CH632496A5 - Process for the preparation of 3-phenyl-5-substituted-4(1H)pyridones, and their use - Google Patents

Abstract

3-Phenyl-5-substituted-4(1H)pyridones of the formula I <IMAGE> are prepared by reacting a compound of the formula IV <IMAGE> with a compound of the formula RNH2 or with an acid addition salt of this compound. By reacting the pyridones of the formula I with phosphorus pentasulphide, the corresponding pyridothiones are obtained. The pyridones, the corresponding pyridothiones and the salts thereof are used as the active component of herbicides. They possess a herbicidal activity against an unusually broad spectrum of weeds.

Description

The present invention relates to a process for the preparation of 3-phenyl-5-substituted-4 (1 H) -pyridones and their salts.

These new pyridones are used as active ingredient components of herbicidal agents. The herbicidal compositions obtained in this way can be used as leading herbicides or trailing herbicides 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 so far that are closely related to the compounds of the present formula I. The polyhalopyridones, the pyridine ring of which is substituted by two or more cioratoms and also other alkyl and halogen substituents, are known herbicides. However, they are obviously quite different from the compounds of the 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 last-mentioned work also describes 3,5-di (substituted-benzylidene) tetrahydro-4-pyridones. These compounds are also not herbicidally active.

From J.Org.Chem. 25,538-546 (1960) discloses a series of 4-pyridone compounds including 2,6-diphenyl-1-methyl-4 (1H) -pyridone and related compounds substituted on the phenyl ring, but none of these compounds have herbicidal activity.

An interesting article was recently published in J. Straight.

Chem. 10,665-667 (1973). This describes a synthesis for 3,5-diphenyl-1-methyl-4 (1 H) -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-pro-panon 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. Reaction of this pyrone with ammonium acetate at an elevated temperature then gives the desired end product, namely 3,5-diphenyl-4 (1H) pyridone.

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:

R

wherein

X means oxygen

R is hydrogen, an alkyl radical with 1 to 3 carbon atoms, an alkyl radical with halogen, cyano, carboxy or methoxycarbonyl 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 an 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 R '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 groups with 1-8 carbon atoms, alkenyl groups with 2-8 carbon atoms, halogen-substituted alkenyl groups with 2-8 carbon atoms, alkynyl groups with 2-8 carbon atoms, halogen-substituted alkynyl groups with 2-8 carbon atoms, cycloalkyl groups with 3-6 carbon atoms , Cycloalkenyl residues with 4-6 carbon atoms, cycloalkylalkyl residues with 4-8 carbon atoms, alkanoyloxy residues with 1-3 carbon atoms, alkylsulfonyloxy residues with 1-3 carbon atoms, phenyl residues, by halogen, alkyl with 1-3 carbon atoms, alkoxy with 1-3 carbon atoms or nitro monosubstituted phenyl radicals, nitro, cyano, carboxy or hydroxyl groups, alkoxycarbonyl groups with 1-3 carbon atoms, or groupings of the formulas:

Mean -O-R3, -S-R3, -SO-R3 or SO2-R3,

wherein

R3 is an alkyl radical with 1-12 carbon atoms, halogen-substituted alkyl radical with 1-12 carbon atoms, phenyl, cyano or an alkoxy group with 1-3 carbon atoms monosubstituted alkyl radical with 1 to 12 carbon atoms, a phenyl radical, one with 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, one Alkynyl radical having 2-12 carbon atoms or a halogen-substituted alkynyl radical having 2-12 carbon atoms, with the proviso that the radical R3 contains a total of at most 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 radical with 2-6 carbon atoms, one with Halogen or alkoxy with 1-3 carbon atoms substituted alkenyl radical with 2-6 carbon atoms,

an alkynyl radical, a cycloalkyl radical with 3-6 Koh8

5

10th

15

20th

25th

30th

35

40

45

50

55

60

65

9

632496

lenstoffatomen, a by halogen, alkyl with 1-3 carbon atoms or alkoxy with 1-3 carbon atoms substituted cycloalkyl radical with 3-6 carbon atoms, a cycloalkenyl radical with 4-6 carbon atoms, a cycloalkyl alkyl 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 -SO2-R4, wherein

R4 is 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:

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 = O, R2 is an unsubstituted phenyl radical and 5 R is a hydrogen atom, namely 3,5-diphenyl-4 (1 H) -pyridone, is already from the publication mentioned above by Benary and Bitter in Ber. 61, 1058 (1928). The corresponding 1-methyl derivative, namely 3,5-diphenyl-1-methyl-4- (1H) -pyridone, has also 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

15

<

20th

R m

£

>

0 II

"0 - O - Oll II

IV

fr is where the residues

R5 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, by halogen, Alkyl with 1-3 carbon atoms, alkoxy with 1-3 carbon atoms monosubstituted phenyl groups, or nitro, cyano, carboxy or hydroxyl groups, alkoxycarbonyl groups with 1 to 3 carbon atoms or groups of the formulas:

-O-R6, -S-R6, -SO-R6 or -SO2-R6

mean what

R6 is an alkyl group with 1-12 carbon atoms, a halogen-substituted alkyl group with 1-12 carbon atoms, an alkyl group with 1-12 carbon atoms monosubstituted by phenyl, cyano or an alkoxy group with 1-3 carbon atoms, a phenyl group, one with halogen, an alkyl group with 1 -3 carbon atoms, an alkoxy group with 1-3 carbon atoms or a nitro group monosubstituted phenyl group, a cycloalkyl group with 3-6 carbon atoms, a cycloalkylalkyl group with 4-8 carbon atoms, an alkenyl group with 2-12 carbon atoms, a halogen-substituted alkenyl group with

2-12 carbon atoms, an alkynyl group with 2-12 carbon atoms or a halogen-substituted alkynyl group with 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 , however, the index m stands for 1 or 2 if R represents a hydrogen atom or a methyl group, and in which

R1, R2 and m have the meaning given in formula Ia, and

25 each of the two substituents Q1 and Q2 is a grouping of the formula: = CH-OH,

with a compound of the formula:

RNH2

30th

wherein R has the same meaning as in formula Ia, or an acid addition salt of this compound cyclizes.

The process according to the invention for the preparation of the pyridones of the formula Ia is therefore an analogous process to that described in the publication by Benary and Bitter, in

Ber. 61, 1058 (1928). If the cyclization is carried out with the ammonium acetate used in this publication, an end product of the formula Ia is obtained in which R is a hydrogen atom. 40 When carrying out the process according to the invention, ammonia (R means a hydrogen atom), hydroxylamine (R means hydroxy), dimethylhydrazine (R means dimethylamino), or a 45 corresponding amine or a salt thereof can be used as the cyclizing agent for cyclizing the starting materials of the formula IV Connections are used.

If the cyclization is carried out with ammonia or an acid addition salt thereof, then a compound of the formula Ia is obtained in which R is a hydrogen atom.

According to one embodiment of the process according to the invention, a compound of the formula Ia in which R is a hydrogen atom can first be prepared and then converted into a compound of the formula Ia in which R is an alkyl radical having 1-3 carbon atoms, one by halogen, Cyano, carboxy or methoxycarbonyl substituted alkyl radical with 1-3 carbon atoms, an alkenyl radical with 2 or 3 carbon atoms or an alkynyl radical with 2 or 3 carbon atoms is by introducing the corresponding radical on the nitrogen 60 atom by the method of N-alkylation.

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 65 with a halide or, in the case of corresponding alkyl radicals, with a dialkyl sulfate.

Subsequent alkylation on the nitrogen atom can, however, also be carried out by

632496

10th

The corresponding 1-unsubstituted pyridone of the formula I a is first converted into the corresponding 4-halogen derivative or the corresponding 4-alkoxy derivative by reaction with a halogenating agent or an alkylating agent. POCb, POBn or PCls, for example, 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, whereby the 1 -R-substituted-4-substituted-pyridinium salt is formed. The salt obtained is then hydrolyzed to form the desired product with either a mineral acid or an alkali metal hydroxide. For more details, see Pharm. Bull. (Japan) 1,70-74 (1953).

If hydroxylamine or a salt thereof is used as the cyclizing agent in carrying out the process according to the invention, a corresponding pyridone of the formula Ia is obtained, in which R is likewise a hydroxyl radical. This product can then be esterified, for example subjected to acetylation, a corresponding 3-phenyl-5-substituted-4 (1 H) -pyridone of the formula V being used

S1 "i R

(V)

^ -sN /

i receives what

R 'is an acetoxy radical, and the radicals R1, R2 and m have the same meaning as in formula Ia,

and of course a salt of the compound of formula V can also be prepared.

In preferred compounds of the formula lab 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:

III

on, with the remains

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

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 II:

X

II

O

/ \

R

, x_y

, • <—- O:

10th

IS

II

R

wherein

X means oxygen

20 R ° represents Ci-C3-alkyl, C2-C3-alkenyl, acetoxy or methoxy,

q and p independently of one another represent 0.1 or 2, the radicals R7 independently of one another represent halogen, C1-C3-alkyl, trifluoromethyl or C1-C3-alkoxy,

2s the radicals R8 are, independently of one another, halogen, C1-C3-alkyl, trifluoromethyl or C1-C3-alkoxy or two radicals R8 are adjacent to one another in the o- and m-positions and together with the phenyl ring to which they are attached, one Form 1-naphthyl group.

30 In the above formulas, the general chemical terms are used in their normal meanings. The information Ci-C3-alkyl, C2-C3-alkenyl, C2-C3-alkynyl, Ci-C3-alkoxy, Ci-Cs-alkyl, Cï-Cs-alkenyl, C2-Cs-alkynyl, Ci-Ce-alkyl, C2-C6-alkenyl and C2-C6-alkynyl refer, for example, to radicals such as methyl, ethyl, isopropyl, vinyl, allyl, methoxy, isopropoxy, propargyl, isobutyl, hexyl, octyl, 1,1-dimethylpentyl, 2-octenyl , Pentyl, 3-hexynyl, l-ether-2-hexenyls, 3-octynyl, 5-heptenyl, l-propyl-3-butynyl and crotyl.

40 C3-C6-cycloalkyl and C4-C6-cycloalkenyl are understood to mean, for example, radicals such as cyclopropyl, cyclobutyl, cyclohexyl, cyclobutenyl, cyclopentenyl and cyclo-hexadienyl.

The statement C4-Cs-cycloalkylalkyl refers to residues, 45 such as cyclopropylmethyl, cyclobutylmethyl, cyclohexylmethyl and cyclohexylethyl.

Ci-C3-alkanoyloxy means residues such as formyloxy, acetoxy and propionyloxy.

Ci-C3-alkoxycarbonyl refers, for example, to residues such as methoxycarbonyl, ethoxycarbonyl and isopropoxycarbonyl.

Ci-C3-alkylsulfonyloxy means residues such as e.g. Methylsulfonyloxy and propylsulfonyloxy.

The term halogen means fluorine, chlorine, bromine and 55 iodine.

The compounds described above can form salts, especially 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.

As already mentioned, 65 as starting materials for carrying out the process according to the invention requires compounds of the formula IV in which both the radical Q1 and the radical Q2 stand for a grouping of the formula = CH-OH. These starting materials can thus by the following formula XII

11

632496

R '

m

0

II

^ ^ ^ ^ f * \ - ^ ^

O TS

XII

H1

oÏh hE

OH

are reproduced.

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

wise selected from the agents commonly used for such reactions. The preferred agents are esters of formic acid of the formulas

5 Ï

H-C-0- (Ci-Cs alkyl) or

0

"« /

I 1 - A A

II "" \ s ^ ~ \ s

/ - \ »

<> —CH —0 — CH Rs

V / 8 8

R1 • = '

m

\

>

VIII

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

R1 m

K °

V ""> —O — O — CH —Rs

\ =. / "

./ H

HIGH

IX

receives.

As can be seen from formula VIII of the starting material used, one of the two CHi groups of the starting material is converted into the corresponding hydroxymethylene group in the formylation reaction. However, the intermediate of formula IX mentioned here is only one of the two possible substitutions, and depending on the activating properties of the substituents R 'or R2, of the starting material, the other of the two CH: groups mentioned can also be substituted in the formulation reaction . However, this is of no importance for the continuation of the production of the starting material, because in any case the second CH2 group of this intermediate of formula IX must be converted into the second hydroxymethylene group of the required starting material of formula IV by a further formylation.

The intermediate of formula IX is generally not isolated, and optionally the reaction of the ketone of formula VIII with the formylating agent is allowed to continue until both CH2 groups of the ketone of formula VIII into the desired hydroxymethylene groups of the starting material of formula IV , or XII, are transferred.

The ketones of the formula VIII required for the preparation of the starting material of the formula IV 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, American Laboratory 49-56 (June 1974); Collmann 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 Intermediates in The Synthesis of Aldehydes and Ketones", J.Am. Chem. Soc. 94, 2516-18 (1972).

The formylating agents required for the preparation of the starting materials of the formula IV are expediently

15 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 2o 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. 25 Reactions with formylating agents are carried out in generally aprotic solvents, as are normally used in chemical syntheses. The normally preferred solvent is ethyl ether. Ethers can generally be used as solvents for formylations, 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 used in the formulation reactions, the best results are generally 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 come to room temperature after the reaction 40 has partially ended. Reaction times of about 1 to about 24 hours are usually sufficient to achieve economic yields in the formylation reactions.

The starting materials of the formula IV are cyclized by the process according to the invention by reaction with an amine of the formula RNH2 or an acid addition salt of this amine. This reaction is preferably carried out in a protic solvent, with alkanols being preferred, and ethanol is particularly suitable for this purpose. The reaction can be carried out, for example, at a temperature in the range from -20 ° C to 100 ° C, and in general working at about room temperature is preferred.

In many cases it has proven to be advantageous not to use the 55 amines of the formula RNH2 in free form, but in the form of their acid addition salts to carry out the process according to the invention. Examples of such acid addition salts are hydrohalides, such as hydrobromides and hydrochlorides. A preferred amine used for the cyclization is methylamine or an acid addition salt thereof, and compounds of the formula Ia in which R is a methyl group are then obtained when the cyclization reaction is carried out.

Another object of the present invention is a process for the preparation of the pyridothiones which are analogous to the pyridones of the formula Ia, that is to say the following formula Ib:

632496

12

JR?

(Ib)

In an analogous manner, this can be done in two stages

Process also produce the following pyridothiones:

the 1-methyl-3-phenyl-5- (3-trifluoromethylphenyl) -4 (1 H) -s pyridothione and the 3,5-diphenyl-1-methyl-4 (1 H) -pyridine thione.

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

correspond.

In these pyridothions of the formula Ib, the radicals R, 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 compounds mentioned are also new compounds.

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

A

\ /

O

II

-Ru

(I)

m il

9 *

IV

in which

R1, R2 and m have the meaning given in formula Ia, and each of the two substituents Q1 and Q2 represents a group of the formula: = CH-OH,

with a compound of the formula:

RNHÎ

wherein R has the meaning given above, to a compound of formula Ia, in which

X is an oxygen atom or a sulfur atom,

30 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 Is methyl group, and furthermore X 35 represents an oxygen atom, and also R2 represents an unsubstituted phenyl radical, or of salts of the compounds of the formula I, as active ingredient of a herbicidal agent.

Those active ingredients of formula I which are of the following formula II are again particularly preferred:

45

/ \ / = \

,,. X—

VX

50

(la)

R

II

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

This two-stage process can be used, for example, to prepare 3- (3-chlorophenyl) -1-methyl-5-phenyl-4 (1 H) -pyrididinion by adding 2- (3-chlorophenyl) -1,5- dihydroxy-4-phenyl-l, 4-pentadien-3-one with methylamine to the 3- (3-chlorophenyl) -1-methyl-5-phenyl-4 (1 H) -pyridone and then treated with phosphorus pentasulfide.

In the same way, the 3,5-bis (3-chlorophenyl) -l-methyl-4 (1H) -pyridinthione can be prepared by first making the 2,4-bis (3-chlorophenyl) -1,5-dihydroxy Cyclized -1,4-pentadien-3-one with methylamine to give the 3,5-bis (3-chlorophenyl) -1-methyl-4 (1 H) -pyridone and then treated with phosphorus pentasulfide.

55

R

o correspond, where in this formula X represents an oxygen atom or sulfur atom,

R ° for an alkyl radical with 1-3 carbon atoms,

is an alkenyl radical having 2 or 3 carbon atoms or a 60 methoxy group, and p and q are identical or different and are 0.1 or 2,

the radicals R7 are identical or different and stand for halogen, alkyl groups with 1-3 carbon atoms, trifluoromethyl-65 groups or alkoxy groups with 1 to 3 carbon atoms,

The radicals R8 are the same or different and are halogen, alkyl groups with 1-3 carbon atoms, trifluoromethyl

are groups or alkoxy groups with 1-3 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 a 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 are particularly important as a trifluoromethyl group are very particularly preferred as the 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.

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

3- (2,6-dimethylphenyl) -1-isopropyl-5- (1-naphthyl) -4 (1H) -pyridone,

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

3- (3,5-difluorophenyl) -1-methoxy-5-phenyl-4 (1 H) -pyridone l-propyl-3- (4-trifluoromethylphenyl) -5- (3-trifluoromethylene phenyl) -4 (1 H) pyridone,

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

3- (3,5-dibromophenyl) -5- (3-isopropoxyphenyl) -1-propyl-4 (1H) -pyridone,

3- (3-bromophenyl) -l-methyl-5-phenyl-4 (1H) -pyridone 3- (4-chlorophenyl) -5- (2,4-dimethoxyphenyl) -1-propyl-4 (1H) -pyridone

1-acetoxy-3- (4-chlorophenyl) -5- (1-naphthyl-4 (1 H) -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] -1 -me-thoxy-4 (1 H) -pyridone

3-Benzyloxy-1-chloromethyl-5- (3-ethynylphenyl) -4 (1H) pyridone

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

3-BenzylsulfinyI-1-ethyl-5- (3-fluoro-5-propylphenyl) -4 (1 H) pyridone

3-benzylsulfonyl-5- (3-octylphenyl) -1-propyl-4 (1 H) -pyridone 3- (2-butylphenyl) 1 -trifluoromethyl-4 (1 H) -pyridone-hydrobromide

3- (3-Hexylphenyl) -1-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-1-methyl-4 (1H) pyridone

1-Methyl-3- [3- (1-propylpentyl) phenyl] -5-propyl-4 (1H) -pyridone 1- (2-cyanoethyl) -3- (3-octyl-4-methylphenyl) -5-propoxy -car-bonyl-4 (1 H) pyridone

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

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

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

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

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

3- (3-hexylphenyl) -5-methoxymethyl-1-methyl-4 (1 H) -

13 632496

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

3- (6-ethoxyhexyl) -5- (3-ethyl-5-iodophenyl) -l- (3-iodopropyl) -s 4 (1H) -pyridone 3- [4- (8-cyanooctyl) phenyl] -l- methyl-5- (2-pentenyl) -4 (1H) pyridone

3- (2,2-dichlorovinyl) -1-methyl-5- [3- (3-propoxyheptyl) phenyl] -4 (1 H) -pyridone io 3- (2-bromo-1-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 (1 H) -pyridone 1-methoxycarbonylmethyl-3- [3- ( 3-octenyl) phenyl] -5-phenyl-15 4 (1H) pyridone methanesulfonate

3- (2-butynyl) -5- (2,4-diiodophenyl) -1-ethoxy-4 (1H) -pyridone 3- [4- (2,6-dibromo-2-heptenyl) phenyl] -1,5 -dimethyl-4 (1H) pyridone

3- (2-Hexenyl) -1-methyl-5- [3- (1,1,2,2-tetrachloro-4-octenyl) -20 phenyl] -4 (1H) pyridone

3-Cyclobutyl-5- [4- (2-iodovinyl) phenyl] -1-propoxy-4 (1H) pyridone

1 - (1-Carboxyethyl) -3- (2-chlorocyclopropyl) -5- [3- (3-chloropropargyl) phenyl] -4 (1 H) -pyridone 25 3- [4- (1,1-dibromo -4-pentinyl) phenyl] -1-isopropoxy-5- (2-me-thylcyclobutyl) -4 (1 H) -pyridone

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

3- [2- (1,1-dichloro-4-heptinyl) phenyl] -5- (4-methoxycyclo-30 hexyl) -l-methoxy-4 (1H) -pyridone 3- (3-chyclohexenyl) -5- (3-cyclohexylphenyl) -1 "dimethylamino- ^ 1 H) pyridone

3- [4- (1-Cyclobutenyl) phenyl] 5-methoxy-1-vinyl-4 (1H) pyridone toluenesulfonate 35 3- [4- (2-cyclohexenyl) phenyl] -5-isopropoxy-l-trifluoro -methyl-4 (1 H) -pyridone l-dichloromethyl-3- (2-iodoethoxy) -5- (4-isopropylsulfonyl-oxyphenyl) -4 (1 H) -pyridone

3-allyloxy-5- [4- (2-chlorophenyl) phenyl] -1-isopropyl-4 (1H) -40 pyridone hydrochloride 3- (2,2-dichlorovinyloxy) -5- [2- (3-iodophenyl) phenyl] -1-methyl-4 (1H) pyridone

3- (2-bromoallyloxy) -5- [3- (3-bromophenyl) phenyl] -1-vinyl-4 (1H) pyridone

45 l-Allyl-3- [4- (2-methylphenyl) phenyl] -5- (3,3,3-trifluoro-l-pro-penyloxy-4 (1 H) pyridone

1-methoxy-3-phenoxy-5- [3- (4-propylphenyl) phenyl] -4 (1H) pyridone

3- (2-chlorophenoxy) -5- [4-methoxyphenyl) phenyl] -1 -proso pargyl-4 (1H) -pyridone 3- (4-bromophenoxy) -5- [4- [2-ethoxyphenyl) phenyl] - 1-ethyl-4 (1H) pyridone

3- (2-iodophenoxy) -5- [3- (4-isopropoxyphenyl) phenyl] -l-methoxycorbony imethyl-4 (1 H) -pyridone ss 1 -methyl-3- (4-nitrophenyl) -5- (3- propylphenoxy) -4 (1H) pyridone

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

3- (3-carboxyphenyl) -5- (2-ethoxyphenoxy) -1 -isopropyl- «o 4 (1H) -pyridone hydrofluoride l- (2-carboxyethyl) -3- (4-hydroxyphenyl) -5- (3rd -propoxyphe-noxy) -4 (1 H) -pyridone

3-benzyl-5- (2-methoxycarbonylphenyl) -1-methyl-4 (1H) -pyridon es l-dimethylamino-3- (3-phenylpropyl) -5- (4-propoxycar-bony l) phenyl) -4 ( 1 H) -py ridon

3- (3-butoxyphenyl) -5- (2-furyl) -1-trifluoromethyl-4 (1H) pyridone

632496

3- (1-EthylpentyI) -5- (3-furyl) -1-methyl-4 (1 H) -pyridone 3- [4- (2-Propylhexyloxy) phenyl] -1-methoxycarbonylmethyl-5- (2-thienyI ) -4 (1 H) pyridone

3- [3- (5,5-Dibromopentoxy) phenyl] -5- (3,5-dicyclopropylphenyl) -1-ethyl-4 (1 H) -py ridone

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

3- (4-Butoxy-2-difluoromethylphenyl) -1 -cyanomethyl-5- [3- (6-methoxyhexyloxy) phenyl] -4 (1H) -pyridone 3- (2-cyclohexyl-4-ethylphenyl) -1 - methoxy carbonylmethyl

5- [2- (6-propoxy nonyloxy) phenyl] -4 (1 H) pyridone 3- (2,4-diallyloxyphenyl) -1 - (2,2-dichloropropyl-5- (2-methyl-

6-nitrophenyl) -4 (1 H) -pyridone l-allyl-3- (4-cyano-3-ethoxycarbonylphenyl) -5- [4- (4,4,4-tri-fluoro-2-butenyloxy) phenyl] -4 (1 H) -pyridone 1 -ethoxy-3- [3- (9-iodo-1-nonenyloxy) phenyl] -5-phenyl-4 (1 H) -pyridone

3- [3- (4-Chloro-2-butynyloxy) phenyl] -l-ethoxy-5- (3-fluoro-4-isobutoxyphenyl) -4 (1H) -pyridone

1-Acetoxy-3- (2,4-dibromophenyl) -5- [3- (l, 1,2,2-tetrafluoro-3-decynyloxy) phenyl] -4 (1 H) pyridone

3- [2- (10-dodecynyloxy) phenyl] -1-methyl-5- (2-propyl-4-propylsulfonyloxyphenyl) -4 (1 H) -pyridone 3- (2,4-di (3- pentenyl) phenyl] -5- (3-phenoxyphenyl) -1 - (1,1,2,2-tetrafluoroethyl) -4 (1 H) -pyridone l- (3-chloropropyl) -3- (3-cyanomethyl-5 -ethylphenyl) -5- [3- (3-iodophenoxy) phenyl] -4 (1 H) -pyridone 3- (3-octyl-4-fluorophenyl) -5- [2- (3-ethylphenoxy) phenyl] -l trifluoromethyl 1-4 (1 H) pyridone

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

3- (3-chloro-4-heptylthiophenyl) -5- [3- (4-cyanopentyl) phenyl] -1-methyl-4 (I H) pyridone

1-Methyl-3-phenyl-5- [2- (3-ethylhexylthio) phenyl] -4 (1 H) pyridone hydrofluoride

3- (2-chloro-4-ethylphenyl) -1-ethyl-5- (3-nonylthio-4-vynil-phenyl) -4 (1 H) -pyridone l-ethynyl-3-phenyl-5- [3- (2-ethylpentylthio) phenyl] -4 (1H) pyridone

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

3- [3,5-bis (4-phenylbutylthio) phenyl] -5- (2-methylphenyl) -l- (1,1,2,2-tetrafluoroethyl) -4 (1 H) -pyridone 3- [4- (6-cyanoheptylthio) phenyl] -1-fluoromethyl-4 (1H) pyridone

3- (3-Acetoxy-5-ethylphenyl) -5- [2- (8-cyanoundecyIthio) phenyl] -1 -chlorodifluoromethyl-4 (1 H) -pyridone 3- (4-benzyl-2-ethoxyethoxyphenyl) -l - (2-carboxyethyl) -5- [3- (2-ethoxyethoxy) -5-propargylphenyl] -4 (1 H) -pyridonotoluene sulfonate l-isopropenyl-3- [3- (3-phenylpentyl) phenyl] -5- [4- (6-isopro-pynonylthio) phenyl] -4 (1 H) -pyridone 3- (2-cyanomethyl-4-vinylthiophenyl) -l-ethyl-5- [2- (7-phe-nylheptyl ) phenyl] -4 (1 H) -pyridone 3- (3-allylthio-4-methoxymethylphenyl) -5- [2- (6-cyano-hexyl) -4-vinylphenyl] -1-methyl-4 (1 H) -py ridone 3- [3- (2-decenylthio) -5- (2,4-hexadienyl) phenyl] -1-ethoxy-5-phenyl-4 (1 H) -pyridone

3- [4- (l, l-DichloralIyIthio) phenyl] -5- [3- (4-octenyl) -2-propylphenyl] -1-trifluoromethyl-4 (1 H) -pyridone 3- (4-carboxy -2-hydroxyphenyl) -5- [3- (2-chloro-3-butenylthio) -5-nitrophenyl] -1-vinyl-4 (1 H) -pyridone 3- [4- (5,5-dibromo -3-heptenylthio) phenyl] -l-methyl-5-phenyl-4 (1H) pyridone

14

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

3- (3-chlorophenyl) -5- [2- (3-fluorophenylthio) phenyl] -1-methyl-4 (1H) -pyridone l-carboxymethyl-3- [3- (2-iodophenylthio) phenyl] -5- (3-io methyl-5-methoxycarbonylphenyl) -4 (1 H) -pyridone l- (2-chloroethyl) -3- (2,4-diethylphenyl) -5- [4- (4-ethylphenyl) thio) - 2-methoxyphenyl] -4 (1 H) -pyridone 3- [3- (3-isopropylphenylthio) phenyl] -5-phenyl-l-trifluoromethyl-4 (1 H) -pyridone as 3- (2-methyl- 6-propoxyphenyl) -3- [4- (3-propoxyphenylthio) phenyl] -1-propargyl-4 (1 H) -pyridone 3- [3-chloro-5- (4-nitrophenylthio) phenyl] -l- methyl-5- (2,4-divinylphenyl) -4 (1 H) pyridone

3- (4-butylsulfinylphenyl) -5-phenyl-l-propargyl-4 (1H) -2o pyridone l-ethyl-3- (3-heptylsulfinylphenyl) -5- (4-propoxycarbonyl-phenyl-4 (1H) - pyridone l-ethoxy-3- [3- (4-propylnonylsulfinyl) phenyl] -5-phenyl-4 (1H) pyridone

25 3- (2-Ethoxyphenyl) -1-isopropyl-5- [4- (2-fluoroethylsufinyl) -2-isopropylphenyl] -4 (1 H) -pyridone

3- [3,5-Di (4-chlorophenyl) phenyl] -3- [4- (5,5-dibrompentylsulfinyl-2-ethoxyphenyl] -1-ethynyl-4 (1 H) -py ridone 3- [ 3- (12-iodododecylsulfinyl) phenyl] -5-phenyl-1-propargyl-30 4 (1H) pyridone hydroiodide

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

3- [3,5-Di (methylsulfonyloxy) phenyl] -5- [3- (5-phenylpentylsulfinyl) phenyl] -1-vinyl-4 (1 H) -pyridone 35 3- (3-acetoxyphenyl) -5 - [2- (7-cyanoheptylsulfonyl) phenyl] -1-methoxycarbonylmethyl-4 (1H) -pyridone l- (2-carboxyethyl) -3- [3- (3-cyclohexenyl) -5- (3-cyanoundece-nylfulfinyl) phenyl] -4 (1 H) pyridone

1 - (2-Chloroethyl) -3 [4- (6-methoxyhexylsulfinyl) phenyl] -4 (1 H) -40 pyridone

3- (4-Cyclopropylphenyl) -l-iodomethyl-5- [3- (6-propoxynonylfylfinyl) phenyl] -4 (1 H) -pyridone 3- [3,5-di (allylsulfinyl) phenyl] -5 -phenyl-l-propyl-4 (1H) -pyridone hydrofluoride 45 1 -dimethylamino-3- [2- (5-dodecenylsulfinyl) phenyl] -5- (3-isobutylphenyl) -4 (1 H) -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] -1 -propargyI-5- [3-50 (l, 2,3-triiod-6-dodecenylsulfînyl) phenyl] -4 (1H) -pyridone 3- [3- (4- Bromo-2-butynylsulfinyl) -5-methylphenyl] -5 [2-iodo-3- (1,2,3-trichloropentyl) phenyl] -l-vinyl-4 (1 H) -pyridone l-allyl-3- [ 2- (2,2-dibromo-4-hexynylsufmyl) phenyl] -5-phenyl-4 (1H) pyridone

55 3- (4-Benzyl-2-bromophenyl) -1 - (2-carboxyethyl) -5- [3- (l-chlorobutyl) -5 - (6-dodecynylsulfinyl) phenyl] -4 (1 H) -pyridone 1-cyanomethyl-3- [4- (3-fluorophenylsulfinyl) phenyl] -5- [3- (4-octenyl) phenyl] -4 (1 H) -pyridone

1-Chloromethyl-3- [3- (1,1-dichloro-4-octenyl) -4-nitrophenyl] -5-60 [3- (2-iodophenylsulfinyl) phenyl] -4 (1 H) pyridone

3- [3- (2-chlorovinyl) -5- (4-methylphenylsulfonyl) phenyl] -1-ethoxy-5- [3- (8-iodo-4-octenyl) phenyl] -4 (1H) -pyridone 3- [4- (3-isopropylphenylsulfinyl) phenyl] -5-phenyl-1-propyl-4 (1H) pyridone

65 3- [3- (2-Ethoxyphenylsulfinyl) phenyl] -1-methyl-5- [4- (2-propoxyphenoxy) phenyl] -4 (1 H) -pyridone l-ethyl-3- (3-hexylsulfonylphenyl) ) -5- (4-hydroxyphenyl) -4 (1H) pyridone

3- (2-Carboxy-4-ethylphenyl) -1 -dimethylamino-5- [4- (3-ethyl-heptylsulfonyl) phenyl] -4 (1 H) -pyridone l-acetoxy-3- (2-hexyl -5-fluorophenyI) -5- (3-nitro-5-nonyIsul-fonylphenyl) -4 (1 H) -pyridone

3-phenyl-1-propoxy-5- [2- (3-propylnonylsulfonyl) phenyl] -4 (lH) -py ridone l-ethoxy-3-phenyI-5- (3-trifluoromethyl-5-trifluoromethylsulfonylphenyl) - 4 (1 H) -pyridone 3- (3-bromo-5-nitrophenyl) -1 -ethynyl-5- [4-cyano-2- (6,6-dibromohexylsulfonyI) phenyl] -4 (1 H) -pyridone 3- [3- (4,4-Diiododecyisulfonyl) phenyl] -5- (2-naphthyl) -1 - (1-propynyl) -4 (1 H) -pyridone

3- [5-Chloromethyl-4- (2-propylphenyl) phenyl] -1-vinyl-5- [4- (3-phenylbutylsulfonyl) phenyl] -4 (1 H) pyridone 3- [3- (3-cyanopropylsulfonyl ) phenyl] -1-methoxycarbonyl-methyl-5-phenyl-4 (1 H) -pyridone l- (2-carboxyethyl) -3- [4- (7-cyanoheptylsulfonyl) phenyI] -5- [3- (4- chlorophenylphenyl] -4 (1 H) -pyridone 1-cyanomethyl-3- [3- (1-cyanoundecylsulfonyl) -5-fluorophenyl] -5- (4-propylsulfonyloxyphenyl) -4 (1 H) -pyridone 3- ( 2-acetoxy-4-ethoxyethysulfonylphenyl) -1-chloromethyl-5- (5-cyclopropyl-2-trifluoromethylphenyl) -4 (1H) -pyridone 3- [4- (3-cyclohexenyl) phenyl] -1-propyl-5- [3- (9-propoxynonylsulfonyl) phenyl] -4 (1H) pyridone 1-acetoxy-3- [4- (2,3-hexadienylsulfonyl) phenyl] -5-phenyl-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 (1 H) pyridone 3- [4- (6-HeptinyI) -3-methylphenyl] -1-ethyl-5- [3- (1,1,2-triiod-3-butenylsulfonyl) -5-chlorophenylj-4 (1 H) -pyridone 3- [2- (5,5-dibromo-2-pentynyl) phenyl] -1-dimethylamino-5- [3- (5-fluoro-2-nonenyisulfonyl) phenyl] -4 (1 H) -pyridone l-acetoxy -3- [2-ethyl-4- (5-methoxypentyl) phenyl] -5- [3- (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] -1-methoxy-4 (1 H) pyridone 3- [4- (6,6-dibromo-3-hexynylsulfonyl) phenyl] -5-phenyl-1-propoxy-4 (1 H) pyridone

3- [3- (2-Cyanoethyl) phenyl] -l-ethynyl-5- [l, 1,2,2-tetrafluoro-6-decinylsulfonyl) phenyl] -4 (1 H) -pyridone l-cyanomethyl-3- [3- (6-dodecynylsulfonyl) -5-methylphenyl] -5- [2-methyl-4- (l, 1,2,2-tetrafluoroethyl) phenyl] -4 (l H) pyridone l- (2-carboxyethyl ) -3-phenyl-5- (3-phenylsulfopylphenyl) -4 (1H) pyridone

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

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

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

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

3- (2-Cyclopentylsulfinylphenyl) -5- (3-hexylphenyl) -1-propoxy-4 (1 H) -pyridone hydrochloride 3- (3-Cyclohexylsulfonylphenyl) -5- (3,5-difluorophenyl) -1 -tri-fluoromethyl-4 (1 H) -pyridone 1-cyanomethyl-3- (2-cyclopropylmethoxyphenyl) -5- (trifluoro-

15 632496

methylphenyl) -4 (1 H) pyridone 1-acetoxy-3- [3- (2-cyclohexylethoxy) phenyl] -5-phenyl-4 (1 H) pyridone hydrobromide

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

3-t4- (2-Cyclohexylethylsulfonyl) phenyl] -l-ethyl-5- (3-propyl-phenyl) -4 (1 H) -pyridone io 3-cyclopropylmethyl-5- (3-fluorophenyl) -l-methoxy- 4 (1H) pyridone methanesulfonate

3- (4-chlorophenyl) -3- (2-cyclohexylethyl) -1-ethoxy-4 (1H) pyridone

3- (3-fluorophenyl) -1-methyl-5-phenylthio-4 (1 H) -pyridone 15 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) -1 -dimethylamino-5- (4-ethylphenyl-20 sulfinyl) -4 (1H) pyridone

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

3- (2-chloroethylsulfinyl) -1-chloromethyl-5- (3-methylphenyl) -25 4 (1H) pyridone

1 - (1-Carboxyethyl) -3- (2,4-dimethylphenyl) -5-vinylthio-4 (1H) -pyridone l- (2-bromoethyl) -3- (2-chloro-3-fluorophenyl) -5 - (l, 2-difluoral-ly lsulfiny l) -4 (1 H) -py ridone 30 1 -dimethylamino-3- (4-methoxy-2-butenyl) -5-phenyl-4 (1H) -pyridone l- Ethynyl-3- (2-propoxyvinyl) -5- (3-trifluoromethylphenyl-4 (1H) pyridone.

Preferred compounds of the formula I are given below.

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

40 3- (3-fluorophenyl) -1-methyl-5-phenyl-4 (1H) -pyridone 3- (3-chlorophenyl) -l-methyl-5-phenyl-4 (1H) -pyridone 3,5-bis (3-chlorophenyl) -1-methyl-4 (1 H) -pyridone 3- (3-chlorophenyl) -5- (3-fluorophenyl) -l-methyl-4 (1H) -pyridone

45 1-methyl-3- (3-methylphenyl) -5-phenyl-4 (1 H) -pyridone 3,5-diphenyl-1-methyl-4 (1 H) -pyridone 1-methyl-3,5-bis (3-trifluoromethylphenyl) -4 (1H) pyridone 3- (3-bromophenyl) -1-methyl-5-phenyl-4 (1 H) -pyridone 3- (3-methoxyphenyl) -1-methyl-5-phenyl -4 (1 H) -pyridone so 3- (3-ethoxyphenyl) -1-methyl-5-phenyl-4 (1 H) -pyridone 1-methyl-3-phenyl-5- (3-propoxyphenyl) -4 ( 1 H) -pyridone 3- (3-isopropoxyphenyl) -1-methyl-5-phenyl-4 (1 H) -pyridone 1-methyl-3-phenyl-5- [3- (1,1,2,2- tetrafluoroethoxy) phenyl] -4 (1H) pyridone 55 3,5-bis (3-fluorophenyl) -1-methyl-4 (1H) pyridone

3- (2-chlorophenyl) -1-methyl-5- (3-trifluoromethylphenyl) -4 (1 H) -py ridone

3- (3-chlorophenyl) -1-methyl-5- (3-trifluoromethylphenyl) -4 (1H) -py ridone

60 3- (4-chlorophenyl) -1-methyl-5- (3-trifluoromethylphenyl) -4 (1H) -pyridone

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

3- (3-fluorophenyl) -1-methyl-5- (3-trifluoromethylphenyl) -65 4 (1H) pyridone

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

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

632 496

l-ethyl-3-phenyl-5- (3-trifluoromethylphenyl) -4 (lH) -pyridone 1-allyl-3-phenyl-5- (3-trifluoromethylphenyl) -4 (lH) -pyridone l-methyl-3 - (3-trifluoromethylphenyl) -4 (1H) pyridone 3-chloro-1-methyl-5- (3-trifluoromethylphenyl) -4 (1 H) pyridone 3-bromo-l-methyl-5- (3-trifluoromethylphenyl ) -4 (lH) -pyridone 1,3-dimethyl-5- (3-trifluoromethylphenyl) -4 (lH) -pyridone 3-ethyl-l-methyl-5- (3-trifluoromethylphenyl) -4 (lH) - pyridone 3-isopropyl-1-methyl-5- (3-trifluoromethylphenyl) -4 (1 H) -pyridone.

If one carries out the cyclization with hydroxylamine or a salt thereof when carrying out the process according to the invention, corresponding compounds of the formula Ia are obtained in which R is a hydroxyl group, which is then converted back into the corresponding pyridothione of the formula Ib by reaction with phosphorus pentasulfide can be converted. It is then possible to acetylate them subsequently to the corresponding 1-acetoxy compounds, and it is also also possible to prepare pyridones of the formula Ia, in which R is a hydroxy group, prepared by the process according to the invention, first to the corresponding pyridones, in which R is an acetoxy group means to acetylate, and then convert it to the corresponding pyridothiones by subsequent treatment with phosphorus pentasulfide.

As a result, pyridothiones of the formula Ib which can be prepared by the process according to the invention

S

(ib)

• R

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 (3-methoxyphenyl) -4 (1H) -pyridine thione, 1-ethyl-3- (4-ethoxyphenyl) -5-phenyl-4 (1 H) -pyridine thione, 3- (3rd , 5-Diiodophenyl) -5- (3-propylphenyl) -1-propyl-4 (1H) -pyridinethione,

l-allyl-3- (3-chlorophenyl) -5- (2,3-diethoxyphenyl) -4 (1H) -pyridinethione,

3,5-diphenyl-1-ethyl-4 (1 H) -pyridine thione, l-acetoxy-3- (3,5-diethylphenyl) -5- (2,4-diethylphenyl) -4 (1 H) -pyridine thione,

1 - allyl-3- (1-naphthyl) -5- (4-propoxyphenyl) -4 (1 H) -pyridine-thione,

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

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

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

3- (2-J odphenyl) -5- (3-isopropylphenyl) -1-methoxy-4 (1H) -

pyridinthion,

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

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

3- (2-iodo-4-propylphenyl) -l-methyl-5- (4-trifluoromethyl-phenyl) -4 (1 H) -py ridinthione,

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

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

1 - (2-chloroethyl) -3-cyano-5-phenyl-4 (1 H) -pyridinthione, 3,5-diphenyl-l-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 (1 H) -py ridinthion,

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

l-dimethylamino-3,5-bis (3-trifluoromethylphenyl) -4 (lH) -

pyridinthion,

1 - (2-chloroethyl) -3- (4- (2-cyanoethyl) phenyI) -4 (1 H) -pyridinethione,

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) -pyri-

dinthion,

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

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

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

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

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

3- (2-ethyl-3-fluorophenyl) -5-ethynyl-1-methyl-4 (1H) -pyrididinion,

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

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

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

I-acetoxy-3- (4-propylcyclohexyl) -5- (3- (6,6,6-trifluoro-2-hexynyl) phenyl) -4 (1 H) -pyridinethione, 3- (3- (4-octynyl ) phenyl) -5- (2-methoxycyclophenyl) -1-methyl-4 (1 H) -pyridinethione,

3- (4-Cyclopropylphenyl) -l- (2-methoxycarbonylmethyl) -5- (2-propoxycyclobutyl) -4 (1 H) -pyridinthione, 3- (2-Cyclobutenyl) -5- (3-cyclopentylphenyl) -l- ethoxy-4 (lH) pyridine thione,

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

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

3- (1,2-dibromopropoxy) -1-ethoxy-5- (2-methylsulfonyloxy-phenyl) -4 (1 H) -pyridine thione,

3- (3-Diphenylyl) -l-methyl-5-vinyloxy-4 (lH) -pyridinthione, l-cyanomethyl-3- (2-methylphenoxy) -5- (3- (4-nitro-phenyl) phenyl) - 4 (1 H) -pyridinthione, 1-methyl-3- (4-nonyloxyphenyl) -5- (3-thienyl) -4 (1 H) -pyrididinion,

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-isopropoxy-4 (1 H) -pyridinethione,

3- (2,4-Dimethoxyphenyl) -1 - (2-methoxycarbonylmethyl-5- (2- (12-iodododecyloxy) phenyl) -4 (1H) -pyridinethione, 3- (4-benzyloxyphenyl) -1 -cyanomethyl-5 - (3,5-di (isopropenyl) phenyl) -4 (1 H) -pyridinethione, 3- (2,4-diformyloxyphenyl) -1 -ethoxy-5- (4- (3-phenyl) hexy-

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loxy) phenyl) -4 (1 H) -pyridinethione,

3- (4- (3-cyanopropoxy) phenyl) -5- (3-ethoxy-5-iodophenyl) -1-methyl-4 (1 H) -pyridinethione,

3- (4- (7-cyanoheptyloxy) phenyl) -1-ethyl-5-phenyl-4 (1H) -pyridinethione,

3- (3- (4-Cyanoundecyloxy) phenyl) -5- (2,4-di (2-ethoxyethyl) phenyl) -1-methoxy-4 (1 H) -pyridinethione, 3- (2- (2 -Ethoxyethoxy) phenyl) -1 - (2-iodoethyl) -5- (3,4-diaceto-xyphenyl) -4 (1 H) -py ridinthion,

3- (2,4-di (2-pentinyl) phenyl) -1-isopropoxy-5- (2-vinyloxy-phenyl) -4 (1 H) -py ridinthion,

3- (3- (2,4-hexadienyloxy) phenyl) -1-isopropyl) -5-phenyl-4 (I H) -pyridinthione hydroiodide,

1- (2-Carboxyethyl) -3- (2,6-dipropylphenyl) -5- (4- (5-dodecenylyloxy) phenyl) -4 (1 H) -pyridinethione, 3- (2- (2-chloroallyloxy) ) phenyl) -l- (2,2-dichloroethyl) -5- (2,4-diethoxyphenyl-4 (1 H) -pyridinethione, l-chloromethyl-3- (3-methylsulfonyloxy-5-vinyIphenyl-5- (3rd - (2,2-dibromo-3-heptenyloxy) phenyl) -4 (1 H) -pyridinethione, l-chlorodifluoromethyl-3- (2,4-di (chloromethyl) phenyl) -5- (2- (1,2 , 3-trichloro-6-dodecenyloxy) phenyl) -4 (1 H) -pyridinethione,

3- (3- (6,6-dibromo-3-hexynyloxy) phenyl) -1-methyl-5- (3-nitro-

4-propylpheny I) -4 (1 H) -pyridine thione, 3- (3-ethynyloxyphenyl) -1-methyl-5-phenyl-4 (1 H) -pyridine-thione hydrobromide,

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

l-Chloromethyl-3- (2,4-difiuorphenyl) -5- (2- (3-propoxyphe-noxy) phenyl) -4 (1 H) -pyridinethione, 1-methyl-3- (4- (2-nitrophenoxy ) phenyl) -5-phenyl-4 (1 H) -pyridinethione,

3- (3-isobutylthiophenyl) -1-isopropyl-5-phenyl-4 (1 H) -pyrididinion,

l- (2-methoxycarbonylmethyl) -3- (4- (3-iodophenyl) phenyl) -5- (3-trifluoromethylthiophenyl) -4 (lH) -pyridinethione, l-acetoxy-3- (3-cyclopentylphenyl) -5- (3- (2-fluoroethylthio) phenyl) -4 (1 H) pyridine thione,

3- (3-benzylthio-5-ethynylphenyl) -1 -cyanomethyl-5- (2-hexylphenyl) -4 (1 H) -pyridinethione,

3- (2-Bromo-4- (6-phenylhexylthio) phenyl) -5- (4- (2-cyanopro-pylthio) -2-ethylphenyl) -1-methyl-4 (1 H) -pyridinethione, 1-ethyl -3- (4- (6-methoxyhexylthio) phenyl) -5-phenyl-4 (1H) pyridine thione,

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

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

1-ethyl-3- (3-fluorophenyl) -5- (4- (12,12,12-trichloro-2,6-dode-cadienylthio) phenyl) -4 (1 H) -pyridinethione, 1 - (2- Chloropropyl) -3 (2-cyclopropyI-4- (1,1,2,2-tetrafluoro-5-decinylthio) phenyl) -5-phenyl-4 (1 H) -pyridinethione, 3- (4- (4-decinylthio ) -2-methylphenyl) -1-ethoxy-5- (5-fluoro-3-trifluoromethylphenyl) -4 (1H) -pyridinethione, 1-cyanomethyl-3- (4-phenylthiophenyI) -5-phenyl-4 (1H) pyridinthione hydrochloride,

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

3 - (2-Carboxyphenyl) -1 -dimethylamino-5- (2-hydroxy-4- (2-propylpentylsulfinyl) phenyl) -4 (1 H) -py ridinthione, l-acetoxy-3- (2-cyano-5 -nonylsulfinylphenyl) -5- (3,5-dinitro-phenyI) -4 (1 H) -pyridinthione,

l-methoxy-3- (2-nitrophenyl) -5- (4-trifluoromethylsulfinyl-phenyl) -4 (1 H) -pyridinethione,

3- (2- (3-cyanopropylsulfinyl) phenyl) -1-methoxycarbonyl-methyl-5-phenyl-4 (1 H) -pyridinethione, 3- (2-chloro-4-cyclohexylphenyl) -5- (3-chloro 5- (2-ethoxyethylsulfonyl) phenyl) -1 - (2-cyanoethyl) -4 (1 H) -pyridinethione, 3- (3- (2-chloro-6-undecynylsulfinyl) phenyl) -l- (2, 2-dibromo

17 632496

ethyl) -5- (2-ethyl-5-vinylsulfinylphenyl) -4 (1H) -pyridine-thione,

3- (3- (2,4-HexadienyIsulfinyl) phenyl) -l-methyl-5-phenyl-4 (1 H) -pyridinethione, s 1 - acetoxy-3- (4- (2-bromallylsulfinyl) phenyl) -5 - (2,4-dimethylphenyl) -4 (1 H) -pyridinethione,

1-isopropyl-3-phenyl-5- (4- (1,1,2-trichlor-3-heptenylsul-finyl) phenyl) -4 (1 H) -pyridinethione,

l-methoxycarbonylmethyl-3- (3-ethyl-5- (9,9,10,10-tetrafluoro-îo 3-decinylsulfinyl) phenyl) -5-phenyl-4 (1 H) -pyridinethione, l- (2-cyanoethyl ) -3- (4-phenyIsulfinylphenyl) -5-phenyl-4 (1 H) -pyridinethione,

3- (4- (2,4-Cyclohexadienyl) -3-fluorophenyl) -1-ethyl-5- (3-hydroxy-5- (nitrophenylsulfinyl) phenyl) -4 (1 H) -pyridinethione, 15 l-methyl- 3- (4-methylsulfonylphenyI) -5-phenyI-4 (1H) -pyrididinion,

3- (4- (2-Chloroethylsulfonyl) phenyl) -5- (3-fluoro-4-octylphenyl) -1-methoxy-4 (1 H) -pyridinethione, 3- (3-ethoxyhexylsulfonylphenyl) -5-phenyl -1-trifluoromethyl-20 4 (1H) -pyridinethione,

3- (3-Cyanomethyl-4- (1 -cyclobutenyI) phenyl) -1 -methyl-5- (4-vinylisulfonylphenyl) -4 (1 H) -pyridinethione, 3- (2-allylsulfonyl-4-chlorophenyl) - 5- (2-allyl-3-cyclohexyl-phenyl) -1 -dimethylamino-4 (1 H) -pyridinethione, 2s 3- (3-benzyl-5-ethynesulfonylphenyl) -5- (2- (7-phenyl-heptyOpheny 1) -1-vinyl-4 (1 H) -pyridinethione, l-ethyl-3- (3-ethyl-5- (4-methylphenylsulfonyl) phenyl) -5- (4-iodo-3- (2-propylbutyl) phenyl) -4 (1 H) -pyridinethione, 1 - (1-cyanoethyl) -3- (3- (2-propylphenylsulfonyl) phenyl) -5-30 phenyl-4 (1H) -pyridinethione,

3- (5-Butyl-2- (3-methoxyphenylsulfonyl) phenyl) -l- (l-carboxy-ethyl) -5-phenyl-4 (1 H) -pyridinethione, 3- (2-cyclopropoxyphenyl) -1-ethyl -5- (2-fluorophenyl) -4 (1H) pyridinethione,

35 3- (4-cyclopropylsulfonylphenyl) -5- (2,4-diethylphenyl) -1-propyl-4 (1 H) -pyridinethione,

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

l-cyanomethyl-3-phenyl-5- (3-propoxyphenylsulfinyl) -40 4 (1H) -pyridinethione,

3- (2-chlorophenyl) -1-methyl-5-propylsulfinyl-4 (1 H) -pyri-dinthione hydrofluoride,

1-ethoxy-3- (4-fluorophenyl) -5-trifluoromethylthio-4 (1 H) -pyri-dinthione-toluenesulfonate,

45 3- (2-bromopropylsulfonyl) -1-chlorodifluoromethyl I-5-phenyl-4 (1 H) -pyridinethione,

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

1-methyl-3- (2-trifluoromethylphenyl) -5-vinylsulfonyl-4 (1 H) -50 pyridine thione,

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

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

55 3- (6-Ethoxy-2-hexenyl) -1-methyl-5-phenyl-4 (1 H) -pyridine-thione hydrochloride.

Of these pyridine thiones, l-methyl-3-phenyI-5- (3-trifluorom-60 thylphenyl) -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 in degrees Celsius 65. The nuclear magnetic resonance spectra, ie the NMR spectra, were determined on a 60 megahertz instrument using tetramethylsilane as an internal reference source and are given in cycles per second (CPS).

632496

give. The melting points have been determined with a heating block.

example 1

A) Preparation of the starting material of formula IV

100 g l, 3-diphenyl-2-propanone are dissolved in 35 g ethyl

miat dissolved, and this solution is added over a period of 30 minutes at a temperature of 0 to 5 ° C with 25 g of sodium methoxide in 500 ml of ethyl ether. The reaction mixture is then allowed to come to room temperature and is stirred overnight. By filtering the mixture obtained in this way, 460 g of the disodium salt of 1,5-dihydroxy-2,4-diphenyl-1,4-pentadien-3-one is obtained, which is used for the next process step without purification.

B) Cyclization

20 g of the above crude salt are added to a solution of 20 g propylamine and 5 ml concentrated hydrochloric acid in 75 ml water. The mixture is stirred at room temperature for 0.5 hours. The reaction mixture is then extracted with ethyl ether and the aqueous layer is evaporated to dryness. The residue is extracted with chloroform and the combined organic extracts are evaporated to dryness. By recrystallizing the residue obtained from benzene-hexane, 3.05 g of 3,5-diphenyl-1-propyl-4 (1 H) -pyridone is obtained, which melts at 172 to 174 ° C.

In the following examples, the corresponding starting material of the formula IV was prepared in step A) by the process described in example 1, step A).

In step B) the cyclization then took place, using a corresponding amine of the formula RNH2, by the process described in Example 1, step B).

Example 2

A) The starting material of the formula IV used was the 1,5-dihydroxy-2,4-diphenyl-1,4-pentadien-3-one, and it is thus identical to the starting material of the formula IV used in Example 1.

B) Cyclization

The starting material obtained according to A) was cyclized with methoxyamine to give the 3,5-diphenyl-l-methoxy-4 (1H) pyridone. The melting point was 165 ° C; the yield was 95%.

Example 3

A) The starting material of the formula IV prepared was the 1,5-dihydroxy-2- (3-fluorophenyl) -4-phenyl-1,4-penta-dien-3-one.

B) Cyclization

The product obtained according to A) was cyclized using methylamine to give the 3- (3-fluorophenyl) -l-methyl-5-phenyl-4 (1H) -pyridone. The melting point was 133.5 ° C and the yield was 69%.

Example 4

A) The starting material of the formula IV prepared was 2- (4-bromophenyl) -1,5-dihydroxy-4-phenyl-1,4-penta-dien-3-one.

B) Cyclization

The product obtained according to A) was cyclized using methylamine to give the 3- (4-bromophenyl) -1-methyl-5-phenyl-4 (1 H) -pyridone. The melting point was 172 ° C and the yield was 63%.

Example 5

A) The starting material of the formula IV prepared was the 1,5-dihydroxy-2- (4-methoxyphenyl) -4-phenyl-1,4-pen-tadien-3-one.

B) Cyclization

The product obtained according to A) was cyclized using methylamine to give the 3- (4-methoxyphenyl) -l-methyl-5-phenyl-4 (1H) pyridone. The melting point was 165 ° C and the yield was 33%.

Example 6

A) The starting material of the formula IV prepared was 2- (3-chlorophenyl) -1,5-dihydroxy-4-phenyl-1,4-penta-dien-3-one.

B) Cyclization

The product obtained according to A) was cyclized using methylamine to give the 3- (3-chlorophenyl) -1-methyl-5-phenyl-4 (1 H) -pyridone. The melting point was 172.5 ° C and the yield was 27%.

Example 7

A) The starting material of formula IV prepared was 2- (4-chlorophenyl) -1,5-dihydroxy-4-phenyl-1,4-penta-dien-3-one.

B) Cyclization

The product obtained according to A) was cyclized using methylamine to give the 3- (4-chlorophenyl) -1-methyl-5-phenyl-4 (1 H) -pyridone. The melting point was 141.5 ° C and the yield was 76%.

Example 8

A) The starting material of the formula IV produced was 1,5-dihydroxy-2- (1-naphthyl)) - 4-phenyl-1,4-pentadien-3-one.

B) Cyclization

The product obtained according to A) was cyclized using methylamine to give the l-methyl-3- (l-naphthyl) -5-phenyl-4 (1H) -pyridone.

In NMR, this product showed maxima at 204 and 483 CPS and aromatic protons at 430 to 470 CPS. The yield was 12%.

Example 9

A) The starting material of the formula IV prepared was the 2,4-bis (3-chlorophenyl) -1,5-dihydroxy-1,4-pentadien-3-one.

B) Cyclization

The starting material prepared according to A) was cyclized to the 3,5-bis (3-chlorophenyl) -1-methyl-4 (1H) -pyridone using methylamine. The melting point was 164 to 167 ° C and the yield was 59%.

Example 10

A) The starting material of formula IV prepared was 1,5-dihydroxy-2- (3-methylphenyl) -4-phenyl-1,4-penta-dien-3-one.

B) Cyclization

The product prepared according to A) was cyclized using methylamine to give the l-methyl-3- (3-methylphenyl) -5-phenyl-4 (1H) pyridone. This formed a complex with 0.5 mol of benzene. The melting point was 79.5 ° C and the yield was 25%.

Example 11

A) The starting material of the formula IV prepared was 1,5-dihydroxy-2- (4-methylphenyl) -4-phenyl-1,4-penta-dien-3-one.

B) Cyclization

The product obtained according to A) was converted to l-methyl-3- (4-methylphenyl) - using methylamine

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5-phenyl-4 (1 H) -pyridone cyclized. The melting point was 144.5 ° C and the yield was 28%.

Example 12

A) The starting material of the formula IV prepared was 1,5-dihydroxy-2- (2-methylphenyl) -4-phenyl-1,4-penta-dien-3-one.

B) Cyclization

The starting material obtained according to A) was cyclized using methylamine to give the l-methyl-3- (2-methylphenyl) -5-phenyl-4 (1 H) -pyridone. The NMR showed maxima at 133 and 201 CPS and aromatic protons at 420 to 440 and 442 to 460 CPS. The yield was 16%.

Example 13

A) The starting material of formula IV produced was 1,5-dihydroxy-2- (4-fluorophenyl) -4-phenyl-1,4-penta-dien-3-one.

B) Cyclization

The product obtained according to A) was cyclized with methylamine to give the 3- (4-fluorophenyl) -1-methyl-5-phenyl-4 (1H) pyridone. The melting point was 166 ° C and the yield was 60%.

Example 14

A) The starting material of the formula IV prepared was 1,5-dihydroxy-2-phenyl-4- (3-trifluoromethylphenyl) -1,4-pentadien-3-one.

B) Cyclization

The starting material obtained according to A) was cyclized using methylamine to give the 1-methyl-3-phenyl-5- (3-trifluoromethylphenyl) -4 (1H) -pyridone. The melting point was 152 to 156 ° C and the yield was 52%.

Example 15

A) The starting material of the formula IV prepared was 1,5-dihydroxy-2- (3-methoxyphenyl) -4-phenyl-1,4-pen-tadien-3-one.

B) Cyclization

The product obtained according to A) was cyclized using methylamine to give the 3- (3-methoxyphenyl) -l-methyl-5-phenyl-4 (1 H) -pyridone. The NMR showed maxima at 200 and 220 CPS and aromatic protons at 420 to 440 and 442 to 460 CPS. The yield was 33%.

Example 16

A) The starting material of the formula IV prepared was 2- (3,4-dichlorophenyl) -1,5-dihydroxy-4-phenyl-1,4-pen-tadien-3-one.

B) Cyclization

The product obtained according to A) was cyclized using methylamine to give the 3- (3,4-dichlorophenyl) -l-methyl-5-phenyl-4 (1 H) -pyridone. The melting point was 166.5 ° C and the yield was 54%.

Example 17

A) The starting material of the formula IV produced was 2- (2,5-dichlorophenyl) -1,5-dihydroxy-4-phenyl-1,4-pen-tadien-3-one.

B) Cyclization

The product obtained according to A) was cyclized using methylamine to give the 3- (2,5-dichlorophenyl) -1-methyl-5-phenyl-4 (1H) pyridone. The melting point was 155.5 ° C and the yield was 22%.

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Example 18

A) The starting material of the formula IV prepared was 2- (2-chlorophenyl) -l, 5-dihydroxy-4-phenyl-l, 4-penta-dien-3-one.

s B) Cyclization

The product obtained according to A) was cyclized with methylamine to give the 3- (2-chlorophenyl) -1-methyl-5-phenyl-4 (1H) pyridone. The melting point was 145 ° C and the yield was 29%.

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Example 19

A) The starting material of the formula IV prepared was 1,5-dihydroxy-2,4-bis (3-fluorophenyl) -1,4-pentadien-3-one.

i5 B) Cyclization

The product obtained according to A) was cyclized to 3,5-bis (3-fluorophenyl) -1-methyl-4 (1 H) -pyridone using methylamine. The melting point was 149 to 151 ° C and the yield was 60%.

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Example 20

A) The starting material of the formula IV prepared was 2- (3-chlorophenyl) -1, 5-dihydroxy-4- (3-fluorophenyl) -1, 4-pentadien-3-one.

25 B) Cyclization

The product obtained according to A) was cyclized with methylamine to give the 3- (3-chlorophenyl) -5- (3-fluorophenyl) -1-methyl-4 (1H) pyridone. The melting point was 145 to 146 ° C and the yield was 64%.

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Example 21

A) The starting material of the formula IV prepared was 2- (3,5-dichlorophenyl) -1,5-dihydroxy-4-phenyl-1,4-pen-tadien-3-one.

35 B) Cyclization

The starting material obtained according to A) was cyclized using methylamine to give the 3- (3,5-dichlorophenyl) -1-methyl-5-phenyl-4 (1 H) -pyridone. The melting point was 131 to 135 ° C and the yield was 28%.

40

Example 22

A) The starting material of formula IV prepared was the 2,4-bis (3-bromophenyl) -1,5-dihydroxy-1,4-pentadien-3-one.

45 B) Cyclization

The product obtained according to A) was cyclized with methylamine to give the 3,5-bis (3-bromophenyl) -1-methyl-4 (1H) pyridone. The melting point was 216.5 ° C and the yield was 43%.

see example 23

A) The starting material of formula IV prepared was das2- (3-bromophenyl) -l, 5-dihydroxy-4-phenyl-l, 4-penta-dien-3-one.

B) Cyclization

55 The product obtained according to A) was cyclized using methylamine to give the 3- (3-bromophenyl) -l-methyl-5-phenyl-4 (1 H) -pyridone. The melting point was 172 ° C and the yield was 38%.

«O Example 24

A) The starting material of formula IV produced was 1,5-dihydroxy-2- (2-fluorophenyl) -4-phenyl-1,4-penta-dien-3-one.

B) Cyclization

65 The product obtained according to A) was cyclized using methylamine to give the 3- (2-fluorophenyl) -l-methyl-5-phenyl-4 (1 H) -pyridone. The melting point was 165 ° C and the yield was 19%.

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Example 25

A) The starting material of formula IV produced was 2- (3-bromophenyl) -1,5-dihydroxy-4- (3-trifluoromethyl-phenyl) -1,4-pentadien-3-one.

B) Cyclization

The product obtained according to A) was cyclized using methylamine to give the 3- (3-bromophenyl) -1-methyl-5- (3-trifluoromethylphenyl) -4 (1H) -pyridone. The melting point was 151 to 153 ° C and the yield was 37%.

Example 26

A) The starting material of the formula IV prepared was 1,5-dihydroxy-2-phenyl-4- (3-trifluoromethylphenyl) -1,4-pentadien-3-one.

B) Cyclization

The product obtained according to A) was cyclized using 2-aminopropionic acid to give the 1- (1-carboxyethyl) -3-phenyl-5- (3-trifluoromethylphenyl) -4 (1 H) -pyridone. The melting point was 236 to 237 ° C and the yield was 13%.

Example 27

A) The starting material of formula IV was 1,5-dihydroxy-2,4-diphenyl-1,4-pentadien-3-one.

B) Cyclization

The product obtained according to A) was cyclized using 1,1-dimethylhydrazine and 1-dimethylamino-3,5-diphenyl-4 (1H) -pyridone. The melting point was 143 ° C and the yield was 94%.

Example 28

A) The starting material of formula IV prepared was 1,5-dihydroxy-2- (2-naphthyl) -4-phenyl-1,4-pentadien-3-one.

B) Cyclization

The product obtained according to A) was cyclized using methylamine to give the l-methyl-3- (2-naphthyI) -5-phenyl-4 (1 H) -pyridone. The melting point was 101 to 105 ° C and the yield was 45%.

Example 29

A) The starting material of the formula IV prepared was 1,5-dihydroxy-2-phenyl-4- (3-trifluoromethylphenyl) -1,4-pentadien-3-one.

B) Cyclization

The product obtained according to A) was cyclized using ethylamine to give the 1-ethyl-3-phenyl-5- (3-trifluoromethylphenyl) -4 (1H) -pyridone. The melting point was 98 to 100 ° C and the yield was 66%.

Example 30

A) The starting material of the formula IV prepared was 1,5-dihydroxy-2-phenyl-4- (3-trifluoromethylphenyl) -1,4-pentadien-3-one.

B) Cyclization

The product obtained according to A) was cyclized using propylamine to give the 3-phenyl-l-propyl-5- (3-trifluoromethylphenyl) -4 (1H) -pyridone. This showed triplet maxima at 60 and 230 CPS and a sextuplet at 114 CPS in the NMR. The yield was 42%.

Example 31

A) The starting material of the formula IV prepared was 1,5-dihydroxy-2-phenyl-4- (3-trifluoromethylphenyl) -1,4-pentadien-3-one.

B) Cyclization

The product obtained according to A) was cyclized using methoxyamine to the 1-methoxy-3-phenyl-5- (3-trifluoromethylphenyl) -4 (1H) -pyridone. This showed a maximum at 248 CPS in the NMR.

Example 32

A) The starting material of formula IV prepared was das2- (3-chlorophenyl) -l, 5-dihydroxy-4- (3-trifluoromethyl-phenyl) -1,4-pentadien-3-one.

B) Cyclization

The product obtained according to A) was cyclized using methylamine to give the 3- (3-chlorophenyl) -1-methyl-5- (3-trifluoromethylphenyl) -4 (1H) pyridone. The melting point was 133 to 135 ° C and the yield was 28%.

Example 33

A) The starting material of the formula IV was 2- (4-biphenylyl) -1,5-dihydroxy-4-phenyl-1,4-pentadien-3-one.

B) Cyclization

The starting material obtained according to A) was cyclized using methylamine to give the 3- (4-biphenylylL) -l-methyl-5-phenyl-4 (1H) -pyridone. The melting point was 186 to 190 ° C and the yield was 1%.

Example 34

A) The starting material of the formula IV prepared was 2- (3-biphenylyl) -1,5-dihydroxy-4-phenyl-1,4-pentadien-3-one.

B) Cyclization

The product obtained according to A) was cyclized using methylamine to give the 3- (3-biphenylyl) -l-methyl-5-phenyl-4 (1 H) -pyridone. The melting point was 186 to 190 ° C and the yield was 2%.

The following examples are used to subsequently describe reactions to which the products prepared by the cyclization process according to the invention can be subjected in order to exchange substituents in the phenyl nucleus for other substituents.

Example 35

2 g of the 3 - (3-methoxyphenyl) -1-methyl-5-phenyl-4 (1 H) -py ri-dones prepared by the process according to Example 15 are mixed with 15 g of pyridine hydrochloride, whereupon the mixture is about Heated to reflux temperature for 1 hour. The mixture is then poured into a large amount of water and the precipitated solids are separated by filtration. After recrystallizing the solids from ethanol-ethyl ether, 1.1 g of 3- (3-hydroxyphenyi) -1-methyl-5-phenyl-4 (1 H) -pyridone are obtained. Another 0.65 g of product are obtained by concentrating the above filtrate.

This product melts at 223-225 ° C.

Example 36

The 3-cyclohexyl-5- (3-methoxyphenyl) -1-methyl-4 (1 H) -pyridone was prepared by cyclization according to the procedure described in Example 1.

Following the procedure described in Example 35, this product was converted to the 3-cyclohexyl-5- (3-hydroxyphenyl) -l-methyl-4 (1 H) -pyridone. The melting point was 155-165 ° C and the yield was 13%.

Example 37

This example explains the etherification of a hydroxy substituent in the benzene nucleus, whereby further products are obtained, all of which fall under the formula Ia.

2.2 g of the product obtained according to the procedure in Example 35

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3- (3-Hxdroxyphenyl) -1-methyl-5-phenyl-4 (1 H) -pyridones 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, whereupon the filtrate is evaporated to dryness under vacuum. 2.2 g of the 3- (3-ethoxyphenyl) -1-methyl-5-phenyl-4 (1 H) -pyridone, which melts at 133 to 135 ° C., are obtained as the product.

The following further compounds are produced in an analogous manner to the example described above:

3- (3-Allyloxyphenyl) -1-methyl-5-phenyl-4 (1 H) -pyridone, NM R maxima at 211 and 270 CPS, broad maxima at 296 to 328.341 to 378 and 399 to 458 CPS, the yield is 10%;

3- [3- (1-Fluoro-2-iodovinyloxy) phenyl] -1 -methyl-5-phenyl-4 (1H) pyridone, NMR maximum at 218 CPS, a broad maximum at 270 to 316 CPS, aromatic protons 416 to 464 CPS, the yield is 67%;

3- (3-isopropoxyphenyl) -1-methyl-5-phenyl-4 (1 H) -pyridone, NMR maxima at 81.209 and 276 CPS, aromatic protons at 401 to 468 CPS, the yield is 18%;

3- (3-cyanomethoxyphenyl) -1-methyl-5-phenyl-4 (1H) -pyridone, NMR maxima at 207 and 275 CPS, aromatic protons at 396 to 456 CPS, the yield is 6%;

3- (3-Dodecyloxyphenyl) -l-methyl-5-phenyI-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, the Yield is 26%;

1-Methyl-3- [3- (4-nitrophenoxy) phenyl] -5-phenyl-4 (1H) -pyridone, NMR maxima at 222 and 488.5 CPS, aromatic protons at 414 to 463 CPS, the yield is 14%;

l-methyl-3- (3-methylsulfonyloxyphenyl) -5-phenyl-4 (1H) -pyridone, NMR maximum at 185 and 213 CPS, aromatic protons at 422 to 472 CPS, the yield is 20%;

1-Methyl-3-phenyl-5- [3- (1,1,2,2-tetrafluoroethoxy) phenyl] -4 (1 H) -pyridone, melting point 119 to 121 ° C, the yield is 84% using tetrafluoroethylene in the presence of potassium hydroxide:

3- (3-acetoxyphenyl) -1-methyl-5-phenyl-4 (1 H) -pyridone, NMR maxima at 134 and 210 CPS, aromatic protons at 415 to 466 CPS, the yield is 28%, produced using of acetic anhydride;

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

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

1-methyl-3-phenyl-5- (3-propoxyphenyl) -4 (1 H) -pyridone, NMR maxima at 54,101,5,208 and 232 CPS, aromatic protons at 400 to 463 CPS, the yield is 31%;

1-Methyl-3-phenyl-5- (3-propargyloxyphenyl) -4 (1 H) -pyridone, NMR maxima at 150 and 215 CPS, a broad maximum at 280 to 285 CPS, aromatic protons at 430 to 470 CPS, the Yield is 6%;

3- (3-cyclohexylmethoxyphenyl) -1-methyl-5-phenyl-4 {1 H) -pyridone, NMR maxima at 214 and 226 CPS, a broad maximum at 35 to 124 CPS, aromatic protons at 402 to 466 CPS, the yield is 16%;

1-methyl-3- (3-octyloxyphenyl) -5-phenyl-4 (1 H) -pyridone, NMR maxima at 52.218 and 239 CPS, a broad maximum at 58 to 122 CPS, aromatic protons at 403 to 467 CPS, the yield is 19%;

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

Example 38

A) The starting material of the formula IV prepared was 1,5-dihydroxy-2-phenyl-4- (3-trifluoromethyl-phenyl) -1,4-pentadien-3-one.

B) Cyclization

The starting material of formula IV obtained according to A) was obtained using ammonium acetate according to the method described by Benary and Bitter in Ber. 61,1058 (1928) described cyclized. The 3-phenyl-5- (3-tri-fluoromethylphenyl) -4 (1 H) -pyridone was obtained.

Example 39

This example is used to explain the subsequent N-alkylation of the product according to Example 38 (in this product R is a hydrogen atom), the corresponding 1-methyl-pyridone being obtained by this N-methylation.

39 g of the 3-phenyl-5- (3-trifluoromethylphenyl) -4 (1 H) -pyri-done prepared by the process according to Example 38 are mixed with 100 ml of phosphorus oxychloride and

5 ml of dimethylformamide heated to reflux. The excess phosphorus oxychloride is then removed under vacuum and the residue is taken up in chloroform. The solution is then poured into ice-water and the mixture is stirred until room temperature is reached. The aqueous mixture is then extracted with chloroform, whereupon the organic solution is washed with dilute sodium hydroxide solution and dried. The organic layer is then evaporated to dryness under vacuum. By recrystallizing the resulting residue from hexane, 4-chloro-4-phenyl-5- (3-trifluoromethylphenyl) pyridone is obtained.

2 g of the above compound are dissolved in 20 ml of chloroform and 10 ml of methyl iodide are added. The mixture is left to stand for 4 days. The mixture is then evaporated to dryness. By recrystallizing the residue obtained from chloroform-hexane, pure is obtained

4-chloro-3-phenyl-5- (3-trifluoromethylphenyl) -1-methylpyridinium iodide. A portion of the above product is dissolved in methanol and the solution obtained is made basic with aqueous sodium hydroxide solution. The basic mixture is heated to reflux for 1 hour and then cooled, after which the solids are separated off by filtration. The product obtained here is l-methyl-3-phenyl

5- (3-trifluoromethylphenyl) -4 (1H) pyridone, which melts at 153 to 155 ° C.

Example 40

8 g of the 3-phenyl-5- (3-trifluoromethylphenyl) -4 (1 H) -pyri-dones prepared by the process according to Example 38 are suspended in 30 ml of chloroform, followed by

6 g of methyl trifluoromethanesulfonate are added. The reaction mixture is stirred for 3 hours, whereupon a further 10 g of the sulfonate mentioned are added and the mixture is stirred overnight. In the morning the reaction mixture is poured into aqueous sodium carbonate solution. The aqueous mixture is filtered and the residue is washed with further chloroform. The organic layer of the filtrate is separated off, dried over magnesium sulfate and evaporated to dryness. The residue obtained is an oily, rubbery mass, which according to NMR analysis prak5

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is a 3-phenyl-5- (3-trifluoromethylpheny]) - 1-methyl-4-methoxypyridinium trifluoromethanesulfonate.

The residue is mixed with 30 ml of ethanol and 3 ml of concentrated hydrochloric acid, and the mixture is stirred at reflux temperature for 2 hours. The reaction mixture is then concentrated in vacuo to an oil which is taken up in methylene chloride. The mixture is washed with aqueous sodium carbonate solution and the organic layer is again evaporated to dryness under vacuum. The precipitate remaining by treating the residue with ethyl acetate is removed and combined with the later separated product. The ethyl acetate solution is concentrated in vacuo, whereupon the residue obtained is mixed with 30 ml of ethanol and 10 ml of 10% sodium hydroxide solution and the mixture is stirred at reflux temperature for 2 hours. The reaction mixture is then poured into water, whereupon the insoluble product is separated off by filtration and the solids are recrystallized from acetone. The product obtained is 1-methyl-3-phenyl-5- (3-trifluoromethylphenyl) -4 (1H) -pyridone, which melts at 152 to 156 ° C.

Example 41

A) The starting material of the formula IV prepared was 1,5-dihydroxy-2-phenyl-4- (3-trifluoromethyl-phenyl) -1,4-pentadien-3-one.

B) Cyclization

The product obtained according to A) was cyclized with methylamine to give the l-methyl-3-phenyl-5- (3-trifluoromethylphenyl) -4 (1 H) -pyridone. This product had a melting point of 152 ° to 156 ° C. and was identical to the product obtained according to Example 40 by the subsequent N-methylation.

Example 42

A) The starting material of formula IV was. the 1,5-dihydroxy-2,4-diphenyl-1,4-pentadien-3-one. It was therefore identical to the starting material described in Example 1 under A).

B) Cyclization

The starting material of the formula IV obtained according to A) was cyclized using hydroxylamine,

to obtain the 3,5-diphenyl-l-hydroxy-4 (1H-pyridone.

Example 43

This example is used to explain the subsequent acetylation of a radical R in the meaning of a hydroxyl group, with the formation of a pyridone, which differs from the corresponding compounds of the formula Ia in that the radical R is an acetoxy group.

2.4 g of the 3,5-diphenyl-1-hydroxy-4 (1H) -pyridone prepared by the process according to Example 42 are mixed with 25 ml of acetic anhydride and the mixture is heated on the steam bath for about 1 hour. The volatile constituents are then evaporated off under vacuum, whereupon the residue is washed with benzene and then recrystallized first from benzene and then from chloroform-hexane. This gives 2.1 g of the 1-acetoxy-3,5-diphenyl-4 (1H) pyridone, which melts at 197 to 199 ° C.

Example 44

The l-acetoxy-3-phenyl-5- (3-trifluoromethylphenyl) -4 (1H) -pyridone was prepared by an acetylation process which is analogous to the process described in Example 43. The melting point was 232 to 235 ° C and the yield was 5%.

Example 45

A) The starting material of the formula IV prepared was the 1,5-dihydroxy-2,4-bis (3-trifluoromethylphenyl) -1,4-pen-tadien-3-one.

s B) Cyclization

The product prepared according to A) was cyclized with methylamine to give the l-methyl-3,5-bis (3-trifluoromethylphenyl) -4 (1H) pyridone. The melting point was 152 to 154 ° C.

io Example 46

A) The starting material of the formula IV prepared was 1,5-dihydroxy-2-phenyl-4 (3-trifluoromethyl-phenyl) -1,4-pentadien-3-one.

B) Cyclization ls The product prepared according to A) was converted to 3-phenyl-1- (2,2,2-trifluoroethyl) -5- (3-trifluoromethylphenyl) -4 (1H. Using 2,2,2-trifluoroethylamine ) pyridone cyclized.

This showed a centered quartet 20 in the NMR at 256 CPS and aromatic protons at 420 to 468 CPS.

Example 47

A) The starting material of the formula IV prepared was 2- (3-bromophenyl) -4- (3-chlorophenyl) -l, 5-dihydroxy-l, 4-

25 pentadien-3-one.

B) Cyclization

The product obtained according to A) was cyclized using methylamine to give the 3- (3-bromophenyl) -5- (3-chlorophenyl) l-methyl-4 (1H) pyridone. The melting point was 192 ° C.

Example 48

A) The starting material of the formula IV prepared was 2- (3-chlorophenyl) -4- (4-chlorophenyl) -l, 5-dihydroxy-l, 4-

35 pentadien-3-one,

B) Cyclization

The product obtained according to A) was cyclized using methylamine to give the 3- (3-chlorophenyl) -5- (4-chlorophenyl) -1-methyl-4 (1H) pyridone. The melting point was 170 to 172 ° C.

Example 49

A) The starting material of the formula IV produced was 1,5-dihydroxy-2- (2-fluorophenyl) -4- (3-trifluoromethyl-

45 phenyl) 1,4-pentadien-3-one.

B) Cyclization

The product obtained according to A) was cyclized using methylamine to give the 3- (2-fluorophenyl) -1-methyl-5- (3-trifluoromethylphenyl) -4 (1 H) -pyridone. The melting point was 152 to 154 ° C.

Example 50

A) The starting material of the formula IV prepared was 2- (2-chlorophenyl) -4- (3-chlorophenyl) -l, 5-dihydroxy-l, 4-

55 pentadien-3-one.

B) Cyclization

The product obtained according to A) was cyclized with methylamine to give the 3- (2-chlorophenyl) -5- (3-chlorophenyl) -1-methyl-4 (1H) pyridone. The melting point was 160 to 60 161 ° C.

Example 51

A) The starting material of the formula IV prepared was 1,5-dihydroxy-2- (3-methoxyphenyl) -4- (3-trifluoromethyl)

65 phenyl) -1,4-pentadien-3-one.

B) Cyclization

The starting material obtained according to A) was converted to the 3- (3-methoxyphenyl) - using methylamine

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Cyclized 1-methyl-5- (3-trifluoromethylphenyl) -4 (1 H) pyridone. The melting point was 113 to 115 ° C.

Example 52

A) The starting material of formula IV produced was 2- (4-chlorophenyl) -1,5-dihydroxy-4- (3-trifluoromethyl-phenyl) -1,4-pentadien-3-one.

B) Cyclization

The product prepared according to A) was cyclized using methylamine to give the 3- (4-chlorophenyl) -l-methyl-5- (3-trifluoromethylphenyl) -4 (1H) -pyridone. The melting point was 153 to 155 ° C.

Example 53

A) The starting material of the formula IV was 1,5-dihydroxy-2-phenyl-4- (3-trifluoromethyl-phenyl) 1,4-pentadien-3-one.

B) Cyclization

The product prepared according to A) was cyclized with allylamine to give the 1-allyl-3-phenyl-5- (3-trifluoromethylphenyl) -4 (1H) -pyridone. The melting point was 107 to 109 ° C.

Example 54

A) The starting material of formula IV prepared was 1,5-dihydroxy-2- (4-isopropylphenyl) -4-phenyl-1,4-pen-tadien-3-one.

B) Cyclization

The product obtained according to A) was cyclized using methylamine to give the 3- (4-isopropylphenyl) -l-methyl-5-phenyl-4 (1H) -pyridone. The melting point was 159 ° C.

Example 55

A) The starting material of formula IV prepared was 2- (2-chlorophenyl) -1,5-dihydroxy-4- (3-trifluoromethyl-phenyl) -1,4-pentadien-3-one.

B) Cyclization

The product obtained according to A) was cyclized using methylamine to give the 3- (2-chlorophenyl) -1-methyl-5- (3-trifluoromethylphenyl) -4 (1H) -pyridone. The melting point was 191 to 193 ° C.

Example 56

A) The starting material of formula IV produced was 1,5-dihydroxy-2- (3-fluorophenyl) -4- (3-trifluoromethyl-phenyl) 1,4-pentadien-3-one.

B) Cyclization

The product obtained according to A) was cyclized using methylamine to give the 3- (3-fluorophenyl) -l-methyl-5- (3-trifluoromethylphenyl) -4 (1H) -pyridone. The melting point was 94 to 96 ° C.

Example 57

A) The starting material of the formula IV prepared was 1,5-dihydroxy-2- (4-fluorophenyl) -4- (3-trifluoromethyl-phenyl) -1,4-pentadien-3-one.

B) Cyclization

The product obtained according to A) was cyclized using methylamine to give the 3- (4-fluorophenyl) -l-methyl-5- (3-trifluoromethylphenyl) -4 (1H) -pyridone. The melting point was 133 to 134 ° C.

Example 58

A) The starting material of formula IV prepared was 1,5-dihydroxy-2- (4-methoxyphenyl) -4- (3-trifluoromethyl-phenyl) -1,4-pentadien-3-one.

B) Cyclization

The product obtained according to A) was cyclized using methylamine to give the 3- (4-methoxyphenyl) -l-methyl-5- (3-trifluoromethylphenyl) -4 (1 H) -pyridone. The melting point was 162 to 163 ° C.

5 Example 59

A) The starting material of the formula IV prepared was 1,5-dihydroxy-2- (3-methylthiophenyl) -4-phenyl-1,4-pentadien-3-one.

B) Cyclization io The product obtained according to A) was cyclized using methylamine to the l-methyl-3- (3-methylthio-phenyl) -5-phenyl-4 (1 H) -pyridone.

This showed maxima at 144 and 227 CPS and aromatic at 420 to 440 and 442 to 458 CPS in the NMR spectrum

15 protons.

The methylthiophenyl compound thus obtained was oxidized using m-chloroperbenzoic acid. The following products were obtained:

20 the l-methyl-3- (3-methylsulfinylphenyl) -5-phenyl-4 (1H) -pyridone, melting point 161 to 164 ° C., yield 57%; the 1-methyl-3- (3-methylsulfonylphenyl) -5-phenyl-4 (1 H) -pyridone, melting point 176 to 181 ° C, yield 31%.

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Example 60

A) The starting material of the formula IV prepared was 1,5-dihydroxy-2-phenyl-4- (4-trifluoromethylphenyl) -l, 4-pentadien-3-one.

B) Cyclization

The starting product obtained according to A) was cyclized using methylamine to give the 1-methyl-3-phenyl-5- (4-trifluoromethylphenyl) -4 (1 H) -pyridone.

Example 61

35 A) The starting material of formula IV prepared was das2- (3-benzyloxyphenyl) -l, 5-dihydroxy-4-phenyl-l, 4-pen-tadien-3-one.

B) Cyclization

The product obtained according to A) was cyclized with methylamine 40 to give the 3- (3-benzyloxyphenyl) -l-methyl-5-phenyl-4 (1H) pyridone. This product has a melting point of 158 to 160 ° C.

Example 62

45 A) The starting material of the formula IV was 1,5-dihydroxy-2-phenyl-4- (2-thienyl) -1,4-pentadien-3-one.

B) Cyclization

The product obtained according to A) was also cyclized with methylamine to l-methyl-3-phenyl-5- (2-thienyl) -4 (1H) -pyridone. The melting point was 147 to 148 ° C.

Example 63

A) The starting material of the formula IV prepared was 55 the 1,5-dihydroxy-2- (3-isobutylphenyl) -4-phenyl-1,4-penta-

serve-3-one.

B) Cyclization

The product obtained according to A) was cyclized using methylamine to give the 3- (3-isobutylphenyl) -l-60 methyl-5-phenyl-4 (1H) pyridone. This showed doublets at 54 and 147 CPS in NMR, a septet at 113 CPS and aromatic protons at 420 to 460 CPS.

Example 64

65 Following the example of the cyclization process described in 38, the 3- (2,4-dichlorophenyl) -5-phenyl-4 (1H) pyridone was first prepared.

This product was then added to that with methyl iodide

632496

Methylated 3- (2,4-dichlorophenyl) -l-methyl-5-phenyl-4 (1H) -pyridone.

Example 65

According to the in the publication by Benary and Bitter in Ber. 61,1058 (1928), the 3,5-diphenyl-4 (1H) -pyridone described there was prepared.

This product, described in the literature, was then subjected to N-alkylation to give the following compounds of formula Ia.

It was ethylated to the 3,5-diphenyl-1-ethyl-4 (1H) -pyridone with ethyl iodide.

Allyl bromide was used to allylate the l-allyl-3,5-diphenyl-4 (1 H) -pyridone.

It was propylated to the 3,5-diphenyl-1-iso-propyl-4 (1H) -pyridone with 2-bromopropane.

It was reacted with bromoacetonitrile to give the l-cyanomethyl-3,5-diphenyl-4 (1 H) -pyridone.

Example 66

The following further compounds of the formula Ia were prepared by the process described in Example 1:

1-Methyl-3- (3-nitrophenyl) -5-phenyl-4 (1 H) -pyridone, melting point 135 to 136.5 ° C.

3- (2,4-dichlorophenyl) -5-phenyl-4 (1H) -pyridone, which is identified by infrared analysis and magnetic resonance measurement.

3- (2,4-dichlorophenyl) -1-methyl-5-phenyl-4 (1 H) -pyridone, which melts at 202 to 204 ° C and is identified by its nuclear magnetic resonance spectrum and by infrared analysis. The following data is obtained in micro elemental analysis:

Calc .: C 66.68%; H 3.83%; N 4.09%

Found: C 66.84%; H 4.05%; N 4.01%

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

l-Allyl-3,5-diphenyl-4 (1H) -pyridone, melting point 174 ° C.

3,5-diphenyl-l-isopropyl-4 (1H) -pyridone, melting point 152 ° C

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

l-Methyl-3-phenyl-4 (1H) pyridone that melts at 123 to 125 ° C.

1-Methyl-3- (3-trifluoromethylphenyl) -4 (1 H) -pyridone, melting point 122 to 123 ° C.

3- (3-Carboxyphenyl) -l-methyl-5-phenyl-4 (1H) -pyridone hydrochloride, melting point 266 to 268 ° C.

3- (3-cyanophenyl) -1-methyl-5-phenyl-4 (1 H) -pyridone, melting point 164 to 166 ° C.

3- (3-ethoxycarbonylphenyl) -1-methyl-5-phenyl-4 (1H) -pyridone, melting point 167 to 168 ° C.

3,5-bis (3-cyanophenyl) -l-methyl-4 (1H) -pyridone, melting point 322 to 327 ° C.

1-Methyl-3-phenyl-5- (3-thienyl) -4 (1 H) -pyridone, NMR maxima at 204 and 495 CPS, aromatic protons at 430 to 460 CPS.

3-Cyano-l-methyl-5-phenyl-4 (1 H) pyridone, which melts at 209-210 ° C.

1,3-Dimethyl-5- (3-trifluoromethylphenyl) -4 (1H) pyridone, melting point 130 to 131 ° C.

1,3-dimethyl-5-phenyl-4 (1 H) -pyridone, melting point 111 to 113 ° C.

3- (3-chlorophenyl) -1, 5-dimethyl-4 (1H) -pyridone, melting point 143 to 143.5 ° C.

3-ethyl-l-methyl-5- (3-trifluoromethylphenyl) -4 (1 H) -pyridone, melting point 95.5 to 96.5 ° C.

3-Cyclohexyl-l-methyl-5- (3-trifluoromethylphenyl) -4 (1H) -s pyridone, melting point 174 to 175 ° C. !

3-isopropyl-l-methyl-5- (3-trifluoromethylphenyl) -4 (1H> pyridone, melting point 98.5 to 99.5 ° C.

3-Hexyl-1-methyl-5- (3-trifluoromethylphenyl) -4 (1H) -pyridone, melting point 89.5 to 90.5 ° C. io 3-Benzyl-l-methyl-5- (3-trifluoromethylphenyl) -4 (1H) -pyridone, melting point 98 to 100 ° C.

3-Butyl-l-methyl-5- (3-trifluoromethylphenyl) -4 (1H) pyridone, melting point 82.5 to 84 ° C.

3- (3-Cyclohexenyl) -l-methyl-5- (3-trifluoromethylphenyl) -is 4 (1 H) -pyridone, melting point 194 to 195 ° C.

l-Methyl-3-propyl-5- (3-trifluoromethylphenyl) -4 (1H) -pyridone, melting point 45 to 47 ° C.

1-Methyl-3- (4-nitrophenyl) -5-phenyl-4 (1 H) -pyridone, melting point 212 to 214 ° C. 2o 3,5-bis (3,4-dimethoxyphenyl) -l-methyl-4 (1 H) -pyridone, melting point 182 to 184 ° C.

3-ethoxycarbonyl-l-methyl-5-phenyl-4 (1H) -pyridone, melting point 107 to 108 ° C.

3- (2-furyl) -l-methyl-5-phenyl-4 (1H) -pyridone, melting point 25 191 to 192 ° C.

3-cyano-l-methyl-5- (3-trifluoromethylphenyl) -4 (1H) pyridone, melting point 228 to 229 ° C.

3- (3,4-Dimethoxyphenyl) -1-methyl-5-phenyl-4 (1H) -pyridone, melting point 154 to 157 ° C. 30 3- (3,4-dibromocyclohexyl) -1-methyl-5- (3-trifluoromethyl-phenyl) -4 (1H) -pyridone hydrobromide, melting point 196 to 198 ° C.

3- (3-isopropenylphenyl) -l-methyl-5-phenyl-4 (1H) -pyridone, NMR maxima at 125,214,302 and 327 CPS, aro-35 matic protons at 420 to 470 CPS.

3- (3-ethylphenyl) -l-methyl-5-phenyl-4 (1H) -pyridone, melting point 135 to 137 ° C.

3- (3-Hexylphenyl-1-methyl-5-phenyl-4 (1 H) -pyridone, melting point 93 to 95 ° C.

40 3- (4-ethylphenyl) -1-methyl-5-phenyl-4 (1 H) -pyridone, melting point 143 to 145 ° C.

3- (3-Cyclohexylmethylphenyl) -1-methyl-5-phenyl-4 (1H) -pyridone, melting point I47 to 148 ° C.

1-Methyl-3-phenyl-5-benzylthio-4 (1 H) -pyridone, melting point 45 to 155 to 157 ° C.

l-Methyl-3-phenyl-5-phenylthio-4 (1 H) -pyridone, melting point 164 to 165 ° C.

l-Methyl-3-phenoxy-5-phenyl-4 (1 H) -pyridone, melting point 176 to 177 ° C. so 3-methoxy-l-methyl-5-phenyl-4 (1H) -pyridone, which melts at 153-155 ° C.

3- (3-ethoxyphenyl) -l-methyl-5-phenyl-4 (1H) -pyridone, which melts at 133 to 135 ° C.

3- (3-Isopropoxyphenyl) -l-methyl-5-phenyl-4 (1H) -55 pyridone, NMR max. 81.209 and 276 CPS, aromatic protons at 401 to 468 CPS.

3- (3-cyanomethoxyphenyl) -l-methyl-5-phenyl-4 (1H) -pyridone, NMR maxima at 207 and 275 CPS, aromatic protons at 396 to 456 CPS. 60 3- (3-dodecyloxyphenyl) -1-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.

l-Methyl-3- [3- (4-nitrophenoxy) phenyl] -5-phenyl4 (1H) -65 pyridone, NMR maxima at 222 and 488.5 CPS, aromatic protons at 414 to 463 CPS.

1-Methyl-3- (3-methylsulfonyloxyphenyl) -5-phenyl-4 (1H) -pyridone, NMR max. 185 and 213 CPS, aromatic

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632496

Protons at 422 to 472 CPS.

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

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

1-Methyl-3-phenyl-5- (3-propoxyphenyl) -4 (1 H) -pyridone, NMR maxima at 54, 101, 5, 208 and 232 CPS, aromatic protons at 400 to 463 CPS.

3- (3-Cyclohexylmethoxyphenyl-1-methyl-5-phenyl-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.

1-Methyl-3- (3-octyloxyphenyl) -5-phenyl-4 (1 H) -pyridone, NMR maxima at 52.218 and 239 CPS, a broad maximum at 58 to 122 CPS, aromatic protons at 403 to 467 CPS.

1-Methyl-3- (3-phenoxyphenyl) -5-phenyl-4 (1 H) -pyridone, NMR maximum at 214 CPS, aromatic protons at 410 to 470 CPS.

Example 67

The 1-methyl-3,5-diphenyl-4 (1H) -pyridone was prepared according to the procedure described in Example 1.

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.

The following salts were prepared from the pyridone obtained:

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

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

Example 68

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 67 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 (1 H) -pyridothione is obtained, which melts at 168 to 171 ° C.

Example 69

The pyridothiones listed below were prepared from the corresponding pyridones by the process described in Example 68:

3- (3-bromophenyl) -1-methyl-5-phenyl-4 (1 H) -pyridothione, melting point 185 to 188 ° C., yield 59%,

l-methyl-3- (4-chlorophenyl) -5- (3-trifluoromethylphenyl) -4 (1 H) -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 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) -pyridothione, melting point 145 to 148 ° C., yield 40%, s 1 -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 55%, ^

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

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

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

The herbicidal activity of the new 3-phenyl-5-substituted 4 (1 H) -pyridones or 3-phenyl-5-substituted 4 (1H) -pyridothiones produced by the process according to the invention is illustrated by the following examples. All of the compounds examined correspond to the following formula I.

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Ii in which all the substituents have the meaning given in claim 66.

The numbers of the compounds tested and their 40 chemical names are summarized in Table A below.

The preparation of the compounds described in Table A has either already been explained in the preceding examples or it can be carried out by the cyclization process described in Example 1 45 or the subsequent reaction with phosphorus pentasulfide, which is described in Example 68. However, it should be pointed out that the compounds examined here and listed in Table A can also be produced by those manufacturing processes which are described in Swiss Patent No. 630 356 or in Swiss Patent No. 632 247 or in Swiss Patent No. 632 497, or described in Swiss Patent No. 632 248.

ss table A

No.

Surname

1 1 -methyl-3-phenyl-5- (3-trifluoromethylphenyl) -60 4 (1 H) -py ridone

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

3 3-phenyl-1 - (2,2,2-trifluoroethyl) -5- (3-trifluoromethylphenyl) -4 (1 H) pyridone

65 4 3- (3-bromophenyl) -5- (3-chlorophenyl) -l-methyl-4 (1H) -pyridone

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

632496

Table A (continued)

No. Name

6 3- (2-fluorophenyl) -1-methyl-5- (3-trifluoromethyl-phenyl) -4 (1 H) -pyridone

7 3- (2-chlorophenyl) -5- (3-chlorophenyl) -1-methyl-4 (1H) pyridone

8 3- (3-Methoxyphenyl) -1-methyl-5- (3-trifluoromethyl-phenyl) -4 (1 H) pyridone

9 3- (4-chlorophenyl) -1-methyl-5- (3-trifluoromethyl-phenyl) -4 (1 H) -py ridone

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

11 3- (4-Isopropylphenyl) -l-methyl-5-phenyl-4 (1H) -pyridone

12 3- (2-chlorophenyl) -1-methyl-5- (3-trifluoromethyl-phenyl) -4 (1 H) -pyridone

13 3- (3-fluorophenyl) l -methyl-5- (3-trifluoromethyl-phenyl) -4 (1 H) -pyridone

14 3- (4-fluorophenyl) -l-methyl-5- (3-trifluoromethyl-phenyl) -4 (1 H) pyridone

15 3- (4-methoxyphenyl) -1-methyl-5- (3-trifluoromethyl-phenyl) -4 (1 H) pyridone

16 1-methyl-3- (3-methylthiophenyl) -5-phenyl-4 (1 H) -pyridone

17 l-Methyl-3 - (- methylsulfinylphenyl) -5-phenyl-4 (1H) pyridone

18 1-methyl-3- (3-methylsulfonylphenyl) -5-phenyl-4 (1H) pyridone

19 1-Methyl-3-phenyl-5- (4-trifluoromethylphenyl) -4 (1H) pyridone

20 3- (3-Benzyloxyphenyl) -l-methyl-5-phenyl-4 (1H) -pyridone

21 1-methyl-3-phenyl-5- (2-thienyl) -4 (1 H) -pyridone

22 3- (3-isobutylphenyl) -1-methyl-5-phenyl-4 (1 H) pyridone

23 l-Methyl-3- (3-nitrophenyl) -5-phenyl-4 (1H) pyridone

23a 1-methyl-3-allylthio-5- (3-trifluoromethylphenyl) -

4 (IH) pyridone

23b 3- (4-chloro-3-trifluoromethylphenyl) -1-methyl-5-phe-noxy-4 (1 H) -pyridone

23c 1-methyl-3-phenyl-5-allylthio-4 (1 H) pyridone

24 3- (2,4-dichloropheny 1) -1-methyl-5-phenyl-4 (1H) pyridone

25 3,5-diphenyl-1-ethyl-4 (1 H) -pyridone

26 l-Allyl-3,5-diphenyl-4 (1 H) -pyridone

27 2,5-diphenyl-1-isopropyl-4 (1 H) -pyridone

28 1-cyanomethyl-3,5-diphenyl-4 (1 H) pyridone

29 3,5-diphenyl-1-propyl-4 (1 H) -pyridone

30 3,5-diphenyl-1-methoxy-4 (1 H) -pyridone

31 3- (3-fluorophenyl) -1-methyl-5-phenyl-4 (1 H) -pyridone

32 3- (4-bromophenyl) -l-methyl-5-phenyl-4 (1H) -pyridone

33 3- (4-methoxyphenyl) -l-methyl-5-phenyl-4 (1H) -pyridone

34 3- (3-chlorophenyl) -1-methyl-5-phenyl-4 (1 H) -pyridone

35 3- (4-chlorophenyl) -1-methyl-5-phenyl-4 (1 H) -pyridone

36 1-methyl-3- (1-naphthyl) -5-phenyl-4 (1 H) -pyridone

37 3,5-bis (3-chlorophenyl) -l-methyl-4 (1 H) -pyridone

38 1-methyl-3- (3-methylphenyl-5-phenyl-4 (1 H) pyridone

39 1-methyl-3- (4-methylphenyl) -5-phenyl-4 (1 H) pyridone

40 l-methyl-3- (2-methylphenyl) -5-phenyl-4 (1 H) pyridone

41 3- (4-fluorophenyl) -l-methyl-5-phenyl-4 (1H) -pyridone

Table A (continued)

No. Name

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

43 3- (3-methoxyphenyl) -l-methyl-5-phenyl-4 (1H) -pyridone

44 3- (3,4-dichlorophenyl) -l-methyl-5-phenyl-4 (1H) -pyridone

45 3- (2,5-dichlorophenyl) -l-methyl-5-phenyl-4 (1H) -pyridone

46 3- (2-chlorophenyl) -1-methyl-5-phenyl-4 (1H) pyridone

47 3,5-bis (3-fluorophenyl) -l-methyl-4 (1H) -pyridone

48 3- (3-Chlorophenyl) -5- (3-fluorophenyl) -l-methyl-4 (1H) -pyridone

49 3- (3,5-dichlorophenyl) -l-methyl-5-phenyl-4 (1H) -pyridone

50 3,5-bis (3-bromophenyl) -1-methyl-4 (1 H) -py ridone

51 3- (3-bromophenyl) -1-methyl-5-phenyl-4 (1 H) -pyridone

52 3- (2-fluorophenyl) -1-methyl-5-phenyl-4 (1 H) -pyridone

53 3- (3-Bromophenyl) -l-methyl-5- (3-trifluoromethyl-phenyl) -4 (1H) pyridone

54 l- (l-carboxyethyl) -3-phenyl-5- (3-trifluoromethyl-phenyl) -4 (1 H) pyridone

55 l-Dimethylamino-3,5-diphenyl-4 (1 H) pyridone

56 1-methyl-3- (2-naphthyl) -5-phenyl-4 (1 H) -pyridone

57 1-Ethyl-3-phenyl-5- (3-trifluoromethylphenyl) -4 (1 H) pyridone

58 3-Phenyl-l-propyl-5- (3-trifluoromethylphenyl) -4 (1H) pyridone

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

60 3- (3-chlorophenyl) -l-methyl-5- (3-trifluoromethyl-phenyl) -4 (1 H) -pyridone

61 3- (4-Biphenylyl) -l-methyl-5-phenyl-4 (1 H) -pyridone

62 3- (3-Biphenylyl) -l-methyl-5-phenyl-4 (1H) -pyridone

63 1-methyl-3-phenyl-4 (1 H) pyridone

64 3-bromo-1-methyl-5-phenyl-4 (1 H) -pyridone

65 3-bromo-1-methyl-5- (3-trifluoromethylphenyl) -4 (1H) pyridone

66 1-Methyl-3- (3-trifluoromethylphenyl) -4 (1 H) pyridone

67 3-chloro-l-methyl-5- (3-trifluoromethylphenyl) -4 (1H) pyridone

68 3- (3-Carboxyphenyl) -l-methyl-5-phenyl-4 (1H) -pyridone hydrochloride

69 3- (3-Cyanophenyl) -l-methyl-5-phenyl-4 (1H) -pyridone

70 3- (3-ethoxycarbonylphenyl) -1-methyl-5-phenyl-4 (1H) pyridone

71 3,5-bis (3-cyanophenyl) -l-methyl-4 (1H) -pyridone

72 l-methyl-3-phenyl-5- (3-thienyl) -4 (1H) -pyridone 72a l-methyl-3- (2-methylphenyl) -5- (3-trifluoromethyl-

phenyl) -4 (1 H) -pyridone 72b l-methyl-3- (3-methylphenyl) -5- (3-trifluoromethyl-

phenyl) -4 (1 H) -pyridone 72c l-methyl-3- (4-methylphenyl) -5- (3-trifluoromethyl-

phenyl) -4 (1H) -pyridone 72d 5- (3-methoxycarbonylphenyl) -l-methyl-3- (4-

methyl-phenyl) -4 (1 H) -pyridone 72e 5- (3-methoxycarbonylphenyl) -l-methyl-3- (3-

methyl-phenyl) -4 (1H) -pyridone 72f 3-methoxy-1-methyl-5- (3-trifluoromethylphenyl) -

4 (1H) -pyridone 72g 3- (4-bromophenyl) -l-methyl-5- (3-methylphenyl) -4 (1H) -pyridone

72h 3- (3,4-dichlorophenyl) -l-methyl-5- (3-trifluoromethyl-phenyl) -4 (1 H) pyridone

26

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65

Table A (continued)

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632496

Table A (continued)

No. Name

72i 3,5-bis (3,5-dichlorophenyl) -l-methyl-4 (1H) -pyridone 72j 3- (3,4-dichlorophenyl) -1-methyl-5- (3-methylphenyl) -

4 (lH) -py ridone 72k 3- (3,4-dichlorophenyl) -5- (3,4-dimethylphenyl) -l-

methyl-4 (1 H) -pyridone 721 3- (3-chlorophenyl) -1-methyl-5- (2-methylphenyl) -

4 (1H) pyridone 72m 3- (4-bromophenyl) -1-methyl-5- (3-trifluoromethyl)

phenyl) -4 (1 H) -pyridone 72n 3- (4-bromophenyl) -5- (3-carboxyphenyl) -1 -methyl-

4 (1H) pyridone 72o 3- (3-chlorophenyl) -1-methyl-5- (4-trifluoromethyl-

pheny l) -4 (1 H) -py ridone 72p 3- (2-methylphenyl) -5- (4-methylphenyl) -1 -methyl-

4 (1H) -pyridone 72q 3- (3-methylphenyl) -5- (4-methylphenyl) -1 -methyl-

4 (1 H) -py ridone 72r 3- (2-chlorophenyl) -5- (2-methylphenyl) -1 -methyl-

4 (1H) -pyridone 72s 1 -methyl-3,5-bis (4-methylphenyl) -4 (1H) -pyridone 72t 1 -methyl-3- (3-chlorophenyl) -5- (3,4-dichlorophenyl -4 (1H) pyridone

72u 1-methyl-3- (3,4-dichlorophenyl) -5- (2-methylphenyl) -

4 (lH) -pyridone 72v l-methyl-3- (2-chlorophenyl) -5- (3,4-dichlorophenyl) -

4 (lH) -py ridone 72w 1 -methyl-3- (3-bromophenyl) -5- (3,4-dichlorophenyl) -4 (1 H) -py ridone

72x 1-methyl-3- (3,5-dichlorophenyl) -5- (3-trifluoromethyl-

phenyl) -4 (1 H) -pyridone 72y 1 -methyl-3- (3-bromophenyl) -5- (3-methylphenyl) -

4 (1H) -pyridone 72z 1-methyl-3,5-bis (3-methylphenyl) -4 (1H) -pyridone 72aa 1-methyl-3- (3-fluorophenyl) -5- (2,5-dimethylphenyl ) -

4 (1H) -pyridone 72bb 3- (3-bromophenyl) -1-methyl-5- (2-methylphenyl) -

4 (1H) -pyridone 72cc 3- (3-bromophenyl) -5- (2-chlorophenyl) -l-methyl-

4 (1H) pyridone 72dd 3- (2-bromophenyl) -1-methyl-5- (3-trifluoromethyl-

pheny l) -4 (1 H) -py ridone 72ee 3- (2,3-dimethoxyphenyl) -1-methyl-5- (3-trifluorme-

thylphenyl) -4 (1 H) -pyridone 72ff 3- (2-methoxyphenyl) -l-methyl-5- (trifluoromethyl-

phenyl-4 (1 H) -py ridone 72gg 3- (2-ethylphenyl) -1-methyl-5- (3-trifluoromethyl)

phenyl) -4 (1 H) -pyridone 72hh 3- (3-bromo-4-methylphenyl) -1-methyl-5- (trifluorme-

thylphenyl) -4 (1 H) pyridone 72ii 3- (3-ethoxy-4-methoxyphenyl) -1-methyl-5- (3-tri-

fluoromethylphenyl) -4 (1 H) -pyridone 72jj 3- (1-hydroxyethyl) -1-methyl-5- (3-trifluoromethyl-

phenyl) -4 (1 H) -pyridone 72kk 3- (l-methoxyethyl) -l-methyl-5- (3-trifluoromethyl-phenyl) -4 (1 H) -pyridone

73 3-Cyano-1-methyl-5-phenyl-4 (1 H) -pyridone

74 1,3-dimethyl-5- (3-trifluoromethylphenyl) -4 (1 H) pyridone

7 5 1,3-dimethyl-5-phenyl-4 (1 H) pyridone

76 3- (3-chlorophenyl) -1,5-dimethyl-4 (1H) pyridone

77 3-ethyl-1-methyl-5- (3-trifluoromethylphenyl) -4 (1H) pyridone

78 3-Cyclohexyl-1-methyl-5- (3-trifluoromethylphenyl) -4 (1H) pyridone

79 3-isopropyl-1-methyl-5- (3-trifluoromethylphenyl) -

No. Name

4 (1H) pyridone

80 3-Hexyl-l-methyl-5- (3-trifluoromethylphenyl) -4 (1H) pyridone

81 3-Benzyl-1-methyl-5- (3-trifluoromethylphenyl) -4 (1H) -py ridone

82 3-Butyl-l-methyl-5- (3-trifluoromethylphenyl) -4 (1H) pyridone

83 3- (3-Cyclohexenyl) -1-methyl-5- (3-trifluoromethyl-phenyl) -4 (1 H) -pyridone

84 1-Methyl-3-propyl-5- (3-trifluoromethylphenyl) -4 (1H) -py ridone

85 1-methyl-3- (4-nitrophenyl) -5-phenyl-4 (1 H) pyridone

86 3,5-bis (3,4-dimethoxyphenyl) -1-methyl-4 (1H) pyridone

87 3-ethoxycarbonyl-l-methyl-5-phenyl-4 (1 H) pyridone

88 3- (2-furyl) -1-methyl-5-phenyl-4 (1 H) -pyridone

89 3-Cyano-1-methyl-5- (3-trifluoromethylphenyl) -4 (1H) pyridone

90 3- (3,4-Dimethoxyphenyl) -l-methyl-5-phenyl-4 (1H) pyridone

91 3- (3,4-Dibromocyclohexyl) -1-methyl-5- (3-trifluoromethylphenyl) -4 (1 H) -pyridone hydrobromide

92 3- (3-isopropenylphenyl) -l-methyl-5-phenyl-4 (1H) -pyridone

93 3- (3-ethylphenyl) -l-methyl-5-phenyl-4 (1 H) -pyridone

94 3- (3-Hexylphenyl) -l-methyl-5-phenyl-4 (1H) -pyridone

95 3- (4-ethylphenyl) 1-methyl-5-phenyl-4 (1H) pyridone

96 3- (3-Cyclohexylmethylphenyl) -1-methyl-5-phenyl-4 (1H) -py ridone

97 1-methyl-3-phenyl-5-benzylthio-4 (1 H) pyridone

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

99 1-methyl-3-phenoxy-5-phenyl-4 (1 H) pyridone

100 1-methyl-3-phenyl-5-phenylsulfonyi-4 (1 H) -pyridone 100a 3-methoxy-1-methyl-5-phenyl-4 (1 H) -pyridone 100b 3- (4-methoxy-3- methylphenyl) -1-methyl-5-phenyl-

4 (1H) -pyridone 100c 3- (3-bromo-4-methylphenyl) -l-methyl-5-phenyl-

4 (lH) -pyridone 100d l-methyl-3- (3-nitrophenyl) -5- (3-trifluoromethyl-

phenyl) -4 (1 H) pyridone 100e 1-methyl-3-phenyl-5- (3-phenylthiophenyl) -4 (1H) pyridone

1 OOf 1 -methyl-3-phenyl-5- (3-phenylsulfonylphenyl) -4 (1H) pyridone

100g of 3- (2-chloro-4-fluorophenyl) -1-methyl-5-phenyl-4 (1 H) -pyridone

100 h 3- (3,4-dimethylphenyl) -1-methyl-5-phenyl-4 (l H) -pyridone 100i 3- (3,5-dimethylphenyl) -l-methyl-5-phenyl-4 (l H) -pyridone

1 OOj 3- (3-butylphenyl) -1-methyl-5-phenyl-4 (1 H) -pyridone 100k 3- (2,5-dimethylphenyl) -l-methyl-5-phenyl-4 (1H) -pyridone

1001 3- (2,4-dimethylphenyl) -l-methyl-5-phenyl-4 (1 H) -pyridone

100m 1 -methyl-3-phenoxy-5- (3-trifluoromethylphenyl) -

4 (lH) -pyridone 100 3-ethoxycarbonyl-l-methyl-5- (3-trifluoromethyl-

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

4 (1H) -py ridone 100p 3- (2,4-dichlorophenoxy) -1 -methyl-5- (3-trifluoromethylphenyl) -4 (1H) -py ridone

5

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632496

Table A (continued)

28

Table A (continued)

No. Name

100q 1-methyl-3- (2-thienyl) -5- (3-trifluoromethylphenyl) -

4 (1 H) -py ridone 1 OOr 3-ethylthio-1-methyl-5-phenyl-4 (1 H) -pyridone 100s 3-ethylthio-1-methyl-5- (3-trifluoromethylphenyl> 4 (1H) - pyridone

100 t of 3- (5-bromo-2-fluorophenyl) -1-methyl-5-phenyl-4 (1H) pyridone

1 OOu 1 -methyl-3- (5-nitro-2-methylphenyl) -5-phenyl-4 (1H) pyridone

, 1 OOv 3-cyano-5- (2,5-dimethoxyphenyl) -1-methyl-4 (1 H) -pyridone

1 OOw 3- (2,6-dichlorophenyl) -1-methyl-5-phenyl-4 (1 H) -pyridone

1 OOx 3-ethoxycarbonyl-1-methyl-5-phenyl-4 (1H) -pyridone

1 OOy 1 -methyl-3-propylthio-5- (3-trifluoromethylphenyl) -

pentadien-3-one.

1 OOaa 1 -methyl-3-methylthio-5- (3-trifluoromethylphenyl) -

4 (1 H) -pyridone 1 OObb 1 -methyl-3- (3-trifluoromethylphenyl) -5- (4-trifluoro-

methylphenyl) -4 (1 H) -pyridone 1 OOcc 1 -methyl-3-phenyl-5- (2,3,6-trichlorophenyl) -4 (1H) -pyridone

1 odod 3- (3,4-dimethoxyphenyl) -1-methyl-5- (3-trifluoro-

methylphenyl) -4 (1 H) -pyridone 100 mixture of 3- (5-fluoro-2-iodophenyl) -l-methyl-5-phenyl-4 (1H) -pyridone and 3- (2-bromo-5-fluoro -phenyl) -1-methyl-5-phenyl-4 (1 H) -pyridone 1 OOff 3-benzylthio-1-methyl-5- (3-trifluoromethylphenyl) -

4 (1H) -pyridone 1 OOgg 1,3-diethyl-5- (3-trifluoromethylphenyl) -4 (1H) -pyridone 100hh 3- (4-chloro-3-trifluoromethylphenyl) -5-ethoxy-l-

methyl-4 (1 H) -pyridone 1 OOii 1 -methyl-3-isopropylthio-5- (3-trifluoromethyl-

phenyl) -4 (1 H) -pyridone 1 OOjj 3- (4-chloro-3-trifluoromethylphenyl) -5-ethylthio-1 -

methyl-4 (1 H) -pyridone 1 OKk 3- (4-chloro-3-trifluoromethylphenyl) -1-methyl-5-

phenyl-4 (1 H) -pyridone 10011 3- (4-benzyloxyphenyl) -1 -methyl-5- (3-trifluoro-

methylphenyl) -4 (1 H) -pyridone 100mm 3- (4-hydroxyIphenyl) -1 -methyl-5- (3-trifluoromethyl-

phenyl) -4 (1 H) -pyridone 1 OOnn 3- (2,5-dimethylphenyl) -1-methyl-5- (3-trifluoro-

methylphenyl) -4 (1 H) -pyridone 100- 3- (3,5-dimethylphenyl-1-methyl-5- (3-trifluoro-

methylphenyl) -4 (1 H) -pyridone 1 OOpp 3- (2,4-dichlorophenyl) -1-methyl-5- (3-trifluoromethyl-

phenyl) -4 (1 H) -pyridone 1 OOqq 1 -methyl-3-phenyl-5- (2-trifluoromethylphenyl) -

4 (lH) -pyridone 1 OOrr 1 -methyl-3- (2-trifluoromethylphenyl) 5- (3-trifluoro-

methylphenyl) -4 (1 H) -pyridone 1 OOss 3- (3,4-dimethylphenyl) -1-methyl-5- (3-trifluoro-

methylphenyl) -4 (1 H) -pyridone 1 OOtt 3- (3-iodophenyl) -1 -methyl-5- (3-trifluoromethyl-

phenyl) -4 (1 H) -pyridone 1 OOuu 3-ethyl-1-methyl-5- (3-methoxyphenyl) -4 (1 H) -pyridone 100vv 1-methyl-3- (3-iodophenyl) -5 -phenyl-4 (1H) -pyridone 1 OOww 1 -methyl-3- (4-methoxyphenoxy) -5- (3-trifluoro-

methylphenyl) -4 (1 H) -pyridone 1 OOxx 1 -methyl-3- (2-chloro-4-fluorophenyl) -5- (3-trifluoromethylphenyl) -4 (1 H) -pyridone

No.Name lOOyy 3-ethylsulfonyl-l-methyl-5- (3-trifluoromethyl-s phenyl) -4 (lH) -pyridon lOOzz l-methyl-3- (4-chloro-3-trifluoromethylphenyl) -5-tri-

fluoromethyl-4 (1 H) -pyridone 100 from 1-methyl-3- (4-chloro-3-trifluoromethylphenyl) 5-propyl-4 (1 H) -pyridone 1000ac 1-methyl-3-isopropylthio-5- (4th -chloro-3-trifluoromethylphenyl) -4 (1 H) -pyridone 1 OOad 1 -methyl-3- (4-chloro-3-trifluoromethylphenyl) -5-pro-

pylthio-4 (1 H) -pyridone 100a l-methyl-3- (4-chloro-3-trifluoromethylphenyl) -5- (2-15 thienyl) -4 (1H) -pyridone

1 OOaf 3-ethyl-1-methyl-5- (4-chloro-3-trifluoromethyl-

phenyl) -4 (l H) -pyridone lOOag l-methyl-3- (2,4-dimethylphenyl) -5- (3-trifluoromethylphenyl) -4 (l H) -pyridone 20 lOOah 3-isopropoxy-l- methyl-5- (3-trifluoromethylphenyl) -4 (1H) -pyridone 1 OOai 1 -methyl-3- (4-chlorophenoxy) -5-trifluoromethyl-

phenyl-4 (1 H) -pyridone 100aj 1-methyl-3- (3-methylthiophenyl-5- (3-trifluoro-25 methylphenyl) -4 (1 H) -pyridone 100ak 1-methyl-3- (3-methylsulfonylphenyl ) -5- (3-trifluoro-

methylphenyl) -4 (l H) -pyridone lOOal 3-ethylsulfinyl-l-methyl-5- (3-trifluoromethyl-phenyl) -4 (l H) -pyridone 30 lOOam l-methyl-3- (3-trifluoromethylphenoxy) - 5- (3-trifluoromethylphenyl) -4 (1 H) -pyridone 100- 3- (4-methoxyphenyl-l-methyl-5- (3-trifluoromethyl-

phenyl) -4 (1 H) -pyridone 1 OOao 3- (2,3-dichlorophenoxy) -1-methyl-5- (3-trifluoro-35 methylphenyl) -4 (1H) -py ridone

1 OOap 3- (3,5-dichlorophenoxy) -l -methyl-5- (3-trifluoro-

methylphenyl) -4 (1 H) -pyridone 100aq 3- (3,4-dichlorophenoxy) -l-methyl-5- (3-trifluoromethylphenyl) -4 (1 H) -pyridone 40 100% 3- (4-chloro -3-trifluoromethylphenyl) -l-methyl-5-iso-propyl-4 (1 H) -pyridone 1 OOas 3- (2,5-dichlorophenoxy) -1-methyl-5- (3-trifluoro-

methylphenyl) -4 (1 H) -pyridone 100at l-methyl-3- (3-trifhiormethylphenyl) -5-trifluoro-45 methylthio-4 (1H) -pyridone

1 OOau 1 -methyl-3- (4-methylthiophenoxy) -5- (3-trifluoro-

methylphenyl) -4 (1 H) -pyridone 1 OOav 3-isobutylthio-1-methyl-5- (3-trifluoromethylphenyl) -4 (1 H) -py ridone so 100% 3-tert-butylthio-1-methyl-5 - (3-trifluoromethyl-phenyl) -4 (1 H) -pyridone 100aw 3-s-butylthio-1-methyl-5- (3-trifluoromethylphenyl) -

4 (1H) -pyridone 100ay 1-methyl-3- (4-nitrophenoxy) -5- (3-trifluoromethyl-55 phenyl) -4 (1H) -pyridone

1 OOaz 3-ethyl-1-hydroxy-5- (3-trifluoromethylphenyl) -

4 (1H) -pyridone 1 OOba 1 -methyl-3-trifluoromethylsulfonyl-5 (3-trifluoromethylphenyl) -4 (1H) -pyridone 60 100Bc l-methyl-3- (3-trifluoromethylphenyl) -5- (3rd -trifluoromethylthiophenyl) -4 (1 H) -pyridone 1 OObd 1-methyl-3- (3-trifluoromethylphenyl) -5- (3-trifluoro-

methylsulfonylphenyl) -4 (1 H) -pyridone 1 OObe 1 -methyl-3- (2,2,2-trifluoroethoxy) -5- (3-trifluoro-65 methylphenyl) -4 (1 H) -py ridone

1 OObf 1 -methyl-3- (2-nitrophenyl) -5- (3-trifluoromethyl-

phenyl) -4 (1 H) -pyridone 101 3-methoxy-1-methyl-5-phenyl-4 (1 H) -pyridone

Table A (continued)

29

632496

Table A (continued)

No. Name

101a 3-ethoxy-l-methyl-5- (3-trifluoromethylphenyl) -4 (1 H) -py ridone

102 3- (3-Hydroxyphenyl) 1-methyl-5-phenyl-4 (1 H) pyridone

103 3-CyclohexyI-5- (3-hydroxyphenyl) -1-methyl-4 (1H) -pyridone

104 3- (3-ethoxyphenyl) -l-methyl-5-phenyl-4 (1 H) -pyridone

105 3- (3-allyloxyphenyl) -1-methyl-5-phenyl-4 (1H) pyridone

106 2- [3- (1-fluoro-2-iodovinyloxy) phenyl] -1-methyl-5-phenyl-4 (1 H) pyridone

107 3- (3-isopropoxyphenyl) -1-methyl-5-phenyl-4 (1H) pyridone

108 3- (3-cyanomethoxyphenyl) -1-methyl-5-phenyl-4 (1H) -py ridone

109 3- (3-Dodecyloxyphenyl) -1-methyl-5-phenyl-4 (1 H) -pyridone

110 1 -methyl-3- [3- (4-nitrophenoxy) phenyl] -5-phenyl-4 (1H) pyridone

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

112 1-methyl-3-phenyl-5-3- (l, 1,2,2-tetrafluoroethoxy) phenyl] -4 (1 H) pyridone

113 3- (3-acetoxyphenyl) -l-methyl-5-phenyl-4 (1H) -pyridone

114 3- (3-Hexyloxyphenyl) -1-methyl-5-phenyl-4 (1H) -pyridone

115 3- (3-Decyloxyphenyl) -1-methyl-5-phenyl-4 (1H) pyridone

116 1-methyl-3-phenyl-5- (3-propoxyphenyl) -4 (1H) pyridone

117 l-methyl-3-phenyl-5- (3-propargyloxyphenyl) -4 (1H) -py ridone

118 3- (3-Cyclohexylmethoxyphenyl) -1-methyl-5-phenyl-4 (1H) pyridone

119 1-Methyl-3- (3-octyloxyphenyl) -5-phenyl-4 (1H) pyridone

120 I-methyl-3- (3-phenoxyphenyl) -5-phenyl-4 (1 H) pyridone

121 1-methyl-3-phenyl-5- (3-trifluoromethylphenyl) -4 (1H) pyridone

121a 1 -hydroxy-3-phenyl-5- (3-trifluoromethylphenyl) -4 (1H) pyridone

122 1-Methyl-3-phenyl-5- (3-trifluoromethylphenyl) -4 (1H) pyridone

123 3,5-diphenyl-4 (1H) pyridone

124 1-methyl-3-phenyl-5- (3-trifluoromethylphenyl) -4 (1H) pyridone

124a 1-methyl-3- (1-methyl-butylthio) -5- (3-trifluoromethyl-phenyl) -4 (1 H) -pyridone

124b 3- (2-hydroxypropyl) -1-methyl-5- (3-trifluoromethyl-phenyl) -4 (1 H) -pyridone

124c 1-Methyl-3- (2-methyl-2-propenylthio) -5- (3-trifluoromethylphenyl) -4 (1 H) -pyridone

124d 3-ethylthio-5- (2-chloro-5-trifluoromethylphenyl) -l-methyl-4 (1 H) pyridone

124e 3- (2-chloro-5-trifluoromethylphenyl) -1-methyl-5-phenyl-4 (1 H) -py ridone

124f 3- (2-Chloro-5-trifluoromethylphenyl) -1-methyl-5- (3-trifluoromethylphenyl) -4 (1 H) -pyridone

125 1-methyl-3-phenyl-5- (3-trifluoromethylphenyl) -4 (1H) pyridone

126 1-methyl-3-phenyl-5 (3-trifluoromethylphenyl) -4 (1H) pyridone

No. Name

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

128 3,5-bis (3-chlorophenyl) -1-methyl-4 {1 H) -py ridone

129 1 - acetoxy-3,5-diphenyl-4 (1 H) pyridone

129a 1-acetoxy-3-phenyl-5 (3-trifluoromethylphenyl) -4 (1H) pyridone

130 1-methyl-3,5-diphenyl-4 (1 H) -pyridone hydroiodide

131 1-Methyl-3,5-diphenyl-4 (1 H) -pyridone hydrochloride

132 3,5-diphenyl-1-methyl-4 (1 H) -pyridinethione 132a 3- (3-bromophenyl) -l-methyl-5-phenyl-4 (1H) -pyri-

dinthion

132b 1-methyl-3- (4-chlorophenyl) -5- (3-trifluoromethyl-

phenyl) -4 (1 H) -pyridinethione 132c 1-methyl-3- (3-methylphenyl) -5- (3-trifluoromethyl-

phenyl) -4 (1 H) -py ridinthion 132d 1 -methyl-3- (2-methylphenyl-5- (3-trifluoromethyl-

phenyl) -4 (1 H) -pyridinethione 132e 1 -methyl-3-propyl-5- (3-trifluoromethylphenyl) -

4 (1 H) -py ridinthion 132f 1 -methyl-3-phenoxy-5- (3-trifluoromethylphenyl) -

4 (1 H) -pyridinethione 132g 3-ethylthio-1-methyl-5- (3-trifluoromethylphenyl) -

4 (1 H) -pyridinthione 132h 3-ethoxy-l-methyl-5- (3-trifluoromethylphenyl) -4 (1 H) -pyridinthione

133 3,5-bis (3-chlorophenyl) -1-methyl-4 (1 H) -pyridinethione

134 3- (3-chlorophenyl) -1-methyl-5-phenyl-4 (1 H) -pyrididinion

135 1-methyl-3-phenyl-5- (3-trifluoromethylphenyl) -4 (1 H) -pyridine thione

135a 3- (3-carboxyphenyl) -1-methyl-5-phenyl-4 (1H) pyridone

The compounds listed in Table A were tested in a series of herbicidal test systems to determine the range of their herbicidal activity. The excellent results obtained with the respective compounds in the typical experiments described below, which are reported below, are examples of the excellent activity of the new compounds of the formula I.

The application quantities for the active ingredients are expressed in kg of the respective compound per ha of soil (kg / ha).

Blank spaces in the following tables mean that the respective compound has not been tested for the species listed. In some cases, the test values given for repeated testing of a particular compound against a plant species are averaged.

Untreated control plants or control plots were also used in all experiments. The control achieved by the compounds of the formula I is assessed by comparing the treated plants or plots with the controls.

In the experiments of Examples 70 to 74 described below, the plants were assessed on a scale from 1 to 5, with the specification 1 standing for normal plants and the specification 5 indicating that the plants had died or none at all Casserole came.

In the investigations of the following examples 75 to 77 and 80 to 82, a scale from 0 to 10 was used for the evaluation, the specification 0 standing for normal plants and the value 10 being given,

5

10th

15

20th

25th

30th

35

40

45

50

55

fiO

65

632496

30th

that the plants have died or that there has been no emergence.

In the tests of Examples 78 and 79 and 84 below, the results were evaluated as a percentage control of the plants.

The evaluation criteria used for the experiments in Example 83 below are given in the description of this example.

Example 70

Broad spectrum greenhouse experiment

Rectangular plastic pots are filled with a sterilized sandy loam soil and planted with seeds of tomatoes, big finger grass and goose foot. Each pot is fertilized individually.

The compounds to be examined are applied to some pots before emergence and to other pots after emergence. In post-emergence application, the compounds are sprayed over the emerged plants about 12 days after planting the seeds. The pre-emergence treatment is carried out by spraying the soil the day after sowing.

Each compound examined is dissolved in a 1: 1 mixture of acetone and ethanol in an amount of 2 g per 100 ml. The solution also contains 2 g of an anionic nonionic surface-active mixture per 100 ml. 1 ml of the solution is diluted to 4 ml with deionized water, and 1.5 ml of the solution obtained is applied to each pot, resulting in an application rate of 16.8 kg / ha of test compound.

After treatment with the active ingredients, the pots are placed in the greenhouse, watered if necessary and observed and assessed about 10 to 13 days after the compounds have been used. Untreated control plants are used as standards in each experiment.

The results obtained in these experiments with typical compounds of the formula I are summarized in Table I below. The compounds used for this are identified by their respective example numbers.

Table I

Table I (continued)

10th

15

20th

25th

30th

35

40

Connection no.

24th

25th

26

27th

29

30th

31

32

33

35

36 129

37

38

39

40

41 1

43

44

45

Pre-emergence effect

Tomato Large goose finger foot grass

Post-emergence effect

Tomato Large goose finger foot in grass

3 5 2

2 1 5 5 5

3rd

4th

5

3 5 5

4th

5 5 5 5 5 5

3 5

4 2 1

5 5 5

4th

5 5

4th

5 5

4th

5 5 5 5 5 5

4th

4th

3rd

2 1

5 5 5

3 5 5 3 5 5 3 5 5 5 5 5 5

3rd

4 2

2nd

1

3rd

5 5

2 5 5

3 5 5

4th

5 5

4th

5

4th

5

3 3

3 2

1

4th

5 4

2 4

4th

3rd

5 5

4th

5 5 4 4

4th

5

3 3 2

2nd

1

3rd

4 4

2 4 4

3rd

4 4 4

4th

5 4 4

4th

5

45

50

55

60

65

connection

Pre-emergence effect

Post-emergence effect

No.

tomato

Big one

Geese

tomato

Big one

Geese

Finger foot

Finger foot

grass

grass

46

5

5

5

4th

4th

4th

47

5

5

5

5

5

5

48

5

5

5

5

5

5

49

4th

5

5

5

5

5

50

4th

5

5

3rd

4th

4th

51

5

5

5

4th

4th

4th

52

4th

5

5

4th

4th

4th

132

4th

4th

3rd

3rd

3rd

3rd

2nd

4th

4th

4th

5

4th

3rd

5

5

5

5

5

5

3rd

6

4th

4th

4th

3rd

4th

4th

10th

4th

4th

4th

3rd

4th

3rd

11

1

1

1

1

2nd

2nd

15

4th

4th

4th

4th

4th

4th

28

1

4th

3rd

1

1

1

53

4th

4th

4th

4th

4th

3rd

55

1

1

1

3rd

2nd

3rd

56

2nd

3rd

2nd

3rd

2nd

2nd

57

4th

4th

4th

3rd

4th

3rd

58

2nd

4th

3rd

2nd

3rd

3rd

59

5

5

5

3rd

3rd

2nd

61

1

1

1

1

1

1

130

4th

4th

4th

3rd

3rd

3rd

131

3rd

4th

4th

3rd

3rd

3rd

133

3rd

4th

4th

4th

4th

3rd

134

4th

4th

4th

4th

4th

3rd

135

4th

4th

4th

3rd

4th

3rd

63

4th

4th

4th

3rd

2nd

3rd

64

2nd

4th

3rd

3rd

3rd

3rd

74

4th

4th

4th

5

5

4th

79

5

5

5

5

5

5

85

2nd

3rd

3rd

2nd

2nd

2nd

87

1

4th

3rd

3rd

2nd

3rd

88

2nd

2nd

2nd

2nd

2nd

2nd

90

2nd

3rd

2nd

2nd

2nd

2nd

17th

5

4th

4th

4th

4th

5

18th

3rd

3rd

4th

3rd

3rd

2nd

19th

2nd

2nd

2nd

2nd

1

3rd

21st

3rd

4th

2nd

3rd

3rd

2nd

23

5

5

5

4th

4th

4th

102

4th

4th

3rd

3rd

4th

3rd

103

1

1

2nd

2nd

2nd

2nd

72a

5

5

5

4th

4th

4th

72c

5

5

5

4th

4th

4th

72d

5

5

2nd

3rd

2nd

3rd

72g

4th

4th

4th

3rd

2nd

2nd

72h

4th

5

5

4th

4th

4th

72i

1

1

1

1

1

1

72j

3rd

5

5

4th

4th

4th

100c

4th

5

5

3rd

4th

3rd

lOOd

4th

5

5

4th

4th

4th

100e

3rd

5

5

3rd

3rd

3rd

lOOf

3rd

5

5

3rd

2nd

3rd

100 g

5

5

5

4th

4th

4th

lOOi

5

5

5

3rd

4th

3rd

lOOj

5

5

5

3rd

4th

3rd

100k

5

5

5

4th

4th

4th

100m

5

5

5

4th

4th

4th

72k

1

4th

4th

3rd

2nd

3rd

lOOq

3rd

5

5

4th

4th

4th

100s

5

5

5

4th

4th

4th

31

632496

Table I (continued)

Connection pre-emergence effect post-emergence effect no.

Tomato big goose- Tomato big goose- finger foot finger foot grass grass

721

5

5

5

4th

4th

4th

lOOv

1

1

1

1

1

1

122

1

1

2nd

2nd

2nd

2nd

lOOy

5

5

5

2nd

3rd

2nd

lOOaa

5

5

5

5

3rd

3rd

lOObb

3rd

5

4th

2nd

3rd

2nd

lOOcc

1

1

1

1

1

1

lOOdd

3rd

3rd

4th

2nd

2nd

2nd

101a

5

5

5

3rd

3rd

3rd

100mm

2nd

5

4th

2nd

2nd

2nd

lOOii

5

5

5

3rd

4th

3rd

lOOjj

5

5

5

5

5

5

Example 71

Greenhouse experiment can be solved using seven plant species containing solvents containing active agents

This experiment is generally carried out in a manner similar to that described in Example 1 and approximately a part of the organic solution obtained in game 70. In this case, diluted with 12 parts of water before the boxes are used, the seeds are planted in flat metal boxes and treated. The compounds are in a lot of and not in pots. The compounds are applied after the »9.0 kg / ha. The values formulated in the investigation of the above-described methods, the values obtained being different from the plant species, however, result from the following - of which 6 g / 100 ml of the compound in which the surface Table II emerges.

Table!!

Connection pre-emergence effect post-emergence effect

No.

Corn Large Goose - Fox - Semolina - Purple Zinnia Corn Large Goose - Fox - Semolina - Purple Zinnia

Finger foot tail root winder Finger foot tail root winder grass grass

24th

1

4th

4th

2nd

2nd

1

1

1

1

1

1

1

1

25th

1

3rd

2nd

2nd

2nd

1

2nd

2nd

2nd

3rd

2nd

2nd

2nd

2nd

26

1

3rd

2nd

2nd

2nd

1

2nd

1

1

1

1

1

1

1

27th

1

1

1

1

1

1

1

2nd

1

2nd

3rd

2nd

2nd

2nd

29

1

1

1

1

1

1

1

1

1

2nd

2nd

1

1

1

33

1

1

1

1

1

1

1

1

1

2nd

1

1

2nd

1

34

3rd

4th

4th

4th

4th

3rd

3rd

4th

3rd

4th

3rd

3rd

3rd

35

1

3rd

3rd

2nd

2nd

1

1

2nd

2nd

2nd

2nd

2nd

2nd

2nd

36

2nd

4th

4th

2nd

2nd

1

1

3rd

3rd

4th

4th

3rd

3rd

3rd

129

2nd

3rd

2nd

3rd

3rd

2nd

2nd

1

2nd

2nd

2nd

2nd

2nd

2nd

37

3rd

4th

5

5

4th

2nd

3rd

3rd

4th

3rd

3rd

3rd

3rd

3rd

38

4th

5

3rd

5

3rd

3rd

3rd

4th

4th

3rd

3rd

4th

3rd

3rd

39

1

3rd

3rd

3rd

2nd

1

1

2nd

2nd

2nd

2nd

1

2nd

1

40

2nd

4th

3rd

4th

3rd

2nd

2nd

3rd

3rd

4th

3rd

4th

3rd

3rd

41

4th

4th

4th

5

4th

2nd

2nd

4th

4th

3rd

4th

3rd

3rd

3rd

1

5

5

5

5

5

5

5

3rd

4th

3rd

4th

3rd

2nd

2nd

43

4th

5

5

4th

3rd

3rd

2nd

3rd

4th

3rd

4th

3rd

3rd

3rd

44

3rd

4th

2nd

2nd

2nd

2nd

2nd

3rd

4th

5

3rd

3rd

3rd

3rd

45

2nd

4th

3rd

3rd

2nd

2nd

1

3rd

5

5

5

5

3rd

3rd

46

1

3rd

2nd

2nd

2nd

1

2nd

3rd

4th

4th

3rd

3rd

3rd

3rd

47

3rd

4th

2nd

3rd

4th

2nd

3rd

4th

5

5

5

5

4th

4th

48

3rd

5

4th

4th

3rd

3rd

3rd

4th

5

5

5

5

4th

4th

49

3rd

5

4th

4th

2nd

2nd

1

2nd

3rd

3rd

2nd

3rd

3rd

3rd

50

1

4th

4th

3rd

2nd

1

1

2nd

3rd

3rd

3rd

3rd

2nd

3rd

51

3rd

5

5

4th

4th

4th

2nd

4th

3rd

3rd

3rd

3rd

3rd

3rd

52

2nd

5

4th

4th

3rd

2nd

2nd

2nd

2nd

2nd

2nd

2nd

2nd

2nd

132

1

2nd

2nd

2nd

1

1

1

2nd

2nd

2nd

2nd

2nd

3rd

2nd

2nd

4th

5

5

5

5

3rd

3rd

3rd

3rd

3rd

2nd

3rd

2nd

3rd

3rd

1

5

1

1

2nd

3rd

2nd

1

1

1

1

1

1

1

4th

3rd

5

5

5

5

5

5

2nd

3rd

3rd

2nd

2nd

3rd

2nd

5

3rd

5

5

5

5

5

4th

2nd

3rd

3rd

3rd

3rd

2nd

2nd

6

5

5

5

5

5

5

5

3rd

2nd

2nd

3rd

3rd

2nd

2nd

7

5

5

5

5

5

5

5

3rd

4th

3rd

4th

4th

3rd

3rd

No.

~ 8

9

10th

11

12

13

14

15

28

53

54

56

57

58

59

60

61

130

131

133

134

135

63

64

65

66

67

68

69

70

73

74

75

76

77

78

79

80

81

82

84

85

86

87

88

89

90

16

17th

19th

20th

21st

23

102

103

104

105

106

107

108

109

110

111

Table!! (Continuation)

Pre-emergence effect Post-emergence effect

Corn

Big one

Geese

Fox

Semolina

purple

zinnia

Corn

Big one

Geese

Fox

Semolina

purple

Room

Fingers foot tail root winds

Fingers foot tail root winds

grass

grass

4th

5

5

5

5

5

5

3rd

3rd

2nd

3rd

3rd

3rd

2nd

3rd

5

5

5

5

5

4th

3rd

3rd

2nd

2nd

2nd

2nd

2nd

4th

5

5

5

5

4th

3rd

4th

3rd

3rd

3rd

3rd

2nd

3rd

1

2nd

2nd

2nd

2nd

1

1

2nd

2nd

2nd

3rd

1

1

1

5

5

5

5

5

5

5

4th

4th

3rd

4th

3rd

3rd

3rd

5

5

5

5

5

5

5

4th

4th

2nd

4th

3rd

3rd

3rd

4th

5

5

5

5

5

5

3rd

2nd

2nd

2nd

1

2nd

2nd

3rd

5

5

5

5

5

5

2nd

2nd

2nd

2nd

2nd

2nd

2nd

2nd

3rd

3rd

2nd

2nd

1

2nd

1

1

1

1

1

1

1

3rd

5

5

5

5

4th

5

2nd

2nd

2nd

2nd

2nd

2nd

2nd

3rd

5

5

5

5

4th

3rd

2nd

2nd

2nd

2nd

2nd

2nd

2nd

1

1

1

1

1

1

1

1

1

1

1

1

1

1

5

5

5

5

5

4th

4th

3rd

4th

2nd

3rd

3rd

2nd

2nd

2nd

4th

2nd

2nd

2nd

1

1

2nd

2nd

2nd

2nd

2nd

2nd

2nd

3rd

5

4th

4th

4th

4th

3rd

3rd

3rd

2nd

2nd

2nd

2nd

2nd

5

5

5

5

5

5

5

3rd

2nd

2nd

2nd

2nd

2nd

2nd

1

1

1

1

1

1

1

1

1

1

2nd

1

2nd

1

1

5

3rd

4th

3rd

2nd

2nd

3rd

3rd

3rd

3rd

3rd

3rd

2nd

3rd

4th

4th

4th

3rd

3rd

2nd

4th

3rd

3rd

3rd

3rd

2nd

2nd

4th

5

5

5

4th

4th

4th

2nd

2nd

2nd

2nd

2nd

2nd

2nd

4th

5

5

5

5

4th

4th

2nd

2nd

2nd

2nd

2nd

2nd

2nd

3rd

5

3rd

5

3rd

3rd

2nd

3rd

4th

3rd

3rd

3rd

2nd

2nd

1

2nd

2nd

2nd

2nd

2nd

2nd

2nd

2nd

2nd

2nd

2nd

2nd

2nd

2nd

5

5

4th

5

4th

5

2nd

2nd

2nd

2nd

2nd

2nd

2nd

5

5

5

5

5

4th

5

3rd

3rd

2nd

3rd

3rd

3rd

3rd

5

5

5

5

5

4th

5

3rd

3rd

3rd

3rd

3rd

3rd

3rd

5

5

5

5

5

5

5

4th

4th

3rd

3rd

3rd

3rd

3rd

I.

1

1

1

1

1

1

2nd

1

2nd

1

2nd

2nd

1

5

5

5

5

5

5

5

4th

4th

4th

3rd

3rd

3rd

3rd

3rd

5

4th

4th

5

2nd

5

2nd

2nd

2nd

2nd

2nd

2nd

2nd

2nd

3rd

3rd

2nd

3rd

3rd

2nd

2nd

2nd

2nd

2nd

2nd

2nd

2nd

5

5

5

5

5

5

5

3rd

3rd

2nd

3rd

2nd

3rd

2nd

1

4th

5

3rd

3rd

4th

3rd

2nd

3rd

4th

2nd

2nd

2nd

2nd

5

5

5

5

5

5

5

3rd

4th

4th

3rd

3rd

3rd

3rd

5

5

5

5

5

5

5

4th

3rd

3rd

3rd

2nd

3rd

3rd

3rd

5

5

5

5

4th

4th

2nd

2nd

2nd

2nd

1

2nd

2nd

5

5

5

5

5

5

5

4th

4th

3rd

4th

3rd

3rd

3rd

2nd

5

5

3rd

4th

3rd

1

2nd

2nd

2nd

2nd

2nd

2nd

2nd

3rd

5

5

5

5

4th

5

2nd

4th

3rd

3rd

2nd

2nd

2nd

5

5

5

5

5

5

5

4th

4th

3rd

3rd

3rd

3rd

3rd

5

5

5

5

5

5

5

3rd

4th

3rd

4th

3rd

3rd

3rd

1

3rd

2nd

2nd

2nd

1

1

1

1

1

1

1

1

1

1

1

1

1

1

1

1

1

1

1

1

1

1

1

2nd

4th

3rd

2nd

2nd

1

2nd

2nd

2nd

2nd

2nd

2nd

2nd

2nd

1

3rd

3rd

2nd

2nd

2nd

2nd

1

1

1

1

1

1

1

4th

5

5

5

5

5

5

2nd

2nd

2nd

2nd

2nd

3rd

2nd

1

1

1

1

1

1

1

1

1

1

1

1

1

1

3rd

5

5

5

5

5

5

3rd

3rd

3rd

3rd

2nd

2nd

2nd

4th

5

5

5

4th

5

5

2nd

2nd

2nd

3rd

2nd

2nd

2nd

2nd

2nd

1

2nd

2nd

1

1

1

1

1

1

1

1

l

3rd

5

5

4th

5

1

2nd

2nd

2nd

2nd

2nd

2nd

2nd

2nd

2nd

4th

2nd

2nd

1

1

1

1

1

1

1

1

1

1

3rd

4th

2nd

2nd

3rd

2nd

2nd

2nd

2nd

2nd

2nd

2nd

2nd

2nd

2nd

5

5

3rd

4th

2nd

4th

2nd

2nd

2nd

2nd

2nd

2nd

2nd

1

1

1

1

1

1

1

1

1

1

1

1

1

1

4th

5

4th

5

5

4th

4th

3rd

3rd

3rd

3rd

3rd

3rd

3rd

5

5

5

5

5

5

5

3rd

2nd

2nd

2nd

2nd

3rd

2nd

3rd

5

5

4th

4th

4th

3rd

3rd

2nd

2nd

3rd

3rd

3rd

3rd

5

5

5

5

5

5

5

4th

4th

3rd

3rd

3rd

4th

3rd

4th

5

4th

4th

5

3rd

4th

3rd

3rd

3rd

2nd

2nd

2nd

2nd

1

1

4th

1

I.

1

1

2nd

2nd

3rd

2nd

1

2nd

2nd

2nd

4th

4th

3rd

4th

2nd

2nd

2nd

2nd

3rd

2nd

2nd

2nd

2nd

5

4th

5

4th

4th

3rd

2nd

2nd

2nd

2nd

2nd

2nd

2nd

2nd

Connect

No.

ÏÏ2 ~

113

114

115

116

72b

72c

72d

72e

72f

72g

72h

72i

72k

100a

100b

100c 100d

100e lOOf

100h looi lOOj

100k

1001

100m lOOn

135a

72j

100g lOOo

100p lOOq lOOr

100s

721

100t loou lOOw

72m lOOx

55

69

70

80

88

89

90

91

92

93

94

95

96

97

104

122

123

124

125

lOOy

2nd

1

2nd

2nd

2nd

2nd

2nd

2nd

2nd

2nd

1

3rd

1

2nd

3rd

1

2nd

2nd

2nd

2nd

2nd

2nd

2nd

2nd

2nd

2nd

2nd

1

2nd

2nd

2nd

2nd

3rd

2nd

2nd

2nd

2nd

1

1

2nd

2nd

3rd

1

2nd

2nd

1

2nd

3rd

2nd

2nd

2nd

1

1

2nd

2nd

3rd

1

2nd

2nd

3rd

3rd

2nd

2nd

33

Table II (continued)

Pre-emergence effect

Corn

Big finger

Goose foot

Fox semolina tail root

Purple zinnia winds

Post-emergence effect

Big goose finger foot

Corn

Fox semolina tail root

grass

grass

5

5

5

5

5

5

5

4th

4th

3rd

3rd

3rd

1

3rd

2nd

2nd

2nd

2nd

4th

2nd

2nd

2nd

1

1

1

5

5

3rd

2nd

1

1

2nd

3rd

3rd

2nd

2nd

1

2nd

3rd

1

1

2nd

2nd

2nd

2nd

3rd

2nd

2nd

4th

5

5

4th

5

3rd

4th

3rd

2nd

2nd

3rd

2nd

4th

5

4th

5

4th

4th

5

3rd

3rd

2nd

3rd

2nd

3rd

5

4th

5

4th

2nd

2nd

2nd

2nd

2nd

2nd

1

2nd

4th

2nd

4th

3rd

2nd

2nd

2nd

2nd

2nd

2nd

1

4th

4th

4th

4th

4th

2nd

3rd

2nd

2nd

2nd

2nd

1

5

5

5

5

4th

4th

5

3rd

3rd

3rd

3rd

3rd

2nd

4th

2nd

3rd

3rd

2nd

1

2nd

2nd

2nd

2nd

2nd

4th

5

5

5

5

5

5

3rd

4th

3rd

3rd

3rd

1

1

1

1

1

1

1

1

1

1

1

1

1

3rd

3rd

2nd

2nd

1

1

2nd

2nd

2nd

2nd

2nd

1

3rd

4th

3rd

5

4th

5

2nd

2nd

4th

2nd

4th

2nd

4th

2nd

4th

3rd

1

2nd

1

1

1

1

1

3rd

5

3rd

4th

4th

2nd

3rd

2nd

1

2nd

2nd

1

4th

5

5

4th

4th

4th

3rd

2nd

2nd

2nd

2nd

2nd

2nd

5

5

4th

4th

4th

4th

2nd

2nd

2nd

2nd

2nd

1

4th

4th

3rd

4th

3rd

2nd

2nd

2nd

3rd

3rd

1

2nd

4th

2nd

3rd

1

1

1

2nd

2nd

2nd

2nd

1

4th

5

3rd

5

5

2nd

2nd

2nd

3rd

2nd

2nd

2nd

2nd

4th

2nd

3rd

2nd

1

1

2nd

3rd

3rd

2nd

3rd

1

4th

2nd

2nd

2nd

1

1

1

1

2nd

1

1

1

4th

1

2nd

1

1

1

1

1

2nd

1

1

5

5

5

5

5

5

5

3rd

2nd

2nd

2nd

2nd

4th

5

5

5

5

2nd

4th

3rd

2nd

2nd

2nd

2nd

2nd

3rd

3rd

3rd

2nd

2nd

1

1

1

1

1

1

2nd

4th

4th

4th

4th

2nd

2nd

3rd

2nd

3rd

2nd

2nd

5

5

5

5

5

5

4th

3rd

2nd

2nd

2nd

2nd

3rd

5

5

4th

4th

3rd

2nd

1

2nd

2nd

2nd

1

3rd

5

5

4th

3rd

2nd

2nd

2nd

3rd

3rd

2nd

2nd

3rd

5

5

4th

4th

3rd

4th

3rd

3rd

2nd

2nd

2nd

4th

4th

4th

4th

4th

4th

4th

1

1

2nd

1

2nd

4th

5

5

5

5

5

5

3rd

2nd

2nd

2nd

2nd

4th

5

5

5

5

5

5

3rd

2nd

2nd

2nd

2nd

4th

5

4th

5

5

4th

4th

2nd

1

1

2nd

1

2nd

3rd

3rd

2nd

3rd

1

1

2nd

1

1

1

1

1

1

1

1

1

1

1

1

1

1

1

1

3rd

5

5

4th

3rd

2nd

2nd

2nd

2nd

2nd

2nd

2nd

2nd

4th

3rd

2nd

2nd

1

2nd

2nd

2nd

2nd

2nd

1

2nd

5

4th

4th

4th

3rd

3rd

3rd

4th

4th

4th

3rd

1

1

1

1

1

1

1

1

1

1

1

1

3rd

5

4th

4th

3rd

3rd

3rd

2nd

2nd

2nd

2nd

2nd

3rd

5

4th

4th

5

4th

3rd

2nd

3rd

3rd

3rd

2nd

1

1

1

1

1

1

1

1

2nd

1

1

3rd

4th

5

5

5

5

5

5

3rd

4th

3rd

3rd

3rd

5

5

5

5

5

5

5

4th

4th

3rd

3rd

2nd

1

4th

5

3rd

2nd

1

1

2nd

2nd

3rd

2nd

2nd

2nd

4th

2nd

3rd

1

2nd

2nd

1

1

2nd

1

2nd

1

3rd

4th

3rd

3rd

2nd

1

2nd

2nd

3rd

2nd

2nd

1

1

1

1

1

1

1

1

2nd

2nd

1

1

3rd

5

3rd

4th

4th

3rd

4th

2nd

1

2nd

1

1

3rd

4th

3rd

3rd

2nd

2nd

3rd

2nd

3rd

2nd

2nd

2nd

1

1

2nd

1

1

1

1

2nd

2nd

2nd

1

1

4th

5

5

5

5

4th

3rd

4th

4th

3rd

3rd

3rd

1

1

1

1

1

1

1

1

1

1

1

1

1

1

1

1

1

1

1

2nd

2nd

2nd

2nd

2nd

1

1

1

1

1

1

1

2nd

2nd

2nd

2nd

2nd

4th

5

5

5

5

3rd

4th

3rd

4th

3rd

3rd

3rd

4th

5

5

5

4th

4th

4th

3rd

2nd

2nd

3rd

2nd

5

5

4th

5

4th

5

5

2nd

2nd

2nd

2nd

1

3rd

5

5

4th

4th

2nd

2nd

2nd

2nd

2nd

2nd

2nd

632 496 34

Tabèlle II (continued)

Connection pre-emergence effect post-emergence effect

^ r 'Corn Large Geese - Fox- Semolina- Purple-Zinnia Corn Large Geese- Fox- Semolina- Purple-Zinnia Finger-foot tail seasoning! winch finger-foot tail seasoning) winch grass grass

~ 72n 1 ï ï ï Ï 2 Ì 2 Ì 2 î Î 2 2

72o 4555555 2222222

lOOcc 1121111 1212211

lOOdd 1342321 1121131

lOOee 2433432 22 2 2122

lOOff 2542311 2221121

101a 5555555 3333333

10011 3554444 3333322

lOOgg 4555555 3333223

100mm 2554322 2232322

lOOhh 5545555 3323222

lOOii 5555555 3433222

lOOjj 3555455 233 3 222

lOOkk 4555555 33 33222

129a 3343232 3222222

Connection advance effect follow-up effect

^ r "Corn Large Geese - Fox- Semolina- Purple-Zinnia Corn Large Geese- Fox- Semolina- Purple-Zinnia 'Finger-foot tail root winds Finger-foot tail root winds grass grass

~ 23a 5 5 5 5 5 5 5 3 ~ 3 3 3 2 2 2

23b 4555555 3332222

23c 2444323 1121111

72p 1423332 2222222

72q 2555543 1222121

72r 1433112 2222222

72s 1332311 1222222

72t 3555443 2343332

72u 5555555 2333222

72v 555443 2232222

72w 2553332 2232222

72x 3515333 3333222

72y 4555545 2322222

72z 4554524 3333222

72aa 3545532 2 222222

72bb 5555555 2222222

72cc 5555555 3332222

72dd 5555555 3333333

72ee 3555555 2222222

72ff 55 55 5 55 3332222

72gg 5555555 3343322

72h 2554434 2222222

72ii 3554312 2232222

lOOnn 4555555 4333222

lOOoo 3555555 3333222

lOOpp 3555555 2323222

lOOqq 3323322 1111111

LOOR 5555555 3433 3 22

lOOss 3555443 1222222

lOOtt 4555555 2232222

lOOuu 4555422 2332322

lOOvv 4555544 2323322

lOOww 2343321 1221121

lOOxx 3 4 3 3 2 2 2

lOOyy 3443422 1111111

lOOab 4555511 3323222

lOOac 2555513 2222 222

lOOad 3555443 2222222

lOOae 2333211 222222 2

lOOaf 45555 33 3333323

lOOag 3555422 223222 2

lOOah 4555555 3333 223

lOOai 3554322 2222222

35

Table II (continued)

632496

Connection no.

Lead effect

Run-on effect

Corn

Big finger grass

Goose foot

Fox semolina tail root

Purple zinnia winds

Corn

Big finger grass

Goose foot

Fox semolina tail root

Purple winds

Zinnia looaj

4th

5

5

4th

5

3rd

3rd

2nd

3rd

3rd

2nd

2nd

2nd

2nd

looak

1

5

5

5

5

1

2nd

2nd

2nd

2nd

2nd

2nd

2nd

2nd

looal

5

5

5

5

5

5

5

2nd

2nd

2nd

2nd

2nd

2nd

2nd

lOOam

3rd

5

5

5

5

4th

4th

3rd

3rd

3rd

3rd

3rd

3rd

2nd

lOOan

3rd

5

5

5

5

4th

2nd

1

2nd

2nd

2nd

2nd

2nd

2nd

lOOao

3rd

5

5

3rd

4th

3rd

2nd

2nd

2nd

2nd

2nd

2nd

3rd

lOOap

1

4th

5

4th

2nd

1

1

2nd

2nd

2nd

2nd

2nd

2nd

lOOaq

2nd

4th

4th

4th

3rd

2nd

1

2nd

2nd

2nd

2nd

3rd

2nd

looar

4th

5

5

5

4th

3rd

2nd

3rd

2nd

2nd

3rd

2nd

2nd

lOOas

4th

5

5

5

5

5

5

3rd

3rd

3rd

3rd

3rd

2nd

2nd

132a

4th

5

5

5

4th

4th

4th

2nd

3rd

3rd

2nd

2nd

2nd

2nd

132b

3rd

4th

4th

4th

2nd

1

1

2nd

2nd

2nd

2nd

2nd

2nd

2nd

132c

3rd

5

5

5

3rd

3rd

2nd

2nd

2nd

2nd

2nd

1

2nd

2nd

132d

4th

5

5

5

5

4th

3rd

3rd

3rd

2nd

2nd

3rd

2nd

2nd

132e

5

5

5

5

5

5

5

4th

4th

3rd

3rd

3rd

3rd

3rd

132f

4th

5

5

4th

5

5

4th

3rd

2nd

3rd

2nd

1

2nd

2nd

132g

3rd

5

5

4th

4th

4th

4th

2nd

3rd

3rd

2nd

2nd

3rd

2nd

132h

3rd

5

2nd

4th

2nd

3rd

2nd

2nd

2nd

3rd

1

2nd

3rd

2nd

lOOap

5

5

5

5

5

5

5

4th

4th

4th

3rd

3rd

3rd

3rd

lOOat

1

4th

2nd

2nd

2nd

2nd

1

1

1

1

1

1

1

1

lOOav

4th

5

5

5

4th

5

4th

2nd

3rd

3rd

2nd

2nd

2nd

2nd

lOOaw

4th

5

5

4th

5

5

4th

2nd

3rd

2nd

3rd

2nd

2nd

2nd

lOOax

4th

5

5

5

5

5

4th

3rd

3rd

3rd

3rd

3rd

3rd

3rd

looay

1

3rd

3rd

1

1

1

1

1

1

1

1

1

1

1

looaz

3rd

4th

2nd

3rd

3rd

3rd

4th

1

1

1

1

1

1

1

lOOba

1

3rd

3rd

2nd

1

1

1

2nd

1

2nd

1

2nd

2nd

2nd

lOObc

3rd

5

5

5

3rd

3rd

2nd

3rd

4th

3rd

3rd

3rd

3rd

lOObd

3rd

5

5

4th

4th

2nd

2nd

2nd

4th

3rd

2nd

2nd

2nd

lOObe

5

5

5

5

5

5

5

3rd

3rd

2nd

3rd

3rd

2nd

2nd

lOObf

4th

3rd

3rd

2nd

2nd

2nd

2nd

2nd

4th

2nd

1

2nd

2nd

72y

4th

5

4th

5

5

5

4th

3rd

3rd

3rd

3rd

2nd

2nd

2nd

72kk

5

5

5

5

5

4th

5

3rd

2nd

3rd

3rd

3rd

2nd

3rd

121a

2nd

4th

2nd

2nd

2nd

1

1

1

1

1

1

1

1

1

124a

4th

5

5

5

5

5

4th

3rd

2nd

2nd

2nd

2nd

2nd

2nd

124b

5

5

4th

4th

3rd

3rd

3rd

3rd

4th

2nd

2nd

3rd

2nd

124c

5

5

5

5

4th

5

5

3rd

4th

3rd

2nd

3rd

3rd

124d

3rd

5

4th

5

5

4th

4th

2nd

3rd

2nd

3rd

3rd

3rd

124e

5

5

5

5

5

5

5

4th

3rd

3rd

3rd

3rd

3rd

124f

4th

5

5

5

5

5

4th

3rd

4th

3rd

3rd

3rd

3rd

Example 72

Greenhouse experiment with many plant species The test method used is generally the same as the method described in the experiment above. Different compounds of formula I are examined before and after emergence under different application amounts, which are listed in the following tables. A number of other weed * and crop species are used for the pre-emergence studies, as indicated in Table III below. The results obtained in these experiments are shown in Tables III and IV below.

Contract pre-impact binding amount

No. in kg / ha s a

Bs

S o e? i> <u a? * 5 «C P

5 N k, £ *. £?

03 O * 'J5 & -C% _ ^ s M h s £ f (r, 2 S <£

- ì3, S5E5 8feSg> 3 M £ gl ^ s

O § S -S 2 8 V <§ iE g .a— s

—S iw g? S S t S a <2 -S

- - ïï? Ä r *, b. £ C C o 3 »J5 g>

- * SLqg_g 3 ||| f ||

ä ° «Il

24th

31

32

1.1 21224422224423323222 0.56 21324312324434435242

2.2 11112211222323222211

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n 3'q fit i c

3 OQ

3'§ Ì

12f 3 s?

s

ïï «?

On M Kl

ê ® \

Corn

cotton

Soybean

wheat

alfalfa

sugar beet

rice

cucumber

tomato

Chicken millet

White goose foot

Big finger grass

mustard

Goose foot

Foxtail

Wild oats

Semolina

Common thorn apple

Purple winch zinnia ff o-

O w T1 on o a

$

I ä

37

Table III (continued)

632 496

connection

Order quantity

Preflow effect

No.

in kg / ha

Corn

cotton

Soybean

wheat

alfalfa

Sugar beet vi

'S C4

cucumber

tomato

Chicken millet

White goose foot

Big finger grass

mustard

Goose foot

Foxtail

Wild oats

Semolina

Common thorn apple

Purple winds

zinnia

104

0.14

1

1

3rd

4th

4th

4th

i

1

2nd

4th

3rd

3 3

3rd

4th

1

2nd

2 2

2nd

105

0.56

3rd

1

3rd

5

5

5

i

3rd

5

5

5

5 5

5

5

2nd

4th

4 4

3rd

106

0.28

2nd

1

2nd

2nd

4th

4th

2nd

2nd

2nd

4th

5

5 4

5

4th

2nd

4th

4 4

2nd

107

1.1

4th

4th

4th

5

5

3rd

5

5

5

5

5 5

5

5

5

5

5 5

5

110

1.1

1

1

1

2nd

2nd

2nd

1

1

2nd

2nd

4th

4 4

4th

2nd

2nd

2nd

2 2

2nd

111

1.1

2nd

1

2nd

2nd

4th

4th

1

2nd

3rd

2nd

4th

4 4

4th

3rd

2nd

2nd

3 2

2nd

112

1.1

4th

1

4th

4th

5

5

3rd

5

5

4th

5

5 5

5

5

4th

4th

4 4

5

114

4.5

1

1

1

2nd

4th

3rd

1

2nd

1

3rd

4th

5 5

5

3rd

1

2nd

1 2

2nd

116

0.14

2nd

1

2nd

4th

4th

5

1

2nd

2nd

3rd

3rd

4 4

4th

5

2nd

2nd

3 1

2nd

72a

0.28

3rd

1

2nd

3rd

5

5

2nd

3rd

3rd

4th

4th

4 3

4th

5

5

5

5 4

4th

72b

0.56

4th

1

3rd

3rd

5

5

2nd

2nd

5

4th

5

5 5

5

5

3rd

5

5 3

4th

72c

1.1

3rd

1

2nd

4th

5

5

2nd

2nd

4th

4th

4th

5 4

5

5

2nd

2nd

3 2

2nd

72d

4.5

1

1

1

2nd

2nd

2nd

3rd

1

1

2nd

3rd

4 2

4th

3rd

2nd

2nd

1 1

1

72f

0.56

1

1

2nd

2nd

4th

3rd

1

2nd

2nd

2nd

3rd

3 3

2nd

4th

2nd

2nd

2 2

2nd

72h

1.1

3rd

1

3rd

3rd

5

5

2nd

4th

5

4th

5

5 5

5

5

3rd

3rd

4 5

5

100a

4.5

1

2nd

1

2nd

3rd

2nd

3rd

1

1

3rd

2 2

2nd

1

2nd

2nd

2 1

3rd

100b

4.5

1

1

2nd

2nd

3rd

2nd

2nd

2nd

2nd

2nd

3rd

5 2

2nd

3rd

1

4th

2 1

2nd

100c

2.2

2nd

1

1

3rd

5

2nd

1

2nd

4th

4th

4th

5 3

2nd

3rd

2nd

4th

3 3

2nd

lOOd

1.1

3rd

1

2nd

3rd

3rd

3rd

1

2nd

3rd

3rd

4th

4 3

4th

3rd

3rd

3rd

2 2

3rd

100e

2.2

1

1

1

1

2nd

4th

1

2nd

2nd

3rd

4th

4 3

4th

3rd

2nd

4th

3 2

2nd

lOOf

4.5

1

1

1

1

2nd

5

2nd

1

2nd

1

3rd

2 2

5

3rd

1

4th

3 3

2nd

looi

0.56

2nd

1

1

2nd

4th

1

2nd

2nd

5

5

5 3

3rd

3rd

2nd

4th

3 2

2nd

100m

1.1

3rd

1

2nd

4th

5

5

4th

3rd

3rd

4th

4th

5 4

4th

5

5

3rd

4 4

5

lOOn

2.2

4th

1

2nd

2nd

2nd

4th

1

2nd

1

4th

4th

3 3

3rd

4th

3rd

2nd

3 3

4th

72j

2.2

2nd

1

1

2nd

3rd

3rd

2nd

1

2nd

3rd

4th

4 2

3rd

3rd

1

2nd

1 1

1

100 g

1.1

4th

1

3rd

3rd

4th

5

2nd

2nd

4th

4th

3rd

4 3

5

5

3rd

5

4 4

4th

lOOo

1.1

2nd

1

1

2nd

2nd

3rd

1

1

2nd

3rd

4th

4 2

4th

4th

1

3rd

2 2

2nd

100p

2.2

2nd

1

1

2nd

3rd

4th

3rd

1

2nd

3rd

5

4 2

4th

4th

3rd

3rd

2 2

2nd

lOOq

1.1

3rd

l

1

2nd

2nd

5

2nd

2nd

3rd

4th

5

5 4

4th

5

3rd

3rd

3 3

2nd

100s

2.2

3rd

1

2nd

4th

5

5

1

4th

5

4th

5

5 5

5

5

4th

4th

4 5

5

721

1.1

4th

4th

3rd

4th

5

3rd

4th

5

4th

4th

5 4

5

4th

5

4th

3 4

3rd

100t

2.2

4th

1

3rd

2nd

3rd

5

1

2nd

3rd

3rd

4th

5 3

4th

3rd

3rd

4th

2 3

2nd

72m

2.2

3rd

1

2nd

2nd

3rd

5

2nd

2nd

4th

3rd

4th

5 5

4th

3rd

3rd

3rd

2 2

2nd

69

4.5

2nd

1

1

1

2nd

3rd

1

2nd

1

1

3rd

3 4

2nd

2nd

1

2nd

2 2

2nd

lOOy

1.1

2nd

2nd

3rd

3rd

5

1

5

5

4th

5

5 5

5

5

4th

3rd

3 5

4th

lOOaa

0.56

2nd

1

2nd

2nd

2nd

4th

1

3rd

3rd

3rd

4th

5 2

2nd

2nd

2nd

1

2 2

2nd

lOObb

1.1

2nd

1

1

2nd

3rd

4th

1

1

2nd

3rd

5

5 3

5

3rd

2nd

2nd

2 2

1

lOOee

1.1

1

1

1

1

1

3rd

1

1

2nd

1

3rd

3 2

3rd

2nd

1

2nd

2 2

1

101a

1.1

4th

1

3rd

4th

5

5

3rd

5

5

5

5

5 5

5

5

5

4th

4 5

5

10011

1.1

2nd

1

2nd

2nd

3rd

3rd

2nd

2nd

4th

4th

4th

4 5

5

5

2nd

3rd

4 3

2nd

lOOgg

1.1

3rd

1

3rd

5

5

3rd

2nd

2nd

5

5

5

5 5

5

5

4th

5

3 5

5

100mm

2.2

1

1

1

1

1

3rd

1

1

2nd

3rd

4th

3 2

4th

4th

2nd

3rd

2 2

1

loohh

0.56

3rd

1

1

2nd

3rd

5

2nd

2nd

3rd

3rd

5

4 3

3rd

5

3rd

2nd

2 2

2nd

lOOii

0.28

1

1

1

2nd

2nd

5

1

3rd

5

3rd

5

4 4

4th

5

2nd

3rd

3 4

3rd

lOOkk

1.1

3rd

1

3rd

3rd

5

5

2nd

3rd

3rd

4th

5

5 5

5

5

2nd

5

4 5

4th

Table IV

Table IV (continued)

Connection-on- post-emergence effect

No. of maize Large goose, fox, semolina, purple, zinc 68 in finger base, tail root, never win kg / ha grass

40

41 1

43

44

31

2.2

2nd

3rd

3rd

3rd

3rd

3rd

3rd

32

2.2

2nd

2nd

2nd

2nd

2nd

2nd

2nd

34

2.2

3rd

3rd

3rd

3rd

3rd

3rd

3rd

36

2.2

2nd

2nd

3rd

2nd

3rd

2nd

3rd

38

1.1

2nd

3rd

3rd

3rd

3rd

2nd

3rd

45

46 65 47

48 2 7

1.1

2.2 2.2 2.2

2 2 4 4 2 2

2 4

3 3 2

2nd

2nd

3 3 3 3 2

2nd

3 2 2

2nd

2 4 4

3 2

2nd

3 3 2 2

2nd

2nd

3 3 3 3 3 3 3 2 2

2nd

2nd

3 3 3 3 2

2nd

3 2 2

2nd

2nd

3 3 3 2

2nd

3 3 3 2

632496

Table IV (continued)

38

Table V (continued)

Connection load-bearing

Post-emergence effect

Connections No.

Pre-emergence effect at 9 kg / ha

Post-emergence effect at 9 kg / ha

Semolina- Purple- Zin

No quantity

Corn Big Goose Fox

in

Finger foot tail root never winds

5

4th

3rd

3rd

kg / ha of grass

5

3rd

3rd

6

5

5

12 1.1

4 3 2 2

3 3 3

7

5

5

13 1.1

4 3 2 3

3 3 2

8th

5

5

67 1.1

3 3 2 3

2 2 2

10th

9

5

4th

76 1.1

2 2 3 2

2 3 2

10th

5

4th

79 0.56

3 4 3 3

3 2 3

11

2nd

1

107 1.1

3 4 3 3

3 3 3

14

5

5

112 1.1

3 3 3 3

2 2 3

15

4th

3rd

100a 4.5

13 3 2

3 3

15

28 53

1 4

4th

54

3rd

3rd

55

4th

Example 73

56

1

Examination with yellow cyper grass

20th

57

5

4th

Typical compounds of formula I are in the greenhouse

58

1

2nd

with regard to their effect on yellow cypress grass

59

3rd

3rd

examined. The procedure used generally corresponds

60

5

5

mean the procedure described in Example 70, where

61

1

1

however, the acetone-ethanol solution deviates from this 1.5 g /

25th

130

4th

4th

Contains 100 ml of test compound and one before use

131

3rd

4th

Dilute part of the organic solution with 9 parts of water

133

3rd

3rd

becomes. Both pre-emergence and post-emergence

134

4th

3rd

investigations with the respective connections

135

5

4th

leads, namely with application quantities of 9.0 kg / ha. The one there

30th

63

2nd

Results obtained are shown in Table V below

64

1

2nd

forth.

65

66

5 5

4 4

Table V

67

5

5

35

68

1

1

links

Pre-emergence effect

Post-emergence effect

69

4th

4th

No.

at 9 kg / ha at 9 kg / ha

70

2nd

2nd

74

5

4th

24th

2nd

1

75

1

1

25th

2nd

1

40

78

3rd

3rd

26

1

1

79

5

4th

27th

1

1

80.

1

2nd

29

1

81

3rd

2nd

30th

3rd

85

2nd

1

31

4th

45

87

5

2nd

32

1

89

5

4th

33

1

90

1

1

34

4th

17th

2nd

1

35

3rd

18th

2nd

1

36

3rd

50

19th

1

1

129

1

20th

2nd

2nd

37

5

4th

23

3rd

3rd

38

5

4th

102

1

1

39

1

1

103

1

1

41

5

4th

55

105

4th

3rd

1

5

5

106

3rd

3rd

43

5

4th

107

5

4th

44

3rd

2nd

109

1

1

45

3rd

2nd

110

1

2nd

46

4th

2nd

60

111

2nd

1

47

5

4th

112

4th

4th

48

5

4th

113

1

2nd

49

3rd

3rd

114

1

2nd

50

4th

4th

116

4th

4th

51

5

5

65

72a

5

4th

52

3rd

1

lOOj

3rd

2nd

132

2nd

1

100k

1

1

2nd

4th

4th

39

632496

Example 74

Studies with broad-leaved weeds A number of typical compounds of the formula I are investigated in the greenhouse against broad-leaved weeds, which are representatives of weed families and are resistant to a number of known herbicides. The procedure used for these studies is generally the same as the procedure of Example 73, except that the compounds are used only before emergence. All compounds are tested at active ingredient concentrations of 9.0 kg / ha.

Table VI

Table VI (continued)

10th

15

Compound No. Garden- Canadian Common Heidelberg- Goose- Ambrosia berry cress

Spiny Black Sida Nightshade

24th

3rd

2nd

4th

25th

4th

3rd

5

26

2nd

2nd

3rd

27th

2nd

1

2nd

29

2nd

2nd

2nd

30th

3rd

3rd

4th

31

5

5

5

32

2nd

5

4th

33

2nd

3rd

2nd

34

5

5

5

35

5

3rd

4th

36

5

2nd

4th

129

1

1

1

37

5

4th

5

38

5

5

5

39

3rd

2nd

3rd

41

5

5

5

1

5

5

5

43

5

5

5

44

3rd

3rd

4th

45

5

4th

5

46

5

4th

5

47

5

5

5

48

5

5

5

49

4th

3rd

4th

50

4th

3rd

3rd

51

5

5

5

52

3rd

4th

5

132

3rd

3rd

3rd

2nd

. 5

4th

4th

4th

5

2nd

4th

5

5

5

4th

6

5

5

5

7

5

5

5

8th

5

5

5

9

5

5

5

10th

5

5

5

11

4th

3rd

4th

14

5

5

5

15

5

3rd

3rd

28

3rd

1

53

5

4th

4th

54

5

2nd

3rd

55

1

1

1

56

1

1

1

57

5

5

5

58

3rd

2nd

5

60

5

5

5

61

1

1

1

25th

30th

35

40

45

Connection no.

garden

Canadian

Common

Prickly

Black

heidel

Geese

Ambrosia

Sida

night

berry cress

shadow

130

5

5

5

131

5

5

5

133

4th

2nd

3rd

134

5

2nd

4th

135

5

5

5

63

3rd

3rd

3rd

64

5

4th

3rd

65

5

5

5

66

5

5

5

68

2nd

1

2nd

69

5

5

5

70

3rd

1

1

74

5

5

5

75

4th

3rd

4th

78

4th

2nd

4th

80

2nd

2nd

3rd

81

4th

4th

4th

85

2nd

1

2nd

87

2nd

2nd

5

89

5

5

5

90

2nd

2nd

2nd

17th

5

5

5

18th

2nd

2nd

2nd

19th

1

1

1

20th

5

3rd

3rd

21st

2nd

2nd

2nd

23

5

2nd

5

102

3rd

1

2nd

103

1

1

1

105

5

5

5

106

5

3rd

5

107

5

5

5

109

2nd

1

2nd

110

3rd

2nd

2nd

111

5

5

5

112

5

5

5

113

1

4th

4th

114

1

3rd

3rd

116

5

5

5

72a

5

4th

5

lOOj

2nd

2nd

5

100k

2nd

2nd

4th

50

55

«0

65

Example 75

Investigation of the effectiveness against 14 plant species with active ingredients incorporated into the soil

This experiment serves to determine the effectiveness of typical compounds of the formula I against a number of crop and weed species. The compounds are examined in the greenhouse in the various concentrations shown in the following table. In all cases, the application to the plants to be examined is carried out before emergence, the active compounds being incorporated into the soil before the seeds are planted. The formulation of the compounds and the sowing and the observation of the plants to be examined is generally carried out according to the method described in Example 73, but the compounds are, however, in solution in acetone-ethanol in a concentration of 1 g per 100 ml, before being diluted with water for use.

632496

40

Table VII

Order amount Qty.

Corn

Corn grain millet sorghum

Wild rice oats

Chicken Wheat Purple Soybean Millet Bean

Stachel- Baum- Geese-lige wool foot Sida

Cucumber Common Datura

34

0.28

10th

9.5

10th

10th

9.8

10th

10th

9.8

9

9.5

0

10th

2nd

7.5

37

0.14

8th

5

6

8th

6

7

8th

2nd

2nd

1

0

8th

0

4th

1

0.14

10th

9

9.5

10th

8.5

10th

10th

9

10th

10th

0

10th

10th

10th

43

0.28

9

9

9

10th

6

10th

10th

8.5

8.5

6

0

0

3rd

5

47

0.14

10th

9.5

9.5

10th

9.8

10th

10th

10th

10th

6

0

0

8th

8th

48

0.28

10th

10th

10th

10th

10th

10th

10th

9.5

10th

10th

0

10th

10th

10th

49

0.56

8th

5

7

9

4th

8th

9

1

1

0

0

0

0

0

50

0.56

8.5

5

7

9.5

9.5

9.5

9.5

3rd

2nd

1

0

8th

0

4th

51

0.28

10th

9.5

9.5

10th

9.5

10th

10th

7

7

6

0

10th

9

10th

52

1.1

9.8

9.5

7

7

1

9

9

8th

9.5

4th

0

4th

3rd

3rd

2nd

0.14

7

5

6

9

8th

8th

9

2nd

2nd

4th

0

10th

9.5

9

4th

0.28

9

8th

9

9

7

9

9

5

5

2nd

0

8th

2nd

7

5

0.28

5

3rd

3rd

5

0

6

5

0

0

0

0

7

0

1

6

0.14

10th

10th

9.5

10th

10th

10th

10th

9.8

10th

10th

0

8th

10th

10th

7

0.14

9.5

7

7

9.5

4th

8th

9

4th

6

8th

0

3rd

0

2nd

8th

0.14

9

6

6

10th

8th

9

9

5

5

0

0

0

9

8th

9

0.28

9

6

8th

9.5

7

8th

9

2nd

2nd

1

0

6

6

5

10th

0.28

6

3rd

5

6

2nd

5

7

0

0

0

0

7

0

0

12

0.14

10th

9.5

9.5

10th

9.5

9.5

9.5

8.5

9.5

10th

0

8th

9.5

10th

13

0.14

10th

8.5

9.5

10th

9.5

10th

10th

10th

8.5

10th

0

9.5

10th

10th

14

0.28

10th

10th

10th

10th

10th

10th

10th

10th

9.5

10th

10th

10th

10th

15

0.56

6

5

4th

7

2nd

7

7

0

0

0

0

5

5

5

53

0.28

9

9

8th

9

8th

9

9

5

5

3rd

0

9

4th

7

57

0.28

10th

9.5

9.5

10th

9.5

10th

10th

8.5

9.5

10th

0

10th

10th

10th

59

0.56

6

2nd

1

3rd

1

2nd

7

0

2nd

0

0

2nd

1

0

60

0.28

9

9

8.5

10th

9

9.5

9.5

8th

6.5

6

0

9.5

8th

8th

130

1.1

10th

9.8

7

9.5

1

9

9.5

9.8

8th

10th

9.5

3rd

2nd

131

0.56

4th

5

3rd

4th

1

4th

4th

5

6

2nd

1

2nd

3rd

1

133

0.28

5

5

4th

6

5

7

7

2nd

0

0

0

3rd

0

3rd

134

0.56

9.5

8th

7

7

3rd

8th

8th

3rd

3rd

2nd

0

2nd

0

3rd

135

0.14

5

4th

3rd

5

2nd

6

4th

0

2nd

0

0

3rd

0

3rd

65

0.14

10th

9.5

9

9

6

9.5

9.5

8th

10th

8th

0

0

10th

8th

66

0.14

9.5

10th

9

9.5

9

10th

9

9

10th

9

0

0

10th

10th

67

0.14

10th

10th

10th

10th

9

10th

10th

9

10th

9

0

0

10th

10th

74

0.14

10th

10th

9

10th

8th

10th

9.5

9

10th

8th

0

2nd

10th

10th

76

0.28

3rd

3rd

0

0

0

3rd

2nd

5

5

5

0

5

6

7

77

0.14

10th

10th

10th

10th

9

10th

10th

9

9

8th

0

5

10th

9

78

0.56

5

5

3rd

2nd

0

3rd

8th

0

0

0

0

0

0

2nd

79

0.14

10th

10th

10th

10th

8th

10th

10th

9

8th

10th

0

4th

6

7

80

0.28

0

0

0

0

0

0

0

0

0

0

0

0

0

0

89

0.14

6

9

2nd

2nd

0

3rd

3rd

5

5

8th

0

4th

5

7

16

1.1

2nd

4th

1

0

0

8th

1

6

5

3rd

0

1

5

5

17th

1.1

1

3rd

0

0

2nd

7

1

5

5

3rd

0

1

5

4th

18th

1.1

0

1

0

0

0

0

0

1

2nd

1

0

1

2nd

2nd

20th

0.56

5

3rd

2nd

6

4th

7

7

0

0

0

0

6

0

2nd

104

0.28

9.5

9

9.5

10th

9

10th

10th

8th

10th

7

0

7

8th

8th

105

0.28

8.5

9

8th

8th

7

9

10th

6

6

7

0

4th

9

9

106

0.28

9

9

8.5

9

8th

9

9

4th

4th

7

0

8th

6

9

107

0.28

10th

9

9.5

10th

9

10th

10th

10th

9

9.5

2nd

9

10th

9

112

0.28

10th

9.5

9.5

10th

9.5

9.5

10th

9

8th

10th

0

10th

10th

10th

116

0.28

9

8th

8th

8th

8th

9.5

10th

2nd

7

5

0

10th

10th

10th

Example 76

Study of 14 plant species followed in the greenhouse. The active ingredients are used in various

In this experiment, the respective active ingredients of the concentrations as shown in the following Table Formula I before emergence of the plants to be examined 6s. Applied to the soil surface for the investigation of various active substances. Various plant species are generally used / The meanings again refer to the process search results described in Example 73 are summarized in Table VIII.

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Connection no.

Application quantity in kg / ha

Canadian goose cress

Garden bilberry

cotton

Ambrosia

Soybean

Venetian mallow

Purple winds

Common thorn apple

Forage millet

Goose foot

Corn

White goose foot

Finger grass

Semolina root

Spiny sida

Kornsorghum Wild Oat Rice

Chicken millet

Wheat Sugar Beet

632496 42

Example 77

Tests with active ingredients incorporated into the soil are followed. Various compounds are used for the investigation. It is drawn, and the individual active ingredients are examined against the general various plant species described in Example 73

Table IX

Connection no.

Application quantity in kg / ha

Common thorn apple

Garden bilberry

Goose foot

Ì

cotton

Prickly Sida

Ì

White 1 goose foot

Purple winds

Fingergrass

Yellow cypress grass

Forage millet

Semolina

Chicken millet

Hollyhock

Venetian mallow

Edible marshmallow

Burdock

31

0.28

8th

10th

4th

0

10th

10th

10th

10th

5

10th

10th

10th

7

0.56

10th

10th

7

3rd

10th

10th

10th

10th

8th

10th

10th

10th

9

1.1

10th

10th

10th

4th

10th

10th

10th

10th

10th

10th

10th

10th

10th

2.2

10th

10th

10th

8th

10th

10th

10th

10th

10th

10th

10th

10th

10th

34

0.21

0

9

9

8th

10th

8th

0

0.28

10th

10th

10th

0

10th

10th

10th

10th

8th

10th

10th

10th

10th

10th

0

8th

0.56

10th

10th

10th

0

10th

10th

10th

10th

10th

10th

10th

10th

10th

10th

2nd

9

37

0.28

10th

10th

10th

0

10th

10th

10th

10th

8th

10th

10th

10th

9

0.56

10th

10th

10th

0

10th

10th

10th

10th

10th

10th

10th

10th

10th

38

0.28

7

8th

2nd

0

10th

9

8th

10th

3rd

10th

10th

10th

5

0.56

10th

10th

4th

0

10th

10th

10th

10th

5

10th

10th

10th

8th

1.1

10th

10th

7

3rd

10th

10th

10th

10th

8th

10th

10th

10th

10th

1

0.21

8th

10th

0

10th

10th

10th

10th

9

10th

10th

4th

0.56

9

10th

0

10th

10th

10th

10th

10th

10th

10th

7

48

0.21

7

9

0

7

10th

10th

10th

0.56

8th

9

0

8th

10th

10th

10th

2nd

0.21

5

8th

0

7

6

8th

7

0.42

7

10th

0

8th

7

10th

10th

0.56

7

10th

0

8th

7

10th

10th

Example 78

Surface application of the active ingredient to determine the effect on several crop plants

Typical compounds of formula I are examined against a number of typical useful plants in a field screening, the plots to be examined being artificially sown with weeds. Seeds of the crops shown in the following table are planted in rows in a medium weight soil from the Midwest. The compounds listed below are applied in strips over the rows of crop seeds, immediately after sowing. The strips are about 1 m wide, so that each test plot consists of a 1 m long row of each useful plant specified below. The compounds are sprayed onto the soil surface in the form of an aqueous dispersion which is similar to the dispersion described in Example 71 above and which is similar to the dispersion described in Example 71 above.

All test plots are covered with goose foot and foxtail immediately before sowing the plots, and then treated with the compounds. Untreated control plots are compared to the treated plots.

39 days after sowing and treatment, the plots are observed by an experienced plant scientist, assessing the percentage weed control and the percentage damage to crops. The results obtained are shown in Table X below.

Table X

it

O W> C

German

4>

N C

CS

40

9

•O

B

IS

ü C

> e.g.

Application mi in kg / ha

Cotton II

peanuts

Sorghum tn

(2nd

wheat

£ o l / l t / 5

• £ 5

Goose foot

Soybean

45

31

M

7

7

13

20th

23

92

78

3rd

2.2

0

17th

50

43

27th

99

94

52

4.5

30th

30th

90

57

62

99

99

100

34

1.1

7

7

27th

20th

3rd

99

98

30th

2.2

10th

43

80

57

43

99

96

67

50

4.5

25th

47

93

77

77

100

98

90

37

1.1

15

3rd

20th

17th

13

99

97

40

2.2

27th

10th

47

17th

13

99

99

50

4.5

70

30th

67

50

53

99

99

89

38

1.1

3rd

0

7

27th

10th

87

68

0

55

2.2

10th

3rd

33

13

7

95

83

23

4.5

10th

27th

80

27th

67

100

97

73

1

0.56

35

33

37

10th

3rd

97

98

63

Example 79

«O Investigations with several crop plants and active ingredients incorporated into the soil

The procedure of Example 78 is followed, but the compounds of the formula I are incorporated with a rotary tiller immediately after application.

“Immediately after the application and incorporation of the compounds, crop and weed seeds are sown.

43

632496

Table XI

CO

c o eo e o

M

3rd

• o c

• Q

4) **

•> z

Application in kg / ha

"3 S E s rt

CO

peanuts

Sorghum

(5th

wheat

Foxtail

Goose foot

1

Soybean

31

0.28

10th

0

3rd

25th

17th

13

30th

3rd

0.56

20th

27th

23

23

47

83

10th

33

1.1

0

63

57

63

80

97

20th

50

2.2

0

63

85

90

100

99

32

73

34

0.28

0

30th

27th

30th

37

55

10th

23

0.56

7

7

37

60

83

96

17th

27th

1.1

0

50

73

83

100

99

78

83

2.2

0

50

92

93

100

100

94

80

37

0.28

0

0

17th

40

33

37

0

13

0.56

10th

7

33

70

50

72

10th

30th

1.1

0

17th

33

77

93

95

67

47

2.2

17th

30th

60

87

97

100

94

70

38

0.28

0

0

20th

30th

13

0

0

7

0.56

13

20th

23

43

47

60

10th

20th

1.1

20th

10th

33

57

63

94

0

30th

2.2

0

33

67

95

90

98

7

57

I.

0.56

0

53

50

83

93

98

78

70

Example 80

Investigation of perennial weeds

Compound No. 1 is tested against typical perennial weeds. The compound is formulated according to the procedure of Example 70. The formulated compound is applied to plastic pots of greenhouse earth, which are planted with winches, canine grass, Aleppo millet and field grass. Winch rootstocks and Aleppo millet and field hemp rhizomes come from plants growing in the field, and dog tooth grass tolos are uprooted from dog tooth grass grown in prick boxes in the greenhouse.

In the formulated state, the compound is sprayed uniformly over the pots immediately after the weeds have been planted and is lightly watered into the soil. The pots are fertilized individually a few days after the treatment.

The pots are kept in the greenhouse and the plants are examined 5 weeks after treatment with the active ingredient. Weed control is rated on a 0 to 10 scale.

Application quantity in kg / ha

Winds

Dog tooth grass

Aleppo millet

Field couch

0.28

10th

5

1

8th

0.56

10th

7

3rd

10th

1.1

10th

7

5

9

2.2

10th

8th

5

9

The same compound is also tested against the same weeds in a post-emergence trial in which the weeds are allowed to grow 30 to 60 days after planting before applying the active ingredient. Before applying the active ingredient, the plants are cut back to a height of 10.2 to 20.3 cm and the winch runners are cut back to the edge of the pot. The plants are observed 4 weeks after treatment. The following results are obtained.

Order quantity

Winds

Dog tooth

Aleppo millet

Field in kg / ha

grass

quecke

0.28

8th

8th

8th

5

0.56

8th

8th

8th

10th

1.1

8th

8th

8th

10th

2.2

8th

7

8th

10th

Example 81

Testing with perennial weeds The weeds and test conditions used for these tests are similar to those of Example 80. A number of typical compounds of the formula I are used. The weeds are observed about 4 weeks after the compounds are used.

Before the plants emerge, the following results are obtained:

connection

assignment

Winds

Dog tooth

Aleppo millet

Field

No.

quantity in kg / ha

grass

quecke

1

1.1

10th

9.8

10th

10th

0.56

10th

9.8

10th

10th

0.28

10th

8th

10th

10th

0.14

10th

8th

9.5

10th

51

1.1

10th

9.5

10th

10th

0.56

10th

9

10th

10th

0.28

10th

5

7

6

0.14

10th

4th

7

12th

1.1

10th

9.5

9.5

10th

0.56

10th

8th

9

10th

0.28

10th

8th

8th

8th

0.14

10th

6

8th

14

1.1

10th

9.5

10th

10th

0.56

10th

9

10th

10th

0.28

10th

9

7

9

0.14

10th

7

7

7

57

1.1

10th

9.5

10th

10th

0.56

10th

9

9.5

10th

0.28

10th

7

10th

9

0.14

10th

5

7

7

After emergence you get the following results:

Connection order - winch dog tooth - Aleppo millet field no. amount of grass hemp in kg / ha

1

1.1

9.5

9.5

0.56

9

9.5

8th

9

0.28

8th

9.5

0.14

3rd

9

51

1.1

9

9

0.56

9

8th

7

9

0.28

7

5

0.14

5

4th

12

1.1

9

9

0.56

9.5

9

8th

7

0.28

8th

5

0.14

7

4th

14

1.1

9

9

0.56

9.8

9

8th

9

5

10th

15

20th

25th

30th

35

40

45

50

55

«0

45

632496

44

connection

assignment

Winds

Dog tooth

Aleppo millet

No.

amount

grass

quecke

in kg / ha

0.28

8th

8 s

0.14

7

6

57

1.1

9

9

0.56

9.5

9

7

8th

0.28

5

6

0.14

4th

3 10

Connection no.

Application quantity in kg / ha

evaluation

4.5

10th

57

1.1

0

2.2

0

4.5

4th

Example 82

Investigations on the mesquite tree

Typical compounds of formula I are tested for their activity against mesquite trees that grow in the greenhouse. As soon as they are 12.7 to 30.5 cm high, the trees are transplanted into 3.8 liter metal pots. After the saplings in the pots have started to grow vigorously, the compounds are applied in the form of an earth trough. The compounds are formulated for use by dissolving them in acetone: ethanol as described in Example 70, followed by the appropriate amount of solution distributed in 25 ml water for use over each pot. The mequit trees are examined approximately 90 days after the active ingredient has been applied, the control values obtained being assessed on a scale ranging from 0 to 10.

Example 83

Investigations on a grapefruit plantation

Compound # 1 is being studied on a grapefruit plantation in a tropical climate. The soil is sandy and the trees grow in bed culture under sprinkling with a sprinkler. The trees are about 2 years old when you use the compound.

The compound is formulated according to the method described in Example 70 and applied in the form of a surface spray to a 1 square meter plot around the stick of each tree.

Tree damage is assessed approximately 14 weeks after application of the compounds on a 0 to 10 scale, with the following results:

Application quantity in kg / ha

0.14 0.21 0.28 0.4

5.56 1.1 2.2 4.5

39

Connection no.

Application quantity in kg / ha

Assessment 0.0 0.0 0.0 0.0 0.0 0.7 0.0 0.0

34 37 1

47

48

51 6

12

13

14

1.1

2.2 4.5

1.1

2.2 4.5

1.1

2.2 4.5

1.1

2.2 4.5

1.1

2.2 4.5

1.1

2.2 4.5

1.1

2.2 4.5

1.1

2.2 4.5

1.1

2.2 4.5

1.1

2.2 4.5

1.1

2.2 4.5

1.1

2.2

6

6

7.5

7

4th

8.5

Weed control is also determined approximately 14 weeks after application of the compound. This gives the following results, which are expressed as a percentage control in relation to the weed population of untreated control plots.

40

9.9 9.9 9

Application quantity in kg / ha

Bahia gras

Dog tooth grass

Purple night watch herb candle

Florida purslane

Black nightshade

9.5

9.9

45 0.14

0

0

83

100

63

97

10th

0.21

0

40

100

100

53

97

9.9

0.28

13

13

100

100

62

100

10th

0.42

80

73

98

100

100

100

0

0.56

87

88

100

100

100

100

4th

50 1.1

90

73

100

100

95

100

7

2.2

100

80

100

100

90

100

10th

4.5

98

98

100

100

100

100

9.5 9.9

2nd

7.5 4

6

7

9.9

3 9 6

10 10 10 10 10

55

Example 84

Control of purple cyber grass in cotton Compound No. I of Table A is investigated in a cotton growing in the field which is infested with purple-60 cyper grass. The cotton grows on loamy earth in flat culture without radiation in a subtropical climate. The active ingredient is used in the form of an 80 percent wetted powder dispersed in water and incorporated into the soil immediately before the cotton is planted. About 8 weeks after application of the active ingredient, the percentage damage to the crop and the percentage weed control are determined. The following results are obtained.

45

632496

Order quantity

Useful

Combat

Combat

Planting in kg / ha d. prickly of red

damage

Star burdock

Purple cyper

Ruppies

grass

0.56

0

27th

20th

33

0.84

0

60

67

80

1.1

0

68

73

90

1.7

0

90

90

100

2.2

0

99

99

100

3.4

0

99

99

100

Example 85

Try weed control over coffee

The compound of No. 1 is also applied to adult coffee trees, and these experiments are very similar to those of the immediately preceding example, but the compound is applied to the surface differently. If the compound is used in amounts of up to 2 kg per ha, the coffee is not damaged if the plants are examined about 6 weeks and about 4 months after treatment with the active ingredient. An excellent control of the annual grasses, annual broad-leaved weeds, the Paraguay burdock, the spiny star burdock, the hairy burdock, the southern pointed burdock and the purple cyper grass is obtained in this experiment.

The excellent broadband activity of the compounds of the formula I is clearly demonstrated by the above examples. The examples show the effectiveness of the compounds against annual grasses, the relatively easy to control broad-leaved weeds, such as goose foot, and the more difficult to kill broad-leaved grasses, such as the nightshade, the ambrosia or the Canadian goose. The active ingredients also control perennial weeds, such as Aleppo millet, field grass, winds, dog tooth grass and cyper grass, which are extremely difficult to control. These compounds can also be used to combat algae and aquatic weeds, coontail and hydrilla. Wood-like plants, such as mesquite shrubs, which are harmful weeds in areas with a dry climate, are also killed by the active compounds according to the invention. For the plant specialist, it is thus readily apparent that he can also use the compounds according to the invention for controlling undesirable woody plants where such plants are not desired. The plant specialist recognizes that the compounds according to the invention can be used to control all types of weeds on account of the activity indicated.

However, these active ingredients are preferably used for the selective killing of herbaceous weeds.

The compounds of formula I, which is extremely unusual, are effective herbicides in both pre-emergence and post-emergence applications. So to kill the weeds, you can either put them on the ground when the weed seeds germinate and emerge,

or they can also be used to kill weeds by direct contact with the parts of the weeds protruding from the ground. In a pre-emergence application of the active compounds according to the invention, the weeds are destroyed either during germination or shortly after emergence.

The compounds of the formula I can be effectively brought into contact with aquatic weeds by either suspending or dissolving the particular active compound in the water in which the weeds grow, or by

10th

15

20th

25th

30th

35

45

50

55

60

65

applies the active ingredient to the submerged soil in which the weeds are rooted.

Because of their outstanding effectiveness, the use of the compounds of the formula I or their salts as an active component of a herbicidal composition is an important object of the present invention. The herbicidal compositions containing the active ingredient are used in an amount suitable for selectively killing the weeds. The compositions in question also exert their desired efficacy against weed seeds when they are combined with these when the compositions are used pre-emergence.

Pre-emergence applications of the compounds are effective, as the examples show, regardless of whether the active ingredients are applied to the soil surface or incorporated into the soil.

As can also be seen from the above examples, a number of the compounds of the formula I are sufficiently safe against a number of useful plants, such as peanuts, soybeans, sorghum, wheat or useful trees, when used in suitable amounts and at appropriate times. Many of these compounds are surprisingly safe against directly sown or transplanted rice, regardless of whether it is grown on a common rice field or on the highlands. The compounds according to the invention are above all and extremely harmless to cotton, as can be seen from the above experiments. Because of the safety with which this crop can be treated with the active compounds according to the invention, the use of this method for killing weeds in bamboo plantings is a preferred embodiment of the invention.

The compounds of the formula I can also be used in suitable application amounts for the complete control of vegetation. Such control is often desirable if, for example, you want to have idle land for a certain period of time, or also on industrial sites and public roads. The ability of the compounds to control perennial weeds and woody plants makes them particularly suitable as total control agents for vegetation.

The process excels in its ability to selectively kill weeds. The indication of weeds is not to be understood in a restrictive sense, but rather refers very broadly to unwanted and unwanted plants, and thus to any harmful vegetation. For example, the method can be used on cotton plantations not only to kill plants that are undesirable per se, such as Aleppo millet or ambrosia, but also to control wild crops that one does not want to have in a cotton field. In order to achieve a selective control of weeds, the appropriate application quantities must of course be used, which is a matter of course for the plant specialist.

The proportion of the weed population which is killed by application of one of the compounds of the formula I depends on the species of the weed and the identity and amount of the compound used. In some cases, of course, the entire population is also killed. In other cases, some of the weeds are killed and some are damaged, as some of the examples above show. Of course, the use of one of the compounds is of course effective and useful even if only part of the weed population is killed and the other part of the population is only damaged. The sole damage to a weed is useful because the surrounding and normally growing crops are better

632496

46

spread and kill the slower growing damaged weeds.

The most favorable application amount for controlling a certain weed with a certain compound of formula I depends, of course, on the particular application process, the climate, the type of soil, the water content and the content of organic constituents of the soil and other factors known to the plant scientist. In any case, the optimal application rate is in the range from about 0.025 to about 20 kg / ha. The optimal application rates are usually within the preferred range of about 0.025 to about 5 kg / ha.

The time at which the compounds are to be applied to the soil or the weeds is highly variable, since the compounds according to the invention are suitable for both pre-emergence and post-emergence treatment. At least some weed control results from using the active ingredients at all times when the weeds grow or germinate. The active ingredients can also be applied to the soil during the winter time to kill weeds that germinate during the following warmer time.

If the active ingredients are used to control weeds in annual crops, then the best way to apply the active ingredient is normally before they hit the ground at the time of planting the crop. If the active ingredient is to be worked into the soil, it is normally applied and worked in immediately before sowing. For surface applications, it is usually easiest to apply the active ingredient immediately after sowing.

The active ingredients are applied to the soil or to weeds that have sprung up in the manner customary in agrochemistry. They can be applied to the floor either in the form of water-dispersed formulations or in the form of granules, and the preparation of such formulations is discussed below. Formulations dispersed in water are normally used to apply the compounds to emerged weeds. The formulations can be applied with any known spray and granule applicator which are widely used to distribute agrochemicals over the soil or over standing vegetation. If a connection is to be worked into the soil, this can be done with any conventional tillage device, such as disc harrows or driven rotary hoes.

The compounds are normally used in the form of the herbicidal preparations which are an important embodiment of the invention. A herbicidal preparation according to the invention consists of a compound of the formula I and an inert carrier. The preparations are generally formulated in the manner customary in agrochemistry and are only new because of the presence of the new herbicidal compounds.

Very often the compounds are also formulated in the form of concentrated preparations which are applied either to the soil or to the foliage in the form of aqueous dispersions or emulsions which contain about 0.1 to about 5% of active ingredient. Water-dispersible or emulsifiable preparations are either solids known as wettable powders or liquids which are normally known as emulsifiable concentrates. These concentrated preparations are used in the following composition:

Percent by weight

Compound of formula I.

10-80

.Surfactant

3-10

Inert carrier

87-10

Wettable powders consist of an intimate, finely divided mixture of the active ingredient, an inert carrier and surface-active agents. The drug concentration is usually between about 10 and about 90%. Attapulgite clays, kaolin clays, montmorrilonite clays, diatomaceous earths and purified silicates are usually used as inert carriers. Suitable surfactants which make up about 0.5 to about 10% of the wettable powder are, for example, the sulfonated lignins, the condensed naphthalenesulfonates, the naphthalenesulfonates, the alkylbenzenesulfonates, the alkyl sulfates and nonionic surfactants, such as ethylene oxide adducts of phenol.

Typical emulsifiable concentrates of the compounds of formula I contain a suitable concentration of active ingredient, for example about 100 to about 500 g of active ingredient per liter of liquid, dissolved in an inert carrier, such as a mixture of a water-immiscible solvent and emulsifier. Suitable organic solvents are, for example, aromatic compounds, in particular the xylenes, and the petroleum fractions, in particular the high-boiling naphthalene and olefinic fractions of the petroleum. Some other organic solvents, such as the thermal solvent, or the complex alcohols, such as 2-ethoxyethanol, can also be used. Suitable emulsifiers for the preparation of 35 emulsifiable concentrates are selected from the same surface-active agents as are used for the preparation of wettable powders.

If a compound is to be applied to the floor, for example for an application of the compound before emergence, then the use of a granular formulation is recommended. Such a formulation typically contains the active ingredient dispersed on a granular inert carrier, such as coarsely ground clay. The particle size of the granules is normally between about 45 0.1 and about 3 mm. The usual formulation process for granules consists in dissolving the compound in a cheap solvent and applying the solution to the carrier in a suitable solid mixer. Granular preparations usually have the following composition:

Percent by weight

Compound of formula I.

1-10

Surface active agent

0-2

Inert carrier

99-88

60

In a somewhat less economical manner, the compound can also be dispersed in a dough-like mass, which is composed of a moist clay or other inert carrier, and from which the desired granular product is obtained after drying and rough-grinding.

B

Claims (65)

632496 PATENT CLAIMS 1. Process for the preparation of 3-phenyl-5-substituted-4 (1 H) -pyridones of the formula Ia R in which X is oxygen, R for hydrogen is Ci-C3-alkyl, by halogen, cyano, carboxy or Methoxycarbonyl substituted Ci-C3-alkyl, C2-C3-alkenyl, C2-C3-alkynyl, Ci-C3-alkoxy, hydroxy or dimethylamino, with the proviso that the substituent R contains no more than 3 carbon atoms, the radicals R1 independently from each other halogen, Ci-Cs-alkyl, halogen-substituted Ci-Cs-alkyl, Ci-Cs-alkyl monosubstituted with phenyl, cyano or Ci-C3-alkoxy, C2-C8-alkenyl, halogen-substituted C2-Cs-alkenyl, C2-C8- Alkynyl, halogen-substituted C2-Cs-alkynyl, C3-C6-cycloalkyl, C4-C6-cycloalkenyl, C4-Cs-cycloalkylalkyl, Ci-C3-alkanoyloxy, Ci-C3-alkylsulfonyloxy, phenyl, by halogen, Ci-C3- Alkyl, Ci-C3-alkoxy or nitro are monosubstituted phenyl, nitro, cyano, carboxy, hydroxy, C1-C3-alkoxycarbonyl, -O-R3, -S-R3, -SO-R3 or -SO2-R3, where R3 is Ci-Ci2-alkyl, h alogen-substituted Ci-Ci2-alkyl, substituted by phenyl, cyano or Ci-C3-alkoxy Ci-Ci2-alkyl, phenyl, by halogen, Ci-C3-alkyl, C1-C3-alkoxy or nitro monosubstituted phenyl, C3-C6-cyclo -alkyl, C4-C8-cycloalkylalkyl, C2-Ci2-alkenyl, halogen-substituted C2-Ci2-alkenyl, C2-Ci2-alkynyl or halogen-substituted C2-Ci2-alkynyl, with the proviso that the substituent R3 contains at most 12 carbon atoms, R3 for halogen, hydrogen, cyano, Ci-C3-alkoxycarbonyl, Ci-Ce-alkyl, Ci-Co-alkyl substituted by halogen or Ci-C3-alkoxy, C2-C6-alkenyl, C2 substituted by halogen or Ci-C3-alkoxy -Có-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl, C3-C6-cycloalkyl substituted by halogen, Ci-C3-alkyl or C1-C3-alkoxy, C4-C6-cycloalkenyl, C4-Cs- Cycloalkylalkyl, phenyl-Ci-C3-alkyl, furyl, naphthyl, thienyl, -O-R4, -S-R4, -SO-R4, -SO2-R4 or halogen, Ci-C3-alkyl, Ci-C3-alkoxy or Nitro monosubstituted phenyl, nitro, cyano, carboxy, hydroxy, C1-C3 alkoxycarbo nyl, -O-R6, -S-R6, -SO-R6 or -SO2-R6, where 5 R6 for Ci-Ci2-alkyl, halogen-substituted Ci-Ci2-alkyl, by phenyl, cyano or Ci-C3-alkoxy monosubstituted Ci-Ci2-alkyl, phenyl, by halogen, Ci-C3-alkyl, C1-C3-alkoxy or nitro monosubstituted phenyl, C3-C6-cyclo-alkyl, C4-C8-cycloalkylalkyl, C2-Ci2-alkenyl, halosub- 1 »substituted C2-Ci2-alkenyl, C2-Ci2-alkynyl or halogen-substituted C2-Ci2-alkynyl, with the proviso that the substituent R6 contains at most 12 carbon atoms, the indices m and n independently of one another denote 0.1 or 2, where the index m is 1 or 2 if R is is hydrogen or methyl and R2 is unsubstituted phenyl, and the salts of the compounds of the formula Ia, characterized in that a compound of the formula IV 1-Methyl-3-phenyl-5- (3-trifluoromethylphenyl) -4 (1 H) -pyrididinion 1-Methyl-3-phenyl-5- [3- (l, 1,2,2-tretrafluoroethoxy) phenyl] -45 4 (1H) pyridone, 3- (3-acetoxyphenyl) -l-methyl-5-phenyl -4 (1H) -pyridone, 3- (3-hexyloxyphenyl) -1-methyl-5-phenyl-4 (1 H) -pyridone, 3- (3-decyloxyphenyl) -l-methyl-5-phenyl-4 ( 1H) -pyridone, 1-methyl-3-phenyl-5- (3-propoxyphenyl) -4 (1H) -pyridone, so 1-methyl-3-phenyl-5- (3-propargyloxyphenyl) -4 (1H) -pyridone, 1-methyl-3-propyl-5- (3-trifluoromethylphenyl) -4 (1H) -pyridone, io 1-Methyl-3- (4-nitrophenyl) -5-phenyl-4 (1 H) -pyridone, 3,5-bis (3,4-dimethoxyphenyl) -l-methyl-4 (1H) -pyridone, 3 -Ethoxycarbonyl-1-methyl-5-phenyl-4 (1H) -pyridone, 3- (2-furyl) -l-methyl-5-phenyl-4 (1H) -pyridone, 3-cyano-1-methyl-5 - (3-trifluoromethylphenyl) -4 (1H) -îs pyridone, 1-methyl-3-phenyl-4 (1 H) -pyridone, 1-methoxy-3-phenyl-5- (3-trifluoromethylphenyl) -4 (1 H) -pyridone, 1-dimethylamino-3,5-diphenyl-4 (1 H) -pyridone, 1-methyl-3- (2-naphthyl) -5-phenyl-4 (1 H) -pyridone, 1-ethyl-3-phenyl- 5- (3-trifluoromethylphenyl) -4 (1 H) -pyridone, 3-phenyl-1-propyl-5- (3-trifluoromethylphenyl) -4 (1H) -pyridone, 1 - (1-carboxyethyl) -3-phenyl-5- (3-trifluoromethylphenyl) -4 (1H) -pyridone, 1-methyl-3- (3-methylthiophenyl) -5-phenyl-4 (1 H) -pyridone, 1-methyl-3- (3-methylsulfinylphenyl) -5-phenyl-4 (1 H) -65 pyridone, l-methyl-3- (3-methylsulfonylphenyl) -5-phenyl-4 (1H) -pyridone, l-methyl-3-phenyl-5- (4-trifluoromethylphenyl) -4 (lH) - pyridone, 1-methyl-3-phenyl-5- (3-trifluoromethylphenyl) -4 (1 H) -pyridone, l-methyl-3,5-bis (3-trifluoromethylphenyl) -4 (1H) -pyridone, 3-phenyl-l- (2,2,2-trifluoroethyl) -5- (3-trifluoromethylphenyl) -40 4 (1H ) -pyridone, "1, Stki .. IA 0 in which SI 1-methyl-3-phenyl-5- (4-trifluoromethyIphenyI) -4 (1H) -pyridone, characterized in that 1,5-dihydroxy- 1-methyl-3-phenyl-5- (3-trifluoromethylphenyl) -4 (1H) -pyridone, characterized in that 1,5-dihydroxy- 1- (l-carboxyethyl) -3-phenyl-5- (3-trifluoromethylphenyl) -4 (lH) -pyridone, characterized in that 1,5-dihydroxy-2-phenyl-4- (3-trifluoromethylphenyl ) -1,4-pentadiene- 1,5-dihydroxy-4-phenyl-1,4-pentadien-3-one cyclized with methylamine. 1-methyl-3- (l-naphthyl) -5-phenyl-4 (lH) -pyridone, characterized in that l, 5-dihydroxy-2- (l-naphthyl) -4-phenyl-l, 4- Pentadien-3-one cyclized with methylamine. 2-phenyl-4- (4-trifluoromethylphenyl) -l, 4-pentadien-3-one cyclized with methylamine. 2-phenyl-4- (3-trifluoromethylphenyl) -1,4-pentadien-3-one cyclized with methylamine. 2-phenyl-4- (3-trifluoromethylphenyl) -1,4-pentadien-3-one cyclized with methoxyamine. 2-phenyl-4- (3-trifluoromethylphenyl) -1,4-pentadien-3-one cyclized with propylamine. 2-phenyl-4- (3-trifluoromethylphenyl) -1,4-pentadien-3-one cyclized with methylamine. 2. The method according to claim 1, characterized in 3- (3-cyclohexylmethoxyphenyl) -l-methyl-5-phenyl-4 (1H) -pyridone, l-methyl-3- (3-octyloxyphenyl) -5-phenyl-4 (1H) -pyridone, 55 1 -methyl-3- (3-phenoxyphenyl) -5-phenyl-4 (1H) -pyridone, 1 - Acetoxy-3,5-diphenyl-4 (1 H) -pyridone, 1-methyl-3,5-diphenyl-4 (1 H) -pyridone hydroiodide, 1-methyl-3,5-diphenyl-4 (1H) -pyridone hydrochloride, 3,5-diphenyl-l-methyl-4 (lH) -pyridinthione, 60 3,5-bis (3-chlorophenyl) -l-methyl-4 (lH) -pyridinthione, 3- (3- Chlorphenyl) -l-methyl-5-phenyl-4 (1 H) -pyridinthione, or 3- (3-dodecyloxyphenyl) -l-methyl-5-phenyl-4 (lH) -pyridone, 40 l-methyl-3- [3- (4-nitrophenoxy) phenyI] -5-phenyl-4 (lH) - pyridone, l-methyl-3- (3-methylsulfonyloxyphenyl) -5-phenyl-4 (1H) -pyridone, 3- (3-isopropoxyphenyl) -1-methyl-5-phenyl-4 (1 H) -pyridone, 3- (3-cyanomethoxyphenyl) -1-methyl-5-phenyl-4 (1H) -pyridone, 3- (3,4-Dimethoxyphenyl) -l-methyl-5-phenyl-4 (1H) -pyridone, 3- (3,4-dibromocyclohexyl) -l-methyl-5- (3-trifluoromethyl-phenyl) -4 (1 H) -pyridone hydrobromide, 3- (3-isopropenylphenyl) -l -methyl-5-phenyl-4 (1H) -pyridone, 2o 3- (3-ethylphenyl) -1 -methyl-5-phenyl- 4 (1 H) -pyridone, 3- (3-hexylphenyl) -l-methyl-5-phenyl-4 (1H) -pyridone, 3- (4-ethylphenyl) -1-methyl-5-phenyl-4 (1 H) -pyridone, 3- (3-cyclohexylmethylphenyl) -l -methyl-5-phenyl-4 (1 H) -pyridone, 3-benzyl-l-methyl-5- (3-trifluoromethylphenyl) -4 (lH) - pyridone, s 3-butyl-1-methyl-5- (3-trifluoromethylphenyl) -4 (1 H) -pyridone, 3- (3-cyclohexenyl) -l-methyl-5- (3-trifluoromethylphenyl) -4 (1 H) -pyridone, 3-hexyl-1-methyl-5- (3-trifluoromethylphenyl) -4 (1 H) -pyridone, 3-isopropyl-1-methyl-5- (3-trifluoromethylphenyl) -4 (1H) - 3-ethyl-1-methyl-5- (3-trifluoromethylphenyl) -4 (1 H) -pyridone, 3-cyclohexyl-l-methyl-5- (3-trifluoromethylphenyl) -4 (1H) -pyridone, 3- (3-chlorophenyl) -1,5-dimethyl-4 (1 H) -pyridone, 3-cyano-1-methyl-5-phenyl-4 (1 H) -pyridone, 1,3-dimethyl-5- (3-trifhiormethylphenyl) -4 (1H) -pyridone, 1,3-dimethyl-5-phenyl -4 (1 H) pyridone, 3,5-bis (3-cyanophenyl) -1-methyl-4 (1 H) -pyridone, 1-methyl-3-phenyl-5- (3-thienyl) -4 (1 H) -pyridone, 3- (3-ethoxycarbonylphenyl) -1-methyl-5-phenyl-4 (1H) - pyridone, 3- (3-cy anopheny 1) -1-methyl-5-phenyl-4 (1 H) -pyridone, 3- (3-carboxyphenyl) -1-methyl-5-phenyl-4 (1 H) -pyridone, 3-chloro-l-methyl-5- (3-trifluoromethylphenyl) -4 (1H) -pyridone, 3-bromo-1-methyl-5- (3-trifluoromethylphenyl) -4 (1 H) -pyridone, l-methyl-3- (3-trifluoromethylphenyl) -4 (1H) -pyridone, 3-bromo-1-methyl-5-phenyî-4 (1 H) -pyridone, 3- (3-biphenylyl) -1-methyl-5-phenyl-4 (1 H) -pyridone, 3- (4-biphenylyl) -l-methyl-5-phenyl-4 (1H) -pyridone, 3- (3-chlorophenyl) -1-methyl-5- (3-trifluoromethylphenyl) -4 (1H) -pyridone, 3- (3,5-dichlorophenyl) -1-methyl-5-phenyl-4 (1 H) -pyridone, 3,5-bis (3-bromophenyl) -1-methyl-4 (1 H) -pyridone, 3 - (3-bromophenyl) -1-methyl-5-phenyl-4 (1 H) -pyridone, 3- (2-fluorophenyl) -1-methyl-5-phenyl-4 (1 H) -pyridone, 3- ( 3-bromophenyl) -1-methyl-5- (3-trifluoromethylphenyl-4 (1H) -pyridone, 3,5-diphenyl-1-methoxy-4 (1 H) -pyridone, 3- (3-fluorophenyl) -l-methyl-5-phenyl-4 (1H) -pyridone, 3- (4-bromophenyl) -1 -methyl-5-phenyl-4 (1 H) -pyridone, 3- (4-methoxyphenyl) -l-methyl-5-phenyl-4 (1H) -pyridone, 3- (3-chlorophenyl) -l-methyl- 5-phenyl-4- (1H) -pyridone, 3- (4-chlorophenyl) - 1-methyl-5-phenyl-4 (1H) -pyridone, 1-methyl-3- (1-naphthyl) -5- phenyl-4 (1 H) -pyridone, 3,5-bis (3-chlorophenyl) -l-methyl-4 (1H) -pyridone, 1-methyl-3- (3-methylphenyl) -5-phenyl-4 ( 1 H) -pyridone, l-methyl-3- (4-methylphenyl) -5-phenyl-4 (1H) -pyridone, 1-methyl-3- (2-methylphenyl) -5-phenyl-4 (1 H) -pyridone, 3- (4-fluorophenyl) -1-methyl-5-phenyl-4 (1H) -pyridone, 3- (3-methoxyphenyl) -1-methyl-5-phenyl-4 (1H) -pyridone, 3- (3,4-dichlorophenyl) -l-methyl-5-phenyl-4 (1 H) -pyridone, 3- (2,5-dichlorophenyl) -l-methyl-5-phenyl-4 (1H) -pyridone , 3- (2-chlorophenyl) -1-methyl-5-phenyl-4 (1 H) -pyridone, 3,5-bis (3-fluorophenyl) -1-methyl-4 (1 H) -pyridone, 3- (3-chlorophenyl) -5- (3-fluorophenyl) -l-methyl-4 (1 H) -pyridone, 3,5-diphenyl-1-propyl-4 (1 H) -pyridone, 3- (3-benzyloxyphenyl) -1-methyl-5-phenyl-4 (1 H) -pyridone, 1-methyl-3-phenyl-5- (2-thienyl) -4 (1 H) -pyridone, 3- (3-isobutylphenyl) -1-methyl-5-phenyl-4 (1 H) -pyridone, 1-methyl-3- (3-nitrophenyl) -5-phenyl-4 (1 H) -pyridone, 3- (2nd , 4-dichlorophenyl) -1-methyl-5-phenyl-4 (1 H) -pyridone, 3,5-diphenyl-1-ethyl-4 (1 H) -pyridone, 1-allyl-3,5-diphenyl- 4 (1 H) -pyridone, 3,5-diphenyl-1-isopropyl-4 (1H) -pyridone, 1-cyanomethyl I-3,5-diphenyl-4 (1 H) -pyridone, 3- (4-methoxyphenyl) -l-methyl-5- (3-trifluoromethylphenyl) -4 (1H) -pyridone, 3- (4-fluorophenyl) -1-methyl-5- (3-trifluoromethylphenyl) -60 4 (1H) -pyridone, 3- (3-fluorophenyl) -l-methyl-5- (3-trifluoromethylphenyl) -4 (1H) -pyridone, 3- (3-methoxyphenyl) -l-methyl-5- (3-trifluoromethylphenyl) -50 4 (1H) -pyridone, 3- (4-chlorophenyl) -l-methyl-5- (3-trifluoromethylphenyl) -4 ( lH) -pyridone, l-allyl-3-phenyl-5- (3-trifluoromethylphenyl) -4 (1H) -pyridone, 3- (4-isopropylphenyl) -1-methyl-5-phenyl-4 (1H) -pyridone, 55 3- (2-chlorophenyl) -l-methyl-5- (3-trifluoromethylphenyl) -4 (1H) -pyridone, 3- (2-chlorophenyl) -5- (3-chlorophenyl) -l-methyl-4 (1H) -pyridone, 3- (3-chlorophenyl) -5- (4-chlorophenyl) -1-methyl-4 (1 H) -pyridone, 3- (3-bromophenyl) -5- (3-chlorophenyl) -l-methyl-4 (1H) -pyridone, 3,5-Diphenyl-1-ethyl-4 (1H) -pyridone ethylated. 3- (3-Benzyloxyphenyl) -l-methyl-5-phenyl-4 (1H) -pyridone, characterized in that 2- (3-benzyloxyphenyl) -l, 5-dihydroxy-4-phenyl-l, 4- Pentadien-3-one cyclized with methylamine. 3- (4-chlorophenyl) -1-methyl-5- (3-trifluoromethylphenyl) -4 (1H) -pyridone, characterized in that 2- (4-chlorophenyl) -1,5-dihydroxy-4- (3rd -trifluoromethylphenyl) -1,4-pentadien-3-one cyclized with methylamine. 3-phenyl-1 - (2,2,2-trifluoroethyl) -5- (3-trifluoromethylphenyl) -4 (1H) pyridone, characterized in that 1,5-dihydroxy-2-phenyl-4- (3-trifluoromethylphenyl) -l, 4-pentadien-3-one cyclized with 2,2,2-trifluoroethylamm. 3rd 3- (3-chlorophenyl) -1-methyl-5- (3-trifluoromethylphenyl) -4 (1H) -pyridone, characterized in that 2- (3-chlorophenyl) -1,5-dihydroxy-4- (3rd -trifluoromethylphenyl) -1,4-pentadien-3-one cyclized with methylamine. 3-one cyclized with 2-aminopropionic acid. 3- (3-bromophenyl) -l-methyl-5-phenyl-4 (1H) pyridone, characterized in that 2- (3-bromophenyl) -l, 5-dihydroxy- 3- (3-methoxyphenyl) -1-methyl-5-phenyl-4 (1 H) -pyridone, characterized in that 1,5-dihydroxy-2- (3-methoxyphenyl) -4-phenyl-l , 4-pentadien-3-one cyclized with methylamine. 3- (3-chlorophenyl) -1-methyl-5-phenyl-4 (1 H) -pyridone, characterized in that 2- (3-chlorophenyl) -l, 5-dihydroxy-4-phenyl-1,4 -pentadien-3-one cyclized with methylamine. 4th 4- (3-trifluoromethylphenyl) -l, 4-pentadien-3-one cyclized with allylamine. 4 (1 H) -pyridone, characterized in that 1,5-dihydroxy-2- (2-fluorophenyl) -4- (3-trifluoromethylphenyl) -1,4-penadien-3-one with methylamine cyclized. 4- (3-trifluoromethylphenyl) -1,4-pentadien-3-one cyclized with ethyl amine. 4-phenyl-l, 4-pentadien-3-one cyclized with methylamine. 4. The method according to claim 1 for the preparation of so 3,5-diphenyl-l-methoxy-4 (lH) -pyridone, characterized in that l, 5-dihydroxy-2,4-diphenyl-l, 4-penta- dien-3-one cyclized with methoxyamine. 5 rows A \ / 0 II m where II Q1 IV R1, R2 and m have the meanings given above, and 10 in which Q1 and Q2 stand for = CHOH, with a compound of the formula RNH2, 5 «5 632496 5 5. The method according to claim 1 for the preparation of 3- (3-fluorophenyl) -l-methyl-5-phenyl-4 (lH) -pyridone, 6. The method according to claim 1 for the preparation of 3- (4-bromophenyl) -l-methyl-5-phenyl-4 (lH) -pyridone, 7 632496 pyridone, 7 M • « ■ / V "\ -X 7. The method according to claim 1 for the preparation of 3- (4-methoxyphenyl) -l-methyl-5-phenyl-4 (lH) -pyridone, 65 characterized in that l, 5-dihydroxy-2- (4-methoxyphenyl) -4-phenyl-l, 4-pentadien-3-one cyclized with methylamine. 8. The method according to claim 1 for the production of 9. The method according to claim 1 for the preparation of 3- (4-chlorophenyl) -1-methyl-5-phenyl-4 (l H) pyridone, characterized in that 2- (4-chlorophenyl) -1, 5- dihydroxy-4-phenyl-l, 4-pentadien-3-one cyclized with methylamine. 10th IS FT XI R used where X represents an oxygen atom or a sulfur atom, R ° represents Ci-C3-alkyl, C2-C3-alkenyl or methoxy, q and p are identical or different and denote 0.1 or 2 20, the radicals R7 are identical or different and represent halogen, Ci-C3-alkyl, trifluoromethyl or Ci-C3-alkoxy, the radicals R8 are identical or different and are halogen, Ci-C3-alkyl, trifluoromethyl or Ci-C3-alkoxy or 2s two R8 radicals in the o- and m-positions are adjacent to one another and together with the phenyl ring to which they are attached form a 1-naphthyl group. 68. Use according to claim 66, characterized in that in the active ingredient component 10th Î5 10th 10. The method according to claim 1 for the production of 11. The method according to claim 1 for the preparation of 3,5-bis (3-chlorophenyl) -l-methyl-4 (1 H) -pyridone, characterized in that 2,4-bis (3-chlorophenyl) -l, 5-dihydroxy-l, 4-pentadien-3-one cyclized with methylamine. 12. The method according to claim 1 for the preparation of 1-methyl-3- (3-methylphenyl) -5-phenyl-4 (l H) pyridone, characterized in that l, 5-dihydroxy-2- (3-me -thylphenyl) -4-phenyl-l, 4-pentadien-3-one cyclized with methylamine. 13. The method according to claim 1 for the preparation of 1-methyl-3- (4-methylphenyl) -5-phenyl-4 (1 H) -pyridone, characterized in that l, 5-dihydroxy-2- (4-methylphenyl ) -4-phenyl-l, 4-pentadien-3-one cyclized with methylamine. 14. The method according to claim 1 for the preparation of 1-methyl-3- (2-methylphenyl) -5-phenyl-4 (1 H) -pyridone, characterized in that l, 5-dihydroxy-2- (2-me -thylphenyl) -4-phenyl-l, 4-pentadien-3-one cyclized with methylamine. 15 where R has the meaning given in formula Ib, or the acid addition salt of this compound is a 3-phenyl-5-substituted 4 (1H-pyridone) of the formula Ia, R4 represents Ci-C3-alkyl, halogen-substituted Ci-C3-alkyl, C2-C3-alkenyl, halogen-substituted C2-C3-alkenyl, benzyl, phenyl or phenyl substituted by halogen, Ci-C3-alkyl or Ci-C3-alkoxy, the radicals R5 independently of one another halogen, Ci-Cs-alkyl, halogen-substituted Ci-Cs-alkyl, Ci-Cs-alkyl monosubstituted by phenyl, cyano or Ci-C3-alkoxy, C2-C8-alkenyl, halogen-substituted C2-Cs-alkenyl, C2-C8-alkynyl, halogen-substituted C2-Cs-alkynyl, C3-C6-cycloalkyl, C4-C6-cycloalkenyl, C4-Cs-cycloalkylalkyl, C1-C3-alkanoyloxy, Ci-C3-alkylsulfonyloxy, phenyl, by halogen, Ci-Cî-alkyl, Ci-C3-alkoxy or nitro monosubstituted phenyl, nitro, cyano, carboxy, hydroxy, C1-C3-alkoxycarbonyl, -O-R6, -S-R6, -SO-R6 or -SO2-R6 mean , in which R6 for Ci-Ci2-alkyl, halogen-substituted Ci-Ci2-alkyl, Ci-Cu-alkyl monosubstituted by phenyl, cyano or Ci-C3-alkoxy, phenyl, by halogen, Ci-C3-alkyl, C1-C3-alkoxy or nitro monosubstituted phenyl, C3-C6-cycloalkyl, C4-C8-cycloalkylalkyl, C2-Ci2-alkenyl, halogen-substituted C2-Ci2-alkenyl, C2-Ci2-alkynyl or halogen-substituted C2-Ci2-alkynyl, with the proviso that the Substituent R6 contains at most 12 carbon atoms, the indices m and n independently of one another denote 0.1 or 2, and salts of the compounds of formula Ib, characterized in that a compound of formula IV (Ia) 15 15. The method according to claim 1 for the preparation of 3- (4-fluorophenyl) -1-methyl-5-phenyl-4 (1 H) -pyridone, characterized in that l, 5-dihydroxy-2- (4-fluorophenyl ) -4-phenyl-l, 4-pentadien-3-one cyclized with methylamine. 16. The method according to claim 1 for the preparation of 1-methyl-3-phenyl-5- (3-trifluoromethylphenyl) -4 (1H) -pyridone, characterized in that 1,5-dihydroxy- 17. The method according to claim 1 for the production of 18. The method according to claim 1 for the preparation of 3- (3,4-dichlorophenyl) -l-methyl-5-phenyl-4 (lH) pyridone, characterized in that 2- (3,4-dichlorophenyl) -l, 5-dihydroxy-4-phenyl-l, 4-pentadien-3-one cyclized with methylamine. 19. The method according to claim 1 for the preparation of 3- (2,5-dichlorophenyl) -1-methyl-5-phenyl-4 (1 H) -pyridone, characterized in that 2- (2,5-dichlorophenyl) - 1,5-dihydroxy-4-phenyl-1,4-pentadien-3-one cyclized with methylamine. 20th 20th 20. The method according to claim 1 for the preparation of 3- (2-chlorophenyl) -1-methyl-5-phenyl-4 (1 H) -pyridone, characterized in that 2- (2-chlorophenyl) -l, 5- dihydroxy-4-phenyl-l, 4-pentadien-3-one cyclized with methylamine. 20th 21. The method according to claim 1 for the preparation of 3,5-bis (3-fluorophenyl) -l-methyl-4 (lH) -pyridone, characterized in that l, 5-dihydroxy-2,4-bis (3- fluorophenyl) -l, 4-pentadien-3-one cyclized with methylamine. 22. The method according to claim 1 for the preparation of 3- (3-chlorophenyl) -5- (3-fluorophenyl) -1-methyl-4 (1 H) - 632496 pyridone, characterized in that 2- (3-chlorophenyl) -1,5-dihydroxy-4- (3-fluorophenyl) -1,4-pentadien-3-one is cyclized with methylamine. 23. The method according to claim 1 for the preparation of 3- (3,5-dichlorophenyl) -1-methyl-5-phenyl-4 (1 H) -pyridone, characterized in that 2- (3,5-dichlorophenyl) - 24. The method according to claim 1 for the preparation of 3,5-bis (3-bromophenyl) -1-methyl-4 (1 H) -pyridone, characterized in that 2,4-bis (3-bromophenyl) -l, 5-dihy-droxy-l, 4-pentadien-3-one cyclized with methylamine. 25 1-methyl-3-phenyl-5-benzylthio-4 (1 H) -pyridone, 1-methyl-3-phenyl-5-phenylthio-4 (1 H) -pyridone, 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 (1 H) -pyridone , 30 3- (3-Hydroxyphenyl) -l-methyl-5-phenyl-4 (1H) -pyridone, 3-cyclohexyl-5- (3-hydroxyphenyl) -1-methyl-4 (1H) -pyridone, 3rd - (3-ethoxyphenyl) -l-methyl-5-phenyl-4 (1H) -pyridone, 3- (3-allyloxyphenyl) -l-methyl-5-phenyl-4 (1H) -pyridone, 3- [3- (l-fluoro-2-iodovinyloxy) phenyl] -l-methyl-5-phenyl-35 4 (1H) -pyridone, 25th 25th 25. The method according to claim 1 for the production of 25th A > m 0 left -C — C — C —- FT II II "1 -s IV < V stands for R4 for Ci-C3-alkyl, halogen-substituted Ci-C3-alkyl, C2-C3-alkenyl, halogen-substituted C2-C3-alkenyl, benzyl, Phenyl or phenyl substituted by halogen, Ci-C3-alkyl or Ci-C3-alkoxy, the radicals R5 independently of one another halogen, Ci-Cs-alkyl, halogen-substituted Ci-Cs-alkyl, Ci-Cs-alkyl monosubstituted by phenyl, cyano or Ci-C3-alkoxy, C2-C8-alkenyl, halogen-substituted C2-Cs-alkenyl, C2-C8-alkynyl, halogen-substituted C2-Cs-alkynyl, C3-Có-cycloalkyl, C4-C6-cycloalkenyl, C4-Cs-cycloalkylalkyl, C1-C3-alkanoyloxy, Ci-C3-alkylsulfonyloxy, phenyl, through which R ', R2 and m have the meanings given above, and in which Q1 and Q2 are = CHOH, with a compound of the formula 26. The method according to claim 1 for the preparation of 3- (2-fluorophenyl) -l-methyl-5-phenyl-4 (lH) -pyridone, characterized in that l, 5-dihydroxy-2- (2-fluorophenyl) -4-phenyl-l, 4-pentadien-3-one cyclized with methylamine. 27. The method according to claim 1 for the preparation of 3- (3-bromophenyl) -1-methyl-5- (3-trifluoromethylphenyl) -4 (lH) -pyridone, characterized in that 2- (3-bromophenyl) -1 , 5-dihydroxy-4- (3-trifluoromethylphenyl) -1,4-pentadien-3-one cyclized with methylamine. 28. The method according to claim 1 for the production of 29. The method according to claim 1 for the preparation of 1-dimethylamino-3,5-diphenyl-4 (1 H) -pyridone, characterized in that 1,5-dihydroxy-2,4-diphenyl-1,4-pentadiene- 3-one cyclized with 1,1-dimethylhydrazine. 30 Formula I X is an oxygen atom and the radical R1 is in the m position and preferably has the meaning of a trifluoromethyl radical. 69. Use according to claim 66, characterized in that the compound of formula I 30th reacted and treated with phosphorus pentasulfide, forming the compound of formula Ib, which is isolated in free form or in the form of its salts. 30th 30th 30. The method according to claim 1 for the preparation of 1-methyl-3- (2-naphthyl) -5-phenyl-4 (1 H) -pyridone, characterized in that l, 5-dihydroxy-2- (2-naphthyl ) -4-phenyl-l, 4-pentadien-3-one cyclized with methylamine. 30 RNH2, wherein R has the meaning given above, or the acid addition salt of this compound, cyclized. 31. The method according to claim 1 for the preparation of 1-ethyl-3-phenyl-5- (3-trifluoromethylphenyl) -4 (1 H) -pyridone, characterized in that l, 5-dihydroxy-2-phenyl- 32. The method according to claim 1 for the preparation of 3-phenyl-l-propyl-5- (3-trifluoromethylphenyl) -4 (lH) -pyridone, characterized in that 1,5-dihydroxy- 33. The method according to claim 1 for the preparation of 1-methoxy-3-phenyl-5- (3-trifluoromethylphenyl) -4 (1H) -pyridone, characterized in that 1,5-dihydroxy- 34. The method according to claim 1 for the production of 35 35 35 35. The method according to claim 1 for the preparation of 3- (4-biphenylyl) -1-methyl-5-phenyl-4 (1 H) -pyridone, characterized in that 2- (4-biphenylyl) -l, 5- dihydroxy-4-phenyl-l, 4-pentadien-3-one cyclized with methylamine. 35 shows that compounds of the formula Ia are prepared in which R is an alkyl radical with 1-3 carbon atoms optionally substituted by halogen, cyano, carboxy or methylcarbonyl, an alkenyl or alkynyl radical with 2 or 3 carbon atoms by cyclization With 36. The method according to claim 1 for the preparation of 3- (3-biphenylyl) -1-methyl-5-phenyl-4 (1 H) -pyridone, characterized in that 2- (3-biphenylyl) -l, 5- dihydroxy-4-phenyl-l, 4-pentadien-3-one cyclized with methylamine. 37. The method according to claim 1 for the production of 38. The method according to claim 1 for the preparation of 1-methyl-3,5-bis (3-trifluoromethylphenyl) -4 (1 H) -pyridone, characterized in that 1,5-dihydroxy-2,4-bis (3rd -trifluoromethylphenyl) -l, 4-pentadien-3 one cyclized with methylamine. 39. The method according to claim 1 for the production of 40 65. The method according to claim 63, characterized in that the 2- (3-chlorophenyl) -l, 5-dihydroxy-4-phenyl-l, 4-pentadien-3-one with methylamine to the 3- (3- Chlorophenyl) -1-methyl-5-phenyl-4 (1 H) -pyridone cyclizes and this is converted with phosphorus pentasulfide to the 3 (3-chloro-45 phenyl) -l-methyl-5-phenyl-4 (1H) -pyridine thione . 66. Use of the new 3-phenyl-5-substituted 4 (1 H) -pyridones or 3-phenyl-5-substituted 4 (1H) -pyridothiones of the formula I. I # in which X is an oxygen atom or a sulfur atom, R represents hydrogen, Ci-C3-alkyl, Ci-C3-alkyl substituted by halogen, cyano, carboxy or methoxycarbonyl, 65 C2-C3-alkenyl, C2-C3-alkynyl, Ci-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, Ci-Cs-alkyl, 632496 halogen-substituted Ci-Cs-alkyl, Ci-Cs-alkyl monosubstituted with phenyl, cyano or Ci-C3-alkoxy, Cî-Cs-alkenyl, halogen-substituted C2-Cs-alkenyl, C2-C8-alkynyl, halogen-substituted C2-Cs-alkynyl, C3-Câ-cyclo-alkyl, C4-C6-cycloalkenyl, Ci-Cs-cycloalkylalkyl, C1-C3-alkanoyloxy, Ci-C3-alkylsulfonyloxy, phenyl, by halogen, Ci-C3-alkyl, Ci-C3-alkoxy or nitro monosubstituted phenyl, nitro, cyano, carboxy, hydroxy, C1-C3-alkoxycarbonyl, -O-R3, -S-R3, -SO-R3 or -S02-R3, where R3 for Ci-Ci2-alkyl, halogen-substituted Ci-Ci2-alkyl, Ci-Ci2-alkyl monosubstituted by phenyl, cyano or Ci-C3-alkoxy, phenyl, by halogen, Ci-C3-alkyl, C1-C3-alkoxy or nitro monosubstituted phenyl, C3-C6-cycloalkyl, C4-C8-cycloalkylalkyl, C2-Ci2-alkenyl, halogen-substituted C2-Ci2-alkenyl, C2-Ci2-alkynyl or halogen-substituted C2-Ci2-alkynyl, with the proviso that the Substituent R3 contains at most 12 carbon atoms, R2 for halogen, hydrogen, cyano, Ci-C3-alkoxycarbonyl, Ci-Cö-alkyl, Ci-Có-alkyl substituted by halogen or Ci-C3-alkoxy, C2-Có-alkenyl, substituted by halogen or Ci-C3-alkoxy C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl, C3-Ce-cycloalkyl substituted by halogen, Ci-C3-alkyl or C1-C3-alkoxy, C4-C6-cycloalkenyl, C4-Cs Cycloalkylalkyl, phenyl-Ci-C3-alkyl, furyl, naphthyl, thienyl, -O-R4, -S-R4, -SO-R4, -SO2-R4 or is, R4 represents Ci-C3-alkyl, halogen-substituted Ci-C3-alkyl, C2-C3-alkenyl, halogen-substituted C2-C3-alkenyl, benzyl, phenyl or phenyl substituted by halogen, Ci-C3-alkyl or Ci-C3-alkoxy, the radicals Rs independently of one another halogen, Ci-Cs-alkyl, halogen-substituted Ci-Cs-alkyl, Ci-Cs-alkyl monosubstituted by phenyl, cyano or Ci-C3-alkoxy, C2-C8-alkenyl, halogen-substituted C2-Cs-alkenyl, C2-C8-alkynyl, halogen-substituted C2-Cs-alkynyl, C3-C6-cycloalkyl, C4-C6-cycloalkenyl, C4-Cs-cycloalkylalkyl, C1-C3-alkanoyloxy, Ci-C3-alkylsulfonyloxy, phenyl, by halogen, Ci-C3-alkyl, Ci-C3-alkoxy or nitro mean monosubstituted phenyl, nitro, cyano, carboxy, hydroxy, C1-C3-alkoxycarbonyl, -O-R6, -S-R6, -SO-R6 or -SO2-R6 , in which R6 for Ci-Ci2-alkyl, halogen-substituted Ci-Ci2-alkyl, Ci-Ci2-alkyl monosubstituted by phenyl, cyano or Ci-C3-alkoxy, phenyl, by halogen, Ci-C3-alkyl, C1-C3-alkoxy or nitro monosubstituted phenyl, C3-C6-cycloalkyl, C4-C8-cycloalkylalkyl, C2-Ci2-alkenyl, halogen-substituted C2-Ci2-alkenyl, C2-Ci2-alkynyl or halogen-substituted C2-Ci2-alkynyl, with the proviso that the Substituent R6 contains at most 12 carbon atoms, the indices m and n independently of one another denote 0.1 or 2, where the index m stands for 1 or 2 if X is an oxygen atom and R represents hydrogen or methyl and furthermore R2 represents unsubstituted phenyl, or of salts of the compounds of formula I, as an active ingredient of a herbicidal composition. 67. Use according to claim 66, characterized in that a compound of the following formula II À / 40 40. The method according to claim 1 for the preparation of 3- (3-bromophenyl) -5- (3-chlorophenyl) -1-methyl-4 (lH) -pyridone, characterized in that 2- (3-bromophenyl) -4- (3-chlorophenyl) -l, 5-dihydroxy-l, 4-pentadien-3-one cyclized with methylamine. 40 40 ammonia or its acid addition salt is carried out, and converted into the compound of formula I obtained, in which R is a hydrogen atom, by the N-alkylation method into the product correspondingly substituted on the nitrogen atom. 41. The method according to claim 1 for the preparation of 3- (3-chlorophenyl) -5- (4-chlorophenyl) -1-methyl-4 (1H) -pyridone, characterized in that 2- (3-chlorophenyl) -4- (4-chlorophenyl) -1,5-dihydroxy-1,4-pentadien-3-one cyclized with methylamine. 42. The method according to claim 1 for the preparation of 3- (2-fluorophenyl) -l-methyl-5- (3-trifluoromethylphenyl) - 43. The method according to claim 1 for the preparation of 3- (2-chlorophenyl) -5- (3-chlorophenyl) -1-methyl-4 (lH) -pyridone, characterized in that 2- (2-chlorophenyl) -4- (3-chlorophenyl) -l, 5-dihydroxy-l, 4-pentadien-3-one cyclized with methylamine. 44. The method according to claim I for the preparation of 3- (3-methoxyphenyl) -1-methyl-5- (3-trifluoromethylphenyl) -4 (lH) -pyridone, characterized in that 1,5-dihydroxy-2 - (3-methoxyphenyl) -4- (3-trifluoromethylphenyl) -l, 4-pentadien-3-one cyclized with methylamine. 45 3- (2-fluorophenyl) -l-methyl-5- (3-trifluoromethylphenyl) -4 (1H) -pyridone, 45 45. The method according to claim 1 for the production of 45 45 3. The method according to claim 1, for the preparation of 3,5-diphenyl-l-propyl-4 (l H) -pyridone, characterized in that l, 5-dihydroxy-2,4-diphenyl-l, 4- penta-dien-3-one cyclized with propylamine. 46. The method according to claim 1 for the preparation of I -AllyI-3-phenyl-5- (3-trifluoromethyl-phenyl) -4 (1 H) -pyridone, characterized in that l, 5-dihydroxy-2-phenyl- 47. The method according to claim 1 for the preparation of 3- (4-isopropylphenyl) -1-methyl-5-phenyl-4 (1 H) -pyridone, characterized in that 1,5-dihydroxy-2- (4-iso -propylphenyl) -4-phenyl-l, 4-pentadien-3-one cyclized with methylamine. 48. The method according to claim 1 for the preparation of 3- (2-chlorophenyl) -1-methyl-5- (3-trifluoromethylphenyl) -4 (lH) -pyridone, characterized in that 2- (2-chlorophenyl) - i , 5-dihydroxy-4- (3-trifluoromethylphenyl) -1,4-pentadien-3-one cyclized with methylamine. 49. The method according to claim 1 for the preparation of 3- (3-fluorophenyl) -l-methyl-5- (3-trifluoromethylphenyl) -4 (lH) -pyridone, characterized in that 1,5-dihydroxy-2 - (3-fluorophenyl) -4- (3-trifluoromethylphenyl) -1,4-pen-tadien-3-one cyclized with methylamine. 50 50. The method according to claim 1 for the preparation of 3- (4-fluorophenyl) -1-methyl-5- (3-trifluoromethylphenyl) -4 (lH) -pyridone, characterized in that 1,5-dihydroxy-2 - (4-fluorophenyl) -4- (3-trifluoromethylphenyl) -1,4-pen- cyclized tadien-3-one with methylamine. 50 51. The method according to claim 1 for the preparation of 3- (4-methoxyphenyl) -1-methyl-5- (3-trifluoromethylphenyl) -4 (lH) -pyridone, characterized in that 1,5-dihydroxy-2 - (4-methoxyphenyl) -4- (3-trifluoromethylphenyl) -1,4-pentadien-3-one cyclized with methylamine. 52. The method according to claim 1 for the preparation of l-methyl-3- (3-methylthiophenyl) -5-phenyl-4 (lH) pyridone, characterized in that l, 5-dihydroxy-2- (3-me- thylthiophenyl) -4-phenyl-l, 4-pentadien-3-one cyclized with methylamine. 53. The method according to claim 1 for the production of 54. The method according to claim 1 for the production of 55 55. The method according to claim 1 for the preparation of 1-methyl-3-phenyl-5- (2-thienyl) -4 (1 H) -pyridone, characterized in that l, 5-dihydroxy-2-phenyl-4- (2-thienyl) -l, 4-pentadien-3-one cyclized with methylamine. 55 <0 55 characterized in that l, 5-dihydroxy-2- (3-fhiorphenyl) -4-phenyl-l, 4-pentadien-3-one cyclized with methylamine. 56. The method according to claim 1 for the preparation of 3- (3-isobutylphenyl) -l-methyl-5-phenyl-4 (lH) -pyridone, characterized in that l, 5-dihydroxy-2- (3-iso- butylphenyl) -4-phenyl-l, 4-pentadien-3-one cyclized with methylamine. 57. The method according to claim 2, characterized in that first the 3- (2,4-dichlorophenyl) -5-phenyl-4- (1H) -pyridone is prepared and this then with methyl iodide to the 3- (2, 4-dichlorophenyl) -l-methyl-5-phenyl-4 (1H) -pyridone methylated. 58. The method according to claim 2, characterized in that firstly the 3,5-diphenyl-4 (1H) -pyridone is produced and this then with ethyl iodide 59. The method according to claim 2, characterized in that first the 3,5-diphenyl-4 (1H) -pyridone is produced and this then with allyl bromide to the l-allyl-3,5-diphenyl-4 (1H) -pyridone allylated. 60 6S 632496 R represents hydrogen, Ci-C3-alkyl, Ci-C3-alkyl substituted by halogen, cyano, carboxy or methoxycarbonyl, C2-C3-alkenyl, C2-C3-alkynyl, Ct-C3-alkoxy, hydroxy or dimethylamino, with which Provided that the substituent R contains no more than 3 carbon atoms, the radicals R 'independently of one another halogen, Ci-Ca-alkyl, halogen-substituted Ci-Cs-alkyl, Ci-Cs-alkyl monosubstituted with phenyl, cyano or Ci-Cî-alkoxy, C2-C8-alkenyl, halogen-substituted C2-Cs-alkenyl , C2-C8-alkynyl, halogen-substituted C2-Cs-alkynyl, C3-Có-cyclo-alkyl, C4-C6-cycloalkenyl, C4-Cs-cycloalkyIalkyl, C1-C3-alkanoyloxy, Ci-C3-alkylsulfonyloxy, phenyl, by halogen , Ci-C3-alkyl, Ci-C3-alkoxy or nitro monosubstituted phenyl, nitro, cyano, carboxy, hydroxy, C1-C3-alkoxycarbonyl, -O-R3, -S-R3, -SO-R3 or -SO2-R3 mean where R3 for Ci-Cn-alkyl, halogen-substituted Ci-Cn-alkyl, Ci-Ci2-alkyl monosubstituted by phenyl, cyano or Ci-C3-alkoxy, phenyl, by halogen, Ci-C3-alkyl, C1-C3-alkoxy or nitro monosubstituted phenyl, C3-Có-cyclo-alkyl, C4-C8-cycloalkylalkyl, C2-Ci2-alkenyl, halogen-substituted C2-Ci2-alkenyl, C2-Ci2-alkynyl or halogen-substituted C2-Ci2-alkynyl, with the proviso that the Substituent R3 contains at most 12 carbon atoms, R2 for halogen, hydrogen, cyano, Ci-C3-alkoxycarbonyl, Ci-C6-alkyl, Ci-Cé-alkyl substituted by halogen or Ci-C3-alkoxy, C2-C6-alkenyl, substituted by halogen or Ci-Cs-alkoxy Ci-Ct-alkenyl, Cì-Có-alkynyl, C3-C6-cycloalkyl, Cì-Có-cycloalkyl substituted by halogen, Ci-C3-alkyl or C1-C3-alkoxy, C4-C6-cycloalkenyl, C4-Cs -Cycloalkylalkyl, phenyl-Ci-C3-alkyl, furyl, naphthyl, thienyl, -O-R4, -S-R4, -SO-R4, -SO2-R4 or 60. The method according to claim 2, characterized in that firstly the 3,5-diphenyl-4 (1H) -pyridone is prepared and this then with the 2-bromopropane to the 3,5-diphenyl-1-isopropyl-4 (1H ) -pyridone propylated. 60 characterized in that 2- (4-bromophenyl) -l, 5-dihydroxy-4-phenyl-l, 4-pentadien-3-one cyclized with methylamine. 61. The method according to claim 2, characterized in that firstly the 3,5-diphenyl-4 (1H) -pyridone is prepared and this then with bromoacetonitrile to the 1-cyano-nomethyl-3,5-diphenyl-4 (1H ) -pyridone. 62. The method according to claim 1, characterized in that the compounds of the formula I are converted into their salts by treating them with a suitable acid or base. 63. Process for the preparation of 3-phenyl-5-substituted-4 (1H) -pyridothiones of the formula Ib S 64. The method according to claim 63, characterized in that the 2,4-bis (3-chlorophenyl) -l, 5-dihydroxy-l, 4-pentadien-3-one with methylamine to the 3, Cyclized 5-bis (3-chlorophenyl) -1-methyl-4 (1 H) -pyridone and this with phosphorus pentasulfide to the 3,5-bis (3-chlorophenyl) -l-methyl 1-4 (1 H) -pyridine thione implements. 65 used. 632496