A class of 3-phenyl-4(1H)-pyridones and pyridinethiones are broad-spectrum herbicides. The new compounds are characterized by a small substituent on the nitrogen, and usually bear a 5-substituent chosen from a class described herein. The phenyl ring may be substituted. The compounds are effective herbicides when applied both before and after the emergence of weeds, and are particularly useful for the control of weeds in cotton and rice cropland.

BACKGROUND OF THE INVENTION 
This invention belongs to the field of agriculture chemistry, and provides 
to the art new preemergence, postemergence, and aquatic herbicides, and 
methods for the use of the compounds for the control of weeds. Since the 
control of weeds is known to be a vital step in the maximization of crop 
yields, herbicides are now established as vital tools of the farmer and 
new and improved herbicidal compounds are in constant demand. 
Despite the great amount of research which has been performed in the field 
of agricultural chemistry, active compounds closely related to the 
compounds of the present invention have not been previously discovered. 
The polyhalopyridones, which have two or more chlorine atoms as well as 
other alkyl and halo substituents on the pyridine ring, are known 
herbicides, but are obviously quite distinct from the present invention. 
The organic chemical art has explored the pyridones rather extensively. For 
example, Ishibe et al., J. Am. Chem. Soc. 95, 3396-3397 (1973), disclosed 
a rearrangement of 3,5-diphenyl-1,2,6-trimethyl-4(1H)-pyridone. Such 
compounds, however, are not herbicides. Leonard et al., J. Am. Chem. Soc. 
77, 1852-1855 (1955), taught the synthesis of 
3,5-dibenzyl-1-methyl-4(1H)-pyridones, which compounds also have no 
herbicidal activity. The same principal author also disclosed 
3,5-di(substituted-benzylidene)tetrahydro-4-pyridones, J. Am. Chem. Soc. 
79, 156-160 (1957). 
Light et al., J. Org. Chem. 25, 538-546 (1960), taught a number of 
4-pyridone compounds including 2,6-diphenyl-1-methyl-4(1H)-pyridone, and 
related compounds bearing phenyl-ring substituents, none of which are 
herbicidally active. 
An interesting recent article was published by El-Kholy et al. in J. 
Hetero. Chem. 10, 665-667 (published September 7, 1973). El-Kholy 
described a synthesis of 3,5-diphenyl-1-methyl-4(1H)-pyridone and related 
compounds by the reaction with methylamine of the sodium salt of 
1,5-dihydroxy-2,4-diphenyl-1,4-pentadien-3-one. 
A counterpart of the parent application Ser. No. 591,661, has been patented 
as Belgian Patent 832,702 (1976). 
Articles reporting the herbicidal use of compounds of this invention 
include the following: 
Berard and Rainey, Weed Sci. Soc. of Am. Abstracts 28, p. 13 (1977); 
Waldrep and Taylor, J. Agric. Food Chem. 24, 1250-51 (1976); 
Waldrep and Taylor, Weed Sci. Soc. of Am. Abstracts 266, p. 109 (1977); 
Webster, Proc. Southern Weed Sci. Soc. 30, 103-12 (1977); 
Wills, Proc. Southern Weed Sci. Soc. 30, 113-18 (1977). 
SUMMARY OF THE INVENTION 
A series of new 3-phenyl-4(1H)-pyridones(thiones) are herbicides which are 
active against an unusually wide range of weeds. New methods and 
compositions using the compounds for the control of weeds, which methods 
are particularly useful in cotton and rice cropland, are also disclosed. 
The new compounds are of the formula 
##STR1## 
wherein X represents oxygen or sulfur; 
R represents C.sub.1 -C.sub.3 alkyl, 
C.sub.1 -c.sub.3 alkyl substituted with halo, cyano, carboxy or 
methoxycarbonyl, 
C.sub.2 -c.sub.3 alkenyl, 
C.sub.2 -c.sub.3 alkynyl, 
C.sub.1 -c.sub.3 alkoxy, 
acetoxy or 
dimethylamino, 
provided that R comprises no more than 3 carbon atoms; 
the R.sup.1 group independently represent halo, 
C.sub.1 -c.sub.8 alkyl, 
C.sub.1 -c.sub.8 alkyl substituted with halo, 
C.sub.1 -c.sub.8 alkyl monosubstituted with phenyl, cyano 
or C.sub.1 -C.sub.3 alkoxy, 
C.sub.2 -c.sub.8 alkenyl, 
C.sub.2 -c.sub.8 alkenyl substituted with halo, 
C.sub.2 -c.sub.8 alkynyl, 
C.sub.2 -c.sub.8 alkynyl substituted with halo, 
C.sub.3 -c.sub.6 cycloalkyl, 
C.sub.4 -c.sub.6 cycloalkenyl, 
C.sub.4 -c.sub.8 cycloalkylalkyl, 
C.sub.1 -c.sub.3 alkanoyloxy, 
C.sub.1 -c.sub.3 alkylsulfonyloxy, 
phenyl, 
phenyl monosubstituted with halo, C.sub.1 -C.sub.3 
alkyl, C.sub.1 -C.sub.3 alkoxy or nitro, 
nitro, 
cyano, 
carboxy, 
hydroxy, 
C.sub.1 -c.sub.3 alkoxycarbonyl, 
--O--R.sup.3, 
--s--r.sup.3, 
--so--r.sup.3 or 
--SO.sub.2 --R.sup.3 ; 
R.sup.3 represents C.sub.1 -C.sub.12 alkyl, 
C.sub.1 -c.sub.12 alkyl substituted with halo, 
C.sub.1 -c.sub.12 alkyl monosubstituted with phenyl, cyano or C.sub.1 
-C.sub.3 alkoxy, 
phenyl, 
phenyl monosubstituted with halo, C.sub.1 -C.sub.3 alkyl, C.sub.1 -C.sub.3 
alkoxy or nitro, 
C.sub.3 -c.sub.6 cycloalkyl, 
C.sub.4 -c.sub.8 cycloalkylalkyl, 
C.sub.2 -c.sub.12 alkenyl, 
C.sub.2 -c.sub.12 alkenyl substituted with halo, 
C.sub.2 -c.sub.12 alkynyl or 
C.sub.2 -c.sub.12 alkynyl substituted with halo, 
provided that R.sup.3 comprises no more than 12 carbon atoms; 
R.sup.2 represents halo, 
hydrogen, 
cyano, 
C.sub.1 -c.sub.3 alkoxycarbonyl, 
C.sub.1 -c.sub.6 alkyl, 
C.sub.1 -c.sub.6 alkyl substituted with halo or C.sub.1 -C.sub.3 alkoxy, 
C.sub.2 -c.sub.6 alkenyl, 
C.sub.2 -c.sub.6 alkenyl substituted with halo or C.sub.1 -C.sub.3 alkoxy, 
C.sub.2 -c.sub.6 alkynyl, 
C.sub.3 -c.sub.6 cycloalkyl, 
C.sub.3 -c.sub.6 cycloalkyl substituted with halo, C.sub.1 -C.sub.3 
alkyl or C.sub.1 -C.sub.3 alkoxy, 
C.sub.4 -c.sub.6 cycloalkenyl, 
C.sub.4 -c.sub.8 cycloalkylalkyl, 
phenyl--C.sub.1 -C.sub.3 alkyl, 
furyl, 
naphthyl, 
thienyl, 
--O--R.sup.4, 
--s--r.sup.4, 
--so--r.sup.4, 
--so.sub.2 --r.sup.4 or 
##STR2## 
R.sup.4 represents C.sub.1 -C.sub.3 alkyl, C.sub.1 -C.sub.3 alkyl 
substituted with halo, 
C.sub.2 -c.sub.3 alkenyl, 
C.sub.2 -c.sub.3 alkenyl substituted with halo, 
benzyl, 
phenyl or 
phenyl substituted with halo, C.sub.1 -C.sub.3 alkyl or C.sub.1 -C.sub.3 
alkoxy; 
the R.sup.5 groups independently represent halo, 
C.sub.1 -c.sub.8 alkyl, 
C.sub.1 -c.sub.8 alkyl substituted with halo, 
C.sub.1 -c.sub.8 alkyl monosubstituted with phenyl, 
cyano or 
C.sub.1 -c.sub.3 alkoxy, 
C.sub.2 -c.sub.8 alkenyl, 
C.sub.2 -c.sub.8 alkenyl substituted with halo, 
C.sub.2 -c.sub.8 alkynyl, 
C.sub.2 -c.sub.8 alkynyl substituted with halo, 
C.sub.3 -c.sub.6 cycloalkyl, 
C.sub.4 -c.sub.6 cycloalkenyl, 
C.sub.4 -c.sub.8 cycloalkylalkyl, 
C.sub.1 -c.sub.3 alkanoyloxy, 
C.sub.1 -c.sub.3 alkylsulfonyloxy, 
phenyl, 
phenyl monosubstituted with halo, C.sub.1 -C.sub.3 alkyl, C.sub.1 -C.sub.3 
alkoxy or nitro, 
nitro, 
cyano, 
carboxy, 
hydroxy, 
C.sub.1 -c.sub.3 alkoxycarbonyl, 
--O--R.sup.6, 
--s--r.sup.6, 
--so--r.sup.6 or 
--SO.sub.2 --R.sup.6 ; 
R.sup.6 represents C.sub.1 -C.sub.12 alkyl, 
C.sub.1 -c.sub.12 alkyl substituted with halo, 
C.sub.1 -c.sub.12 alkyl monosubstituted with phenyl, cyano or 
C.sub.1 -c.sub.3 alkoxy, 
phenyl, 
phenyl monosubstituted with halo, 
C.sub.1 -c.sub.3 alkyl, C.sub.1 -C.sub.3 alkoxy or nitro, 
C.sub.3 -c.sub.6 cycloalkyl, 
C.sub.4 -c.sub.8 cycloalkylalkyl, 
C.sub.2 -c.sub.12 alkenyl, 
C.sub.2 -c.sub.12 alkenyl substituted with halo, 
C.sub.2 -c.sub.12 alkynyl or 
C.sub.2 -c.sub.12 alkynyl substituted with halo, provided 
that R.sup.6 comprises no more than 12 carbon atoms; 
m and n independently represent 0-2; and the acid addition salts thereof. 
A preferred group of compounds comprises those wherein m represents 1, and 
the single R.sup.1 group is located at the meta position of the phenyl 
ring to which it is attached. Highly preferred compounds are those of the 
above group wherein R.sup.1 represents trifluoromethyl. 
A particularly preferred class of compounds are those of the formula 
##STR3## 
wherein X represents oxygen or sulfur; 
R.sup.9 represents C.sub.1 -C.sub.3 alkyl; 
R.sup.10 represents hydrogen, trifluoromethyl, C.sub.1 -C.sub.3 alkyl, 
halo, methoxy or methylthio; 
R.sup.11 represents C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.3 alkoxy, 
C.sub.1 -C.sub.3 alkylthio, phenyl, phenoxy, phenylthio, or phenyl, 
phenoxy or phenylthio monosubstituted with trifluoromethyl, C.sub.1 
-C.sub.3 alkyl, halo, methoxy or methylthio. 
A further preferred group of compounds are of the formula 
##STR4## 
wherein X represents oxygen or sulfur; 
R.degree. represents C.sub.1 -C.sub.3 alkyl, C.sub.2 -C.sub.3 alkenyl, 
acetoxy or methoxy; 
q and p independently represent 0-2; the R.sup.7 groups independently 
represent halo, C.sub.1 -C.sub.3 alkyl, trifluoromethyl or C.sub.1 
-C.sub.3 alkoxy; the R.sup.8 groups independently represent halo, C.sub.1 
-C.sub.3 alkyl, trifluoromethyl or C.sub.1 -C.sub.3 alkoxy, or two R.sup.8 
groups occupying adjacent o and m positions combine with the phenyl ring 
to which they are attached to form a 1-naphthyl group. 
Within all of the above-described classes of compounds of this invention, 
the pyridones wherein X represents oxygen are a preferred subclass, and 
the pyridinethiones wherein X represents sulfur are another preferred 
subclass. Further preferred subclasses within all of the above classes of 
compounds are those wherein the 1-substituent, R, R.degree. or R.sup.9, 
represents methyl or ethyl, and wherein the 1-substituent represents 
methyl. 
DESCRIPTION OF THE PREFERRED EMBODIMENT 
In the above formula, the general chemical terms are used in their normal 
meanings. For example, the terms C.sub.1 -C.sub.3 alkyl, C.sub.2 -C.sub.3 
alkenyl, C.sub.2 -C.sub.3 alkynyl, C.sub.1 -C.sub.3 alkoxy, C.sub.1 
-C.sub.3 alkylthio, C.sub.1 -C.sub.8 alkyl, C.sub.2 -C.sub.8 alkenyl, 
C.sub.2 -C.sub.8 alkynyl, C.sub.1 -C.sub.6 alkyl, C.sub.2 -C.sub.6 alkenyl 
and C.sub.2 -C.sub.6 alkynyl refer to such groups as methyl, ethyl, 
isopropyl, vinyl, allyl, methoxy, isopropoxy, methylthio, isopropylthio, 
propargyl, isobutyl, hexyl, octyl, 1,1-dimethylpentyl, 2-octenyl, pentyl, 
3-hexynyl, 1-ethyl-2-hexenyl, 3-octynyl, 5-heptenyl, 1-propyl-3-butynyl 
and crotyl. 
The terms C.sub.3 -C.sub.6 cycloalkyl and C.sub.4 -C.sub.6 cycloalkenyl 
refer to such groups as cyclopropyl, cyclobutyl, cyclohexyl, cyclobutenyl, 
cyclopentenyl and cyclohexadienyl. 
The term C.sub.4 -C.sub.8 cycloalkylalkyl refers to such groups as 
cyclopropylmethyl, cyclobutylmethyl, cyclohexylmethyl and cyclohexylethyl. 
The term C.sub.1 -C.sub.3 alkanoyloxy refers to groups such as formyloxy, 
acetoxy and propionyloxy. 
The term C.sub.1 -C.sub.3 alkoxycarbonyl refers to groups such as 
methoxycarbonyl, ethoxycarbonyl and isopropoxycarbonyl. 
The term C.sub.1 -C.sub.3 alkylsulfonyloxy refers to such groups as 
methylsulfonyloxy and propylsulfonyloxy. 
The term halo refers to fluoro, chloro, bromo, and iodo. 
The compounds described above can form acid addition salts, and such salts 
are useful embodiments of the invention. The preferred salts are the 
hydrohalides such as hydroiodides, hydrobromides, hydrochlorides and 
hydrofluorides. Salts of the sulfonic acids are also particularly 
desirable. Such salts include sulfonates, methylsulfonates and 
toluenesulfonates. 
Although the above general description of the compounds is believed to 
describe them unambiguously, a group of exemplary compounds of the 
invention will be named below to assure that the invention is understood 
by those skilled in the art. 
1-methyl-3,5-bis(3-methoxyphenyl)-4(1H)-pyridinethione 
1-ethyl-3-(4-ethoxyphenyl)-5-phenyl-4(1H)-pyridinethione 
3-(3,5-diiodophenyl)-5-(3-propylphenyl)-1-propyl-4(1H)-pyridinethione 
3-(2,6-dimethylphenyl)-1-isopropyl-5-(1-naphthyl)-4(1H)-pyridone 
3-(4-methylphenyl)-5-phenyl-1-vinyl-4(1H)-pyridone, hydroiodide 
1-allyl-3-(3-chlorophenyl)-5-(2,3-diethoxyphenyl)-4(1H)-pyridinethione 
3,5-diphenyl-1-ethyl-4(1H)-pyridinethione 
3-(3,5-difluorophenyl)-1-methoxy-5-phenyl-4(1H)-pyridone 
1-acetoxy-3-(3,5-diethylphenyl)-5-(2,4-diethylphenyl)-4(1H)-pyridinethione 
1-allyl-3-(1-naphthyl)-5-(4-propoxyphenyl)-4(1H)-pyridinethione 
1-propyl-3-(4-trifluoromethylphenyl)-5-(3-trifluoromethylphenyl)-4(1H)-pyri 
done 
3-(2,6-difluorophenyl)-5-(3-iodophenyl)-1-vinyl-4(1H)-pyridone 
3-(3,5-dibromophenyl)-5-(3-isopropoxyphenyl)-1-propyl-4(1H)-pyridone 
1-methyl-3-phenyl-5-(2-propylphenyl)-4(1H)-pyridinethione, hydrochloride 
3-(3-bromophenyl)-1-methyl-5-phenyl-4(1H)-pyridone 
3-(4-chlorophenyl)-5-(2,4-dimethoxyphenyl)-1-propyl-4(1H)-pyridone 
1-allyl-3-phenyl-5-(3-trifluoromethylphenyl)-4(1H)-pyridinethione 
1-acetoxy-3,5-diphenyl-4(1H)-pyridinethione 
3-(2-iodophenyl)-5-(3-isopropylphenyl)-1-methoxy-4(1H)-pyridinethione 
3-(2-iodo-4-methylphenyl)-5-phenyl-1-vinyl-4(1H)-pyridinethione 
1-acetoxy-3-(4-chlorophenyl)-5-(1-naphthyl)-4(1H)-pyridone 
3,5-diphenyl-1-isopropyl-4(1H)-pyridinethione 
3-(3-bromo-5-ethylphenyl)-5-(3-methylphenyl)-1-propyl-4(1H)-pyridinethione 
3-(4-ethoxy-2-fluorophenyl)-1-methoxy-5-phenyl-4(1H)-pyridone 
1-allyl-3,5-bis(3-ethyl-4-methoxyphenyl)-4(1H)-pyridone 
3-(2-iodo-4-propylphenyl)-1-methyl-5-(4-trifluoromethylphenyl)-4(1H)-pyridi 
nethione 
1-methyl-3-(3-methyl-5-propylphenyl)-5-phenyl-4(1H)-pyridinethione 
3-(2-chloro-4-iodophenyl)-5-(3-fluorophenyl)-1-propyl-4(1H)-pyridinethione 
3-(3-chlorophenyl)-5-[2,4-bis(trifluoromethyl)-phenyl]-1-methoxy-4(1H)-pyri 
done 
3-benzyloxy-1-chloromethyl-5-(3-ethynylphenyl)-4(1H)-pyridone 
3-benzylthio-1-(2-bromoethyl)-5-(2,4-dimethylphenyl)-4(1H)-pyridone 
3-benzylsulfinyl-1-ethyl-5-(3-fluoro-5-propylphenyl)-4(1H)-pyridone 
3-benzylsulfonyl-5-(3-octylphenyl)-1-propyl-4(1H)-pyridone 
3-(2-butylphenyl)-1-trifluoromethyl-4(1H)-pyridone, hydrobromide 
1-(2-chloroethyl)-3-cyano-5-phenyl-4(1H)-pyridinethione 
3-(3-hexylphenyl)-1-methyl-5-(2-methylphenyl)-4(1H)-pyridone 
1-(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-propoxycarbonyl-4(1H)-pyridon 
e 
3-[3-(2-ethylpentyl)phenyl]-1-carboxymethyl-5-(3-trifluoromethylphenyl)-4(1 
H)-pyridone 
3-(2-chloromethylphenyl)-1-methoxycarbonylmethyl-4(1H)-pyridone 
3,5-diphenyl-1-ethynyl-4(1H)-pyridinethione 
3-(4-heptafluoropropylphenyl)-5-hexyl-1-methyl-4(1H)-pyridinethione 
3-(3,5-diethylphenyl)-1-propargyl-5-[3-(5,5-dibromopentyl)phenyl]-4(1H)-pyr 
idone 
3-(2,4-dipropylphenyl)-1-methyl-5-trifluoromethyl-4(1H)-pyridone 
3-(4-benzylphenyl)-1-ethoxy-5-(2-fluoroethyl)-4(1H)-pyridone 
3-(2-chloroethyl)-5-[4-(2,2-diiodooctyl)phenyl]-1-methoxy-4(1H)-pyridinethi 
one 
3-(3-chloro-2-methoxyphenyl)-5-(1,1-dibromopentyl)-1-methyl-4(1H)-pyridone 
3-(6-iodohexyl)-1-isopropoxy-5-phenyl-4(1H)-pyridinethione 
3-(3-hexylphenyl)-5-methoxymethyl-1-methyl-4(1H)-pyridone 
1-dimethylamino-3,5-bis(3-trifluoromethylphenyl)-4(1H)-pyridinethione 
1-methyl-3-[4-(4-phenylhexyl)phenyl]-5-(3-propylphenyl)-4(1H)-pyridone 
3-(3-hexenyl)-5-[2-(2-methoxyethyl)phenyl]-1-methyl-4(1H)-pyridinethione 
3-(2,2-dichlorovinyl)-1-methyl-5-[3-(3-propoxyheptyl)phenyl]-4(1H)-pyridone 
3-(2-bromo-1-butenyl)-5-[3-(6-ethoxyheptyl)phenyl]-1-ethoxy-4(1H)-pyridone 
3-(2-iodo-1-hexenyl)-1-methyl-5-(3-vinylphenyl)-4(1H)-pyridinethione 
3-(4-allylphenyl)-1-dimethylamino-5-phenyl-4(1H)-pyridinethione 
3-(2-methoxyallyl)-1-methyl-5-(4-trifluoromethylphenyl)-4(1H)-pyridinethion 
e 
3-(4-ethoxy-2-pentenyl)-5-[2-(2,4-hexadienyl)phenyl]-1-methoxy-4(1H)-pyrido 
ne 
1-methoxycarbonylmethyl-3-[3-(3-octenyl)phenyl]-5-phenyl-4(1H)-pyridone, 
methanesulfonate 
3-[3-(2-hexenyl)phenyl]-1-methyl-5-(3-propylphenyl)-4(1H)-pyridinethione 
3-(2-ethyl-3-fluorophenyl)-5-ethynyl-1-methyl-4(1H)-pyridinethione 
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)phenyl]-4(1H)-py 
ridone 
3-cyclopropyl-5-[2-(2-fluoro-1-pentenyl)phenyl]-1-methoxy-4(1H)-pyridinethi 
one 
1-(2-chloroethyl)-3-[4-(2-cyanoethyl)phenyl]-4(1H)-pyridinethione 
1-methyl-3-(2-propoxyethyl)-5-phenyl-4(1H)-pyridinethione, hydrofluoride 
3-(6-ethoxyhexyl)-5-(3-ethyl-5-iodophenyl)-1-(3-iodopropyl)-4(1H)-pyridone 
1-methyl-3-phenyl-5-vinyl-4(1H)-pyridinethione 
3-allyl-5-[4-(3-cyanohexyl)phenyl]-1-propoxy-4(1H)-pyridinethione 
3-[4-(8-cyanooctyl)phenyl]-1-methyl-5-(2-pentenyl)-4(1H)-pyridone 
3-cyclobutyl-5-[4-(2-iodovinyl)phenyl]-1-propoxy-4(1H)-pyridone 
3-cyclohexyl-5-(3-ethynylphenyl)-1-iodomethyl-4(1H)-pyridinethione 
1-(1-carboxyethyl)-3-(2-chlorocyclopropyl)-5-[3-(3-chloropropargyl)phenyl]- 
4(1H)-pyridone 
3-(2,2-dibromocyclohexyl)-1-methyl-5-[2-(3-pentynyl)phenyl]-4(1H)-pyridinet 
hione 
3-[4-(1,1-dibromo-4-pentynyl)phenyl]-1-isopropoxy-5-(2-methylcyclobutyl)-4( 
1H)-pyridone 
3-(2,4-diiodocyclopentyl)-1-ethyl-5-[4-(2-octynyl)phenyl]-4(1H)-pyridone 
1-acetoxy-3-(4-propylcyclohexyl)-5-[3-(6,6,6-trifluoro-2-hexynyl)phenyl]-4( 
1H)-pyridinethione 
3-[3-(4-octynyl)phenyl]-5-(2-methoxycyclopropyl)-1-methyl-4(1H)-pyridinethi 
one 
3-[2-(1,1-dichloro-4-heptynyl)phenyl]-5-(4-methoxycyclohexyl)-1-methoxy-4( 
1H)-pyridone 
3-(4-cyclopropylphenyl)-1-(2-methoxycarbonylmethyl)-5-(2-propoxycyclobutyl) 
-4(1H)-pyridinethione 
3-(2-cyclobutenyl)-5-(3-cyclopentylphenyl)-1-ethoxy-4(1H)-pyridinethione 
3-(3-cyclohexenyl)-5-(3-cyclohexylphenyl)-1-dimethylamino-4(1H)-pyridone 
3-[4-(1-cyclobutenyl)phenyl]-5-methoxy-1-vinyl-4(1H)-pyridone, 
toluenesulfonate 
3-chloromethoxy-1-cyanomethyl-5-(2-formyloxyphenyl)-4(1H)-pyridinethione 
1-(2-carboxyethyl)-3-(3-propionyloxyphenyl)-5-trifluoromethoxy-4(1H)-pyridi 
nethione 
3-[4-(2-cyclohexenyl)phenyl]-5-isopropoxy-1-trifluoromethyl-4(1H)-pyridone 
3-(1,2-dibromopropoxy)-1-ethoxy-5-(2-methylsulfonyloxyphenyl)-4(1H)-pyridin 
ethione 
1-dichloromethyl-3-(2-iodoethoxy)-5-(4-isopropylsulfonyloxyphenyl)-4(1H)-py 
ridone 
3-(3-biphenylyl)-1-methyl-5-vinyloxy-4(1H)-pyridinethione 
3-allyloxy-5-[4-(2-chlorophenyl)phenyl]-1-isopropyl-4(1H)-pyridone, 
hydrochloride 
3-(2,2-dichlorovinyloxy)-5-[2-(3-iodophenyl)phenyl]-1-methyl-4(1H)-pyridone 
3-(2-bromoallyloxy)-5-[3-(3-bromophenyl)phenyl]-1-vinyl-4(1H)-pyridone 
1-allyl-3-[4-(2-methylphenyl)phenyl]-5-(3,3,3-trifluoro-1-propenyloxy)-4(1H 
)-pyridone 
1-methoxy-3-phenoxy-5-[3-(4-propylphenyl)phenyl]-4(1H)-pyridone 
3-(2-chlorophenoxy)-5-[4-methoxyphenyl)phenyl]-1-propargyl-4(1H)-pyridone 
3-(4-bromophenoxy)-5-[4-(2-ethoxyphenyl)phenyl]-1-ethyl-4(1H)-pyridone 
3-(2-iodophenoxy)-5-[3-(4-isopropoxyphenyl)-phenyl]-1-methoxycarbonylmethyl 
-4(1H)-pyridone 
1-cyanomethyl-3-(2-methylphenoxy)-5-[3-(4-nitrophenyl)phenyl]-4(1H)-pyridin 
ethione 
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-4(1H)-pyridone, 
hydrofluoride 
1-(2-carboxyethyl)-3-(4-hydroxyphenyl)-5-(3-propoxyphenoxy)-4(1H)-pyridone 
3-benzyl-5-(2-methoxycarbonylphenyl)-1-methyl-4(1H)-pyridone 
1-dimethylamino-3-(3-phenylpropyl)-5-(4-propoxycarbonylphenyl)-4(1H)-pyrido 
ne 
3-(3-butoxyphenyl)-5-(2-furyl)-1-trifluoromethyl-4(1H)-pyridone 
3-(1-ethylpentyl)-5-(3-furyl)-1-methyl-4(1H)-pyridone 
3-[4-(2-propylhexyloxy)phenyl]-1-methoxycarbonylmethyl-5-(2-thienyl)-4(1H)- 
pyridone 
1-methyl-3-(4-nonyloxyphenyl)-5-(3-thienyl)-4(1H)-pyridinethione 
1-methyl-3-[4-(2-propylnonyloxy)phenyl]-5-(4-trifluoromethylphenyl)-4(1H)-p 
yridinethione 
3-(3,5-diethylphenyl)-1-ethyl-5-(4-trifluoromethoxyphenyl)-4(1H)-pyridineth 
ione 
3-(2,4-divinylphenyl)-5-[4-(2-fluoroethoxy)phenyl]-1-isopropoxy-4(1H)-pyrid 
inethione 
3-[3-(5,5-dibromopentoxy)phenyl]-5-(3,5-dicyclopropylphenyl)-1-ethyl-4(1H)- 
pyridone 
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(1H)-py 
ridinethione 
3-(2,6-dinitrophenyl)-1-methoxy-5-[5-phenylpentoxy)phenyl]-4(1H)-pyridone 
3-(2,4-diformyloxyphenyl)-1-ethoxy-5-[4-(3-phenylhexyloxy)phenyl]-4(1H)-pyr 
idinethione 
3-[4-(3-cyanopropoxy)phenyl]-5-(3-ethoxy-5-iodophenyl)-1-methyl-4(1H)-pyrid 
inethione 
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 
(1H)-pyridinethione 
3-[2-(2-ethoxyethoxy)phenyl]-1-(2-iodoethyl)-5-(3,4-diacetoxyphenyl)-4(1H)- 
pyridinethione 
3-(4-butoxy-2-difluoromethylphenyl)-1-cyanomethyl-5-[3-(6-methoxyhexyloxy)p 
henyl]-4(1H)-pyridone 
3-(2-cyclohexyl-4-ethylphenyl)-1-methoxycarbonylmethyl-5-[2-(6-propoxynonyl 
oxy)phenyl]-4(1H)-pyridone 
3-[2,4-di(2-pentynyl)phenyl]-1-isopropoxy-5-(2-vinyloxyphenyl)-4(1H)-pyridi 
nethione 
3-(2,4-diallyloxyphenyl)-1-(2,2-dichloropropyl)-5-(2-methyl-6-nitrophenyl)- 
4(1H)-pyridone 
3-[3-(2,4-hexadienyloxy)phenyl]-1-isopropyl-5-phenyl-4(1H)-pyridinethione, 
hydroiodide 
1-(2-carboxyethyl)-3-(2,6-dipropylphenyl)-5-[4-(5-dodecenyloxy)phenyl]-4(1H 
)-pyridinethione 
3-[2-(2-chloroallyloxy)phenyl]-1-(2,2-dichloroethyl)-5-(2,4-diethoxyphenyl) 
-4(1H)-pyridinethione 
1-allyl-3-(4-cyano-3-ethoxycarbonylphenyl)-5-[4-(4,4,4-trifluoro-2-butenylo 
xy)phenyl]-4(1H)-pyridone 
1-chloromethyl-3-(3-methylsulfonyloxy-5-vinylphenyl)-5-[3-(2,2-dibromo-3-he 
ptenyloxy)phenyl]-4(1H)-pyridinethione 
1-ethoxy-3-[3-(9-iodo-1-nonenyloxy)phenyl]-5-phenyl-4(1H)-pyridone 
1-chlorodifluoromethyl-3-[2,4-di(chloromethyl)phenyl]-5-[2-(1,2,3-trichloro 
-6-dodecenyloxy)phenyl]-4(1H)-pyridinethione 
3-[3-(4-chloro-2-butynyloxy)phenyl]-1-ethoxy-5-(3-fluoro-4-isobutoxyphenyl) 
-4(1H)-pyridone 
3-[3-(6,6-dibromo-3-hexynyloxy)phenyl]-1-methyl-5-(3-nitro-4-propylphenyl)- 
4(1H)-pyridinethione 
1-acetoxy-3-(2,4-dibromophenyl)-5-[3-(1,1,2,2-tetrafluoro-3-decynyloxy)phen 
yl]-4(1H)-pyridone 
3-(3-ethynyloxyphenyl)-1-methyl-5-phenyl-4(1H)-pyridinethione, hydrobromide 
3-[2-(10-dodecynyloxy)phenyl]-1-methyl-5-(2-propyl-4-propylsulfonyloxypheny 
l)-4(1H)-pyridone 
3-[2,4-di(3-pentenyl)phenyl]-5-(3-phenoxyphenyl)-1-(1,1,2,2-tetrafluoroethy 
l)-4(1H)-pyridone 
3-[4-(4-fluorophenoxy)phenyl]-1-isopropyl-5-phenyl-4(1H)-pyridinethione 
1-(3-chloropropyl)-3-(3-cyanomethyl-5-ethylphenyl)-5-[3-(3-iodophenoxy)phen 
yl]-4(1H)-pyridone 
3-(3-octyl-5-fluorophenyl)-5-[2-(3-ethylphenoxy)phenyl]-1-trifluoromethyl-4 
(1H)-pyridone 
3-(2-ethyl-4-propylsulfonyloxyphenyl)-1-ethynyl-5-[2-(4-isopropylphenoxy)ph 
enyl]-4(1H)-pyridone 
1-carboxymethyl-3-(2,4-dinonyloxyphenyl)-5-[3-(4-methoxyphenoxy)phenyl]-4(1 
H)-pyridone 
1-chloromethyl-3-(2,4-difluorophenyl)-5-[2-(3-propoxyphenoxy)phenyl]-4(1H)- 
pyridinethione 
1-methyl-3-[4-(2-nitrophenoxy)phenyl]-5-phenyl-4(1H)-pyridinethione 
3-(3-isobutylthiophenyl)-1-isopropyl-5-phenyl-4(1H)-pyridinethione 
3-(3-chloro-4-heptylthiophenyl)-5-[3-(4-cyanopentyl)phenyl]-1-methyl-4(1H)- 
pyridone 
1-methyl-3-phenyl-5-[2-(3-ethylhexylthio)phenyl]-4(1H)-pyridone, 
hydrofluoride 
3-(2-chloro-4-ethylphenyl)-1-ethyl-5-(3-nonylthio-4-vinylphenyl)-4(1H)-pyri 
done 
1-ethynyl-3-phenyl-5-[3-(2-ethylpentylthio)phenyl]-4(1H)-pyridone 
1-(2-methoxycarbonylmethyl)-3-[4-(3-iodophenyl)phenyl]-5-(3-trifluoromethyl 
thiophenyl)-4(1H)-pyridinethione 
1-acetoxy-3-(3-cyclopentylphenyl)-5-[3-(2-fluoroethylthio)phenyl]-4(1H)-pyr 
idinethione 
3-(2-cyano-4-hydroxyphenyl)-1-dimethylamino-5-[3-(5,5-dibromopentylthio)-4- 
nitrophenyl]-4(1H)-pyridone 
3-[4-(4,4-diiodododecylthio)phenyl]-1-methyl-5-phenyl-4(1H)-pyridone 
3-(3-benzylthio-5-ethynylphenyl)-1-cyanomethyl-5-(2-hexylphenyl)-4(1H)-pyri 
dinethione 
3-[3,5-bis(4-phenylbutylthio)phenyl]-5-(2-methylphenyl)-1-(1,1,2,2-tetraflu 
oroethyl)-4(1H)-pyridone 
3-[2-bromo-4-(6-phenylhexylthio)phenyl]-5-[4-(2-cyanopropylthio)-2-ethylphe 
nyl]-1-methyl-4(1H)-pyridinethione 
3-[4-(6-cyanoheptylthio)phenyl]-1-fluoromethyl-4(1H)-pyridone 
3-(3-acetoxy-5-ethylphenyl)-5-[2-(8-cyanoundecylthio)phenyl]-1-chlorodifluo 
romethyl-4(1H)-pyridone 
3-(4-benzyl-2-ethoxyethoxyphenyl)-1-(2-carboxyethyl)-5-[3-(2-ethoxyethoxy)- 
5-propargylphenyl]-4(1H)-pyridone, toluenesulfonate 
1-ethyl-3-[4-(6-methoxyhexylthio)phenyl]-5-phenyl-4(1H)-pyridinethione 
1-isopropenyl-3-[3-(3-phenylpentyl)phenyl]-5-[4-(6-isopropoxynonylthio)phen 
yl]-4(1H)-pyridone 
3-(2-cyanomethyl-4-vinylthiophenyl)-1-ethyl-5-[2-(7-phenylheptyl)phenyl]-4( 
1H)-pyridone 
3-(3-allylthio-4-methoxymethylphenyl)-5-[2-(6-cyanohexyl)-4-vinylphenyl]-1- 
methyl-4(1H)-pyridone 
1-methoxycarbonylmethyl-3-[3-(2-pentenylthio)-phenyl]-5-phenyl-4(1H)-pyridi 
nethione 
3-[3-(2-decenylthio)-5-(2,4-hexadienyl)phenyl]-1-ethoxy-5-phenyl-4(1H)-pyri 
done 
3-[4-(1,1-dichloroallylthio)phenyl]-5-[3-(4-octenyl)-2-propylphenyl]-1-trif 
luoromethyl-4(1H)-pyridone 
3-(4-carboxy-2-hydroxyphenyl)-5-[3-(2-chloro-3-butenylthio)-5-nitrophenyl]- 
1-vinyl-4(1H)-pyridone 
3-[4-(5,5-dibromo-3-heptenylthio)phenyl]-1-methyl-5-phenyl-4(1H)-pyridone 
3,5-bis[4-(9-iodo-8-nonenylthio)phenyl]-1-isopropyl-4(1H)-pyridinethione 
1-ethyl-3-(3-fluorophenyl)-5-[4-(12,12,12-trichloro-2,6-dodecadienylthio)ph 
enyl]-4(1H)-pyridinethione 
3-[2-(1-chloropropargylthio)phenyl]-1-dimethylamino-5-[3-(4-pentenyl)-5-met 
hoxycarbonylphenyl]-4(1H)-pyridone 
3-[4-(3,3-dibromo-5-hexynylthio)phenyl[-1-methoxy-5-phenyl-4(1H)-pyridone 
1-(2-chloropropyl)-3-[2-cyclopropyl-4-(1,1,2,2-tetrafluoro-5-decynylthio)ph 
enyl]-5-phenyl-4(1H)-pyridinethione 
1-acetoxy-3-(3-ethynylthiophenyl)-5-(3-ethynyl-5-fluorophenyl)-4(1H)-pyrido 
ne 
3-[4-(4-decynylthio)-2-methylphenyl]-1-ethoxy-5-(5-fluoro-3-trifluoromethyl 
phenyl)-4(1H)-pyridinethione 
1-cyanomethyl-3-(4-phenylthiophenyl)-5-phenyl-4(1H)-pyridinethione, 
hydrochloride 
3-(3-chlorophenyl)-5-[2-(3-fluorophenylthio)phenyl]-1-methyl-4(1H)-pyridone 
1-carboxymethyl-3-[3-(2-iodophenylthio)phenyl]-5-(3-methyl-5-methoxycarbony 
lphenyl)-4(1H)-pyridone 
1-(2-chloroethyl)-3-(2,4-diethylphenyl)-5-[4-(4-ethylphenylthio)-2-methoxyp 
henyl]-4(1H)-pyridone 
3-[3-(3-isopropylphenylthio)phenyl]-5-phenyl-1-trifluoromethyl-4(1H)-pyrido 
ne 
1-acetoxy-3-(4-butylphenyl)-5-[4-(3-methoxyphenylthio)phenyl]-4(1H)-pyridin 
ethione 
3-(2-methyl-6-propoxyphenyl)-3-[4-(3-propoxyphenylthio)phenyl]-1-propargyl- 
4(1H)-pyridone 
3-[3-chloro-5-(4-nitrophenylthio)phenyl]-1-methyl-5-(2,4-divinylphenyl)-4(1 
H)-pyridone 
3-(4-butylsulfinylphenyl)-5-phenyl-1-propargyl-4(1H)-pyridone 
1-ethyl-3-(3-heptylsulfinylphenyl)-5-(4-propoxycarbonylphenyl)-4(1H)-pyrido 
ne 
3-(2-carboxyphenyl)-1-dimethylamino-5-[2-hydroxy-4-(2-propylpentylsulfinyl) 
phenyl]-4(1H)-pyridinethione 
1-acetoxy-3-(2-cyano-5-nonylsulfinylphenyl)-5-(3,5-dinitrophenyl)-4(1H)-pyr 
idinethione 
1-ethoxy-3-[3-(4-propylnonylsulfinyl)phenyl]-5-phenyl-4(1H)-pyridone 
1-methoxy-3-(2-nitrophenyl)-5-(4-trifluoromethylsulfinylphenyl)-4(1H)-pyrid 
inethione 
3-(2-ethoxyphenyl)-1-isopropyl-5-[4-(2-fluoroethylsulfinyl)-2-isopropylphen 
yl]-4(1H)-pyridone 
3-[3,5-di(4-chlorophenyl)phenyl]-3-[4-(5,5-dibromopentylsulfinyl)-2-ethoxyp 
henyl]-1-ethynyl-4(1H)-pyridone 
3-[3-(12-iodododecylsulfinyl)phenyl]-5-phenyl-1-propargyl-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(1H)-pyridone 
3-[2-(3-cyanopropylsulfinyl)phenyl]-1-methoxycarbonylmethyl-5-phenyl-4(1H)- 
pyridinethione 
3-(3-acetoxyphenyl)-5-[2-(7-cyanoheptylsulfinyl)phenyl]-1-methoxycarbonylme 
thyl-4(1H)-pyridone 
1-(2-carboxyethyl)-3-[3-(3-cyclohexenyl)-5-(3-cyanoundecenylsulfinyl)phenyl 
]-4(1H)-pyridone 
3-(2-chloro-4-cyclohexylphenyl)-5-[3-chloro-5-(2-ethoxyethylsulfinyl)phenyl 
]-1-(2-cyanoethyl)-4(1H)-pyridinethione 
1-(2-chloroethyl)-3-[4-(6-methoxyhexylsulfinyl)-phenyl]-4(1H)-pyridone 
3-(4-cyclopropylphenyl)-1-iodomethyl-5-[3-(6-propoxynonylsulfinyl)phenyl]-4 
(1H)-pyridone 
3-[3-(2-chloro-6-undecynylsulfinyl)phenyl]-1-(2,2-dibromoethyl)-5-(2-ethyl- 
5-vinylsulfinylphenyl)-4(1H)-pyridinethione 
3-[3,5-di(allylsulfinyl)phenyl]-5-phenyl-1-propyl-4(1H)-pyridone, 
hydrofluoride 
3-[3-(2,4-hexadienylsulfinyl)phenyl[-1-methyl-5-phenyl-4(1H)-pyridinethione 
1-dimethylamino-3-[2-(5-dodecenylsulfinyl)phenyl]-5-(3-isobutylphenyl)-4(1H 
)-pyridone 
1-acetoxy-3-[4-(2-bromoallylsulfinyl)phenyl]-5-(2,4-dimethylphenyl)-4(1H)-p 
yridinethione 
1-ethoxy-3-(3-iodo-4-pentylphenyl)-5-[3-(3,3,4,4-tetrafluoro-1-butenylsulfi 
nyl)-5-hexylphenyl]-4(1H)-pyridone 
1-isopropoxy-3-phenyl-5-[4-(1,1,2-trichloro-3-heptenylsulfinyl)phenyl]-4(1H 
)-pyridinethione 
3-[4-(9-bromo-4-nonenylsulfinyl)phenyl]-5-[2-(3-ethylhexyl)phenyl]-1-ethyny 
l-4(1H)-pyridinethione 
3-[2,4-di(chlorodifluoromethyl)phenyl-1-propargyl-5-[3-(1,2,3-triiodo-6-dod 
ecenylsulfinyl)phenyl]-4-(1H)-pyridone 
3-[3-(4-bromo-2-butynylsulfinyl)-5-methylphenyl]-5-[2-iodo-3-(1,2,3-trichlo 
ropentyl)phenyl]-1-vinyl-4(1H)-pyridone 
1-allyl-3-[2-(2,2-dibromo-4-hexynylsulfinyl)phenyl]-5-phenyl-4(1H)-pyridone 
1-methoxycarbonylmethyl-3-[3-ethyl-5-(9,9,10,10-tetrafluoro-2-decynylsulfin 
yl)phenyl]-5-phenyl-4(1H)-pyridinethione 
3-(4-benzyl-2-bromophenyl)-1-(2-carboxyethyl)-5-[3-(1-chlorobutyl)-5-(6-dod 
ecynylsulfinyl)phenyl]-4-(1H)-pyridone 
1-(2-cyanoethyl)-3-(4-phenylsulfinylphenyl)-5-phenyl-4(1H)-pyridinethione 
1-cyanomethyl-3-[4-(3-fluorophenylsulfinyl)phenyl]-5-[3-(4-octenyl)phenyl]- 
4(1H)-pyridone 
1-chloromethyl-3-[3-(1,1-dichloro-4-octenyl)-4-nitrophenyl]-5-[3-(2-iodophe 
nylsulfinyl)phenyl]-4(1H)-pyridone 
3-[3-(2-chlorovinyl)-5-(4-methylphenylsulfinyl)-phenyl]-1-ethoxy-5-[3-(8-io 
do-4-octenyl)phenyl]-4(1H)-pyridone 
3-[4-(3-isopropylphenylsulfinyl)phenyl]-5-phenyl-1-propyl-4(1H)-pyridone 
3-[3-(2-ethoxyphenylsulfinyl)phenyl]-1-methyl-5-[4-(2-propoxyphenoxy)phenyl 
]-4(1H)-pyridone 
3-[4-(2,4-cyclohexadienyl)-3-fluorophenyl]-1-ethyl-5-[3-hydroxy-5-(3-nitrop 
henylsulfinyl)phenyl]-4(1H)-pyridinethione 
1-methyl-3-(4-methylsulfonylphenyl)-5-phenyl-4(1H)-pyridinethione 
1-ethyl-3-(3-hexylsulfonylphenyl)-5-(4-hydroxyphenyl)-4(1H)-pyridone 
3-(2-carboxy-4-ethylphenyl)-1-dimethylamino-5-[4-(3-ethylheptylsulfonyl)phe 
nyl]-4(1H)-pyridone 
1-acetoxy-3-(2-hexyl-5-fluorophenyl)-5-(3-nitro-5-nonylsulfonylphenyl)-4(1H 
)-pyridone 
3-phenyl-1-propoxy-5-[2-(3-propylnonylsulfonyl)-phenyl]-4(1H)-pyridone 
1-ethoxy-3-phenyl-5-(3-trifluoromethyl-5-trifluoromethylsulfonylphenyl)-4(1 
H)-pyridone 
3-[4-(2-chloroethylsulfonyl)phenyl]-5-(3-fluoro-4-octylphenyl)-1-methoxy-4( 
1H)-pyridinethione 
3-(3-bromo-5-nitrophenyl)-1-ethynyl-5-[4-cyano-2-(6,6-dibromohexylsulfonyl) 
phenyl]-4(1H)-pyridone 
3-[3-(4,4-diiodododecylsulfonyl)phenyl]-5-(2-naphthyl)-1-(1-propynyl)-4(1H) 
-pyridone 
3-(4-benzylsulfonylphenyl)-5-[3-(2-ethoxyphenyl)phenyl]-1-isopropenyl-4(1H) 
-pyridinethione 
3-[5-chloromethyl-4-(2-propylphenyl)phenyl]-1-vinyl-5-[4-(3-phenylbutylsulf 
onyl)phenyl]-4(1H)-pyridone 
3-[3-(3-cyanopropylsulfonyl)phenyl]-1-methoxycarbonylmethyl-5-phenyl-4(1H)- 
pyridone 
1-(2-carboxyethyl)-3-[4-(7-cyanoheptylsulfonyl)phenyl]-5-[3-(4-chlorophenyl 
)phenyl]-4(1H)-pyridone 
1-cyanomethyl-3-[3-(11-cyanoundecylsulfonyl)-5-fluorophenyl]-5-(4-propylsul 
fonyloxyphenyl)-4(1H)-pyridone 
3-(2-acetoxy-4-ethoxyethylsulfonylphenyl)-1-chloromethyl-5-(5-cyclopropyl-2 
-trifluoromethylphenyl)-4(1H)-pyridone 
3-(3-ethoxyhexylsulfonylphenyl)-5-phenyl-1-trifluoromethyl-4(1H)-pyridineth 
ione 
3-[4-(3-cyclohexenyl)phenyl]-1-propyl-5-[3-(9-propoxynonylsulfonyl)phenyl]- 
4(1H)-pyridone 
3-[3-cyanomethyl-4-(1-cyclobutenyl)phenyl]-1-methyl-5-(4-vinylsulfonylpheny 
l)-4(1H)-pyridinethione 
3-(2-allylsulfonyl-4-chlorophenyl)-5-(2-allyl-3-cyclohexylphenyl)-1-dimethy 
lamino-4(1H)-pyridinethione 
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-tetraflu 
oro-2-octynyl)phenyl]-4(1H)-pyridone 
3-[4-(6-heptynyl)-3-methylphenyl]-1-ethyl-5-[3-(1,1,2-triiodo-3-butenylsulf 
onyl)-5-chlorophenyl]-4(1H)-pyridone 
3-[2-(5,5-dibromo-2-pentynyl)phenyl]-1-dimethylamino-5-[3-(5-fluoro-2-nonen 
ylsulfonyl)phenyl]-4(1H)-pyridone 
1-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(1H)-pyridone 
3-[4-(6,6-dibromo-3-hexynylsulfonyl)phenyl]-5-phenyl-1-propoxy-4(1H)-pyrido 
ne 
3-[3-(2-cyanoethyl)phenyl]-1-ethynyl-5-[1,1,2,2-tetrafluoro-6-decynylsulfon 
yl)phenyl]-4(1H)-pyridone 
3-(3-benzyl-5-ethynylsulfonylphenyl)-5-[2-(7-phenylheptyl)phenyl]-1-vinyl-4 
(1H)-pyridinethione 
1-cyanomethyl-3-[3-(6-dodecynylsulfonyl)-5-methylphenyl]-5-[2-methyl-4-(1,1 
,2,2-tetrafluoroethyl)-phenyl]-4(1H)-pyridone 
1-(2-carboxyethyl)-3-phenyl-5-(3-phenylsulfonyl-phenyl)-4(1H)-pyridone 
3-[3-(4,4-diidobutyl)phenyl]-5-[4-(4-fluorophenylsulfonyl)phenyl]-1-trifluo 
romethyl-4(1H)-pyridone 
3-[2-chloromethyl-3-(6,6-dibromohexyl)phenyl]-5-[3-(3-iodophenylsulfonyl)ph 
enyl]-1-methyl-4(1H)-pyridone 
1-ethyl-3-[3-ethyl-5-(4-methylphenylsulfonyl)-phenyl]-5-[4-iodo-3-(2-propyl 
butyl)phenyl]-4(1H)-pyridinethione 
1-(1-cyanoethyl)-3-[3-(2-propylphenylsulfonyl)-phenyl]-5-phenyl-4(1H)-pyrid 
inethione 
3-[5-butyl-2-(3-methoxyphenylsulfonyl)phenyl]-1-(1-carboxyethyl)-5-phenyl-4 
(1H)-pyridinethione 
3-(3-isopropyl-4-trifluoromethylphenyl)-1-methyl-5-[3-(2-propoxyphenylsulfo 
nyl)phenyl]-4(1H)-pyridone 
3-[2-chloro-4-(4-nitrophenylsulfonyl)phenyl]-1-ethyl-5-[3-fluoro-5-(4-hepty 
l)phenyl]-4(1H)-pyridone 
3-(3-cyclopropylmethylphenyl)-1-methyl-5-(2-trifluoromethylphenyl)-4(1H)-py 
ridone 
3,5-bis[3-(2-cyclopentylethyl)phenyl]-1-methoxy-4(1H)-pyridone 
3-(2-cyclopropoxyphenyl)-1-ethyl-5-(2-fluorophenyl)-4(1H)-pyridinethione 
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(1H)-pyridone, 
hydrochloride 
3-(4-cyclopropylsulfonylphenyl)-5-(2,4-diethylphenyl)-1-propyl-4(1H)-pyridi 
nethione 
3-(3-cyclohexylsulfonylphenyl)-5-(3,5-difluorophenyl)-1-trifluoromethyl-4(1 
H)-pyridone 
1-cyanomethyl-3-(2-cyclopropylmethoxyphenyl)-5-(3-trifluoromethylphenyl)-4( 
1H)-pyridone 
1-acetoxy-3-[3-(2-cyclohexylethoxy)phenyl]-5-phenyl-4(1H)-pyridone, 
hydrobromide 
3-[4-(2-cyclobutylethylthio)phenyl]-1-dimethylamino-5-(3,5-dimethylphenyl)- 
4(1H)-pyridone 
3-(3-cyclopentylmethylsulfinylphenyl)-1-methyl-5-(3-trifluoromethylphenyl)- 
4(1H)-pyridone 
3-[4-(2-cyclohexylethylsulfonyl)phenyl]-1-ethyl-5-(3-propylphenyl)-4(1H)-py 
ridone 
3-cyclopropylmethyl-5-(3-fluorophenyl)-1-methoxy-4(1H)-pyridone, 
methanesulfonate 
3-(4-chlorophenyl)-3-(2-cyclohexylethyl)-1-ethoxy-4(1H)-pyridone 
3-(3-fluorophenyl)-1-methyl-5-phenylthio-4(1H)-pyridone 
3-(3-chloro-5-methylphenyl)-1-ethoxy-5-phenylsulfinyl-4(1H)-pyridone 
1-acetoxy-3-phenylsulfonyl-5-(4-trifluoromethylphenyl)-4(1H)-pyridinethione 
3-(2-butylphenyl)-5-(3,5-dichlorophenylthio)-1-(1-propenyl)-4(1H)-pyridone 
3-(2,4-dibromophenyl)-1-dimethylamino-5-(4-ethylphenylsulfinyl)-4(1H)-pyrid 
one 
1-cyanomethyl-3-phenyl-5-(3-propoxyphenylsulfinyl)-4(1H)-pyridinethione 
3-methylthio-5-phenyl-1-(1-propynyl)-4(1H)-pyridone 
3-(2-chlorophenyl)-1-methyl-5-propylsulfinyl-4(1H)-pyridinethione, 
hydrofluoride 
3-ethylsulfonyl-1-isopropyl-5-(3-trifluoromethylphenyl)-4(1H)-pyridone 
1-ethoxy-3-(4-fluorophenyl)-5-trifluoromethyl-thio-4(1H)-pyridinethione, 
toluenesulfonate 
3-(2-chloroethylsulfinyl)-1-chloromethyl-5-(3-methylphenyl)-4(1H)-pyridone 
3-(2-bromopropylsulfonyl)-1-chlorodifluoromethyl-5-phenyl-4(1H)-pyridinethi 
one 
1-(1-carboxyethyl)-3-(2,4-dimethylphenyl)-5-vinylthio-4(1H)-pyridone 
3-allylsulfinyl-3-(3,5-diiodophenyl)-1-methyl-4(1H)-pyridinethione 
1-methyl-3-(2-trifluoromethylphenyl)-5-vinylsulfonyl-4(1H)-pyridinethione 
3-(3-allylphenyl)-5-(2-chlorovinylthio)-1-ethoxy-4(1H)-pyridinethione 
1-(2-bromoethyl)-3-(2-chloro-3-fluorophenyl)-5-(1,2-difluoroallylsulfinyl)- 
4(1H)-pyridone 
3-(2-bromo-1-propenylsulfonyl)-1-methyl-5-(3-methylphenyl)-4(1H)-pyridineth 
ione 
1-dimethylamino-3-(4-methoxy-2-butenyl)-5-phenyl-4(1H)-pyridone 
1-ethynyl-3-(2-propoxyvinyl)-5-(3-trifluoromethylphenyl)-4(1H)-pyridone 
3-(6-ethoxy-2-hexenyl)-1-methyl-5-phenyl-4(1H)-pyridinethione, 
hydrochloride 
The following are the preferred compounds of the invention. 
1-methyl-3-phenyl-5-(3-trifluoromethylphenyl)-4(1H)-pyridone 
3-(3-fluorophenyl)-1-methyl-5-phenyl-4(1H)-pyridone 
3-(3-chlorophenyl)-1-methyl-5-phenyl-4(1H)-pyridone 
3,5-bis(3-chlorophenyl)-1-methyl-4(1H)-pyridone 
3-(3-chlorophenyl)-5-(3-fluorophenyl)-1-methyl-4(1H)-pyridone 
1-methyl-3-(3-methylphenyl)-5-phenyl-4(1H)-pyridone 
3,5-diphenyl-1-methyl-4(1H)-pyridone 
1-methyl-3,5-bis(3-trifluoromethylphenyl)-4(1H)-pyridone 
3-(3-bromophenyl)-1-methyl-5-phenyl-4(1H)-pyridone 
3-(3-methoxyphenyl)-1-methyl-5-phenyl-4(1H)-pyridone 
3-(3-ethoxyphenyl)-1-methyl-5-phenyl-4(1H)-pyridone 
1-methyl-3-phenyl-5-(3-propoxyphenyl)-4(1H)-pyridone 
3-(3-isopropoxyphenyl)-1-methyl-5-phenyl-4(1H)-pyridone 
1-methyl-3-phenyl-5-[3-(1,1,2,2-tetrafluoroethoxy)phenyl]-4(1H)-pyridone 
3,5-bis(3-fluorophenyl)-1-methyl-4(1H)-pyridone 
3-(2-chlorophenyl)-1-methyl-5-(3-trifluoromethylphenyl)-4(1H)-pyridone 
3-(3-chlorophenyl)-1-methyl-5-(3-trifluoromethylphenyl)-4(1H)-pyridone 
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)-4(1H)-pyridone 
3-(4-fluorophenyl)-1-methyl-5-(3-trifluoromethylphenyl)-4(1H)-pyridone 
3-(3-chlorophenyl)-5-(4-chlorophenyl)-1-methyl-4(1H)-pyridone 
1-ethyl-3-phenyl-5-(3-trifluoromethylphenyl)-4(1H)-pyridone 
1-methyl-3-(3-trifluoromethylphenyl)-4(1H)-pyridone 
3-chloro-1-methyl-5-(3-trifluoromethylphenyl)-4(1H)-pyridone 
3-bromo-1-methyl-5-(3-trifluoromethylphenyl)-4(1H)-pyridone 
1,3-dimethyl-5-(3-trifluoromethylphenyl)-4(1H)-pyridone 
3-ethyl-1-methyl-5-(3-trifluoromethylphenyl)-4(1H)-pyridone 
1-methyl-3-(3-methylthiophenyl)-5-phenyl-4(1H)-pyridone 
3-(4-chloro-3-trifluoromethylphenyl)-1-methyl-5-phenyl-4(1H)-pyridone 
3-(2-chlorophenyl)-5-(3-chlorophenyl)-1-methyl-4(1H)-pyridone 
3-(3-bromophenyl)-5-(3-chlorophenyl)-1-methyl-4(1H)-pyridone 
3-(3-bromophenyl)-1-methyl-5-(2-methylphenyl)-4(1H)-pyridone 
3-(3-chlorophenyl)-1-methyl-5-(2-methylphenyl)-4(1H)-pyridone 
1-methyl-3,5-bis(3-methylphenyl)-4(1H)-pyridone 
3-(2-bromophenyl)-1-methyl-5-(3-trifluoromethylphenyl)-4(1H)-pyridone 
1-methyl-3-(2-methylphenyl)-5-(3-trifluoromethylphenyl)-4(1H)-pyridone 
3-(2-ethylphenyl)-1-methyl-5-(3-trifluoromethylphenyl)-4(1H)-pyridone 
1-methyl-3-(2-trifluoromethylphenyl)-5-(3-trifluoromethylphenyl)-4(1H)-pyri 
done 
3-(2-methoxyphenyl)-1-methyl-5-(3-trifluoromethylphenyl)-4(1H)-pyridone 
3-(3-bromophenyl)-1-methyl-5-(3-trifluoromethylphenyl)-4(1H)-pyridone 
1-methyl-3-(3-methylphenyl)-5-(3-trifluoromethylphenyl)-4(1H)-pyridone 
1-methyl-3-(4-methylphenyl)-5-(3-trifluoromethylphenyl)-4(1H)-pyridone 
3-(3-isobutylphenyl)-1-methyl-5-phenyl-4(1H)-pyridone 
1-methyl-3-propyl-5-(3-trifluoromethylphenyl)-4(1H)-pyridone 
3-methoxy-1-methyl-5-(3-trifluoromethylphenyl)-4(1H)-pyridone 
3-ethoxy-1-methyl-5-(3-trifluoromethylphenyl)-4(1H)-pyridone 
3-isopropoxy-1-methyl-5-(3-trifluoromethylphenyl)-4(1H)-pyridone 
1-methyl-3-phenoxy-5-(3-trifluoromethylphenyl)-4(1H)-pyridone 
3-(4-chloro-3-trifluoromethylphenyl)-5-ethoxy-1-methyl-4(1H)-pyridone 
1-methyl-3-(4-chloro-3-trifluoromethylphenyl)-5-propyl-4(1H)-pyridone 
3-ethyl-1-methyl-5-(4-chloro-3-trifluoromethylphenyl)-4(1H)-pyridone 
3-ethylthio-1-methyl-5-(3-trifluoromethylphenyl)-4(1H)-pyridone 
1-methyl-3-propylthio-5-(3-trifluoromethylphenyl)-4(1H)-pyridone 
1-methyl-3-allylthio-5-(3-trifluoromethylphenyl)-4(1H)-pyridone 
1-methyl-3-isopropylthio-5-(3-trifluoromethylphenyl)-4(1H)-pyridone 
3-ethylsulfinyl-1-methyl-5-(3-trifluoromethylphenyl)-4(1H)-pyridone 
1-methyl-3-(3-trifluoromethylphenyl)-5-trifluoromethylthio-4(1H)-pyridone 
1-methyl-3-(2-chloro-4-fluorophenyl)-5-(3-trifluoromethylphenyl)-4(1H)-pyri 
done 
3-(2,5-dimethylphenyl)-1-methyl-5-(3-trifluoromethylphenyl)-4(1H)-pyridone 
3-(3,4-dimethylphenyl)-1-methyl-5-(3-trifluoromethylphenyl)-4(1H)-pyridone 
1-methyl-3-(3-methylthiophenyl)-5-(3-trifluoromethylphenyl)-4(1H)-pyridone 
1,3-diethyl-5-(3-trifluoromethylphenyl)-4(1H)-pyridone 
1-ethyl-3,5-bis(3-trifluoromethylphenyl)-4(1H)-pyridone 
3-isopropyl-1-methyl-5-(3-trifluoromethylphenyl)-4(1H)-pyridone 
1-methyl-3-phenyl-5-(3-trifluoromethylphenyl)-4(1H)-pyridinethione 
The compounds of this invention can be prepared by various synthetic 
routes. Benary and Bitter, Ber. 61, 1058 (1928) taught the synthesis of an 
intermediate disodium salt of 
1,5-dihydroxy-2,4-diphenyl-1,4-pentadien-3-one by the condensation of 
1,3-diphenyl-2-propanone with ethyl formate in the presence of sodium 
methoxide. The intermediate pentadienone is neutralized by strong acid and 
forms 3,5-diphenyl-4-pyrone. Reaction of the pyrone with ammonium acetate 
at an elevated temperature produces 3,5-diphenyl-4(1H)-pyridone. 
Alternatively, 3,5-diphenyl-4(1H)-pyridones can be prepared by the reaction 
of an appropriately ring-substituted 1,3-diphenyl-2-propanone with 
formamide and formamidine acetate. Reaction at reflux temperature produces 
the corresponding 3,5-diphenyl-4(1H)-pyridone, which is reacted with a 
halide of the desired 1-substituent in the presence of a suitable strong 
base to form the desired compound. 
A preferred synthesis of the compounds is adapted from the methods of 
Benary and Bitter and of El-Kholy et al., cited above. An appropriately 
substituted 1-phenyl-2-propanone is formylated at low temperature with 
sodium methoxide and ethyl formate in ether, and the product is treated 
with an amine salt of the desired R substituent in aqueous medium. The 
resulting intermediate is predominantly a 
1-(R-amino)-2-phenyl-1-buten-3-one. Some pyridone is also formed at this 
step, as reported by El-Kholy et al. The butenone is reformylated as 
before, and spontaneously cyclizes to form the 
1-substituted-3-phenyl-4(1H)-pyridone. 
Another preferred synthesis is similar to the above, but uses an 
aminoformylation step instead of formylation. A preferred aminoformylation 
agent is a formiminium halide, such as the reaction product of phosgene 
and dimethylformamide. The propanone is di-aminoformylated, and the 
intermediate is exchanged with an amine or an amine salt of the R 
substituent and hydrolyzed with acid or alkali to form the 
1-substituted-3-phenyl-4(1H)-pyridone. 
The starting 2-propanones may be prepared by syntheses in the literature. 
For example, see Coan et al., J. Am. Chem. Soc. 76, 501 (1954); Sullivan 
et al., "Disodium Tetracarbonylferrate", American Laboratory 49-56 (June 
1974); Collman et al., "Synthesis of Hemifluorinated Ketones using 
Disodium Tetracarbonylferrate," J. Am. Chem. Soc. 95, 2689-91 (1973); 
Collman et al., "Acyl and Alkyl Tetracarbonylferrate Complexes as 
Intermediates in the Synthesis of Aldehydes and Ketones", J. Am. Chem. 
Soc. 94, 2516-18 (1972). 
The general synthesis methods of the compounds proceed from either ketone 
starting compounds or form carbonyl halides. The general process is the 
same, whichever starting compound is used. The general process, of which 
the preferred synthesis described above is an embodiment, will be 
discussed first. Reagents and reaction conditions will then be explained 
in detail, and some preparative examples will be illustrated. The 
synthesis proceeds through an intermediate of the formula 
##STR5## 
wherein Q.sup.1 and Q.sup.2 independently represent 2 hydrogen atoms, 
.dbd.CHOH, or an alkali metal salt thereof, .dbd.CHN(R.sup.9).sub.2 or 
.dbd.CHNHR, provided that only one of Q.sup.1 and Q.sup.2 represents 
.dbd.CHNHR. 
The R.sup.9 groups independently represent C.sub.1 -C.sub.3 alkyl, or the 
R.sup.9 groups combine with the nitrogen atom to which they are attached 
to form pyrrolidino, piperidino, morpholino, N-methylpiperazino and the 
like. 
The .dbd.CHOH groups, which may be in the form of alkali metal salts, are 
provided by reaction with formylating agents which will be defined below. 
The .dbd.CHN(R.sup.9).sub.2 groups are provided by reaction with 
aminoformylating agents, and the .dbd.CHNHR groups are provided by 
exchanging either .dbd.CHOH groups or .dbd.CHN(R.sup.9).sub.2 groups with 
amines of the formula RNH.sub.2. 
The intermediates described above are prepared from either ketones or 
carbonyl halides, as will be explained below. When Q.sup.1 and Q.sup.2 
each represent 2 hydrogen atoms, the pyridones are prepared by either 
1. reacting with a formylating or aminoformylating agent; 
2. reacting again with a formylating or aminoformylating agent; and 
3. reacting with an amine of the formula RNH.sub.2 ; or 
1. reacting with a formylating or aminoformylating agent; 
2. reacting with an amine of the formula RNH.sub.2 ; and 
3. reacting again with a formylating or aminoformylating agent. 
When one of Q.sup.1 and Q.sup.2 represents either .dbd.CHOH or 
.dbd.CHN(R.sup.9).sub.2, and the other represents 2 hydrogen atoms, the 
pyridones are prepared by either 
1. reacting with a formylating or aminoformylating agent; and 
2. reacting with an amine of the formula RNH.sub.2 ; or 
1. reacting with an amine of the formula RNH.sub.2 ; and 
2. reacting with a formylating or aminoformylating agent. 
When each of Q.sup.1 and Q.sup.2 represent either .dbd.CHOH or 
.dbd.CHN(R.sup.9).sub.2, the pyridones are prepared by reacting with an 
amine of the formula RNH.sub.2. 
The variations of the synthesis, and the preparation of the intermediates, 
will be sketched below. 
When the process starts with a ketone of the general formula 
##STR6## 
the first step is the formylation or aminoformylation of one of the 
methylene groups. If a formylating agent is used, a ketone of the formula 
##STR7## 
is produced. Reaction with an aminoformylating agent produces an 
enaminoketone such as (III) below. 
##STR8## 
Organic chemists will understand that, although the sketches above show the 
first formylation or aminoformylation as occurring on a certain side of 
the ketone, it may in fact occur on either side of the ketone, depending 
on the activating characteristics of R.sup.1 and R.sup.2. The course of 
the reaction is the same in either case. It will also be understood that, 
in many instances, the product of the formylation or aminoformylation step 
will actually be a mixture containing the two possible monosubstituted 
compounds and the disubstituted compound. 
The monosubstituted product is formylated or aminoformylated again, and 
exchanged with an amine of the formula RNH.sub.2. The steps may be 
performed in either order. If the exchange is performed first, the 
intermediate product is an enaminoketone of the formula 
##STR9## 
Either formylation or aminoformylation of the above enaminoketone affords 
the pyridone product, as the intermediate cyclizes as soon as the second 
group is introduced on the other methylene group. 
Alternatively, either of compounds (II) or (III) may be either formylated 
or aminoformylated to provide intermediates of any of the formulae below. 
##STR10## 
It will be understood that the compound similar to (VI), wherein the 
formyl and aminoformyl groups are reversed, is equivalent in all respects 
to compound (VI). Pyridones are formed from any of the above three 
intermediates by simple contact of the intermediate with an amine of the 
formula RNH.sub.2. 
When the starting compound is a carbonyl halide, the process proceeds 
essentially as described above, except for a first step performed as 
follows: 
##STR11## 
It will be understood that reaction (A) can also be performed in the 
opposite manner, as shown below: 
##STR12## 
It is also possible to form intermediates using phosgene as the carbonyl 
halide when the 3- and 5-substituents of the pyridone product are 
identical. 
##STR13## 
The enaminoketones formed in equations (A), (B) and (C) above are identical 
to the intermediates described in (III) and (VII) above, and are converted 
to the pyridone products as described above. 
Alternatively, it is possible to prepare the 1-unsubstituted pyridones by 
using NH.sub.3 in place of RNH.sub.2 in the process, or by using the 
process of Benary and Bitter. The pyridone is then alkylated at the 
1-position with a halide of R, or with a dialkyl sulfate, according to 
common procedures. 
An alternative method of alkylation proceeds by converting the 
1-unsubstituted pyridone to the 4-halo or 4-alkoxy derivative by reaction 
with a halogenating agent, or an O-alkylating agent. Suitable halogenating 
agents include such agents as POCl.sub.3, POBr.sub.3, PCl.sub.5 and the 
like. O-alkylating agents include such reagents as methyl 
trifluoromethanesulfonate, methyl fluorosulfonate and the like, as well as 
alkyl halides used in the presence of base. In the next step, the 4-halo 
or 4-alkoxy compound is reacted with a halide of R to form the 
1-R-substituted, 4-substituted pyridinium salt. The salt is then 
hydrolyzed with either a mineral acid or an alkali metal hydroxide to 
produce the desired product. See, for example, Takahashi et al., Pharm. 
Bull. (Japan) 1, 70-74 (1953). 
As a chemist would expect, the amines, RNH.sub.2, may be used in the form 
of salts, preferably hydrohalide salts, including hydrochlorides, 
hydrobromides and the like. Such salts are often more convenient than the 
free amines. 
The formylating agents used in the process are chosen from the common 
agents used for such reactions. The preferred formylating agents are 
esters of formic acid of the formulae 
##STR14## 
Similar formylations are discussed in Organic Syntheses 300-02 (Collective 
Vol. III 1955). 
The esters are used in the presence of strong bases, of which alkali metal 
alkoxides are preferred, such as sodium methoxide, potassium ethoxide and 
lithium propoxide. Other bases may also be used, including alkali metal 
hydrides, alkali metal amides, and inorganic bases including alkali metal 
carbonates and hydroxides. Such strong organic bases as diazabicyclononane 
and diazabicycloundecane are also useful. 
Reactions with formylating agents are performed in aprotic solvents such as 
are regularly used in chemical synthesis. Ethyl ether is usually the 
preferred solvent. Ethers in general, including solvents such as ethyl 
propyl ether, ethyl butyl ether, 1,2-dimethoxyethane and tetrahydrofuran, 
aromatic solvents such as benzene and xylene, and alkanes such as hexane 
and octane can be used as formylation solvents. 
Because of the strong bases used in the formylation reactions, low 
temperatures produce the best yields. Reaction at temperatures in the 
range of from about -25.degree. C. to about 10.degree. C. is preferred. 
The reaction mixture may be allowed to warm to room temperature, however, 
after the reaction has proceeded part way to completion. Reaction times 
from about 1 to about 24 hours are adequate for economic yields in the 
formylation reactions. 
The aminoformylating agents used in these syntheses may be any compounds 
capable of reacting with an active methylene group to introduce a 
.dbd.CHN(R.sup.9).sub.2 group, or its acid addition salt. Such agents are 
chosen from among s-triazine, the orthoformamides, 
EQU HC[N(R.sup.9).sub.2 ].sub.3 
the formate ester aminals, 
##STR15## 
the formamide acetals, 
##STR16## 
the tris(formylamino)methanes, 
##STR17## 
and preferably from the formiminium halides, 
##STR18## 
Q.sup.3 in the structures above represents oxygen or sulfur, and R.sup.10 
represents C.sub.1 -C.sub.6 alkyl or phenyl. 
Useful references on the aminoformylating agents include DeWolfe, 
Carboxylic Acid Derivatives 420-506 (Academic Press 1970), and Ulrich, 
Chemistry of Imidoyl Halides 87-96 (Plenum Press 1968). Bredereck et al. 
have written many papers on such agents and reactions, of which the 
following are typical. Ber. 101, 4048-56 (1968); Ber. 104, 2709-26 (1971); 
Ber. 106, 3732-42 (1973); Ber. 97, 3397-406 (1964); Ann. 762, 62-72 
(1972); Ber. 97, 3407-17 (1964); Ber. 103, 210-21 (1970); Angew. Chem. 78, 
147 (1966); Ber. 98, 2887-96 (1965); Ber. 96, 1505-14 (1963); Ber. 104, 
3475-85 (1971); Ber. 101, 41-50 (1968); Ber. 106, 3725-31 (1973); and 
Angew. Chem. Int'l. Ed. 5, 132 (1966). Other notable papers on the subject 
include Kreutzberger et al., Arch. der Pharm. 301, 881-96 (1968), and 302, 
362-75 (1969), and Weingarten et al., J. Org. Chem. 32, 3293-94 (1967). 
Aminoformylations are usually carried out without solvent, at elevated 
temperatures from about 50.degree. C. to about 200.degree. C. Solvents 
such as dimethylformamide are sometimes used, however, particularly when 
it is desirable to raise the boiling point of the reaction mixture. 
When aminoformylating with formiminium halides, however, aprotic solvents, 
such as described above in the description of solvents for formylation, 
are used at temperatures from about 0.degree. C. to about 80.degree. C., 
preferably above room temperature. Halogenated solvents such as chloroform 
and methylene chloride can also be used in such aminoformylations if 
desired. 
The exchange reactions with RNH.sub.2 are best performed in protic solvents 
of which alkanols are preferred and ethanol is most appropriate. 
Temperatures from about -20.degree. C. to about 100.degree. C. can be used 
for the exchange reactions. Room temperature is satisfactory and is 
preferred. 
In general, intermediate compounds in the synthesis are not purified, but 
are simply used in successive steps after separation by extraction, 
neutralization or removal of excess solvent or reactant as appropriate. 
The enamine acylation reactions, A-C, are performed in the presence of 
bases such as tertiary amines, alkali metal carbonates, magnesium oxide 
and the like, and in aprotic solvents as described above. 
In some instances, as organic chemists will understand, it is necessary to 
apply additional synthetic steps after the pyridone compound has been 
formed. For example, it is convenient to form compounds having alkoxy, 
alkanoyloxy and like R.sup.1 and R.sup.5 substituents by first making the 
corresponding hydroxy-substituted compound, and then substituting on the 
oxygen atom. 
The pyridinethiones of this invention are readily prepared by the treatment 
of the corresponding pyridones with P.sub.2 S.sub.5 in pyridine at reflux 
temperature, according to known methods. 
The 1-acetoxy compounds are made by first making the corresponding 
1-hydroxypyridone, using NH.sub.2 OH as the amine, and esterifying it with 
acetic anhydride. The other 1-substituents are provided by appropriate R 
substituents on the amines, RNH.sub.2, used to prepare the pyridones. 
The following preparative examples are presented to assure that those 
skilled in organic chemistry can obtain any desired compound of this 
invention. 
The examples below show the various processes by which compounds of the 
invention have been made. It will be understood, however, that all of the 
various processes can be used, with appropriate variations, to make any 
compound of the invention. 
Many exemplary compounds are indicated as made by the general process of a 
previous exemplary compound. In such instances, an ordinarily skilled 
organic chemist will readily see the minor changes to the exemplary 
process which will be needed to prepare the other exemplary compounds.