TREA

Pyridine derivatives, process for preparing the same and their use for controlling animal pests and harmful fungi

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Information

  • Patent Grant
  • 6228810
  • Patent Number
    6,228,810
  • Date Filed
    Wednesday, March 17, 1999
    25 years ago
  • Date Issued
    Tuesday, May 8, 2001
    23 years ago
Information
Abstract
Pyridine derivatives of the formula I and their salts, their preparation, and their use for controlling animal pests and harmful fungi.
Description




The present invention relates to pyridine derivatives of the formula I











where the index and the substituents have the following meanings:




X is cyano, nitro, halogen, C


1


-C


4


-alkyl, C


1


-C


4


-haloalkyl, C


1


-C


4


-alkoxy, C


1


-C


4


-haloalkoxy and C


3


-C


6


-cycloalkyl;




n is 0, 1, 2 or 3, it being possible for the substituents X to be different when n is greater than 1;




Y is oxygen or nitrogen, the nitrogen atom having attached to it a hydrogen atom or a C


1


-C


4


-alkyl group;




R is C(CO


2


CH


3


)═CHCH


3


, C(CO


2


CH


3


)═CHOCH


3


, C(CO


2


CH


3


)═NOCH


3


, C (CONH


2


)═NOCH


3


or C (CONHCH


3


)═NOCH


3


;




R


1


is hydrogen, hydroxyl, cyano, halogen,




C


1


-C


6


-alkyl, C


1


-C


6


-haloalkyl, C


1


-C


6


-alkoxy, C


1


-C


6


-haloalkoxy, C


1


-C


6


-alkylthio, C


3


-C


6


-cycloalkyl, C


3


-C


6


-cycloalkyl-C


1


-C


4


-alkyl,




aryl, aryl-C


1


-C


4


-alkyl, aryloxy-C


1


-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, C


1


-C


6


-alkyl, C


1


-C


6


-haloalkyl, C


1


-C


6


-alkoxy, C


1


-C


6


-haloalkoxy, and C (CH


3


)═N—A


1


—Ra;




R


a


is C


1


-C


6


-alkyl,




A


1


is oxygen or nitrogen, the nitrogen atom having attached to it a hydrogen atom or a C


1


-C


4


-alkyl group;




R


2


is hydrogen, cyano,




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




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




unsubstituted or substituted arylthio and hetarylthio;




—Q—C(R


3


)═N—Y


1


—R


4


or —Q—O—N═CR


5


R


6


where




Q is a direct bond, CH


2


, CH(CH


3


), CH(CH


2


CH


3


) or 1,1-cyclopropyl;




Y


1


is oxygen or nitrogen, the nitrogen atom having attached to it a hydrogen atom or a C


1


-C


4


-alkyl group;




R


3


is one of the groups mentioned for R


1


, or unsubstituted or substituted cycloalkoxy, heterocyclyloxy, aryloxy, hetaryloxy, arylthio and hetarylthio;




R


4


is unsubstituted or substituted C


1


-C


10


-alkyl, C


3


-C


6


-cycloalkyl, C


2


-C


10


-alkenyl, C


2


-C


10


-alkynyl, C


1


-C


10


-alkylcarbonyl, C


2


-C


10


-alkenylcarbonyl, C


2


-C


10


-alkynylcarbonyl or C


1


-C


10


-alkylsulfonyl; unsubstituted or substituted aryl, hetaryl, arylcarbonyl, hetarylcarbonyl, arylsulfonyl or hetarylsulfonyl;




R


5


, R


6


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, C


1


-C


6


-alkyl, C


1


-C


6


-haloalkyl, C


1


-C


6


-alkoxy and C


1


-C


6


-haloalkoxy;




R


1


and R


2


together with the carbon atom to which they are bonded are a four- to eight-membered ring which, in addition to carbon atoms, can 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, C


1


-C


6


-alkyl or C


1


-C


4


-alkoxyimino;




R


1


and R


2


not being bonded simultaneously to the carbon atom via hetero atoms;




and the salts thereof.




Moreover, the invention relates to processes for the preparation of these compounds, to compositions comprising them, and to their use for controlling animal pests and harmful fungi.




Compounds of the type I where Y is oxygen and R


2


is unsubstituted or substituted aryl or hetaryl are described in the literature in general form as fungicides (WO-A 95/06,033). However, only compounds which have attached to them an unsubstituted or substituted aryl group which is bonded to the pyridyl radical via oxygen, sulfur, oxymethylene or CH


2


—ON═C(CH


3


)— are disclosed in this publication.




It was an object of the present invention to provide compounds with an improved activity and a broadened spectrum of action.




We have found that this object is achieved by the compounds I defined at the outset. Furthermore, we have found processes for the preparation of these compounds, compositions comprising them, and their use for controlling animal pests and harmful fungi.




The compounds I can be prepared by various routes, it generally being irrelevant whether the group —Y—N═CR


1


R


2


or the radical R is first synthesized.




1. In the preparation of the compounds I where R is C(CO


2


CH


3


)═CHCH


3


, C(CO


2


CH


3


)═CHOCH


3


or C(CO


2


CH


3


)═NOCH


3


, a procedure is followed, for example, in which a pyridinecarboxylic acid of the formula IIa is first converted in a manner known per se into the acid chloride IIb and subsequently into the acid cyanide IIc; IIc is reacted via a Pinner reaction to give the corresponding α-keto ester IIIa; IIIa is subsequently reacted with an oxime of the formula IV in the presence of a base to give the corresponding α-keto ester IIIb; and IIIb is subsequently converted in a manner known per se either




a) with a Wittig or Wittig-Horner reagent of the formula Va into the corresponding compound Ia [R=C(CO


2


CH


3


)═CHOCH


3


], or




b) with a Wittig or Wittig-Horner reagent of the formula Vb into the corresponding compound Ib [R=C(CO


2


CH


3


)═CHCH


3


], or




c) with O-methylhydroxylamine or a salt thereof (Vc) into the corresponding compound Ic [R=C(CO


2


CH


3


)═NOCH


3


].











L


1


in formula IIa is a nucleophilically exchangeable leaving group such as [lacuna]




R# in formula IIa is hydrogen or a C


1


-C


4


-alkyl group, in particular hydrogen.




P* in formulae Va and Vb is a phosphonate or a phosphonium halide radical which is suitable for a Wittig or Wittig-Horner reaction, in particular PO(OCH


3


)


2


, PO(OCH


2


CH


3


)


2


and [(C


6


H


5


)


3


P


+


Cl


−


].




Z


−


in formula Vc is the anion of an inorganic acid, especially a halide anion, in particular chloride.




1A. The reaction of the pyridinecarboxylic acid IIa to give the acid chloride IIb is carried out in a manner known per se [Houben-Weyl, Supplementary Volume 5, p.59 et seq., 225 et seq. and 664 et seq.; J.Heterocycl.Chem, 30, (1993), 771] by means of customary chlorinating agents at from 0° C. to 150° C., preferably 10° C. to 100° C., in the presence or absence of an inert organic solvent.











Suitable chlorinating agents are all reagents customary for this purpose, in particular SOCl


2


, (COCl)


2


, PCl


3


, AlCl


3


and PCl


5


. In general, the chlorinating agents are used in an excess or, if appropriate, as the solvent.




Suitable solvents are aliphatic hydrocarbons such as pentane, hexane, cyclohexane and petroleum ether, aromatic hydrocarbons such as toluene, o-, m- and p-xylene, halogenated hydrocarbons such as methylene chloride, chloroform and chlorobenzene, nitrites such as acetonitrile and propionitrile, especially preferably halogenated hydrocarbons or mixtures of these.




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




The starting materials required for the preparation of the compounds I which are not already known from the literature [WO-A 95/06,033; J.Heterocycl.Chem. 30, (1993), 717; DE Appl. No. 19 540 989.2; DE Appl. No. 19 548 370.7] can be prepared in accordance with the literature cited.




1B. The reaction of the acid chloride IIb to give the cyanide IIc is carried out in a manner known per se [DE Appl. No. 19 603 990.8] at from 0° C. to 150° C., preferably 10° C. to 100° C., using an inorganic cyanide in an inert organic solvent, if appropriate as a mixture with water, in the presence of a customary phase-transfer catalyst (eg. tetraalkylammonium halides such as tetrabutylammonium chloride or tetrabutylammonium bromide).











Suitable inorganic cyanides are cyanides of metals of the first main group or of the sub-groups of the Periodic Table, for example lithium, sodium, potassium, copper and silver, in particular copper and sodium, and inorganic cyanides such as trimethylsilyl cyanide.




Suitable solvents are aromatic hydrocarbons such as toluene, o-, m- and p-xylene, nitrites such as acetonitrile and propionitrile, especially preferably methylene chloride and acetonitrile. Mixtures of these may also be used.




When using organic cyanides such as trimethylsilyl cyanide, it may be advantageous to carry out the reaction in the presence of an acidic catalyst. Acidic catalysts which are used are Lewis acids such as boron trifluoride, aluminum trichloride, iron(III) chloride, tin(IV) chloride, titanium(IV) chloride and zink(II) chloride, in particular tin(IV) chloride.




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 IIb.




1C. The reaction of the cyanide IIc to give the α-keto ester IIIa is carried out in a manner known per se via a Pinner reaction [DE Appl. No. 19 603 990.8] at from 0° C. to 150° C., preferably 10° C. to 100° C., in the presence of an acid in methanol as the solvent.











Acids which are used are inorganic acids such as hydrofluoric acid, hydrochloric acid, hydrobromic acid, sulfuric acid and perchloric acid. In general, the acids are used in equimolar amounts or in an excess.




The reaction is usually carried out in such a way that the cyanide IIc is first hydrolyzed with aqueous acids (eg. hydrochloric acid) at from 10° C. to 100° C. and the product is subsequently esterified by reaction with methanol, in the presence or absence of a reaction auxiliary (eg. sulfuric acid) and in the presence or absence of a diluent (eg. toluene) at from 10° C. to 150° C. by methods similar to known processes [EP-A 493 711].




1D. The reaction of the α-keto ester IIIa with the oxime of the formula IV is carried out in a manner known per se at from 0° C. to 150° C., preferably 10° C. to 100° C., in an inert organic solvent in the presence of a base.











Suitable solvents are alcohols such as methanol, ethanol, n-propanol, isopropanol, n-butanol and tert-butanol, and also dimethyl sulfoxide, dimethylformamide and dimethylacetamide, especially preferably dimethylformamide, dimethylacetamide, dimethyl sulfoxide and tert-butanol. Mixtures of these may also be used.




Bases which are generally suitable are 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, and also alkali metal hydrogen carbonates such as sodium hydrogen carbonate, and also 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. Potassium tert-butoxide, potassium carbonate and sodium methoxide are especially preferred.




In general, the bases are 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 IV in an excess based on IIIa.




1E. The reaction of the α-keto ester IIIb to give the compound Ia is carried out in a manner known per se [EP-A 513 580; tetrahedron 3727 (1988); GB-A 2,172,595; DE Appl. No. 19 603 990.8] via a Wittig or Wittig-Horner reaction at from 0° C. to 150° C., preferably 10° C. to 100° C., in an inert organic solvent in the presence of a base.











Suitable solvents are ethers such as diethyl ether, diisopropyl ether, tert-butyl methyl ether, dioxane, anisole and tetrahydrofuran, alcohols such as methanol, ethanol, n-propanol, isopropanol, n-butanol and tert-butanol, and also dimethyl sulfoxide, dimethylformamide and dimethylacetamide, especially preferably dimethylformamide, dimethylacetamide and tetrahydrofuran. 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 carbonates and alkaline earth metal carbonates such as lithium carbonate and calcium carbonate, and 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. Sodium methoxide and potassium tert-butoxide are especially preferred.




In general, the bases are 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 Va in an excess based on IIIb.




1F. The reaction of the α-keto ester IIIb to give the compound Ib is carried out a manner known per se (cf. the references cited under 1E.) via a Wittig or Wittig-Horner reaction at from 0° C. to 150° C., preferably 10° C. to 100° C., in an inert organic solvent in the presence of a base.











Suitable solvents are ethers such as diethyl ether, diisopropyl ether, tert-butyl methyl ether, dioxane, anisole and tetrahydrofuran, alcohols such as methanol, ethanol, n-propanol, isopropanol, n-butanol and tert-butanol, and also dimethyl sulfoxide, dimethylformamide and dimethylacetamide, especially preferably dimethyl sulfoxide, dimethylformamide, dimethylacetamide and tetrahydrofuran. Mixtures of these can 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 carbonates and alkaline earth metal carbonates such as lithium carbonate and calcium carbonate, and alkali metal hydrogen carbonates such as sodium hydrogen carbonate, organometallic compounds, in particular alkali metal alkyls such as methyllithium, butyllithium and phenyllithium, alkylmagnesuim 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. Sodium methoxide and potassium tert-butoxide are especially preferred.




In general, the bases are 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 Vb in an excess based on IIb.




1G. The reaction of the α-keto ester IIIb to give the compound Ic is carried out in a manner known per se (EP-A 493 711) at from 0° C. to 150° C., preferably 10° C. to 100° C., in an inert organic solvent in the presence of a base using O-methylhydroxylamine or a salt thereof (Vc).











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




Bases which are generally suitable are 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, furthermore organic bases, eg. tertiary amines such as trimethylamine, triethylamine, tri-isopropylethylamine and N-methylpiperidine, pyridine, substituted pyridines such as collidine, lutidine and 4-dimethylaminopyridine, and also bicyclic amines. Tertiary amines are especially preferred.




The bases are generally employed in catalytic amounts, but they can 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 Vc in an excess based on IIIb.




2. In a further process, the compounds Ia, Ib and Ic are obtained, for example, by converting a pyridine derivative of the formula VI with a compound VII in a manner known per se in the presence of a catalyst into the corresponding pyridine derivative of the formula VIII and subsequently reacting VIII with an oxime of the formula IV in the presence of a base to give Ia, Ib or Ic. The pyridine derivatives VIII are also obtained in a similar manner by reacting a halogenated pyridine of the formula VIa with an organometallic compound VIIa.











L


1


in formulae VI, VIa and VIII is a nucleophilically exchangeable leaving group, such as aliphatic and aromatic sulfonates and halogen atoms, in particular fluorine and chlorine.




M in formulae VI and VIIa is an organometallic radical, eg. tributyltin(IV), trimethyltin(IV), zink(II) chloride (ZnCl) or boron(II) hydroxide [B(OH)


2


], in particular tributyltin(IV) and boron(II) hydroxide [B(OH)


2


]. With a view to the high toxicity of trimethyltin(IV), this substance is preferred only under certain conditions.




T in formulae VII, VIIa, VIII and Ia, Ib or Ic is CH, CHO or NO.




Hal in formulae VIa and VII is a halogen atom, in particular bromine or iodine.




2A. The reaction of the compound VI, or VIa, with the carbonyl derivative VII, or VIIa, is carried out in a manner known per se at from 0° C. to 150° C., preferably 10° C. to 100° C., in an inert organic solvent in the presence or absence of a cocatalyst such as CuI. In the event that the reaction is carried out with the compound VI or VIIa where M is B(OH)


2


, the reaction is carried out in the presence of at least equimolar amounts of a base.











Suitable solvents are aromatic hydrocarbons such as toluene, o-, m- and p-xylene, ethers such as diethyl ether, diisopropyl ether, tert-butyl methyl ether, dioxane, anisole and tetrahydrofuran, and also dimethylformamide and dimethylacetamide, especially preferably N-methylpyrrolidone. Mixtures of the abovementioned solvents can also be used.




Bases which are suitable for coupling compounds where M is B(OH)


2


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 carbonates and alkaline earth metal carbonates such as lithium carbonate and calcium carbonate, and also alkali metal hydrogen carbonates such as sodium hydrogen carbonate, and also 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, tri-isopropylethylamine and N-methylpiperidine, pyridine, substituted pyridines such as collidine, lutidine and 4-dimethylaminopyridine, and also bicyclic amines. Sodium carbonate, sodium hydrogen carbonate and lithium hydroxide are especially preferred.




In general, the bases are 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 VI or VIIa in an excess based on VII or VIa.




Those starting materials required for the preparation of the compounds I which are not already known from the literature [WO-A 95/20,569; WO-A 94/24,085; Synlett (1) (1995) 32-33; Synlett (4) (1996) 356-357; J.Gen.Chem.USSR 59 (1989) 264-272; Heterocycles 31 (1990) 1543-1548; Tetrahedron 49 (1993) 49-64; J.Chem.Res.Miniprint 11 (1980) 4658-4667] can be prepared in accordance with the literature cited.




2B. The reaction of the compound VIII with the oxime derivative IV is carried out in a manner known per se at from 0° C. to 150° C., preferably 10° C. to 100° C., in an inert organic solvent in the presence of a base.











Suitable solvents are alcohols such as methanol, ethanol, n-propanol, isopropanol, n-butanol and tert-butanol, and also dimethyl sulfoxide, dimethylformamide and dimethylacetamide, especially preferably dimethyl sulfoxide, dimethylformamide and dimethylacetamide. Mixtures of these can 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 carbonates and alkaline earth metal carbonates such as lithium carbonate and calcium carbonate, and also alkali metal hydrogen carbonates such as sodium hydrogen carbonate, and also 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, tri-isopropylethylamine and N-methylpiperidine, pyridine, substituted pyridines such as collidine, lutidine and 4-dimethylaminopyridine, and also bicyclic amines. Potassium tert-butoxide, sodium methoxide and potassium carbonate are especially preferred.




In general, the bases are 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 IV in an excess based on VIII.




2.1 In accordance with the above-described reaction conditions, the compounds Ia, Ib and Ic are also especially preferably obtained by first converting the pyridine VIa with the oxime IV into the corresponding derivative VIIIa and subsequently reacting VIIIa with VIIa to give Ia, Ib or Ic.











3. The compounds of the formula I where R is C(CONHCH


3


)═NOCH


3


are advantageously obtained by reacting a compound of the formula Ic in a manner known per se with methylamine or a salt thereof (IX).











Z


−


in formula IX is the anion of an inorganic acid, especially a halide anion, in particular chloride.




This reaction is carried out in a manner known per se (EP-A 477 631) at from 0° C. to 150° C., preferably 10° C. to 100° C., in an inert organic solvent and 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, o-, 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, alcohols such as methanol, ethanol, n-propanol, isopropanol, n-butanol and tert-butanol, and also dimethyl sulfoxide, dimethylformamide and dimethylacetamide, especially preferably tetrahydrofuran. Mixtures of these can also be used.




Suitable bases 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 carbonates and alkaline earth metal carbonates such as lithium carbonate and calcium carbonate, and also alkali metal hydrogen carbonates such as sodium hydrogen carbonate, furthermore organic bases, eg. tertiary amines such as trimethylamine, triethylamine, tri-isopropylethylamine and N-methylpiperidine, pyridine, substituted pyridines such as collidine, lutidine and 4-dimethylaminopyridine, and also bicyclic amines. Tertiary amines are especially preferred.




The bases are generally 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 Ic.




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




In the definitions of the symbols given in the above formulae, 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-1-methylpropyl and 1-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, 1-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 (—CO—);




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


—);




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 (—SO


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 (—O—);




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 (—O—);




Alkoxycarbonyl: an alkoxy group having 1 to 6 carbon atoms (as mentioned above) which is bonded to the skeleton via a carbonyl group (—CO—);




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 (—ON=);




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 (—S—);




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 (—NH—);




Dialkylamino: two straight-chain or branched alkyl groups, independent of one another, which have in each case 1 to 6 carbon atoms (as mentioned above) and 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 (—CO—);




Dialkylaminocarbonyl: a dialkylamino group having two C


1


-C


6


-alkyl groups (as mentioned above), independent of one another, which is bonded to the skeleton via a carbonyl group (—CO—);




Alkylaminothiocarbonyl: an alkylamino group having 1 to 6 carbon atoms (as mentioned above) which is bonded to the skeleton via a thiocarbonyl group (—CS—);




Dialkylaminothiocarbonyl: a dialkylamino group having two C


1


-C


6


-alkyl groups (as mentioned above), independent of one another, which is bonded to the skeleton via a thiocarbonyl group (—CS—);




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, 1-methyl-1-propenyl, 2-methyl-1-propenyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-methyl-1-butenyl, 2-methyl-1-butenyl, 3-methyl-1-butenyl, 1-methyl-2-butenyl, 2-methyl-2-butenyl, 3-methyl-2-butenyl, 1-methyl-3-butenyl, 2-methyl-3-butenyl, 3-methyl-3-butenyl, 1,1-dimethyl-2-propenyl, 1,2-dimethyl-1-propenyl, 1,2-dimethyl-2-propenyl, 1-ethyl-1-propenyl, 1-ethyl-2-propenyl, 1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, 5-hexenyl, 1-methyl-1-pentenyl, 2-methyl-1-pentenyl, 3-methyl-1-pentenyl, 4-methyl-1-pentenyl, 1-methyl-2-pentenyl, 2-methyl-2-pentenyl, 3-methyl-2-pentenyl, 4-methyl-2-pentenyl, 1-methyl-3-pentenyl, 2-methyl-3-pentenyl, 3-methyl-3-pentenyl, 4-methyl-3-pentenyl, 1-methyl-4-pentenyl, 2-methyl-4-pentenyl, 3-methyl-4-pentenyl, 4-methyl-4-pentenyl, 1,1-dimethyl-2-butenyl, 1,1-dimethyl-3-butenyl, 1,2-dimethyl-1-butenyl, 1,2-dimethyl-2-butenyl, 1,2-dimethyl-3-butenyl, 1,3-dimethyl-1-butenyl, 1,3-dimethyl-2-butenyl, 1,3-dimethyl-3-butenyl, 2,2-dimethyl-3-butenyl, 2,3-dimethyl-1-butenyl, 2,3-dimethyl-2-butenyl, 2,3-dimethyl-3-butenyl, 3,3-dimethyl-1-butenyl, 3,3-dimethyl-2-butenyl, l-ethyl-1-butenyl, 1-ethyl-2-butenyl, 1-ethyl-3-butenyl, 2-ethyl-1-butenyl, 2-ethyl-2-butenyl, 2-ethyl-3-butenyl, 1,1,2-trimethyl-2-propenyl, 1-ethyl-1-methyl-2-propenyl, 1-ethyl-2-methyl-1-propenyl and 1-ethyl-2-methyl-2-propenyl;




Alkenyloxy: unsaturated 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 (—O—);




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 (—CO—);




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. C


2


-C


6


-alkynyl such as ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methyl-2-propynyl, 1-pentynyl, 2-pentynyl, 3-pentynyl, 4-pentynyl, 1-methyl-2-butynyl, 1-methyl-3-butynyl, 2-methyl-3-butynyl, 3-methyl-1-butynyl, 1,1-dimethyl-2-propynyl, 1-ethyl-2-propynyl, 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 1-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 (—O—);




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 (—CO—);




Cycloalkyl: monocyclic saturated hydrocarbon groups having 3 to 6 or 10 carbon ring members, eg. C


3


-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 atom (—O—);




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


-cycloalkenyl such as cyclopentenyl, cyclohexenyl, cycloheptenyl and cyclooctenyl;




Heterocyclyl: 5- or 6-membered heterocycles containing, in addition to carbon ring members, one to three nitrogen atoms and/or one 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, 5-thiazolidinyl, 2-imidazolidinyl, 4-imidazolidinyl, 1,2,4-oxadiazolidin-3-yl, 1,2,4-oxadiazolidin-5-yl, 1,2,4-thiadiazolidin-3-yl, 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-isoxazolin-5-yl, 3,4-isoxazolin-5-yl, 4,5-isoxazolin-5-yl, 2,3-isothiazolin-3-yl, 3,4-isothiazolin-3-yl, 4,5-isothiazolin-3-yl, 2,3-isothiazolin-4-yl, 3,4-isothiazolin-4-yl, 4,5-isothiazolin-4-yl, 2,3-isothiazolin-5-yl, 3,4-isothiazolin-5-yl, 4,5-isothiazolin-5-yl, 2,3-dihydropyrazol-1-yl, 2,3-dihydropyrazol-2-yl, 2,3-dihydropyrazol-3-yl, 2,3-dihydropyrazol-4-yl, 2,3-dihydropyrazol-5-yl, 3,4-dihydropyrazol-1-yl, 3,4-dihydropyrazol-3-yl, 3,4-dihydropyrazol-4-yl, 3,4-dihydropyrazol-5-yl, 4,5-dihydropyrazol-1-yl, 4,5-dihydropyrazol-3-yl, 4,5-dihydropyrazol-4-yl, 4,5-dihydropyrazol-5-yl, 2,3-dihydrooxazol-2-yl, 2,3-dihydrooxazol-3-yl, 2,3-dihydrooxazol-4-yl, 2,3-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 (—O—);




Aryl: a mono- to trinuclear aromatic ring system containing 6 to 14 carbon ring members, eg. phenyl, naphthyl and anthracenyl;




Aryloxy: a mono- to trinuclear aromatic ring system (as mentioned above) which is bonded to the skeleton via an oxygen atom (—O—);




Arylthio: a mono- to trinuclear aromatic ring system (as mentioned above) which is bonded to the skeleton via a sulfur atom (—S—);




Arylcarbonyl: a mono- to trinuclear aromatic ring system (as mentioned above) which is bonded to the skeleton via a carbonyl group (—CO—);




Arylsulfonyl: a mono- to trinuclear aromatic ring system (as mentioned above) which is bonded to the skeleton via a sulfonyl group (—SO


2


—);




Arylsulfoxyl: a mono- to trinuclear aromatic ring system (as mentioned above) which is bonded to the skeleton via a sulfoxyl group (—O—SO


2


—);




Hetaryl: a mono- or binuclear, 5-, 6-, 9- or 10-membered aromatic ring system which, in addition to carbon ring members, contains hetero atoms selected 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 one sulfur or oxygen atom: 5-membered hetaryl ring groups which, in addition to carbon atoms, can contain one to four nitrogen atoms or one to three nitrogen atoms and one 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, 5-isothiazolyl, 3-pyrazolyl, 4-pyrazolyl, 5-pyrazolyl, 2-oxazolyl, 4-oxazolyl, 5-oxazolyl, 2-thiazolyl, 4-thiazolyl, 5-thiazolyl, 2-imidazolyl, 4-imidazolyl, 1,2,4-oxadiazol-3-yl, 1,2,4-oxadiazol-5-yl, 1,2,4-thiadiazol-3-yl, 1,2,4-thiadiazol-5-yl, 1,2,4-triazol-3-yl, 1,3,4-oxadiazol-2-yl, 1,3,4-thiadiazol-2-yl and 1,3,4-triazol-2-yl;




benzo-fused 5-membered hetaryl containing one to three nitrogen atoms or one nitrogen atom and one oxygen or sulfur atom: 5-membered hetaryl ring groups which, in addition to carbon atoms, can contain one to four nitrogen atoms or one to three nitrogen atoms and one sulfur or oxygen atom as ring members and in which two adjacent carbon ring members or a nitrogen and an adjacent carbon ring member can 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: 5-membered hetaryl ring groups which, in addition to carbon atoms, can 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 can 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, in addition to carbon atoms, can contain one to three, or one to four, nitrogen atoms as ring members, eg. 2-pyridinyl, 3-pyridinyl, 4-pyridinyl, 3-pyridazinyl, 4-pyridazinyl, 2-pyrimidinyl, 4-pyrimidinyl, 5-pyrimidinyl, 2-pyrazinyl, 1,3,5-triazin-2-yl and 1,2,4-triazin-3-yl;




Hetaryloxy: a mono- or binuclear heteroaromatic ring system (as mentioned above) which is bonded to the skeleton via an oxygen atom (—O—);




Hetarylthio: a mono- or binuclear heteroaromatic ring system (as mentioned above) which is bonded to the skeleton via a sulfur atom (—S—);




Hetarylcarbonyl: a mono- or binuclear heteroaromatic ring system (as mentioned above) which is bonded to the skeleton via a carbonyl group (—CO—);




Hetarylsulfonyl: a mono- or binuclear heteroaromatic ring system (as mentioned above) which is bonded to the skeleton via a sulfonyl group (—SO


2


—).




Hetarylsulfoxyl: a mono- or binuclear heteroaromatic ring system (as mentioned above) which is bonded to the skeleton via a sulfoxyl group (—O—SO


2


—).




The addition “unsubstituted or substituted” when relating to alkyl, alkenyl and alkynyl groups is intended to express that these groups can be partially or fully halogenated [ie. some or all of the hydrogen atoms of these groups can be replaced by identical or different halogen atoms as mentioned above (preferably fluorine, chlorine or bromine)] and/or can 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 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 containing preferably 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, 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 6 ring members and the alkyl groups in these radicals containing preferably 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 can be partially or fully halogenated [ie. some or all of the hydrogen atoms of these groups can be replaced by identical or different halogen atoms as mentioned above (preferably fluorine, chlorine or bromine, in particular fluorine or chlorine)] and/or can have attached to them one to four (in particular one to three) 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 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 containing preferably 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 containing preferably 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 containing preferably 1 to 6 carbon atoms, in particular 1 to 4 carbon atoms,




and/or one or two (in particular one) of the following radicals:




formyl,




CR


v


=NOR


vi


[where R


v


is hydrogen, alkyl, cycloalkyl and aryl and R


vi


is alkyl, alkenyl, haloalkenyl, alkynyl and arylalkyl (the alkyl groups mentioned preferably containing 1 to 6 carbon atoms, in particular 1 to 4 carbon atoms, and the cycloalkyl groups, alkenyl groups and alkynyl groups mentioned preferably containing 3 to 8, in particular 3 to 6, carbon atoms) and aryl, in particular phenyl, which is unsubstituted or which can be substituted by customary groups] or




NR


vii


-CO-D-R


viii


[where R


vii


is hydrogen, hydroxyl, C


1


-C


6


-alkyl, C


2


-C


6


-alkenyl, C


2


-C


6


-alkynyl, C


1


-C


6


-alkoxy, C


2


-C


6


-alkenyloxy, C


2


-C


6


-alkynyloxy, C


1


-C


6


-alkoxy-C


1


-C


6


-alkyl, C


1


-C


6


-alkoxy-C


1


-C


6


-alkoxy and C


1


-C


6


-alkoxycarbonyl, R


viii


is hydrogen, C


1


-C


6


-alkyl, C


2


-C


6


-alkenyl, C


2


-C


6


-alkynyl, C


3


-C


6


-cycloalkyl, C


3


-C


6


-cycloalkenyl, aryl, aryl-C


1


-C


6


-alkyl, hetaryl and hetaryl-C


1


-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 for R


vi


],




and/or where two adjacent C atoms of the cyclic systems can have attached to them a C


3


-C


5


-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, C


1


-C


4


-haloalkyl, C


1


-C


4


-alkoxy, C


1


-C


4


-haloalkoxy and C


1


-C


4


-alkylthio.




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


1


-C


4


-alkyl, C


1


-C


4


-haloalkyl, C


1


-C


4


-alkoxy, C


1


-C


4


-haloalkoxy, C


1


-C


4


-alkylamino, di-C


1


-C


4


-alkylamino and C


1


-C


4


-alkylthio.




Preferred compounds of the formula I with a view to their biological activities are those where R


2


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, amino thiocarbonyl,




C


1


-C


6


-alkylsulfonyl, C


1


-C


6


-alkylsulfoxyl, C


1


-C


6


-alkylcarbonyl, C


3


-C


6


-cycloalkyl, C


1


-C


6


-alkoxy, C


1


-C


6


-haloalkoxy, C


1


-C


6


-alkoxycarbonyl, C


1


-C


6


-alkylthio, C


1


-C


6


-alkylamino, di-C


1


-C


6


-alkylaminocarbonyl, C


1


-C


6


-alkylaminorothicaboyl di-C


1


-C


6


-alkylaminothiocarbonyl, C


2


-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, amino thiocarbonyl,




C


1


-C


6


-alkyl, C


1


-C


6


-haloalkyl, C


1


-C


6


-alkylsulfonyl, C


1


-C


6


-alkylsulfoxyl, C


1


-C


6


-alkylcarbonyl, C


3


-C


6


-cycloalkyl, C


1


-C


6


-alkoxy, C


1


-C


6


-haloalkoxy, C


1


-C


6


-alkoxycarbonyl, C


1


-C


6


-alkylthio, C


1


-C


6


-alkylamino, di-C


1


-C


6


-alkylamino, C


1


-C


6


-alkylaminocarbonyl, di-C


1


-C


6


-alkylaminocarbonyl, C


1


-C


6


-alkylaminothiocarbonyl, di-C


1


-C


6


-alkylaminothiocarbonyl, C


2


-C


6


-alkenyl, C


2


-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,




C


1


-C


6


-alkyl, C


1


-C


6


-haloalkyl, C


1


-C


6


-alkylsulfonyl, C


1


-C


6


-alkylsulfoxyl, C


1


-C


6


-alkylcarbonyl, C


3


-C


6


-cycloalkyl, C


1


-C


6


-alkoxy, C


1


-C


6


-haloalkoxy, C


1


-C


6


-alkoxycarbonyl, C


1


-C


6


-alkylthio, C


1


-C


6


-alkylamino, di-C


1


-C


6


-alkylamino, C


1


-C


6


-alkylaminocarbonyl, di-C


1


-C


6


-alkylaminocarbonyl, C


1


-C


6


-alkylaminothiocarbonyl, di-C


1


-C


6


-alkylaminothiocarbonyl, 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(═NOR


i


)—A


m


—R


ii


or NR


iii


—CO—D—R


iv


;




A is oxygen, sulfur or nitrogen, the nitrogen having attached to it hydrogen or C


1


-C


6


-alkyl;




m is 0 or 1;




R


i


is hydrogen, C


1


-C


6


-alkyl, C


3


-C


6


-alkenyl or C


3


-C


6


-alkynyl;




R


ii


is hydrogen or C


1


-C


6


-alkyl;




D is a direct bond, oxygen or NR


b


(R


b


=hydrogen, C


1


-C


6


-alkyl, C


2


-C


6


-alkenyl, C


2


-C


6


-alkynyl, C


3


-C


6


-cycloalkyl, C


3


-C


6


-cycloalkenyl, aryl, aryl-C


1


-C


6


-alkyl, hetaryl and hetaryl-C


1


-C


6


-alkyl);




R


iii


is hydrogen, hydroxyl, C


1


-C


6


-alkyl, C


2


-C


6


-alkenyl, C


2


-C


6


-alkynyl, C


1


-C


6


-alkoxy, C


2


-C


6


-alkenyloxy, C


2


-C


6


-alkynyloxy, C


1


-C


6


-alkoxy-C


1


-C


6


-alkyl, C


1


-C


6


-alkoxy-C


1


-C


6


-alkoxy and C


1


-C


6


-alkoxycarbonyl;




R


iv


is hydrogen, C


1


-C


6


-alkyl, C


2


-C


6


-alkenyl, C


2


-C


6


-alkynyl, C


3


-C


6


-cycloalkyl, C


3


-C


6


-cycloalkenyl, aryl, aryl-C


1


-C


6


-alkyl, hetaryl and hetaryl-C


1


-C


6


-alkyl.




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




R


1


is hydrogen, cyano,




C


1


-C


6


-alkyl, C


1


-C


6


-haloalkyl, C


3


-C


6


-cycloalkyl, C


3


-C


6


-cycloalkyl-C


1


-C


4


-alkyl,




aryl, aryl-C


1


-C


4


-alkyl and aryloxy-C


1


-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, C


1


-C


6


-alkyl, C


1


-C


6


-haloalkyl, C


1


-C


6


-alkoxy, C


1


-C


6


-haloalkoxy, and C(CH


3


)═N—A


1


—R


a


;




R


2


is unsubstituted or substituted aryl, hetaryl, aryloxy, hetaryloxy, arylthio and hetarylthio;




—Q—C(R


3


)═N—Y


1


—R


4


or —Q—O—N═CR


5


R


6


,




R


1


and R


2


together with the carbon atom to which they are bonded are a four- to eight-membered ring which, in addition to carbon atoms, can 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, C


1


-C


6


-alkyl or C


1


-C


4


-alkoxyimino, where




R


1


and R


2


are not simultaneously bonded to the carbon atoms via hetero atoms.




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




R


1


is hydrogen, cyano, halogen,




C


1


-C


6


-alkyl, C


1


-C


6


-haloalkyl, C


1


-C


6


-alkoxy, C


1


-C


6


-haloalkoxy, C


1


-C


6


-alkylthio, C


3


-C


6


-cycloalkyl, C


3


-C


6


-cycloalkyl-C


1


-C


4


-alkyl,




aryl, aryl-C


1


-C


4


-alkyl, aryloxy-C


1


-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, C


1


-C


6


-alkyl, C


1


-C


6


-haloalkyl, C


1


-C


6


-alkoxy, C


1


-C


6


-haloalkoxy, and C(CH


3


)═N—A


1


—R


a


;




R


2


is unsubstituted or substituted aryl and hetaryl;




—Q—C(R


3


)═N—Y


1


—R


4


or —Q—O—N═CR


5


R


6


,




R


1


and R


2


are not simultaneously bonded to the carbon atom via hetero atoms.




Especially preferred with a view to biological efficacy are compounds I where the radical R and the group —Y—N═CR


1


R


2


are bonded to adjacent C atoms of the pyridyl ring.




Moreover, especially preferred compounds I are those where n is 0 or 1.




In the event that n is 1, preferred compounds I are those where X is cyano, halogen (in particular fluorine and chlorine), C


1


-C


3


-alkyl (in particular methyl and ethyl), C


1


-C


2


-haloalkyl (in particular difluoromethyl and trifluoromethyl), C


1


-C


3


-alkoxy (in particular methoxy), C


1


-C


2


-haloalkoxy (in particular difluoromethoxy and trifluoromethoxy) or cyclopropyl.




Moreover, especially preferred compounds I are those where Y is oxygen.




In the event that Y is nitrogen, preferred compounds I are those where the nitrogen atom additionally has attached to it a hydrogen atom or a C


1


-C


3


-alkyl group (in particular methyl, ethyl or isopropyl).




Additionally preferred compounds I are those where R 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


.




The following compounds Ia.1-Id.4 are particularly preferred.

























Particularly preferred with a view to use against animal pests and harmful fungi are compounds of the formula I.4











where substituents and the index have the following meanngs:




R 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


;




X is cyano, halogen, C


1


-C


4


-alkyl, C


1


-C


2


-haloalkyl, C


1


-C


4


-alkoxy, C


1


-C


2


-haloalkoxy and C


3


-C


6


-cycloalkyl;




n is 0 or 1;




R


1


is hydrogen, hydroxyl, cyano, C


1


-C


4


-alkyl, C


1


-C


2


-haloalkyl, C


1


-C


4


-alkoxy, C


1


-C


2


-haloalkoxy, C


3


-C


6


-cycloalkyl, C


3


-C


6


-cycloalkyl-C


1


-C


4


-alkyl, or benzyl which can be substituted by customary groups;




R


2


is hydrogen, C


3


-C


6


-cycloalkyl,




C


1


-C


6


-alkyl or C


1


-C


6


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


1


-C


4


-alkoxy, C


3


-C


6


-cycloalkyl, or phenyl, naphthyl, pyridinyl, pyrazinyl, thienyl, pyrazolyl or isoxazolyl, in each case unsubstituted or substituted by customary groups;




phenyl, naphthyl, pyridinyl, pyrazinyl, thienyl, pyrazolyl or isoxazolyl, unsubstituted or substituted by customary groups;




phenoxy, naphthyloxy, pyridinyloxy, pyrazinyloxy, thienyloxy, pyrazolyloxy or isoxazolyloxy, unsubstituted or substituted by customary groups; or




R


1


and R


2


together with the carbon atom to which they are bonded are a saturated or partially unsaturated, four- to eight-membered ring which, in addition to hydrocarbon ring members, can contain a hetero atom selected from the group consisting of oxygen, sulfur and nitrogen and which can be partially halogenated and/or can have attached to it one to three of the following groups: C


1


-C


4


-alkyl, C


1


-C


4


-haloalkyl, C


1


-C


4


-alkoxy, C


1


-C


4


-haloalkoxy, oxo (═O) and C


1


-C


4


-alkoxyimino (═N-alkoxy), where




R


1


and R


2


are not simultaneously bonded to the carbon atom via hetero atoms;




Moreover, particularly preferred with a view to use against animal pests and harmful fungi are compounds of the formula I.8











where the substituents and the index have the following meanings:




R 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


;




X is cyano, halogen, C


1


-C


4


-alkyl, C


1


-C


2


-haloalkyl, C


1


-C


4


-alkoxy, C


1


-C


2


-haloalkoxy and C


3


-C


6


-cycloalkyl;




n is 0 or 1;




R


1


is hydrogen, cyano, halogen, C


1


-C


4


-alkyl, C


1


-C


2


-haloalkyl, C


1


-C


4


-alkoxy, C


1


-C


2


-haloalkoxy and C


3


-C


6


-cycloalkyl;




R


3


is hydrogen, cyano, halogen, C


1


-C


4


-alkyl, C


1


-C


2


-haloalkyl, C


1


-C


4


-alkoxy, C


1


-C


2


-haloalkoxy and C


3


-C


6


-cycloalkyl;




Y


1


is O, NH or N(CH


3


);




R


4


is hydrogen,




C


1


-C


6


-alkyl which can have attached to it one of the following groups: C


1


-C


4


-alkoxy, C


3


-C


6


-cycloalkyl, unsubstituted or substituted by customary groups, or phenyl, unsubstituted or substituted by customary groups;




C


3


-C


6


-alkenyl, C


3


-C


6


-haloalkenyl, C


3


-C


6


-alkynyl, C


3


-C


6


-haloalkynyl, or C


3


-C


6


-cycloalkyl, unsubstituted or substituted by customary groups.




Furthermore, particularly preferred with a view to use against animal pests and harmful fungi are compounds of the formula I.12











where the substituents and the index have the following meanings:




R 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


;




X is cyano, halogen, C


1


-C


4


-alkyl, C


1


-C


2


-haloalkyl, C


1


-C


4


-alkoxy, C


1


-C


2


-haloalkoxy and C


3


-C


6


-cycloalkyl;




n is 0 or 1;




R


1


is hydrogen, cyano, halogen, C


1


-C


4


-alkyl, C


1


-C


2


-haloalkyl, C


1


-C


4


-alkoxy, C


1


-C


2


-haloalkoxy and C


3


-C


6


-cycloalkyl;




R


x


is hydrogen, cyano, halogen, C


1


-C


4


-alkyl, C


1


-C


2


-haloalkyl, C


1


-C


4


-alkoxy, C


1


-C


2


-haloalkoxy and C


3


-C


6


-cycloalkyl;




R


y


is hydrogen,




C


1


-C


6


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


1


-C


4


-alkoxy, C


3


-C


6


-cycloalkyl, unsubstituted or substituted by customary groups, or phenyl, unsubstituted or substituted by customary groups;




C


1


-C


6


-alkoxy, C


1


-C


6


-haloalkoxy,




C


3


-C


6


-cycloalkyl, unsubstituted or substituted by customary groups; phenyl, unsubstituted or substituted by customary groups, pyridyl, unsubstituted or substituted by customary groups, or pyrimidyl, unsubstituted or substituted by customary groups;




R


z


is hydrogen, cyano, halogen, C


1


-C


4


-alkyl, C


1


-C


2


-haloalkyl and C


3


-C


6


-cycloalkyl, or




R


y


and R


x


together with the double bond to which they are bonded are C


4


-C


6


-cycloalkenyl.




Particularly preferred with a view to their use are the compounds I compiled in the tables which follow. Moreover, the groups mentioned in the tables for a substituent are, in their own right and independent of the combination in which they are mentioned, an especially preferred embodiment of the substituent in question.




Table 1




Compounds of the formula Ia.1 where X


n


is hydrogen and the combination of the radicals R


1


and R


2


for each compound corresponds to one line of Table A











Table 2




Compounds of the formula Ia.2 where X


n


is hydrogen and the combination of the radicals R


1


and R


2


for each compound corresponds to one line of Table A











Table 3




Compounds of the formula Ia.3 where X


n


is hydrogen and the combination of the radicals R


1


and R


2


for each compound corresponds to one line of Table A











Table 4




Compounds of the formula Ia.4 where X


n


is hydrogen and the combination of the radicals R


1


and R


2


for each compound corresponds to one line of Table A











Table 5




Compounds of the formula Ia.4 where X


n


is 6-CF


3


and the combination of the radicals R


1


and R


2


for each compound corresponds to one line of Table A




Table 6




Compounds of the formula Ia.4 where X


n


is 6-CH(CH


3


)


2


and the combination of the radicals R


1


and R


2


for each compound corresponds to one line of Table A




Table 7




Compounds of the formula Ib.1 where X


n


is hydrogen and the combination of the radicals R


1


and R


2


for each compound corresponds to one line of Table A











Table 8




Compounds of the formula Ib.2 where X


n


is hydrogen and the combination of the radicals R


1


and R


2


for each compound corresponds to one line of Table A











Table 9




Compounds of the formula Ib.3 where X


n


is hydrogen and the combination of the radicals R


1


and R


2


for each compound corresponds to one line of Table A











Table 10




Compounds of the formula Ib.4 where X


n


is hydrogen and the comination of the radicals R


1


and R


2


for each compound corresponds to one line of Table A











Table 11




Compounds of the formula Ib.4 where X


n


is 6-CF


3


and the combination of the radicals R


1


and R


2


for each compound corresponds to one line of Table A




Table 12




Compounds of the formula Ib.4 where X


n


is 6-CH(CH


3


)


2


and the combination of the radicals R


1


and R


2


for each compound corresponds to one line of Table A




Table 13




Compounds of the formula Ic.1 where X


n


is hydrogen and the combination of the radicals R


1


and R


2


for each compound corresponds to one line of Table A











Table 14




Compounds of the formula Ic.2 where X


n


is hydrogen and the combination of the radicals R


1


and R


2


for each compound corresponds to one line of Table A











Table 15




Compounds of the formula Ic.3 where X


n


is hydrogen and the combination of the radicals R


1


and R


2


for each compound corresponds to one line of Table A











Table 16




Compounds of the formula Ic.4 where X


n


is hydrogen and the combination of the radicals R


1


and R


2


for each compound corresponds to one line of Table A











Table 17




Compounds of the formula Ic.4 where X


n


is 6-CF


3


and the combination of the radicals R


1


and R


2


for each compound corresponds to one line of Table A




Table 18




Compounds of the formula Ic.4 where X


n


is 6-CH(CH


3


)


2


and the combination of the radicals R


1


and R


2


for each compound corresponds to one line of Table A




Table 19




Compounds of the formula Id.1 where X


n


is hydrogen and the combination of the radicals R


1


and R


2


for each compound corresponds to one line of Table A











Table 20




Compounds of the formula Id.2 where X


n


is hydrogen and the combination of the radicals R


1


and R


2


for each compound corresponds to one line of Table A











Table 21




Compounds of the formula Id.3 where X


n


is hydrogen and the combination of the radicals R


1


and R


2


for each compound corresponds to one line of Table A











Table 22




Compounds of the formula Id.4 where X


n


is hydrogen and the combination of the radicals R


1


and R


2


for each compound corresponds to one line of Table A











Table 23




Compounds of the formula Id.4 where X


n


is 6-CF


3


and the combination of the radicals R


1


and R


2


for each compound corresponds to one line of Table A




Table 24




Compounds of the formula Id.4 where X


n


is 6-CH(CH


3


)


2


and the combination of the radicals R


1


and R


2


for each compound corresponds to one line of Table A




Table 25




Compounds of the formula Ia.5 where X


n


is hydrogen, Y


1


is oxygen and the combination of the radicals R


1


, R


3


and R


4


for each compound corresponds to one line of Table B











Table 26




Compounds of the formula Ia.5 where X


n


is hydrogen, Y


1


is NH and the combination of the radicals R


1


, R


3


and R


4


for each compound corresponds to one line of Table B




Table 27




Compounds of the formula Ia.5 where X


n


is hydrogen, Y


1


is NCH


3


and the combination of the radicals R


1


, R


3


and R


4


for each compound corresponds to one line of Table B




Table 28




Compounds of the formula Ia.6 where X


n


is hydrogen, Y


1


is oxygen and the combination of the radicals R


1


, R


3


and R


4


for each compound corresponds to one line of Table B











Table 29




Compounds of the formula Ia.6 where X


n


is hydrogen, Y


1


is NH and the combination of the radicals R


1


, R


3


and R


4


for each compound corresponds to one line of Table B




Table 30




Compounds of the formula Ia.6 where X


n


is hydrogen, Y


1


is NCH


3


and the combination of the radicals R


1


, R


3


and R


4


for each compound corresponds to one line of Table B




Table 31




Compounds of the formula Ia.7 where X


n


is hydrogen, Y


1


is oxygen and the combination of the radicals R


1


, R


3


and R


4


for each compound corresponds to one line of Table B











Table 32




Compounds of the formula Ia.7 where X


n


is hydrogen, Y


1


is NH and the combination of the radicals R


1


, R


3


and R


4


for each compound corresponds to one line of Table B




Table 33




Compounds of the formula Ia.7 where X


n


is hydrogen, Y


1


is NCH


3


and the combination of the radicals R


1


, R


3


and R


4


for each compound corresponds to one line of Table B




Table 34




Compounds of the formula Ia.8 where X


n


is hydrogen, Y


1


is oxygen and the combination of the radicals R


1


, R


3


and R


4


for each compound corresponds to one line of Table B











Table 35




Compounds of the formula Ia.8 where X


n


is hydrogen, Y


1


is NH and the combination of the radicals R


1


, R


3


and R


4


for each compound corresponds to one line of Table B




Table 36




Compounds of the formula Ia.8 where X


n


is hydrogen, Y


1


is NCH


3


and the combination of the radicals R


1


, R


3


and R


4


for each compound corresponds to one line of Table B




Table 37




Compounds of the formula Ia.8 where X


n


is 6-CF


3


, Y


1


is oxygen and the combination of the radicals R


1


, R


x


, R


y


and R


z


for each compound corresponds to one line of Table C




Table 38




Compounds of the formula Ia.8 where X


n


is 6-CH(CH


3


)


2


, Y


1


is oxygen and the combination of the radicals R


1


, R


3


and R


4


for each compound corresponds to one line of Table B




Table 39




Compounds of the formula Ia.8 where X


n


is 6-CF


3


, Y


1


is NH and the combination of the radicals R


1


, R


3


and R


4


for each compound corresponds to one line of Table B




Table 40




Compounds of the formula Ia.8 where X


n


is 6-CH(CH


3


)


2


, Y


1


is NH and the combination of the radicals R


1


, R


3


and R


4


for each compound corresponds to one line of Table B




Table 41




Compounds of the formula Ia.8 where X


n


is 6-CF


3


, Y


1


is NCH


3


and the combination of the radicals R


1


, R


3


and R


4


for each compound corresponds to one line of Table B




Table 42




Compounds of the formula Ia.8 where X


n


is 6-CH(CH


3


)


2


, Y


1


is NCH


3


and the combination of the radicals R


1


, R


3


and R


4


for each compound corresponds to one line of Table B




Table 43




Compounds of the formula Ib.5 where X


n


is hydrogen, Y


1


is oxygen and the combination of the radicals R


1


, R


3


and R


4


for each compound corresponds to one line of Table B











Table 44




Compounds of the formula Ib.5 where X


n


is hydrogen, Y


1


is NH and the combination of the radicals R


1


, R


3


and R


4


for each compound corresponds to one line of Table B




Table 45




Compounds of the formula Ib.5 where X


n


is hydrogen, Y


1


is NCH


3


and the combination of the radicals R


1


, R


3


and R


4


for each compound corresponds to one line of Table B




Table 46




Compounds of the formula Ib.6 where X


n


is hydrogen, Y


1


is oxygen and the combination of the radicals R


1


, R


3


and R


4


for each compound corresponds to one line of Table B











Table 47




Compounds of the formula Ib.6 where X


n


is hydrogen, Y


1


is NH and the combination of the radicals R


1


, R


3


and R


4


for each compound corresponds to one line of Table B




Table 48




Compounds of the formula Ib.6 where X


n


is hydrogen, Y


1


is NCH


3


and the combination of the radicals R


1


, R


3


and R


4


for each compound corresponds to one line of Table B




Table 49




Compounds of the formula Ib.7 where X


n


is hydrogen, Y


1


is oxygen and the combination of the radicals R


1


, R


3


and R


4


for each compound corresponds to one line of Table B











Table 50




Compounds of the formula Ib.7 where X


n


is hydrogen, Y


1


is NH and the combination of the radicals R


1


, R


3


and R


4


for each compound corresponds to one line of Table B




Table 51




Compounds of the formula Ib.7 where X


n


is hydrogen, Y


1


is NCH


3


and the combination of the radicals R


1


, R


3


and R


4


for each compound corresponds to one line of Table B




Table 52




Compounds of the formula Ib.8 where X


n


is hydrogen, Y


1


is oxygen and the combination of the radicals R


1


, R


3


and R


4


for each compound corresponds to one line of Table B











Table 53




Compounds of the formula Ib.8 where X


n


is hydrogen, Y


1


is NH and the combination of the radicals R


1


, R


3


and R


4


for each compound corresponds to one line of Table B




Table 54




Compounds of the formula Ib.8 where X


n


is hydrogen, Y


1


is NCH


3


and the combination of the radicals R


1


, R


3


and R


4


for each compound corresponds to one line of Table B




Table 55




Compounds of the formula Ib.8 where X


n


is 6-CF


3


, Y


1


is oxygen and the combination of the radicals R


1


, R


3


and R


4


for each compound corresponds to one line of Table B




Table 56




Compounds of the formula Ib.8 where X


n


is 6-CH(CH


3


)


2


, Y


1


is oxygen and the combination of the radicals R


1


, R


3


and R


4


for each compound corresponds to one line of Table B




Table 57




Compounds of the formula Ib.8 where X


n


is 6-CF


3


, Y


1


is NH and the combination of the radicals R


1


, R


3


and R


4


for each compound corresponds to one line of Table B




Table 58




Compounds of the formula Ib.8 where X


n


is 6-CH(CH


3


)


2


, Y


1


is NH and the combination of the radicals R


1


, R


3


and R


4


for each compound corresponds to one line of Table B




Table 59




Compounds of the formula Ib.8 where X


n


is 6-CF


3


, Y


1


is NCH


3


and the combination of the radicals R


1


, R


3


and R


4


for each compound corresponds to one line of Table B




Table 60




Compounds of the formula Ib.8 where X


n


is 6-CH(CH


3


)


2


, Y


1


is NCH


3


and the combination of the radicals R


1


, R


3


and R


4


for each compound corresponds to one line of Table B




Table 61




Compounds of the formula Ic.5 where X


n


is hydrogen, Y


1


is oxygen and the combination of the radicals R


1


, R


3


and R


4


for each compound corresponds to one line of Table B











Table 62




Compounds of the formula Ic.5 where X


n


is hydrogen, Y


1


is NH and the combination of the radicals R


1


, R


3


and R


4


for each compound corresponds to one line of Table B




Table 63




Compounds of the formula Ic.5 where X


n


is hydrogen, Y


1


is NCH


3


and the combination of the radicals R


1


, R


3


and R


4


for each compound corresponds to one line of Table B




Table 64




Compounds of the formula Ic.6 where X


n


is hydrogen, Y


1


is oxygen and the combination of the radicals R


1


, R


3


and R


4


for each compound corresponds to one line of Table B











Table 65




Compounds of the formula Ic.6 where X


n


is hydrogen, Y


1


is NH and the combination of the radicals R


1


, R


3


and R


4


for each compound corresponds to one line of Table B




Table 66




Compounds of the formula Ic.6 where X


n


is hydrogen, Y


1


is NCH


3


and the combination of the radicals R


1


, R


3


and R


4


for each compound corresponds to one line of Table B




Table 67




Compounds of the formula Ic.7 where X


n


is hydrogen, Y


1


is oxygen and the combination of the radicals R


1


, R


3


and R


4


for each compound corresponds to one line of Table B











Table 68




Compounds of the formula Ic.7 where X


n


is hydrogen, Y


1


is NH and the combination of the radicals R


1


, R


3


and R


4


for each compound corresponds to one line of Table B




Table 69




Compounds of the formula Ic.7 where X


n


is hydrogen, Y


1


is NCH


3


and the combination of the radicals R


1


, R


3


and R


4


for each compound corresponds to one line of Table B




Table 70




Compounds of the formula Ic.8 where X


n


is hydrogen, Y


1


is oxygen and the combination of the radicals R


1


, R


3


and R


4


for each compound corresponds to one line of Table B











Table 71




Compounds of the formula Ic.8 where X


n


is hydrogen, Y


1


is NH and the combination of the radicals R


1


, R


3


and R


4


for each compound corresponds to one line of Table B




Table 72




Compounds of the formula Ic.8 where X


n


is hydrogen, Y


1


is NCH


3


and the combination of the radicals R


1


, R


3


and R


4


for each compound corresponds to one line of Table B




Table 73




Compounds of the formula Ic.8 where X


n


is 6-CF


3


, Y


1


is oxygen and the combination of the radicals R


1


, R


3


and R


4


for each compound corresponds to one line of Table B




Table 74




Compounds of the formula Ic.8 where X


n


is 6-CH(CH


3


)


2


, Y


1


is oxygen and the combination of the radicals R


1


, R


3


and R


4


for each compound corresponds to one line of Table B




Table 75




Compounds of the formula Ic.8 where X


n


is 6-CF


3


, Y


1


is NH and the combination of the radicals R


1


, R


3


and R


4


for each compound corresponds to one line of Table B




Table 76




Compounds of the formula Ic.8 where X


n


is 6-CH(CH


3


)


2


, Y


1


is NH and the combination of the radicals R


1


, R


3


and R


4


for each compound corresponds to one line of Table B




Table 77




Compounds of the formula Ic.8 where X


n


is 6-CF


3


, Y


1


is NCH


3


and the combination of the radicals R


1


, R


3


and R


4


for each compound corresponds to one line of Table B




Table 78




Compounds of the formula Ic.8 where X


n


is 6-CH(CH


3


)


2


, Y


1


is NCH


3


and the combination of the radicals R


1


, R


3


and R


4


for each compound corresponds to one line of Table B




Table 79




Compounds of the formula Id.5 where X


n


is hydrogen, Y


1


is oxygen and the combination of the radicals R


1


, R


3


and R


4


for each compound corresponds to one line of Table B











Table 80




Compounds of the formula Id.5 where X


n


is hydrogen, Y


1


is NH and the combination of the radicals R


1


, R


3


and R


4


for each compound corresponds to one line of Table B




Table 81




Compounds of the formula Id.5 where X


n


is hydrogen, Y


1


is NCH


3


and the combination of the radicals R


1


, R


3


and R


4


for each compound corresponds to one line of Table B




Table 82




Compounds of the formula Id.6 where X


n


is hydrogen, Y


1


is oxygen and the combination of the radicals R


1


, R


3


and R


4


for each compound corresponds to one line of Table B











Table 83




Compounds of the formula Id.6 where X


n


is hydrogen, Y


1


is NH and the combination of the radicals R


1


, R


3


and R


4


for each compound corresponds to one line of Table B




Table 84




Compounds of the formula Id.6 where X


n


is hydrogen, Y


1


is NCH


3


and the combination of the radicals R


1


, R


3


and R


4


for each compound corresponds to one line of Table B




Table 85




Compounds of the formula Id.7 where X


n


is hydrogen, Y


1


is oxygen and the combination of the radicals R


1


, R


3


and R


4


for each compound corresponds to one line of Table B











Table 86




Compounds of the formula Id.7 where X


n


is hydrogen, Y


1


is NH and the combination of the radicals R


1


, R


3


and R


4


for each compound corresponds to one line of Table B




Table 87




Compounds of the formula Id.7 where X


n


is hydrogen, Y


1


is NCH


3


and the combination of the radicals R


1


, R


3


and R


4


for each compound corresponds to one line of Table B




Table 88




Compounds of the formula Id.8 where X


n


is hydrogen, Y


1


is oxygen and the combination of the radicals R


1


, R


3


and R


4


for each compound corresponds to one line of Table B











Table 89




Compounds of the formula Id.8 where X


n


is hydrogen, Y


1


is NH and the combination of the radicals R


1


, R


3


and R


4


for each compound corresponds to one line of Table B




Table 90




Compounds of the formula Id.8 where X


n


is hydrogen, Y


1


is NCH


3


and the combination of the radicals R


1


, R


3


and R


4


for each compound corresponds to one line of Table B




Table 91




Compounds of the formula Id.8 where X


n


is 6-CF


3


, Y


1


is oxygen and the combination of the radicals R


1


, R


3


and R


4


for each compound corresponds to one line of Table B




Table 92




Compounds of the formula Id.8 where X


n


is 6-CH(CH


3


)


2


, Y


1


is oxygen and the combination of the radicals R


1


, R


3


and R


4


for each compound corresponds to one line of Table B




Table 93




Compounds of the formula Id.8 where X


n


is 6-CF


3


, Y


1


is NH and the combination of the radicals R


1


, R


3


and R


4


for each compound corresponds to one line of Table B




Table 94




Compounds of the formula Id.8 where X


n


is 6-CH(CH


3


)


2


, Y


1


is NH and the combination of the radicals R


1


, R


3


and R


4


for each compound corresponds to one line of Table B




Table 95




Compounds of the formula Id.8 where X


n


is 6-CF


3


, Y


1


is NCH


3


and the combination of the radicals R


1


, R


3


and R


4


for each compound corresponds to one line of Table B




Table 96




Compounds of the formula Id.8 where X


n


is 6-CH(CH


3


)


2


, Y


1


is NCH


3


and the combination of the radicals R


1


, R


3


and R


4


for each compound corresponds to one line of Table B




Table 97




Compounds of the formula Ia.9 where X


n


is hydrogen and the combination of the radicals R


1


, R


x


, R


y


and R


z


for each compound corresponds to one line of Table C











Table 98




Compounds of the formula Ia.10 where X


n


is hydrogen and the combination of the radicals R


1


, R


x


, R


y


and R


z


for each compound corresponds to one line of Table C











Table 99




Compounds of the formula Ia.11 where X


n


is hydrogen and the combination of the radicals R


1


, R


x


, R


y


and R


z


for each compound corresponds to one line of Table C











Table 100




Compounds of the formula Ia.12 where X


n


is hydrogen and the combination of the radicals R


1


, R


x


, R


y


and R


z


for each compound corresponds to one line of Table C











Table 101




Compounds of the formula Ia.12 where X


n


is 6-CF


3


and the combination of the radicals R


1


, R


x


, R


y


and R


z


for each compound corresponds to one line of Table C




Table 102




Compounds of the formula Ia.12 where X


n


is 6-CH(CH


3


)


2


and the combination of the radicals R


1


, R


x


, R


y


and R


z


for each compound corresponds to one line of Table C




Table 103




Compounds of the formula Ib.9 where X


n


is hydrogen and the combination of the radicals R


1


, R


x


, R


y


and R


z


for each compound corresponds to one line of Table C











Table 104




Compounds of the formula Ib.10 where X


n


is hydrogen and the combination of the radicals R


1


, R


x


, R


y


and R


z


for each compound corresponds to one line of Table C











Table 105




Compounds of the formula Ib.11 where X


n


is hydrogen and the combination of the radicals R


1


, R


x


, R


y


and R


z


for each compound corresponds to one line of Table C











Table 106




Compounds of the formula Ib.12 where X


n


is hydrogen and the combination of the radicals R


1


, R


x


, R


y


and R


z


for each compound corresponds to one line of Table C











Table 107




Compounds of the formula Ib.12 where X


n


is 6-CF


3


and the combination of the radicals R


1


, R


x


, R


y


and R


z


for each compound corresponds to one line of Table C




Table 108




Compounds of the formula Ib.12 where X


n


is 6-CH(CH


3


)


2


and the combination of the radicals R


1


, R


x


, R


y


and R


z


for each compound corresponds to one line of Table C




Table 109




Compounds of the formula Ic.9 where X


n


is hydrogen and the combination of the radicals R


1


, R


x


, R


y


and R


z


for each compound corresponds to one line of Table C











Table 110




Compounds of the formula Ic.10 where X


n


is hydrogen and the combination of the radicals R


1


, R


x


, R


y


and R


z


for each compound corresponds to one line of Table C











Table 111




Compounds of the formula Ic.11 where X


n


is hydrogen and the combination of the radicals R


1


, R


x


, R


y


and R


z


for each compound corresponds to one line of Table C











Table 112




Compounds of the formula Ic.12 where X


n


is hydrogen and the combination of the radicals R


1


, R


x


, R


y


and R


z


for each compound corresponds to one line of Table C











Table 113




Compounds of the formula Ic.12 where X


n


is 6-CF


3


and the combination of the radicals R


1


, R


x


, R


y


and R


z


for each compound corresponds to one line of Table C




Table 114




Compounds of the formula Ic.12 where X


n


is 6-CH(CH


3


)


2


and the combination of the radicals R


1


, R


x


, R


y


and R


z


for each compound corresponds to one line of Table C




Table 115




Compounds of the formula Id.9 where X


n


is hydrogen and the combination of the radicals R


1


, R


x


, R


y


and R


z


for each compound corresponds to one line of Table C











Table 116




Compounds of the formula Id.10 where X


n


is hydrogen and the combination of the radicals R


1


, R


x


, R


y


and R


z


for each compound corresponds to one line of Table C











Table 117




Compounds of the formula Id.11 where X


n


is hydrogen and the combination of the radicals R


1


, R


x


, R


y


and R


z


for each compound corresponds to one line of Table C











Table 118




Compounds of the formula Id.12 where X


n


is hydrogen and the combination of the radicals R


1


, R


x


, R


y


and R


z


for each compound corresponds to one line of Table C











Table 119




Compounds of the formula Id.12 where X


n


is 6-CF


3


and the combination of the radicals R


1


, R


x


, R


y


and R


z


for each compound corresponds to one line of Table C




Table 120




Compounds of the formula Id.12 where X


n


is 6-CH(CH


3


)


2


and the combination of the radicals R


1


, R


x


, R


y


and R


z


for each compound corresponds to one line of Table C
















TABLE A











No.




R


1






R


2















A.1




H




CH


3









A.2




H




CH


2


CH


3









A.3




H




CH


2


CH


2


CH


3









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


5









A.9




H




2-F—C


6


H


4









A.10




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









A.15




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







A.20




H




CH


2


CH


2


Cl







A.21




H




CH


2


CH


2


CH


2


CN







A.22




H




CH


2


—C


6


H


5









A.23




H




CH


2


CH


2


CH


2


CH


2


—OCH


3









A.24




H




CH


2


CH


2


—OCH


2


CH


3









A.25




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




3-CN—C


6


H


4









A.29




H




3,5-(CH


3


)


2


—C


6


H


3









A.30




H




3-COCH


3


—C


6


H


4









A.31




H




3-[C(CH


3


)═NOCH


3


]—C


6


H


4









A.32




H




1-naphthyl







A.33




H




CH


2


CH


2


—O—C


6


H


5









A.34




H




CH


2


—(3-Cl-pyridin-5-yl]







A.35




H




4-OCH


3


-pyridin-2-yl







A.36




H




CH


2


—[5-Cl-pyrazin-2-yl]







A.37




H




2-thienyl







A.38




H




3-CH(CH


3


)


2


-isoxazol-5-yl







A.39




H




3-C


6


H


5


-pyrazol-1-yl







A.40




H




OCH(CH


3


)


2









A.41




H




OCH


2


CH


2


CH


2


CH


2


CH


3









A.42




H




O-[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]







A.45




H




O—CO-[4-Cl—C


6


H


4


]







A.46




H




NH-[4-Cl—C


6


H


4


]







A.47




CH


3






CH


3









A.48




CH


3






CH


2


CH


3









A.49




CH


3






CH


2


CH


2


CH


3









A.50




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


5









A.55




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




CH


3






3-CF


3


—C


6


H


4









A.61




CH


3






3-Cl—C


6


H


4









A.62




CH


3






2-CH


3


—C


6


H


4









A.63




CH


3






4-CH


3


—C


6


H


4









A.64




CH


3






cyclopropyl







A.65




CH


3






cyclohexyl







A.66




CH


3






CH


2


CH


2


Cl







A.67




CH


3






CH


2


CH


2


CH


2


CN







A.68




CH


3






CH


2


—C


6


H


5









A.69




CH


3






CH


2


CH


2


CH


2


CH


2


—OCH


3









A.70




CH


3






CH


2


CH


2


—OCH


2


CH


3









A.71




CH


3






CH


2


C(CH


3


)═NOCH


3









A.72




CH


3






CH


2


-[4-F—C


6


H


4


]







A.73




CH


3






CH


2


-[3-CN—C


6


H


4


]







A.147




CH


3






3-CN—C


6


H


4









A.148




CH


3






3,5-(CH


3


)


2


—C


6


H


3









A.149




CH


3






3-COCH


3


—C


6


H


4









A.150




CH


3






3-[C(CH


3


)═NOCH


3


]—C


6


H


4









A.151




CH


3






1-naphthyl







A.152




CH


3






CH


2


CH


2


—O—C


6


H


5









A.153




CH


3






CH


2


-[3-Cl-pyridin-5-yl]







A.154




CH


3






4-OCH


3


-pyridin-2-yl







A.155




CH


3






CH


2


-[5-Cl-pyrazin-2-yl]







A.156




CH


3






2-thienyl







A.157




CH


3






3-CH(CH


3


)


2


-isoxazol-5-yl







A.158




CH


3






3-C


6


H


5


-pyrazol-1-yl







A.159




CH


3






OCH(CH


3


)


2









A.160




CH


3






OCH


2


CH


2


CH


2


CH


2


CH


3









A.161




CH


3






O-[4-F—C


6


H


4


]







A.162




CH


3






OCH


2


-[4-F—C


6


H


4


]







A.163




CH


3






O-[6-CH


3


-pyridin-2-yl]







A.164




CH


3






O—CO-[4-Cl—C


6


H


4


]







A.165




CH


3






NH-[4-Cl—C


6


H


4


]







A.166




OH




CH


3









A.167




OH




CH


2


CH


2


CH


2


CH


3









A.168




OH




CH(CH


3


)


2









A.169




OH




3-CH


3


—C


6


H


4









A.170




OH




CH


2


—C


6


H


5









A.171




OH




3,5-Cl


2


—C


6


H


3









A.172




OCH


3






CH


3









A.173




OCH


3






CH


2


CH


2


CH


2


CH


3









A.174




OCH


3






CH(CH


3


)


2









A.175




OCH


3






CH


2


CH


2


CH


2


CH


2


CH


2


CH


3









A.176




OCH


3






3-CH


3


—C


6


H


4









A.177




OCH


3






CH


2


—C


6


H


5









A.178




OCH


3






3,5-Cl


2


—C


6


H


3









A.179




OCH


2


CH


3






CH


3









A.180




OCH


2


CH


3






CH


2


CH


2


CH


3









A.181




OCH


2


CH


3






CH(CH


3


)


2









A.182




OCH


2


CH


3






CH


2


CH


2


CH


2


CH


2


CH


3









A.183




OCH


2


CH


3






3-CH


3


—C


6


H


4









A.184




OCH


2


CH


3






CH


2


-[4-F—C


6


H


4


]







A.185




OCH


2


CH


3






2,4-F


2


—C


6


H


3









A.186




cyclopropyl




CH


3









A.187




cyclopropyl




CH


2


CH


2


CH


3









A.188




cyclopropyl




OCH


2


CH


3









A.189




cyclopropyl




C


6


H


5









A.190




Cl




C


6


H


5









A.191




Cl




CH


3









A.192




Cl




CH(CH


3


)


2









A.193




Cl




3-CH


3


—C


6


H


4









A.194




Cl




3-CN—C


6


H


4









A.195




Cl




CH


2


CH


2


—O—C


6


H


5









A.196




Cl




CH


2


CH


2


—OCH


2


CH


3









A.197




Cl




CH


2


-[4-F—C


6


H


4


]







A.198




SCH


3






CH


3









A.199




SCH


3






C


6


H


5









A.200




SCH


3






CH(CH


3


)


2









A.201




CH(CH


3


)


2






CH


3









A.202




CH(CH


3


)


2






CH


2


CH


3









A.203




CH(CH


3


)


2






C


6


H


5









A.204




CH(CH


3


)


2






OCH


3









A.205




CH(CH


3


)


2






OCH(CH


3


)


2









A.206




CH(CH


3


)


2






3-CH


3


—C


6


H


4









A.207




CN




CH


3









A.208




CN




3-CH


3


—C


6


H


4









A.209




CN




CH


2


-[2,4-Cl


2


—C


6


H


3


]







A.210




CN




CH


2


CH


2


CH


2


CH


3









A.211




CN




CH(CH


3


)


2









A.212




CH


2


CH


3






CH


3









A.213




CH


2


CH


3






CH


2


CH


3









A.214




CH


2


CH


3






CH


2


CH


2


CH


3









A.215




CH


2


CH


3






CH(CH


3


)


2









A.216




CH


2


CH


3






CH


2


CH


2


CH


2


CH


3









A.217




CH


2


CH


3






C(CH


3


)


3









A.218




CH


2


CH


3






CH(CH


3


)CH


2


CH


3









A.219




CH


2


CH


3






C


6


H


5









A.220




CH


2


CH


3






2-F—C


6


H


4









A.221




CH


2


CH


3






3-F—C


6


H


4









A.222




CH


2


CH


3






4-F—C


6


H


4









A.223




CH


2


CH


3






3-CH


3


—C


6


H


4









A.224




CH


2


CH


3






3-OCH


3


—C


6


H


4









A.225




CH


2


CH


3






3-CF


3


—C


6


H


4









A.226




CH


2


CH


3






3-Cl—C


6


H


4









A.227




CH


2


CH


3






2-CH


3


—C


6


H


4









A.228




CH


2


CH


3






4-CH


3


—C


6


H


4









A.229




CH


2


CH


3






cyclopropyl







A.230




CH


2


CH


3






cyclohexyl







A.231




CH


2


CH


3






CH


2


CH


2


Cl







A.232




CH


2


CH


3






CH


2


CH


2


CH


2


CN







A.233




CH


2


CH


3






CH


2


—C


6


H


5









A.234




CH


2


CH


3






CH


2


CH


2


CH


2


CH


2


—OCH


3









A.235




CH


2


CH


3






CH


2


CH


2


—OCH


2


CH


3









A.236




CH


2


CH


3






CH


2


C(CH


3


)═NOCH


3









A.237




CH


2


CH


3






CH


2


-[4-F—C


6


H


4


]







A.238




CH


2


CH


3






CH


2


-[3-CN—C


6


H


4


]







A.239




CH


2


CH


3






3-CN—C


6


H


4









A.240




CH


2


CH


3






3,5-(CH


3


)


2


—C


6


H


3









A.241




CH


2


CH


3






3-COCH


3


—C


6


H


4









A.242




CH


2


CH


3






3-[C(CH


3


)═NOCH


3


]—C


6


H


4









A.243




CH


2


CH


3






1-naphthyl







A.244




CH


2


CH


3






CH


2


CH


2


—O—C


6


H


5









A.245




CH


2


CH


3






CH


2


-[3-Cl-pyridin-5-yl]







A.246




CH


2


CH


3






4-OCH


3


-pyridin-2-yl







A.247




CH


2


CH


3






CH


2


-[5-Cl-pyrazin-2-yl]







A.248




CH


2


CH


3






2-thienyl







A.249




CH


2


CH


3






3-CH(CH


3


)


2


-isoxazol-5-yl







A.250




CH


2


CH


3






3-C


6


H


5


-pyrazol-1-yl







A.251




CH


2


CH


3






OCH(CH


3


)


2









A.252




CH


2


CH


3






OCH


2


CH


2


CH


2


CH


2


CH


3









A.253




CH


2


CH


3






O-[4-F—C


6


H


4


]







A.254




CH


2


CH


3






OCH


2


-[4-F—C


6


H


4


]







A.255




CH


2


CH


3






O-[6-CH


3


-pyridin-2-yl]







A.256




CH


2


CH


3






O—CO-[4-Cl—C


6


H


4


]







A.257




CH


2


CH


3






NH-[4-Cl—C


6


H


4


]







A.258




CH


3






CH


2


ON═C(CH


3


)


2









A.259




CH


3






CH


2


ON═C(CH


3


)—CH


2


CH


3









A.260




CH


3






CH


2


ON═C(CH


3


)—C


6


H


5









A.261




CH


3






CH


2


ON═C(CH


3


)-[4-Cl—C


6


H


4


]







A.262




CH


2


CH


3






CH


2


ON═C(CH


3


)


2









A.263




CH


2


CH


3






CH


2


ON═C(CH


3


)—CH


2


CH


3









A.264




CH


2


CH


3






CH


2


ON═C(CH


3


)—C


6


H


5









A.265




CH


2


CH


3






CH


2


ON═C(CH


3


)-[4-Cl—C


6


H


4


]







A.266




CH


2


—C


6


H


5






CH


2


ON═C(CH


3


)


2









A.267




CH


2


—C


6


H


5






CH


2


ON═C(CH


3


)—CH


2


CH


3









A.268




CH


2


—C


6


H


5






CH


2


ON═C(CH


3


)—C


6


H


5









A.269




CH


2


—C


6


H


5






CH


2


ON═C(CH


3


)-[4-Cl—C


6


H


4


]







A.270




H




CH═CH—C


6


H


5









A.271




H




CH═C(CH


3


)—C


6


H


5









A.272




H




CH═CCl—C


6


H


5









A.273




H




C(CH


3


)═CH—C


6


H


5









A.274




H




CCl═CH—C


6


H


5









A.275




H




CH═CH-[4-F—C


6


H


4


]







A.276




H




CH═C(CH


3


)-[4-F—C


6


H


4


]







A.277




H




CH═CCl-[4-F—C


6


H


4


]







A.278




H




CCl═CH-[4-F—C


6


H


4


]







A.279




H




C(CH


3


)═CH-[4-F—C


6


H


4


]







A.280




CH


3






CH═CH—C


6


H


5









A.281




CH


3






CH═C(CH


3


)—C


6


H


5









A.282




CH


3






CH═CCl—C


6


H


5









A.283




CH


3






C(CH


3


)═CH—C


6


H


5









A.284




CH


3






CCl═CH—C


6


H


5









A.285




CH


3






CH═CH-[4-F—C


6


H


4


]







A.286




CH


3






CH═C(CH


3


)-[4-F—C


6


H


4


]







A.287




CH


3






CH═CCl-[4-F—C


6


H


4


]







A.288




CH


3






CCl═CH-[4-F—C


6


H


4


]







A.289




CH


3






C(CH


3


)═CH-[4-F—C


6


H


4


]







A.290




CH


2


CH


3






CH═CH—C


6


H


5









A.291




CH


2


CH


3






CH═C(CH


3


)—C


6


H


5









A.292




CH


2


CH


3






CH═CCl—C


6


H


5









A.293




CH


2


CH


3






C(CH


3


)═CH—C


6


H


5









A.294




CH


2


CH


3






CCl═CH—C


6


H


5









A.295




CH


2


CH


3






CH═CH-[4-F—C


6


H


4


]







A.296




CH


2


CH


3






CH═C(CH


3


)-[4-F—C


6


H


4


]







A.297




CH


2


CH


3






CH═CCl-[4-F—C


6


H


4


]







A.298




CH


2


CH


3






CCl═CH-[4-F—C


6


H


4


]







A.299




CH


2


CH


3






C(CH


3


)═CH-[4-F—C


6


H


4


]







A.300




CH


2


—C


6


H


5






CH═CH—C


6


H


5









A.301




CH


2


—C


6


H


5






CH═C(CH


3


)—C


6


H


5









A.302




CH


2


—C


6


H


5






CH═CCl—C


6


H


5









A.303




CH


2


—C


6


H


5






C(CH


3


)═CH—C


6


H


5









A.304




CH


2


—C


6


H


5






CCl═CH—C


6


H


5









A.305




CH


2


—C


6


H


5






CH═CH-[4-F—C


6


H


4


]







A.306




CH


2


—C


6


H


5






CH═C(CH


3


)-[4-F—C


6


H


4


]







A.307




CH


2


—C


6


H


5






CH═CCl-[4-F—C


6


H


4


]







A.308




CH


2


—C


6


H


5






CCl═CH-[4-F—C


6


H


4


]







A.309




CH


2


—C


6


H


5






C(CH


3


)═CH-[4-F—C


6


H


4


]







A.310




H




CH(CH


3


)—C(CH


3


)═NOCH


3









A.311




H




CH(CH


3


)—C(CH


3


)═NOCH


2


CH


3









A.312




H




CH(CH


3


)—C


6


H


5









A.313




H




CH(CH


3


)-[4-F—C


6


H


4


]







A.314




H




1-C


6


H


5


-cyclopropyl







A.315




H




1-[4-Cl—C


6


H


4


]-cyclopropyl







A.316




H




CH


2


C(CH


3


)═NOCH


3









A.317




H




CH


2


C(CH


3


)═NOCH


2


CH


3









A.318




H




1-[C(CH


3


)═NOCH


3


)-cyclopropyl







A.319




CH


3






CH(CH


3


)—C(CH


3


)═NOCH


3









A.320




CH


3






CH(CH


3


)—C(CH


3


)═NOCH


2


CH


3









A.321




CH


3






CH(CH


3


)—C


6


H


5









A.322




CH


3






CH(CH


3


)-[4-F—C


6


H


4


]







A.323




CH


3






1-C


6


H


5


-cyclopropyl







A.324




CH


3






1-[4-Cl—C


6


H


4


]-cyclopropyl







A.325




CH


3






CH


2


C(CH


3


)═NOCH


3









A.326




CH


3






CH


2


C(CH


3


)═NOCH


2


CH


3









A.327




CH


3






1-[C(CH


3


)═NOCH


3


]-cyclopropyl







A.328




CH


2


CH


3






CH(CH


3


)—C(CH


3


)═NOCH


3









A.329




CH


2


CH


3






CH(CH


3


)—C(CH


3


)═NOCH


2


CH


3









A.330




CH


2


CH


3






CH(CH


3


)—C


6


H


5









A.331




CH


2


CH


3






CH(CH


3


)-[4-F—C


6


H


4


]







A.332




CH


2


CH


3






1-C


6


H


5


-cyclopropyl







A.333




CH


2


CH


3






1-[4-Cl—C


6


H


4


)-cyclopropyl







A.334




CH


2


CH


3






CH


2


C(CH


3


)═NOCH


3









A.335




CH


2


CH


3






CH


2


C(CH


3


)═NOCH


2


CH


3









A.336




CH


2


CH


3






1-[C(CH


3


)═NOCH


3


]-cyclopropyl







A.337




CH


2


—C


6


H


5






CH(CH


3


)—C(CH


3


)═NOCH


3









A.338




CH


2


—C


6


H


5






CH(CH


3


)—C(CH


3


)═NOCH


2


CH


3









A.339




CH


2


—C


6


H


5






CH(CH


3


)—C


6


H


5









A.340




CH


2


—C


6


H


5






CH(CH


3


)-[4-F—C


6


H


4


]







A.341




CH


2


—C


6


H


5






1-C


6


H


5


-cyclopropyl







A.342




CH


2


—C


6


H


5






1-[4-Cl—C


6


H


4


]-cyclopropyl







A.343




CH


2


—C


6


H


5






CH


2


C(CH


3


)═NOCH


3









A.344




CH


2


—C


6


H


5






CH


2


C(CH


3


)═NOCH


2


CH


3









A.345




CH


2


—C


6


H


5






1-[C(CH


3


)═NOCH


3


]-cyclopropyl














A.346




—(CH


2


)


4


—







A.347




—(CH


2


)


5


—







A.348




—(CH


2


)


2


—O—(CH


2


)


2


—







A.349




—(CH


2


)


2


—S—(CH


2


)


2


—







A.350




—(CH


2


)


2


—CH(CH


3


)—(CH


2


)


2


—







A.351




—(CH


2


)


2


—C(═O)—(CH


2


)


2


—







A.352




—(CH


2


)


2


—C(═NOCH


3


)—(CH


2


)


2


—







A.353




—(CH


2


)


2


—C(OCH


3


)


2


—(CH


2


)


2


—







A.354




—CH


2


—CH(CH


3


)—CH


2


—CH(CH


3


)—CH


2


—







A.355




—(CH


2


)


3


—CH(CH


3


)—CH


2


—







A.356




—CH═CH—C(═NOCH


3


)—CH═CH—







A.357




—CH


2


—C(═NOCH


3


)—(CH


2


)


3


—















A.358




CH


3






CF


3









A.359




H




CF


3









A.360




CF


3






CH


3









A.361




CF


3






H




























TABLE B











No.




R


1






R


3






R


4















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







B.5




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







B.10




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







B.14




CH


3






CF


3






H







B.15




CH


3






CHF


2






H







B.16




CH


3






CH


2


F




H







B.17




CH


3






Cl




H







B.18




CH


3






OCH


3






H







B.19




CH


3






OCH


2


CH


3






H







B.20




CH


3






CN




H







B.21




CF


3






H




H







B.22




CF


3






CH


3






H







B.23




CF


3






CH


2


CH


3






H







B.24




CF


3






CF


3






H







B.25




CF


3






CHF


2






H







B.26




CF


3






CH


2


F




H







B.27




CF


3






Cl




H







B.28




CF


3






OCH


3






H







B.29




CF


3






OCH


2


CH


3






H







B.30




CF


3






CN




H







B.31




Cl




H




CH


3









B.32




Cl




CH


3






CH


3









B.33




Cl




CH


2


CH


3






CH


3









B.34




Cl




CF


3






CH


3









B.35




Cl




CHF


2






CH


3









B.36




Cl




CH


2


F




CH


3









B.37




Cl




Cl




CH


3









B.38




Cl




OCH


3






CH


3









B.39




Cl




OCH


2


CH


3






CH


3









B.40




Cl




CN




CH


3









B.41




CH


3






H




CH


3









B.42




CH


3






CH


3






CH


3









B.43




CH


3






CH


2


CH


3






CH


3









B.44




CH


3






CF


3






CH


3









B.45




CH


3






CHF


2






CH


3









B.46




CH


3






CH


2


F




CH


3









B.47




CH


3






Cl




CH


3









B.48




CH


3






OCH


3






CH


3









B.49




CH


3






OCH


2


CH


3






CH


3









B.50




CH


3






CN




CH


3









B.51




CF


3






H




CH


3









B.52




CF


3






CH


3






CH


3









B.53




CF


3






CH


2


CH


3






CH


3









B.54




CF


3






CF


3






CH


3









B.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









B.59




CF


3






OCH


2


CH


3






CH


3









B.60




CF


3






CN




CH


3









B.61




Cl




H




CH


2


CH


3









B.62




Cl




CH


3






CH


2


CH


3









B.63




Cl




CH


2


CH


3






CH


2


CH


3









B.64




Cl




CF


3






CH


2


CH


3









B.65




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









B.70




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









B.75




CH


3






CHF


2






CH


2


CH


3









B.76




CH


3






CH


2


F




CH


2


CH


3









B.77




CH


3






Cl




CH


2


CH


3









B.78




CH


3






OCH


3






CH


2


CH


3









B.79




CH


3






OCH


2


CH


3






CH


2


CH


3









B.80




CH


3






CN




CH


2


CH


3









B.81




CF


3






H




CH


2


CH


3









B.82




CF


3






CH


3






CH


2


CH


3









B.83




CF


3






CH


2


CH


3






CH


2


CH


3









B.84




CF


3






CF


3






CH


2


CH


3









B.85




CF


3






CHF


2






CH


2


CH


3









B.86




CF


3






CH


2


F




CH


2


CH


3









B.87




CF


3






Cl




CH


2


CH


3









B.88




CF


3






OCH


3






CH


2


CH


3









B.89




CF


3






OCH


2


CH


3






CH


2


CH


3









B.90




CF


3






CN




CH


2


CH


3









B.91




Cl




H




CH


2


CH


2


CH


3









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






CH


2


CH


2


CH


3









B.95




Cl




CHF


2






CH


2


CH


2


CH


3









B.96




Cl




CH


2


F




CH


2


CH


2


CH


3









B.97




Cl




Cl




CH


2


CH


2


CH


3









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




CH


2


CH


2


CH


3









B.101




CH


3






H




CH


2


CH


2


CH


3









B.102




CH


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




CH


3






CF


3






CH


2


CH


2


CH


3









B.105




CH


3






CHF


2






CH


2


CH


2


CH


3









B.106




CH


3






CH


2


F




CH


2


CH


2


CH


3









B.107




CH


3






Cl




CH


2


CH


2


CH


3









B.108




CH


3






OCH


3






CH


2


CH


2


CH


3









B.109




CH


3






OCH


2


CH


3






CH


2


CH


2


CH


3









B.110




CH


3






CN




CH


2


CH


2


CH


3









B.111




CF


3






H




CH


2


CH


2


CH


3









B.112




CF


3






CH


3






CH


2


CH


2


CH


3









B.113




CF


3






CH


2


CH


3






CH


2


CH


2


CH


3









B.114




CF


3






CF


3






CH


2


CH


2


CH


3









B.115




CF


3






CHF


2






CH


2


CH


2


CH


3









B.116




CF


3






CH


2


F




CH


2


CH


2


CH


3









B.117




CF


3






Cl




CH


2


CH


2


CH


3









B.118




CF


3






OCH


3






CH


2


CH


2


CH


3









B.119




CF


3






OCH


2


CH


3






CH


2


CH


2


CH


3









B.120




CF


3






CN




CH


2


CH


2


CH


3









B.121




Cl




H




CH(CH


3


)


2









B.122




Cl




CH


3






CH(CH


3


)


2









B.123




Cl




CH


2


CH


3






CH(CH


3


)


2









B.124




Cl




CF


3






CH(CH


3


)


2









B.125




Cl




CHF


2






CH(CH


3


)


2









B.126




Cl




CH


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






CH(CH


3


)


2









B.130




Cl




CN




CH(CH


3


)


2









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




CN




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




CH


2


CH═CH


2









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









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






CH


2


CH═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—Cl (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—Cl (transY







B.197




CH


3






Cl




CH


2


CH═CH—Cl (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






H




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)







B.209




CF


3






OCH


2


CH


3






CH


2


CH═CH—Cl (trans)







B.210




CF


3






CN




CH


2


CH═CH—Cl (trans)







B.211




Cl




H




CH


2


CCl═CH


2









B.212




Cl




CH


3






CH


2


CCl═CH


2









B.213




Cl




CH


2


CH


3






CH


2


CCl═CH


2









B.214




Cl




CF


3






CH


2


CCl═CH


2









B.215




Cl




CHF


2






CH


2


CCl═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




OCH


3






CH


2


CCl═CH


2









B.219




Cl




OCH


2


CH


3






CH


2


CCl═CH


2









B.220




Cl




CN




CH


2


CCl═CH


2









B.221




CH


3






H




CH


2


CCl═CH


2









B.222




CH


3






CH


3






CH


2


CCl═CH


2









B.223




CH


3






CH


2


CH


3






CH


2


CCl═CH


2









B.224




CH


3






CF


3






CH


2


CCl═CH


2









B.225




CH


3






CHF


2






CH


2


CCl═CH


2









B.226




CH


3






CH


2


F




CH


2


CCl═CH


2









B.227




CH


3






Cl




CH


2


CCl═CH


2









B.228




CH


3






OCH


3






CH


2


CCl═CH


2









B.229




CH


3






OCH


2


CH


3






CH


2


CCl═CH


2









B.230




CH


3






CN




CH


2


CCl═CH


2









B.231




CF


3






H




CH


2


CCl═CH


2









B.232




CF


3






CH


3






CH


2


CCl═CH


2









B.233




CF


3






CH


2


CH


3






CH


2


CCl═CH


2









B.234




CF


3






CF


3






CH


2


CCl═CH


2









B.235




CF


3






CHF


2






CH


2


CCl═CH


2









B.236




CF


3






CH


2


F




CH


2


CCl═CH


2









B.237




CF


3






Cl




CH


2


CCl═CH


2









B.238




CF


3






OCH


3






CH


2


CCl═CH


2









B.239




CF


3






OCH


2


CH


3






CH


2


CCl═CH


2









B.240




CF


3






CN




CH


2


CCl═CH


2









B.241




Cl




H




CH


2


C≡CH







B.242




Cl




CH


3






CH


2


C≡CH







B.243




Cl




CH


2


CH


3






CH


2


C≡CH







B.244




Cl




CF


3






CH


2


C≡CH







B.245




Cl




CHF


2






CH


2


C≡CH







B.246




Cl




CH


2


F




CH


2


C≡CH







B.247




Cl




Cl




CH


2


C≡CH







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




CH


3






CN




CH


2


C≡CH







B.261




CF


3






H




CH


2


C≡CH







B.262




CF


3






CH


3






CH


2


C≡CH







B.263




CF


3






CH


2


CH


3






CH


2


C≡CH







B.264




CF


3






CF


3






CH


2


C≡CH







B.265




CF


3






CHF


2






CH


2


C≡CH







B.266




CF


3






CH


2


F




CH


2


C≡CH







B.267




CF


3






Cl




CH


2


C≡CH







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≡CH







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









B.279




Cl




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≡CCH


3









B.282




CH


3






CH


3






CH


2


C≡CCH


3









B.283




CH


3






CH


2


CH


3






CH


2


C≡CCH


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




CH


3






CH


2


F




CH


2


C≡CCH


3









B.287




CH


3






Cl




CH


2


C≡CCH


3









B.288




CH


3






OCH


3






CH


2


C≡CCH


3









B.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









B.293




CF


3






CH


2


CH


3






CH


2


C≡CCH


3









B.294




CF


3






CF


3






CH


2


C≡CCH


3









B.295




CF


3






CHF


2






CH


2


C≡CCH


3









B.296




CF


3






CH


2


F




CH


2


C≡CCH


3









B.297




CF


3






Cl




CH


2


C≡CCH


3









B.298




CF


3






OCH


3






CH


2


C≡CCH


3









B.299




CF


3






OCH


2


CH


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







B.311




CH


3






H




CH


2


C≡C—I







B.312




CH


3






CH


3






CH


2


C≡C—I







B.313




CH


3






CH


2


CH


3






CH


2


C≡C—I







B.314




CH


3






CF


3






CH


2


C≡C—I







B.315




CH


3






CHF


2






CH


2


C≡C—I







B.316




CH


3






CH


2


F




CH


2


C≡C—I







B.317




CH


3






Cl




CH


2


C≡C—I







B.318




CH


3






OCH


3






CH


2


C≡C—I







B.319




CH


3






OCH


2


CH


3






CH


2


C≡C—I







B.320




CH


3






CN




CH


2


C≡C—I







B.321




CF


3






H




CH


2


C≡C—I







B.322




CF


3






CH


3






CH


2


C≡C—I







B.323




CF


3






CH


2


CH


3






CH


2


C≡C—I







B.324




CF


3






CF


3






CH


2


C≡C—I







B.325




CF


3






CHF


2






CH


2


C≡C—I







B.326




CF


3






CH


2


F




CH


2


C≡C—I







B.327




CF


3






Cl




CH


2


C≡C—I







B.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







B.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≡CH







B.348




CH


3






OCH


3






CH(CH


3


)C≡CH







B.349




CH


3






OCH


2


CH


3






CH(CH


3


)C≡CH







B.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≡CH







B.353




CF


3






CH


2


CH


3






CH(CH


3


)C≡CH







B.354




CF


3






CF


3






CH(CH


3


)C≡CH







B.355




CF


3






CHF


2






CH(CH


3


)C≡CH







B.356




CF


3






CH


2


F




CH(CH


3


)C≡CH







B.357




CF


3






Cl




CH(CH


3


)C≡CH







B.358




CF


3






OCH


3






CH(CH


3


)C≡CH







B.359




CF


3






OCH


2


CH


3






CH(CH


3


)C≡CH







B.360




CF


3






CN




CH(CH


3


)C≡CH







B.361




Cl




H




CH


2


CH


2


—O—CH


2


CH


3









B.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









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


—O—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


5









B.392




Cl




CH


3






CH


2


—C


6


H


5









B.393




Cl




CH


2


CH


3






CH


2


—C


6


H


5









B.394




Cl




CF


3






CH


2


—C


6


H


5









B.395




Cl




CHF


2






CH


2


—C


6


H


5









B.396




Cl




CH


2


F




CH


2


—C


6


H


5









B.397




Cl




Cl




CH


2


—C


6


H


5









B.398




Cl




OCH


3






CH


2


—C


6


H


5









B.399




Cl




OCH


2


CH


3






CH


2


—C


6


H


5









B.400




Cl




CN




CH


2


—C


6


H


5









B.401




CH


3






H




CH


2


—C


6


H


5









B.402




CH


3






CH


3






CH


2


—C


6


H


5









B.403




CH


3






CH


2


CH


3






CH


2


—C


6


H


5









B.404




CH


3






CF


3






CH


2


—C


6


H


5









B.405




CH


3






CHF


2






CH


2


—C


6


H


5









B.406




CH


3






CH


2


F




CH


2


—C


6


H


5









B.407




CH


3






Cl




CH


2


—C


6


H


5









B.408




CH


3






OCH


3






CH


2


—C


6


H


5









B.409




CH


3






OCH


2


CH


3






CH


2


—C


6


H


5









B.410




CH


3






CN




CH


2


—C


6


H


5









B.411




CF


3






H




CH


2


—C


6


H


5









B.412




CF


3






CH


3






CH


2


—C


6


H


5









B.413




CF


3






CH


2


CH


3






CH


2


—C


6


H


5









B.414




CF


3






CF


3






CH


2


—C


6


H


5









B.415




CF


3






CHF


2






CH


2


—C


6


H


5









B.416




CF


3






CH


2


F




CH


2


—C


6


H


5









B.417




CF


3






Cl




CH


2


—C


6


H


5









B.418




CF


3






OCH


3






CH


2


—C


6


H


5









B.419




CF


3






OCH


2


CH


3






CH


2


—C


6


H


5









B.420




CF


3






CN




CH


2


—C


6


H


5









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







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-Cl


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-Cl


2


-cyclopropyl)







B.454




Cl




CF


3






CH


2


-(2,2-Cl


2


-cyclopropyl)







B.455




Cl




CHF


2






CH


2


-(2,2-Cl


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-Cl


2


-cyclopropyl)







B.462




CH


3






CH


3






CH


2


-(2,2-Cl


2


-cyclopropyl)







B.463




CH


3






CH


2


CH


3






CH


2


-(2,2-Cl


2


-cyclopropyl)







B.464




CH


3






CF


3






CH


2


-(2,2-Cl


2


-cyclopropyl)







B.465




CH


3






CHF


2






CH


2


-(2,2-Cl


2


-cyclopropyl)







B.466




CH


3






CH


2


F




CH


2


-(2,2-Cl


2


-cyclopropyl)







B.467




CH


3






Cl




CH


2


-(2,2-Cl


2


-cyclopropyl)







B.468




CH


3






OCH


3






CH


2


-(2,2-Cl


2


-cyclopropyl)







B.469




CH


3






OCH


2


CH


3






CH


2


-(2,2-Cl


2


-cyclopropyl)







B.470




CH


3






CN




CH


2


-(2,2-Cl


2


-cyclopropyl)







B.471




CF


3






H




CH


2


-(2,2-Cl


2


-cyclopropyl)







B.472




CF


3






CH


3






CH


2


-(2,2-Cl


2


-cyclopropyl)







B.473




CF


3






CH


2


CH


3






CH


2


-(2,2-Cl


2


-cyclopropyl)







B.474




CF


3






CF


3






CH


2


-(2,2-Cl


2


-cyclopropyl)







B.475




CF


3






CHF


2






CH


2


-(2,2-Cl


2


-cyclopropyl)







B.476




CF


3






CH


2


F




CH


2


-(2,2-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-Cl


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-Cl


2


-cyclopropyl)







B.481




H




CH


3






H







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






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






CH


3






H







B.507




OCH


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




CH


3






H







B.512




CN




CH


2


CH


3






H







B.513




CN




CF


3






H







B.514




CN




Cl




H







B.515




CN




OCH


3






H







B.516




H




CH


3






CH


3









B.517




H




CH


2


CH


3






CH


3









B.518




H




CF


3






CH


3









B.519




H




Cl




CH


3









B.520




H




OCH


3






CH


3









B.521




CH


2


CH


3






CH


3






CH


3









B.522




CH


2


CH


3






CH


2


CH


3






CH


3









B.523




CH


2


CH


3






CF


3






CH


3









B.524




CH


2


CH


3






Cl




CH


3









B.525




CH


2


CH


3






OCH


3






CH


3









B.526




CHF


2






CH


3






CH


3









B.527




CHF


2






CH


2


CH


3






CH


3









B.528




CHF


2






CF


3






CH


3









B.529




CHF


2






Cl




CH


3









B.530




CHF


2






OCH


3






CH


3









B.531




CH


2


F




CH


3






CH


3









B.532




CH


2


F




CH


2


CH


3






CH


3









B.533




CH


2


F




CF


3






CH


3









B.534




CH


2


F




Cl




CH


3









B.535




CH


2


F




OCH


3






CH


3









B.536




OCH


3






CH


3






CH


3









B.537




OCH


3






CH


2


CH


3






CH


3









B.538




OCH


3






CF


3






CH


3









B.539




OCH


3






Cl




CH


3









B.540




OCH


3






OCH


3






CH


3









B.541




OCH


2


CH


3






CH


3






CH


3









B.542




OCH


2


CH


3






CH


2


CH


3






CH


3









B.543




OCH


2


CH


3






CF


3






CH


3









B.544




OCH


2


CH


3






Cl




CH


3









B.545




OCH


2


CH


3






OCH


3






CH


3









B.546




CN




CH


3






CH


3









B.547




CN




CH


2


CH


3






CH


3









B.548




CN




CF


3






CH


3









B.549




CN




Cl




CH


3









B.550




CN




OCH


3






CH


3









B.551




H




CH


3






CH


2


CH


3









B.552




H




CH


2


CH


3






CH


2


CH


3









B.553




H




CF


3






CH


2


CH


3









B.554




H




Cl




CH


2


CH


3









B.555




H




OCH


3






CH


2


CH


3









B.556




CH


2


CH


3






CH


3






CH


2


CH


3









B.557




CH


2


CH


3






CH


2


CH


3






CH


2


CH


3









B.558




CH


2


CH


3






CF


3






CH


2


CH


3









B.559




CH


2


CH


3






Cl




CH


2


CH


3









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






CH


2


CH


3









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






CH


2


CH


3









B.584




CN




Cl




CH


2


CH


3









B.585




CN




OCH


3






CH


2


CH


3









B.586




H




CH


3






CH


2


CH


2


CH


3









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


CH


2


CH


3









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






CH


2


CH


2


CH


3









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









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









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


3









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


2


CH


3









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






CH


2


CH


2


CH


3









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




Cl




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









B.638




CH


2


F




CF


3






CH(CH


3


)


2









B.639




CH


2


F




Cl




CH(CH


3


)


2









B.640




CH


2


F




OCH


3






CH(CH


3


)


2









B.641




OCH


3






CH


3






CH(CH


3


)


2









B.642




OCH


3






CH


2


CH


3






CH(CH


3


)


2









B.643




OCH


3






CF


3






CH(CH


3


)


2









B.644




OCH


3






Cl




CH(CH


3


)


2









B.645




OCH


3






OCH


3






CH(CH


3


)


2









B.646




OCH


2


CH


3






CH


3






CH(CH


3


)


2









B.647




OCH


2


CH


3






CH


2


CH


3






CH(CH


3


)


2









B.648




OCH


2


CH


3






CF


3






CH(CH


3


)


2









B.649




OCH


2


CH


3






Cl




CH(CH


3


)


2









B.650




OCH


2


CH


3






OCH


3






CH(CH


3


)


2









B.651




CN




CH


3






CH(CH


3


)


2









B.652




CN




CH


2


CH


3






CH(CH


3


)


2









B.653




CN




CF


3






CH(CH


3


)


2









B.654




CN




Cl




CH(CH


3


)


2









B.655




CN




OCH


3






CH(CH


3


)


2









B.656




H




CH


3






CH


2


CH═CH


2









B.657




H




CH


2


CH


3






CH


2


CH═CH


2









B.658




H




CF


3






CH


2


CH═CH


2









B.659




H




Cl




CH


2


CH═CH


2









B.660




H




OCH


3






CH


2


CH═CH


2









B.661




CH


2


CH


3






CH


3






CH


2


CH═CH


2









B.662




CH


2


CH


3






CH


2


CH


3






CH


2


CH═CH


2









B.663




CH


2


CH


3






CF


3






CH


2


CH═CH


2









B.664




CH


2


CH


3






Cl




CH


2


CH═CH


2









B.665




CH


2


CH


3






OCH


3






CH


2


CH═CH


2









B.666




CHF


2






CH


3






CH


2


CH═CH


2









B.667




CHF


2






CH


2


CH


3






CH


2


CH═CH


2









B.668




CHF


2






CF


3






CH


2


CH═CH


2









B.669




CHF


2






Cl




CH


2


CH═CH


2









B.670




CHF


2






OCH


3






CH


2


CH═CH


2









B.671




CH


2


F




CH


3






CH


2


CH═CH


2









B.672




CH


2


F




CH


2


CH


3






CH


2


CH═CH


2









B.673




CH


2


F




CF


3






CH


2


CH═CH


2









B.674




CH


2


F




Cl




CH


2


CH═CH


2









B.675




CH


2


F




OCH


3






CH


2


CH═CH


2









B.676




OCH


3






CH


3






CH


2


CH═CH


2









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




Cl




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—Cl (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—Cl (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—Cl (trans)







B.708




CH


2


F




CF


3






CH


2


CH═CH—Cl (trans)







B.709




CH


2


F




Cl




CH


2


CH═CH—Cl (trans)







B.710




CH


2


F




OCH


3






CH


2


CH═CH—Cl (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)







B.716




OCH


2


CH


3






CH


3






CH


2


CH═CH—Cl (trans)







B.717




OCH


2


CH


3






CH


2


CH


3






CH


2


CH═CH—Cl (trans)







B.718




OCH


2


CH


3






CF


3






CH


2


CH═CH—Cl (trans)







B.719




OCH


2


CH


3






Cl




CH


2


CH═CH—Cl (trans)







B.720




OCH


2


CH


3






OCH


3






CH


2


CH═CH—Cl (trans)







B.721




CN




CH


3






CH


2


CH═CH—Cl (trans)







B.722




CN




CH


2


CH


3






CH


2


CH═CH—Cl (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


CCl═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


CCl═CH


2









B.732




CH


2


CH


3






CH


2


CH


3






CH


2


CCl═CH


2









B.733




CH


2


CH


3






CF


3






CH


2


CCl═CH


2









B.734




CH


2


CH


3






Cl




CH


2


CCl═CH


2









B.735




CH


2


CH


3






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


CCl═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


CCl═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


CCl═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


CCl═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.754




OCH


2


CH


3






Cl




CH


2


CCl═CH


2









B.755




OCH


2


CH


3






OCH


3






CH


2


CCl═CH


2









B.756




CN




CH


3






CH


2


CCl═CH


2









B.757




CN




CH


2


CH


3






CH


2


CCl═CH


2









B.758




CN




CF


3






CH


2


CCl═CH


2









B.759




CN




Cl




CH


2


CCl═CH


2









B.760




CN




OCH


3






CH


2


CCl═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≡CH







B.778




CH


2


F




CF


3






CH


2


C≡CH







B.779




CH


2


F




Cl




CH


2


C≡CH







B.780




CH


2


F




OCH


3






CH


2


C≡CH







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≡CH







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≡CH







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≡CCH


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≡CCH


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≡CCH


3









B.823




OCH


2


CH


3






CF


3






CH


2


C≡CCH


3









B.824




OCH


2


CH


3






Cl




CH


2


C≡CCH


3









B.825




OCH


2


CH


3






OCH


3






CH


2


C≡CCH


3









B.826




CN




CH


3






CH


2


C≡CCH


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







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




CH


2


CH


3






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




OCH


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







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




Cl




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






Cl




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









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




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




CN




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




CN




Cl




CH


2


CH


2


—O—CH


2


CH


3









B.935




CN




OCH


3






CH


2


CH


2


—O—CH


2


CH


3









B.936




H




CH


3






CH


2


—C


6


H


5









B.937




H




CH


2


CH


3






CH


2


—C


6


H


5









B.938




H




CF


3






CH


2


—C


6


H


5









B.939




H




Cl




CH


2


—C


6


H


5









B.940




H




OCH


3






CH


2


—C


6


H


5









B.941




CH


2


CH


3






CH


3






CH


2


—C


6


H


5









B.942




CH


2


CH


3






CH


2


CH


3






CH


2


—C


6


H


5









B.943




CH


2


CH


3






CF


3






CH


2


—C


6


H


5









B.944




CH


2


CH


3






Cl




CH


2


—C


6


H


5









B.945




CH


2


CH


3






OCH


3






CH


2


—C


6


H


5









B.946




CHF


2






CH


3






CH


2


—C


6


H


5









B.947




CHF


2






CH


2


CH


3






CH


2


—C


6


H


5









B.948




CHF


2






CF


3






CH


2


—C


6


H


5









B.949




CHF


2






Cl




CH


2


—C


6


H


5









B.950




CHF


2






OCH


3






CH


2


—C


6


H


5









B.951




CH


2


F




CH


3






CH


2


—C


6


H


5









B.952




CH


2


F




CH


2


CH


3






CH


2


—C


6


H


5









B.953




CH


2


F




CF


3






CH


2


—C


6


H


5









B.954




CH


2


F




Cl




CH


2


—C


6


H


5









B.955




CH


2


F




OCH


3






CH


2


—C


6


H


5









B.956




OCH


3






CH


3






CH


2


—C


6


H


5









B.957




OCH


3






CH


2


CH


3






CH


2


—C


6


H


5









B.958




OCH


3






CF


3






CH


2


—C


6


H


5









B.959




OCH


3






Cl




CH


2


—C


6


H


5









B.960




OCH


3






OCH


3






CH


2


—C


6


H


5









B.961




OCH


2


CH


3






CH


3






CH


2


—C


6


H


5









B.962




OCH


2


CH


3






CH


2


CH


3






CH


2


—C


6


H


5









B.963




OCH


2


CH


3






CF


3






CH


2


—C


6


H


5









B.964




OCH


2


CH


3






Cl




CH


2


—C


6


H


5









B.965




OCH


2


CH


3






OCH


3






CH


2


—C


6


H


5









B.966




CN




CH


3






CH


2


—C


6


H


5









B.967




CN




CH


2


CH


3






CH


2


—C


6


H


5









B.968




CN




CF


3






CH


2


—C


6


H


5









B.969




CN




Cl




CH


2


—C


6


H


5









B.970




CN




OCH


3






CH


2


—C


6


H


5









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







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




OCH


2


CH


3






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






OCH


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




Cl




cyclopropyl







B.1005




CN




OCH


3






cyclopropyl







B.1006




H




CH


3






CH


2


-(2,2-Cl


2


-cyclopropyl)







B.1007




H




CH


2


CH


3






CH


2


-(2,2-Cl


2


-cyclopropyl)







B.1008




H




CF


3






CH


2


-(2,2-Cl


2


-cyciopropyl)







B.1009




H




Cl




CH


2


-(2,2-Cl


2


-cyclopropyl)







B.1010




H




OCH


3






CH


2


-(2,2-Cl


2


-cyclopropyl)







B.1011




CH


2


CH


3






CH


3






CH


2


-(2,2-Cl


2


-cyclopropyl)







B.1012




CH


2


CH


3






CH


2


CH


3






CH


2


-(2,2-Cl


2


-cyclopropyl)







B.1013




CH


2


CH


3






CF


3






CH


2


-(2,2-Cl


2


-cyclopropyl)







B.1014




CH


2


CH


3






Cl




CH


2


-(2,2-Cl


2


-cyclopropyl)







B.1015




CH


2


CH


3






OCH


3






CH


2


-(2,2-Cl


2


-cyclopropyl)







B.1016




CHF


2






CH


3






CH


2


-(2,2-Cl


2


-cyclopropyl)







B.1017




CHF


2






CH


2


CH


3






CH


2


-(2,2-Cl


2


-cyclopropyl)







B.1018




CHF


2






CF


3






CH


2


-(2,2-Cl


2


-cyclopropyl)







B.1019




CHF


2






Cl




CH


2


-(2,2-Cl


2


-cyclopropyl)







B.1020




CHF


2






OCH


3






CH


2


-(2,2-Cl


2


-cyclopropyl)







B.1021




CH


2


F




CH


3






CH


2


-(2,2-Cl


2


-cyclopropyl)







B.1022




CH


2


F




CH


2


CH


3






CH


2


-(2,2-Cl


2


-cyclopropyl)







B.1023




CH


2


F




CF


3






CH


2


-(2,2-Cl


2


-cyclopropyl)







B.1024




CH


2


F




Cl




CH


2


-(2,2-Cl


2


-cyclopropyl)







B.1025




CH


2


F




OCH


3






CH


2


-(2,2-Cl


2


-cyclopropyl)







B.1026




OCH


3






CH


3






CH


2


-(2,2-Cl


2


-cyclopropyl)







B 1027




OCH


3






CH


2


CH


3






CH


2


-(2,2-Cl


2


-cyclopropyl)







B.1028




CCH


3






CF


3






CH


2


-(2,2-Cl


2


-cyclopropyl)







B.1029




OCH


3






Cl




CH


2


-(2,2-Cl


2


-cyclopropyl)







B.1030




OCH


3






OCH


3






CH


2


-(2,2-Cl


2


-cyclopropyl)







B.1031




OCH


2


CH


3






CH


3






CH


2


-(2,2-Cl


2


-cyclopropyl)







B.1032




OCH


2


CH


3






CH


2


CH


3






CH


2


-(2,2-Cl


2


-cyclopropyl)







B.1033




OCH


2


CH


3






CF


3






CH


2


-(2,2-Cl


2


-cyclopropyl)







B.2067




OCH


2


CH


3






Cl




CH


2


-(2,2-Cl


2


-cyclopropyl)







B.2068




OCH


2


CH


3






OCH


3






CH


2


-(2,2-Cl


2


-cyclopropyl)







B.2069




CN




CH


3






CH


2


-(2,2-Cl


2


-cyclopropyl)







B.2070




CN




CH


2


CH


3






CH


2


-(2,2-Cl


2


-cyclopropyl)







B.2071




CN




CF


3






CH


2


-(2,2-Cl


2


-cyclopropyl)







B.2072




CN




Cl




CH


2


-(2,2-Cl


2


-cyclopropyl)







B.2073




CN




OCH


3






CH


2


-(2,2-Cl


2


-cyclopropyl)



























TABLE C









No.




R


1






R


x






R


y






R


z













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






C.5




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






C.10




CH


3






H




OC


2


H


5






H






C.11




CH


3






H




CH


2


—C


6


H


5






H






C.12




CH


3






H




CH(CH


3


)C


6


H


5






H






C.13




CH


3






H




C


6


H


5






H






C.14




CH


3






H




4-F—C


6


H


5






H






C.15




CH


3






H




4-Cl-2-pyridyl




H






C.16




CH


3






H




F




H






C.17




CH


3






H




CN




H






C.18




CH


3






CH


3






H




H






C.19




CH


3






CH


3






CH


3






H






C.20




CH


3






CH


3






C


2


H


5






H






C.21




CH


3






CH


3






C


3


H


7






H






C.22




CH


3






CH


3






C


4


H


9






H






C.23




CH


3






CH


3






CH(CH


3


)


2






H






C.24




CH


3






CH


3






cyclopropyl




H






C.25




CH


3






CH


3






CF


3






H






C.26




CH


3






CH


3






OCH


3






H






C.27




CH


3






CH


3






OC


2


H


5






H






C.28




CH


3






CH


3






CH


2


—C


6


H


5






H






C.29




CH


3






CH


3






CH(CH


3


)C


6


H


5






H






C.30




CH


3






CH


3






C


6


H


5






H






C.31




CH


3






CH


3






4-F—C


6


H


5






H






C.32




CH


3






CH


3






4-Cl-2-pyridyl




H






C.33




CH


3






CH


3






F




H






C.34




CH


3






CH


3






CN




H






C.35




CH


3






C


2


H


5






H




H






C.36




CH


3






C


2


H


5






CH


3






H






C.37




CH


3






C


2


H


5






C


2


H


5






H






C.38




CH


3






C


2


H


5






C


3


H


7






H






C.39




CH


3






C


2


H


5






C


4


H


9






H






C.40




CH


3






C


2


H


5






CH(CH


3


)


2






H






C.41




CH


3






C


2


H


5






cyclopropyl




H






C.42




CH


3






C


2


H


5






CF


3






H






C.43




CH


3






C


2


H


5






OCH


3






H






C.44




CH


3






C


2


H


5






OC


2


H


5






H






C.45




CH


3






C


2


H


5






CH


2


—C


6


H


5






H






C.46




CH


3






C


2


H


5






CH(CH


3


)C


6


H


5






H






C.47




CH


3






C


2


H


5






C


6


H


5






H






C.48




CH


3






C


2


H


5






4-F—C


6


H


5






H






C.49




CH


3






C


2


H


5






4-Cl-2-pyridyl




H






C.50




CH


3






C


2


H


5






F




H






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






C.55




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






C.60




CH


3






cyclopropyl




OCH


3






H






C.61




CH


3






cyclopropyl




OC


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






C.65




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






cyclopropyl




CN




H






C.69




CH


3






CF


3






H




H






C.70




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


H


9






H






C.74




CH


3






CF


3






CH(CH


3


)


2






H






C.75




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






OC


2


H


5






H






C.79




CH


3






CF


3






CH


2


—C


6


H


5






H






C.80




CH


3






CF


3






CH(CH


3


)C


6


H


5






H






C.81




CH


3






CF


3






C


6


H


5






H






C.82




CH


3






CF


3






4-F—C


6


H


5






H






C.83




CH


3






CF


3






4-Cl-2-pyridyl




H






C.84




CH


3






CF


3






F




H






C.85




CH


3






CF


3






CN




H






C.86




CH


3






Cl




H




H






C.87




CH


3






Cl




CH


3






H






C.88




CH


3






C1




C


2


H


5






H






C.89




CH


3






Cl




C


3


H


7






H






C.90




CH


3






Cl




C


4


H


9






H






C.91




CH


3






Cl




CH(CH


3


)2




H






C.92




CH


3






Cl




cyclopropyl




H






C.93




CH


3






Cl




CF


3






H






C.94




CH


3






Cl




OCH


3






H






C.95




CH


3






Cl




OC


2


H


5






H






C.96




CH


3






Cl




CH


2


—C


6


H


5






H






C.97




CH


3






Cl




CH(CH


3


)C


6


H


5






H






C.98




CH


3






Cl




C


6


H


5






H






C.99




CH


3






Cl




4-F—C


6


H


5






H






C.100




CH


3






Cl




4-Cl-2-pyridyl




H






C.101




CH


3






Cl




F




H






C.102




CH


3






Cl




CN




H






C.103




CH


3






F




H




H






C.104




CH


3






F




CH


3






H






C.105




CH


3






F




C


2


H


5






H






C.106




CH


3






F




C


3


H


7






H






C.107




CH


3






F




C


4


H


9






H






C.108




CH


3






F




CH(CH


3


)


2






H






C.109




CH


3






F




cyclopropyl




H






C.110




CH


3






F




CF


3






H






C.111




CH


3






F




OCH


3






H






C.112




CH


3






F




OC


2


H


5






H






C.113




CH


3






F




CH


2


—C


6


H


5






H






C.114




CH


3






F




CH(CH


3


)C


6


H


5






H






C.115




CH


3






F




C


6


H


5






H






C.116




CH


3






F




4-F—C


6


H


5






H






C.117




CH


3






F




4-Cl-2-pyridyl




H






C.118




CH


3






F




F




H






C.119




CH


3






F




CN




H






C.120




CH


3






OCH


3






H




H






C.121




CH


3






OCH


3






CH


3






H






C.122




CH


3






OCH


3






C


2


H


5






H






C.123




CH


3






OCH


3






C


3


H


7






H






C.124




CH


3






OCH


3






C


4


H


9






H






C.125




CH


3






OCH


3






CH(CH


3


)2




H






C.126




CH


3






OCH


3






cyclopropyl




H






C.127




CH


3






OCH


3






CF


3






H






C.128




CH


3






OCH


3






OCH


3






H






C.129




CH


3






OCH


3






OC


2


H


5






H






C.130




CH


3






OCH


3






CH


2


—C


6


H


5






H






C.131




CH


3






OCH


3






CH(CH


3


)C


6


H


5






H






C.132




CH


3






OCH


3






C


6


H


5






H






C.133




CH


3






OCH


3






4-F—C


6


H


5






H






C.134




CH


3






OCH


3






4-Cl-2-pyridyl




H






C.135




CH


3






OCH


3






F




H






C.136




CH


3






OCH


3






CN




H






C.137




CH


3






H




H




CH


3








C.138




CH


3






H




CH


3






CH


3








C.139




CH


3






H




C


2


H


5






CH


3








C.140




CH


3






H




C


3


H


7






CH


3








C.141




CH


3






H




C


4


H


9






CH


3








C.142




CH


3






H




CH(CH


3


)2




CH


3








C.143




CH


3






H




cyclopropyl




CH


3








C.144




CH


3






H




CF


3






CH


3








C.145




CH


3






H




OCH


3






CH


3








C.146




CH


3






H




OC


2


H


5






CH


3








C.147




CH


3






H




CH


2


—C


6


H


5






CH


3








C.148




CH


3






H




CH(CH


3


)C


6


H


5






CH


3








C.149




CH


3






H




C


6


H


5






CH


3








C.150




CH


3






H




4-F—C


6


H


5






CH


3








C.151




CH


3






H




4-Cl-2-pyridyl




CH


3








C.152




CH


3






H




F




CH


3








C.153




CH


3






H




CN




CH


3








C.154




CH


3






CH


3






H




CH


3








C.155




CH


3






CH


3






CH


3






CH


3








C.156




CH


3






CH


3






C


2


H


5






CH


3








C.157




CH


3






CH


3






C


3


H


7






CH


3








C.158




CH


3






CH


3






C


4


H


9






CH


3








C.159




CH


3






CH


3






CH(CH


3


)


2






CH


3








C.160




CH


3






CH


3






cyclopropyl




CH


3








C.161




CH


3






CH


3






CF


3






CH


3








C.162




CH


3






CH


3






OCH


3






CH


3








C.163




CH


3






CH


3






OC


2


H


5






CH


3








C.164




CH


3






CH


3






CH


2


—C


6


H


5






CH


3








C.165




CH


3






CH


3






CH(CH


3


)C


6


H


5






CH


3








C.166




CH


3






CH


3






C


6


H


5






CH


3








C.167




CH


3






CH


3






4-F—C


6


H


5






CH


3








C.168




CH


3






CH


3






4-Cl-2-pyridyl




CH


3








C.169




CH


3






CH


3






F




CH


3








C.170




CH


3






CH


3






CN




CH


3








C.171




CH


3






C


2


H


5






H




CH


3








C.172




CH


3






C


2


H


5






CH


3






CH


3








C.173




CH


3






C


2


H


5






C


2


H


5






CH


3








C.174




CH


3






C


2


H


5






C


3


H


7






CH


3








C.175




CH


3






C


2


H


5






C


4


H


9






CH


3








C.176




CH


3






C


2


H


5






CH(CH


3


)


2






CH


3








C.177




CH


3






C


2


H


5






cyclopropyl




CH


3








C.178




CH


3






C


2


H


5






CF


3






CH


3








C.179




CH


3






C


2


H


5






OCH


3






CH


3








C.180




CH


3






C


2


H


5






OC


2


H


5






CH


3








C.181




CH


3






C


2


H


5






CH


2


—C


6


H


5






CH


3








C.182




CH


3






C


2


H


5






CH(CH


3


)C


6


H


5






CH


3








C.183




CH


3






C


2


H


5






C


6


H


5






CH


3








C.184




CH


3






C


2


H


5






4-F—C


6


H


5






CH


3








C.185




CH


3






C


2


H


5






4-Cl-2-pyridyl




CH


3








C.186




CH


3






C


2


H


5






F




CH


3








C.187




CH


3






C


2


H


5






CN




CH


3








C.188




CH


3






cyclopropyl




H




CH


3








C.189




CH


3






cyclopropyl




CH


3






CH


3








C.190




CH


3






cyclopropyl




C


2


H


5






CH


3








C.191




CH


3






cyclopropyl




C


3


H


7






CH


3








C.192




CH


3






cyclopropyl




C


4


H


9






CH


3








C.193




CH


3






cyclopropyl




CH(CH


3


)


2






CH


3








C.194




CH


3






cyclopropyl




cyclopropyl




CH


3








C.195




CH


3






cyclopropyl




CF


3






CH


3








C.196




CH


3






cyclopropyl




OCH


3






CH


3








C.197




CH


3






cyclopropyl




OC


2


H


5






CH


3








C.198




CH


3






cyclopropyl




CH


2


—C


6


H


5






CH


3








C.199




CH


3






cyclopropyl




CH(CH


3


)C


6


H


5






CH


3








C.200




CH


3






cyclopropyl




C


6


H


5






CH


3








C.201




CH


3






cyclopropyl




4-F—C


6


H


5






CH


3








C.202




CH


3






cyclopropyl




4-Cl-2-pyridyl




CH


3








C.203




CH


3






cyclopropyl




F




CH


3








C.204




CH


3






cyclopropyl




CN




CH


3








C.205




CH


3






CF


3






H




CH


3








C.206




CH


3






CF


3






CH


3






CH


3








C.207




CH


3






CF


3






C


2


H


5






CH


3








C.208




CH


3






CF


3






C


3


H


7






CH


3








C.209




CH


3






CF


3






C


4


H


9






CH


3








C.210




CH


3






CF


3






CH(CH


3


)


2






CH


3








C.211




CH


3






CF


3






cyclopropyl




CH


3








C.212




CH


3






CF


3






CF


3






CH


3








C.213




CH


3






CF


3






OCH


3






CH


3








C.214




CH


3






CF


3






OC


2


H


5






CH


3








C.215




CH


3






CF


3






CH


2


—C


6


H


5






CH


3








C.216




CH


3






CF


3






CH(CH


3


)C


6


H


5






CH


3








C.217




CH


3






CF


3






C


6


H


5






CH


3








C.218




CH


3






CF


3






4-F—C


6


H


5






CH


3








C.219




CH


3






CF


3






4-Cl-2-pyridyl




CH


3








C.220




CH


3






CF


3






F




CH


3








C.221




CH


3






CF


3






CN




CH


3








C.222




CH


3






Cl




H




CH


3








C.223




CH


3






Cl




CH


3






CH


3








C.224




CH


3






CI




C


2


H


5






CH


3








C.225




CH


3






Cl




C


3


H


7






CH


3








C.226




CH


3






Cl




C


4


H


9






CH


3








C.227




CH


3






Cl




CH(CH


3


)


2






CH


3








C.228




CH


3






Cl




cyclopropyl




CH


3








C.229




CH


3






Cl




CF


3






CH


3








C.230




CH


3






Cl




OCH


3






CH


3








C.231




CH


3






Cl




OC


2


H


5






CH


3








C.232




CH


3






Cl




CH


2


—C


6


H


5






CH


3








C.233




CH


3






Cl




CH(CH


3


)C


6


H


5






CH


3








C.234




CH


3






Cl




C


6


H


5






CH


3








C.235




CH


3






Cl




4-F—C


6


H


5






CH


3








C.236




CH


3






Cl




4-Cl-2-pyridyl




CH


3








C.237




CH


3






CI




F




CH


3








C.238




CH


3






Cl




CN




CH


3








C.239




CH


3






F




H




CH


3








C.240




CH


3






F




CH


3






CH


3








C.241




CH


3






F




C


2


H


5






CH


3








C.242




CH


3






F




C


3


H


7






CH


3








C.243




CH


3






F




C


4


H


9






CH


3








C.244




CH


3






F




CH(CH


3


)


2






CH


3








C.245




CH


3






F




cyclopropyl




CH


3








C.246




CH


3






F




CF


3






CH


3








C.247




CH


3






F




OCH


3






CH


3








C.248




CH


3






F




OC


2


H


5






CH


3








C.249




CH


3






F




CH


2


—C


6


H


5






CH


3








C.250




CH


3






F




CH(CH


3


)C


6


H


5






CH


3








C.251




CH


3






F




C


6


H


5






CH


3








C.252




CH


3






F




4-F—C


6


H


5






CH


3








C.253




CH


3






F




4-Cl-2-pyridyl




CH


3








C.254




CH


3






F




F




CH


3








C.255




CH


3






F




CN




CH


3








C.256




CH


3






OCH


3






H




CH


3








C.257




CH


3






OCH


3






CH


3






CH


3








C.258




CH


3






OCH


3






C


2


H


5






CH


3








C.259




CH


3






OCH


3






C


3


H


7






CH


3








C.260




CH


3






OCH


3






C


4


H


9






CH


3








C.261




CH


3






OCH


3






CH(CH


3


)


2






CH


3








C.262




CH


3






OCH


3






cyclopropyl




CH


3








C.263




CH


3






OCH


3






CF


3






CH


3








C.264




CH


3






OCH


3






OCH


3






CH


3








C.265




CH


3






OCH


3






OC


2


H


5






CH


3








C.266




CH


3






OCH


3






CH


2


—C


6


H


5






CH


3








C.267




CH


3






OCH


3






CH(CH


3


)C


6


H


5






CH


3








C.268




CH


3






OCH


3






C


6


H


5






CH


3








C.269




CH


3






OCH


3






4-F—C


6


H


5






CH


3








C.270




CH


3






OCH


3






4-Cl-2-pyridyl




CH


3








C.271




CH


3






OCH


3






F




CH


3








C.272




CH


3






OCH


3






CN




CH


3








C.273




H




CH


3






H




H






C.274




H




CH


3






CH


3






H






C.275




H




CH


3






C


2


H


5






H






C.276




H




CH


3






C


3


H


7






H






C.277




H




CH


3






C


4


H


9






H






C.278




H




CH


3






CH(CH


3


)


2






H






C.279




H




CH


3






cyclopropyl




H






C.280




H




CH


3






CF


3






H






C.281




H




CH


3






OCH


3






H






C.282




H




CH


3






OC


2


H


5






H






C.283




H




CH


3






CH


2


—C


6


H


5






H






C.284




H




CH


3






CH(CH


3


)C


6


H


5






H






C.285




H




CH


3






C


6


H


5






H






C.286




H




CH


3






4-F—C


6


H


5






H






C.287




H




CH


3






4-Cl-2-pyridyl




H






C.288




H




CH


3






F




H






C.289




H




CH


3






CN




H






C.290




H




CH


3






H




CH


3








C.291




H




CH


3






CH


3






CH


3








C.292




H




CH


3






C


2


H


5






CH


3








C.293




H




CH


3






C


3


H


7






CH


3








C.294




H




CH


3






C


4


H


9






CH


3








C.295




H




CH


3






CH(CH


3


)


2






CH


3








C.296




H




CH


3






cyclopropyl




CH


3








C.297




H




CH


3






CF


3






CH


3








C.298




H




CH


3






OCH


3






CH


3








C.299




H




CH


3






OC


2


H


5






CH


3








C.300




H




CH


3






CH


2


—C


6


H


5






CH


3








C.301




H




CH


3






CH(CH


3


)C


6


H


5






CH


3








C.302




H




CH


3






C


6


H


5






CH


3








C.303




H




CH


3






4-F—C


6


H


5






CH


3








C.304




H




CH


3






4-Cl-2-pyridyl




CH


3








C.305




H




CH


3






F




CH


3








C.306




H




CH


3






CN




CH


3








C.307




H




CF


3






H




H






C.308




H




CF


3






CH


3






H






C.309




H




CF


3






C


2


H


5






H






C.310




H




CF


3






C


3


H


7






H






C.311




H




CF


3






C


4


H


9






H






C.312




H




CF


3






CH(CH


3


)


2






H






C.313




H




CF


3






cyclopropyl




H






C.314




H




CF


3






CF


3






H






C.315




H




CF


3






OCH


3






H






C.316




H




CF


3






OC


2


H


5






H






C.317




H




CF


3






CH


2


—C


6


H


5






H






C.318




H




CF


3






CH(CH


3


)C


6


H


5






H






C.319




H




CF


3






C


6


H


5






H






C.320




H




CF


3






4-F—C


6


H


5






H






C.321




H




CF


3






4-Cl-2-pyridyl




H






C.322




H




CF


3






F




H






C.323




H




CF


3






CN




H






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


H


9






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






OC


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




CF


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


H


9






H






C.346




CF


3






CH


3






CH(CH


3


)


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






OC


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


H


9






CH


3








C.363




CF


3






CH


3






CH(CH


3


)


2






CH


3








C.364




CF


3






CH


3






cyclopropyl




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






OC


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-Cl-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


H


9






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






OC


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.394




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


H


9






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






OC


2


H


5






CH


3








C.402




CF


3






CF


3






CH


2


—C


6


H


5






CH


3








C.403




CF


3






CF


3






CH(CH


3


)C


6


H


5






CH


3








C.404




CF


3






CF


3






C


6


H


5






CH


3








C.405




CF


3






CF


3






4-F—C


6


H


5






CH


3








C.406




CF


3






CF


3






4-Cl-2-pyridyl




CH


3








C.407




CF


3






CF


3






F




CH


3








C.408




CF


3






CF


3






CN




CH


3








C.409




Cl




CH


3






H




H






C.410




Cl




CH


3






CH


3






H






C.411




Cl




CH


3






C


2


H


5






H






C.412




Cl




CH


3






C


3


H


7






H






C.413




Cl




CH


3






C


4


H


9






H






C.414




Cl




CH


3






CH(CH


3


)


2






H






C.415




Cl




CH


3






cyclopropyl




H






C.416




Cl




CH


3






CF


3






H






C.417




Cl




CH


3






OCH


3






H






C.418




Cl




CH


3






OC


2


H


5






H






C.419




Cl




CH


3






CH


2


—C


6


H


5






H






C.420




Cl




CH


3






CH(CH


3


)C


6


H


5






H






C.421




Cl




CH


3






C


6


H


5






H






C.422




Cl




CH


3






4-F—C


6


H


5






H






C.423




Cl




CH


3






4-Cl-2-pyridyl




H






C.424




Cl




CH


3






F




H






C.425




Cl




CH


3






CN




H






C.426




Cl




CH


3






H




CH


3








C.427




Cl




CH


3






CH


3






CH


3








C.428




Cl




CH


3






C


2


H


5






CH


3








C.429




Cl




CH


3






C


3


H


7






CH


3








C.430




Cl




CH


3






C


4


H


9






CH


3








C.431




Cl




CH


3






CH(CH


3


)


2






CH


3








C.432




Cl




CH


3






cyclopropyl




CH


3








C.433




Cl




CH


3






CF


3






CH


3








C.434




Cl




CH


3






OCH


3






CH


3








C.435




Cl




CH


3






OC


2


H


5






CH


3








C.436




Cl




CH


3






CH


2


—C


6


H


5






CH


3








C.437




Cl




CH


3






CH(CH


3


)C


6


H


5






CH


3








C.438




Cl




CH


3






C


6


H


5






CH


3








C.439




Cl




CH


3






4-F—C


6


H


5






CH


3








C.440




Cl




CH


3






4-Cl-2-pyridyl




CH


3








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


7






H






C.447




Cl




CF


3






C


4


H


9






H






C.448




Cl




CF


3






CH(CH


3


)


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






OC


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






OC


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-Cl-2-pyridyl




CH


3








C.475




Cl




CF


3






F




CH


3








C.476




Cl




CF


3






CN




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






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


5








C.488




H




CH


3






CH


3






C


2


H


5








C.489




H




CH


3






C


2


H


5






C


2


H


5








C.490




H




CH


3






C


3


H


7






C


2


H


5








C.491




H




CH


3






CH(CH


3


)


2






C


2


H


5








C.492




H




CH


3






cyclopropyl




C


2


H


5








C.493




H




CH


3






CF


3






C


2


H


5








C.494




H




CH


3






OCH


3






C


2


H


5








C.495




H




CH


3






C


6


H


5






C


2


H


5








C.496




H




CH


3






4-F—C


6


H


5






C


2


H


5








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






CN






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






C.519




H




CH


3






C


2


H


5






Cl






C.520




H




CH


3






C


3


H


7






Cl






C.521




H




CH


3






CH(CH


3


)


2






Cl






C.522




H




CH


3






cyclopropyl




Cl






C.523




H




CH


3






CF


3






Cl






C.524




H




CH


3






OCH


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






CH


3






F






C.529




H




CF


3






C


2


H


5






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






C


6


H


5






F






C.536




H




CF


3






4-F—C


6


H


5






F






C.537




H




CF


3






H




C


2


H


5








C.538




H




CF


3






CH


3






C


2


H


5








C.539




H




CF


3






C


2


H


5






C


2


H


5








C.540




H




CF


3






C


3


H


7






C


2


H


5








C.541




H




CF


3






CH(CH


3


)


2






C


2


H


5








C.542




H




CF


3






cyclopropyl




C


2


H


5








C.543




H




CF


3






CF


3






C


2


H


5








C.544




H




CF


3






OCH


3






C


2


H


5








C.545




H




CF


3






C


6


H


5






C


2


H


5








C.546




H




CF


3






4-F—C


6


H


5






C


2


H


5








C.547




H




CF


3






H




CF


3








C.548




H




CF


3






CH


3






CF


3








C.549




H




CF


3






C


2


H


5






CF


3








C.550




H




CF


3






C


3


H


7






CF


3








C.551




H




CF


3






CH(CH


3


)


2






CF


3








C.552




H




CF


3






cyclopropyl




CF


3








C.553




H




CF


3






CF


3






CF


3








C.554




H




CF


3






OCH


3






CF


3








C.555




H




CF


3






C


6


H


5






CF


3








C.556




H




CF


3






4-F—C


6


H


5






CF


3








C.557




H




CF


3






H




CN






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


5








C.588




CF


3






CH


3






CH


3






C


2


H


5








C.589




CF


3






CH


3






C


2


H


5






C


2


H


5








C.590




CF


3






CH


3






C


3


H


7






C


2


H


5








C.591




CF


3






CH


3






CH(CH


3


)


2






C


2


H


5








C.592




CF


3






CH


3






cyclopropyl




C


2


H


5








C.593




CF


3






CH


3






CF


3






C


2


H


5








C.594




CF


3






CH


3






OCH


3






C


2


H


5








C.595




CF


3






CH


3






C


6


H


5






C


2


H


5








C.596




CF


3






CH


3






4-F—C


6


H


5






C


2


H


5








C.597




CF


3






CH


3






H




CF


3








C.598




CF


3






CH


3






CH


3






CF


3








C.599




CF


3






CH


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(CH


3


)


2






CF


3








C.602




CF


3






CH


3






cyclopropyl




CF


3








C.603




CF


3






CH


3






CF


3






CF


3








C.604




CF


3






CH


3






OCH


3






CF


3








C.605




CF


3






CH


3






C


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






CH


3






CN






C.609




CF


3






CH


3






C


2


H


5






CN






C.610




CF


3






CH


3






C


3


H


7






CN






C.611




CF


3






CH


3






CH(CH


3


)


2






CN






C.612




CF


3






CH


3






cyclopropyl




CN






C.613




CF


3






CH


3






CF


3






CN






C.614




CF


3






CH


3






OCH


3






CN






C.615




CF


3






CH


3






C


6


H


5






CN






C.616




CF


3






CH


3






4-F—C


6


H


5






CN






C.617




CF


3






CH


3






H




Cl






C.618




CF


3






CH


3






CH


3






Cl






C.619




CF


3






CH


3






C


2


H


5






Cl






C.620




CF


3






CH


3






C


3


H


7






Cl






C.621




CF


3






CH


3






CH(CH


3


)


2






Cl






C.622




CF


3






CH


3






cyclopropyl




Cl






C.623




CF


3






CH


3






CF


3






Cl






C.624




CF


3






CH


3






OCH


3






Cl






C.625




CF


3






CH


3






C


6


H


5






Cl






C.626




CF


3






CH


3






4-F—C


6


H


5






Cl






C.627




CF


3






CF


3






H




F






C.628




CF


3






CF


3






CH


3






F






C.629




CF


3






CF


3






C


2


H


5






F






C.630




CF


3






CF


3






C


3


H


7






F






C.631




CF


3






CF


3






CH(CH


3


)


2






F






C.632




CF


3






CF


3






cyclopropyl




F






C.633




CF


3






CF


3






CF


3






F






C.634




CF


3






CF


3






OCH


3






F






C.635




CF


3






CF


3






C


6


H


5






F






C.636




CF


3






CF


3






4-F—C


6


H


5






F






C.637




CF


3






CF


3






H




C


2


H


5








C.638




CF


3






CF


3






CH


3






C


2


H


5








C.639




CF


3






CF


3






C


2


H


5






C


2


H


5








C.640




CF


3






CF


3






C


3


H


7






C


2


H


5








C.641




CF


3






CF


3






CH(CH


3


)


2






C


2


H


5








C.642




CF


3






CF


3






cyclopropyl




C


2


H


5








C.643




CF


3






CF


3






CF


3






C


2


H


5








C.644




CF


3






CF


3






OCH


3






C


2


H


5








C.645




CF


3






CF


3






C


6


H


5






C


2


H


5








C.646




CF


3






CF


3






4-F—C


6


H


5






C


2


H


5








C.647




CF


3






CF


3






H




CF


3








C.648




CF


3






CF


3






CH


3






CF


3








C.649




CF


3






CF


3






C


2


H


5






CF


3








C.650




CF


3






CF


3






C


3


H


7






CF


3








C.651




CF


3






CF


3






CH(CH


3


)


2






CF


3








C.652




CF


3






CF


3






cyclopropyl




CF


3








C.653




CF


3






CF


3






CF


3






CF


3








C.654




CF


3






CF


3






OCH


3






CF


3








C.655




CF


3






CF


3






C


6


H


5






CF


3








C.656




CF


3






CF


3






4-F—C


6


H


5






CF


3








C.657




CF


3






CF


3






H




CN






C.658




CF


3






CF


3






CH


3






CN






C.659




CF


3






CF


3






C


2


H


5






CN






C.660




CF


3






CF


3






C


3


H


7






CN






C.661




CF


3






CF


3






CH(CH


3


)


2






CN






C.662




CF


3






CF


3






cyclopropyl




CN






C.663




CF


3






CF


3






CF


3






CN






C.664




CF


3






CF


3






OCH


3






CN






C.665




CF


3






CF


3






C


6


H


5






CN






C.666




CF


3






CF


3






4-F—C


6


H


5






CN






C.667




CF


3






CF


3






H




Cl






C.668




CF


3






CF


3






CH


3






Cl






C.669




CF


3






CF


3






C


2


H


5






Cl






C.670




CF


3






CF


3






C


3


H


7






Cl






C.671




CF


3






CF


3






CH(CH


3


)


2






Cl






C.672




CF


3






CF


3






cyclopropyl




Cl






C.673




CF


3






CF


3






CF


3






Cl






C.674




CF


3






CF


3






OCH


3






Cl






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


5








C.688




Cl




CH


3






CH


3






C


2


H


5








C.689




Cl




CH


3






C


2


H


5






C


2


H


5








C.690




Cl




CH


3






C


3


H


7






C


2


H


5








C.691




Cl




CH


3






CH(CH


3


)


2






C


2


H


5








C.692




Cl




CH


3






cyclopropyl




C


2


H


5








C.693




Cl




CH


3






CF


3






C


2


H


5








C.694




Cl




CH


3






OCH


3






C


2


H


5








C.695




Cl




CH


3






C


6


H


5






C


2


H


5








C.696




Cl




CH


3






4-F—C


6


H


5






C


2


H


5








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




Cl




CH


3






CH(CH


3


)


2






CN






C.712




Cl




CH


3






cyclopropyl




CN






C.713




Cl




CH


3






CF


3






CN






C.714




Cl




CH


3






OCH


3






CN






C.715




Cl




CH


3






C


6


H


5






CN






C.716




Cl




CH


3






4-F—C


6


H


5






CN






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(CH


3


)


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


5








C.738




Cl




CF


3






CH


3






C


2


H


5








C.739




Cl




CF


3






C


2


H


5






C


2


H


5








C.740




Cl




CF


3






C


3


H


7






C


2


H


5








C.741




Cl




CF


3






CH(CH


3


)


2






C


2


H


5








C.742




Cl




CF


3






cyclopropyl




C


2


H


5








C.743




Cl




CF


3






CF


3






C


2


H


5








C.744




Cl




CF


3






OCH


3






C


2


H


5








C.745




Cl




CF


3






C


6


H


5






C


2


H


5








C.746




Cl




CF


3






4-F—C


6


H


5






C


2


H


5








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


H


7






CF


3








C.751




Cl




CF


3






CH(CH


3


)


2






CF


3








C.752




Cl




CF


3






cyclopropyl




CF


3








C.753




Cl




CF


3






CF


3






CF


3








C.754




Cl




CF


3






OCH


3






CF


3








C.755




Cl




CF


3






C


6


H


5






CF


3








C.756




Cl




CF


3






4-F—C


6


H


5






CF


3








C.757




Cl




CF


3






H




CN






C.758




Cl




CF


3






CH


3






CN






C.759




Cl




CF


3






C


2


H


5






CN






C.760




Cl




CF


3






C


3


H


7






CN






C.761




Cl




CF


3






CH(CH


3


)


2






CN






C.762




Cl




CF


3






cyclopropyl




CN






C.763




Cl




CF


3






CF


3






CN






C.764




Cl




CF


3






OCH


3






CN






C.765




Cl




CF


3






C


6


H


5






CN






C.766




Cl




CF


3






4-F—C


6


H


5






CN






C.767




Cl




CF


3






H




Cl






C.768




Cl




CF


3






CH


3






Cl






C.769




Cl




CF


3






C


2


H


5






Cl






C.770




Cl




CF


3






C


3


H


7






Cl






C.771




Cl




CF


3






CH(CH


3


)


2






Cl






C.772




Cl




CF


3






cyclopropyl




Cl






C.773




Cl




CF


3






CF


3






Cl






C.774




Cl




CF


3






OCH


3






Cl






C.775




Cl




CF


3






C


6


H


5






Cl






C.776




Cl




CF


3






4-F—C


6


H


5






Cl






C.777




CH


3






H




H




F






C.778




CH


3






H




CH


3






F






C.779




CH


3






H




C


2


H


5






F






C.780




CH


3






H




C


3


H


7






F






C.781




CH


3






H




CH(CH


3


)


2






F






C.782




CH


3






H




cyclopropyl




F






C.783




CH


3






H




CF


3






F






C.784




CH


3






H




OCH


3






F






C.785




CH


3






H




C


6


H


5






F






C.786




CH


3






H




4-F—C


6


H


5






F






C.787




CH


3






CH


3






H




F






C.788




CH


3






CH


3






CH


3






F






C.789




CH


3






CH


3






C


2


H


5






F






C.790




CH


3






CH


3






C


3


H


7






F






C.791




CH


3






CH


3






CH(CH


3


)


2






F






C.792




CH


3






CH


3






cyclopropyl




F






C.793




CH


3






CH


3






CF


3






F






C.794




CH


3






CH


3






OCH


3






F






C.795




CH


3






CH


3






C


6


H


5






F






C.796




CH


3






CH


3






4-F—C


6


H


5






F






C.797




CH


3






C


2


H


5






H




F






C.798




CH


3






C


2


H


5






CH


3






F






C.799




CH


3






C


2


H


5






C


2


H


5






F






C.800




CH


3






C


2


H


5






C


3


H


7






F






C.801




CH


3






C


2


H


5






CH(CH


3


)


2






F






C.802




CH


3






C


2


H


5






cyclopropyl




F






C.803




CH


3






C


2


H


5






CF


3






F






C.804




CH


3






C


2


H


5






OCH


3






F






C.805




CH


3






C


2


H


5






C


6


H


5






F






C.806




CH


3






C


2


H


5






4-F—C


6


H


5






F






C.807




CH


3






cyclopropyl




H




F






C.808




CH


3






cyclopropyl




CH


3






F






C.809




CH


3






cyclopropyl




C


2


H


5






F






C.810




CH


3






cyclopropyl




C


3


H


7






F






C.811




CH


3






cyclopropyl




CH(CH


3


)


2






F






C.812




CH


3






cyclopropyl




cyclopropyl




F






C.813




CH


3






cyclopropyl




CF


3






F






C.814




CH


3






cyclopropyl




OCH


3






F






C.815




CH


3






cyclopropyl




C


6


H


5






F






C.816




CH


3






cyclopropyl




4-F—C


6


H


5






F






C.817




CH


3






CF


3






H




F






C.818




CH


3






CF


3






CH


3






F






C.819




CH


3






CF


3






C


2


H


5






F






C.820




CH


3






CF


3






C


3


H


7






F






C.821




CH


3






CF


3






CH(CH


3


)


2






F






C.822




CH


3






CF


3






cyclopropyl




F






C.823




CH


3






CF


3






CF


3






F






C.824




CH


3






CF


3






OCH


3






F






C.825




CH


3






CF


3






C


6


H


5






F






C.826




CH


3






CF


3






4-F—C


6


H


5






F






C.827




CH


3






Cl




H




F






C.828




CH


3






Cl




CH


3






F






C.829




dH3




Cl




C


2


H


5






F






C.830




CH


3






Cl




C


3


H


7






F






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(CH


3


)


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






F






C.857




CH


3






H




H




C


2


H


5








C.858




CH


3






H




CH


3






C


2


H


5








C.859




CH


3






H




C


2


H


5






C


2


H


5








C.860




CH


3






H




C


3


H


7






C


2


H


5








C.861




CH


3






H




CH(CH


3


)


2






C


2


H


5








C.862




CH


3






H




cyclopropyl




C


2


H


5








C.863




CH


3






H




CF


3






C


2


H


5








C.864




CH


3






H




OCH


3






C


2


H


5








C.865




CH


3






H




C


6


H


5






C


2


H


5








C.866




CH


3






H




4-F—C


6


H


5






C


2


H


5








C.867




CH


3






CH


3






H




C


2


H


5








C.868




CH


3






CH


3






CH


3






C


2


H


5








C.869




CH


3






CH


3






C


2


H


5






C


2


H


5








C.870




CH


3






CH


3






C


3


H


7






C


2


H


5








C.871




CH


3






CH


3






CH(CH


3


)


2






C


2


H


5








C.872




CH


3






CH


3






cyclopropyl




C


2


H


5








C.873




CH


3






CH


3






CF


3






C


2


H


5








C.874




CH


3






CH


3






OCH


3






C


2


H


5








C.875




CH


3






CH


3






C


6


H


5






C


2


H


5








C.876




CH


3






CH


3






4-F—C


6


H


5






C


2


H


5








C.877




CH


3






C


2


H


5






H




C


2


H


5








C.878




CH


3






C


2


H


5






CH


3






C


2


H


5








C.879




CH


3






C


2


H


5






C


2


H


5






C


2


H


5








C.880




CH


3






C


2


H


5






C


3


H


7






C


2


H


5








C.881




CH


3






C


2


H


5






CH(CH


3


)


2






C


2


H


5








C.882




CH


3






C


2


H


5






cyclopropyl




C


2


H


5








C.883




CH


3






C


2


H


5






CF


3






C


2


H


5








C.884




CH


3






C


2


H


5






OCH


3






C


2


H


5








C.885




CH


3






C


2


H


5






C


6


H


5






C


2


H


5








C.886




CH


3






C


2


H


5






4-F—C


6


H


5






C


2


H


5








C.887




CH


3






cyclopropyl




H




C


2


H


5








C.888




CH


3






cyclopropyl




CH


3






C


2


H


5








C.889




CH


3






cyclopropyl




C


2


H


5






C


2


H


5








C.890




CH


3






cyclopropyl




C


3


H


7






C


2


H


5








C.891




CH


3






cyclopropyl




CH(CH


3


)


2






C


2


H


5








C.892




CH


3






cyclopropyl




cyclopropyl




C


2


H


5








C.893




CH


3






cyclopropyl




CF


3






C


2


H


5








C.894




CH


3






cyclopropyl




OCH


3






C


2


H


5








C.895




CH


3






cyclopropyl




C


6


H


5






C


2


H


5








C.896




CH


3






cyclopropyl




4-F—C


6


H


5






C


2


H


5








C.897




CH


3






CF


3






H




C


2


H


5








C.898




CH


3






CF


3






CH


3






C


2


H


5








C.899




CH


3






CF


3






C


2


H


5






C


2


H


5








C.900




CH


3






CF


3






C


3


H


7






C


2


H


5








C.901




CH


3






CF


3






CH(CH


3


)


2






C


2


H


5








C.902




CH


3






CF


3






cyclopropyl




C


2


H


5








C.903




CH


3






CF


3






CF


3






C


2


H


5








C.904




CH


3






CF


3






OCH


3






C


2


H


5








C.905




CH


3






CF


3






C


6


H


5






C


2


H


5








C.906




CH


3






CF


3






4-F—C


6


H


5






C


2


H


5








C.907




CH


3






Cl




H




C


2


H


5








C.908




CH


3






Cl




CH


3






C


2


H


5








C.909




CH


3






Cl




C


2


H


5






C


2


H


5








C.910




CH


3






Cl




C


3


H


7






C


2


H


5








C.911




CH


3






Cl




CH(CH


3


)


2






C


2


H


5








C.912




CH


3






Cl




cyclopropyl




C


2


H


5








C.913




CH


3






Cl




CF


3






C


2


H


5








C.914




CH


3






Cl




OCH


3






C


2


H


5








C.915




CH


3






Cl




C


6


H


5






C


2


H


5








C.916




CH


3






Cl




4-F—C


6


H


5






C


2


H


5








C.917




CH


3






F




H




C


2


H


5








C.918




CH


3






F




CH


3






C


2


H


5








C.919




CH


3






F




C


2


H


5






C


2


H


5








C.920




CH


3






F




C


3


H


7






C


2


H


5








C.921




CH


3






F




CH(CH


3


)


2






C


2


H


5








C.922




CH


3






F




cyclopropyl




C


2


H


5








C.923




CH


3






F




CF


3






C


2


H


5








C.924




CH


3






F




OCH


3






C


2


H


5








C.925




CH


3






F




C


6


H


5






C


2


H


5








C.926




CH


3






F




4-F—C


6


H


5






C


2


H


5








C.927




CH


3






OCH


3






H




C


2


H


5








C.928




CH


3






OCH


3






CH


3






C


2


H


5








C.929




CH


3






OCH


3






C


2


H


5






C


2


H


5








C.930




CH


3






OCH


3






C


3


H


7






C


2


H


5








C.931




CH


3






OCH


3






CH(CH


3


)


2






C


2


H


5








C.932




CH


3






OCH


3






cyclopropyl




C


2


H


5








C.933




CH


3






OCH


3






CF


3






C


2


H


5








C.934




CH


3






OCH


3






OCH


3






C


2


H


5








C.935




CH


3






OCH


3






C


6


H


5






C


2


H


5








C.936




CH


3






OCH


3






4-F—C


6


H


5






C


2


H


5








C.937




CH


3






H




H




CF


3








C.938




CH


3






H




CH


3






CF


3








C.939




CH


3






H




C


2


H


5






CF


3








C.940




CH


3






H




C


3


H


7






CF


3








C.941




CH


3






H




CH(CH


3


)


2






CF


3








C.942




CH


3






H




cyclopropyl




CF


3








C.943




CH


3






H




CF


3






CF


3








C.944




CH


3






H




OCH


3






CF


3








C.945




CH


3






H




C


6


H


5






CF


3








C.946




CH


3






H




4-F—C


6


H


5






CF


3








C.947




CH


3






CH


3






H




CF


3








C.948




CH


3






CH


3






CH


3






CF


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




CH


3






CH


3






cyclopropyl




CF


3








C.953




CH


3






CH


3






CF


3






CF


3








C.954




CH


3






CH


3






OCH


3






CF


3








C.955




CH


3






CH


3






C


6


H


5






CF


3








C.956




CH


3






CH


3






4-F—C


6


H


5






CF


3








C.957




CH


3






C


2


H


5






H




CF


3








C.958




CH


3






C


2


H


5






CH


3






CF


3








C.959




CH


3






C


2


H


5






C


2


H


5






CF


3








C.960




CH


3






C


2


H


5






C


3


H


7






CF


3








C.961




CH


3






C


2


H


5






CH(CH


3


)


2






CF


3








C.962




CH


3






C


2


H


5






cyclopropyl




CF


3








C.963




CH


3






C


2


H


5






CF


3






CF


3








C.964




CH


3






C


2


H


5






OCH


3






CF


3








C.965




CH


3






C


2


H


5






C


6


H


5






CF


3








C.966




CH


3






C


2


H


5






4-F—C


6


H


5






CF


3








C.967




CH


3






cyclopropyl




H




CF


3








C.968




CH


3






cyclopropyl




CH


3






CF


3








C.969




CH


3






cyclopropyl




C


2


H


5






CF


3








C.970




CH


3






cyclopropyl




C


3


H


7






CF


3








C.971




CH


3






cyclopropyl




CH(CH


3


)


2






CF


3








C.972




CH


3






cyclopropyl




cyclopropyl




CF


3








C.973




CH


3






cyclopropyl




CF


3






CF


3








C.974




CH


3






cyclopropyl




OCH


3






CF


3








C.975




CH


3






cyclopropyl




C


6


H


5






CF


3








C.976




CH


3






cyclopropyl




4-F—C


6


H


5






CF


3








C.977




CH


3






CF


3






H




CF


3








C.978




CH


3






CF


3






CH


3






CF


3








C.979




CH


3






CF


3






C


2


H


5






CF


3








C.980




CH


3






CF


3






C


3


H


7






CF


3








C.981




CH


3






CF


3






CH(CH


3


)


2






CF


3








C.982




CH


3






CF


3






cyclopropyl




CF


3








C.983




CH


3






CF


3






CF


3






CF


3








C.984




CH


3






CF


3






OCH


3






CF


3








C.985




CH


3






CF


3






C


6


H


5






CF


3








C.986




CH


3






CF


3






4-F—C


6


H


5






CF


3








C.987




CH


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(CH


3


)


2






CF


3








C.992




CH


3






Cl




cyclopropyl




CF


3








C.993




CH


3






Cl




CF


3






CF


3








C.994




CH


3






Cl




OCH


3






CF


3








C.995




CH


3






Cl




C


6


H


5






CF


3








C.996




CH


3






Cl




4-F—C


6


H


5






CF


3








C.997




CH


3






F




H




CF


3








C.998




CH


3






F




CH


3






CF


3








C.999




CH


3






F




C


2


H


5






CF


3








C.1000




CH


3






F




C


3


H


7






CF


3








C.1001




CH


3






F




CH(CH


3


)


2






CF


3








C.1002




CH


3






F




cyclopropyl




CF


3








C.1003




CH


3






F




CF


3






CF


3








C.1004




CH


3






F




OCH


3






CF


3








C.1005




CH


3






F




C


6


H


5






CF


3








C.1006




CH


3






F




4-F—C


6


H


5






CF


3








C.1007




CH


3






OCH


3






H




CF


3








C.1008




CH


3






OCH


3






CH


3






CF


3








C.1009




CH


3






OCH


3






C


2


H


5






CF


3








C.1010




CH


3






OCH


3






C


3


H


7






CF


3








C.1011




CH


3






OCH


3






CH(CH


3


)


2






CF


3








C.1012




CH


3






OCH


3






cyclopropyl




CF


3








C.1013




CH


3






OCH


3






CF


3






CF


3








C.1014




CH


3






OCH


3






OCH


3






CF


3








C.1015




CH


3






OCH


3






C


6


H


5






CF


3








C.1016




CH


3






OCH


3






4-F—C


6


H


5






CF


3








C.1017




CH


3






H




H




CN






C.1018




CH


3






H




CH


3






CN






C.1019




CH


3






H




C


2


H


5






CN






C.1020




CH


3






H




C


3


H


7






CN






C.1021




CH


3






H




CH(CH


3


)


2






CN






C.1022




CH


3






H




cyclopropyl




CN






C.1023




CH


3






H




CF


3






CN






C.1024




CH


3






H




OCH


3






CN






C.1025




CH


3






H




C


6


H


5






CN






C.1026




CH


3






H




4-F—C


6


H


5






CN






C.1027




CH


3






CH


3






H




CN






C.1028




CH


3






CH


3






CH


3






CN






C.1029




CH


3






CH


3






C


2


H


5






CN






C.1030




CH


3






CH


3






C


3


H


7






CN






C.1031




CH


3






CH


3






CH(CH


3


)


2






CN






C.1032




CH


3






CH


3






cyclopropyl




CN






C.1033




CH


3






CH


3






CF


3






CN






C.1034




CH


3






CH


3






OCH


3






CN






C.1035




CH


3






CH


3






C


6


H


5






CN






C.1036




CH


3






CH


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






CN






C.1039




CH


3






C


2


H


5






C


2


H


5






CN






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






CN






C.1042




CH


3






C


2


H


5






cyclopropyl




CN






C.1043




CH


3






C


2


H


5






CF


3






CN






C.1044




CH


3






C


2


H


5






OCH


3






CN






C.1045




CH


3






C


2


H


5






C


6


H


5






CN






C.1046




CH


3






C


2


H


5






4-F—C


6


H


5






CN






C.1047




CH


3






cyclopropyl




H




CN






C.1048




CH


3






cyclopropyl




CH


3






CN






C.1049




CH


3






cyclopropyl




C


2


H


5






CN






C.1050




CH


3






cyclopropyl




C


3


H


7






CN






C.1051




CH


3






cyclopropyl




CH(CH


3


)


2






CN






C.1052




CH


3






cyclopropyl




cyclopropyl




CN






C.1053




CH


3






cyclopropyl




CF


3






CN






C.1054




CH


3






cyclopropyl




OCH


3






CN






C.1055




CH


3






cyclopropyl




C


6


H


5






CN






C.1056




CH


3






cyclopropyl




4-F—C


6


H


5






CN






C.1057




CH


3






CF


3






H




CN






C.1058




CH


3






CF


3






CH


3






CN






C.1059




CH


3






CF


3






C


2


H


5






CN






C.1060




CH


3






CF


3






C


3


H


7






CN






C.1061




CH


3






CF


3






CH(CH


3


)


2






CN






C.1062




CH


3






CF


3






cyclopropyl




CN






C.1063




CH


3






CF


3






CF


3






CN






C.1064




CH


3






CF


3






OCH


3






CN






C.1065




CH


3






CF


3






C


6


H


5






CN






C.1066




CH


3






CF


3






4-F—C


6


H


5






CN






C.1067




CH


3






Cl




H




CN






C.1068




CH


3






Cl




CH


3






CN






C.1069




CH


3






Cl




C


2


H


5






CN






C.1070




CH


3






Cl




C


3


H


7






CN






C.1071




CH


3






Cl




CH(CH


3


)


2






CN






C.1072




CH


3






Cl




cyclopropyl




CN






C.1073




CH


3






Cl




CF


3






CN






C.1074




CH


3






Cl




OCH


3






CN






C.1075




CH


3






Cl




C


6


H


5






CN






C.1076




CH


3






Cl




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






CN






C.1080




CH


3






F




C


3


H


7






CN






C.1081




CH


3






F




CH(CH


3


)


2






CN






C.1082




CH


3






F




cyclopropyl




CN






C.1083




CH


3






F




CF


3






CN






C.1084




CH


3






F




OCH


3






CN






C.1085




CH


3






F




C


6


H


5






CN






C.1086




CH


3






F




4-F—C


6


H


5






CN






C.1087




CH


3






OCH


3






H




CN






C.1088




CH


3






OCH


3






CH


3






CN






C.1089




CH


3






OCH


3






C


2


H


5






CN






C.1090




CH


3






OCH


3






C


3


H


7






CN






C.1091




CH


3






OCH


3






CH(CH


3


)


2






CN






C.1092




CH


3






OCH


3






cyclopropyl




CN






C.1093




CH


3






OCH


3






CF


3






CN






C.1094




CH


3






OCH


3






OCH


3






CN






C.1095




CH


3






OCH


3






C


6


H


5






CN






C.1096




CH


3






OCH


3






4-F—C


6


H


5






CN






C.1097




CH


3






H




H




Cl






C.1098




CH


3






H




CH


3






Cl






C.1099




CH


3






H




C


2


H


5






Cl






C.1100




CH


3






H




C


3


H


7






Cl






C.1101




CH


3






H




CH(CH


3


)


2






Cl






C.1102




CH


3






H




cyclopropyl




Cl






C.1103




CH


3






H




CF


3






Cl






C.1104




CH


3






H




OCH


3






Cl






C.1105




CH


3






H




C


6


H


5






Cl






C.1106




CH


3






H




4-F—C


6


H


5






Cl






C.1107




CH


3






CH


3






H




Cl






C.1108




CH


3






CH


3






CH


3






Cl






C.1109




CH


3






CH


3






C


2


H


5






Cl






C.1110




CH


3






CH


3






C


3


H


7






Cl






C.1111




CH


3






CH


3






CH(CH


3


)


2






Cl






C.1112




CH


3






CH


3






cyclopropyl




Cl






C.1113




CH


3






CH


3






CF


3






Cl






C.1114




CH


3






CH


3






OCH


3






Cl






C.1115




CH


3






CH


3






C


6


H


5






Cl






C.1116




CH


3






CH


3






4-F—C


6


H


5






Cl






C.1117




CH


3






C


2


H


5






H




Cl






C.1118




CH


3






C


2


H


5






CH


3






Cl






C.1119




CH


3






C


2


H


5






C


2


H


5






Cl






C.2239




CH


3






C


2


H


5






C


3


H


7






Cl






C.2240




CH


3






C


2


H


5






CH(CH


3


)


2






Cl






C.2241




CH


3






C


2


H


5






cyclopropyl




Cl






C.2242




CH


3






C


2


H


5






CF


3






Cl






C.2243




CH


3






C


2


H


5






OCH


3






Cl






C.2244




CH


3






C


2


H


5






C


6


H


5






Cl






C.2245




CH


3






C


2


H


5






4-F—C


6


H


5






Cl






C.2246




CH


3






cyclopropyl




H




Cl






C.2247




CH


3






cyclopropyl




CH


3






Cl






C.2248




CH


3






cyclopropyl




C


2


H


5






Cl






C.2249




CH


3






cyclopropyl




C


3


H


7






Cl






C.2250




CH


3






cyclopropyl




CH(CH


3


)


2






Cl






C.2251




CH


3






cyclopropyl




cyclopropyl




Cl






C.2252




CH


3






cyclopropyl




CF


3






Cl






C.2253




CH


3






cyclopropyl




OCH


3






Cl






C.2254




CH


3






cyclopropyl




C


6


H


5






Cl






C.2255




CH


3






cyclopropyl




4-F—C


6


H


5






Cl






C.2256




CH


3






CF


3






H




Cl






C.2257




CH


3






CF


3






CH


3






Cl






C.2258




CH


3






CF


3






C


2


H


5






Cl






C.2259




CH


3






CF


3






C


3


H


7






Cl






C.2260




CH


3






CF


3






CH(CH


3


)


2






Cl






C.2261




CH


3






CF


3






cyclopropyl




Cl






C.2262




CH


3






CF


3






CF


3






Cl






C.2263




CH


3






CF


3






OCH


3






Cl






C.2264




CH


3






CF


3






C


6


H


5






Cl






C.2265




CH


3






CF


3






4-F—C


6


H


5






Cl






C.2266




CH


3






Cl




H




Cl






C.2267




CH


3






Cl




CH


3






Cl






C.2268




CH


3






Cl




C


2


H


5






Cl






C.2269




CH


3






Cl




C


3


H


7






Cl






C.2270




CH


3






Cl




CH(CH


3


)


2






Cl






C.2271




CH


3






Cl




cyclopropyl




Cl






C.2272




CH


3






Cl




CF


3






Cl






C.2273




CH


3






Cl




OCH


3






Cl






C.2274




CH


3






Cl




C


6


H


5






Cl






C.2275




CH


3






Cl




4-F—C


6


H


5






Cl






C.2276




CH


3






F




H




Cl






C.2277




CH


3






F




CH


3






Cl






C.2278




CH


3






F




C


2


H


5






Cl






C.2279




CH


3






F




C


3


H


7






Cl






C.2280




CH


3






F




CH(CH


3


)


2






Cl






C.2281




CH


3






F




cyclopropyl




Cl






C.2282




CH


3






F




CF


3






Cl






C.2283




CH


3






F




OCH


3






Cl






C.2284




CH


3






F




C


6


H


5






Cl






C.2285




CH


3






F




4-F—C


6


H


5






Cl






C.2286




CH


3






OCH


3






H




Cl






C.2287




CH


3






OCH


3






CH


3






Cl






C.2288




CH


3






OCH


3






C


2


H


5






Cl






C.2289




CH


3






OCH


3






C


3


H


7






Cl






C.2290




CH


3






OCH


3






CH(CH


3


)


2






Cl






C.2291




CH


3






OCH


3






cyclopropyl




Cl






C.2292




CH


3






OCH


3






CF


3






Cl






C.2293




CH


3






OCH


3






OCH


3






Cl






C.2294




CH


3






CCH


3






C


6


H


5






Cl






C.2295




CH


3






OCH


3






4-F—C


6


H


5






Cl














C.2296




CH


3






CH


3






CH


2


CH


2








C.2297




CH


3






CF


3






CH


2


CH


2








C.2298




CF


3






CH


3






CH


2


CH


2








C.2299




CH


3






C


2


H


5






CH


2


CH


2








C.2300




C


2


H


5






CH


3






CH


2


CH


2








C.2301




Cl




CH


3






CH


2


CH


2








C.2302




CH


3






Cl




CH


2


CH


2








C.2303




CH


3






CH


3






CH


2


CH


2


CH


2








C.2304




CH


3






CF


3






CH


2


CH


2


CH


2








C.2305




CF


3






CH


3






CH


2


CH


2


CH


2








C.2306




CH


3






C


2


H


5






CH


2


CH


2


CH


2








C.2307




C


2


H


5






CH


3






CH


2


CH


2


CH


2








C.2308




Cl




CH


3






CH


2


CH


2


CH


2








C.2309




CH


3






Cl




CH


2


CH


2


CH


2








C.2310




CH


3






CH


3






CH


2


CH


2


CH


2


CH


2








C.2311




CH


3






CF


3






CH


2


CH


2


CH


2


CH


2








C.2312




CF


3






CH


3






CH


2


CH


2


CH


2


CH


2








C.2313




CH


3






C


2


H


5






CH


2


CH


2


CH


2


CH


2








C.2314




C


2


H


5






CH


3






CH


2


CH


2


CH


2


CH


2








C.2315




Cl




CH


3






CH


2


CH


2


CH


2


CH


2








C.2316




CH


3






Cl




CH


2


CH


2


CH


2


CH


2

















C.2317




CH


2


CH


3






CH


3






H




H






C.2318




CH


2


CH


3






CH


3






CH


3






H






C.2319




CH


2


CH


3






CH


3






C


2


H


5






H






C.2320




CH


2


CH


3






CH


3






C


3


H


7






H






C.2321




CH


2


CH


3






CH


3






C


4


H


9






H






C.2322




CH


2


CH


3






CH


3






CH(CH


3


)


2






H






C.2323




CH


2


CH


3






CH


3






cyclopropyl




H






C.2324




CH


2


CH


3






CH


3






CF


3






H






C.2325




CH


2


CH


3






CH


3






OCH


3






H






C.2326




CH


2


CH


3






CH


3






OC


2


H


5






H






C.2327




CH


2


CH


3






CH


3






CH


2


—C


6


H


5






H






C.2328




CH


2


CH


3






CH


3






CH(CH


3


)C


6


H


5






H






C.2329




CH


2


CH


3






CH


3






C


6


H


5






H






C.2330




CH


2


CH


3






CH


3






4-F—C


6


H


5






H






C.2331




CH


2


CH


3






CH


3






4-Cl-2-pyridyl




H






C.2332




CH


2


CH


3






CH


3






F




H






C.2333




CH


2


CH


3






CH


3






CN




H






C.2334




CH


2


CH


3






C


2


H


5






H




H






C.2335




CH


2


CH


3






C


2


H


5






CH


3






H






C.2336




CH


2


CH


3






C


2


H


5






C


2


H


5






H






C.2337




CH


2


CH


3






C


2


H


5






C


3


H


7






H






C.2338




CH


2


CH


3






C


2


H


5






C


4


H


9






H






C.2339




CH


2


CH


3






C


2


H


5






CH(CH


3


)


2






H






C.2340




CH


2


CH


3






C


2


H


5






cyclopropyl




H






C.2341




CH


2


CH


3






C


2


H


5






CF


3






H






C.2342




CH


2


CH


3






C


2


H


5






OCH


3






H






C.2343




CH


2


CH


3






C


2


H


5






OC


2


H


5






H






C.2344




CH


2


CH


3






C


2


H


5






CH


2


—C


6


H


5






H






C.2345




CH


2


CH


3






C


2


H


5






CH(CH


3


)C


6


H


5






H






C.2346




CH


2


CH


3






C


2


H


5






C


6


H


5






H






C.2347




CH


2


CH


3






C


2


H


5






4-F—C


6


H


5






H






C.2348




CH


2


CH


3






C


2


H


5






4-Cl-2-pyridyl




H






C.2349




CH


2


CH


3






C


2


H


5






F




H






C.2350




CH


2


CH


3






C


2


H


5






CN




H






C.2351




CH


2


CH


3






CF


3






H




H






C.2352




CH


2


CH


3






CF


3






CH


3






H






C.2353




CH


2


CH


3






CF


3






C


2


H


5






H






C.2354




CH


2


CH


3






CF


3






C


3


H


7






H






C.2355




CH


2


CH


3






CF


3






C


4


H


9






H






C.2356




CH


2


CH


3






CF


3






CH(CH


3


)


2






H






C.2357




CH


2


CH


3






CF


3






cyclopropyl




H






C.2358




CH


2


CH


3






CF


3






CF


3






H






C.2359




CH


2


CH


3






CF


3






OCH


3






H






C.2360




CH


2


CH


3






CF


3






OC


2


H


5






H






C.2361




CH


2


CH


3






CF


3






CH


2


—C


6


H


5






H






C.2362




CH


2


CH


3






CF


3






CH(CH


3


)C


6


H


5






H






C.2363




CH


2


CH


3






CF


3






C


6


H


5






H






C.2364




CH


2


CH


3






CF


3






4-F—C


6


H


5






H






C.2365




CH


2


CH


3






CF


3






4-Cl-2-pyridyl




H






C.2366




CH


2


CH


3






CF


3






F




H






C.2367




CH


2


CH


3






CF


3






CN




H






C.2368




CH


2


CH


3






Cl




H




H






C.2369




CH


2


CH


3






Cl




CH


3






H






C.2370




CH


2


CH


3






Cl




C


2


H


5






H






C.2371




CH


2


CH


3






Cl




C


3


H


7






H






C.2372




CH


2


CH


3






Cl




C


4


H


9






H






C.2373




CH


2


CH


3






Cl




CH(CH


3


)


2






H






C.2374




CH


2


CH


3






Cl




cyclopropyl




H






C.2375




CH


2


CH


3






Cl




CF


3






H






C.2376




CH


2


CH


3






Cl




OCH


3






H






C.2377




CH


2


CH


3






Cl




OC


2


H


5






H






C.2378




CH


2


CH


3






Cl




CH


2


—C


6


H


5






H






C.2379




CH


2


CH


3






Cl




CH(CH


3


)C


6


H


5






H






C.2380




CH


2


CH


3






Cl




C


6


H


5






H






C.2381




CH


2


CH


3






Cl




4-F—C


6


H


5






H






C.2382




CH


2


CH


3






Cl




4-Cl-2-pyridyl




H






C.2383




CH


2


CH


3






Cl




F




H






C.2384




CH


2


CH


3






Cl




CN




H






C.2385




CH


2


CH


3






OCH


3






H




H






C.2386




CH


2


CH


3






OCH


3






CH


3






H






C.2387




CH


2


CH


3






OCH


3






C


2


H


5






H






C.2388




CH


2


CH


3






OCH


3






C


3


H


7






H






C.2389




CH


2


CH


3






OCH


3






C


4


H


9






H






C.2390




CH


2


CH


3






OCH


3






CH(CH


3


)


2






H






C.2391




CH


2


CH


3






OCH


3






cyclopropyl




H






C.2392




CH


2


CH


3






OCH


3






CF


3






H






C.2393




CH


2


CH


3






OCH


3






OCH


3






H






C.2394




CH


2


CH


3






OCH


3






OC


2


H


5






H






C.2395




CH


2


CH


3






OCH


3






CH


2


—C


6


H


5






H






C.2396




CH


2


CH


3






OCH


3






CH(CH


3


)C


6


H


5






H






C.2397




CH


2


CH


3






OCH


3






C


6


H


5






H






C.2398




CH


2


CH


3






OCH


3






4-F—C


6


H


5






H






C.2399




CH


2


CH


3






OCH


3






4-Cl-2-pyridyl




H






C.2400




CH


2


CH


3






OCH


3






F




H






C.2401




CH


2


CH


3






OCH


3






CN




H






C.2402




CH


2


CH


3






CH


3






H




CH


3








C.2403




CH


2


CH


3






CH


3






CH


3






CH


3








C.2404




CH


2


CH


3






CH


3






C


2


H


5






CH


3








C.2405




CH


2


CH


3






CH


3






C


3


H


7






CH


3








C.2406




CH


2


CH


3






CH


3






C


4


H


9






CH


3








C.2407




CH


2


CH


3






CH


3






CH(CH


3


)


2






CH


3








C.2408




CH


2


CH


3






CH


3






cyclopropyl




CH


3








C.2409




CH


2


CH


3






CH


3






CF


3






CH


3








C.2410




CH


2


CH


3






CH


3






OCH


3






CH


3








C.2411




CH


2


CH


3






CH


3






OC


2


H


5






CH


3








C.2412




CH


2


CH


3






CH


3






CH


2


—C


6


H


5






CH


3








C.2413




CH


2


CH


3






CH


3






CH(CH


3


)C


6


H


5






CH


3








C.2414




CH


2


CH


3






CH


3






C


6


H


5






CH


3








C.2415




CH


2


CH


3






CH


3






4-F—C


6


H


5






CH


3








C.2416




CH


2


CH


3






CH


3






4-Cl-2-pyridyl




CH


3








C.2417




CH


2


CH


3






CH


3






F




CH


3








C.2418




CH


2


CH


3






CH


3






CN




CH


3








C.2419




CH


2


CH


3






C


2


H


5






H




CH


3








C.2420




CH


2


CH


3






C


2


H


5






CH


3






CH


3








C.2421




CH


2


CH


3






C


2


H


5






C


2


H


5






CH


3








C.2422




CH


2


CH


3






C


2


H


5






C


3


H


7






CH


3








C.2423




CH


2


CH


3






C


2


H


5






C


4


H


9






CH


3








C.2424




CH


2


CH


3






C


2


H


5






CH(CH


3


)


2






CH


3








C.2425




CH


2


CH


3






C


2


H


5






cyclopropyl




CH


3








C.2426




CH


2


CH


3






C


2


H


5






CF


3






CH


3








C.2427




CH


2


CH


3






C


2


H


5






OCH


3






CH


3








C.2428




CH


2


CH


3






C


2


H


5






OC


2


H


5






CH


3








C.2429




CH


2


CH


3






C


2


H


5






CH


2


—C


6


H


5






CH


3








C.2430




CH


2


CH


3






C


2


H


5






CH(CH


3


)C


6


H


5






CH


3








C.2431




CH


2


CH


3






C


2


H


5






C


6


H


5






CH


3








C.2432




CH


2


CH


3






C


2


H


5






4-F-C


6


H


5






CH


3








C.2433




CH


2


CH


3






C


2


H


5






4-Cl-2-pyridyl




CH


3








C.2434




CH


2


CH


3






C


2


H


5






F




CH


3








C.2435




CH


2


CH


3






C


2


H


5






CN




CH


3








C.2436




CH


2


CH


3






CF


3






H




CH


3








C.2437




CH


2


CH


3






CF


3






CH


3






CH


3








C.2438




CH


2


CH


3






CF


3






C


2


H


5






CH


3








C.2439




CH


2


CH


3






CF


3






C


3


H


7






CH


3








C.2440




CH


2


CH


3






CF


3






C


4


H


9






CH


3








C.2441




CH


2


CH


3






CF


3






CH(CH


3


)


2






CH


3








C.2442




CH


2


CH


3






CF


3






cyclopropyl




CH


3








C.2443




CH


2


CH


3






CF


3






CF


3






CH


3








C.2444




CH


2


CH


3






CF


3






OCH


3






CH


3








C.2445




CH


2


CH


3






CF


3






OC


2


H


5






CH


3








C.2446




CH


2


CH


3






CF


3






CH


2


—C


6


H


5






CH


3








C.2447




CH


2


CH


3






CF


3






CH(CH


3


)C


6


H


5






CH


3








C.2448




CH


2


CH


3






CF


3






C


6


H


5






CH


3








C.2449




CH


2


CH


3






CF


3






4-F—C


6


H


5






CH


3








C.2450




CH


2


CH


3






CF


3






4-Cl-2-pyridyl




CH


3








C.2451




CH


2


CH


3






CF


3






F




CH


3








C.2452




CH


2


CH


3






CF


3






CN




CH


3








C.2453




CH


2


CH


3






Cl




H




CH


3








C.2454




CH


2


CH


3






Cl




CH


3






CH


3








C.2455




CH


2


CH


3






Cl




C


2


H


5






CH


3








C.2456




CH


2


CH


3






Cl




C


3


H


7






CH


3








C.2457




CH


2


CH


3






Cl




C


4


H


9






CH


3








C.2458




CH


2


CH


3






Cl




CH(CH


3


)


2






CH


3








C.2459




CH


2


CH


3






Cl




cyclopropyl




CH


3








C.2460




CH


2


CH


3






Cl




CF


3






CH


3








C.2461




CH


2


CH


3






Cl




OCH


3






CH


3








C.2462




CH


2


CH


3






Cl




OC


2


H


5






CH


3








C.2463




CH


2


CH


3






Cl




CH


2


—C


6


H


5






CH


3








C.2464




CH


2


CH


3






Cl




CH(CH


3


)C


6


H


5






CH


3








C.2465




CH


2


CH


3






Cl




C


6


H


5






CH


3








C.2466




CH


2


CH


3






Cl




4-F—C


6


H


5






CH


3








C.2467




CH


2


CH


3






Cl




4-Cl-2-pyridyl




CH


3








C.2468




CH


2


CH


3






Cl




F




CH


3








C.2469




CH


2


CH


3






Cl




CN




CH


3








C.2470




CH


2


CH


3






OCH


3






H




CH


3








C.2471




CH


2


CH


3






OCH


3






CH


3






CH


3








C.2472




CH


2


CH


3






OCH


3






C


2


H


5






CH


3








C.2473




CH


2


CH


3






OCH


3






C


3


H


7






CH


3








C.2474




CH


2


CH


3






OCH


3






C


4


H


9






CH


3








C.2475




CH


2


CH


3






OCH


3






CH(CH


3


)


2






CH


3








C.2476




CH


2


CH


3






OCH


3






cyclopropyl




CH


3








C.2477




CH


2


CH


3






OCH


3






CF


3






CH


3








C.2478




CH


2


CH


3






OCH


3






OCH


3






CH


3








C.2479




CH


2


CH


3






OCH


3






OC


2


H


5






CH


3








C.2480




CH


2


CH


3






OCH


3






CH


2


—C


6


H


5






CH


3








C.2481




CH


2


CH


3






OCH


3






CH(CH


3


)C


6


H


5






CH


3








C.2482




CH


2


CH


3






OCH


3






C


6


H


5






CH


3








C.2483




CH


2


CH


3






OCH


3






4-F—C


6


H


5






CH


3








C.2484




CH


2


CH


3






OCH


3






4-Cl-2-pyridyl




CH


3








C.2485




CH


2


CH


3






OCH


3






F




CH


3








C.2486




CH


2


CH


3






OCH


3






CN




CH


3
















The compounds I are suitable as fungicides.




The compounds I are distinguished by outstanding efficacy against a broad spectrum of phytopathogenic fungi, in particular from the classes of the Ascomycetes, Deuteromycetes, Phycomycetes and Basidiomycetes. Some of them act systemically and can be employed 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


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 95, 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.




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. Normal 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, eg. 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 compounds 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) dimethyldithiocarbamate, zinc dimethyldithiocarbamate, zinc ethylenebisdithiocarbamate, manganese ethylenebisdithiocarbamate, manganese zinc ethylenediaminebisdithiocarbamate, tetramethylthiuram disulfide, ammonia complex of zinc (N,N-ethylenebisdithiocarbamate), ammonia complex of zinc (N,N′-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 5-nitro-isophthalate;




heterocyclic substances, such as 2-heptadecyl-2-imidazoline acetate, 2,4-dichloro-6-(o-chloroanilino)-2-triazine, O,O-di-ethyl phthalimidophosphonothioate, 5-amino-1-[bis(dimethylamino)phosphinyl]-3-phenyl-1,2,4-triazole, 2,3-dicyano-1,4-dithioanthraquinone, 2-thio-1,3-dithiolo[4,5-b]quinoxaline, methyl 1-(butylcarbamoyl)-2-benzimidazolecarbamate, 2-methoxycarbonyl-aminobenzimidazole, 2-(2-furyl)benzimidazole, 2-(4-thiazolyl)-benzimidazole, N-(1,1,2,2-tetrachloroethylthio)-tetrahydrophthalimide, N-trichloromethylthiotetrahydrophthalimide, N-trichloromethylthiophthalimide,




N-dichlorofluoromethylthio-N′,N′-dimethyl-N-phenylsulfodiamide, 5-ethoxy-3-trichloromethyl-1,2,3-thiadiazole, 2-thiocyanatomethylthiobenzothiazole, 1,4-dichloro-2,5-dimethoxybenzene, 4-(2-chlorophenylhydrazono)-3-methyl-5-isoxazolone, pyridine-2-thiol oxide, 8-hydroxyquinoline or its copper salt, 2,3-dihydro-5-carboxanilido-6-methyl-1,4-oxathiine, 2,3-di-hydro-5-carboxanilido-6-methyl-1,4-oxathiine 4,4-dioxide, 2-methyl-5,6-dihydro-4H-pyran-3-carboxanilide, 2-methylfuran-3-carboxanilide, 2,5-dimethylfuran-3-carboxanilide, 2,4,5-trimethylfuran-3-carboxanilide, N-cyclohexyl-2,5-dimethylfuran-3-carboxamide, N-cyclohexyl-N-methoxy-2,5-dimethylfuran-3-carboxamide, 2-methylbenzanilide, 2-iodobenzanilide, N-formyl-N-morpholine-2,2,2-trichloroethyl acetal, piperazine-1,4-diylbis(2,2,2-trichloroethyl)formamide, 1-(3,4-di-chloroanilino)-1-formylamino-2,2,2-trichloroethane, 2,6-dimethyl-N-tridecylmorpholine or its salts, 2,6-dimethyl-N-cyclododecylmorpholine or its salts, N-[3-(p-tert-butylphenyl)-2-methylpropyl]-cis-2,6-dimethylmorpholine, N-[3-(p-tert-butylphenyl)-2-methylpropyl]piperidine, 1-[2-(2,4-dichlorophenyl)-4-ethyl-1,3-dioxolan-2-ylethyl]-1H-1,2,4-triazole, 1-[2-(2,4-dichlorophenyl)-4-n-propyl-1,3-dioxolan-2-ylethyl]-1H-1,2,4-triazole, N-(n-propyl)-N-(2,4,6-trichlorophenoxy-ethyl)-N′-imidazolylurea, 1-(4-chlorophenoxy)-3,3-dimethyl-1-(1H-1,2,4-triazol-1-yl)-2-butanone, 1-(4-chlorophenoxy)-3,3-dimethyl-1-(1H-1,2,4-triazol-1-yl)-2-butanol, (2RS,3RS)-1-[3-(2-chlorophenyl)-2-(4-fluorophenyl)oxiran-2-ylmethyl]-1H-1,2,4-triazole, α-(2-chlorophenyl)-α-(4-chlorophenyl)-5-pyrimidinemethanol, 5-butyl-2-dimethylamino-4-hydroxy-6-methylpyrimidine, bis(p-chlorophenyl)-3-pyridinemethanol, 1,2-bis(3-ethoxycarbonyl-2-thioureido)benzene, 1,2-bis(3-methoxycarbonyl-2-thioureido)benzene,




strobilurins such as methyl E-methoxyimino-[α-(o-tolyloxy)-o-tolyl]acetate, methyl E-2-{2-[6-[(2-cyanophenoxy)pyrimidin-4-yloxy]phenyl}-3-methoxyacrylate, N-methyl-E-methoxyimino-[α-(2-phenoxyphenyl]acetamide, N-methyl-E-methoxyimino-[α-(2,5-dimethylphenoxy)-o-tolyl]acetamide, anilinopyrimidines such as N-(4,6-dimethylpyrimidin-2-yl)-aniline, N-[4-methyl-6-(1-propynyl)pyrimidin-2-yl]aniline, 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)acryloylmorpholine,




and a variety of fungicides such as dodecylguanidine acetate, 3-[3-(3,5-dimethyl-2-oxycyclohexyl)-2-hydroxyethyl]-glutarimide, hexachlorobenzene, methyl-N-(2,6-dimethylphenyl)-N-(2-furoyl)-DL-alaninate, DL-N-(2,6-dimethylphenyl)-N-(2′-methoxyacetyl)-alanine methyl ester, N-(2,6-dimethylphenyl)-N-chloroacetyl-D,L-2-amino-butyrolactone, DL-N-(2,6-dimethylphenyl)-N-(phenylacetyl)-alanine methyl ester, 5-methyl-5-vinyl-3-(3,5-dichlorophenyl)-2,4-dioxo-1,3-oxazolidine, 3-[3,5-dichlorophenyl-(5-methyl-5-methoxymethyl]-1,3-oxazolidine-2,4-dione, 3-(3,5-dichlorophenyl)-1-isopropylcarbamoylhydantoin, N-(3,5-dichlorophenyl)-1,2-dimethylcyclopropane-1,2-dicarboximide, 2-cyano-[N-(ethylaminocarbonyl)-2-methoximino]-acetamide, 1-[2-(2,4-dichlorophenyl)-pentyl]-1H-1,2,4-triazole, 2,4-difluoro-a-(1H-1,2,4-triazolyl-1-methyl)-benzhydryl alcohol, N-(3-chloro-2,6-dinitro-4-trifluoromethylphenyl)-5-trifluoromethyl-3-chloro-2-aminopyridine, 1-((bis-(4-fluorophenyl)methylsilyl)methyl)-1H-1,2,4-triazole.




The compounds of the formula I are furthermore suitable for effectively controlling pests from the classes 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, Trichoplusiani, 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, Otiorrhynchus 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 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.






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 nordmannianae, 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.






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 1.0, kg/ha.




Substances which are suitable for the preparation of ready-to-spray 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, 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 naphthalenesulfonic acid with phenol and formaldehyde, polyoxyethylene octylphenyl ether, ethoxylated isooctylphenol, octylphenol, nonylphenol, alkylphenyl polyglycol ethers, tributylphenyl polyglycol ether, alkylaryl polyether alcohols, isotridecyl alcohol, fatty alcohol/ethylene oxide condensates, ethoxylated castor oil, polyoxyethylene alkyl ethers, ethoxylated polyoxypropylene, lauryl alcohol polyglycol ether acetal, sorbitol esters, ligninsulfite 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.




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 has 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 isooctylphenyl 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 80% 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-α-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, 20 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 dispersion which comprises 0.02% by weight of the active ingredient.




VIII. 20 parts by weight of a compound according to the invention are mixed thoroughly with 3 parts by weight of sodium diisobutylnaphthalene-α-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 silicas, silica gels, 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 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 compounds as required. The resulting compounds are listed in the tables which follow together with physical data.




1. Preparation of methyl methoxyimino-[2-(2-ethoxyimino-1-methyl-propylideneaminooxy)pyridin-3-yl]acetate











1.a 2-Chloro-3-pyridinecarboxylic acid chloride











1131 g (9.5 mol) of thionyl chloride were slowly added dropwise at 90° C. to 500 g (3.17 mol) of 2-chloronicotinic acid. The reaction mixture was stirred for 1 hour at 90° C. and freed from thionyl chloride under reduced pressure (“high vacuum”) at approximately 40° C. This gave 561 g (100%) of the title compound as colorless crystals.






1


H NMR (CDCl


3


; δ in ppm): 7.45 (m, 1H, pyridyl); 8.42 (dd, 1H, pyridyl); 8.62 (dd, 1H, pyridyl);




IR: 3060, 1786, 1570, 1556, 1392, 1261, 1188, 865, 816, 746, 726 cm


−1


.




1.b 2-(2-Chloropyridin-3-yl)glyoxylic acid cyanide











A mixture of 558 g (3.18 mol) of 2-chloro-3-pyridinecarboxylic acid chloride, 566 g (6.23 mol) of copper(I) cyanide and 4000 ml of acetonitrile was stirred for 1 hour at room temperature and then refluxed for 2 hours. The reaction mixture was freed from solvent under reduced pressure (“high vacuum”) at approximately 40° C. and the residue was boiled up twice with approximately 1 l of toluene and filtered off. The combined organic phases were freed from solvent under reduced pressure (“high vacuum”) at approximately 40° C. This gave 348 g (62%) of the title compound as brown crystals.




IR: 2220, 1730, 1574, 1559, 1399, 1259, 1066, 871, 746, 728 cm


−1


.




1.c Methyl 2-(2-chloropyridin-3-yl)glyoxylate











A mixture of 83 g (0.47 mol) of 2-(2-chloropyridin-3-yl)glyoxylic acid cyanide and 500 ml of concentrated HCl was stirred for 8 hours at 50° C. The reaction solution was concentrated at approximately 40° C. under reduced pressure (“high vacuum”), treated twice with 100 ml of toluene, and the solvent was removed at approximately 40° C. under reduced pressure (“high vacuum”). The residue was dissolved in 500 ml of methanol and 5 ml of concentrated H


2


SO


4


and refluxed for 20 hours. The solvent was removed at approximately 40° C. under reduced pressure (“high vacuum”), and the residue was taken up in 500 ml of ethyl acetate and washed with saturated sodium hydrogen carbonate solution. The organic phase was dried over sodium sulfate and the solvent was removed under reduced pressure. The resulting residue was subjected to fractional distillation over a packed column 20 cm in length. This gave 18.3 g (19%) of the title compound as a yellow oil of boiling point 105-115° C. at 0.2-0.3 mbar.






1


H NMR (CDCl


3


; δ in ppm): 4.0 (s, 3H, OCH


3


); 7.45 (m, 1H, pyridyl); 8.1 (dd, 1H, pyridyl); 8.6 (dd, 1H, pyridyl);




MS m/z (intensity): 199 (M


+


, 8), 186 (20), 142 (50), 140 (100), 114 (18), 112 (40), 76 (24), 50 (10), 18 (16).




1. d Methyl [2-(2-ethoxyimino-1-methyl-propylideneaminooxy)pyridin-3-yl]glyoxylate











A mixture of 3.25 g (22.6 mmol) of 2-ethoxyimino-3-hydroxyiminobutane and 25 ml of tert-butanol was treated with 2.53 g (22.6 mmol) of potassium tert-butoxide at 60° C. and stirred for 1 hour at the same temperature. The reaction mixture was freed from solvent under reduced pressure (“high vacuum”) at approximately 40° C. The residue was introduced into 15 ml of dimethyl sulfoxide, and 4.5 g (22.6 mmol) of methyl 2-(2-chloropyridin-3-yl)glyoxylate, dissolved in 5 ml of dimethyl sulfoxide, were added at 50° C. The mixture was stirred for 20 hours at room temperature, and the reaction mixture was poured onto approximately 150 g of ice and extracted repeatedly with ethyl acetate. The organic phases were combined, washed with water and dried over sodium sulfate, and the solvent was removed under reduced pressure. The resulting residue was purified by column chromatography over silica gel using cyclohexane/ethyl acetate (4/1) as the eluent. This gave 1.56 g (23%) of the title compound as a white solid.






1


H NMR (CDCl


3


; δ in ppm): 1,3 (t, 3H, CH


3


); 2.04 (s, 3H, CH


3


); 2.3 (s, 3H, CH


3


); 3.82 (s, 3H, OCH


3


); 4.28 (q, 2H, OCH


2


); 7.22 (m, 1H, pyridyl); 8.1 (dd, 1H, pyridyl); 8.5 (dd, 1H, pyridyl);




M.P.: 75° C.




1.e Methyl methoxyimino-[2-(2-ethoxyimino-1-methylpropylideneaminooxy)pyridin-3-yl]-glyoxylate











A mixture of 800 mg (2.6 mmol) of methyl [2-(2-ethoxyimino-1-methylpropylideneaminooxy)pyridin-3-yl]-glyoxylate and 410 mg of pyridine in 10 ml of methanol was treated with 240 mg (2.9 mmol) of O-methylhydroxylamine hydrochloride and heated for 1 hour to 50° C. The reaction mixture was freed from solvent under reduced pressure, and the residue was taken up in ethyl acetate and washed with dilute aqueous NaCl solution. The organic phase was dried over sodium sulfate and the solvent was removed under reduced pressure. The resulting residue was purified by column chromatography over silica gel using cyclohexane/ethyl acetate (4/1) as the eluent. This gave 480 mg (55%) of the title compound as a white solid.






1


H NMR (CDCl


3


; δ in ppm): 1.3 (t, 3H, CH


3


); 2.1 (s, 3H, CH


3


); 2.2 (s, 3H, CH


3


); 3.82 (s, 3H, OCH


3


); 4.06 (s, 3H, OCH


3


); 4.12 (q, 2H, OCH


2


); 7.1 (m, 1H, pyridyl); 7.7 (dd, 1H, pyridyl); 8.38 (dd, 1H, pyridyl);




M.p.: 71° C.




150 mg (17%) of methyl Z-methoxyimino-[2-E,E-(2-ethoxyimino-1-methylpropylideneaminooxy)pyridin-3-yl]glyoxylate were isolated as a second product in the form of a yellow oil.













1


H NMR (CDCl


3


; δ in ppm): 1.3 (t, 3H, CH


3


); 2.18 (s, 3H, CH


3


); 2.24 (s, 3H, CH


3


); 3.8 (s, 3H, OCH


3


); 4.06 (s, 3H, OCH


3


); 4.12 (q, 2H, OCH


2


); 7.14 (m, 1H, pyridyl); 8.0 (dd, 1H, pyridyl); 8.4 (dd, 1H, pyridyl);




IR: 2980, 2940, 1752, 1587, 1418, 1252, 1227, 1209, 1048, 1027, 913, 893 cm


−1


.




2. Preparation of N-methyl-methoxyimino-[2-(2-ethoxyimino-1-methylpropylideneaminooxy)pyridin-3-yl]acetamide











A mixture of 260 mg (0.77 mmol) of methyl oxyimino-[2-(2-ethoxyimino-1-methylpropylideneaminooxy)pyridin-3-yl]glyoxylate and 2 g of 40% strength aqueous methylamine solution in 3 ml of tetrahydrofuran was refluxed for 2 hours. The reaction mixture was freed from solvent under reduced pressure; the residue was taken up in ethyl acetate; and the mixture was washed with dilute aqueous NaCl solution. The organic phase was dried over sodium sulfate and the solvent was removed under reduced pressure. This gave 240 mg (93%) of the title compound as a white solid.






1


H NMR (CDCl


3


; δ in ppm): 1.3 (t, 3H, CH


3


); 2.1 (s, 3H, CH


3


); 2.2 (s, 3H, CH


3


); 2.90, 2.92 (in each case s, 3H, NCH


3


); 3.95 (s, 3H, OCH


3


); 4.25 (q, 2H, OCH


2


); 6.8 (m, 1H, NH); 7.1 (m, 1H, pyridyl); 7.65 (dd, 1H, pyridyl); 8.35 (dd, 1H, pyridyl);




M.p.: 110° C.




3. Preparation of methyl methoxyimino-[2-(2-ethoxyimino-1-methylpropylideneaminooxy)pyridin-3-yl]acrylate











A mixture of 650 mg (1.9 mmol) of methoxymethyltriphenyl-phosphonium chloride and 340 g (1.9 mmol) of sodium methoxide solution (30% strength in methanol) in 8 ml of dimethylformamide was stirred for 10 minutes at room temperature. The reaction mixture was subsequently treated with 400 mg (0.95 mmol) of methyl [2-(2-ethoxyimino-1-methylpropylideneaminooxy)pyridin-3-yl]glyoxylate, dissolved in 4 ml of dimethylformamide. The reaction mixture was stirred for 4 hours at room temperature, hydrolyzed with 20 ml of water, and the aqueous phase was extracted with ethyl acetate. The combined organic phases were dried over sodium sulfate and the solvent was removed under reduced pressure. This gave 120 mg (38%) of the title compound as a yellow oil.






1


H NMR (CDCl


3


; δ in ppm): 1.3 (t, 3H, CH


3


); 2.16 (s, 3H, CH


3


); 2.2 (s, 3H, CH


3


); 3.7 (s, 3H, OCH


3


); 3.84 (s, 3H, OCH


3


); 4.22 (q, 2H, OCH


2


); 7.1 (m, 1H, pyridyl); 7.58 (s, 1H, CH); 7.6 (dd, 1H, pyridyl); 8.25 (dd, 1H, pyridyl);




IR: 2950, 2920, 2850, 1713, 1435, 1416, 1291, 1263, 1238, 1132, 1105, 1050, 914 cm


−1


.













TABLE























(1.8)
























No.




R




R


1






R


3






Y


1






R


4








1


H NMR [δ in ppm; CDCl


3


]









1




Ic




CH


3






CH


3






O




CH


3






2.1 (s, 3H, CH


3


); 2.2 (s, 3H, CH


3


);












3.82 (s, 3H, OCH


3


); 4.0 (s, 3H,












OCH


3


); 4.05 (s, 3H, OCH


3


); 7.15 (m,












1H, Py); 7.7 (dd, 1H, Py); 8.35 (dd,












1H, Py)






2




Ic




CH


3






CH


3






O




CH(CH


3


)


2






1.3 (d, 6H, 2XCH


3


); 2.1 (s, 3H,












CH


3


); 2.2 (s, 3H, CH


3


); 3.84 (s, 3H,












OCH


3


); 4.06 (s, 3H, OCH


3


); 4.45 (m,












1H, CH); 7.14 (m, 1H, Py); 7.7 (dd,












1H, Py); 8.38 (dd, 1H, Py)






3




Ic




CH


3






CH


3






O




CH


2


C═CH




2.1 (s, 3H, CH


3


); 2.2 (s, 3H, CH


3


);












2.5 (s, 1H, CH); 3.82 (s, 3H, OCH


3


);












4.05 (s, 3H, OCH


3


); 4.8 (s, 2H,












OCH


2


); 7.1 (m, 1H, Py); 7.7 (dd, 1H,












Py); 8.38 (dd, 1H, Py)






4




Ic




CH


3






CH


3






O




CH


2


—C


6


H


5






2.1 (s, 3H, CH


3


); 2.2 (s, 3H, CH


3


);












3.8 (s, 3H, OCH


3


); 4.05 (s, 3H,












OCH


3


); 5.2 (s, 2H, OCH


2


); 7.1 (m,












1H, Py); 7.32 (m, 5H, benzyl); 7.7












(dd, 1H, Py); 8.35 (dd, 1H, Py)






5




Id




CH


3






CH


3






O




CH


3






2.1 (s, 3H, CH


3


); 2.2 (s, 3H, CH


3


);












2.89; 2.90 (in each case s, 3H,












NCH


3


); 3.95 (s, 3H, OCH


3


); 4.0 (s,












3H, OCH


3


); 6.95 (m, 1H, NH); 7.1 (m,












1H, Py); 7.65 (dd, 1H, Py); 8.3 (dd,












1H, Py)






6




Id




CH


3






CH


3






O




CH(CH


3


)


2






1.35 (d, 6H, 2xCH


3


); 2.1 (s, 3H,












CH


3


); 2.2 (s, 3H, CH


3


); 2.90; 2.92












(in each case s, 3H, NCH


3


); 3.95 (s,












3H, OCH


3


); 4.4 (m, 1H, CH); 6.85 (m,












1H, NH); 7.1 (m, 1H, Py); 7.65 (dd,












1H, Py); 8.35 (dd, 1H, Py)






7




Id




CH


3






CH


3






O




CH


2


C≡CH




2.1 (s, 3H, CH


3


); 2.2 (s, 3H, CH


3


);












2.5 (s, 1H, CH); 2.90; 2.92 (in each












case s, 3H, NCH


3


); 3.95 (s, 3H,












OCH


3


); 2.5 (s, 1H, CH); 4.8 (s, 2H,












OCH


2


); 6.75 (m, 1H, NH); 7.1 (m, 1H,












Py); 7.7 (dd, 1H, Py); 8.35 (dd, 1H,












Py)






8




Id




CH


3






CH


3






O




CH


2


—C


6


H


5






2.1 (s, 3H, CH


3


); 2.2 (s, 3H, CH


3


);












2.90; 2.92 (in each case s, 3H,












NCH


3


); 3.95 (s, 3H, OCH


3


); 5.22 (s,












2H, OCH


2


); 6.75 (m, 1H, NH); 7.1 (m,












1H, Py); 7.38 (m, 5H, benzyl); 7.64












(dd, 1H, Py); 8.36 (dd, 1H, Py)






9




Ic




CH


2


CH


3






CH


3






O




CH


3






1.1 (t, 3H, CH


3


); 2.1 (s, 3H, CH


3


);












2.75 (q, 2H, CH


2


); 3.84 (s, 3H,












OCH


3


); 4.0 (s, 3H, OCH


3


); 4.06 (s,












3H, OCH


3


); 7.12 (m, 1H, Py); 7.65












(dd, 1H, Py); 8.38 (dd, 1H, Py)






10




Ic




CH


2


CH


3






CH


3






O




CH(CH


3


)


2






1.12 (t, 3H, CH


3


); 1.3 (d, 6H,












2xCH


3


); 2.05 (s, 3H, CH


3


); 2.75 (q,












2H, CH


2


); 3.82 (s, 3H, OCH


3


); 4.06












(s, 3H, OCH


3


); 4.45 (m, 1H, CH); 7.1












(m, 1H, Py); 7.65 (dd, 1H, Py); 8.36












(dd, 1H, Py)






11




Ic




CH


2


CH


3






CH


3






O




CH


2


C≡CH




1.1 (t, 3H, CH


3


); 2.1 (s, 3H, CH


3


);












2.5 (s, 1H, CH); 2.75 (q, 2H, CH


2


);












3.86 (s, 3H, OCH


3


); 4.06 (s, 3H,












OCH


3


); 4.8 (s, 2H, OCH


2


); 7.14 (m,












1H, Py); 7.65 (dd, 1H, Py); 8.38












(dd, 1H, Py)






12




Id




CH


2


CH


3






CH


3






O




CH


3






1.1 (t, 3H, CH


3


); 2.06 (s, 3H, CH


3


);












2.75 (q, 2H, CH


2


); 2.90; 2.92 (in












each case s, 3H, NCH


3


); 3.94 (s, 3H,












OCH


3


); 4.0 (s, 3H, OCH


3


); 6.8 (m,












1H, NH); 7.1 (m, 1H, Py); 7.65 (dd,












1H, Py); 8.36 (dd, 1H, Py)






13




Id




CH


2


CH


3






CH


3






O




CH(CH


3


)


2






1.1 (t, 3H, CH


3


); 1.25 (d, 6H,












2xCH


3


); 2.05 (s, 3H, CH


3


); 2.75 (q,












2H, CH


2


); 2.90; 2.92 (in each case












s, 3H, NCH


3


); 3.94 (s, 3H, OCH


3


)












4.42 (m, 1H, CH); 6.8 (m, 1H, NH);












7.1 (m, 1H, Py); 7.65 (dd, 1H, Py);












8.36 (dd, 1H, Py)






14




Id




CH


2


CH


3






CH


3






O




CH


2


C≡CH




1.12 (t, 3H, CH


3


); 2.1 (s, 3H, CH


3


);












2.5 (s, 1H, CH); 2.75 (q, 2H, CH


2


);












2.90; 2.92 (in each case s, 3H,












NCH


3


); 3.96 (s, 3H, OCH


3


); 4.8 (s,












2H, OCH


2


); 6.8 (m, 1H, NH); 7.12 (m,












1H, Py); 7.65 (dd, 1H, Py); 8.35












(dd, 1H, Py)






15




Ic




CH


3






CH


3






O




CH


2


CH


3






1.3 (t, 3H, CH


3


); 2.1 (s, 3H, CH


3


);












2.2 (s, 3H, CH


3


); 3.82 (s, 3H,












OCH


3


); 4.06 (s, 3H, OCH


3


); 4.12 (q,












2H, OCH


2


); 7.1 (m, 1H, Py); 7.7 (dd,












1H, Py); 8.38 (dd, 1H, Py)






16




Id




CH


3






CH


3






O




CH


2


CH


3






1.3 (t, 3H, CH


3


); 2.1 (s, 3H, CH


3


);












2.2 (s, 3H, CH


3


); 2.90; 2.92 (in












each case s, 3H, NCH


3


); 3.95 (s, 3H,












OCH


3


); 4.25 (q, 2H, OCH


2


); 6.8 (m,












1H, NH); 7.1 (m, 1H, Py); 7.65 (dd,












1H, Py); 8.35 (dd, 1H, Py)






17




Ia




CH


3






CH


3






O




CH


2


CH


3






1.3 (t, 3H, CH


3


); 2.16 (s, 3H, CH


3


);












2.2 (s, 3H, CH


3


); 3.7 (s, 3H, OCH


3


);












3.84 (s, 3H, OCH


3


); 4.22 (q, 2H,












OCH


2


); 7.1 (m, 1H, Py); 7.58 (s, 1H,












CH); 7.6 (dd, 1H, Py); 8.25 (dd, 1H,












Py)






18




Ic




CH


2


CH


3






CH


3






O




CH


2


CH


3






1.1 (t, 3H, CH


3


); 1.3 (t, 3H, CH


3


);












2.1 (s, 3H, CH


3


); 2.75 (q, 2H, CH


2


);












3.85 (s, 3H, OCH


3


); 4.06 (s, 3H,












OCH


3


); 4.24 (q, 2H, OCH


2


); 7.1 (m,












1H, Py); 7.68 (dd, 1H, Py); 8.38












(dd, 1H, Py)






19




Ia




CH


2


CH


3






CH


3






O




CH(CH


3


)


2






1.1 (t, 3H, CH


3


); 1.15 (d, 6H,












2xCH


3


); 2.1 (s, 3H, CH


3


); 2.74 (q,












2H, CH


2


); 3.7 (s, 3H, OCH


3


); 3.84












(s, 3H, OCH


3


); 4.42 (m, 1H, CH); 7.1












(m, 1H, Py); 7.58 (m, 2H, 1xCH,












1xPy); 8.3 (dd, 1H, Py)














Ia=C[CO


2


CH


3


]=CHOCH


3


; Ib=C[CO


2


CH


3


]=CHCH


3


;




Ic=C[CO


2


CH


3


]=NOCH


3


; Id=C[CONHCH


3


]=NOCH


3






Py=pyridyl




Examples of the Action Against Harmful Fungi




The fungicidal function of the compounds of the general formula I was demonstrated by the following experiments:




The active ingredients were formulated, separately or jointly, as a 10% 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 Wettol® EM (nonionic emulsifier based on ethoxylated castor oil) and diluted with water to give the desired concentration.




Activity Against


Erysiphe graminis


var.


tritici


(powdery mildew of wheat)




Leaves of wheat seedlings (cultivar: “Frühgold”) were first treated with the aqueous preparation of the active ingredients (rate of application: 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 20-22° C. and a relative atmospheric humidity of 75-80%. The extent of fungal development was subsequently determined.




In this test, the infection level of plants which had been treated with the compounds 1, 3 and 7 according to the invention was 15% and less, while the infection level of the untreated (control) plants was 75%.




Activity Against


Plasmopara viticola


(downy mildew grapevines)




Grapevines in pots (cultivar: “Müller Thurgau”) were sprayed to run off with the preparation of active ingredient (rate of application: 250 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. Thereupon, prior to assessment, the plants were kept for 16 hours at high atmospheric humidity. The test was evaluated visually.




In this test, the infection level of the plants which had been treated with the compounds 1, 3 and 7 according to the invention was 15% and less, while the infection level of the untreated (control) plants was 70%.




Examples of the Action Against Animal Pests




The activity of the compounds of the general formula I against animal pests was demonstrated by the following experiments:




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 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 Wettol® EM (non-ionic emulsifier based on ethoxylated castor oil)




and diluted to give the desired concentration, 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 to 100% inhibition, or mortality, in comparison with untreated controls was determined (limit or minimal concentration).



Claims
  • 1. A pyridine compound of the formula I wherein:X is cyano, nitro, halogen, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy and C3-C6-cycloalkyl; n is 0, 1, 2 or 3, it being possible for the substituents X to be different when n is greater than 1; Y is oxygen or nitrogen, the nitrogen atom having attached to it a hydrogen atom or a C1-C4-alkyl group; R is C(CO2CH3)═CHCH3, C(CO2CH3)═CHOCH3, C(CO2CH3)═NOCH3, C(CONH2)═NOCH3 or C(CONHCH3)═NOCH3; R1 is hydrogen, hydroxyl, cyano, halogen, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkylthio, C3-C6-cycloalkyl, C3-C6-cycloalkyl-C1-C4-alkyl, aryl, aryl-C1-C4-alkyl, aryloxy-C1-C4-alkyl and aryl-C1-C4-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, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, and C(CH3)═N-A1-Ra; Ra is C1-C6-alkyl, A1 is oxygen or nitrogen, the nitrogen atom having attached to it a hydrogen atom or a C1-C4-alkyl group; R2 is unsubstituted or substituted alkenyl, or —Q—C(R3)═N-Y1-R4 where Q is a direct bond, CH2, CH(CH3), CH(CH2CH3) or 1,1-cyclopropyl; Y1 is oxygen or nitrogen, the nitrogen atom having attached to it a hydrogen atom or a C1-C4-alkyl group; R3 is one of the groups listed under R1, or unsubstituted or substituted cycloalkoxy, heterocyclyloxy, aryloxy, hetaryloxy, arylthio and hetarylthio; R4 is unsubstituted or substituted C1-C10-alkyl, C3-C6-cycloalkyl, C2-C10-alkenyl, C2-C10-alkynyl, C1-C10-alkylcarbonyl, C2-C10-alkenylcarbonyl, C2-C10-alkynylcarbonyl or C1-C10-alkylsulfonyl; unsubstituted or substituted aryl, hetaryl, arylcarbonyl, hetarylcarbonyl, arylsulfonyl or hetarylsulfonyl; or a salt thereof.
  • 2. A compound of the formula I as claimed in claim 1 wherein R2 is a substituted alkenyl, the substituents being from one to three of the following radicals has the following meanings:cyano, nitro, hydroxyl, mercapto, amino, carboxyl, aminocarbonyl, aminothiocarbonyl, C1-C6-alkylsulfonyl, C1-C6-alkylsulfoxyl, C1-C6-alkylcarbonyl, C3-C6-cycloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkoxycarbonyl, C1-C6-alkylthio, C1-C6-alkylamino, di-C1-C6-alkylamino, C1-C6-alkylaminocarbonyl, di-C1-C6-alkylaminocarbonyl, C1-C6-alkylaminothiocarbonyl, di-C1-C6-alkylaminothiocarbonyl, C2-C6-alkenyloxy, benzyloxy, aryl, aryloxy, hetaryl and hetaryloxy, wherein the aromatic ring are substituted or unsubstituted.
  • 3. A compound of the formula I as claimed in claim 1 where R2 is the group —C(R3)═N—Y1—R4 wherein:Y1 is O, NH or N(CH3); R4 is hydrogen, C1-C6-alkyl which optionally has attached to it one of the following groups: C1-C4-alkoxy, C3-C6-cycloalkyl which is unsubstituted or substituted or phenyl which is unsubstituted or substituted; C3-C6-alkenyl, C3-C6-haloalkenyl, C3-C6-alkynyl, C3-C6-haloalkynyl or C3-C6-cycloalkyl which is unsubstituted or substituted by customary groups, R3 is hydrogen, cyano, halogen, C1-C4-alkyl, C1-C2-haloalkyl, C1-C4-alkoxy, C1-C2-haloalkoxy or C3-C6-cycloalkyl.
  • 4. A compound of the formula I.8 as claimed in claim 1wherein:R is C(CO2CH3)═CHCH3, C(CO2CH3)═CHOCH3, C(CO2CH3)═NOCH3 or C(CONHCH3═NOCH3; X is cyano, halogen, C1-C4-alkyl, C1-C2-haloalkyl, C1-C4-alkoxy, C1-C2-haloalkoxy and C3-C6-cycloalkyl; n is 0 or 1; R1 is hydrogen, cyano, halogen, C1-C4-alkyl, C1-C2-haloalkyl, C1-C4-alkoxy, C1-C2-haloalkoxy and C3-C6-cycloalkyl; R3 is hydrogen, cyano, halogen, C1-C4-alkyl, C1-C2-haloalkyl, C1-C4-alkoxy, C1-C2-haloalkoxy and C3-C6-cycloalkyl; Y1 is O,NH or N(CH3); R4 is hydrogen, C1-C6-alkyl which may have attached to it one of the following groups: C1-C4-alkoxy, C3-C6-cycloalkyl which is unsubstituted or substituted by customary groups or phenyl which is unsubstituted or substituted; C3-C6-alkenyl, C3-C6-haloalkenyl, C3-C6-alkynyl, C3-C6-haloalkynyl or C3-C6-cycloalkyl which is unsubstituted or substituted by customary groups.
  • 5. A compound of the formula I as claimed in claim 1 where R2 is the group —C(Rx)═CRyRz with the following meanings:Rx is hydrogen, cyano, halogen, C1-C4-alkyl, C1-C2-haloalkyl, C1-C4-alkoxy, C1-C2-haloalkoxy and C3-C6-cycloalkyl; Ry is hydrogen, C1-C6-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: C1-C4-alkoxy, C3-C6-cycloalkyl which is unsubstituted or substituted by customary groups or phenyl which is unsubstituted or substituted; C1-C6-alkoxy, C1-C6-haloalkoxy, C3-C6-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; Rz is hydrogen, cyano, halogen, C1-C4-alkyl, C1-C2-haloalkyl and C3-C6-cycloalkyl, or Ry and Rx together with the double bond to which they are attached are C4-C6-cycloalkenyl.
  • 6. A compound of the formula I.12 as claimed in claim 1wherein:R is C(CO2CH3)═CHCH3, C(CO2CH3)═CHOCH3, C(CO2CH3)═NOCH3 or C(CONHCH3═NOCH3; X is cyano, halogen, C1-C4-alkyl, C1-C2-haloalkyl, C1-C4-alkoxy, C1-C2-haloalkoxy and C3-C6-cycloalkyl; n is 0 or 1; R1 is hydrogen, cyano, halogen, C1-C4-alkyl, C1-C2-haloalkyl, C1-C4-alkoxy, C1-C2-haloalkoxy and C3-C6-cycloalkyl; Rx is hydrogen, cyano, halogen, C1-C4-alkyl, C1-C2-haloalkyl, C1-C4-alkoxy, C1-C2-haloalkoxy and C3-C6-cycloalkyl; Ry is hydrogen, C1-C6-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: C1-C4-alkoxy, C3-C6-cycloalkyl which is unsubstituted or substituted by customary groups or phenyl which is unsubstituted or substituted; C1-C6-alkoxy, C1-C6-haloalkoxy, C3-C6-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; Rz is hydrogen, cyano, halogen, C1-C4-alkyl, C1-C2-haloalkyl and C3-C6-cycloalkyl, or Ry and Rx together with the double bond to which they are attached are C4-C6-cycloalkenyl.
  • 7. A compound as claimed in claim 1 where n is 0 or 1 and, when n is 1, X is fluorine, chlorine, methyl or trifluoromethyl.
  • 8. A compound as claimed in any of claim 1 where R1 is C1-C3-alkyl.
  • 9. A compound as claimed in claim 4 whereR3 is C1-C3-alkyl, Y1 is oxygen and R4 is C1-C4-alkyl, C3-C4-alkynyl or benzyl.
  • 10. A compound as claimed in claim 6 whereRx is C1-C4-alkyl, Ry is C1-C4-alkyl or phenyl which for its part may have attached to it one to three of the following radicals: halogen, C1-C4-alkyl or haloalkyl; and Rz is hydrogen.
  • 11. A compound of the formula I as claimed in claim 1 where the radical R and the group —Y—N═CR1R2 are bonded to two adjacent C atoms of the pyridyl ring.
  • 12. A process for the preparation of the pyridine compounds of the formula I as claimed in claim 1 where R is C(CO2CH3)═CHCH3, C(CO2CH3)═CHOCH3 or C(CO2CH3)═NOCH3, which comprises first converting a pyridinecarboxylic acid of the formula IIa where L1 is a nucleophilically exchangeable leaving group and R# is hydrogen or a C1-C4-alkyl group into the acid chloride IIb and subsequently into the acid cyanide IIc reacting IIc via a Pinner reaction to give the corresponding α-keto ester IIIa subsequently reacting IIIa with an oxime of the formula IV in the presence of a base to give the corresponding α-keto ester IIIb and subsequently converting IIIb eithera) with a Wittig or Wittig-Horner reagent of the formula Va CH3—O—CH2—P*  (Va) where P* is a phosphonate or a phosphonium halide radical into the corresponding compound Ia, [R=C(CO2CH3)═CHOCH3, or b) with a Wittig or Wittig-Horner reagent of the formula Vb CH3—CH2—P*  (Vb) into the corresponding compound Ib [R=C(CO2CH3)═CHCH3], or c) with O-methylhydroxylamine or a salt thereof (Vc) CH3—O—NH2CH3—O—NH3⊖Z⊕  (Vc) where Z− is a halide anion into the corresponding compound Ic, wherein R is C(CO2CH3)═NOCH3.
  • 13. A process for the preparation of the compounds Va and Vc as set forth in claim 12, which comprises converting a pyridine compound of the formula VI where L1 is a nucleophilically exchangeable leaving group and M is an organometallic radical with a compound VII where T is CH, CHO or NO and Hal is a halogen atom in the presence of a catalyst into the corresponding pyridine derivative of the formula VIII and subsequently reacting VIII with an oxime of the formula IV as set forth in claim 12 in the presence of a base to give Ia or Ic.
  • 14. A process for the preparation of the compounds I as claimed in claims 12 where R is C(CONHCH3)═NOCH3, which comprises converting a compound of the formula Ic as set forth in claim 12 with methylamine or a salt thereof (IX)CH3—NH2CH3—NH3⊕Z⊖  (IX) where Z− is a halide anion into the corresponding compound Id, wherein R is C(CONHCH3) NOCH3].
  • 15. A composition which is suitable for controlling animal pests or harmful fungi, comprising a solid or liquid carrier and a compound of the formula I as claimed in claim 1.
  • 16. A method of controlling harmful fungi, which comprises treating the fungi, or the materials, the 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.
  • 17. A method of controlling animal pests, which comprises treating 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 any of claim 1.
Priority Claims (1)
Number Date Country Kind
196 38 038 Sep 1996 DE
PCT Information
Filing Document Filing Date Country Kind 102e Date 371c Date
PCT/EP97/04710 WO 00 3/17/1999 3/17/1999
Publishing Document Publishing Date Country Kind
WO98/12179 3/26/1998 WO A
US Referenced Citations (3)
Number Name Date Kind
5633268 Kirstgen et al. May 1997
5780506 Bayer et al. Jul 1998
5889059 Bayer et al. Mar 1999
Foreign Referenced Citations (3)
Number Date Country
9506033 Mar 1995 WO
9521153 Aug 1995 WO
9521154 Aug 1995 WO
Non-Patent Literature Citations (1)
Entry
Chem. Abstracts, Kirstgen et al. 1995:220182, 122:9667.