SULPHONYLAMINOCARBONYLTRIAZOLINONES HAVING SUBSTITUENTS BONDED VIA OXYGEN

SULFONYLAMINOCARBONYLTRIAZOLINONES RENFERMANT DES GROUPES DE SUBSTITUTION LIES PAR L'INTERMEDIAIRE DE L'OXYGENE

English Abstract

The invention relates to novel sulphonylaminocarbonyl-
triazolinones having substituents bonded via oxygen and
to salts thereof, to a plurality of processes and novel
intermediates for their preparation, and to their use as
herbicides.
The active substances are those of the formula (I)
<IMG> (I)
in which
R1 represents hydrogen, amino, or an optionally
substituted radical from the series comprising
alkyl, alkenyl, alkinyl, cycloalkyl, aralkyl,
aryl, alkylamino, cycloalkylamino,
dialkylamino,
R2 represents an optionally substituted radical
from the series comprising alkyl, alkenyl,
alkinyl, cycloalkyl, cycloalkenyl, aralkyl,
aryl, and .

French Abstract

L'invention concerne de nouvelles sulfonylaminocarbonyltriazolinones portant des substituants liés par l'oxygène et des sels de ces dernières, un ensemble de procédés et de nouveaux intermédiaires pour leur préparation et leur utilisation comme herbicides. Les ingrédients actifs correspondent à la formule (I) <IMG> (I) où R1 représente un hydrogène, un amino ou un radical facultativement substitué de la série alkyle, alkényle, alkynyle, cycloalkyle, aralkyle, aryle, alkylamino, cycloalkylamino, dialkylamino, R2 représente un radical facultativement substitué de la série alkyle, alkényle, alkynyle, cycloalkyle, cycloalkényle, aralkyle, aryle, et R3 représente un radical facultativement substitué de la série alkyle, aralkyle, aryle, hétéroaryle, à l'exception de la 2-(2-méthoxycarbonylphénylsulfonyl-aminocarbonyl)-4-méthyl-5-méthoxy-2,4-dihydro-3H-1,2,4-triazol-3-one.

Claims

THE EMBODIMENTS OF THE INVENTION IN WHICH AN EXCLUSIVE
PROPERTY OR PRIVILEGE IS CLAIMED ARE DEFINED AS FOLLOWS:
1. A sulphonylaminocarbonyltriasolinone having a
substituent bonded via oxygen, of the general formula (I)
<IMG> (I)
in which
R1 represents hydrogen, amino, or optionally
substituted alkyl, alkenyl, alkinyl, cycloalkyl, aralkyl, aryl,
alkylamino, cycloalkylamino or dialkylamino,
R2 represents optionally substituted alkyl, alkenyl,
alkinyl, cycloalkyl, cycloalkenyl, aralkyl or aryl, and
R3 represents optionally substituted alkyl, aralkyl,
aryl or heteroaryl,
or a salt thereof, with the exception of compound 2-(2-methoxy-
carbonyl-phenylsulphonylaminocarbonyl)-4-methyl-5-methoxy-2,4-
dihydro-3H-1,2,4-triazol-3-one.
2. A sulphonylaminocarbonyltriazolinone according to
Claim 1, wherein
R1 represents hydrogen, amino, or represents C1-C6-
alkyl which is optionally substituted by fluorine, chlorine,
bromine, cyano, C1-C4-alkoxy, C1-C4-alkylcarbonyl or C1-C4-alkoxy-
carbonyl, or represents C3-C6-alkenyl or C3-C6-alkinyl, each of
which is optionally substituted by fluorine, chlorine and/or
bromine, or represents C3-C6-cycloalkyl which is optionally
- 86 -

substituted by fluorine, chlorine, bromine and/or C1-C4-alkyl,
or represents phenyl-C1-C3-alkyl which is optionally substituted
by fluorine, chlorine, bromine, cyano, nitro, C1-C4-alkyl,
trifluoromethyl, C1-C4-alkoxy and/or C1-C4-alkoxy-carbonyl, or
represents phenyl which is optionally substituted by fluorine,
chlorine, bromine, cyano, nitro, C1-C4-alkyl, trifluoromethyl,
C1-C4-alkoxy, fluorine- and/or chlorine-substituted C1-C3-alkoxy,
C1-C4-alkylthio, fluorine- and/or chlorine-substituted C1-C3-
alkylthio, C1-C4-alkylsulphinyl, C1-C4-alkylsulphonyl and/or
C1-C4-alkoxy-carbonyl, or represents C1-C4-alkylamino which is
optionally substituted by fluorine, cyano, C1-C4-alkoxy or C1-C4-
alkoxy-carbonyl, or represents C3-C6-cycloalkylamino or
di-(C1-C4-alkyl)-amino,
R2 represents C1-C6-alkyl which is optionally
substituted by fluorine, chlorine, bromine, cyano, C3-C6-cycloalkyl,
C1-C4-alkoxy or C1-C4-alkoxy-carbonyl, or represents C3-C6-alkenyl
or C3-C6-alkinyl, each of which is optionally substituted by
fluorine, chlorine and/or bromine, or represents C3-C6-cycloalkyl
which is optionally substituted by fluorine, chlorine, bromine
and/or C1-C4-alkyl, or represents cyclohexenyl, or represents
phenyl-C1-C3-alkyl which is optionally substituted by fluorine,
chlorine, bromine, cyano, nitro, C1-C4-alkyl, trifluoromethyl,
C1-C4-alkoxy and/or C1-C4-alkoxy-carbonyl, or represents phenyl
which is optionally substituted by fluorine, chlorine, bromine,
cyano, nitro, C1-C4-alkyl, trifluoromethyl, C1-C4-alkoxy, fluorine-
and/or chlorine-substituted C1-C3-alkoxy, C1-C4-alkylthio,
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fluorine- and/or chlorine-substituted C1-C3-alkylthio, C1-C4-
alkyl-sulphinyl, C1-C4-alkyl-sulphonyl and/or C1-C4-alkoxy-
carbonyl, and
R3 represents the group <IMG> in which R4 and R5
are identical or different and represent hydrogen, fluorine,
chlorine, bromine, iodine, nitro, C1-C6-alkyl (which is option-
ally substituted by fluorine, chlorine, bromine, cyano, carboxyl,
C1-C4-alkoxy-carbonyl, C1-C4-alkylamino-carbonyl, di-(C1-C4-
alkyl)amino-carbonyl, hydroxyl, C1-C4-alkoxy, formyloxy, C1-C4-
alkyl-carbonyloxy, C1-C4-alkoxy-carbonyloxy, C1-C4-alkylamino-
carbonyloxy, C1-C4-alkylthio, C1-C4-alkylsulphinyl, C1-C4-alkyl-
sulphonyl, di-(C-C4-alkyl)-aminosulphonyl, C3-C6-cycloalkyl or
phenyl), or represent C2-C6-alkenyl (which is optionally
substituted by fluorine, chlorine, bromine, cyano, C1-C4-alkoxy-
carbonyl, carboxyl or phenyl), or represent C2-C6-alkinyl (which
is optionally substituted by fluorine, chlorine, bromine, cyano,
C1-C4-alkoxy-carbonyl, carboxyl or phenyl), or represent C1-C4-
alkoxy (which is optionally substituted by fluorine, chlorine,
bromine, cyano, carboxyl, C1-C4-alkoxy-carbonyl, C1-C4-alkoxy,
C1-C4-alkylthio, C1-C4-alkylsulphinyl or C1-C4-alkylsulphonyl), or
represent C1-C4-alkylthio (which is optionally substituted by
fluorine, chlorine, bromine, cyano, carboxyl, C1-C4-alkoxy-carbonyl,
C1-C4-alkylthio, C1-C4-alkylsulphinyl or C1-C4-alkylsulphonyl), or
represent C3-C6-alkenyloxy (which is optionally substituted by
fluorine, chlorine, bromine, cyano or C1-C4-alkoxy-carbonyl), or
- 88 -

represent C2-C6-alkenylthio (which is optionally substituted by
fluorine, chlorine, bromine, cyano, nitro, C1-C3-alkylthio or
C1-C4-alkoxycarbonyl), C3-C6-alkinyloxy, C3-C6-alkinylthio or the
radical -S(O)p-R6 where
P represents the numbers 1 or 2 and
R6 represents C1-C4-alkyl (which is optionally substituted
by fluorine, chlorine, bromine, cyano or C1-C4-alkoxy-
carbonyl), C3-C6-alkenyl, C3-C6-alkinyl, C1-C4-alkoxy, C1-C4-
alkoxy-C1-C4-alkylamino, C1-C4-alkylamino, di-(C1-C4-alkyl)-amino,
phenyl or the radical -NHOR7 where
R7 represents C1-C12-alkyl (which is optionally
substituted by fluorine, chlorine, cyano, C1-C4-alkoxy, C1-C4-
alkylthio, C1-C4-alkylsulphinyl, C1-C4-alkylsulphonyl, C1-C4-
alkyl-carbonyl, C1-C4-alkoxy-carbonyl, C1-C4-alkylamino-carbonyl
or di-(C1-C4-alkyl)-amino-carbonyl), or represents C3-C6-alkenyl
(which is optionally substituted by fluorine, chlorine or bromine),
C3-C6-alkinyl, C3-C6-cycloalkyl, C3-C6-cycloalkyl-C1-C2-alkyl,
phenyl-C1-C2-alkyl (which is optionally substituted by fluorine,
chlorine, nitro, cyano, C1-C4-alkyl, C1-C4-alkoxy or C1-C4-
alkoxy-carbonyl), or represents benzhydryl, or represents phenyl
(which is optionally substituted by fluorine, chlorine, nitro,
cyano, C1-C4-alkyl, trifluoromethyl, C1-C4-alkoxy, C1-C2-fluoro-
alkoxy, C1-C4-alkylthio, trifluoromethylthio or C1-C4-alkoxy-
carbonyl),
R4 and/or R5 furthermore represent phenyl or phenoxy,
or represent C1-C4-alkylcarbonylamino, C1-C4-
- 89 -

alkoxycarbonylamino, C1-C4-alkylamino-carbonyl-amino,
di-(C1-C4-alkyl)-amino-carbonylamino, or the radical
-CO-R8 where
R8 represents C1-C6-alkyl, C1-C6-alkoxy, C3-C6-
cycloalkoxy, C3-C6-alkenyloxy, C1-C4-alkylthio,
C1-C4-alkylamino, C1-C4-alkoxyamino, C1-C4-alkoxy-
C1-C4-alkyl-amino or di-(C1-C4-alkyl)-amino
(which are optionally substituted by fluorine
and/or chlorine),
R4 and/or R5 furthermore represent trimethylsilyl,
thiazolinyl, C1-C4-alkylsulphonyloxy, di-(C1-C4-
alkyl)-aminosulphonylamino or the radical -CH=N-R9
where
R9 represents C1-C6-alkyl which is optionally
substituted by fluorine, chlorine, cyano,
carboxyl, C1-C4-alkoxy, C1-C4-alkylthio, C1-C4-
alkylsulphinyl or C1-C4-alkylsulphonyl, or
represents benzyl which is optionally
substituted by fluorine or chlorine, or
represents C3-C6-alkenyl or C3-C6-alkinyl, each
of which is optionally substituted by fluorine
or chlorine, or represents phenyl which is
optionally substituted by fluorine, chlorine,
bromine, C1-C4-alkyl, C1-C4-alkoxy,
trifluoromethyl, trifluoromethoxy or
trifluoromethylthio, or represents optionally
fluorine- and/or chlorine-substituted
- 90 -

C1-C6-alkoxy, C3-C6-alkenoxy, C3-C6-alkinoxy or
benzyloxy, or represents amino,
C1-C4-alkylamino, di-(C1-C4-alkyl)-amino, phenylamino,
C1-C4-alkyl-carbonyl-amino,
C1-C4-alkoxy-carbonylamino or C1-C4-alkyl-sulphonylamino, or
represents phenylsulphonylamino which is
optionally substituted by fluorine, chlorine,
bromine or methyl,
furthermore
R3 represents the radical <IMG> where
R10 represents hydrogen or C1-C4-alkyl,
R11 and R12 are identical or different and represent
hydrogen, fluorine, chlorine, bromine, nitro,
cyano, C1-C4-alkyl (which is optionally
substituted by fluorine and/or chlorine),
C1-C4-alkoxy (which is optionally substituted by
fluorine and/or chlorine), carboxyl,
C1-C4-alkoxy-carbonyl, dimethylaminocarbonyl,
C1-C4-alkylsulphonyl or
di-(C1-C4-alkyl)-aminosulphonyl;
furthermore
- 91 -

R3 represents the radical <IMG> where
R13 and R14 are identical or different and represent
hydrogen, fluorine, chlorine, bromine, nitro, cyano,
C1-C4-alkyl (which is optionally substituted by fluorine
and/or chlorine) or C1-C4-alkoxy (which is optionally
substituted by fluorine and/or chlorine);
furthermore
R3 represents the radical <IMG> in which
R15 and R16 are identical or different and represent
hydrogen, fluorine, chlorine, bromine, nitro,
cyano, C1-C4-alkyl (which is optionally
substituted by fluorine and/or chlorine),
C1-C4-alkoxy (which is optionally substituted by
fluorine and/or chlorine), or represent
C1-C4-alkylthio, C1-C4-alkylsulphinyl or
C1-C4-alkylsulphonyl (which are optionally
substituted by fluorine and/or chlorine), or
represent aminosulphonyl, mono-(C1-C4-alkyl)-
aminosulphonyl, di-(C1-C4-alkyl)-aminosulphonyl
or C1-C4-alkoxycarbonyl or
dimethylamino-carbonyl;
furthermore
- 92 -

R3 represents the radical <IMG> where
R17 and R18 are identical or different and represent
hydrogen, fluorine, chlorine, bromine,
C1-C4-alkyl (which is optionally substituted by
fluorine and/or bromine), C1-C4-alkoxy (which is
optionally substituted by fluorine and/or
chlorine), or represent C1-C4-alkylthio,
C1-C4-alkylsulphinyl or C1-C4-alkylsulphonyl (which
are optionally substituted by fluorine and/or
chlorine), or represent di-(C1-C4-alkyl)-amino-
sulphonyl;
furthermore
R3 represents the radical <IMG> where
R10 and R20 are identical or different and represent
hydrogen, fluorine, chlorine, bromine, cyano,
nitro, C1-C4-alkyl (which is optionally
substituted by fluorine and/or chlorine),
C1-C4-alkoxy (which is optionally substituted by
fluorine and/or chlorine), C1-C4-alkylthio,
C1-C4-alkylsulphinyl or C1-C4-alkylsulphonyl
(which is optionally substituted by fluorine
- 93 -

and/or chlorine), di-(C1-C4-alkyl)-amino-sulphonyl,
C1-C4-alkoxy-carbonyl or dimethylamino-carbonyl,
and
A represents oxygen, sulphur or the group N-Z1,
where
Z1 represents hydrogen, C1-C4-alkyl (which is
optionally substituted by fluorine,
chlorine, bromine or cyano),
C3-C6-cycloalkyl, benzyl, phenyl (which is
optionally substituted by fluorine,
chlorine, bromine or nitro), C1-C4-alkyl-
carbonyl, C1-C4-alkoxy-carbonyl or
di-(C1-C4-alkyl)-aminocarbonyl;
furthermore
R3 represents the radical <IMG> where
R21 and R22 are identical or different and represent
hydrogen, C1-C4-alkyl, halogen,
C1-C4-alkoxycarbonyl, C1-C4-alkoxy or
C1-C4-halogenoalkoxy,
Y1 represents sulphur or the group N-R23, where
R23 represents hydrogen or C1-C4-alkyl;
furthermore
- 94 -

R3 represents the radical <IMG> where
R24 represents hydrogen, C1-C4-alkyl, benzyl,
pyridyl, quinolinyl or phenyl,
R25 represents hydrogen, halogen, cyano, nitro,
C1-C4-alkyl (which is optionally substituted by
fluorine and/or chlorine), C1-C4-alkoxy (which
is optionally substituted by fluorine and/or
chlorine), dioxolanyl or C1-C4-alkoxy-carbonyl
and
R25 represents hydrogen, halogen or C1-C4-alkyl;
furthermore
R3 represents one of the groups listed below
<IMG> ; <IMG>
<IMG> .
- 95 -

3. A sulphonylaminocarbonyltriazolinone according to
Claim 1, wherein
R1 represents hydrogen, amino, C1-C4-alkyl which is
optionally substituted by fluorine, cyano, methoxy or ethoxy, or
represents allyl, C3-C6-cycloalkyl, benzyl, phenyl,
C1-C3-alkyl-amino, C3-C6-cycloalkylamino or di-(C1-C3-alkyl)-amino,
R2 represents hydrogen, C1-C4-alkyl which is
optionally substituted by fluorine and/or chlorine, methoxy or ethoxy,
or represents C3-C4-alkenyl which is optionally substituted by
fluorine and/or chlorine, or represents C3-C6-cycloalkyl, or
represents benzyl which is optionally substituted by fluorine,
chlorine and/or methyl, and
R3 represents the group <IMG> where
R4 represents fluorine, chlorine, bromine, methyl,
trifluoromethyl, methoxy, difluoromethoxy, trifluoromethoxy,
2-chloro-ethoxy, 2-methoxy-ethoxy, C1-C3-alkylthio,
C1-C3-alkyl-sulphinyl, C1-C3-alkylsulphonyl, dimethylaminosulphonyl,
diethylaminosulphonyl, N-methoxy-N-methylaminosulphonyl,
methoxyaminosulphonyl, phenyl, phenoxy or C1-C3-alkoxy-carbonyl and
R5 represents hydrogen, fluorine, chlorine or bromine,
furthermore
R3 represents the radical <IMG> where
- 96 -

R10 represents hydrogen,
R11 represents fluorine, chlorine, bromine, methyl,
methoxy, difluoromethoxy, trifluoromethoxy, ethoxy,
methoxy-carbonyl, ethoxycarbonyl, methylsulphonyl or
dimethylaminosulphonyl and
R12 represents hydrogen;
furthermore
R3 represents the radical <IMG> where
R represents C1-C4-alkyl, or
represents the radical <IMG> where
R represents C1-C4-alkyl.
4. The compound 2-(2-methoxycarbonyl-phenylsulphonyl-
aminocarbonyl)-4-methyl-5-phenoxy-2,4-dihydro-3H-1,2,4-trazol-
3-one of the formula
<IMG> .
5. A compound of the formula I according to claim 1
wherein R1 is <IMG> , R2 is C2H5 and R3 is <IMG>.
- 97 -

6. A compound of the formula I according to claim 1
wherein R1 is CH3, R2 is <IMG> and R3 is <IMG> .
7. A compound of the formula I according to claim 1
wherein R1 is CH3, R2 is <IMG> and R3 is <IMG> .
8. A compound of the formula I according to claim 1
wherein R1 is CH3, R2 is CH3 and R3 is <IMG>
9. A compound of the formula I as defined in any one of
claims 1 to 8 in which the compound is in the form of a salt
selected from the sodium, potassium, magnesium, calcium,
ammonium, C1-C4-alkyl-ammonium, di-(C1-C4-alkyl)-ammonium,
tri-(C1-C4-alkyl)-ammonium, C5- or C6-cycloalkyl-ammonium and
di-(C1-C2-alkyl)-benzyl-ammonium salts.
10. A herbicidal composition comprising a herbicidally
effective amount of a compound according to any one of claims
1 to 8 in admixture with a suitable carrier or diluent.
11. A herbicidal composition comprising a herbicidally
effective amount of a compound according to any one of claims 1
to 8 in admixture with a solid diluent or carrier, a liquified
normally gaseous diluent or carrier, or a liquid diluent or
carrier containing a surface active agent.
- 98 -

12. A method of combating weeds which comprises applying
to the weeds, or to a habitat thereof, a herbicidally effective
amount of a compound according to any one of claims 1 to 8.
13. A method of combating weeds which comprises applying
to the weeds, or to a habitat thereof, a herbicidally effective
amount of a composition containing a compound according to any
one of claims 1 to 8 in admixture with a suitable carrier or
diluent.
14. A method of combating weeds which comprises applying
to the weeds, or to a habitat thereof, a herbicidally effective
amount of a composition containing between 0.1 and 95% by weight
of a compound according to any one of claims 1 to 8 in admixture
with a suitable carrier or diluent.
15. A method of combating weeds which comprises applying
to the weeds, or to a habitat thereof, a herbicidally effective
amount of a composition containing between 0.5 and 90% by weight
of a compound according to any one of claims 1 to 8 in admixture
with a suitable carrier or diluent.
16. A method of combating weeds which comprises applying
to the weeds, or to a habitat thereof, a herbicidally effective
amount of a compound according to any one of claims 1 to 8 wherein
the compound is applied as a pre-emergence herbicide.
17. A method of combating weeds which comprises applying
to the weeds, or to a habitat thereof, a herbicidally effective
- 99 -

amount of a compound according to any one of claims 1 to 8
wherein the compound is applied as a post-emergence herbicide.
18. A method of combating weeds which comprises applying
to the weeds, or to a habitat thereof, a herbicidally effective
amount of a compound according to any one of claims 1 to 8
wherein the compound is applied to an area of cultivation at a
rate of between 1 g/ha and 10 kg/ha.
19. A method of combating weeds which comprises applying
to the weeds, or to a habitat thereof, a herbicidally effective
amount of a compound according to any one of claims 1 to 8
wherein the compound is applied to an area of cultivation at a
rate of between 5 g/ha and 5 kg/ha.
20. A process for preparing a compound according to claim
1 wherein R1, R2 and R3 are as defined in claim 1, which process
comprises
(a) reacting a triazolinone of the general formula
(II)
<IMG> (II)
in which
R1 and R2 have the meanings given in claim 1 with a
sulphonyl isocyanate of the general formula (III)
R3-SO2-N=C=O (III)
in which
- 100 -

R3 has the meaning given in claim 1, or
(b) reacting a triazolinone derivative of the general
formula (IV)
<IMG> (IV)
in which
R1 and R2 have the meanings given in claim 1, and
Z represents halogen, alkoxy, araloxy or aryloxy,
with a sulphonamide of the general formula (V)
R3-SO2-NH2 (V)
in which
R3 has the meaning given in claim 1, or
(c) reacting a triazolinone of the general formula
(II)
<IMG> (II)
in which
R1 and R2 have the meanings given in claim 1
with a sulphonamide derivative of the general formula (VI)
R3-SO2-NH-CO-Z (VI)
in which
R3 has the meaning given in claim 1 and
Z represents halogen, alkoxy, araloxy or aryloxy,
and, where required, forming a salt thereof.
21. A process for preparing a herbicidal composition
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comprising admixing a compound according to any one of claims 1
to 8 with a diluent and/or surface-active agent.
22. A triazolinone of the general formula (II)
<IMG> (II)
in which
R1 is as defined in claim 1 and
R2 represents optionally substituted cycloalkyl,
cycloalkenyl, aralkyl and aryl.
- 102 -

Description

2~6~63~
The invention relates to new sulphonylaminocarbonyl-
triazolinones having substituents bonded via oxygen, tc
a plurality of processes and novel intermediates for
their pxeparation, and to their use as h~rbicides.
It has been disclosed that certain substituted sulphonyl-
aminocarbonyltriazolinones such as, for example,
2- ( 2-chloro-phenylsulphonylaminocarbonyl ) -4, 5-dimethyl-
2, 4-dihydro-3H-1, 2, 4-triazol-3-one have herbicidal
properties (cf. EP-A 341,489). However, the action of
these compounds is not sati~factory in all respects.
Further sulphonylaminocarbonyltriazolinones such as, for
example, 2- ~ 2-methoxycarbonyl-phenylsulphonylamino-
carbonyl ) -4-methyl-5-methoxy-2, 4-dihydro-
3H-1,2,4-triazol-3-one are the subject of an earlier, but
non-prior-published Patent Application (cf. Gennan Patent
3, g34, 081 dated 12 .10 .1989 ) .
There have now baen found the novel
sulphonylaminocarbonyltriazolinones having substituents
bonded via oxygen, of the general formula ( I )
R3-502-NH-Co-NJ ~N-Rl
( I )
N~o - RZ
Le A 28 318 - 1 -

2~63~
in which
Rl represents hydrogenr amino, or an optionally sub-
stituted radical from the series comprising alkyl,
alkenyl, alkinyl, cycloalkyl, aralkyl, aryl, alkyl-
S amino, cycloalkylamino, dialkylamino,
R2 represents an optionally substituted radical from
the series comprising alkyl, alkenyl, alkinyl,
cycloalkyl, cycloalkenyl, aralkyl, aryl, and
R3 represents an optionally substituted radical from
the series comprising alkyl, aralkyl, aryl, hetero-
aryl,
and salts of compounds of the formula (I), with the
exception of 2-(2-methoxycarbonyl-phenylsulphonylamino-
carbonyl ) -4-methyl-S methoxy-2, 4-dihydro-
3H-1,2,4-triazol-3-one (cf. G~ ~n Patent 3,934,081).
~he new sulphonylaminocarbonyltriazolinones having
substituents bonded via oxygen, of the general formula
(I), are obtained when
Le A 28 318 - 2 -

~463~
a) triazolinones of the general formula (II)
H-N~N-Rl ( II )
1~0 - R2
in which
R1 and R2 have the abovementioned meanings
are reacted with sulphonyl isocyanates of the
general formula (III)
R3-So2-N=C=o (III)
in which
R3 has the abov,- -ntioned meaning,
if appropriate in the presence of a diluent, or when
(b) triazolinone derivatives of the general formula (IV)
Z -CO-NJ~N-Rl
. I I (IV)
N=='~o _R2
Le A 28 318 - 3 -

2~6~36
in which
R~ and R2 have the abovementioned meanings and
Z represents halogen, alkoxy, araloxy or aryloxy,
are reacted with sulphonamides of the general
formula (V)
R3-So2-NH2 (V)
in which
R3 has the abovementioned -~ning,
if appropriate in the presence of an acid acceptor
and if appropriate in the presence of a diluent, or
when
(c) triazolinones of the general formula (II)
HN ~ N-R1 (II)
_ R 2
in which
Le A 28 318 - 4 -

~6~3~
Rl and R2 have the abovemenl:ioned meanings
are reacted with sulphonalnide derivatives of the
general formula (VI)
R3-Soz-NH-Co~Z (VI)
in which
R3 has the abovementioned meanlng and
Z represents halogen, alkoxy, araloxy or aryloxy,
if appropriate in the presence of an acid acceptor
and if appxopriate in the presence of a diluent and,
if appropriate, salts are formed, by customary
methods, of the compounds of the formula (I) which
have been prepared by process (a), (b) or (c).
The new sulphonylaminocarbonyltriazolinones having
substituents bonded via oxygen, of the general formula
(I), and their salts are distinguished by a powerful
herbicidal activity.
Surprisingly, the new compounds of the formula (I) show
a considerably bett~r herbicidal action than the known
compound 2-(2-chlorophenylsulphonylaminocarbonyl)-
4,5-dimethyl-2,4-dihydro-3H-1,2,4-triazol-3-one, which
has a sLmilar structure.
Le A 28 318 - 5 -

2~6~636
The invention preferably relat.es to compounds of the
formula (I) in which
Rl represents hydro~en, amino, or represents Cl-C6-al~yl
which is optionally substituted by fluorine,
S chlorine, bromine, cyano, Cl-C4-alkoxy, Cl-C4-alkyl-
carbonyl or Cl-C4-alkoxy-carbonyl, or represents
C3-C6-alkenyl or C3-C6-alk:inyl, each of which is
optionally substituted by fluorine, chlorine and/or
bromine, or represents C3-C6-cycloalkyl which is
optionally substituted by fluorine, chlorine,
bromine and/or Cl-C4-alkyl, or represents phenyl-
Cl-C3-alkyl which is optionally substituted by
fluorine, chlorine, bromine, cyano, nitro, Cl-C4-
alkyl, trifluoromethyl, Cl-C4-alko~y and/or Cl-C4-
alkoxy-carbonyl, or represents phenyl which is
optionally substituted by fluorine, chlorine,
bromine, cyano, nitro, Cl-C4-alkyl, trifluoromethyl,
Cl-C4-alkoxy, fluorine- and/or chlorine-substituted
C1-C3-alkoxy, Cl-C4-alkylthio, fluorine- and/or
chlorine-substituted C1-C3-alkylthio, C1-C4-alkyl-
sulphinyl, Cl-C4 alkylsulphonyl and/or Cl-C4-alkoxy-
carbonyl, or represents Cl-C4-alkylamino which is
optionally substituted by fluorine, cyano, C1-C4-
alkoxy or Cl-C4-alkoxy-carbonyl, or represents C3-C6-
2S cycloalkylamino or di-(Cl-C4-alkyl)-amino,
R2 repre~ents C1-C6-alkyl which is optionally sub ti-
tuted by fluorine, chlorine, bromine, cyano, C3-C6-
cycloalkyl, Cl-C4-alkoxy or Cl-C4-alkoxycarbonyl, or
Le A 28 318 - 6 -

2 ~ 3 6
represents C3-C6-alkenyl or C3-C6-alkinyl, each of
which is optionally substituted by fluorine,
chlorine and/or bromine, or represents C3-C6-cyclo-
alkyl which is optionally ~ubstituted by fluorine,
chlorine, bromine and/or C~-C4-alkyl, or represents
cyclohexenyl, or represent~ phenyl-C1-C3-alkyl which
is optionally substituted by fluorine, chlorine,
bromine, cyano, nitro, C~-C4-alkyl, trifluoromethyl,
C~-C4-alkoxy and/or C~-C4-alkoxy-carbonyl, or repre-
sents phenyl which i8 optionally substituted by
fluorine, chlorine, bll- in~ cyano, nitro, C1-C4-
alkyl, trifluoromethyl, C,-C4-alkoxy, fluorine-
and/or chlorine-substituted C,-C3-alkoxy, C,-C4-
alkylthio, fluorine- andJor chlorine-substituted
C,-C3-alkylthio, C,-C4-alkyl-sulphinyl, Cl-C4-alkyl-
sulphonyl and/or Cl-C4-alkoxy-carbonyl, and
R3 represents the group ~ in which
R4 and R5 are identical or different and represent
hydrogen, fluorine, chlorine, b~'- ine, iodine,
nitro, C~-C6-alkyl (which is optionally
substituted by fluorine, chlorine, bL. ine,
cyano, carboxyl, C~-C4-alkoxycarbonyl, C,-C4-
alkylamino-carbonyl, di-(C~-C4-alkyl)amino-
carbonyl, hydroxyl, C,-C4-alkoxy, formyloxy,
Cl-C~-alkyl-carbonyloxy, Cl-C4-alkoxy-
carbonyloxy, C1-C~-alkylamino-carbonyloxy,
Cl-C4-alkylthio, C~-C4-alkyl~ulphinyl, C~-C4-
Le A 28 318 - 7 -

2~64~3S
alkylsulphonyl, di-(C~-C4-alkyl)-aminosulphonyl,
C3-C6-cycloalkyl or phenyl), or represent C2-C6-
alkenyl (which is optionally substituted by
fluorine, chlorine, bromine, cyano, Cl-C4-
~ 5 alkoxy-carbonyl, ca:rboxyl or phenyl), or
represent C2-C6-alkinyl (which is optionally
substituted by fluo;rine, chlorine, b-l- i n~,
cyano, Cl-C4-alkoxy-carbonyl, carboxyl or
phenyl)~ or represent Cl-C4-alkoxy (which is
optionally ~ubstituted by fluorine, chlorine,
bromine,cyano,carboxyl,Cl-C4-alkoxy-carbonyl,
Cl-C4-alkoxy, Cl-C4-alkylthio, Cl-C4-
alkylsulphinyl or Cl-C4-alkylsulphonyl), or
represent C1-C4-alkylthio (which is optionally
substituted by fluorine, chlorine, bL~- ine,
cyano, carboxyl, Cl-C4-alkoxy-carbonyl, Cl-C4-
alkylthio, C1-C4-alkylsulphinyl or Cl-C4-
alkylsulphonyl), or represent C3-C6-alkenyloxy
(which is optionally substituted by fluorine,
chlorine, bromine, cyano or Cl-C4-alkoxy-
carhonyl), or represent C~-C6-alkenylthio (which
is optionally substituted by fluorine,
chlorine, bromine, cyano, nitro, C1-C3-alkylthio
or Cl-C4-alkoxycarbonyl), C3-C6-alkinyloxy, C3-C6-
alkinyl~hio or the radical -S(O)p-R6 where
p represents the numbers 1 or 2 and
R6 represents C1-C4-alkyl (which is optionally
substituted by fluorine, chlorine,
Le A 28 318 - 8 -

2~6.~3~
bromine, cyano or Cl-C4-alkoxy-carbonyl),
C3-C6-alkenyl,C3--C6-alkinyl, Cl-C4-alkoxy,
Cl-C4-alkoxy-Cl-C4-alkylamino, Cl-C4-
alkylamino, di-(Cl-C4-alkyl)-amino, phenyl
or the radical -NHoR7 where
R7 represents C,-Cl2-alkyl (which is
optionally substituted by fluorine,
chlorine, cyano, C1-C4-alkoxy, C1-C4-
alkylthio, C1-C4-alkylsulphinyl, Cl-C4-
alkylsulphonyl, Cl-C4-alkyl-carbonyl, Cl-C4-
alkoxy-carbonyl,C1-C4-alkylamino-carbonyl
or di-(Cl-C4-alkyl)-amino-carbonyl), or
represents C3-C6-alkenyl (which is
optionally substituted by fluorine,
chlorine or bromine), C3-C6-alkinyl, C3-C6-
cycloalkyl, C3-C6-cycloalkyl-Cl-C2-alkyl,
phenyl-Cl-C2-alkyl (which is optionally
substituted by fluorine, chlorine, nitro,
cyano, C1-C4-alkyl, C1-C4-alkoxy or C1-C4-
alkoxy-carbonyl), or represents
benzhydryl, or represents phenyl (which is
optionally substituted by fluorine,
chlorine, nitro, cyano, Cl-C4-alkyl,
trifluoromethyl, C1-C4-alkoxy, C1-C2-
fluoroalkoxy, C1-C4-alkylthio, trifluoro-
methylthio or C1-C4-alkoxy-carbonyl),
R4 and/or R5 furthermore represent phenyl or phenoxy, or
~ represent Cl-C4-alkylcarbonylamino, Cl-C4-alkoxy-
Le A 28 318 - 9 -

206~63~
carbonylamino, Cl-C4-al:kylamino-carbonyl-amino,
di-(Cl-C4-alkyl)-amino-carbonylamino, or the radical
-CO-Ra where
R3 represents Cl-C6-al~l, C~-C6-alkoxy, C3-C6-
cycloalkoxy, C3-C6-alkenyloxy, Cl-C4-alkylthio,
C1-C4-alkylamino, C~-C4-alko~y ino, C1-C4-alkoxy-
C~-C4-alkyl-amino or di-(Cl-C4-alkyl)-amino
(which are optionally substituted by fluorine
and/or chlorine),
R4 and/or R5 furthermore represent trimethylsilyl, thia-
zolinyl, Cl-C4-alkylsulphonyloxy, di-(Cl-C4-alkyl)-
aminosulphonylamino or the radical -CH=N-R9 where
R9 represents C1-C6-alkyl which is optionally
substituted by fluorine, chlorine, cyano,
carboxyl, Cl-C4-alkoxy, Cl-C4-alkylthio, Cl-C4-
alkylsulphinyl or C1-C4-alkylsulphonyl, or
represents benzyl which is optionally
substituted by fluorine or chlorine, or
represent3 C3-C6-alkenyl or C3-C6-alkinyl, each
of which is optionally substituted by fluorine
or chlorine, or represents phenyl which is
optionally substituted by fluorine, chlorine,
bromine, C1-C4-alkyl, C1-C4-alkoxy,
trifluoromethyl, trifluoromethoxy or
trifluoromethylthio, or represents optionally
fluorine- and/or chlorine-~ubstituted Cl-C6-
- alkoxy, C3-C5-alkenoxy, C3-C6-alkinoxy or
Le A 28 318 - 10 -

2~6~3~
benzyloxy, or represents amino, C1-C4-
alkylamino, di-(C1 C4-alkyl)-amino, phenylamino,
Cl-C4-alkyl-carbony:L-amino, Cl-C4-alkoxy-
carbonylamino or Cl-C~-alkyl-sulphonylamino, or
S represents phenylsulphonylamino which is
optionally substitutled by fluorine, chlorine,
bromine or methyl,
furthermore
lz
R3 represents the radical I ~ where
R10 R11
R10 represents hydrogen or C1-C4-alkyl,
R11 and R12 are identical or different and represent
hydrogen, fluorine, chlorine, bromine, nitro,
cyano, C1-C4-alkyl (which is optionally sub~
stituted by fluorine and/or chlorine), C1-C4-
alkoxy (which is optionally substituted by
fluorine and/or chlorine), carboxyl, C1-C4-
alkoxy-carbonyl, dimethylaminocarbonyl, C1-C4-
alkylsulphonyl or di-(Cl-C4-alkyl)-amino-
sulphonyl;
furthermore-
Le A 28 318 - 11 -

2 ~ 3
,~.
~3 represents the radical R13 t 11 ~R14 where
R13 and Rl4 are identical or different and represent
hydrogen, fluorine, chlorine, bL,- ine, nitro,
cyano, C1-C4-alkyl (wh.ich is optionally sub-
stituted by fluorine and/or chlorine) or C1-C4-
alkoxy (which is optionally substituted by
fluorine and/or chlorine);
furthermore
R 1 5
R3 represents the radical ~ where
R16
R1~ and R16 are identical or different and represent
hydrogen, fluorine, chlorine, bromine, nitro,
cyano, C1-C4-alkyl (which is optionally sub-
stituted by fluorine and/or chlorine), C1-C4-
alkoxy (which is optionally substituted by
fluorine and/or chlorine), or represent C1-C4-
alkylthio, Cl-C4-alkylsulphinyl or C1-C4-alkyl-
sulphonyl (which are optionally substituted by
fluorine and/or chlorine), or represent amino-
Rulphonyl, mono-(C1-C4-alkyl)-aminosulphonyl,
di-(Cl-C~alkyl)-aminosulphonyl or Cl-C4-alkoxy-
- carbonyl or dimethylaminocarbonyl;
Le A 28 318 - 12 -

2~ ~63~
furthermore
R3 represents the radical R17 ~ R18 where
Rl7 and R1~ are identical or different and represent
hydrogen, fluorine, chlorine, bromine, Cl-C4-
alkyl (which is optionally substituted by
fluorine and/or bL~ ine), Cl-C4-alkoxy (which is
optionally substituted by fluorine and/or
chlorine), Cl-C4-alkylthio, Cl-C4-alkylsulphinyl
or Cl-C4-alkylsulphonyl (which are optionally
substituted by fluorine and/or chlorine), or
represent di-(Cl-C4-alkyl)-aminosulphonyl;
furthermore
R19
R3 represents the radical ~ R20 where
Rl9 and R20 are identical or different and represent
hydrogen, fluorine, chlorine, bl. ;ne, cyano,
nitro, Cl-C4-alkyl (which is optionally sub-
stituted by fluorine and/or chlorine), C1-C4-
alkoxy (which i8 optionally substituted by
fluorine and/or chlorine), Cl-C4-alkylthio,
Cl-C4-alkylsulphinyl or C~-C4-alkylsulphonyl
Le A 28 318 - 13 -

2~64~3~
(which is optionally substituted by fluorine
and/or chlorine), di-(Cl-C4-alkyl)-amino-sul-
phonyl, C~-C4-alkoxy-carbonyl or dimethylamino-
carbonyl, and
A represents oxygen, ~~ulphur or the group N-Z1,
where
z1 repre~ents hydrogen, Cl-C4-alkyl (which i8
optionally sub~tituted by fluorine,
chlorine, bromine or cyano), C3-C6-cyclo-
alkyl, benzyl, phenyl (which is optionally
substituted by fluorine, chlorine, bl~- in~
or nitro), Cl-C4-alkylcarbonyl, Cl-C4-
alkoxy-carbonyl or di-(C1-C4-alkyl~-amino-
carbonyl;
furthermore
R21
R3 represents the radical ~ ~ R22 where
R2l and R22 are identical or different and represent
hydrogen, C1-C4-alkyl, halogen, Cl-C4-alkoxy-
carbonyl, Cl-C4-alkoxy or Cl-C4-halogenoalkoxy,
yl represents sulphur or the group N-R23, where
R23 represents hydrogen or C1-C4-alkyl;
furthermore
Le A 28 318 - 14 -

2~&~3~
R26
R3 represents the radical 7 R25where
R24
R2~ represents hydrogen, Cl-C4-alkyl, benzyl,
pyridyl, quinolinyl or phenyl,
R25 represents hydrogen, halogen, cyano, nitro,
S Cl-C4-alkyl (which is optionally substituted by
fluorine and/or chlorine), C1-C4-alkoxy (which
is optionally substituted by fluorine and/or
chlorine), dioxolanyl or C1-C4-alkoxy-carbonyl
and
R26 represents hydrogen, halogen or Cl-C4-alkyl;
furthermore
R3 represents one of the groups listed below
H3CO ~ H3C ~
~S~N-C4H9 ; N~S~OCH2CF3
~~
o
The invention furthermore preferably relates to the
Le A 28 318 - 15 -

2~6~636
sodium, potas~ium, magnesium, calcium, ammonium, Cl-C4-
alkyl-ammonium, di-(Cl-C4-alkyl)-ammonium, tri-(Cl-C4-
alkyl)-ammonium, C5- or C6-cycloalkyl-ammonium and
di-(C,-C2-alkyl)~benzyl-ammonium ~alt~ of compounds of the
formula (I) in which R1, R2 and R3 have the meaning~
mentioned above as being preferred.
In particular, the invention relates to compounds of the
formula (I) in which
Rl represents hydrogen, amino, C~-C4-alkyl which is
optionally substituted by fluorine, cyano, methoxy
or ethoxy, or represent~ allyl, C3-C6-cycloalkyl,
benzyl, phenyl, Cl-C3-alkylamino, C3-C6-cycloalkyl-
amino or di-(Cl-C3-alkyl)-amino,
R2 represents hydrogen, C1-C4-alkyl which i5 optionally
lS substituted by fluorine and/or chlorine, methoxy or
ethoxy, or represents C3-C4-alXenyl which is
optionally substituted by fluorine and/or chlorine,
or represents C3-C6-cycloalkyl, or represents benzyl
which is optionally substituted by fluorine,
chlorine and/or methyl, and
3 R5
R represents the group ~ where
R4
R4 represents fluorine, chlorine, b-~ ine, methyl,
trifluoromethyl, methoxy, difluoromethoxy,
Le A 28 318 - 16 -

2~6~3~
trifluoromethoxy, 2-chloro-ethoxy, 2-methoxy-
ethoxy, C1-C3-alkylthio, C1-C3-alkylsulphinyl,
C~-C3-alkylsulphonyl, dimethylaminosulphonyl,
diethylaminosulphonyl, N-methoxy-N-methylamino-
sulphonyl, methoxyaminosulphonyl, phenyl,
phenoxy or C,-C3-alkoxy-carbonyl and
R~ represents hydrogen, fluorine, chlorine or
b~l- inP;
furthermore
Rl I
10 R3 represents the radical -fH~ where
RlO
R10 represents hydrogen,
Rl1 represents fluorine, chlorine, bL~- ine~ methyl,
methoxy, difluoromethoxy, trifluoromethoxy,
ethoxy, methoxycarbonyl, ethoxycarbonyl,
methylsulphonyl or dimethylaminosulphonyl and
R12 represents hydrogen;
furthermore
Le A 28 318 - 17 -

2 ~ 3 ~
~3
R3 represents the radical RO- 1l S
where R represents C~-C4-alkyl, or
RO - C~,
represents the radical
N'N
CH3
where R represents Cl-C4-alkyl.
The abovementioned definitions of radicals, in general or
mentioned in preferred ranges, can be combined with each
other in any desired way, that is to say also between the
particular preferred ranges.
Examples of the compounds according to the invention are
listed in Table 1 below - cf. also the Preparation
Examples.
o
R3-sO2-NH-Co-N ~ N-R1 (I)
N~o _R2
Le A 28 318 - 18 -

~a~636
Table 1: Examples of the compounds of the formula (I)
Rl RZ R3
CH
CH3 ~
COOC2H5
CH3 C2H5 ~
OCHF2
CH3 CH2-CH=CH2 ~
502N(CH3~2
CH3 CH3 ~
COOCH3
CH3 CH3 ~ H2_
~ COOC2H5
CH3 C2H5 N~N
CH3
Le A 28 318 - 19 -

2 ~ 6 ~ 6 3 6
Table 1: (Continuation)
R 1 R2 R3
CH3 CZH5 [~COOCH3
CH3 C2H5 Q
~3
C2H5 C2H5 ~
C2H5 C3H7 ~CF3
OCF 3
CH3 ~H2-
OCH2CH2C 1
' C2~5 ~
~ CH(CH:3)2 ~CON(CH3)2
Le A 28 318 ~ 20 -

2a~3~
Table l: ~Con~inuation)
R I R2 1?3
~5~2NH2
CH3 CH(CH3)2 b~
sCH ( CH3 ) 2
CH3 CH2-CH=CH2 ~
502CH3
C2H5 CH3
C2H5 C2H5 ~
Si (CH3)3
CH3 C2H5 <~
OCF3
C2H5 C31~7 <~H2-
~ CON(CH3)2
CH3 C2H5 ~N--'
Le A 28 31a - 21 -

2 ~ 3 ~
Table 1: ( Continuation )
Rl R2 R3
Br
CH2~3 CH3 ~
OCHzCH2 OCH3
/\ ~
C2H5 ~
CH3 ~r
-- N~N~
_
CH3
S02N ( CH3 ) 2
{~ C2H5 ~
OCHF2
3H7~n ~CH2-
COOCH ( CH3 ) 2
CH3 C2HS ~=
- Cl
Le A 28 318 - 22 -

2a64s3~
Table 1: (Continuation)
Rl R2 IR3
COOC2H5
C~3 CH3 ~
F2CHO
CH3 C2H5 ~
o~3
CH3 S-CH2-C-CH ~
s
NJ
O-CHZ-cF3
CH3 C2H5 ~
C2H5 ~ COOCH3
N~N~--~
[~
CH3 ~ COOCH3
N~N'
N
Le A 28 318 - 23 -

2~4~3~
Table 1: (Continuation)
Rl RZ R3
CH3 CH3 ~ Cl
N~S
~CON(CH3)2
CH3 C3H7 H3C ~
C2H5 C2H5 ~'-'COOCH3
COOCH3
CH2-CH-CH2 C2H5 ~H2
CH2-CH=c~2 CH3 ~ r
CH3
COOCH3
C2H5 CH3 ~
502NCH3(ocH3)
C2H5 C2H5 ~
Le A 28 318 - 24 -

2~6~636
Table l: (Continuation)
R1 R2 R3
C 3H7 CH2 - CH= CH2 ~
OCH3
CH3 CH3 ~
/\ ~
C2H5 y
CH3
CzH5 CH3
C 2H s C 2H 5
CH3
CH3 C2H5 So2~3
Le A 28 318 - 25 -

2~63g
Table 1: (Continuation)
R1 R2 R3
OCHF2
~H3 C3H7 ~ H2_
C3H7 CH3 ~
S OOCH3
OCH3
C3H7 CH3 ~
OCH2CH2-C1
C3H7 C2H
C3H7 C2H
CH3 C2H5 ~
N
O~GI
c~3 CH3 ~ CF3
Le A 28 318 - 26 -

2~63~
Table 1: (Continuation)
Rl R2 R3
NtCH3)2 CH3 ~
~11 502NH2
CH3 C2H5 ~ ~A~
~I S~2NH2
CzH5 CzH5 ~N ~
CH3 ~ 502NH2
CH3 C2H5 ~
S~-~O-CFz-CFzC1
OCHzCHz-C
N(CH3)z CH3
Le A 28 318 - 27 -

2 ~
If, for example, 2,6-difluoro-phenylsulphonyl isocyanate
and 5-ethoxy-4-methyl-2,4~dihydro-3H-1,2,4-triazol-3-one
are used as starting substances, the course of the
reaction in process (a) according to the invention can be
outlined by the following equation:
F O
S02-N=C=0 + H~N N'CH3
F ~C2H5
F O
~ 11
S02-NH-CO'N~-'N'CH3
F C2H5
If, for example, 2-methylthio-benzenesulphonamide and
2-chlorocarbonyl-4-di~ethylamino-5-propyloxy-2,4-dihydro-
3H-1,2,4-triazol-3-one are used as starting substances,
the course of the reaction in process (b~ according to
the invention can be outlined by the following equation:
SCH3
~< J~
S02-NH2 ~ Cl-CO'N N'N(CH3)2 -HCl
N='--OC 3H 7
SCH3 ~
~< J~
502-NH-Co~N N'N(CH3)2
N==a~OC3H7
Le A 28 318 - 28 -

2 ~ 3 ~
If, for example, N-methoxycarbonyl-2-methoxy benzene-
sulphonamide and S-methoxy-4-di:Eluoromethyl-2,4-dihydro-
3H-1,2,4-triazol-3-one are used as starting substances,
the course of the reaction in process (c) according to
the invention can be outlined by the following equation:
OCH3 ~
H'N N~CHF2
502-NH-COOCH3 ~ ~ CH3
OCH3 O
~S02 -NH - CO~NJ~N~CHF2
-HOCH l l
~ OCH3
Formula (II) provides a general definition of the triazo-
linone~ to be used as starting substances in processes
(a) and (c) according to the inYention for the prepara-
tion of compounds of the formula (I).
In formula (II), R1 and R2 preferably, or in particular,
have tho~e -~n i ngs which have already been mentioned
above in connection with the description of the compounds
of the formula (I) according to the invention as being
preferred, or particularly preferred, for R1 and R2.
Le A 28 318 - 29 -

2~ 63~
Examples of the starting substances of the formula (II)
are listed in Table 2 below.
HNJ~N'R 1 ( I I )
N~ _R2
Le ~ 28 318 - 30 -

2~64~3~
Table 2: Examples of the starting subs~ances of the
formula (II~
Rl R2
H CH3
CH3 CH3
C2H5 CH3
C3H7 CH3
CH(CH3)2 CH3
C4Hg CH3
~\
CH3
CH3 C2H5
CH3 C3H7
CH3 CH(CH3)2
C~3 CH2-CH=CH2
CH3 CH2
Le A 28 318 - 31 -

2~6~36
Table 2: (Continuation)
Rl R2
CH3 CH2-C--CH
C2H5 C2H5
C3H7 C2H5
C2H5
CHz-CH=CH2 C2~5
CH2-CHBr-CH2Br CzH5
/~
C3H7
CH2-CH=CH2
~\
CH ( CH 3 ) 2
C2H5 CH ( CH3 ~ 2
C3H7 CH(CH3)2
CH2-CH=CH2 C3H7
C2H5 C3H7
C2H5 -CH2-C-CH
C3H7 C3H7
I.e A 28 318 - 32 -

3 6
Some of the starting substance-; of the formula (II) are
the subject of an earlier, but non~prior-published,
Patent Application (cf. German Patent 4,030,063, dated
~2.09.19gO).
S The compounds of the gPneral formula ~II) in which R1 has
the abovementioned meaning and:RZ represents in each case
optionally substituted cycloalkyl, cycloalkenyl, aralkyl
or aryl, are new and a subject of the present Patent
Application.
The compounds of the formula (II) are obtained when
hydrazinoformic esters of the general formula (VII)
H2N-NH-Co-o-R4 (VII)
in which
R4 has the abov.- ontioned meaning
are reacted with alkyliminocarbonic diesters of the
general formula (VIII)
,~_R2 (VIII)
Rl -tl=C~
o _R2
in which
R1 and R2 have the abovementioned meaning, if appropriate
Le A 28 318 - 33 -

2~6~63~
in the presence of a diluent such as, for example,
methanol, at temperatures between 0~C and 50~C, and the
compounds formed in this process, of the general formula
(IX)
,o-RZ
R4-o-co-NH-N=c~ (IX)
NH_Rl
in which
Rl, R2 and R4 have the aboY, ?ntioned -~ning,
are, if appropriate, isolated by customary methods and
heated to temperatures between 50~C and 150~C, if appro-
priate in the presence of a diluent such as, for example,toluene, xylene or o-dichlorobenzene (cf. Preparation
Examples).
The starting substances of the formulae (VII) and (VIII)
are known chemicals.
The intermediates of the formula (IX) are new compounds.
Formula (III) provides a general definition of the
sulphonyl isocyanates furthermore to be used as starting
substances in process (a) according to the invention for
the preparation of compounds of the formula (I).
In formula (III), R3 preferably, or in particular, has
Le A 28 31~ 34 -

2~ 163~
that meaning which has already been mentioned above in
connection with the description of the compounds of the
formula (I) according to the invention as being pre-
ferred, or particularly preferred, for R3.
5 Examples of the starting substances of the formula (III)
which may be mentioned are:
2-fluoro-, 2-chloro-, 2-bromo-, 2-methyl-, 2-metho~y-,
2-trifluoromethyl-, 2-difluoro-methoxy-, 2-trifluoro-
methoxy-, 2-methylthio-, 2-ethylthio-, 2-propylthio-,
2-methylsulphinyl-, 2-methylsulphonyl-, 2-dimethylamino-
sulphonyl-, 2-diethylamino~ulphonyl-, 2-(N-methoxy-
N-methyl)-aminosulphonyl-, 2-phenyl-, 2-phenoxy-,
2-methoxycarbonyl-,2-ethoxycarbonyl-,2~propoxycarbonyl-
and 2-isopropoxycarbonyl-phenylsulphonyl isocyanate,
2-fluoro-, 2-chloro-, 2-difluoromethoxy-, 2-trifluoro-
methoxy-,2-methoxycarbonyl- and 2-ethoxycarbonyl-benzyl-
sulphonyl isocyanate, 2-methoxycarbonyl-3-thienyl-sul-
phonyl isocyanate, 4-methoxycarbonyl- and 4-ethoxy-
carbonyl-1-methyl-pyrazol-S-yl-sulphonyl isocyanate.
The sulphonyl isocyanates of the formula (III) are known
and/or can be prepared by processes known per se (cf. US
Patent 4,127,405, 4,169,719, 4,371,391; EP-A 7,687,
13,480, 21,641, 23,141, 23,422, 30,139, 35,893, 44,808,
44,809, 48,143, 51,466, 64,322, 70,041, 173,312).
Process (a) according to the invention for the prepara-
tion of the new compounds of the formula (I) is
preferably carried out using diluents. Diluents which are
Le A 28 318 - 35 -

2~4~3~
suitable for this purpose are virtually all inert organic
solvents. These preferably include aliphatic and
aromatic, optionally halogenat:ed hydrocarbons such as
pentane, hexane, heptane, cyclohexane, petroleum ether,
benzine, ligroine, benzene, toluene, xylene, methylene
chloride, ethylene chloride, chloroform, carbon
tetrachloride, chlorobenzene and o-dichlorobenzene,
ethers such as die~hyl ether and dibutyl ether, glycol
dimethyl ether and diglycol dimethyl ether,
tetrahydrofuran and dioxane, ketones such as acetone,
methyl eth~l ketone, methyl isopropyl ketone and methyl
isobutyl ketone, esters such as methyl acetate and ethyl
acetate, nitriles such as, for example, acetonitrile and
propionitrile, amides such as, for example,
dimethylformamide, dimethylacetamide and N-methyl-
pyrrolidone, and also dimethyl sulphoxide, tetramethylene
sulphone and hexamethylphosphoric triamide.
When carrying out process ~a) according to the invention,
the reaction temperatures can be varied within a substan-
tial range. In general, the process is carried out attemperatures between 0~C and 150~C, pre~erably at tem-
peratures between 10~C and 80~C.
In general, process (a~ according to the invention is
carried out under atmospheric pressure.
For carrying out proce4s (a) according to the invention,
between 1 and 3 moles, preferably between 1 and 2 moles,
of sulphonyl isocyanate of the formula (III) are
Le A 28 318 - 36 -

2~63~
generally employed per mole or triazolinone of the
formula (II).
The reactants can be combined in any desired sequence.
The reaction mixture is stirred until the reaction is
complete and the product is isolated by filtration with
suction. In another processing varian~, the mixture is
concentrated, and the crude product which remains in the
residue is brought to crystallisation with a suitable
solvent such as, for example, diethyl ether. The product
of the formula (I) which is obtained in this way in
crystalline form is isolated by filtration with suction.
Formula (IV) provides a general definition of the triazo-
linone derivatives to be used as starting substances in
process (b) accordinq to the invention for the prepara-
tion of compounds of the formula (I).
In formula (IV), Rl and ~2 preferably, or in particular,have those ~n; ngs which have already been mentioned
above in connection with description of the compounds of
the formula (I) according to the invention as being
preferred, or particularly preferred, for R1 and R2 and
Z preferably represent~ chlorine, Cl-C4-alkoxy, benzyl-
oxy or phenoxy, in particular methoxy or phenoxy.
Examples of the starting substances of the formula (IV)
which are possible are the compounds of the formula (IV)
which are to be prepared from the compounds of the
Le A 28 318 - 37 -

2~636
formula (II) listed in Table 2 and phosgene, methyl
chloroformate, benzyl chloroformate, phenyl chloroformate
or dipheny' carbonate.
The starting substances of the formula (IV) were hitherto
unknown.
The new triazolinone derivatives of the formula (IV) are
obtained when triazolinones of the general formula ~II)
HN ~ N~Rl (II)
RZ
in which
R1 and R2 have the abovementioned -~nings
are reacted ~ith carbonic acid derivatives of the general
formula (X)
z_co-zl (X)
in which
Z has the abov~ -ntioned -~ni ng and
Z1 represents a leaving group such as chlorine,
Le A 28 318 - 38 -

3 ~
methoxy, benzyloxy or phenoxy,
if appropriate in the presence of a diluent such a~, for
example, tetrahydrofuran, and, if appropriate, in the
presence of an acid acceptor such as, for example, sodium
hydride or potassium tert-butylate, at temperatures
between -20~~ and +100~C.
Formula (V) provides a general definition of the
sulphonamides furthermore to be used as starting sub-
stances in process (b) accordin~ to the invention for the
preparation of compounds of the formula (I).
In formula (V), R3 preferably, or in particular, has that
meaning which has already been mentioned above in connec-
tion with the description of the compounds of the formula
(I) according to the invention as being preferred, or
particularly preferred, for R3.
~he following may be mentioned as examples of the star-
ting substances of the formula (V):
2-fluoro-, 2-chloro-, 2-bromo-, 2-methyl-, 2-methoxy-,
2-trifluoromethyl-, 2-difluoro-methoxy-, 2-trifluoro-
methoxy-, 2-methylthio-, 2-ethylthio-, 2-propylthio-,
2-methylsulphinyl-, 2-methylsulphonyl-, 2-dimethylamino-
sulphonyl-, 2-diethylaminosulphonyl-, 2-(N-methoxy-
N-methyl)-aminosulphonyl-, 2-phenyl-, 2-phenoxy-,
2-methoxycarbonyl-,2-ethoxycarbonyl-,2-propoxycarbonyl-
and 2-isopropoxycarbonyl-benzenesulphonamide, 2-fluoro-,
2-chloro , 2-difluoromethoxy-, 2-trifluoromethoxy-,
Le A 28 31a - 39 -

2~63~
2-methoxycarbonyl- and 2-ethoxycarbonyl-phenylmethane-
sulphonamide, 2-methoxycarbonyl--3-thiophenesulphonamide,
4-methoxycarbonyl- and 4-ethoxycarbonyl-1-methyl-pyra-
zole-S-sulphonamide.
The sulphonamides of the formula (V) are known and/or can
be prepared by processes known per se (cf. US Patent
4,127,405, 4,169,719, 4,371,391; EP-A 7,587, 13,480,
21,641, 23,141, 23,422, 30,139, 35,893, 44,808, 44,809,
48,143, 51,466, 64,322, 70,041, 173,312).
Process (b) according to the invention for the prepara-
tion of ~he new compounds of the formula (I) is pre-
ferably carried out using diluents. Diluents which are
suitable for this purpose are virtually all inert organic
solvents as have been indicated, for example, above in
the case of process (a) according to the invention.
Acid acceptors which can be employed in process (b)
according to the invention are all acid-binding agents
which can customarily be employed for reactions of this
type. The following are preferably suitable: alkali metal
hydroxides such as, for ex~mple, sodium hydroxide and
potassium hydroxide, alkaline earth metal hydroxides such
as, for example, calcium hydroxide, alkali metal car-
bonates and alkali metal alcoholates such as sodium
carbonate, potas~ium carbonate, sodium tert-butylate and
potassium tert-butylate, furthermore aliphatic, aromatic
or heterocyclic amines, for example triethylamine,
trimethylamine, dime~hylaniline, dimethylbenzylamine,
Le A 28 318 - 40 -

pyridin~, 1,5-diazabicy~1O-[4.3.0]-non-5-ene (DBN),
1,8-diazabicyclo-[5.4.0]-undec-7-ene (DBU) and 1,4-diaza-
bicyclo[2.2.2]-octane (DABCO).
When carrying out process ~b) according to the invention,
the reaction temperatures can be varied within a substan-
tial range. In general, the p:rocess is carried out at
temperatures between 0~C and 100~C, preferably at tem-
peratures between 10~C and 60~C.
Process (b) according to the invention is generally
ln carried out under atmospheric pressure. However/ it can
also be carried out under increased or reduced pressure.
For carrying out process (b) according to the invention,
the starting substances required in each case are
generally employed in approximately equimolar amounts.
However, it is also possible to use one of the two
components employed in each case in a larger excess. In
general, the reactions are carried out in a suitable
diluent in the presence of an acid acceptor, and the
reaction mixture is stirred for several hours at the
particular temperature required. Working-up in process
(b) according to the invention is carried out in each
case by customary methods.
The triazolinones of the formula tII) to be used as
starting substances in process (c) according to the
invention for the preparation of compounds of the formulA
(I) have already been described as starting substances
Le A 28 318 - 41 -

2 ~ 3 ~
for process (a) according to the invention.
Formula (YI) provides a general definition of the sul-
phonamide derivatives furthermore to be used as starting
substances in process (c) according to the invention for
the preparation of compounds of the formula (I).
In formula (VI), R3 and Z preferably, or in particular,
have those ~ni ngs which have already been mentioned
above in connection with the description of the compounds
of the formula (I) or (IV) according to the invention 8S
being preferred, or particularly preferred, for R3 and Z.
Process (c) according to the invention is preferably
carried out using diluents. Solvents which are suitable
fox this purpose are the same organic solvents as have
been mentioned above in connection with the description
of process (a) according to the invention.
If appropriate, process (c) is carried out in the pre-
sencs of an acid acceptor. Acid-binding agents which are
suitable for this purpose are the same as have been
mentioned above in connection with the description of
process (b) according to the invention.
When carrying out process (c), the reaction temperatures
can vary within a substantial range. In general, the
process is carried out at temperatures between 0~C and
100~C, preferably at temperatures between 10~C and 60~C.
Le A 28 318 - 42 -

2~6~636
In general, process (c) according to the invention is
carried out under atmospheric pressure. However, the
process can also be carried out under increased or
reduced prassure.
S For carrying out process (c) accordin~ to ~he invention,
the starting substances required in each case are
generally employed in approximately equimolar amounts.
However, it is also possible to use one of the two
components employed in each case in a larger excess. The
reactions are generally carrîed out in a suitable diluent
in the presence of an acid acceptor, and the reaction
mixture is stirred for several hours at the particular
temperature required. Working-up is carried out in
process (c) according to the invention in each case by
customary methods.
To convert the compounds of the formula ~I) into salts,
they are stirred with suitable salt formers such as, for
example, sodium hydroxide, sodium methylate, sodium
ethylate, potassium hydroxide, potassium methylate or
potassium ethylate, ammonia, isopropylamine, dibutylamine
or triethylamine, in suitable diluents s~ch as, for
example, water, methanol or ethanol. ~he salts can be
isolated in the form of crystalline products, if appro-
priate after concentration.
The active compounds according to the invention can be
used as defoliants, desiccants~ agents for destroying
broad-leaved plants and, especially, as weed-killers. By
Le A 28 318 - 43 -

2~ ~S3~)
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 sele!ctive 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 qenera: 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, Centaurea, Trifolium,
Ranunculus and Taraxacum.
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 qenera: 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.
Le A 28 318 - 44 -

2a~ 3~
Monoco-tyledon cultures of the genera: Oryza, Zea,
Triticum, Hordeum, Avena, Secalel 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 concentra-
tion, for the total combating of weeds, for example on
industrial terrain and rail tracks, and on paths and
squares with or without tree plantings. Egually, the
compounds can be employed for combating weeds in peren-
nial cultures, for example afforestations, 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 hopfieldsl on
lawns, turf and pasture-land, and fox the selective
combating of weeds in annual cultures.
Some of the compounds of the formula (I~ according to the
invention are suitable for total or semi-total weed
control, some for the selective control of monocotyledon
and dicotyledon weeds in monocotyledon and dicotyledon
cultures, both pre-emergence and post-emergence.
The active compounds can be converted into the customary
formulations, ~uch as solutions, emulsions, wettable
powders, suspensions, powders, dusting agents, pastes,
Le A 28 318 - ~5 -

2 ~ 3 ~
soluble powders, granules, suspension-emulsion concen-
trates, natural and synthetic materials impregnated with
active compound, and ~ery fin~e capsule~ in polymeric
substances.
These formulations are producecl in a known manner, for
example by mixing the active compounds with extenders,
that is liquid solvents and/or solid carriers, optionally
with the use of surface-active agents, that is emulsi-
fying 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 alkyl-
lS naphthalenes, chlorinated aromatics and chlorinatedaliphatic hydrocarbons, such as chlorobenzenes, chloro-
ethylenes or methylene chloride, aliphatic hydrocarbons,
such as cyclohexane or paraffins, for example petroleum
fractions, mineral and vegetable oils, 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 sol-
vents, such as dimethylformamide and dimethyl sulphoxide,
as well as water.
~5 As solid carriers there are suitable: for example
ammonium salt~ and ground natural minerals, such as
kaolins, clays, talc, chalk, ~uartz, attapulgite, mont-
Le A 28 3i8 - 46 -

2 ~ 3 ~
morillonite 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 a.q calcite, marble, pumice, sepiolite and
dolomite, as well a~ synthetic granules of inorganic snd
organic meals, and granules of organic material such as
sawdust, coconut shells, maize cobs and tobacco stalks;
as emulsifying and/or foam-forming agen~s there are
suitable: for example non-ionic and anionic emul~ifiers,
such as polyoxyethylene fatty acid esters, polyoxy-
ethylene fatty alcohol ethers, for example alkylaryl
polyglycol ethers, alkylsulphonates, alkyl sulphates,
arylsulphonates as well as albumen 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
latexes, 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. Further additives can be
mineral and vegetable oils.
It is possible to use colorants such as inorganic pig-
ments, for example iron oxide, titanium oxide and
Prussian Blue, and organic dyestuffs, such as alizarin
dyestuffs, azo dyestuffs and me~al phthalocyanine dye-
stuffs, and trace nutrients such as salts of iron,
Le A 28 318 - 47 -

2a~4~
manganese, boron, copper, cobalt, molybdenum and zinc.
The formulation~ in general contain between 0.1 and 95
per cent by weight of active co:mpound, preferably between
0.5 and 90~.
For combating weeds, the ac~ive compounds according to
the invention, as such or in the form of their formula-
tion~, can also be used as mixtures with known hexbi-
cides, finished formulations or tank mixes being pQS-
sible.
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(lH,3H)-dione
(AMETXYDIONE) or N-(2-benzothiazolyl)-N,N'-dimethyl-urea
(METABENZTHIAZURON) for combating weeds in cereals; 4-
amino-3-methyl-6 phenyl-1,2,4-triazin-5(4~)-one
(METAMITRON) for combating weeds in sugar beet and 4-
amino-6-(1,1-dimethylethyl)-3-methylthio-1,2,4-triazin-
5(4H)-one (METRIBUZIN) for combating weeds in soya beans;
furthermore also 2,4-dichlorophenoxyacetic acid (2,4-D);
4-(2,4-dichlorophenoxy)-butyric acid (2,4-DB); 2/4-
dichlorophenoxypropionic acid (2,4-DP); 5-(2-chloro-4-
trifluoromethyl-phenoxy)-2-nitro-benzoic acid
~ACIFLUORFEN); N-(methoxy-methyl)-2,6-diethyl-chloro-
acetanilide (AT.Ar~T.OR); methyl-6,6-dimethyl-2,4-dioxo-3-
[1-(2-propenylo~y i no )-butylidene]-cycloh~x~necarboxylic
acid (ALLOXYDIM); 4-amino-benzenesulphonyl-methyl carba-
mate (ASUhAM); 2-chloro-4-ethylamino-6-isopropylamino-
Le A 28 318 - 48 -

2 ~ 3 ~
1,3,5-triazine (ATRAZINE); methyl 2-[[[[~(4,6-dimethoxy-
pyrimidin-2-yl)-amino]-carbonyl~-amino]-sulphonyl]-
methyl]-benzoate ~BENSULFURON); 3-isopropyl-2,1,3~benzo-
thiadiazin-4-one 2,2 dioxide (sENTAzoNE); methyl 5-(2,4-
dichlorophenoxy)-2-nitrobenzoate (sIFENox); 3,5-dibromo-
4-hydroxy-benzonitrile; (BROMOXYNIL); N-(butoxymethyl)-
2-chloro-N-(2,6-diethylphenyl)--acetamide (BUTACHLOR);
5-amino-4-chloro-2-phenyl-2,3-dihydro-3-oxy-pyridazine
(CHLORIDAZON); ethyl 2-{[(4-chloro-6-methoxy-2-pyrimi-
dinyl)-aminocarbonyl]-aminosulphonyl}-benzoate
(CHLORIMVRON); N-(3-chlorophenyl)-isopropyl carbamate
(CHLOROPROPHAM); 2-chloro-N-{[(4-methoxy-6-methyl-1,3,5-
triazin-2-yl)-amino]-carbonyl}-benzenesulphonamide
(CHLORSULFURON); N,N-dimethyl-N'-(3-chloro-4-methyl-
phenyl)-urea (CHLORTOLURON); exo-l-methyl-4-(1-methyl-
ethyl)-2-(2-methylphenyl-methoxy)-7-oxabicyclo-~2,2,1)-
heptane (CINMETHYLIN); 3,6-dichloro-2-pyridinecarboxylic
acid (CLOPYRALID); 2-chloro-4-ethylamino-6-(3-cyanopro-
pylamino)-1,3,5-triazine (CYANAZINE); NrS-diethyl
N-cyclohexyl-thiocarbamate(CYCLOATE);2-[1-(ethoxi i n~ ) _
butyl]-3-hydroxy-5-[tetrahydro-(2H)-thiopyran-3-yl]-
2-cyclohexen-1-one (CYCLOXYDIM); 2-[4-(2,4-dichloro-
phenoxy)-phenoxy]-propionic acid, its methyl ester or its
ethyl ester (DICLOFOP); 2-[(2-chlorophenyl)-methyl]-4,4-
dimethylisoxazolidin-3-one (DIMETHAZONE); S-ethyl N,N-di-
n-propyl-thiocarbamidate (EPTAME); 4-amino-6-t-butyl-3-
ethylthio-1,2,4-triazin-5(4H)-one (ETHIOZIN); 2-{4-[(6-
chloro-2-benzoxazolyl)-oxy]-phenoxy}-propanoic acid, its
methyl ester or its ethyl ester (FENOXAPROP); 2-[4-(5-
trifluoromethyl-2-pyridyloxy)-phenoxy]-propanoic acid or
Le A 28 318 - 49 -

2 ~ 3 6
its butyl ester (FLUAZIFOP); N,N-dimethyl-N'-(3-tri-
fluoromethylphenyl~-urea (FLUOMETURON); l-methyl-
3-phenyl-5-(3-trifluoromethylphenyl)-4-pyridone
(FLURIDONE); [(4-amino-3,5-dichloro-6-fluoro-2-pyri-
dinyl)-oxyl-acetic acid or its l-methylheptyl ester
(FLUROXYPYR); 5-(2-chloro-4-trifluoromethyl-phenoxy)-N-
methylsulphonyl-2-nitrobenzamide (FOMESAFEN); N-phos-
phonomethyl-~lycine (GLYPHOSATE); 2-{4-[(3-chloro-5-
(trifluoromethyl)-2~pyridinyl)-oxy]-phenoxy}-propanoic
acid or its ethyl ester (HALOXYFOP); 3-cyclohexyl-
6-dimethylamino-1-methyl-1,3,5-triazine-2,4-dione
(HEXAZINONE);methyl2-[4,5-dihydro-4-methyl-4-(l-methyl-
ethyl)-s-oxo-lH-imidazol-2-yl]-4(5)-methylbenzoate
(IMAZAMETHABENZ); 2-(4,5-dihydro-4-methyl-4-isopropyl-
5-oxo-lH-imidazol-2-yl)-pyridine-3-carboxylic acid
(IMAZAPYR); 2-[5-methyl-5-(1-methylethyl)-4-oxo-2-imida-
zolin-2-yl]-3-quinolinecarboxylic acid (IMAZAQUIN~; 2-
[4,5-dihydro-4-methyl-4-isopropyl-5-oxo-(lH)-imidazol-2-
yl]-5-ethylpyridin-3-carboxylic acid (IMAZETHAPYR); 3,5-
diiodo-4-hydroxybenzonitrile (IOXYNIL); N,N-dimethyl-N'-
(4-isopropylphenyl)-urea (ISOPROTURON); 2-ethoxy-1-
methyl-2-oxo-ethyl 5-[2-chloro-4-(trifluoromethyl)-
phenoxy]-2-nitrobenzoate (LACTOFEN); (2-methyl-4-chloro-
phenoxy)-acetic acid (MCPA); (4-chloro-2-methylphenoxy)-
propionic acid (MCPP); N-methyl-2-(1,3-benzothiazol-2-
yloxy)-acetanilide(MEFENACE~);2-chloro-N-(2,6-dimethyl-
phenyl)-N-[(lH)-pyrazol-1-yl-methyl]-acetamide
(METAZACHLOR); 2-ethyl-6-methyl-N-(1-methyl-2-methoxy-
ethyl)-chloroacetanilide(METOT.~CHT.OR);2-{[[((4-methoxy-
6-methyl-1,3~5-triazin-2-yl)-amino)-carbonyl]-amino]-
Le A 28 318 - 50 -

2 ~ 6
sulphonyl}-benzoic acid or its methyl ester
(METSULFURON); S-ethyl N,N-hexamethylene-thiocarbamate
(MOLINATE); 1-(3-trifluoromethyl-phenyl)-4-methylamino-
5-chloro-6-pyridazone (NORFLU~ZON); 4-(di-n-propyl-
amino)-3,5-dinitrobenzenesulphonamide (ORYZALIN); 2-
chloro-4-trifluoromethylphenyl 3-ethoxy-4-nitro-phenyl
ether (OXYFLUORFEN); N-(l-ethylpropyl)-3,4-dimethyl-2,6-
dinitroaniline (PENDIMETHALIN); 3-(ethoxycarbonylamino-
phenyl) N-(3'-methylphenyl)-carbamate (PHENMEDIPHAM);
4-amino-3,5,6-trichloropyridine-2-carboxylic acid
(PICLORAM); ~-chloro-2',6'-diethyl-N-(2-propoxyethyl)-
acetanilide (PRETILACHLOR); 2-chloro-N-isopropyl-
acetanilide (PROPACHLOR); isopropyl-N-phenyl-carbamate
(PROPHAM); 0-(6-chloro-3-phenyl-pyridazin-4-yl) S-octyl
thiocarbonate ~PYRID~TE); ethyl 2-[4-(6-chloro-quinoxa-
lin-2-yl-oxy)-phenoxy]-propionate (QUIZALOFOP-ETHYL); 2-
[1-(ethoxamino)-butylidene]-5-(2-ethylthiopropyl)-1,3-
cyclohexadione (SETHOXYDIM); 2-chloro-4,6-bis-(ethyl-
amino)-1,3,5-triazine(SIMAZINE);2,4-bis-[N-ethylamino]-
6-methylthio-1,3,5-triazine (SIMETRYNE); methyl
2-{[(4,6-dimethyl-2-pyrimidinyl)-aminocarbonyl]-amino-
sulphonyl}-benzoate (SULFOMETURON); 4-ethylamino-2-t-
butylamino-6-methylthio-s-triazine ~TERBUTRYNE); methyl
3-[[[[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)-amino]-
carbonyl]-amino]-sulphonyl]-thiophene-2-carboxylate
(THIAMETURON); S-[(4-chlorophenyl)-methyl] N,N-diethyl.-
thiocarbamate (THIOBENCARB); S-(2,3,3-trichloroallyl)
N,N-dii~oprbpylthiocarbamate (TRIALLATE); 2l6-dinitro-4-
trifluoromethyl-N,N-dipropylaniline (TRIFLURALIN).
Le A 28 318 - 51 -

2 ~ 3 ~
Surprisingly, some mixtures also show a synergistic
action.
Mixtures with other kno~l active compounds, such as
fungicides, insecticides, acarlcides, nematicides, bird
repellants, plant nutrients and agents which improve soil
~tructure, 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, atomising 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 1 g and 10 kg of active compound per hectare of
soil surface, preferably between 5 g and 5 kg per ha.
The preparation and use of the active compounds according
to the invention can be seen from the following examples.
Le A 28 318 - 52 -

~~ 2~16~63
PreParation ~xample~
Exam~le l
COOCH3 O
~502-NH-CO-~' N-CH3
~Proces~ (a) ~
A mixture of 2.0 g (10.5 mmol) of 4-methyl-5-phenoxy-
2,4-dihydro-3H-1,2,4-triazol-3-one, 3.5 g (14.5 mmol) of
2-methoxycarbonyl-phenyl~ulphonyl i~ocyanate and 60 ml of
acetonitrile i8 ~tirred for 6 hour~ at 20aC and ~ub-
sequently concentrated under a watex pump vacuum. The
residue i8 ~tirred ~ith diethyl ether and the product
which ha~ precipitated in crystalline form i~ i~olated by
filtration with ~uction.
4.1 g (g0~ of theory) of 2-(2-methoxycarbonyl-phenyl-
sulphonylaminocarbonyl)-4-methyl-5-phenoxy-2~4-dihydro-
3H-1,2,4-triazol-3-one of melting point 161~C are
obtained.
Other example~ of compounds of the formul~ (I) which can
bè prepared anRlogously to Example 1 and following the
general descriptton of the preparation processes accor-
ding to the invention are those listed in Table 3 below.
Le A 28 318 - 53 -

2~6~3~
.
R3 - SOz -NH- CO-NJ~N-RI
N==CL~o_R2 (I)
Table 3: Preparation Example~ of the compound~ of the
~ formula (I~
Example Rl RZ R3 M~ltin~
No. point ( C)
COOCH3
~ ' ~
2 C2H5 ~ 1~3
CH3
3 CH3 ~ ~ 190
4 CH3 C3H7 1 l~COOCzH5 120
N'N
CH3
F
5 CH3 C3H7 ~ ~34
Le A 2~ 318 - 54 ~

2~6~36
Table 3 - Continuation
ExampleRl R2 R3 Meltin~
No. point ( C)
6 CH3 C3H7 ~ 122
COOC3H7
7 CH~ C3H7 ~ 125
8 CH3 CzH5 ~ COOC2H5 166-167
~'N
CH3
COOCH3
9 CH3 C2H5 ~ 131-132
CH3 C2H5 ~ 147-148
Br
11 CH3 C2H5 ~ 186-187
COOC3H7
12 CH3 C2H5 ~ 125-126
COOCzH5
13 CH3 C2H5 ~ 123-124
Le A 28 318 - 55 -

2 ~ 3 ~
Table 3 - Continuation
ExampleRl ~2 R3 Meltin~
14 CH3 C2H5 ~ ~ 188-189
Cl
CH3 C2H5 ~ H3 175-176
OCF~
16 CH3 C2H5 ~ 152-153
CF3
17 CH3 C2~5 ~ 17Z-173
OCHF2
18 CH3 CzH5 ~ 147-148
Cl
19 CH3 C2H5 ~ H2_ 183-184
CH3 C2H5 ~ 178-183
5 OOCH3
OCF3
21 CH3 C2H5 ~ H2_ 155-156
Le A 28 318 - 56 -

2~ 3~
Table 3 - Continuation
Example Rl R2 R3 Melting
No. point ( ~C)
22 CH3 ~ ~ 162-163
CH3
23 CH3 CzH5 ~ 146-147
COOCH3
24 C3H7 CH3 ~ 129-130
F
C3H7 C~3 ~ 150-151
Br
26 C3H7 CH3 ~ 130-131
COOC3H7
27 ~3H7 CH3 ~ 135-136
COOC2H5
28 C3H7 CH3 ~ 126-127
2-9 C3H7 CH3 ~ 116-117
Le A 28 318 - 57 -

2~6~3~
Table 3 - Continuation
Example R1 R2 R3 Melting
No. point ( ~C)
C3H7 CH3 ~ ~ COOCzH5129-130
CH3C 1
31 C3H7 CH3 ~ 156-157
CH~
OCF3
3Z C~H7 CH3 ~ 117-118
CF3
33 C3H7 CH3 ~ 139-140
OCHF2
34 C3H7 ~H3 ~ 1 115-116
35 C3H7 CH3 ~ H2_ 183-184
36 C3H7 C~3 ~ 130-131
5'~COOCH3
- OCF3
37 C3H7 CH3 ~ H2_ 108-109
Le A 28318 - 58 -

2 0 64G3 6
Table 3 - Continuation
No. Rl R2 R3polnt ( C)
38 C3H7 CH3 ~ ~ 122-lZ3
CH3
39 C3H7 Cff3 ~ lZ8-129
COOCH3
CH3 C4H9 ~ 76
COOC 2H5
41 CH3 C4H9 N'N~A~ 197
CH3
42 CH3 C4H9 ~ 153
COOC3H7
43 CH3 C4H9 ~ 105
COOC2H5
44 CH C4H9 ~ 81
OCF3
CH3 C4H9 ~ 137
Le A 28 318 - 59 -

2 ~ ~ ~ 6 3 ~
Table 3 - Continuation
Example Rl R2 R3 Melting
No. point ( C)
CF3
46 CH3 C4H9 ~ 148
OCHF2
47 CH3 C4H9 ~ 114
48 CH3 C4H9 ~ 147
5~A~COOCH3
CH3
49 CH3 C4H9 ~ 139
~ ~COOC2H5
~ C2H5 N~N 114
CH3
Br
51 C2H5 ~ 135
COOC H7
~ ~ 3
52 C2H5 ~ 108
53 CH3 ~ ~ 209
CH3
Le A 28 318 - 60 -

2~636
Table 3 - Continuation
Example Rl RZ R3 Meltin~
No. point ( C)
oc~3
f=C\ /~<
54 CH3 ~ ~ 191
~r
Cl13 ~ ~ 207
c~3
56 CH3 CH~ ~ 154
~r
57 CH3 C~3 ~ 187
Cl
58 CH3 CH3 ~ 179
CH3
COOCH3
59-CH2~CH~c~2 CH3 ~ 124
Cl
60-CH2-CH~H2 CH3 ~ 153
CH3
61 -CH2-CH-CHz CH3 ~ 150
Le A 2~ 318 - 61 -

2~4~36
Table 3 - Continuation
Example Rl ~2 R3 ~eltin~
No. point ( C)
CH3
6z -CH2-CH~CHz CH3 ~ 103
CF3
~<
63-C~2-CH=CHz CH3 ~ 130
CF3
64 CH3 , CH3 ~ 196
COOCH3
CH3 CH3 ~ 136
COOCH3
66-cHz-cH~cH2 CH3 ~ 130
CF3
67 CH3 ~ ~ Zll
COOC2H5
6a CH3 ~ ~ 179
~ OCHF2
69 CH3C~3 ~ l 71
Le ~ 28 31~ - 62 -

2~63~
Table 3 - Continuation
Example R1 R2 R3 Melting
No. point (~C)
OCHF2
70-CH2-CH=CH2 CH3 ~ 115
OCHF2
71 CH3 ~ ~ 16Z
COOCH3
72 CH3 C3H7 ~ 141
COOC3H7
73 CH3 CH3 ~ 148
COOC3H7
79 CH3 ~ ~ 174
COOC3H7
75-CH2-CH=CH2 CH3 ~ 138
OCHF
/~ ~< Z
76 C~3 ~ 14
CF3
77 CH3 ~ 15C
Le A 28 318 - 63 -

2a~36
Table 3 - Continuation
Example Rl R2 R3 point (~C)
OCF3
78 -CH2-CH=CH2 CH3 ~ 125
OCF3
79 CH3 CH3 ~ 145
COzCH3
~2H5 CH3 ~ 153-154
81 C2H5 CH3 ~ 15i-152
Br
8Z C2H5 CH3 ~ 1167-168
83 C2H5 CH3 ~ 1155-156
84 C2H5 C~3 ~ 174-175
CH3
C2~5 CH3 ~ CO2C2H5
CH3
Le A 28 318 - 64 -

2 ~ 3 ~
Table 3 - Continuation
Example Rl R2 R3 Melting
No . point ( C )
C02C2H5
86 C2H5 CH3 ~ 160
OCF3
87 C2~5 CH3 ~ 146-147
CF3
88 C2H5 CH3 ~ 156-157
OCHF2
89 C2H5 CH3 ~ 125-lZ6
OCF3
C2~5 CH3 ~ H2_ 137-138
91 C2H5 CH3 ~ H2_ 203-204
C 1
92 CH3 C4H9 ~ 118-119
93 CH3 C4H9 ~ 146-147
Le A 28 318 - 65 -

2~6~3~
Table 3 - Continuation
Example Rl R2 R3 Melting
No. point ( C)
94 CH3 C4H9 ~ 110-111
C~3
OCF3
CH3 C4H9 ~ H2- 123-124
~ ~<
9S C2H5 ~ 15Z-153
~ C02C2H5
97 CZH5 ~ 116-117
Cl
98 C2H5 ~ 145-146
99 C2H5 ~ 13Z-133
CH3
~ OCF3
100 C2H5 ~ 88-89
Le A 28 318 - 66 -

2~6 ~S3~
Table 3 - Continuation
Example Rl R2 R3 Melting
No. point (~C)
CF3
101 C2H5 ~ 128-129
OCHF2
/\ f\
102 C2H5 ~ 79-77
COOCH3
103 -CH2-CH=CH2 C2H5 ~ 114-115
COOC 2H5
104 -CH2-CH=CH2 C2H5 r~ 104-106
N'N~
CH3
105 -CH2-CH=CH2 C2H5 ~ 85-86
Br
106 -CH2-CH=CH2 C2H5 ~ 121-122
COOC3H7
107 -CH2-CH=CH2 C2H5 ~ 107-108
COOC2H5
108 -CH2-CH=CH2 C2H5 ~ 123-124
Le A 28 318 - 67 -

2~6l~
Table 3 - CQntinuation
Example R1 R2 R3Melting
Cl
109 -CH2-CH=CH2 C2H5 ~ 131-132
110 -CH2-CH=CH2 C2H5 ~ H3118-119
OCF3
111 -CH2-CH=CH2 C2H5 ~110-111
112 -CH2-CH=CH2 C2H5 ~123-124
OCHF2
113 -CH2-CH=CH2 C2H5 ~ 1103-104
114 -CH2-CH=CH2 C2H5 ~ ~250
Cl
OCF3
115 -CH2-CH=CH2 C2H5 ~ CH2- 114-115
CH3
116 -CH2-CH=CH2 C2H5 ~ 122-123
Le A 28 318 - 68 -

2 ~ 3 ~
Table 3 - Continuation
Example R~ R2 R3 Melting
No. point (~C)
COOCH3
117 CH(CH3)2 C2H5 ~ 188-190
COOC2H5
118 CH(CH3)2 C2H5 ~ 230-231
N~N
CH3F
119 CH~CH3)2 C2H5 ~ 129-130
Br
120 CH(CH3)2 C2H5 ~ 207
(Zers. )
COOC2H5
121 CH(CH3)2 C2H5 ~ ~ 113-114
122 CH(CH3)2 C2H5 ~ ~ 195-200
123 CH(CH3)2 C2H5 ~ 133-134
CH3
CF3
124 CH(CH3)2 C2H5 ~ 139-140
Le A 28 318 - 69 -

2 ~ 3 6
Table 3 - Continuation
Example Rl RZ R3 Melting
OCHF2
125 CH(CH3)2 C2H5 ~ 105-106
CH3
126 CH(CH3)2 C2H5 ~ 123-124
COOCH3
127 -(CH2)3-0CH3 CH3 ~ 112-114
COOC 2H5
128 ~CH2)3 oCH3 CH3 N'N'A~ 92-95
CH3
129 -(CH2)3-0CH3 CH3 ~ 126-127
Br
130 -(CH2)3-0CH3 CH3 ~ 115-116
COOC2H5
131 -(CH2)3-0CH3 CH3 ~ 112-113
OCF3
132 (CH2)3-0CH3 CH3 ~ 81-82
Le A 28 318 - 70 -

2~6~63g
Table 3 - Continuation
Example Rl R~ R3 Melting
133 -tCH2)3-0cH3 CH3 ~ 104-105
OCHF2
134 -(CH2)3-0CH3 CH3 ~ 113-114
CH3
135 -(CH2)3-0CH3 CH3 ~ 91-92
COOCH3
136 n-C3H7 C2H5 ~ 108
COOC2~5
137 n-C3H7 C~H5 ~ 212-213
N~N'~
CH3F
138 n-C3H7 C2H5 ~ 106-107
Br
139 n-C3H7 C2H5 ~ 127-128
COOC2H5
140 n-C3H7 C2H5 ~ (7ers.)
Le A 28 318 - 71 -

2 ~ 3 6
Table 3 - Continuation
~x~mple R' R2 R3 Melting
No. point (~C)
141 n-C~H7 C2H5 ~ ~ 132-135
142 n-C3H7 C2H5 ~ H3 138-140
OCF3
143 n-C3H7 C2H5 ~ 87-88
CF3
144 n-C3H7 C2H5 ~ 108-109
OCHF2
n-C3H7 C2H5 ~ 154-157
CH3
146 n-C3H7 C2H5 ~ 130-133
COOCH3
147 CH(CH3)2 CH3 ~ 150-151
COOC2H5
148 CH(CH3)2 CH3 N ~ 160-161
CH3
Le A 28 318 - 72 -

2 ~ 3 ~
Table 3 - Continuation
Example R~ RZ R3 point (~C)
149 CH~CH3)2 CH3 ~ 147-148
Br
150 CH(CH3)2 CH3 ~ 148-150
COOC2H5
151 CH(CH3)2 CH3 ~ 1 143-144
152 CH(CH3)2 CH3 ~ l 134-135
153 CH(CH3)2 CH3 ~ 147-150
CH3
OCF3
154 CH(CH3)2 CH3 ~ 148-150
CF3
155 CH(CH3)2 CH3 ~ 143-145
OCHF2
156 CH(CH3)2 CH3 ~ 114-116 -
Le A 28 318 - 73 -

2 ~ 3 ~
Table 3 - Continuation
Example Rl RZ R3 Melting
No. point (~C)
CH3
157 CH(CH3)2 CH3 ~ 125-128
COOCH3
158 CH3 CH(CH3)2 ~ 95-97
159 CH3 CH(CH3)2~ - 158-160
COOC2H5
160 CH3 CH(CH3)2 ~ 152-153
OCF3
161 CH3 CH(CH3)2 ~ 150-152
CF3
162 CH3 CH(CH3)2 ~ 128-130
CH3
163 CH3 CH(CH3)2 ~ 150-152
COOCH~
164 CH3 ~ ~ 117-118
Le A 28 318 - 74 -

2~6~3~
Table 3 - Continuation
Example Rl R2 F~3 Meltin~
No. point ( C)
165 Cl~3 ~ ~ 130-132
166 ~ C2l~5 ~ 148-150
S'A~COOCH3
167 C2H5 CH3 ~ ¦ 172-173
168 -CH2-CH=CH2 C2H5 ~ 130-132
S~COOCH3
169 CH(CH3)2 C2H5 ~ 142-1q4
S COOCH3
170 -(CH2)3-0CH3 CH3 ~ COOCH3 127-130
171 n-C3H7 C2H5 ~ 127-130
S~ COOCH3
172 CH(CH3)2 CH3 ~ 156--157
5-A~COOCH3
173 CH3 CH(CH3)2 ~ 198-200
S COOCH3
cOOc3H7 -n
174 CH(CH3)2 C2H5 ~ 122-124
Le A 28 318 - 75 -

2a6 i~s3"
Table 3 - Continuation
Example R1 R2 R3 Melting
No. point (~C)
COOC3H7 n
175 -(CH2)3-0CH3 CH3 ~ 97-98
COOC3H7 n
176 n-C3H7 C2H5 ~ 128-130
COOC3H7 n
177 CH(CH3)2 CH3 ~ 148-150
C~~C3H7-n
178 CH3 CH(CH3)2 ~ 154
C~~C3H7-n
179 C2Hs CH3 ~ 145
OCHF2
180 CH3 C2H5 ~ CH2- 134-136
S02N(CH3)2
181 CH3 C2H5 ~ 178
OCHF~
182 CH3 n C4H5 ~ CH2- 142-143
Le A 28 318 - 76 -

2~4~3~
Table 3 - Continuation
Example Rl RZ R3 Melting
No. point (~C)
OCHF2
183 C2Hs CH3 ~ H2_ 115-118
OCHF2
184 -CH2-CH=CH2 C2H5 ~ CH2- 98-99
COOCH3
185 CH3 C2H5 ~ (Na-Salz)
C~~C3H7-n
~ 135-140
186 CH3 C2H5 ~ (Na-Salz)
CF3 161-163
187 CH3 CH3 ~ (Na-Salz)
Le A 28 318 - 77 -

2~636
Startinq substances of the formula (II):
Example (II-1)
o
H-NJ~N-cH2-cH=cH2
~ -CH
A mixture of 5.0 g (0.02 mol) of 1-phenoxycarbonyl-
4-allyl-O-methyl-iso~emicarbazide and 30 ml of toluene is
refluxed for 15 minutes and subsequently concentrated
under a water pump vacuum. The residue is trituratPd with
diethyl ether/petroleum ether, and the product which has
been obtained in crystalline form is isolated by filtra-
tion with suction.
2.0 g (64~ of theory) of 4-allyl-5-methoxy-2,4-dihydro-
3~-1,2,4-triazol-3-one of melting point 111~C are
obtained.
~e A 28 318 - 78 -

2~4~3~
Example (II-2~
J~
H-N N-CH3
CH3
50.2 g ~0.33 mol) of phenyl hydrazinoformate and 36.6 g
(0.33 mol, 93% strength) of trimethyl iminocarbonate are
heated to 60~C in 100 ml of absolute o-dichlorobenzene,
and thP mixture is stirred for 2 hours, during which
process a clear solution is formed. In the course of two
hours, it is heated to 120~C, during which process
methanol distilled off. A vacuum is applied carefully,
during which process more methanol and finally phenol
distil off. Further distillation results in a fraction
which solidifies in the receiving vessel in crystalline
form.
After recrystallisation from toluene, 7.0 g (0.054 mol,
16~ of theory) of 4-methyl-5-methoxy-2,4-dihydro-
3H-1,2,4-triazol-3-one of melting point 142-144~C are
obtained in the form of colourless crystals.
Other examples of compounds of the formula (II) which can
be prepared analogously to Examples (II-l) and (II-2~ are
those listed in Table 4 below.
- 79 -
Le A 28 318

2 ~ 3 ~
H-N ~ N-Rl tII)
~ 2
l'able 4: Examples of the starting substances of the
formula (II)
Example R1 R2 Nelting
No. point ( C~
II-3 CH3 ~ 163
II-4 CH3 C3H7
~ 149
II-5 CH3
~ 130
II-6 C2H5
80-81
II-7 CH(CH3)2 CH3
(b.p : 120~C
II-8 C2H5 CH3 at 1,5 mbar~
(b.p.: 130-150~C
II-9 C3H7 CH3 at 1,5 mbar)
152-153
Il-10 CH3 C4Hg
~4-85
II-11 tCH2)30CH3 CH3
(b.p.: 140-150~C
II-12 CH3 C2H5 at 1,5 mbar)
II-13 CH(CH3)2 C2H5 66-67
~b.p.: 140-150~C
II-14 C3H7 C2H5 at 1,5 mbar~
II-15 CH2=CH-CH2 C2H5 at 1,5 mbar)
- 80 -
Le A 28 318

2~63~
Intermediates of the formula ( rx
Example (IX-1)
~==~ ,~-CH3
~0- CO-NI~-N=C~,
Nl-l - CH2 - CH= C~2
A mixture of 30.4 g (0.2 mol) of phenyl hydrazinoformate,
26.0 g (0.2 mol) of methyl N-allyl-iminocarbonate and
150 ml of methanol is stirred for 12 hours at 20~C and
subsequently concentrated under a water pump vacuum. The
residue is triturated with diethyl etherJethanol (1/l by
vol.), and the crystalline product is isolated by filtra-
tion with suction.
11.0 g (22% of theory) of 1-phenoxycarbonyl-4-allyl-
O-methyl-isosemicarbazide of melting point 114~C are
obtained.
Other examples of compounds of the formula (IX) which can
be prepared analogously to Example (IX-1) are those
listed in Table 5 below.
Le A 28 318

2 ~ 3 ~
,o-R2 ( tx)
R4-o-Co-NH-N=C~
NH-E~l
Table 5: Examples of the compounds of the forrnula ( IX )
Example Rl R2 R4 Melting
No. point ( ~C)
IX-Z CH3 CH3 ~ 123
IX-3 C2H5 CH3 C2H5 137
IX-4 CH3 CH3 CH3 134
IX-5 C~3 CH3 C2H5 135
IX-6 C2~5 CH3 ~ 133-134
Le A 28 318 - 82 -

2 ~ 3 ~
Use Examples:
In the Use Examples, the following compound (A) is used
as compari~on substance:
Cl ~
S02-NH-CO-N~ ~N-CH3 (A)
H?
2-(2-chloro-phenylsulphonylaminocarbonyl)-4,5-dimethyl-
2,4-dihydro-3H-1,2,4-triazol-3-one (disclosed in
EP A 341,489).
Example A
Post-emergence test
Solvent: 5 parts by weight of acetone
Emulsifier: 1 part by weight of alkylaryl polyglycol
ether
To produce a suitable preparation of active compound, 1
part by weight of active compound is mixed with the
stated amount of solvent, the stated amount of emulsifier
is added and the concentrate is diluted with water to the
desired concentration.
Test plants which have a height of 5 - 15 cm are sprayed
with the preparation of the active compound in such a way
as to apply the particular amounts of active compound
- 83 -
Le A 28 318

2 ~ 3 ~
desired per unit area. The concentration of the spray
liquor is 90 chosen that the particular amounts of active
compound de~ired are applied in 1,000 1 of water/ha.
After three weeks, the degree of damage to the plants is
rated in % damage in comparison to the development of the
untreated control. The figures denote:
0% = no action (like untreated control)
100% = total destruction
In this test, a considerably more powerful action against
weeds than the known compound (A) is shown, for example,
by the compounds of Preparation Examples 1, 2, 3, 53, 54,
55, 56, 57, 58, 64, 65 and 67, while having, in some
cases, good crop plant compatibility.
Example B
Pre-emergence test
Solvent: 5 parts by weight of acetone
- Emulsifier: 1 part by weight of alkylaryl polyglycol
ether
To produce a suitable preparation of active compound, 1
part by weight of active compound is mixed with the
stated amount of solvent, the stated amount of emulsifier
is added and the concentrate is diluted with water to the
desired concentration.
Seeds of the test plant~ are sown in normal 80il and,
after 24 hours, watered with the preparation o~ the
- 84 -
Le A 28 318

2~ 3~
active compound. It is expedient to keep constant the
amount of water per unit area. The concentration of the
active compound in the preparation is of no importance,
only the amount of active compound applied per unit area
S being deci~ive~ After three weeks, the degree of damage
to the plants i5 rated in % damage in comparison to the
development of the untreated control. The figures denote:
0~ = no action (like untreated control)
100~ = total destruction
In this test, a considerably more powerful action against
weeds than the known compound (A) is shown, for example,
by the compounds of Preparation Examples 2, 54 and 69,
while having, in some ca~es, good crop plant compati-
bility.
Le A 28 318

Representative Drawing