AU658862B2 - Sulphonylaminocarbonyltriazolinones having substituents bonded via oxygen - Google Patents

Description

X Our Ref: 423365 P/00/011 Regulation 3:2 AUSTRALIA 6 8862 Patents Act 1990

ORIGINAL

COMPLETE SPECIFICATION STANDARD PATENT a a .a a a Applicant(s): Address for Service: Invention Title: Bayer Aktiengesellschaft D-5090 Leverkusen Bayerwerk

GERMANY

DAVIES COLLISON CAVE Patent Trade Mark Attorneys Level 10, 10 Barrack Street SYDNEY NSW 2000 Sulphonylaminocarbonyltriazolinones having substituents bonded via oxygen The following statement is a full description of this invention, including the best method of performing it known to me:- 5020 The invention relates to new suiphonylaninocarbonyltriazolinones having substituents bonded via oxygen, to a plurality of processes anC novel intermediates for their preparation, and to their use as herbicides.

It has been disclosed that certain substituted suiphonylaminocarbonyltriazolinones such as, for example, 2- (2-chloro-phenylsulphonylaninocarbonyl 1-4, 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 satisfactory in all respects.

P. Further sulphonylaminocarbonyltriazolinones such as, for example, 2- (2-methoxycarbonyl-phenylsulphonylauinocarbonyl) -4-methyl-5-niethoxy-2, 4-dihydroo 15 31-1,2,4-triazol-3-one are the subject of an earlier, butt non-prior-published Patent Application (cf. German Patent 3,934,081 dated 12.10.1989)o *.:There have now been found the novel sulphonylaminocarbonyltriazolinones having substituents bonded via oxygen, of the general formula (I) 0 0 Ps-O -R 2 Le A 28 318-1 1 I I in which

R

1 represents hydrogen, amino, or an optionally substituted radical from the series comprising alkyl, alkenyl, alkinyl, cycloalkyl, aralkyl, aryl, alkylamino, cycloalkylamino, dialkylamino,

R

2 represents an optionally substituted radical from the series comprising alkyl, alkenyl, alkinyl, cycloalkyl, cycloalkenyl, aralkyl, aryl, and

R

3 represents an optionally substituted radical from the series comprising alkyl, aralkyl, aryl, heteroaryl, and salts of compounds of the formula with the exception of 2- (2-methoxycarbonyl-phenylsulphonylaminocarbonyl)-4-methyl-5-methoxy-2,4-dihydro- 3H-1,2,4-triazol-3-one (cf. German Patent 3,934,081).

The new sulphonylaminocarbonyltriazolinones having substituents bonded via oxygen, of the general formula are obtained when *0

S

Le A 28 318 2 triazolinones of the general formula (II) H-

-R

in which R1 and R 2 have the abovenientioned meanings are reacted with suiphonyl isocyanates of the general formula (III)

RR

3 -S0-NC0 (I :in which R 3 has the abovementioned meaning, 10 if appropriate in the presence of a diluent, or when triazolinone derivatives of the general f ormii Yi (IV) Z -Co NANN -R I

(IV)

Le A 28 318 3in which R' and R 2 have the abovementioned meanings and Z represents halogen, alkoxy, aralkoxy or aryloxy, are reacted with sulphonamides of the general formula (V) R R 3

S

2

-N

2

(V)

in which

:R

3 has the abovementioned meaning, if appzopriate in the presence of an acid acceptor and if appropriate in the presence of a diluent, or when triazolinones of the general formula (II) C 0 HN, N(-In NAR2 in which 4

R

1 and R 2 have the abovementioned meanings are reacted with sulphonamide derivatives of the general formula (VI) R'-SOg-NH-CO-Z

(VI)

in which

R

3 has the abovementioned meaning and 2 represents halogen, alkoxy, aralkoxy or aryloxy, if appropriate in the presence of an acid acceptor and if appropriate in the presence of a diluent and, if appropriate, salts are formed, by customary methods, of the compounds of the formula which have been prepared by process or The new sulphonylaminocarbonyltriazolinones having substituents bonded via oxygen, of the general formula S: 15 and their salts are distinguished by a powerful herbicidal activity.

Surprisingly, the new compounds of the formula show Q a considerably better herbicidal action than the known compound 2-(2-chlorophenylsulphonylaminocarbonyl)- 4,5-dimethyl-2,4-dihydro-3H- 2,4-triazol-3-one, which has a similar structure.

Le A 28 318 5 The invention preferably relates to compounds of the formula in which Ri represents hydrogen, amino, or represents Cl-C 5 -alkyl which is optionally substituted by fluorine, chlorine, bromine, cyano, C 1

-C

4 -alkoxy, C-C 4 -alkylcarbonyl or Cl-C 4 -alkoxy-carbonyl, or represents

C

3 -C-alkenyl or C 3 -C-alkinyl, each of which is optionally substituted by fluorine, chlorine and/or bromine, or rep:esents C 3

-C

6 -cycloalkyl which is optionally substituted by fluorine, chlorine, bromine and/or Cl-C 4 -alkyl, or represents phenyl- Cl-C 3 -alkyl which is optionally substituted by fluorine, chlorine, bromine, cyano, nitro, C 1 -C4alkyl, trifluoromethyl, Cl-C 4 -alkoxy and/or C 1 -C4,- S 15 alkoxy-carbonyl, or represents phenyl which is .o ptionally substituted by fluorine, chlorine, .i bromine, cyano, nitro, C 1

-C

4 -alkyl, trifluoromethyl,

C.-C

4 -alkoxy, fluorine- and/or chlorine-substituted

C,-C

3 -alkoxy, Cl-C 4 -alkylthio, fluorine- and/or chlorine-substituted C-C 3 -alkylthio, Cl-C 4 -alkylsulphinyl, Cl-C 4 -alkylsulphonyl and/or Cl-C 4 -alkoxycarbonyl, or represents Cl-C 4 -alkylamino which is optionally substituted by fluorine, cyano, C 1 -C4alkoxy or Cl-C 4 -alkoxy-carbonyl, or represents C 3

-C

6 25 cycloalkylamino or di-(Cl-C 4 -alkyl)-amino, R represents Cl-C 6 -alkyl which is optionally substituted by fluorine, chlorine, bromine, cyano, C 3

-C

6 cycloalkyl, C 1

-C

4 -alkoxy or C-C 4 -alkoxycarbonyl, or Le A 28 318 6 I I I represents C 3

-C

6 ,-alkenyl or C 3

-C

6 ,-alkinyl, each of which is optionally substituted by fluorine, chlorine and/or bromine, or represents C 3

-C

5 -cycloalkyl which is optionally substituted by fluorine, chlorine, bromine and/or Cl-C 4 -alkyl, or represents cyclohexenyl, or represents phenyl-Cl-C 3 -alkyl which is optionally substituted by fluorine, chlorine, bromine, cyano, nitro, Cl-C 4 -alkyl, trifluoromethyl, Cl-C 4 -alkoxy and/or Cl-C 4 -alkoxy-carbonyl, or represents phenyl which is optionally substituted by fluorine, chlorine, bromine, cyano, nitro, C 1

-C

4 alkyl, trifluoromethyl, Cl-C 4 -alkoxy, fluorineand/or chlorine-substituted Cl-C 3 -alkoxy, C 1

-C

4 alkylthio, fluorine- and/or chl1orine-substituted Cl-C 3 -alkylthio, Cl-C 4 -alkyl-sulphinyl, Cl-C 4 -alkylsulphonyl and/or Cl-C 4 -alkoxy-carbonyl, and R 3 represents the group in which R 4 and R 5 are identical or different and represent hydrogen, fluorine, chlorine, bromine, iodine, nitro, Cl-C 6 -alkyl (which is optionally substituted by fluorine, chlorine, bromine, cyano, carboxyl, C,-C 4 -alkoxycarbonyl, CI-C 4 alkylamino-carbonyl, di- (Cl-C 4 -alkyl aminocarbonyl, hydroxyl, C-C 4 -alkoxy, formyloxy,

C

1

-C

4 -alkyl-carbonyloxy, C-C 4 -alkoxycarbonyloxy, C 1

-C

4 -a 1kyl amino -carbonyloxy, Cl-C 4 -alkylthio, C.-C-alkylsulphinyl, C1-C4_ Le A 28 318-- 7 alkylsuiphonyl, di- (C 1

-C

4 alkyl) -aminosuiphonyl,

C

3 -C-cycloalkyl or phenyl), or represent C 2

-C

5 alkenyl (which is optionally substituted by fluorine, chlorine, bromine, cyano, C 1

-C

4 alkoxy-carbonyl, carboxyl or phenyl), or represent C 2

-C

6 -alkinyl (which is optionally substituted by fluorine, chlorine, bromine, cyano, C-C 4 -alkoxy-carbonyl, carboxyl or phenyl), or represent Cl-C 4 -alkoxy (which is optionally substituted by fluorine, chlorine, bromine, cyano, carboxyl, Cl-C 4 -alkoxy-carbonyl, Cl-C4-alkoxy, Cl-C 4 -alkylthio, C-4 alkylsuiphinyl. or C-C 4 -alkylsulphonyl), or represent Cl-C 4 -alkylthio (which is optionally substituted by fluorine, chlorine, bromine, cyano, carboxyl, Cl-C 4 -alkoxy-carbonyl, C1-C 4 ****alkylthio, Cl-C 4 -alkylsulphinyl or C 1

-C

4 alkylsulphonyl), or represent C.-C.-alkenyloxy :(which is optionally substituted by fluorine, chlorine, bromine, cyano or Cl-C 4 -alkoxycarbonyl), or represent C 2 -C,,-alkenylthio (which is optionally substituted by fluorine.

:chlorine, bromine, cyano, nitro, Cl-C 3 -alkylthio ~or C 1 C-alkoxycarbonyl), C 3 C-alkinyloxy, Calkinylthio or the radical -S(O)P-R6 where represents tenmrs1or 2 n R6 represents Cl-C 4 -alkyl (w1bich is optionally substituted by fluorine, chlorine, Le A 28 318,-8 8 bromine, cyano or Cl-C 4 -alkoxy-carbonyl), C.-C-alkenylI C 3

-C

6 -alkinyl, Cl-C 4 -alkoxy, C- .C 4 -alkoxy-C, -C 4 -alkyl amino, C_4 aikylamino, di- (Cl-C 4 -alkyl) -amino, phenyl or the radical -NHOR' where R 7 represents C 1

-C

12 -alkyl (which is optionally substituted by fluorine, chlorine, cyano, Cl-C 4 -alkoxy, C 1

-C

4 alkylthio, C-C 4 -alkylsulphinyl, C 1 -C4alkylsulphonyl, C-C 4 -alkyl-carbonyl, C 1

-C

4 alkoxy-carbonyl, Cl-C 4 -alkylamino-carbonyl or di-(Cl-C 4 -alkyl)-amino-carbonyl), or represents C 3

-C

6 -alkenyl (which is optionally substituted by fluorine, 15 chlorine or bromine) C 3

-C

6 -alkinyl, C 3

-C

6 *.cycloalkyl, C 3 -C-cyc loalkyl -Cl-C 2 -alkyl, phenyl-C 1

-C

2 -alkyl (which is optionally substituted by fluorine, chlorine, nitro, *yl Ske or CCcyano, Cl-C 4 -a±lky C 1

-C

4 -a x C14 alkoxy-carbonyl), or represents benzhydryl, or represents phenyl (which is :optionally substituted by fluorine, *chlorine, nitro, cyano, Cl-C 4 -alkyl, trifluoromethyl, C-C 4 -alkoxy, C_2 fluoroalkoxy, Cl-C 4 -alkylthio, trifluoromethylthio or Cl-C 4 -alkoxy-carbonyl), R4 and/or R 5 furthermore represent phenyl or phenoxy, or -represent CI-C 4 -alkylc arbonyl amino, Cl-C 4 -alkoxy- Le A 28 318- 9 carbonylamino, C 1

-C

4 -a lkyl amino -c arbonyl -amino, di- (Cl-C.-alkyl) -amino-c arbonyl amino, or the radical -CO-R 8 where R8 represents C,-C-alkyl, C,-C-alkoxy, C 3 -C6cycloalkoxy, C,-C 6 -alkenyloxy, C,-C-alkylthio,

C

1

-C

4 -alkyl amino, C,-C 4 -alkoxyamino, C,-C 4 -alkoxcy- Cl-C 4 -alkyl -amnino or di- (Cl-C 4 -alkyl) -amino (which are optionally substituted by fluorine and/or chlorine), R 4 and/or R5 furthermore represent triinethylsilyl, thiazolinyl, Cl-C 4 -alkylsulphonyloxy, di-(C 1

-C

4 -alkyl) amnino su lphonyl amino or the radical -CH=N-Rg where R9 represents C,-C.-alkyl which is optior:-'ly substituted by fluorine, chlorine, cyano, carboxyl, Cl-C 4 -alkoxy, Cl-C 4 -alkylthio, C 1

-C

4 alkylsulphinyl or C,-C 4 -alkylsulphonyl, or represents benzyl which is optionally substituted by fluorine or chlorine, or represents C 3 -C-alkenyl or C-C-alkinyl, each 20 of which is optionally substituted by fluorine *0 or chlorine, or represents phenyl which is optionally substituted by fluorine, chlorine, bromine, Cl-C 4 -alkyl, C 1 -C,-alkoxy, trifluoromethyl, trifluoromethoxy or trifluoromethylthio, or represents optionally *.fluorine- and/or chlorine- substituted C 1

-C

6 alkoxy, C 3

-C

6 -alkenoxy, C-C 6 -alkinoxy or Le A 28 318 10 benzyloxy, or represents amino, C 1

-C

4 alkylamino, di- (Cl-C 4 -alkyl) -amino, phenylanino,

CI-C

4 -alkyl -carbonyl -amino, C,-C 4 -alkoxycarbonylamino or Cl-C 4 -alkyl-sulphonylanino, or phenylsuiphonylamino which is optionally substituted by fluorine, chlorine, bromine or methyl, furthermore R12 R3 represents the radical -'CH where R1 0 represents hydrogen or Cl-C 4 -alkyl,

R

11 and R 1 2 are identical or different and represent hydrogen, fluorine, chlorine, bromine, nitro, cyano, C 1

-C

4 -alkyl (which is optionally substituted by fluorine and/or chlorine), C 1

-C

4 alkoxy (which is optionally substituted by fluorine and/or chlorine), carboxyl, C 1

-C

4 alkoxy-carbonyl, dimethylaminocarbonyl, C 1

-C

4 alkylsuiphonyl or di- (Cl-C 4 -alkyl) -aminosulphonyl; furthermore- Le A 28 318 11 I I

R

3 represents the radical R 1 3 -14 where

R

13 and R" are identical or different and represent hydrogen, fluorine, chlorine, bromine, nitro, cyano, Cl-C 4 -alkyl (which is optionally substituted by fluorine and/or chlorine) or C 1 alkoxy (which is optionally substituted by fluorine and/or chlorine); 0 furthermore

R

3 represents the radical where 10 R 15 and R 16 are identical or different and represent hydrogen, fluorine, chlorine, bromine, nitro, cyano, C 1

-C

4 -alkyl (which is optionally substituted by fluorine and/or chlorine), C 1

-C

4 alkoxy (which is optionally substituted by i .5 fluorine and/or chlorine), or represent C 1

-C

4 alkylthio, Ci-C 4 -alkylsulphinyl or Ci-C 4 -alkylsulphonyl (which are optionally substituted by fluorine and/or chlorine), or represent aminosulphonyl, mono-(Ci-C 4 -alkyl)-aminosulphonyl, di-(Ci-C 4 -alkyl) -aminosulphonyl or Ci-C 4 -alkoxycarbonyl or dimethylaminocarbonyl; Le A 28 318 12 (I I' furthermore

R

3 represents the radical R17 j 18 where

R

17 and R 18 are identical or different and represent hydrogen, fluorine, chlorine, bromine, Ci-C 4 alkyl (which is optionally substituted by fluorine and/or bromine), Ci-C 4 -alkoxy (which is optionally substituted by fluorine and/or chlorine), Ci-C 4 -alkylthio, Ci-C,-alkylsulphinyl W or C 1

-C

4 -alkylsulphonyl (which are optionally substituted by fluorine and/or chlorine), or represent di-(Cl-C 4 -alkyl)-aminosulphonyl; furthermore *1

R

1 9

R

3 represents the radical 20 where

R

19 and R 20 are identical or different and represent 15 hydrogen, fluorine, chlorine, bromine, cyano, nitro, Ci-C 4 -alkyl (which is optionally substituted by fluorine and/or chlorine), CI-C 4 alkoxy (which is optionally substituted by fluorine and/or chlorine), Ci-C 4 -alkylthio, 20 Ci-C 4 -alkylsulphinyl or Ci-C 4 -alkylsulphonyl Le A 28 318 13 St I (which is optionally substituted by fluorine and/or chlorine), di-(C,-C 4 -alkyl)-amino-sulphonyl, Cl-C 4 -alkoxy-carbonyl or dimethylaminocarbonyl, and A represents oxygen, sulphur or the group N-Z 1 where

Z

1 represents hydrogen, Ci-C-alkyl (which is optionally substituted by fluorine, chlorine, bromine or cyano), C 3

-C

6 -cycloalkyl, benzyl, phenyl (which is optionally Ssubstituted by fluorine, chlorine, bromine or nitro), C 1

-C

4 -alkylcarbonyl, C 1

-C

4 alkoxy-carbonyl or di-(Ci-C 4 -alkyl)-aminocarbonyl; 15 furthermore R21

N

R represents the radical 22 where

YI

R

21 and R 22 are identical or different and represent hydrogen, Ci-C 4 -alkyl, halogen, C 1

-C

4 -alkoxycarbonyl, Ci-C 4 -alkoxy or C 1

-C

4 -halogenoalkoxy, 1 represents sulphur or the group N-R 23 where

R

23 represents hydrogen or Ci-C 4 -alkyl; furthermore Le A 28 318 14 1 4'

R

2 6

R

3 represents the radical R2 5 where R24

R

24 represents hydrogen, Ci-C 4 -alkyl, benzyl, pyridyl, quinolinyl or phenyl,

R

25 represents hydrogen, halogen, cyano, nitro,

C

1

-C

4 -alkyl (which is optionally substituted by fluorine and/or chlorine), Ci-C 4 -alkoxy (which is optionally substituted by fluorine and/or e chlorine), dioxolanyl or Ci-C 4 -alkoxy-carbonyl and

R

26 represents hydrogen, halogen or Ci-C 4 -alkyl; furthermore e S. R 3 represents one oZ the groups listed below

S-'N-C

4 H NS/^ IOCH2CF3 I 02 The invention furthermore preferably relates to the The invention furthermore preferably relates to the *ee2 Le A 28 318 15 sodium, potassium, magnesium, calcium, ammonium, C 1 alkyl-ammonium, di- (Cl-C 4 -alkyl) -ammonium, tri- (Cl-C 4 alkyl)-ammonium, C 5 or C.-cyc loalkyl -ammonium and di-(Cl-C 2 -alkyl) -ben zyl -ammonium salts of compounds of the formula in which R 2 and R 3 have the meanings mentioned above as being preferred.

In particular, the invention relates to compounds of the formula in which

R

1 represents hydrogen, amino, Cl-C 4 -alkyl which is optionally substituted by fluorine, cyano, methoxy or ethoxy, or represents allyl, C 3 -Cr,,-cycloalkyl, benzyl, pherqyl, C 1

-C

3 -a lkyl amino, C 3

-C

6 -Cclakylamino or di-(C 1

-C

3 -alkyl) -amnino, R represents hydrogen, C-C 4 -alkyl which is optionally substituted by fluorine and/or chlorine, methoxy or ethoxy, or represents C 3

-C

4 -alkenyl which is optionally substituted by fluorine and/or chlorine, or represents C 3 -C-cycloalkyl, or represents benzyl which is optionally substituted by fluorine, chlorine and/or methyl, and

R

3 represents the group where R4 represents fluorine, chlorine, bromine, methyl, *0trifluoromethyl, methoxy, difluoromethoxy, Le A28 318 16 trifluoromethoxy, 2-chloro-ethoxy, 2-methoxyethoxy, Cl-C 3 -alkylthio, Cl-C 3 -alkyl suiphinyl, Cl-C 3 -alkylsulphonyl, dimethylaminosuiphonyl, diethylaminosuiphonyl, W-methoxy-N-methylaminosuiphonyl, methoxyaminosuiphonyl, phenyl, phenoxy or Cl-C 3 -alkoxy-carbonyl and represents hydrogen, fluorine, chlorine or bromine; furthermore R 3 represents the radical R12 where I Ri represents hydrogen, R" represents fluorine, chlorine, bromine, methyl, **methoxy, difluoro,iothoxy, trifluororaethoyy, ethoxy, methoxycarbonyl, ethoxycarbonyl, methylsuiphonyl or dimethylaminosuiphonyl and R 2 represents hydrogen; furthermore Le A 28 318 17 I I I

R

3 represents the radical Ro -cI s

II

o where R represents Ci-C 4 -alkyl, or 0

II

RO -C-rlzepresents the radical RO-C

I

CH3 where R represents Ci-C 4 -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.

*o Examples of the compounds according to the invention are listed in Table 1 below cf. also the Preparation Examples.

0 R3-SO2-NH-CO-N N-R1 (I) I -_R2 Le A 28 318 18 I I I Table 1: Examples of the compounds of the formula (I)

R

1

R

2 3

CH

3

CH

3

F

C 1 0:- C00C 2

H

CH

3

C

2

H

5 S S 5

*SSSSS

S

55*5**

CH

3

CH

3 5* 9 S S 5 5

S

CH

2

-CH=CH

2

CH

3

CH

3

OCI-F

2

SO

2 N (CH 3 2

COOCH

3 GJ%-CH2 F n T'C OOC2H

CH

3

CH

3

CM

3

C

2

H

5 Le A 28 318 19 f I I Table 1: (Continuation)

CH

3

CH

3 C 2

H

C

2

H

c 2 8 5 *o 0 0 0 *000*6 0 0* 0 0* *0 *0**00 c 2 8

C

3

H

7

CH

3

CF

3

OCF

3

H

2

OCH

2

CJH

2

C]

CON(CH3) 2

C

2

H

5 00 00 i 00 00 S 0 0

C

2

H

C4 (CH 3 2 Le A 28 318 20 Table 1: (Continuation) Pa R 2

R

3

CH

3

CH

3

C

2 1' 5

CH(CH-

3 '2

CH

2

-CM=CH

2

CM

3 a a.

a a aa 6 0 0* S a S a

OS

0 a NS02NH2 SCH(C8 3 2

SO

2

CH

3

F

S i (CM 3

OCF

3 GJ-CH 2 ,N-N CON (CH 3 2

C

2

H

5

CH

3 S. S

SO

o So 0*OS OSSi 50 0 a 5050 a

OS..

S

OS..

flog...

C

2

H

C

2

H

C 3

H

7

C

2

H

C

2 1' 5

CM

3 Le A 28 318 21 Table 1: (Continuation) Rl R2R 3 Br CH CH3

J

OCH

2

CH

2

OCH

3

C

2

H

LII-

CH

3 SO113 o S CH3 3 *1 "Get: S S2 .ea.

*c I Le A28 318 22 Table 1: (Continuation) Pi R2R 3

CM

3

CH

3

C

2

H

COOC

2

H

F

2

CHO

N

0-CH 2

-CF

3

S*

.Se 0S*

S

CH

3

CM

3

S-CM

2

-CECH

C2H

C

2

H

CH

3 KCOOCM3 Le A 28 318 23 Table 1: (Continuation)

CH

3

CH

3

CM

3

C

3

H

7 C2H

CM

2 CM =CH 2

CM

2 CH= CH 2 C2H

C

2

H

C2H

CM

3

CH

3 3

CCON(CH

3 2 S-'--CO0 C H 3

COOCH

3

H

2

CM

3

COOCH

3

SO

2

NCH

3 (0CM 3 0 S

S

55.5

C

2

H

5

CZH

Le A28 318 24 Table 1: (Continuation)

C

3

H

7

CH-

3

CH-

2

-CH=CHZ

CH

3

CH

3

OCH

3

C

2

H

C

2

H

C

ci Br

CH

3 c 1 U1-1 3 so

C

2

H

5

CH

3

C

2

H

C2H Le A 28 318 -2 25 Table 1: (Continuation)

CH

3 C3H c 3

H

7

C

3

H

7

CH

3

CH

3

OCHF

2 c ~H2

OCH

3

C

3

H

7

C

2

H

C

2 H C 3

H

7

S

OCH

2

CH

2

-C?

F

0

NCF

3

CH

3 c 2

H

5

CH

3

CH

3 Le A 28 318, 26 b I I Table 1: (Continuation) N CH 3 2

CE

3

C

2

H

5

CH

3

C

2

H

C

2

H

rNSC 2

NH

2

SO

2

NH

2

CE

3

CH

3 N C C 3 2

C

2

H

C S 2

NH

2 cS- -O-CF 2

-CF

2 C2

OCH

2

CH-

2 -C 1

CE

3 Le A28 318 27 If, for example, 2,6-difluoro-phenylsulphonyl isocyanate and 5-ethoxy-4-methyl-2, 4-dihydro-3H-l, 2, 4-triazol-3-one are used as starting substances, the course of the reaction in process according to the invention can be outlined by the following equation:

F

/SO

2

-N=C=O

F

0 CH3 O 2 H3 F 0 /S0 2 -NH-CO*-N'j LN'CH 3 F

C

2

H

If, for example, 2-methylthio-benzenesulphonanide and 2-chlorocarbonyl-4-dinethylamino-5-propyloxy-2 ,4-dihydro- 3H-1,2,4-triazol-3-one are used as starting substances, the course of the reaction in process according to the invention can be outlined by the following equation:

SCH

3 0-N4 0 14 -C 3

H

7 -HC1

SCM

3 0 G S 0 -NH -C ONN)%N-N~

CM

3

H

SO WK C 3

H

7 Le A28 318 28- If, for example, N-methoxycarbonyl-2-methoxy-benzenesulphonamide and 5-methoxy-4-difluoromethyl-2,4-dihydro- 3H-1,2,4-triazol-3-one are used as starting substances, the course of the reaction in process according to the invention can be outlined by the following equation: OCH3 S0 2 -NH-COOCH3 0 H1N-1N-CHF 2

"-,CM

3 a a a a a s a a .o 9 a u o a o a o e a r a a

OCH

3 0 SONH-CON- NCHF 2 -HOCH3 IjCH3 Formula (II) provides a general definition of the triazolinones to be used as starting substances in processes and according to the invention for the preparation of compounds of the formula 10 In formula R 1 and R 2 preferably, or in particular, have those meanings which have alreaiy been mentioned above in connection with the description of the compounds of the formula according to the invention as being preferred, or particularly preferred, for R' and R 2 Le A 28 318 29 Examples of the starting substances of the formul.a (I are listed in Table 2 below.

0 I 0 0 0 0 0 Le A 28 318 30 Table 2: Examples of the starting substances of the formula (II) H CH3

CH

3 CM 3 c 2 5 CM 3 C3H

CM

3 ClH(C- 3 2 CH 3

C

4

H

9 CH 3

CH

3 cH 3 C 2

H

CH

3

C

3

H

7

CHCH(CH

3 CH,

CI-

2

-CHCH

2

CH

3

CH

2 Le A 28 318 31 Table 2: (Continuation) cH.

3

C

2

H

5

C

3

H-

7

CH

2 cH

C

2

H

C

2

H

CM

2

-CH=CH

2 cH 2 -CHEr-CH 2 Br

C

2

H

C 2 H

C

2

H

%3H 7 9* V.

S.

*5 S

S

*5 S S

S

S

CZH

5

CH

2

-CH=CH

2

C

2

H

5 C 3

H

7

CR

2

CHC-

2 CHC (C 3 2 CH (CH 3 2 CH (CH 3 2 C 3

H

7

C

3

H

7

-CH

2

-'C=CH

C3H Le A 28 318 32 Some of the starting substances of the formula (II) are the subject of an earlier, but non-prior-published, Patent Application (cf. German Patent 4,030,063, dated 22.09.1990).

The compounds of the general formula (II) in which R 1 has the abovementioned meaning and R 2 represents in each case optionally substituted cycloalkyl, cycloalkenyl, aralkyl or aryl, are new and a subject of the present Patent Application.

*o The compounds of the formula (II) are obtained when .hydrazinoformic esters of the general formula (VII) 27

H

2 N-NH-CO-O-R (ViI)

S

in which 27

R

7 represents methyl, ethyl or phenyl, S. 15 are reacted with alkyliminocarbonic diesters of the general formula (VIII) ,o-R 2

(VIII)

0

R

1 -NzCo-R2 O-R2 in which

R

1 and R 2 have the abovementioned meaning, if appropriate 33 in the presence of a diluent such as, for example, methanol, at temperatures between O'C and 50"C, and the compounds formed in this process, of the general formula

(IX)

27 0-R2 R -o-CO-NH-NUC (IX)

NH-R

1 in which

R

1 R' and R 27 have the abovementioned meaning, are, if appropriate, isolated by customary methods and heated to temperatures between 50*C and 150*C, if appro- S 10 priate in the presence of a diluent such as, for example, toluene, xylene or o-dichlorobenzene (cf. Preparation Examples).

SThe starting substances of the formulae (VII) and (VIII) S: are known chemicals.

15 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 according to the invention for the preparation of compounds of the formula In formula (III), R 3 preferably, or in particular, has Le A 28 318 34 that meaning which has already been mentioned above in connection with the description of the compounds of the formula according to the invention as being preferred, or particularly preferred, for R.

Examples of the starting substances of the formula (III) which may be mentioned are: 2-f luoro-, 2-chloro-, 2-bromo-, 2-methyl-, 2-methoxy-, 2-trifluoromethyl-, 2-difluoro-.methoxy-, 2-trifluoromethoxy-, 2-methylthio-, 21-ethylthio-, 2-propylthio-, 2-methylsulphinyl-, 2-methylsuiphonyl-, 2-dimethylaminosulphonyl-, 2-diethylaminosuiphonyl-, 2- (N-methoxy- N-methyl) -aminosuiphonyl-, 2-phenyl-, 2-phenoxy-, 2-methoxycarbonyl-, 2-ethoxycarbonyl-, 2-propoxycarbony.and 2-isopropoxycarbonyl-phenylsulphonyl isocyanate, 2-f luoro-, 2-chioro-, 2-difluoromethoxy-, 2-trifluoro- "OOVOmethoxy-, 2-methoxycarbonyl- and 2-ethoxycarbonyl-benzylsuiphonyl isocyanate, 2-methoxycarbonyl-3-thienyl-sul- 'so phonyl isocyanate, 4-methoxycarbonyl- and 4-ethoxy- 0 carbonyl-1-methyl-pyrazol-5-yl-sulphonyl isocyanate.

4. 1.

0*040: 20 The suiphonyl 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; BP-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).

,some,* 25 Process according to the invention for the preparati on of the new compounds of the formula is s~s**preferably carried out using diluents. Diluents which are Le A 28 318 35 suitable for this purpose are virtually all inert organic solvents. These preferably include aliphatic and aromatic, optionally halogenated 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 diethyl ether and dibutyl ether, glycol dimethyl ether and diglycol dimethyl ether, tetrahydrofuran and dioxane, ketones such as acetone, methyl ethyl ketone, methyl isopropyl ketone and methyl Sisobutyl 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-methylpyrrolidone, and also dimethyl sulphoxide, tetramethylene sulphone and hexamethylphosphoric triamide.

When carrying out process according to the invention, the reaction temperatures can be varied within a substan- 20 tial range. In general, the process is carried out at temperatures between 0 C and 150 0 C, preferably at temperatures between 10 0 C and 8 0"C.

iia In general, process according to the invention is carried out under atmospheric pressure.

For carrying out process 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 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 variant, 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 which is obtained in this way in crystalline form is isolated by filtration with suction.

Formula (IV) provides a general definition of the triazolinone derivatives t, be used as starting substances in process according to the invention for the preparation of compounds ok the formula *0 formula R I and R 2 preferably, or in particular, have those meanings which have already been mentioned above in connection with description of the compounds of the formula according to the invention being preferred, or particularly preferred, for R 1 and R and Z preferably represents chlorine, C 1

-C

4 -alkoxy, benzyloxy 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 formula (II) listed in Table 2 and phosgene, methyl chloroformate, benzyl chloroformate, phenyl chloroformate or diphenyl 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) 0

HN-'N-R

1 in which 1 10 R 1 and R 2 have the abovementioned meanings are reacted with carbonic acid derivatives of the general formula (X)

Z-CO-Z

1

(X)

in which 15 Z has the abovementioned meaning and

Z

1 represents a leaving group such as chlorine, Le A 28 318 38 methoxy, benzyloxy or phenoxy, if appropriate in the presence of a diluent such as, 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"C and +100°C.

Formula provides a general definition of the sulphonamides furthermore to be used as starting substances in process according to the invention for the preparation of compounds of the formula In formula R 3 preferably, or in particular, has that meaning which has already been mentioned above in connection with the description of the compounds of the formula according to the invention as being preferred, or 15 particularly preferred, for R 3 The following may be mentioned as examples of the starting substances of the formula .2-fluoro-, 2-chloro-, 2-bromo-, 2-methyl-, 2-methoxy-, 2-trifluoromethyl-, 2-difluoro-methoxy-, 2-trifluoromethoxy-, 2-methylthio-, 2-ethylthio-, 2-propylthio-, 2-methylsulphinyl-, 2-methylsulphonyl-, 2-dimethylaminosulphonyl-, 2-diethylaminosulphonyl-, 2-(N-methoxy- N-methyl)-aminosulphonyl-, 2-phenyl-, 2-phenoxy-, 2-methoxycarbonyl-, 2-ethoxycarbonyl-, 2-propoxycarbonyland 2-isopropoxycarbonyl-benzenesulphonamide, 2-fluoro-, 2-chloro-, 2-difluoromethoxy-, 2-trifluoromethoxy-, Le A 28 318 39 2-methoxycarbonyl- and 2-ethoxycarbonyl-phenylmethanesulphonamide, 2-methoxycarbonyl-3-thiophenesulphonamide, 4-methoxycarbonyl- and 4-ethoxycarbonyl-l-methyl-pyra- The sulphonamides of the formula 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 according to the invention for the prepara- O tion of the new compounds of the formula is preferably 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 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 example, sodium hydroxide and potassium hydroxide, alkaline earth metal hydroxides such as, for example, calcium hydroxide, alkali metal carbonates and alkali metal alcoholates such as sodium carbonate, potassium carbonate, sodium tert-butylate and 25 potassium tert-butylate, furthermore aliphatic, aromatic or heterocyclic amines, for example triethylamine, trimethylamine, dimethylaniline, dimethylbenzylamine,

I

Le A 28 318 40 pyridine, 1,5-diazabicyclo-[4.3.0]-non-5-ene

(DBN),

1,8-diazabicyclo-[5.4.0]-undec-7-ene (DBU) and 1,4-diazabicyclo[2.2.2]-octane (DABCO).

When carrying out process 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°C and 100"C, preferably at temperatures between 10°C and 60 0

C.

Process according to the invention is generally carried out under atmospheric pressure. However, it can also be carried out under increased or reduced pressure.

For carrying out process according to the invention, the starting substances required in each case are generally employed in approximately equimolar amounts.

15 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 according to the invention is carried out in each case by customary methods.

The triazolinones of the formula (II) to be used as starting substances in process according to the invention for the preparation of compounds of the formula have already been described as starting substances Le A 28 318 41 for process according to the invention.

Formula (VI) provides a general definition of the sulphonamide derivatives furthermore to be used as starting substances in process according to the itnvention for the preparation of compounds of the formula In formula R 3 and Z preferably, or in particular, have those meanings which have already been mentioned above in connection with the description of the compounds of the formula or (IV) according to the invention as being preferred, or particularly preferred, for R 3 and Z.

Process according to the invention is preferably carried out using diluents. Solvents which are suitable for this purpose are the same organic solvents as have been mentioned above in connection with the description 15 of process according to the invention.

If appropriate, process is carried out in the presence 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 according to the invention.

When carrying out process the reaction temperatures can vary within a substantial range. In general, the e process is carried out at temperatures between 0°C and 100 0 C, preferably at temperatures between 10 0 C and Le A 28 318 42 In general, process according to the invention is carried out under atmospheric pressure. However, the process can also be carried out under increased or reduced pressure.

For carrying out process 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. The reactions are generally carried out in a suitable diluent in the presence of an acid acceptor, and the reaction O mixture is stirred for several hours at the particular temperature required. Working-up is carried out in process according to the invention in each case by customary methods.

To convert the compounds of the formula 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 such as, for example, water, methanol or ethanol. The salts can be isolated in the form of crystalline products, if appropriate after concentration.

25 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 *•o Le A 28 318 43 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, 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 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.

Le A 28 318 44 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 O compounds can be employed for combating weeds in perennial 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 hopfields, on lawns, turf and pasture-land, and for the selective combating of weeds in annual cultures.

Some of the compounds of the formula according to the invention are suitable for total or semi-total weed control, some for the selective control of monocotyledon and dicotyledon weeds in 'nonocotyledon and dicotyledon cultures, both pre-emergence and post-emergence.

a The active compounds can be converted into the customary 25 formulations, such as solutions, emulsions, wettable powders, suspensions, powders, dusting agents, pastes, Le A 28 318 45 soluble powders, granules, suspension-emulsion concentrates, natural and synthetic materials impregnated with active compound, and very fine capsules in polymeric substances.

These formulations are produced 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 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 and chlorinated oaliphatic hydrocarbons, such as chlorobenzenes, chloroethylenes or methylene chloride, aliphatic hydrocarbons, such as cyclohexane or paraffins, for example petroleum fractions, mineral and vegetable oils, alcohols, such as 20 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.

25 As solid carriers there are suitable: for example ammonium salts and ground natural minerals, such as kaolins, clays, talc, chalk, quartz, attapulgite, mont- Le A 28 318 46 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 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, maize 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 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 20 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 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, Le A 28 318 47 manganese, boron, copper, cobalt, molybdenum and zinc.

The formulations in general contain between 0. 1 and per cent by weight of active compound, preferably between and 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.

.P 10 Suitable herbicides for the mixtures are known herbicides, such as, for example, 1-amino-6-ethylthio-3- 2-dimethylpropyl) 5-triazine-2, 4 H, 3H) -dione (AMETHYDIONE) or N-(2-benzothiazolyl) -dimethyl-urea (METABENZTHIAZURQN) for combating weeds in cereals; 4- 15 amino-3-methyl-6-phenyl-1,2,4-triazin-5(4H)-one (METAMITRON) for combating weeds in sugar beet and 4amino-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 4-(2,4-dichlorophenoxy)-butyric acid 2,4dichlorophenoxypropionic acid (2 2-chloro-4- :trifluoromethyl-phenoxy)-2-nitro-benzoic acid (ACIFLUORFEN); N- (methoxy-methyl) -2 ,6-diethyl-chloroacetanilide (ALACHLOR); methyl-6, 6-dimethyl-2 ,4-dioxo-3- V. 25 2 -propenyloxyam ino) -butyl idene -cycl1ohexanec arboxyl ic acid (ALLOXYDIM); 4-amino-benzenesulphonyl-methyl carbamate (ASULAM); 2-chloro-4-ethylamino-6-isopropylamino- Le A 28 318 48 1,3,5-triazine (ATRAZINE); methyl 2-[[([[[(4,6-dimethoxypyrimidin-2-yl) -amino) -carbonyl J-amino] -suiphonyl) methyl]-benzoate (BENSULFURON); 3-isopropyl-2, 1, 3-benzothiadiazin-4-one 2,2-dioxide (BENTAZONE); methyl 5-(2 ,4dichiorophenoxy) -2-nitrobenzoate (BIFENOX); 3, 4-hydroxy-benzonitrile; (BROMOXYNIL); N- (butoxymethyl) 2-chloro-N- 6-diethyiphenyl) -acetamide (BUTACHLOR); 5-amino-4-chloro-2-phenyl-2, 3-dihydro-3-oxy-pyridazine (CHLORIDAZON); ethyl 2- (4-chloro-6-methoxy-2-pyrimidinyl)-aminocarbonyl]-aminosulphonyl}-benzoate (CHLORIMURON); N- (3-chlorophenyl) -isopropyl carbamate (CHILOROPROPHAM); 2-chloro-N-{ [(4-methoxy-6-methyl-1, triazin-2-yl)-amino]-carbonyl}-benzenesulphonamide (CHLQRSULFURON); N,N-diinethyl-N' 3-chloro-4-methylphenyl) -urea (CHLORTOLURON); exo- I-methyl-4- -methylethyl) (2-methylphenyl-methoxy) -7-oxabicyc10- heptane (CINMETHYLIN); 3,6-dichloro-2-pyridinecarboxylic acid (CLOPYRALID); 2-chloro-4-ethylamino-6-( 3-cyanopropylamino)-1,3,5-triazine (CYANAZINE); N,S-diethy.

-cyclolexyl-Lf1ocarbamfate (CYCLsA); 2- etnoximino) buty1]-3-hydroxy-5-[tetrahydro-(2H)-thiopyral-3-yl]- 2-cyclohexen-l-one (CYCLOXYDIM); 2-[4-(2,4-dichlorophenoxy)-phenoxy]-propionic acid, its methyl ester or its ethyl ester (DICLOFOP); (2-chiorophenyl) -methyl]-4, 4- 25 dimethylisoxazolidin-3-one (DIMETHAZONE); S-ethyl N,N-din-propyl-thiocarbanidate (EPTAME); 4 -amino- 6-t-butyl-3ethylthio-1, 2,4-triazin-5 (4H) -one (ETHIOZIN); 2-j4-[(6- 0 6chloro-2-benzoxazolyl) -oxy] -phenoxy}-propanoic acid, its methyl ester or its ethyl ester (FENOXAPROP); 30 trifluoromethyl-2-pyridyloxy)-phenoxy]-propanoic acid or Le A 28 318 -449 its butyl ester (FLUAZIFOP); N,N-dimethyl-N'- (3-trifluoromethylphenyl) -urea (FLUOMETURON); 1-methyl- (3-trifluoromethyiphenyl) -4-pyridone (FLURIDONE); [(4-amino-3,5-dichloro-6-fluoro-2-pyridinyl)-oxy]-acetic acid or its 1-methyiheptyl ester (FLUROXYPYR); 5-(2-chloro-4-tnifluoromethyl-phenoxy) -Nmethylsulphonyl-2-nitrobenzamide (FOMESAFEN); N-phosphonomethyl-glycine (GLYPHOSATE); (trifluoromethyl)-2-pyridinyl) -oxy]-phenoxy}-propanoic acid or its ethyl ester (HALOXYFOP); 3-cyclohexyl- 6-dimethylamino-1-methyl-l, 3, 5-triazine-2 ,4-dione (HEXAZINONE) methyl 2-[4,5-dihydro-4-methyl-4-(l-iethylethyl)-5-oxo-lH-imidazol-2-yl]-4(5)-nethylbenzoate (IXAZAMETHABENZ); 2-(4,5-dihydro-4-methyl-4-isopropyl- 5-oxo-1H-imidazol-2-yl)-pyridine-3-carboxylic acid (IMAZAPYR); 2-[5-nethyl-5-(l-methylethyl)-4-oxo-2-imidazolin-2-yl]-3-quinolinecarboxylic acid (IMAZAQUIN); 2- [4,5-dihydro-4-methyl-4-isopropyl-5-oxo-( 1H)-imidazol-2yl]-5-ethylpyridin-3-carboxylic acid (IMAZETHAPYR); 20 diiodo-4-hydroxybenzonitnile (IOXYNIL); N,N-dimethyl-N'- *9(4-isopropylphenyl)-urea (ISOPROTURON); 2-ethoxy-l- *methyl-2-oxo-ethyl 5-[2-chloro-4-(tnifluoromethyl)phenoxy3-2-nitrobenzoate (LACTOFEN); (2-methyl-4-chlorophenoxy) -acetic acid (MCPA); (4-chloro-2-methylphenoxy) 25 propionic acid (MCPP); N-methyl-2-(1,3-benzothiazol-2yloxy) -acetanilide (MEFENACET); 2-chloro-N-( 2, 6-diniethylphenyl)-N-[(lH)-pyrazol-1-yl-methylj-acetamide (METAZACHLOR); 2-ethyl-6-methyl-N- (l-nethyl-2-methoxyethyl) -chloroacetanilide (METOLACHLsOR) (4-methoxy- 6- methyl-1, 3, 5-triazin-2 -yl) -amino) -carbonyl ]-amino- Le A 28 318 50 sulphoniyl}-benzoic acid or its methyl ester (METSULFURON); S-ethyl N,N-hexamethylene-thiocarbanate (MOLINATE); 1-(3-trifluoromethyl-phenyl) -4-methylamino- 5-chloro-6-pyridazone (NORFLURAZON); 4- (di-n-propylamino) 5-dinitrobenzenesulphonamide (ORYZALIN); 2chloro-4-trifluoromethylphenyl 3-ethoxy-4-nitro-phenyl ether (OXYFLUORFEN); N- -ethylpropyl) 4-dimethyl-2, 6dinitroaniline (PEND IMETHALIN) 3 -(ethoxyc arbonyl amino phenyl) N- -metnylphenyl) -carbamtate (PHENMEDIPHAM); 4-amino-3,5,6-trichloropyridine-2-carboxylic acid (PICLORAM); ca-chloro-2 6' -diethyl-N-( 2-propoxyethyl) acetanilide (PRETILACHLOR); 2-chloro-N-isopropyl- 0 acetanilide (PROPACHLOR); isopropyl-N-phenyl-carbanate (PROPHAM); 6-chloro-3-phenyl-pyridazin-4-yl) S-octyl thiocarbonate (PYRIDATE); ethyl 6-chloro-quinoxalin-2-yl-oxy) -phenoxy]-propionate (QUIZALOFOP-ETHYL); 2- [l-(ethoxamino)-butylidene]-5-(2-ethylthiopropyl) -1,3- "86:44cyclohexadione (SETHOXYDIM); 2-chloro-4,6-bis-(ethylof, 4 4**'**amino) -1,3,5-triazine (SIMAZINE); 2,4-bis-[N-ethy.Lamino]- 6-nethylthio-1,3,5-triazine (SIMETRYNE); methyl 6-dimethyl-2-pyrimidinyl.) -aminocarbonyl ]-aminosulphonyl}-benzoate (SULFOMETURON),- 4-ethylamino-2-tbutyl amino- 6-methylthio- s-tria zine (TERBUTRYNE); methyl 3-[[[[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)-amino]- 25 carbonyl3-amino]-sulphonyl]-thiophene-2-carboxylate (THIAMETURON); (4-chiorophenyl) -methyl] N,N-diethylthiocarbamate (THIOBENCARB); S-(2,3,3-trichloroallyl) N,N-diisopropylthiocarbamate (TRIALLATE); 2, 6-dinitro-4- S....trifluoromethyl-N,N-dipropylaniline (TRIFLURALIN).

Le A 28 318 51 t I t Surprisingly, some mixtures also show a synergistic action.

Mixtures with other known active compounds, such as fungicides, insecticides, acaricides, nematicides, bird repellants, 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, atomising or scattering.

The active compounds according to the invention can be applied either before or after emergence of the plants.

o. 15 They can also be incorporated into the soil before

C.

sowing.

C

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 20 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.

C

C

Le A 28 318 52 Preparation Examples Example 1

COOCH

3 0 C S02-NH-CO-N-"N-CH3 (Process A mixture of 2.0 g (10.5 mmol) of 2,4-dihydro-3H-l,2,4-triazol-3-one, 3.5 g (14.5 mmol) of 2-methoxycarbonyl-phenylsulphonyl isocyanate and 60 ml of acetonitrile is stirred for 6 hours at 20 0 C and subsequently concentrated under a water pump vacuum. The residue is stirred with diethyl ether and the product 0 which has precipitated in crystalline form is isolated by filtration with suction.

e* 4.1 g (90% of theory) of 2-(2-methoxycarbonyl-phenylsulphonylaminocarbonyl)-4-methyl-5-phenoxy-2,4-dihydro- 3H-1,2,4-triazol-3-one of melting point 161°C are 15 obtained.

Other examples of compounds of the formula which can be prepared analogously to Example 1 and following the general description of the preparation processes according to the invention are those listed in Table 3 below.

ee* Le A 28 318 53 0 R- so 2 -NH -Co -N.A N-R' I_ "(I)R Table 3: Preparation Examples of the compounds of the formula (I) Example R R 2 R 3 Melting No. point (OC)

COOCH

3 2 C 2

H

5 /183 3CM 19Q 4CM 3

C

3

M

7

CC

2 5 120

CH

3

C

3

H

7 /134 Le A 28 318 54 Table 3 Continuation Example

R

No.

Melt ing' point C)

CH

3

CH-

3

CH

3

CH

3

CH

3

CH

3

CH

3

CH

3

C

3

H

7 C3H

C

2

H

5

C

2

H

5

C

2

H

5

C

2

H

5

CZH

5

CH

5 Br

COOC

3

H

7

CM

3

COOCH

3

F

Br COOc 3

H

7

COOCZH

0 166-167 131 -132 147- 148 1 86-187 125- 126 123- 124 125 0 Le A 28 318 55 Table 3 Continuation Example R No.

Melt ing point C)

CH

3

CH

3

CH

3

C

2

H

5 c 2

H

5

C

2 5

CI

Cl-

CH

3

OCF

3 188-189 175-176 152-153 0 000000

CH

3 c]- 3 c'- 3

CH

3

CH

3

C

2 5

C

2

H

5

C

2

H

5

C

2

H

5 c 2

H-

5

CF

3

OCHF

2

H

2

C'

ULOOCH

3

OCF

3 O-CH2- 172-173 147-148 183-184 178-183 155-156 0 Le A 28 318 56 Table 3 Continuation Example R R2R 3 No.

Melting point OC)

CH-

3

CH

3

C

3

H

7

C

3

H

7

C

2

H

5

C

2

H.

5

CH

3

CH

3 a a a. a

CM

3

COOCH

3

F

Br

COOC

3

H

7

COC

2

H

Ki 162-163 146-147 129-130 150-151 130-131 1 35-136 126-127 116-117

C

3

H

7 CM 3 a S

S

C

3

H

7

C

3

H

7 C 3

H

7

CH

3

CH

3

CM

3 Le A 28 318 57 Table 3 E xamnpl1e \1o Continuation Melting point

C

3

H

7 cH 3 c3H7

OH

3 c3H7

OH

3

C

3

H

7

C

3

H

7

C

3

H

7 CH3

CH

3 Cu 3 FFT COOC2

H

5

C

3

OCF

3

CF

3 /7

OCHF

2 Cl- K

H

2 Cl S--'C0

OCH

3

OCF

3 CJ-CH2- 129-130 156-157 117-118 139- 140 115-116 183-184 130 -131 108-109 C 3

.H

7

ON

3 c 3

H

7 083 Le A 28 318 58 1 1 Table 3 Continuatiun Example R No.

Melting point (OC)

C

3

H

7

CH-

3 c 3 7 cH- 3 a. C *0

CH

3

CH-

3

CH

3

CH

3

CH

3

C

4

H

9

C

4

H

9

C

4

H

9 c 4 8 9

C

4

H

9

C

4

H

9 g

CH

3

COOCH

3

C

3 Br COOC3H

COOC

2

H

0

OCF

3 0 197 153 105 81 122-123 128-129 a. a o a.

C.

a C a

C

CC..

a 137 Le A 28 318 59 Table 3 Continuation Example

R

No.

Meltin 7 point C)

CH

3

CH

3

CH

3

CH

3

C

4 9

C

4

H

9

C

4 iq

C

2

H

5 0e

CCC...

CF

3

OCHF

2

CH

3 1ICOOC 2

H

C1 3 Br

COOC

3

H

7 0

CM

3 148 114 147 139 114 135 108 209

C

2

H

5 CC CC C C

C

C

C 2

H

5

CH

3 -0 Le A 28 318 60

I

Table 3 Continuation Examrple R No.

Melting point C)

CH

3

CH

3

CH-

3

-KD

60 *0 0 *0 0 0*000* 0 00 0 o 0* *00*00

CH

3

CH

3 ~0 *0 ~0 0* 0

S

0 0000 59

-CH

2

-CH-=CH

2 60

-CH

2

-CH=CHZ

CH

3

CH

3

CH

3

CH

3

CH

3

OCF

3 Br

CH

3 /7 Br

CH

3

COOCH

3 C l

CH

3 Br 207 154 187 179 124 153 150 61

-CH

2

-CH=CH

2 Le A 28 318 61 Table 3 Continuation Example R No.

R 2 R3Meltin 9 point C) 62 -CH 2

-CH=CH

2 63 -CI- 2 -CH=C8 2

CM

3

CH

3 *4 0* o 9* o 99090 9. 9 9* 0*9~9o 9

CH

3

CH

3

CH

3

CH

3

CM

3 c'q 3

CM

3

CF

3

CF

3 /7

COOCH

3

COOCH

3

CF

3 c00c 2

H

OCHF

2 0 1 96 103 136 130 66 -CM 2

-CM=CH

2 130 sees 060

CM

3

CH

3

CH

3 211 179 Le A 28 318 62 Table 3 Continuation Exam~ple

R

No.

Melting point OC)

-CHZ-CH=CH

2

CH-

3

CH

3

CH

3

CM

3

CH

3 -Kr0

C

3

H

7

CM

3 -Kj0

CH

3 0* P Pp OP P. P 6p a.

PP p

P

OCHF

2

OCHF

2

COOCH

3

COOC

3

H

7 /OcH

COOC

3

H

7

OCHF

2

CF

3 0 115 162 141 148 1 74 138 148 150

-CH

2

-CH=CH

2 Amok got* o

CM

3

CH

3 Le A 28 318, 63 Table 3 Continuation Example R No.

Melting point 0

C)

78 -CH 2

-CH-=CH

2 s..a 0 @9 0 .00.

0 0*60e

CR

3 C 2

H

5

C

2

H

5

C

2

H

5

C

2

H

5 C 2

H

5 c 2

H

5

CH

3

CH

3

CH

3

CH

3

CH

3

CH

3

CH

3

CH

3

OCF

3

OCF

3 C0 2

CH

3

F

Br CH3 F C0 2

C

2

H

5

CR

3 125 145 153-154 151-152 167-168 155-156 174-175 140-141 of 0 00 q9 0 0 Le A 28 318 64 Table 3 Continuation Example

R

No.

Melting point 86

CZH

5 87

C

2

H

5 88

C

2

H

5 89

C

2

H

5

C

2

H

5 91

C

2

H

5 92

CH-

3

CH

3

CH

3

CH

3

CM

3

CH

3

CM

3

C

4

H

9

CO

2 C 2

H

07-

CF

3

CF

3

OCHF

2 /7

OCF

3

H

2 CH2

F

160 146-147 156-157 125-126 137-138 203- 204 118-119 Cl 0 93

CH

3

C

4

H

9 146- 147 Le A 28 318 65 Table 3 Continuation Example R No.

Melting point OC) 94

CH

3

CH

3 96 97

C

4

H

9

C

4

H

9

C

2

H

5

C

2

H

5 Cl

CH

3

OCF

3 ,H 2

F

/7 C0 2

C

2

H

/7 110-111 123-124 152-153 116-117 S S .5

S.

C

2

H

5 C2H C 1 C l

CH

3

OCF

3 0 145- 146 132-133 88-89 100 c 2

H-

5

S

Le A 28 318 66 Table 3 Continuation E xampl1e No.

Melting point 0

C)

C 2

H

5 102 c2H 103 -CH- 2

-CH=CH

2 C2H 104 -CH 2

-CH=CH

2 105 -CH 2

-CH-=CH

2 106 -CH 2

-CH=CH

2 C2H

C

2

H

5

C

2

H

5

CF

3

OCRF'

2 /7 COaCH 3

COOC

2

H

CH

3

F

Br

COOC

3

H

7

COOC

2

H

104- 106 85-86 121-122 128-129 79-77 114-115

S

107 -CH 2

-CH=CH

2 108 -CH 2

-CH=CH

2

C

2

H

5 107- 108

C

2

H

5 123-124 Le A 28 318 -6 67 Table 3 Continuation Example No.

Melting point Cl 109 -CH 2

-CH-=CH

2

C

2

H

5 131-132 a.

110 -CH 2

-CH=CH-

2 111 -CI- 2

-CH=CH

2 112 -CH 2 -CH=cH 2 113 -CH 2

-CH=CH

2 114 -CH 2

-CH=CH

2 115 -CH 2

-CH=CH

2

C

2

H-

5 C 2HS

C

2

H

5

C

2

H

5 C2H

C

2

H

5 Cl

CH

3

OCF

3

CF

3

OCHF

2 Cl-

I

OCF

3 H C 2 118-119 110-111 123-124 103- 104 250 114-115 a a a

CH

3 116 -CH 2

-CH=CH

2 C2H 122-123 Le A 28 318 -6 68 Table 3 -Continuation Example R No.

Melting point 0

C)

117

C(H)

118 C C3 119 CH(CH 3 2 120 CH (CH 3 2 121 CH(CH- 3 2

C

2

HS

C

2

H

5 c 2 ?1 5

C

2

H

5 CoH

COOCH

3 C00C 2

H

CH

3

F

Br c00C 2

H

188-190 230- 23 1 129-130 207 (Zers.

113-114 5.5555 122 CH(CH 3 2

C

2

H

5 S S

S

123 CH(CH 3 2 124 CH(CH 3 2 C 2

H

5

C

2

H-S

1 1

CH

3

CF'

3 /5\ 133-134 139-140 195-200 Le AL 28 318 -6 69 Table 3 -Continuation Example R No.

Melting point 0

C)

125 CH(CH- 3 2 126 CH (CH 3 2 127 -(CH 2 3

-OCH

3 128 -(CH 2 3

-OCH

3 129 -(CH 2 3

-OCH

3

C

2

H

5 C 2

H

5

CH

3

CH-

3

CH

3

CH

3

COOC

2

H

C;H

3 105-106 123-124 112-114 92-95 126-127 SC CCC 130 (H 30,-3 Br

CH

3 115-116

C

COOC

2

H

131 -(CH 2 3

-OCH

3 132 -(CH 2 3

-OCH

3

CH

3 112-113 81-82

OCF

3

CH

3 Le A 28 318 -7 70 _Table 3 Continuation Example No.

Melting point OC)

CF

3 133 -(CH 2 3

-OCH

3 134 -(CH 2 3

-OCH

3 135 -(CH 2 3

OCH

3 136 n-C 3

H-

7 137 n-C 3

H

7

CH

3 OCH-F 2

CH

3

CH

3

C

2

H

5 C 2

H

5 0 *0

CH

3

COOCH

3

COOC

2

H

CH

3 104-105 113-114 91-92 108 (Zers.

212- 213 138 n-C 3

H

7 139 n-C 3

H

7 140 n-C 3

H

7

C

2 ,Hq

C

2

H

5 Br 106- 107 127-128 a Gflat.

COOC

2

H

CHr- (Zers.

Le A 28 318 -7 71 Table 3 Continuation Ex-aipl e No.

Melting point OC) Cl 141 n-C 3

H

7

C

2

H

5 132-135 S. 142 n-C 3

H

7 143 n-C 3

H

7 144 n-C 3

H

7 145 n-C 3

H

7 146 n-C 3

H

7 147 CH (CH 3 2

C

2

HS

C2H

C

2

H

5

C,,H

5

C

2

H

5

CH

3 1

CH

3 0CF 3

CF

3 o CHF 2 CO0CH 3

COOC

2

H

CH

3 138-140 87-88 108-109 154- 157 130-133 150-151 5148 CH (CH 3 2

OH

3 160-161 Le A 28 318 -7 72 Table 3 Continuation Ex amnple No.

Melting point 149 CH (CH 3 2 150 CH(CH 3 2

CH

3

CR

3

F

Br 147-148 148- 150

S

151 CH(CH 3 2 152 CR(CR 3 2 153 CH (CH 3 2

CH

3

CH

3

CR

3 COOc 2

H

Cl- CH3

OCF

3

CF

3

OCHF

2 143-144 134-135 147-150 154 CH(CR 3 2 155 CH (CR 3 2 156 CH (CH 3 2

CR

3 CR.3

CR

3 148-150 143- 145 114-116 in S..

Le A 28 318 73 Table 3 -Continuation Example R a R 3 No.

Melting point OC)

S

9 a 157 CH(CH 3 )2 158

CH

3 159

CH-

3 160

CH

3 161

CH-

3 162

CH

3 163

CH

3 164

CH

3

CH

3 CH (CH 3 2

CH(CH

3 2

CH(CCH

3 2

CH(CH

3 2

CHCI

3 2

CH(CH

3 2 -Kil]

CH

3

COOCH

3 Br 0CF 3

CF

3

CH

3

COOCH

3 125-128 95-97 158-160 152- 153 150-152 128- 130 150-152 117-118 *a Le A 28 318 74 Table 3 Continuation Example No.

Melting point OC) 165

CH

3 -Kil

CH

3 130-132 166 167 C 2

H

5 168 -CH 2

-C-=CH

2 169 CH(CH 3 2 170 -(CH 2 3

-OCH

3 171 n-C 3

H

7 172 CH(CH 3 2 173

CH

3 C 2

H

5

CR

3

C

2

H

5 C2H

CR

3

C

2 5

CH

3 C CH 3 2

C

2

HS

s -COOCH- 3 Et7- COOCH 3

QICCOOCH

3 s 3

COOC

3

H-

7 -n 148-150 172-173 130-132 142- 144 127-130 127-130 156- 157 198- 200 122-124 a 174 CH(CH 3 2 Le A 28 318 75 I I Table Continuation Example

R

No.

Melting point 0

C)

i **St at

V.

175 -(CH 2 3

-OCH

3 176 n-C 3

H

7 177 CH(CH 3 2 178

CH

3 179 C 2

H

5 180

CH

3 181

CH

3 182

CH

3

CH

3

C

2

H

5

CH

3 CH CCH 3 2

CH

3 C2H

C

2

H

5 n-C 4

H

9

COOC

3

H

7 -n C:5\ 97-98

COOC

3

H

7 -n 128-130

COOC

3

H

7 -n 148-150

COOC

3

R

7 -n 154

COOC

3

H

7 -n 145

OCHF

2

H

2 134-136

SO

2 N CCH 3 2 L 178

OCHF

2

"'CH

2 142-143 a a 'V V a *t Le A 28 318 76 Table Continuation Examiple R z R 3 No.

Melting point (OC) 183

C

2

HS

184 -CH- 2

-CH=CH

2

CH

3

C

2

H

5

OCHF

2

H

2 115-118 98-99

S.

6* S 469, 5 185

CH

3 186

CH

3 187

CH

3

C

2

H

5

C

2

CH

3

COOCH

3

COOC

3

H

7 -n

CF

3 114-115 (Na-Salz) 135- 140 (Na-salz) 161- 163 (Na-Salz) *i S a 6 *64

S

*e*i Le A 28 318 -7 77 Tbc3- Continuation Example No.

Melting point

CH

3

CH

3

C

6

H

5

C

6

H

5 S S

S

a. S S S

S.

S

CH

3

*SS*

Oe S S

.*S

a.

S S

S

a a S S S 191 CR 3

C

2

H

5

C

2

H

5

CR

3

NN

4-N S ICOOCH 3 cl

C

OCH

2

OCF

3 OCF2 160 (sodium salt) 144 (sodium salt) 180 (sodium salt) 270 (sodium salt) 124 (sodium salt)

C

2

H

5

CR

3

CH

3 n-C 4

H

9

C

2

H

5 LeA 28 318 78 Table 3 Continuation Example No.

Melting point *000 *0 ~0 0 0 *0 0 o 0* 00 0 0*0000 0 000* 0000 .0.0 0p 00 09 .000 0 0 #000 0* 0 @000 0 0 0000

CH

3

CH

3 Cl' 3

CH

3 Cl' 3 Cl' 3 i-C 3

H

7 i-C 3

H

7 i-C 3

H

7 i-C 3

H

7 i-C 3

H

7

-C

2

H

4 0C 2

H

-C

2 J1 4 0C 2

H

F

cI

CH

3 OcBF 2

SCH'

3 0CF 3

COOCH

3

CH

3 LeA 28 318 79 TIt 3J Continuation Example No.

N R3 Melting point 9* a &too*

CH

3

CH

3

CH

3

CH

3

CH

3

-C

2

H

4

OC

2

F-

-C

2 1-L 1

C

2

H

5

-C

2

H

4 0C 2

H

5

-C

2

H

4 0C 2

H

5

-C

2

H

4 0C 2

H

5

-C

2

H

4 0C 2

H

5

-C

2

H

4 0C 2

H

5

COOCAH

COOC3H7-n

F

SCAH

QCF

3 BrH 103 114 105 135 147 127 130 207 208 CH 3 ~r

'A

LeA 28 318 Table3 Continuation Example No.

Melting point

CH

3

-C

2

H

4 0C 2

H

OCBF

2 9 9* S S S

S

S S S 55 5555

S

S S @5 .5

S

210 CH 3

CH

3

CH

3

CH

3

-C

2

H

4 0C 2

H

5

-C

2

H

4 OC2H 5

-C

2

H

4 0C 2

H

5

-C

2

H

4

OCH

3 Cl

CH

3

CF

3 S COOCH 3 COOCAH-n 127 155 150 120 214 215

CH

3

CH

3

-C

2

H

4 0CH 3

-C

2

H

4

OCH

3

SCH

3 cH 3 LeA 28 318 81 Taibe Continuation Example No.

Melting point 0

GQ

216 9* 4e 9.

9 9 4

J

9e~44 9* 9 4* 44 4 4 4 4494*4 .94.

49 a.

4.9.

9 a 9444 49 44 4494 9 9 9 44..

CH

3

CH

3

CH

3

CH

3

CH

3 C-1 3

CH

3

-C'

2 1- 4 0CH 3

-G

2

H

4

OCH

3

-C

2

H

4

OCH

3

-C

2

H

4

OCH

3

-C

2

H

4

OCH

3

-C

2

H

4

OCH

3

-C

2 H4L 1

CH

3

CF

3 S COOCH 3

OCF

3

SCAH

F

LeA 28 318 -8 -82- Table 3 Continuation Example No.

Melting point 0

CQ

CH

3

CH

3 6*S@ S S S S

S.

S

55 S S

S.

S

S

OS**

9* 4.

Se S 5 .5.5 *s

S.

SiRS S S

S

5050 226

C

2

H

5

C

2

H

5

C

2

H

5

-C

2

H

4

OCH

3

-C

2

H

4

OCH

3

-C

2

H

4

OCH

3

-C

2

H

4

OCH

3

-C

2

H

4

OCH

3

COOCH

3 COOC3H7-n SCf 3 a4 3

C

2

H

5

C

2

H

5

-C

2

H

4

OCH

3

-C

2

H

4

OCH

3 ci

CH

3

OCHF

2 83 Table-3 Continuation Example R No.

Melting point (TC) 230 CH 3

-C

2 H4L 1

C

2

H

cl 231

CH

3

-C

2

H

4 0C 2

H

S

S S *5O# S a S o 5

S

*QSS

S a 232 233 234

CH

3

CR

3

CH

3

-C

2

H

4 0CH 3

-C

2

H

4

OCH

3

-C

2

H

4

OCH

3

OCHF

2

CI

Cl

CF

3 235

C

2

H

5

-C

2

H

4

OCH

3 236

C

2

H

5

-C

2

H

4 0CH 3 84 Tak-3. Continuation Example No.

Melting point (TC) a 9,.

V

a a *0 a.

a, a a a Oa*a a S *0C~ a

C

2

H

5

C

2

H

5

C

2

H

5

C

2

H

5

C

2

H

5

-C

2 H40~CH 3

-C

2

H

4

OCH

3

-C

2

H

4

OCH

3

-C

2

H

4

OCH

3

-C

2

F

4

OCH

3 S COOCH 3

OCF

3

SCAH

F

COOC

2

H

coocH cl 242 243

C

2

H

5

C

2

H

5

-C

2

H

4

OCH

3

-C

2

H

4

OCH

3 LeA 28 3 18 -8 Table 3 Continuation Example Pr No.

Melting point (TC)

C

2

H

5

-C

2

H

4

OCH

3 Cl Cl 9**

C

a a a a a C a a a a

CH

3

-C

2

H

4 0C 3

H

7 -i COOCl -n 246 247 Cl' 3 Cl' 3

CFI

3

-C

2

H

4 0C 3

H

7 -i

-C

2

H

4 0C 3

H

7 -i

-C

2

H

4 0C 3

H

7 -i

SCH

3

QCHF

2

CI

CH

3

CF

3 Cl' 3

-C

2

H

4

OC

3 H-;-i

CH

3

-C

2 1 4

C

3

H

7 -i ILqA 28 318 86 Table 3 Continuation Example No.

Melting point (TC) 0*

B

B.

CH

3

-C

2

H

4 0C 3

H

7 -i

CH

3

-C

2

H

4 0C 3

H

7 -i

CH

3

-C)H

4 0C 3

H

7 -i C4 3

CH

3 -C,4CHOCIH

BOB.

0400 0* 4* *000 a 0 0*

B

B

*.Btj 9*40

B

0*

B

B

253 254 255 256 257 cS COOCH 3

OCF

3

COOC

3 1 -n cl Cl

CI

CH

3

-C

2

H

4 0C 3

H

7 -i

CH

3

CH

3

CH

3

-C

2 r-4U 1 CIIh 3 C4 3

-CH

2

CHOCH

3 C4 3

-CH

2 CHOCqM3

CH

3

CI

"7: LeA 28 318 87 IabjC_ Continuation Example R No.

Melting point (TC) 259 CH 3 Gil 3 i-C 3 il 7

G

2 il 5 C C C CC C

CC

C

C C C C

C

CC.C

260 Gil 3

C

2

H

5 262 Gil 3 Gil 3

CH

3 Gil 3

GB

3 -GICHOGB3

-OCHCI

GOOCH

3

OGF

3

QCF

3 Q B3

QGHF

2 Cl GB4

CF

3 140 (sodium salt) 145 (sodium salt) 140 (sodium salt) 88 Ta ble.3 -Continuation Example No.

Melting point

CH

3 cH 3

-CHCHOCI

S

S.

S S S S

S.

S

S. S 5*

S.

S

555555 5 *Se.

S.

S.

*555 55 a S

S

SSSS

I S S S S

S

S

267 CH 3 268 269

CH

3

CR

3

-CH

2

CHOCAH

CH

3

-CH

2

CHQC.H

II

OCF

3

F

QOCBF

2 coocH

F

cfxOcH

OCBF

2

C

2 11

-CH

2

CHOCH

3 CH 3 89 Table-3 Continuation Exampie No.

Melting point (TC) 9* 9 9.

9 0 9 9

S.

9 9 0 9* 9 9 a 9.9* *999 999* 9* 4* 0S*0 9* 0* 9995

S

9 9 9990 9999 99 99 9*9* 9 9 090*

CH

3

CH

3

CH

3

CH

3

CH

3

CH

3

CH

3 -CR3 CHOC-1

C

2

-CHCHOCH

C

2 c 2 1- -CR3CHOC4 C24 -CR3CHOCAR

OCF

3

F

Cl COOC37-n Cl CR3 A~i LeA 28 318 90 Table 3 Continuation Example No.

Melting point (TC) Gil 3

CH

3 9* 9* 989@9t 9* 9O 9 9999 *9 @9 9.

a 9* 9 9 9 99 *9 9999 9 o 9 Gil 3 Gil 3 Cil 3

CH

3

-CHCC

-CH

2

CHOG

2

H

CH

3 n-G 3 il 7

QCF

3

OGF

3

H

3

CO

SGH

GOOCf; scH 284 285 286 n-G 3 il 7 Gil- Gil 3 L~eA 28 318 -1 -91- IahJe- Continuation Example RIR 2

R

3 Melting No. point (TC) 287 CF! 3

CF!

3 SA176 :288 CH 3

CH

3 178 q*55tSOC21 29 n-379 S. SA pe 289 C318 -92-17 Table Continuation Example RR2R 3 Melting No. point (TC) 294 CH 3

CH

3 170

SO

2

N(CH

3 (sodium salt) 00295 CH 3

CH-

3 166 4 4 29 CH 00H 2

OCB

300 CH 337 4 *A 2831 -3 Table 3 Continuation Example RI R R 3 Melting No. point (TC) 301 CH 3 n-C 3

H

7 131

OCF

3 302 CH 3 n-C 3

H

7 156

OCH

3 303 CH 3 n-C 3

H

7 131 304 CH- 3 n-C 3

H-

7 94 Tabe-3 Continuation Example RI R R 3 Melting No. point (TC)

OCH

3 308 CIT 3 n-C 3

H

7 /\124

H

3

CO

OCAH

309 CH 3 n-C 3

H-

7 ,'\112 5 H C 2

O-

9#**3101 -K n-C3H 7 118 COOC3 2 7 3114 n-C 3 H1 7 116 S 7 28 31- Ta2IL Continuation Example R No.

Melting point

-K

n-C 3

H

7 Qcl ft.

ft ft ft.

ft ft ft ft ft.

1 ft ft Oft ft *0 ft.

ft ft ftftftft ft...

ft...

ft ft.

ft ft ft...

Oft ft ft ft...

ft ft *ftftft *ft Oft ft *ft ft ft.

ft...

ft ft ft ft...

CH

3

CH

3 n-C 3

H

7 n-C -HI n-C 3

H

7

CH

3 n-C 3

H

7

CH

3 Cl

OCH

3 F1 3

CO

QOCBF

2

COOCHJ

OCF

3 107 143 132 121 (sodium salt) 188 (sodium salt) 175 (sodium salt) LeA 28 318 96 aIrc.. Continuation Example No.

Melting point (TC) 322 n-C 3

H

7 0 00*S *0*0 0* ~0 000* 0* 0 0 .0.0 0*

CO

00 323 324

CH

3

CH

3

CH

3 CH1 3 i-C 4 Hq i-C 4 Hq

QOCHF

2

OCBF

2 QOcHF 2

COOCH

cOOcH 3 326

CH

3

OCBF

2 130 (sodium salt) ~.LeA 28 318 97 Startingi substances of the formula UUV: Example (lI-1) 0

H-N)"-NCH

2 -CH-CH2 N'%O

-CH

A mixture of 5.0 g (0.02 mci) of 1-phenoxycarbonyl- 4-'aJlyl-O-methyl-isosemicarbazide and 30 ml of toluene is ref luxed for 15 minutes and subsequently concentrated under a water pump vacuum. The residue is triturated with diethyl ether/petroleum ether, and the product which has been obtained in crystalline form is isolated by filtration with suction.

g (64% of theory) oi 4-allyl-5-methoxy-2,4-dihydzo- 3H-112f4-triazol-3-one of melting point l111C are ob~tained.

171L .A 29318 -98- Example (II-2) 0 H-N

-CH

3

OCH

3 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 the mixture is stirred for 2 hours, during which process a clear solution is formed. In the course of two be' 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 b 10 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- 15 3H-l,2,4-triazol-3-one of melting point 142-1448C are obtained in the form of colourless crystals.

Other examples of compounds of the formula (II) which can be prepared analogously to Examples (II-1) and (I1-2) are w C those listed in Table 4 below.

S-99 S1A A 28 318 0 H -WNN-

(II)

Examples of the starting substances of the formula (II) Example No.

Meltin point C) ft ft ft.

~7) ft ft.

ft ft 4.

*0 ft ft. *Sft ft ft *ft@O ft ft...

ft ft ft ft ft ft...

ft ft ft ft...

ft ft .ft ft ft ft ft.

ft ft ft ''ft.

11-3 11-4 11-5 11-6 11-7 11-8 11-9 C8 3

CH

3 "-ft.

1-10 1I-11 Z1-12 11-13 11-14 11-15 -o CH (CH 3 2

C

2

H

5

C

3

H

7

CH

3

(CH

2 3 0CH 3

CH

3

CH(CH

3 2

C

3

H

7 CHi 2 zCH-CH 2 C3H

CH

3

C,

2

H,

CH

3

CH

3

CH

3

C

4

H

9

CH

3

C

2

HS

C

2

H

5 C 2

H

5 11-0 80-81 12e0C at 1#5i mbar-) 130-1500C at 1,5 mbar') 152-153 84-85 140-1500C at 1,*5 anbar) 66-67 140-150 0

C

at 1.*5 mbar) 150 0

C

at 195 mbar) 149

A

100 Iable 4 Continuation Example R No.

Melting point (TC) S S *5

S

S.

S

4*5555

S

SS

S

S S o *5*

S

S

.5*5

S

S S 11-16 11-17 H-18 11-19 11-20 11-21 11-22 11-23

CH

3

CH

3

CH

3

C

2

H

0 2 H3

CH

3

CH

3

CH

3

CH

3

CH

3

CH

3 n-C 3

H

7 i-C 3

H

7

-C

2

H

4 0C 2 H51

-C

2

H

4

OCH

3

-C

2

H

4

OGH

3

-C

2

H

4 0C 3

H

7 -i

CH

3 -CHL OC 1 3

CH

-cf HOCAH

CA~

-CH

2

CHOCH

3

-CH

2

CH(CH

3 2

-CH

2

CH=CH

2

-CH

2

CH

2

CH(CH

3 2 134 125 94 92 73 (Oil) (Oil) 37 (amorphous) 69 82 11-24 11-25 11-26 11-27 11-28 -11-29 LeA 28 318 101 Table 4 Continuation Example No.

Melting point 0

CQ

11-30 H1-31

CH

3

CH

3

H-(

-CH

2

C(CH

3 3 S S

S*

S

S

*5 55

S

S. S 0* *5

S

*aS~aS a *Sa.

*a*S a.

Sa jaGa

S*

45

S

S

S.

5S*a a S I,.A L 28 318 102 Intermediates of the formula (IM:

SO

S

9e S 9* 09

S

0 0005 0* 005* 0*

S

9 *55S 9058 *9 *5

S.

5050

C

Example (IIX-1i

CH

3 (D -0 CONH-NC1%NH-CH 2

-CH=CHZ

A mixture of 30.4 g (0.2 mol) of phenyl hydrazinoformate, 26.-0 g 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 ether/ethanol (1/1 by vol.), and the crystalline product is isolated by filtration with suction.

11.0 g (22% of theory) of 1-phanoxycarbonyl-4-allyl- 0-methyl-isosemicarbazide of melting point 1140C are obtained.

Other examples of compounds of the formula (IX) which can be prepared analogously to Bxample (IX-1) are those 15 listed in Table 5 below.

103 Le A 28 318 r7 1- R 2 Fi'-O-CO-HH-N=C,,NHR

(IX)

Table 5: Example No.

Examples of the compounds of the formula (IX) 27 R Meltinv point

C)

GA

A A

A.

131)

A.

A

A. A A A

A.

A

A

AR. A

A

*AA*

.AAA

A A

A.

A

A

A

A A A A

A.

A

A

C)

Ix-2 IX-3 IX-4 IX-5 IX-6

CH

3

C

2

H

5

CH

3

CM

3

C

2

H

5

CH

3

CH

3

CH

3

CM

3

CH

3

-Q

C

2

H

5

CM

3

-Q

123 137 134 135 133- 134 Le A28 318 104 Use Examples: In the Use Examples, the following compound is used as comparison substance: Cl 0 CJSO2-NH-CO-N---CH 3 H3 a i i io o ii a ee c *o *o i ft 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: Emulsifier: 5 parts by weight of acetone 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 15 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 105 SLe A 28 318 v desired per unit area. The concentration of the spray liquor is so chosen that the particular .iounts of active compound desired 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 is shown, for example, by the compounds of Preparation Examples 1, 2, 3, 53, 54, 56, 57, 58, 64, 65 and 67, while having, in aome cases, good crop plant compatibility.

e 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 .o 20 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 plants are sown in normal soil and, after 24 hours, watered with the preparation of the 106 A-'Le A 28 318 4

-Y

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 being decisive. 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 denotez 0% no action (like untreated control) 100% total destruction In this test, a considerably more powerful action against weeds than the known compound is shown, for example, by the compounds of Preparation Examples 2, 54 and 69, 0 bility.

The scope of the invention is as defined in the proposed amended (restricted) claims immediately below. The definitions in the foregoing introductory description substantially correspond to the claims as filed and have been retained in this form to preserve the fullness of the original disclosure. The description has also ":been amended to include additional Examples which fall within the scope of the original disclosure.

c*o 107

Claims (4)

1. Sulphonylaminocarbonyltriazolinones having sub- stituents bonded via oxygen, of the general formula 0 R3_S0 2 NH-C4J)&N-R± I in which R1 represents hydrogen, amino, or represents alkyl whicnh is optionally substituted by fluorine, chlorine, bromine, cyanol Cl-CA- alkoxy, C,-C.-alkylcarbonyl or C 1 -C 4 -alkoxy- carbonyl, or represents C 3 -Ce-alkenyl Or C 3 -CS-' alkinyl, each of which is optionally substi- tuted by fluorine, chlorine and/or bromine, or represents C 3 -CS-cycloalkyl which is optionally substituted by fluorine, chlorine, bromine and/or Cl-C.-alkyl, or represents phenyl-C 1 C 3 G alkyl which is optionally substituted by fluorine, chlorine, bromine, cyano, nitro, C 1 -C.-alkyl, trif luoromethyl, C,-C,-alkozy and/or C-C-alkoxy-carbonyl, or represents phenyl which is optionally substituted by fluorine, chlorine, bromine, cyano, nitro, C,-C 4 ,-alkyl, trifluoromethyl, CI-C.-alkoxy, fluorine- and/or chlorine -substituted C 1 -C 3 alkoxy, C,-C.-alkyl- thio, fluorine- and/or chlorine-substituted Cl-C 3 -alkylthio, Cl-C.-alkylsulphinyl,1 Cl.-Cb, alkylsulphonyl, and/or C,-C-alkoxy-carbonyl, or represents Cl-C-al kyl amino which is optionally 1' 1 /substituted by fluorine, cyano, C-C 4 -alkoxy or VI. C-C-alkoxy-carbonyl, or represents ~Vcycloalkylamino or di- (C 1 -C-alkyl) -amino, 108 R 2 represents C,-Ce-alkyl which is optionally substituted by fluorine, chlorine, bromine, cyano, C 3 -CO-cycloalkyl,, C,-C.-alkoxy or alkoxycarbonyl,. or represents C 3 -C 6 ,-alkenyl or C 3 -C.-alkinyl, each of which is optionally substituted by fluorine, chlorine and/or bromine, or represents C 3 -C,-CYCloalkyl which is optionally substituted by fluorine, chlorine, bromine and/or C,-C 4 ,-alkyl, or represents cyclohexenyl, or represento phenyl-C 1 -C 3 -alkyl which is optionally substituted by fluorine, chlorine, bromine, cyano, nitro, C 1 -C4-alkyl, trifluoromethyl, Cl-C.-alkoxy and/or C 1 ,-C 4 alkoxy-carbonyl, or represents phenyl which is is1 optionally substituted by fluorine, chlorine, 4 bromine, cyano, nitro, C,-C 4 -alkyl, trifluoro- methyl, C 1 -C.-alkoxy, fluorine- and/or chlorine- substituted C 1 -C 3 -alkoxy, Cl-C-ilkylthio, fluorine- and/or chlorine -substituted CI-C 3 alkylthio, C,-C-alkyl-sulphinyl, C 1 -C-alkyl- suiphonyl and/or Cl-C-alkoxy-carbonyl, and 3 R represents the group in which R 4 and R3 are identical or dif ferent and represent hydrogen, fluorine, chlorine, bromine, iodine, nitro, C,-Cs-alkyl (which is optionally sub- stituted by fluorine, chlorine, bromine, cyano, 109 SLe A 28 318 carboxyl, Cl-C-alkoxycarbonyl, C,-C-alkylamino- carbonyl, di- (C 1 -C,,-alkyl) amino- carbonyl,, hydroxyl, Cl--Cb-alkoxy, formyloxy, CI-C-alkcyl-o carbonyloxy, Cl-C4-alkoxy-carbonyloxy, C 1 -C 4 alkylamino-carbonyloxy, C,-C,,-alkylthio, C 1 alk'ylsulphinyl, C 1 -C 4 -alkyloulphonyl, di- (C 1 -C 4 alkyl) -aminosuiphonyl, C 3 -C-CYCloalkyl or phenyl), or represent C 2 t-C-alkenyl (which is optionally substituted by fluorine, chloriLne, bromine, cyano, Cl-C.-alkoxy-carbonyl, carboxyl or phenyl), or represent C.-C, 8 -alkinyl (which is optionally substituted by fluorine, chlorine, bromine, cyano, C,-C4-alkoxy--carbonyl,, carboxyl or phenyl), or represent C,-C.-alkoxy (which is optionally substituted by fluorine, chlorine, bromine, cyano, carboxyl, Cl-C-alkoxy-carbonyl, suiphinyl or. Cl-C 4 -alkylsulphonyl) or represent Cl-C-alkylthio (which is optionally substituted by fluorine, chlorine, bromine, cyano, car- boxyl, C,-C-alkoxy-carbonyl,. Cl-C-alkylthio, C-C-alkylsulphinyl or Cl-C-alkylaulphonyl) or represent C 3 -C 5 -alkenyloxy (which is optionally substituted by fluorine, chlorine, bromine, cyano or Cl-C 4 -alkoxy-carbonyl), or represent 0 C.-C-alkenylthio (which is optionally sub- stituted by fluorine, chlorine, bromine, cyano, nitro, C-C 3 -alkylthio or C-C-alkoxycarbonyl), C 3 -C-alkinyloxy,, C 3 -C-alkinylthio or the radical 6 where 155TN\ L .28 31 110 p represents the numbers 1 or 2 and RG represents C, 1 -C4-alkyl (which is optionally substituted by fluorine, chlorine, bromine, cyano, or C-C-alkoxy-carbonyl), C-S tklkenyl, C 3 -C-alkinyl, Cl-C,-alkoxy, Cl 1 -C 4 -alkoxy- C-C.-alkyl amino, Cl-C-alkyl amino, di- (C 1 -C 4 alkyl) -amino, phenyl or the radical -NHOR7 where R7 represents C,-Cl.-alky1 (which is optionally substituted by fluorine, chlorine, cyano, CICb- 10 alkoxy, C,-.C-alkylthio, Cl-C-alkylsulphinyl, C-C-alkyleulphonyl, C-C,,-alkyl-carbonyl, C 1 -C4- alkoxy-carbsonyl, C-C-alkylamino-carbonyl or di-(C,-C-alkyl)-amino-carbonyl), or represents *.0 to* C 3 -C-alkenyl (which is optionally substituted *too. f luorine, chlorine or bromine) C 3 -C 6 alkinyl, C 3 -CB-cyc loalkyl, C 3 -C 6 -cycloalkyl- Cl-C 2 -alkyl, phenyl-C,-C 2 ,-alkyl (which is optionally substituted by fluorine, chlorine, *nitro, cyano, C,-C 4 -alkyl I C,-C,,-alkoxy or C-. alkoxy-carbonyl), or represents benzhydryl, or *e0represents phenyl (which is optionally substituted by fluorine, chlorine, nitro, cyano, C,-C.-alkyl, trifluoromethyl, C 1 -C 4 alkoxy, C 1 -C 2 fluoroalkoxy, Cl-C 4 -alkylthio, trifluoromethylthio or C-C 4 -alkoxy-carbonyl), R 4 and/or R 5 furthermore represent phenyl or phenoxy, or represent C,-C-alkylcarbonyl amino, C 1 -C4- ill Le A 28 318 a lkoxycarbonylaxnino,' C,-C-alkylamino-carbonyl-amino,, di-(Cl-C,-alkyl)-amino-carbonylamino,. or the radical -CO-Re where Ra represents C,-C-alkyl, C,-C 6 -alkoxy, cyc loalkoxy, C 3 -C-alkenyloxy, Cl-C-alkylthio, C-C 4 -alkylamino, Cl-C-alkoxyamino, C 1 -C-alkoxy- C,-C-alkyl -amiino or di- (C-C-alkyl) -amino (which are optionally substituted by fluorine and/or chlorine), R 4 and/or R 5 furthermore represent trimethylsilyl, thiazolinyl, C 1 -C.-alkylsulphonyloxy, di- C 1 -C4- alkyl) -aminosulphonyl amino or the radiA.cal -CH=N-Ro 99 where *RD represents C,-C-alkyl which is optionally substituted by fluorine, chlorine, cyano, carboxyl, C-C-alkoxy, C,-C 4 -alkylthio, C 1 C,- alkylsulphinyl or C 1 C-alkylsulphonyl, or represents benzyl which is optionally substituted by fluorine or chlorine, or represents C 3 -C 6 -alkenyl or C 3 -C 6 -alkinyl, each of which is optionally substituted by fluorine or chlorine, or represents 1r.henyl which is C) optionally substituted by fluorine, chlorine, bromine, Cl-C-alkyl, C,-C-alkoxy, tri- fluoromethyl, trifluoromethoxy or tri- fluoromethylthio, or represents optionally fluorine- and/or chlorine-substituted C 1 -Ce- -112- v- LeAAQ 2 1 alkoxy, C 3 -C-alkenoxy, C.-C-alkinoxy or benzyloxy, or represents amino, C 1 alkylamino, di- (Cl-C.-alkyl) -aminc. ,phenylastino, C,-C-alkyl -c arbonyl -ayaino, C,-C-alkoxy- carbonylamino or C 1 =C-alkyl -su lphonyl amino, or represents phenylsulphonylaniino which is optionally substituted by fluorine, chlorine, bromine or methyl, furthermore R2 R 3 represents the radical where a. RIOE R11

6. 0: R1 0 represents hydrogen or C,-C,,-alky1, R" and R12 are identical or different and represent hydrogen, fluorine, chlorine, bromine, nitro,, so cyano, Cl-C4-alkyl (which is optionally substituted by fluorine and/or chlorine), alkoxy (which is optionally substituted by f luorine and/or chlorine), carboxyl, C 1 alkoxy-carbonyl, dinethylazinocarbonyl, C1-C4- a:alkylsulphonyl or di- (C,-C 4 -alkyl) aminosuiphonyl; furthermore 113 ~Le A 28 318 R 3 represents the radical R tjL 4 where R13 and R" are identical or different anid represent hydrogen, fl-uorine, chlorine, bromine, nitro, cyano, C 1 -C,--nI'y1V (which is optionally substituted by fluorine an( c ilorine) or CI-C4-alkoxy (which is optionally substitcuted by fluorine and/or chlorine); furthermnore RI R 3 represents the radical in which V, 0: R' nS r dnia o ifrn n ersn 04000:I R 15 and (whaeidicali orpifferent andstrepresent chlorine, brermientroC clylsulph-Coanyl (hich ise optionally substituted by fluorine and/or chlorine), C oCr flurisn anochone), mo representCl- diC-Ca-iclupiyl -aior C 1 -C 4 oxaonyl wc re opmtinll o~~cr C- -loxcrbnl or dmehlaio furthermore 114 Le A 28 318 R 3 represents the radical .17 (jJ _Rl8 where R 1 7 and R" 8 are identical or different and represent hyd~rogen, fluorine, chlorine, bromaine, alkyl (which is optionally substituted by fluorine and/or bromine), C 1 -C4-alkoxy (which is optionally substituted by fluorine and/or chlorine), or represent C,-C.-alkylthio, CI-C4,- alkylsulphinyl or C,-C-alkylsulphonyl (which are optionally substituted by fluorine and/or chlorine), or represent di-(Cj-C,,-alkyl) -amino- .~sulphonyl; 5 furthermore R 19 31 :::represents the radical 0where R1 n 2 reietclordfeetan.ersn 2 C-.are idepntcl or differentand reupesnt alo(which is optionally substituted by urn -115 Le A f31 and/or chlorine), di-(C 1 -C,-alkyl)-amino-oul- phonyl,, C,-C-alkoxy-carbonyl or dimethylamino- carbonyl, and A represents oxygen, sulphur or the group where ZI represents hydrogen, CI 1 -C 4 -alkyl (which is optionally substituted by fluorine, chlorine, bromine or cyano), C 3 cycloalkyl, benzyl, phenyl (which is optionally substituted by fluorine, chlorine, bromine or nitro), C,-C.-alkyl- carbonyl, C-C-alkoxy-carbonyl or di- (Cl-CA-alkyl -aminocarbonyl; furthermore R 21 R3 represents the raia t-2 where

8. R 21 and R22 are identical or dif ferent and represent hydrgen C,-C.-alkyl, halogen, C-4 :.:aikoxycarbonyl, CI-C4,-alkoxy or C-4 Y' represents sulphur or the group where R 23 represents hydrogen or Cl-C-alkyl; furthermore

116- Xi A2 18 R 2 6 R 3 represents the radical I R2 5 where R24 04 S S 5 S 4 o o *S C R 2 represents hydrogen, C 1 -C4-alkyl, benzyl, pyridyl, quinolinyl or phenyl, R 25 represents hydrogen, halogen, cyano, nitro, C,-C-alkyl (which is optionally substituted by fluorine and/or chlorine), C 1 -C,-alkoxy (which is optionally substituted by fluorine and/or chlorine), dioxolanyl or C 1 -C 4 -alkoxy-carbonyl and R 26 represents hydrogen, halogen or Ci-C 4 -alkyl; furthermore R 3 represents one of the groups listed below H 3 C C -t I O~H H3C-- 5 -KOCH 2 CF 3 0 0 117 Le A 28 318 1; 118 with the exception of the compounds: 2-(2-methoxycarbonyl-phenylsulphonylaminocarbonyl)-4-methyl-5-methoxy-2 ,4- dihydro-3H- 1,2,4-trial-3-one; 2-(2-trifluoromethoxy-phenylsulphonylarninocarbonyl)-4-cyclopropyl-5-methoxy- 2,4-dihydro-3H-1 ,2,4-triazol-3-one; and 2-(2-difluoromethoxy-phenylsulphonylaminocarbonyl)-4-cyclobutyl-5-ethoxy-2 ,4- dihydro-3H-1 ,2,4-triazol-3-one. 2. Process for the preparation of sulphonylaminotriazo- linones of the general formula according to Claim 1 and salts thereof, characterized in that triazolinones of the general formula (II) 0 5 in which RI and R 2 have the meanings given in Claim I are reacted with 8ulphoflyl isocyanate8 of the general formula (III) R 3 _S0 2 -N=C=0 III in which W 3 has the meaning given in Claim 1, if appropriate in the presence of a diluent, or in that triazolinone derivatives of the general formula (IV) 0 Z -CO I WNA=LO -R2 (IV) in which R 1 and R 2 have the meanings given in Claim 1 and Z represents halogen, alkoxy, aralkoxy or aryloxy, are reacted with sulphonamnides of the general formula (V) I'.9 0.: to. 0 t R'-S0 2 -NH 2 in which re has the meaning given in Claim 1, if appropriate in the presence of an acid acceptor and if.appropriate in the presence of a diluent, or in that Le A 28 31.8 triazolinones of the general formula (II) 0 HN~ t sN R 1 (I in which R1 and R 2 have the meanings given in Claim 1 are reacted with sUiphonamide derivatives of the *general formula (VI) R '-S0 2 -NH-CO-Z (VI) in which *R 3 has the meaning given in Claim 1 and Z represents halogen, alkoxy, aralkoxy or aryloxy, 90 if appropriate in the presence of an acid acceptor and if awipropriate in the presence of a diluent and, if appropriate, salts are formed, by customary methods, of the compounds of the formula which have been prepared by process or 120 3. Sulphonylaminocarbanyltriazolinoies of the formula according to Claim 1, characterised. in that, in this formula, RI represents hydrogen, amino, C,-C-alkyl which is optionally substituted by fluorine, cyano, methoxy or ethoxy, or represents allyl, C 3 -CG-CYCloalkyl, benzyl, phenyl, C 1 -C 3 -alkylamino, cycloalkylamino or di- (C.1-C 3 -alkyl) -amino, R 2 represents C1 4 alk yl which is optionally substituted by fluorine and/or chlorine, methoxy or ethoxy, or represents C 3 -C-alkenyl which is optionally substituted by fluorine and/or chlorine, or represents C 3 -C-cycloalkyl, or represents benzyl which is optionally substituted by fluorine, chlorine and/or methyl, and R~ represents the group where 4444 represents fluorine, chlorine, bromine, methyl, trifluoromethyl, methoxy, difluoromethoxy, trifluoromethoxy, 2-chloro-ethoxy, 2-methoxy- ethoxy, C-C 3 -alkylthio, Cl-C 3 -alkylsulphinyl, Cl-C 3 -alkylsulphonyl, dimethylaminosulphonyl, diethylaminosulphonyl, N-methoxy-N-methyl- aminosulphonyl, methoxyaminosulphonyl, phenyl,phenoxy or C-C 3 -alkoxy-carbonyl and -121 A 28 318 R' represents hydrogen, fluorine, chlorine or bromine; furthermore R 1 1 R 3 represents the radical I where 0o 0 S S *0S* S SO A R" represents hydrogen, R 1 represents fluorine, chlorine, bromine, methyl, methoxy, difluoromethoxy, trifluoromethoxy, ethoxy, methoxycarbonyl, ethoxycarbonyl, methylsulphonyl or dimethylaminosulphonyl and R 12 represents hydrogen; furthermore R 3 represents the radical Ro-C S where R represents C,-C-alkyl, or 122 Le-> A 28 318 if 1 represents the radical 0 CH" 3 4 4. 0 4 40 4 0* S Ce S4 00 S S 5*0* 0~*t 44 0*#4 where R represents Cl-C 4 -allcyl. 4. Herbicidal agents, characterised in that they contain at least one suiphonyl- aminocarbonyltriazolinone of the formula according to Claim I in admixture with extenders and/or surface active agents. 5. Method of combating weeds, characterised in that suiphonylamino- carbonyltriazolinones of the general formula according to Claim 1 are allowed to act on weeds cr their environment. 6. Process for the preparation of herbicidal agents, characterised in that sulphonyl- arninocarbonyltriazolinones of the general formula according to Claim 1 are mixed with extenders and/or surface-active agents. 20 7. Triazolinones of the general formula (11) 0 H -N.'kN -R 1 I P (II) in which R1 represents amino, or an optionally substituted radical from the series comprising alkyl, alkenyl, alkinyl, cycloalkyl, aralkyl, aryl, alkylamino, cycloalkylamino and dialkylamino and 123 p-\wpdoca\cr%\423365\jgs 124 R 2 represents an optionally substituted radical from the series comprising alkyl, cycloalkyl, cycloalkenyl, aralkyl and aryl, with the exception of the compounds: 4-methyl-5-methoxy-2 ,4-dihydro-3H- 1,2 ,4-triazol-3-one; and 4-amino-5-methoxy-2, 4-dihydro-3H- 1,2 ,4-triazol-3-one. 8. 2-(2-Methoxycarbonyl-phenysulphonylaminocarbonyl)-4-methyl-5-(n-propyloxy)- 2,4-dihydro-3H-1,2,4-triazol-3-one of the formula COOCH 3 0 S0 2 -NH- CO N AN--CH 3 N 9. 2-(2-iuoromeoxy-pienysuponyamnocarony)-4-mety--netboxy-L ,4- dihydro-3{- 1 ,2,4-triazol-3-one of the formula OCF 3 0 SO-NHCO-N N C NOCH 3 DATED this 24th day of February, 1995. BAYER AKTEENGESELLSCHAFT I- By Its Patent Attorneys, V'11 C II 6t PTDAVIES COLLISON CAVE pAwpdocskgrsk4233651jgs Sulphonvlaminocarbonyltriazolinones having substituents bonded via oxygen Ab s t r a c t 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) .0. 0o 0 0 II R3-SO2-NH-CO-N N-R 1 I I_ I 2 in which R i represents hydrogen, amino, or an optionally substituted radical from the series comprising alkyl, alkenyl, alkinyl, cycloalkyl, aralkyl, aryl, alkylamino, cycloalkylamino, dialkylamino, R 2 represents an optionally substituted radical from the series comprising alkyl, alkenyl, alkinyl, cycloalkyl, cycloalkenyl, aralkyl, aryl, and Le A 28 318 R3 represents an optionally substituted radical from the series comprising alkyl, aralkyl, aryl, heteroaryl, with the exception of 2-(2-methoxycarbonyl- phenylsulphonylaminocarbonyl) -4-methyl- 5-xnethoxy-2 ,4-dihydro-3H- 1,2, 4-triazol-3-one. C Le A 28 318