Pyridine derivatives and their use for controlling undesirable plant growth

Pyridine derivatives of the formulae ##STR1## wherein W, X, Y and Z are each C--R.sup.4, N or N.fwdarw.O, with the proviso that the ring contains only one heteroatom, and the substituents R.sup.1, R.sup.2 and R.sup.3 have the following meanings: PA0 R.sup.1 is alkoxy, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted alkenyl, or substituted or unsubstituted alkynyl, PA0 R.sup.2 is hydrogen, PA0 R.sup.3 is formyl, 4,5-dihydrooxazol-2-yl or --CO--A--R.sup.5 or --CO--NR.sup.6.sup.R.sup.7, where PA0 R.sup.4 is halogen, nitro, cyano, substituted or unsubstituted alkyl, substituted or unsubstituted benzyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, alkoxy, alkylthio, haloalkoxy, haloalkylthio, alkenyloxy, alkynyloxy, alkylsulfinyl, alkylsulfonyl, haloalkylsulfonyl, substituted or unsubstituted phenoxy or phenylthio, a substituted or unsubstituted 5- or 6-membered heterocyclic radical having one or two heteroatoms selected from the group consisting of oxygen, sulfur and nitrogen, or is substituted or unsubstituted phenyl, PA0 A is oxygen or sulfur, PA0 R.sup.5 is hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted benzyl, cycloalkyl, substituted or unsubstituted phenyl, PA0 one equivalent of a cation or the radical --N.dbd.CR.sup.8 R.sup.9 and PA0 R.sup.6 and R.sup.7 are hydrogen or alkyl or together denote a methylene chain having 4 or 5 members, their agriculturally utilizable salts, and their use for controlling unwanted plant growth.

The present invention relates to novel pyridine derivatives, processes for 
their preparation and their use for controlling undesirable plant growth. 
N-substituted pyridinedicarboximides and their derivatives are known. 
EP-A-128 006 describes, inter alia, N-cycloalkylenepyridinecarboximides 
and their use as soil fungicides. 
DE-A-31 22 635 discloses 2,6-dichloropyridine-3,4-dicarboxylic acid 
N-alkylimides which are suitable as coupling components for azo dyes. 
U.S. Pat. No. 3,539,568 describes a process for the preparation of 2,3- and 
3,4-pyridinedicarboximides and their conversion into isomeric 
dicarboxamides, which can U.S. Pat. No. 4,261,730 discloses 
3-carboxypyridine-2-N-(aryl)-carboxamides and phthalamic acids having a 
growth-regulating action. 
U.S. Pat. No. 4,658,030 discloses a process for the preparation of 
herbicidal 2-(imidazolin-2-yl)-nicotinic acids based on 
3-carboxypyridin-2-(N-carbamido-3-methyl-2-butyl)-carboxamides. 
Helv. Chim. Acta 71 (1988), 486 and 493 discloses a cycloaddition process 
for the preparation of pyridine-2,3-dicarboximides. These substances are 
not known to have herbicidal properties. 
We have found that pyridine derivatives of the formulae I'a, I'b and I'c 
##STR2## 
where W, X, Y and Z are each C--R.sup.4, N or N.fwdarw.O, with the proviso 
that the ring contains only one hetero atom, and R.sup.1 is hydrogen, 
hydroxyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.6 -alkyl which may 
carry from one to three of the following groups: C.sub.1 -C.sub.4 -alkoxy, 
C.sub.1 --C.sub.4 -haloalkoxy, C.sub.1 -C.sub.4 -alkylthio, C.sub.1 
-C.sub.4 -haloalkylthio, C.sub.1 -C.sub.4 -dialkylamino, C.sub.3 -C.sub.8 
-cycloalkyl, halogen, cyano, C.sub.3 -C.sub.8 -cycloalkyl or phenyl which 
may be substituted by halogen, cyano, nitro, C.sub.1 -C.sub.4 -alkyl, 
C.sub.1 -C.sub.4 -haloalkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 
-haloalkoxy, C.sub.1 -C.sub.4 -alkylthio or C.sub.1 -C.sub.4 
-haloalkylthio; 
C.sub.3 -C.sub.8 -cycloalkyl which may carry from one to three of the 
following groups: C.sub.1 -C.sub.6 -alkyl, C.sub.1 -C.sub.6 -haloalkyl, 
C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -haloalkoxy, halogen, nitro or 
cyano; 
C.sub.3 -C.sub.6 -alkenyl or C.sub.3 -C.sub.6 -alkynyl, each of which may 
be monosubstituted to trisubstituted by halogen and/or monosubstituted by 
phenyl which may carry from one to three of the following groups: C.sub.1 
-C.sub.4 -alkyl, C.sub.1 -C.sub.4 -haloalkyl, C.sub.1 -C.sub.4 -alkoxy, 
C.sub.1 -C.sub.4 -haloalkoxy, C.sub.1 -C.sub.4 -alkylthio, C.sub.1 
-C.sub.4 -haloalkylthio, halogen, cyano or nitro; 
C.sub.1 -C.sub.4 -dialkylamino; 
a 5-membered or 6-membered heterocyclic radical having one or two 
heteroatoms selected from the group consisting of oxygen, sulfur and 
nitrogen, which may be up to trisubstituted by C.sub.1 -C.sub.4 -alkyl or 
halogen; 
phenyl which may carry from one to four of the following groups: C.sub.1 
-C.sub.4 -alkyl, C.sub.1 -C.sub.4 -haloalkyl, C.sub.1 -C.sub.4 -alkoxy, 
C.sub.1 -C.sub.4 -haloalkoxy, C.sub.1 -C.sub.4 -alkylthio, C.sub.1 
-C.sub.4 -haloalkylthio, halogen, nitro, cyano, formyl, C.sub.2 -C.sub.5 
-alkanoyl, C.sub.2 -C.sub.5 -haloalkanoyl or C.sub.2 -C.sub.5 
-alkoxycarbonyl, or 
naphthyl which may be monosubstituted to trisubstituted by C.sub.1 -C.sub.4 
-alkyl or halogen; 
R.sup.2 is hydrogen or C.sub.1 -C.sub.6 -alkyl which may carry from one to 
three of the following substituents: hydroxyl, halogen, C.sub.1 -C.sub.4 
-alkoxy, C.sub.1 -C.sub.4 -alkylthio or C.sub.1 -C.sub.4 -dialkylamino; 
C.sub.3 -C.sub.8 -cycloalkyl which may be monosubstituted to 
trisubstituted by C.sub.1 -C.sub.4 -alkyl, halogen or C.sub.1 -C.sub.4 
-haloalkyl, or 
R.sup.1 and R.sup.2 together form a radical having the structure 
--(CH.sub.2).sub.n --Y.sub.p --(CH.sub.2).sub.q --, where n and q are each 
1, 2 and 3, p is 0 or 1 and Y is oxygen or sulfur or N-methyl or the 
radical of the formula --(CH.sub.2).sub.3 --CO--; 
R.sup.3 is formyl, 4,5-dihydrooxazol-2-yl or one of the radicals 
--COAR.sup.5 or --CONR.sup.6 R.sup.7 ; 
R.sup.4 is hydrogen, halogen, nitro, cyano or C.sub.1 -C.sub.6 -alkyl which 
may be substituted by one to five halogen atoms and/or one or two of the 
following radicals: C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 
-haloalkoxy, C.sub.1 -C.sub.4 -alkylthio, C.sub.1 -C.sub.4 -haloalkylthio, 
C.sub.3 -C.sub.6 -cycloalkyl or cyano; 
benzyl which may be monosubstituted to trisubstituted by C.sub.1 -C.sub.4 
-alkyl, C.sub.1 -C.sub.4 -haloalkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 
-C.sub.4 -haloalkoxy, C.sub.1 -C.sub.4 -alkylthio, C.sub.1 -C.sub.4 
-haloalkylthio, halogen, cyano or nitro; 
C.sub.3 -C.sub.8 -cycloalkyl which may be monosubstituted to trisubstituted 
by C.sub.1 -C.sub.4 -alkyl or halogen; 
C.sub.2 -C.sub.8 -alkenyl which may be monosubstituted to trisubstituted by 
halogen and/or monosubstituted by C.sub.1 -C.sub.3 -alkoxy or by phenyl 
which may carry from one to three of the following groups: C.sub.1 
-C.sub.4 -alkyl, C.sub.1 -C.sub.4 -haloalkyl, C.sub.1 -C.sub.4 -alkoxy, 
C.sub.1 -C.sub.4 -haloalkoxy, C.sub.1 -C.sub.4 -alkylthio, C.sub.1 
-C.sub.4 -haloalkylthio, halogen, cyano or nitro; 
C.sub.2 -C.sub.6 -alkynyl which may be monosubstituted to trisubstituted by 
halogen or C.sub.1 -C.sub.3 -alkoxy and/or monosubstituted by phenyl which 
may carry from one to three of the following groups: C.sub.1 -C.sub.4 
-alkyl, C.sub.1 -C.sub.4 -haloalkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 
-C.sub.4 -haloalkoxy, C.sub.1 -C.sub.4 -alkylthio, C.sub.1 -C.sub.4 
-haloalkylthio, halogen, cyano or nitro; 
C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -alkylthio, C.sub.1 -C.sub.4 
-haloalkoxy, C.sub.1 -C.sub.4 -haloalkylthio, C.sub.2 -C.sub.5 
-alkenyloxy, C.sub.2 -C.sub.5 -alkynyloxy, C.sub.1 -C.sub.4 
-alkylsulfinyl, C.sub.1 -C.sub.4 -alkylsulfonyl or C.sub.1 -C.sub.4 
-haloalkylsulfonyl; 
phenoxy or phenylthio, each of which may be monosubstituted to 
trisubstituted by C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -haloalkyl, 
C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -haloalkoxy, C.sub.1 -C.sub.4 
-alkylthio, C.sub.1 -C.sub.4 -haloalkylthio, halogen, cyano or nitro; 
a 5-membered or 6-membered heterocyclic radical having one or two 
heteroatoms selected from the group consisting of oxygen, sulfur and 
nitrogen, which may carry one or two substituents of the following groups: 
C.sub.1 -C.sub.3 -alkyl, halogen, C.sub.1 -C.sub.3 -alkoxy or C.sub.2 
-C.sub.4 -alkoxycarbonyl, or 
phenyl which may carry from one to three of the following groups: C.sub.1 
-C.sub.6 -alkyl, C.sub.1 -C.sub.6 -haloalkyl, C.sub.1 -C.sub.6 -alkoxy, 
C.sub.1 -C.sub.6 -haloalkoxy, C.sub.1 -C.sub.6 -alkylthio, C.sub.1 
-C.sub.6 -haloalkylthio, halogen, nitro or cyano; 
A is oxygen or sulfur; 
R.sup.5 is hydrogen or C.sub.1 -C.sub.6 -alkyl which may be one to five 
halogen atoms or one to five hydroxyl groups 
and/or one of the following radicals: C.sub.1 -C.sub.4 -alkoxy, C.sub.1 
-C.sub.4 -alkoxy-C.sub.2 -C.sub.4 -alkoxy, cyano, trimethylsilyl, C.sub.1 
-C.sub.3 -alkylthio, C.sub.1 -C.sub.3 -alkylamino, C.sub.1 -C.sub.3 
-dialkylamino, C.sub.1 -C.sub.3 -alkylsulfinyl, C.sub.1 -C.sub.3 
-alkylsulfonyl, carboxyl, C.sub.1 -C.sub.3 -alkoxycarbonyl, C.sub.2 
-C.sub.4 -alkoxycarbonyl-C.sub.1 -C.sub.3 -alkoxy, C.sub.2 -C.sub.4 
-alkoxycarbonyl-C.sub.1 -C.sub.3 -alkoxycarbonyl, C.sub.1 -C.sub.3 
-dialkylaminocarbonyl, C.sub.1 -C.sub.3 -dialkoxyphosphonyl, alkaniminoxy, 
thienyl, furyl, tetrahydrofuryl, phthalimido, pyridyl, benzyloxy or 
benzoyl which may carry from one to three of the following groups: C.sub.1 
-C.sub.3 -alkyl, C.sub.1 -C.sub.3 -alkoxy or halogen; 
benzyl which may carry from one to three of the following groups: C.sub.1 
-C.sub.3 -alkyl, C.sub.1 -C.sub.3 -alkoxy, C.sub.1 -C.sub.3 -haloalkyl, 
halogen, nitro or cyano; 
C.sub.3 -C.sub.8 -cycloalkyl; 
phenyl which may carry from one to three of the following groups: C.sub.1 
-C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -haloalkyl, 
C.sub.1 -C.sub.4 -haloalkoxy, C.sub.1 -C.sub.4 -alkoxycarbonyl, halogen, 
nitro or cyano; 
C.sub.3 -C.sub.8 -alkenyl, C.sub.5 - or C.sub.6 -cycloalkenyl, C.sub.3 
-C.sub.6 -alkynyl, each of which may be monosubstituted by hydroxyl, 
C.sub.1 -C.sub.4 -alkoxy, halogen or phenyl, which may carry from one to 
three of the following groups: C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 
-alkoxy, C.sub.1 -C.sub.4 -haloalkyl, halogen, nitro or cyano; 
a 5-membered or 6-membered heterocyclic radical having one or two 
heteroatoms selected from the group consisting of oxygen, sulfur and 
nitrogen, or benzotriazolyl; 
phthalimido, tetrahydrophthalimido, succinimido or maleimido; 
one equivalent of a cation from the group consisting of the alkali or 
alkaline earth metals, manganese, copper, iron, ammonium and substituted 
ammonium, or a radical --N.dbd.CR.sup.8 R.sup.9, where 
R.sup.8 and R.sup.9 independently of one another are each hydrogen, C.sub.1 
-C.sub.4 -alkyl, C.sub.1 -C.sub.6 -cycloalkyl, phenyl or furyl or together 
may form a methylene chain having 4 to 7 members; 
R.sup.6 is hydrogen, C.sub.1 -C.sub.6 -alkyl or C.sub.3 -C.sub.8 
-cycloalkyl and 
R.sup.7 is hydrogen or C.sub.1 -C.sub.6 -alkyl, or R.sup.6 and R.sup.7 may 
form a methylene chain having 4 or 5 members, 
and salts thereof which can be used in agriculture possess herbicidal 
activity and are selective with respect to crops. 
Pyridine derivatives of the formulae Ia, Ib and Ic 
##STR3## 
where 
X, Y and Z are each C--R.sup.4, N or N.fwdarw.O, with the proviso that the 
ring contains only one heteroatom, and 
R.sup.1 is C.sub.1 -C.sub.4 -alkoxy or is C.sub.3 -C.sub.6 -alkyl which may 
carry from one to three of the following groups: C.sub.1 -C.sub.4 -alkoxy, 
C.sub.1 -C.sub.4 -haloalkoxy, C.sub.1 -C.sub.4 -alkylthio, C.sub.1 
-C.sub.4 -haloalkylthio, C.sub.1 -C.sub.4 -dialkylamino, C.sub.3 -C.sub.8 
-cycloalkyl or halogen, 
C.sub.3 -C.sub.8 -cycloalkyl which may carry from one to three of the 
following groups: C.sub.1 -C.sub.6 -alkyl, C.sub.1 -C.sub.6 -haloalkyl, 
C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -haloalkoxy, halogen, nitro or 
cyano, 
C.sub.3 -C.sub.6 -alkenyl or C.sub.3 -C.sub.6 -alkynyl, each of which may 
be monosubstituted to trisubstituted by halogen, 
R.sup.2 is hydrogen, 
R.sup.3 is formyl, 4,5-dihydrooxazol-2-yl or one of the radicals 
--CO--A--R.sup.5 or --CO--NR.sup.6 R.sup.7, 
A is oxygen or sulfur, 
R.sup.4 is halogen, nitro, cyano or C.sub.1 C.sub.6 -alkyl which may be 
substituted by one to five halogen atoms and/or one or two of the 
following radicals: C.sub.1 -C.sub.4 -alkoxy, C.sub.1 C.sub.4 -haloalkoxy, 
C.sub.1 -C.sub.4 -alkylthio, C.sub.1 -C.sub.4 -haloalkylthio, C.sub.3 
-C.sub.5 -cycloalkyl or cyano, 
benzyl which may be monosubstituted to trisubstituted by C.sub.1 -C.sub.4 
-alkyl, C.sub.1 -C.sub.4 -haloalkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 
-C.sub.4 -haloalkoxy, C.sub.1 -C.sub.4 -alkylthio, C.sub.1 -C.sub.4 
-haloalkylthio, halogen, cyano or nitro, 
C.sub.3 -C.sub.8 -cycloalkyl which may be monosubstituted to trisubstituted 
by C.sub.1 -C.sub.4 -alkyl or halogen, 
C.sub.2 -C.sub.6 -alkenyl which may be monosubstituted to trisubstituted by 
halogen and/or monosubstituted by C.sub.1 -C.sub.3 -alkoxy or by phenyl 
which may carry from one to three of the following groups: C.sub.1 
-C.sub.4 -alkyl, C.sub.1 -C.sub.4 -haloalkyl, C.sub.1 -C.sub.4 -alkoxy, 
C.sub.1 -C.sub.4 -haloalkoxy, C.sub.1 -C.sub.4 -alkylthio, C.sub.1 
-C.sub.4 -halalkylthio, halogen, cyano or nitro, 
C.sub.2 -C.sub.6 -alkynyl which may be monosubstituted to trisubstituted by 
halogen or C.sub.1 -C.sub.3 -alkoxy and/or monosubstituted by phenyl which 
may carry from one to three of the following groups: C.sub.1 -C.sub.4 
-alkyl, C.sub.1 -C.sub.4 -haloalkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 
-C.sub.4 -haloalkoxy, C.sub.1 -C.sub.4 -alkylthio, C.sub.1 -C.sub.4 
-haloalkylthio, halogen, cyano or nitro, 
C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -alkylthio, C.sub.1 -C.sub.4 
-haloalkoxy, C.sub.1 -C.sub.4 -haloalkylthio, C.sub.2 -C.sub.5 
-alkenyloxy, C.sub.2 -C.sub.5 -alkynyloxy, C.sub.1 -C.sub.5 
-alkylsulfinyl, C.sub.1 -C.sub.4 -alkylsulfonyl or C.sub.1 -C.sub.4 
-haloalkylsulfonyl, 
phenoxy or phenylthio, each of which may be monosubstituted to 
trisubstituted by C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -haloalkyl, 
C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -haloalkoxy, C.sub.1 -C.sub.4 
-alkylthio, C.sub.1 -C.sub.4 -haloalkylthio, halogen, cyano or nitro, 
a 5-membered or 6-membered heterocyclic radical having one or two 
heteroatoms selected from the group consisting of oxygen, sulfur and 
nitrogen, which may carry one or two substituents of the following groups: 
C.sub.1 -C.sub.3 -alkyl, halogen, C.sub.1 -C.sub.3 -alkoxy or C.sub.2 
-C.sub.4 -alkoxycarbonyl, phenyl which may carry from one to three of the 
following groups: C.sub.1 -C.sub.6 -alkyl, C.sub.1 -C.sub.6 -haloalkyl, 
C.sub.1 -C.sub.6 -alkoxy, C.sub.1 -C.sub.6 -haloalkoxy, C.sub.1 -C.sub.6 
-alkylthio, C.sub.1 -C.sub.6 -haloalkylthio, halogen, nitro or cyano, 
R.sup.5 is hydrogen or C.sub.1 -C.sub.6 -alkyl which may be substituted by 
one to five halogen atoms or one to five hydroxyl groups and/or one of the 
following radicals: C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 
-alkoxy-C.sub.2 -C.sub.4 -alkoxy, cyano or C.sub.1 -C.sub.3 -alkylthio, 
benzyl which may carry from one to three of the following groups: C.sub.1 
-C.sub.3 -alkyl, C.sub.1 -C.sub.3 -alkoxy, C.sub.1 -C.sub.3 -haloalkyl, 
halogen, nitro or cyano, 
C.sub.3 -C.sub.8 -cycloalkyl, 
phenyl which may carry from one to three of the following groups: C.sub.1 
-C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -haloalkyl, 
C.sub.1 -C.sub.4 -haloalkoxy, C.sub.2 -C.sub.5 -alkoxycarbonyl, halogen, 
nitro or cyano; one equivalent of a cation from the group consisting of 
the alkali or alkaline earth metals, manganese, copper, iron, ammonium and 
substituted ammonium, or a radical --N.dbd.CR.sup.8 R.sup.9, 
R.sup.8 and R.sup.9 independently of one another are each hydrogen, C.sub.1 
-C.sub.4 -alkyl or C.sub.3 -C.sub.6 -cycloalkyl or together may form a 
methylene chain having 4 to 7 members, 
R.sup.6 and R.sup.7 are each hydrogen or C.sub.1 -C.sub.6 -alkyl or 
together may form a methylene chain having 4 or 5 members, with the 
proviso 
that X and Z in formula Ia are not simultaneously C--R.sup.4, 
where R.sup.4 is halogen, or independently of one another C--R.sup.4, 
where R.sup.4 is halogen or hydroxyl, when Y is N, 
and that X in formula Ia is not C--R.sup.4, where R.sup.4 is phenyl, when Y 
is N, 
and salts thereof which can be used in agriculture are novel. 
The pyridine derivatives Ia, Ib and Ic or I'a, I'b and I'c may form 
addition salts, for example with inorganic and organic acids or with alkyl 
halides, or, if one of the substituents has acidic properties, said 
derivatives can be reacted with inorganic and organic bases to form salts. 
The present invention also relates to the corresponding salts. 
Pyridine derivatives which are preferred as herbicidal active ingredients 
are those of the formulae I'b and I'c where R.sup.2 is hydrogen. 
Further preferred pyridine derivatives of the formulae I'b and I'c are 
those in which one of the ring members W, X, Y and Z is N and the others 
are each C--R.sup.4, R.sup.1 is C.sub.3 -C.sub.6 -alkyl, C.sub.3 -C.sub.6 
-alkenyl, C.sub.3 -C.sub.6 -alkynyl or C.sub.3 -C.sub.6 -cycloalkyl, 
R.sup.2 is hydrogen, R.sup.3 is a radical --CO--A--R.sup.5 and R.sup.4 is 
hydrogen, halogen, nitro, cyano, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 
-alkoxy, C.sub.1 -C.sub.4 -alkylthio, C.sub.1 -C.sub.4 -alkylsulfonyl, 
C.sub.1 -C.sub.4 -haloalkyl, C.sub.1 -C.sub.4 -haloalkoxy or C.sub.1 
-C.sub.4 -haloalkylthio. In these compounds, R.sup.5 is preferably 
hydrogen, C.sub.1 -C.sub.4 -alkyl, phenyl which is unsubstituted or 
substituted by C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -haloalkyl, 
C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -alkylthio or halogen, or a 
radical --N.dbd.CR.sup.8 R.sup.9, where R.sup.8 and R.sup. 9 are each 
preferably C.sub.1 -C.sub.4 -alkyl. A is preferably oxygen; the C.sub.1 
-C.sub.4 -haloalkyl radical R.sup.4 may be substituted by one to five, 
preferably 3, halogen atoms. 
The pyridine derivatives of the formulae Ia, Ib and Ic can be prepared by 
various methods: 
1. The compounds Id and Ie are converted into the pyridine derivatives of 
the formula Ia by dehydration with water-eliminating agents, for example 
acetic anhydride or inorganic acid halides. The reaction is advantageously 
carried out by a procedure in which the carboxamides in an inert organic 
solvent are initially taken and about molar amounts of a water-eliminating 
agent, if necessary likewise dissolved in an inert solvent, are added 
dropwise. The mixture can be worked up in a conventional manner, for 
example by hydrolysis with water and filtration of the product under 
suction or by extraction of the product with an organic solvent and 
evaporation of the organic solvent: 
##STR4## 
Advantageously, solvents such as halohydrocarbons, e.g. tetrachloroethane, 
methylene chloride, chloroform, dichloroethane, chlorobenzene and 
1,2-dichlorobenzene, ethers, e.g. diethyl ether, methyl tert-butyl ether, 
dimethoxyethane, diethylene glycol diethyl ether, tetrahydrofuran and 
dioxane, dipolar aprotic solvents, e.g. acetonitrile, dimethylformamide, 
dimethylacetamide, dimethyl sulfoxide, N-methylpyrrolidone, 
1,3-dimethyltetrahydro-2(1H)-pyrimidinone and 
1,3-dimethylimidazolidin-2-one, aromatics, e.g. benzene, toluene, xylene, 
pyridine and quinoline, ketones, e.g. acetone and methyl ethyl ketone, and 
corresponding mixtures are used for these reactions. 
The reaction can be carried out at from -10.degree. C. to the reflux 
temperature of the particular solvent, preferably from 0.degree. to 
150.degree. C. 
The molar ratios in which the required starting compounds are reacted with 
one another are in general from 0.9:1 to 5:1 for the ratio of 
water-eliminating agent to acid amide. 
The concentration of the educts in the solvent (mixture) is in general from 
0.1 to 5, preferably from 0.2 to 2, mol/l. 
2. A process for the preparation of compounds of the formulae Ib and Ic in 
which R.sup.3 is a radical --CO--A--R.sup.5, A is oxygen and R.sup.5 is 
hydrogen, is based on the reaction of a substituted pyridinedicarboxylic 
anhydride with an amine. 
The reaction is advantageously carried out by a procedure in which the 
anhydride II in an inert solvent is initially taken and about molar 
amounts of an amine III, if necessary likewise dissolved in an inert 
solvent, are added dropwise. After the end of the reaction, the reaction 
product is filtered off under suction or is isolated by evaporating the 
solvent used, the amides Ib or their isomers Ic being obtained. 
##STR5## 
The isomer distribution is essentially determined by the position of the 
heteroatom. For example, Z.dbd.N leads to preferential formation of Ic 
whereas the formation of Ib takes place preferentially in the case of 
Y.dbd.N. 
Advantageously, solvents such as halohydrocarbons, e.g. tetrachloroethane, 
methylene chloride, chloroform, chlorobenzene and 1,2-dichlorobenzene, 
ethers, e.g. diethyl ether, methyl tert-butyl ether, dimethoxyethane, 
diethylene glycol dimethyl ether, tetrahydrofuran and dioxane, dipolar 
aprotic solvents, e.g. acetonitrile, dimethylformamide, dimethylacetamide, 
dimethyl sulfoxide, N-methylpyrrolidone, 
1,3-dimethyltetrahydro-2(1H)-pyrimidinone and 
1,3-dimethylimidazolidin-2-one, aromatics, e.g. benzene, toluene, xylene, 
pyridine and quinoline, ketones, e.g. acetone and methyl ethyl ketone, and 
corresponding mixtures are used for these reactions. 
The reaction can be carried out at from -10.degree. C. to the reflux 
temperature of the particular solvent or solvent mixture, preferably from 
-20.degree. to 120.degree. C. 
The molar ratios in which the required starting compounds are reacted with 
one another are from 0.9:1 to 3:1 for the ratio of amine III to anhydride 
II. The concentration of the educts in the solvent is from 0.1 to 5, 
preferably from 0.2 to 2, mol/l. 
The pyridinedicarboxylic acids or anhydrides required as starting materials 
for this process are commercially available or known from the literature 
or can be prepared by conventional methods. An overview appears in 
Beilstein H 22, 150-160, E I 531-536, E II 104-111, H 27 261, E I 319, E 
II 299, R. C. Elderfield, Heterocyclic Compounds, Vol. I, Chapter 8, J. 
Wiley and Sons, N.Y., and E. Klingberg, Pyridine and its Derivatives, Part 
3, Chapter X, in The Chemistry of Heterocyclic Compounds, 1962, 
Interscience Publishers, and in EP-A-299 362. 
3. A process for the synthesis of compounds of the formulae Ib and Ic, in 
which R.sup.3 is a radical --CO--A--R.sup.5, A is oxygen and R.sup.5 is 
hydrogen or C.sub.1 -C.sub.6 -alkyl which is unsubstituted or substituted 
by one to five halogen atoms or one to five hydroxyl groups and/or one of 
the radicals C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -alkoxy-C.sub.1 
-C.sub.4 -alkoxy, cyano or C.sub.1 -C.sub.3 -alkylthio, comprises reacting 
a pyridinedicarboxylic mono- or diester IV with an amine III. 
Particularly suitable mono- or dialkyl esters IV are lower alkyl esters, 
preferably dimethyl esters or diethyl esters. The reaction is carried out 
by a method in which a dicarboxylic mono- or dialkyl ester IV is treated 
with about one equivalent of a primary or secondary amine III at from 
0.degree. to 130.degree. C., preferably from 50.degree. to 100.degree. C., 
in an organic solvent. After the reaction is complete, the mixture is 
cooled and the product is filtered off under suction or the solution is 
evaporated down. The resulting products of the formulae Ib and Ic can be 
further purified by conventional standard methods, such as 
recrystallization or chromatography. 
##STR6## 
The isomer distribution is essentially determined by the position of the 
heteroatom. For example, in the case of a dialkyl ester, Z.dbd.N leads to 
the preferential formation of Ic whereas the formation of Ib takes place 
preferentially when Y.dbd.N. In the case of a monoalkyl ester IV, the 
particular ester radical is displaced regardless of the position of the 
heteroatom. 
Ethers, e.g. diethyl ether, methyl tert-butyl ether, dimethoxyethane, 
diethylene glycol dimethyl ether, tetrahydrofuran and dioxane, aromatics, 
e.g. benzene, toluene, xylene and mesitylene, alcohols, e.g. methanol, 
ethanol, n-propanol, isopropanol and tert-butanol, and corresponding 
mixtures are used as solvents for these reactions. 
The molar ratio in which the mono- or diester IV and the amine III are used 
is from 0.9:1 to 2:1, preferably from 1:1 to 1:1.2. 
The concentration of the educts in the solvent (mixture) is in general from 
0.1 to 5, preferably from 0.2 to 2, mol/l. 
4. Compounds of the formula Ia may also be prepared by reacting a monoalkyl 
pyridinedicarboxylate V with a halogenating agent and then reacting the 
product with an amine III. 
##STR7## 
The reaction is carried out by a method in which a half ester V is 
converted in a conventional manner with an inorganic acid halide, such as 
thionyl chloride, phosgene, phosphorus trichloride, phosphorus tribromide 
or phosphorus pentachloride, preferably thionyl chloride, into the acid 
halide VI. 
Advantageously, the inorganic acid halide is used in an amount of from 1 to 
5, preferably from 1 to 2, molar equivalents, based on carboxylic acid V 
used. 
It is also possible to carry out the reaction without a solvent or in the 
presence of an inert inorganic solvent; halohydrocarbons, e.g. 
tetrachloroethane, methylene chloride, chloroform, dichloroethane, 
chlorobenzene and 1,2-dichlorobenzene, and aromatics, e.g. benzene, 
toluene and xylene, are advantageously used. The reaction is carried out 
at from 0.degree. C. to the boiling point of the inorganic acid halide or 
of the solvent used, preferably at from 20.degree. to 120.degree. C. 
In some cases, the addition of a catalyst, such as dimethylformamide or 
4-dimethylaminopyridine, may be advantageous. The concentration of the 
catalyst is from 0.3 to 20 mol %, based on carboxylic acid V used. 
The reaction is particularly preferably carried out without a solvent, in 
thionyl chloride as the inorganic acid halide, at from 60.degree. to 
90.degree. C., in the presence of from 1 to 10 mol % of dimethylformamide 
as the catalyst. 
The conversion of the carbonyl halides VI into the pyridine derivatives Ia 
is carried out by a procedure in which the carbonyl halide, in an inert 
organic solvent, such as dichloromethane or an ether, e.g. diethyl ether 
or methyl tert-butyl ether, is reacted with the amine III, likewise 
dissolved in an inorganic solvent. The amine is advantageously used in 
from 2 to 5 times the molar amount, in order to bind the hydrogen halide 
formed. It is also possible to carry out the reaction in the presence of 
an auxiliary base, for example a tertiary amine (triethylamine). In this 
case, from 1 to 1.5 molar equivalents of amine are sufficient. The 
reaction temperature may be from 0.degree. to 50.degree. C., preferably 
from 0.degree. to 20.degree. C. The reaction is generally complete after 
from 1 to 12 hours. The mixture can be worked up in a conventional manner, 
for example by hydrolysis with water and extraction of the product Ia with 
an organic solvent and evaporation of the organic solvent. The product of 
the formula Ia can be purified by recrystallization or chromatography. 
5. A process for the preparation of compounds Ib in which R.sup.3 is formyl 
or a radical --CO--A--R.sup.5, where A is oxygen and R.sup.5 is hydrogen, 
is based on the reaction of a pyridinecarbonyl halide VII with an amine 
III. Preferred carbonyl halides are the chlorides. 
In an advantageous procedure, the carbonyl halide VII, in an inert organic 
solvent, such as dichloromethane or an ether, e.g. diethyl ether or methyl 
tert-butyl ether, is reacted with an amine III, likewise dissolved in an 
organic solvent. The amine is advantageously used in from 2 to 5 times, 
preferably from 2 to 3 times, the molar amount in order to bind the 
hydrogen halide formed. It is also possible to carry out the reaction in 
the presence of an auxiliary base, for example a tertiary amine 
(triethylamine). In this case, from 1 to 1.5 molar equivalents of amine 
are sufficient. The reaction temperature may be from 0.degree. to 
50.degree. C., preferably from 0.degree. to 20.degree. C. The reaction is 
complete in general after from 1 to 12 hours. The mixture can be worked up 
in a conventional manner, for example by hydrolysis with water and 
extraction of the product VIII with an organic solvent and evaporation of 
the organic solvent. 
##STR8## 
The pyridinedicarboxylic acid semi-amides of the formula Ib are obtained 
from the pyridineamides VIII by reaction with alkyllithium, preferably 
with the addition of a solvent which is inert under the reaction 
conditions, such as diethyl ether, methyl tert-butyl ether, 
dimethoxyethane, diethylene glycol dimethyl ether, dioxane or 
tetrahydrofuran. As a rule, the reaction is carried out under a nitrogen 
atmosphere at from -80.degree. to 30.degree. C. In this process, the 
alkyllithium compound is generally used in from 2 to 3 times the molar 
amount, based on amide of the formula VIII used. After the reaction is 
complete, the mixture is treated with carbon dioxide, preferably in an 
inert solvent, such as diethyl ether or, for example, tetrahydrofuran, the 
desired products of the formula Ib, where R.sup.3 is carboxyl, being 
obtained. 
Suitable alkyllithium compounds are methyllithium, n-butyllithium, 
sec-butyllithium and tert-butyllithium. In this process, the 
organometallic base is used in from 2 to 4 times, preferably from 2 to 2.5 
times, the molar amount, based on amide VIII employed. 
Pyridinecarboxamides of the formula Ib, in which R.sup.3 is formyl, can 
also be obtained by the same process if dimethylformamide is used instead 
of carbon dioxide. Substituted pyridinecarboxamides or 
formylpyridinecarboxamides of the formula Ib are obtained after working up 
in a conventional manner. The concentration of the educts in the solvent 
is in general from 0.1 to 5, preferably from 0.2 to 2, mol/l. 
6. A further process for the preparation of the compounds Ib comprises 
treating a semi-amide of the formula If with an alcohol of the formula IX 
in the presence of a strong mineral acid, e.g. hydrochloric acid or 
sulfuric acid. 
##STR9## 
The process leads to compounds Ib in which R.sup.3 is a radical 
--CO--A--R.sup.5, A is oxygen and R.sup.5 is C.sub.1 -C.sub.6 -alkyl which 
may be substituted by one to five halogen atoms or one to five hydroxyl 
groups and/or one of the following radicals: C.sub.1 -C.sub.4 -alkoxy, 
C.sub.1 -C.sub.4 -alkoxy-C.sub.2 -C.sub.4 -alkoxy, cyano or C.sub.1 
-C.sub.3 -alkylthio; 
benzyl which may carry from one to three of the following groups: C.sub.1 
-C.sub.3 -alkyl, C.sub.1 -C.sub.3 -alkoxy, C.sub.1 -C.sub.3 -haloalkyl, 
halogen, nitro or cyano; 
C.sub.3 -C.sub.8 -cycloalkyl; 
phenyl which may carry from one to three of the following groups: C.sub.1 
-C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -haloalkyl, 
C.sub.1 -C.sub.4 -haloalkoxy, C.sub.2 -C.sub.5 -alkoxycarbonyl, halogen, 
nitro or cyano; 
a radical --N.dbd.CR.sup.8 R.sup.9, 
where R.sup.8 and R.sup.9 independently of one another are each hydrogen, 
C.sub.1 -C.sub.4 -alkyl or C.sub.3 -C.sub.6 -cycloalkyl or together may 
form a methylene chain having from 4 to 7 members. 
As a rule, the alcohol is used in excess, for example from 2 to 50 moles 
per mole of amide If. However, it is also possible to use an inert 
solvent, such as methylene chloride, dichloroethane, chlorobenzene or 
1,2-dichlorobenzene, an ether, e.g. diethyl ether, methyl tert-butyl 
ether, diethylene glycol dimethyl ether, tetrahydrofuran or dioxane, or 
corresponding mixtures. 
The reaction can be carried out at from 0.degree. to 100.degree. C., 
preferably from 20.degree. to 60.degree. C. 
7. A further process for the preparation of the compounds of formula Ib 
comprises reacting an acid If with an alcohol or thiol X in the presence 
of a dehydrating agent (e.g. dicyclohexylcarbodiimide (DCC)) at from 
-20.degree. to 50.degree. C., preferably from 0.degree. to 30.degree. C. 
As a rule, the starting materials are reacted in roughly stoichiometric 
amounts. The reaction is preferably carried out in the presence of one of 
the abovementioned inert solvents, e.g. tetrahydrofuran, dichloromethane 
or toluene. 
##STR10## 
A is oxygen or sulfur and R.sup.5 has the meanings stated for process 6. 
The molar ratios in which the required starting compounds are reacted with 
one another are in general from 0.9:1 to 2:1 for the ratio of carboxylic 
acid If to alcohol or thiol and from 1 : 1 to 1 : 3 for the ratio of 
carboxylic acid If to dehydrating agent. 
The concentration of the educts in the solvent is in general from 0.1 to 5, 
preferably from 0.2 to 2, mol/l. 
8. A further process for the preparation of the compounds of the formula Ib 
comprises reacting a pyridine derivative Ia with an alcohol in the 
presence of an organic base and of an inert solvent, for example in one of 
the abovementioned hydrocarbons or an alcohol at from 0.degree. to 
80.degree. C., preferably from 20.degree. to 50.degree. C. Examples of 
suitable organic bases are triethylamine, tri-n-butylamine, pyridine, 
N,N-dimethylaniline and N,N-dimethylcyclohexylamine. 
##STR11## 
The novel substituent is preferentially introduced meta to the heteroatom. 
Compounds Ic in which R.sup.2 is hydrogen, R.sup.3 is a radical 
--CO--A--R.sup.5, A is oxygen and R.sup.5 has the meanings stated for 
formula Ic can be prepared in this manner. 
The molar ratios in which the required starting compounds are reacted with 
one another are in general from 0.9:1 to 200:1 for the ratio of alcohol IX 
to pyridine derivative Ia, depending on whether the alcohol is used 
directly as a solvent, and from 0.9:1 to 2:1 for the ratio of the base to 
the pyridine derivative Ia. 
The concentration of the educts in the solvent is in general from 0.1 to 5, 
preferably from 0.2 to 2, mol/l. 
9. A process for the preparation of compounds of the formulae Ib and Ic in 
which R.sup.2 is hydrogen and R.sup.3 is a radical --CO--NR.sup.6 R.sup.7 
comprises reacting a pyridine derivative Ia with an amine XI in the 
presence of one of the abovementioned inert solvents, for example an ether 
or an alcohol, at from 0.degree. to 80.degree. C., preferably from 
10.degree. to 40.degree. C. The weaker basic amine is preferentially 
introduced meta to the heteroatom. Isomeric compounds can be separated in 
a conventional manner, for example by chromatography. 
The molar ratios in which the required starting compounds are reacted with 
one another are in general from 0.9:1 to 20:1 for the ratio of amine XI to 
pyridine derivative Ia. The concentration of the educts in the solvent is 
in general from 0.1 to 5, preferably from 0.2 to 2, mol/l. 
##STR12## 
10. Compounds of the formula Ic in which R.sup.3 is a radical 
--CO--A--R.sup.5 and R.sup.5 is one equivalent of a cation are obtained by 
reacting a pyridine derivative Ic, where R.sup.3 is a radical 
--CO--A--R.sup.5 and R.sup.5 is hydrogen, with one equivalent of the 
corresponding salt-forming cation. If this is an inorganic cation, e.g. 
sodium, potassium or calcium, the acid Ic is advantageously dissolved or 
suspended in water or in a lower alcohol or in a mixture of these, and one 
equivalent of the salt-forming cation is added. The salt-forming cation 
can be used, for example, in the form of its hydroxide, carbonate or 
bicarbonate, preferably in the form of its hydroxide. The reaction is 
generally complete after a few minutes and the reaction mixture can be 
worked up in a conventional manner, for example by precipitation and 
filtration under suction or by evaporating down the solution. For the 
preparation of compounds Ic in which R.sup.5 is ammonium or organic 
ammonium, the acid Ic is dissolved or suspended in an organic solvent, 
e.g. diethyl ether, tetrahydrofuran or dioxane, and the mixture is treated 
with one equivalent of ammonia, an amine or a tetraalkylammonium 
hydroxide. 
Examples of amines which may be used are methylamine, ethylamine, 
n-propylamine, isopropylamine, n-butylamine, isobutylamine, 
sec-butylamine, n-amylamine, isoamylamine, hexylamine, heptylamine, 
octylamine, nonylamine, decylamine, undecylamine, dodecylamine, 
tridecylamine, tetradecylamine, pentadecylamine, hexadecylamine, 
heptadecylamine, octadecylamine, methylethylamine, methylisopropylamine, 
methylhexylamine, methylnonylamine, methylpentadecylamine, 
methyloctadecylamine, ethylbutylamine, ethylheptylamine, ethyloctylamine, 
hexylheptylamine, hexyloctylamine, dimethylamine, diethylamine, 
di-n-propylamine, diisopropylamine, di-n-amylamine, diisoamylamine, 
dihexylamine, diheptylamine, dioctylamine, trimethylamine, triethylamine, 
tri-n-propylamine, triisopropylamine, tri-n-butylamine, tri-isobutylamine, 
tri-sec-butylamine, tri-n-amylamine, ethanolamine, n-propanolamine, 
isopropanolamine, diethanolamine, N,N-di-ethylethanolamine, 
N-ethylpropanolamine, N-butylethanolamine, allylamine, n-buten-2-ylamine, 
n-penten-2-ylamine, 2,3-dimethylbuten-2-ylamine, dibuten-2-ylamine, 
n-hexen-2-ylamine, propenylenediamine, tallow amine, cyclopentylamine, 
cyclohexylamine, dicyclohexylamine, piperidine, morpholine and 
pyrrolidine. 
In the case of the tetraalkylammonium hydroxides, it is possible to use, 
for example, tetramethyl-, tetraethyl- or trimethylbenzylammonium 
hydroxide. As a rule, the ammonium salt or organic ammonium salt is 
precipitated from the solution and can be isolated by conventional 
methods. Alternatively, the salt of the formula Ic can also be obtained by 
evaporating down the solvent. 
The reaction can be carried out at from -10.degree. to 80.degree. C., 
preferably from 20.degree. to 40.degree. C. 
11. A process for the preparation of the compounds of the formula Ia in 
which one of the ring members X, Y and Z is N and another is C--R.sup.4 
where R.sup.4 is halogen comprises first reacting a pyridine derivative of 
the formula Ia where one of the ring members Y, X and Z is N with an 
oxidizing agent, for example m-chloroperbenzoic acid or hydrogen peroxide, 
in an inert organic solvent, for example one of the abovementioned 
halohydrocarbons, such as methylene chloride, or an alkanecarboxylic acid, 
such as glacial acetic acid, to give the N-oxide at from 0.degree. to 
100.degree. C., preferably from 20.degree. to 60.degree. C., and then 
reacting said N-oxide with a phosphorus oxyhalide, for example phosphorus 
oxychloride, to give the halogen compound at from 80.degree. to 
120.degree. C. 
##STR13## 
The molar ratios in which the required starting compounds are reacted with 
one another are in general from 1:0.9 to 1:1.5 for the ratio of imide Ia 
to the oxidizing agent. In the subsequent halogenation step, an inert 
solvent, such as chlorobenzene, may be used, but the reaction is 
advantageously carried out directly in excess phosphorus oxyhalide as a 
reaction medium. 
The concentration of the educts in the solvent (mixture) is in general from 
0.1 to 5, preferably from 0.2 to 2, mol/l. 
The individual process steps are known from the literature or can be 
carried out by methods generally known from the literature (J. Org. Chem. 
19 (1954), 1633). 
12. A process for the preparation of the compounds of the formula Ia 
comprises reacting a haloimide of the formula Ia where one or more of the 
ring members W, X, Y or Z are C--R.sup.4 in which R.sup.4 is halogen with 
the salt of an alcohol or of a thiol XII in the presence of excess alcohol 
or of an inert organic solvent. 
##STR14## 
In formulae Ia and XII, 
R.sup.4 is C.sub.1 -C.sub.4 -alkoxy or C.sub.1 -C.sub.4 -alkylthio, each of 
which may be monosubstituted to trisubstituted by halogen, 
C.sub.3 - or C.sub.4 -alkenyloxy, 
C.sub.3 - or C.sub.4 -alkynyloxy 
or phenoxy or phenylthio, each of which may be monosubstituted to 
trisubstituted by C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -haloalkyl, 
C.sub.1 -C.sub.4 -alkylthio, C.sub.1 -C.sub.4 -haloalkylthio, halogen, 
cyano or nitro. 
Me is an alkali metal or alkaline earth metal ion, for example lithium, 
sodium, potassium, magnesium or calcium. 
Solvents such as halohydrocarbons, e.g. tetrachloroethane, methylene 
chloride, chloroform, dichloroethane, chlorobenzene and 
1,2-dichlorobenzene, ethers, e.g. diethyl ether, methyl tert-butyl ether, 
dimethoxyethane, diethylene glycol dimethyl ether, tetrahydrofuran and 
dioxane, dipolar aprotic solvents, e.g. acetonitrile, dimethylformamide, 
dimethylacetamide, dimethyl sulfoxide, N-methylpyrrolidone, 
1,3-dimethyltetrahydro-2(1H)-pyrimidinone and 
1,3-dimethylimidazolidin-2-one, aromatics, e.g. benzene, toluene, xylene, 
pyridine and quinoline, ketones, e.g. acetone and methyl ethyl ketone, 
alcohols, e.g. methanol, ethanol, isopropanol and tertbutanol, and 
corresponding mixtures are advantageously used for these reactions. 
The reaction can be carried out at from 20.degree. C. to the reflux 
temperature of the particular solvent or solvent mixture, preferably at 
from 40.degree. to 150.degree. C. 
The bases used are hydrides and alkoxides of alkali metal and alkaline 
earth metal cations, in particular NaH, KH, CaH.sub.2, LiH and potassium 
butoxide. It is sometimes also useful to use combinations of the 
abovementioned bases. 
The molar ratios in which the required starting compounds are reacted with 
one another are in general from 0.9:1 to 1.5:1 for the ratio of alcohol or 
thiol to halogenated imide Ia and from 1:1 to 1:3 for the ratio of alcohol 
or thiol to the effective base. 
The concentrations of the educts in the solvent are in general from 0.1 to 
5, preferably from 0.2 to 2, mol/l. 
The process can be carried out by methods generally known from the 
literature (U.S. Pat. No. 4647301). 
13. Pyridine derivatives Ia in which R.sup.4 in C--R.sup.4 is C.sub.1 
-C.sub.4 -haloalkyl, C.sub.1 -C.sub. -haloalkoxy or C.sub.1 C.sub.4 
-haloalkylmercapto can be obtained in a first step by halogenation of a 
pyridinedicarboxylic anhydride of the formula II, where R.sup.4 is C.sub.1 
-C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy or C.sub. -C.sub.4 -alkylthio, 
at from 60.degree. to 150.degree. C., preferably from 80.degree. to 
130.degree. C., in the presence of one of the abovementioned inert 
aromatic halohydrocarbons, e.g. chlorobenzene, and in the presence or 
absence of a free radical initiator, such as 
.alpha.,.alpha.'-azoisobutyronitrile. This is followed, in a second step, 
by halogen exchange by antimony(III) fluoride in the presence or absence 
of a catalytic amount of antimony(V) chloride. For this purpose, a mixture 
of anhydride II' and antimony(III) fluoride is heated to about 80.degree. 
C., if necessary the catalyst is then added a little at a time and the 
mixture is heated further until the exothermic reaction continues by 
itself, preferably at from 110.degree. to 140.degree. C. After stirring 
has been carried out for from 20 to 60 minutes, the reaction solution is 
taken up in a chlorohydrocarbon, decomposition is effected in a 
conventional manner with hydrochloric acid and the organic phase is worked 
up. The anhydride II" thus obtained is then converted into the 
corresponding imide Ia by processes 1 and 2. 
##STR15## 
The molar ratios in which the required starting compounds are reacted with 
one another are in general from 0.9 to 3 moles of halogen for the C--H 
bond to be halogenated in II and from 0.25 to 0.33 mole of antimony-(III) 
fluoride for the halogen equivalent to be exchanged in II. 
The concentration of the educts in the solvent (mixture) is in general from 
0.1 to 5, preferably from 0.2 to 2, mol/l. 
The process can be carried out by methods generally known from the 
literature (DE-A-2 914 915), and the degree of fluorination can be 
controlled by the amount of fluorinating agent. 
14. Compounds of the formula Ia in which R.sup.4 in C--R.sup.4 is C.sub.1 
-C.sub.4 -haloalkyl are obtained if imides I"a substituted .alpha. to the 
heteroatom by C.sub.1 -C.sub.6 -alkyl are reacted, in a first step, with 
an oxidizing agent, for example m-chloroperbenzoic acid or hydrogen 
peroxide, in an inert organic solvent, for example one of the 
abovementioned halohydrocarbons, such as methylene chloride or 
chlorobenzene, or an alkanecarboxylic acid, such as glacial acetic acid, 
or an aromatic, such as toluene, to give the corresponding N-oxides at 
from 0.degree. to 100.degree. C., preferably from 20.degree. to 60.degree. 
C., and the latter are then converted into the halogen compounds I"'a with 
a phosphorus oxyhalide, for example phosphorus oxychloride, at from 
80.degree. to 120.degree. C. For the pyridine-2,3-dicarboximides, the 
reaction takes place in accordance with the following scheme: 
##STR16## 
The molar ratios and the procedure are based on the reaction conditions of 
process 11. The individual process steps can be carried out by methods 
generally known from the literature. 
In view of the intended use of the compounds I'a, I'b and I'c, for example, 
the following radicals are suitable substituents: 
W, X, Y and Z are each C--R.sup.4, nitrogen or N-oxide; 
R.sup.1 is hydrogen, hydroxyl, C.sub.1 -C.sub.4 -alkoxy, such as methoxy, 
ethoxy, propoxy, 1-methylethoxy, butoxy, 1-methylpropoxy, 2-methylpropoxy 
or 1,1-dimethylethoxy, in particular methoxy, ethoxy, 1-methylethoxy or 
1,1-dimethylethoxy; C.sub.1 -C.sub.6 -alkyl, such as methyl, ethyl, 
propyl, 1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl, 
1,1-dimethylethyl, pentyl, 1-methylbutyl, 2-methylbutyl 3-methylbutyl, 
1,1-dimethylproypl, 1,2-dimethylpropyl, 2,2-dimethylpropyl, 1-ethylpropyl, 
hexyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 
1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl, 
2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl, 
2-ethylbutyl, 1,1,2-trimethylpropyl, 1,2,2-trimethylpropyl, 
1-ethyl-1-methylpropyl or 1-ethyl-2-methylpropyl, in particular methyl, 
ethyl, propyl, 1-methylethyl or 1,1-dimethylethyl, which may carry from 
one to three of the following groups: 
C.sub.1 -C.sub.4 -alkoxy as stated above, in particular methoxy or ethoxy; 
haloalkoxy, such as difluoromethoxy, trifluoromethoxy, 
chlorodifluoromethoxy, dichlorofluoromethoxy, 1-fluoroethoxy, 
2-fluoroethoxy, 2,2-difluoroethoxy, 1,1,2,2-tetrafluoroethoxy, 
2,2,2-trifluoroethoxy, 2-chloro-1,1,2-trifluoroethoxy or 
pentafluoroethoxy, in particular trifluoromethoxy or pentafluoroethoxy; 
alkylthio, such as methylthio, ethylthio, propylthio, 1-methylethylthio, 
n-butylthio, 1-methylpropylthio, 2-methylpropylthio or 
1,1-dimethylethylthio, in particular methylthio or ethylthio; 
haloalkylthio, such as difluoromethylthio, trifluoromethylthio, 
chlorodifluoromethylthio, 1-fluoroethylthio, 2-fluoroethylthio, 
2,2-difluoroethylthio, 2,2,2-trifluoroethylthio, 
2-chloro-2,2-difluoroethylthio, 2,2-dichloro-2-fluoroethylthio, 
2,2,2-trichloroethylthio or pentafluoroethylthio, in particular 
trifluoromethylthio or pentafluoroethylthio; 
dialkylamino, such as dimethylamino, diethylamino, dipropylamino, 
diisopropylamino, dibutylamino or methylethylamino, in particular 
dimethylamino or methylethylamino; 
cyano; 
halogen, such as fluorine, chlorine, bromine or iodine, in particular 
fluorine or chlorine; 
cycloalkyl, such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, 
cycloheptyl or cyclooctyl, in particular cyclopropyl, cyclopentyl or 
cyclohexyl, or phenyl which may be substituted by halogen, cyano, nitro, 
alkyl as stated above, in particular methyl or ethyl, haloalkyl as stated 
above, in particular trifluoromethoxy; 
alkoxy, as stated above, in particular methoxy or ethoxy, haloalkoxy as 
stated above, in particular trifluoro-methoxy, or haloalkylthio; C.sub.3 
-C.sub.8 -cycloalkyl as stated above, in particular cyclopropyl, 
cyclobutyl, cyclopentyl or cyclohexyl, which may carry from one to three 
of the following groups: alkyl as stated above, in particular methyl, 
ethyl or isopropyl, haloalkyl as stated above, in particular 
trifluoromethyl, alkoxy as stated above, in particular methoxy or ethoxy, 
haloalkoxy as stated above, in particular trifluoromethoxy, halogen as 
stated above, in particular fluorine or chlorine, nitro or cyano; 
C.sub.3 -C.sub.6 -alkenyl, such as 2-propenyl, 2-methylethenyl, 2-butenyl, 
3-butenyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl, 2-pentenyl, 
3-pentenyl, 4-pentenyl, 3-methyl-2-butenyl, 1-methyl-2-butenyl, 
2-methyl-2-butenyl, 1-methyl-3-butenyl, 2-methyl-3-butenyl, 
3-methyl-3-butenyl, 1,1-dimethyl-2-propenyl, 1,2-dimethyl-2-propenyl, 
1-ethyl-2-propenyl, 1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, 5-hexenyl, 
1-methyl-2-pentenyl, 2-methyl-2-pentenyl, 3-methyl-2-pentenyl, 
4-methyl-2-pentenyl, 1-methyl-3-pentenyl, 2-methyl-3-pentenyl, 
3-methyl-3-pentenyl, 4-methyl-3-pentenyl, 1-methyl-4-pentenyl, 
2-methyl-4-pentenyl, 3-methyl-4-pentenyl, 4-methyl-4-pentenyl, 
1,1-dimethyl-2-butenyl, 1,1-dimethyl-3-butenyl, 1,2-dimethyl-2-butenyl, 
1,2-dimethyl-3-butenyl, 1,3-dimethyl-2-butenyl, 
1,3-dimethyl-3-buteny1,2,2-dimethyl-3-butenyl, 2,3-dimethyl-2-butenyl, 
2,3-dimethyl-3-butenyl, 1-ethyl-2-butenyl, 1-ethyl-3-butenyl, 
2-ethyl-2-buteny1,2-ethyl-3-butenyl, 1,1,2-trimethyl-2-propenyl, 
1-ethyl-1-methyl-2-pentenylorethyl-2-methyl-2-pentenyl, in particular 
ethenyl, 2-propenyl, 1-methylethenyl, 2-butenyl, 3-butenyl, 
1-methylpropyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl, which may be 
monosubstituted to trisubstituted by halogen as stated above, in 
particular fluorine or chlorine, and/or monosubstituted by phenyl, where 
the phenyl radical in turn may carry from one to three of the following 
groups: alkyl as stated above, in particular trifluoromethyl or 
chlorodifluoromethyl, alkoxy as stated above, in particular methoxy or 
ethoxy, haloalkoxy as stated above, in particular trifluoromethoxy, 
trichloromethoxy or pentafluoroethoxy, alkylthio as stated above, in 
particular methylthio or ethylthio, haloalkylthio as stated above, in 
particular difluoromethylthio, trifluoromethylthio or 
pentafluoromethylthio, halogen as stated above, in particular fluorine or 
chlorine, cyano or nitro; C.sub.3 -C.sub.6 -alkynyl, such as propargyl, 
2-butynyl, 3-butynyl, 1-methyl-2-propynyl, 2-pentynyl, 3-pentynyl, 
4-pentynyl, 1-methyl-3-butynyl, 2-methyl-3-butynyl, 1-methyl-2-butynyl, 
3-methyl-1-butynyl, 1,1-dimethyl-2-propynyl, 1-ethyl-2-propynyl, 
2-hexynyl, 3-hexynyl, 4-hexynyl, 5-hexynyl, 1-methyl-2-pentynyl, 
1-methyl-3-pentynyl, 1-methyl-4-pentynyl, 3-methyl-4-pentynyl, 
4-methyl-2-pentynyl, 1,1-dimethyl-2-butynyl, 1,1-dimethyl-3-butynyl, 
1,2-dimethyl-3-butynyl, 2,2-dimethyl-3-butynyl, 1-ethyl-2-butynyl, 
1-ethyl-3-butynyl, 2-ethyl-3-butynyl or 1-ethyl-1-methyl-2-propynyl, in 
particular 1-methyl-2-propynyl or 1,1-dimethyl-2-propynyl, which may be 
monosubstituted to trisubstituted by halogen as stated above, in 
particular fluorine or chlorine, and/or monosubstituted by phenyl, where 
the phenyl radical in turn may carry from one to three of the following 
groups: alkyl as stated above, in particular methyl, ethyl or 
1-methylethyl, haloalkyl as stated above, in particular trifluoromethyl or 
chlorodifluoromethyl, alkoxy as stated above, in particular methoxy or 
ethoxy, haloalkoxy as stated above, in particular trifluoromethoxy, 
trichloromethoxy or pentafluoroethoxy, alkylthio as stated above, in 
particular methylthio or ethylthio, haloalkylthio as stated above, in 
particular difluoromethylthio, trifluoromethylthio or 
pentafluoromethylthio, halogen as stated above, in particular fluorine or 
chlorine, cyano or nitro; C.sub.1 -C.sub.4 -dialkylamino as stated above, 
in particular dimethylamino, diethylamino or diisopropylamino; 
a 5-membered or 6-membered saturated or aromatic heterocyclic radical 
containing one or two hetero atoms selected from the group consisting of 
oxygen, sulfur and nitrogen, such as tetrahydrofuryl, tetrahydropyranyl, 
furyl, thienyl, thiazolyl, pyrazolyl, pyrrolyl, pyridyl, morpholino, 
piperidino or pyrimidyl, for example 2-tetrahydrofuranyl, 
3-tetrahydrofuranyl, 2-tetrahydrothienyl, 3-tetrahydrothienyl, 
2-tetrahydropyranyl, 3-tetrahydropyranyl, 4-tetrahydropyranyl, 2-furyl, 
3-furyl, 2-thienyl, 3-thienyl, 3-isoxazolyl, 4-isoxazolyl, 5-isoxazolyl, 
3-isothiazolyl, 4-isothiazolyl, 5-isothiazolyl, 2-oxazolyl, 4-oxazolyl, 
5-oxazolyl, 2-thiazolyl, 4-thiozolyl, 5-thiazolyl, 2-imidazolyl, 
4-imidazolyl, 5-imidazolyl, 2-pyrrolyl, 3-pyrrolyl, 3-pyrazolyl, 
4-pyrazolyl, 5-pyrazolyl, 2-pyridyl, 3-pyridyl or 4-pyridyl, which may 
carry from one to three of the following substituents: alkyl as stated 
above, in particular methyl or ethyl, or halogen as stated above, in 
particular fluorine or chlorine; 
phenyl which may carry from one to four of the following groups: alkyl as 
stated above, in particular methyl, ethyl or isopropyl, haloalkyl as 
stated above, in particular trifluoromethyl or chlorodifluoromethyl, 
alkoxy as stated above, in particular methoxy or ethoxy, haloalkoxy as 
stated above, in particular trifluoromethoxy, trichloromethoxy or 
pentafluoroethoxy, alkylthio as stated above, in particular methylthio or 
ethylthio, haloalkylthio as stated above, in particular 
difluoromethylthio, trifluoromethylthio or pentafluoromethylthio, halogen 
as stated above, in particular fluorine or chlorine, cyano, nitro, formyl, 
C.sub.1 -C.sub.4 -alkanoyl, such as acetyl, propionyl or butyryl, in 
particular acetyl, haloalkanoyl, such as trifluoroacetyl, trichloroacetyl, 
or pentafluoropropionyl, in particular trifluoroacetyl, or alkoxycarbonyl 
as stated under R.sup.1, in particular methoxycarbonyl; 
naphthyl which may be monosubstituted to trisubstituted by alkyl as stated 
under R.sup.1, in particular methyl or ethyl, or halogen as stated under 
R.sup.1, in particular fluorine or chlorine; 
R.sup.2 is hydrogen; 
C.sub.1 -C.sub.6 -alkyl as stated under R.sup.1, in particular methyl, 
ethyl, 1-methylethyl, which may carry from one to three of the following 
substituents: hydroxyl, halogen as stated under R.sup.1, in particular 
fluorine or chlorine, alkoxy as stated under R.sup.1, in particular 
methoxy or ethoxy, alkylthio as stated under R.sup.1, in particular 
methylthio or ethylthio, or dialkylamino as stated under R.sup.5, in 
particular dimethylamino; 
C.sub.3 -C.sub.8 -cycloalkyl as stated under R.sup.1, in particular 
cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl, which may be 
monosubstituted to trisubstituted by alkyl as stated under R.sup.1, in 
particular methyl, ethyl or isopropyl, halogen as stated under R.sup.1, in 
particular fluorine or chlorine, or haloalkyl as stated under R.sup.1, in 
particular trifluoromethyl, or 
R.sup.1 and R.sup.2 together form a C.sub.2 -C.sub.6 -methylene chain which 
may be interrupted by oxygen, sulfur or N-methyl, such as 
--(CH.sub.2).sub.3 --, --(CH.sub.2).sub.4 --, --(CH.sub.2).sub.6 --, 
--(CH.sub.2).sub.6 --, --CH.sub.2 --O--CH.sub.2 --, --CH.sub.2 --CH.sub.2 
--O--CH.sub.2 --CH.sub.2 --, --CH.sub.2 --S--CH.sub.2 --, --CH.sub.2 
--CH.sub.2 --S--CH.sub.2 --CH.sub.2 --, --CH.sub.2 --CH.sub.2 
--N(CH.sub.3)--CH.sub.2 --CH.sub.2 --, in particular --(CH.sub.2).sub.5 -- 
or --CH.sub.2 --CH.sub.2 --O--CH.sub.2 --CH.sub.2 --, or the radical of 
the formula --(CH.sub.2).sub.3 --CO--; 
R.sup.3 is formyl 4,5-dihydrooxazol-2-yl or a radical --COAR.sup.5 or 
--CONR.sup.6 R.sup.7 ; 
A is oxygen or sulfur; 
R.sup.1 is hydrogen; 
alkyl as stated for R.sup.1, in particular methyl, ethyl, propyl, 
1-methylethyl or hexyl, which may carry from one to five halogen atoms as 
stated under R.sup.1, in particular fluorine or chlorine, from one to five 
hydroxyl groups and/or one of the following radicals: alkoxy as stated 
under R.sup.1, in particular methoxy or ethoxy; 
alkoxyalkoxy, such as methoxyethoxy, ethoxyethoxy or propoxyethoxy, in 
particular methoxyethoxy, cyano, trimethylsilyl, alkylthio as stated under 
R.sup.1, in particular methylthio or ethylthio, alkylamino, such as 
methylamino, ethylamino, propylamino or 1-methylethylamino, in particular 
methylamino or ethylamino, dialkylamino, such as dimethylamino, 
diethylamino, dipropylamino, diisopropylamino or methylethylamino, in 
particular dimethylamino or methylethylamino, alkylsulfinyl, such as 
methylsulfinyl, ethylsulfinyl, propylsulfinyl or 1-methylethylsulfinyl, in 
particular methylsulfinyl or ethylsulfinyl, alkylsulfonyl, such as 
methylsulfonyl, ethylsulfonyl, propylsulfonyl or 1-methylethylsulfonyl, in 
particular methylsulfonyl or ethylsulfonyl, carboxyl, alkoxycarbonyl, such 
as methoxycarbonyl or ethoxycarbonyl, alkoxycarbonylalkoxy, such as 
methoxycarbonylmethoxy, methoxycarbonylethoxy or ethoxycarbonylethoxy, 
alkoxycarbonylalkoxycarbonyl, such as methoxycarbonylmethoxycarbonyl, 
methoxycarbonylethoxycarbonyl or ethoxycarbonylethoxycarbonyl, 
dialkylaminocarbonyl, such as dimethylaminocarbonyl, diethylaminocarbonyl, 
dipropylaminocarbonyl, diisopropylaminocarbonyl or 
methylethylaminocarbonyl, in particular dimethylaminocarbonyl or 
diethylaminocarbonyl, dialkoxyphosphonyl, such as dimethoxyphosphonyl, 
diethoxyphosphonyl, dipropoxyphosphonyl or diisopropoxyphosphonyl, in 
particular dimethoxyphosphonyl or diethoxyphosphonyl, alkaniminoxy, such 
as 2-propaniminoxy, thienyl, furanyl, tetrahydrofuranyl, N-phthalimido, 
pyridyl, benzyloxy or benzoyl, where these cyclic radicals may carry from 
one to three of the following groups: halogen, in particular fluorine or 
chlorine, alkoxy, in particular methoxy or ethoxy, or alkyl, in particular 
methyl or ethyl; 
benzyl which may carry from one to three of the following groups: nitro, 
cyano, halogen, in particular fluorine or chlorine, alkyl as stated under 
R.sup.1, in particular methyl or ethyl, alkoxy as stated under R.sup.1, in 
particular methoxy or ethoxy, or haloalkyl as stated in general and in 
particular under R.sup.1 ; 
cycloalkyl as stated under R.sup.1, in particular cyclopentyl or 
cyclohexyl; 
phenyl which may carry from one to three of the following groups alkyl as 
stated under R.sup.1, in particular methyl or ethyl, alkoxy as stated 
under R.sup.1, in particular methoxy or ethoxy, haloalkyl as stated under 
R.sup.1, in particular trifluoromethyl, haloalkoxy as stated under 
R.sup.1, in particular trifluoromethoxy, alkoxycarbonyl as stated above, 
in particular methoxycarbonyl, halogen as stated under R.sup.1, in 
particular fluorine, chlorine or bromine, nitro or cyano; 
C.sub.3 -C.sub.8 -alkenyl as stated under R.sup.1, in particular 2-propenyl 
or 2-butenyl, C.sub.3 - or C.sub.6 -cycloalkenyl, such as 2-cyclopentenyl 
or 2-cyclohexenyl, in particular 2-cyclohexenyl, C.sub.3 -C.sub.8 -alkynyl 
as stated under R.sup.1, in particular 2-propynyl, where the three 
last-mentioned groups may carry one of the following radicals: hydroxyl, 
alkoxy as stated under R.sup.1, in particular methoxy or ethoxy, halogen 
as stated under R.sup.1, in particular fluorine or chlorine, phenyl which 
in turn may carry from one to three of the following groups: alkyl as 
stated under R.sup.1, in particular methyl or ethyl, alkoxy as stated 
under R.sup.1, in particular methoxy or ethoxy, haloalkyl as stated under 
R.sup.1, in particular trifluoromethyl, halogen as stated under R.sup.1, 
in particular fluorine or chlorine, nitro or cyano; 
a five-membered or six-membered heterocyclic radical having one or two 
hetero atoms selected from the group consisting of oxygen, sulfur and 
nitrogen, as stated under R.sup.1, in particular tetrahydrofuranyl or 
tetrahydropyranyl, or benzotriazolyl; 
N-phthalimido, tetrahydrophthalimido, succinimido or maleimido; 
one equivalent of a cation from the group consisting of the alkali metal or 
alkaline earth metals, manganese, copper, iron, ammonium and substituted 
ammonium, or --N.dbd.CR.sup.8 R.sup.9, where 
R.sup.8 and R.sup.9 are each hydrogen, alkyl as stated under R.sup.2, in 
particular methyl, ethyl or isopropyl; 
cycloalkyl as stated under R.sup.1, in particular cyclopropyl; 
phenyl or furyl, or together form a methylene chain having from 4 to 7 
members; 
R.sup.6 is hydrogen, C.sub.1 -C.sub.6 -alkyl as stated under R.sup.1, in 
particular methyl or ethyl, or C.sub.3 -C.sub.6 -cycloalkyl as stated 
under R.sup.1, in particular cyclopropyl; 
R.sup.7 is hydrogen or C.sub.1 -C.sub.6 -alkyl as stated under R.sup.1, in 
particular methyl, ethyl, propyl, 1-methylethyl or 1,1-dimethylethyl, or 
R.sup.6 and R.sup.7 together form a methylene chain having 4 or 5 members; 
R.sup.4 is hydrogen, halogen as stated under R.sup.1, in particular 
fluorine or chlorine, nitro, cyano, alkyl as stated under 
R.sup.1, in particular methyl, ethyl, propyl, 1-methylethyl or 
1,1-dimethylethyl, which may carry from one to five halogen atoms as 
stated under R.sup.1, in particular fluorine or chlorine, and/or one or 
two of the following radicals: cyano, alkoxy as stated under R.sup.1, in 
particular methoxy, ethoxy, 1-methylethoxy or 1,1-dimethylethoxy, 
haloalkoxy as stated under R.sup.1, in particular difluoromethoxy or 
trifluoromethoxy, alkylthio as stated under R.sup.1, in particular 
methylthio or ethylthio, haloalkylthio as stated under R.sup.1, in 
particular difluoromethylthio or trifluoromethylthio; 
cycloalkyl as stated under R.sup.1, in particular cyclopropyl; benzyl which 
may be monosubstituted to trisubstituted by alkyl of 1 to 4 carbon atoms 
as stated under R.sup.1, in particular methyl, ethyl or 1-methylethyl, 
haloalkyl as stated under R.sup.1, in particular trifluoromethyl or 
chlorodifluoromethyl, alkoxy as stated under R.sup.1, in particular 
methoxy or ethoxy, haloalkoxy as stated under R.sup.1, in particular 
trifluoromethoxy, trichloromethoxy or pentafluoroethoxy, alkylthio as 
stated under R.sup.1, in particular methylthio or ethylthio, haloalkylthio 
as stated under R.sup.1, in particular difluoromethylthio, 
trifluoromethylthio or pentafluoromethylthio, halogen as stated under 
R.sup.1, in particular fluorine or chlorine, cyano or nitro; 
C.sub.3 -C.sub.6 -cycloalkyl as stated under R.sup.1, in particular 
cyclopropyl, cyclopentyl or cyclohexyl, which may be monosubstituted to 
trisubstituted by alkyl as stated under R.sup.1, in particular methyl or 
ethyl, or halogen as stated under 
R.sup.1, in particular fluorine or chlorine; 
C.sub.2 -C.sub.6 -alkenyl as stated under R.sup.1, and 1-ethenyl, 
1-propenyl, 1-methyl-1-propenyl, 2-methyl-1-propenyl, 1-pentenyl, 
1-methyl-1-butenyl, 2-methyl-1-butenyl, 1-ethyl-1-propenyl, 
1-methyl-1-pentenyl, 2-methyl-1-pentenyl, 3-methyl-1-pentenyl, 
4-methyl-1-pentenyl, 1,2-dimethyl-1-butenyl, 1,3-dimethyl-1-butenyl, 
2,3-dimethyl-1-butenyl, 3,3-dimethyl-1-butenyl, ethyl-1-butenyl, 
2-ethyl-1-butenyl or 1-ethyl-2-methyl-1-pentenyl, in particular ethenyl, 
1-propenyl, 2-propenyl, 1-methylethenyl, 1-butenyl, 2-butenyl, 3-butenyl, 
1-methylpropenyl, 1-methyl-2-propenyl, 2-methyl-1-propenyl or 
2-methyl-2-propenyl, which may be monosubstituted to trisubstituted by 
halogen as stated under R.sup.1, in particular fluorine or chlorine, or 
alkoxy as stated under R.sup.1, in particular methoxy or ethoxy, and/or 
monosubstituted by phenyl, where the phenyl radical in turn may carry from 
one to three of the following groups: alkyl as stated under R.sup.1, in 
particular methyl, ethyl or 1-methylethyl, haloalkyl as stated under 
R.sup.1, in particular trifluoromethyl or chlorodifluoromethyl, alkoxy as 
stated under R.sup.1, in particular methoxy or ethoxy, haloalkoxy as 
stated under R.sup.1, in particular trifluoromethoxy, trichloromethoxy or 
pentafluoroethoxy, alkylthio as stated under R.sup.1, in particular 
methylthio or ethylthio, haloalkylthio as stated under R.sup.1, in 
particular difluoromethylthio, trifluoromethylthio or 
pentafluoromethylthio, halogen as stated under R.sup.1, in particular 
fluorine or chlorine, cyano or nitro; 
alkynyl as stated under R.sup.1, and ethynyl, 1-propynyl, 1-butynyl, 
1-pentynyl, 1-hexynyl, 3-methyl-1-pentynyl or 4-methyl-1-pentynyl, in 
particular ethynyl, 1-propynyl or propargyl, which may be monosubstituted 
to trisubstituted by halogen as stated above, in particular fluorine or 
chlorine, or alkoxy as stated above, in particular methoxy or ethoxy, 
and/or monosubstituted by phenyl, where the phenyl radical in turn may 
carry from one to three of the following groups: alkyl as stated above, in 
particular methyl, ethyl or 1-methylethyl, haloalkyl as stated above, in 
particular trifluoromethyl or chlorodifluoromethyl, alkoxy as stated 
above, in particular methoxy or ethoxy, haloalkoxy as stated above, in 
particular trifluoromethoxy, trichloromethoxy or pentafluoroethoxy, 
alkylthio as stated above, in particular methylthio or ethylthio, 
haloalkylthio as stated above, in particular difluoromethylthio, 
trifluoromethylthio or pentafluoromethylthio, halogen as stated above, in 
particular fluorine or chlorine, cyano or nitro; 
C.sub.1 -C.sub.4 -alkoxy as stated under R.sup.1, in particular methoxy or 
ethoxy; 
C.sub.1 -C.sub.4 -haloalkoxy as stated above, in particular 
trifluoromethoxy, trichloromethoxy or pentafluoroethoxy; 
C.sub.2 -C.sub.4 -alkenyloxy, such as vinyloxy, 2-propenyloxy, 
1-methylethenyloxy or 2-methyl-3-butenyloxy, in particular 2-propenyloxy 
or 2-methyl-3-butenyloxy; 
C.sub.2 -C.sub.4 -alkynyloxy, such as ethynyloxy, 2-propynyloxy, 
1-methylethynyloxy or 2-methyl-3-butynyloxy, in particular 2-propynyloxy 
or 2-methyl-3-butynyloxy; 
C.sub.1 -C.sub.4 -alkylthio as stated under R.sup.1, in particular 
methylthio or ethylthio; 
C.sub.1 -C.sub.4 -haloalkylthio as stated under R.sup.1, in particular 
difluoromethylthio, trifluoromethylthio or pentafluoroethylthio; 
C.sub.1 -C.sub.4 -alkylsulfinyl, such as methylsulfinyl, ethylsulfinyl, 
n-propylsulfinyl, isopropylsulfinyl, n-butylsulfinyl or 
tert-butylsulfinyl, in particular methylsulfinyl; 
C.sub.1 -C.sub.4 -alkylsulfonyl, such as methylsulfonyl, ethylsulfonyl, 
n-propylsulfonyl, isopropylsulfonyl, n-butylsulfonyl or 
tert-butylsulfonyl, in particular methylsulfonyl; 
C.sub.1 -C.sub.4 -haloalkylsulfonyl, such as trifluoromethylsulfonyl, 
pentafluoroethylsulfonyl or monofluorobutylsulfonyl, in particular 
trifluoromethylsulfonyl; 
phenoxy or phenylthio which may be monosubstituted to trisubstituted by 
alkyl as stated under R.sup.1, in particular methyl, ethyl or isopropyl, 
haloalkyl as stated under R.sup.1, in particular trifluoromethyl or 
chlorodifluoromethyl, alkoxy as stated above, in particular methoxy or 
ethoxy, haloalkoxy as stated above, in particular trifluoromethoxy, 
trichloromethoxy or pentafluoroethoxy, alkylthio as stated above, in 
particular methylthio or ethylthio, haloalkylthio as stated above, in 
particular difluoromethylthio, trifluoromethylthio or 
pentafluoromethylthio, halogen as stated above, in particular fluorine or 
chlorine, cyano or nitro; 
a 5-membered or 6-membered saturated or aromatic heterocyclic radical 
containing one or two hetero atoms selected from the group consisting of 
oxygen, sulfur and nitrogen, as stated under R.sup.1, which may carry one 
or two of the following substituents: alkyl as stated under R.sup.1, in 
particular methyl, halogen as stated under R.sup.1, in particular fluorine 
or chlorine, alkoxy as stated under R.sup.1, in particular methoxy or 
ethoxy, or alkoxycarbonyl, such as methoxycarbonyl or ethoxycarbonyl, in 
particular methoxycarbonyl; 
phenyl which may carry from one to three of the following groups: alkyl as 
stated under R.sup.1, in particular methyl, ethyl or isopropyl, haloalkyl 
as stated under R.sup.1, in particular trifluoromethyl or 
chlorodifluoromethyl, alkoxy as stated under R.sup.1, in particular 
methoxy or ethoxy, haloalkoxy as stated under R.sup.1, in particular 
trifluoromethoxy, trichloromethoxy or pentafluoroethoxy, alkylthio as 
stated under R.sup.1, in particular methylthio or ethylthio, haloalkylthio 
as stated under R.sup.1, in particular difluoromethylthio, 
trifluoromethylthio or pentafluoromethylthio, halogen as stated under 
R.sup.1, in particular fluorine or chlorine, cyano or nitro. 
Examples of herbicidal compounds of the formulae I'a, I'b and I'c are shown 
in the Tables below: 
##STR17## 
R.sup.4 monosubstituted in the 2-, 5- or 6-position, radicals R.sup.4 
independently of one another disubstituted in the 2,5-, 2,6- or 
5,6-position or trisubstituted in the 2,5,6-position or monosubstituted in 
the 4-, 5- or 6-position or independently of one another disubstituted in 
the 4,5-, 5,6- or 4,6-position or trisubstituted in the 4,5,6-position 
______________________________________ 
R.sup.4 
______________________________________ 
H 
F 
Cl 
Br 
I 
Methyl 
Ethyl 
n-Propyl 
Isopropyl 
n-Butyl 
Isobutyl 
sec-Butyl 
tert-Butyl 
Cyclopropyl 
Cyclobutyl 
Cyclopentyl 
Cyclohexyl 
Cycloheptyl 
Cyclooctyl 
1-Methylcyclopropyl 
Cyclopropylmethyl 
1-(Cyclopropyl)-ethyl 
Dichloromethyl 
Trichloromethyl 
Chlorodifluoromethyl 
Trifluoromethyl 
Pentafluoroethyl 
Difluoromethyl 
Methoxymethyl 
1-Methylmethoxymethyl 
1-Methyl-2-methoxyethyl 
1-Methylethoxymethyl 
Ethoxymethyl 
Vinyl 
Allyl 
Methallyl 
Crotyl 
Propargyl 
Cinnamyl 
1-Methyl-2-propenyl 
1-Methyl-2-propynyl 
Methoxy 
Ethoxy 
n-Propoxy 
Isopropoxy 
n-Butoxy 
Isobutoxy 
sec-Butoxy 
tert-Butoxy 
Methylthio 
Ethylthio 
Chlorodifluoromethoxy 
Trifluoromethoxy 
Chlorodifluoromethylthio 
Trifluoromethylthio 
Difluoromethoxy 
Difluoromethylthio 
Trichloromethoxy 
Trichloromethylthio 
Allyloxy 
Allylthio 
Propargyloxy 
Propargylthio 
Cyanomethyl 
2-Cyanoethyl 
1-Methyl-2-cyanoethyl 
1-Methyl-1-cyanoethyl 
1,1-Dimethyl-2-cyanoethyl- 
Methylsulfinyl 
Ethylsulfinyl 
n-Propylsulfinyl 
Isopropylsulfinyl 
Methylsulfonyl 
Ethylsulfonyl 
n-Propylsulfonyl 
Isopropylsulfonyl 
Trifluoromethylsulfonyl 
Chloromethyl 
2-Chloroethyl 
1-Methyl-2-chloroethyl 
1-Methyl-1-chloroethyl 
Nitro 
Cyano 
Phenyl 
2-F-phenyl 
3-F-phenyl 
4-F-phenyl 
2-Cl-phenyl 
3-Cl-phenyl 
4-Cl-phenyl 
2-CH.sub.3 -phenyl 
3-CH.sub.3 -phenyl 
4-CH.sub.3 -phenyl 
2-CF.sub.3 -phenyl 
3-CF.sub.3 -phenyl 
4-CF.sub.3 -phenyl 
2-OCH.sub.3 -phenyl 
3-OCH.sub.3 -phenyl 
4-OCH.sub.3 -phenyl 
2,4-Dichlorophenyl 
Phenoxy 
Phenylthio 
2-Cl-phenoxy 
3-Cl-phenoxy 
4-Cl-phenoxy 
2,4-dichlorophenoxy 
Benzyl 
2-Cl-benzyl 
3-Cl-benzyl 
4-Cl-benzyl 
2-Thienyl 
3-Thienyl 
2-Pyridyl 
3-Pyridyl 
______________________________________ 
##STR18## 
R.sup.4 monosubstituted in the 2-, 5- or 6-position, radicals R.sup.4 
independently of one another disubstituted in the 2,5-, 2,6- or 
5,6-position or trisubstituted in the 2,5,6-position or monosubstituted in 
the 4-, 5- or 6-position or independently of one another disubstituted in 
the 4,5-, 5,6- or 4,6-position or trisubstituted in the 4,5,6-position 
______________________________________ 
R.sup.4 
______________________________________ 
H 
F 
Cl 
Br 
I 
Methyl 
Ethyl 
n-Propyl 
Isopropyl 
n-Butyl 
Isobutyl 
sec-Butyl 
tert-Butyl 
Cyclopropyl 
Cyclobutyl 
Cyclopentyl 
Cyclohexyl 
Cycloheptyl 
Cyclooctyl 
1-Methylcyclopropyl 
Cyclopropylmethyl 
1-(Cyclopropyl)-ethyl 
Dichloromethyl 
Trichloromethyl 
Chlorodifluoromethyl 
Trifluoromethyl 
Pentafluoroethyl 
Difluoromethyl 
Methoxymethyl 
1-Methylmethoxymethyl 
1-Methyl-2-methoxyethyl 
1-Methylethoxymethyl 
Ethoxymethyl 
Vinyl 
Allyl 
Methallyl 
Crotyl 
Propargyl 
Cinnamyl 
1-Methyl-2-propenyl 
1-Methyl-2-propynyl 
Methoxy 
Ethoxy 
n-Propoxy 
Isopropoxy 
n-Butoxy 
Isobutoxy 
sec-Butoxy 
tert-Butoxy 
Methylthio 
Ethylthio 
Chlorodifluoromethoxy 
Trifluoromethoxy 
Chlorodifluoromethylthio 
Trifluoromethylthio 
Difluoromethoxy 
Difluoromethylthio 
Trichloromethoxy 
Trichloromethylthio 
Allyloxy 
Allylthio 
Propargyloxy 
Propargylthio 
Cyanomethyl 
2-Cyanoethyl 
1-Methyl-2-cyanoethyl 
1-Methyl-1-cyanoethyl 
1,1-Dimethyl-2-cyanoethyl 
Methylsulfinyl 
Ethylsulfinyl 
n-Propylsulfinyl 
Isopropylsulfinyl 
Methylsulfonyl 
Ethylsulfonyl 
n-Propylsulfonyl 
Isopropylsulfonyl 
Trifluoromethylsulfonyl 
Chloromethyl 
2-Chloroethyl 
1-Methyl-2-chloroethyl 
1-Methyl-1-chloroethyl 
Nitro 
Cyano 
Phenyl 
2-F-phenyl 
3-F-phenyl 
4-F-phenyl 
2-Cl-phenyl 
3-Cl-phenyl 
4-Cl-phenyl 
2-CH.sub.3 -phenyl 
3-CH.sub.3 -phenyl 
4-CH.sub.3 -phenyl 
2-CF.sub.3 -phenyl 
3-CF.sub.3 -phenyl 
4-CF.sub.3 -phenyl 
2-OCH.sub.3 -phenyl 
3-OCH.sub.3 -phenyl 
4-OCH.sub.3 -phenyl 
2,4-Dichlorophenyl 
Phenoxy 
Phenylthio 
2-Cl-phenoxy 
3-Cl-phenoxy 
4-Cl-phenoxy 
2,4-dichlorophenoxy 
Benzyl 
2-Cl-benzyl 
3-Cl-benzyl 
4-Cl-benzyl 
2-Thienyl 
3-Thienyl 
2-Pyridyl 
3-Pyridyl 
______________________________________ 
For example, further compounds having the general structure 
##STR19## 
where 
W, X, Y or Z are together from one to 3 radicals C--R.sup.4, N or 
N.fwdarw.O, with the proviso that the ring contains a hetero atom and, for 
example, 
R.sup.4 is a radical from the group consisting of Q.sup.1 to Q.sup.133, 
R.sup.1 is a radical from the group consisting of L.sup.1 to L.sup.200, 
R.sup.2 is a radical from the group consisting of P.sup.1 to P.sup.21, 
R.sup.3 is formyl, 4,5-dihydrooxazol-2-yl or a radical --CO--AR.sup.5 or 
--CO--NR.sup.6 R.sup.7, 
A is oxygen or sulfur, 
R.sup.5 is a radical from the group consisting of M.sup.1 to M.sup.90, 
R.sup.6 and R.sup.7 independently of one another are each a radical from 
the group consisting of S.sup.1 to S.sup.15 or together form a radical 
from the group consisting of S.sup.16 to S.sup.19 
and W, X, Y, Z, Q, L, P, M and S may be combined as desired, 
can also be prepared in a similar manner. 
R.sup.4, R.sup.1, R.sup.2, R.sup.5, R.sup.6 and R.sup.7 may be, for 
example, the following radicals: 
______________________________________ 
compound no. 
R.sup.4 
______________________________________ 
Q1 H 
Q2 F 
Q3 Cl 
Q4 Br 
Q5 I 
Q6 CH.sub.3 
Q7 C.sub.2 H.sub.5 
Q8 n-C.sub.3 H.sub.7 
Q9 i-C.sub.3 H.sub.7 
Q10 n-C.sub.4 H.sub.9 
Q11 i-C.sub.4 H.sub.9 
Q12 s-C.sub.4 H.sub.9 
Q13 tert.-C.sub.4 H.sub.9 
Q14 cyclo-C.sub.3 H.sub.5 
Q15 cyclo-C.sub.4 H.sub.7 
Q16 cyclo-C.sub.5 H.sub.9 
Q17 cyclo-C.sub.6 H.sub.11 
Q18 cyclo-C.sub.7 H.sub.13 
Q19 cyclo-C.sub.8 H.sub.15 
Q20 1-Methyl-cyclo-C.sub.3 H.sub.5 
Q21 cyclo-C.sub.3 H.sub.5 -methyl 
Q22 1-(cyclo-C.sub.3 H.sub.5)-ethyl 
Q23 CHCl.sub.2 
Q24 CCl.sub.3 
Q25 CF.sub.2 Cl 
Q26 CF.sub.3 
Q27 C.sub.2 F.sub.5 
Q28 CF.sub.2 H 
Q29 CH.sub.2 OCH.sub.3 
Q30 CH(CH.sub.3)OCH.sub.3 
Q31 CH(CH.sub.3)OC.sub.2 H.sub.5 
Q32 CH(CH.sub.3)CH.sub.2 OCH.sub.3 
Q33 CH.sub.2 OC.sub.2 H.sub.5 
Q34 CHCH.sub.2 
Q35 CH.sub.2 CHCH.sub.2 
Q36 CH(CH.sub.3)CHCH.sub.2 
Q37 CH.sub.2 CHCHCH.sub.3 
Q38 C CH 
Q39 CHCHC.sub. 6 H.sub.5 
Q40 C CC.sub.6 H.sub.5 
Q41 CH(CH.sub.3)C CH 
Q42 neo-C.sub.5 H.sub.11 
Q43 CH.sub.3 O 
Q44 C.sub.2 H.sub.5 O 
Q45 n-C.sub.3 H.sub.7 O 
Q46 i-C.sub.3 H.sub.7 O 
Q47 n-C.sub.4 H.sub.9 O 
Q48 s-C.sub.4 H.sub.9 O 
Q49 i-C.sub.4 H.sub.9 O 
Q50 tert.-C.sub.4 H.sub.9 O 
Q51 CH.sub.3 S 
Q52 C.sub.2 H.sub.5 S 
Q53 n-C.sub.3 H.sub.7 S 
Q54 i-C.sub.3 H.sub.7 S 
Q55 s-C.sub.4 H.sub.9 S 
Q56 tert.-C.sub.4 H.sub.9 S 
Q57 ClCF.sub.2 O 
Q58 CF.sub.3 O 
Q59 ClCF.sub.2 S 
Q60 CF.sub.3 S 
Q61 HCF.sub.2 O 
Q62 HCF.sub.2 S 
Q63 CCl.sub.3 O 
Q64 CCl.sub.3 S 
Q65 CH.sub.2 CHCH.sub.2 O 
Q66 CH.sub.2 CHCH.sub.2 S 
Q67 HC CHCH.sub.2 O 
Q68 HC CHCH.sub.2 S 
Q69 CH.sub.2 CHCH(CH.sub.3)O 
Q70 HC CHCH(CH.sub.3)O 
Q71 CH.sub.2 CN 
Q72 CH.sub.2 CH.sub.2 CN 
Q73 CH(CH.sub.3)CH.sub.2 CN 
Q74 C(CH.sub.3).sub.2 CN 
Q75 C(CH.sub.3).sub.2 CH.sub.2 CN 
Q76 CH.sub.2 Cl 
Q77 CH.sub.2 CH.sub.2 Cl 
Q78 CH(CH.sub.3).sub.2 Cl 
Q79 C(CH.sub.3).sub.2 Cl 
Q80 NO.sub.2 
Q81 CN 
Q82 C.sub.6 H.sub.5 
Q83 2-FC.sub.6 H.sub.4 
Q84 3-FC.sub.6 H.sub.4 
Q85 4-FC.sub.6 H.sub.4 
Q86 2-ClC.sub.6 H.sub.4 
Q87 3-ClC.sub.6 H.sub.4 
Q88 4-ClC.sub.6 H.sub.4 
Q89 2-CH.sub.3 C.sub.6 H.sub.4 
Q90 3-CH.sub.3 C.sub.6 H.sub.4 
Q91 4-CH.sub.3 C.sub.6 H.sub.4 
Q92 2-CF.sub.3 C.sub.6 H.sub.4 
Q93 3-CF.sub.3 C.sub.6 H.sub.4 
Q94 4-CF.sub.3 C.sub.6 H.sub.4 
Q95 2-OCH.sub.3 C.sub.6 H.sub.4 
Q96 3-OCH.sub.3 C.sub.6 H.sub.4 
Q97 4-OCH.sub.3 C.sub.6 H.sub.4 
Q98 4-SCH.sub.3 C.sub.6 H.sub.4 
Q99 4-SCF.sub.3 C.sub.6 H.sub.4 
Q100 4-NO.sub.2 C.sub.6 H.sub.4 
Q101 4-CNC.sub.6 H.sub.4 
Q102 2,4-(Cl,Cl)C.sub.6 H.sub.4 
Q103 2,4-(CH.sub.3 CH.sub.3)C.sub.6 H.sub.4 
Q104 C.sub.6 H.sub.5 O 
Q105 C.sub.6 H.sub.5 S 
Q106 2-ClC.sub.6 H.sub.4 O 
Q107 3-ClC.sub.6 H.sub.4 O 
Q108 4-ClC.sub.6 H.sub.4 O 
Q109 C.sub.6 H.sub.5 CH.sub.2 
Q110 2-ClC.sub.6 H.sub.4CH.sub.2 
Q111 3-ClC.sub.6 H.sub.4CH.sub.2 
Q112 4-ClC.sub.6 H.sub.4CH.sub.2 
Q113 4-FC.sub.6 H.sub.4 CH.sub.2 
Q114 2-Thienyl 
Q115 3-Thienyl 
Q116 2-Furyl 
Q117 3-Furyl 
Q118 1-Methyl-5-pyrazolyl 
Q119 2-Oxazolyl 
Q120 2-Thiazolyl 
Q121 2-Pyridyl 
Q122 3-Pyridyl 
Q123 4-Pyridyl 
Q124 2-Tetrahydrofuryl 
Q125 Methylsulfinyl 
Q126 Ethylsulfinyl 
Q127 n-Propylsulfinyl 
Q128 i-Propylsulfinyl 
Q129 Methylsulfonyl 
Q130 Ethylsulfonyl 
Q131 n-Propylsulfonyl 
Q132 i-Propylsulfonyl 
Q133 Trifluoromethylsulfonyl 
______________________________________ 
comp. no. R.sup.1 
______________________________________ 
L1 H 
L2 CH.sub.3 
L3 C.sub.2 H.sub.5 
L4 n-C.sub.3 H.sub.7 
L5 i-C.sub.3 H.sub.7 
L6 n-C.sub.4 H.sub.9 
L7 i-C.sub.4 H.sub.9 
L8 sec-C.sub.4 H.sub.9 
L9 tert.-C.sub.4 H.sub.9 
L10 n-C.sub.5 H.sub.11 
L11 CH(CH.sub.3)C.sub. 3 H.sub.7 
L12 CH(C.sub.2 H.sub.5)C.sub.2 H.sub.5 
L13 n-C.sub.6 H.sub.13 
L14 CH(CH.sub.3)C.sub.4 H.sub.9 
L15 CH(C.sub.2 H.sub.5)C.sub.3 H.sub.7 
L16 n-C.sub.7 H.sub.15 
L17 CH(CH.sub.3)C.sub.5 H.sub.11 
L18 CH(C.sub.2 H.sub.5)C.sub.4 H.sub.9 
L19 n-C.sub.8 H.sub.17 
L20 CH(CH.sub.3)C.sub.6 H.sub.13 
L21 CH(C.sub.2 H.sub.5)C.sub.5 H.sub.11 
L22 C(CH.sub.3).sub.2 CH.sub.2 C(CH.sub.3).sub.3 
L23 cyclo-C.sub.3 H.sub.5 
L24 cyclo-C.sub.4 H.sub.7 
L25 cyclo-C.sub.5 H.sub.9 
L26 cyclo-C.sub.6 H.sub.11 
L27 cyclo-C.sub.7 H.sub.13 
L28 cyclo-C.sub.8 H.sub.15 
L29 1-Methylcyclohexyl 
L30 1-Ethylcyclohexyl 
L31 3,5-Dimethylcyclohexyl 
L32 3-Trifluoromethylcyclohexyl 
L33 Tetrahydropyran-4-yl 
L34 4-Methyl-tetrahydropyran-2-yl 
L35 4-Methyl-tetrahydropyran-4-yl 
L36 CH.sub.2 CHCH.sub.2 
L37 CH(CH.sub.3)CHCH.sub.2 
L38 C(CH.sub.3).sub.2 CHCH.sub.2 
L39 C(CH.sub.3 C.sub.2 H.sub.5)CHCH.sub.2 
L40 C(CH.sub.3).sub.2C.sub.2 H.sub.5 
L41 C(CH.sub.3 ,C.sub.2 H.sub. 5)C.sub.2 H.sub.5 
L42 C(CH.sub.3).sub.2 C.sub.3 H.sub.7 
L43 C(CH.sub.3).sub.2 cycloC.sub.6 H.sub.11 
L44 CH.sub.2 C(CH.sub.3)CH.sub.2 
L45 CH.sub.2 CHCHCH.sub.3 
L46 CH(CH.sub.3)CHCHCH.sub.3 
L47 C(CH.sub.3).sub.2 CHCHCH.sub.3 
L48 CH.sub.2 C CH 
L49 CH(CH.sub.3)C CH 
L50 C(CH.sub.3).sub.2 C CH 
L51 C(CH.sub.3 ,C.sub.2 H.sub.5)C CH 
L52 C(C.sub.2 H.sub.5).sub.2 C CH 
L53 CH.sub.2 C CCH.sub.3 
L54 CH(CH.sub.3)C CCH.sub.3 
L55 C(CH.sub.3).sub.2 C CCH.sub.3 
L56 CH.sub.2 C.sub.6 H.sub.5 
L57 CH(CH.sub.3)C.sub.6 H.sub.5 
L58 C(CH.sub.3).sub.2 C.sub.6 H.sub.5 
L59 CH.sub.2 CH.sub.2 C.sub.6 H.sub.5 
L60 CH.sub.2 CH.sub.2 SCH.sub.3 
L61 CH(CH.sub.3)CH.sub.2 SCH.sub.3 
L62 C(CH.sub.3).sub.2 CH.sub.2 SCH.sub.3 
L63 CH.sub.2 CH.sub.2 CH.sub.2 SCH.sub.3 
L64 CH.sub.2 CH.sub.2 Cl 
L65 CH(CH.sub.3)CH.sub.2 Cl 
L66 C(CH.sub.3).sub.2 CH.sub.2 Cl 
L67 CH.sub.2 CH.sub.2 OCH.sub.3 
L68 CH(CH.sub.3)CH.sub.2 OCH.sub.3 
L69 C(CH.sub.3).sub.2 CH.sub.2 OCH.sub.3 
L70 CH.sub.2 CH.sub.2 N(CH.sub.3).sub.2 
L71 CH.sub.2 CH.sub.2 N(C.sub.2 H.sub.5).sub.2 
L72 CH.sub.2 CH.sub.2 CH.sub.2 OCH.sub.3 
L73 CH.sub.2 CH.sub.2 CH.sub.2 N(CH.sub.3).sub.2 
L74 CH.sub.2 CH.sub.2 CH.sub.2 N(C.sub.2 H.sub.5).sub.2 
L75 2-CH.sub.3 C.sub.6 H.sub.4 
L76 3-CH.sub.3 C.sub.6 H.sub.4 
L77 4-CH.sub.3 C.sub.6 H.sub.4 
L78 2-C.sub.2 H.sub.5 C.sub.6 H.sub.4 
L79 3-C.sub.2 H.sub.5 C.sub.6 H.sub.4 
L80 4-C.sub.2 H.sub.5 C.sub.6 H.sub.4 
L81 3-tert.-C.sub.4 H.sub.9 C.sub.6 H.sub.4 
L82 4-tert.-C.sub.4 H.sub.9 C.sub.6 H.sub.4 
L83 2,3-(CH.sub.3).sub.2 C.sub.6 H.sub.3 
L84 2,4-(CH.sub.3).sub.2 C.sub.6 H.sub.3 
L85 2,5-(CH.sub.3).sub.2 C.sub.6 H.sub.3 
L86 2,6-(CH.sub.3).sub.2 C.sub.6 H.sub.3 
L87 3,4-(CH.sub.3).sub.2 C.sub.6 H.sub.3 
L88 3,5-(CH.sub.3).sub.2 C.sub.6 H.sub.3 
L89 2,3,4-(CH.sub.3).sub.3 C.sub.6 H.sub.2 
L90 2,3,5-(CH.sub.3).sub.3 C.sub.6 H.sub.2 
L91 2,4,5-(CH.sub.3).sub.3 C.sub.6 H.sub.2 
L92 2,4,6-(CH.sub.3).sub.3 C.sub.6 H.sub.2 
L93 3,4,5-(CH.sub.3).sub.3 C.sub.6 H.sub.2 
L94 2-CF.sub.3 C.sub.6 H.sub.4 
L95 3-CF.sub.3 C.sub.6 H.sub.4 
L96 4-CF.sub.3 C.sub.6 H.sub.4 
L97 2-FC.sub.6 H.sub.4 
L98 3-FC.sub.6 H.sub.4 
L99 4-FC.sub.6 H.sub.4 
L100 2-ClC.sub.6 H.sub.4 
L101 3-ClC.sub.6 H.sub.4 
L102 4-ClC.sub.6 H.sub.4 
L103 2-BrC.sub.6 H.sub.4 
L104 3-BrC.sub.6 H.sub.4 
L105 4-BrC.sub.6 H.sub.4 
L106 2,3-F.sub.2 C.sub.6 H.sub.3 
L107 2,4-F.sub.2 C.sub.6 H.sub.3 
L108 2,5-F.sub.2 C.sub.6 H.sub.3 
L109 2,6-F.sub.2 C.sub.6 H.sub.3 
L110 2,3-Cl.sub.2 C.sub.6 H.sub.3 
L111 2,4-Cl.sub.2 C.sub.6 H.sub.3 
L112 2,5-Cl.sub.2 C.sub.6 H.sub.3 
L113 2,6-Cl.sub.2 C.sub.6 H.sub.3 
L114 3,4-Cl.sub.2 C.sub.6 H.sub.3 
L115 3,5-Cl.sub.2 C.sub.6 H.sub.3 
L116 2,3,4-Cl.sub.3 C.sub.6 H.sub.2 
L117 2,3,5-Cl.sub.3 C.sub.6 H.sub.2 
L118 2,4,6-Cl.sub.3 C.sub.6 H.sub.2 
L119 3,4,5-Cl.sub.3 C.sub.6 H.sub.2 
L120 2-CNC.sub.6 H.sub.4 
L121 3-CNC.sub.6 H.sub.4 
L122 4-CNC.sub.6 H.sub.4 
L123 2-OCH.sub.3 C.sub.6 H.sub.4 
L124 3-OCH.sub.3 C.sub.6 H.sub.4 
L125 4-OCH.sub.3 C.sub.6 H.sub.4 
L126 2-OC.sub.2 H.sub.5 C.sub.6 H.sub.4 
L127 3-OC.sub.2 H.sub.5 C.sub.6 H.sub.4 
L128 4-OC.sub. 2 H.sub.5 C.sub.6 H.sub.4 
L129 2-O-n-C.sub.3 H.sub.7 C.sub.6 H.sub.4 
L130 3-O-n-C.sub.3 H.sub.7 C.sub.6 H.sub.4 
L131 4-O-n-C.sub.3 H.sub.7 C.sub.6 H.sub.4 
L132 2-O-i-C.sub.3 H.sub.7 C.sub.6 H.sub.4 
L133 3-O-i-C.sub.3 H.sub.7 C.sub.6 H.sub.4 
L134 4-O-i-C.sub.3 H.sub.7 C.sub.6 H.sub.4 
L135 2,3-(OCH.sub.3).sub.2 C.sub.6 H.sub.3 
L136 2,4-(OCH.sub.3).sub.2 C.sub.6 H.sub.3 
L137 2,5-(OCH.sub.3).sub.2 C.sub.6 H.sub.3 
L138 2,6-(OCH.sub.3).sub.2 C.sub.6 H.sub.3 
L139 3,4-(OCH.sub.3).sub.2 C.sub.6 H.sub.3 
L140 3,5-(OCH.sub.3).sub.2 C.sub.6 H.sub.3 
L141 3,4,5-(OCH.sub.3).sub.3 C.sub.6 H.sub.2 
L142 2-OCF.sub.3 C.sub.6 H.sub.4 
L143 3-OCF.sub.3 C.sub.6 H.sub.4 
L144 4-OCF.sub.3 C.sub.6 H.sub.4 
L145 2-OCF.sub.2 CHF.sub.2 C.sub.6 H.sub.4 
L146 3-OCF.sub.2 CHF.sub.2 C.sub.6 H.sub.4 
L147 4-OCF.sub.2 CHF.sub.2 C.sub.6 H.sub.4 
L148 2-SCH.sub.3 C.sub.6 H.sub.4 
L149 3-SCH.sub.3 C.sub.6 H.sub.4 
L150 4-SCH.sub.3 C.sub.6 H.sub.4 
L151 2-SC.sub.2 H.sub.5 C.sub.6 H.sub.4 
L152 3-SC.sub.2 H.sub.5 C.sub.6 H.sub.4 
L153 4-SC.sub.2 H.sub.5 C.sub.6 H.sub.4 
L154 2-S-i-C.sub.3 H.sub.7 C.sub.6 H.sub.4 
L155 3-S-i-C.sub.3 H.sub.7 C.sub.6 H.sub.4 
L156 4-S-i-C.sub.3 H.sub.7 C.sub.6 H.sub.4 
L157 2,4-(SCH.sub.3).sub.2 C.sub.6 H.sub.3 
L158 2-SCF.sub.3 C.sub.6 H.sub.4 
L159 3-SCF.sub.3 C.sub.6 H.sub.4 
L160 4-SCF.sub.3 C.sub.6 H.sub.4 
L161 2-NO.sub.2 C.sub.6 H.sub.4 
L162 3-NO.sub.2 C.sub.6 H.sub.4 
L163 4-NO.sub.2 C.sub.6 H.sub.4 
L164 2,3-(NO.sub.2).sub.2 C.sub.6 H.sub.3 
L165 2,4-(NO.sub.2).sub.2 C.sub.6 H.sub.3 
L166 2,5-(NO.sub.2).sub.2 C.sub.6 H.sub.3 
L167 2,6-(NO.sub.2).sub.2 C.sub.6 H.sub.3 
L168 3,4-(NO.sub.2).sub.2 C.sub.6 H.sub.3 
L169 3,5-(NO.sub.2).sub.2 C.sub.6 H.sub.3 
L170 2-CHOC.sub.6 H.sub.4 
L171 3-CHOC.sub.6 H.sub.4 
L172 4-CHOC.sub.6 H.sub.4 
L173 
##STR20## 
L174 
##STR21## 
L175 
##STR22## 
L176 
##STR23## 
L177 
##STR24## 
L178 
##STR25## 
L179 
##STR26## 
L180 
##STR27## 
L181 
##STR28## 
L182 
##STR29## 
L183 
##STR30## 
L184 
##STR31## 
L185 1-Naphthyl 
L186 2-Naphthyl 
L187 C.sub.6 H.sub.5 
L188 Piperidino 
L189 Tetrahydrofur-3-yl 
L190 Thiazol-2-yl 
L191 5-Methyl-thiazol-2-yl 
L192 5-Ethyl-thiazol-2-yl 
L193 5-n-Propyl-thiazol-2-yl 
L194 4-Methyl-5-carboxy-thiazol-2-yl 
L195 Cyclopropylmethyl 
L196 1-(Cyclopropyl)-ethyl 
L197 CH(CH.sub.3)CH.sub.2 CN 
L198 C(CH.sub.3).sub.2 CN 
L199 C(CH.sub.3).sub.2 CH.sub.2 CN 
L200 C(CH.sub.3).sub.2 CH.sub.2 F 
______________________________________ 
comp. no. R.sup.2 
______________________________________ 
P1 H 
P2 CH.sub.3 
P3 C.sub.2 H.sub.5 
P4 n-C.sub.3 H.sub.7 
P5 i-C.sub.3 H.sub.7 
P6 n-C.sub.4 H.sub.9 
P7 s-C.sub.4 H.sub.9 
P8 t-C.sub.4 H.sub.9 
P9 CH.sub.2 CH.sub.2 OH 
P10 CH.sub.2 CH.sub.2 Cl 
P11 CH.sub.2 OCH.sub.3 
P12 CH.sub.2 OC.sub.2 H.sub.5 
P13 CH.sub.2 CH.sub.2 OCH.sub.3 
P14 CH.sub.2 SCH.sub.3 
P15 CH.sub.2 SC.sub.2 H.sub.5 
P16 CH.sub.2 CH.sub.2 SCH.sub.3 
P17 CH.sub.2 CH.sub.2 N(CH.sub.3).sub.2 
P18 CH.sub.2 CH.sub.2 N(C.sub.2 H.sub.5).sub.2 
P19 cyclo-C.sub.3 H.sub.5 
P20 cyclo-C.sub.6 H.sub.11 
P21 1-Methyl-cyclo-C.sub.6 H.sub.10 
______________________________________ 
comp. no. R.sup.5 
______________________________________ 
M1 H 
M2 CH.sub.3 
M3 C.sub.2 H.sub.5 
M4 n-C.sub.3 H.sub.7 
M5 i-C.sub.3 H.sub.7 
M6 n-C.sub.4 H.sub.9 
M7 s-C.sub. 4 H.sub.9 
M8 t-C.sub.4 H.sub.9 
M9 CH(CH.sub.3)C.sub.6 H.sub.13 
M10 CH.sub.2 CH.sub.2 OCH.sub.3 
M11 CH.sub.2 CH.sub.2 OC.sub.2 H.sub.5 
M12 Succinimido 
M13 Li.sup..sym. 
M14 Na.sup..sym. 
M15 K.sup..sym. 
M16 NH.sub.4.sup..sym. 
M17 H.sub.3 N.sup..sym. i-C.sub.3 H.sub.7 
M18 H.sub.2 N.sup..sym. (i-C.sub.3 H.sub.7).sub.2 
M19 H.sub.3 N.sup..sym. CH.sub.2 CH.sub.2 OH 
M20 CH.sub.2 CHCH.sub.2 
M21 CH.sub.2 C(CH.sub.3)CH.sub.2 
M22 CH.sub.2 C(Cl)CH.sub.2 
M23 CH.sub.2 C CH 
M24 CH.sub.2 C CCH.sub.2 OH 
M25 NC(CH.sub.3).sub.2 
M26 NC(C.sub.2 H.sub.5).sub.2 
M27 CH.sub.2 CH.sub.2 N(CH.sub.3).sub.2 
M28 CH.sub.2 CH.sub.2N(C.sub.2 H.sub.5).sub.2 
M29 CH.sub.2 CH.sub.2 N.sup..sym. (CH.sub.3).sub.3 I.sup..crclbar. 
6 
M30 CH.sub.2 CF.sub.3 
M31 Phenyl 
M32 Phenylethyl 
M33 CH.sub.2 CH.sub.2 Si(CH.sub.3).sub.3 
M34 CH.sub.2 CH.sub.2 ONC(CH.sub.3).sub.2 
M35 CH.sub.2 PO(OC.sub.2 H.sub.5).sub.2 
M36 CH(CH.sub.3)CH.sub.2 OCH.sub.3 
M37 CH.sub.2 CON(C.sub.2 H.sub.5).sub.2 
M38 CH.sub.2 CH.sub.2 N(C.sub.2 H.sub.5).sub.2 
M39 CH.sub.2 OCH.sub.2 C.sub.6 H.sub.5 
M40 CH.sub.2 COOCH.sub.3 
M41 NC(cyclo-C.sub.3 H.sub.5).sub.2 
M42 
##STR32## 
M43 Cyclohexanimino 
M44 Cyclooctanimino 
M45 CH.sub.2 CH.sub.2 Cl 
M46 CH.sub.2 CH.sub.2 CN 
M47 CH.sub.2 CCl.sub.3 
M48 Pyrid-3-ylmethyl 
M49 Thien-2-yl-methyl 
M50 CH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.2 OCH.sub.3 
M51 
##STR33## 
M52 CH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.3 
M53 CH(C.sub.6 H.sub.5)CO.sub.2 CH.sub.3 
M54 cyclo-C.sub.6 H.sub.11 
M55 CH.sub.2 OCH.sub.2 (4-ClC.sub. 6 H.sub.4) 
M56 Tetrahydropyran-2-yl 
M57 Tetrahydrofur-2-yl 
M58 (4-Bromo-benzoyl)methyl 
M59 (4-Methoxybenzoyl)methyl 
M60 CH.sub.2 CH.sub.2 COOCH.sub.3 
M61 Phthalimidomethyl 
M62 Fur-2-ylmethyl 
M63 Tetrahydrofur-2-yl-methyl 
M64 Pyrid-2-yl-methyl 
M65 Pyrid-4-yl-methyl 
M66 Pyrid-3-yl-methyl 
M67 Thien-2-yl-methyl 
M68 CH(C.sub.6 H.sub.5)COOCH.sub.3 
M69 Piperidino 
M70 Phthalimido 
M71 Benzotriazol-1-yl 
M72 NCHC.sub.6 H.sub.5 
M73 Fur-2-yl-methylenimino 
M74 2-NO.sub.2 -4-FC.sub.6 H.sub.3 
M75 3,5-(CF.sub.3).sub.2 C.sub.6 H.sub.3 
M76 CH.sub.2 CH.sub.2 SCH.sub.3 
M77 4-NHCOCH.sub.3 C.sub.6 H.sub.4 
M78 2,4-Dichlorobenzyl 
M79 cyclo-C.sub.3 H.sub.5 
M80 1-(cyclo-C.sub.3 H.sub.7)-ethyl 
M81 CH(CH.sub.3)CHCH.sub.2 
M82 CH(CH.sub.3)CH.sub.2 CN 
M83 C(CH.sub.3).sub.2 CN 
M84 CH(CH.sub.3)CH.sub.2 Cl 
M85 C(CH.sub.3).sub.2 CH.sub.2 Cl 
M86 CH.sub.2 CH.sub.2 OCH.sub.2 CO.sub.2 CH.sub.3 
M87 CH.sub.2 CH.sub.2 OCH(CH.sub.3)CO.sub.2 CH.sub.3 
M88 CH.sub.2 CH.sub.2 OCH(CH.sub.3)CO.sub.2 C.sub.2 H.sub.5 
M89 CH(CH.sub.3)CO.sub.2 CH.sub.2 CO.sub.2 CH.sub.3 
M90 CH(CH.sub.3)CO.sub.2 CH(CH.sub.3)CO.sub.2 CH.sub.3 
______________________________________ 
comp. no. R.sup.6 and R.sup.7 independently of one another 
______________________________________ 
S1 H 
S2 CH.sub.3 
S3 C.sub.2 H.sub.5 
S4 n-C.sub.3 H.sub.7 
S5 i-C.sub.3 H.sub.7 
S6 cyclo-C.sub.3 H.sub.5 
S7 n-C.sub.4 H.sub.9 
S8 i-C.sub.4 H.sub.9 
S9 s-C.sub.4 H.sub.9 
S10 tert.-C.sub.4 H.sub.9 
S11 cyclo-C.sub.5 H.sub.9 
S12 cyclo-C.sub.6 H.sub.11 
S13 C.sub.6 H.sub.5 
S14 2-Furyl 
S15 3-Furyl 
S16 (CH.sub.2).sub.4 * 
S17 (CH.sub.2).sub.5 * (*R.sup.6 and R.sup.7 together) 
S18 (CH.sub.2).sub.6 * 
S19 (CH.sub.2).sub.7 * 
______________________________________

PREATION EXAMPLES 
1. 2-Isopropylaminocarbonyl-5-methylpyridine-3-carboxylic acid 
3.25 g of isopropylamine are added to 8.1 g of 
5-methylpyridine-2,3-dicarboxylic anhydride in 50 ml of methylene chloride 
at from 20.degree. to 30.degree. C. while stirring, and the stirred 
mixture is refluxed for 3 hours. The reaction mixture is evaporated down 
under reduced pressure and the residue is stirred in a 1:1:1 mixture of 
ether, methyl tert-butyl ether and petroleum ether. Filtration under 
suction and drying give 10.1 g of the title compound as colorless crystals 
of melting point 95.degree.-105.degree. C. 
Active ingredient Example No. 1.026 
2. N-isopropyl-5-methylpyridine-2,3-dicarboximide 
3 g of the carboxylic acid from 1. in 30 ml of acetic anhydride are 
refluxed for 3 hours while stirring. The reaction mixture is evaporated 
down under reduced pressure, the residue is stirred with water and taken 
up in methylene chloride and the solution is dried over magnesium sulfate. 
Chromatography over alumina, evaporation under reduced pressure and 
washing with 1:1 petroleum ether/ether give 2.3 g of the title compound of 
melting point 127.degree.-128.degree. C. 
Active ingredient Example No. 3.05 
3. 
a) 2-Carbomethoxy-6-methylpyridine-3-carboxylic acid 
48.9 g of 6-methylpyridine-2,3-dicarboxylic anhydride in 200 ml of methanol 
are refluxed for 3 hours while stirring. Evaporating down the mixture 
under reduced pressure gives 57.9 g of the title compound of melting point 
133.degree.-158.degree. C. (decomposition). 
b) 2-Carbomethoxy-6-methylpyridine-3-carbonyl chloride 
44 g of thionyl chloride are added to 57.7 g of the carboxylic acid from a) 
in 250 ml of 1,2-dichloroethane at 60.degree. C. while stirring, and the 
mixture is refluxed for 6 hours. 64 g of the title compound are obtained 
as a semicrystalline mass. According to the NMR spectrum, it contains 
about 20% of the isomeric 3-carbomethoxy compound. 
c) N-sec-butyl-6-methylpyridine-2,3-dicarboximide 
43 g of sec-butylamine are added dropwise to 64 g of the acyl chloride from 
b) in 300 ml of methylene chloride at from 15.degree. to 20.degree. C. 
while stirring, and stirring is continued for 12 hours at 25.degree. C. 
Washing with water and evaporating down under reduced pressure give 43 g 
of a semicrystalline mass. The latter is dissolved in methylene chloride 
and the solution is stirred over active carbon and then chromatographed 
over alumina. 36 g of the title compound are obtained as colorless 
crystals of melting point 105.degree.-106.degree. C. 
Active ingredient Example No. 3.017 
4. 2-(2-Chlorophenyl)-aminocarbonyl-6-methylpyridine-3-carboxylic acid 
54.5 g of the title compound of melting point 155.degree.-160.degree. C. 
are obtained from 32.6 g of 6-methylpyridine-2,3-dicarboxylic anhydride 
and 28.1 g of 2-chloroaniline by the method used in 1. 
Active ingredient Example No. 1.010 
5. Methyl 2-(2-chlorophenyl)-aminocarbonyl-6-methylpyridine-3-carboxylate 
12.8 g of N,N-dicyclohexylcarbodiimide are added to a mixture of 15 g of 
carboxylic acid from 4., 100 ml of diisopropyl ether and 50 ml of methanol 
at from 15.degree. to 20.degree. C., and stirring is carried out for 3 
hours at 50.degree. C. The precipitated urea is filtered off under 
suction, the filtrate is evaporated down under reduced pressure and the 
residue is chromatographed over alumina. Washing with pentane gives 7.5 g 
of the title compound as colorless crystals of melting point 
105.degree.-107.degree. C. 
Active ingredient Example No. 1.007 
N-sec-butyl-5-methylpyridine-2,3-dicarboximide is obtained as colorless 
crystals of melting point 96.degree.-99.degree. C. in the preparation by 
the methods of Preparation Examples 1 and 2 in ring cleavage of 
pyridine-2,3-dicarboxylic anhydride with sec-butylamine and subsequent 
cyclization in acetic anhydride. 
Active ingredient Example No. 3.018 
7. Methyl 2-sec-butylaminocarbonyl-5-methylpyridine-3-carboxylate 
3 g of triethylamine are added dropwise to 4.3 g of the imide from 6. in 
130 ml of methanol at from 20.degree. to 25.degree. C., and the mixture is 
stirred for 2 hours at 50.degree. C. The reaction mixture is evaporated 
down under reduced pressure, the residue is taken up in methylene chloride 
and the solution is chromatographed over silica gel. 2.8 g of the title 
compound of melting point 58.degree.-60.degree. C. are obtained as 
colorless crystals. 
Active ingredient Example No. 1.023 
8. 2-Sec-butylaminocarbonyl-5-methylpyridine-3-carboxamide 
8 g of gaseous ammonia are passed into a solution of 10 g of the imide from 
6. in 200 ml of isopropanol in the course of one hour at 0.degree. C., and 
stirring is carried out for 12 hours at 25.degree. C. The mixture is 
evaporated down under reduced pressure and the residue is stirred with 
methyl tert-butyl ether. 8.3 g of the title compound of melting point 
119.degree.-123.degree. C. are obtained. According to the NMR spectrum, 
20% of the isomeric 3-sec-butylaminocarbonyl compound was formed at the 
same time. 
Active ingredient Example No. 7.003 
9 
2-Tert-butylaminocarbonyl-6-methylpyridine-3-carboxylic acid is obtained as 
colorless crystals of melting point 100.degree.-102.degree. C. on ring 
cleavage of 6-methylpyridine-2,3-dicarboxylic anhydride with 
tert-butylamine by the method of Preparation Example 1. 
Active ingredient Example No. 1.003 
10. Tri-n-butylammonium 
2-tert-butylaminocarbonyl-6-methylpyridine-3-carboxylate 
8.5 g of tri-n-butylamine are added to 9.4 g of the carboxylic acid from 9. 
in 100 ml of methylene chloride at from 20.degree. to 24.degree. C. in the 
course of 10 minutes while stirring, and stirring is continued for a 
further 10 minutes. The reaction mixture is partitioned between water and 
saturated sodium chloride solution. The organic phase is dried and 
evaporated down under reduced pressure and the residue is stirred with 
ether to give 17.7 g of the title compound of melting point 
85.degree.-87.degree. C. 
Active ingredient Example No. 1.020 
11. N-isopropylpyridine-2,3-dicarboximide-1-oxide 
79.7 g of 55% strength 3-chloroperbenzoic acid are added to 22 g of 
N-isopropylpyridine-2,3-dicarboximide in 100 ml of methylene chloride in 
the course of 2 hours while refluxing and stirring, and stirring is 
continued for a further 2 hours. The reaction mixture is extracted three 
times with 10% strength sodium carbonate solution and then with water and 
saturated sodium chloride solution, dried, and evaporated down under 
reduced pressure. The residue is stirred with methyl tert-butyl ether, 
11.2 g of the title compound of melting point 138.degree.-142.degree. C. 
being obtained. 
Active ingredient Example No. 5.003 
12. N-isopropyl-6-chloropyridine-2,3-dicarboximide 
6.5 g of the imide from 11. are added a little at a time to 100 ml of 
phosphorus oxychloride, and the mixture is heated stepwise until it 
refluxes and is stirred for 5 hours. The reaction mixture is evaporated 
down under reduced pressure, the residue is stirred with water and is 
taken up in methylene chloride, and the solution is washed in succession 
with 10% strength sodium carbonate solution, with water and with saturated 
sodium chloride solution. Evaporation gives 4.1 g of the title compound as 
colorless crystals of melting point 122.degree.-23.degree. C. 
Active ingredient Example No. 3.023 
13. N-isopropylpyridine-3,4-dicarboximide-1-oxide 
The title compound is obtained as colorless crystals of melting point 
169.degree.-173.degree. C. by the method of Preparation Example 11, in the 
oxidation of the N-isopropyl-3,4-dicarboximide with 3-chloroperbenzoic 
acid. 
Active ingredient Example No. 6.001 
14. N-isopropyl-6-chloropyridine-3,4-dicarboximide 
The title compound is obtained as colorless crystals of melting point 
94.degree.-96.degree. C. by the method of Preparation Example 12 on 
reacting the N-oxide from 13. with phosphorus oxychloride. According to 
the NMR spectrum, about 15% of the isomeric 1-chloro compound was formed 
at the same time. 
Active ingredient Example No. 4.006 
15. N-isopropyl-6-methoxypyridine-3,4-dicarboximide 
12 g of 30% strength sodium methylate solution are added to 5 g of the 
chlorine compound from 14. in 100 ml of methanol, and the mixture is 
refluxed for 16 hours. The reaction mixture is evaporated down under 
reduced pressure and then partitioned between water/methylene chloride. 
The organic phase is evaporated down and the residue is stirred with 
ether/petroleum ether to give 1.6 g of the title compound of melting point 
150.degree.-152.degree. C. 
Active ingredient Example No. 4.011 
The aqueous phase is neutralized with concentrated hydrochloric acid and 
evaporated down and the residue is stirred with methanol. The organic 
extract is evaporated down to give 4.4 g of sodium 
3-isopropylaminocarbonyl-6-methoxypyridine-4-carboxylate of melting point 
56.degree. C. (decomposition). 
Active ingredient Example No. 2.007 
16 
a) 6-Trichloromethylpyridine-2,3-dicarboxylic anhydride 
A mixture of 200 g of 6-methylpyridine-2,3-dicarboxylic anhydride and 600 
ml of 1,2-dichlorobenzene is gassed at 120.degree. C. for about 1 hour 
with hydrogen chloride, after which 2 g of 
.alpha.,.alpha.-azoisobutyronitrile are added and chlorine gas is passed 
in over 10 hours. The reaction solution is evaporated down and the residue 
is stirred with n-pentane. 311.6 g of the title compound are obtained as 
colorless crystals of melting point 126.degree.-127.degree. C. 
b) 6-Chlorodifluoromethylpyridine-2,3-dicarboxylic anhydride 
A stirred mixture of 53.3 g of the anhydride of a) and 39.3 g of 
antimony(III) fluoride is heated to 120.degree. C. and 5 ml of antimony(V) 
chloride are then slowly added, the exothermic reaction being slowed down 
at 130.degree. C. by removing the heating bath. Stirring is continued for 
a further 30 minutes at 125.degree. C., the mixture is cooled and 100 ml 
of 1,2-dichloroethane are added. 100 ml of 6N hydrochloric acid are then 
slowly run in at from 0.degree. to 10.degree. C. and the aqueous phase is 
extracted with twice 100 ml of methylene chloride. The organic extract is 
washed once with 6N hydrochloric acid. Drying and evaporation give 29.5 g 
of the title compound as a yellowish oil [IR: C.dbd.O 1796 cm.sup.- ]. 
c) 2-Tert-butylaminocarbonyl-6-chlorodifluoromethylpyridine-3-carboxylic 
acid 
28.5 g of the title compound are obtained as a colorless mass from 23.4 g 
of the anhydride from b) and 8 g of tert-butylamine in 200 ml of dioxane 
by the method of Preparation Example 1; .sup.1 H-NMR (CDCl.sub.3) [ppm] 
1.52 (s, 9H), 7.9 (d, 1H), 8.8 (d, 1H). 
Active ingredient Example No. 1.027 
17. N-tert-butyl-6-chlorodifluoromethylpyridine-2,3-dicarboximide 
15.5 g of the title compound are obtained as colorless crystals of melting 
point 138.degree.-140.degree. C. from 28.3 g of the amide from 16 c) in 
300 ml of acetic anhydride by the method of Preparation Example 2. 
Active ingredient Example No. 3.031 
18. N-tert-butyl-6-chloromethylpyridine-3,4-dicarboximide 
31.5 g of N-tert-butyl-6-methylpyridine-3,4-dicarboximide-1-oxide from 
6.004 are added a little at a time to 300 ml of phosphorus oxychloride, 
and the mixture is heated stepwise until it refluxes and is stirred for 3 
hours. The reaction mixture is evaporated down under reduced pressure, the 
residue is taken up in methylene chloride and the solution is stirred into 
ice water. The organic phase is washed several times with water, dried, 
filtered over alumina and evaporated down under reduced pressure. 28.9 g 
of the title compound of melting point 62.degree.-64.degree. C. are 
obtained. 
Active ingredient Example No. 4.010 
19. Methyl 4-tert-butylaminocarbonyl-6-methoxymethylpyridine-3-carboxylate 
44.8 g of 30% strength sodium methylate solution are added to 21.0 g of the 
imide from 18. in 250 ml of methanol at from 25.degree. to 30.degree. C. 
in the course of 15 minutes while stirring, and the mixture is refluxed 
for 6 hours. After cooling, the mixture is brought to a pH of about 6.5 
with 2N methanolic hydrochloric acid and the precipitated sodium chloride 
is filtered off under suction. The filtrate is evaporated down under 
reduced pressure and the residue is triturated with 3:1 methyl tert-butyl 
ether/petroleum ether to give 15.6 g of the title compound of melting 
point 138.degree.-142.degree. C. 
Active ingredient Example No. 9.001 
The pyridine derivatives of the formulae Ia, Ib and Ic listed in the Tables 
below were obtained by these processes described in Examples 1 to 19. 
TABLE 1 
__________________________________________________________________________ 
##STR34## 
phys. data 
No. 
R.sup.1 
R.sup.2 
R.sup.4 
R.sup.5 
A mp. (.degree.C.), IR (cm.sup.-1), NMR 
__________________________________________________________________________ 
(ppm) 
1.001 
i-C.sub.3 H.sub.7 
H H H O 130-136 decomp. 
1.002 
i-C.sub.3 H.sub.7 
H 6-CH.sub.3 
H O 74-75 
1.003 
tert.-C.sub.4 H.sub.9 
H 6-CH.sub.3 
H O 100-102 decomp. 
1.004 
3-Cl-Phenyl 
H 6-CH.sub.3 
H O 162 decomp. 
1.005 
tert.-C.sub.4 H.sub.9 
H 5-C.sub.2 H.sub.5 
H O 60 
1.006 
3-Cl-Phenyl 
H H H O 155 decomp. 
1.007 
2-Cl-Phenyl 
H 6-CH.sub.3 
CH.sub.3 
O 105-107 
1.008 
C.sub.2 H.sub.5 
H H H O 116 decomp. 
1.009 
i-C.sub.3 H.sub.7 
H 5-C.sub.2 H.sub.5 
H O 113-118 
1.010 
2-Cl-Phenyl 
H 6-CH.sub.3 
H O 155-160 
1.011 
tert.-C.sub.4 H.sub. 9 
H H CH.sub.3 
O 70-71 
1.012 
cyclo-Propyl 
H 6-CH.sub.3 
H O 75-80 
1.013 
sec.-C.sub.4 H.sub.9 
H 6-CH.sub.3 
H O resin 
IR: CO 1718, 1662 
1.014 
tert.-C.sub.4 H.sub.9 
H 6-CH.sub.3 
CH.sub.3 
O 84-87 
1.015 
4-Cl-Phenyl 
H 6-CH.sub.3 
H O 140-147 
1.016 
Phenyl H 6-CH.sub.3 
H O 135-142 
1.017 
tert.-C.sub.4 H.sub.9 
H 6-CCl.sub.3 
H O 107-109 
1.018 
4-Cl-Phenyl 
H 6-CCl.sub.3 
H O 200 decomp. 
1.019 
tert.-C.sub.4 H.sub.9 
H 5-CH.sub.3 
H O 105 decomp. 
1.020 
tert.-C.sub.4 H.sub.9 
H 
6-CH.sub.3 
##STR35## 
H 
85-87 
1.021 
Tert.-C.sub.4 H.sub.9 
H 5-CCl.sub.3 
H O 121-125 
1.022 
sec.-C.sub.4 H.sub.9 
H 6-CH.sub.3 
CH.sub.3 
O oel 
IR: CO 1736, 1674 
1.023 
sec.-C.sub.4 H.sub.9 
H 5-CH.sub.3 
CH.sub.3 
O 58-60 
1.024 
i-C.sub.4 H.sub.9 
H 5-CH.sub.3 
CH.sub.3 
O oel 
IR: CO 1736, 1674 
1.025 
i-C.sub.4 H.sub.9 
H 5-CH.sub.3 
H O 65-70 
1.026 
i-C.sub.3 H.sub.7 
H 5-CH.sub.3 
H O 95-105 
1.027 
tert.-C.sub.4 H.sub.9 
H 6-CF.sub.2 Cl 
H O resin 
1, 52 (s; 9H), 7, 9 (d; 1H) 
8, 8 (d; 1H) 
1.028 
i-C.sub.3 H.sub.7 
H HCH.sub.3 
CH.sub.3 
O resin; IR:CO 1736, 1716, 1706, 1677 
1.029 
1-cyclo- 
H 6-CH.sub.3 
CH.sub.3 
O n.sub.D.sup.23 =1.5300 
Propyl-ethyl 
1.030 
tert.-C.sub.4 H.sub.9 
H 6-OCH.sub.3 
CH.sub.3 
O 82-84 
1.031 
tert.-C.sub.4 H.sub.9 
H 6-tert.- 
CH.sub.3 
O n.sub.D.sup.24 =1.5300 
C.sub.4 H.sub.9 
1.032 
sec.-C.sub.4 H.sub.9 
H 6-tert.- 
CH.sub.3 
O 78-83 
C.sub.4 H.sub.9 
1.033 
sec.-C.sub.4 H.sub.9 
H 5-i-C.sub.3 H.sub.7 
H O 28-32 
1.034 
tert.-C.sub.4 H.sub.9 
H 5-i-C.sub.3 H.sub.7 
H O 127-131 
1.035 
sec.-C.sub.4 H.sub.9 
H 5-C.sub.3 H.sub.7, 
CH.sub.3 
O 105 
6-OCH.sub.3 
1.036 
tert.-C.sub.4 H.sub.9 
H 5-C.sub.2 H.sub.5, 
CH.sub.3 
O 136 decomp. 
6-OCH.sub.3 
1.037 
tert.-C.sub.4 H.sub.9 
H 5-C.sub.2 H.sub.5, 
H O 172-175 
6-Cl 
__________________________________________________________________________ 
TABLE 2 
__________________________________________________________________________ 
##STR36## Ic 
No. 
R.sup.1 
R.sup.2 
R.sup.4 
R.sup.5 
A mp. (.degree.C.) 
__________________________________________________________________________ 
2.001 
tert.-C.sub.4 H.sub.9 
H H H O 144-148 
as a mixture with 25% of isomeric 4-amide 
2.002 
i-C.sub.3 H.sub.7 
H H H O 155-161 
as a mixture with 33% of isomeric 4-amide 
2.003 
sec.-C.sub.4 H.sub.9 
H H H O 186-189 
as a mixture with 33% of isomeric 4-amide 
2.004 
tert.-C.sub.4 H.sub.9 
H 6-CH.sub.3 
H O 191 (decomp.) 
as a mixture with 34% of isomeric 4-amide 
2.005 
i-C.sub.3 H.sub.7 
H 6-CH.sub.3 
H O 183 (decomp.) 
as a mixture with 30% of isomeric 4-amide 
2.006 
tert.-C.sub. 4 H.sub.9 
H 6-OCH.sub.3 
CH.sub.3 
O 108-111 
2.007 
i-C.sub.3 H.sub.7 
H 6-OCH.sub.3 
Na O 56 (decomp.) 
__________________________________________________________________________ 
TABLE 3 
______________________________________ 
##STR37## Ia 
phys. data 
mp. (.degree.C.), 
No. R.sup.1 R.sup.4 IR (cm.sup.-1) 
______________________________________ 
3.001 
tert.-C.sub.4 H.sub.9 
H 58-60 
3.002 
i-C.sub.3 H.sub.7 
H 102-104 
3.003 
tert.-C.sub.4 H.sub.9 
6-CH.sub.3 160-161 
3.004 
i-C.sub.3 H.sub.7 
6-CH.sub.3 153-154 
3.005 
i-C.sub.3 H.sub.7 
5-CH.sub.3 127-128 
3.006 
tert.-C.sub.4 H.sub.9 
5-CH.sub.3 120-121 
3.007 
3-Cl-Phenyl H 188-190 
3.008 
Phenyl 6-CH.sub.3 200-205 
3.009 
C.sub.2 H.sub.5 6-CH.sub.3 169-170 
3.010 
tert.-C.sub.4 H.sub.9 
5-C.sub.2 H.sub.5 
82-83 
3.011 
3-Cl-Phenyl 6-CH.sub.3 211-212 
3.012 
C.sub.2 H.sub.5 H 109-111 
3.013 
4-Cl-Phenyl 6-CH.sub.3 244-245 
3.014 
i-C.sub.3 H.sub.7 
6-C.sub.2 H.sub.5 
104-105 
3.015 
cyclo-Propyl 6-CH.sub.3 174-175 
3.016 
2-Cl-Phenyl 6-CH.sub.3 250-253 
3.017 
sec.-C.sub.4 H.sub.9 
6-CH.sub.3 105-106 
3.018 
sec.-C.sub.4 H.sub.9 
5-CH.sub.3 96-99 
3.019 
4-Cl-Phenyl 6-CCl.sub.3 181-182 
3.020 
sec.-C.sub.4 H.sub.9 
H 52-53 
3.021 
tert.-C.sub.4 H.sub.9 
6-CCl.sub.3 148-149 
3.022 
tert.-C.sub.4 H.sub.9 
6-Cl 127-129 
3.023 
i-C.sub.3 H.sub.7 
6-Cl 122-123 
3.024 
sec.-C.sub.4 H.sub.9 
6-Cl 78-80 
3.025 
sec.-C.sub.4 H.sub.9 
5-CH.sub.3, 6-Cl 
104-105 
3.026 
tert.-C.sub.4 H.sub.9 
5-C.sub.2 H.sub.5, 6-Cl 
135-136 
3.027 
tert.-C.sub.4 H.sub.9 
5-CH.sub.3, 6-Cl 
118-121 
3.028 
tert.-C.sub.4 H.sub.9 
5-CCl.sub.3 76-81 
3.029 
tert.-C.sub.4 H.sub.9 
5-CH.sub.3, 6-CH.sub.3 
146-149 
3.030 
sec.-C.sub.4 H.sub.9 
5-CCl.sub.3 resin 
IR: CO 
1720 
3.031 
tert.-C.sub.4 H.sub.9 
6-CF.sub.2 Cl 
138-140 
3.032 
i-C.sub.4 H.sub.9 
5-CH.sub.3 148-151 
3.033 
i-C.sub.4 H.sub.9 
H 93-97 
3.034 
tert.-C.sub.4 H.sub.9 
4-CH.sub.3 131-132 
3.035 
i-C.sub.3 H.sub.7 
4-CH.sub.3 89-90 
3.036 
1-(cyclo-Propyl)ethyl 
6-CH.sub.3 110-112 
3.037 
tert.-C.sub.4 H.sub.9 
4-C.sub.2 H.sub.5 
130-132 
3.038 
i-C.sub.3 H.sub. 7 
4-C.sub.2 H.sub.5 
84-87 
3.039 
i-C.sub.3 H.sub.7 
HCH.sub.3, 6-Cl 
101-103 
3.040 
sec.-C.sub.4 H.sub.9 
6-tert.-C.sub.4 H.sub.9 
n.sub.D.sup.23 =1.5211 
3.041 
tert.-C.sub.4 H.sub.9 
6-tert.-C.sub.4 H.sub.9 
63-67 
3.042 
tert.-C.sub.4 H.sub.9 
6-OCH.sub.3 131-133 
3.043 
tert.-C.sub.4 H.sub.9 
6-CF.sub.3 82-87 
3.044 
tert.-C.sub.4 H.sub.9 
5-tert.-C.sub.4 H.sub.9 
128-132 
3.045 
sec.-C.sub.4 H.sub.9 
5-i-C.sub.3 H.sub.7 
n.sub.D.sup.23 =1.5300 
3.046 
tert.-C.sub.4 H.sub.9 
5-i-C.sub.3 H.sub.7 
60-62 
3.047 
i-C.sub.3 H.sub.7 
5-CH.sub.2 C.sub.6 H.sub.5 
64-67 
3.048 
tert.-C.sub.4 H.sub.9 
5-CH.sub.2 C.sub.6 H.sub.5 
n.sub.D.sup.23 =1.5779 
3.049 
tert.-C.sub.4 H.sub.9 
5-i-C.sub.3 H.sub.7, 6-Cl 
93-95 
3.050 
sec.-C.sub.4 H.sub.9 
6-OCH.sub.3 91-95 
3.051 
C(CH.sub.3).sub.2C.sub.2 H.sub.5 
5-CH.sub.3, 6-CH.sub.3 
84-87 
3.052 
sec.-C.sub.4 H.sub.9 
5-i-C.sub.3 H.sub.7 
n.sub.D.sup.23 =1.5361 
6-OCH.sub.3 
3.053 
tert.-C.sub.4 H.sub.9 
5-C.sub.2 H.sub.5, 
105-107 
6-SO.sub.2 CH.sub.3 
3.054 
tert.-C.sub.4 H.sub.9 
5-C.sub.2 H.sub.5, 
93-97 
6-SCH.sub.3 
3.055 
tert.-C.sub.4 H.sub.9 
5-C.sub.2 H.sub.5, 
94-97 
6-OCH.sub.3 
3.056 
C(CH.sub.3).sub.2 -i-C.sub.3 H.sub.7 
5-CH.sub.3, 6-OCH.sub.3 
125-130 
3.057 
sec.-C.sub.4 H.sub.9 
5-CH.sub.3, 6-OCH.sub.3 
104-106 
3.058 
tert.-C.sub.4 H.sub.9 
5-CH.sub.3, 6-OCH.sub.3 
124-127 
3.059 
tert.-C.sub.4 H.sub.9 
6-OCH.sub.2 CHCH.sub.2 
52-57 
3.060 
C(CH.sub.3)(i-C.sub.3 H.sub.7)CN 
H 92-96 
3.061 
C(CH.sub.3)(CH.sub.2 OCH.sub.3)CN 
H 152-156 
______________________________________ 
TABLE 4 
______________________________________ 
##STR38## Ia 
phys. data 
No. R.sup.1 R.sup.4 mp. (.degree.C.), IR (cm.sup.-1) 
______________________________________ 
4.001 
i-C.sub.3 H.sub.7 
H 103-106 
4.002 
sec.-C.sub.4 H.sub.9 
H oel 
IR:CO 1716 
4.003 
tert.-C.sub.4 H.sub.9 
H 46-49 
4.004 
tert.-C.sub.4 H.sub.9 
6-Cl 73-76 
4.005 
sec.-C.sub.4 H.sub.9 
6-Cl 30-35 
4.006 
i-C.sub.3 H.sub.7 
6-Cl 94-96 
4.007 
tert.-C.sub.4 H.sub.9 
6-CH.sub.3 89-91 
4.008 
i-C.sub.3 H.sub.7 
6-CH.sub.3 91-94 
4.009 
i-C.sub.3 H.sub.7 
6-CH.sub.2 Cl 
63-65 
4.010 
tert.-C.sub.4 H.sub.9 
6-CH.sub.2 Cl 
62-64 
4.011 
i-C.sub.3 H.sub.7 
6-OCH.sub.3 150-152 
4.012 
tert.-C.sub.4 H.sub.9 
6-OCH.sub.3 101-103 
4.013 
tert.-C.sub.4 H.sub.9 
6-CH.sub.2 OCH.sub.3 
38-41 
4.014 
n-C.sub.3 H.sub.7 
2,6-Cl.sub.2 74-78 
4.015 
C(CH.sub.3).sub.2 CN 
H 84-86 
______________________________________ 
TABLE 5 
______________________________________ 
##STR39## Ia 
No. R.sup.1 R.sup.4 mp. (.degree.C.) 
______________________________________ 
5.001 sec.-C.sub.4 H.sub.9 
H 103-104 
5.002 tert.-C.sub.4 H.sub.9 
H 118-122 
5.003 i-C.sub.3 H.sub.7 
H 138-142 
5.004 tert.-C.sub.4 H.sub.9 
5-CH.sub.3 
118-122 
5.005 tert.-C.sub.4 H.sub.9 
5-C.sub.2 H.sub.5 
128-131 
5.006 sec.-C.sub.4 H.sub.9 
5-CH.sub.3 
195-198 
______________________________________ 
TABLE 6 
______________________________________ 
##STR40## Ia 
No. R.sup.1 R.sup.4 mp. (.degree.C.) 
______________________________________ 
6.001 i-C.sub.3 H.sub.7 
H 172-174 
6.002 tert.-C.sub.4 H.sub.9 
H 194-199 
6.003 sec.-C.sub.4 H.sub.9 
H 120-125 
6.004 tert.-C.sub.4 H.sub.9 
6-CH.sub.3 
227-229 
______________________________________ 
TABLE 7 
______________________________________ 
##STR41## Ia 
No. R.sup.1 R.sup.2 
R.sup.4 
R.sup.6 
R.sup.7 
mp. (.degree.C.) 
______________________________________ 
7.001 
sec.-C.sub.4 H.sub.9 
H 6-CH.sub.3 
H H 131-133 
7.002 
tert.-C.sub.4 H.sub.9 
H 6-Cl H H 85 (decomp.) 
7.003 
sec.-C.sub.4 H.sub.9 
H 5-CH.sub.3 
H H 119-123 as a mixture 
with 20% of isomeric 
2-amide 
7.004 
i-C.sub.4 H.sub.9 
H 5-CH.sub.3 
H H 118-122 as a mixture 
with 20% of isomeric 
2-amide 
______________________________________ 
TABLE 8 
______________________________________ 
##STR42## Ib 
No. R.sup.1 R.sup.2 
R.sup.4 R.sup.5 
A mp. (.degree.C.) 
______________________________________ 
8.001 
i-C.sub.4 H.sub.9 
H 5-CH.sub.3 
H O 125-129 
(decomp.) 
8.002 
tert.-C.sub.4 H.sub.9 
H 6-tert.-C.sub.4 H.sub.9 
CH.sub.3 
O 57-61 
______________________________________ 
TABLE 9 
______________________________________ 
##STR43## Ib 
No. R.sup.1 R.sup.2 
R.sup.4 R.sup.5 
A mp. (.degree.C.) 
______________________________________ 
9.001 
tert.-C.sub.4 H.sub.9 
H 6-CH.sub.2 OCH.sub.3 
H O 172-178 
9.002 
tert.-C.sub.4 H.sub.9 
H 6-CH.sub.2 OCH.sub.3 
CH.sub.3 
O 138-142 
______________________________________ 
The compounds I'a, I'b and I'c, or herbicidal agents containing them, may 
be applied for instance in the form of directly sprayable solutions, 
powders, suspensions (including high-percentage aqueous, oily or other 
suspensions), dispersions, emulsions, oil dispersions, pastes, dusts, 
broadcasting agents, or granules by spraying, atomizing, dusting, 
broadcasting or watering. The forms of application depend entirely on the 
purpose for which the agents are being used, but they must ensure as fine 
a distribution of the active ingredients according to the invention as 
possible. 
The compounds I'a, I'b and I'c are suitable for the preparation of 
solutions, emulsions, pastes and oil dispersions to be sprayed direct. 
Examples of inert additives are mineral oil fractions of medium to high 
boiling point, such as kerosene or diesel oil, further coal-tar oils, and 
oils of vegetable or animal origin, aliphatic, cyclic and aromatic 
hydrocarbons such as toluene, xylene, paraffin, tetrahydronaphthalene, 
alkylated naphthalenes and their derivatives, methanol, ethanol, propanol, 
butanol, cyclohexanol, cyclohexanone, chlorobenzene, isophorone, etc., and 
strongly polar solvents such as N,N-dimethylformamide, dimethyl sulfoxide, 
N-methylpyrrolidone and water. 
Aqueous formulations may be prepared from emulsion concentrates, pastes, 
oil dispersions, wettable powders or water-dispersible granules by adding 
water. To prepare emulsions, pastes and oil dispersions the ingredients as 
such or dissolved in an oil or solvent may be homogenized in water by 
means of wetting or dispersing agents, adherents or emulsifiers. 
Concentrates which are suitable for dilution with water may be prepared 
from active ingredient, wetting agent, adherent, emulsifying or dispersing 
agent and possibly solvent or oil. 
Examples of surfactants are: alkali metal, alkaline earth metal and 
ammonium salts of aromatic sulfonic acids, e.g., ligninsulfonic acid, 
phenolsulfonic acid, naphthalenesulfonic acid and 
dibutylnaphthalenesulfonic acid, and of fatty acids, alkyl and alkylaryl 
sulfonates, and alkyl, lauryl ether and fatty alcohol sulfates, and salts 
of sulfated hexadecanols, heptadecanols, and octadecanols, salts of fatty 
alcohol glycol ethers, condensation products of sulfonated naphthalene and 
naphthalene derivatives with formaldehyde, condensation products of 
naphthalene or naphthalenesulfonic acids with phenol and formaldehyde, 
polyoxyethylene octylphenol ethers, ethoxylated isooctylphenol, 
ethoxylated octylphenol and ethoxylated nonylphenol, alkylphenol 
polyglycol ethers, tributylphenyl polyglycol ethers, alkylaryl polyether 
alcohols, isotridecyl alcohol, fatty alcohol ethylene oxide condensates, 
ethoxylated caster oil, polyoxyethylene alkyl ethers, ethoxylated 
polyoxypropylene, lauryl alcohol polyglycol ether acetal, sorbitol esters, 
lignin-sulfite waste liquors and methyl cellulose. 
Powders, dusts and broadcasting agents may be prepared by mixing or 
grinding the active ingredients with a solid carrier. 
Granules, e.g., coated, impregnated or homogeneous granules, may be 
prepared by bonding the active ingredients to solid carriers. Examples of 
solid carriers are mineral earths such as silicic acids, silica gels, 
silicates, talc, kaolin, attapulgus clay, limestone, lime, chalk, bole, 
loess, clay, dolomite, diatomaceous earth, calcium sulfate, magnesium 
sulfate, magnesium oxide, ground plastics, fertilizers such as ammonium 
sulfate, ammonium phosphate, ammonium nitrate, and ureas, and vegetable 
products such as grain meals, bark meal, wood meal, and nutshell meal, 
cellulosic powders, etc. 
The formulations contain from 0.01 to 95, and preferably 0.1 to 90, % by 
weight of active ingredient. The active ingredients are used in a purity 
of from 90 to 100, and preferably from 95 to 100, %. 
The pyridine derivatives I'a, I'b and I'c may be formulated for instance as 
follows: 
I. 90 parts by weight of compound no. 3.003 is mixed with 10 parts by 
weight of N-methyl-alpha-pyrrolidone. A mixture is obtained which is 
suitable for application in the form of very fine drops. 
II. 20 parts by weight of compound no. 3.003 is dissolved in a mixture 
consisting of 80 parts by weight of xylene, 10 parts by weight of the 
adduct of 8 to 10 moles of ethylene oxide and 1 mole of oleic 
acid-N-monoethanolamide, 5 parts by weight of the calcium salt of 
dodecylbenzenesulfonic acid, and 5 parts by weight of the adduct of 40 
moles of ethylene oxide and 1 mole of castor oil. By pouring the solution 
into 100,000 parts by weight of water and uniformly distributing it 
therein, an aqueous dispersion is obtained containing 0.02% by weight of 
the active ingredient. 
III. 20 parts by weight of compound no. 3.004 is dissolved in a mixture 
consisting of 40 parts by weight of cyclohexanone, 30 parts by weight of 
isobutanol, 20 parts by weight of the adduct of 7 moles of ethylene oxide 
and 1 mole of isooctylphenol, and 10 parts by weight of the adduct of 40 
moles of ethylene oxide and 1 mole of castor oil. By pouring the solution 
into 100,000 parts by weight of water and finely distributing it therein, 
an aqueous dispersion is obtained containing 0.02% by weight of the active 
ingredient. 
IV. 20 parts by weight of compound no. 3.003 is dissolved in a mixture 
consisting of 25 parts by weight of cyclohexanone, 65 parts by weight of a 
mineral oil fraction having a boiling point between 210.degree. and 
280.degree. C., and 10 parts by weight of the adduct of 40 moles of 
ethylene oxide and 1 mole of castor oil. By pouring the solution into 
100,000 parts by weight of water and uniformly distributing it therein, an 
aqueous dispersion is obtained containing 0.02% by weight of the active 
ingredient. 
V. 20 parts by weight of compound no. 3.004 is well mixed with 3 parts by 
weight of the sodium salt of diisobutylnaphthalene-alpha-sulfonic acid, 17 
parts by weight of the sodium salt of a lignin-sulfonic acid obtained from 
a sulfite waste liquor, and 60 parts by weight of powdered silica gel, and 
triturated in a hammer mill. By uniformly distributing the mixture in 
20,000 parts by weight of water, a spray liquor is obtained containing 
0.1% by weight of the active ingredient. 
VI. 3 parts by weight of compound no. 1.001 is intimately mixed with 97 
parts by weight of particulate kaolin. A dust is obtained containing 3% by 
weight of the active ingredient. 
VII. 30 parts by weight of compound no. 2.002 is intimately mixed with a 
mixture consisting of 92 parts by weight of powdered silica gel and 8 
parts by weight of paraffin oil which has been sprayed onto the surface of 
this silica gel. A formulation of the active ingredient is obtained having 
good adherence. 
VIII. 20 parts by weight of compound no. 3.010 is intimately mixed with 2 
parts of the calcium salt of dodecylbenzenesulfonic acid, 8 parts of a 
fatty alcohol polyglycol ether, 2 parts of the sodium salt of a 
phenolsulfonic acid-urea-formaldehyde condensate and 68 parts of a 
paraffinic mineral oil. A stable oily dispersion is obtained. 
The active ingredients or the herbicidal agents containing them may be 
applied pre- or postemergence. If certain crop plants tolerate the active 
ingredients less well, application techniques may be used in which the 
herbicidal agents are sprayed from suitable equipment in such a manner 
that the leaves of sensitive crop plants are if possible not touched, and 
the agents reach the soil or the unwanted plants growing beneath the crop 
plants (post-directed, lay-by treatment). 
The application rates depend on the objective to be achieved, the time of 
the year, the plants to be combated and their growth stage, and are from 
0.001 to 5, preferably 0.01 to 2, kg of active ingredient per hectare. 
In view of the numerous application methods possible, the compounds 
according to the invention may be used in a large number of crops for 
removing unwanted plant growth. 
To increase the spectrum of action and to achieve synergistic effects, the 
compounds I'a, I'b and I'c may be mixed with each other, or mixed and 
applied together with numerous representatives of other herbicidal or 
growth-regulating active ingredient groups. Examples of suitable 
components are diazines, 4H-3,1-benzoxazine derivatives, 
benzothiadiazinones, 2,6-dinitroanilines, N-phenylcarbamates, 
thiolcarbamates, halocarboxylic acids, triazines, amides, ureas, diphenyl 
ethers, triazinones, uracils, benzofuran derivatives, 
cyclohexane-1,3-dione derivatives, quinolinecarboxylic acids, 
(hetero)-aryloxyphenoxypropionic acids and salts, esters, amides thereof, 
etc. 
It may also be useful to apply the pyridine derivatives I'a, I'b and I'c, 
either alone or in combination with other herbicides. In admixture with 
other crop protection agents, e.g., agents for combating pests or 
phytopathogenic fungi or bacteria. The compounds may also be mixed with 
solutions of mineral salts used to remedy nutritional or trace element 
deficiencies. Non-phytotoxic oils and oil concentrates may also be added. 
USE EXAMPLES 
The herbicidal action of the pyridine derivatives I'a, I'b and I'c is 
demonstrated in greenhouse experiments: 
The vessels employed were plastic flowerpots having a volume of 300 
cm.sup.3 and filled with a sandy loam containing about 3.0% humus. The 
seeds of the test plants were sown separately, according to species. 
For the preemergence treatment, the active ingredients, suspended or 
emulsified in water, were applied through finely distributing nozzles to 
the surface of the soil immediately after the seeds had been sown. After 
the agents had been applied, the vessels were lightly sprinkler-irrigated 
to induce germination and growth. Transparent plastic covers were then 
placed on the vessels until the plants had taken root. The cover ensured 
uniform germination of the plants, insofar as this was not impaired by the 
active ingredients. 
For the postemergence treatment, the plants were grown, depending on growth 
form, to a height of 3 to 15 cm before being treated with the compounds, 
suspended or emulsified in water. 
The pots were set up in the greenhouse, heat-loving species at 20.degree. 
to 35.degree. C., and species from moderate climates at 10.degree. to 
25.degree. C. The experiments were run for from 2 to 4 weeks. During this 
period the plants were tended and their reactions to the various 
treatments addressed. The assessment scale was 0 to 100, 100 denoting 
nonemergence or complete destruction of at least the visible plant parts, 
and 0 denoting no damage or normal growth. 
The plants used in the greenhouse experiments were Abutilon theophrast, 
Bromus inermis, Chenopodium album, Chrysanthemum coronarium and Stellaria 
media. 
For instance pyridine derivatives 3.003 and 3.004, applied postemergence at 
a rate of 1.0 kg/ha, provided excellent control of unwanted plants.