 B.164 CH 3

CF

3

CH

2

CH=CH

2 B.165 CH 3

CHF

2

CH

2

CH=CH

2 B.166 CH 3

CH

2 F CH7CH=CH? B.167 CH 3 Cl CH 2

CH=CH

2 B.168 CH 3

OCH

3

CH

2

CH=CH

2 B.169 CH 3

OCH

2

CH

3

CH

2

CH=CH

2 0050/46490 No. R3R 5

R

6 B. 170 CH 3 CN CH 2

CH=CH

2 B.171 CF 3 H CH 2

CH=CH

2 B.172 CF 3 CH 3

CH

2

CH=CH

2 B. 173 CF 3

CH

2

CH

3

CH

2

CH=CH

2 B.174 CF 3 CF 3

CH

2

CH=CH

2 B.175 CF 3

CHF

2

CH

2

CH=CH

2 B.176 CF 3

CH

2 F CH 2

CH=CH

2 B.177 CF 3 Cl CH 2

CH=CH

2 B.178 CF 3

OCH

3

CHCH=CH

2 B.179 CF 3

OCH

2

CH

3

CH

2

CH=CH

2 B.180 CF 3 CN CH 2

CH=CH

2 B.181 Cl H- CH 2 CH=CH-Cl (trans) B.182 Cl CH 3

CH

2 CH=CH-Cl (trans) B.183 Cl CH 2

CH

3

CH

2 CH=CH-Cl (trans) B.184 Cl CF 3

CH

2 CH=CH-C1 (trans) B.185 Cl CHF 2

CH

2 CH=CH-Cl (trans) B.186 Cl CH 2 F CH 2 CH=CH-Cl (trans) B.187 Cl Cl CH 2 CH=CH-Cl (trans) B.188 Cl OCH 3

CH

2 CH=CH-Cl (trans) B.189 Cl OCH 2

CH

3

CH

2 CH=CH-Cl (trans) B.190 Cl CN CH 2 CH=CH-Cl (trans) B.191 CH 3 H CH 2 CH=CH-Cl (trans) B.192 CH 3

CH

3

CH

2 CH=CH-Cl (trans) B.193 CH 3

CH

2

CH

3

CH

2 CH=CH-Cl (trans) B.194 CH 3

CF

3

CH

2 CH=CH-Cl (trans) B.195 CH 3

CHF

2

CH

2 CH=CH-Cl (trans) B.196 CH 3

CH

2 F CH 2 CH=CH-C1 (trans) B.197 CH 3 Cl CH 2 CH=CH-C1 (trans) B.198 CH 3

OCH

3

CH

2 CH=CH-Cl (trans) B.199 CH 3

OCH

2

CH

3

CH

2 CH=CH-Cl (trans) B.200 CH 3 CN CH 2 CH=CH-Cl (trans) B.201 CF 3 JH CH 2 CH=CH-Cl (trans) B.202 CF 3

CH

3

CH

2 CH=CH-Cl (trans) B.203 CF 3

CH

2

CH

3

CH

2 CH=CH-Cl (trans) B.204 CF 3

CF

3

CH

2 CH=CH-Cl (trans) B.205 CF 3

CHF

2

CH

2 CH=CH-Cl (trans) B.206 CF 3

CH

2 F CH 2 CH=CH-Cl (trans) B.207 CF 3 Cl CH 2 CH=CH-Cl (trans) B.208 CF 3

OCH

3

CH

2 CH=CH-Cl (trans) 0050/46490 No. R 3 RS6 B.209 CF 3

OCH

2

CH

3

CH

2 CH=CH-C1 (trans) B.210 CF 3 ON CH 2 CHOCH-Cl (trans) B.211 Cl H CH 2 CCl=CH 2 B.212 Cl

CH

3

CH

2 00l=CH 2 B.213 Cl

CH

2

CH

3

CH

2 CC1=CH 2 B.214 Cl

CF

3

CH

2 CCl=CH 2 B.215 Cl

CHF

2

CH

2 00l=CH 2 B.216 Cl

CH

2 F CH 2 CCl=CH 2 B.217 Cl Cl CH 2 CCl=CH 2 B.218 Cl 00H 3

CH

2 CCl=CH 2 B.219 Cl OCH 2

CH

3

CH

2 CCl=CH 2 B.220 Cl ON CH 2 CCl=CH 2 B.221 OH 3 H CH 2 CC1=CH 2 B.222 OH 3

OH

3

CH

2 CC1=CH 2 B.223 OH 3

CH

2

CH

3

CH

2 CC1=CH 2 B.224 OH 3

CF

3

OH

2 Cl=CH 2 B.225 OH 3

CHF

2

CH

2 CCl=CH 2 B.226 CH 3

CH

2 F CH 2 00l=CH 2 B.227 CH 3 Cl CH 2 CCl=CH 2 B.228 OH 3 00H 3

CH

2 CC1=CH 2 B.229 OH 3 00H 2

CH

3

CH

2 CC1=0H 2 B.230 OH 3 ON 0H 2 CC1=CH 2 B.231 CF 3 H 0H 2 CC1=CH 2 B.232 CF 3 OH 3

CH

2 CCl=CH 2 B.233 CF 3

CH

2

CH

3

CH

2 001=CH 2 B.234 OF 3 OF 3

CH

2 CC1=CH 2 B.235 OF 3

CHF

2 0H 2 CC1=0H 2 B.236 OF 3 CH 2 F OH 2 C0l=0H 2 B.237 OF 3 Cl 0H 2 CC1=0H 2 B.238 OF 3 00H 3

OH

2 CCl=0H 2 B.239 CF 3 00H 2

CH

3

CH

2 001=CH 2 B.240 OF 3 ON CH 2 CC1=CH 2 B.241 01 H CH 2 C CH B.242 Cl OH 3

CH

2 C CH B.243 Cl CH 2

CH

3

CH

2 C CH B.244 01 CF 3

CH

2 C CH B.245 Cl CHF 2

CH

2 C CH B.246 01 CH 2 F CH 2 C CH B.247 Cl Cl CH 2 C M H 0050/46490 No. R SR B.248 Cl OCH 3

CH

2 C CH B.249 Cl OCH 2

CH

3

CH

2 C CH B.250 Cl CN CH 2 C CH B.251 CH 3 H CH 2 C CH B.252 CH 3

CH

3

CH

2 C CH B.253 CH 3

CH

2

CH

3

CH

2 C CH B.254 CH 3

CF

3

CH

2 C CH B.255 CH 3

CHF

2

CH

2 C CH B.256 CH 3

CH

2 F CH 2 C CH B.257 CH 3 Cl CH 2 C CH B.258 CH 3

OCH

3

CH

2 C CH B.259 CH 3

OCH

2

CH

3

CH

2 C CH B.260 I CH 3 CN CH 2 C MCH B.261 CF 3 H CH 2 C MCH B.262 CF 3

CH

3

CH

2 C -=CH B.263 CF 3

CH

2

CH

3

CH

2 C MCH B.264 CF 3

CF

3

CH

2 C MCH B.265 CF 3

CHF

2

CH

2 C MCH B.266 CF 3

CH

2 F CH 2 C CH B.267 CF 3 Cl CH 2 C MCH B.268 CF 3

OCH

3

CH

2 C CH B.269 CF 3

OCH

2

CH

3

CH

2 C CH B.270 CF 3 CN CH 2 C MCH B.271 Cl H CH 2 C =CCH 3 B.272 Cl

CH

3

CH

2 C CCH 3 B.273 Cl

CH

2

CH

3

CH

2 C CCH 3 B.274 Cl

CF

3

CH

2 C CCH 3 B.275 Cl

CHF

2

CH

2 C CCH 3 B.276 Cl

CH

2 F CH 2 C CCH 3 B.277 Cl Cl CH 2 C CCH 3 B.278 Cl

OCH

3

CH

2 C CCH 3 B29Cl

OCH

2

CH

3

CH

2 C CCH 3 B.280 Cl CN CH 2 C CCH 3 B.281 CH 3 H CH 2 C MCCH 3 B.282 CH 3 CH 3

CH

2 C =-CCH 3 B.283 CH 3

CH

2

CH

3

CH

2 C MCCH 3 B.284 CH 3 CF 3

CH

2 C CCH 3 B.285 CH 3 CHF 2

CH

2 C CCH 3 B.286 I CH 3

CH

2 F CH 2 C =-CCH 3 0050/46490 No. R 3 RS6 B.287 CH 3 Cl CH 2 C CCH 3 B.288 CH 3

OCH

3

CH

2 C CCH 3 5B.289 CH 3

OCH

2

CH

3

CH

2 C CCH 3 B.290 CH 3 CN CH 2 C CCH 3 B.291 CF 3 H CH 2 C CCH 3 B.292 CF 3 CH 3

CH

2 C CCH 3 10B.293 CF 3

CH

2

CH

3

CH

2 C CCH 3 1 09 F 3C 3C H C C H B.295 CF 3 CHF CH 2 C CCH 3 B.296 CF 3 CH2F CH 2 C CCH 3 B.297 CF 3 CH 2

CH

2 C CCH 3 15B.298

CF

3 OCH

CH

2 C =CCH 3 15B.299

CF

3

OHCH

3

CH

2 C CCH 3 B.300 CF 3 CN CH 2 C CCH 3 B.301 Cl H CH 2 C C-I B.302 Cl CH 3

CH

2

C=C-I

B.303 Cl CH 2

CH

3

CH

2 C C-I B.304 Cl CF 3

CH

2 C C-I B.305 Cl CHF 2

CH

2 C C-I B.306 Cl CH 2 F CH 2 C C-I B.307 Cl Cl CH 2

C=C-I

B.308 Cl OCH 3

CH

2 C C-I B.309 Cl OCH 2

CH

3

CH

2 C C-I B.310 Cl CN CH 2 C C-I B31C 3

HC

2 B.311 CH 3 CH CH 2 C C-I B.312 CH 3

CHCH

3

CH

2 C C-I B.313 CH 3

CHC

3

CH

2 C C-I 35B.314 CH 3 CHF3 CH 2 C C-I 35B.315

CH

3 CH 2

CH

2 C C-I B.316 CH 3 Cl2 CH 2 C C-I B.317 CH 3 OCH CH 2 C C-I 40B.318 CH 3

OHCH

3

CH

2 C C-I 40B.319 C.H 3 OCH2CH CH 2 C C-I B.320 CF 3 HN CH 2 C C-I B.321 CF 3 H 3

CH

2 C C-I B.322 CF 3

CHCH

3

CH

2 C C-I 45B.2 F HC3 C2=- B.324 CF 3 CF 3

CH

2 C C-I B.325 CF 3

CHF

2

ICH

2

C=C-I

0050/46490 No. R 3

R

5

R

B.326 CF 3

CH

2 F CH 2 C C-I B.327

CF

3 Cl CH 2

C=C-I

5B.328 CF 3

OCH

3

CH

2 )C C-I B.329

CF

3 OCH 2

CH

3

CH

2 C C-I B.330

CF

3 CN CH 2 C C-I B.331 Cl H CH (CH 3 C CH 10B.332 Cl CH 3 CH (CH 3 C CH B.333 Cl CH 2

CH

3 CH (CH 3 C CH B.334 Cl

CF

3 CH (CH 3 C CH B.335 Cl CHF 2 CH (CH 3 C CH B.336 Cl

CH

2 F CH (CH 3 C CH B.337 Cl Cl CH (CH 3 C CH B.338 Cl OCH 3 CH (CH 3 C CH B.339 Cl OCH 2

CH

3 CH (CH 3 C CH B.340 Cl CN CH(CH 3

)C=-CH

B.341 CH 3 H CH (CH 3 C CH B.342 CH 3

CH

3 CH (CH 3 C CH B.343 CH 3

CH

2

CH

3 CH (CH 3 C CH B.344 CH 3

CF

3 CH (CH 3 C CH B.345 CH 3

CHF

2 CH (CH 3 C CH B.346 CH 3

CH

2 F CH (CH 3 C CH B.347 CH 3 Cl CH (CH 3 C MCH B.348 CH 3

OCH

3 CH (CH 3 C CH 30B.349 CH 3

OCH

2

CH

3 CH (CH 3 C CH 30B.350 CH 3 CN CH(CH 3

)C=CH

B.351 CF 3 H CH (CH 3 C =CH B.352 CF 3 CH 3 CH (CH 3 C MCH B.353 CF 3

CH

2

CH

3 CH (CHA)C -=CH B.354 CF 3 CF 3 CH (CH 3 C MCH B.355 CF 3

CHF

2 CH (CH 3 C MCH B.356 CF 3

CH

2 F CH (CH 3 C MCH B.357 CF 3 Cl CH (CHA)C =-CH B.358 CF 3

OCH

3 CH (CH 3 C MCH B.359 CF 3

OCH

2

CH

3 CH (CH 3 C CH B.360 CF 3 CN CH (CH 3

CCH

B.361 Cl H CH 2

CH

2

-O-CH

2

CH

3 45B.362 Cl CH 3

CH

2

CH

2

-O-CH

2

CH

3 B.363 Cl

CH

2

CH

3

CH

2

CH

2

-O--CH

2

CH

3 [B.364 Cl

CF

3

CH

2

CH

2

-O-CH

2

CH

3 0050/46490 No. R3R 5

R

6 B.365 Cl CHF 2

CH

2

CH

2

-O-CH

2

CH

3 B.366 Cl CH 2 F CH 2

CH

2

-O-CH

2

CH

3 B.367 Cl Cl CH 2

CH

2

-O-CH

2

CH

3 B.368 Cl

OCH

3

CH

2

CH

2

-O-CH

2

CH

3 B.369 Cl OCH 2

CH

3

CH

2

CH

2

-O-CH

2

CH

3 B.370 Cl CN CH 2

CH

2

-O-CH

2

CH

3 B.371 CH 3 H CH 2

CH

2

-O-CH

2

CH

3 B.372 CH 3 CH 3

CH

2

CH

2

-O-CH

2

CH

3 B.373 CH 3

CH

2

CH

3

CH

2

CH

2

-O-CH

2

CH

3 B.374

CH

3 CF 3

CH

2

CH

2

-O-CH

2

CH

3 B.375 CH 3 CHF 2

CH

2

CH

2

-O-CH

2

CH

3 B.376 CH 3 CH 2 F CH 2

CH

2

-Q-CH

2

CH

3 B.377 CH 3 Cl CH 2

CH

2

-O-CH

2

CH

3 B.378 CH 3 OCH 3

CH

2

CH

2

-O-CH

2

CH

3 B.379 CH 3

OCH

2

CH

3

CH

2

CH

2

-O-CH

2

CH

3 B.380 CH 3 CN CH 2

CH

2

-O-CH

2

CH

3 B.381 CF 3 H CH 2

CH

2

-O-CH

2

CH

3 B.382 CF 3 CH 3

CH

2

CH

2

-O-CH

2

CH

3 B.383 CF 3

CH

2

CH

3

CH

2

CH

2

-O-CH

2

CH

3 B.384 CF 3

CF

3

CH

2

CH

2

-O-CH

2

CH

3 B.385 CF 3

CHF

2

CH

2

CH

2

-O-CH

2

CH

3 B.386 CF 3

CH

2 F CH 2

CH

2

-O-CH

2

CH

3 B.387 CF 3 Cl CH 2

CH

2

-O-CH

2

CH

3 B.388 CF 3 OCH 3

CH

2

CH

2

-O-CH

2

CH

3 B.389 CF 3

OCH

2

CH

3

CH

2

CH

2

-O-CH

2

CH

3 B.390 CF 3 CN CH 2

CH

2

-O-CH

2

CH

3 B.391 Cl H CH 2

-C

6

H

B.392 Cl

CH

3

CH

2

-C

6

H

B.393 Cl

CH

2

CH

3

CH

2

C

6

H

B.394 Cl

CF

3

CH

2

-C

6

H

B.395 Cl

CHF

2

CH

2

-C

6

H

B.396 Cl

CH

2 F ICH 2

-C

6

H

B.397 Cl Cl CH 2

-C

6

H

B.398 Cl

OCH

3

CH

2

-C

6

H

B.399 Cl OCH 2

CH

3

CH

2

-C

6

H

B.400 Cl CN CH 2

-C

6

H

B.401 CH 3 H CH 2

-C

6

H

B.402 CH 3 CH 3

CH

2

-C

6

H

B.403 CH 3

CH

2

CH

3

ICH

2

-C

6

H

0050/46490 No. R 3 R56 B.404 CH 3

CF

3

CH

2

-C

6

H

B.405 CH 3

CHF

2

CH

2

-C

6

H

B.406 CH 3

CH

2 F CH 2

-C

6

H

B.407 CH 3 Cl CH 2

-C

6

H

B.408 CH 3

OCH

3

CH

2

-C

6

H

B.409 CH 3

OCH

2

CH

3

CH

2

-C

6

H

B.410 CH 3 CI'I CH 2

-C

6

H

B.411 CF 3 H CH 2

-C

6

H

B.412 CF 3

CH

3

CH

2

-C

6

H

B.413 CF 3

CH

2

CH

3

CH

2

-C

6

H

B.414 CF 3

CF

3

CH

2

-C

6

H

B.415 CF 3

CHF-

2

CH

2

-C

6

H

B.416 CF 3

CH

2 F CH 2

-C

6

H

B.417 CF 3 Cl CH 2

-C

6

H

B.418 CF 3

OCH

3

CH

2

-C

6

H

B.419 CF 3

OCH

2

CH

3

CH

2

-C

6

H

B..420 CF 3 CN CH 2

-C

6

H

B.421 Cl H cyclopropyl B.422 Cl CH 3 cyclopropyl B.423 Cl CH 2

CH

3 cyclopropyl B.424 Cl CF 3 cyclopropyl B.425 Cl CHF 2 cyclopropyl B.426 Cl CH 2 F cyclopropyl B.427 Cl Cl cyclopropyl B.428 Cl OCH 3 cyclopropyl B.429 Cl OCH 2

CH

3 cyclopropyl B.430 Cl CN cyclopropyl B.431 CH 3 H cyclopropyl B.432 CH 3

CH

3 cyclopropyl B.433 CH 3

CH

2

CH

3 cyclopropyl B.434 CH 3

CF

3 cyclopropyl B.435 CH 3

CHF

2 cyclopropyl B.436 CH 3

CH

2 F cyclopropyl B.437 CH 3 Cl cyclopropyl B.438 CH 3

OCH

3 cyclopropyl B.439 CH 3

OCH

2

CH

3 cyclopropyl B.440 CH 3 CN cyclopropyl B.441 CF 3 H cyclopropyl B.442 CF 3

CH

3 cyclopropyl 0050/46490 No. R3R 5

R

6 B.443 CF 3

CH

2

CH

3 cyclopropyl B.444 CF 3

CF

3 cyclopropyl B..445 CF 3

CHF

2 cyclopropyl B.446 CF 3

CH

2 F cyclopropyl B.447 CF 3 Cl cyclopropyl B.448 CF 3

OCH

3 cyclopropyl B.449 CF 3

OCH

2

CH

3 cyclopropyl B.450 CF 3 CN cyclopropyl B.451 Cl H CH 2 -(2,2-C1 2 -cyclopropyl) B.452 Cl CH 3

CH

2 -(2,2-Cl 2 -CYClopropyl) B.453 Cl CH 2

CH

3

CH

2 -(2,2-C1 2 -CYClopropyl) B.454 Cl CF 3

CH

2 -(2,2-C1 2 -CYClopropyl) B.455 Cl CHF 2

CH

2 -(2,2-C1 2 -CYClopropyl) B.456 Cl CH 2 F CH 2 -(2,2-Cl 2 -CYClopropyl) B.457 Cl Cl CH 2 -(2,2-Cl 2 CYClopropyl) B.458 Cl OCH 3

CH

2 -(2,2-Cl 2 -CYClopropyl) B.459 Cl OCH 2

CH

3

CH

2 -(2,2-Cl 2 -CYClopropyl) B.460 Cl CN CH 2 -(2,2-Cl 2 -CYClopropyl) B.461 CH 3 H CH 2 (2,2-C1 2 -CYClopropyl) B.462 CH 3

CH

3

CH

2 -(2,2-Cl 2 -CYClopropyl) B.463 CR 3

CH

2

CH

3

CH

2 -(2,2-Cl 2 -CYClopropyl) B.464 CR 3

CF

3

CH

2 -(2,2-C1 2 CYClopropyl) B.465 CR 3

CHF

2

CH

2 -(2,2-Cl 2 -CYClopropyl) B.466 CR 3

CH

2 F CH 2 -(2,2-C1 2 -CYClopropyl) B.467 CH 3 Cl CH 2 -(2,2-C1 2 -CYClopropyl) B.468 CH 3

OCH

3

CH

2 2-Cl 2 -CYClopropyl) B.469 CH 3

OCH

2

CR

3

CH

2 (2 2-Cl 2 -CYClopropyl) B.470 CH 3 CN CH 2 -(2,2-C1 2 -cyclopropyl) B.471 CF 3 H CR 2 -(2,2-C1 2 -CYClopropyl) B.472 CF 3

CH

3

CH

2 -(2,2-C1 2 -CYClopropyl) B.473 CF 3

CH

2

CH

3 jCH 2 -(2,2--C1 2 -CYClopropyl) B.474 CF 3

CF

3 jCH 2 -(2,2-C1 2 -CYClopropyl) B.475 CF 3

CHF

2

CH

2 -(2,2-Cl 2 -CYClopropyl) B.476 CF 3

CH

2 F CH 2 2-Cl 2 -CYClopropyl) B.477 CF 3 Cl CH 2 -(2,2-Cl 2 -CYClopropyl) B.478 CF 3

OCH

3

CH

2 -(2,2--C1 2 -CYClopropyl) B.479 CF 3

OCH

2

CH

3

CH

2 -(2,2-Cl 2 -CYClopropyl) B.480 CF 3 CN CH 2 -(2,2-C1 2 -CYClopropyl) B.481 H CR 3

H

0050/46490 No. R 3 RS R B.482 H CH 2

CH

3

H

B.483 H CF 3

H

B.484 H Cl H B.485 H OCH 3

H

B.486 CH 2

CH

3

CH

3

H

B.487 CH 2

CH

3

CH

2

CH

3

H

B.488 CH 2

CH

3

CF

3

H

B.489 CH 2

CH

3 Cl H B.490 CH 2

CH

3

OCH

3

H

B.491 CHF 2

CH

3

H

B.492 CHF 2 E CH 2

CH

3

H

B.493 CHF 2

CF

3

H

B.494 CHF 2 Cl H B.495 CHF 2

OCH

3

H

B.496 CH 2 F CH 3

H

B.497 CH 2 F CH 2

CH

3

H

B.498 CH 2 F CF 3

H

B.499 CH 2 F Cl H B.500 CH 2 F OCH 3

H

B.501 OCH 3

CH

3

H

B.502 OCH 3

CH

2

CH

3

H

B.503 OCH 3

CF

3

H

B.504 OCH 3 Cl H B.505 OCH 3

OCH

3

H

B.506 OCH 2

CH

3

OH

3

H

B.507 QCH 2

CH

3

CH

2

CH

3

H

B.508 OCH 2

CH

3

CF

3

H

B.509 OCH 2

CH

3 Cl H B.510 OCH 2

CH

3

OCH

3

H

B.511 CN OH 3

H

B.512 CN CH 2

CH

3

H

B.513 CII CF 3

H

B.514 ON Cl H B.515 ON 00H 3

H

B.516 H OH 3

OH

3 B.517 H CH 2

CH

3

OH

3 B.518 H CF 3

CH

3 B.519 H Cl CH 3 B.520 H OCH 3

ICH

3 0050/46490 No. R SR B. 521 CH 2

CH

3

OH

3

OH

3 B.522 CH 2

CH

3

CH

2 0H 3

OH

3 B.523 CH 2

CH

3

OF

3

OH

3 B.524 CH 2

CH

3 Cl OH 3 B.525 CH 2

CH

3

OCH

3

OH

3 B.526 CHF 2

OH

3

OH

3 B.527 CHF 2 0H 2

CH

3

OH

3 B.528 CHF 2

CF

3

CH

3 B.529 CHF 2 01 OH 3 B.530 CHF 2

OCH

3

OH

3 B.531 CH 2 F OH 3

OH

3 B.532 CH 2 F CH 2

CH

3

OH

3 B.533 CH 2 F OF 3

OH

3 B.534 CH 2 F 01 OH 3 B.535 CH 2 F 00H 3

OH

3 B.536 00H 3

OH

3

OH

3 B.537 00H 3 0H 2

CH

3

OH

3 B.538 00H 3

CF

3

OH

3 B.539 00H 3 Cl OH 3 B.540 00H 3 00H 3

OH

3 B.541 00H 2

CH

3

OH

3

OH

3 B.542 OCH 2

CH

3

CH

2

CH

3

OH

3 B.543 OCH 2

CH

3

CF

3

OH

3 B.544 OCH 2

CH

3 01 OH 3 B.545 OCH 2

OH

3

OOH

3

OH

3 B.546 ON OH 3

OH

3 B.547 ON 0H 2 0H 3

OH

3 B.548 ON OF 3

OH

3 B.549 ON 01 OH 3 B.550 ON 00H 3

OH

3 B.551 H OH 3

CH

2 0H 3 B.552 H 0H 2

CH

3

CH

2 0H 3 B.553 H CF 3

CH

2

OH

3 B.554 H 01 CH 2

OH

3 B.555 H OCH 3

CH

2 0H 3 B.556 OH 2

CH

3

OH

3 0H 2 0H 3 B.557 CH 2 0H 3

CH

2

OH

3

CH

2 0H 3 B.558 0H?0H 3 A CF 3

CH

2

CH

3 B.559 0H 2 0H 3 01 0H 2

CH

3 0050/46490 No. R 3

R

5

R

B.560 CH 2

CH

3

OCH

3

CH

2

CH

3 B.561 CHF 2

CH

3

CH

2

CH

3 B.562 CHF 2

CH

2

CH

3

CH

2

CH

3 B.563 CHF 2

CF

3

CH

2

CH

3 B.564 CHF 2 Cl CH 2

CH

3 B.565 CHF 2

OCH

3

CH

2

CH

3 B.566 CH 2 F CH 3

CH

2

CH

3 B.567 CH 2 F CH 2

CH

3

CH

2

CH

3 B.568 CH 2 F CF 3

CH

2

CH

3 B.569 CH 2 F Cl CH 2

CH

3 B.570 CH 2 F OCH 3

CH

2

CH

3 B.571 OCH 3

CH

3

CH

2

CH

3 B.572 OCH 3

CH

2

CH

3

CH

2

CH

3 B.573 OCH 3

CF

3

CH

2

CH

3 B.574 OCH 3 Cl CH 2

CH

3 B.575 OCH 3

OCH

3

CH

2

CH

3 B.576 OCH 2

CH

3

CH

3

CH

2

CH

3 B.577 OCH 2

CH

3

CH

2

CH

3

CH

2

CH

3 B.578 OCH 2

CH

3

CF

3

CH

2

CH

3 B.579 OCH 2

CH

3 Cl CH 2

CH

3 B.580 OCH 2

CH

3

OCH

3

CHCH

3

A

B.581 CN CH 3

CH

2

CH

3 B.582 CN CH 2

CH

3

CH

2

CH

3 B.583 CN CF 3

CHCH

3 i B.584 CN Cl CH 2

CH

3 B.585 CN OCH 3

CH

2

CH

3 B.586 H CH 3

CHCHCH

3

A

B.587 H CH 2

CH

3

CH

2

CH

2

CH

3 B.588 H CF 3

CH

2

CH

2

CH

3 B.589 H Cl CH 2

CHCH

3

A

B.590 H OCH 3

CH

2

CH

2

CH

3 B.591 CH 2

CH

3

CH

3

CH

2

CH

2

CH

3 B.592 CH 2

CH

3

CH

2

CH

3

CHCHCH

3

A

B.593 CH 2

CH

3

CF

3

CH

2

CH

2

CH

3 B.594 CH 2

CH

3 Cl CH 2

CH

2

CH

3 B.595 CH 2

CH

3

OCH

3

CH

2

CH-

2

CH

3

A

B.596 CHF 2

CH

3

CH

2

CH

2

CH

3 B.597 CHF 2

CH

2

CH

3

CH

2

CH

2

CH

3 B.598 CHF 2

CF

3

CH

2

CH

2

CH

3 0050/46490 No. R 3 R56 B. 599 CHF 2 Cl CH 2

CH

2

CH

3 B.600 CHF 2

OCH

3

CH

2

CH

2

CH

3 B.601 CH 2 F CH 3

CH

2

CH

2

CH-A

B.602 CH 2 F CH 2

CH

3

CH

2

CH

2

CH

3 B.603 CH 2 F CF 3

CH

2

CH

2

CH

3 B.604 CH 2 F Cl CH 2 CH-gCH-; B.605 CH 2 F OCH 3

CH

2

CH

2

CH

3 B.606 OCH 3

CH

3

CH

2

CH

2

CH

3 B.607 OCH 3

CH

2

CH

3 CHqCHqCH 3

A

B.608 OCH 3

CF

3

CH

2

CH

2

CH

3 B.609 OCH 3 Cl CH 2

CH

2

CH

3 B.610 OCH 3

OCH

3

CH

2

CH

2

CH

3 B.611 OCH 2

CH

3

CH

3

CH

2

CH

2

CH

3 B.612 OCH 2

CH

3

CH

2

CH

3

CH

2

CH

2

CH

3 B.613 OCH 2

CH

3

CF

3

CH

2

CH

2

CH

3 B.614 OCH 2

CH

3 Cl CH 2

CH

2

CH

3 B.615 OCH 2

CH

3

OCH

3

CH

2

CH

2

CH

3 B.616 CN CH 3

CH

2

CH

2

CH

3 B.617 CN CH 2

CH

3

CH

2

CH

2

CH

3 B.618 CN CF 3

CH

2

CH

2

CH

3 B.619 CN ci CH 2

CH

2

CH

3 B.620 CN OCH 3

CH

2

CH

2

CH

3 B.621 H CH 3

CH(CH

3 2 B.622 H CH 2

CH

3

CH(CH

3 2 B-.623 H CF 3

CH(CH

3 2 B.624 H Cl CH(CH 3 2 B.625 H OCH 3

CH(CH

3 2 B.626 CH 2

CH

3

CH

3

CH(CH

3 2 B.627 CH 2

CH

3

CH

2

CH

3

CH(CH

3 2 B.628 CH 2

CH

3

CF

3

CH(CH

3 2 B.629 CH 2

CH

3 Cl CH(CH 3 2 B.630 CH 2

CH

3

OCH

3

CH(CH

3 2 B.631 CHF 2

CH

3

CH(CH

3 2 B.632 CHF 2

CH

2

CH

3

CH(CH

3 2 B.633 CHF 2

CF

3

CH(CH

3 2 B.634 CHF 2 Cl CH(CH 3 2 B.635 CHF 2

OCH

3

CH(CH

3 2 B.636 CH 2 F CH 3

CH(CH

3 2 B.637 CH 2 F CH 2

CH

3

CH(CH

3 2 0050/46490 No. R R R 6 B.638 CH 2 F OF 3

CH(CH

3 2 B.639 CH 2 F 01 CH(CH 3 2 B.640 CH 2 F 00H 3

CH(CH

3 2 B.641 OCH 3

CH

3

CH(CH

3 2 B.642 00H 3

CH

2

CH

3

CH(CH

3 2 B.643 00113 CF 3

CH(CH

3 2 B.644 00H 3 Cl CH(CH 3 2 B.645 00113 OCH 3

CH(CH

3 2 B.646 OCH 2

CH

3

OH

3

CH(CH

3 2 B.647 OCH 2

CH

3

CH

2

CH

3

CH(CH

3 2 B.648 00H 2

CH

3

CF

3

CH(CH

3 2 B.649 00H 2

CH

3 01 CH(CH 3 2 B.650 OCH 2

CH

3

OCH

3

CH(CH

3 2 B.651 ON CH 3

OH(CH

3 2 B.652 ON 0H 2

CH

3

CH(CH

3 2 B.653 ON OF 3

OH(CH

3 2 B.654 ON 01 OH(CH 3 2 B.655 ON O0H 3 CH(0H 3 2 B.656 H OH 3

CH

2

CH=CH

2 B.657 H CH 2

CH

3

CH

2

CH=CH

2 B.658 H OF 3

CH

2

CH=CH

2 B.659 H 01 CH 2

CH=CH

2 B.660 H O0H 3

OH

2

CH=CH

2 B.661 0112013 OH 3 0H2CH=CH2 B.662 CH 2

CH

3

CH

2

CH

3

CH

2

CH=CH

2 B.663 0112013 OF 3

CH

2

CH=CH

2 B.664 CH 2

CH

3 01 CH 2

CH=CH

2 B.665 0H 2

CH

3 00113 0H 2 011=CH 2 B.666 CHF 2

OH

3

OH

2

CH=CH

2 B.667 CHF 2

CH

2 011 3

CH

2

CH=CH

2 B.668 CHF 2

OF

3

CHCH=CH

2 B.669 OHF 2 01 CH 2 011=CH 2 B.670 CHF 2 00113 CH 2

CH=CH

2 B.671 011 2 F OH 3

OH

2

CH=CH

2 B.672 OH 2 F 0H 2 0H 3

CH

2

CH=CH

2 B.673 CH 2 F OF 3

CH

2

CH=CH

2 B.674 OH 2 F Cl CH2CH=CH2 B.675 OH 2 F 00113 CH 2 0H=CH 2 B.676 00113 013 CH 2 CH=0H 2 0050/46490 No. R SR 6 B. 677 OCH 3

CH

2

CH

3

CH

2

CH=CH

2 B.678 OCH 3

CF

3

CH

2

CH=CH

2 B.679 OCH 3 Cl CH 2

CH=CH

2 B.680 OCH 3

OCH

3

CH

2

CH=CH

2 B.681 OCH 2

CH

3

CH

3

CH

2

CH=CH

2 B.682 OCH 2

CH

3

CH

2

CH

3

CH

2

CH=CH

2 B.683 OCH 2

CH

3

CF

3

CH

2

CH=CH

2 B.684 OCH 2

CH

3 Cl CH 2

CH=CH

2 B.685 OCH 2

CH

3

OCH

3

CH

2

CH=CH

2 B.686 CN CH 3

CH

2

CH=CH

2 B.687 CN CH 2

CH

3

CH

2

CH=CH

2 B.688 CN CF 3

CH

2

CH=CH

2 B.689 CN

CH

2

CH=CH

2 B.690 CN OCH 3

CH

2

CH=CH

2 B.691 H CH 3

CH

2 CH=CH-Cl (trans) B.692 H CH 2

CH

3

CH

2 CH=CH-Cl (trans) B.693 H CF 3

CH

2 CH=CH-Cl (trans) B.694 H Cl CH 2 CH=CH-Cl (trans) B.695 H OCH 3

CH

2 CH=CH-C1 (trans) B.696 CH 2

CH

3

CH

3

CH

2 CH=CH-Cl (trans) B.697 CH 2

CH

3

CH

2

CH

3

CH

2 CH=CH-C1 (trans) B.698 CH 2

CH

3

CF

3

CH

2 CH=CH-Cl (trans) B.699 CH 2

CH

3 Cl CH 2 CH=CH-Cl (trans) B.700 CH 2

CH

3

OCH

3

CH

2 CH=CH-Cl (trans) B.701 CHF 2

CH

3

CH

2 CH=CH-Cl (trans) B.702 CHF 2

CH

2

CH

3

CH

2 CH=CH-Cl (trans) B.703 CHF 2

CF

3

CH

2 CH=CH-Cl (trans) B.704 CHF 2 Cl CH 2 CH=CH-Cl (trans) B.705 CHF 2

OCH

3

CH

2 CH=CH-Cl (trans) B.706 CH 2 F CH 3

CH

2 CH=CH-Cl (trans) B.707 CH 2 F CH 2

CH

3

CH

2 CH=CH-C1 (trans) B.708 CH 2 F CF 3

CH

2 CH=CH-Cl (trans) B.709 CH 2 F Cl CH 2 CH=CH-C1 (trans) B.710 CH 2 F OCH 3

CH

2 CH=CH-C1 (trans) B.711 OCH 3

CH

3

CH

2 CH=CH-Cl (trans) B.712 OCH 3

CH

2

CH

3

CH

2 CH=CH-Cl (trans) B.713 OCH 3

CF

3

CH

2 CH=CH-Cl (trans) B.714 OCH 3 Cl CH 2 CH=CH-Cl (trans) B.715 OCH 3

OCH

3

CH

2 CH=CH-Cl (trans) 0050/46490 No. R 3

RSR

6 B.716 OCH 2

CH

3

CH

3

CH

2 CH=CH-C1 (trans) B.717 OCH 2

CH

3

CH

2

CH

3

CH

2 CH=CH-C1 (trans) B.718 OCH 2

CH

3

CF

3

CH

2 CH=CH-C1 (trans) B.719 OCH 2

CH

3 Cl CH 2 CH=CH-C1 (trans) B.720 OCH 2

CH

3

OCH

3

CH

2 CH=CH-Cl (trans) B.721 CN CH 3

CH

2 CH=CH-C1 (trans) B.722 CN CH 2

CH

3

CH

2 CH=CH-C1 (trans) B.723 CN CF 3

CH

2 CH=CH-Cl (trans) B.724 CN Cl CH 2 CH=CH-Cl (trans) B.725 CN OCH 3

CH

2 CH=CH-Cl (trans) B.726 H CH 3

CH

2 CCl=CH 2 B.727 H CH 2

CH

3

CH

2 CCl=CH 2 B.728 H CF 3

CH

2 CC1=CH 2 B.729 H Cl CH 2 CCl=CH 2 B.730 H OCH 3

CH

2 CCl=CH 2 B.731 CH 2

CH

3

CH

3

CH

2 CC1=CH 2 B.732 CH 2

)CH

3 i CH 2

CH

3

CH

2 CCl=CH 2 B.733 CH 2

CH

3

CF

3

CH

2 CC1=CH 2 B.734 CH 2

CH

3 Cl CH 2 CC1=CH 2 B.735 CH 2

)CH

3 A OCH 3

CH

2 CCl=CH 2 B.736 CHF 2

CH

3

CH

2 CCl=CH 2 B.737 CHF 2

CH

2

CH

3

CH

2 CCl=CH 2 B.738 CHF 2

CF

3

CH

2 CCl=CH 2 B.739 CHF 2 Cl CH 2 CC1=CH 2 B.740 CHF 2

OCH

3

CH

2 CCl=CH 2 B.741 CH 2 F CH 3

CH

2 CCl=CH 2 B.742 CH 2 F CH 2

CH

3

CH

2 CC1=CH 2 B.743 CH 2 F CF 3

CH

2 CCl=CH 2 B.744 CH 2 F Cl CH 2 CCl=CH 2 B.745 CH 2 F OCH 3

CH

2 CC1=CH 2 B.746 OCH 3

CH

3

CH

2 CCl=CH 2 B.747 OCH 3

CH

2

CH

3

CH

2 CCl=CH 2 B.748 OCH 3

CF

3

CH

2 CCl=CH 2 B.749 OCH 3 Cl CH 2 CC1=CH 2 B.750 OCH 3

OCH

3

CH

2 CCl=CH 2 B.751 OCH 2

CH

3

CH

3

CH

2 CCl=CH 2 B.752 OCH 2

CH

3

CH

2

CH

3

CH

2 CCl=CH 2 B.753 OCH 2

CH

3

CF

3

CH

2 CCl=CH 2 B.754i OCH 2

CH

3 Cl ICH 2 CCl=CH 2 0050/46490 No. R 3 RS6 B.755 OCH 2

CH

3

OCH

3

CH

2 CC1=CH 2 B.756 CN CH 3

CH

2 CC1=CH 2 B.757 CN CH 2

CH

3

CH

2 CC1=CH 2 B.758 CN CF 3

CH

2 CC1=CH 2 B.759 CN Cl CH 2 CC1=CH 2 B.760 CN OCH 3

CH

2 CC1=CH 2 B.761 H CH 3

CH

2 C CH B.762 H CH 2

CH

3

CH

2 C CH B.763 H CF 3

CH

2 C CH B.764 H Cl CH 2 C CH B.765 H OCH 3

CH

2 C CH B.766 CH 2

CH

3

CH

3

CH

2 C CH B.767 CH 2

CH

3

CH

2

CH

3

CH

2 C CH B.768 CH 2

CH

3

CF

3

CH

2 C CH B.769 CH 2

CH

3 Cl CH 2 C CH B.770 CH 2

CH

3

OCH

3

CH

2 C CH B.771 CHF 2

CH

3

CH

2 C CH B.772 CHF 2

CH

2

CH

3

CH

2 C CH B.773 CHF 2

CF

3

CH

2 C CH B.774 CHF 2 Cl CH 2 C CH B.775 CHF 2

OCH

3

CH

2 C CH B.776 CH 2 F CH 3

CH

2 C CH B.777 CH 2 F CH 2

CH

3

CH

2 C MCH B.778 CH 2 F CF 3

CH

2 C MCH B.779 CH 2 F Cl CH 2 C -=CH B.780 CH 2 F OCH 3

CH

2 C MCH B.781 OCH 3

CH

3

CH

2 C CH B.782 OCH 3

CH

2

CH

3

CH

2 C CH B.783 OCH 3

CF

3

CH

2 C CH B.784 OCH 3 Cl CH 2 C CH B.785 OCH 3

OCH

3

CH

2 C CH B.786 OCH 2

CH

3

CH

3

CH

2 C MCH B.787 OCH 2

CH

3

CH

2

CH

3

CH

2 C CH B.788 OCH 2

CH

3

CF

3

CH

2 C CH B.789 OCH 2

CH

3 Cl CH 2 C CH B.790 OCH 2

CH

3

OCH

3

CH

2 C CH B.791 CN CH 3

CH

2

C=CH

B.792 CN CH 2

CH

3

CH

2 C -=CH B.793 CN CF 3

CH

2 C MCH 0050/46490

RA

No. R 3 R56 B.794 CN Cl CH 2 C CH B.795 CN OCH 3

CH

2 C CH B. 796 H CH 3

CH

2 C CCH 3 B.797 H CH 2

CH

3

CH

2 C CCH 3 B.798 H CF 3

CH

2 C CCH 3 B.799 H Cl CH 2 C CCH 3 B.800 H OCH 3

CH

2 C CCH 3 B. 801 CH 2

CH

3

CH

3

CH

2 C CCH 3 B. 802 CH 2

CH

3

CH

2

CH

3

CH

2 C MCCH 3 B. 803 CH 2

CH

3

CF

3

CH

2 C CCH 3 B. 804 CH 2

CH

3 Cl CH 2 C CCH 3 B. 805 CH 2

CH

3

OCH

3

CH

2 C CCH 3 B. 806 CHF 2

CH

3

CH

2 C CCH 3 B. 807 CHF 2

CH

2

CH

3

CH

2 C CCH 3 B. 808 CHF 2

CF

3

CH

2 C CCH 3 B. 809 CHF 2 Cl CH 2 C CCH 3 B.810 CHF 2

OCH

3

CH

2 C CCH 3 B.811 CH 2 F CH 3

CH

2 C CCH 3 B. 812 CH 2 F CH 2

CH

3

CH

2 C MCCH 3 B.813 CH 2 F CF 3

CH

2 C CCH 3 B. 814 CH 2 F Cl CH 2 C CCH 3 B. 815 CH 2 F OCH 3

CH

2 C CCH 3 B.816 OCH 3

CH

3

CH

2 C CCH 3 B. 817 OCH 3

CH

2

CH

3

CH

2 C CCH 3 B. 818 OCH 3

CF

3

CH

2 C CCH 3 B. 819 OCH 3 Cl CH 2 C CCH 3 B.820 OCH 3

OCH

3

CH

2 C CCH 3 B.821 OCH 2

CH

3

CH

3

CH

2 C CCH 3 B.822 OCH 2

CH

3

CH

2

CH

3

CH

2 C MCCH 3 B.823 OCH 2

CH

3

CF

3

CH

2 C MCCH 3 B.824 OCH 2

CH

3 Cl CH 2 C MCCH 3 B.825 OCH 2

CH

3

OCH

3

CH

2 C MCCH 3 B.826 CN CH 3

CH

2 C MCCH 3 B.827 CN CH 2

CH

3

CH

2 C CCH 3 B.828 CN CF 3

CH

2 C CCH 3 B.829 CN Cl CH 2 C CCH 3 B.830 CN OCH 3

CH

2 C CCH 3 B.831 H CH 3

CH

2 C C-I 0050/46490 No. R 3 R56 B.832 H CH 2

CH

3

CH

2 C C-I B.833 H CF 3

CH

2 C C-I B. 834 H Cl CH 2 C C-I B.835 H OCH 3

CH

2 C C-I B. 836 CH 2

CH

3

CH

3

CH

2 C C-I B. 837 CH 2

CH

3

CH

2

CH

3

CH

2 C C-I B. 838 CHqCH 3 A CF 3

CH

2 C C-I B.839 CH 2

CH

3 Cl CH 2

C=C-I

B.840 CH 2

CH

3

OCH

3

CH

2 C C-I B.841 CHF 2

CH

3

CH

2

C=C-I

B.842 CHF 2

CH

2

CH

3

CH

2 C C-I B.843 CHF 2

CF

3

CH

2 C C-I B.844 CHF 2 Cl CH 2 C C-I B. 845 CHF 2

OCH

3

CH

2 C C-I B.846 CH 2 F CH 3

CH

2 C C- I B.847 CH 2 F CH 2

CH

3

CH

2 C C-I B.848 CH 2 F CF 3

CH

2 C C-I B.849 CH 2 F Cl CH 2 C C-I B.850 CH 2 F OCH 3

CH

2 C C-I B. 851 OCH 3

CH

3

CH

2 C C-I B. 852 OCH 3

CH

2

CH

3

CH

2 C C-I B.853 OCH 3

CF

3

CH

2 C C-I B. 854 OCH 3 Cl CH 2 C C-I B. 855 OCH 3

OCH

3

CH

2 C C-I B.856 OC H 2

CH

3

CH

3

CH

2 C C-I B. 857 OCH 2

CH

3

CH

2

CH

3

CH

2 C C-I B.858 OCH 2

CH

3

CF

3

CH

2 C C-I B.859 OCH 2

CH

3 Cl CH 2 C C-I B.860 OCH 2

CH

3

OCH

3

CH

2 C C-I B.861 CN CH 3

CH

2 C C-I B.862 CN CH 2

CH

3

CH

2 C C-I B.863 CN CF 3

CH

2

C=C-I

B.864 CN Cl CH 2 C C-I B.865 CN OCH 3

CH

2 C C-I B.866 H CH 3

CH(CH

3

)C=-CH

B.867 H CH 2

CH

3 CH (CH 3 C =CH B.868 H CF 3 CH (CH 3 C CH B.869 H cl CH (CH 3 C CH B.870 H OCH 3 CH (CH 3 C CH 0050/46490 No. R 3 RS6 B. 871 CH 2

CH

3

CH

3

CH(CH

3 )C CH B. 872 CH 2

CH

3

CH

2

CH

3 CH (CH 3 C CH B. 873 CH 2

CH

3

CF

3 CH (CH 3 C CH B. 874 CH 2

CH

3 Cl CH (CH 3 C CH B.875 CH 2

CH

3

OCH

3

CH(CH

3 )C CH B.876 CHF 2

CH

3

CH(CH

3 )C CH B.877 CHF 2

CH

2

CH

3 CH (CH 3 C CH B.878 CHF 2

CF

3 CH (CH 3 C CH B.879 CHF 2 Cl CH (CH 3 C CH B. 880 CHF 2

OCH

3 CH (CH 3 C CH B.881 CH 2 F CH 3 CH (CH 3 C CH B.882 CH 2 F CH 2

CH

3

CH(CH

3

)C-CH

B.883 CH 2 F CF 3

CH(CH

3 )C CH B.884 CH 2 F C 1 CH(CH 3 )C CH B.885 CH 2 F OCH 3 CH (CH 3 C CH B.886 OCH 3

CH

3 CH (CH 3 C CH B.887 OCH 3

CH

2

CH

3 CH (CH 3 C CH B.888 OCH 3

CF

3

CH(CH

3 )C CH B.889 OCH 3 Cl1 CH (CH 3 C CH B. 890 OCH 3

OCH

3 CH (CH 3 C CH B.891 OCH 2

CH

3

CH

3 CH (CH 3 C CH B.892 OCH 2

CH

3

CH

2

CH

3 CH (CH 3 C CH B.893 OCH 2

CH

3

CF

3 CH (CH 3 C CH B.894 OCH 2

CH

3 Cl CH (CH 3 C CH B.895 OCH 2

CH

3

OCH

3 CH (CH 3 C CH B.896 CN CH 3 CH (CH 3 C CH B.897 CN CH 2

CH

3 CH (CH 3 C CH B.898 CN CF 3

CH(CH

3 )C CH B.899 CN Cl CH (CH 3 C CH B.900 CN OCH 3 CH (CH 3 C CH B..901 H CH 3

CH

2

CH

2

-O-CH

2

CH

3 B.902 H CH 2

CH

3

CH

2

CH

2

-O-CH

2

CH

3 B.903 H CF 3

CH

2

CH

2

-O-CH

2

CH

3 B.904 H Cl CH 2

CH

2

-O-CH

2

CH

3 B.905 H OCH 3

CH

2

CH

2

-O-CH

2

CH

3 B.906 CH 2

CH

3

CH

3

CH

2

CH

2

-O-CH

2

CH

3 B.907 CH 2

CH

3

CH

2

CH

3

CH

2

CH

2

-O-CH

2

CH

3 B.908 CH 2

CH

3

CF

3

CH

2

CH

2

-O-CH

2

CH

3 B.909 CH 2

CH

3 Cl CH 2

CH

2

-O-CH

2

CH

3 0050/46490 No. R 3

R

5

R

B.910 CH 2

CH

3

OCH

3

CH

2

CH

2

-O-CH

2

CH

3 B.911 CHF 2

CH

3

CH

2

CH

2

-O-CH

2

CH

3 B.912 CHF 2

CH

2

CH

3

CH

2

CH

2

-O-CH

2

CH

3 B.913 CHF 2

CF

3

CH

2

CH

2

-O-CH

2

CH

3 B.914 CHF 2 Cl CH 2

CH

2

-O-CH

2

CH

3 B.915 CHF 2

OCH

3

CH

2

CH

2

-O-CH

2

CH

3 B.916 CH 2 F CH 3

CH

2

CH

2

-O-CH

2

CH

3 B.917 CH 2 F CH 2

CH

3

CH

2

CH

2

-O-CH

2

CH

3 B.918 CH 2 F CF 3

CH

2

CH

2

-O-CH

2

CH

3 B.919 CH 2 F Cl CH 2

CH

2

-O-CH

2

CH

3 B.920 CH 2 F OCH 3

CH

2

CH

2

-O-CH

2

CH

3 B.921 OCH 3

CH

3

CH

2

CH

2

-O-CH

2

CH

3 B.922 OCH 3

CH

2

CH

3

CH

2

CH

2

-O-CH

2

CH

3 B.923 OCH 3

CF

3

CH

2

CH

2

-O-CH

2

CH

3 B.924 OCH 3 Cl CH 2

CH

2

-O-CH

2

CH

3 B.925 OCH 3

OCH

3

CH

2

CH

2

-O-CH

2

CH

3 B.926 OCH 2

CH

3

CH

3

CH

2

CH

2

-O-CH

2

CH

3 B.927 OCH 2

CH

3

CH

2

CH

3

CH

2

CH

2

-O-CH

2

CH

3 B.928 OCH 2

CH

3

CF

3

CH

2

CH

2

-O-CH

2

CH

3 B.929 I OCH 2

CH

3 Cl CH 2

CH

2

-O-CH

2

CH

3 B.930 OCH 2

CH

3

OCH

3

CH

2

CH

2

-O-CH

2

CH

3 B.931 CN CH 3

CH

2

CH

2

-O-CH

2

CH

3 B.932 ON CH 2

CH

3

CH

2

CH

2

-O-CH

2

CH

3 B.933 CN CF 3

CH

2

CH

2

-O-CH

2

CH

3 B.934 ON Cl CH 2

CH

2

-Q-CH

2

CH

3 B.935 ON OCH 3

CH

2

CH

2

-O-CH

2

CH

3 B.936 H OH 3

CH

2

-C

6

H

B.937 H CH 2

CH

3

CH

2

-C

6

H

B.938 H CF 3

CH

2

-C

6

H

B.939 H Cl CH 2

-C

6

H

B.940 H OCH 3

CH

2

-C

6

H

B.941 CH 2

CH

3

OH

3

CH

2

-C

6

H

B.942 CH 2

CH

3

CH

2

CH

3

CH

2

-C

6

H

B.943 CH 2

CH

3

CF

3

CH

2

-C

6

H

B.944 CH 2

CH

3 Cl CH 2

-C

6

H

B.945 CH 2

CH

3

OCH

3

CH

2

-C

6

H

B.946 CHF 2

OH

3

CH

2

-C

6

H

B.947 CHF 2

CH

2

CH

3

CH

2

-C

6

H

B.948 CHF 2 I CF 3

CH

2

-C

6

H

0050/46490 No. R 3 R56 B.949 CHF 2 Cl CH 2

-C

6

H

B. 950 CHF 2

OCH

3

CH

2

-C

6

H

B. 951 CH 2 F CH 3

CH

2

-C

6

H

B. 952 CH 2 F CH 2

CH

3

CH

2

-C

6

H

B.953 CH 2 F CF 3

CH

2

-C

6

H

B.954 CH 2 F Cl CH 2

-C

6

H

B.955 CH 2 F OCH 3

CH

2

-C

6

H

B.956 QCH 3

CH

3

CH

2

-C

6

H

B.957 OCH 3

CH

2

CH

3

CH

2

-C

6

H

B.958 OCH 3

CF

3

CH

2

-C

6

H

B.959 QCH 3 Cl CH 2

-C

6

H

B.960 OCH 3

OCH

3

CH

2

-C

6

H

B.961 OCH 2

CH

3

CH

3

CH

2

-C

6

H

B.962 OCH 2

CH

3

CH

2

CH

3

CH

2

-C

6

H

B.963 OCH 2

CH

3

CF

3

CH

2

-C

6

H

B.964 OCH 2

CH

3 Cl CH 2

-C

6

H

B.965 OCH 2

CH

3

OCH

3

CH

2

-C

6

H

B.966 CN CH 3

CH

2

-C

6

H

B.967 CN CH 2

CH

3

CH

2

-C

6

H

B.968 CN CF 3

CH

2

-C

6

H

B.969 CN Cl CH 2

-C

6

H

B.970 CN OCH 3

CH

2

-C

6

H

B.971 H CH 3 cyclopropyl B.972 H CH 2

CH

3 cyclopropyl B.973 H CF 3 cyclopropyl B.974 H Cl cyclopropyl B.975 H OCH 3 cyclopropyl B.976 CH 2

CH

3

CH

3 cyclopropyl B.977 CH 2

CH

3

CH

2

CH

3 cyclopropyl B.978 CH 2

CH

3

CF

3 cyclopropyl B.979 CH 2

CH

3 Cl cyclopropyl B.980 CH 2

CH

3

OCH

3 cyclopropyl B.981 CHF 2

CH

3 cyclopropyl B.982 CHF 2

CH

2

CH

3 cyclopropyl B.983 CHF 2

CF

3 cyclopropyl B.984 CHF 2 Cl cyclopropyl B.985 CHF 2

OCH

3 cyclopropyl B.986 CH 2 F CH 3 cyclopropyl B.987 CH 2 F CH 2

CH

3 cyclopropyl 0050/46490 No. R3R 5

R

B.988 CH 2 F CF 3 cyclopropyl B.989 CH 2 F Cl cyclopropyl B.990 CH 2 F OCH 3 cyclopropyl B.991 OCH 3

CH

3 cyclopropyl B.992 OCH 3

CH

2

CH

3 cyclopropyl B.993 OCH 3

CF

3 cyclopropyl B.994 OCH 3 Cl cyclopropyl B.995 OCH 3

OCH

3 cyclopropyl B.996 OCH 2

CH

3

CH

3 cyclopropyl B.997 OCHqCH 3 i CH 2

CH

3 cyclopropyl B.998 OCH 2

CH

3

CF

3 cyclopropyl B.999 OCH 2

CH

3 Cl cyclopropyl B.1000 OCH 2

CH

3 0OCH 3 cyclopropyl B.1001 CN CH 3 cyclopropyl B.1002 CN CH 2

CH

3 cyclopropyl B.1003 CN CF 3 cyclopropyl B.1004 CN clcyclopropyl B.1005 CN OCH 3 cyclopropyl B.1006 H CH 3

CH

2 (2,2-C1 2 CYClopropyl) B.1007 H CH 2

CH

3

CH

2 (2,2-C1 2 -CYClopropyl) B.1008 H CF 3 CH2-(2,2-C1 2 -CYClopropyl) B.1009 H Cl CH2-(2,2-C1 2 -CYClopropyl) B.1010 H OCH 3 CH2- 2-Cl 2 -CYClopropyl) B. 1011 CH 2

CH

3

CH

3

CH

2 2-C1 2 -CYClopropyl) B.1012 CH 2

CH

3

CH

2

CH

3 CH2-(2,2-Cl 2 -CYClopropy1) B. 1013 CH 2

CH

3

CF

3

CH

2 (2,2-C1 2 -CYClopropyl) B.1014 CH 2

CH

3 Cl CH 2 2-Cl 2 -cyclopropyl) B.1015 CH 2

CH

3

OCH

3

CH

2 2--C1 2 -CYClopropyl) B.1016 CHF 2

CH

3

CH

2 -(2,2-C1 2 -CYClopropyl) B.1017 CHF 2

CH

2

CH

3

CH

2 2-C1 2 -CYClopropyl) B.1018 CHF 2

CF

3

CH

2 -(2,2-C1 2 -CYClopropyl) B.1019 CHF 2 Cl CH 2 -(2,2-C1 2 -CYClopropyl) B. 1020 CHF 2

OCH

3 CH2-(2,2-C1 2 -CYClopropyl) B.1021 CH 2 F CH 3

CH

2 -(2,2-C1 2 -CYClopropyl) B. 1022 CH 2 F CH 2

CH

3 CH2-(2,2-Cl 2 -CYClopropyl) B.1023 CH 2 F CF 3 CH2-(2,2-C1 2 -CYClopropyl) B.1024 CH 2 F Cl CH 2 -(2,2-C1 2 -CYClopropyl) B.1025 CH 2 F OCH 3

CH

2 -(2,2-C1 2 CYClopropyl) B.1026 OCH 3

CH

3

CH

2 -(2,2-C1 2 -CYClopropyl) 0050/ 46490 No. R 3

R

5

R

B.1027 OCH 3

CH

2

CH

3

CH

2 -(2,2-Cl 2 -CYClopropyl) B.1028 OCH 3

CF

3

CH

2 -(2,2-C1 2 -cyclopropyl) B.1029 OCH 3 Cl CH 2 -(2,2-C 2 -CYClopropyl) B.1030 OCH 3

OCH

3

CH

2 -(2,2--C1 2 -CYClopropyl) B. 1031 OCH 2

CH

3

CH

3

CH

2 -(2,2-C1 2 CYClopropyl) B. 1032 OCH 2

CH

3

CH

2

CH

3

CH

2 ,2-C12-CYClopropyl) B. 1033 OCH 2

CH

3

CF

3

CH

2 -(2,2-C1 2 -CYClopropyl) B.1034 OCH 2

CH

3 Cl CH 2 -(2,2-C1 2 -CYClopropyl) B.1035 OCH 2

CH

3

OCH

3

CH

2 -(2,2-C1 2 cyclopropyl) B.1036 CN CH 3

CH

2 -(2,2-C1 2 CYClopropyl) B.1037 CN CH 2

CH

3

CH

2 -(2,2-C1 2 -CYClopropyl) B.1038 CN CF 3

CH

2 -(2,2-C1 2 -CYClopropyl) B.1039 CN Cl CH 2 -(2,2-C1 2 -CYClopropyl) B.1040 CN OCH 3

CH

2 -(2,2-C1 2 -CYClopropyl) B.1041 Cl H CH 2 C C-Cl B.1042 Cl CH 3

CH

2 C=C-Cl B.1043 Cl CH 2

CH

3

CH

2 C=C-C1 B.1044 Cl CF 3

CH

2 C C-Cl B.1045 Cl CHF 2

CH

2 C C-Cl B.1046 Cl CH 2 F CH 2 C=C-Cl B.1047 Cl Cl CH 2 C C-Cl B.1048 Cl OCH 3

CH

2 C=C-Cl B.1049 Cl OCH 2

CH

3

CH

2 C=C-Cl B.1050 Cl CN CH 2 C C-Cl B.1051 CH 3 H CH 2 C=C-Cl B.1052 CH 3

CH

3

CH

2 C=C-C1 B.1053 CH 3

CH

2

CH

3

CH

2 C C-Cl B.1054 CH 3

CF

3

CH

2 C C-Cl B.1055 CH 3

CHF

2

CH

2 C=C-Cl B.1056 CH 3

CH

2 F CH 2 C=C-Cl B.1057 CH 3 Cl CH 2 C=C-Cl B.1058 CH 3

OCH

3

CH

2 C=C-Cl B.1059 CH 3

OCH

2

CH

3

CH

2 C C-Cl1 B.1060 CH 3 CN CH 2 C C-Cl B.1061 CF 3 H CH 2 C=C-Cl B.1062 CF 3

CH

3

CH

2 C C-Cl B.1063 CF 3

CH

2

CH

3

CH

2 C C-Cl B.1064 I CF 3

CF

3

CH

2 C C-Cl IB. 1065] CF 3 I CHF 2

CH

2 C C-Cl 0050/46490 No. R 3

R

5

R

6 B. 1066 CF 3

CH

2 F CH 2 C C-C1 B. 1067 CF 3 Cl CH 2 C C-C1 B. 1068 CF 3

OCH

3

CH

2 C C-C 1 B. 1069 CF 3

OCH

2

CH

3

CH

2 C=C-Cl B.1070 CF 3 Cli CH 2 C=C-Cl B.1071 H CH 3

CH

2 C-=C-Cl B.1072 H CH 2

CH

3

CH

2 C=C-Cl B.1073 H CF 3

CH

2 C=C-Cl B.1074 H Cl CH 2 C C-Cl B.1075 H OCH 3

CH

2 C=C-C1 B.1076 CH 2

CH

3

CH

3

CH

2 C=C-Cl B.1077 CH 2

CH

3

CH

2

CH

3

CH

2 C=C-Cl B.1078 CH 2

CH

3

CF

3

CH

2 C C-Cl B.1079 CH 2

CH

3 Cl CH 2 C=C-Cl B.1080 CH 2

CH

3

OCH

3

CH

2 C=C-Cl B.1081 CHF 2

CH

3

CH

2 C C-Cl B.1082 CHF 2

CH

2

CH

3

CH

2 C C-Cl B.1083 CHF 2

CF

3

CH

2 C=C-Cl B.1084 CHF 2 Cl CH 2 C C-C 1 B.1085 CHF 2

OCH

3

CH

2 C=C-Cl B.1086 CH 2 F CH 3

CH

2 C=C-Cl B.1087 CH 2 F CH 2

CH

3

CH

2 C-=C-Cl B.1088 CH 2 F CF 3

CH

2 C=C-Cl B.1089 CH 2 F Cl CH 2 C=C-Cl B.1090 CH 2 F OCH 3

CH

2 C C-C1 B.1091 OCH 3

CH

3

CH

2 C C-Cl B.1092 OCH 3

CH

2

CH

3

CH

2 C C-Cl B.1093 OCH 3

CF

3

CH

2 C C-Cl B.1094 OCH 3 Cl CH 2 C=C-Cl B.1095 OCH 3

OCH

3

CH

2 C C-Cl B.1096 OCH 2

CH

3

CH

3

CH

2 C C-Cl B.1097 OCH 2

CH

3

CH

2

CH

3

CH

2 C C-Cl B.1098 OCH 2

CH

3

CF

3

CH

2 C=C-Cl B.1099 OCH 2

CH

3 Cl CH 2 C=C-Cl B.1100 OCH 2

CH

3

OCH

3

CH

2 C=C-Cl B.1101 CII CH 3

CH

2 C=C-Cl B.1102 CII CH 2

CH

3

CH

2 C=C-Cl EB.1103 CN

CF

3

ICH

2 C=C-Cl CII Cl CH 2 C=-C-Cl 0050/46490 No. R 3

R

5

R

B. 1105 ON

OCH

3

CH

2 C C-Cl B. 1106 01 H CH 2 C C-CH 2

CH

3 B. 1107 01 CH 3

CH

2

C-HCH

B. 1108 01 CH 2

CH

3

CH

2 C C-CH 2

CH

3 B.1109 01

CF

3

OH

2 C C-CH 2

CH

3 B. 1110 Cl

CHF

2

CH

2 C C-CH 2

CH

3 B. 1111 Cl CH 2 F CH 2 C C-CH 2

CH

3 B. 1112 Cl Cl CH 2 C MC-CH 2

CH

3 B.1113 01 00H 3

CH

2 C MC-CH 2

CH

3 B. 1114 01 OCH 2

CH

3

CH

2 C MC-CH 2

CH

3 B.1115 01 CN CH 2 C MC-CH 2

CH

3 B.1116 CH 3 HCH 2 C C-CH 2

CH

3 B.1117 OH 3 OH 3

CH

2 C C-CH 2

CH

3 B.1118 OH 3

CH

2

CH

3

CH

2 C MC-CH 2

CH

3 B.1119 CH 3

CF

3

CH

2 C MC-CH 2

CH

3 B.1120 OH 3

CHF

2

CH

2 C C-CH 2

CH

3 B.1121 CH 3

CH

2 F CH 2 C C-CH 2

CH

3 B.1122 CH 3 01 CH 2 C C-CH 2

CH

3 B.1123 CH 3

OCH

3

CH

2 C C-CH 2

CH

3 B.1124 OH 3

OOH

2

CH

3

CH

2 C C-CH 2

CH

3 B.1125 OH 3 ON CH 2 C M -CH 2

CH

3 B.1126 OF 3 H CH 2 C C-CH 2

CH

3 B.1127 OF 3 OH 3

CH

2 C C-CH 2

CH

3 B.1128

OF

3

CH

2

CH

3

CH

2 C C-CH 2

CH

3 B. 1129 OF 3

OF

3

CH

2 C C-CH 2

CH

3 B.1130 OF 3

CHF

2

CH

2 C C-CH 2

CH

3 B.1131 CF 3 CH 2 F CH 2 C MC-CH 2

CH

3 B.1132

OF

3 Cl CH 2 C -=C-CH 2

CH

3 B. 1133 CF 3 00H 3

CH

2 C MC-CH 2

CH

3 B. 1134 CF 3

OCH

2

CH

3

CH

2 C C-CH 2

CH

3 B.1135 CF 3 ON CH 2 C C-CH 2

CH

3 B.1136 H

OH

3

CH

2 C M -CH 2

CH

3 B.1137 H

CH

2

CH

3

CH

2 C C-CH 2

CH

3 B.1138 H

OF

3

CH

2 C C-CH 2

CH

3 B.1139 H Cl CH 2 C C-CH 2

CH

3 B.1140 H 00H 3

CH

2 C C-CH 2

CH

3 B. 1141 CH 2

CH

3

OH

3

CH

2 C C-CH 2

CH

3 B. 1142 CH 2

CH

3

CH

2

CH

3

CH

2 C C-H 2

CH

3 1143 CH 2 0H 3

OF

3

CH

2 C C-CH 2

CH

3 0050/46490 No. R SR B.1144 CH 2

CH

3 Cl CH 2 C C-CH 2

CH

3 B. 1145 CH 2

CH

3 OCH 3

CH

2 C C-CH 2

CH

3 1146 CHF 2

CH

3

CH

2 C C-CH 2

CH

3 B. 1147 CHF 2

CH

2

CH

3

CH

2 C C-CH 2

CH

3 B. 1148 CHF 2 CF 3

CH

2 C C-CH 2

CH

3 B. 1149 CHF 2 Cl CH 2 C C-CH 2

CH

3 B. 1150 CHF 2 OCH 3

CH

2 C C-CH 2

CH

3 B. 1151 CH 2 F

CH

3

CH

2 C C-CH 2

CH

3 B.1152

CH

2 F

CH

2

CH

3

CH

2 C C-CH 2

CH

3 B. 1153 CH 2 F

CF

3

CH

2 C C-CH 2

CH

3 B. 1154 CH 2 F Cl CH 2 C C-CH 2

CH

3 B. 1155 CH 2 F

OCH

3

CH

2 C C-CH 2

CH

3 B. 1156 OCH 3 CH 3

CH

2 C C-CH 2

CH

3 B. 1157 OCH 3 CH 2

CH

3

CH

2 C C-CH 2

CH

3 B. 1158 OCH 3 CF 3

CH

2 C C-CH 2

CH

3 B. 1159 OCH 3 cl CH 2 C C-CH 2

CH

3 B. 1160 OCH 3 OCH 3

CH

2 C C-CH 2

CH

3 B. 1161 OCH 2

CH

3

CH

3

CH

2 C C-CH 2

CH

3 B.1162 OCH 2

CH

3

CH

2

CH

3

CH

2 C C-CH 2

CH

3 B. 1163 OCH 2

CH

3 CF 3

CH

2 C MC-CH 2

CH

3 B. 1164 OCH 2

CH

3 Cl CH 2 C C-CH 2

CH

3 B. 1165 OCH 2

CH

3 OCH 3

CH

2 C C-CH 2

CH

3 B1166 CN

CH

3

CHCC-CH

2

CH

3 B. 1167 CN

CH

2

CH

3

CH

2 C MC-CH 2

CH

3 B.1168 ON

CF

3

CH

2 C C-CH 2

CH

3 B.1169 CN Cl CH 2 C C-CH 2

CH

3 B.1170 CN

OCH

3

CH

2 C C-CH 2

CH

3 B.1171 Cl H CH 2 C C-CF 3 B.1172 Cl

CH

3

CH

2 C C-CF 3 B.1173 Cl

CH

2

CH

3

CH

2 C C-CF 3 B.1174 Cl

CF

3

CH

2 C C-CF 3 B.1175 Cl

CHF

2

CH

2 C C-CF 3 B.1176 Cl

CH

2 F CH 2 C C-CF 3 B.1177 Cl Cl CH 2 C C-CF 3 B.1178 Cl

OCH

3

CH

2 C =C-CF 3 B.1179 Cl

OCH

2

CH

3

CH

2 C C-CF 3 B.1180 Cl ON CH 2 C C-CF 3 B.1181

CH

3 H CH 2 C MC-CF 3 B.12CH 3 OH 3

CH

2 C =-C-CF 3 0050/46490 No. R 3 R5R 6 B. 1183 CU 3 CH 2

CH

3

CH

2 C MC-CF 3 B. 1184 CU 3

CF

3

CH

2 C C-CF 3 1185 CU 3

CHF

2

CH

2 C C-CF 3 B. 1186 CU 3 CU 2 F CH 2 C C-CF 3 B. 1187 CU 3 Cl CH 2 C C-CF 3 B. 1188 CH 3 OCH 3

CHU

2 C C-CF 3 1B. 1189 CU 3

OCH

2

CH

3

CH

2 C C-CF 3 B.1190

CU

3 CN CH 2 C C-CF 3 B.1191

CF

3 H CH 2 C MC-CF 3 B.1192

CF

3 CU 3

CH

2 C -C-CF 3 B.1193

CF

3 CU 2

CU

3

CH

2 C MC-CF 3 B.1194

CF

3 CF 3

CH

2 C -=C-CF 3 B.1195

CF

3 CHF 2

CH

2 C MC-CF 3 B.1196

CF

3 CH 2 F CU 2 C MC-CF 3 B.1197

CF

3 Cl CH 2 C -=C-CF 3 B.1198 CF 3

OCH

3

CH

2 C MC-CF 3 B.1199 CF 3

OCH

2

CH

3

CU

2 C C-CF 3 B.1200

CF

3 CN CH 2 C C-CF 3 B.1201 H

CU

3

CU

2 C C-CF 3 B.1202 U CH 2

CH

3

CH

2 C C-CF 3 B.1203 H

CF

3

CH

2 C C-CF 3 B.1204 H Cl CH 2 C C-CF 3 B.1205 H

OCH

3

CH

2 C C-CF 3 B.1206

CH

2

CH

3 CU 3

CH

2 C C-CF 3 30B.27

CC

3

CUC

3

CCC-

3 B.1207

CH

2

CH

3 CF2C 3

CH

2 C C-CF 3 B.1208

CH

2

CU

3 Cl3 CH 2 C C-CF 3 B.1209 CU 2

CH

3 OCH CH 2 C C-CF 3 3B.1210

CH

2 OCU 3

CH

2 C C-CF 3 3B.1211

CHF

2 CHC 3

CH

2 C C-CF 3 B.1212

CUF

2 CF2C 3

CU

2 C C-CF 3 B.1213

CHF

2 Cl3 CH 2 C C-CF 3 4B.1214

CUF

2 OCU

CH

2 C C-CF 3 4B.1215 CH 2

OCU

3

C

2 C C-CF B.1216 CU 2 F

CF

3

CU

2 C C-CF 3 B.1217

CH

2 F Cl2H CU 2 C C-CF 3 4B.1220

CH

2 F

OCH

3 CH 2 C C-CF 3 1B.12 21 OCU 3 CU 3

CU

2 C C-CF 3 0050/46490 No. R 3 RS6 B. 1222 OCH 3

CH

2

CH

3

CH

2 C C-CF 3 B. 1223 OCH 3

CF

3

CH

2 C C-CF 3 B.12241 OCH 3 Cl CH 2 C C-CF 3 B. 1225 0GB 3

OCH

3

CH

2 C C-CF 3 B. 1226 OCH 2

CH

3

CH

3

CH

2 C C-CF 3 B. 1227 OCH 2

CH

3

CH

2

CH

3

CH

2 C MC-CF 3 B. 1228 OCH7CH 3 i CF 3

CH

2 C C-CF 3 B.1229 OCH 2

CB

3 Cl CH 2 C C-CF 3 B. 1230 QCH 2

CH

3 0GB 3

CH

2 C C-CF 3 B.1231 CN GB 3

CH

2 C G-CF 3 B.1232 GN CH 2

CH

3

CH

2 C C-CF 3 B.1233 CN CF 3

CH

2 C C-CF 3 B.1234 CN Cl GH 2 C C-CF 3 B.1235 CN OCH 3

CH

2 C C-CF 3 B.1236 Cl H CH 2 C MC-C (CH 3 3 B.1237 Cl GB 3

CH

2 C MC-C (CH 3 3 B.1238 Cl CB 2

CH

3

CH

2 C MC-C (CH 3 3 B.1239 Cl CF 3

CH

2 C C-C (CH 3 3 B.1240 Cl CHF 2

GH

2 C C-C (CH 3 3 B.1241 Cl CH 2 F CH 2 C G-C (CH 3 3 B.1242 Cl Cl CH 2 C C-C (CH 3 3 B.1243 Cl 0GB 3

CH

2

C=G-C(CH

3 3 B.1244 Cl OCH 2

CB

3

CH

2 G G-C (CH 3 3 B.1245 Cl CN CH 2 C C-G (CH 3 3 B.1246 GB 3 H CH 2 C C-C (CH 3 3 B.1247 GB 3

CH

3

CH

2 C C-C (CH 3 3 B.1248 GB 3

CH

2

CH

3

CH

2 C C-C (CH 3 3 B.1249 GB 3

CF

3

CH

2 C MC-C (CH 3 3 B.1250 GB 3

CHF

2

CH

2 C MC-C (CH 3 3 B.1251 GB 3

CH

2 F CH 2 C MC-C (CH 3 3 B.1252 GB 3 Cl CH 2 C MC-C (CH 3 3 B.1253 GB 3

OCH

3

CH

2 C C-C (CH 3 3 B.1254 CH 3

OCH

2

CH

3

CH

2 C C-C (CH 3 3 B.1255 GB 3 GN CH 2 C C-C (CH 3 3 B.1256 CF 3 H CH 2 G C-C (CB 3 3 B.1257 CF 3

CH

3

CH

2 C C-C (CH 3 3 B.1258 CF 3

CH

2

CB

3

CH

2 C MC-C (CH 3 3 B.12591 CF 3

CF

3

CH

2 C C-C (CH 3 3 B.12601 CF 3

CHF

2

CB

2 C C-C (CH 3 3 0050 /46490 No. R SR B. 1261 CF 3

CH

2 F CH 2 C C-C (CH 3 3 B. 1262 CF 3 Cl CH 2 C C-C (CH 3 3 B. 1263 CF 3

OCH

3

CH

2 C C-C (CH 3 3 B. 1264 CF 3

OCH

2

CH

3

CH

2 C SO-C (OH 3 3 B.1265 CF 3 CN CH 2 C C-C (CH 3 3 B.1266 H OH 3

CH

2 C C-C (CH 3 3 B.1267 H CH 2

CH

3

CH

2 C C-C (CH 3 3 B.1268 H CF 3

CH

2 C C-C (CH 3 3 B.1269 H Cl CH 2 C C-C (CH 3 3 B.1270 H OCH 3

CH

2 C C-C (CH 3 3 B.1271 CH 2

CH

3

OH

3

CH

2 C C-C (CH 3 3 B. 1272 CH 2

CH

3

CH

2

CH

3

CH

2 C C-C (OH 3 3 B. 1273 CH 2

CH

3

CF

3

CH

2 C C-C (CH 3 3 B.1274 CH 2

CH

3 Cl CH 2 C C-C (CH 3 3 B.1275 CH 2

CH

3

OCH

3

CH

2 C C-C (CH 3 3 B.1276 CHF 2

OH

3

CH

2 C C-C (CH 3 3 B. 1277 CHF 2

CH

2

CH

3

CH

2 C C-C (CH 3 3 B.1278 CHF 2

CF

3

CH

2 C C-C (CH 3 3 B.1279 CHF 2 Cl CH 2 C C-C (CH 3 3 B.1280 CHF 2

OCH

3

CH

2 C C-C (CH 3 3 B.1281 CH 2 F CH 3

CH

2

CMC-C(CH

3 3 1282 CH 2 F CH 2

CH

3

CH

2 C SC-C(OH 3 B.1283 CH 2 F CF 3

CH

2 C C-C (CH 3 3 B.1284 CH 2 F Cl CH 2 C C-C (CH 3 3 B.1285 CH 2 F 00H 3

CH

2 C C-C (CH 3 3 B.1286 OCH 3

OH

3

CH

2 C C-C (CH 3 3 B.1287 00H 3

CH

2

CH

3

CH

2 C C-C (CH 3 3 B.1288 00H 3

CF

3

CH

2 C C-C (CH 3 3 B.1289 OCH 3 Cl CH 2 C C-C (CH 3 3 B.1290 OCH 3

OCH

3

CH

2 C C-C (CH 3 3 B.1291 OCH 2

CH

3

OH

3

CH

2 C C-C (CH 3 3 B. 1292 OCH7C 3 2

H

C

HHC C-C (OH 3 3 B. 1293 OCH 2

CH

3

C

3

CH

2

CC-CH)

B.1293 00H 2

CH

3 Cl3 CH 2 C MC-C (CH 3 3 B.1294 OCH 2

CH

3 00H CH 2 C C-C (CH 3 3 B.1296 ON OH 3

CH

2 C C-C (CH 3 3 B.1297 ON CH 2

CH

3

CH

2 C C-C (CH 3 3 B.1298 ON CF 3

CH

2 C C-C (CH 3 3 B.1299 ON 01 CH 2 C C-C (CH 3 3 0050/46490 No. R 3 IsR B. 1300 CN OCH 3

CH

2 C C-C (CH 3 3 B. 1301 Cl H CH 2 C C-C 6

H

5B.1302 Cl CH 3

CH

2 C C-C 6

H

B.1303 Cl CH 2

CH

3

CH

2 C C-C 6

H

B.1304 Cl CF 3

CH

2 C C-C0H B.1305 Cl CHF 2

CH

2 C C-C 6

H

10B.1306 Cl CH 2 F CH 2 C C-C 6

H

B.1307 Cl Cl CH 2 C C-C 6

H

B.1308 Cl OCH 3

CH

2 C C-C 6

H

B.1309 Cl OCH 2

CH

3

CH

2 C C-CrHR B.1310 Cl CN CH 2 C C-C 6

H

B.1311 CH 3 H CH 2 C C-C 6

H

B.1312 CH 3

CH

3

CH

2 C C-C 6

H

B.1313 CH 3

CH

2

CH

3

CH

2 C C-C 6

H

B.1314 CH 3 CF 3

CH

2 C C-C 6

H

B.1315 CH 3

CHF

2

CH

2 C C-C 6

H

B.1316 CH 3

CH

2 F CH 2 C C-C 6

H

B.1317 CH 3 Cl CH 2 C C-C 6

H

B.1318 CH 3

OCH

3

CH

2 C C-CrH 5 B.1319 CH 3

OCH

2

CH

3

CH

2 C C-C0H B.1320 CH 3 CN CH 2 C C-C0H B.1321 CF 3 H CH 2 C C-CrH 5 B.1322 CF 3

CH

3

CH

2 C C-C 6

H

30B.1323 CF 3

CH

2

CH

3

CH

2 C C-C 6

H

30B.1324 CF 3

CF

3

CH

2 C C-CrH 5 B.1325 CF 3

CHF

2

CH

2 C C-C 6

H

B.1326 CF 3 CH 2 F CH 2 C C-C0H B.1327 CF 3 Cl CH 2 C C-CrH 5 B.1328 CF 3 OCH 3

CH

2

C=C-C

6

H

B.1329 CF 3

OCH

2

CH

3

CH

2

C==C-C

6

H

B.1330 CF 3 CN CH 2 C= C-C 6

H

B.13311 H

CH

3

CH

2

C=C-C

6

H

B.1332 H CH 2

CH

3

CH

2

C=C-C

6

H

B.1333 H CF 3

CH

2 C C-C0H B.1334 H Cl CH 2 C C-C 6

H

B.1335 H OCH 3

CH

2

C=C-C

6

H

45B.1336 CH 2

CH

3

CH

3

CH

2

C=C-C

6

H

4 53 7C 2 H H 2 H H C C C H IB.13381 CH 2

CH

3

C

2

C

3

CH

2 C C-C 6

H

0050/46490 NO. R 3 RS6 B.1339

CH

2

CH

3 Cl CH 2

C=C-C

6

H

B.1340

CH

2

CH

3 OCH 3

CH

2 C =C-C 6

H

B.1341

CHF

2 CHCHCCCH B.32 H 2

CH

3

CH

2

C=C-C

6

H

B.1342

CHF

2 CHC 3

CH

2

C=C-C

6

H

B.1343 CHF 2 Cl3 CH 2 C= C-C 6

H

B.1344

CHF

2 OCH CH 2

C=C-C

6

H

10B.35 CF C3 C2 CCH B.1346

CH

2 F

CH

3

CH

2

C=C-C

6

H

B.1347

CH

2 F

CH

2

CH

3

CH

2 C C-C0H B.1348

CH

2 F

CF

3

CH

2 C C-C 6

H

B.1349

CH

2 F Cl CH 2 C C-C 6

H

B.1350

CH

2 F

OCH

3

CH

2

C=C-C

6

H

B.1351

OCH

3 CH 3

CH

2 C C-Crw 6

H

B.1352

OCH

3 CH 2

CH

3

CH

2

C=C-C

6

H

B.1353

OCH

3 CF 3

CH

2 C =C-C 6

H

B.1354 OCH 3 Cl CH 2 C C-CrHr, B.1355

OCH

3 OCH 3

CH

2

C=C-C

6

H

B.1356 OCH 2

CH

3 CH 3

CH

2

C=C-C

6

H

B. 1357 OCH 2

CH

3

CH

2

CH

3

CH

2 CaC-C 6

H

B.1358 OCH 2

CH

3

CF

3

CH

2 C C-C 6

H

B.1359

OCH

2

CH

3 Cl CH 2 C C-C 6

H

B.1360

OCH

2

CH

3 OCH 3

CH

2 C C-C 6

H

B.1361 CN

CH

3

CH

2

C=C-C

6

H

B.1362 CN'

CH

2

CH

3

CH

2

C=C-C

6

H

30B.33CCFCHCCCH B.1363 CN Cl3 CH 2

C=C-C

6

H

B.1364 CN OCH CH 2

C=C-C

6

H

B.1365 Cl OH3

CH

2 C=C-(Cl-- 6

H

3B.1366 Cl CH CH2C C- (2-C1-C 6

H

4 3B.1367 Cl

CHCH

3

CH

2 C C- (2-Cl-C 6

H

4 B.1368 Cl CF2C 3

CH

2 C C- (2-Cl-C 6

H

4 B.1369 Cl CHF3 CH 2 C C- (2-Cl-C 6

H

4 4B.1370 Cl

CH

2

CH

2 C=C-(2-Cl-C 6

H

4 40B.13 71 Cl Cl2 CH 2 C C- (2-Cl-C 6

H

4 B.1372 Cl OCH CH 2 C C- (2-Cl-C 6

H

4 B.1373 Cl

OHCH

3

CH

2 C C- (2-Cl-C 6

H

4 B.1375 Cl CN CH 2 C=C-(2-Cl-C 6

H

4 4B.1376

CH

3 H

CH

2 C c- (2-Cl-C 6

H

4 B.1377

CH

3 CH 3

CH

2 C C- (2-Cl-C 6

H

4 0050/46490 No. R 3 RS6 B. 1378 CH 3

CH

2

CH

3

CH

2 C (2-C1--C 6

H

4 B. 1379 CH 3 CF 3

CH

2 C (2-Cl-C 6

H

4 B. 1380 CH 3 CHF 2

CH

2 C 2-C1-C 6

H

4 B. 1381 CH 3 CH 2 F CH 2 C MC- (2-Cl-C 6

H

4 B. 1382 CH 3 Cl CH 2 C MC- (2-Cl-C 6

H

4 B. 1383 CH 3 OCH 3

CH

2 C 2-Cl-C 6

H

4 1384 CH 3

OCH

2

CH

3

CH

2 C (2-C1-C 6

H

4 B.1385

CH

3 CN CH 2 C C- (2-C1-C 6

H

4 B.1386

CF

3 H CH 2 C C- (2-Cl-C 6

H

4 B.1387

CF

3 CH 3

CH

2 C C- (2-Cl-C 6

H

4 B. 1388 CF 3

CH

2

CH

3

CH

2 C C- (2-C1-C 6

H

4 B.1389 CF 3 CF 3

CH

2 C C- (2-Cl-C 6

H

4 B.1390

CF

3 CHF 2

CH

2 C MC- (2-Cl-C 6

H

4 B.1391

CF

3 CH 2 F CH 2 C C- (2-Cl-C 6

H

4 B.1392 CF 3 Cl CH 2 C C-(2-Cl-C 6

H

4 B.1393

CF

3 OCH 3

CH

2 C MC- (2-Cl-C 6

H

4 B. 1394 CF 3

OCH

2

CH

3

CH

2 C M C- (2-C1-C 6

H

4 B.1395

CF

3 CN CH 2 C C- (2-Cl-C 6

H

4 B.1396 H

CH

3

CH

2 C C- (2-C1-C 6

H

4 B.1397 H CH 2

CH

3

CH

2 C C- (2-Cl-C 6

H

4 B.1398 H

CF

3

CH

2 C C- (2-Cl-C 6

H

4 B.1399 H Cl CH 2 C C- (2-Cl-C 6

H

4 B.1400 H

OCH

3

CH

2 C C- (2-Cl-C 6

H

4 B.1401 CH 2

CH

3

CH

3

CH

2 C C- (2-Cl-C 6

H

4 B.1402 CH 2

CH

3

CH

2

CH

3

CH

2 C C- (2-Cl-C 6

H

4 B. 1403 CH 2

CH

3

CF

3

CH

2 C C- (2-Cl-C 6

H

4 B.1404 CHCH 3 i Cl CH 2 C C- (2-C1-C 6

H

4 B. 1405 CH 2

CH

3

OCH

3

CH

2 C C- (2-Cl-C 6

H

4 B. 1406 CHF 2 CH 3

CH

2 C C- (2-C1-C 6

H

4 B. 1407 CHF 2

CH

2

CH

3

CH

2 C 2-C1-C 6

H

4 B.1408

CHF

2 CF 3

CH

2 C C- (2-Cl-C 6

H

4 B.1409

CHF

2 Cl CH 2 C- (2-Cl-C 6

H

4 B.1410 CHF 2 OCH 3

CH

2 C C- (2-C1-C 6

H

4 B. 1411 CH 2 F CH 3

CH

2 C C- (2-Cl-C 6

H

4 B.1412 CH 2 F CH 2

CH

3

CH

2 C 2-C1-C 6

H

4 B.1413

CH

2 F

CF

3

CH

2 C C-(2-Cl-COO 4 B.1414 CH 2 F Cl CH 2 C C- (2-Cl-C 6

H

4 B.1415 CH 2 F

OCH

3

CH

2 C C- (2-C1-C 6

H

4 B.1416 OCH 3 CH 3

CH

2 C 2-Cl-COH 4 0050/46490 No. R3R 5

R

B. 1417 OCH 3 CH 2

CH

3

CH

2 C C- (2-C1-C 6

H

4 B. 1418 OCH 3 CF 3

CH

2 C C- (2-Cl-C 6

H

4 1419 OCH 3 Cl CH 2 C C-(2-Cl-C 6

H

4 B. 1420 OCH 3 OCH 3

CH

2 C C- (2-Cl-C 6

H

4 B. 1421 OCH 2

CH

3 CH 3

CH

2 C (2-C--C 6

H

4 B. 1422 OCH 2

CH

3

CH

2

CH

3

CH

2 C C- 2-Cl-C 6

H

4 1423 OCH 2

CH

3

CF

3

CH

2 C (2-C1--C 6

H

4 4 4 O H CH lC 2 2 C 6 4 B.1425 OCH 2

CH

3 OCl CH 2 C C- (2-Cl-C 6

H

4 B.1426 OCH

OCH

3

CH

2 C C- (2-Cl-C 6

H

4 B.1427 CN

CHC

3

CH

2 C C- (2-C1-C 6

H

4 15B.1428 CN

C

2

C

3

CH

2 C C- (2-Cl-C 6

H

4 15B.1429 CN

CF

3

CH

2 C C- (2-C1-C 6

H

4 B.1430 CN OCl CH 2 C C- (2-Cl-C 6

H

4 Table 41 Compounds of the general f ormula Ia. 5 where R 2 is hydrogen and the combination of the radicals R 3 Rx, RY and Rz for each compound corresponds to one line of Table C

R

2 m Rx R 011

OH

3 1---NO 0H 3 C

NR

3 Rz 0 Table 42 Compounds of the general formula Ib.5 where R 2 is hydrogen and the combination of the radicals R 3 Rx, RY and RZ for each compound corresponds to one line of Table C

R

2 m m

RY

CH

3 NH- _-OCH 3

NR

3 Rz 0 Table 43 Compounds of the general formula Ic. 5 where R 2 m is hydrogen and the combination of the radicals R 3 Rx, RY and Rz f or each compound corresponds to one line of Table C 0050/46490

R

2 m

RX

R2 ON RY

H

2 N NOCH 3 N OCH 3 Rz 0 O Table 44 Compounds of the general formula Id.5 where R 2 m is hydrogen and the combination of the radicals R 3 Rx, RY and Rz for each compound corresponds to one line of Table C

R

2 m N RX 0

OCH

3

R

3

RZ

0- Table Compounds of the general formula Ie.5 where R 2 m is hydrogen and the combination of the radicals R 3 Rx, RY and Rz for each compound corresponds to one line of Table C

R

2 mO

RX

R

2 mo Y O1 N RY

R

3

RZ

C H 30C93 R

O

Table 46 Compounds of the general formula Ia.6 where R 2 m is hydrogen and the combination of the radicals R 3 Rx, RY and Rz for each compound corresponds to one line of Table C

RX

R

2 m IRz

CH

3 )C RY 1 a.6) 4 N--Y3R

O

Table 47 Compounds of the general Lormula Ib.6 where R 2 m is hydrogen and the combination of the radicals R 3 RX, RY and Rz for each compound corresponds to one line of Table C

R

2 m R O Rz

CH

3 N )CI (lb.6) S R3 RY

O

0050/46490 91 Table 48 Compounds of the general formula Ic.6 where R 2 m is hydrogen and the combination of the radicals R 3 Rx, RY and Rz for each compound corresponds to one line of Table C

R

2 m Rz

H

2 N OCH 3 (1c.6) 0 Table 49 Compounds of the general formula Id.6 where R 2 m is hydrogen and the combination of the radicals R 3 Rx, RY and Rz for each compound corresponds to one line of Table C

R

2 m^ Rz

CH

3 3OCH 3 R RY (id.6)

R

3

RY

0 Table Compounds of the general formula Ie.6 where R 2 m is hydrogen and the combination of the radicals R 3 RX, RY and Rz for each compound corresponds to one line of Table C

R

2 m Rz

CH

3

CH

3 S R le .6)

R

3

RY

0 Table C: No. R 3 RX RY Rz C.1 CH 3 H H H C.2 CH 3 H CH 3

H

C.3 CH 3 H C 2

H

5

H

C.4 CH 3 H C 3

H

7

H

CH

3 H C 4

H

9

H

C.6 CH 3 H CH(CH 3 2

H

C.7 CH 3 H cyclopropyl H C.8 CH 3 H CF 3

H

C.9 CH 3 H OCH 3

H

CH

3 H OC 2

H

5

H

C.11 CH 3 H CH 2

-C

6

H

5

H

0050/46490 No. R 3 Rx RY RZ C. 12 OH 3 H CH(CH 3

)C

6

H

5

H

0. 13 CH 3 H C 6

H

5

H

0. 14 CH 3 H 4-F-0 6

H

5

H

0. 15 CH 3 H 4-Cl-2-pyridyl H C.16 OH 3 H F H 0.17 CH 3 H ON H 0.18 CH 3

OH

3 H H 0.19 OH 3

OH

3

OH

3

H

CH

3

CH

3

C

2

H

5

H

0.21 OH 3

OH

3

C

3

H

7

H

0.22 OH 3

OH

3

C

4

H

9

H

0.23 OH 3

OH

3

OH(CH

3 2

H

0.24 OH 3

OH

3 cyclopropy. H 0.25 OH 3

OH

3

OF

3

H

0.26 OH 3

OH

3 00H 3

H

0.27 OH 3

OH

3 00 2

H

5

H

0.28 OH 3

OH

3 0H 2

-C

6

H

5

H

0.29 OH 3

OH

3 CH(0H 3

)C

6

H

5

H

0.30 OH 3

OH

3 0 6

H

5

H

0.31 OH 3

OH

3 4-F- 6

H

5

H

0.32 OH 3

OH

3 4-Cl-2-pyridyl H 0.33 OH 3

OH

3 F H 0.34 OH 3

OH

3 ON H 0.35 OH 3

C

2

H

5 H H 0.36 OH 3

C

2

H

5

OH

3

H

0.37 OH 3

C

2

H

5 0 2

H

5

H

0.38 OH 3

C

2

H

5

C

3

H

7

H

0.39 OH 3 0 2

H

5

C

4

H

9

H

0.40 OH 3 0 2

H

5 OH(0H 3 2

H

0.41 OH 3

C

2

H

5 cyclopropyl H 0.42 OH 3 0 2

H

5

OF

3

H

0.43 OH 3 0 2

H

5 00H 3

H

0.44 OH 3

C

2

H

5 00 2

H

5

H

0.45 OH 3 0 2

H

5 0H 2

-C

6

H

5

H

0.46 OH 3 0 2

H

5

CH(CH

3

)C

6

H

5

H

0.47 OH 3 0 2

H

5 0 6

H

5

H

0.48 OH 3

C

2 HS 4-F-0 6

H

5

H

0.49 OH 3 0 2

H

5 4-01-2-pyridyl H 0.50 OH 3 I 2

H.

5 F H 0050/46490 No. R 3 RxRY Rz C. 51 CH 3

C

2

H

5 CN H C. 52 CH 3 cyclopropyl H

H

C.53 CH 3 cyclopropyl

CH

3

H

C.54 CH 3 cyclopropyl

C

2

H

5

H

CH

3 cyclopropyl

C

3

H

7

H

C.56 CH 3 cyclopropyl

C

4

H

9

H

C.57 CH 3 cyclopropyl

CH(CH

3 2

H

C.58 CH 3 cyclopropyl cyclopropyl

H

C.59 CH 3 cyclopropyl

CF

3

H

CH

3 cyclopropyl

OCH

3

H

C.61 CH 3 cyclopropyl 0C 2

H.

5

H

C.62 CH 3 cyclopropyl-

CH

2

-C

6

H

5

H

C.63 CH 3 cyclopropyl

CH(CH

3

)C

6

H

5

H

C.64 CH 3 cyclopropyl

C

6

H

5

H

CH

3 cyclopropyl 4-F-C 6

H

5

H

C.66 CH 3 cyclopropyl 4-Cl-2-pyridyl

H

C.67 CH 3 cyclopropyl F H C.68 CH 3 cyclopropy. CN H C.69 CH 3

CF

3 H H

CH

3

CF

3

CH

3

H

C.71 CH 3

CF

3

C

2

H

5

H

C.72 CH 3

CF

3

C

3

H

7

H

C.73 CH 3

CF

3

C

4 H9 H C.74 CH 3

CF

3 CH (CH 3 2

H

CH

3

CF

3 cyclopropyl

H

C.76 CH 3

CF

3

CF

3

H

C.77 CH 3

CF

3

OCH

3

H

C.78 CH 3

CF

3 0C 2

H

5

H

C.79 CH 3

CF

3

CH

2

-C

6

H

5

H

CH

3

CF

3 CH (CH 3

C

6

H

5

H

C.81 CH 3

CF

3

C

6

H

5

H

C.2 CH 3

CF

3 4-F-C 6

H

5

H

C.83 CH 3

CF

3 4-C1-2-pyridyl

H

C.84 CH 3

CF

3 F H

CH

3

CF

3 CN H C.86 CH 3 H H C.87 CH 3 Cl CH 3

H

C.88 CH 3 Cl C 2

H

5

H

C.89 CH 3 Cl C 3

H

7

H

0050/46490 No. R 3 RX RY

RZ

0. 90 CH 3 01

C

4

H

9 H 0. 91 OH 3 01 CH (01 3 2 H 0.92 OH 3 Cl cyclopropyl

H

0.93 OH 3 01

CF

3 H C.94 CH 3 Cl 00113

H

0.95 OH 3 01 002115

H

0.96 OH 3 01

CH

2

-C

6 1 5 H C.97 OH 3 01 CH(0H 3

)C

6

H

5 H 0.98 CH 3 01 06115

H

0.99 OH 3 01 4-F- 6

H

5 H 0.100 OH 3 01 4-C1-2-pyridyl

H

C.101 OH 3 01 F

H

C.102 OH 3 01 ON

H

0.103 OH 3 F H

H

0.104 O H 3 F 0113

H

C.105 OH 3 F 02115

H

C.106 OH 3 F 03117 H1 0.107 0113 F 04119

H

0.108 0113 F CH(0H 3 2 H 0.109 0113 F cyclopropyl

H

0.110 0113 F

OF

3 H 0.111 0113 F 00113

H

C.112 0113 F 002115 H1 0.113 0113 F 0112-0615 H1 C.114 0113 F 011(0113)06115

H

C.115 0113 F 06115 H1 C.116 0113 F 4-F-C 6

H

5 11 C.117 0113 F 4 -Cl-2--pyridyl H1 C.118 0113 F F

H

C.119 0113 F ON

H

C.120 0113 00113 H

H

C.121 0113 0013 0113 H1 C.122 0113 00113 02115

H

C.123 0113 00113 03117

H

C.124 0113 00113 04119

H

C.125 0113 00113 CH1(113)2

H

C.126 0113 00113 cyclopropyl

H

C.127 0113 00113

OF

3 H C.128 0113 00113 00113

H

0050/46490 No. R 3 RxRY

RZ

C.129 OH 3

OCH

3 00 2

H

5 H 0. 130 OH 3 00H 3 0H 2

-C

6

H

5

H

C.131 OH 3 00113 CH(011 3

)C

6

H

5

H

C.132 OH 3 00H 3 06115

H

C.133 OH 3 O0H 3 4-F- 6

H

5 H C.134 OH 3

OCH

3 4-C1-2-pyridyl

H

C.135 OH 3 00H 3 F

H

C.136 OH 3 00H 3 ON

H

C.137 OH 3 H H

OH

3 C.138 OH 3 H

OH

3 OH 3 C.139 OH 3 H 02115 0113 C.140 OH 3 H

O

3

H

7 OH 3 0.141 OH 3 H 04119

OH

3 0.142 OH 3 H CH (0H 3 2 OH 3 0.143 OH 3 H cyclopropyl

OH

3 0.144 OH 3 H

OF

3 OH 3 0.145 OH 3 H O0H 3 OH 3 0.146 0113 H 00 2

H

5 0113 0.147 0113 H

CH

2

-C

6

H

5 0113 0.148 0113 H CH (011 3 6

H

5 0113 0.149 0113 H 06115 0113 C.150 0113 H 4-F- 6 1 5 0113 0.151 0113 H1 4-01-2--pyridyl 0113 0.152 OH 3 H F 0113 0.153 C11 3 H ON 0113 0.154 0113 0113 H 0113 0.155 0113 0113 0113 0113 0.156 0113 0113 02115 0113 C.157 0113 0113 03117 0113 0.158 0113 0113 04119 0113 0.159 0113 0113 011(0113)2 0113 0.160 0113 0113 cyclopropyl 0113 C.161 0113 0113

OF

3 0113 C.162 0113 0113 00113 0113 C.163 0113 0113 002115 0113 C.164 0113 0113 0112-0615 0113 C.165 0113 0113 1(0113)06115 0113 C.166 0113 0113 06115 0113 C.167 0113 0113 4-F- 6 1 5 0113 0050/46490 No. R 3 Rx RY R 2 C. 168 OH 3

OH

3 4-C1-2-pyridyl

OH

3 C.169 CH 3

OH

3 F

OH

3 C.170 CH 3

OH

3 ON OH 3 C.171 OH 3 0 2

H

5 H

OH

3 C.172 OH 3

C

2

H

5 OH 3 OH 3 C.173 OH 3

C

2

H

5 C 2

H

5 OH 3 C.174 OH 3

C

2

H

5 C 3 H7

OH

3 C.175 OH 3

C

2

H

5 0 4

H

9

OH

3 C.176 OH 3

C

2

H

5 CH (0H 3 2

OH

3 0.177 OH 3

C

2

H

5 cyclopropyl

OH

3 C.178 OH 3

C

2

H

5 OF 3 OH 3 C.179 OH 3

C

2

H

5 00H 3

OH

3 0.180 OH 3

C

2

H

5 00 2

H

5

OH

3 C.181 OH 3

O

2

H

5 OH 2

-C

6

H

5

OH

3 0.182 OH 3

O

2

H

5

CH(CH

3

)C

6

H

5

OH

3 0.183 OH 3 0 2

H

5 C 6

H

5 OH 3 0.184 OH 3

O

2

H

5 4-F-0 6

H

5

OH

3 0.185 OH 3 0 2

H

5 4-01-2-pyridyl

OH

3 0.186 OH 3

C

2

H

5 F

OH

3 C.187 OH 3 0 2

H

5 ON

OH

3 0.188 OH 3 cyclopropyl H

OH

3 C.189 OH 3 cyclopropyl

OH

3

OH

3 0.190 OH 3 cyclopropyl

C

2

H

5

OH

3 0.191 OH 3 cyclopropyl

C

3

H

7

OH

3 C.192 OH 3 cyclopropyl 0 4

H

9

OH

3 C.193 OH 3 cyclopropyl CH (CH 3 2

OH

3 0.194 OH 3 cyclopropyl cyclopropyl

OH

3 C.195 OH 3 cyclopropyl

OF

3

OH

3 0.196 OH 3 cyclopropyl 00H 3

OH

3 0.197 OH 3 cyclopropyl 00 2

H

5

OH

3 0.198 OH 3 cyclopropyl 0H 2

-C

6

H

5

OH

3 0.9 H 3 cyclopropyl

OH(CH

3

)C

6

H

5

OH

3 0.200 OH 3 cyclopropyl

C

6

H

5

OH

3 0.201 OH 3 cyclopropyl 4-F-0 6

H

5

OH

3 0.202 OH 3 cyclopropyl 4-01-2-pyridyl

OH

3 C.203 OH 3 cyclopropyl F OH 3 0.204 OH 3 cyclopropyl ON OH 3 .205

H

3

CF

3 H

H

3 0a20 OH 3

OF

3

OH

3

OH

3 0050/46490 No. R 3 Rx RY Rz C.207 OH 3

OF

3

C

2

H

5

CH

3 C.208 OH 3

CF

3

C

3

H

7

CH

3 C.209 CH 3

CF

3

C

4

H

9

OH

3 C.210 CH 3

OF

3 CH (CH 3 2

OH

3 C.211 OH 3

OF

3 cyclopropyl CH 3 C.212 OH 3

OF

3

CF

3

OH

3 C.213 MH OF0H 3

OH

3 C.214 OH 3

OF

3 00 2

H

5

CH

3 C.215 CH 3

CF

3

CH

2

-C

6

H

5

OH

3 C.216 OH 3

CF

3

CH(CH

3

)C

6

H

5

OH

3 C.217 OH 3

CF

3

C

6

H

5

OH

3 C.218 OH 3

CF

3 4-F-C 6

H

5

OH

3 C.219 OH 3

OF

3 4-01-2-pyri Idyl OH 3 C.220 OH 3

OF

3 F OH 3 C.221 OH 3

OF

3 ON OH 3 0.222 OH 3 Cl H OH 3 C.223 OH 3 01 OH 3

OH

3 0.224 OH 3 0 1 0 2

H

5

OH

3 0.225 OH 3 01 O 3

H

7

OH

3 0.226 OH 3 01 C 4

H

9

OH

3 0.227 OH 3 01 CH(CH 3 2

OH

3 0.228 OH 3 01 cyclopropyl OH 3 0.229 OH 3 01 OF 3

OH

3 0.230 OH 3 01 00H 3

OH

3 0.231 OH 3 01 00 2

H

5

OH

3 0.232 OH 3 01 CH 2

-C

6

H

5

OH

3 C.233 OH 3 Cl OH(CH 3

)C

6

H

5

OH

3 0.234 OH 3 01 C 6

H

5

OH

3 0.235 OH 3 Cl 4-F-C 6

H

5

OH

3 C.236 OH 3 01 4-01-2-pyridyl OH 3 0.237 OH 3 01 F OH 3 0.238 OH 3 01 ON O H 3 0.239 OH 3 F H OH 3 C.240 OH 3 F OH 3

OH

3 C.241 OH 3 F 0 2

H

5

OH

3 0.242 OH 3 F 0 3

H

7

OH

3 0.243 OH 3 F 04H9 OH 3 0.244 OH 3 F CH (CH 3 2

OH

3 0.245 OH 3 F cyclopropyl OH 3 0050/46490 No. R 3 RX Ry RZ C.246 CH 3 F CF 3

CR

3 C.247 CH 3 F OCH 3

CR

3 C.248 CR 3 F 0C 2

H

5

CR

3 C.249 CH 3 F CH 2

-C

6

H

5

CH

3 C.250 CR 3 F CH(CH 3 )C6H 5

CH

3 C.251 CH 3 F C 6

R

5

CH

3 C.252 CH 3 F 4-F-C 6

H

5

CH

3 C.253 CH 3 F 4-C1-2-pyridyl CH 3 C.254 CR 3 F F CH 3 C.255 CR 3 F CN CR 3 C.256 CR 3

OCH

3 H CR 3 C.257 CR 3

OCR

3

CR

3

CR

3 C.258 CR 3

OCR

3

C

2

H

5

CR

3 C.259 CR 3

OCR

3

C

3

H

7

CR

3 C.260 CR 3

OCR

3

C

4

H

9

CR

3 C.261 CR 3

OCR

3 CH (CH 3 2

CR

3 C.262 CR 3

OCR

3 cyclopropyl CR 3 C..263 CH 3

OCR

3

CF

3

CR

3 C.264 CR 3

OCH

3

OCR

3

CR

3 C.265 CR 3

OCR

3 0C 2

H

5

CR

3 C.266 CR 3

OCR

3

CR

2

-C

6

H

5

CR

3 C.267 CR 3

OCR

3

CR(CR

3

)C

6

R

5

CR

3 C.268 CR 3

OCR

3

C

6

R

5

CR

3 C.269 CR 3

OCR

3 4-F-C 6

R

5

CR

3 C.270 CR 3

OCR

3 4-Cl-2-pyridyl CR 3 C.271 CR 3

OCR

3 F CR 3 C.272 CR 3

OCR

3 CN CR 3 C.273 H CR 3 H H C.274 R CR 3

CR

3

R

C.275 H CR 3

C

2

R

5

R

C26 H CR 3

C

3

R

7

H

C27 H CR 3

C

4

R

9

H

C.278 R CR 3 CH (CHA) 2

H

C.279 H CR 3 cyclopropyl H C.280 H CR 3

CF

3

H

C.281 R CR 3

OCR

3

R

C.282 H CR 3 0C 2

H

5

R

C.283 R CR 3

CH

2

-C

6

H

5

H

C.284 H CR 3

CH(CH

3

)C

6

H

5

R

0050/46490 No. R 3 Rx Ry Rz C.285 H OH 3

C

6

H

5

H

C.286 H 0H3 4-F-0 6

H

5

H

C.287 H OH 3 4-Cl-2-pyridyl H C.288 H CH 3 F H C.289 H OH 3 CN H C.290 H CH 3 H OH 3 C.291 H OH 3 OH 3

OH

3 C.292 H CH 3 C 2

H

5

CH

3 C.293 H CH 3 C 3

H

7

OH

3 0.294 H OH 3 C 4

H

9

OH

3 C.295 H OH 3 CH (CH 3 2

OH

3 C.296 H OH 3 cyclopropyl

OH

3 C.297 H OH 3 CF 3

CH

3 C.298 H CH 3 00H 3

OH

3 C.299 H CH 3 0C 2

H

5

OH

3 0.300 H OH 3 CH 2

-C

6

H

5

OH

3 0.301 H OH 3 CH (CH 3

C

6

H

5

CH

3 C.302 H OH 3

C

6

H

5

OH

3 C.303 H OH 3 4-F- 6

H

5

OH

3 C.304 H CH 3 4-C1-2-pyridyl

OH

3 C.305 H OH 3 F CH 3 C.306 H OH 3 ON CH 3 C.307 H CF 3 H H C.308 H CF 3

CH

3

H

C.309 H OF 3

C

2

H

5

H

C.310 H OF 3

C

3

H

7

H

0.311 H OF 3

C

4

H

9

H

C.312 H OF 3 CH (CH 3 2

H

C.313 H OF 3 cyclopropyl

H

C.314 H OF 3

OF

3

H

C.315 H OF 3 00H 3

H

0.316 H OF 3 00 2

H

5

H

0.317 H OF 3 0H 2 -0 6

H

5

H

0.318 H OF 3

OH(CH

3

)C

6

H

5

H

0.319 H OF 3

C

6

H

5

H

0.320 H OF 3 4-F- 6

H

5

H

0.321 H OF 3 4-C1-2-pyridyl H 0.322 H OF 3 F H 0 .323 H OF 3 ON H 0050/46490 100 No. R XRY

R

C.324 H CF 3 H CH 3 C.325 H CF 3

CH

3

CH

3 C.326 H CF 3

C

2

H

5

CH

3 C.327 H CF 3

C

3

H

7

CH

3 C.328 H CF 3

C

4 H9 CH 3 C.329 H CF 3 CH (CH 3 2

CH

3 C.330 H CF 3 cyclopropyl CH 3 C.331 H CF 3

CF

3

CH

3 C.332 H CF 3

OCH

3

CH

3 C.333 H CF 3 0C 2

H

5

CH

3 C.334 H CF 3

CH

2

-C

6

H

5

CH

3 C.335 H CF 3

CH(CH

3

)C

6

H

5

CH

3 C.336 H CF 3

C

6

H

5

CH

3 C.337 H CF 3 4-F-C 6

H

5

CH

3 C.338 H CF 3 4-Cl-2-pyridyl CH 3 C.339 H CF 3 F CH 3 C.340 H CF 3 CN CH 3 C.341 ICF 3

CH

3 H H C.342 CF 3

CH

3

CH

3

H

C.343 CF 3

CH

3

C

2

H

5

H

C.344 CF 3

CH

3

C

3

H

7

H

C.345 CF 3

CH

3

C

4 H9 H C.346 CF 3

CH

3 CH (CHA) 2

H

C.347 CF 3

CH

3 cyclopropyl H C.348 CF 3

CH

3

CF

3

H

C.349 CF 3

CH

3

OCH

3

H

C.350 CF 3

CH

3 0C 2

H

5

H

C.351 CF 3

CH

3

CH

2

-C

6

H

5

H

C.352 CF 3

CH

3 CH (CH 3

C

6

H

5

H

C.353 CF 3

CH

3

C

6

H

5

H

C.354 CF 3

CH

3 4-F-C 6

H

5

H

C.355 CF 3

CH

3 4-Cl-2-pyridyl H C.356 CF 3

CH

3 F H C.357 CF 3

CH

3 CN H C.358 CF 3

CH

3 H CH 3 C.359 CF 3

CH

3

CH

3

CH

3 C.360 CF 3

CH

3

C

2

H

5

CH

3 C.361 CF 3

CH

3

C

3

H

7

CH

3 C.362 CF 3

CH

3

C

4 H9 CH 3 0050/46490 No. R 3 Rx RY Rz C.363 CF 3

CH

3 CH(CH 3 2 CH 3 C.364 CF 3

CH

3 cycJlopropyl

CH

3 C.365 CF 3

CH

3 CF 3 CH 3 C.366 CF 3

CH

3 OCH 3 CH 3 C.367 CF 3

CH

3 0C 2

H

5 CH 3 C.368 CF 3

CH

3 CH 2

-C

6

H

5 CH 3 C.369 CF 3

CH

3 CH(CH 3

)C

6

H

5 CH 3 C.370 CF 3

CH

3 C 6

H

5 CH 3 C.371 CF 3

CH

3 4-F-C 6

H

5 CH 3 C.372 CF 3

CH

3 4-C1-2-pyridyl

CH

3 C.373 CF 3

CH

3 F

CH

3 C.374 CF 3

CH

3 CN

CH

3 C.375 CF 3

CF

3 H

H

C.376 CF 3

CF

3 CH 3 H C.377 CF 3

CF

3 C 2

H

5 H C.378 CF 3

CF

3 C 3

H

7 H C.379 CF 3

CF

3 C 4 H9

H

C.380 CF 3

CF

3 CH (CH 3 2 H C.381 CF 3

CF

3 cyclopropyl

H

C.382 CF 3

CF

3 CF 3 H C.383 CF 3

CF

3 OCH 3 H C.384 CF 3

CF

3 0C 2

H

5 H C.385 CF 3

CF

3 CH 2

-C

6

H

5 H C.386 CF 3

CF

3 CH(CH 3

)C

6

H

5

H

C.387 CF 3

CF

3 C 6

H

5 H C.388 CF 3

CF

3 4-F-C 6

H

5 H C.389 CF 3

CF

3 4 -Cl-2-pyridyl

H

C.390 CF 3

CF

3 F

H

C.391 CF 3

CF

3 CN

H

C.392 CF 3

CF

3 H

CH

3 C.393 CF 3

CF

3 CH 3 CH 3 C.39.4 CF 3

CF

3 C 2

H

5 CH 3 C.395 CF 3

CF

3 C 3

H

7 CH 3 C.396 CF 3

CF

3 C 4 H9

CH

3 C.397 CF 3

CF

3 CH (CH 3 2

CH

3 C.398 CF 3

CF

3 cyclopropyl

CH

3 C.399 CF 3

CF

3 CF 3 CH 3 C.400 CF 3

CF

3 OCH 3 CH 3 C.401 CF 3

CF

3 0C 2

H

5 CH 3 0050/46490 102 No. R x Ry RZ C.402 CF 3

CF

3

CH

2

-C

6

H

5

OH

3 C.403 OF 3

CF

3

CH(CH

3

)C

6

H

5

CH

3 C.404 OF 3

CF

3

C

6

H

5

CH

3 C.405 OF 3

CF

3 4-F-C 6

H

5

OH

3 C.406 OF 3

OF

3 4-C1-2-pyridyl CH 3 C.407 OF 3

OF

3 F OH 3 C.408 O'F 3

OF

3 ON OH 3 C.409 Cl OH 3 H H C.410 Cl OH 3

OH

3

H

C.411 01 OH 3

C

2

H

5

H

C.412 01 OH 3

C

3

H

7

H

C.413 Cl OH 3

C

4 Hq H C.414 01 OH 3 CH (CH 3 2

H

C.415 Cl OH 3 cyclopropyl H C.416 02. OH 3

CF

3

H

C.417 01 OH 3 00H 3

H

0.418 01 OH 3 00 2

H

5

H

C.419 01 OH 3

CH

2

-C

6

H

5

H

0.420 Cl OH 3

CH(CH

3

)C

6

H

5

H

C.421 01 OH 3 0 6

H

5

H

C.422 01 OH 3 4-F-C 6

H

5

H

C.423 01 OH 3 4-01-2-pyridyl H 0.424 01 OH 3 F H C.425 01 OH 3 ON H C.426 01 OH 3 H OH 3 C.427 01 OH 3

OH

3

OH

3 C.428 01 OH 3

C

2

H

5 g OH 3 C.429 01 OH 3

C

3 H, OH 3 C.430 01 OH 3

C

4

H

9

OH

3 C.431 01 OH 3 CH (CH 3 2

OH

3 C.432 01 OH 3 cyclopropyl OH 3 C. 433 01 OH 3

OF

3

OH

3 C.434 01 OH 3 00H 3

OH

3 C.435 01 OH 3 00 2

H

5

OH

3 C.436 01 OH 3

CH

2

-C

6

H

5

OH

3 C.437 01 OH 3 OH(0H 3

)C

6

H

5

OH

3 C.438 01 OH 3 0 6

H

5

OH

3 C.439 01 OH 3 4-F-0 6

H

5

OH

3 I0.440 01 OlI H 3 4-01-2-pyridyl OH 3 0050/ 46490 103 No. R3RX RY RZ C.441 Cl CH 3 F

CH

3 C.442 Cl CH 3 CN

CH

3 C.443 Cl CF 3 H

H

C. 444 Cl CF 3 CH 3

H

C.445 Cl CF 3 C 2

H

5

H

C.446 Cl CF 3 C 3 H C.447 Cl CF 3 C 4

H

9 H C.448 Cl CF 3 CH (CHA) 2

H

C.449 Cl CF 3 cyclopropyl

H

C.450 Cl CF 3 CF 3

H

C.451 Cl CF 3 OCH 3

H

C.452 Cl CF 3 0C 2

H

5

H

C.453 Cl CF 3

CH

2

-C

6

H

5

H

C.454 Cl CF 3

CH(CH

3

)C

6

H

5

H

C.455 Cl CF 3

C

6

H

5

H

C.456 Cl CF 3 4-F-C 6

H

5

H

C.457 Cl CF 3 4-Cl-2-pyridyl

H

C.458 Cl CF 3 F H C.459 Cl CF 3 CN H C.460 Cl CF 3 H

CH

3 C.461 Cl CF 3 CH 3 CH 3 C.462 Cl CF 3 C 2

H

5 CH 3 C.463 Cl CF 3 C 3

H

7 CH 3 C.464 Cl CF 3 C 4

H

9 CH 3 C.465 Cl CF 3 CH(CH 3 2

CH

3 C.466 Cl CF 3 cyclopropyl

CH

3 C.467 Cl CF 3 CF 3 CH 3 C.468 Cl CF 3 OCH 3 CH 3 C.469 Cl CF 3 0C 2

H

5

CH

3 C.470 Cl CF 3 CH 2

-C

6

H

5

CH

3 C.471 Cl CF 3 CH(CH 3

)C

6

H

5

CH

3 C.472 Cl CF 3 .C 6

H

5

CH

3 C.473 Cl CF 3 4-F-C 6

H

5

CH

3 C.474 Cl CF 3 4-Cl1-2-pyridyl

CH

3 C.475 Cl CF 3 F

CH

3 C.476 Cl CF 3 CIN CH 3 C.477 H CH 3 H F C.478 H CH 3

CH

3

F

C.479 H CH 3

C

2

H

5

F

0050/46490 104 No. R 3 Rx Ry

RZ

C.480 H CH 3 C 3

H

7 F C.481 H CH 3 CH (CH 3 2

F

C.482 H CH 3 cyclopropyl

F

C.483 H CH 3 CF 3 F C.484 H CH 3 OCH 3 F c.485 H CH 3 C 6

H

5

F

c.486 H CH 3 4-F-C 6

H

5

F

c.487 H CH 3 H C 2

H

c.488 H CH 3 CH 3 C 2

H

C.489 H CH 3 C 2

H

5 C 2

H

c.490 H CH 3 C 3

H

7 C 2

H

C.491 H CH 3 CH (CH 3 2

C

2

H

C.492 H CH 3 cyclopropyl

C

2

H

c.493 H CH 3 CF 3 C 2

H

C.494 H CH 3 OCH 3 C 2

H

C.495 H CH 3 C 6

H

5

C

2

H

c.496 H CH 3 4-F-C 6

H

5

C

2

H

c.497 H CH 3 H

CF

3 c.498 H CH 3 CH 3 CF 3 C.499 H CH 3 C 2

H

5 CF 3 C.500 H CH 3 C 3

H

7 CF 3 C.501 H CH 3 CH (CH 3 2

CF

3 C.502 H CH 3 cyclopropyl

CF

3 C.503 H CH 3 CF 3 CF 3 C.504 H CH 3 OCH 3

CF

3 C.505 H CH 3 C 6

H

5 CF 3 C.506 H CH 3 4-F-C 6

H

5

CF

3 C.507 H CH 3 H CN C.508 H CH 3 CH 3

CN

C.509 H CH 3

C

2

H

5

CN

C.510 H CH 3 C 3

H

7

CN

C.511 H CH 3 CH (CH 3 2

CN

C.512 H CH 3 cyclopropyl

CN

C.513 H CH 3

CF

3

CN

C.514 H CH 3

OCH

3

CN

C.515 H CH 3

C

6

H

5

CU

C.516 H CH 3 4-F-C 6

H

5

CN

C.517 H CH 3 H Cl C.518 H CH 3

CH

3 Cl 0050/46490 105 No. R 3 RX Ry Rz C.519 H OH 3 0 2

H

5 Cl C.520 H OH 3 0 3

H

7 Cl C.521 H CH 3 CH (CH 3 2 cl C.522 H OH 3 cyclopropyl Cl C.523 H CH 3

CF

3 Cl C.524 H OH 3 00H 3 Cl C.525 H CH 3

C

6

H

5 Cl C.526 H CH 3 4-F-C 6

H

5 Cl C.527 H CF 3 H F C.528 H CF 3

OH

3

F

C.529 H CF 3 02115 F C.530 H CF 3

C

3

H

7

F

C.531 H CF 3 CH (CH 3 2

F

C.532 H CF 3 cyclopropyl

F

C.533 H CF 3

CF

3

F

C.534 H CF 3

OCH

3

F

C.535 H CF 3 0 6

H

5

F

C.536 H CF 3 4-F- 6

H

5

F

0.537 H CF 3 H

C

2

H

0.538 H CF 3 OH 3

C

2

H

0.539 H CF 3

C

2

H

5 02115 C.540 H CF 3

C

3

H

7 02115 C.541 H CF 3 CH(CH 3 2

C

2

H

0.542 H CF 3 cyclopropyl C 2

H

C.543 H CF 3 CF 3

C

2

H

C.544 H CF 3 00113

C

2

H

0.545 H CF 3 06115 C 2

H

0.546 H CF 3 4-F-C 6 1 5

C

2

H

0.547 H CF 3 H

CF

3 0.548 H CF 3 OH 3

CF

3 0.549 H CF 3 02115

CF

3 H CF 3 03117 CF 3 0.551 H CF 3 CH1(0113) 2 CF 3 0.552 H CF 3 cyclopropyl

OF

3 C.553 H CF 3 CF 3

CF

3 C.554 H CF 3 00113

OF

3 C.555 H CF 3 0 6

H

5

CF

3 C.556 H CF 3 4-F-C 6

H

5

CF

3 0.557 H CF 3 H ON 0050/46490 106 No. R x RY Rz C.558 H CF 3

CH

3

CN

C.559 H CF 3

C

2

H

5

CN

C.560 H CF 3

C

3

H

7

CN

C.561 H CF 3 CH (CH 3 2

CN

C.562 H CF 3 cyclopropyl CN C.563 H CF 3

CF

3

CN

C.564 H CF 3

OCH

3

CN

C.565 H CF 3

C

6

H

5

CN

C.566 H CF 3 4-F-C 6

H

5

CN

C.567 H CF 3 H Cl C.568 H CF 3

CH

3 Cl C.569 H CF 3

C

2

H

5 Cl C.570 H CF 3

C

3

H

7 Cl C.571 H CF 3 CH (CH 3 2 Cl C.572 H CF 3 cyclopropyl Cl C.573 H CF 3

CF

3 Cl C.574 H CF 3

OCH

3 Cl C.575 H CF 3

C

6

H

5 Cl C.576 H CF 3 4-F-C 6

H

5 Cl C.577 CF 3

CH

3 H F C.578 CF 3

CH

3

CH

3

F

C.579 CF 3

CH

3

C

2

H

5

F

C.580 CF 3

CH

3

C

3

H

7

F

C.581 CF 3

CH

3 CH (CH 3 2

F

C.582 CF 3

CH

3 cyclopropyl F C.583 CF 3

CH

3

CF

3

F

C.584 CF 3

CH

3

OCH

3

F

C.585 CF 3

CH

3

C

6

H

5

F

C.586 CF 3

CH

3 4-F-C 6

H

5

F

C.587 CF 3

CH

3 H C 2

H

C.588 CF 3

CH

3 CH 3

C

2

H

C.589 CF 3

CH

3

C

2

H

5

C

2

H

C.590- CF 3

CH

3

C

3

H

7

C

2

H

C.591 CF 3

CH

3 CH (CH 3 2

C

2

H

C.592 CF 3

CH

3 cyclopropyl C 2

H

C.593 CF 3

CH

3

CF

3

C

2

H

C.594 CF 3

CH

3

OCH

3

C

2

H

C.595 CF 3

CH

3

C

6

H

5

C

2

H

C.596 CF 3 I CH 3 4-F-C 6

H

5

C

2

H

0050/46490 107 No. R 3 Rx Ry RZ C.597 CF 3

CH

3 H CF 3 C.598 CF 3

CH

3 CH 3

CF

3 C.599 CF 3

OH

3

C

2

H

5

CF

3 C.600 CF 3

CH

3 C 3

H

7

CF

3 C.601 CF 3

CH

3 CH (CHA) 2

CF

3 C.602 CF 3 CH3 cyclopropyl CF 3 C.603 CF 3

CH

3

CF

3

CF

3 C.604 CF 3

CH

3 00H 3

CF

3 C.605 CF 3

CH

3 0 6

H

5

CF

3 C.606 CF 3

CH

3 4-F-C 6

H

5

CF

3 C.607 CF 3

CH

3 H CN C.608 CF 3

CH

3

OH

3

CN

C.609 CF 3

CH

3 0 2 HS CN C.610 CF 3

OH

3

C

3

H

7

CN

C.611 CF 3

CH

3 CH (0H 3 2

CN

C.612 CF 3

OH

3 cyclopropyl ON 0.613 OF 3

OH

3

OF

3

ON

C.614 OF 3

OH

3 00H 3

ON

C.615 OF 3

OH

3 0 6

H

5

ON

0.616 OF 3

OH

3 4-F-C 6

H

5

ON

C.617 OF 3

OH

3 H 01 0.618 OF 3

OH

3

OH

3 Cl C.619 OF 3

OH

3

C

2

H

5 Cl1 0.620 OF 3

OH

3

C

3 H, Cl1 0.621 OF 3

OH

3 CH (CH 3 2 0 1 0.622 OF 3

OH

3 cyclopropyl Cl 0.623 CF 3

OH

3

OF

3 01 C.624 CF 3

OH

3 00H 3 01 C.625 OF 3

OH

3 0 6

H

5 C 1 0.626 CF 3

OH

3 4-F-C 6

H

5 0 1 0.627 CF 3

OF

3 H F 0.628 OF 3

CF

3 0H3 F 0.629 OF 3

OF

3

C

2

H

5

F

C.630 OF 3

OF

3

C

3

H

7

F

C.631 OF 3

OF

3 CH (CHA) 2

F

C.632 OF 3

CF

3 cyclopropyl F C.633 CF 3

OF

3

OF

3

F

0.634 OF 3

CF

3 00H 3

F

C.635 OF 3

CF

3 0 6

H

5

F

0050/46490 108 No. R 3 R y Rz 0.636 CF 3

CF

3 4-F-C 6

H

5

F

C.637 CF 3

OF

3 H

C

2

H

c.638 OF 3

CF

3 CH 3 C 2

H

c.639 CF 3

CF

3 C 2

H

5 C 2

H

c.640 CF 3

CF

3 C 3

H

7 C 2

H

c.641 CF 3

OF

3 CH (CH 3 2 C 2

H

0.642 OF 3

CF

3 cyclopropyl

C

2

H

C.643 CF 3

OF

3 OF 3 C 2

H

C.644 CF 3

CF

3 OCH 3 C 2

H

C.645 CF 3

CF

3 C 6

H

5 C 2

H

C.646 CF 3

OF

3 4-F- 6

H

5 C 2

H

C.647 CF 3

CF

3 H

CF

3 C.648 OF 3

OF

3 OH 3 CF 3 C.649 CF 3

CF

3 C 2

H

5 OF 3 C.650 OF 3

CF

3 C 3

H

7 CF 3 C.651 CF 3

CF

3 CH (CH 3 2

CF

3 C.652 OF 3

OF

3 cyclopropyl

CF

3 C.653 CF 3

CF

3 CF 3 CF 3 C.654 OF 3

OF

3 00H 3 CF 3 C.655 CF 3

CF

3 C 6

H

5 OF 3 C.656 OF 3

OF

3 4-F-C 6

H

5

CF

3 C.657 CF 3

CF

3 H CN C.658 CF 3

OF

3 CH 3

CN

C.659 OF 3

OF

3 C 2

H

5

ON

C.660 CF 3

CF

3 C 3

H

7

ON

0.661 OF 3

CF

3

CH(CH

3 2

CN

C.662 CF 3

OF

3 cyclopropyl

CN

0.663 OF 3

CF

3 CF 3

ON

C.664 CF 3

OF

3 00H 3

ON

0.665 CF 3

CF

3 0 6

H

5

ON

0.666 CF 3

CF

3 4-F- 6

H

5

ON

0.667 OF 3

CF

3 H Cl C.668 CF 3

CF

3 OH 3 Cl 0.669 CF 3

CF

3 C 2

H

5 Cl 0.670 CF 3

OF

3

C

3 Cl 0.671 CF 3

CF

3

CH(CH

3 2 Cl C.672 OF 3

CF

3 cyclopropyl Cl C.673 CFP 3

OF

3

OF

3 01 C.674 OF 3 O F 3 I00H 3 01 0050/46490 109 No. R xRY Rz C.675 CF 3

CF

3

C

6

H

5 Cl C.676 CF 3

CF

3 4-F-C 6

H

5 Cl C.677 Cl CH 3 H F C. 678 Cl CH 3

CH

3

F

C. 679 Cl CH 3

C

2

H

5

F

C.680 Cl CH 3

C

3

H

7

F

C.681 Cl CH 3 CH (CH 3 2

F

C. 682 Cl CH 3 cyclopropyl

F

C.683 Cl CH 3

CF

3

F

C.684 Cl CH 3

OCH

3

F

C.685 Cl CH 3

C

6

H

5

F

C.686 Cl CH 3 4-F-C 6

H

5

F

C.687 Cl CH 3 H C 2

H

C.688 Cl CH 3

CH

3

C

2

H

C.689 Cl CH 3

C

2

H

5

C

2

H

C.690 Cl CH 3

C

3

H

7

C

2

H

C.691 Cl CH 3 CH (CHA) 2

C

2

H

C.692 Cl CH 3 cyclopropyl C 2

H

C.693 Cl CH 3

CF

3

C

2

H

C.694 Cl CH 3

OCH

3

C

2

H

C.695 Cl CH 3

C

6

H

5

C

2

H

C.696 Cl Cl 3 4-F-C 6

H

5

C

2

H

C.697 Cl CH 3 H CF 3 C.698 Cl CH 3

CH

3

CF

3 C.699 Cl CH 3

C

2

H

5

CF

3 C.700 Cl CH 3

C

3

H

7

CF

3 C.701 Cl CH 3 CH (CH 3 2

CF

3 C.702 Cl CH 3 cyclopropyl CF 3 C.703 Cl CH 3

CF

3

CF

3 C.704 Cl CH 3

OCH

3

CF

3 C.705 Cl CH 3

C

6

H

5

CF

3 C.706 Cl CH 3 .4-F-C 6

H

5

CF

3 C.707 Cl CH 3 H

CN

C.708 Cl CH 3

CH

3

CN

C.709 Cl CH 3

C

2

H

5

CN

C.710 Cl CH 3

C

3

H

7

CN

C.711 I Cl CH 3

CH(CH

3 2

CN

C.7l2 Cl CH 3 cyclopropyl

CN

C.7l3 Cl CH 3

CF

3

CN

0050/46490 110 No. R 3 RX RY RZ C. 714 Cl CH 3

OCH

3

CN

C. 715 Cl CH 3 C6ll 5

CN

C.716 Cl CH 3 4-F-C 6

H

5

C

C. 717 Cl CH 3 H Cl C. 718 Cl CH 3

CH

3 Cl C.719 Cl CH 3

C

2

H

5 Cl C.720 Cl CH 3

C

3

H

7 Cl C.721 Cl CH 3 CH (CH 3 2 Cl C.722 Cl CH 3 cyclopropyl Cl C.723 Cl CH 3

CF

3 Cl C.724 Cl CH 3

OCH

3 Cl C.725 Cl CH 3

C

6

H

5 Cl C.726 Cl CH 3 4-F-C 6

H

5 Cl C.727 Cl CF 3 H F C.728 Cl CF 3

CH

3

F

C.729 Cl CF 3

C

2

H

5

F

C.730 Cl CF 3

C

3

H

7

F

C.731 Cl CF 3 CH (CHA) 2

F

C.732 Cl CF 3 cyclopropyl F C.733 Cl CF 3

CF

3

F

C.734 Cl CF 3

OCH

3

F

C.735 Cl CF 3

C

6

H

5

F

C.736 Cl CF 3 4-F-C 6

H

5

F

C.737 Cl CF 3 H C 2

H

C.738 Cl CF 3

CH

3

C

2

H

C.739 Cl CF 3

C

2

H

5

C

2

H

C.740 Cl CF 3

C

3

H

7

C

2

H

C.741 Cl CF 3

CH(CH

3 2

C

2

H

C.742 Cl CF 3 cyclopropyl C 2

H

C.743 Cl CF 3

CF

3

C

2

H

C.744 Cl CF 3

OCH

3

C

2

H

C.745 Cl CF 3

C

6

H

5

C

2

H

C.746 Cl CF 3 4-F-C 6 HS C 2

H

C.747 Cl CF 3 H CF 3 C.748 Cl CF 3

CH

3

CF

3 C.749 Cl CF 3

C

2

H

5

CF

3 C.750 Cl CF 3

C

3 H7 CF 3 C.751 Cl CF 3 CH (CH 3 2

CF

3 C.752 Cl CF 3 cyclopropyl CF 3 0050/46490 No. R 3 Rx RY Rz C.753 Cl

CF

3 CF 3 CF 3 C.754 Cl CF 3 OCH 3

CF

3 C.755 C1 CF 3 C 6

H

5 CF 3 C.756 01 CF 3 4-F-C 6

H

5

CF

3 C.757 Cl OF 3 H

CN

C.758 Cl CF 3 CH 3

CU

C.759 Cl CF 3 02115

CN

C.760 Cl CF 3 C 3

H

7

CN

C.761 Cl CF 3 CH (0113)2

CN

C.762 01 CF 3 cyclopropyl

CN

C.763 Cl CF 3 CF 3 CN C.764 01 OF 3 00113 CN 0.765 Cl CF 3 0 6

H

5

CN

C.766 01 CF 3 4-F-0 6

H

5

CN

C.767 01 CF 3 H Cl C.768 Cl CF 3

OH

3 01 C.769 Cl OF 3 02115 Cl C.770 Cl CF 3 C 3

H

7 Cl C.771 Cl CF 3 CH (CH 3 2 Cl 0.772 Cl CF 3 cyclopropyl

C).

C.773 01 CF 3 CF 3 01 C.774 Cl CF 3 OCH 3 01 0.775 Cl CF 3 06115 Cl C.776 Cl OF 3 4-F-C 6

H

5 Cl C.777 0113 H H

F

C.778 OH 3 H

OH

3 F C.779 OH 3 H 0 2

H

5

F

C.780 OH 3 H 03117

F

C.781 OH 3 H CH (0H 3 2

F

0.782 OH 3 H cyclopropyl

F

C.783 OH 3 H

OF

3

F

0.784 OH 3 H 00113

F

0.785 OH 3 H 06115

F

0.786 OH 3 H 4-F-C 6

H

5

F

0.787 OH 3

OH

3 H F C.788 OH 3

OH

3

OH

3

F

C.789 OH 3

OH

3 C 2

H

5

F

0.790 OH 3

OH

3 0 3

H

7

F

0.791 OH 3

OH

3 CH1(0113) 2 F 4> bt 0 0050/46490 112 No. R 3 Rx RY

RZ

C.792 OH 3

OH

3 cyclopropyl

F

C.793 CH 3

OH

3 OF 3 F C.794 OH 3

OH

3 OCH 3 F C.795 CH 3

OH

3 C 6

H

5 F C.796 OH 3

OH

3 4-F- 6

H

5 F C.797 OH 3

C

2

H

5 H

F

C.798 OH 3

C

2

H

5 OH 3 F C.799 OH 3

C

2

H

5 C 2

H

5 F C.800 OH 3

C

2

H

5 C 3 F C.801 OH 3

C

2

H

5 CH (CH 3 2 F C.802 OH 3

C

2

H

5 cyclopropyl

F

C.803 OH 3

C

2

H

5 OF 3 F 0.804 OH 3

O

2

H

5 00H 3 F C.805 OH 3 0 2

H

5 C 6

H

5 F 0.806 OH 3 0 2

H

5 4-F- 6

H

5 F 0.807 OH 3 cyclopropyl H

F

0.808 OH 3 cyclopropyl

OH

3 F 0.809 OH 3 cyclopropyl

C

2

H

5 F 0.810 OH 3 cyclopropyl

C

3

H

7 F 0.811 OH 3 cyclopropyl CH (CH 3 2 F 0.812 OH 3 cyclopropyl cyclopropyl

F

0.813 OH 3 cyclopropyl

OF

3 F 0.814 OH 3 cyclopropyl 00H 3 F 0.815 OH 3 cyclopropyl 0 6

H

5 F 0.816 OH 3 cyclopropyl 4-F- 6

H

5 F 0.817 OH 3

OF

3 H

F

0.818 OH 3

OF

3 OH 3 F 0.819 OH 3

OF

3 C 2

H

5 F 0.820 OH 3

OF

3 C 3

H

7 F 0.821 OH 3

OF

3 CH (CH 3 2 F 0.822 OH 3

OF

3 cyclopropyl

F

0.82 3 O'H 3

OF

3 OF 3 F 0.824 OH 3

CF

3 00H 3 F 0.825 OH 3

OF

3 0 6

H

5 F 0.826 OH 3

OF

3 4-F- 6

H

5 F 0.827 OH 3 01 H

F

0.828 OH 3 01

OH

3 F 0.829 OH 3 01

C

2

H

5 F 0.830 OH 3 01

C

3

H

7 F 0050/46490 113 No. R x RY Rz C.831 CH 3 Cl CH (CH 3 2

F

C.832 CH 3 Cl cyclopropyl

F

C.833 CH 3 Cl

CF

3 F C.834 CH 3 Cl

OCH

3 F C.835 CH 3 Cl

C

6

H

5 F C.836 CH 3 Cl 4-F-C 6

H

5

F

C.837 CH 3 F H

F

C.838 CH 3 F

CH

3 F C.839 CH 3 F

C

2

H

5 F C.840 CH 3 F

C

3

H

7 F C.841 CH 3 F CH (CH 3 2 F C.842 CH 3 F cyclopropyl

F

C.843 CH 3 F

CF

3 F C.844 CH 3 F

OCH

3 F C.845 CH 3 F

C

6

H

5 F C.846 CH 3 F 4-F-C 6

H

5 F C.847 CH 3

OCH

3 H

F

C.848 CH 3

OCH

3 CH 3 F C.849 CH 3

OCH

3 C 2

H

5 F C.850 CH 3

OCH

3 C 3

H

7 F C.851 CH 3

OCH

3 CH (CHA) 2

F

C.852 CH 3

OCH

3 cyclopropyl

F

C.853 CH 3

OCH

3 CF 3 F C.854 CH 3

OCH

3 OCH 3 F C.855 CH 3

OCH

3 C 6

H

5 F C.856 CH 3

OCH

3 4-F-C 6

H

5 q F C.857 CH 3 H H

C

2

H

C.858 CH 3 H

CH

3 C 2

H

C.859 CH 3 H

C

2

H

5 C 2

H

C.860 CH 3 H

C

3

H

7 C 2

H

C.861 CH 3 H CH (CH 3 2

C

2

H

C.862 CH 3 H cyclopropyl

C

2

H

C.863 CH 3 H

CF

3 C 2

H

C.864 CH 3 H

OCH

3 C 2

H

C.865 CH 3 H

C

6

H

5 C 2

H

c.866 CH 3 H 4-F-C 6

H

5 g C 2

H

C.867 CH 3

CH

3 H

C

2

H

C.868 CH 3

CH

3 CH 3 C 2

H

C.869 CH 3

CH

3 C 2

H

5 C 2

H

0050/46490 114 NO. R 3 RXRY Rz C.870 CH 3

CH

3 C37C 2

H

0.871 OH 3

CH

3 CH (CH 3 2

C

2

HS

C.872 OH 3

OH

3 cyclopropyl

C

2

H

C.873 OH 3

CH

3 CF 3 C 2

H

C.874 OH 3

CH

3 00H 3

C

2

H

C.875 CH 3

CH

3

C

6

H

5

C

2

H

0876 OH 3

CH

3 4-F- 6

H

5

C

2

H

C.877 CH 3

C

2

H

5 H 0 2

H

C.878 OH 3

C

2

H

5 OH 3

C

2

H

C.879 OH 3

C

2

H

5 C 2

H

5

C

2

H

0.880 OH 3

C

2

H

5 C 3

H

7 C 2

H

C.881 OH 3

C

2

H

5 CH (CH 3 2

C

2

H

C.882 CH 3

C

2

H

5 cyclopropyl

C

2

H

C.883 CH 3

C

2

H

5 CF 3 0 2

H

C.884 CH 3

C

2

H

5

QCH

3 0 2

H

C.885 CH 3

C

2

H

5 C 6

H

5

C

2

H

C.886 OH 3

C

2

H

5 4-F- 6

H

5

C

2

H

C.887 OH 3 cyclopropyl H C 2

H

C.888 OH 3 cyclopropyl CH 3

C

2

H

C. 889, OH 3 cyclopropyl

C

2

H

5

C

2

H

C.890 OH 3 cyclopropyl

C

3

H

7

C

2

H

C.891 CH 3 cyclopropyl

OH(CH

3 2 0 2

H

C.892 CH 3 cyclopropyl cyclopropyl

O

2

H

C.893 OH 3 cyclopropyl

OF

3 C 2

H

C.894 CH 3 cyclopropyl 00H 3

C

2

H

C.895 OH 3 cyclopropyl 0 6

H

5

C

2

H

C.896 CH 3 cyclopropyl 4-F-C 6

H

5

C

2

H

C.897 OH 3

CF

3 H C 2

H

C.898 OH 3

OF

3 OH 3

C

2

H

C.899 OH 3

OF

3 O 2

H

5

C

2

H

0.900 OH 3

OF

3 0 3

H

7

O

2

H

0.901 OH 3

OF

3 CH(0H 3 2 0 2

H

0.902 OH 3

OF

3 cyclopropyl 0 2

H

0.903 OH 3

OF

3 OF 3

C

2

H

0.904 O'H 3

OF

3 OOH 3 0 2

H

0.905 OH 3

OF

3 C 6

H

5 0 2

H

.906 OH 3 OF 3 4-F- 6

H

5 C 2

H

0.907 OH 3 01 H

C

2

H

0050/46490 115 No. R 3 Rx Ry Rz C.908 CH 3 OH 3 0 2

H

C.909 OH 3 01

C

2

H

5

C

2

H

C.910 CH 3 Cl C3H7

C

2

H

C.911 OH 3 Cl CH (CH 3 2

C

2

H

C.912 OH 3 Cl cyclopropyl

C

2

H

C.913 CH 3 Cl

CF

3

C

2

H

C.914 CH 3 Cl

OCH

3

C

2

H

C.915 CH 3 Cl

C

6

H

5

C

2

H

C.916 CH 3 Cl 4-F-C 6

H

5

C

2

H

C.917 CH 3 F H

C

2

H

C.918 CH 3 F CH 3

C

2

H

C.919 CH 3 F

C

2

H

5

C

2

H

C.920 CH 3 F

C

3

H

7

C

2

H

C.921 CH 3 F CH (CH 3 2

C

2

H

C.922 CH 3 F cyclopropyl

C

2

H

C.923 CH 3 F

CF

3

C

2

H

C.924 CH 3 F OCH 3

C

2

H

C.925 OH 3 F

C

6

H

5

C

2

H

C.926 OH 3 F 4-F-C 6

H

5

C

2

H

C.927 CH 3 00H 3 H 0 2

H

C.928 CH3 00H 3

CH

3

C

2

H

C.929 CH 3 00H 3 0 2

H

5

C

2

H

C.930 CH 3 00H 3 C 3

H

7

C

2

H

C.931 CH 3

OCH

3 CH (0H 3 2

C

2

H

C.932 OH 3

OCH

3 cyclopropyl

C

2

H

C.933 OH 3

OCH

3 CF 3

C

2

H

C.934 OH 3 00H 3 OCH 3

C

2

H

C.935 CH 3

OCH

3 C 6

H

5

C

2

H

C.936 OH 3

OCH

3 4-F-C 6

H

5

C

2

H

C.937 OH 3 H H CF 3 C.938 OH 3 H

OH

3

CF

3 0.939 OH 3 H

C

2

H

5

CF

3 0.940 OH 3 H

C

3

H

7

CF

3 0.941 OH 3 H CH (CH 3 2

OF

3 0.942 OH 3 H cyclopropyl

OF

3 0.943 OH 3 H

OF

3

CF

3 C.944 OH 3 H 00H 3

CF

3 0.945 OH 3 H

C

6

H

5

CF

3 0.4 CH 3 H 4-F-0 6

H

5

OF

3 0050/46490 116 No. R 3 Rx RY Rz 0.947 CH 3

CH

3 H CF 3 C.948 OH 3

CH

3 OH 3

OF

3 C.949 CH 3

CH

3

C

2

H

5

CF

3 C.950 CH 3

CH

3 C 3

H

7

CF

3 C.951 CH 3

CH

3 CH (CH 3 2

CF

3 C.952 OH 3

OH

3 cyclopropyl CF 3 C.953 CH 3

OH

3

OF

3

CF

3 C.954 CH 3

OH

3 00H 3

OF

3 C.955 OH 3

OH

3

C

6

H

5

OF

3 C.956 CH 3

OH

3 4-F-C 6

H

5

CF

3 C.957 OH 3

O

2

H

5 H CF 3 C.958 CH 3

C

2

H

5

CH

3

CF

3 C.959 OH 3

C

2

H

5

C

2

H

5

CF

3 C.960 OH 3

C

2

H

5

C

3

H

7

CF

3 0.961 OH 3

O

2

H

5 CH (CH 3 2

OF

3 0.962 OH 3

C

2

H

5 cyclopropyl OF 3 0.963 OH 3

C

2

H

5

OF

3

OF

3 0.964 OH 3 0 2

H

5 00H 3

OF

3 0.965 OH 3

C

2

H

5 0 6

H

5

OF

3 C.966 OH 3

C

2

H

5 4-F- 6

H

5

OF

3 0.967 OH 3 cyclopropyl H OF 3 0.968 OH 3 cyclopropyl

OH

3

OF

3 0.969 OH 3 cyclopropyl 0 2

H

5

CF

3 0.970 OH 3 cyclopropyl

C

3 H, OF 3 0.971 OH 3 cyclopropyl CH (CH 3 2

OF

3 0.972 OH 3 cyclopropyl cyclopropyl

OF

3 0.973 OH 3 cyclopropyl

OF

3

OF

3 0.974 OH 3 cyclopropyl 00H 3

OF

3 0.975 OH 3 cyclopropyl 0 6

H

5

OF

3 0.976 OH 3 cyclopropyl 4-F-C 6

H

5

OF

3 0.977 OH 3

OF

3 H OF 3 0.978 OH 3

OF

3

OH

3

OF

3 0.979 OH 3

OF

3

C

2

H

5

OF

3 C.980 OH 3

CF

3

C

3

H

7

OF

3 C.981 OH 3

CF

3 CH (0H 3 2

OF

3 0.982 OH 3

OF

3 cyclopropyl OF 3 0.983 OH 3

OF

3

OF

3

CF

3 0.984 OH 3

OF

3 00H 3

OF

3 0.985 OH 3

OF

3

C

6

H

5

OF

3 0050/46490 117 No. R xRY Rz C. 986 OH 3

CF

3 4-F-C 6

H

5

CF

3 C.987 OH 3 Cl H CF 3 C.988 CH 3 Cl

CH

3

CF

3 C.989 CH 3 Cl

C

2

H

5

CF

3 C.990 CH 3 Cl

C

3

H

7

CF

3 C.991 CH 3 Cl CH (CHA) 2

CF

3 C.992 CH 3 Cl cyclopropyl

CF

3 C.993 CH 3 01

CF

3

CF

3 C.994 CH 3 01

OCH

3

CF

3 C.995 CH 3 Cl

C

6

H

5

OF

3 C.996 OH 3 Cl 4-F-C 6

H

5

CF

3 C.997 CH 3 F H CF 3 C.998 OH 3 F

OH

3

CF

3 0.999 OH 3 F

C

2

H

5

CF

3 C.1000 OH 3 F

C

3

H

7

OF

3 C.1001 OH 3 F CH (CH 3 2

CF

3 C.1002 OH 3 F cyclopropyl OF 3 C.1003 OH 3 F OF 3

OF

3 C.1004 OH 3 F OCH 3

CF

3 C.1005 OH 3 F C 6 HS OF 3 0.1006 OH 3 F 4-F-0 6

H

5

OF

3 C.1007 OH 3 00H 3 H OF 3 C.1008 OH 3 00H 3

OH

3

OF

3 0.1009 OH 3 00H 3

C

2

H

5

CF

3 0.1010 OH 3 00H 3 0 3

H

7

CF

3 0.1011 OH 3 00H 3 CH (0H 3 2

OF

3 0.1012 OH 3 00H 3 cyclopropyl

OF

3 0.1013 OH 3 00H 3

OF

3

OF

3 0.1014 OH 3 00H 3 00H 3

CF

3 0.1015 OH 3 00H 3 0 6

H

5

OF

3 0.1016 OH 3 00H 3 4-F-C 6

H

5

OF

3 0.1017 OH 3 H H ON 0.1018 OH 3 H OH 3

ON

0.1019 OH 3 H C 2

H

5

ON

0.1020 OH 3 H 0 3

H

7

ON

0.1021 OH 3 H CH (0H 3 2

ON

0.1022 OH 3 H cyclopropyl ON 0.1023 OH 3 H OF 3

ON

0.-1024 OH 3 H 00H 3

ON

0050/46490 118 No. R x RY RZ C. 1025 OH 3 H C 6

H

5

ON

C. 1026 OH 3 H 4-F-C 6

H

5

ON

C. 1027 CH 3

CH

3 H ON C. 1028 OH 3

OH

3

OH

3

ON

C. 1029 OH 3

CH

3

C

2

H

5

ON

C.1030 OH 3

OH

3

C

3

H

7

ON

C.1031 OH 3

OH

3 CH (CHA) 2

ON

C.1032 OH 3

OH

3 cyclopropyl CN C.1033 OH 3

OH

3

CF

3

CN

C.1034 CH 3

CH

3 00H 3

CN

C.1035 OH 3

CH

3

C

6

H

5

CN

C.1036 CH 3

OH

3 4-F-C 6

H

5

CN

C.1037 CH 3

C

2

H

5 H CN C.1038 CH 3

C

2

H

5

CH

3

ON

C.1039 CH 3

C

2

H

5

C

2

H

5

ON

C.1040 CH 3

C

2

H

5

C

3

H

7

CN

C.1041 CH 3

C

2

H

5 CH (CH 3 2

ON

C.1042 OH 3

C

2

H

5 cyclopropyl ON C.1043 CH 3

C

2

H

5

CF

3

CN

C.1044 CH 3

C

2

H

5 00H 3

CN

C.1045 CH 3

C

2

H

5

C

6

H

5

CN

C.1046 OH 3 0 2

H

5 4-F- 6

H

5

CN

C.1047 CH 3 cyclopropyl H ON C.1048 OH 3 cyclopropyl CH 3

ON

C.1049 OH 3 cyclopropyl C 2

H

5

CN

0.1050 OH 3 cyclopropyl C 3

H

7

ON

0.1051 OH 3 cyclopropyl CH (0H 3 2

ON

C.1052 OH 3 cyclopropyl cyclopropyl ON 0.1053 OH 3 cyclopropyl OF 3

ON

0.1054 OH 3 cyclopropyl 00H 3

ON

0.1055 OH 3 cyclopropyl 0 6

H

5

ON

0.1056 OH 3 cyclopropyl 4-F-C 6

H

5

ON

0.1057 OH 3

OF

3 H ON C.1058 OH 3

OF

3

OH

3

ON

0.1059 OH 3

OF

3

CAS

5

ON

0.1060 CH 3

CF

3

C

3

H

7

ON

0.1061 OH 3

OF

3 CH (0H 3 2

ON

0.1062 OH 3

OF

3 cyclopropyl ON 0.06 H 3

CF

3

OF

3

ON

0050/46490 119 No. R 3 Rx Ry Rz C.1064 OH 3

CF

3 00H3 CN C.1065 CH 3

CF

3

C

6

H

5

CN

0.1066 OH 3

CF

3 4-F-C 6

H

5

CN

C.1067 OH 3 01 H CN C.1068 CH 3 Cl CH 3

ON

C.1069 CH 3 Cl C 2

H

5

CN

0.1070 CH 3 Cl C 3

H

7

CN

C.1071 CH 3 Cl CH (CH 3 2

CN

C.1072 CH 3 01 cyclopropyl CN C.1073 OH 3 01 CF 3

CN

C.1074 OH 3 Cl OCH 3

CN

C.1075 CH 3 01 C 6

H

5

CN

C.1076 OH 3 01 4-F-C 6

H

5

CN

C.1077 CH 3 F H CN C.1078 CH 3 F CH 3

CN

C.1079 CH 3 F C 2

H

5

ON

C.1080 CH 3 F C 3 H7 CN C.1081 CH 3 F CH(CH 3 2

CN

C.1082 CH 3 F cyclopropyl CN C.1083 OH 3 F CF 3

ON

C.1084 OH 3 F 00H 3

ON

0.1085 OH 3 F C 6

H

5

ON

0.1086 OH 3 F 4-F-C 6

H

5

ON

0.1087 OH 3 00H 3 H ON 0.1088 OH 3 00H 3

OH

3

ON

C.1089 OH 3 00H 3

C

2 HS ON C.1090 OH 3 00H 3

C

3 H, ON 0.1091 OH 3 00H 3 CH (CH 3 2

ON

0.1092 OH 3 00H 3 cyclopropyl ON C.1093 OH 3 00H 3

OF

3

ON

0.1094 OH 3 00H 3 00H 3

ON

0.1095 OH 3

OOH

3

C

6

H

5

ON

0.1096 OH 3 00H 3 4-F-C 6

H

5

ON

0.1097 OH 3 H H 01 0.1098 OH 3 H OH 3 01 0.1099 OH 3 H 0 2

H

5 01 0.1100 OH 3 H 0 3

H

7 01 0.1101 OH 3 H CH (0H 3 2 01 0.1102 OH 3 H cyclopropyl 01 0050/46490 120 No. R3R y Rz C.1103 OH 3 H CF 3 01 C. 1104 CH 3 H OCH 3 01 C. 1105 CH 3 H C 6

H

5 01 C. 1106 CH 3 H 4-F-C 6

H

5 01 C. 1107 CH 3

CH

3 H 01 C. 1108 CH 3

CH

3

CH

3 01 C. 1109 CH 3

CH

3

C

2

H

5 01 C.1110 CH 3

CH

3

C

3

H

7 01 0.1111 CH 3

OH

3 CH (CHA) 2 Cl C.1112 CH 3

CH

3 cyclopropyl 01 C.1113 OH 3

CH

3

CF

3 01 C.1114 CH 3

CH

3

OCH

3 01 C.1115 CH 3

OH

3

C

6

H

5 Cl C.1116 CH 3

CH

3 4-F-C 6

H

5 01 C.1117 OH 3

C

2

H

5 H Cl C.1118 CH 3

C

2

H

5

OH

3 Cl C.1119 CH 3

C

2

H

5

C

2

H

5 Cl C.1120 OH 3

C

2

H

5

C

3

H

7 Cl C.1121 CH 3

C

2

H

5 CH (CHA) 2 01 C.1122 CH 3

C

2

H

5 cyclopropyl 01 C.1123 OH 3 0 2

H

5

OF

3 Cl C.1124 OH 3

C

2

H

5

OCH

3 01 C.1125 CH 3

C

2

H

5

C

6

H

5 Cl C.1126 CH 3

C

2

H

5 4-F-C 6

H

5 01 C.1127 OH 3 cyclopropyl H 01 C.1128 OH 3 cyclopropyl OH 3 01 C.1129 OH 3 cyclopropyl C 2

H

5 01 C.1130 OH 3 cyclopropyl C 3

H

7 01 C.1131 OH 3 cyclopropyl CH (CH 3 2 01 C.1132 OH 3 cyclopropyl cyclopropyl Cl C.1133 OH 3 cyclopropyl CF 3 Cl C.1134 OH 3 cyclopropyl 00H 3 01 C.1135 OH 3 cyclopropyl C 6

H

5 01 0.1136 OH 3 cyclopropyl 4-F-C 6

H

5 Cl 0.1137 OH 3

CF

3 H 01 0.1138 CH 3

CF

3

OH

3 Cl 0.1139 OH 3

OF

3

C

2

H

5 01 0.1140 OH 3

OF

3

C

3

H

7 01 C.1141 OH 3

OF

3 CH (CHA) 2 Cl 0050/46490 121 No. R 3 RX Ry RZ C. 1142 CH 3

CF

3 cyclopropyl Ci C.1143 CH 3

CF

3

CF

3 Ci C.1144 CH 3

CF

3

OCH

3 Ci C.1145 CH 3

CF

3

C

6

H

5 Ci C.1146 CH 3

CF

3 4-F-C 6

H

5 Ci C.1147 CH 3 Cl H Ci C.1148 CH 3 Cl CH 3 Ci C.1149 CH 3 Cl C 2

H

5 Ci C.1150 CH 3 Cl C 3

H

7 Ci C.1151 CH 3 Ci CH (CH 3 2 Ci C.1152 CH 3 Ci cyciopropyl Cl C.1153 CH 3 Ci CF 3 Cl C.1154 CH 3 Cl OCH 3 Cl C.1155 CH 3 Cl C 6

H

5 Ci C.1156 CH 3 Cl 4-F-C 6

H

5 Ci C.1157 CH 3 F H Cl C.1158 CH 3 F CH 3 Ci C.1159 CH 3 F C 2

H

5 Cl C.1160 CH 3 F C 3

H

7 Ci C.1161 CH 3 F CH (CH 3 2 Ci C.1162 CH 3 F cyciopropyl Ci C.1163 CH 3 F CF 3 Ci C.1164 CH 3 F OCH 3 Ci C.1165 CH 3 F C 6

H

5 Ci C.1166 CH 3 F 4-F-C 6

H

5 Ci C.1167 CH 3

OCH

3 H Cl C.1168 CH 3

OCH

3

CH

3 Cl C.1169 CH 3

OCH

3

C

2

H

5 Cl C.1170 CH 3

OCH

3

C

3

H

7 Cl C.1171 CH 3

OCH

3 CH (CHA) 2 Cl C.1172 CH 3

OCH

3 cyclopropyl Cl C.1173 CH 3

OCH

3

CF

3 Cl C.1174 CH 3

OCH

3

OCH

3 Cl C.1175 CH 3

OCH

3

C

6

H

5 Cl C.1176 CH 3

OCH

3 4-F-C 6

H

5 Ci C.1177 CH 3

CH

3

CH

2

CH

2 C.1178 CH 3

CF

3

CH

2

CH

2 C 1179 CF 3

CH

3

CH

2

CH

2

CH

3

C

2

H

5

CH

2

CH

2 0050/46490 122 No. R3R Y RZ C.1181 0 2

.H

5

OH

3 CH 2

CH

2 C.1182 Cl OH 3 CH 2

CH

2 C.1183 CH 3 01

CH

2

CH

2 C.1184 OH 3

CH

3 CH 2

CH

2

CH

2 C.1185 CH 3

CF

3 CH 2

CH

2

CH

2 C.1186 CF 3

OH

3 CH 2

CH

2

CH

2 C.1187 CH 3

C

2

H

5 CH 2

CH

2

CH

2 0.1188 CZH 5

CH

3 CH 2

CH

2

CH

2 C.1189 01 OH 3 CH 2

CH

2

CH

2 C.1190 CH 3 01

CH

2

CH

2

CH

2 C.1191 CH 3

CH

3 CH 2

CH

2

CH

2

CH

2 C.1192 CH 3

CF

3 CH 2

CH

2

CH

2

CH

2 C.1193 CF 3

CH

3 CH 2

CH

2

CH

2

CH

2 C.1194 CH 3

C

2

H

5 CH 2

CH

2

CH

2

CH

2 C.1195 0 2

H

5

CH

3 CH 2

CH

2

CH

2

CH

2 C.1196 Cl CH 3 CH 2

CH

2

CH

2

CH

2 C.1197 CH 3 Cl

CH

2

CH

2

CH

2

CH

2 C.1198 CH 2 0Hi CH 3 H H C.1199 CH 2

CH

3

CH

3

CH

3

H

C.1200 CH 2

CH

3

CH

3

C

2

H

5

H

C.1201 CH CH 3

CH

3

C

3

H

7

H

C.1202 CH 2

CH

3

CH

3

C

4

H

9

H

C.1203 CH 2

CH

3

CH

3 CH (CH 3 2

H

C.1204 CH 2

CH

3

OH

3 cyclopropy.

H

C.1205 CH 2

CH

3

OH

3 CF 3

H

C.1206 CH 2

OH

3

OH

3

OCH

3

H

C.1207 CHqCH 3

OH

3 00 2

H

5

H

C.1208 CH 2

CH

3

OH

3

CH

2

-C

6

H

5

H

0.1209 CH 2

CH

3

OH

3

CH(CH

3

)C

6

H

5

H

0.1210 CH 2

CH

3

OH

3

C

6

H

5

H

C.1211 CH 2 0H 3

OH

3 4-F-C 6

H

5

H

0.1212 OH 2

OH

3

OH

3 4-01-2-pyridyl

H

C.1213 OH 2

OH

3

OH

3 F H C.1214 OH 2

OH

3

OH

3 ON H C.1215 0H 2 0H 3 0 2

H

5 H H 0.1216 OH 2

CH

3 0 2

H

5

OH

3

H

C.1217 CH 2

OH

3

C

2

H

5

C

2

H

5

H

0.1218 CH 2 0H 3 0 2

H

5 0 3

H

7

H

C.1219 I0H 2 0H 3 0 2 Hs C 4

H

9

H

0050/46490 123 No. R 3 Rx RY RZ C. 1220 CH 2

CH

3

C

2

H

5 CH (CHA) 2

H

C. 1221 CH 2

CH

3

C

2

H

5 cyclopropyl H C.1222 CH 2

CH

3

C

2

H

5

CF

3

H

C.1223 CH 2

CH

3

C

2

H

5

OCH

3

H

C.1224 CH 2

CH

3

C

2

H

5 0C 2

H

5

H

C.1225 CH 2

CH

3

C

2

H

5

CH

2

-C

6

H

5

H

C.1226 CH 2

CH

3

C

2

H

5

CH(CH

3

)C

6

H

5

H

C.1227 CH 2

CH

3

C

2

H

5

C

6

H

5

H

C.1228 CH 2

CH

3

C

2

H

5 4-F-C 6

H

5

H

C.1229 CH 2

CH

3

C

2

H

5 4-Cl-2-pyridyl H C.1230 CH 2

CH

3

C

2

H

5 F H C.1231 CH 2

CH

3

C

2

H

5 CN H C.1232 CH 2

CH

3

CF

3 H H C.1233 CH 2

CH

3

CF

3

CH

3

H

C.1234 CH 2

CH

3

CF

3

C

2

H

5

H

C.1235 CH 2

CH

3

CF

3

C

3

H

7

H

C.1236 CH 2

CH

3

CF

3

C

4 H9 H C.1237 CH 2

CH

3

CF

3 CH (CH 3 2

H

C.1238 CH 2

CH

3

CF

3 cyclopropyl H C.1239 CH 2

CH

3

CF

3

CF

3

H

C.1240 CH 2

CH

3

CF

3

OCH

3

H

C.1241 CH 2

CH

3

CF

3 0C 2

H

5

H

C.1242 CH 2

CH

3

CF

3

CH

2

-C

6

H

5

H

C.1243 CH 2

CH

3

CF

3

CH(CH

3

)C

6

H

5

H

C.1244 CH 2

CH

3

CF

3

C

6

H

5

H

C.1245 CH 2

CH

3

CF

3 4-F-C 6

H

5

H

C.1246 CH 2

CH

3

CF

3 4-C1-2-pyridyl H C.1247 CH 2

CH

3

CF

3 F H C.1248 CH 2

CH

3

CF

3 CN H C.1249 CH 2

CH

3 Cl H H C.1250 CH 2

CH

3 Cl CH 3

H

C.1251 CH 2

CH

3 Cl C 2

H

5

H

C.1252 CH 2

CH

3 Cl C 3

H

7

H

C.1253 CH 2

CH

3 Cl C 4

H

9

H

C.1254 CH 2

CH

3 Cl CH(CH 3 2

H

C.1255 CH 2

CH

3 Cl cyclopropyl H C.1256 CH 2

CH

3 Cl CF 3

H

C.1257 CH 2

CH

3 Cl OCH 3

H

C.1258 CH 2

CH

3 Cl 0C 2

H

5

H

0050/46490 124 No. R x RY RZ C. 1259 CH 2

CH

3 Cl CH 2

-C

6

H

5

H

C. 1260 CH 2

CH

3 Cl CH(CH 3

)C

6

H

5

H

C. 1261 CH 2

CH

3 Cl C 6

H

5

H

C. 1262 CH 2

CH

3 Cl 4-F-C 6

H

5

H

C. 1263 CH 2

CH

3 Cl 4-Cl-2-pyridyl H C.1264 CHCH 3 i Cl F H C.1265 CHqCH 3 A Cl CN H C.1266 CHqCH 3 A OCH 3 H H C.1267 CH 2

CH

3

OCH

3

CH

3

H

C.1268 CH 2

CH

3

OCH

3

C

2

H

5

H

C.1269 CH 2

CH

3

OCH

3

C

3 H, H C.1270 CHqCH 3 A OCH 3

C

4 H9 H C.1271 CH 2

CH

3

OCH

3 CH (CHA) 2

H

C.1272 CH 2

CH

3

OCH

3 cyclopropyl H C.1273 CH 2

CH

3

OCH

3

CF

3

H

C.1274 CH 2

CH

3

OCH

3

OCH

3

H

C.1275 CH 2

CH

3

OCH

3 0C 2

H

5

H

C.1276 CH 2

CH

3

OCH

3

CH

2

-C

6

H

5

H

C.1277 CH 2

CH

3

OCH

3

CH(CH

3

)C

6

H

5

H

C.1278 CH 2

CH

3

OCH

3

C

6

H

5

H

C.1279 CH 2

CH

3

OCH

3 4-F-C 6

H

5

H

C.1280 CH 2

CH

3

OCH

3 4-C1-2-pyridyl H C.1281 CH 2

CH

3

OCH

3 F H C.1282 CH 2

CH

3

OCH

3 CN H C.1283 CH 2

CH

3

CH

3 H CH 3 C.1284 CHqCHq CH 3

CH

3

CH

3 C.1285 CH 2

CH

3

CH

3

C

2

H.

5

CH

3 C.1286 CH 2

CH

3

CH

3

C

3

H

7

CH

3 C.1287 CH 2

CH

3

CH

3

C

4

H

9

CH

3 C.1288 CH 2

CH

3

CH

3 CH (CHA) 2

CH

3 C.1289 CH 2

CH

3

CH

3 cyclopropyl CH 3 C.1290 CH 2

CH

3

CH

3

CF

3

CH

3 C.1291 CH 2

CH

3

CH

3

OCH

3

CH

3 C.1292 CH 2

CH

3

CH

3 0C 2

H

5

CH

3 C.1293 CH 2

CH

3

CH

3

CH

2

-C

6

H

5

CH

3 C.1294 CH 2

CH

3

CH

3

CH(CH

3

)C

6

H

5

CH

3 C.1295 CH 2

CH

3

CH

3

C

6 HS CH 3 C.1296 CH 2

CH

3

OH

3 4-F-C 6

H

5

CH

3 C.1297 CH 2

CH

3

OH

3 4-Cl-2-pyridyl LCH 3 0050/46490 125 No. R 3 Rx Ry RZ C. 1298 CH 2

CH

3

CH

3 F CH 3 C.1299 CH 2

CH

3

CH

3 CN CH 3 C.1300 ICH 2

CH

3

C

2

H

5 H CH 3 C.1301 CH 2

CH

3

C

2

H

5

CH

3

CH

3 C.1302 CH 2

CH

3

C

2

H

5

C

2

H

5

CH

3 C.1303 CH 2

CH

3

C

2

H

5

C

3

H

7

CH

3 C.1304 CH7CH 3 A C 2

H

5

C

4

H

9

CH

3 C.1305 CH 2

CH

3

C

2

H

5 CH (CH 3 2

CH

3 C.1306 CH 2

CH

3

C

2

H

5 cyclopropyJ. CH 3 C.1307 CHqCH-i C 2

H

5

CF

3

CH

3 C.1308 CH 2

CH

3

C

2

H

5

OCH

3

CH

3 C.1309 CH 2

CH

3

C

2

H

5 0C 2

H

5

CH

3 C.1310 CH 2

)CH

3 A C 2

H

5

CH

2

-C

6

H

5

CH

3 C.1311 CH 2

CH

3

C

2

H

5 CH (CH 3

C

6

H

5

CH

3 C.1312 CH 2

CH

3

C

2

H

5

C

6

H

5

CH

3 C.1313 CH 2

CH

3

C

2

H

5 4-F-C 6

H

5

CH

3 C ,.1314 CH 2

CH

3

C

2

H

5 4-C1-2-pyridyJ. CH 3 C.1315 CH 2

CH

3

C

2

H.

5 F CH 3 C.1316 CH 2

CH

3

C

2

H

5 CN CH 3 C.1317 CH 2

CH

3

CF

3 H CH 3 C.1318 CH 2

CH

3

CF

3

CH

3

CH

3 C.1319 CH 2

CH

3

CF

3

C

2

H

5

CH

3 C.1320 CHqCH 3 A CF 3

C

3

H

7

CH

3 C.1321 CH 2

CH

3

CF

3

C

4

H

9

CH

3 C.1322 MMCH CF 3 CH (CH 3 2

CH

3 C.1323 MMCH CF 3 cyclopropyl CH 3 C.1324 CH 2

CH

3

CF

3

CF

3

CH

3 C.1325 CH 2

CH

3

CF

3

OCH

3

CH

3 C.1326 CH 2

CH

3

CF

3 0C 2

H

5 Cl 3 C.1327 CH 2

CH

3

CF

3

CH

2

-C

6

H

5

CH

3 C.1328 CH 2

-CH

3 A CF 3

CH(CH

3

)C

6

H

5

CH

3 C.1329 CHCHi CF 3

C

6

H

5

CH

3 C.1330 CHqCH 3 A CF 3 4-F-C 6

H

5

CH

3 C.1331 CH 2

CH

3

CF

3 4-C1-2-pyridyl CH 3 C.1332 CH 2

CH

3

CF

3 F CH 3 C.1333 CH 2

CH

3

CF

3 CN CH 3 C.1334 CH 2

CH

3 Cl H CH 3 C.1335 CH 2

CH

3

CH

3

CH

3 C.36 CHqCH 3 A C) C 2

H

5

CH

3 126 No. R RY R C.1337 CH 2

CH

3 Cl

C

3

H

7 CH 3 C.1338 CH 2

CH

3 Cl C 4 H9 CH 3 C.1339 CH 2

CH

3 Cl CH (CH 3 2

CH

3 C.1340 CH 2

CH

3 Cl cyclopropyl

CH

3 C.1341 CH 2

CH

3 Cl

CF

3 CH 3 C.1342 CH 2

CH

3 Cl

OCH

3 CM 3 10C.1343 CH 2

CH

3 Cl 0C 2

H

5

CH

3 C.1344 CH 2

CH

3 Cl

CH

2

-C

6

H

5

CH

3 C.1345 CH 2

CH

3 Cl CH (CH 3

C

6 HS CH 3 C.1346 CH 2

CH

3 Cl

C

6

H

5

CM

3 C.1347 CH 2

CH

3 Cl 4-F-C 6

H

5 CH3 C.1348 CH 2

CH

3 Cl 4-Cl-2-pyridyl

CM,

C.1349 CH 2

CH

3 Cl F CH3 C.1350 CM 2

CM

3 Cl CN CM, C.1351 CH 2

CM

3 0CM, H CH3 C.1352 CH 2

CH

3 0CM, CH3 CM, C.1353 CM 2

CH

3 0CM, C 2

H

5

CM,

C.1354 CH 2

CH

3 OCJi3 C3H 7 CH3 C.1355 CH 2 CH3 0CM,

C

4

H

9 CH3 C.1356 CH 2 CH.3 OCH3 CH (CH3) 2

CM,

C.1357 CH 2

CH

3 0CM, cyclopropyl

CH,

C.1358 CM 2

CH

3 0CM 3

CF

3

CH,

C.1359 CH 2

CH

3 0CM, 0CM,

CH,

C.1360 CM 2 CH3 0CM, 0C 2

H

5 CH3 30 C.1361 CH 2

CH

3

OCH

3 CH 2

-C

6

H

5 CH3 C.1362 CH 2

CH

3 OCH3 CH (CH 3

C

6

H

5 CH3 C.1363 CH 2

CH

3 0CM,

C

6

M

5

CM,

C.1364 CH 2

CH

3 0CM, 4-F-C 6 Hs, CH3 35 C.1365 CM 2 CH3 OCH3 4-Cl-2--pyridyl

CM

3 C.1366 CH 2 CH3 0CH 3 F CM 3 C.1367 ICH 2

CH

3 0CM 3 CN CM 3 4It is known that inhibitors of mitochondrial respiration of fungi can be employed as fungicides, eg. antimycin (cf. "Inhibitors of Mitochondrial Function", Eds.: Rieske et al.; Pergamon Press, Oxford 1981, p. 110). However, the practical use of antimycin is impeded by various disadvantages, eg. the difficult 4and complicated preparation and the insufficient stability under application conditions, eg. in crop protection.

0050/46490 127 Mitochondrial respiration is essential for the metabolism. In the mitochondria, energy is stored, with the aid of respiration, in the form of adenosine triphosphate (ATP). Inhibition of mitochondrial respiration finally results in inhibition of ATP formation.

For example, the compounds I according to the invention inhibit the mitochondrial respiration of harmful fungi. In fungi which have been treated with the compounds I according to the invention, the ATP metabolism, or energy-dependent metabolic processes, cease, which results in a standstill of fungal growth and thus in the death of the fungi.

The mitochondrial respiration of animal pests is inhibited in a similar manner.

The compounds I are therefore suitable for controlling animal pests, in particular from the class of the insects, arachnids and nematodes, and harmful fungi.

The compounds I are distinguished by an outstanding activity against a broad spectrum of phytopathogenic fungi, in particular from the class of the Ascomycetes, Deuteromycetes, Phycomycetes and Basidiomycetes. Some of them act systemically and can be employed in crop protection as foliar- and soil-acting fungicides.

They are especially important for controlling a large number of fungi on a variety of crop plants such as wheat, rye, barley, oats, rice, maize, grass, bananas, cotton, soybeans, coffee, sugar cane, grapevines, fruit species, ornamentals and vegetables such as cucumbers, beans, tomatoes, potatoes and cucurbits, and on the seeds of these plants.

Specifically, they are suitable for controlling the following plant diseases: Erysiphe graminis (powdery mildew) in cereals, Erysiphe cichoracearum and Sphaerotheca fuliginea on cucurbits, Podosphaera leucotricha on apples, Uncinula necator on grapevines, Puccinia species on cereals, Rhizoctonia species on cotton, rice and lawns, Ustilago species on cereals and sugar cane, Venturia inaequalis (scab) on apples, Helminthosporium species on cereals, Septoria nodorum on wheat, Botrytis cinerea (gray mold) on strawberries, vegetables, ornamentals and grapevines, Cercospora arachidicola on peanuts, Pseudocercosporella herpotrichoides on wheat, barley, Pyricularia oryzae on rice, Phytophthora infestans on potatoes and tomatoes, Fusarium and Verticillium species on a variety of plants, Plasmopara viticola 0050/46490 128 on grapevines, Pseudocercosporella species in hops and cucumbers, Alternaria species on vegetables and fruit and Mycosphaerella species in bananas.

Moreover, the compounds I are suitable for controlling harmful fungi in the protection of materials (eg. wood, paper, paint dispersions, fibers or tissues) and in the protection of stored products.

The compounds I are applied by treating the fungi, or the plants, seeds, materials or the soil to be protected against fungal infection, with a fungicidally active amount of the active ingredients. Application is effected before or after infection of the materials, plants or seeds by the fungi.

They can be converted into the customary formulations, such as solutions, emulsions, suspensions, dusts, powders, pastes and granules. The use form depends on the specific intended use; in any case, it should guarantee fine and uniform distribution of the compound according to the invention. The formulations are prepared in a known manner, eg. by extending the active ingredient with solvents and/or carriers, if desired using emulsifiers and dispersants, it also being possible to use other organic solvents as auxiliary solvents if water is used as the diluent.

Suitable auxiliaries are essentially: solvents such as aromatics (eg. xylene), chlorinated aromatics (eg. chlorobenzenes), paraffins (eg. mineral oil fractions), alcohols (eg. methanol, butanol), ketones (eg. cyclohexanone), amines (eg. ethanolamine, dimethylformamide) and water; carriers such as ground natural minerals (eg. kaolins, clays, talc, chalk) and ground synthetic minerals (eg. highly disperse silica, silicates); emulsifiers such as nonionic and anionic emulsifiers (eg. polyoxyethylene fatty alcohol ethers, alkylsulfonates and arylsulfonates), and dispersants such as lignin-sulfite waste liquors and methylcellulose.

The fungicidal compositions generally comprise from 0.1 to preferably from 0.5 to 90, by weight of active ingredient.

Depending on the nature of the desired effect, the rates of application in crop protection are from 0.01 to 2.0 kg of active ingredient per ha.

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

129 when used in the protection of materials or stored products, the rate of application of active ingredient depends on the nature of the field of application and on the desired effect. NIormal rates of application in the protection of materials are, for example, 0.001 g to 2 kg, preferably 0.005 g to 1 kg, of active ingredient per cubic meter of material treated.

In the use form as fungicides, the compositions according to the invention can also exist together with other active ingredients, e.g. with herbicides, insecticides, growth regulators, fungicides, or else with fertilizers.

A mixture with fungicides frequently results in a widened fungicidal spectrum of action.

The following list of fungicides together with which the comnpounds according to the invention can be used is intended to illustrate the possible combinations, but not to impose any limitation: sulfur, dithiocarbamates and their derivatives, such as iron(III) dimethyldithiocarbanate, zinc dimethyldithiocarbamate, zinc ethylenebisdithiocarbamate, manganese ethylenebisdithiocarbamate, manganese zinc ethylenediaminebisdithiocarbamate, tetramethylthiuram disulf ides, ammonia complex of zinc (N,N-ethylenebisdithiocarbamate), ammonia complex of zinc propylenebisdithiocarbamate), zinc (N,N'-propylenebisdithiocarbamate), N,N'-polypropylenebis (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, diisopropyl 0:* heterocyclic substances, such as 2 -heptadecyl-2-imidazoline acetate, 2 4 -dichloro- 6 -(o-chloroanilino)..5-triazine, 0,0-di- 00ethylphthalimidophosphonothioate, 5-amino---(bis (dimethylamino)phosphinylj-3-phenyl-1,2,4..triazole, 2, 3-dicyano-1, 4-dithioanthraquinone, 2-thio-1, 3-dithiolo(4 ,5-b Iquinoxaline, methyl 1- (butylcarbamoyl)-2-benzimidazolecarbamate, 2-methoxycarbonylaminobenzimidazole, 2 2 -furyl)benzimidazole, 2-(4-thiazolyl)benzimidazole, li 2 2 -tetrachloroethylthio)tetrahydrophthalimide, N-trichloromethylthiotetrahydrophthalimide, N-trichloromethylthiophthalimide, N-dichlorofluoromethylthio-N' ,N'-dimethyl-N-phenylsulfodiamide, 5-ethoxy--3-trichloromethyl- 1, 2,3-thiadiazole, 2-thiocyanato- 0050/46490 130 methylthiobenzothiazole, 1, 4-dichloro-2, 4- (2-chiorophenyihydrazono) -3-methyl--5-isoxazolone, pyridine- 2-thio-1-oxide, 8-hydroxyquinoline or its copper salt, 2,3dihydro-5-carboxanilido-6-nethyl-1, 4-oxathiine, 2, 3-dihydro-5-carboxanilido-6-methyl-1, 4-oxathiine 4,4-dioxide, 6-dihydro-4H-pyran-3-carboxanilide, 2-methylfuran-3-carboxanilide, 2, 5-dimethylfuran-3-carboxanilide, 2,4, 5 -trimethylfuran-3-carboxanilide, N-cyclohexyl-2, furan-3-carboxamide, N-cyclohexyl-N-methoxy-2 ran-3-carboxamide, 2-methylbenzanilide, 2-iodobenzanilide, N-formyl-N-morpholine-2, 2, 2-trichioroethyl acetal, piperazine-1,4-diylbis( l-( 2 ,2,2-trichloro-ethyl)formamide [sic), 1- 4-dichioroanilino )-1-formylamino-2 2-trichioroethane, 2,6-dimethyl--N-tridecylmorpholine or its salts, 2,6-dimethyl- N-cyclododecylmorpholine or its salts, N-[3-(p-tert-butylphenyl)-2-methylpropyl ]-cis-2, 6-dimethylmorpholine, 3-(p--tertbutylphenyl)-2-methylpropyl ]piperidine, ,4-dichlorophenyl)-4-ethyl-1,3-dioxolan-2-ylethyl]lH-1,2,4-triazole, 1- (2 ,4-dichlorophenyl) -4-n-propyl-1 ,3-dioxolan-2-ylethyl] 1H-1,2,4-triazole, N-(n-propyl)-N-(2,4,6-trichlorophenoxyethyl)-N'-imidazolylurea, 1-(4-chlorophenoxy)-3,3-dimethyllH-1,2,4-triazol-1-yl)-2-butanone, 1-(4-chlorophenoxy)- 3, 3-dimethyl-1- H-1, 2, 4-triazol-1-yl )-2-butanol, (2RS, 3RS (2-chlorophenyl (4-f luorophenyl )oxiran-2-ylmethyl]-lH-1,2,4-triazole, c-(2-chlorophenyl)-a-(4-chlorophenyl )-5-pyrimidinemethanol, 5-butyl-2-dimethylamino-4-hydroxy-6-methylpyrinidine, bis (p-chlorophenyl )-3-pyridinemethanol, 1, 2-bis (3-ethoxycarbonyl-2-thioureido)benzene, 1, 2-bis (3-methoxycarbonyl-2-thioureido)benzene, strobilurins such as methyl E-methoxyimino-[a-(o-tolyloxy)-otolyl]acetate, methyl E-2-{2-[6-(2-cyanophenoxy)pyrimidin-4-yloxy] phenyl }-3-methoxyacrylate, N-methyl-E-methoxyimino- (2-phenoxyphenyl Iacetamide, N-methyl-E-methoxyimino-[a-( 2, 5-dimethylphenoxy)-o-tolyl ]acetamide, anilinopyrimidines such as N- 6-dimethylpyrimidin-2-yl aniline, N- [4-methyl-6-( l-propynyl)pyrimidin-2-yl Janiline, N- [4-methyl-6-cyclopropylpyrimidin-2-yl ]aniline, phenylpyrroles such as 4-(2,2-difluoro-1,3-benzodioxol-4-yl)pyrrole-3-carbonitrile, cinnamamides such as 3-(4-chlorophenyl)-3-(3,4-dimethoxyphenyl )acryloylmorpholide, and a variety of fungicides such as dodecylguanidine acetate, 0050/46490 131 3- 5-dimethyl-2-oxycyclohexyl) -2-hydroxyethyl Iglutarimide, hexachlorobenzene, methyl 6-dimethylphenyl)-N-( 2furoyl)-DL-alaninate, DL-N-(2 ,6-dimethylphenyl)-N-(2 '-methoxyacetyl)alanine methyl ester, 6-dimethylphenyl)-N-chloroacetyl-D, L-2-aminobutyrolactone, DL-N- 6-dimethyiphenyl (phenylacetyl) alariine methyl ese, nyl-3- 5-dichiorophenyl ,4-dioxo-1, 3-oxazolidine, 3- 5-dichlorophenyl (-5-methyl-5-methoxymethyl]1-1 ,3-oxazolidine-2,4-dione [sic], moylhydantoin, 3, 5-dichlorophenyl)-1, 2-dimethylcyclopropane-i, 2-dicarboximide, 2-cyano- (ethylaminocarbonyl )-2-methoximino]acetamide, ,4-dichlorophenyl)pentyl]-lH-1,2,4-triazole, 2,4-difluoro-a-(lH-1,2,4-triazolyl-1-methyl)benzhydryl alcohol, N-(3-chloro-2, 6-dinitro-4-trifluoromethylphenyl )-5-trifluoromethyl-3-chloro-2-aminopyridine, (bis(4-fluorophenyl)methylsilyl)methyl)-lH-1,2,4-triazole.

The compounds of the formula I are furthermore suitable for effectively controlling pests from the class of the insects, arachnids and nematodes. They can be employed as pesticides in crop protection and in the hygiene, stored-product and veterinary sector.

The harmful insects -include, from the order of the lepidopterans (Lepidoptera), for example, Agrotis ypsilon, Agrotis segetum, Alabama argillacea, Anticarsia gemmatalis, Argyresthia conjugella, Autographa gamma, Bupalus piniarius, Cacoecia murinana, Capua reticulana, Cheimatobia brumata, Choristoneura fumiferana, Choristoneura occidentalis, Cirphis unipuncta, Cydia pomonella, Dendrolimus pini, Diaphania nitidalis, Diatraea grandiosella, Earias insulana, Elasmopalpus lignosellus, Eupoecilia ambiguella, Evetria bouliana, Feltia subterranea, Galleria mellonella, Grapholitha funebrana, Grapholitha molesta, Heliothis armigera, Heliothis virescens, Heliothis zea, Hellula undalis, Hibernia defoliaria, Hyphantria cunea, Hyponomeuta malinellus, Keiferia lycopersicella, Lambdina fiscellaria, Laphygma exigua, Leucoptera coffeella, Leucoptera scitella, Lithocolletis blancardella, Lobesia botrana, Loxostege sticticalis, Lymantria dispar, Lymantria monacha, Lyonetia clerkella, Malacosoma neustria, Mamestra brassicae, Orgyia pseudotsugata, Ostrinia nubilalis, Panolis flammea, Pectinophora gossypiella, Peridroma saucia, Phalera bucephala, Phthorimaea operculella, Phyllocnistis citrella, Pieris brassicae, Plathypena scabra, Plutella xylostella, Pseudoplusia includens, Rhyacionia frustrana, Scrobipalpula absoluta, Sitotroga cerealella, Sparganothis pilleriana, Spodoptera frugiperda, Spodoptera littoralis, Spodoptera litura, Thaumatopoea pityocampa, Tortrix viridana, Trichoplusia ni, 0050/46490 132 Zeiraphera canadensis.

From the order of 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 rufimanus, Bruchus pisorum, Bruchus lentis, Byctiscus betulae, Cassida nebulosa, Cerotoma trifurcata, Ceuthorrhynchus assimilis, Ceuthorrhynchus napi, Chaetocnema tibialis, Conoderus vespertinus, Crioceris asparagi, Diabrotica longicornis, Diabrotica 12-punctata, Diabrotica virgifera, Epilachna varivestis, Epitrix hirtipennis, Eutinobothrus brasiliensis, Hylobius abietis, Hypera brunneipennis, Hypera postica, Ips typographus, Lema bilineata, Lema melanopus, Leptinotarsa decemlineata, Limonius californicus, Lissorhoptrus oryzophilus, Melanotus communis, Meligethes aeneus, Melolontha hippocastani, Melolontha melolontha, Oulema oryzae, Ortiorrhynchus [sic] sulcatus, Otiorrhynchus ovatus, Phaedon cochleariae, Phyllotreta chrysocephala, Phyllophaga sp., Phyllopertha horticola, Phyllotreta nemorum, Phyllotreta striolata, Popillia japonica, Sitona lineatus, Sitophilus granaria.

From the order of the dipterans (Diptera), for example, Aedes aegypti, Aedes vexans, Anastrepha ludens, Anopheles maculipennis, Ceratitis capitata, Chrysomya bezziana, Chrysomya hominivorax, Chrysomya macellaria, Contarinia sorghicola, Cordylobia anthropophaga, Culex pipiens, Dacus cucurbitae, Dacus oleae, Dasineura brassicae, Fannia canicularis, Gasterophilus intestinalis, Glossina morsitans, Haematobia irritans, Haplodiplosis equestris, Hylemyia platura, Hypoderma lineata, Liriomyza sativae, Liriomyza trifolii, Lucilia caprina [sic], Lucilia cuprina, Lucilia sericata, Lycoria pectoralis, Mayetiola destructor, Musca domestica, Muscina stabulans, Oestrus ovis, Oscinella frit, Pegomya hysocyami, Phorbia antiqua, Phorbia brassicae, Phorbia coarctata, Rhagoletis cerasi, Rhagoletis pomonella, Tabanus bovinus, Tipula oleracea, Tipula paludosa.

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

From the order of the hymenopterans (Hymenoptera), for example, Athalia rosae, Atta cephalotes, Atta sexdens, Atta texana, Hoplocampa minuta, Hoplocampa testudinea, Monomorium pharaonis, Solenopsis geminata, Solenopsis invicta.

0050/46490 133 From the order of the heteropterans (Heteroptera), for example, Acrosternum hilare, Blissus leucopterus, Cyrtopeltis notatus, Dysdercus cingulatus, Dysdercus intermedius, Eurygaster integriceps, Euschistus impictiventris, Leptoglossus phyllopus, Lygus lineolaris, Lygus pratensis, Nezara viridula, Piesma quadrata, Solubea insularis, Thyanta perditor.

From the order of the homopterans (Homoptera), for example, Acyrthosiphon onobrychis, Adelges laricis, Aphidula nasturtii, Aphis fabae, Aphis pomi, Aphis sambuci, Brachycaudus cardui, Brevicoryne brassicae, Cerosipha gossypii, Dreyfusia nordnannianae, Dreyfusia piceae, Dysaphis radicola, Dysaulacorthum pseudosolani, Empoasca fabae, Macrosiphum avenae, Macrosiphum euphorbiae, Macrosiphon rosae, Megoura viciae, Metopolophium dirhodum, Myzodes persicae, Myzus cerasi, Nilaparvata lugens, Pemphigus bursarius, Perkinsiella saccharicida, Phorodon humuli, Psylla mali, Psylla piri, Rhopalomyzus ascalonicus, Rhopalosiphum maidis, Sappaphis mala, Sappaphis mali, Schizaphis graminum, Schizoneura lanuginosa, Trialeurodes vaporariorum, Viteus vitifolii.

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

From the order of the orthopterans (Orthoptera), for example, Acheta domestica, Blatta orientalis, Blattella germanica, Forficula auricularia, Gryllotalpa gryllotalpa, Locusta migratoria, Melanoplus bivittatus, Melanoplus femur-rubrum, Melanoplus mexicanus, Melanoplus sanguinipes, Melanoplus spretus, Nomadacris septemfasciata, Periplaneta americana, Schistocerca americana, Schistocerca peregrina, Stauronotus maroccanus, Tachycines asynamorus.

From the class of the Arachnoidea, for example, arachnids (Acarina) such as Amblyomma americanum, Amblyomma variegatum, Argas persicus, Boophilus annulatus, Boophilus decoloratus, Boophilus microplus, Brevipalpus phoenicis, Bryobia praetiosa, Dermacentor silvarum, Eotetranychus carpini, Eriophyes sheldoni, Hyalomma truncatum, Ixodes ricinus, Ixodes rubicundus, Ornithodorus moubata, Otobius megnini, Paratetranychus pilosus, Dermanyssus gallinae, Phyllocoptruta oleivora, Polyphagotarsonemus latus, Psoroptes ovis, Rhipicephalus appendiculatus, Rhipicephalus evertsi, Sarcoptes scabiei, Tetranychus cinnabarinus, Tetranychus kanzawai, Tetranychus pacificus, Tetranychus telarius, Tetranychus urticae.

0050/46490 134 From the class of the nematodes, for example, root knot nematodes, eg. Meloidogyne hapla, Meloidogyne incognita, Meloidogyne javanica, cyst-forming nematodes, eg. Globodera rostochiensis, Heterodera avenae, Heterodera glycines, Heterodera schachtii, Heterodera trifolii, stem eelworms and foliar nematodes, eg.

Belonolaimus longicaudatus, Ditylenchus destructor, Ditylenchus dipsaci, Heliocotylenchus multicinctus, Longidorus elongatus, Radopholus similis, Rotylenchus robustus, Trichodorus primitivus, Tylenchorhynchus claytoni, Tylenchorhynchus dubius, Pratylenchus neglectus, Pratylenchus penetrans, Pratylenchus curvitatus, Pratylenchus goodeyi.

The active ingredients can be used as such, in the form of their formulations or the use forms prepared therefrom, for example in the form of ready-to-spray solutions, powders, suspensions or dispersions, emulsions, oil dispersions, pastes, dusts, materials for spreading or granules, by means of spraying, atomizing, dusting, spreading or pouring. The use forms depend entirely on the intended purposes; in any case, they should guarantee the finest possible distribution of the active ingredients according to the invention.

The concentrations of active ingredient in the ready-to-use preparations can be varied within substantial ranges.

In general, they are from 0.0001 to 10%, preferably from 0.01 to 1%.

The active ingredients can also be used successfully in the ultra-low-volume method (ULV), it being possible to apply formulations with over 95% by weight of active ingredient, or even the active ingredient without additives.

Under field conditions, the rate of application of active ingredient for controlling pests is 0.1 to 2.0, preferably 0.2 to kg/ha.

Substances which are suitable for the preparation of ready-tospray solutions, emulsions, pastes or oil dispersions are mineral oil fractions of medium to high boiling point such as kerosene or diesel oil, furthermore coal tar oil and oils of vegetable or animal origin, aliphatic, cyclic and aromatic hydrocarbons, eg. benzene, toluene, xylene, paraffin, tetrahydronaphthalene, alkylated naphthalenes or their derivatives, methanol, ethanol, propanol, butanol, chloroform, carbon tetrachloride, cyclohexanol, cyclohexanone, chlorobenzene, isophorone, strongly polar solvents, eg. dimethylformamide, dimethyl sulfoxide, 135 n-methylpyrrolidone and water.

Aqueous use forms can be prepared from emulsion concentrates, pastes or wettable powders (sprayable powders, oil dispersions) by adding water. To prepare emulsions, pastes or oil dispersions, the substances, as such or dissolved in an oil or solvent, can be homogenized in water by means of wetting agent, tackifier, dispersant or emulsifier. However, it is also possible to prepare concentrates composed of active ingredient, wetting agent, tackifier, dispersant or emulsifier and, if desired, solvent or oil, which are suitable for dilution with water.

Suitable surfactants are alkali metal, alkaline earth metal and ammonium salts of lignosulfonic acid, naphthalenesulfonic acid, phenolsulfonic acid, dibutylnaphthalenesulfonic acid, alkylarylsulfonates, alkyl sulfates, alkylsulfonates, fatty alcohol sulfates and fatty acids and their alkali metal and 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 naphthalenesulfc'nic acid with phenol and formaldehyde, polyoxyethylene octylphenol ether, ethoxylated isooctylphenol, octylphenyl, nonylphenol, alkylphenol, polyglycol ethers, tributylphenyl polyglycol ether, alkylaryl polyether alcohols, isotridecyl alcohol, fatty alcohol/ethylene oxide condensates, ethoxylated castcr oil, polyoxyethylene alkyl ethers, ethoxylated polyoxypropylene, lauryl alcohol polyglycol ether acetal, sorbitol esters, lignin-sulfite waste liquors and methylcellulose.

Powders, materials for spreading and dusts can be prepared by mixing or concomitantly grinding the active substances with a solid carrier.

In general, the formulations comprise from 0.01 to 95% by weight., preferably from 0.1 to 90% by weight, of the active ingredient. The active ingredients are employed in a purity of from 90% to 100%, preferably 95% to 100% (according to NMR spectrum)..

Examples of the formulations are: I. 5 parts by weight of a compound according to the invention are mixed intimately with 95 parts by weight of finely divided kaolin. This gives a dust which comprises 5% by -weight of the active ingredient.

C -9 ^gs^ 0050/46490 136 II. 30 parts by weight of a compound according to the invention are mixed intimately with a mixture of 92 parts by weight of pulverulent silica gel and 8 parts by weight of paraffin oil which have been sprayed onto the surface of this silica gel. This gives a preparation of the active ingredient with good adhesion (comprises 23% by weight of active ingredient).

III. 10 parts by weight of a compound according to the invention are dissolved in a mixture composed of 90 parts by weight of xylene, 6 parts by weight of the adduct of 8 to 10 mol of ethylene oxide and 1 mol of oleic acid N-monoethanolamide, 2 parts by weight of calcium dodecylbenzenesulfonate and 2 parts by weight of the adduct of 40 mol of ethylene oxide and 1 mol of castor oil (comprises 9% by weight of active ingredient).

IV. 20 parts by weight of a compound according to the invention are dissolved in a mixture composed of 60 parts by weight of cyclohexanone, 30 parts by weight of isobutanol, 5 parts by weight of the adduct of 7 mol of ethylene oxide and 1 mol of isooctylphenol and 5 parts by weight of the adduct of 40 mol of ethylene oxide and 1 mol of castor oil (comprises 16% by weight of active ingredient).

V. 80 parts by weight of a compound according to the invention are mixed thoroughly with 3 parts by weight of sodium diisobutylnaphthalene-alpha-sulfonate, 10 parts by weight of the sodium salt of a lignosulfonic acid from a sulfite waste liquor and 7 parts by weight of pulverulent silica gel, and the mixture is ground in a hammer mill (comprises by weight of active ingredient).

VI. 90 parts by weight of a compound according to the invention are mixed with 10 parts by weight of N-methyl-a-pyrrolidone, which gives a solution which is suitable for use in the form of microdrops (comprises 90% by weight of active ingredient).

VII. 20 parts by weight of a compound according to the invention are dissolved in a mixture composed of 40 parts by weight of cyclohexanone, 30 parts by weight of isobutanol, parts by weight of the adduct of 7 mol of ethylene oxide and 1 mol of isooctylphenol and 10 parts by weight of the adduct of 40 mol of ethylene oxide and 1 mol of castor oil.

Pouring the solution into 100,000 parts by weight of water and finely distributing it therein gives an aqueous disper- UWU/049OW 137 sion which comprises 0.02% by weight of the active ingredient.

parts by weight of a compound according to the invention are mixed thoroughly with 3 parts by weight of sodium diisobutylnaphthalene-a-sulfonate, 17 parts by weight of the sodium salt of a lignosulfonic acid from a sulfite waste liquor and 60 parts by weight of pulverulent silica gel, and the mixture is ground in a hammer mill. Finely distributing the mixture in 20,000 parts by weight of water gives a spray mixture which comprises 0.1% by weight of the active ingredient.

Granules, eg. coated granules, impregnated granules and homogeneous granules, can be prepared by binding the active ingredients onto solid carriers, examples of solid carriers are mineral earths such as silica gel, silicas, silica gel, silicates, talcs, kaolin, attaclay, limestone, lime, chalk, bole, loess, clay, dolomite, diatomaceous earth, calcium sulfate, magnesium sulfate, magnesium oxide, ground synthetic materials, fertilizers such as ammonium sulfate, ammonium phosphate, ammonium nitrate, ureas, and products of vegetable origin such as cereal meal, tree bark meal, wood meal and nut shell meal, cellulose powders, and other solid carriers.

Various types of oils, or herbicides, fungicides, other pesticides, or bactericides, can be added to the active ingredients, if appropriate also only just prior to use (tank mix). These agents can be admixed with the agents according to the invention 30 in a weight ratio of 1:10 to 10:1.

Synthesis examples The protocols given in the synthesis examples which follow were used for obtaining further compounds I by altering the starting o compounds as required. The resulting compounds are listed in the tables which follow together with physical data.

The chemical shifts (in ppm) of the 1 H NMR spectra were recorded t 40 against tetramethylsilane (br broad signal, s singlet, d doublet, m multiplet).

o 0050/46490 138 1. Preparation of the intermediates: l.a Synthesis of 2-fluorobenzaldehyde cyanohydrin H

C=-N

First, 171 g of 2-fluorobenzaldehyde are added dropwise at room temperature to a stirred suspension of 179 g of potassium cyanide in 500 ml of diethyl ether, and then, in the 1 course of 5 minutes and with ice-cooling, a solution of 148 g of ammonium chloride in 600 ml of water. After the mixture has been stirred for 2 hours at room temperature (approx. 25 0 the phases are separated, and the ether phase is washed once with dilute NaCl solution and three 2 times with H20, dried and concentrated. This gives 191 g of the title compound as an oil.

1 H NMR (CDC1 3 4.20 br, 1H, OH); 5.75 1H, CHOH); 7.05-7.75 4H, phenyl H).

l.b Synthesis of methyl 2-fluoromandelimidate hydrochloride

F

H OCH 3

HO

NH

2

CIE

235 g of the cyanohydrin of 1 are dissolved in 1000 ml of diethyl ether and 100 g of methanol. 126 g of a 55 percent strength solution of HC1 in ether 69 g HC1) are added dropwise to this solution with ice-cooling in the course of minutes. After the mixture has been left to stand for hours at room temperature (approx. 25 0 the precipitate is filtered off and dried in a stream of nitrogen. Yield: 108 g of the title compound.

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

0050/46490 139 l.c Synthesis of methyl 2-fluoromandelate

F'

HO OCH3

HO

The product of .b (108 g) is refluxed with stirring for half an hour in 450 ml of H 2 0. When cold, the mixture is extracted three times with ether, and the ether phase is dried and concentrated. This gives 77 g of the title compound.

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

l.d Synthesis of methyl 2-fluorophenylglyoxylate O OCH3 0 3.2 g of KBr, 8.7 g of Na 2 HP0 4 7.6 g of NaH 2

PO

4 x 2H 2 0, 2.8 g of 2,2,6,6-tetramethylpiperidine N-oxide and 600 ml of

H

2 0 are added to 77.1 g of the product of l.c in 700 ml of

CH

2 C12. 343 g of a 12.5 percent strength NaOCl solution are added dropwise at 20 0 C in the course of 1/2 hour to this mixture, with stirring. Stirring is continued for 1 hour.

The organic phase is separated off and the aqueous phase is re-extracted with CH 2 C12. The combined organic phases are washed three times with H 2 0, dried and concentrated. This gives 72.3 g of the title compound.

1 H NMR (CDC1 3 3.97 3H, OCH 3 7.08 (dd, 1H, phenyl H), 7.16 (dd, 1H, phenyl 7.33 (dd, 1H, phenyl H), 7.93 ppm (dd, 1H, phenyl H).

0050/46490 140 l.e Synthesis of N-methyl-2-fluorophenylglyoxylamide

F

.NHCH 3 17.1 g (0.22 mol 1.1 eq.) of methylamine solution strength in water) were added at approx. 25°C to a solution of 36 g (0.2 mol) of the product of 1.d in 150 ml of tetrahydrofuran. After the mixture had been stirred for 3 hours, the solvent was removed under reduced pressure. The resulting residue crystallized. This gave 30.0 g of the title compound 98-100°C).

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

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

CH

3

H

3 CO' N N OH CH3 43.8 g of pyridine are added to 18.7 g of (E)-diacetylmonoxime in 100 ml of methanol, and 17 g of o-methylhydroxylamine [sic] hydrochloride, dissolved in 50 ml of methanol, are subsequently added dropwise with stirring. After 3 hours, the mixture is evaporated to dryness, the residue is taken up in ether and washed with dilute hydrochloric acid, and the ether phase is subsequently dried and concentrated. This gives 24 g of the title compound.

1 H NMR (CDC13): 2.01 2.09 (2 x s, 6H, CH 3 3.98 3H,

OCH

3 8.59 1H, OH).

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

OH

3 H3- N OH

CH

3 CH3 0050/46490 141 g (1 mol) of pyridine and 35 g (0.5 mol) of hydroxylamine hydrochloride were added to a solution of 50 g (0.5 mol) of 3-methylpent-3-en-2-one in 500 ml of methanol. After the reaction mixture had been stirred for 12 hours at room temperature (approx. 25 0 it was freed from solvent under reduced pressure. The residue was taken up in tert-butyl methyl ether. The organic phase was washed with water and dilute hydrochloric acid, dried and concentrated under reduced pressure. This gave 48.0 g of the title compound as white crystals 70-72°C).

1 H NMR (CDC1 3 1.78 3H, CH 3 1.85 3H, CH 3 2.04 3H, CH 3 6.01 3H, 9.98 1H, OH).

l.h Synthesis of methyl 2 -oxo-[ 2 -(1-meta-tolylethylideneaminooxy)phenyl]acetate

N-

0 CH 3 CH3 aO CH3

O

0 3.0 g of potassium tert-butanoxide are added at 20°C to a mixture of 4.0 g of 3-methylacetophenone oxime in 20 ml of N,N-dimethylacetamide (DMA), the mixture is stirred for 1/2 hour, and a mixture of 5.9 g of methyl 2-fluorophenylglyoxalate in 20 ml of DMA is subsequently added dropwise at 15°C. After 3 hours at 20°C, a sufficient amount of methyl tert-butyl ether and aqueous NH 4 C1 solution are added, the phases are separated, and the organic phase is washed three times with NH 4 C1 solution and then dried and concentrated.

After column chromatography on silica gel, 4.1 g of the title compound are obtained.

1 H NMR (CDC13): 2.40 2.41 (2 x s, 6H, CH 3 3.85 3H,

OCH

3 7.14 1H, phenyl 7.22-7.63 6H, phenyl 7.80 (dd, 1H, phenyl H).

0050/46490 142 l.i Synthesis of methyl 2 -methoxyimino-l-methylpropylideneaminooxy)phenyl]oxoacetate SO H ,OCH 3 CH3 -O

CH

0 g of potassium tert-butoxide are added to 2.3 g of the product of 1.f in 15 ml of DMA, the mixture is stirred for 1/2 hour, and 3 g of the methyl 2 -fluorophenylglyoxalate of 1.d, dissolved in 6 ml of DMA (dimethylformamide), are subsequently added dropwise at 20°C, during which process the temperature is held at 20 0 C by means of ice-cooling. Stirring is then continued for 2 hours. For work-up, the reaction mixture is transferred into NH 4 C1 solution and the aqueous phase is extracted repeatedly with ether. The combined organic phases are washed with ammonium chloride solution, dried and concentrated. This gives 3.9 g of the title compound.

1 H NMR (CDC1 3 2.09 2.22 (2 x s, 6H, CH 3 3.88 4.01 (2 x s, 6H, OCH 3 7.50 (dd, 2H, phenyl 7.82 1H, phenyl H).

l.j Synthesis of N-methyl- 2 -oxo[2-(2-methoxyimino-l-methylpropylideneaminooxy)phenyl]acetamide H 3 Q -10 1N

WOCH

3 CHaN 'O C H3 0 A mixture of 1.4 g (10.5 mol) of the product of 1.f, 1.2 g (11 mol) of potassium tert-butoxide and 1.8 g (10 mmol) of the product of 1.e in 30 ml of dimethylacetamide was stirred for 1 hour at 60°C. The resulting reaction mixture was poured into ice-water. The aqueous mixture was extracted twice with CH 2 C1 2 The combined organic phases were dried with Na 2

SO

4 and subsequently concentrated under reduced pressure. This gave 1.3 g of the title compound as a brown oil.

143 1 H NMR (CDC1 3 2.02 2.20 (2 x s, 6H, CH 3 2.91 3H,

NCH

3 3.98 3H, OCH 3 6.89 1H, NCH); 7.09 (d, 1H, phenyl 7.31 1H, phenyl 7.49 1H, phenyl 7.65 1H, phenyl H).

l.k Synthesis of methyl 2-oxo-[2-(l-ethoxyethylideneaminooxy)phenyl]acetate T CH 2

CH

3

CH

3 O 0 0 24.7 g (0.22 mol) of potassium tert-butoxide were added to a solution of 22.7 g of 1-ethoxyethylamine oxime in 300 ml of toluene and the mixture was subsequently stirred for 2 hours. The resulting mixture was concentrated at 40'C under reduced pressure, and the residue obtained was taken up in 500 ml of dimethylformamide.

A solution of 40.1 g (0.22 mol) of l.d in 250 ml of dimethylformamide was added dropwise to the resulting solution at 15°C. After 3 hours, the reaction mixture obtained was treated with ice-water and 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 oil which remained was purified by column chromatography [on silica gel with cyclohexane/ethyl acetate This 30 gave 30 g of the title compound as an oil.

:o 1H NMR (CDC13): 1.28 3H, CH3); 2.08 3H, CH 3 3.83 *3.88 (2 x s, 6H, OCH3); 4.18 2H, OCH 2 7.05 (t, S1H, phenyl 7.38 1H, phenyl 7.54 1H, phenyl 7.76 1H, phenyl H).

0° 1.1 Synthesis of methyl 2-oxo-[2-(3-methylpent-3-en-2-ylidene- *a iminooxy)phenyl]acetate *o CH3 N CH3 *0 ell I^

N

144 A mixture of 3.0 g (20 mmol) of the product of 2.2 g mmol) of potassium tert-butoxide and 20 ml of methanol was stirred for 10 minutes and then evaporated to dryness under reduced pressure at approx. The residue was taken up in 20 ml of dimethylformamide, a solution of 3.5 g (20 mmol) of the product of l.d and 10 ml of dimethylformamide was added, and the resulting mixture was stirred for 2 hours at 50 0 C. The reaction mixture was treated 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 of oil) was purified by column chromatography [silica gel, cyclohexane/ethyl acetate This gave 2.0 g of the title compound as an oil.

1H NMR (CDC13): 1.82 3H, CH 3 1.90 2.04 (2 x s, 6H,

CH

3 3.85 3H, OCH3); 6.14 1H, 7.10 (t, 1H, phenyl 7.52 2H, phenyl 7.80 1H, phenyl H).

2. Preparation of the compounds I: 2.a Synthesis of methyl methoxyimino-[2-(1-meta-tolylethylideneaminooxy)phenyl]acetate I OC CH 3

CH

3 1 .0OCH 3

SCH

3 o 0 0.8 g of the keto ester of l.h together with 0.24 g of o-methylhydroxylamine [sic] hydrochloride and 0.23 g of py- 35 ridine are stirred for 1 hour at 50°C in 7 ml of CH30H. The methanol is then removed in vacuo and the residue is taken up in ethyl acetate, washed with dilute HCl and then with water, dried and concentrated. Crude yield 6.3 g which slowly crystallize. After purification by column chromatography, 40 2.2 g of the title compound are isolated from the second fraction; m.p. 1 H NMR (CDC13): 2.32 2.34 (2 x s, 6H, CH3); 3.82 4.09 (2 x s, 6H), OCH 3 7.10 1H, phenyl 7.21-7.61 7H, phenyl H).

145 2.b Synthesis of 2-methoxyimino-N-methyl-2-(2-(1-meta-tolylethylideneaminooxy)phenyl]acetamide N 0 a

CH

3

CH

3 N OCH3 I NI CH 3 0 2.9 ml of 40 percent strength aqueous methylamine solution are added, a little at a time, at reflux temperature to g of the oxime ether of 2.a in 4 ml of tetrahydrofuran.

Stirring of the mixture is continued overnight, and the mixture is then concentrated under reduced pressure, taken up in ethyl acetate, washed with NaCl solution, dried and evaporated. This gives 0.4 g of the title compound; pale yellow crystals, m.p. 109-111'C.

1 H NMR (CDC13): 2.35 2.40 (2 x s, 6H, CH 3 2.92 3H, NCH3); 4.00 3H, OCH 3 6.68 IH, NH); 7.10 (t, 1H, phenyl 7.22-7.62 7H, phenyl H).

2.c Synthesis of methyl methoxyimino-(2-(2-methoxyimono-l-methylpropylideneaminooxy)phenyl]acetate [sic] CH3 0 L N.OCH3 CH3 N. N /OCHCH 3 3 g of the crude product of 1.i in 20 ml of methanol are S 35 reacted with 0.83 g of o-methylhydroxylamine at room temperature (approx. 25 0 After 3 hours, the solvent is drawn off in vacuo and the residue is subjected to column chromatography on silica gel with cyclohexane/ethyl acetate 15:1 as the eluent. 1.3 g of the title compound of m.p. 93- 40 94°C were isolated as the second fraction.

1 H NMR (D 6 -DMSO): 2.01 2.04 (2 x s, 6H, CH 3 3.71 3H, OCH3); 3.95 6H, OCH 3 7.12 IH, phenyl H); 7.31 1H, phenyl 7.43 2H, phenyl H).

146 2.d Synthesis of N-methyl-methoxyimino-(2-(2-methoxyimino-lmethylpropylideneaminooxy)phenyl]acetamide oN

_N,OCH

3

CH

3 N 1 NOCH3 CH

CH

3 Process A: The product of 2.c (0.6 g) was stirred overnight at room temperature (approx. 25 C) in 10 ml of tetrahydrofuran is (sic] together with 3.6 g of 40 percent strength aqueous methylamine solution. After the solvent had been stripped off under reduced pressure, water had been added, and the resulting crystalline residue had been isolated and dried, 0.3 g of the title compound was obtained 122-123'C).

1H NMR (CDC13): 2.05 2.12 (2 x s, 6H, CH3); 2.90 3H,

NCH

3 3.92 3.98 (2 x s, 6H, OCH 3 6.70 1H, NH); 7.07 1H, phenyl 7.22 IH, phenyl H); 7.38 1H, phenyl 7.49 1H, phenyl H).

Process B: A solution of 1.1 g (4 mmol) of the product of 1.i in 30 ml of methanol was treated with 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 30 under reduced pressure. The residue was taken up in ethyl acetate, and the resulting solution was washed in each case twice with water and dilute hydrochloric acid. The organic phase was dried over Na 2

SO

4 and concentrated under reduced pressure. This gave 1.1 g of the title compound as a yellow S35 oil.

2.e Synthesis of methyl 3 -methoxy-[2-(2-methoxyimono-l-methylpropylideneaminooxy)phenyl] acrylate.

40 H C,0N OCCH3

OCH

3

CH

3 0 0050/46490 147 e) The crude product of Preparation Example 1.i, specifically 2.4 g of this, dissolved in 10 ml of dimethylformamide (DMF), is added dropwise to a mixture of 5.6 g of methoxymethyltriphenylphosphonium chloride and 2.5 g of 30 percent strength sodium methylate solution (in methanol) in 20 ml of DMF. After 3 hours, 30 ml of H 2 0 are added dropwise with ice-cooling, and the resulting precipitate is filtered off with suction. After chromatography over Si02 with cyclohexane/ethyl acetate, 1.8 g of the title compound are obtained from the second fraction as pale yellow solid 101°C).

1 H NMR (CDCl 3 2.09 2.11 (2 x s, 6H, CH 3 3.65 3,82 (2 x s, 6H, OCH 3 7.01 1H, phenyl 7.22 (m, 2H, phenyl 7.45 1H, phenyl 7.49 1H,

CH).

2.f Synthesis of methyl 3-methoxy-[2-(1-ethoxyethylideneaminooxy)phenyl]acrylate 0 T^ TH 2

CH

3

,-OCH

3

CH

3

I

0 A solution of 2.7 g (0.01 mol) of the product of 1.k and ml of dimethylformamide was added dropwise to a solution of 6.9 g (0.02 mol) of methoxymethyltriphenylphosphonium chloride, 3.1 g (0.017 mol) of sodium methoxide strength in methanol) and 30 ml of dimethylformamide. After 3 hours, the reaction mixture was transferred into ice-water and extracted with tert-butyl methyl ether. The combined organic phases are [sic] dried over Na 2

SO

4 and concentrated under reduced pressure. The resulting residue was purified by column chromatography [silica gel, toluene/ethyl acetate This gave 1.9 g of the title compound as an oil.

1 H NMR (CDC1 3 1.26 3H, CH 3 2.00 3H, CH 3 3.65 (s, 3H, OCH3); 3.80 3H, OCH 3 4.18 2H, OCH 2 6.95 1H, phenyl 7.20 1H, phenyl 7.30 (t, 1H, phenyl 7.43 1H, phenyl 7.50 1H,

=CH).

0050/46490 148 2.g Synthesis of methyl 2-methoxyimino-[2-(1-ethoxyethylideneaminooxy)phenyl]acetate N 0 S CH 2

CH

3

CH

3 0 N OH

CH

3 OH 0 A mixture of 1.0 g (4.0 mmol) of the product of l.k and 5 ml of methanol was treated with 0.25 g of 0-methylhydroxylamine and stirred for approximately 24 hours at approximately The resulting reaction mixture was concentrated under reduced pressure, and the residue obtained was taken up in CH2C1 2 The organic phase was washed with water, dried and concentrated under reduced pressure. This gave 1.0 g of the title compound [2:1 isomer mixture].

1 H NMR (CDCl 3 1.26 3H, CH 3 2.01 2.05 (2 x s, 6H,

CH

3 3.86 4.04 (2 x s, 6H, OCH 3 4.10 2H,

OCH

2 6.94-7.50 4H, phenyl H).

2.h Synthesis of methyl 2-methoxyimino-[2-phenylmethylideneaminooxyphenyl]acetate

CH

3 Qe lOCH 3 0 A solution of 1.0 g (3.4 mmol) of the product of l.k and 5 ml of methanol was treated with 1.8 g (17 mmol) of benzaldehyde and 0.33 g of methanesulfonic acid, and the resulting mixture was stirred for 1 hour. The resulting solution was concentrated under reduced pressure and the residue which remained was taken up in CH2C1 2 The organic phase was washed with water, dried and concentrated. The residue obtained thus was purified by column chromatography [toluene/ethyl acetate This gave 400 mg of the title compound as an oil.

1 H NMR (CDC1 3 3.95 3H, OCH 3 4.02 3H, OCH 3 7.30-7.68 9H, phenyl 8.05 1H, =CH).

0050/46490 149 2.i Synthesis of methyl 2 2 -(3-methylpent-3-en-2-ylideneiminooxy)phenyl]but-2-enoate

OOH

3 SNO

CH

3 CH3 IH3

O

C

H

3 0 A mixture of 4.7 g (14.5 mmol) of ethyltriphenylphosphonium chloride in 20 ml of dimethylformamide was treated with 2.2 g (12 mmol) of sodium methoxide solution (30% strength in methanol) at approximately 25 0 C. A solution of 2.0 g of the product of 1.1 in 10 ml of dimethylformamide was subsequently added dropwise to the resulting mixture, and stirring was continued for 2 hours. The reaction mixture was then treated with water and extracted with tert-butyl methyl ether. The combined organic phases were dried and concentrated under reduced pressure. The residue which remained was purified by column chromatography [cyclohexane/ethyl acetate This gave 700 mg of the title compound as a solid 90-93°C).

1 H NMR (CDC1 3 1.72 3H, CH 3 1.80 3H, CH 3 1.89 3H, CH 3 2.03 3H, CH 3 3.68 3H, OCH 3 6,03 (pseudo q, 1H, 6.98-7.35 5H, phenyl H, 7.50 1H, phenyl H).

Table I(1): I R I(i) R1 R 3 No. R 1

R

3

R

4 Physical data I(1).1 Ia CH 3 3-CH 3 -C6H 4 900c I(1).2 Ib CH 3 3-CH 3

-C

6

H

4 109 111°C Ia CH 3 4-CH 3

-C

6

H

4 990C I(1).4 Ib CH 3 4-CH 3 -CsH 4 109 0

C

1(1).5 Id -CH 2

-(CH

2 3

-CH

2 oil I(1).6 Ia CH 3

OC

2

H

5 1 H: 1.32 2.06 (s,3H); 3.92 4.05 4.08 6.95-7.42 (m,4H) 0050/46490 150 No. R 1 RR4Physical data 1(1).7 Id OH 3 0C 2

H

5 1 H: 1.28 2.03 (s,3H); 3.76 3.84 4.08 (cj,2H); 6.98 7.08 7.21 7.42 7.50 (s,1H).

1(1).8 Ia H 3 1280C I(1).9 Tb CH 3 135-1370C Table 1(2):

R

0 Q(1 R) RI

R

3 No. R 1

R

3 R5R 6 Physical data I(2).1 Ia OH 3 4-F-C 6

H

5

CH

3 112 0

C

1(2).2 Ia OH 3

CH

3

OH

3 930C 1(2).3 lb OH 3

OH

3

OH

3 122 1230C 1(2) .4 Id OH 3 4-F-C 6

H

5

OH

3 1410C 1(2) .5 lb OH 3 4-F-C 6

H

5

OH

3 13900 1(2).6 Id OH 3

CH

3

CH(CH

3 2 1030C 1(2).7 Id OH 3

CH

3

CH

3 10100 1(2).8 lb OH 3

OH

3

CH(CH

3 2 97 0

C

1(2).9 Ia OH 3

OH

3

C

2

H

5 106 1090C 1(2).10 Tb OH 3

OH

3

C

2

H

5 119 1230C I(2).11 Ia C 2

H

5

OH

3

OH

3 92 97 0

C

1(2) .12 Tb 02115 OH 3

OH

3 97 10000 1(2).13 Ia OH 3

OH

3

CH(CH

3 2 740C 1(2).14 Id 02115 OH 3

OH

3 1711, 1647, 1542, 1288, 1266, 1132 1(2).15 Id OH 3

OH

3

C

2

H

5 78 8000 1(2).16 Ia OH 3

OH

3 CH2CO=CH 51 5300 1(2).17 Id OH 3

OH

3

CH

2 0-OH 59 6300 1(2).18 lb OH 3

OH

3

CH

2 CmCH 146 14900 1(2).19 Tb OH 3

C

2

H

5

CH

3 11300 1(2).20 Id 0113 C 2

H

5 0113 1713, 1638, 1541, 1258, 1128, 1051.

0050/46490 151 No. R 1

R

3 RR6Physical data 1(2).21 Ia OH 3

C

2

H

5

OH

3 1732, 1453, 1224, 1207, 1050.

1(2).22. lb C 2

H

5

OH

3

C

2

H

5 101 10300 1(2).23 Id 02H5 CH 3

C

2

H

5 88 92 0

C

1(2).24 Ia C 2

H

5

CH

3

C

2

H

5 10200 1(2).25 lb C 2

H

5

CH

3

CH(CH

3 2 92 940C 1(2).26 Id C2H5 OH 3

CH(CH

3 2 74 780C 1(2).27 Ia C 2

H

5

OH

3

CH(CH

3 2 93 960C 1(2).28 lb C 2

H

5

CH

3

CH

2 CmCH 95 -1000C 1(2).29 Id C 2

H

5

OH

3

CH

2 CmCH 1711, 1637, 1542, 1252, 1218, 1129.

1(2).30 Ia C 2

H

5

CH

3

CH

2 C=-CH 1731, 1480, 1453, 1227, 1207, 1072.

1(2).31 lb C 6

H

5

OH

3

OH

3 122 12500 1(2).32 Id C 6

H

5

OH

3

OH

3 116 12000 1(2).33 Ia 0 6

H

5

OH

3

OH

3 107 11300 1(2).34 Ia OH 3 OCH (CH 3 2

OH

3 7800 1(2).35 lb OH 3

CH

2

CH

3

CH

2 C=-CH 100 10300 1(2).36 Ia OH 3 MH-iH CH 2 C=-CH 94 9700 1(2) .37 Id OH 3

OH

2

CH

3

CH

2 C=-CH oil 1(2).38 Ia OH 3

CH

2

CH

3

CH

2

CH

3 91 9500 1(2).39 lb CH 3 MHH 0H 2

CH

3 91 930C 1(2) .40 Id OH 3

CH

2

CH

3

CH

2 0H 3 oil 1(2).41 Ie OH 3

CH

2

CH

3

CH

2 0H 3 oil (2).42 Ia

H

3

CH

2 0CH 3

H

3 oil 1(2).43 lb OHCHH3 3

OH

3 r 95 -1000C Table 1(3): Rx N Ry jy I(v) RiR 3 Rz No. R 1

R

3 Rx RY Rz Physical data I(3).1 Ia OH 3 H C 6

H

5 H 1020C 1(3).2 lb OH 3 H C 6

H

5 H 15500 1(3).3 Ia OH 3 H 4-F-C 6

H

5 H 10900 1(3).4 lb OH 3 H 4-F-C 6

H

5 H 72 750C 1(3).5 Ia OH 3 H 4-01-615 H 14100 1(3).6 lb OH 3 H 4-Cl-C 6

H

5 H 1470C 1(3).7 Ia OH 3 H 0113 0113 58 6000 0050/46490 152Ph s c l d t No. R 1

R

3 RX RY RZPhscldt 1(3).8 Ib CH 3 H CH 3

OH

3 85 -880C 1(3).9 lb' CH 3

CH

3

OH

3 H 83 -8400 1(3).10 lb CH 3

OH

3

CH(CH

3 2 H 69 -7100 I(3).11 Ia- OH 3

OH

3

-CH

3 H 81 -83 0

C

1(3).12 Ia OH 3

OH

3

CH(CH

3 2 H 90 -9200 1(3).13 Id OH 3

OH

3

OH

3 H 90 -93 0 c 1(3).14 Id OH 3

OH

3

CH(CH

3 2 H 78 8000 1(3).15 Ie OH 3

CH

3

CH

3 H 69 720C 1(3).16 Ie CH 3

OH

3

CH(CH

3 2 H 56 59 0

C

1(3).17 Ia OH 3 H H C 6

H

5 8800 1(3).18 Ia OH 3

CH

3

C

2

H

5 H 83 860C 1(3).19 lb' OH 3

OH

3 0 2

H

5 H 81 8600 1(3).20 Id OH 3

OH

3

C

2

H

5 H 77 790C 1(3).21 Ie OH 3

OH

3

C

2

H.

5 H oil 1(3).22 Ia OH 3

CH

3

C

3

H

7 H 80 -8200 1(3).23 lb OH 3

OH

3 0 3

H

7 H 99 -10000 1(3).24 Id OH 3

OH

3

O

3

H

7 H 74 -7600 1(3).25 Ie OH 3

OH

3

C

3

H

7 H 54 -5600 1(3).26 lb OH 3

OH

3 4-F-C 6

H

4 H 140 -14200 1(3).27 Ia OH 3

OH

3

C

6

H

5 H 115 11700 1(3).28 Ia OH 3

OH

3 4-F-0 6

H

4 H 103 10500 1(3).29 Id OH 3

OH

3

C

6

H

5 H 10800 1(3).30 Id OH 3

OH

3 4-F-C 6

H

4 H 10800 1(3).31 le OH 3

OH

3

C

6

H

5 H 1 81 -8300 Te OH 3

OH

3 4-F-C 6

H

4 H 82 -8400 Table VI: OR (I

R

3

-I

0 No. R 2 m R 3

R

4 1 H NMR (CD01 3

PPM)*

VI.1 H OH 3 3-0H 3 -0 6

H

4 2.42 2.44 E 3.85 7.1-7.9 (8H, multiplets) VI.2 H OH 3 C(0H 3

)=NOOH

3 2.1 2.2 E,E 3.75 4.0 (3H,s), 7.1-7,9 (4H, four multi- _____plets) C onfiguration of the double bond 153 Examples of the action against harmful fungi: 1. Action of the compounds as mitochondrial respiration inhibitors To determine the effect of the compounds according to the invention on mitochondrial respiration, it is first necessary to isolate the mitochondria from the test organisms. In the case of the yeast Saccharomyces cerevisiae, a 30 to 40% cell suspension of the fungus is disrupted, to this end, in an aqueous solution of 0.6 M Mannitol 0.01 M tris[hydroxymethyl]aminomethane 0.002 M disodium ethylenediaminetetraacetate (pH 6.8) using a glass bead mill, and the extract is fractionated by means of differential centrifugation at 1000 x g and 12000 x g. The mitochondria are in the precipitate of the 12000 x g centrifugation.

Using similar methods, it is also possible to isolate mitochondria from other fungi, eg. from the phytopathogenic fungus Drechslera sorokiniana (synonym Helminthosphorium sativum), from the dermatophyte Trichophyton mentagrophytes, which is pathogenic to humans, and from other organisms, eg. from the common housefly (musca domestica) as an insect, or from the spider mite Tetranychus urticae.

The effect of the compounds on the respiration chain is determined by adding a solution of the test compound in dimethyl sul- I foxide to a suspension of mitochondria in an aqueous solution of 0.01 M tris(hydroxymethyl]aminomethane 0.65 M sorbitol 0.01 M KH 2

PO

4 0.01 M KC1 0.0004 M disodium ethylenediamine- 30 tetraacetate 0.3% bovine serum albumin 0.0007 M KCN 6 x 10- 6 ubiquinone-50 0.01 M sodium succinate 0.15% cytochrome c (pH and the reduction rate of the cytochrome c is determined photometrically on the basis of the increased absorption at 546 nm. A batch with a corresponding amount of 35 pure DMSO is used as control. The inhibitory value for the active ingredient at the concentration shown in each case is then calculated as follows.

40 A E A E o inhibition 100 o 0050/46490 154 where AE is the difference in absorption, At the difference in time, SA E the reaction rate of the control and A t o I E the reaction rate of the sample x.

x In the table which follows, the action of a series of compounds according to the invention as respiration inhibitors on the mitochondria of the yeast Saccharomyces cerevisiae, the phytopathogenic fungus Drechslera sorokiniana and the common housefly Musca domestica.

In each case, the inhibition of mytochondrial respiration is given as 150 value (this being the concentration of test substance where a 50% inhibition is observed) and as F value, this being a relative value defined as follows: 150 (test substance) F (reference substance) The reference substance is the so-called enol ether stilbene, of the following formula: Z< -OCH 3

I

0 Table II: Inhibition of mitochondrial respiration by compounds of the formula I of Tables I(1)-I(3) 0050/46490 155 No. Saccharom. cerevisiae (Mol/1) F I(1).1 2.7 .10-8 0.96 I(1).2 3.2 10-7 11 I(2).7 3.3 10-9 0.14 I(2).2 1.2 10-8 0.43 I(2).3 2.7 10-7 9.6 The fungicidal activity of the compounds of the general formula I was demonstrated by the following greenhouse experiments: The active ingredients were formulated as a 20% emulsion in a mixture of 70% by weight of cyclohexanone, 20% by weight of Nekanil® LN (Lutensol® AP6, wetting agent having emulsifying and dispersant action based on ethoxylated alkylphenols) and 10% by weight of Emulphor®EL (Emulan® EL, emulsifier based on ethoxylated fatty alcohols) and diluted with water to give the desired concentration.

Activity against Erysiphe graminis var. tritici Leaves of wheat seedlings (variety "Kanzler") were first treated with the aqueous preparation of the active ingredients (strength 250 ppm). After approximately 24 hours, the plants were dusted with spores of powdery mildew of wheat (Erysiphe graminis var.

tritici). The treated plants were subsequently incubated for 7 days at 20-220C and a relative atmospheric humidity of 75-80%.

The extent of fungal development was subsequently determined.

In this test, the disease level of plants which had been treated with the compounds according to the invention was 15% and less, the disease level of the plants which had been treated with a known active ingredient (Compound No. 195, Table 3, EP-A 463 488) was 40% and the disease level of the untreated plants was In a similar test (wheat seedlings cv. "Kanzler", rate of application 63 ppm), in which the plants were first infected and incubated and subsequently treated with the active ingredients, the disease level of the plants which had been treated with the compounds according to the invention was 5% and less, the disease level of the plants which had been treated with a known active ingredient (Compound No. 195, Table 3, EP-A 463 488) was and the disease level of the untreated plants was 156 In a similar test (wheat seedlings cv. "FrQhgold", rate of application 250 ppm), in which the plants were first treated with the active ingredients and subsequently infected and incubated, the disease level of the plants which had been treated with the compounds according to the invention was 15% and less and the disease level of the untreated plants was Activity against Plasmopara viticola (Rebenperonospora) Grapevines in pots (variety: "Mller Thurgau") were sprayed to run-off point with the preparation of active ingredient (rate of application: 63 ppm). After 8 days, the plants were sprayed with a zoospore suspension of the fungus Plasmopara viticola and kept for 5 days at 20-30'C and high atmospheric humidity. Then, prior to assessment, the plants were kept for 16 hours at high atmospheric humidity. Scoring was carried out visually.

In this test, the disease level of the plants which had been treated with the active ingredients according to the invention was 15% and less, while the disease level of the untreated (control) plants was Examples of the activity against animal pests The activity of the compounds of the general for-mula I against insects, arachnids and nematodes was demonstrated by the following greenhouse experiments: 30 The active ingredients were formulated a) as a 0.1% strength solution in acetone or b) as a 10% emulsion in a mixture of 70% by weight of cyclo- 35 hexanol, 20% by weight of Nekanil® LN (Lutensol® AP6, wetting agent having emulsifying and dispersant action based on ethoxylated alkylphenols) and 10% by weight of Emulphor®EL emulsifier based on ethoxylated fatty alcohols) 40 and diluted to give the desired concentraton, using acetone in the case of a) and water in the case of b).

After the experiments had been concluded, in each case the lowest concentration at which the compounds still caused an 80-100% inhibition or mortality in comparison with untreated control experiment was determined (limit or minimum concentration).

0050/46490 157 Aphis fabae (blackbean aphid), contact action Severely infested dwarf beans (Vicia faba) were treated with the aqueous preparation of active ingredient. After 24 hours, the mortality rate was determined.

In this test, a limit concentration of 200 ppm was shown by compound I(2).9.

Heliothis virescens (tobacco budworm), contact/stomach action Tobacco plants approximately 10 cm high were treated with the aqueous preparation of active ingredient. After the plants had dried, they were populated with in each case 10 3rd instar larvae. Mortality and antifeeding effect were assessed after 48 hours.

In this test, a limit concentration of 40 ppm was shown by compound I(2).17.

Nephotettix cincticeps (green rice leafhopper), contact action Circular paper filters were treated with the aqueous preparation of active ingredient and subsequently populated with 5 adult leafhoppers. After 24 hours, the mortality was assessed.

In this test, limit concentrations of 0.2 mg and less were shown by compounds I(2).19, I(2).20, I(2).21, I(2).22, I(2).25, I(2).26, I(2).27, I(2).28 and I(2).29.

Prodenia litura (Egyptian cotton leafworm), contact/stomach action Five L3 instar caterpillars (10-12 mm) which had not suffered noticeable damage in the contact experiment were placed on standard culture media (3.1 1 water, 80 g agar, 137 g brewers' yeast, 515 g cornflour, 130 g wheat germ and customary additives and vitamins (20 g Wesson salt, 5 g Nipagin, 5 g sorbose, 10 g cellulose, 18 g ascorbic acid, 1 g Lutavit® blend (vitamin), 5 ml alcoholic biotin solution)) which had previously been wetted with the aqueous preparation of active ingredient. The caterpillars were observed until the adults had hatched in a control experiment without active ingredient.

In this test, limit concentrations of 0.2 mg and less were shown by compounds I(2).16 and I(2).17.

0050/46490 158 Tetranychus telarius (greenhouse red spider mite), contact action Severely infested dwarf beans, in pots, which showed the second consecutive pair of leaves were treated with aqueous preparations of active ingredient. After 5 days in the greenhouse, the result of the control measures was determined by means of a stereomicroscope.

In this test, limit concentrations of 200 ppm and less were shown by compounds I(2).9, I(2).13, I(2).14, I(2).15, I(2).16, I(2).17, I(2).19, I(2).20 and I(2).21.

0050/46490 159 We claim: 1. 2-Iminooxyphenylacetic acid derivatives of the formula I

(I)

~R

3

R

where the substituents and the index have the following meanings:

R

1 is C(CO 2

CH

3

)=NOCH

3

C(CONHCH

3

)=NOCH

3 (Ib),

C(CONH

2

)=NOCH

3

C(CO

2

CH

3

)=CHOCH

3 (Id) or

C(CO

2

CH

3

)=CHCH

3 (Ie);

R

2 is cyano, nitro, halogen, Cl-C 4 -alkyl, Cl-C 4 -haloalkyl or Cl-C 4 -alkoxy; m is 0, 1 or 2, it being possible for the radicals R 2 to be different when m is 2;

R

3 is hydrogen, cyano, hydroxyl, halogen, Cl-C 6 -alkyl, Cl-C 6 -haloalkyl, Cl-C 6 -alkoxy-Cl-C 6 -alkyl, Cl-C 6 -alkoxy, Cl-C 6 -haloalkoxy, Cl-C 6 -alkylthio, cyclopropyl, C 2

-C

6 alkenyl, aryloxy-Cl-C 6 -alkyl, benzyl or benzyloxy, it being possible for the aromatic rings in these radicals to have attached to them one to three of the following groups: cyano, nitro, halogen, Cl-C 6 -alkyl, Cl-C 6 -haloalkyl, Cj-C 6 -alkoxy, Cl-C 6 -haloalkoxy, or C(CH 3 )=N-Y-Ra where Ra is Cl-C 6 -alkyl and Y is oxygen or nitrogen, the nitrogen atom having attached to it a hydrogen atom or a Cl-C 6 -alkyl group;

R

4 is hydrogen, cyano, unsubstituted or substituted alkyl, alkenyl, alkynyl, cycloalkyl, heterocyclyl, aryl and hetaryl; 0050/46490 160 unsubstituted or substituted alkoxy, alkenyloxy, alkynyloxy, cycloalkoxy, heterocyclyloxy, aryloxy and hetaryloxy; unsubstituted or substituted arylthio and hetarylthio; -Qp-C(R 5

)=N-Y

1

-R

6 or -Q-O-N=CR 7

R

8 where Q is a direct bond, CH 2

CH(CH

3

CH(CH

2

CH

3 or 1,1-cyclopropyl; p is 0 or 1; yl is oxygen or nitrogen, the nitrogen atom having attached to it a hydrogen atom or a C 1

-C

4 -alkyl group;

R

5 is one of the groups mentioned for R 3 or unsubstituted or substituted cycloalkoxy, heterocyclyloxy, aryloxy, hetaryloxy, arylthio and hetarylthio;

R

6 is unsubstituted or substituted C 1 -Clo-alkyl, C3-C 6 -cycloalkyl, C 2 -Clo-alkenyl, C 2 -Clo-alkynyl, Ci-Clo-alkylcarbonyl, C2-Clo-alkenylcarbonyl, C2-Clo-alkynylcarbonyl or Ci-Clo-alkylsulfonyl; unsubstituted or substituted aryl, hetaryl, arylcarbonyl, hetarylcarbonyl, arylsulfonyl or hetarylsulfonyl;

R

7

,R

8 are methyl, ethyl, phenyl and benzyl, it being possible for the aromatic rings to have attached to them one to three of the following substituents: cyano, nitro, halogen, Ci-C 6 -alkyl, Cl-C 6 -haloalkyl, Ci-C 6 -alkoxy and Ci-C6-haloalkoxy;

R

3 and R 4 together with the carbon atom to which they are bonded are a four- to eight-membered ring which, besides carbon atoms, may contain one or two oxygen and/or sulfur atoms and/or NH and/or N(C 1

-C

4 -alkyl) groups and whose carbon atoms can have attached to them one of the following substituents: halogen, Ci-C 6 -alkyl or Ci-C 4 -alkoxyimino;

Claims (8)

1. 2. A compound of the formula I as claimed in claim 1 where R 4 has the following meanings: alkyl, alkenyl, alkynyl, alkoxy, alkenyloxy or alkynyloxy, it being possible for the hydrocarbon groups, in turn, to be partially or fully halogenated and/or to have attached to them one to three of the following radicals: cyano, nitro, hydroxyl, mercapto, amino, carboxyl, aminocarbonyl, axninothiocarbonyl, Cl-C6-alkylsulfonyl, CI-C6-alkylsulfoxyl, Cl-C 6 -alkyl- carbonyl, C3-C 6 -cycloalkyl, Cl-C 6 -alkoxy, Cl-C 6 -haloalkoxy, C1-C6-alkoxycarbonyl, Ci-C 6 -alkylthio, Cl-C6-alkylamino, di-Cl-C 6 -alkylamino, Cl-C6-alkylaminocarbonyl, di-Cl-C 6 alkylaminocarbonyl, Cl-C6-alkylaminothiocarbonyl, di-cl-C 6 alkylaminothiocarbonyl, C2-C 6 -alkenyloxy, benzyloxy, aryl, aryloxy, hetaryl and hetaryloxy, it being possible for the aromatic rings to be substituted by customary groups; cycloalkyl, cycloalkoxy, heterocyclyl or heterocyclyloxy, it being possible for the cyclic groups, in turn, to be partially or fully halogenated and/or to have attached to them one to three of the following radicals: cyano, nitro, hydroxyl, mercapto, amino, carboxyl, amino- carbonyl, aminothiocarbonyl, Cl-C 6 -alkyl, Cl-C 6 -haloalkyl, Cl-C6-alkylsulfonyl, Ci-C 6 -alkylsulfoxyl, Cl-C6-alkylcarbonyl, C 3 -C 6 -cycloalkyl, Cl-C 6 -alkoxy, C 1 -C 6 -haloalkoxy, Cl-C6-alkoxycarbonyl, Cl-C 6 -alkylthio, Cl-C 6 -alkylamino, di-Ci-C 6 -alkylamino, C-C6-alkylaminocarbonyl, di-Cl-C6-alkylaminocarbonyl, Cl-C6-alkylaminothiocarbonyl, di-Cl-C6-alkylaminothiocarbo- nyl, C 2 -C 6 -alkenyl, C2-C 6 -alkenyloxy, benzyl, benzyloxy, aryl, aryloxy, hetaryl and hetaryloxy, it being possible for the aromatic rings to be substituted by customary groups; aryl, hetaryl, aryloxy or hetaryloxy, it being possible for the cyclic groups, in turn, to be partially or fully halogenated and/or to have attached to them one to three of the following radicals: cyano, nitro, hydroxyl, mercapto, amino, carboxyl, amino- carbonyl, aminothiocarbonyl, 162 C-C 6 -alkyl, Cl-C 6 -haloalkyl, Cl-C6-alkylsulfonyl, Cl-C 6 -alkylsulfoxyl, Cl-C-alkylcarbonyl, C3-C6-cycloalkyl, CI-C 6 -alkoxy, Cl-C 6 -haloalkoxy, Cl-C 6 -alkoxycarbonyl, Cl-C 6 -alkylthio, Cl-C6-.alkylamino, di-C 1-C6- al kyl amino, C-C 6 -alkylaminocarbonyl, di-Cl--C6-alkylalninocarbonyl, Cl-C 6 -alkylaminothiocarbonyl, di-C1-C6-alkylaminothiocarbo-. nyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkenyloxy, benzyl, benzyloxy, aryl, aryloxy, hetaryl, hetaryloxy, it being possible for the aromatic rings to be substituted by customary groups, C (=NORi) -An-Rii or NRiii-CO.-D-Riv; A is oxygen, sulfur or nitrogen, the nitrogen having attached to it hydrogen or C 1 -C 6 -alkyl; n is 0orI.- Ri is hydrogen, C 1 -C 6 -alkyl, C3-C 6 -alkenyl or C 3 -C 6 -alkynyl; Rii is hydrogen or C 1 -C 6 -alkyl; D is a direct bond, oxygen or NRb (Rb =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, aryl- C 1 -C 6 -alkyl, hetaryl and hetaryl-Cl-C 6 -alkyl); Riii is hydrogen, hydroxyl, Cl-C 6 -alkyl, C 2 -C 6 -alkenyl, C2C*lknl ClCSloy 2C-leyoy C 2 -C 6 -alkynyl, C-C 6 -alkoxy C-C6-alkylo, CI-C6-alkoxy--Cl-C 6 -alkoxy and Cl-C 6 -alkoxycarbonyl; Riv is hydrogen, CI-C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 3 -C 6 -cycloalkyl, C 3 -C 6 -cycloalkenyl, aryl, aryl-Cl-C 6 -alkyl, hetaryl and hetaryl-Cl-C 6 alkyl. A composition for controlling animal pests or harmful fungi, including a solid or liquid carrier and a compound of the formula I as claimed in claim 1.
2. 4. A method of controlling harmful fungi, which includes trea- ting the fungi, or the materials, plants, the soil or seed to be protected against fungal infection, with an effective amount of a compound of the formula I as claimed in claim 1.- 163 A method of controlling animal pests, which includes trea- ting the pests, or the materials, plants, the soil or seed to be protected against them, with an effective amount of a compound of the formula I as claimed in claim 1.
3. 6. The use of a compound I as claimed in claim 1 for the prepa- ration of a composition for controlling animal pests or harmful fungi.
4. 7. The use of a compound I as claimed in claim 1 for control- ling animal pests or harmful fungi.
5. 8. A process for the preparation of a compound I as claimed in claim 1 where R 1 is C(CO 2 CH3)=NOCH 3 C(C02CH 3 )=CHOCH 3 (Id) or C(CO 2 CH 3 )=CHCH 3 which includes converting a benzoic ester of the formula II (L (Ri O-0 OR where L is a nucleophilically exchangeable leaving group and R is a C 1 -C 4 -alkyl group, in the presence of a base, with an oxime of the formula III R4 N-OH R N- -OH- (IV) R* R hydrolyzing IV to give the corresponding carboxylic acid IVa R;/ 'A- Luj 1 ,9_O 0050/46490 164 R4 R2m (IVa) R 3 OH and subsequently first reacting IVa to the chloride Va R4 j R2m (Va) R 3 CI and then to the cyanide Vb 2 m N-O (Vb) R 3 O0- C-N converting Vb, via a Pinner reaction, into the corresponding a-keto ester VI R4 R2m =N-OO 3 0 OR (VI) R 3 O and subsequently converting VI either a) with O-methylhydroxylamine or a salt thereof (VIIa) CH 3 -O-NH 2 CH 3 -O-NH 3 Ze (Vila) where Z- is a halide ion, to give the corresponding compound Ia [R C(CO 2 CH 3 )=NOCH 3 b) with a Wittig, or Wittig-Horner, reagent of the formula VIIb 165 CH 3 -O-CH 2 -P (Vllb) where P* is a phosphonate or a phosphonium halide radi- cal to give the corresponding compound Id (R C(C0 2 CH 3 )=CHOCH 3 or b) with a Wittig, or Wittig-Horner, reagent of the formula VIIc CH3-CH 2 (VIIc) to give the corresponding compound Ie [R C(C02CH 3 )=CHCH 3
6. 9. A process for the preparation of a compound I as claimed in claim 1 where R1 id C(CONHCH 3 )=NOCH 3 (Ib) or C(CONH 2 )=NOCH 3 (Ic), which includes converting a compound of the formula Ia as claimed in claim 8 in a manner known per se with methylamine or a salt thereof (XIII) CH 3 -NH 2 CH 3 -NH 3 Z G (XIII) where Z- is a halide anion to give the corresponding compound Ib [R C(CONHCH 3 )=NOCH 3 or with ammonia or an ammonium salt to give the corresponding compound Ic [R C(CONH 2 )=NOCH 3
7. 10. An intermediate of the formula Vb as claimed in claim 8.
8. 11. An intermediate of the formula X L°R 2 m O TR (X) 0 *O where R 2 and m have the meanings given in claim 1 and T is oxygen or nitrogen, it being possible for the nitro- gen atom to have attached to it a hydrogen atom or a Ci-C 6 -alkyl group; 166 R is a Cl-C 4 -alkyl group, and L' is a radical -O-N=CR3R 4 Where R 3 and R 4 have the meanings given in claim 1. DATED this 2nd day of July, 1999 B A S F AKTIENGESELLSCHAFT WATERMARK PATENT TRADEMARK ATTORNEYS 290 BURWOOD ROAD HAWTHORN VICTORIA 3122 AUSTRALIA LCG:CLR:PCP Doc 27 AU1372797.WPC 0 0050/46490 Iminooxyphenylacetic acid derivatives, their preparation, inter- mediates for their preparation, and their use Abstract 2 -Iminooxyphenylacetic acid derivatives 10R4R N, I R 3 R iwhere the substituents and th-e- index have the following meanings: R 1 is C(CO 2 CH 3 )=NOCH 3 C(CONHCH 3 )=NOCH 3 (Ib), C(CONH 2 )=NOCH 3 C(CO 2 CH 3 )=CHOCH 3 (Id) or C(CO 2 CH 3 )=CHCH 3 (le); R 2 is cyano, nitro, halogen, alkyl, haloalkyl or alkoxy; m is 0, 1 or 2; R 3 is hydrogen, cyano, hydroxyl, halogen, alkyl, haloalkyl, alkoxyalkyl, alkoxy, haloalkoxy, alkyl- thio, cyclopropyl, alkenyl, unsubstituted or substituted aryloxyalkyl, benzyl or benz- yloxy, 3R 4 is hydrogen, cyano, unsubstituted or substituted alkyl, alkenyl, alkynyl, cyclo- alkyl, heterocyclyl, aryl and hetaryl; unsubstituted or substituted alkoxy, alkenyloxy, alkynyloxy, cycloalkoxy, heterocyclyloxy, aryloxy and hetaryloxy; unsubstituted or substituted arylthio and hetarylthio; A -Q-C (R 5 )=N-Yl-R 6 or -Q-O--N=CR 7 R 8 0050/46490 2 R 3 and R 4 together with the carbon atom to which they are bonded are an unsubstituted or substituted four- to eight- membered ring which, besides carbon atoms, may contain one or two oxygen and/or sulfur atoms and/or NH and/or N(C 1 -C 4 alkyl) groups; R 3 and R 4 not simultaneously being bonded to the carbon atom via hetero atoms; their salts, processes and intermediates for their preparation, and their use.