Herbicidal substituted triazolones of the formula ##STR1## in which R.sup.1 represents hydrogen, alkyl, alkenyl, alkinyl, halogenoalkyl, halogenoalkenyl, halogenoalkinyl, alkoxyalkyl, alkoxy, cycloalkylalkyl or cycloalkyl, or represents in each case optionally substituted aralkyl or aryl, PA0 R.sup.2 represents alkyl, alkenyl, alkinyl, halogenoalkyl, halogenoalkenyl, halogenoalkinyl, alkoxyalkyl, alkoxy, cycloalkyl or cycloalkylalkyl, or represents in each case optionally substituted aryl, aralkyl or heteroaryl, PA1 R.sup.3 and R.sup.4 independently of one another each represent hydrogen or an organic radical, or together with the nitrogen atom to which they are bonded represent an optionally substituted heterocycle, PA0 X represents oxygen or sulphur and PA0 Y represents oxygen or sulphur.

The invention relates to new substituted triazolones, to several processes 
for their preparation, and to their use as herbicides. 
It is known that certain substituted triazolones such as, for example, the 
compound 1-(cyclohexylaminocarbonyl)-3-dimethylamino-4-methyl-1, 
2,4-triazolin-5-one, have herbicidal properties (cf., for example, 
European Patent 283,876). 
However, the herbicidal activity of these previously known compounds 
against problem weeds, as well as their tolerance by important crop 
plants, is not entirely satisfactory in all fields of application. 
New substituted triazolones of the general formula (I) 
##STR2## 
in which 
R.sup.1 represents hydrogen, alkyl, alkenyl, alkinyl, halogenoalkyl, 
halogenoalkenyl, halogenoalkinyl, alkoxyalkyl, alkoxy, cycloalkylalkyl or 
cycloalkyl, or represents in each case optionally substituted aralkyl or 
aryl, 
R.sup.2 represents alkyl, alkenyl, alkinyl, halogenoalkyl, halogenoalkenyl, 
halogenoalkinyl, alkoxyalkyl, alkoxy, cycloalkyl or cycloalkylalkyl, or 
represents in each case optionally substituted aryl, aralkyl or 
heteroaryl, 
R.sup.3 and R.sup.4 independently of one another each represent hydrogen, 
alkyl, alkenyl, alkinyl, halogenoalkyl, halogenoalkenyl, halogenoalkinyl, 
cyanoalkyl, hydroxyalkyl, alkoxyalkyl, alkylaminoalkyl, alkoximinoalkyl, 
alkoxycarbonylalkyl or alkoxycarbonylalkenyl, or represent in each case 
optionally substituted cycloalkyl, cycloalkylalkyl, cycloalkenyl or 
cycloalkenylalkyl, or represent optionally substituted heterocyclylalkyl, 
or represent in each case optionally substituted aralkyl, aroyl or aryl, 
or represent alkoxy, alkenyloxy, alkinyloxy, aralkyloxy or aryloxy, or 
together with the nitrogen atom to which they are bonded represent an 
optionally substituted heterocycle, 
X represents oxygen or sulphur and 
Y represents oxygen or sulphur, have been found. 
Furthermore, it has been found that the new substituted triazolones of the 
general formula (I) 
##STR3## 
in which 
R.sup.1, R.sup.2, R.sup.3, R.sup.4, X and Y are as defined above, are 
obtained when 
a) 1-chloro-(thio)carbonyltriazolones of the formula (II) 
##STR4## 
in which 
R.sup.1, R.sup.2, X and Y are as defined above, are reacted with amines of 
the formula (III) 
##STR5## 
in which 
R.sup.3 and R.sup.4 are as defined above, if appropriate in the presence of 
a diluent and if appropriate in the presence of an acid-binding agent, or 
b) in the event that R.sup.3 in formula (I) represents hydrogen, when 
triazolones which are unsubstituted in the 1-position, of the formula (IV) 
##STR6## 
in which 
R.sup.1, R.sup.2 and X are as defined above, are reacted with 
iso(thio)cyanates of the formula (V) 
EQU R.sup.4 --N.dbd.C.dbd.Y (V) 
in which 
R.sup.4 and Y are as defined above, if appropriate in the presence of a 
diluent and if appropriate in the presence of a reaction auxiliary. 
Finally, it has been found that the new substituted triazolones of the 
general formula (I) have herbicidal properties. 
Surprisingly, the substituted triazolones of the general formula (I) 
according to the invention have a considerably more powerful herbicidal 
potency against problem weeds than the substituted triazolones which are 
known from the prior art, such as, for example, the compound 
1-(cyclohexylaminocarbonyl)-3-dimethylamino-4-methyl-1, 
2,4-triazolin-5-one, which are compounds of a similar chemical structure 
and similar type of action. 
Formula (I) provides a general definition of the substituted triazolones 
according to the invention. Preferred compounds of the formula (I) are 
those in which 
R.sup.1 represents hydrogen, or represents in each case straight-chain or 
branched alkyl having 1 to 8 carbon atoms, alkenyl having 2 to 8 carbon 
atoms, alkinyl having 2 to 8 carbon atoms, halogenoalkyl having 1 to 8 
carbon atoms and 1 to 17 identical or different halogen atoms, 
halogenoalkenyl having 2 to 8 carbon atoms and 1 to 15 identical or 
different halogen atoms, halogenoalkinyl having 2 to 8 carbon atoms and 1 
to 13 identical or different halogen atoms, alkoxyalkyl or alkoxy, each of 
which has 1 to 6 carbon atoms in the individual alkyl moieties, or 
represents cycloalkylalkyl or cycloalkyl, each of which has 3 to 7 carbon 
atoms in the cycloalkyl moiety and, if appropriate, 1 to 6 carbon atoms in 
the straight-chain or branched alkyl moiety, or represents aralkyl or 
aryl, each of which has 6 to 10 carbon atoms in the aryl moiety and, if 
appropriate, 1 to 6 carbon atoms in the straight-chain or branched alkyl 
moiety and each of which is optionally monosubstituted or polysubstituted 
by identical or different substituents, suitable aryl substituents being: 
halogen, cyano, nitro, and in each case straight-chain or branched alkyl, 
alkoxy, alkylthio, halogenoalkyl, halogenoalkoxy or halogenoalkylthio, 
each of which has 1 to 4 carbon atoms and, if appropriate, 1 to 9 
identical or different halogen atoms, 
R.sup.2 represents in each case straight-chain or branched alkyl having 1 
to 8 carbon atoms, alkenyl having 2 to 8 carbon atoms, alkinyl having 2 to 
8 carbon atoms, halogenoalkyl having 1 to 8 carbon atoms and 1 to 17 
identical or different halogen atoms, halogenoalkenyl or halogenoalkinyl, 
each of which has 2 to 8 carbon atoms and 1 to 15, or 13, identical or 
different halogen atoms, alkoxyalkyl or alkoxy, each of which has 1 to 6 
carbon atoms in the individual alkyl moieties, or represents cycloalkyl 
having 3 to 7 carbon atoms, or represents cycloalkylalkyl having 3 to 7 
carbon atoms in the cycloalkyl moiety and 1 to 6 carbon atoms in the alkyl 
moiety, or represents aralkyl which has 6 to 10 carbon atoms in the aryl 
moiety and 1 to 6 carbon atoms in the alkyl moiety and which is optionally 
monosubstituted or polysubstituted by identical or different substituents, 
aryl which has 6 to 10 carbon atoms and which is optionally 
monosubstituted or polysubstituted by identical or different substituents, 
or heteroaryl which has 2 to 9 carbon atoms and 1 to 3 heteroatoms, in 
particular nitrogen, oxygen and/or sulphur, and which is optionally 
monosubstituted or polysubstituted by identical or different substituents, 
suitable substituents in the aryl or heteroaryl moiety in each case being: 
halogen, cyano, nitro and in each case straight-chain or branched alkyl, 
alkoxy, alkylthio, halogenoalkyl, halogenoalkoxy or halogenoalkylthio, 
each of which has 1 to 4 carbon atoms and if appropriate 1 to 9 identical 
or different halogen atoms, 
R.sup.3 and R.sup.4 independently of one another each represents hydrogen, 
or represent in each case straight-chain or branched alkyl having 1 to 18 
carbon atoms, alkenyl having 2 to 8 carbon atoms, alkinyl having 2 to 8 
carbon atoms, halogenoalkyl having 1 to 8 carbon atoms and 1 to 17 
identical or different halogen atoms, halogenoalkenyl or halogenoalkinyl, 
each of which has 2 to 8 carbon atoms and 1 to 15, or 13, identical or 
different halogen atoms, cyanoalkyl having 1 to 8 carbon atoms, 
hydroxyalkyl having 1 to 8 carbon atoms and 1 to 6 hydroxyl groups, 
alkoxyalkyl, alkoxycarbonylalkyl or alkoxycarbonylalkenyl, each of which 
has up to 6 carbon atoms in the individual alkyl or alkenyl moieties, or 
represent alkylaminoalkyl, dialkylaminoalkyl or alkoximinoalkyl, each of 
which has 1 to 8 carbon atoms in the individual alkyl moieties, or 
represent cycloalkyl, cycloalkylalkyl, cycloalkenyl or cycloalkenylalkyl, 
each of which has 3 to 8 carbon atoms in the cycloalkyl or cycloalkenyl 
moiety and if appropriate 1 to 6 carbon atoms in the alkyl moiety and each 
of which is optionally monosubstituted or polysubstituted by identical or 
different substituents, suitable substituents in each case being: halogen, 
cyano and in each case straight-chain or branched alkyl or halogenoalkyl, 
each of which has 1 to 4 carbon atoms and if appropriate 1 to 9 identical 
or different halogen atoms or in each case double-linked alkanediyl or 
alkenediyl, each of which has up to 4 carbon atoms; R.sup.3 and R.sup.4 
furthermore independently of one another represent heterocyclylalkyl which 
has 1 to 6 carbon atoms in the straight-chain or branched alkyl moiety and 
1 to 9 carbon atoms and also 1 to 3 heteroatoms--in particular nitrogen, 
oxygen and/or sulphur--in the heterocyclyl moiety and which is optionally 
monosubstituted or polysubstituted in the heterocyclyl moiety by identical 
or different substituents, suitable substituents being: halogen, cyano, 
nitro, and in each case straight-chain or branched alkyl, alkoxy, 
alkylthio, halogenoalkyl, halogenoalkoxy, halogenoalkylthio or 
alkoxycarbonyl, each of which has 1 to 5 carbon atoms and if appropriate 1 
to 9 identical or different halogen atoms; R.sup.3 and R.sup.4 furthermore 
independently of one another represent in each case straight-chain or 
branched alkoxy having 1 to 8 carbon atoms, alkenyloxy having 2 to 8 
carbon atoms or alkinyloxy having 2 to 8 carbon atoms, and finally 
represent aralkyl, aralkyloxy, aryloxy, aroyl or aryl, each of which has 6 
to 10 carbon atoms in the aryl moiety and if appropriate 1 to 6 carbon 
atoms in the alkyl moiety and each of which is optionally monosubstituted 
or polysubstituted by identical or different substituents, suitable aryl 
substituents in each case being: halogen, cyano, nitro, hydroxyl, in each 
case straight-chain or branched alkyl, alkoxy, alkylthio, halogenoalkyl, 
halogenoalkoxy, halogenoalkylthio, alkylsulphinyl, alkylsulphonyl, 
halogenoalkylsulphinyl, halogenoalkylsulphonyl, alkanoyl or 
alkoxycarbonyl, each of which has 1 to 6 carbon atoms and if appropriate 1 
to 9 identical or different halogen atoms, cycloalkyl having 3 to 6 carbon 
atoms or phenoxy, and, if appropriate, suitable alkyl substituents being: 
halogen or cyano, or 
R.sup.3 and R.sup.4 together with the nitrogen atom to which they are 
bonded represent a five- to ten-membered heterocycle which, if 
appropriate, can contain 1 to 2 further heteroatoms, in particular 
nitrogen, oxygen and/or sulphur, and which is optionally monosubstituted 
or polysubstituted by identical or different substituents, suitable 
substituents being: halogen and in each case straight-chain or branched 
alkyl or halogenoalkyl, each of which have 1 to 4 carbon atoms and if 
appropriate 1 to 9 identical or different halogen atoms and also 1 to 2 
oxo or thiono groups, 
X represents oxygen or sulphur and 
Y represents oxygen or sulphur. 
Particularly preferred compounds of the formula (I) are those in which 
R.sup.1 represents hydrogen, methyl, ethyl, n- or i-propyl, n-, i-, s- or 
t-butyl, n- or i-pentyl or n- or i-hexyl, or represents allyl, propargyl, 
methoxy, ethoxy or methoxymethyl, or represents straight-chain or branched 
halogenoalkyl having 1 to 4 carbon atoms and 1 to 9 identical or different 
halogen atoms, in particular fluorine, chlorine or bromine, or represents 
cyclopentyl, cyclohexyl, cyclopropyl, cyclopropylmethyl, cyclohexylmethyl 
or cyclohexylethyl, or represents benzyl or phenyl, each of which is 
optionally monosubstituted to trisubstituted by identical or different 
substituents, suitable substituents being: fluorine, chlorine, bromine, 
cyano, nitro, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, 
methoxy, ethoxy, methylthio, trifluoromethyl, trifluoromethoxy or 
trifluoromethylthio, 
R.sup.2 represents methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, n- 
or i-pentyl, allyl or propargyl, or represents in each case straight-chain 
or branched halogenoalkyl having 1 to 4 carbon atoms, halogenoalkenyl 
having 3 to 6 carbon atoms or halogenoalkinyl having 3 to 6 carbon atoms 
and in each case 1 to 9 identical or different halogen atoms, or 
represents methoxymethyl, methoxyethyl, methoxy or ethoxy, or represents 
cyclopropyl, cyclopropylmethyl, cyclopentyl, cyclohexyl, cyclohexylmethyl, 
cyclohexylethyl or cyclopentylmethyl, or represents benzyl, phenylethyl or 
phenyl, each of which is optionally monosubstituted to trisubstituted by 
identical or different substituents, suitable substituents in each case 
being: fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, n- or 
i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, methylthio, 
trifluoromethyl, trifluoromethoxy or trifluoromethylthio, 
R.sup.3 and R.sup.4 independently of one another each represent hydrogen, 
methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, n- or i-pentyl, n- 
or i-hexyl, n- or i-heptyl, n- or i-octyl, n- or i-nonyl, n- or i-decyl, 
n- or i-dodecyl, or represent allyl, n- or i-butenyl, n- or i-pentenyl, n- 
or i-hexenyl, propargyl, n- or i-butinyl, n- or i-pentinyl, n- or 
i-hexinyl, or represent straight-chain or branched halogenoalkyl having 1 
to 6 carbon atoms and 1 to 9 identical or different halogen atoms, in 
particular fluorine, chlorine or bromine, or represent in each case 
straight-chain or branched halogenoalkenyl or halogenoalkinyl, each of 
which has 3 to 8 carbon atoms and 1 to 3 halogen atoms, in particular 
fluorine or chlorine, or represent in each case straight-chain or branched 
cyanoalkyl having 1 to 6 carbon atoms in the alkyl moiety, hydroxyalkyl 
having 1 to 6 carbon atoms and 1 to 3 hydroxyl groups, alkoxyalkyl, 
alkoxycarbonylalkyl or alkoxycarbonylalkenyl, alkylaminoalkyl or 
dialkylaminoalkyl, each of which has up to 4 carbon atoms in the 
individual alkyl or alkenyl moieties, or represent in each case optionally 
straight-chain or branched methoximinoalkyl or ethoximinoalkyl, each of 
which has 1 to 5 carbon atoms in the alkyl moiety, or represent 
cyclopropyl, cyclopropylmethyl, cyclopropylethyl, cyclopentyl, cyclohexyl, 
cycloheptyl, cyclooctyl, cyclohexylmethyl, cyclohexylethyl, cyclohexenyl 
or cyclohexenylmethyl, each of which is optionally monosubstituted to 
trisubstituted by identical or different substituents, suitable 
substituents in each case being: fluorine, chlorine, bromine, methyl, 
ethyl, n- or i-propyl, n-, i-, s- or t-butyl, cyano, methanediyl, 
ethanediyl, butanediyl or butadienediyl; R.sup.3 and R.sup.4 furthermore 
independently of one another represent heterocyclylmethyl, 
heterocyclylpropyl, heterocyclylethyl or heterocyclylbutyl, each of which 
is optionally monosubstituted to trisubstituted in the heterocyclyl moiety 
by identical or different substituents, suitable substituents being: 
fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, n- or i-propyl, 
n-, i-, s- or t-butyl, methoxy, ethoxy, methylthio, trifluoromethyl, 
trifluoromethoxy or trifluoromethylthio, and suitable heterocycles in each 
case being: 
##STR7## 
where Z in each case represents oxygen or sulphur; R.sup.3 and R.sup.4 
furthermore independently of one another represent in each case 
straight-chain or branched alkoxy having 1 to 6 carbon atoms, alkenyloxy 
having 3 to 6 carbon atoms or alkinyloxy having 3 to 6 carbon atoms, or 
represent benzyl, phenylethyl, phenylpropyl, phenylbutyl, phenylpentyl, 
phenylhexyl, phenylheptyl, phenylcyanomethyl, phenylcyanoethyl, 
phenylcyanopropyl, benzyloxy, phenylethyloxy, phenoxy, benzoyl, phenyl or 
naphthyl, each of which is optionally monosubstituted to trisubstituted by 
identical or different substituents, suitable phenyl substituents in each 
case being: fluorine, chlorine, bromine, hydroxyl, cyano, nitro, methyl, 
ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, methylthio, 
trifluoromethyl, trifluoromethoxy, trifluoromethylthio, 
trifluoromethylsulphinyl, trifluoromethylsulphonyl, methylsulphinyl, 
methylsulphonyl, acetyl, propionyl, methoxycarbonyl, ethoxycarbonyl, 
cyclohexyl or phenoxy; or 
R.sup.3 and R.sup.4 together with the nitrogen atom to which they are 
bonded represent a heterocycle of the formula 
##STR8## 
optionally monosubstituted to trisubstituted by identical or different 
substituents, suitable substituents in each case being: methyl, ethyl, n- 
or i-propyl, chlorine or trifluoromethyl, 
X represents oxygen or sulphur and 
Y represents oxygen or sulphur. 
If, for example, 1-chlorocarbonyl-3-methylamino-4-methyl-1, 
2,4-triazolin-5-one and allyl amine are used as the starting substances, 
the course of the reaction of process (a) according to the invention may 
be represented by the following equation: 
##STR9## 
If, for example, 3-ethylamino-4-methyl-1H-1, 2,4-triazolin-5-one and 
isopropyl isocyanate are used as the starting substances, the course of 
the reaction of process (b) according to the invention may be represented 
by the following equation: 
##STR10## 
Formula (II) provides a general definition of the 
chloro(thio)carbonyltriazolones required as starting substances for 
carrying out process (a) according to the invention. In this formula (II), 
R.sup.1, R.sup.2, X and Y preferably represent those radicals which have 
already been mentioned in connection with the description of the 
substances of the formula (I) according to the invention as being 
preferred for these substituents. 
The chloro(thio)carbonyltriazolones of the formula (II) were hitherto 
unknown. 
They are obtained when triazolones which are unsubstituted in the 
1-position, of the formula (IV) 
##STR11## 
in which 
R.sup.1, R.sup.2 and X are as defined above, are reacted with 
(thio)phosgene of the formula (VI) 
##STR12## 
in which 
Y is as defined above, if appropriate in the presence of a diluent, such 
as, for example, toluene, chlorobenzene or acetonitrile, and if 
appropriate in the presence of an acid-binding agent, such as, for 
example, triethylamine, at temperatures between +20.degree. C. and 
+150.degree. C. 
Formula (III) provides a general definition of the amines furthermore 
required as starting substances for carrying out process (a) according to 
the invention. In this formula (III), R.sup.3 and R.sup.4 preferably 
represent those radicals which have already been mentioned in connection 
with the description of the substances of the formula (I) according to the 
invention as being preferred for these substituents. 
The amines of the formula (III) are generally known compounds of organic 
chemistry. 
Formula (IV) provides a general definition of the triazolones which are 
unsubstituted in the 1-position and which are required as starting 
substances for carrying out process (b) according to the invention and for 
synthesizing the precursors of the formula (II). In this formula (IV), 
R.sup.1, R.sup.2 and X preferably represent those radicals which have 
already been mentioned in connection with the description of the 
substances of the formula (I) according to the invention as being 
preferred for these substituents. 
The triazolones which are unsubstituted in the 1-position, of the formula 
(IV), are known or can be obtained in analogy to known processes (cf., for 
example, European Patent 283,876; Arch. Pharm. 303, 263-267 [1970]; Arch. 
Pharm. 307, 509-516 [1974]; J. Org. Chem. 34, 1808-1816 [1969]; Chem. Ber. 
107, 454-459 [1974]; J. Heterocycl. Chem. 15, 377-384 [1978]; Pharmazie 
29, 20-25 [1974]; Indian J. Chem. 8, 391-394 [1970]; Indian J. Chem. 6, 
287-293 [1968]; Japanese Patent 46/37,646; Japanese Patent 62/2,248 
Japanese Patent 62/153,850; DE 2,714,880; DE 2,716,707; Indian J. Chem. 
Sect. B 21B, 321-324 [1982]; Helv. Chim. Acta 63, 841-859 [1980]; DE 
2,145,414; J. Chem. Soc. C 1967, 2471-2472; J. Chem. Soc. C 1967, 746-751; 
J. Chem. Soc. C 1968, 1375-1380; J. Chem. Soc. C 1967, 742-746; GB 
1,049,111; Arch. Pharm. 306, 659-664 [1973]; Farmacia 15, 415-419 [1967] 
and the Preparation Examples). 
The compounds of the formula (IV) in which 
(.alpha.) X represents oxygen and R.sup.1 and R.sup.2 represent methyl, or 
in which 
(.beta.) X represents oxygen or sulphur and R.sup.1 represents methyl and, 
simultaneously, R.sup.2 represents ethyl, or R.sup.1 represents ethyl and, 
simultaneously, R.sup.2 represents methyl, or R.sup.1 and R.sup.2 
represent ethyl, are new. 
The new and known compounds of the formula (IV) are obtained, for example, 
when aminoguanidinium hydrochlorides (VIIb) 
##STR13## 
in which 
R.sup.5 and R.sup.6 represent alkyl, in particular methyl or ethyl, and 
R.sup.2 is as defined above, are reacted with iso(thio)cyanates of the 
formula (X) 
EQU R.sup.1 --N.dbd.C.dbd.X (X) 
in which 
R.sup.1 and X are as defined above, if appropriate in the presence of a 
diluent such as, for example, toluene, chlorobenzene or acetonitrile, and 
if appropriate in the presence of an acid-binding agent, such as, for 
example, potassium carbonate or triethylamine, at temperatures between 
20.degree. and 150.degree. C., or when 3alkylthiotriazolones of the 
formula (XI) 
##STR14## 
in which 
R.sup.7 represents alkyl, in particular methyl or ethyl, and 
R.sup.1 and X are as defined above, are reacted with amines of the formula 
(XII) 
EQU R.sup.2 --NH.sub.2 (XII) 
in which 
R.sup.2 is as defined above, if appropriate in the presence of a diluent 
such as, for example, ethanol or acetonitrile, at temperatures between 
50.degree. and 300.degree. C. in pressure ranges between atmospheric 
pressure and 300 bar. 
Aminoguanidinium hydrochlorides of the formula (VIIb) are known or can be 
obtained in analogy to known processes (cf., for example, European Patent 
283,876; J. Org. Chem. 19, 1807 [1954]; Bull. Soc. Chim. France 1975, 
1649; U.S. Pat. No. 2,845,458). 
Iso(thio)cyanates of the formula (X) are generally known compounds of 
organic chemistry. 
3-alkylthiotriazolones of the formula (XI) are likewise known (cf., for 
example, European Patent 283,876; DE 2,527,676; DE 2,250,572; U.S. Pat. 
No. 4,098,896; U.S. Pat. No. 4,110,332; U.S. Pat. No. 4,530,898; J. Chem. 
Soc. C 1967, 746-751). 
Amines of the formula (XII) are generally known compounds of organic 
chemistry. 
Formula (V) provides a general definition of the iso(thio)cyanates 
furthermore required as starting substances for carrying out process (b) 
according to the invention. In this formula (V), R.sup.4 and Y preferably 
represent those radicals which have already been mentioned in connection 
with the description of the substances of the formula (I) according to the 
invention as being preferred for these substituents. 
The iso(thio)cyanates are generally known compounds of organic chemistry 
(cf., for example, Saul Patai, "The Chemistry of Cyanates and their 
Thioderivates" J. Wiley & Sons, New York 1977). 
Preferred suitable diluents for carrying out process (a) according to the 
invention are inert organic solvents. 
These include, in particular, aliphatic, alicyclic or aromatic, optionally 
halogenated hydrocarbons, such as, for example, benzine, ligroin, benzene, 
toluene, xylene, chlorobenzene, petroleum ether, pentane, hexane, heptane, 
cyclohexane, dichloromethane, chloroform and carbon tetrachloride, ethers, 
such as diethyl ether, dioxane, tetrahydrofuran, ethylene glycol dimethyl 
ether or ethylene glycol diethyl ether, ketones, such as acetone or 
butanone, nitriles, such as acetonitrile or propionitrile, amides, such as 
dimethylformamide, dimethylacetamide, N-methylformanilide, 
N-methylpyrrolidone or hexamethylphosphoric triamide, esters, such as 
ethyl acetate, or bases, such as pyridine. 
If appropriate, process (a) according to the invention is carried out in 
the presence of a suitable acid-binding agent. 
Suitable acid-binding agents are all customary inorganic or organic bases. 
These include, for example, alkali metal hydroxides, such as sodium 
hydroxide or potassium hydroxide, alkali metal carbonates, such as sodium 
carbonate, potassium carbonate or sodium hydrogen carbonate, and tertiary 
amines, such as triethylamine, N,N-dimethylaniline, pyridine, 
N,N-dimethylaminopyridine, diazabicyclooctane (DABCO), diazabicyclononene 
(DBN) or diazobicycloundecene (DBU). 
It is also possible to employ the amine of the formula (III), which is used 
as a reactant, in appropriate excess to act simultaneously as an 
acid-binding agent. 
When carrying out process (a) according to the invention, the reaction 
temperatures can be varied within a substantial range. In general, the 
process is carried out at temperatures between 0.degree. C. and 
+150.degree. C., preferably at temperatures between +10.degree. C. and 
+80.degree. C. 
Process (a) according to the invention is customarily carried out under 
atmospheric pressure. However, it is also possible to carry out the 
process under increased pressure. 
For carrying out process (a) according to the invention, 1.0 to 5.0 moles, 
preferably 1.0 to 2.5 moles, of the amine of the formula (III) and if 
appropriate 1.0 to 2.5 moles of acid-binding agent are generally employed 
per mole of 1-chlor-(thio)carbonyltriazolone of the formula (II). The 
reaction is carried out and the reaction products are worked up and 
isolated in analogy to generally known processes. 
Suitable diluents for carrying out process (b) according to the invention 
are likewise inert organic solvents. The diluents which have been 
mentioned in process (a) are preferably used. 
If appropriate, process (b) according to the invention can be carried out 
in the presence of a basic reaction auxiliary. Suitable basic reaction 
auxiliaries are all customary inorganic and organic bases. Tertiary 
amines, such as triethylamine, N,N-dimethylaniline, pyridine, 
N,N-dimethylaminopyridine, diazabicyclooctane (DABCO), diazabicyclononene 
(DBN) or diazabicycloundecene (DBU) are preferably used. 
However, it is not absolutely necessary to add such catalysts. 
When carrying out process (b) according to the invention, the reaction 
temperatures can be varied within a substantial range. In general, the 
process is carried out at temperatures between 0.degree. C. and 
+150.degree. C., preferably at temperatures between +40.degree. C. and 
+120.degree. C. 
Process (b) according to the invention is customarily carried out under 
atmospheric pressure. However, it is also possible to carry out the 
process under increased pressure, in particular in the case of gaseous 
starting compounds. 
For carrying out process (b) according to the invention, 1.0 to 5.0 moles, 
preferably 1.0 to 2.5 moles, of iso(thio)cyanate of the formula (V) and if 
appropriate 1.0 to 2.5 moles of reaction auxiliary are generally employed 
per mole of triazolone which is unsubstituted in the 1-position, of the 
formula (IV). The reaction is carried out and the reaction products are 
worked up and isolated in analogy to generally known processes. 
The active compounds according to the invention can be used as defoliants, 
desiccants, agents for destroying broad-leaved plants and, especially, as 
weedkillers. By weeds, in the broadest sense, there are to be understood 
all plants which grow in locations where they are undesired. Whether the 
substances according to the invention act as total or selective herbicides 
depends essentially on the amount used. 
The active compounds according to the invention can be used, for example, 
in connection with the following plants: 
Dicotyledon weeds of the genera: Sinapis, Lepidium, Galium, Stellaria, 
Matricaria, Anthemis, Galinsoga, Chenopodium, Urtica, Senecio, Amaranthus, 
Portulaca, Xanthium, Convolvulus, Ipomoea, Polygonum, Sesbania, Ambrosia, 
Cirsium, Carduus, Sonchus, Solanum, Rorippa, Rotala, Lindernia, Lamium, 
Veronica, Abutilon, Emex, Datura, Viola, Galeopsis, Papaver and Centaurea. 
Dicotyledon cultures of the genera: Gossypium, Glycine, Beta, Daucus, 
Phaseolus, Pisum, Solanum, Linum, Ipomoea, Vicia, Nicotiana, Lycopersicon, 
Arachis, Brassica, Lactuca, Cucumis and Cucurbita. 
Monocotyledon weeds of the genera: Echinochloa, Setaria, Panicum, 
Digitaria, Phleum, Poa, Festuca, Eleusine, Brachiaria, Lolium, Bromus, 
Avena, Cyperus, Sorghum, Agropyron, Cynodon, Monochoria, Fimbristylis, 
Sagittaria, Eleocharis, Scirpus, Paspalum, Ischaemum, Sphenoclea, 
Dactyloctenium, Agrostis, Alopecurus and Apera. 
Monocotyledon cultures of the genera: Oryza, Zea, Triticum, Hordeum, Avena, 
Secale, Sorghum, Panicum, Saccharum, Ananas, Asparagus and Allium. 
However, the use of the active compounds according to the invention is in 
no way restricted to these genera, but also extends in the same manner to 
other plants. 
The compounds are suitable, depending on the concentration, for the total 
combating of weeds, for example on industrial terrain and rail tracks, and 
on paths and squares with or without tree plantings. Equally, the 
compounds can be employed for combating weeds in perennial cultures, for 
example forests, decorative tree plantings, orchards, vineyards, citrus 
groves, nut orchards, banana plantations, coffee plantations, tea 
plantations, rubber plantations, oil palm plantations, cocoa plantations, 
soft fruit plantings and hopfields, and for the selective combating of 
weeds in annual cultures. 
In this context, the active compounds of the formula (I) according to the 
invention can be employed with particularly good success for combating 
dicotyledon weeds, in particular in monocotyledon cultures, such as, for 
example, maize. 
Moreover, the active compounds according to the invention engage in the 
metabolism of the plants and can therefore be employed as growth 
regulators. 
Experience to date of the mode of action of plant growth regulators has 
shown that an active compound can also exert several different actions on 
plants. The actions of the compounds depend essentially on the point in 
time at which they are used, relative to the stage of development of the 
plant, and on the amount of active compound applied to the plants or their 
environment, and the way in which the compounds are applied. In each case, 
growth regulators are intended to influence the crop plants in the 
particular manner desired. 
Under the influence of growth regulators, the amount of leaf on plants can 
be controlled so that defoliation of the plants at a desired point in time 
is achieved. Such defoliation is of great importance in the mechanical 
harvesting of cotton, but is also of interest for facilitating harvesting 
in other crops, such as, for example, in viticulture. Defoliation of the 
plants can also be carried out to reduce the transpiration of the plants 
before they are transplanted. 
In appropriate application rates, the active compounds according to the 
invention also show a fungicidal activity and can be employed, for 
example, for combating fungal diseases in cereal and rice growing, such 
as, for example, against the pathogen causing mildew on cereals (Erysiphe 
graminis) or against the pathogen causing rice blast disease (Pyricularia 
oryzae) or for combating fungal diseases in fruit and vegetable growing, 
such as, for example, against the pathogen of apple scab (Venturia 
inaequalis), or against Cercospora species. In this field of application, 
the active compounds according to the invention show not only good 
protective properties, but also systemic properties. 
Depending on their particular physical and/or chemical properties, the 
active compounds can be converted to the customary formulations, such as 
solutions, emulsions, suspensions, powders, foams, pastes, granules, 
aerosols, natural and synthetic materials impregnated with active 
compound, very fine capsules in polymeric substances and in coating 
compositions for seed, and ULV cold mist and warm mist formulations. 
These formulations are produced in a known manner, for example by mixing 
the active compounds with extenders, that is, liquid solvents, liquefied 
gases under pressure and/or solid carriers, optionally with the use of 
surface-active agents, that is, emulsifying agents and/or dispersing 
agents and/or foam-forming agents. In the case of the use of water as an 
extender, organic solvents can, for example, also be used as auxiliary 
solvents. As liquid solvents, there are suitable in the main: aromatics, 
such as xylene, toluene, or alkylnaphthalenes, chlorinated aromatics or 
chlorinated aliphatic hydrocarbons, such as chlorobenzenes, 
chloroethylenes or methylene chloride, aliphatic hydrocarbons, such as 
cyclohexane or paraffins, for example mineral oil fractions, alcohols, 
such as butanol or glycol as well as their ethers and esters, ketones, 
such as acetone, methyl ethyl ketone, methyl isobutyl ketone or 
cyclohexanone, strongly polar solvents, such as dimethylformamide and 
dimethyl sulphoxide, as well as water; by liquefied gaseous extenders or 
carriers are meant liquids which are gaseous at ambient temperature and 
under atmospheric pressure, for example aerosol propellants, such as 
halogen hydrocarbons as well as butane, propane, nitrogen and carbon 
dioxide; as solid carriers there are suitable: for example ground natural 
minerals, such as kaolins, clays, talc, chalk, quartz, attapulgite, 
montmorillonite or diatomaceous earth, and ground synthetic minerals, such 
as highly-disperse silica, alumina and silicates; as solid carriers for 
granules there are suitable: for example crushed and fractionated natural 
rocks such as calcite, marble, pumice, sepiolite and dolomite, as well as 
synthetic granules of inorganic and organic meals, and granules of organic 
material such as sawdust, coconut shells, corn cobs and tobacco stalks; as 
emulsifying and/or foam-forming agents there are suitable: for example 
non-ionic and anionic emulsifiers, such as polyoxyethylene fatty acid 
esters, polyoxyethylene fatty alcohol ethers, for example alkylaryl 
polyglycol ethers, alkylsulphonates, alkyl sulphates, arylsulphonates as 
well as albumin hydrolysis products; as dispersing agents there are 
suitable: for example lignin-sulphite waste liquors and methylcellulose. 
Adhesives such as carboxymethylcellulose and natural and synthetic polymers 
in the form of powders, granules or latices, such as gum arabic, polyvinyl 
alcohol and polyvinyl acetate, as well as natural phospholipids, such as 
cephalins and lecithins, and synthetic phospholipids, can be used in the 
formulations. Other additives can be mineral and vegetable oils. 
It is possible to use colorants such as inorganic pigments, for example 
iron oxide, titanium oxide and Prussian Blue, and organic dyestuffs, such 
as alizarin dyestuffs, azo dyestuffs and metal phthalocyanine dyestuffs, 
and trace nutrients such as salts of iron, manganese, boron, copper, 
cobalt, molybdenum and zinc. 
The formulations in general contain between 0.1 and 95 per cent by weight 
of active compound, preferably between 0.5 and 90%. 
For combating weeds, the active compounds according to the invention, as 
such or in the form of their formulations, can also be used as mixtures 
with known herbicides, finished formulations or tank mixes being possible. 
Suitable herbicides for the mixtures are known herbicides, such as, for 
example, 1-amino-6-ethylthio-3-(2, 
2-dimethylpropyl)-1,3,5-triazine-2,4(1H, 3H)-dione (AMETHYDIONE) or 
N-(2-benzothiazolyl)-N,N'-dimethylurea (METABENZTHIAZURON) for combating 
weeds in cereals; 4-amino-3-methyl-6-phenyl-1,2, 4-triazin-5(4H)-one 
(METAMITRON) for combating weeds in sugar beets and 
4-amino-6-(1,1-dimethylethyl)-3-methylthio-1, 2,4-triazin-5(4H)-one 
(METRIBUZIN) for combating weeds in soy beans. Mixtures with 
2,4-dichlorophenoxyacetic acid (2,4-D); 4-(2,4-dichlorophenoxy)-butyric 
acid (2,4-DB); 2,4dichlorophenoxypropionic acid (2,4-DP); 
2-chloro-4-ethylamino-6-isopropylamino-1,3, 5-triazine(ATRAZINE); 
3-isopropyl-2,1, 3-benzothiadiazin-4-one 2,2-dioxide (BENTAZONE); methyl 
5-(2, 4-dichlorophenoxy)-2-nitrobenzoate (BIFENOX); 
3,5-dibromo-4-hydroxy-benzonitrile (BROMOXYNIL); 
2-chloro-N{[(4-methoxy-6-methyl-1, 
3,5-triazin-2-yl)-amino]-carbonyl}benzenesulphonamide (CHLORSULFURON); 
N,N-dimethyl-N'-(3-chloro-4-methylphenyl)-urea (CHLORTOLURON); 
2-chloro-4-ethylamino-6-(3-cyanopropylamino) -1,3,5-triazine (CYANAZIN); 
2-[4-(2, 4-dichlorophenoxy)-phenoxy]-propionic acid, its methyl ester or 
its ethyl ester (DICLOFOP); 
4-amino-6-t-butyl-3-ethylthio-1,24-thiazin-5(44 )-one (ETHIOZIN); 
2-{4-[(6-chloro-2-benzoxazolyl)-oxy]-phenoxy}-propanoic acid, its methyl 
ester or its ethyl ester (FENOXAPROP); [(4-amino-3, 
5-dichloro-6-fluoro-2-pyridinyl)-oxy]-acetic acid or its 1-methylheptyl 
ester (FLUROXYPYR); methyl 2-[4, 
5-dihydro-4-methyl-4-(1-methylethyl)-5-oxo-1H-imidazol-2-yl]-4(5)-methylbe 
nzoate (IMAZAMETHABENZ); 3,5-diiodo-4-hydroxybenzonitrile (IOXYNIL); 
N,N-dimethyl-N'-(4-isopropylphenyl)-urea (ISOPROTURON); 
(2-methyl-4-chlorophenoxy)-acetic acid (MCPA); 
(4-chloro-2-methylphenoxy)-propionic acid (MCPP); N-methyl-2-(1, 
3-benzothiazol-2-yloxy)-acetanilide (MEFENACET); 
2-{[[((4-methoxy-6-methyl-1, 
3,5-triazin-2-yl)amino)-carbonyl]-amino]-sulphonyl}-benzoic acid or its 
methyl ester (METSULFURON); N-(1-ethylpropyl)-3, 
4-dimethyl-2,6-dinitroaniline (PENDIMETHALIN); 
0-(6-chloro-3-phenyl-pyridazin-4-yl) S-octyl thiocarbonate (PYRIDATE); 
4-ethylamino-2-t-butylamino-6-methylthio-striazine (TERBUTRYNE); methyl 
3-[[[[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)-amino]-carbonyl]-amino]-sulp 
honyl]-thiophene-2-carboxylate (THIAMETURON) and S-2,3,3-trichloroallyl 
N,N-diisopropylthiolcarbamate (TRIALLATE) are also possible. Surprisingly, 
some mixtures also show synergistic action. 
Mixtures with other known active compounds, such as fungicides, 
insecticides, acaricides, nematicides, bird repellents, plant nutrients 
and agents which improve soil structure, are also possible. 
The active compounds can be used as such, in the form of their formulations 
or in the use forms prepared therefrom by further dilution, such as 
ready-to-use solutions, suspensions, emulsions, powders, pastes and 
granules. They are used in the customary manner, for example by watering, 
spraying, atomizing or scattering. 
The active compounds according to the invention can be applied either 
before or after emergence of the plants. 
They can also be incorporated into the soil before sowing. 
The amount of active compound used can vary within a substantial range. It 
depends essentially on the nature of the desired effect. In general, the 
amounts used are between 0.01 and 10 kg of active compound per hectare of 
soil surface, preferably between 0.05 and 5 kg per ha.