CH630356A5 - Process for the preparation of 3-phenyl-5-(substituted)-4(1H)-pyridones, and their use - Google Patents

Description

The aim of the present invention was to produce new 3-phenyl-5-substituted-4 (1H) pyridones and also corresponding thiones which can be used in free form or in the form of their salts as active ingredient components of herbicidal compositions.

The present invention therefore relates to a process for the preparation of 3-phenyl-5-substituted-4 (1H) -pyridones of the formula Ia:

The present invention relates to a process for the preparation of 3-phenyl-5-substituted-4 (1H) -pyridones and their use. These new pyridones are used as active ingredient components in herbicidal compositions. These herbicidal agents can be used in agrochemicals as pre-emergence herbicides and post-emergence herbicides, and they are used to control weeds.

Weed control is a vital step in maximizing crop yields, and herbicides have therefore proven to be vital tools in agriculture, with a need for new and better herbicidal compounds.

Despite the great research effort in the field of agrochemistry, no active ingredients have been found to date, which are closely related to the compounds of the present formula I. The polyhalopyridones, the pyridine ring of which is substituted by two or more chlorine atoms and also other alkyl and halogen substituents, are known herbicides. However, they obviously differ considerably from the compounds of formula I.

In organic chemistry, the pyridones have been extensively worked on. For example, in J. Am. Chem. Soc. 95,3396-3397 (1973) describes a rearrangement of 3,5-diphenyl-1,2,6-trimethyl-4 (1 H) -pyridone. However, these compounds are not herbicides. In J. Am. Chem. Soc. 77, 1852-1855 (1955) states the synthesis of 3,5-dibenzyl-1-methyl-4 (1H) -pyridones, but these compounds also have no herbicidal activity. In J. Am.

Chem. Soc. 79, 156-160 (1957), the main author of the 65 last-mentioned work also describes 3,5-di (substituted-benzylidene) te-trahydro-4-pyridones. These compounds are also not herbicidally active.

R?

(Ia)

where X is oxygen,

R represents hydrogen, an alkyl radical with 1 to 3 carbon atoms, an alkyl radical with halogen, cyano, carboxy or methoxy-carbonyl substituted with 1-3 carbon atoms in the alkyl part, an alkenyl radical with 2 or 3 carbon atoms, an alkynyl radical with 2 or 3 carbon atoms, one Alkoxy radical having 1 to 3 carbon atoms, the hydroxyl or dimethylamino radical, with the proviso that the substituent R contains a total of no more than 3 carbon atoms,

the radicals R1 independently of one another halogen, alkyl groups with 1-8 carbon atoms, halogen-substituted alkyl groups with 1-8 carbon atoms, with phenyl, cyano or alkoxy groups with 1-3 carbon atoms monosubstituted alkyl radicals with 1-8 carbon atoms, alkenyl radicals with 2- 8 carbon atoms, halogen-substituted alkenyl radicals with 2-8 carbon atoms, alkynyl radicals with 2-8 carbon atoms, halogen-substituted alkynyl radicals with 2-8 carbon atoms, cycloalkyl radicals with 3-6 carbon atoms, cycloalkenyl radicals with 4-6 carbon atoms, cycloalkylalkyl radicals with 4-8 carbon atoms, alkanoyloxy radicals with 1-3 carbon atoms, alkylsulfonyloxy radicals with 1-3 carbon atoms, phenyl radicals, phenyl radicals monosubstituted by halogen, alkyl with 1-3 carbon atoms, alkoxy with 1-3 carbon atoms or nitro, nitro, cyano, carboxy or hydroxy groups, Alkoxycarbonyl groups with 1-3 carbon atoms, or groupings of the formulas: -O-R3, -S-R3, -SO-R3 or S02-R3 be interpret

630 356

10th

wherein R3 is an alkyl radical having 1-12 carbon atoms, halogen-substituted alkyl radical having 1-12 carbon atoms, by phenyl, cyano or an alkoxy group having 1-3 carbon atoms, monosubstituted alkyl radical having 1 to 12 carbon atoms, a phenyl radical, one by halogen, alkyl with 1-3 carbon atoms, alkoxy with 1-3 carbon atoms or nitro monosubstituted phenyl radical, a cycloalkyl radical with 3-6 carbon atoms, a cycloalkylalkyl radical with 4-8 carbon atoms, an alkenyl radical with 2-12 carbon atoms, a halogen-substituted alkenyl radical with 2-12 carbon atoms, an alkynyl radical with 2-12 carbon atoms or a halogen-substituted alkynyl radical with 2-12 carbon atoms, with the proviso that the radical R3 contains a maximum of 12 carbon atoms,

R2 for halogen, hydrogen, an alkoxycarbonyl group with 1-3 carbon atoms, an alkyl group with 1-6 carbon atoms, an alkyl group with 1-6 carbon atoms substituted by halogen or alkoxy with 1-3 carbon atoms, an alkenyl group with 2-6 carbon atoms, one with Halogen or alkoxy with 1-3 carbon atoms substituted alkenyl group with 2-6 carbon atoms, an alkynyl group, a cycloalkyl group with 3-6 carbon atoms, a cycloalkyl group with 3 substituted by halogen, alkyl with 1-3 carbon atoms or alkoxy with 1-3 carbon atoms -6 carbon atoms, a cycloalkenyl radical with 4-6 carbon atoms, a cycloalkylalkyl radical with 4-8 carbon atoms, a phenyl-substituted alkyl radical with 1-3 carbon atoms in the alkyl group, a furyl, naphthyl or thienyl radical, a grouping of the formulas:

-O-R4, -S-R4, -SO-R4 or -S02-R4,

wherein R4 represents an alkyl radical with 1-3 carbon atoms, a halogen-substituted alkyl radical with 1-3 carbon atoms, an alkenyl radical with 2 or 3 carbon atoms, a halogen-substituted alkenyl radical with 2 or 3 carbon atoms, a benzyl or phenyl radical, or one with halogen, alkyl phenyl radical substituted with 1-3 carbon atoms or alkoxy with 1-3 carbon atoms, or the radical R2 is a phenyl radical of the formula:

an alkyl group monosubstituted by phenyl, cyano or an alkoxy group having 1-3 carbon atoms, a phenyl group, one monosubstituted by halogen, an alkyl group having 1-3 carbon atoms, an alkoxy group having 1 to 3 carbon atoms or a nitro group Phenyl group, a cycloalkyl group of 3-6 carbon atoms, a cycloalkylalkyl group of 4-8 carbon atoms, an alkenyl group of 2-12 carbon atoms, a halogen-substituted alkenyl group of 2-12 carbon -10 atoms, an alkynyl group of 2-12 carbon atoms or a halogen-substituted alkynyl group 2-12 carbon atoms, with the proviso that the substituent R6 contains at most 12 carbon atoms,

and the indices m and n independently of one another represent 0.1 or 2 15, but the index m stands for 1 or 2 if R represents a hydrogen atom or a methyl group and R2 is also an unsubstituted phenyl radical,

or of salts of the compounds of the formula Ia. The corresponding compound of the formula Ia, in which m is 20 = 0, R2 is an unsubstituted phenyl radical and R is a hydrogen atom, namely 3,5-diphenyl-4 (1H) -pyridone, is already known from the publication of Benary and Bitter in Ber. 61, 1058 (1928). The corresponding 1-methyl derivative, namely 3,5-diphenyl-25 l-methyl-4 (1H) -pyridone, has already been described in the literature.

The process according to the invention for the preparation of the new pyridones of the formula Ia is characterized in that a compound of the formula IV

30th

35

IV

is where the residues

Rs independently of one another halogen, alkyl groups with 1-8 carbon atoms, halogen-substituted alkyl groups with 1-8 carbon atoms, alkyl groups with 1-8 carbon atoms monosubstituted by phenyl, cyano or alkoxy with 1-3 carbon atoms, alkenyl groups with 2-8 carbon atoms, halogen-substituted Alkenyl groups with 2 to 8 carbon atoms, alkynyl groups with 2 to 8 carbon atoms, halogen-substituted alkynyl groups with 2-8 carbon atoms, cycloalkyl groups with 3-6 carbon atoms, cycloalkenyl groups with 4-6 carbon atoms, cycloalkylalkyl groups with 4-6 carbon atoms, alkanoyloxy groups with 1-3 Carbon atoms, alkylsulfonyloxy groups with 1 to 3 carbon atoms, phenyl, phenyl groups substituted by halogen, alkyl with 1-3 carbon atoms, alkoxy with 1-3 carbon atoms, or nitro, cyano, carboxy or hydroxyl groups, alkoxycarbonyl groups with 1 to 3 carbon atoms or Groupings of the formulas:

-O-R6, -S-R6, -SO-R6 or-S02-R6

mean what

R6 is an alkyl group with 1-12 carbon atoms, a halogen-substituted alkyl group with 1-12 carbon atoms,

in which

R1, R2 and m have the meaning given in formula Ia, one of the substituents Q1 or Q2 represents two hydrogen -40 atoms, and the other of the two substituents Q1 and Q2 denotes a radical of the formula = CH-NHR,

wherein R has the same meaning as in formula Ia, cyclized with a formylating agent.

The formylating agents which are preferably used in carrying out the process according to the invention are esters of formic acid and of these the corresponding ethyl ester, namely the ethyl formate, is very particularly preferred.

If, when carrying out the process according to the invention, such a starting material of the formula IV is used in which R is a hydrogen atom, that is to say that one of the two radicals Q1 or Q2 stands for a grouping of the formula = CH-NH2, the end product obtained is corresponding pyridone of the formula Ia, in which R is a hydrogen atom. These compounds can then be converted into those compounds of formula Ia in which R is an alkyl radical having 1 to 3 carbon atoms, an alkyl radical having 1 to 3 carbon atoms substituted by halogen, cyano, carboxy or methoxycarbonyl, an alkenyl radical having 2 or 3 Carbon atoms or an alkynyl radical with 2 or 3 carbon atoms is by introducing the corresponding radical on the nitrogen atom by the N-alkylation method.

The N-alkylation of the corresponding compound of the formula Ia, in which R is a hydrogen atom, can be carried out by introducing the corresponding substituent R 65 with a halide or, in the case of corresponding alkyl radicals, with a dialkyl sulfate.

The subsequent alkylation on the nitrogen atom can, however, also be carried out by the appropriate

11

630 356

1-Unsubstituted pyridone of the formula I a first converted into the corresponding 4-halogen derivative or the corresponding 4-alkoxy derivative by reaction with a halogenating agent or an alkylating agent. POCl3, POBr3 or PC15 are suitable as halogenating agents for this purpose. Examples of suitable O-alkylating agents are methyl trifluoromethanesulfonate or methyl fluorosulfonate, and also alkyl halides in the presence of a base. In the next step, the 4-halogen or 4-alkoxy compound is then reacted with a halide of the substituent R, which produces the 1-R-substituted-4-substituted-pyridinium salt. The salt obtained is then hydrolyzed with either a mineral acid or an alkali metal hydroxide to form the desired product. For more details, see Pharm. Bull. (Japan) 1,70-74 (1953).

If, when carrying out the process according to the invention, a starting material of the formula IV is used in which R is a hydroxyl group, then a corresponding pyridone of the formula Ia in which R is also a hydroxyl radical is obtained. This product can then be esterified, for example subjected to acetylation, a corresponding 3-phenyl-5-substituted-4 (1H) ~ pyridone of the formula V being used

(V)

a '■

receives what

R 'is an acetoxy radical, and the radicals R1, R2 and m have the same meaning as in formula Ia, and it is of course also possible to prepare a salt of the compound of the formula V.

In preferred compounds of the formula Ia prepared by the process according to the invention, the substituent R1 is in the m position of the benzene nucleus, and these compounds therefore have the following formula III:

0 II

/ V »-

X

>

III

v i

R

on, with the remains

R, R1 and R2 have the same meaning as in formula

Yes.

Of these compounds of the formula III, those in which the radical R1 has the meaning of a trifluoromethyl group are particularly preferred.

Further preferred pyridones of the formula Ia prepared by the process according to the invention have the following structure:

where X is oxygen,

R ° represents Q-Q-alkyl, Q-Q-alkenyl, acetoxy or methoxy,

q and p independently of one another represent 0.1 or 2, 5 the radicals R7 independently represent halogen, Q-Q-alkyl, trifluoromethyl or Q-Q-alkoxy,

the radicals Rs are independently halogen, QQ-alkyl, trifluoromethyl or QQ-alkoxy or two radicals Rs are in the o- and m-positions adjacent to one another xo and together with the phenyl ring to which they are attached, a 1- Form naphthyl group.

In the above formulas, the general chemical terms are used in their normal meanings. The information QQ-alkyl, QQ-alkenyl, QQ-alkynyl, QQ-15 alkoxy, QQ-alkyl, QQ-alkenyl, QQ-alkynyl, QQ-alkyl, QQ-alkenyl and QQ-alkynyl relate, for example, to residues such as methyl , Ethyl, isopropyl, vinyl, al-lyl, methoxy, isopropoxy, propargyl, isobutyl, hexyl, octyl, 1,1-dimethylpentyl, 2-octenyl, pentyl, 3-hexinyl, l-ethyl-2-20 hexenyl, 3- Octynyl, 5-heptenyl, l-propyl-3-butynyl and crotyl.

Q-Q-cycloalkyl and Q-C5-cycloalkenyl are understood to mean, for example, radicals, such as cyclopropyl, cyclobutyl, cyclohexyl, cyclobutenyl, cyclopentenyl and cyclohexadienyl.

The statement Q-Q-cycloalkylalkyl refers to radicals, such as cyclopropylmethyl, cyclobutylmethyl, cyclohexylmethyl and cyclohexlethyl.

Q-Q-alkanoyloxy is understood to mean residues such as formyloxy, acetoxy and propionyloxy.

The information Q-Q-ÀIkoxycarbonyl refers, for example, to residues such as methoxycarbonyl, ethoxycarbonyl and isopropoxycarbonyl.

Q-Q-alkylsulfonyloxy means residues such as methylsulfonyloxy and propylsulfonyloxy.

The term halogen preferably means fluorine, chlorine, 35 bromine and iodine.

The compounds described above can form salts, for example acid addition salts. The preferred salts are the hydrohalides, such as the hydroiodides, hydrobromides, hydrochlorides and hydrofluorides. Salts of sulfonic acids are also particularly suitable. Such salts include, for example, the sulfonates, methyl sulfonates and toluenesulfonates.

The formylating agents used in the process according to the invention can be selected from the agents usually used for such reactions. The preferred agents are esters of formic acid of the formulas

H — C ~ 0 ^ - (C1-Cs alkyl) or

50

55

Si

\ y

60

II,

Similar formylations are discussed in Organic Syntheses 300-302 (Anthology III, 1955).

The esters are generally used in the presence of strong bases, of which alkali alkoxides are preferred, such as sodium methoxide, potassium ethoxide or lithium propoxide. However, other bases can also be used, such as alkali metal hydrides or alkali amides, or else inorganic bases, such as alkali metal carbonates or alkali metal hydroxides. Strong organic bases such as diazabicyclononane and diazabicycloundecane are also suitable.

Reactions with formylating agents can be carried out in aprotic solvents, as are normally used in chemical syntheses. The normally preferred solvent is ethyl ether. As a solution

630 356

12

Formylation agents can in general be ethers, for example solvents such as tetrahydrofuran, ethyl butyl ether, 1,2-dimethoxyethane and tetrahydrofuran, aromatic solvents such as benzene or xylene, and alkanes such as hexane or octane.

Because of the strong bases generally used for the formylation reactions, the best results can be obtained at low working temperatures. Reaction temperatures in the range of about -25 ° C to about 10 ° C are preferred. The reaction mixture can also be allowed to reach ramp temperature after the reaction has partially ended. In order to achieve economic yields in the formylation reactions, reaction times of from about 1 to about 24 hours are generally sufficient.

As already mentioned, a starting material of the formula IV is used to carry out the process according to the invention

A

\ _ /

0 II

C — R2 II

9T

IV

in which one of the substituents Q1 or Q2 represents two hydrogen atoms and the other of the two substituents Q1 and Q2 denotes a radical of the formula = CH-NHR,

where R has the same meaning as in formula I.

So if in this starting material of formula IV the substituent Q1 stands for the nitrogenous group mentioned and the substituent Q2 has the meaning of two hydrogen atoms, then this enamine ketone has the following formula XI:

XI

HNCH

Sees ketone intermediate of formula IX, one of the two ^> CH2 groups of the starting product of the formula VHI is converted into the grouping of the formula ^> C = CH, while the other of the two CH2-

5 I

OH

Groups are preserved. The intermediate product of formula IX mentioned here represents only one of the two possible substitutions, and depending on the activating properties of the sub-io substituents R1 or R2 of the starting material, the other of the two CH2 groups mentioned can also be substituted during the formylation . However, this is irrelevant for the continuation of the production of the starting material, because it is only necessary that one of the two radicals Q1 or Q2 stands for two 15 hydrogen atoms, while the other must represent the formylated grouping mentioned.

The ketone intermediate of the formula IX is then reacted with ammonia or an amine of the formula RNH2, giving the ena-20 minketone of the formula XI required as the starting product, or the corresponding analogue compound in which the rest Q1 is two hydrogen atoms , while the rest Q2 represents the nitrogenous grouping.

The ketones of the formula VIII required for the preparation of the starting material of the formula IV 25 are 2-propanones, and these can be prepared by syntheses known from the literature. For example, reference is made to the following literature: Coan et al., J. Am. Chem. Soc. 76.501 (1954); Sullivan et al., Disodium Tetracarbonylferrate, Ame-30 Ricican Laboratory 49-56 (June 1974); Collman et al., "Synthesis of Hemifluorinated Ketones Using Disodium Tetracarbonylferrate", J. Am. Chem. Soc. 95, 2689-91 (1973); Collman et al., "Acyl and Alkyl Tetracarbonylferrate Complexes as Interme-diates in The Synthesis of Aldehydes and Ketones", J. Am. 35 Chem. Soc. 94, 2516-18 (1972).

Furthermore, the present invention also relates to the preparation of the pyridothiones constructed analogously to the pyridones of the formula Ia, that is to say the following formula Ib

The preparation of this starting material of formula XI can be carried out by using a ketone of formula VIII

ok

> —CH —0 — CH -

/ B 2

VIII

45

I -R2

(Ib)

with a formylating agent, whereby a ketone intermediate of the following formula IX

Ri

\ ï

> —C — G — CH —Ra / II

* HIGH

IX

receives.

To carry out this formylation reaction, the same formylation reagents can be used as were explained above in connection with the process according to the invention for producing the desired end products of the formula Ia. Preferred formylating agents are therefore the esters of formic acid mentioned and the formylation is expediently carried out under the same conditions as were explained above in connection with the preparation of the end products.

How to match from a comparison of Formula VIII with that.

In these pyridothions of the formula Ib, the radicals R, so R1 and R2, have the same meaning as in the corresponding pyridones of the formula Ia, and m can also be 0.1 or 2. In this case, however, m may also be 0 if R is a hydrogen atom or a methyl group and R2 is also an unsubstituted phenyl radical, because these sulfur-55 compounds mentioned are also new compounds.

The process according to the invention for the preparation of the pyridothione of the formula Ib and the salts thereof is characterized in that a compound of the formula IV

60

IV

65

in which

R1, R2 and m have the meaning given in formula Ia, one of the substituents Q1 or Q2 for two hydrogen

13

630 356

stands for atoms, and the other of the two substituents Q1 and Q2 denotes a radical of the formula = CH-NHR,

wherein R has the same meaning as in formula Ia, with a formylating agent to give a compound of formula Ia

(Ia)

R

cyclized, and reacted with phosphorus pentasulfide to the compounds of formula Ib.

This two-stage process can be used, for example, to prepare 3,5-diphenyl-1-methyl-4 (1H) -pyridinthione by adding 2,4-diphenyl-1-methylamino-1-buten-3-one with ethyl formate to the 3,5-Diphenyl-l-methyl-4 (1H) -pyridone cyclized, and this treated with phosphorus pentasulfide.

Furthermore, the l-methyl-3-phenyl-5- (3-tri-fluoromethylphenyl) -4 (lH) -pyridothione can be prepared by preparing a starting material from l-methylamino-2-phenyl-4- (3-tri -fluoromethylphenyl) -l-buten-3-one and / or l-methylamino-4-phenyl-2- (3-trifluoromethylphenyl) -l-buten-3-one with ethyl formate to give the l-methyl-3-phenyl-5 - (3-trifluoromethylphenyl) -4 (1H) -pyridone cyclized, and treated with phosphorus pentasulfide.

Furthermore, the present invention relates to the use of the new 3-phenyl-5-substituted-4 (1H) -pyridones of the formula Ia, or the corresponding pyridothiones of the formula Ib, which therefore have the following formula I:

y / vP

/

, x_

\ /

/ V

\

X

30th

(i)

R

have in which

X is an oxygen atom or a sulfur atom,

R, R1 and R2 have the same meaning as in formula Ia or Ib, and the indices m and n independently of one another represent 0.1 or 2, where the index m stands for 1 or 2 if R is a hydrogen atom or a methyl group is, and furthermore X represents an oxygen atom, and furthermore R2 represents an unsubstituted phenyl radical, or of salts of the compounds of the formula I, as active ingredient of a herbicidal composition.

The active ingredient components of the formula I are again those which have the following formula II:

X II

II

correspond, being in this formula

X represents an oxygen atom or a sulfur atom,

R ° represents an alkyl radical with 1-3 carbon atoms, an alkenyl radical with 2 or 3 carbon atoms or a meth-5 oxy group, and p and q are identical or different, and mean 0.1 or 2, the radicals R7 are identical or different and represent halogen, alkyl groups with 1-3 carbon atoms, trifluoromethyl groups or alkoxy groups with 1 to 3 carbon atoms, 10 the radicals R8 are identical or different and halogen, alkyl groups with 1-3 carbon atoms, trifluoromethyl groups or alkoxy groups with 1-3 Are carbon atoms, or two radicals R8 which are adjacent to one another in the o- and m-positions and together with the phenyl ring to which they are attached form an 1-naphthyl group.

The compounds of the formula I in which X is an oxygen atom and the substituent R1 is bonded in the m-position of the benzene nucleus, and in particular have the meaning of a trifluoromethyl group, are very particularly preferred as active ingredient component.

The pyridones of the formula Ia or pyridothiones of the formula Ib which can be prepared by the processes according to the invention can be converted into the corresponding salts by treatment with an acid or a base.

25th

The following compounds may be mentioned as examples of pyridones of the formula Ia or their salts which can be prepared by the process according to the invention:

3- (2,6-dimethylphenyl) -l-isopropyl-5- (l-naphthyl) -4 (lH) -py-ridone,

3- (4-methylphenyl) -5-phenyl-1-vinyl-4 (1H) -pyridone-hydrojo-did,

3- (3,5-difluorophenyl) -l-methoxy-5-phenyl-4 (lH) -pyridone, l-propyl-3- (4-trifluoromethylphenyl) -5- (3-trifluoromethylphe-35 nyl) -4 ( lH) -pyridone,

3- (2,6-difluorophenyl) -5- (3-iodophenyl) -1-vinyl-4 (1H) pyridone

3- (3,5-dibromophenyl) -5- (3-isopropoxyphenyl) -l-propyl-

4 (1H) pyridone

3- (3-bromophenyl) -l-methyl-5-phenyl-4 (1H) -pyridone 3- (4-chlorophenyl) -5- (2,4-dimethoxyphenyl) -l-propyl-4 (1H) -pyridone 1- (acetoxy-3- (4-chlorophenyl) -5- (1-naphthyl) -4 (1H) pyridone 3- (4-ethoxy-2-fluorophenyl) -1-methoxy-5-phenyl-4 (1H ) -pyridone l-allyl-3,5-bis (3-ethyl-4-methoxyphenyl) -4 (1H) -pyridone 3- (3-chlorophenyl) -5- [2,4-bis (trifluoromethyl) phenyl ] -l-meth-oxy-4 (1H) pyridone

3-benzyloxy-l-chloromethyl-5- (3-ethynylphenyl) -4 (1H) pyridone

3-Benzylthio-l- (2-bromoethyl) -5- (2,4-dimethylpehnyl) -4 (1H) pyridone

3-BenzyIsulfinyI-l-ethyI-5- (3-fIuor-5-propyIphenyl) -4 (lH) -pyridone

3-benzylsulfonyl-5- (3-octylphenyl) -l-propyl-4 (1H) -pyridone 55 3- (2-butylphenyl) -l-trifluoromethyl-4 (1H) -pyridone-hydrobro-mid

3- (3-Hexylphenyl) -l-methyl-5- (2-methylphenyl) -4 (1H) -pyridone l- (3,3-dibromopropyl) -3- (2,4-dichlorophenyl) -5- methyl-4 (1H) pyridone

3- (2,4-dimethylphenyl) -5-methoxycarbonyl-l-methyl-4 (1H) -pyridone l-methyl-3- [3- (l-propyleptyl) phenyl] -5-propyl-4 (1H) - pyri-don

65 1 - (2-Cyanoethyl) -3- (3-octyl-4-methylphenyl) -5-propoxycar-bonyl-4 (1H) pyridone

3- [3- (2-ethylpentyl) phenyl] -1-carboxymethyl-5- (3-trifluoromethylphenyl) -4 (1 H) pyridone

40

50

60

630 356

3- (2-chloromethylphenyl) -l-methoxycarbonylmethyl-4 (1H) pyridone

3- (3,5-diethylphenyl) -1-propargyl-5- [3- (5,5-dibromopentyl) phenyl] -4 (1 H) pyridone

3- (2,4-Dipropylphenyl) -l-methyl-5-trifluoromethyl-4 (1H) -pyridone

3 - (4-Benzylphenyl) -1 - ethoxy-5 - (2-fluoroethyl) -4 (1 H) -py ridone 3- (3-chloro-2-methoxyphenyl) -5 - (1,1 -dibrompentyl) - 1-methyl-4 (1H) pyridone

3- (3-Hexylphenyl) -5-methoxymethyl-l-methyl-4 (1H) -pyridone l-methyl-3- [4- (4-phenylhexyl) phenyl] -5- (3-propylphenyl) -

4 (1H) pyridone

3- (6-ethoxyhexyl) -5- (3-ethyl-5-iodophenyl) -1- (3-iodopropyl) -4 (1H) pyridone

3- [4- (8-Cyanooctyl) phenyl] -1-methyl-5- (2-pentenyl) -4 (1H) pyridone

3- (2,2-dichlorovinyl) -l-methyl-5- [3- (3-propoxyheptyl) -phe-nyl] -4 (1 H) -py ridone

3- (2-bromo-l-butenyl) -5- [3- (6-ethoxyheptyl) phenyl] -1-ethoxy-4 (1H) pyridone

3- (4-ethoxy-2-pentenyl) -5- [2- (2,4-hexadienyl) phenyl] -1-methoxy-4 (1H) -pyridone 1-methoxycarbonylmethyl-3- [3- (3-octenyl ) phenyl] -5-phenyl-4 (1H) pyridone methanesulfonate

3- (2-butynyl) -5- (2,4-diiodophenyl) -l-ethoxy-4 (1H) -pyridone

3- [4- (2,6-dibromo-2-heptenyl) phenyl] -1,5-dimethyl-4 (1H) -py-

ridon

3- (2-Hexenyl) -l-methyl-5- [3- (l, l, 2,2-tetrachloro-4-octenyl) phenyl] -4 (lH) pyridone

3-Cyclobutyl-5- [4- (2-iodovinyl) phenyl] -l-propoxy-4 (lH) -pyridone l- (l-carboxyethyl) -3- (2-chlorocyclopropyl) -5- [3- (3-chloropropargyl) phenyl] -4 (1H) pyridone

3- [4- (l, l-dibromo-4-pentynyl) phenyl] -l-isopropoxy-5- (2-methylcyclobutyl) -4 (lH) pyridone

3- (2,4-Diiodocyclopentyl) -1-ethyl-5- [4- (2-octynyl) phenyl] -4 (1H) pyridone

3- [2- (l, l-dichloro-4-heptinyl) phenyl] -5- (4-methoxycyclohexyl) -l-methoxy-4 (lH) pyridone

3- (3-Cyclohexenyl) -5- (3-cyclohexylphenyl) -l-dimethylaimno-4 (1H) -pyridone

3- [4- (1-Cyclobutenyl) phenyl] 5-methoxy-1-vinyl-4 (1H) -pyri-don-toluenesulfonate

3- [4- (2-Cyclohexenyl) phenyl] -5-isopropoxy-1-trifluoromethyl-4 (1H) -pyridone 1-dichloromethyl-3- (2-iodoethoxy) -5- (4-isopropylsulfonyloxyphenyl) -4 (lH) pyridone

3-allyloxy-5- [4- (2-chlorophenyl) phenyl] -1-isopropyl-4 (1H) pyridone hydrochloride

3- (2,2-dichlorovinyloxy) -5- [2- (3-iodophenyl) phenyl] -1-methyl-4 (1H) pyridone

3- (2-bromoallyloxy) -5- [3- (3-bromophenyl) phenyl] -l-vinyl-4 (1H) -pyridone l-allyl-3- [4- (2-methylphenyl) phenyl] -5- (3,3,3-trifluoro-1-pro-penyloxy-4 (1H) pyridone 1-methoxy-3-phenoxy-5- [3- (4-propylphenyl) phenyl] -4 (1H) pyridone

3- (2-chlorophenoxy) -5- [4-methoxyphenyl) phenyl] -l-propargyl-4 (1 H) -pyridone

3- (4-bromophenoxy) -5- [4- (2-ethoxyphenyl) phenyl] -l-ethyl-4 (1H) pyridone

3- (2-iodophenoxy) -5- [3- (4-isopropoxyphenyl) phenyl] -l-meth-oxycarbonylmethyl-4 (1H) -pyridone l-methyl-3- (4-nitrophenyl) -5- (3- propylphenoxy) -4 (lH) pyridone

3- (4-cyanophenyl) -l-ethoxy-5- (2-methoxyphenoxy) -4 (1H) -pyridone

3- (3-Carboxyphenyl) -5- (2-ethoxyphenoxy) -l-isopropyl-4 (1H) -pyridone hydrofluoride l- (2-carboxyethyl) -3- (4-hydroxyphenyl) -5- (3-propoxyphene -oxy) -4 (1 H) -pyridone

53-benzyl-5- (2-methoxycarbonylphenyl) -l-methyl-4 (1H) -pyridone l-dimethylamino-3- (3-phenylpropyl) -5- (4-propoxycarbonyl) -phenyl) -4 (l H) pyridone

3- (3-butoxyphenyl) -5- (2-furyl) -l-trifluoromethyl-4 (1H) -pyri-îo don

3- (l-ethylpentyl) -5- (3-furyl) -l-methyl-4 (1H) pyridone

3- [4- (2-propylhexyloxy) phenyll-l-methoxycarbonylmethyl-5-

(2-thienyl) -4 (1H) pyridone 1-methyl-3- [4- (2-propylnonyloxy) phenyl] -5- (4-trifluoromethyl-15 phenyl) -4 (1H) pyridine thione 3-3, 5-diethylphenyl) -l-ethyl-5- (4-trifluoromethoxyphenyl) -4 (1H) -pyridinethione

3- [3- (5,5-Dibromopentoxy) phenyl] -5- (3,5-dicyclopropylphenyl) -l-ethyl-4 (1H) -pyridone 2o3- (2,6-dinitrophenyl) -l-methoxy -5- [5-phenylpentoxy) phenyl] -4 (1H) pyridone

3- (4-Butoxy-2-difluoromethylphenyi) -l-cyanomethyl-5- [3- (6-methoxyhexyloxy) phenyl] -4 (1H) -pyridone 3- (2-cyclohexyl-4-ethylphenyl) -l-methoxycarbonylmethyl -5-25 [2- (6-propoxynonyloxy) phenyl] -4 (1H) pyridone 3- (2,4-diallyloxyphenyl) -1- (2,2-dichloropropyl) -5- (2-methyl-6 -nitrophenyl) -4 (1H) -pyridone l-allyl-3- (4-cyano-3-ethoxycarbonylphenyl) -5- [4- (4,4,4-tri-fluoro-2-butenyloxy) phenyl] -4 (1H) -pyridone 3-ethoxy-3- [3- (9-iodo-1-nonenyloxy) phenyl] -5-phenyl-4 (1H) -pyridone

3- [3- (4-Chloro-2-butynyloxy) phenyl] -l-ethoxy-5- (3-fluoro-4-iso-butoxyphenyl) -4 (1H) -pyridone l-acetoxy-3- (2, 4-dibromophenyl) -5- [3- (l, l, 2,2-tetrafluoro-3-35 decinyloxy) phenyl] -4 (lH) pyridone 3- [2- (10-dodecinyloxy) phenyl] -l- methyl-5- (2-propyl-4-propylsulfonyloxyphenyl) -4 (1H) pyridone 3- (2,4-di (3-pentenyl) phenyl] -5- (3-phenoxyphenyl) -l- (1 , 1,2,2-tetrafluoroethyl) -4 (1H) -pyridone 40 l- (3-chloropropyl) -3- (3-cyanomethyl-5-ethylphenyl) -5- [3- (3-iodophenoxy) phenyl] - 4 (1H) pyridone

3- (3-Octyl-4-fluorophenyl) -5- [2- (3-ethylphenoxy) phenyl] -1-tri-fluoromethyl-4 (1H) pyridone

3- (2-ethyl-4-propylsulfonyloxyphenyl) -l-ethynyl-5- [2- (4-iso-45 propylphenoxy) phenyl] -4 (1 H) -pyridone l-carboxymethyl-3- (2,4- dinonyloxyphenyl) -5- [3- (4-methoxyphenoxy) phenyl] -4 (1H) pyridone

3- (3-chloro-4-heptylthiophenyl) -5- [3- (4-cyanopentyl) phenyl] -l-methyl-4 (1H) -pyridone 50 l-methyl-3-phenyl-5- [2- ( 3-ethylhexylthio) phenyl) -4 (1H) -py-ridone hydrofluoride

3- (2-chloro-4-ethylphenyl) -l-ethyl-5- (3-nonylthio-4-vinylphenyl) -4 (lH) -pyridone l-ethynyl-3-phenyl-5- [3- ( 2-ethylpentylthio) phenyl] -4 (1H) -py-55 ridone

3- (2-Cyano-4-hydroxyphenyl) -l-dimethylamino-5- [3- (5,5-di-brompentlythio) -4-nitrophenyl] -4 (1H) -pyridone 3- [4- (4, 4-Diiodododylthio) phenyl] -l-methyl-5-phenyl-4 (1H) pyridone

60 3- [4- (6-Cyanoheptylthio) phenyl] -1-fluoromethyl-4 (1H) pyridone

3- (3-Acetoxy-5-ethylphenyl) -5- [2- (8-cyanoundecylthio) -phenyl] -l-chlorodifluoromethyl-4 (1H) -pyridone 3- (4-benzyl-2-ethoxyethoxyphenyl) - 1- (2-carboxyethyl) -5- [3-65 (2-ethoxyethoxy) -5-propargylphenyl] -4 (1H) -pyridone-toluenesulfonate l-isopropenyl-3 [3- (3-phenylpentyl) phenyl] -5- [4- (6-isopropoxynonylthio) phenyl] -4 (1H) pyridone

3- (2-Cyanomethyl-4-vinylthiophenyl) -1-ethyl-5- [2- (7-phenyl-heptyl) phenyl] -4 (1 H) -pyridone

3- (3-allylthio-4-methoxymethylphenyl) -5- [2- (6-cyanohexyl) -

4-vinylphenyl] -l-methyl-4 (1H) -pyridone 3- [3- (2-decenylthio) -5- (2,4-hexadienyl) phenyl] -l-ethoxy-5-phenyl-4 (1H ) -pyridone

3- [4- (1,1-dichloroalylthio) phenyl] -5- [3- (4-octenyl) -2-propylphenv I] -1-trif Iuormethyl-4 (1 H) -pyridone 3- (4th ~ Carboxy-2-hydroxyphenyl) -5- [3- (2-chloro-3-butenylthio) -

5-nitrophenyl] -l-vinyl-4 (1 H) -pyridone 3- [4- (5,5-dibromo-3-heptenylthio) phenyI] -l-methyl-5-phenyl-4 (1H) -pyridone

3- [2- (l-chloropropylthio) phenyl] -1-dimethylamino-5- [3- (4-pentenyl) -5-methoxycarbonylphenyl] -4 (1H) pyridone 3- [4- (3,3-dibromo -5-hexynylthio) phenyI] -l-methoxy-5-phenyl-4 (lH) -pyridone l-acetoxy-3- (3-ethynylthiophenyl) -5- (3-ethynyl-5-fluorophenyl) -4 ( l H) pyridone

3- (3-Chlorophenyl) -5- [2- (3-fluorophenyIthio) phenyl] -l-methyl-4 (1H) -pyridone l-carboxymethyl-3- [3- (2-iodophenylthio) phenyl] -5- (3-methyl

5-methoxycarbonylphenyl) -4 (1H) -pyridone l- (2-chloroethyl) -3- (2,4-diethylphenyl) -5- [4- (4-ethylphenyl) -

thio) -2-methoxyphenyl] -4 (1H) pyridone

3- [3- (3-isopropylphenylthio) phenyl] -5-phenyl-l-trifluorme-

thyl-4 (1 H) pyridone

3- (2-Methyl-6-propoxyphenyl) -3- [4- (3-propoxyphenylthio) phenyl] -1-propargyl-4 (1 H) -pyridone

3- [3-Chloro-5 - (4-nitrophenylthio) phenyl] -1-methyl-5 - (2,4-divinylphenyl) -4 (1 H) -pyridone

3 - (4-Butylsulfonylphenyl) -5 -phenyl-1-propargyl-4 (1 H) -pyridone l-ethyl-3- (3-heptylsulfinylphenyl) -5- (4-propoxycarbonylphenyl) -4 ( 1 H) -pyridone l-ethoxy-3- [3- (4-propylnonylsulfinyl) phenyl] -5-phenyl-4 (1H) -pyridone

3- (2-ethoxyphenyl) -1-isopropyl-5- [4- (2-fluoroethylsulfinyl) -2-isopropylphenyl] -4 (1H) pyridone

3- [3,5-di (4-chlorophenyl) phenyl] -3- [4- (5,5-dibrompentylsulfonyl-2-ethoxyphenyl] -l-ethynyl-4 (1H) pyridone 3- [3- (12-iodododylsulfinyl) phenyl] -5-phenyl-l-propargyl-4 (1 H) -pyridone hydro iodide

3- (4-Benzylsulfinylphenyl) -5- (3-biphenylyl) -l-isopropenyl-4 (1H) pyridone

3- [3,5-Di (methylsulfonyloxy) phenyl] -5- [3- (5-phenylpentylsulfinyl) phenyl] -1-vinyl-4 (1H) pyridone 3- (3-acetoxyphenyl) -5- [ 2- (7-cyanoheptylsufinyl) phenyl] -l-methoxycarbonylmethyl-4 (1 H) -pyridone l- (2-carboxyethyl) -3- [3- (3-cyclohexenyl) -5- (3-cyanoundece-nylsulfinyl) phenyl ] -4 (1H) -pyridone l- (2-chloroethyl) -3 [4- (6-methoxyhexylsulfinyl) phenyl] -4 (1H) -pyridone

3- (4-Cyclopropylphenyl) -l-iodomethyl-5- [3- (6-propoxynonylsulfinyl) phenyl] -4 (1H) pyridone

3- [3,5-Di (allylsulfinyl) phenyl] -5-phenyl-l-propyl-4 (1H) -pyridone hydrofluoride l-dimethylamino-3- [2- (5-dodecenylsulfinyl) phenyl] -5 - (3-iso-butylphenyl) -4 (lH) -pyridone l-ethoxy-3- (3-iodo-4-pentylphenyl) -5- [3- (3,3,4,4-tetrafluoro-l-

butenylsulfinyl) -5-hexylphenyl] -4 (1H) pyridone

3- [2,4-di (chlorodifluoromethyl) phenyl] -l-propargyl-5- [3- (l, 2,3-

triiod-6-dodecenylsulfinyl) phenyl] -4 (1H) pyridone

3- [3- (4-bromo-2-butynylsulfinyl) -5-methylphenyl] -5 [2-iodo-3-

(l, 2,3-trichloropentyl) phenyl] -l-vinyl-4 (lH) -pyridone l-allyl-3- [2- (2,2-dibromo-4-hexynylsulfinyl (phenyl) -5-phenyl-

4 (1H) pyridone

3- (4-Benzyl-2-bromophenyl) -1- (2-carboxyethyl) -5- [3- (l-chlorobutyl) -5- (6-dodecynylsulfinyl) phenyl] -4 (1H) pyridone

15 630 356

l-cyanomethyl-3- [4- (3-fluorophenylsulfinyl) phenyl] -5- [3- (4-octenyl) phenyl] -4 (lH) -pyridone l-chloromethyl-3- [3- (l, l- dichloro-4-octenyl) -4-nitrophenyl] -5- [3- (2-iodophenylsulfinyl) phenyl] -4 (1H) -pyridone 5 3- [3- (2-chlorovinyl) -5- (4-methylphenylsulfinyl) phenyl] -l-eth-oxy-5- [3- (8-iodo-4-octenyl) phenyl] -4 (lH) -pyridone 3- [4- (3-isopropylphenylsulfinyl) phenyl] -5-phenyl-l propyl-4 (1H) pyridone

3- [3- (2-Ethoxyphenylsulfinyl) phenyl] -l-methyl-5- [4- (2-prop-io oxyphenoxy) phenyl] -4- (1 H) -pyridone l-ethyl.-3- ( 3-hexylsulfonylphenyl) -5- (4-hydroxyphenyl) -4 (1H) pyridone

3- (2-carboxy-4-ethylphenyl) -l-dimethylamino-5- [4- (3-ethyl-heptylsulfonyl) phenyl-4 (1H) pyridone 15 l-acetoxy-3- (2-hexyl-5- fluorophenyl) -5- (3-nitro-5-nonylsulfonylphenyl) -4 (1H) pyridone

3-phenyl-l-propoxy-5- [2- (3-propylnonylsulfonyl) phenyl] -4 (1H) -pyridone l-ethoxy-3-phenyl-5- (3-trifluoromethyl-5-trifluoromethylsulfo-20 nylphenyl) - 4 (1H) pyridone 3- (3-bromo-5-nitrophenyl) -1-ethynyl-5- [4-cyano-2- (6,6-di-bromohexylsulfonyl) phenyl] -4 (1H) -pyridone 3 - [3- (4,4-Diiodododylsulfonyl) phenyl] -5- (2-naphthyl) -1- (l-propynyl) -4 (1H) -pyridone 25 3- [5-chloromethyl-4- (2-propylphenyl ) phenyl] -l-vinyl-5- [4- (3-phenylbutylsulfonyl) phenyl] -4 (1H) -pyridone 3- [3- (3-cyanopropylsulfonyl) phenyl] -l-methoxycarbonylmethyl-5-phenyl- 4 (1H) -pyridone l- (2-carboxyethyl) -3- [4- (7-cyanoheptylsulfonyl) phenyl] -5- [3-30 (4-chlorophenylphenyl] -4 (1H) -pyridone 1-cyanomethyl-3 - [3- (ll-cyanoundecylsulfonyl) -5-fluorophenyl [-5- (4-propylsulfonyloxyphenyl) -4 (1H) -pyridone 3- (2-acetoxy-4-ethoxyethylsulfonylphenyl) -l-chloromethyl-5- (5- cyclopropyl-2-trifluoromethylphenyl) -4 (1H) -pyridone 35 3- [4- (3-cyclohexenyl) phenyl] -l-propyl-5- [3- (9-propoxynonylsulfonyl) phenyl] -4 (1H) -pyridone (4-vinylsulfonylphenyl) -4 (1H) -pyridinthione 3- (2-allylsulfonyl-4-chlo rphenyl) -5- (2-allyl-3-cyclohexyl-l-acetoxy-3- [4- (2,3-hexadienylsulfonyl) phenyl] -5-phenyl-40 4 (1H) pyridone

3,5-bis [3- (4-decenylsulfonyl) phenyl] 1-methoxy-4 (1H) pyridone

3- [4- (2-bromoallylsulfonyl) -2-methylphenyl] -1-methyl-5- [3- (7,7,8,8-tetrafluoro-2-octynyl) phenyl] -4 (1H) pyridone 45 3- [4- (6-Heptinyl) -3-methylphenyl] -1-ethyl-5- [3- (l, 1,2-triiodo-3-butenylsulfonyl) -5-chlorophenyl] -4 (1H) pyridone 3- [2- (5,5-dibromo-2-pentynyl) phenyl] -l-dimethylamino-5- [3- (5-fluoro-2-nonenylsulfonyl) phenyl] -4 (1H) -pyridone l-acetoxy- 3- [2-ethyl-4 (5-methoxypentyl) phenyl] -5- [3-50 (12,12,12-trichloro-6-dodecenylsulfonyl) phenyl] -4 (1H) -pyridone 3- [2- ( 3-chloro-5-hexynylsulfonyl) -4-nitrophenyl] -5- [3-bromo-5- (6-cyanohexyl) phenyl] -l-methoxy-4 (1H) -pyridone 3- [4- (6.6 -Dibromo-3-hexynylsulfonyl) phenyl] -5-phenyl-l-prop-oxy-4 (lH) -pyridone 55 3- [3- (2-cyanoethyl) phenyl] -l-ethynyl-5- [l, l , 2,2-tetrafluoro-6-decynylsulfonyl) phenyl] -4 (1H) pyridone l-cyanomethyl-3- [3- (6-dodecynylsulfonyl) -5-methylphenyl] -5- [2-methyl-4- ( l, l, 2,2-tetrafluoroethyl) phenyl] -4 (lH) pyridone l- (2-carboxyethyl) -3-phenyl-5- (3-phenylsulfonylphenyl) -60 4 (lH) pyridone

3- [3- (4,4-Diiodobutyl) phenyl] -5- [4- (4-fluorophenylsulfonyl) phenyl] -1-trifluoromethyl-4 (1H) pyridone 3- [2-chloromethyl-3- (6 , 6-dibromohexyl) phenyl] -5- [3- (3-iodophenylsulfonyl) phenyl] -l-methyl-4 (1H) -pyridone 65 3- (3-isopropyl-4-trifluoromethylphenyl) -l-methyl- 5- [3- (2-propoxyphenylsulfonyl) phenyl] -4 (1H) -pyridone 3- [2-chloro-4- (4-nitrophenylsulfonyl) phenyl] -l-ethyl-5- [3-fluoro-5- ( 4-heptyl) phenyl] -4 (1 H) pyridone

630 356

16

3- (3-Cyclopropylmethylphenyl) -l-methyl-5- (2-trifhioromethylphenyl) -4 (1H) pyridone

3,5-bis [3- (2-cyclopentylethyl) phenyl] -l-methoxy-4 (1H) pyridone

3- (4-Cyclohexyloxyphenyl) -l-methyl-5-phenyl-4 (1H) -pyridone methanesulfonate

3- (4-chlorophenyl) -5- (3-cyclobutylthiophenyl) -l-ethoxy-4 (1H) pyridone

3- (2-Cyclopentylsulfinylphenyl) -5- (3-hexylphenyl) -1-propoxy-4 (1H) pyridone hydrochloride

3- (3-CyclohexylsulfonylphenyI) -5- (3,5-difhiorphenyl) -l-tri-fluoromethyl-4 (lH) -pyridone l-cyanomethyl-3- (2-cyclopropylmethoxyphenyI) -5- (3-trifluoromethylphenyl ) -4 (1H) -pyridone l-acetoxy-3- [3- (2-cyclohexylethoxy) phenyl] -5-phenyl-4 (1H) -pyridone hydrobromide

3- [4- (2-Cyclobutylethylthio) phenyl] -1-dimethylamino-5- (3,5-dimethylphenyl) -4 (1H) pyridone

3- (3-Cyclopentlymethylsulfinylphenyl) -l-methyl-5- (3-trifluoromethylphenyl) -4 (1H) pyridone

3- [4- (2-Cyclohexylethylsulfonyl) phenyl] -1-ethyl-5- (3-propylphenyl-4 (1H) pyridone

3-Cyclopropylmethyl-5- (3-fluorophenyl) -l-methoxy-4 (1H) -py-ridone-methane sulfonate

3- (4-chlorophenyl) -3- (2-cyclohexylethyl) -l-ethoxy-4 (1H) -pyri-don

3- (3-fluorophenyl) -l-methyl-5-phenylthio-4 (1H) pyridone

3- (3-chloro-5-methylphenyl) -l-ethoxy-5-phenylsulfinyl-4 (1H) -

pyridone

3- (2-butylphenyl) -5- (3,5-dichlorophenylthio) -1- (l-propenyl) -4 (1H) pyridone

3- (2,4-dibromophenyl) -l-dimethylamino-5- (4-ethylphenylsulfonyl) -4 (1H) pyridone

3-methylthio-5-phenyl-1 - (- propynyl) -4 (1H) -pyridone

3-ethylsulfonyl-l-isopropyl-5- (3-trifluoromethylphenyl) -

4 (1H) pyridone

3- (2-chloroethylsulfinyl) -l-chloromethyl-5- (3-methylphenyl) -4 (lH) -pyridone l- (l-carboxyethyl) -3- (2,4-dimethylphenyl) -5-vinylthio-4 ( lH) -pyridone l- (2-bromoethyl) -3- (2-chloro-3-fluorophenyl) -5- (l, 2-difluoroallyl-sulfinyl) -4 (lH) -pyridone l-dimethylamino-3- (4th -methoxy-2-butenyl) -5-phenyl-4 (1H) -pyridone l-ethynyl-3- (2-propoxyvinyl) -5- (3-trifluoromethylphenyl) -4 (1H) -pyridone and

Preferred compounds of the formula I are given below.

l-methyl-3-phenyl-5- (3-trifluoromethylphenyl) -4 (1H) pyridone

3- (3-fluorophenyl) -l-methyl-5-phenyl-4 (1H) -pyridone

3- (3-chlorophenyl) -l-methyl-5-phenyl-4 (1H) pyridone

3,5-bis (3-chlorophenyl) -l-methyl-4 (1H) -pyridone

3- (3-chlorophenyl) -5- (3-fluorophenyl) -l-methyl-4 (1H) -pyridone l-methyl-3- (3-methylphenyl) -5-phenyl-4 (1H) -pyridone

3,5-diphenyl-1-methyl-4 (1H) pyridone 1-methyl-3,5-bis (3-trifluoromethylphenyl) -4 (1H) pyridone

3- (3-bromophenyl) -l-methyl-5-phenyl-4 (1H) pyridone

3- (3-methoxyphenyl) -l-methyl-5-phenyl-4 (1H) pyridone

3- (3-ethoxyphenyl) -l-methyl-5-phenyl-4 (1H) -pyridone l-methyl-3-phenyl-5- (3-propoxyphenyl) -4- (1H) -pyridone

3- (3-isopropoxyphenyl) -l-methyl-5-phenyl-4 (lH) -pyridone l-methyl-3-phenyl-5- [3- (l, l, 2,2-tetrafluoroethoxy) phenyl] -

4 (1H) pyridone

3,5-bis (3-fluorophenyl) -l-methyl-4 (1H) -pyridone

3- (2-chlorophenyl) -l-methyl-5- (3-trifluoromethylphenyl) -

4 (1H) pyridone

3- (3-chlorophenyl) -l-methyl-5- (3-trifluoromethylphenyl) -4 (1H) pyridone

3- (4-chlorophenyl) -l-methyl-5- (3-trifluoromethylphenyl) -4 (1H) pyridone

3- (2-fluorophenyl) -l-methyl-5- (3-trifluoromethylphenyl) -4 (1H) -pyridone 5 3- (3-fluorophenyl) -l-methyl-5- (3-trifluoromethylphenyl) -4 (1H ) -pyridone

3- (4-fluorophenyl) -l-methyl-5- (3-trifluoromethylphenyl) -4 (1H) pyridone

3- (3-chlorophenyl) -5- (4-chlorophenyl) -l-methyl-4 (lH) -pyridone io l-ethyl-3-phenyl-5- (3-trifluoromethylphenyl) -4 (lH) -pyridone l -AlIyl-3-phenyl-5- (3-trifluoromethylphenyl) -4 (lH) -pyridone l-methyl-3- (3-trifluoromethylphenyl) -4 (lH) -pyridone 3-chloro-l-methyl-5- ( 3-trifluoromethylphenyl) -4 (1H) pyridone 3-bromo-1-methyl-5- (3-trifluoromethylphenyl) -4 (1H) pyridone 15 liters, 3-dimethyl-5- (3-trifluoromethylphenyl) -4 ( lH) pyridone 3-ethyl-l-methyl-5- (3-trifluoromethylphenyl) -4 (lH) pyridone 3-isopropyl-l-methyl-5- (3-trifluoromethylphenyl) -4 (lH) pyridone

It is furthermore possible to subsequently acetylate the pyridothiones of the formula Ib, in which R is a hydroxy group, prepared by the process according to the invention, and the pyridones of the formula Ia prepared by the process according to the invention are also possible, in which R is a hydroxyl group, 25 first to acetylate to the corresponding pyridones, in which R is an acetoxy group, and then convert them to the corresponding pyridothiones by subsequent treatment with phosphorus pentasulfide.

Subsequently, pyridothiones of the formula Ib which can be prepared by the process according to the invention

(Ib)

■ N ^

• R

40

mentioned, which all have a herbicidal activity, and also those compounds which can be prepared from the thio compounds by acetylation:

l-methyl-3,5-bis (-3methoxyphenyl) -4 (1H) -pyridinethione, 45 l-ethyl-3- (4-ethoxyphenyl) -5-phenyl-4 (1H) -pyridinethione, 3- (3, 5-diiodophenyl) -5- (3-propylphenyl) -1-propyl-4 (1 H) -pyrididinion,

l-allyl-3- (3-chlorophenyl) -5- (2,3-diethoxyphenyl) -4 (lH) -pyrididinion,

50 3,5-diphenyl-1-ethyl-4 (1H) -pyridinethione,

l-acetoxy-3- (3,5-diethylphenyl) -5- (2,4-diethylphenyl) -4 (1H) -pyridinethione,

l-allyl-3- (l-naphthyl) -5- (4-propoxyphenyl) -4 (lH) -pyridine-thione,

55 l-methyl-3-phenyl-5- (2-propylphenyl) -4 (1H) -pyridinthione hydrochloride,

l-allyl-3-phenyl-5- (3-trifluoromethylphenyl) -4 (1H) -pyridine-thione,

l-acetoxy-3,5-diphenyl-4 (lH) -pyridinethione, 60 3- (2-iodophenyl) -5- (3-isopropylphenyl) -l-methoxy-4 (lH) -py-ridinthione,

3- (2-iodo-4-methylphenyl) -5-phenyl-1-vinyl-4 (1H) -pyridine-thione,

3,5-diphenyl-l-isopropyl-4 (1H) -pyridine thione, 65 3- (3-bromo-5-ethylphenyl) -5- (3-methylphenyl) -l-propyl-4 (1H) -pyridine thione

3- (2-iodo-4-propylphenyl) -l-methyl-5- (4-trifluoromethylphenyl- (4 (1H) pyridine thione,

l-methyl-3- (3-methyl-5-propylphenyl) -5-phenyl-4 (1H) -pyrididinion,

3- (2-chloro-4-iodophenyl) -5- (3-fluorophenyl) -l-propyl-4 (1H) -pyridinethione,

1- (2-Chloroethyl-3-cyano-5-phenyl-4 (1H) -pyridinthione, 3,5-diphenyl-1-ethynyl-4 (1H) -pyridinthione, 3- (4-heptafluoropropylphenyl) -5-hexyl -l-methyl-4 (1H) -pyrididinion,

3- (2-chloroethyl) -5- (4- (2,2-diiodoctyl) phenyl) -l-methoxy-4 (1H) -pyridinethione,

3- (6-iodohexyl) -l-isopropoxy-5-phenyl-4 (1H) -pyridinethione,

l-DimethyIamino-3,5-bis (3-trifluoromethylphenyI) -4 (lH) -pyri-

dinthion,

l- (2-chloroethyl) -3- (4- (2-cyanoethyl) phenyl) -4 (1H) -pyridine-thione,

l-methyl-3- (2-propoxyethyl) -5-phenyl-4 (1H) -pyridinthione hydrofluoride,

l-methyl-3-phenyl-5-vinyl-4 (1H) -pyridinethione,

3-allyl-5- (4- (3-cyanohexyl) phenyl) -l-propoxy-4 (1H) -pyridine-

thion,

3- (3-hexenyl) -5- (2- (2-methoxyethyl) phenyl) -l-methyl-4 (1H) -pyridinethione,

3- (2-iodo-l-hexenyl) -l-methyl-5- (3-vinylphenyl) -4 (1H) -pyrididinion,

3- (4-allyl-phenyl) -l-dimethylamino-5-phenyl-4 (1H) -pyridine-thione,

3- (2-MethoxyaIlyI) -l-methyl-5- (4-trifluoromethylphenyl) -4 (1 H) -pyridinethione

3- (3- (2-HexenyI) phenyl) -l-methyl-5- (3-propylphenyl) -4 (1H) -pyridinethione,

3- (2-ethyI-3-fluorophenyl) -5-ethyne-1-methyl-4 (1H) -pyridine-thione,

3-cyclopropyI-5- (2- (2-fluoro-l-pentenyl) phenyl) -l-methoxy-4 (1H) -pyridinethione,

3-cyclohexyl-5- (3-ethynylphenyl) -l-iodomethyl-4 (1H) -pyridine-thione,

3- (2,2-dibromocyclohexyl) -1-methyl-5- (2-pentinyl) phenyl) -4 (1 H) -pyridinethione,

l-acetoxy-3- (4-propylcyclohexyl) -5- (3- (6,6,6-trifluoro-2-hexynyl) phenyl) -4 (1H) -pyridinethione,

3- (3- (4-octynyl) phenyl) -5- (2-methoxycyclopropyl) -1-methyl-4 (1H) -pyridinethione,

3- (4-Cyclopropylphenyl) -l- (2-methoxycarbonyImethyl) -5- (2-propoxycyclobutyI) -4 (1H) -pyridinthione, 3- (2-Cyclobutenyl) -5- (3-cyclopentyIphenyl) -l-ethoxy -4 (lH) pyridinthione,

3-chloromethoxy-1-cyanomethyl-5- (2-formyloxyphenyl) -4 (1H) -pyridinethione,

1- (2-carboxyethyl) -3- (3-propionyloxyphenyl) -5-trifluoromethoxy-4 (1H) -pyridinethione,

3- (l, 2-dibromopropoxy) -l-ethoxy-5- (2-methyisulfonyloxyphenyl) -4 (1 H) -pyridinethione,

3- (3-diphenylyl) -1-methyl-5-vinyloxy-4 (1 H) -pyridinethione,

l-cyanomethyl-3- (2-methylphenoxy) -5- (3- (4-nitrophenyl) -

phenyl) -4 (lH) pyridinthione,

l-methyl-3- (4-nonyloxyphenyl) -5- (3-thienyl) -4 (1H) -pyridine-thione,

l-methyl-3- (4- (2-propylnonyloxy) phenyl) -5- (4-trifluoromethylphenyl) -4 (1 H) -pyridinethione,

3- (3,5-diethylphenyl) -l-ethyl-5- (4-trifluoromethoxyphenyl) -4 (1 H) -pyridinethione,

3- (2,4-divinylphenyl) -5- (4- (2-fluoroethoxy) phenyl) -l-iso-propoxy-4 (1 H) -pyridinethione,

3- (2,4-Dimethoxyphenyl) -l- (2-methoxycarbonylmethyl) -5- (2- (12-i oddodecyloxy) phenyl) -4 (1 H) -pyridinthion, 3- (4-benzyloxyphenyl) -l -cyanomethyl-5- (3,5-di (isopropenyl) phenyl) -4 (1 H) -pyridinethione,

17 630 356

3- (2,4-diformyloxyphenyl) -l-ethoxy-5- (4- (3-phenyl) -hexyl-oxy) phenyl) -4 (1H) -pyridinethione,

3- (4- (3-Cyanopropoxy) phenyl) -5- (3-ethoxy-5-iodophenyl) -l-methyl-4 (1H) -pyridinethione, s 3- (4- (7-cyanoheptyloxy) phenyl) - l-ethyl-5-phenyl-4 (lH) -py-ridinthion,

3- (3- (4-Cyanoundecyloxy) phenyl) -5- (2,4-di (2-ethoxyethyl) phenyl) -1-methoxy-4 (1 H) -pyridinethione, 3- (2- (2-ethoxyethoxy) ) phenyl) -l- (2-iodoethyl) -5- (3,4-diacet-îo oxyphenyI) -4 (lH) -pyridinthione, 3- (2,4-di (2-pentinyl) phenyl) -l- isopropoxy-5- (2-vinyloxyphenyl) -4 (1H) pyridinthione,

3- (3- (2,4-Hexadienyloxy) phenyl) -l-isopropyl) -5-phenyl-4 (1H) -pyridinthione hydroiodide, 15 l- (2-carboxyethyl) -3- (2,6-dipropylphenyl ) -5- (4- (5-dodece-nyloxy) phenyl) -4 (1H) -pyridinethione,

3- (2- (2-chloroallyloxy) phenyl) -l- (2,2-dichloroethyl) -5- (2,4-di-ethoxyphenyl-4 (1H) -pyridinethione,

l-chloromethyl-3- (3-methylsulfonyloxy-5-vinylphenyl) -5- (3-20 (2,2-dibromo-3-heptenyloxy) phenyl) -4 (lH) -pyridinethione, l-chlorodifluoromethyl-3- ( 2,4-di (chloromethyl) phenyl) -5- (2- (1,2,3-trichloro-6-dodecenyloxy) phenyl) -4 (1H) -pyridinethione,

3- (3- (6,6-dibromo-3-hexynyloxy) phenyl) -l-methyl-5- (3-nitro-

4-propylphenyl) -4 (1H) pyridinthione,

25 3- (3-ethynyloxyphenyl) -l-methyl-5-phenyl-4 (1H) -pyridine-thione hydrobromide,

3- (4- (4-fluorophenoxy) phenyl) -l-isopropyl-5-phenyl-4 (1H) -pyridinethione,

l-chloromethyl-3- (2,4-difluorophenyl) -5- (2- (3-propoxyphen-30 oxy) phenyl) -4 (1H) -pyridinethione,

l-methyl-3- (4- (2-nitrophenoxy) phenyl) -5-phenyl-4 (1H) -pyrididinion,

3- (3-isobutylthiophenyl) -l-isopropyl-5-phenyl-4 (1H) -pyridine-thione,

35 l- (2-methoxycarbonylmethyl) -3- (4- (3-iodophenyl) phenyl) -5- (3-trifluonomethylthiophenyl) -4 (lH) pyridinthione, i-acetoxy-3- (3-cyclopentylphenyl) -5 - (3- (2-fluoroethylthio) phenyl) -4 (1 H) -pyridinethione,

3- (3-benzylthio-5-ethynylphenyl) -l-cyanomethyl-5- (2-hexyl-40 phenyl) -4 (1H) -pyridinethione,

3- (2-bromo-4- (6-phenylhexylthio) phenyl) -5- (4- (2-cyanopropylthio) -2-ethylphenyl) -l-methyl-4 (lH) -pyridinethione, l-ethyl- 3- (4- (6-methoxyhexylthio) phenyl) -5-phenyl-4 (1H) pyridine thione,

45 l-methoxycarbonylmethyI-3- (3- (2-pentenylthio) phenyl) -5-phenyl-4 (1H) -pyridinethione,

3,5-bis (4- (9-iodo-8-nonenylthio) phenyl) -l-isopropyl-4 (1H) -pyridinethione,

l-ethyl-3- (3-fluorophenyl) -5- (4- (12,12,12-trichloro, 2,6-dode-50 cadienylthio) phenyl) -4 (lH) -pyridinethione,

l- (2-chloropropyl) -3 (2-cyclopropyl-4- (l, l, 2,2-tetrafluoro-5-decinylthio) phenyl) -5-phenyl-4 (lH) -pyridinethione, 3- ( 4- (4-decinylthio) -2-methylphenyl) -l-ethoxy-5- (5-fluoro-3-trifluoromethylphenyl) -4 (1 H) -pyridinthione, ss l-cyanomethyl-3- (4-phenylthiophenyl) -5-phenyl-4 (1H) -pyri-dinthione hydrochloride,

l-acetoxy-3- (4-butylphenyl) -5- (4- (3-methoxyphenylthio) phenyl) -4 (1H) pyridine thione,

3- (2-carboxyphenyl) -1-dimethylamino-5- (2-hydroxy-4- (2-60 propylpentylsulfinyl) phenyl) -4 (1H) -pyridinethione,

l-acetoxy-3- (2-cyano-5-nonylsulfinyîphenyl) -5- (3,5-dinitro-phenyl) -4 (1H) -pyridinethione,

l-methoxy-3- (2-nitrophenyl) -5- (4-trifluoromethylsulfinylphenyl) -4 (1H) pyridinethione, 65 3- (2- (3-cyanopropylsulfinyl) phenyl) -1-methoxycarbonylmethyl-5 -phenyl-4 (lH) -pyridinthione,

3- (2-chloro-4-cyclohexylphenyl) -5- (3-chloro-5- (2-ethoxyethylsulfinyl) phenyl) -l - (2-cyanoethyl) -4 (1 H) -pyridinethione,

630 356

18th

3- (3- (2-chloro-6-undecinyisulfinyl) phenyl) -l- (2,2-dibromo-ethyI) -5- (2-ethy] -5-vinyIsulfinylphenyl) -4 (1H) -pyridinethione, 3 - (3- (2,4-Hexadienylsulfinyl) phenyl) -l-methyl-5-phenyl-4 (1 H) -pyridinethione,

l-acetoxy-3- (4- (2-bromoallylsulfinyl) phenyl) -5- (2,4-dimethylphenyl) -4 (1H) pyridine thione,

l-isopropyl-3-phenyl-5- (4- (l, l, 2-trichloro-3-heptenylisulfinyl) phenyl) -4 (lH) -pyridine thione,

1-methoxycarbonylmethyl-3- (3-ethyl-5- (9.9, l 0,10-tetrafluoro-3-decynylsulfinyl) phenyl) -5-phenyl-4 (lH) -pyridinethione, l- (2-cyanoethyl) -3- (4-phenylsulfinylphenyl) -5-phenyl-4 (1H) pyridinthione,

3- (4- (2,4-Cyclohexadienyl) -3-fluorophenyl) -l-ethyl-5- (3-hydroxy-5- (nitrophenylsulfinyl) phenyl) -4 (lH) -pyridinethione, l-methyl- 3- (4-methylsulfonylphenyl) -5-phenyl-4 (1H) -pyridine-thione,

3- (4- (2-chloroethylsulfonyl) phenyl) -5- (3-fluoro-4-octylphenyl) -1-methoxy-4 (1 H) -pyridinethione,

3- (3-ethoxyhexylisulfonylphenyl) -5-phenyl-1-trifluoromethyl-4 (1H) -pyridinethione,

3- (3-cyanomethyl-4 (l-cyclobutenyl) phenyl) -l-methyl-5- (4-vi

nylsulfonylphenyl) -4 (1H) pyridinthione,

3- (2-allylsulfonyl-4-chlorophenyl) -5- (2-allyI-3-cyclohexylphe-

nyl) -l-dimethylamino-4 (1H) -pyridinethione,

3- (3-benzyl-5-ethynylsulfonylpehnyl) -5- (2- (7-phenylheptyl)

phenyl) -l-vinyl-4 (1H) -pyridinethione,

l-ethyl-3- (3-ethyl-5- (4-methylphenylsulfonyl) phenyl) -5- (4-

iodine-3- (2-propylbutyl) phenyl) -4 (1H) -pyridinethione,

l- (l-cyanoethyl) -3- (3- (2-propylphenylsulfonyl) phenyl) -5-

phenyl-4 (1H) pyridinthione,

3- (5-butyl-2- (3-methoxyphenylsulfonyl) phenyl) -l- (l-carboxy-ethyl) -5-phenyl-4 (lH) -pyridinethione, 3- (2-cyclopropoxyphenyl) -l-ethyl- 5- (2-fluorophenyl) -4 (1H) pyridine thione,

3- (4-cyclopropylsulfonylphenyl) -5- (2,4-diethylphenyl) -l-propyl-4 (1H) -pyridinethione,

l-acetoxy-3-phenylsulfonyl-5- (4-trifluoromethylphenyl) -4 (1H) -pyridinethione,

l-cyanomethyl-3-phenyl-5- (3-propoxyphenylsulfinyl) -4 (1H) -pyridinethione,

3- (2-chlorophenyl) -l-methyl-5-propylsulfinyl-4 (1H) -pyiridine-thione hydrofluoride,

l-ethoxy-3- (4-fluorophenyl) -5-trifluoromethylthio-4 (lH) -pyri-dinthione-toluenesulfonate,

3- (2-bromopropylsulfonyl) -l-chlorodifluoromethyl-5-phenyl-4 (1H) -pyridinethione,

3-allylsulfinyl-3- (3,5-diiodophenyl) l-methyl-4 (1H) -pyridine-thione,

l-methyl-3- (2-trifluoromethylphenyl) -5-vinylsulfonyl-4 (1H) -pyridinethione,

3- (3-allylphenyl) -5- (2-chlorovinylthio) -l-ethoxy-4 (1H) -pyrididinion,

3- (2-bromo-l-propenylsulfonyl) -l-methyl-5- (3-methylphenyl) -4 (1H) -pyridinethione,

3- (6-ethoxy-2-hexenyl) -l-methyl-5-phenyl-4 (1H) -pyridine-thione hydrochloride.

Of these pyridine ions, l-methyl-3-phenyl-5- (3-trifluoromethyl-phenyl) -4 (1H) -pyridine thione is particularly preferred because of its good herbicidal properties.

The invention will now be explained in more detail by means of examples.

Unless expressly stated otherwise, the temperatures given therein are given in ° C. The nuclear magnetic resonance spectra, that is to say the NMR spectra, were determined on a 60 megahertz instrument using tetramethylsilane as the internal reference source and are given in cycles per second (CPS). The melting points have been determined with a heating block.

example 1

A) Preparation of the starting material of the formula IV:

A solution of 4 liters of tetrahydrofuran and 284 g of sodium methoxide is mixed with 556 g of l- (3-trifluoromethylphenyl) -3-5 phenyl-2-propanone at a temperature of 10 to 15 ° C. over a period of 20 minutes. The reaction mixture is stirred for 15 minutes. 370 g of ethyl formate are then added over a period of 30 minutes, after which the reaction mixture is stirred at 10 to 15 ° C. for one hour. 10 A further 296 g of ethyl formate are then added to the mixture over a period of 30 minutes. The reaction mixture is then allowed to come to room temperature and is stirred overnight. A solution of 336 g of methylamine hydrochloride in 11 water is then added. The two-phase mixture is stirred at 30 ° C. for 30 minutes. The mixture is extracted with methylene chloride, whereupon the extracts are combined and concentrated in vacuo. This gives an oily residue from a mixture of 1-methylamino-2-phenyl-4- (3-trifluoromethylphenyl) -l-buten-3-one and 20l-methylamino-4 ~ phenyl-2- (3-trifluoromethylphenyl ) -l-buten-3-one.

B) Cyclization:

The residue obtained by process A) was 25 using ethyl formate (that is, ethyl formate) to the corresponding end product, namely l-methyl-3-phenyl-5- (3-trifluoromethylphenyl) -4 (1H) -py -ridone cyclized.

The reaction was carried out using the same reaction conditions as were explained in connection with the reaction with the ethyl formate in process step A).

The resulting mixture is then dissolved in methylene chloride, washed with water and dried. After drying and removing the solvent, 430 g of solid product are obtained, and thus a yield of 65%. The product is recrystallized from ethyl ether and identified as l-methyl-3-phenyl-5- (3-trifluoromethylphenyl) -4 (1H) -pyri-40 don by infrared analysis, magnetic resonance measurement and thin layer chromatography. It melts at 153 to 155 ° C and gives the following values in elemental analysis:

C.

45 h

N

calculated 69.30% 4.29 4.25

found. 69.48% 4.42 4.27

According to the process described in Example 1, the starting materials of the formula IV were prepared by using ethyl formate and then reacting with an appropriate amine hydrochloride, and these were then cyclized to the corresponding end products of the formula Ia using ethyl formate.

55

Example 2:

A) The starting material of the formula IV prepared was: l-methylamino-2,4-bis (3-trifluoromethylphenyl) -l-buten-3-one.

60 B) Cyclization:

The starting material prepared according to A) was cyclized with ethyl formate to give the l-methyl-3,5 ~ bis (3-trifluoromethylphenyl) -4 (1H) -pyridone.

The melting point of the end product was 152 to 154 ° C.

65

Example 3:

A) The starting material produced was the 2-phenyl-l- (2,2,2-trifluoroethylamino) -4- (3-trifluoromethylphenyl) -l-butene

19th

630 356

3-one and / or the 4-phenyl-l- (2,2,2-trifluoroethylamino) -2- (3-trifluoromethylphenyl-l-buten-3-one.

B) Cyclization:

The starting material prepared according to A) was cyclized with ethyl formate to give the 3-phenyl ~ l- (2,2,2-trifluoroethyl) -5- (3-tri-fluoromethylphenyl) -4 (1H) -pyridone.

NMR: quartet centered at 256 CPS, aromatic protons at 420 to 468 CPS.

Example 4:

A) The starting material of the formula IV was 2- (3-bromophenyl) -4- (3-chlorophenyl) -1-methylamino-1-buten-3-one and / or 4- (3-bromophenyl) -2 - (3-chlorophenyl) -1-methylamino-1-buten-3-one.

B) Cyclization:

This was cyclized with ethyl formate to give the 3- (3-bromophenyl) -5- (3-chlorophenyl) -1-methyl-4 (1H) -pyridone, which had a melting point of 192 ° C.

For example:

A) The starting material of the formula IV prepared was 2- (3-chlorophenyl) -4- (4-chlorophenyl) -1-methylamino-1-buten-3-one or 4- (3-chlorophenyl) -2- ( 4-chlorophenyl) -l-methylamino-l-buten-3-one.

B) Cyclization:

This starting material was cyclized using ethyl formate to give the 3- (3-chlorophenyl) -5- (4-chlorophenyl) -1-methyl-4 (1H) -pyridone, which had a melting point of 170 to 172 ° C.

Example 6:

A) The starting material of the formula IV prepared was 2- (2-fluorophenyl) -1-methylamino-4- (3-trifluoromethylphenyl) -l-buten-3-one and / or 4- (2-fluorophenyl) -l-methylamino-2- (3-trifluoromethylphenyl) -l-buten-3-one.

B) Cyclization:

This starting product was cyclized using ethyl formate to give the 3- (2-fluorophenyl) -l-methyl-5- (3-trifluoromethylphenyl) -4 (1H) -pyridone, which had a melting point of 152 to 154 ° C.

Example 7:

A) The starting product of the formula IV was the 2- (2-chlorophenyl) -4- (3-chlorophenyl) -1-methylamino-1-buten-3-one and / or the 4- (2-chlorophenyl) -2- (3-chlorophenyl) -l-methylamino-l-buten-3-one.

B) Cyclization:

This starting material was cyclized using ethyl formate to give the 3- (2-chlorophenyl) -5- (3-chlorophenyl) -1-methyl-4 (1H) -pyridone, which has a melting point of 160 to 161 ° C.

Example 8:

A) The starting material of the formula IV prepared was 2- (3-methoxyphenyl) -l-methylamino-4- (3-trifluoromethyl-phenyl) -l-buten-3-one and / or 4- (3-methoxyphenyl) -l-methylamino-2- (3-trifluoromethylphenyl) -l-buten-3-one.

B) Cyclization:

Using ethyl formate, this starting material was cyclized to the 3- (3-methoxyphenyl) -l-methyl-5- (3-tri-fluoromethylphenyl) -4 (1H) -pyridone, which had a melting point of 113 to 115 ° C.

Example 9:

The starting material of formula IV prepared was 2- (4-chlorophenyl) -l-methylamino-4- (3-trifluoromethylphenyl) -

1-buten-3-one and / or the 4- (4-chlorophenyl) -l-methylamino

2- (3-trifluoromethylphenyl) -l-buten-3-one.

B) Cyclization:

This starting product was cyclized using ethyl formate to give the 3- (4-chlorophenyl) -l-methyl-5- (3-tri-fluoromethylphenyl) -4 (1H) -pyridone, which had a melting point of 153 to 155 ° C .

Example 10:

A) The starting material produced was 1-allylamino-no-2-phenyl-4- (3-trifluoromethylphenyl) -l-buten-3-one and / 10 or l-allylamino-4-phenyl-2- (3-trifluoromethylphenyl ) -l-buten-3-one, and this was cyclized using ethyl formate to the l-allyl-3-phenyl-5- (3-trifluoromethylphenyl) -4- (lH) -pyridone, which had a melting point of 107 to 109 ° C.

15

Example 11:

A) The starting material produced was the 2- (4-isopropylphenyl) -1-methylamino-4-phenyl-1-buten-3-one and / or the 4- (4-isopropylphenyl) -1-methylamino-2- phenyl-l-butene-

20 3-one.

B) Cyclization:

Using ethyl formate, this was cyclized to the 3- (4-isopropylphenyl) -l-methyl-5-phenyl-4- (1H) -pyridone, which had a melting point of 159 ° C.

25th

Example 12:

A) The starting material of the formula IV prepared was the 2- (2-chlorophenyl) -l-methylamino-4- (3-trifluoromethylphenyl) -l-buten-3-one and / or the 4- (2-chlorophenyl) - l-methyl

30 amino-2- (3-trifluoromethylphenyl) -l-buten-3-one.

B) Cyclization:

Using ethyl formate, this starting material was cyclized to the 3- (2-chlorophenyl) -l-methyl-5- (3-tri-fluoromethylphenyl) -4 (1H) -pyridone, which had a melting point of 191 to 193 ° C .

Example 13:

A) The starting material of the formula IV prepared was the 2- (3-fluorophenyl) -1-methylamino-4- (3-trifluoromethylphe-

40 nyl) -l-buten-3-one and / or the 4- (3-fluorophenyl) -l-methylamino-2- (3-trifluoromethylphenyl) -l-buten-3-one.

B) Cyclization:

Using ethyl formate, this starting product was cyclized to the 3- (3-fluorophenyl) -l-methyl-5- (3-tri-45 fluoromethylphenyl) -4 (1H) -pyridone, which had a melting point of 94 to 96 ° C .

Example 14:

A) The starting material of the formula IV prepared was 50 the 2- (4-fluorophenyl) -l-methylamino-4- (3-trifluoromethylphe-

nyl) -l-buten-3-one and / or the 4- (4-fluorophenyl) -l-methylamino-2- (3-trifluoromethylphenyl) -l-buten-3-one.

B) Cyclization:

Using ethyl formate as the cyclizing agent, this was cyclized to the 3- (4-fluorophenyl) -1-methyl-5- (3-tri-fluoromethylphenyl) -4 (1H) pyridone, which had a melting point of 133 to 134 ° C.

Example 15:

60 A) The starting material of the formula IV prepared was the 2- (4-methoxyphenyl) -l-methylamino-4- (3-trifluoromethyl-phenyl) -l-buten-3-one and / or the 4- (4-methoxyphenyl) -l-methylamino-2- (3-trifluoromethylphenyl) -l-buten-3-one.

B) Cyclization:

65 Using ethyl formate, this starting product was cyclized to the 3- (4-methoxyphenyl) -l-methyl-5- (3-tri-fluoromethylphenyl) -4 (1H) -pyridone, which had a melting point of 162 to 165 ° C .

630 3s

20th

A further process for the preparation of the starting material of the formula IV is explained below.

In the process described above for the preparation of the required starting materials of the formula IV, the corresponding ketone intermediate of the formula IX was first prepared from the ketone of the formula VIII by reaction with a formylating agent, or a corresponding ketone intermediate in which the Qj is two hydrogen atoms, while Q2 is the unsaturated group introduced in the formylation reaction. Then, in the first-mentioned process, reaction with the corresponding amine of the formula RNH2 gives the desired starting product of the formula IV, that is to say, for example, the compound of the formula IX given above, or the corresponding product in which the rest Qi is two hydrogen atoms , while the rest Q2 stands for the corresponding nitrogen-containing group.

However, starting from the compounds of the formula Vm, the desired starting material of the formula IV can also be prepared by a different procedure:

The starting material of the formula Vin

\ «

V-CH-0-CH / a s

0

S "

> —C — 0 — CK

/ M

(R '

a, however, can also be carried out according to the following reaction scheme (A):

CA),

10th

0

V Ii

> —CH C — Ha I o- + (Rb) NCH = CH — Ra

/ ß gev, «

'Ri. 0

WI v 11

V> —CH • —C 0 — Ra

\ / II

* hcn (rb)

It is also possible to carry out the preparation of the enamine ketone in a procedure analogous to reaction (A), namely by carrying out the reaction according to the following reaction scheme (B):

(B).

20th

0

\ 'Halo-Il

• —CH = CHN (R) + gen — C— ■ —-CH 'R8

"\

/

(Re) NÖH

vni,

25th

in which

R1, R2 and m have the meaning given in formula Ia, is first reacted with an aminoformylating agent, the intermediate being the enamine ketone of formula X

If the intermediate of the formula X is prepared by aminoformylation of the starting product of the formula VIII, any compounds which can be used for the reaction with an active methylene group with the introduction of a = CHN (R9) 2- Group or an acid addition salt thereof. Suitable aminoformylating agents can be selected, for example, from the following compounds:

X

1 the orthoformamides

HC [N (R9) 2] 3,

Q3-R11

in which

R1, R2 and m have the same meaning as in formula Ia, and the radicals R9 independently of one another represent alkyl radicals having 1-3 carbon atoms, or the radicals R9 together with the nitrogen atom to which they are attached are a pyrrolidino radical, piperidino radical, morpholino radical form the N-methyl-piperazinorest.

As can be seen from the formula VIII of the starting material used, one of the two CH2 groups of the starting material of the formula VIII is converted into the corresponding nitrogen-containing group when carrying out the aminoformation reaction. However, the intermediate of formula X mentioned here represents only one of the two possible substitutions, and depending on the activating properties of the substituents R1 or R2 of the starting material, the other of the two CH2 groups mentioned can also be substituted in the aminoformylation. However, this is of no importance for the continuation of the production of the starting material, because in each case there must still be a radical Q which has the meaning of two hydrogen atoms.

The enamine ketone of the formula X is then reacted with ammonia or an amine of the formula RNH2, where R has the same meaning as in formula Ia, or an acid addition salt of this amine, giving the desired starting product of the formula IV.

The preparation of the enamine ketone of the formula X required as an intermediate in this procedure can

40

the formate teraminal HC [N (R9) 2] 2,

45

the formamide acetals

50

55

the tris (formylamino) methanes and the formiminium halides

Q3 — Rio

I.

HCN (R9) 2,

I.

Q3 — Rio

Q3

II

HC (NHCH) 3

HC = N (R9) 2 halogen I

halogen

The substituent Q3 in the above formulas stands for oxygen or sulfur, and the substituent R10 means an Al-60 alkyl group with 1-6 carbon atoms or the phenyl radical.

Suitable aminoformylating agents are described, for example, in DeWolfe, Carboxylic Acid Derivatives 420-506 (Acade-mic Press 1970) and Ulrich, Chemistry of Imidoyl Halides 87-96 (Plenum Press 1968). There are a number of publications by Bredereck et al on such means and implementations, of which the following are typical: Ber. 101, 4048-56 (1968); Ber. 104, 2709-26 (1971); Ber. 106, 3732-42 (1973); Ber. 97, 3997-406 (1964); Ann. 762, 62-72 (1972); Ber. 97,

21 630 356

3407-17 (1964); Ber. 103, 210-21 (1970), Angew. Chem. 78, l-methyl-3- (3-methylsulfonylphenyl) -5-phenyl-4 (1H) pyridone

147 (1966); Ber. 98, 2887-96 (1965); Ber. 96.1505-14 with a melting point of 176 to 181 ° C, yield 31%. (1963); Ber. 104, 3475-85 (1971); Beri. 101: 41-50 (1968);

Ber. 106, 3725-31 (1973) and Angew. Chem. Int. Issue 5, Example 17:

132 (1966). Other work on this includes Kreutzber 5 A) Preparation of the starting material of the formula IV:

ger et al. Arch. Der Pharm. 301,881-96 (1968) and 302,362-75 According to the manufacturing process described in Example 16

(1969), as well as Weingarten et al., J. Org. Chem. 32,3293-94 ren, the l-methylamino-2-phenyl-4- (4-trifluoromethyl-

(1967). phenyl) -l-buten-3-one and / or the l-methylamino-4-phenyl-

Aminoformylations are generally prepared without ver 2- (4-trifluoromethylphenyl) -l-buten-3-one.

Reversal of a solvent at elevated temperatures of io B) cyclization:

from about 50 to about 200 ° C. Occasionally, the starting material obtained by process A) also uses solvents such as dimethylformamide, and was converted to the l-methyl-3-phenyl-5- (4-tri-

in particular if one cyclizes the boiling point of the reac-fluoromethylphenyl) -4 (1H) -pyridone, which would like to increase a mixture of ions. If the aminoformylation had a melting point of 164 to 166 ° C.

with formiminium halides, then 15

but conveniently used aprotic solvents, Example 18:

and in particular those as described above in the A) Preparation of the starting material of the formula IV: connection with the implementation of the formylation reaction. The enamine ketone of the formation required as an intermediate in the preparation of the compounds according to the invention XI was prepared according to the reaction scheme explained above (B ) of the formula Ia have been described. In this case, 20 is produced, namely by appropriately reacting 9.6 g of N, N-diethylstyrylamine at temperatures which range from 0 to 14.4 g of (3-benzyloxyphenyl) acetyl chloride. 50 ° C and preferably at about room temperature. If 13 g of the 4- (3-benzyloxyphenyl) -l-diethyl obtained in this way, if desired, amino-2-phenyl-l-buten-3-ones can also be used in 100 ml of methanol, such as chloro, in such aminoformylations - dissolved and mixed with 26 g of methylamine hydrochloride. The reform or methylene chloride. The reaction mixture is heated to reflux temperature overnight. The reaction of the enamine intermediate of the formula is heated. Then the solvent is removed under vacuum, X with ammonia or the amine of the formula RNH2 is added, whereupon 100 ml of water are added and the mixture is conveniently carried out with methy in protic solvent, lench chloride. The extract is washed with dilute chlorine, alkanols, and especially ethanol, using this hydrochloric acid and then with water. The exchange reaction is preferred. For these exchange reactions, the organic layer is separated, dried, filtered and can be evaporated to dryness at temperatures from about -20 ° C. to about 100 ° C. The work obtained as an intermediate product. Working at room temperature is generally sufficient and 4- (3-benzyloxyphenyl) -l-methylamino-2-phenyl-l-buten-3-one is preferred. is dissolved in 125 ml of ethyl ether.

B) Cyclization

Example 16: 35 The solution obtained according to A) is cooled to 5 ° C. and

A) Preparation of the starting material of the formula IV: 12 g of sodium ethoxide are added. The reaction mixture is required as an intermediate enamine ketone of formula X, kept at about 5 ° C and slowly mixed with 50 ml of ethyl formate, namely 2-phenyl-l-diethylamino-4- (3-methylthiophenyl). The mixture is then stirred, 1-buten-3-one being allowed to slowly come to room temperature after the reaction given above. The reaction scheme (B) is prepared, namely by reacting 17.5 g of 40 mixture is then evaporated to dryness, whereupon the N, N-diethylstyrylamine is extracted with 15 g (3-methylthiophenyl) ace residue with chloroform, the extract with water tylchloride. The enaminoketone is dissolved in 300 ml of ethanol, washed and dried. The product obtained is mixed chroma with 20 g of methylamine hydrochloride and stirred for about 24 hours over silica gel using a 50:50 thread. The solvent is then evaporated off and mixed with ethyl acetate and hexane. The product-containing residue is extracted with ethyl ether and the solution with 45 gene fractions are collected, combined and washed to dryness with water. The organic layer is evaporated over water. Dried by recrystallization of the product from ethyl-free sodium sulfate and the dried acetate solution gives 1.5 g of 3- (3-benzyloxyphenyl) -l-methyl-5-is evaporated to dryness, whereby the 1-methylamiphenyl-4 ( lH) -pyridone, which melts at 158 to 160 ° C. no-4- (3-methylthiophenyl) -2-phenyl-l-buten-3-one is obtained.

see example 19

B) Cyclization: A) Preparation of the starting material of the formula IV: The starting material obtained by process A). According to the process described in Example 16, the formula IV was converted to 1-methylamino-2-phenyl-4- ( 2-thienyl) -l-buten-3-one her-

cyclized the method described in Example 1. One creates.

held the l-methyl-3- (3-methylthiophenyl) -5-phenyl- 55 B) cyclization:

4 (1 H) -pyridone, which was identified by the NMR spectrum. The starting material prepared according to A) was combined with de, in which maxima were found at 144 and 227 CPS, with ethyl formate to the l-methyl-3-phenyl -5- (2-thienyl) -4 (1H) -

420 to 440 and 442 to 458 CPS cyclized aromatic protons pre-pyridone, which had a melting point of 147 to. 148 ° C.

From this end product of formula Ia obtained in 60

which is a radical R1 in the meaning of a grouping of example 20:

Formula -SR3 is present, where R3 is a methyl radical, A) The process according to Example 16 was followed by the removal

by oxidation with m-chlorobenzoic acid the corresponding starting material of the formula IV, namely the 4- (3-isobutylphe-

Methylsulfinyl compounds, or methylsulfonyl compounds (nyl) -l-methylamino-2-phenyl-l-buten-3-one,

gene be produced. 65 B) Cyclization:

The products produced in this way were 1-methyl-3- (3-me-). The starting material prepared according to A) was converted to the 3- (3-isobutylphenyl) with ethylsulfinylphenyl) -5-phenyl-4 (1H) -pyridone with an ethyl formate. -l -methyl-5-phenyl-

Melting point of 161 to 164 ° C, yield 57%, and the 4 (1H) pyridone cyclized. In NMR this doublet was 54

630 356

and 147 CPS, a septet at 113 CPS and aromatic protons at 420 to 460 CPS.

Example 21:

A) According to the method according to Example 16, the l-methylamino-4- (3-nitro-phenyl) -2-phenyl-l-buten-3-one was prepared as the starting material of the formula IV.

B) Cyclization:

The starting material prepared according to A) was cyclized with ethyl formate to give the l-methyl-3- (3-nitrophenyl) -5-phenyl-4 (1H) -pyridone. This had a melting point of 135 to 136.5 ° C.

Example 22:

A) Preparation of the starting material of the formula IV:

The l- (2,4-dichlorophenyl) -3-phenyl-2-propanone was reacted with ethyl formate according to the process described in Example 1, process step A). The reaction mixture was then not reacted further with methylamine, but was subjected to a reaction with ammonium acetate, giving a corresponding starting product of the formula IV, in which R is a hydrogen atom.

B) Cyclization:

According to the process described in Example 1, the residue obtained by Process A) above was reacted with ethyl formate in the manner as explained in Process Step A) of Example 1. This gave the corresponding pyridone which is unsubstituted in the 1-position, namely 3- (2,4-dichlorophenyl) -5-phenyl-4 (1H) -pyridone, which was identified by infrared analysis and magnetic nuclear magnetic resonance measurement.

Example 22a

This example is used to explain the subsequent methylation of the pyridone prepared according to Example 22.

1.3 g of the 3- (2,4-dichlorophenyl) -5-phenyl-4 (1H) -pyridone prepared according to Example 22 are added to a solution of 0.5 g of 50% sodium hydride in 60 ml of DMSO, whereupon the whole thing is heated until the pyridone has dissolved. Then an excess of methyl iodide is added, whereupon the mixture is stirred for 0.5 hours. The mixture is poured into water and filtered. The solids are extracted with methylene chloride, which is then dried with magnesium sulfate and evaporated to dryness. By recrystallizing the resulting residue from benzene-hexane, 1.1 g3- (2,4-dichlorophenyl) -l-methyl-5-phenyl-4 (1H) -pyridone is obtained, which melts at 202 to 204 ° C and was identified by its nuclear magnetic resonance spectrum as well as by infrared analysis. The following data is obtained with micro-element analysis:

22

The 1,3-diphenyl-2-propanone was first reacted with ethyl formate by the process described in Example 1, step A), and the intermediate product obtained was subjected to a further reaction with propylamine hydrochloride.

5 This gave 2,4-diphenyl-l-propylamino-l-buten-3-one.

B) Cyclization:

The starting material prepared in accordance with A) was formed with ethyl formate to give the 3,5-diphenyl-1-propyl-4 (1H) -pyridone cy-

10clized, which has a melting point of 172 to 174 ° C.

Example 28:

A) The starting material of formula IV was

15 the 2,4-diphenyl-l-methoxyamino-l-buten-3-one.

B) Cyclization:

The starting material prepared according to A) was cyclized with ethyl formate to give the 3,5-diphenyl-1-methoxy-4 (1H) -pyridone, which has a melting point of 165 ° C.

20th

Example 29:

A) The starting material of the formula IV prepared 2- (3-fluorophenyl) -l-methylamino-4-phenyl-l-buten-3-one and / or the 4- (3-fluorophenyl) -l-methylamino-2-phenyl- l-buten-3-one.

25 B) Cyclization:

The starting material prepared according to A) was cyclized with ethyl formate to give the 3- (3-fluorophenyl) -1-methyl-5-phenyl-4 (1H) -pyridone. This had a melting point of 133.5 ° C.

30th

calculated: found:

C.

66.68 66.84

H

3.83 4.05

N

4.09 4.01

Examples 23 to 26

The following pyridones which are substituted in the 1-position are prepared from the corresponding pyridones which are unsubstituted in the 1-position by natural N-alkylation:

3,5-diphenyl-1-ethyl-4 (1H) -pyridone, melting point 171 ° C.,

l-allyl-3,5-diphenyl-4 (lH) -pyridone, melting point 174 ° C. 3,5-diphenyl-l-isopropyl-4 (lH) -pyridone, melting point 152 ° C.,

l-cyanomethyl-3,5-diphenyl-4 (1H) -pyridone, melting point 221 to 224 ° C.

Example 27:

A) Preparation of the starting material of the formula IV:

Example 30:

A) The starting material of the formula IV prepared was the 2- (4-bromophenyl) -l-methylamino-4-phenyl-l-buten-3-one and / or the 4- (4-bromophenyl) -l-methylamino-2- phenyl-l-

35 buten-3-one.

B) Cyclization:

The starting material prepared according to A) was cyclized with ethyl formate to give the 3- (4-bromophenyl) -1-methyl-5-phenyl-4 (1H) -pyridone, which had a melting point of 40 172 ° C.

Example 31:

A) The starting material of the formula IV prepared was the 2- (4-methoxyphenyl) -l-methylamino-4-phenyl-l-butene-3-

45 on and / or the 4- (4-methoxyphenyl) -l-methylamino-2-phe-nyl-l-buten-3-one.

B) Cyclization:

The starting material prepared according to A) was cyclized with ethyl formate to give the 3- (4-methoxyphenyl) -l-methyl-5-phenyl-50 4 (1H) -pyridone, which has a melting point of 165 ° C.

Example 32:

A) The starting material of the formula IV prepared was 55 the 2- (3-chlorophenyl) -l-methylamino-4-phenyl-l-buten-3-one and / or the 4- (3-chlorophenyl) -l-methylamino- 2-phenyl-l-buten-3-one.

B) Cyclization:

The starting material prepared according to A) was cyclized with 60 ethyl formate to give the 3- (3-chlorophenyl) -l-methyl-5-phenyl-4 (1H) -pyridone, which had a melting point of 172.5 ° C.

Example 33:

65 A) The starting material of formula IV prepared was the 2- (4-chlorophenyl) -l-methylamino-4-phenyl-l-buten-3-one and / or the 4- (4-chlorophenyl) -l-methylamino-2 -phenyl-l-buten-3-one.

23

630 356

B) Cyclization:

The starting material prepared according to A) was cyclized with ethyl formate to give the 3- (4-chlorophenyl) -1-methyl-5-phenyl-4 (1H) -pyridone, which had a melting point of 141.5 ° C.

Example 34:

A) The starting material of the formula IV prepared was l-methylamino-2- (l-naphthyl) -4-phenyl-l-buten-3-one and / or l-methylamino-4- (l-naphthyl) -2-phenyl-l-bu-ten-3-one.

B) Cyclization:

The starting material prepared according to A) was cyclized with ethyl formate to give the l-methyl-3- (l-naphthyl) -5-phenyl-4 (1H) -pyridone. The NMR had maxima at 204 and 483 CPS and aromatic protons at 430 to 470 CPS.

Example 35:

A) The starting material of formula IV produced was 2,4-bis (3-chlorophenyl) -l-methylamino-l-buten-3-one.

B) Cyclization:

The starting material prepared according to A) was cyclized with ethyl formate to give the 3,5-bis (3-chlorophenyl) -l-methyl-4 (1H) -pyridone, which had a melting point of 164 to 167 ° C.

Example 36:

A) The starting material of the formula IV was l-methylamino-2- (3-methylphenyl) -4-phenyl-l-buten-3-one and / or l-methylamino-4- (3-methylphenyl) -2 -phenyl-l-buten-3-one.

B) Cyclization:

The starting material prepared according to A) was cyclized with ethyl formate to give the l-methyl-3- (3-methylphenyl) -5-phenyl-4 (1H) -pyridone, which was isolated in the form of a complex with 0.5 mol of benzene and in this form had a melting point of 79.5 ° C.

Example 37:

A) The starting material of the formula IV was l-methylamino-2- (4-methylphenyl) -4-phenyl-l-buten-3-one and / or l-methylamino-4- (4-methylphenyl) -2 -phenyl-1-buten-one.

B) Cyclization:

The starting material prepared according to A) was cyclized with ethyl formate to give the l-methyl-3- (4-methylphenyl) -5-phenyl-4 (1H) -pyridone, which had a melting point of 144.5 ° C.

Example 38:

A) The starting material of the formula IV prepared was l-methylamino-2- (2-methylphenyl) -4-phenyl-l-buten-3-one and / or l-methylamino-4- (2-methylphenyl) -2 -phenyl-l-buten-3-one.

B) Cyclization:

The starting material prepared according to A) was cyclized with ethyl formate to give the l-methyl-3- (2-methylphenyl) -5-phenyl-4 (1H) pyridone.

In NMR, this product showed maxima at 133 and 201 CPS and aromatic protons at 420 to 440 and 442 to 460 CPS.

Example 39:

A) The starting material of the formula IV prepared was the 2- (4-fluorophenyl) -l-methylamino-4-phenyl-l-buten-3-one and / or the 4- (4-fluorophenyl) -l-methylamino-2- phenyl-l-buten-3-one.

B) Cyclization:

The starting product prepared according to A) was cyclized with ethyl formate to give the 3- (4-fluorophenyl) -l-methyl-5-phenyl-4 (1H) -pyridone.

5 The melting point of the end product was 166 ° C.

Example 40:

A) The starting material of the formula IV prepared was l-methylamino-2-phenyl-4- (3-trifluoromethylphenyl) -l-bu-

10 ten-3-one and / or the l-methylamino-4-phenyl-2- (3-trifluoromethylphenyl) -l-buten-3-one.

B) Cyclization:

The starting material prepared according to A) was converted into the l-methyl-3-phenyl-5- (3-trifluoromethyl

15 phenyl) -4 (1H) -pyridone cyclized, which had a melting point of 152 to 156 ° C.

Example 41:

A) The starting material of formula IV was

20 the 2- (3-methoxyphenyl) -l-methylamino-4-phenyl-l-buten-3-one and / or the 4- (3-methoxyphenyl) -l-methylamino-2-phe-nyl-1-butene -3-one.

B) Cyclization:

The starting material produced according to A) was with

25 ethyl formate to the 3- (3-methoxyphenyl) -l-methyl-5-phenyl-4 (1H) -pyridone cyclized.

This end product showed maxima at 200 and 220 CPS and aromatic protons at 420 to 440 and 442 to 460 CPS in NMR.

30th

Example 42:

A) The starting material of formula IV produced was das2- (3,4-dichlorophenyl) -l-methylamino-4-phenyl-l-buten-3-one.

35 B) Cyclization:

The starting material prepared according to A) was cyclized to the 3- (3,4-dichlorophenyl) -l-methyl-5-phenyl-4 (1H) -pyridone.

The melting point of this end product was 166.5 ° C.

40

Example 43:

A) The starting material of the formula IV prepared was the 2- (2,5-dichlorophenyl) -l-methylamino-4-phenyl-l-buten-3-one and / or the 4- (2,5-dichlorophenyl) -l- methylamino-2-

45 phenyl-1-buten-3-one.

B) Cyclization:

The starting material prepared according to A) was cyclized with ethyl formate to give the 3- (2,5-dichlorophenyl) -l-methyl-5-phenyl-4 (1H) -pyridone.

The melting point of this end product was 155.5 ° C.

Example 44:

A) The starting material of formula IV prepared was the 2- (2-chlorophenyl) -l-methylamino-4-phenyl-l-buten-3-one

55 and / or the 4- (2-chlorophenyl) -l-methylamino-2-phenyl-l-buten-3-one.

B) Cyclization:

The starting material prepared according to A) was converted to the 3- (2-chlorophenyl) -l-methyl-5-phenyl- with ethyl formate

60 4 (1H) pyridone cyclized.

This end product had a melting point of 145 ° C.

Example 45:

A) The starting material of formula IV was

65 the 2,4-bis (3-fluorophenyl) -l-methylamino-l-buten-3-one.

B) Cyclization:

The starting material prepared according to A) was converted to the 3,5-bis (3-fluorophenyl) -l-methyl-4 (1H) - with ethyl formate

630 356

24th

pyridone cyclized, which had a melting point of 149 to 151 ° C.

Example 46:

A) The starting material of the formula IV prepared was the 2- (3-chlorophenyl) -4- (3-fluorophenyl) -1-methylamino-1-bu-ten-3-one and / or the 4- (3-chlorophenyl) - 2- (3-fluorophenyl) -l-methylamino-l-buten-3-one.

B) Cyclization:

The starting material prepared according to A) was cyclized with ethyl formate to give the 3- (3-chlorophenyl) -5- (3-fluorophenyl) -1-methyl-4 (1H) -pyridone.

The melting point of this end product was 145 to 146 ° C.

Example 47:

A) The starting material of the formula IV prepared was the 2- (3,5-dichloroiphenyl) -l-methylamino-4-phenyl-l-buten-3-one and / or the 4- (3,5-dichlorophenyl) -l- methylamino-2-phenyl-l-buten-3-one.

B) Cyclization:

The starting material prepared according to A) was cyclized with ethyl formate to give the 3- (3,5-dichlorophenyl) -1-methyl-5-phenyl-4 (1H) pyridone.

This end product had a melting point of 131 to 135 ° C.

Example 48:

A) The starting material of formula IV prepared was 2,4-bis (3-bromophenyl) -l-methylamino-l-buten-3-one.

B) Cyclization:

The starting material prepared according to A) was cyclized with ethyl formate to give 3,5-bis (3-bromophenyl) -1-methyl-4 (1H) -pyridone.

The melting point of the end product was 216.5 ° C.

Example 49:

A) The starting material of the formula IV prepared was the 2- (3-bromophenyl) -l-methylamino-4-phenyl-l-buten-3-one and / or the 4- (3-bromophenyl) -l-methylamino-2- phenyl-l-buten-3-one.

B) Cyclization:

The starting material prepared according to A) was cyclized with ethyl formate to give the 3- (3-bromophenyl) -l-methyl-5-phenyl-4 (1H) -pyridone.

The melting point of the end product was 172 ° C.

Example 50:

A) The starting material of the formula IV prepared was the 2- (2-fluorophenyl) -l-methylamino-4-phenyl-l-buten-3-one and / or the 4- (2-fluorophenyl) -l-methylamino-2- phenyl-l-buten-3-one.

B) Cyclization:

The starting product prepared according to A) was cyclized with ethyl formate to give the 3- (2-fluorophenyl) -1-methyl-5-phenyl-4 (1H) -pyridone.

The melting point of this end product was 165 ° C.

Example 51:

A) The starting material of the formula IV prepared was 2- (3-bromophenyl) -l-methylamino-4- (3-trifluoromethylphenyl) -l-buten-3-one and / or 4- (3-bromophenyl) -l-methylamino-2- (3-trifluoromethylphenyl) -l-buten-3-one.

B) Cyclization:

The starting material prepared according to A) was cyclized with ethyl formate to give the 3- (3-bromophenyl) -1-methyl-5- (3-tri-fluoromethylphenyl) -4 (1H) -pyridone.

This end product had a melting point of 151 to 153 ° C.

Example 52:

A) The starting material of the formula IV prepared was l- (l-carboxyethylamino) -2-phenyl-4- (3-trifluoromethyl-phenyl) -l-buten-3-one and / or l- (l-carboxyethylamino) -

5 4-phenyl-2- (3-trifluoromethylphenyl) -l-buten-3-one.

B) Cyclization:

The starting material prepared according to A) was cyclized with ethyl formate to give the l- (l-carboxyethyl) -3-phenyl-5- (3-tri-fluoromethylphenyl) -4 (lH) pyridone.

io This end product had a melting point of 236 to 237 ° C.

Example 53:

A) The starting material of the formula IV was prepared by the process described in Example 1, under A), using 1,1-dimethyl-hydrazine hydrochloride as the salt of an amine for the preparation of the starting material of the formula IV. The starting material of formula IV thus obtained was l- (l, l-dimethylhydrazmo) -2,4-diphenyl-l-buten-3-20 one.

B) Cyclization:

The starting material prepared according to A) was cyclized with ethyl formate to give the l-dimethylamino-3,5-diphenyl-4 (1H) pyridone.

25 This end product had a melting point of 143 ° C.

Example 54:

A) The starting material of the formula IV prepared was 30-l-methylamino-2- (2-naphthyl) -4-phenyl-l-buten-3-one and / or l-methylamino-4- (2-naphthyl) - 2-phenyl-l-bu-ten-3-one.

B) Cyclization:

The starting material prepared according to A) was cyclized with 35 ethyl formate to give the l-methyl-3- (2-naphthyl) -5-phenyl-4 (1H) -pyridone.

This end product had a melting point of 101 to 105 ° C.

40 Example 55:

A) The starting material of the formula IV prepared was l-ethylamino-2-phenyl-4- (3-trifluoromethylphenyl) -l-butten-3-one and / or l-ethylamino-4-phenyl-2- ( 3-trifluoromethylphenyl) -l-buten-3-one.

4S B) Cyclization:

The starting material prepared according to A) was cyclized with ethyl formate to give the 1-ethyl-3-phenyl-5- (3-trifluoromethylphenyl) -4 (1 H) -pyridone.

The melting point of this end product was 98 to 50 100 ° C.

Example 56:

A) The starting material of the formula IV prepared was the 2-phenyl-1-propylamino-4- (3-trifluoromethylphenyl) -l-bu-

55 ten-3-one and / or the 4-phenyl-l-propylamino-2- (3-trifluoromethylphenyl) -l-buten-3-one.

B) Cyclization:

The starting material prepared according to A) was cyclized with ethyl formate to give the 3-phenyl-1-propyl-5- (3-trifluoromethyl-60 phenyl) -4 (1H) -pyridone.

This end product showed triplet maxima at 60 and 230 CPS and a sextuplet at 114 CPS.

Example 57:

65 A) The starting material of the formula IV produced was the l-methoxyamino-2-phenyl-4- (3-trifluoromethylphenyl) -l-buten-3-one and / or the l-methoxyamino-4-phenyI-2- (3rd -tri-fluoromethylphenyl) -l-buten-3-one.

25th

630 356

B) Cyclization:

The starting material prepared according to A) was cyclized with ethyl formate to give the l-methoxy-3-phenyl-5- (3-trifluoromethyl-phenyl) -4 (1H) -pyridone.

This end product had a maximum at 248 CPS in NMR.

Example 58:

A) The starting material of the formula IV prepared was the 2- (3-chlorophenyl) -l-methylamino-4- (3-trifluoromethylphenyl) -l-buten-3-one and / or the 4- (3-chlorophenyl) - l-methyl-amino-2- (3-trifluoromethylphenyl) -l-buten-3-one.

B) Cyclization

The starting material prepared according to A) was cyclized with ethyl formate to give the 3- (3-chlorophenyl) -1-methyl-5- (3-tri-fluoromethylphenyl) -4 (1H) pyridone.

This end product had a melting point of 133 to 135 ° C.

B) Cyclization:

The starting material prepared according to A) was cyclized with ethyl formate to give the 3- (3-carboxyphenyl) -l-methyl-5-phenyl-4 (1H) -pyridone.

5 This product had a melting point of 266 to 268 ° C in the form of the hydrochloride.

Example 64:

A) The starting material of the formula IV prepared was io the 2- (3-cyanophenyl) -l-methylamino-4-phenyl-l-buten-3-one and / or the 4- (3-cyanophenyl) -l-methylamino- 2-phenyl-l-buten-3-one.

B) Cyclization:

The starting material prepared according to A) was cyclized with 15 ethyl formate to give the 3- (3-cyanophenyl) -l-methyl-5-phenyl-4 (1H) -pyridone.

This product had a melting point of 164 to 166 ° C.

Example 59:

A) The starting material of the formula IV prepared was the 2- (4-biphenyl) -l-methylamino-4-phenyl-l-buten-3-one and / or the 4- (4-biphenyl) -l-methylamino-2- phenyl-l-bu-ten-3-one.

B) Cyclization:

The starting material prepared according to A) was cyclized with ethyl formate to give the 3- (4-biphenyl) -l-methyl-5-phenyl-4 (1H) -pyridone.

This end product had a melting point of 186 to 190 ° C.

Example 60:

A) The starting material of the formula IV prepared was 2- (3-biphenyl) -l-methylamino-4-phenyl-l-buten-3-one and / or 4- (3-biphenyl) -l-methylamino-2 -phenyl-l-bu-ten-3-one.

B) Cyclization:

The starting material prepared according to A) was cyclized with ethyl formate to give the 3- (3-biphenyl) -l-methyl-5-phenyl-4 (1H) -pyridone.

This end product had a melting point of 186 to 190 ° C.

Example 61:

A) The starting material of the formula IV was 1-methylamino-2-phenyl-l-buten-3-one.

B) Cyclization

The starting material prepared according to A) was cyclized with ethyl formate to give the l-methyl-3-phenyl-4 (1H) pyridone.

This end product had a melting point of 123 to 125 ° C.

Example 62:

A) The starting material of the formula IV was 1-methylamino-2- (3-trifluoromethylphenyl) -l-buten-3-one.

B) Cyclization:

The starting material prepared according to A) was cyclized with ethyl formate to give the l-methyl-3- (3-trifluoromethylphenyl) -4 (1 H) -pyridone.

This end product had a melting point of 122 to 123 ° C.

20 Example 65:

A) The starting material of the formula IV was 2- (3-ethoxycarbonylphenyl) -1-methylamino-4-phenyl-1-buten-3-one and / or 4- (3-ethoxycarbonylphenyl) -l-methylamino -2-phenyl-l-buten-3-one.

25 B) Cyclization:

The starting material prepared according to A) was cyclized with ethyl formate to give the 3- (3-ethoxycarbonylphenyl) -l-methyl-5-phenyl-4 (1H) -pyridone.

This product had a melting point of 167 to 168 ° C.

Example 66:

A) The starting material of the formula IV was 2,4-bis (3-cyanophenyl) -l-methylamino-l-buten-3-one. 35 B) Cyclization:

The starting material prepared according to A) was cyclized with ethyl formate to give the 3,5-bis (3-cyanophenyl) -l-methyl-4 (1H) -pyridone.

The melting point of this product was 322 ° C to 40 327 ° C.

Example 67:

A) The starting material of the formula IV prepared was l-methylamino-2-phenyl-4 (3-thienyl) -l-buten-3-one and /

45 or the l-methylamino-4-phenyl-2- (3-thienyl) -l-buten-3-one.

B) Cyclization:

The starting material prepared according to A) was cyclized with ethyl formate to give the l-methyl-3-phenyl-5- (3-thienyl) -4 (1H) -pyridone.

This end product showed maxima at 204 and 495 CPS as well as aromatic protons at 430 to 460 CPS.

Example 68:

A) The starting material of the formula IV prepared was 55 the 2-cyano-l-methylamino-4-phenyl-l-buten-3-one and / or the 4-cyano-l-methylamino-2-phenyl-l-butene 3-one.

B) Cyclization:

The starting material prepared according to A) was cyclized with ethyl formate to give the 3-cyano-1-methyl-5-phenyl-4 (1H) -pyri-60 don.

This end product had a melting point of 209 to 210 ° C.

Example 63:

A) The starting material of the formula IV was 2- (3-carboxyphenyl) -l-methylamino-4-phenyl-l-buten-3-one and / or 4- (3-carboxyphenyl) -l-methylamino-2 -phe-nyl) -1-butene-3 -one.

Example 69:

A) The starting material of the formula IV prepared was the 2 ~ methyl-l-methylamino-4- (3-trifluoromethylphenyl) -l-butten-3-one and / or the l-methylamino-2- (3-trifluoromethyl-Iphe- nyl) -l-buten-3-one.

630 356

B) Cyclization:

The starting material prepared according to A) was cyclized with ethyl formate to give 1,3-dimethyl-5- (3-trifluoromethylphenyl) -4 (1 H) -pyridone.

This product had a melting point of 130 to 131 ° C.

Example 70:

A) The starting material of the formula IV was 2-methyl-1-methylamino-4-phenyl-1-buten-3-one and / or 1-methylamino-2-phenyl-1-penten-3-one.

B) Cyclization:

The starting material prepared according to A) was cyclized with ethyl formate to give 1,3-dimethyl-5-phenyl-4 (1H) pyridone.

The product had a melting point of III ° C to 113 ° C.

Example 71:

A) The starting material of the formula IV was 2- (3-chlorophenyl) -l-methylamino-1-penten-3-one and / or 4- (3-chlorophenyl) -2-methyl-1-methylamino-1 -butene-3-one.

B) Cyclization:

The starting material prepared according to A) was cyclized with ethyl formate to give the 3- (3-chlorophenyl) -1,5-dimethyl-4 (1H) -pyridone.

This product had a melting point of 143 to 143.5 ° C.

Example 72:

A) The starting material of formula IV prepared was 2-ethyl-l-methylamino-4- (3-trifluoromethylphenyl) -l-butten-3-one and / or l-methylamino-2- (3-trifluoromethylphenyl) ) -l-hexen-3-one.

B) Cyclization:

The starting material prepared according to A) was cyclized with ethyl formate to give the 3-ethyl-l-methyl-5- (3-trifluoromethyl-phenyl) -4 (1H) -pyridone.

The melting point of the product was 95.5 to 96.5 ° C.

Example 73:

A) The starting material of formula IV prepared was 2-cyclohexyl-l-methylamino-4- (3-trifluoromethylphenyl) -l-buten-3-one and / or 4-cyclohexyl-l-methylamino-2- (3-trifluoromethylphenyl ) -l-buten-3-one.

B) Cyclization:

The starting material prepared according to A) was cyclized with ethyl formate to give the 3-cyclohexyl-l-methyl-5- (3-trifluoromethylphenyl) -4 (1H) pyridone.

This end product had a melting point of 174 to 175 ° C.

Example 74:

A) The starting material of formula IV prepared was 2-isopropyl-l-methylamino-4- (3-trifluoromethylphenyl) -l-buten-3-one and / or 5-methyl-l-methylamino-2- (3-tri -fluoromethylphenyl) -l-hexen-3-one.

B) Cyclization:

The starting material prepared according to A) was cyclized with ethyl formate to give the 3-isopropyl-l-methyl-5- (3-trifluoromethylphenyl) -4 (1H) -pyridone.

The melting point of this end product was 98.5 to 99.5 ° C.

Example 75:

A) The starting material of formula IV prepared was 2-hexyl-l-methylamino-4- (3-trifluoromethylphenyl) -l-bu-

26

ten-3-one and / or the l-methylamino-2- (3-trifluoromethylphenyl) -l-decen-3-one.

B) Cyclization:

The starting material prepared according to A) was cyclized with 5 ethyl formate to give the 3-hexyl-l-methyl-5- (3-trifluoromethyl-phenyl) -4 (1H) -pyridone.

The melting point of this end product was 89.5 to 90.5 ° C.

Example 76:

A) The starting material of formula IV prepared was 2-benzyl-l-methylamino-4- (3-trifluoromethylphenyl) -l-butten-3-one and / or l-methylamino-5-phenyl-2- (3 -trifluoromethylphenyl) -l-penten-3-one.

15 B) Cyclization:

The starting material prepared according to A) was cyclized with ethyl formate to give the 3-benzyl-l-methyl-5- (3-trifluoromethyl-phenyl) -4 (1H) -pyridone.

This end product had a melting point of 98 to

20100 ° C.

Example 77:

A) The starting material of the formula IV prepared was 2-butyl-1-methylamino-4- (3-trifluoromethylphenyl) -1-but

25 ten-3-one and / or the 4-butyl-l-methylamino-2- (3-trifluoromethylphenyl) -l-buten-3-one.

B) Cyclization:

The starting material prepared according to A) was mixed with ethyl formate to give the 3-butyl-l-methyl-5- (3-trifluoromethylphe-

30 nyI) -4 (1H) -pyridone cyclized.

The melting point of this end product was 82.5 to 84 ° C.

Example 78:

35 A) The starting material of the formula IV prepared was the 2- (3-cyclohexyl) -l-methylamino-4- (3-trifluoromethylphenyl) -l-buten-3-one and / or the 4- (3-cyclohexyl) -l-methyl-amino-2- (3-trifluoromethyl) -1-buten-3-one.

B) Cyclization:

40 The starting material prepared according to A) was cyclized with ethyl formate to give the 3- (3-cyclohexyl) -l-methyl-5- (3-trifluoromethylphenyl) -4 (1H) -pyridone.

This product had a melting point of 194 to 195 ° C.

Example 79:

A) The starting material of the formula IV prepared was l-methylamino-2-propyl-4- (3-trifluoromethylphenyl) -l-bu-

50 ten-3-one and / or the l-methylamino-4-propyl-2- (3-trifluoromethylphenyl) -l-buten-3-one.

B) Cyclization:

The starting material prepared according to A) was cyclized with ethyl formate to give the l-methyl-3-propyl-5- (3-trifluoromethyl-55 phenyl) -4 (1H) -pyridone.

The end product had a melting point of 45 to 47 ° C.

Example 80:

60 A) The starting material of the formula IV prepared was l-methylamino-2- (4-nitrophenyl) -4-phenyl-l-buten-3-one and / or l-methylamino-4- (4-nitrophenyl) - 2-phenyl-1-buten-3-one.

B) Cyclization:

65 The starting material prepared according to A) was cyclized with ethyl formate to give the l-methyl-3- (4-nitrophenyl) -5-phenyl-4 (1H) -pyridone.

The product had a melting point of 212 to 214 ° C.

27th

630 356

Example 81:

A) The starting material of the formula IV was 2,4-bis (3,4-dimethoxyphenyl) -l-methylamino-1-buten-3-one.

B) Cyclization:

The starting material prepared according to A) was cyclized with ethyl formate to give the 3,5-bis (3,4-dimethoxyphenyl) -l-methyl-4 (1H) -pyridone.

The product had a melting point of 182 to 184 ° C.

Example 82:

A) The starting material of the formula IV was 2-ethoxy-carbonyl-1-methylamino-4-phenyl-1-buten-3-one and / or 4-ethoxycarbonyl-1-methylamino-2-phenyl-1-butene -3-one.

B) Cyclization:

The starting material prepared according to A) was cyclized with ethyl formate to give the 3-ethoxycarbonyl-1-methyl-5-phenyl-4 (1H) -pyridone.

The melting point of the product was 107 to 108 ° C.

Example 83:

A) The starting material of the formula IV was 2- (2-furyl) -l-methylamino-4-phenyl-l-buten-3-one and / or 4- (2-furyl) -l-methylamino-2 -phenyI-l-buten-3-one ..

B) Cyclization:

The starting material prepared according to A) was cyclized with ethyl formate to give the 3- (2-furyl) -l-methyl-5-phenyl-4 (1H) -pyridone.

The melting point of the product was 191 to 193 ° C.

15

Cyclized ethyl formate to the 3- (3-isopropenylphenyl) -l-methyl-5-phenyl-4 (1H) pyridone.

The product showed maxima at 125,214,302 and 327 CPS and aromatic protons at 420 to 470 CPS in the NMR.

Example 88:

A) The starting material of the formula IV prepared was the 2- (3-ethylphenyl) -l-methylamino-4-phenyl-l-buten-3-one and / or the 4- (3-ethylphenyl) -l-methylamino-2- phenyl-l-

) buten-3-one.

B) Cyclization:

The starting material prepared according to A) was cyclized with ethyl formate to give the 3- (3-ethylphenyl) -l-methyl-5-phenyl-4 (1H) -pyridone.

The melting point of the product was 135 to 137 ° C.

Example 84:

A) The starting material of the formula IV prepared was 2-cyano-l-methylamino-4- (3-trifluoromethylphenyl) -l-butten-3-one and / or 4-cyano-l-methylamino-2- ( 3-trifluoromethylphenyl) -l-buten-3-one.

B) Cyclization:

The starting material prepared according to A) was cyclized with ethyl formate to give the 3-cyano-1-methyl-5- (3-trifluoromethyl-phenyl) -4 (1H) -pyridone.

The melting point of this product was 228 to 229 ° C.

Example 85:

A) The starting material of the formula IV prepared was the 2- (3,4-dimethoxyphenyl) -l-methylamino-4-phenyl-l-butten-3-one and / or the 4- (3,4-dimethoxyphenyl) - l-methylamino-no-2-phenyl-l-buten-3-one.

B) Cyclization:

The starting material prepared according to A) was cyclized with ethyl formate to give the 3- (3,4-dimethoxyphenyl) -l-methyl-5-phenyl-4 (1H) -pyridone.

The melting point of the product was 154 to 157 ° C.

Example 86:

The 3- (3-cyclohexenyl) -l-methyl-5- (3-trifluoromethylphenyl) -4 (1H) -pyridone prepared according to Example 78 was converted to the 3- (3,4-dibromocyclohexyl) -l-methyl-5- ( 3-trifluoromethylphenyl) -4 (1H) pyridone hydrobromide brominated.

The melting point of this product was 196 to 198 ° C.

Example 87:

A) The starting material of the formula IV prepared was 2- (3-isopropenylphenyl) -l-methylamino-4-phenyl-l-butten-3-one and / or 4- (3-isopropenylphenyl) -l-methylami -no-2-phenyl-l-buten-3-one.

B) Cyclization:

The starting material produced according to A) was with

Example 89:

A) The starting material of the formula IV prepared was the 2- (3-hexylphenyl) -1-methylamino-4-phenyl-1-buten-3-one

20 and / or the 4- (3-hexylphenyl) -l-methylamino-2-phenyl-l-buten-3-one.

B) Cyclization:

The starting material prepared according to A) was cyclized with ethyl formate to give the 3- (3-hexylphenyl) -l-methyl-5-phenyl-25 4 (1H) -pyridone.

The melting point of the product was 93 to 95 ° C.

Example 90:

A) The starting material of formula IV prepared was 2- (4-ethylphenyl) -l-methylamino-4-phenyl-l-buten-3-one and / or 4- (4-ethylphenyl) -l-methylamino- 2-phenyl-l-buten-3-one.

B) Cyclization:

The starting material prepared according to A) was cyclized with 35 ethyl formate to give the 3- (4-ethylphenyl) -l-methyl-5-phenyl-4 (1H) -pyridone.

The melting point of this product was 143 to 145 ° C.

Example 91

40 A) The starting material of formula IV prepared was the 2- (3-cyclohexylmethylphenyl) -l-methylamino-4-phenyl-l-buten-3-one and / or the 4- (3-cyclohexylmethylphenyl) -l-methylamino -2-phenyl-l-buten-3-one.

B) Cyclization:

45 The starting material prepared according to A) was cyclized with ethyl formate to give the 3- (3-cyclohexylmethylphenyl) -l-methyl-5-phenyl-4 (1 H) -pyridone.

The melting point of this product was 147 to 148 ° C.

50 Example 92:

A) The starting material of the formula IV prepared was l-methylamino-2-phenyl-4-benzylthio-l-buten-3-one and / or l-methylamino-4-phenyl-2-benzylthio-l-buten-3 -on.

B) Cyclization:

55 The starting material prepared according to A) was cyclized with ethyl formate to give the 1-methyl-3-phenyl-5-benzylthio-4 (1H) -pyridone.

The melting point of the product was 155 to 157 ° C.

Example 93:

A) The starting material of the formula IV prepared was l-methylamino-2-phenyl-4-phenylthio-l-buten-3-one and / or l-methylamino-4-phenyl-2-phenylthio-l-buten-3 -on.

65 B) Cyclization:

The starting material prepared according to A) was cyclized with ethyl formate to give the l-methyl-3-phenyl-5-phenylthio-4 (1H) pyridone

630 356

The melting point of this product was 164 to 165 ° C.

The phenylthio compound thus obtained was oxidized to the 1-methyl-3-phenyl-5-phenylsulfonyl-4 (1H) -pyridone with m-chloroperbenzoic acid.

The melting point of the sulfonyl compound was 218 to 220 ° C and the yield was 50%.

Example 94:

A) The starting material of the formula IV prepared was the l-methylamino-2-phenoxy-4-phenyl-l-buten-3-one and / or the l-methylamino-4-phenoxy-2-phenyl-l-buten-3 -on.

B) Cyclization:

The starting material prepared according to A) was cyclized with ethyl formate to give the l-methyl-3-phenoxy-5-phenyl-4 (1H) -py-ridone.

The melting point of this product was 176 to 177 ° C.

Example 95:

A) The starting material of the formula IV produced was 2-methoxy-l-methylamino-4-phenyl-l-buten-3-one and / or 4-methoxy-l-methylamino-2-phenyl-l-buten-3 -on.

B) Cyclization:

The starting material prepared according to A) was cyclized with ethyl formate to give the 3-methoxy-l-methyl-5-phenyl-4 (1H) -py-ridone.

The melting point of this product was 153 to 155 ° C.

Example 96:

1 g of the 3- (3-benzyloxyphenyl) -l-methyl-5-phenyl ~ 4 (1H) -pyridone prepared by the process according to Example 18 is dissolved in 250 ml of acetic acid, whereupon 1 g of 5 percent palladium-on Coal admits. The mixture is hydrogenated for about 45 minutes and then filtered, after which the filtrate is evaporated to dryness. By recrystallizing the product obtained from ethyl acetate-hexane, 0.45 g of 3- (3-hydroxyphenyl) -l-methyl-5-phenyl-4 (1H) -pyridone is obtained, which melts at 223 to 225 ° C.

The same compound is also produced by cleavage with pyridine hydrochloride in the following manner.

2 g of 3- (3-methoxyphenyl) -l-methyl-5-phenyl-4 (1H) -pyridone are mixed with 15 g of pyridine hydrochloride, whereupon the mixture is heated to reflux temperature for about 1 hour. The mixture is then poured into a large amount of water and the precipitated solids are separated by filtration. After recrystallization of the solids from ethanol-ethyl ether, 1.1 g3- (3-hydroxyphenyl) -l-methyl-5-phenyl-4 (1H) -pyridone is obtained. Another 0.65 g of product are obtained by concentrating the above filtrate. The product obtained is identical to the compound obtained in the first part of this example.

The following compound is obtained by a process similar to Example 96:

3-Cyclohexyl-5- (3-hydroxyphenyl) -l-methyl-4 (1H) -pyridone, melting point 155 to 165 ° C, yield 13%.

Example 97:

3.2 g of the product according to Example 96 are added to a suspension of 0.86 g of sodium hydride in 50 ml of dimethyl sulfoxide. The mixture is stirred at room temperature and 3.5 g of ethyl iodide are added. The reaction mixture is stirred for a further 2.5 hours and then poured into water, whereupon the aqueous mixture is extracted with ethyl acetate. The extract is washed with dilute hydrochloric acid and then with water and finally dried. The dried extract is filtered and the filtrate is evaporated to dryness in vacuo. The product obtained is 2.2 g3- (3-ethoxyphenyl) -l-methyl-5-phenyl-4 (1H) -pyridone, which melts at 133 to 135 ° C.

28

The following further compounds are prepared in a manner similar to Example 97.

3- (3-allyloxyphenyl) -l-methyl-5-phenyl-4 (1H) -pyridone, NMR maxima at 211 and 270 CPS, broad maxima at 296 to 5 328.341 to 378 and 399 to 458 CPS, yield 10% .

3- [3- (l-fluoro-2-iodovinyloxy) phenyl] -l-methyl-5-phenyl-4 (1H) pyridone, NMR maxima at 218 CPS, a broad maximum at 270 to 316 CPS, aromatic protons at 416 to 464 CPS, yield 67%. 10 3- (3-isopropoxyphenyl) -l-methyl-5-phenyl-4 (1H) -pyridone, NMR maxima at 81.209 and 276 CPS, aromatic protons at 401 to 468 CPS, yield 18%.

3- (3-Cyanomethoxyphenyl) -l-methyl-5-phenyl-4 (1H) -py-ridone, NMR maxima at 207 and 275 CPS, aromatic protons at 396 to 456 CPS, yield 6%.

3- (3-Dodecyloxyphenyl) -l-methyl-5-phenyl-4 (1H) -pyridone, NMR maxima at 52.207 and 234 CPS, a broad maximum at 60 to 122 CPS, aromatic protons at 396 to 461 CPS , Yield 26%. 20 l-Methyl-3- [3- (4-nitrophenoxy) phenyI] -5-phenyl-4 (1H) -pyridone, NMR maxima at 222 and 488.5 CPS, aromatic protons at 414 to 463 CPS, yield 14 %.

l-Methyl-3- (3-methylsulfonyloxyphenyl) -5-phenyl-4 (1H) -pyridone, NMR maxima at 185 and 213 CPS, aromatic Pro-25 tones at 422 to 472 CPS, yield 20%.

l-Methyl-3-phenyl-5- [3- (l, l, 2,2-tetrafluoroethoxy) phenyl] -4 (lH) pyridone, melting point 119 to 121 ° C, yield 84%, produced using tetrafluoroethylene in the presence of potassium hydroxide. 30 3- (3-acetoxyphenyl) -l-methyl-5-phenyl-4 (1H) -pyridone, NMR maxima at 134 and 210 CPS, aromatic protons at 415 to 466 CPS, yield 28%, produced using acetic anhydride .

3- (3-hexyloxyphenyl) -l-methyl-5-phenyl-4 (1H) -pyridone, 35 NMR maxima at 53.214 and 239 CPS, a broad maximum at 60 to 120 CPS, aromatic protons at 402 to 465 CPS, Yield 55%.

3- (3-decyloxyphenyl) -l-methyl-5-phenyl-4 (1H) -pyridone, NMR maxima at 53.211 and 239 CPS, a broad maximum 40 at 62 to 123 CPS, aromatic protons at 404 to 467 CPS, Yield 24%.

l-Methyl-3-phenyl-5- (3-propoxyphenyl) -4 (1H) -pyridone, NMR maxima at 54,101,5,208 and 232 CPS, aromatic protons at 400 to 463 CPS, yield 31%. 45 l-methyl-3-phenyl-5- (3-propargyloxyphenyl) -4 (1H) -pyridone, NMR maxima at 150 and 215 CPS, a broad maximum at 280 to 285 CPS, aromatic protons at 430 to 470 CPS, yield 6%.

3- (3-Cyclohexylmethoxyphenyl) -l-methyl-5-phenyl-50 4 (1H) -pyridone, NMR maxima at 214 and 226 CPS, a broad maximum at 35 to 124 CPS, aromatic protons at 402 to 466 CPS, Yield 16%.

l-Methyl-3- (3-octyloxyphenyl) -5-phenyl-4 (1H) -pyridone, NMR maxima at 52.218 and 239 CPS, a broad maxi-55 mum at 58 to 122 CPS, aromatic protons at 403 up to 467 CPS, yield 19%.

l-Methyl-3- (3-phenoxyphenyl) -5-phenyI-4 (1H) -pyridone, NMR maximum at 214 CPS, aromatic protons at 410 to 470 CPS, yield 34%.

60

Example 98:

The l-methyl-3,5-diphenyl-4 (1H) -pyridone was prepared according to the procedure described in Example 27. 65 Typical salt compounds into which the pyridones of the formula Ia or pyridothiones of the formula Ib, which are prepared by the process according to the invention, can be converted, are the acid addition salts.

29

630 356

The acid addition salts described in Examples 99 and 100 below were prepared by combining the pyridone of Example 98 with an appropriate acid in aqueous solvent.

Example 99:

1-methyl-3,5-diphenyl-4 (1 H) -pyridone hydroiodide, melting point 110 ° C, yield 100%.

Example 100:

l-methyl-3,5-diphenyl-4 (1H) -pyridone hydrochloride, melting point 187 to 194 ° C, yield 100%.

Example 101:

This example is used to explain the preparation of a pyridothione of the formula Ib by reacting the corresponding pyridone of the formula Ia with phosphorus pentasulfide.

10 g of the 3,5-diphenyl-1-methyl-4 (1H) -pyridone prepared according to Example 98 are mixed with 10 g of phosphorus pentasulfide in 100 ml of pyridine, whereupon the mixture obtained is heated under reflux for 2 hours, then in a large amount Pouring water and stirring for an hour. The mixture is then filtered. By recrystallizing the solids obtained, 9.8 g of 3,5-diphenyl-1-methyl-4 (1H) -pyridothione, which melts at 168 to 171 ° C., is obtained.

Example 102:

The pyridothiones listed below were prepared from the corresponding pyridones by the process described in Example 101:

3- (3-bromophenyl) -l-methyl-5-phenyl-4 (1H) -pyridothione, melting point 185 to 188 ° C, yield 59%, 5 l-methyl-3- (4-chlorophenyl) -5- ( 3-trifluoromethylphenyl) -4 (1H) -pyridothione, melting point 239 to 242 ° C, yield is 25%,

l-methyl-3- (3-methylphenyl) -5- (3-trifluoromethylphenyl) -4 (1H) -pyridothione, melting point 193 to 196 ° C., yield 10 is 50%,

l-methyl-3- (2-methylphenyl) -5- (3-trifluoromethylphenyl) -4 (1H) -pyridothione, melting point 193-195 ° C., yield is 35%,

l-methyl-3-propyl-5- (3-trifluoromethylphenyl) -4 (1H) -pyri-15 dothione, melting point 145 to 148 ° C., yield 40%,

l-methyl-3-phenoxy-5- (3-trifluoromethylphenyl) -4 (1H) -pyridothione, melting point 127 to 131 ° C., yield 40%,

3-ethylthio-l-methyl-5- (3-trifluoromethylphenyl) -4 (1H) -pyridothione, melting point 136 to 138 ° C, yield is 20 55%,

3-ethoxy-l-methyl-5- (3-trifluoromethylphenyl) -4 (1H) -py-ridothion, melting point 153 to 155 ° C., yield 5%,

3,5-bis (3-chlorophenyl) -l-methyl-4 (1H) -pyridothione, melting point 210 to 212 ° C, yield 86%, 25 3- (3-chlorophenyl) -l-methyl-5-phenyl- 4 (1H) -pyridothione, melting point 190 to 193 ° C, yield 71%,

l-Methyl-3-phenyl-5- (3-trifluoromethylphenyl) -4 (1H) -pyridothione, melting point 210 ° C., yield 70%.

C.

Claims (4)

630 356 PATENT CLAIMS 1) Process for the preparation of 3-phenyl-5-substituted-4 (1H) -pyridones of the formula Ia in which X is oxygen, R is hydrogen, C1-C3-alkyl, by halogen, cyano, carboxy or Methoxycarbonyl substituted C1-C3-alkyl, Q-C3-alkenyl, C2-C3-alkynyl, C1-C3-alkoxy, hydroxy or dimethylamino, with the proviso that the substituent R contains no more than 3 carbon atoms, the radicals R1 independently of one another halogen, Q-Cg-alkyl, halo-substituted Q-Cg-alkyl, Q-Cg-alkyl monosubstituted with phenyl, cyano or Cj-C3-alkoxy, Q-Cg-alkenyl, halogen-substituted Q-Cg- Alkenyl, Q-Cg-alkynyl, halogen-substituted C ^ -Cg-alkynyl, C3-C6-cycloalkyl, C4-C6-cycloalkenyl, C4-Cg-cycloalkylalkyl, C1-C3-alkanoyloxy, C1-C3-alkyl-sulfonyloxy, Phenyl, phenyl monosubstituted by halogen, C1-C3-alkyl, Cx-C3-alk-oxy or nitro, nitro, cyano, carboxy, hydroxy, QQ-alkoxycarbonyl, -O-R3, -S-R3, -SO-R3 or Mean -S02-R3, where R3 is Cj-C12-alkyl, halogen substituted C | CX2-alkyl, phenyl, cyano or Ci-C3-alkoxy monosubstituted Ci-C12-alkyl, phenyl, halogen, C1-C3-alkyl, Cx-C3-alkoxy or nitro monosubstituted phenyl, C3-C6-cycloalkyl, C4-C8-cycloalkylalkyl, C2-C12-alkenyl, halogen-substituted C2-CI2-alkenyl, C2-C12-alkynyl or halogen-substituted C2-C12-alkynyl, with the proviso that the substituent R3 contains at most 12 carbon atoms, R2 for halogen, Hydrogen, cyano, C1-C3-alkoxycarbonyl, C1-C6-alkyl, Q-Cg-alkyl substituted by halogen or C1-C3-alkoxy, C ^ -Cg-alkenyl, C2 substituted by halogen or Cx-C3-alkoxy -C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl, C3-C6-cycloalkyl substituted by halogen, Cj-Q-alkyl or QQ-alk-oxy, C4-C6-cycloalkenyl, C4-C8-cycloalkylalkyl, Phenyl-C1-C3-alkyl, furyl, naphthyl, thienyl, -O-R4, -S-R4, -SO-R4, -S02-R4 or Ci-C12-alkyl, phenyl, by halogen, C1-C3 -Alkyl, Q-Cj-alkoxy or nitro monosubstituted phenyl, C3-C6-cycloalkyl, C4-C8-cycloalkylalkyl, QC ^ -Alkenyl, halogen-substituted QC ^ -alkenyl, QC ^ -alkynyl or halogen-substituted C2-C12-alkynyl, with the proviso that the substituent R6 contains at most 12 carbon atoms, the indices m and n independently of one another 0.1 or 2 mean, the index m being 1 or 2 if X is oxygen, R is hydrogen or methyl io and R2 is unsubstituted phenyl, and the salts of the compounds of the formula I, characterized in that a compound of the formula 15-20 Ji> 0 II-C-C-R2-II IV, Q1, R4 is C1-C3-alkyl, halogen-substituted QQ-alkyl, Qr-C3-alkenyl, halogen-substituted C2-C3-alkenyl, benzyl, phenyl or by halogen , QQ-alkyl or QQ-alkoxy substituted phenyl, the radicals R5 independently of one another halogen, Q-Cg-alkyl, halogen-substituted Q-Cg-alkyl, phenyl, cyano or Q-C3-alkoxy monosubstituted Cj-Cg-alkyl, QQ -Alkenyl, halogen-substituted C2-C8-alkenyl, C2-C8-alkynyl, halogen-substituted QC g-alkynyl, C3-C6-cycloalkyl, C4-C6-cyclo-alkenyl, C4-C8-cycloalkylalkyl, C1-C3-alkanoyloxy, Q-C3-alkylsulfonyloxy, phenyl, by halogen, C1-C3-alkyl, Cx-C3 -Alkoxy or nitro are monosubstituted phenyl, nitro, cyano, carboxy, hydroxy, C1-C3-alkoxycarbonyl, -O-R6, -S-R6, -SO-R6 or -SO2-R6, where R6 is Cj-C12-alkyl , halogen-substituted QC ^ alkyl, monosubstituted by phenyl, cyano or C1-C3-alkoxy in which R1, R2 and m have the meanings given above, and one of the substituents Q1 or Q2 represents two hydrogen atoms and the other a radical of the formula = CHNHR means in which R has the meaning given above, cyclized with a formulation agent. 1-methyl-3-phenoxy-5-phenyl-4 (1 H) -pyridone, 1-methyl-3-phenyl-5-phenylsulfonyl-4 (1 H) -pyridone, 3-methoxy-1-methyl-5- phenyl-4 (1H) pyridone, 630 356 3 - (3-Hydroxyphenyl) -1-methyl-5-phenyl-4 (1H) -pyridone, 3-cyclohexyl-5- (3-hydroxyphenyl) -l-methyl-4 (1H) -pyridone, 3- (3rd -Ethoxyphenyl) -l-methyl-5-phenyl-4 (1H) -pyridone, 3 - (3-allyloxyphenyl) -1 -methyl-5 -phenyl-4 (1H) -pyridone, 3- [3- (l -Fluor-2-iodovinyloxy) phenyl] -l-methyl-5-phenyI- 5 4 (lH) pyridone, 3- (3-isopropoxyphenyl) -l-methyl-5-phenyl-4 (1H) -pyridone, 3- (3-cyanomethoxyphenyl) -l-methyl-5-phenyl-4 (1H) -pyridone, 3- (3-dodecyloxyphenyl) -l-methyl-5-phenyl-4 (1H) -pyridone, 10 l-methyl-3- [3- (4-nitrophenoxy) phenyl] -5-phenyl-4 (1H) pyri- Don, l-methyl-3- (3-methylsulfonyloxyphenyl) -5-phenyl-4 (lH) -py-ridone, l-methyl-3-phenyl-5- [3- (l, l, 2,2-tetrafluoroethoxy) phenyl] - 15 4 (lH) -pyridone, 3- (3-acetoxyphenyl) -l-methyl-5-phenyl-4 (1H) -pyridone, 3- (3-hexyloxyphenyl) -l-methyl-5-phenyl-4 (1H) -pyridone, 3- (3-decyloxyphenyl) -l-methyl-5-phenyl-4 (1H) -pyridone, l-methyl-3-phenyl-5- (3-propoxyphenyl) -4 (1H) pyridone, 20 l-methyl-3-phenyl-5- (3-propargyloxyphenyl) -4 (1H) -pyridone, 3- (3-cyclohexylmethoxyphenyl) -l-methyl-5-phenyl-4 (1H) -py- ridon, l-methyl-3- (3-octyloxyphenyl) -5-phenyl-4 (1H) pyridone, l-methyl-3- (3-phenoxyphenyl) -5-phenyl-4 (1H) pyridone, 25 1 - acetoxy -3,5-diphenyl-4 (1H) pyridone, 1-methyl-3,5-diphenyl-4 (1H) pyridone hydroiodide, 1-methyl-3,5-diphenyl-4 (1H-pyridone hydrochloride , 3,5-diphenyl-1-methyl-4 (1H) -pyridine thione, 3,5-bis (3-chlorophenyl) -l-methyl-4 (1H) -pyridine thione, 30 1-penten-3-one cyclized with ethyl formate. indicates that a starting material from 2- (2-furyl) - 65. The method according to claim 2 for the preparation of 45 l-methylamino-4-phenyl-l-buten-3-one and / or 4- (2-furyl) -3- (3-chlorophenyl) -l, 5-dimethyl- 4 (1H) -pyridone, thereby gel-methylamino-2-phenyl-1-buten-3-one with ethyl formate cycli-indicates that a starting material is made from 2- (3-chloro). phenyI) -l-methylamino-l-penten-3-one and / or 4- (3-chloro-77. Process according to claim 2 for the preparation of phenyl) -2-methyl-l-methylamino-l-buten-3- on with ethylfor- 3-cyano-l-methyl-5- (3-trifluoromethylphenyl) -4 (1H) -pyridone, cyclized. 50 characterized in that a starting material 66. The method according to claim 2 for the preparation of 2-cyano-l-methylamino-4- (3-trifluoromethylphenyl) -l-buten-3-ethyl-l-methyl-5- (3-trifluoromethylphenyl) -4 (lH) - pyridone, 3-one and / or 4-cyano-l-methylamino-2- (3-trifluoromethyl-characterized in that one cyclizes a starting material from phenyl) -l-buten-3-one with ethyl formate. 1-methyl-3-phenyl-5- (3-thienyl) -4 (1H) -pyridone, thereby genyl) -l-methylamino-2- (3-trifluoromethyl) -l-buten-3-one that one cyclizes a starting material from 1-methylami- 25 ethyl formate. no-2-phenyl-4- (3-thienyl) -l-buten-3-one and / or 1-methyl- 73. Process according to claim 2 for the preparation of amino-4-phenyl-2- (3-thienyl) -l-buten-3-one with ethyl formate l-methyl-3-propyl-5- (3-trifluoromethylphenyl) -4 (lH) -pyridone, cyclized. characterized in that one is a starting material 62. The method according to claim 2 for the preparation of l-methylamino-2-propyl-4- (3-trifluoromethylphenyl) -l-buten-3-cyano-l-methyl-5-phenyl-4 (lH) -pyridone, characterized thereby - 30 3-one and / or l-methylamino-4-propyl-2- (3-trifluoromethyl) records that a starting material is made from 2-cyano-l-methenyl) -l-buten-3-one with ethyl formate cyclized. thylamino-4-phenyl-l-buten-3-one and / or 4-cyano-l-me-74. Process according to claim 2 for the preparation of thylamino-2-phenyl-l-buten-3-one cyclized with ethyl formate. l-Methyl-3- (4-nitrophenyl) -5-phenyl-4 (1H) -pyridone, thereby 63. The method according to claim 2 for the preparation of characterized in that a starting material from 1-methyl-l, 3-dimethyl-5- (3-trifluoromethylphenyl) -4 (lH) pyridone, 35 amino-2- (4-nitrophenyl ) -4-phenyl-l-buten-3-one and / or characterized in that a starting material from l-methylamino-4- (4-nitrophenyl) -2-phenyl-l-buten-3-one with 1-methyl-3- (3-trifluoromethylphenyl) -4 (lH) -pyridone, thereby 2-hexyl-l-methylamino-4- (3-trifluoromethylphenyl) -l-butene-labeled, that l-methylamino-2- (3-trifluoromethyl-5 3-one and / or l-methylamino-2- (3-trifluoromethylphenyl) -l-phenyl) -l-buten-3-one cyclized with ethyl formate. cyclized decen-3-one with ethyl formate. 58. The method of claim 2 for the preparation of 70. The method of claim 2 for the preparation of 3- (3-cyanophenyl) -l-methyl-5-phenyl-4 (lH) -pyridone, 3-benzyl-l-methyl-5 - (3-trifluoromethylphenyl) -4 (1H) -pyridone, characterized in that a starting material is characterized in that a starting material is made of 1-methylamino-2-phenyl-4- (3-trifluoromethylphenyl) -l-butene-4 (1H) -pyridone, characterized in that an 3-one and / or l-methylamino-4-phenyl-2- (3-trifluoromethyl) starting material from l- (l-carboxyethylamino) -2-phenyl-4- (3-tri-phenyl) -l-butene 3-one cyclized with ethyl formate.fluoromethylphenyl) -l-buten-3-one and / or l- (l-carboxy- 36. The method according to claim 2 for the preparation of ethylamino) -4-phenyl-2- (3-trifluoromethylphenyl) -l-buten-3-3- (3-methoxyphenyl) -l-methyl-5-phenyl-4 (lH) -pyridone, cyclized with ethyl formate. characterized in that a starting material from 48. Process according to claim 2 for the production of 1-Methyl-3-phenyl-5- (3-trifluoromethylphenyl) -4 (lH) -pyridone, 47. Process according to claim 2 for the preparation of, characterized in that a starting material from l- (l-carboxyethyl) -3- phenyl-5- (3-trifluoromethylphenyl) - 1-methylamino-2- (2-methylphenyl) -4-phenyl-l-buten-3-one phenyl) -l-methylamino-4-phenyl-l-buten-3-one and / or 4- (2-and / or l-methylamino-4- (2-methylphenyl) -2-phenyl-l-bu-fluorophenyl) -l-methylamino-2-phenyl-l-buten-3-one with ten-3-one cyclized with ethyl formate. Cyclized ethyl formate. 34. Process according to claim 2 for the production of 5 46. Process according to patent claim 2 for the production of 3- (4-fluorophenyl) -l-methyl-5-phenyl-4 (1H) pyridone, 3- (3-bromophenyl) - l-methyl-5- (3-trifluoromethylphenyl) -4, characterized in that a starting material from (lH) -pyridone, characterized in that an 1-allylamino-2-phenyl-4- (3-trifluoromethylphenyl) -l-buten-3-one and / or l-allylamino-4-phenyI-2- (3-trifluoromethylphenyl) -l-buten-3- cyclized with ethyl formate. 13. The method according to claim 2 for the preparation of 3- (4-isopropylphenyl) -l-methyl-5-phenyl-4 (lH) -pyridone, characterized in that a starting material 2-ethyl-l-methylamino-4- (3-trifluoromethylphenyl) -l-butene-3- 78. The process according to claim 2 for the preparation of on and / or l-methylamino-2- (3-trifluoromethylphenyl) -l-he - 55 3- (3,4-Dimethoxyphenyl) -l-methyl-5-phenyl-4 (1H) -pyridone, xen-3-one cyclized with ethyl formate. characterized in that one is a starting material 67. The method according to claim 2 for the preparation of 2- (3,4-dimethoxyphenyl) -l-methylamino-4-phenyl-l-butene 3-CyclohexyI-l-methyl-5- (3-trifluoromethylphenyl) -4 (1H) -py- 3-one and / or 4- (3,4-dimethoxyphenyl) -l-methylamino-2-ridone, characterized in that that one cyclizes a starting material phenyl-l-buten-3-one with ethyl formate. from 2-cyclohexyl-l-methylamino-4- (3-trifluoromethylphenyl) - 60 79. Process according to claim 2 for the preparation of l-buten-3-one and / or 4-cyclohexyl-l-methylamino-2- (3- tri- 3- (3-isopropenylphenyl) -l-methyl-5-phenyl-4 (1H) -pyridone, Cyclomethylphenyl) -l-buten-3-one cyclized with ethyl formate. characterized in that one is a starting material 68. The method according to claim 2 for the preparation of 2- (3-isopropenylphenyl) -l-methylamino-4-phenyl-l-butene-3-3-isopropyl-l-methyl-5- (3-trifluoromethylphenyl) -4 (lH ) -pyrion and / or 4- (3-isopropenylphenyl) -l-methylamino-2-phe-don, characterized in that a starting material 65 nyl-l-buten-3-one is cyclized with ethyl formate. from 2-isopropyl-l-methylamino-4- (3-trifluoromethylphenyl) -l- 80. Process according to claim 2 for the preparation of buten-3-one and / or 5-methyl-l-methylamino-2- (3-trifluoro - 3- (3-ethylphenyl) -l-methyl-5-phenyl-4 (1H) -pyridone, thereby cyclizing methylphenyl) -l-hexen-3-one with ethyl formate. characterized that a starting material from 2- (3- 630 356 Ethylphenyl) -1-methylamino-4-phenyl-1-buten-3-one and / or 4- (3-ethylphenyl) -l-methylamino-2-phenyl-l-buten-3-one cyclized with ethyl formate. 81. The method according to claim 2 for the production of 3- (3-Hexylphenyl) -l-methyl-5-phenyl-4 (1H) -pyridone, characterized in that a starting material from 2- (3-He-xylphenyl) -l -methylamino-4-phenyl-1 -butene-3-one and / or 4- (3-Hexylphenyl) -l-methylamino-2-phenyl-l-buten-3-one cyclized with ethyl formate. 82. The method according to claim 2 for the production of 3- (4-ethylphenyl) -l-methyl-5-phenyl-4 (1H) -pyridone, characterized in that a starting material from 2- (4-ethylphenyl) -l-methylamino-4-phenyl-l-butene -3-on and / or 4- (4-ethylphenyl) -l-methylamino-2-phenyl-l-buten-3-one cyclized with ethyl formate. 83. The method according to claim 2 for the preparation of 3- (3-cyclohexylmethylphenyl) -l-methyl-5-phenyl-4 (lH) -pyri-don, characterized in that a starting material from 2- (3-cyclohexylmethylphenyl) -l -methylamino-4-phenyl-l-buten-3-one and / or 4- (3-cyclohexylmethylphenyl) -l-methyl-amino-2-phenyl-l-buten-3-one cyclized with ethyl formate. 84. The method according to claim 2 for the preparation of l-methyl-3-phenyl-5-benzylthio-4 (lH) -pyridone, characterized in that a starting material from 1-methylamino-no-2-phenyl-4-benzylthio- Cyclized l-buten-3-one and / or 1-methyl-amino-4-phenyl-2-benzylthio-l-buten-3-one with ethyl formate. 85. The method according to claim 2 for the preparation of l-methyl-3-phenyl-5-phenylthio-4 (lH) pyridone, characterized in that a starting material from 1-methylamino-no-2-phenyl-4-phenylthio- Cyclized l-buten-3-one and / or 1-methylamino-4-phenyl-2-phenylthio-l-buten-3-one with ethyl formate. 86. The method according to claim 2 for the preparation of l-methyl-3-phenoxy-5-phenyl-4 (lH) pyridone, characterized in that a starting material from 1-methylamino-no-2-phenoxy-4-phenyl- Cyclized l-buten-3-one and / or 1-methylamino-4-phenoxy-2-phenyl-l-buten-3-one with ethyl formate. 87. The method according to claim 2 for the preparation of 3-methoxy-l-methyl-5-phenyl-4 (lH) -pyridone, characterized in that a starting material from 2-methoxy-l-methylamino-4-phenyl-l- Cyclized buten-3-one and / or 4-methoxy-l-methylamino-2-phenyl-l-buten-3-one with ethyl formate. 88. The method according to claim 1, characterized in that salts of the compounds of the formula I are prepared by treating the compounds of the formula I with an acid or base. 89. Process for the preparation of new 3-phenyl-5-substituted-4 (1H) -pyridothiones of the formula Ib X Ii the radicals R1 independently of one another halogen, Q-C8-alkyl, halogen-substituted QQ-alkyl, Q-C8-alkyl monosubstituted with phenyl, cyano or C1-C3-alkoxy, C2-C8-alkenyl, halogen-substituted Q-C8- Alkenyl, C2-C8-alkynyl, halo-5-substituted Q-C8-alkynyl, C3-C6-cycloalkyI, C4-C6-cy-cloalkenyl, C4-Cs-cycloalkylalkyl, C1-C3-alkanoyloxy, Q-C3-alkylsulfonyloxy, Phenyl, phenyl, nitro, cyano, carboxy, hydroxy, C1-C3-alkoxycarbonyl, -O-R3, -S-R3, 10 -SO-R3 or - monosubstituted by halogen, C1-C3-alkyl, QQ-alkoxy or nitro S02-R3 mean, where R3 for Cx-C12-alkyl, halogen-substituted Q-C12-alkyl, phenyl, cyano or Q-C3-alkoxy monosubstituted Q-C12-alkyl, phenyl, halogen, C1-C3-alkyl, QQ-alkoxy or nitro monosubstituted phenyl , C3-C6-cycloal-15 alkyl, C4-C8-cycloalkylalkyl, C2-C12-alkenyl, halogen-substituted QC ^ -alkenyl, QC ^ -alkynyl or halogen-substituted C2-C12-alkynyl, with the proviso that the substituent R3 is at most Contains 12 carbon atoms, R2 for halogen, hydrogen, cyano, Q-C3-alkoxycarbo-20 nyl, Q-C6-alkyl, QQ-alkyl substituted by halogen or C1-C3-alkoxy, QQ-alkenyl, C2 substituted by halogen or Q-C3-alkoxy -C6-alkenyl, C2-C6-alkynyl, Q-C6-cycloalkyl, halogen-substituted, Q-C3-alkyl or QQ-alkoxy-C3-C6-cycloalkyl, C4-C6-cycloalkenyl, C4-25 C8-cycloalkylalkyl , Phenyl-C1-C3-alkyl, furyl, naphthyl, thienyl, -O-R4, -S-R4, -SO-R4, -S02-R4 or 30th —R R4 represents C1-C3-alkyl, halogen-substituted Q-Q-alkyl, Cj-Q-alkenyl, halogen-substituted Q-Q-alkenyl, benzyl, phenyl or phenyl substituted by halogen, C1-C3-alkyl or Q-C3-alkoxy, the radicals R5 independently of one another halogen, Q-C8-alkyl, halogen-substituted Q-Cs-alkyl, Q-C8-alkyl monosubstituted by phenyl, cyano or C1-C3-alkoxy, C2-C8-40 alkenyl, halogen-substituted C ^ -Q- Alkenyl, Cj-Cg-alkynyl, halogen-substituted C2-C8-alkynyl, C3-C6-cycloalkyl, C4-C6- 'cycloalkenyl, C4-C8-cycloalkylalkyl, QQ-alkanoyloxy, Ct-C3-alkylsulfonyloxy, phenyl, by halogen, QQ -Alkyl, Q-C3-alkoxy or nitro mean monosubstituted phenyl, nitro, cyano, 45 carboxy, hydroxy, QQ-alkoxycarbonyl, -O-R6, -S-R6-SO-R6 or -S02-R6, where R6 for Ci-C12-alkyl, halogen-substituted Cj-C ^ -alkyl, phenyl, cyano or Q-C3-alkoxy monosubstituted Q-C12-alkyl, phenyl, by halogen, Q-C3-alkyl, Cx-C ^ 50 alkoxy or nitro monosubstituted phenyl, QQ-cycloalkyl, C4-C8-cycloalkylalkyl, C2-C12-alkenyl, halogen-substituted Q-C12-alkenyl, Q-C12-alkynyl or halogen-substituted C2-C12-alkynyl, with the proviso that the Substituent R6 contains at most 12 carbon atoms, 55 the indices m and n are independently of one another 0, 1 or 2, or of salts of the compounds of the formula Ib, characterized (Ib) in that a compound of the formula IV 60 A > 0 II ~ C — C — C — Ra II II IV, in which X is a sulfur atom, R represents hydrogen, C1-C3-alkyl, Q-C3-alkyl substituted by halogen, cyano, carboxy or methoxycarbonyl, C2-C3-alkenyl, QQ-alkoxy, Q-C3-alkynyl, hydroxy or dimethylamino, with which Provided that the substituent R contains no more than 3 carbon atoms, in which «S R1, R2 and m have the meaning given in formula Ib, and one of the substituents Q1 or Q2 represents two hydrogen atoms and the other represents a radical of the formula = CHNHR means in which R has the meaning given in formula Ib, with a formylating agent to give the 3-phenyl-5-substituted 4 (1H) pyridone of the formula Ia (Ia) cyclized, and this is then converted with phosphorus pentasulfide into the corresponding thion of formula Ib. 90. The method according to claim 89, characterized in that the 3,5-diphenyl-l-methyl-4 (lH) -pyridine-thione is prepared by the 2,4-diphenyl-l-methylamino-l-butene 3-one cyclized with ethyl formate to the 3,5-diphenyl-l-methyl-4 (1H) -pyridone, and this treated with phosphorus pentasulfide. 91. The method according to claim 89, characterized in that the l-methyl-3-phenyl-5- (3-trifluoromethyl-phenyl) -4 (lH) -pyridothione is prepared by preparing a starting material from l-methylamino-2- phenyl-4- (3-trifluoromethylphe-nyl) -l-buten-3-one and / or l-methylamino-4-phenyl-2- (3-tri-fluoromethylphenyl) -l-buten-3-one with ethyl formate cyclized the l-methyl-3-phenyl-5- (3-trifluoromethylphenyl) -4 (1H) -pyridone, and treated this with phosphorus pentasulfide. 92. Use of the new 3-phenyl-5-substituted-4 (1H) -pyridones or -pyridothiones of the formula I. X II \ / \ No V I. R in which X is an oxygen atom or a sulfur atom, R represents hydrogen, QQ-alkyl, QQ-alkyl substituted by halogen, cyano, carboxy or methoxycarbonyl, QQ-alkenyl, QQ-alkoxy, QQ-alkynyl, hydroxyl or dimethylamino, with the proviso that the substituent R no longer contains 3 carbon atoms, the radicals R1 independently of one another halogen, Q-C8-alkyl, halogen-substituted QQ-alkyl, QQ-alkyl monosubstituted with phenyl, cyano or QQ-alkoxy, Q-Cg-alkenyl, halogen-substituted Q-C8-alkenyl, QQ-alkynyl, halogen-substituted QQ Alkynyl, Q-C6-cycloalkyl, QQ-cycloalkenyl, QQ-cycloalkylalkyl, QQ-alkanoyloxy, QQ-alkylsulfonyloxy, phenyl, monosubstituted phenyl, nitro, cyano, carboxy by halogen, QQ-alkyl, QQ-alkoxy or nitro, Hydroxy, QQ-alkoxycarbonyl, -O-R3, -S-R3, -SO-R3 or -S02-R3 mean, wherein R3 is Cj-C12-alkyl, halogen-substituted Q-C12-alkyl, Ci-C12-alkyl monosubstituted by phenyl, cyano or C1-C3-alkoxy, phenyl, by halogen, C1-C3-alkyl, QQ-alkoxy or nitro monosubstituted phenyl , QQ-cycloalkyl, QQ-cycloalkylalkyl, Q-C12-alkenyl halogen substituent 7 630 356 ized C2-C12-alkenyl, C2-C12-alkynyl or halogen-substituted Q-C12-alkynyl, with the proviso that the substituent R3 contains at most 12 carbon atoms, R2 for halogen, hydrogen, cyano, QQ-alkoxycarbo-5 nyl, QQ-alkyl, QQ-alkyl substituted by halogen or Q-C3-alkoxy, QQ-alkenyl, QQ-alkenyl substituted by halogen or QQ-alkoxy, QQ-alkynyl , Q- C6-cycloalkyl, C3-C6-cycloalkyI, C4-C6-cycloalkenyl, Q-10 Q-cycloalkylalkyl, phenyl-QQ-alkyl, furyl, naphthyl, thienyl substituted by halogen, QQ-alkyl or QQ-alkoxy , -O-R4, -S-R4, -SO-R4, -S02-R4 or 15 stands, R4 represents Q-Q-alkyl, halogen-substituted Ci-C3-alkyl, Q-C3-alkenyl, halogen-substituted Q-C3-alkenyl, benzyl, Phe-20 nyl or phenyl substituted by halogen, Q-Q-alkyl or Q-Q-alkoxy, the radicals R5 independently of one another are halogen, Q — Q-alkyl, halogen-substituted QQ-alkyl, QQ-alkyl monosubstituted by phenyl, cyano or QQ-alkoxy, QQ-25 alkenyl, halogen-substituted QQ-alkenyl, Q-C8-alkynyl, halogen-substituted Q-C8-alkynyl, QQ-cycloalkyl, QQ-cycloalkenyl, QQ-cycloalkylalkyl, QQ-alkanoyloxy, Q- Q-alkylsuifonyloxy, phenyl, phenyl monosubstituted by halogen, C1-C3-alkyl, Q- C3-alkoxy or nitro, nitro , Cyano, 30 carboxy, hydroxy, QQ-alkoxycarbonyl, -O-R6, -S-R6, -SO-R6 or -S02-R6, where R6 for Q-C12-alkyl, halogen-substituted Q-C12-alkyl, Q-C12-alkyl monosubstituted by phenyl, cyano or QQ-alkoxy, phenyl, by halogen, QQ-alkyl, QQ-alkoxy or nitro monosubstituted phenyl, QQ-cycloal -kyl, QQ-cycloalkylalkyl, C2-Q2-alkenyl, halogen-substituted Q-Q2-alkenyl, Q-C12-alkynyl or halogen-substituted Q-Q2-alkenyl, Q-C12-alkynyl or halogen-substituted Q-C12-alkynyl), with which Provided that the substituent R6 contains a maximum of 12 carbon atoms, the indices m and n independently of one another denote 0.1 or 2, the index m standing for 1 or 2 if R is hydrogen or methyl, X is an oxygen atom and R2 is unsubstituted phenyl, or salts of the compounds of formula I as active ingredient of a herbicidal composition. 93. Use according to claim 92, characterized in that a compound of formula II 35 40 II used in which X represents an oxygen atom or sulfur atom, 65 R ° represents Q-Q-alkyl, Q-Q-alkenyl or methoxy, q and p are the same or different and denote 0.1 or 2, the radicals R7 are identical or different and represent halogen, Q-Q-alkyl, trifluoromethyl or Q-Q-alkoxy, 630 356 8th 20th 25th the radicals R8 are identical or different and are halogen, Cx-C3-alkyl, trifluoromethyl or Cx-C3-alkoxy, or two radicals R 'are in the o- and m-positions adjacent to one another and together with the phenyl ring to which they are attached are, form a 1-naphthyl group. 5 94. Use according to claim 92, characterized in that one uses an active ingredient component of the formula I in which X is an oxygen atom and the substituent R is bonded in the m-position of the benzene nucleus, in particular a trifluoromethyl group. 10th 95. Use according to claim 92, characterized in that the following compounds of the formula I are used as the active ingredient l-methyl-3-phenyl-5- (3-trifluoromethylphenyl) -4 (1H) -pyridone, 15 l-methyl-3,5-bis (3-trifluoromethylphenyl) -4 (lH) pyridone, 3-phenyl-l- (2,2,2-trifluoroethyl) -5- (3-trifluoromethylphenyl) -4 (lH) -pyridone, 3- (3-bromophenyl) -5- (3-chlorophenyl) -l-methyl-4 (1H) -pyridone, 3- (3-chlorophenyl) -5- (4-chlorophenyl) -l-methyl-4 (1H) -pyridone, 3- (2-fluorophenyl) -l-methyl-5- (3-trifluoromethylphenyl) -4 (1H) -pyridone, 3- (2-chlorophenyl) -5- (3-chlorophenyl) -l-methyl-4 (1H) -pyridone, 3- (3-methoxyphenyl) -l-methyl-5- (3-trifluoromethylphenyl) -4 (1H) -pyridone, 3- (4-chlorophenyl) -l-methyl-5- (3-trifluoromethylphenyl) -4 (1H) -pyridone, l-allyl-3-phenyl-5- (3-trifluoromethylphenyl) -4 (1H) -pyridone, 3- (4-isopropylphenyl) -l-methyl-5-phenyl-4 (iH) -pyridone, 3- (2nd -Chlorphenyl) -l-methyl-5- (3-trifluoromethylphenyl) -4 (1H) -pyridone, 3- (3-fluorophenyl) -l-methyl-5- (3-trifluoromethylphenyl) -4 (1H) -pyridone, 3- (4-fluorophenyl) -l-methyl-5- (3-trifluoromethylphenyl) -4 (1H) -pyridone, 3- (4-methoxyphenyl) -l-methyl-5- (3-trifluoromethylphenyl) - 4 (1H) pyridone, 4o 1-methyl-3- (3-methylthiophenyl) -5-phenyl-4 (1H) pyridone, l-methyl-3- (3-methylsulfinylphenyl) -5-phenyl-4 (1H) -pyridone, l-methyl-3- (3-methylsunfonylphenyl) -5-phenyl-4 (lH) -pyri- Don, l-methyl-3-phenyl-5- (4-trifluoromethylphenyl) -4 (lH) pyridone, 45 3- (3-benzyloxyphenyl) -l-methyl-5-phenyl-4 (lH) pyridone, l-methyl -3-phenyl-5- (2-thienyl) -4 (1H) -pyridone, 3- (3-isobutylphenyl) -l-methyl-5-phenyl-4 (1H) -pyridone, l-methyl-3- ( 3-nitrophenyl) -5-phenyl-4 (1H) -pyridone, 3- (2,4-dichlorophenyl) -l-methyl-5-phenyl-4 (1H) -pyridone, 50 3,5-diphenyl, 1 - ethyl-4 (1 H) -pyridone, l-allyl-3,5-diphenyl-4 (lH) -pyridone, 3,5-diphenyl-l-isopropyl-4 (lH) -pyridone, l-cyanomethyl-3, 5-diphenyl-4 (lH) pyridone, 3,5-diphenyl-l-propyl-4 (lH) pyridone, 3,5-diphenyl-l-methoxy-4 (lH) pyridone, 3- (3- Fluorophenyl) -l-methyl-5-phenyl-4 (1H) -pyridone, 3- (4-bromophenyl) -l -methyl-5 -phenyl-4 (1H) -pyridone, 3- (4-methoxyphenyl) -l -methyl-5-phenyl-4 (1H) -pyridone, 3- (3-chlorophenyl) -l-methyl-5-phenyl-4- (1H) -pyridone, 3- (4-chlorophenyl) -l-methyl- 5-phenyl-4 (1H) -pyridone, l-methyl-3- (1-naphthyl) -5-phenyl-4 (1H) -pyridone, 3,5-bis (3-chlorophenyl) -l-methyl-4 (lH) pyridone, l-methyl-3- (3-methylphenyl) -5-phenyl-4 (lH) pyridone, l-methyl-3- (4-methylphenyl) -5-ph enyl-4 (1H) -pyridone, l-methyl-3- (2-methylphenyl) -5-phenyl-4 (1H) -pyridone, 3- (4-fluorophenyl) -l-methyl-5-phenyl-4 ( 1H) pyridone, 3- (3-methoxyphenyl) 1-methyl-5-phenyl-4 (1H) pyridone, 35 55 60 65 3- (3,4-dichlorophenyl) -l-methyl-5-phenyl-4 (1H) -pyridone, 3- (2,5-dichlorophenyl) -l-methyl-5-phenyl-4 (1H) -pyridone, 3- (2-chlorophenyl) -l-methyl-5-phenyl-4 (1H) -pyridone, 3,5-bis (3-fluorophenyl) -l-methyl-4 (1H) -pyridone, 3- (3-chlorophenyl) -5- (3-fluorophenyl) -l-methyl-4 (1H) -pyridone, 3- (3,5-dichlorophenyl) -l-methyl-5-phenyl-4 (1H) -pyridone, 3,5-bis (3-bromophenyl) -l-methyl-4 (1H) -pyridone, 3- (3-bromophenyl) -l-methyl-5-phenyl-4 (1H) -pyridone, 3- (2-fluorophenyl) -l-methyl-5-phenyl-4 (1H) -pyridone, 3- (3-bromophenyl) -l-methyl-5- (3-trifluoromethylphenyl-4 (1H) - pyridone, l- (l-carboxyethyl) -3-phenyl-5- (3-trifluoromethylphenyl) -4 (lH) -pyridone, l-dimethylamino-3,5-diphenyl-4 (1H) -pyridone, l-methyl-3- (2-naphthyl) -5-phenyl-4 (1H) -pyridone, l-ethyl-3-phenyl-5- (3-trifluoromethylphenyl) -4 (1H) -pyridone, 3-phenyl-l-propyl-5- (3-trifluoromethylphenyl) -4 (1H) -pyridone, l-methoxy-3-phenyl-5- (3-trifluoromethylphenyl) -4 (lH) pyri- Don, 3- (3-chlorophenyl) -l-methyl-5- (3-trifluoromethylphenyl) -4 (1H) -pyridone, 3- (4-biphenylyl) -l-methyl-5-phenyl-4 (1H) -pyridone, 3- (3-biphenylyl-l-methyl-5-phenyl-4 (1H) -pyridone, l-methyl-3-phenyl-4 (1H) pyridone, 3-bromo-l-methyl-5-phenyl-4 (1H) pyridone, 3-bromo-l-methyl-5- (3-trifluoromethylphenyl) -4 (1H) -pyridone, l-methyl-3- (3-trifluoromethylphenyl) -4 (1H) -pyridone, 3-chloro-l-methyl-5- (3-trifluoromethylphenyl) -4 (1H) -pyridone, 3- (3-carboxyphenyl) -l-methyl-5-phenyl-4 (1H) -pyridone, 3- (3-cyanophenyl) -l-methyl-5-phenyl-4 (1H) -pyridone, 3- (3-ethoxycarbonylphenyl) -l-methyl-5-phenyl-4 (1H) -pyri- Don, 3,5-bis (3-cy anophenyl) -1-methyl-4 (1 H) -pyridone, l-methyl-3-phenyl-5- (3-thienyl) -4 (1H) -pyridone, 3-cyano-1-methyl-5-phenyl-4 (1 H) -pyridone, 1,3-dimethyl-5- (3-trifluoromethylphenyl) -4 (1H) pyridone, 1,3-dimethyl-5-phenyl-4 (1H) pyridone, 3- (3-chlorophenyl) -1,5-dimethyl-4 (1H) -pyridone, 3-ethyl-l-methyl-5- (3-trifluoromethylphenyl) -4 (1H) -pyridone, 3-cyclohexyl-l-methyl-5- (3-trifluoromethylphenyl) -4 (lH) -py- ridon, 3-isopropyl-l-methyl-5- (3-trifluoromethylphenyl) -4 (1H) -pyridone, 3-hexyl-l-methyl-5- (3-trifluoromethylphenyl) -4 (1H) -pyridone, 3-benzyl-l-methyl-5- (3-trifluoromethylphenyl) -4 (1H) -pyridone, 3-butyl-l-methyl-5- (3-trifluoromethylphenyl) -4 (1H) -pyridone, 3- (3-cyclohexenyl) -l-methyl-5- (3-trifluoromethylphenyl) - 4 (1H) pyridone, l-methyl-3-propyl-5- (3-trifluoromethylphenyl) -4 (1H) -pyridone, l-methyl-3- (4-nitrophenyl) -5-phenyi-4 (1H) -pyridone, 3,5-bis (3,4-dimethoxyphenyl) -l-methyl-4 (1H) -pyridone, 3-ethoxycarbonyl-l-methyl-5-phenyl-4 (1H) -pyridone, 3- (2-fluryl) -l-methyl-5-phenyl-4 (1H) -pyridone, 3-cyano-l-methyl-5- (3-trifluoromethylphenyl) -4 (1H) -pyridone, 3 - (3,4-dimethoxyphenyl) -1-methyl-5-phenyl-4 (1 H) -pyridone, 3- (3,4-dibromocyclohexyl) -1-methyl-5- (3-trifluoromethylphe- nyl) -4 (lH) pyridone hydrobromide, 3- (3-isopropenylphenyl) -1-methyl-5-phenyl-4 (1 H) -pyridone, 3- (3-ethylphenyl) -l-methyl-5-phenyl-4 (1H) -pyridone, 3- (3-hexylphenyl) -l-methyl-5-phenyl-4 (1H) -pyridone, 3- (4-ethylphenyl) -l-methyl-5-phenyl-4 (1H) -pyridone, 3- (3-cyclohexylmethylphenyl) -l-methyl-5-phenyl-4 (1H) -pyri- Don, l-methyl-3-phenyl-5-benzylthio-4 (1H) pyridone, l-methyl-3-phenyl-5-phenylthio-4 (1H) pyridone, Cyclized 2-methyl-l-methylamino-4- (3-trifluoromethylphenyl) -l-butene-ethyl formate. 3-one and / or l-methylamino-2- (3-trifluoromethylphenyl) -l- 75. Process according to claim 2 for the preparation of penten-3-one cyclized with ethyl formate. 3,5-bis (3,4-dimethoxyphenyl) -l-methyl-4 (1H) -pyridone, 64. Process according to claim 2 for the preparation of 40, characterized in that 2,4-bis (3,4-dimethoxyphe-1,3-dimethyl-5-phenyl-4 (1H) -pyridone, characterized thereby-) - Cyclized l-methylamino-l-buten-3-one with ethyl formate. net that a starting material from 2-methyl-l-methylami- 76. Process according to claim 2 for the preparation of no-4-phenyl-l-buten-3-one and / or l-methylamino-2-phenyl-3- (2-furyl) -l-methyl-5-phenyl-4 (1H) -pyridone, thereby 2- (3-cyanophenyl) -l-methylamino-4-phenyl-l-buten-3-one 10 2-benzyl-l-methylamino-4- (3-trifluoromethylphenyl) -l-butene-and / or 4- ( 3-cyanophenyl) -l-methylamino-2-phenyl-l-bu-3-one and / or l-methylamino-5-phenyl-2- (3-trifluoromethyl-ten-3-one cyclized with ethyl formate. Phenyl) - l-penten-3-one cyclized with ethyl formate. 59. The method according to claim 2 for the production of 71. The method according to claim 2 for the production of 3- (3-ethoxycarbonylphenyl) -l-methyl-5-phenyl-4 (lH) -pyri- 3-butyl-l-methyl-5- (3-trifluoromethylphenyl) -4 (lH) -pyridone, don, characterized characterized in that a starting material 15 is characterized in that a starting material consisting of 2- (3-ethoxycarbonylphenyl) -l-methylamino-4-phenyl-l-2-butyl-l-methylamino-4- (3-trifluoromethylphenyl) -l- buten-3-buten-3-one and / or 4- (3-ethoxycarbonylphenyl) -l-methyl-one and / or 4-butyl-l-methylamino-2- (3-trifluoromethylphe-amino-2-phenyl-l -buten-3-one cyclized with ethyl formate.nyl) -l-buten-3-one cyclized with ethyl formate. 60. The method according to claim 2 for the preparation of 72. The method according to claim 2 for the preparation of 3,5-bis (3-cyanophenyl) -l-methyl-4 (1H) -pyridone, thereby ge 20 3- (3-cyclohexenyl ) -l-methyl-5- (3-trifluoromethylphenyl) - indicates that 2,4-bis (3-cyanophenyl) -l-methylami- 4 (lH) -pyridone, characterized in that an Aus-no- Cyclized l-buten-3-one with ethyl formate. starting material from 2- (3-cyclohexenyl) -l-methylamino-4 (3-tri- 61. The method according to claim 2 for the preparation of fluoromethylphenyl) -l-buten-3-one and / or 4- (3-cyclohexe- Cyclized 2- (3,5-dichlorophenyl) -l-methylamino-4-phenyl-l-buten-3-one ethyl formate. and / or 4- (3,5-dichlorophenyl) -l-methylamino-2-phenyl-l- 55 54. Process according to claim 2 for the preparation of buten-3-one cyclized with ethyl formate. 3- (4-Biphenylyl) -l-methyl-5-phenyl-4 (1H) -pyridone, thereby 43. The method according to claim 2 for the production of characterized in that a starting material from 2- (4-Bi-3,5-bis (3-bromophenyl) -l-methyl-4 (1H) -pyridone, thereby phenyl) -l-methylamino-4-phenyl-l-buten-3-one and / or 4- (4-indicates that 2,4-bis (3-bromophenyl) -l-methylami- biphenyl) -l-methylamino- Cyclized 2-phenyl-l-buten-3-one with ethyl-no-l-buten-3-one with ethyl formate. 60 cyclized formate. 44. The method according to claim 2 for the production of 55. The method according to claim 2 for the production of 3- (3-bromophenyl) -l-methyl-5-phenyl-4 (1H) -pyridone, thereby 3- (3-biphenylyl) -l-methyl-5-phenyl-4 (1H) -pyridone, characterized in that that a starting material is made from 2- (3-, that a starting material is made from 2- (3-bi-bromophenyl) -l-methylamino-4-phenyl-l-buten-3-one and / or phenylyl) -l- methylamino-4-phenyl-l-buten-3-one and / or 4- (3-bromophenyl) -l-methylamino-2-phenyl-l-buten-3-one with 65 4- (3-biphenylyl) -l-methylamino-2-phenyl-l-buten-3-one with ethyl formate cyclized. Cyclized ethyl formate. 45. Process according to claim 2 for the production of 56. Process according to patent claim 2 for the production of 3- (2-fluorophenyl) -l-methyl-5-phenyl-4 (lH) ~ pyridone, thereby l-methyl-3-phenyl- 4 (lH) pyridone, characterized in that 5 630 356 that cyclized l-methylamino-2-phenyl-l-buten-3-one with ethyl 69-. Process according to claim 2 for the preparation of miat. 3-hexyl-l-methyl-5- (3-trifluoromethylphenyl) -4 (1H) -pyridone, 57. The method according to claim 2 for the production of characterized in that a starting material 2- (3-chlorophenyl) -4- (3-fluorophenyl) -l-methylamino-l-butene 53. 3-one and / or 4- (3-chlorophenyl) -2- (3-fluorophenyl) -l-methyl- 3- (3-chlorophenyl) -l-methyl-5- (3-trifluoromethylphenyl) -amino-l- cyclized buten-3-one with ethyl formate. 50 4 (lH) pyridone, characterized in that an 42. The method according to claim 2 for the production of starting material from 2- (3-chlorophenyl) -l-methylamino-4- (3-tri-3- (3,5-dichlorophenyl) -l-methyl-5-phenyl-4 ( lH) -pyridone, fluoromethylphenyl) -l-buten-3-one and / or 4- (3-chlorophenyl) - characterized in that a starting material from l-methylamino-2- (3-trifluoromethylphenyl) -l-butene 3-one with 2- (2,5-dichlorophenyl) -l-methylamino-4-phenyl-l-buten-3-one, characterized in that a starting material from and / or 4- (2,5-dichlorophenyl) -l-methylamino- Cyclized 2-phenyl-l-l-ethylamino-2-phenyl-4- (3-trifluoromethylphenyl) -l-buten-3-buten-3-one with ethyl formate. on and / or l-ethylamino-4-phenyl-2- (3-trifluoromethylphe- 39. The method according to claim 2 for the preparation of 35 nyl) -l-buten-3-one cyclized with ethyl formate. 3- (2-chlorophenyl) -l-methyl-5-phenyl-4 (lH) -pyridone, characterized in 51. Process according to claim 2 for the production of characterized in that a starting material from 2- (2- 3-phenyl-l -propyl-5- (3-trifluoromethylphenyl) -4 (1H) -pyridone, chlorophenyl) -l-methylamino-4-phenyl-1-buten-3-one and / or characterized in that a starting material 4- (2-Chlorophenyl) -l-methylamino-2-phenyl-l-buten-3-one cyclized with 2-phenyl-l-propylamino-4- (3-trifluoromethylphenyl) -l-butene-ethyl formate. 40 3-one and / or 4-phenyl-l-propylamino-2- (3-trifluoromethyl- 40. The method according to claim 2 for the production of phenyl) -l-buten-3-one cyclized with ethyl formate. 3,5-bis (3-fluorophenyl) -l-methyl-4 (1H) -pyridone, thereby 52. The method according to claim 2 for the production of characterizes that 2,4-bis (3-fluorophenyl) -l -methylami- l-methoxy-3-phenyl-5- (3-trifluoromethylphenyl) -4 (1H) -pyri-no-l-buten-3-one cyclized with ethyl formate. don, characterized in that one is a raw material 41. The method according to claim 2 for the preparation of 45 from l-methoxyamino-2-phenyl-4- (3-trifluoromethylphenyl) -l-3- (3-chlorophenyl) -5- (3-fluorophenyl) -l-methyl-l (lH) -pyridone, buten-3-one and / or l-methoxyamino-4-phenyl-2- (3-trifluoro-characterized in that one cyclizes a starting material from methylphenyl) -l-buten-3-one with ethyl formate . 2- (3,4-dichlorophenyl) -l-methylamino-4-phenyl-l-buten-3-one no-2- (2-naphthyl) -4-phenyl-l-buten-3-one and / or 1 -Methyl and / or 4- (3,4-dichlorophenyl) -l-methylamino-2-phenyl-l-amino-4- (2-naphthyl) -2-phenyl-l-buten-3-one with ethyl formate butene -3-one cyclized with ethyl formate. cyclized. 38. The method according to claim 2 for the production of 3- (2,5-dichlorophenyl) -l-methyl-5-phenyl-4 (lH) -pyridone, 30 50. Process according to claim 2 for the production of characterized in that a starting material from l-ethyl-3-phenyl -5- (3-trifluoromethylphenyl) -4 (1H) pyridone, 2- (3-methoxyphenyl) -l-methylamino-4-phenyl-l-buten-3-one 20 l-dimethylamino-3,5-diphenyl-4 (lH) -pyridone, thereby ge and / or 4- ( 3-methoxyphenyl) -l-methylamino-2-phenyl-l- indicates that l- (l, l-dimethylhydrazino) -2,4-diphe-buten-3-one is cyclized with ethyl formate. Cyclized nyl-l-buten-3-one with ethyl formate. 37. The method of claim 2 for the production of 49. The method of claim 2 for the production of 3- (3,4-dichlorophenyl) -l-methyl-5-phenyl-4 (1H) -pyridone, l-methyl-3- (2-naphthyl) -5-phenyl-4 (1H) -pyridone, thereby ge - characterized in that one marks a starting material from 25, one marks a starting material from 1-methylami- 2- (4-fluorophenyl) -l-methylamino-4-phenyl-l-buten-3-one starting material from 2- (3-bromophenyl) -l-methylamino-4- (3-tri-and / or 4- ( 4-fluorophenyl) -l-methylamino-2-phenyl-l-bu-fluoromethylphenyl) -l-buten-3-one and / or 4- (3-bromophenyl) -ten-3-one cyclized with ethyl formate. 10 l-methylamino-2- (3-trifluoromethylphenyl) -l-buten-3-one with 35. The method according to claim 2 for the production of ethyl formate cyclized. 2- (4-isoporpylphenyl) -l-methylamino-4-phenyl-l-buten-3-one and / or 4- (4-isoporpylphenyl) -1-methylamino-2-phenyl-1-buten-3-one with Cyclized ethyl formate. 14. The method according to claim 2 for the preparation of 3 - (2-chlorophenyl) -1-methyl-5 - (3-trifluoromethylphenyl) -4 (lH) -pyridone, characterized in that a starting material from 2- (2-chlorophenyl) ) -l-methylamino-4- (3-trifluoromethylphenyl) -l-buten-3-one and / or 4- (2-chlorophenyl) -l-methylamino-2- (3-trifluoromethylphenyl) -l-butene 3-one cyclized with ethyl formate. 15. The method according to claim 2 for the production of 3- (3-fluorophenyl) -l-methyl-5- (3-trifluoromethylphenyl) -4 (1H) -pyridone, characterized in that a starting material from 2- (3-fluorophenyl) -l-methylamino-4- ( 3-tri-fluoromethylphenyl) -l-buten-3-one and / or 4- (3-fluorophenyl) -l-methylamino-2- (3-trifluoromethylphenyl) -l-buten-3-one cyclized with ethyl formate. 16. The method according to claim 2 for the preparation of 3- (4-fluorophenyl) -l-methyl-5- (3-trifluoromethylphenyl) -4 (lH) -pyridone, characterized in that a starting material from 2- (4-fluorophenyl ) -l-methylamino-4- (3-tri-fluoromethylphenyl) -l-buten-3-one and / or 4- (4-fluorophenyl) -l-methylamino-2- (3-trifluoromethylphenyl) -l-butene 3-one cyclized with ethyl formate. 17. The method according to claim 2 for the preparation of 3- (4-methoxyphenyl) -l-methyl-5- (3-trifluoromethylphenyl) -4 (lH) -pyridone, characterized in that a starting material from 2- (4-methoxyphenyl ) -l-methylamino-4- (3-trifluoromethylphenyl) -l-buten-3-one and / or 4- (4-methoxyphenyl) -1 -methylamino-2- (3-trifluoromethylphenyl) -1 -butene- 3 -one cyclized with ethyl formate. 18. The method according to claim 2 for the preparation of 3- (3-benzyloxyphenyl) -l-methyl-5-phenyl-4 (lH) -pyridone, characterized in that 4- (3-benzyloxyphenyl) -l-methylamino-2 -phenyl-l-buten-3-one cyclized with ethyl formate. 19. The method according to claim 2 for the preparation of l-methyl-3-phenyl-5- (2-thienyl) -4 (lH) -pyridone, characterized in that l-methylamino-2-phenyl-4- (2- cyclized thie-nyl) -l-buten-3-one with ethyl formate. 20. The method according to claim 2 for the preparation of 3 - (3-isobutylphenyl) -1-methyl-5-phenyl-4 (1H) -pyridone, characterized in that 4- (3-isobutylphenyl) -l-methylamino-2-phenyl-l-buten-3-one is cyclized with ethyl formate. 21. The method according to claim 2 for the preparation of l-methyl-3- (3-nitrophenyl) -5-phenyl-4 (lH) pyridone, thereby 5 characterized in that l-methylamino-4- (3-nitrophenyl) -2-phenyl-l-buten-3-one cyclized with ethyl formate. 22. The method according to claim 2 for the preparation of 3,5-diphenyl-l-propyl-4 (lH) -pyridone, characterized in that 2,4-diphenyl-l-propylamino-l-buten-3-one with 10 ethyl formate cyclized. 23. The method according to claim 2 for the preparation of 3,5-diphenyl-l-methoxy-4 (lH) -pyridone, characterized in that 2,4-diphenyl-l-methoxyamino-l-buten-3-one with ethyl formate cyclized. 15 24. The method according to claim 2 for the preparation of 3- (3-fluorophenyl) -l-methyl-5-phenyl-4 (lH) -pyridone, characterized in that a starting material from 2- (3-FIuor-phenyl) -l-methylamino-4-phenyl-l-buten-3-one and / or 4- (3-fluorophenyl) -1-methylamino-2-phenyl-1-buten-3 -one with Cyclized 20 ethyl formate. 25. The method according to claim 2 for the preparation of 3- (4-bromophenyl) -l-methyl-5-phenyl-4 (1H) -pyridone, characterized in that a starting material from 2- (4-bromophenyl) -l- methylamino-4-phenyl-l-buten-3-one and / or 25 4- (4-bromophenyl) -l-methylamino-2-phenyl-l-buten-3-one cyclized with ethyl formate. 26. The method according to claim 2 for the preparation of 3- (4-methoxyphenyl) -l-methyl-5-phenyl-4 (lH) -pyridone, characterized in that a starting material 30 2- (4-methoxyphenyl) -l-methylamino-4-phenyl-l-buten-3-one and / or 4- (4-methoxyphenyl) -l-methylamino-2-phenyl-l-buten-3-one cyclized with ethyl formate. 27. The method according to claim 2 for the production of 3- (3-Chlorophenyl) -l-methyl-5-phenyl-4 (1H) -pyridone, thereby 35 characterized that a starting material from 2- (3- Chlorphenyl) -1-methylamino-4-phenyl-1-buten-3 -one and / or Cyclized 4- (3-chlorophenyl) -l-methylamino-2-phenyl-l-buten-3-one with ethyl formate. 28. The method according to claim 2 for the production of 40 3- (4-chlorophenyl) -l-methyl-5-phenyl-4 (1H) -pyridone, characterized in that a starting material from 2- (4-chlorophenyl) -1-methylamino-4-phenyl-1 - cyclized buten-3-one and / or 4- (4-chlorophenyl) -l-methylamino-2-phenyl-l-buten-3-one with ethyl formate. 45 29. The method according to claim 2 for the preparation of l-methyl-3- (l-naphthyl) -5-phenyl-4 (lH) -pyridone, characterized in that a starting material from 1-methyl-amino-2- ( l-naphthyl) -4-phenyl-l-buten-3-one and / or 1-methylamino-4- (l-naphthyl) -2-phenyl-l-buten-3-one with ethyl 50 cyclized formate. 30. The method according to claim 2 for the preparation of 3,5-bis (3-chlorophenyl) -l-methyl-4 (lH) -pyridone, characterized in that 2,4-bis (3-chlorophenyl) -l-methylami -no-1-buten-3-one cyclized with ethyl formate. 55 31. The method according to claim 2 for the preparation of l-methyl-3- (3-methylphenyl) -5-phenyl-4 (lH) -pyridone, characterized in that a starting material from 1-methylamino-2- (3 - methylphenyl) -4-phenyl-l-buten-3-one and / or l-methylamino-4- (3-methylphenyl) -2-phenyI-l-bu- 60 ten-3-one cyclized with ethyl formate. 32. The method according to claim 2 for the preparation of l-methyl-3- (4-methylphenyl) -5-phenyl-4 (lH) pyridone, characterized in that a starting material from l-methylamino-2- (4-methylphenyl ) -4-phenyl-l-buten-3-one 65 and / or l-methylamino-4- (4-methylphenyl) -2-phenyl-l-butten-3-one cyclized with ethyl formate. 33. The method according to claim 2 for the preparation of l-methyl-3- (2-methylphenyl) -5-phenyl-4 (lH) pyridone, 630 356 4 characterized in that a starting material is characterized in that a starting material is made of 2- (2-fluorine 2. The method according to claim 1, characterized in that an ester of formic acid, preferably the ethyl ester (ethyl formate) is used as the formulation agent. 3. The method according to claim 2 for the preparation of 30l-methyl-3-phenyl-5- (3-trifluoromethylphenyl) -4 (lH) pyridone, characterized in that a starting material from l-methylamino-2-phenyl-4- (3-trifluoromethylphenyl) -l-buten-3-one and / or l-methylamino-4-phenyl-2- (3-trifluoromethyl-phenyl ) -l-buten-3-one cyclized with ethyl formate. 35 4. The method according to claim 2 for the preparation of l-methyl-3,5-bis (3-trifluoromethylphenyl) -4 (lH) pyridone, characterized in that l-methylamino-2,4-bis- (3- trifluoromethylphenyl) -l-buten-3-one cyclized with ethyl formate. 5. The method according to claim 2 for the preparation of 40 3-phenyl-l- (2,2,2-trifluoroethyl) -5- (3-trifluoromethylphenyl) - 4 (lH) -pyridone, characterized in that a starting material from 2-phenyl-l- (2,2,2-trifluoroethylamino) -4- (3-trifluoromethylphenyl) -l-buten-3-one and / or 4 -Phenyl-l- (2,2,2-triQuoräthylamino) -2- (3-trifluoromethylphenyl) -l-buten-45 3-one cyclized with ethyl formate. 6. The method according to claim 2 for the preparation of 3- (3-bromophenyl) -5- (3-chlorophenyl) -l-methyl-4 (lH) -pyri-don, characterized in that a starting material from 2- (3- Bromophenyl) -4- (3-chlorophenyl) -l-methylamino-l- 50 buten-3-one and / or 4- (3-bromophenyl) -2- (3-chlorophenyl) -l-methylamino-l-buten-3-one cyclized with ethyl formate. 7. The method according to claim 2 for the preparation of 3- (3-chlorophenyl) -5- (4-chlorophenyl) -l-methyl-4 (lH) -pyri-don, characterized in that a starting material 55 from 2- (3-chlorophenyl) -4- (4-chlorophenyl) -l-methylamino-l-buten-3-one and / or 4- (3-chlorophenyl) -2- (4-chlorophenyl) -l- cyclized methylamino-l-buten-3-one with ethyl formate. 8. The method according to claim 2 for the preparation of 3- (2-fluorophenyl) -l-methyl-5- (3-trifluoromethylphenyl) - 60 4 (lH) -pyridone, characterized in that a starting material from 2- (2-fluorophenyl) -l-methylamino-4- (3-tri-fluoromethylphenyl) -l-buten-3-one and / or 4- Cyclized (2-fluorophenyl) -l-methylamino-2- (3-trifluoromethylphenyl) -l-buten-3-one with ethyl formate. 65 9. The method according to claim 2 for the preparation of 3- (2-chlorophenyl) -5- (3-chlorophenyl) -l-methyl-4 (lH) -pyri-don, characterized in that a starting material from 2- (2 -Chlorphenyl) -4- (3-chlorophenyl) -l-methylamino-l- Cyclized buten-3-one and / or 4- (2-chlorophenyl) -2- (3-chlorophenyl) -1-methylamino-1-buten-3-one with ethyl formate. 10. The method according to claim 2 for the preparation of 3 - (3-methoxyphenyl) -1-methyl-5- (3-trifluoromethylphenyl) -4 (lH) -pyridone, characterized in that a starting material from 2- (3-methoxyphenyl ) -l-methylamino-4- (3-trifluoromethylphenyl) -l-buten-3-one and / or 4- (3-methoxyphenyl) -l -methylamino-2- (3-trifluoromethylphenyl) -l -butene- 3-one cyclized with ethyl formate. 11. The method according to claim 2 for the preparation of 3- (4-chlorophenyl) -l-methyl-5- (3-trifluoromethylphenyl) -4 (lH) -pyridone, characterized in that a starting material as 2- (4-chlorophenyl ) -l-methylamino-4- (3-tri-fluoromethylphenyl) -l-buten-3-one and / or 4- (4-chlorophenyl) -l-methylamino-2- (3-trifluoromethylphenyl) -l-butene 3-one cyclized with ethyl formate. 12. The method according to claim 2 for the preparation of l-allyl-3-phenyl-5- (3-trifluoromethylphenyl) -4 (lH) -pyridone, characterized in that a starting material 3- (3-Chlorophenyl) -l-methyl-5-phenyl-4 (1H) -pyridine thione, l-methyl-3-phenyl-5- (3-trifluoromethylphenyl) -4 (1H) -pyridine-thione. From J. Org. Chem. 25,538-546 (1960) a number of 4-pyridone compounds including 2,6-diphenyl-1-methyl-4 (1H) -pyridone and related compounds which are substituted on the phenyl ring, but none of these compounds has herbicidal activity. An interesting article was recently published in J. Hetero. Chem. 10,665-667 (1973). This describes a synthesis for 3,5-diphenyl-1-methyl-4 (1H) -pyridone and related compounds by using the sodium salt of 1,5-dihydroxy-2,4-diphenyl-1,4-pentadiene- 3-one reacted with methylamine. In the publication by Benary and Bitter in Ber. 61, 1058 (1928) describes a process for the preparation of 3,5-diphenyl-4 (1H) pyridone. According to this process, the 1,5-dihydroxy-2,4-diphenyl-1,4-pentadien-3-one is first prepared by condensation of 1,3-diphenyl-2-propanone with ethyl formate in the presence of sodium methoxide. This intermediate pentadienone is then neutralized with a strong acid, which forms the 3,5-diphenyl-4-pyrone. The desired end product, namely 3,5-diphenyl-4 (1H) pyridone, is then obtained by reacting this pyron with ammonium acetate at elevated temperature.