AU623284B2

AU623284B2 - Halogenated sulphonylaminocarbonyltriazolinones

Info

Publication number: AU623284B2
Application number: AU63602/90A
Authority: AU
Inventors: Peter Babczinski; Klaus-Helmut Muller; Hans-Joachim Santel; Robert R. Schmidt
Original assignee: Bayer AG
Current assignee: Bayer AG
Priority date: 1989-11-03
Filing date: 1990-09-27
Publication date: 1992-05-07
Anticipated expiration: 2010-09-27
Also published as: CA2029105C; EP0661262B1; JP2965661B2; DE59010850D1; DE59009966D1; JPH03153674A; EP0661262A1; CA2029105A1; AU6360290A; ZA908799B; DK0661262T3; EP0425948A3; EP0425948A2; DK0425948T3; EP0425948B1; ES2121240T3; KR910009675A; BR9005570A; ES2081334T3; DE3936622A1

Description

Our Ref: 341399 j Our Ref: 341399 623 2ORM AUSTRALIA Patents Act COMPLETE SPECIFICATION

(ORIGINAL)

Application Number: Lodged: Complete Specification Lodged: Accepted: Published: SPriority: S Related Art: Applicant(s): Address for Service: Bayer Aktiengesellschaft D-5090 Leverkusen Bayerwerk FEDERAL REPUBLIC OF GERMANY ARTHUR S. CAVE CO.

Patent Trade Mark Attorneys Level 10, 10 Barrack Street SYDNEY NSW 2000 Complete specification for the invention entitled "Halogenated sulphonylaminocarbonyltriazolinones".

The following statement is a best method of performing it full description of this invention, including the known to me:- 1 5020 The invention relates to new halogenated sulphonylaminocarbonyltriazolinones, to several processes for their preparatio.i, and to their use as herbicides.

It is known that certain substituted aminocarbonylimidazolinones, such as, for example, 1-isobutylaminocarbonyl-2-imidazolidinone (isocarbamid), have herbicidal properties (cf. R. Wegler, Chemie der Pflanzenschutz- und Schadlingsbekmpfungsmittel [Chemistry of Plant Protection Agents and Pesticides], Vol. 5, p. 219, Springer- Verlag, Berlin-Heidelberg-New York, 1977). However, the action of this compound is not satisfactory in all respects.

The new halogenated sulphonylaminocarbonyltriazolinones of the general formula (I) So o 15 R3-SO2-NH-CO-N

N-R

1

(I)

N'

^R

2 S"in which

R

1 represents hydrogen, hydroxyl or amino, or represents an optionally substituted radical from the series comprising alkyl, alkenyl, alkinyl, cyclo- 2' '0 alkyl, aralkyl, aryl, alkoxy, alkenyloxy, alkylamino, cycloalkylamino and dialkylamino,

R

2 represents halogen and

R

3 represents an optionally substituted radical from the series comprising alkyl, aralkyl, aryl and Le A 27 155 ]a heteroaryl, as well as salts of compounds of the formula have now been found.

The new halogenated sulphonylaminocarbonyltriazolinones of the general formula are obtained when a) halogenated triazolinones of the general formula

(II)

0

R

2 j in which

R

1 and R 2 have the abovementioned meanings are reacted with sulphonyl isocyanates of the general formula (III) R -S0 2 -N=C=O (III) I in which S 15 R 3 has the abovementioned meaning, if appropriate in the presence of a diluent, or when b) halogenated triazolinone derivatives of the general formula (IV) i 0 Z-CO-N N-R1 (IV) I 'N R 2 i Le A 27 155 2

__I

in which

R

1 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

3 -S0 2

-NH

2 (V) in which

R

3 has the abovementioned meaning, if 'appropriate in the presence of an acid acceptor and if appropriate in the presence of a diluent, or when c) halogenated triazolinones of the general formula

(II)

0 HN N-R 1

(II)

in which

R

1 and R 2 have the abovementioned meanings are reacted with sulphonamide derivatives of the general formula (VI)

R

3 -S0 2 -NH-CO-Z (VI) in which

R

3 has the abovementioned meaning and Z represents halogen, alkoxy, aralkoxy or Le A 27 155 3 ;Ii II_ aryloxy, if appropriate in the presence of an acid acceptor and if appropriate in the presence of a diluent, and, if desired, salts are formed by customary methods from the compounds of the formula (I) prepared by process or The new halogenated sulphonylaminocarbonyltriazolinones of the general formula and their salts are distinguished by a powerful herbicidal activity.

Surprisingly, the new compounds of the formula have a considerably better herbicidal action than the known herbicide l-isobutylaminocarbonyl-2-imidazolidinone (isocarbamid), which has a similar structure.

The invention preferably relates to compounds of the formula in which

R

1 represents hydrogen, hydroxyl or amino, or represents C 1

C

6 -alkyl which is optionally substituted by fluorine, chlorine, bromine, cyano, Ci-C 4 -alkoxy,

C

1

-C

4 -alkylcarbonyl or C 1 -C-alkoxy-carbonyl, or represents C 3 -C-alkenyl or C 3

-C

6 -alkinyl, each of which is optionally substituted by fluorine, chlorine and/or bromine, or represents C 3 -Cs-cycloalkyl which is optionally substituted by fluorine, chlorine, bromine and/or Ci-C 4 -alkyl, or represents phenyl-C 1

-C

3 -alkyl which is optionally substituted by fluorine, chlorine, bromine, cyano, nitro, Ci-C 4 alkyl, trifluoromethyl, C 1

-C

4 -alkoxy and/or Cl-C 4 alkoxy-carbonyl, or represents phenyl which is optionally substituted by fluorine, chlorine, bromine, cyano, nitro, Ci-C 4 -alkyl, trifluoromethyl, t I 61 Le A 27 155 4 Cl-C 4 -alkoxy, fluorine- and/or chlorine -subs tituted Cl-C 3 -alkoxy, Cl-C 4 -alkylthio, f luorine- arid/or chlorine- substituted Cl-C 3 -alkylthio, Cl-C 4 -alkylsulphinyl, Cl-C 4 -alkylsulphonyl and/or Cl-C-alkoxycarbonyl, or represents Cl-C.-alkoxy which is optionally substituted by fluorine, chlorine, cyano, C 1

-C

4 alkoxy or Cl-C 4 -alkoxy-c.-rbonyl, or represents C 3

-C

4 alkenyloxy, or represents fluorine-, cyano-, phenyl-, Cl-C 4 -alkoxy- or Cl-C 4 -alkoxy-carbonylsubstituted Cl-C 4 -alkylainino, C 3

-C

6 CYC loalkyl amino, or represents di- Cl-C 4 -alkyl) -amino, R 2 represents fluorine, chlorine, bromine or iodine and R 3 represents the group ,where

R

4

R

4 and R 5 are identical or different and represent hydrogen, fluorine, chlorine, bromine, iodine, nitro, C-C 6 -alkyl (which is optionally substituted by fluorine, chlorine,~ bromine, cyano, carboxyl, C 1

-C

4 -alkoxycarbonyl, Cl-C 4 -alkylainino-carbonyl, di- (C 1

-C

4 -alkyl)ainino-carbonyl, hydroxyl, Cl-C 4 -alkoxy, formyloxy, Cl-C 4 -alkylcarbonyloxy, Cl-C 4 -alkoxy-carbonyloxy, C 1

-C

4 a lkyl amino -c arbonyloxy, Cl-C 4 -alkylthio, Cl-C 4 alkylsulphinyl, C-C 4 -alkylsulphonyl, di- (Cl-C 4 alkyl)-aminosulphonyl, C 3

-C

6 -cycloalkyl or phenyl) or represent C 2

-C

6 -alkenyl (which is optionally substituted by fluorine, chlorine, bromine, cyano, Cl-C 4 -alkoxy-carbonyl, carboxyl or phenyl), or represent C 2

-C,

6 -alkinyl (which is Le A 27 155-5 5 optionally substituted by fluorine, chlorine, brcomine, cyano, C 1 -C,-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-C 4 -alkoxy, Cl-C 4 -alkylthio, CI-C 4 -alkylsulphinyl or C 1

-C

4 -alkylsulphonyl) or represent Cl-C 4 -alkylthio (which is optionally substituted by fluorine, chlorine, bromine, cyano, carboxyl, C-C 4 -alkoxy-carbonyl, Cl-C 4 -alkylthio, Cl-C 4 -alkylsulphinyl or Cl-C 4 -alkylsulphonyl) or represent C 3 -C.-alkenyloxy (which is optionally substituted by fluorine, chlorine, bromine, cyano or Cl-C 4 -alkoxy-carbonyl), or represent

C

2 -C,-alkenylthio (which is optionally substituted by fluorine, chlorine, bromine, cyano, nitro, C 1

-C

3 -alkylthio or Cl-C 4 -alkoxycarbonyl)

C

3

-C

6 -alkinyloxy, C 3 -Cr 6 -alkinylthio or the radical -S(O)P-R 8 where p represents the numbers 1 or 2 and R6 represents Cj-C 4 -alkyl (which is optionally substituted by fluorine, chlorine, bromine, cyano or Cl-C 4 -alkoxy-carbonyl) C 3 -C6alkenyl, C 3

-C

6 -alkinyl, C 1

-C

4 -alkoxy, C 1

-C

4 a lkoxy-C 1

-C

4 -al kyl amino, Cl-C-alkylamino, di- (Cl-C 4 -alkyl) -amino and phenyl, or represents the radical -NHOR where R7 represents Cl-C 12 -alkyl (which is optionally substituted by fluorine, chlorine, cyano, Cl-C-alkoxy, C 1 -C4- Le A 27 155-- 6 alkylthio, C-C 4 -alkylsulphinyl, CI-C 4 alkylsuiphonyl, Cl-C 4 -alkyl-carbonyl, Cl-C 4 -alkoxycarbonyl, C 1

-C

4 -alkyl aminocarbonyl or di- (Cl-C 4 -alkyl) -amninocarbonyl) ,or represents C 3

-C

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

-C

6 alkinyl, C 3 -C.-cycloalkyl, C 3

-C

6 cycloalkyl-Cl-C 2 -alkyl, phenyl-Cl-C 2 alkyl (which is optionally substituted by fluorine, chlorine, nitro, cyano, Cl-C 4 alkyl, Cl-C,-alkoxy or Cl-C 4 -alkoxy-carbcjnyl) or represents benzhydryl, or represents phenyl (which is optionally substituted by fluorine, chlorine, nitro, cyano, Cl-C 4 -alkyl, trifluoromethyl, C 1

-C

4 alkoxy, C 1

-C

2 f luoroalkoxy, 0 1

-C

4 alkylthio, trifluorometiiylthio or

C

1 -C-alkoxycarbonyl)

R

4 and/or R 5 furthermore represent phenyl. or phenoxy, or represent Cl-C-alkylcarbonylamino, C 1

-C

4 alkoxy.-c arbonyl amino, C 1

-C

4 -alkylamino-carbonylamino and di- (Cl-C.4-alkyl) -aiio-carbonylcamino or represent the radical -CO-R where R8 represents C,-C.-alkyl, C,-C.-alkoxy, C 3

C

6 cycloalkoxy, C 3 -C,-alkenyloxy, Cl-C 4 -alkylthio, Cl-C-alkylamino, Cl-C 4 -alkoxyamino, Cj-C-alkoxy-C 1

-C

4 -alkyl -amino or di-(Cl-C4alkyl)-amino (which are optionally Le A 27 155-- 7 substituted by fluorine and/or chlorine), R and/or R 5 furthermore represent trimethylsilyl, thiazolinyl, C,-C 4 -alkylsulphonyloxy or di- (Cl-C 4 -alkyl)-aminosulphonylamino or represent the radical -CH=N-Rg, where R9 is Cl-C 6 -alkyl which is optionally substituted by fluorine, chlorine, cyano, carboxyl, Cl-C 4 -alkoxy, Cl-C 4 -alkylthio, Cl-C 4 -alkylsulphinyl or Cl-C 4 -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 phenyl which is optionally substituted by fluorine, chlorine, bromine, Cl-C 4 -alkyl, Cl-C 4 -alkoxy, trifluoromethyl, trifluoromethoxy or trifluoromethylthio, or represent C 1 -Cr,-alkoxy,

C

3 -C,-alkenoxy, C-C-alkinoxy or benzyloxy, each of which is optionally substituted by fluorine and/or chlorine, or represents amino, C 1

-C

4 -alkylamino, di-(C 1

-C

4 -alkyl)amino, phenylamino, Cl-C -alkyl-carbonylamino, C-C 4 -alkoxy-carbonyl-amino or C 1

-C

4 alkyl-sulphonylamino, or represents phenylsulphonylamino which is optionally substituted by fluorine, chlorine, bromine or methyl, furthermore Le A 27 155 8-

R

1 2

R

3 represents the radical where R1 0

R

1 1

R

10 represents hydrogen or C 1

-C

4 -alkyl,

R

n and R 12 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 alkoxy (which is optionally substituted by fluorine and/or chlorine), carboxyl, C 1 alkoxy-carbonyl, dimethylaminocarbonyl, Ci-C,alkylsulphonyl or di- C-C 4 -alkyl) -aminosulphonyl,; furthermore

R

3 represents the radical R 1 3 I R 1 4 where

R

13 and R" 3 are identical or different and represent hydrogen, fluorine, chlorine, bromine, nitro, cyano, Ci-C 4 -alkyl (which is optionally substituted by fluorine and/or chlorine) or alkoxy (which is optionally substituted by fluorine and/or chlorine); furthermore

R

1

R

3 represents the radical where R16

R'

5 and R' 6 are identical or different and represent hydrogen, fluorine, chlorine, bromine, nitro, cyano, Ci-C4-alkyl (which is optionally substituted by fluorine and/or chlorine), Ci-C 4 -alkoxy 4 e« Le A 27 155 9 c (which is optionally substituted by fluorine and/or chlorine), or represent C 1

-C

4 -alkylthio,

C-C

4 -alkylsulphinyl or Cl-C 4 -alkylsulphonyl (which are optionally substituted by fluorine and/or chlorine), or represent aminosulphonyl, mono- (Ci-C 4 -alkyl) -aminosulphonyl, di-(C 1

-C

4 alkyl)-aminosulphonyl or C 1

-C

4 -alkoxy-carbonyl or dimethylaminocarbonyl; furthermore

R

3 represents the radical R 17 R where

R

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

-C

4 -alkylthio, Ci-C,alkylsulphinyl or Ci-C 4 -alkylsulphonyl (which are optionally substituted by fluorine and/or chlorine), or represent di-(Ci-C 4 -alkyl)-aminosulphonyl; furthermore R1 9

R

3 represents the radical R20 where

R'

1 and R 20 are identical or different and represent hydrogen, fluorine, chlorine, bromine, cyano, nitro, Ci-C 4 -alkyl (which is optionally substituted by fluorine and/or chlorine), CI-C 4 Le A 27 155 10 I alkoxy (which is optionally substituted by fluorine and/or chlorine), C 1

-C

4 -alkylthio,

C-C

4 -alkylsulphinyl or C 1

-C

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

-C

4 -alkoxy-carbonyl or dimethylaminocarbonyl, and A represents oxygen, sulphur or the group N-Z 1 where

Z

i represents hydrogen, C 1

-C

4 -alkyl (which is optionally substituted by fluorine, chlorine, bromine or cyano), C 3

-C

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

C

1

-C

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

R

3 represents the radical

R

2 1

YI

where

R

21 and R 22 are identical or different and represent hydrogen, C 1

-C

4 -alkyl, halogen, Cl-C4-alkoxycarbonyl, C--C 4 -alkoxy or C 1

-C

4 -halogenoalkoxy, Y1 represents sulphur or the group N-R 23 where

R

23 represents hydrogen or Ci-C 4 -alkyl; furthermore represents the radical R26

N~

R

2 4 where Le A 27 155 11 i

R

24 represents hydrogen, C 1

-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 chlorine), dioxolanyl or Cl-C 4 -alkoxy-carbonyl and

R

26 represents hydrogen, halogen or C 1

-C

4 -alkyl; furthermore

R

3 represents one of the groups listed below:

H

3

H

3

C

'NS-Cq N-s^ OCH 2

CF

3 I 02 The invention also preferably relates to sodium Ssalts, potassium salts, magnesium salts, calcium salts, ammonium salts, Ci-C 4 -alkyl-ammonium salts, di-(Cl-C 4 alkyl)-ammonium salts, tri-(Ci-C 4 -alkyl) -ammonium salts,

C

5 or C 6 -cycloalkyl-ammonium salts and di-(C 1

-C

2 -alkyl)benzyl-ammonium salts of compounds of the formula in which R 1

R

2 and R 3 have the meanings indicated above as being preferred.

The invention particularly relates to compounds of the formula in which Le A 27 155 12- R represents hydrogen, or represents C,-C,-alkyl which is optionally substituted by fluorine, cyano, j methoxy or ethoxy, or represents allyl, or represents C 3 -C6-cycloalkyl, or represents phenyl, or represents C,-C-alkoxy, C 3 -C-alkenyloxy, or represents C,-C 3 -alkylaxnino, C 3 -C-cycloalkyl amino, or represents di- (C 1

-C

3 -alkyl) -amino, R 2 represents chlorine or bromine, and

R

3 represents the group 2where R 4 represents fluorine, chlorine, bromine, methyl, 20 25 trifluoromethoxy, 2-chloro-ethoxy, 2-methoxyethoxy-, Cl-C 3 -alkylthio, C 1

-C

3 -alkylsulphinyl, Cl'-C 3 -alkylsulphonyl, dimethylaminosulphonyl, diethylaxninosulphonyl, N-methoxy-N-methylaminosulphonyl, N-methoxyaminosulphonyl, phenyl, phenoxy or C,-C 3 -alkoxy-carbonyl, and

R

5 represents hydrogen, fluorine, chlorine or bromine; furthermore R 3 represents the radical 12

RIO

where R0represents hydrogen, R" represents fluorine, chlorine, bromine, methyl, methoxy, difluoromethoxy, trifluoromethoxy, ethoxy, methoxycarbonyl, ethoxycarbonyl, methylsulphonyl or dixnethylaminosulphonyl, and Le A 27 155 13

R

12 represents hydrogen; furthermore

R

3 represents the radical RO-C 0 where R represents Ci-C 4 -alkyl, or 0 I I RO-C represents the radical

N-N

where R represents Cl-C 4 -alkyl. CH 3 Examples of the compounds according to the invention are listed in Table 1 below cf. also the Preparation Examples.

I I B c t Le A 27 155 14 0

(II

Table 1: Examples of the compounds of the formula (I)

F

Br ClI

COOCH

3 3

F

CH C I 0CF 3 B

SCH

3

C

2

H

5

F

O-CH

2

CH

2 C 1

CH

2

-CH=CH

2 C I Le A27 155 Table 1: (continuation) 2 R 3

COOC

2

H

E 0 0 CH

COOCH

3 ci K CH 2

OCHF

2 2 CH 3 Br CH 2 I COOCH 3 CH 3 B r H 2 0CF 3 0C 2

H

5 C I C

COOCH

3

OCH

3 Cl S0 2

CH

3 a. -CH 2

-CH=CH

2 Cl Le A 27 155 16 Ta

KR

CH

Dle 1: (continuation)

F

3 Cl 3

SO

2

-NCCH

3 2 S02,NHOCH 3

COOC

2

H

CHF

2 0

C

2

H

00 a

C

3

H

7

CH

3 FF "COOCH 3 I I N-y

(COOC

2 9'

CH

3 4 4 Le A 27 155 17 Table 1: (continuation) Rl R 2 N(CH3)2 C I S COOCH3

CF

3 N(CH3)2 F CON (CH3 2 C 1 CH3 S02NH2 CH3 C 1 C ON C H3'2 C I H 3 N,- OCH,-CH -OCH 2 3 Br C> O-CH -CH -Cl 2 2 Cl Br

F

6 4

CH

3 C 1 Le A 27 155 18 Table 1: (continuation)

OCH

3

CH

2 Br 1

CH

3 Br

CH-

3

I

F

N(CH

3 2 Cl

CH

3 ClC/ 3 CH Cl Br Le A 27 155 19 Table 1: (continuation) R I R2

CH

3 C

CH

2 0

CH

3

ICH

3 C- CH 2 0C 2

H

CH

3 S i (CH 3 2 CON (CH 3 2 004.

444

CH

2

-CH=CH

2

COOCH

3

CH$

3 Le A 27 155 20 Table 1: (continuation)

R

1 R 3

OCHF

2

CH

2 -CHBr-CH 2 -Br Br "'CH 2

CH

3 Cl S0 2

NCH

3

(OCH

3

CH

3 Br 2

CH

3

CH

3 Cl 1402

CH

3 F Cl

C

2

H

5 Cl -CH 2 Cl

OCHF

2

C

2

H

5 Br

OCHF

2

OCF

3

C

3

H

7 -n BrCi Le A 27 155 21- Table 1: (continuation) R1 R 2

CH

3

CN

3 SCH (CH 3 2 If, for exa-mple, 2,6-difluoro-phenylsulphonyl isocyanate and 5-bromo-4-ethyl-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:

F

SO-, -N=C=0 0 H-N

N-C

2 N Br F 0 So -NH-CON N-C H F Br *0 4 cIa S 4 Le A 27 155 22 If, for example, 2-methoxy-benzenesulphonamide and 5-chloro-2-chlorocarbonyl-4-methoxy-2 ,4-dihydro-3Hl,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: 0CH 3 2

-NH

2

-HCI

0 C I CO N)N -OCH 3

OCH

3 0 S0 2 NH -CO0*NKN OCH 3 C 1 Tf, for example, 5-bromo-4-dimethylanino-2,4dihydro-3H-l ,2 ,4-triazol-3-one and N-methoxycarbonyl-2trifluoromethyl-benzenesulphonamide are used as starting substances, the course of the reaction in process (c) according to the invention can be outlined by the following equation:

CF

3 0 2 -NH-COOCH3 0 H Ni"N -N (C CH 3 )2 B r

-HOCH

3

CF

3 0 -S2NH- CO'-N1N-N

(CH

3 2 1II N r Le A 27 155 23 Formula (II) provides a general definition of the halogenated triazolinones to be used as starting substances in processes and according to the invention for the preparation of compounds of the formula In formula R 1 and R 2 preferably, or in particular, have those meanings which have already been given above in connection with the description of the compounds of the formula according to the invention as being preferred, or particularly preferred, for R 1 and

R.

2 -xamples of the starting substances of the formula (II) are listed in Table 2 below.

0 HN- N/R 1 R2 (II) Table 2: Examples of the starting substances of the formula (II):

R

l

R

2 H Br

CH

3 Br

C

2

H

5 Br

C

3

H

7 Br

CH(CH

3 2 C1

C

4

H

9 C1

CH

3 C1

C

2

H

5 Ci Br

CH

2

-CH=CH

2 Br Le A 27 155 24- 1 Table 2: (continuation) CH (CH 3 2

CH

3

C

3

H

7

C

2 N (CH 3 )2 NC CH 3 2 NH- CH 3

OCH

3

OCH

3

C

2

H

C

3

H

7 0C 2

H

0C 2

H

C H2 C (CH 3

CH

2

-CH(CCH

3 )2

CH

2

-CH(CCH

3 )2

O-C

3

H

7 -n Le A 27 1-5 Br 25 Table 2: (continuation)

CH

2 -1 CBr C 1

C

2

HS

C

4

H

9 Er

CH-C

2

H

5 Br U11 3 C 'H -C 2

H

5 C 1

CH

3

CH(CH

3 2 C I

CH

2 -CHBr-CH 2 Br Br

CH

2 -CHBr-CH 2 Br Cl Br

CH

3 Cl

CH

3

F

Cl Br Le A 27 155 -2 26 i i r i Table 2: (continuation) -C7)

OC

3

H

7 The starting substances of the formula (II) are known and/or can be prepared by processes known per se (cf. Chem. Ber. 102 (1969), 755-766 and the Preparation Examples).

Formula (III) provides a general definition of the sulphonyl isocyanates also 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 the 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 3 The following may be mentioned as examples of the starting substances of the formula (III): 2-fluoro-, 2- Le A 27 155 27 0MMO T -aun ~aiuPrar~aman*l-- chloro-, 2-bromo-, 2-methyl-, 2-methoxy-, 2-trifluoromethyl-, 2-difluoro-methoxy-, 2-trifluoromethoxy-, 2methylthio-, 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-propoxycarbonyl- and 2isopropoxycarbonyl-phenylsulphonyl isocyanate, 2-fluoro-, 2-chloro-, 2-difluoromethoxy-, 2-trifluoromethoxy-, 2methoxycarbonyl- and 2-ethoxycarbonyl-benzylsulphonyl isocyanate, 2-methoxycarbonyl-3-thienyl-sulphonyl isocyanate, 4-methoxycarbonyl- and 4-ethoxycarbonyl-lisocyanate.

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 according to the invention for the preparation of new compounds of the formula is preferably carried out using diluents. Suitable diluencs Sfor 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, o ligroin, 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, Le A 27 155 28 ketones, such as acetone, methyl ethyl 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 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 150"C, preferably at temperatures between 10 0 C and 80 0

C.

Process according to the invention is generally 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 generally employed per mole of triazolinone of the formula (II).

The reactants can be combined in any desired sequence. The reaction mixture is stirred until the reaction is complete, concentrated, and the crude product which remains in the residue is crystallized using a suitable solvent, such as, for example, diethyl ether.

The product of the formula which is obtained as crystals is isolated by filtration with suction.

Formula (IV) provides a general definition of the triazolinone derivatives to be used as starting substances in process according to the invention for the Le A 27 155 29 preparation of compounds of the formula In formula R 1 and R 2 preferably, or in particular, have those meanings which have 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 1 and

R

2 and Z preferably represents chlorine, Ci-C 4 -alkoxy, benzyloxy or phenoxy, in particular methoxy or phenoxy.

Examples which may be given for the starting substances of the formula (IV) are the compounds of the formula (IV) to be prepared from the compounds of the formula (II) listed in Table 2 and phosgene, methyl chloroformate, benzyl chlorofrmate, phenyl chloroformate or diphenyl carbonate.

The starting substances of the formula (IV) were hitherto unknown.

The new halogenated triazolinone derivatives of the formula (IV) are obtained when triazolinones of the general formula (II) 0

N

(II)

in which

R

1 and R 2 have the abovementioned meanings, are reacted with carbonic acid derivatives of the general 4 4 Le A 27 155 30 formula (XI)

Z-CO-Z

1

(XI)

in which Z has the abovementioned meaning and Z represents a leaving group, such as chlorine, 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 (cf. also the Preparation Examples).

Formula provides a general definition of the sulphonamides also 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 the 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 3 The following may be mentioned as examples of the starting substances of the formula 2-fluoro-, 2chloro-, 2-bromo-, 2-methyl-, 2-methoxy-, 2-trifluoromethyl-, 2-difluoro-methoxy-, 2-trifluoromethoxy-, 2methylthio-, 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-propoxycarbonyl- and 2- Le A 27 155 31 isopropoxycarbonyl-benzenesulphonamide, 2-fluoro-, 2chloro-, 2-difluoromethoxy-, 2-trifluoromethoxy-, 2methoxycarbonyl- and 2-ethoxycarbonyl-phenylmethanesulphonamide, 2-methoxycarbonyl-3-thiophenesulphonamide, 4-methoxycarbonyl- and 4-ethoxycarbonyl-1-methyl- 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 preparation of the new compounds of the formula is preferably carried out using diluents. Suitable diluents for this purpose are virtually all inert organic solvents, for example those which are indicated above for process according to the invention.

Acid acceptors which can be employed in process 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 potassium tert-butylate, furthermore aliphatic, aromatic or heterocyclic amines, for example triethylamine, o trimethylamine, dimethylaniline, dimethylbenzylamine, J0 pyridine, 1,5-diazabicyclo-[4.3.0]-non-5-ene (DBN), 1,8l I Le A 27 155 32 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 Process according to the invention is generally carried out under atmospheric pressure. However, it is also possible to carry ouc the process under increased or reduced pressure.

For carrying out process according to the invention, the specifically required starting substances are generally employed in approximately equimolar amounts. However, it is also possible to use one of the two specifically employed components in a substantial excess. The reactions are generally carried out in a suitable diluent in the presence of an acid acceptor, and the reaction mixture is stirred for several hours at the specifically required temperature. Working-up in process according to the invention is carried out in each case by customary methods.

The halogenated 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 for process according to the invention.

Formula (VI) provides a general definition of the sulphonamide derivatives also to be used as starting substances in process according to the invention for Le A 27 155 33-

J

__11

I

the preparation of compounds of the formula In formula R 3 and Z preferably, or in particular, have those meanings which have already been indicated above in connection with the description of the compounds of the formula or 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. Suitable diluents for this purpose are the same organic solvents which have been mentioned above in connection with the description of process according to the invention.

If appropriate, process is carried out in the presence of an acid acceptor. Suitable acid-binding 15 agents for this purpose are the same which have been mentioned above in connection with the description of process according to the invention.

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 0 C and 60 0

C.

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

For carrying out process according to the invention, the specifically required starting substances are generally employed in approximately equimolar amounts. However, it is also possible to use one of the Le A 27 155 -34 two specifically employed components in a substantial excess. The reactions are generally carried out in a suitable diluent in the presence of an acid acceptor, and the reaction mixture is stirred for several hours at the specifically required temperature. Working-up in process according to the invention is carried out in each case by customary methods.

To convert the compounds of the formula to 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 then be isolated as crystalline products, if necessary after concentration.

The active compounds according to the invention can be used as defoliants, desiccants, agents for destroying broad-leaved plants and, especially, as weedkillers. By weeds, in the broadest sense, there are to be understood all plants which grow in locations where they are undesired. Whether the substances according to the invention act as total or selective herbicides depends essentially on the amount used.

The active compounds according to the invention can be used, for example, in connection with the following plants: Dicotyledon weeds of the Qenera: Sinapis, Lepidium, Galium, Stellaria, Matricaria, Anthemis, Galinsoga, Chenopodium, Urtica, Senecio, Amaranthus, Le A 27 155 35 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.

Monocotyledon cultures of the genera: Oryza, Zea, Triticum, Hordeum, Avena, Secale, Sorghum, Panicum, Saccharum, Ananas, Asparagus and Allium.

However, the use of the active compounds according to the invention is in no way restricted to these genera, but also extends in the same manner to other plants.

The compounds are suitable, depending on the concentration, for the total combating of weeds, for example on industrial terrain and rail tracks, and on paths and squares with or without tree plantings.

Equally, the compounds can be employed for combating weeds in perennial cultures, for example afforestations, decorative tree plantings, orchards, vineyards, citrus groves, nut orchards, banana plantations, coffee plantations, tea plantations, rubber plantations, oil palm Le A 27 155 36 _II plantations, cocoa plantations, soft fruit plantings and hopfields, in ornamental lawns, sports fields and grazing land, and for the selective combating of weeds in annual cultures.

The compounds of the formula according to the invention are particularly suitable for selectively combating monocotyledon and dicotyledon weeds in monocotyledon crops, using the pre-emergence or the postemergence method. They are markedly more effective than, for example, isocarbamid.

To a certain extent, the compounds according to the invention also have a fungicidal action, for example against powdery mildew on vines and against Pyricularia oryzae on rice.

The active compounds can be converted into the customary formulations, such as solutions, emulsions, wettable powders, suspensions, powders, dusting agents, pastes, 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- -ing 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 Le A 27 155 -37suitable in the main: aromatics, such as xylene, toluene, or alkylnaphthalenes, chlorinated aromatics and chlorinated aliphatic 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 butanol or glycol as well as their ethers and esters, ketones, such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents, such as dimethylformamide and dimethyl sulphoxide, as well as water.

As solid carriers there are suitable: for example ammonium salts and ground natural minerals, such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth, and ground synthetic minerals, such as highly disperse silica, alumina and silicates, as solid carriers for granules there are suitable: for example crushed and fractionated natural rocks such as calcite, marble, pumice, sepiolite and dolomite, as well as synthetic granules of inorganic and organic meals, and granules of organic material such as sawdust, coconut shells, maize cobs and tobacco stalks; as emulsifying and/or foamforming 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 ligninsulphite waste liquors and methylcellulose.

Le A 27 155 38 L bn~c 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 pigments, for example iron oxide, titanium oxide and Prussian Blue, and organic dyestuffs, such as alizarin dyestuffs, azo dyestuffs and metal phthalocyanine dyestuffs, and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc.

The formulations in general contain between 0.1 and 95 per cent by weight of active compound, preferably between 0.5 and For combating weeds, the active compounds according to the invention, as such or in the form of their formulations, can also be used as mixtures with known herbicides, finished formulations or tank mixes being possible.

Suitable herbicides for the mixtures are known herbicides, such as, for example, l-amino-6-ethylthio-3- (2,2-dimethylpropyl)-1,3,5-triazine-2,4(lH,3H)-dione (AMETHYDIONE) or N-(2-benzothiazolyl)-N,N'-dimethylurea (METABENZTHIAZURON) for combating weeds in cereals; 4amino-3-methyl-6-phenyl-l,2,4-triazin-5(4H)-one (METAMITRON) for combating weeds in sugar beet, and 4amino-6- (1,1-dimethylethyl)-3-methylthio-l,2,4-triazin- 5(4H)-one (METRIBUZIN) for combating weeds in soya beans; Le A 27 155 39 L furthermore also 2, 4-dichiorophenoiyacetic acid 4-D); 4-(2,4-dichlorophenoxy)-butyric acid 2,4dichlorophenoxypropionic acid 4-DP); 3-isopropyl- 2, 1,.1-benzothiadiazin-4-one 2,2-dioxide (BENTAZONE); methyl 5 ,4-dichlorophenoxy) -2 -nitrobenzoate (BIFENOX); 3, 5-dibromo-4-hydroxy-benzonitrile (BROMOXYNIL); 2chloro-N{ (4 -methoxy- 6-methyl 3,5-triaz in-2-yl) -aminocarbonyl }-benzenesulphonamide (CHILORSULFURON); N, N-dimethyl-N' (3-chloro-4-methylphenyl) -urea (CHLORTOLURON); 4-amino-6-t-butyl-3-ethylthio-1,2,4-triazin-5(4H)-one (ETHIOZIN); -amino- 3, 5-dichloro-6 fluoro-2 -pyridinyl) oxy]-acetic acid or its 1-methylheptyl ester (FLUROXYPYR) ;methyl 2- 5-dihydro-4-methyl-4-( 1-methylethyl) -5-oxo-lH-imidazol-2-yl] -methylbenzoate (IMAZAMETHABENZ); 3,5-diiodo-4-hydroxybenzonitrile (IOXYNIL); N,N-dimethyl-N'-(4-isopropylphenyl)-urea (ISOPROTURON); (2-methyl-4-chlorophenoxy) -acetic acid (MCPA) (4-chloro-2-methylphenoxy) -propionic acid (MCPP); N-methyl-2- 3-benzothiazol-2-yloxy) -acetanilide (MEFENACET); (4-methoxy-6-methyl-1,3,5-triazin-2yl)-amino)-carbonyl]-amino]-sulphonyl}-benzoic acid or its methyl ester (METSULFURON); N- (l-ethylpropyl ,4-dimethyl-2 ,6-dinitroaniline (PENDIMETHALIN) 6-chloro- 3-phenyl-pyridazin-4-yl) S-octyl thiocarbonate

(PYRIDATE);

4-ethylamino-2-t-butylamino-b-met~i jlthio-s-triazine (TERBUTRYNE); methyl 3-[[[[(4-methoxy-6-methyl-1,3,5triazin-2-yl)--amino]-carbonyl]-amino]-sulphonyl]thiophene-2-carboxylate (THIAMETURON) and S- (2,3,3trichloroallyl) N, N-diisopropylthiocarbamate (TRI- Le A 27 155 40 i ALLATE). Surprisingly, some mixtures also show synergistic action.

Mixtures with other known active compounds, such as fungicides, insecticides, acaricides, nematicides, bird repellents, plant nutrients and agents which improve soil structure, are also possible.

The active compounds can be used as such, in the form of their formulations or in the use forms prepared therefrom by further dilution, such as ready-to-use solutions, suspensions, emulsions, powders, pastes and granules. They are used in the customary manner, for example by watering, spraying, atomizing or scattering.

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

They can also be incorporated into the soil before sowing.

The amount of active compound used can vary within a substantial range. It depends essentially on the nature of the desired effect. In general, the amounts used are between 0.01 and 15 kg of active compound per hectare of soil surface, preferably between 0.05 and kg per ha.

The preparation and use of the active compounds according to the invention can be seen from the following examples.

Le A 27 155 41 Preparation Examples Example 1

COOCH

3 0 SO 0NH-CO-NY -NN(CH 3 (Process 2.8 g (17.2 mmol) of 5-chloro-4-dimethylam-no- 2,4-dihydro-3H-1,2,4-triazol-3-one are dissolved in 6 )ml of acetonitrile and 6.6 g (27.4 riol) of 2-xethxycarbonyl-phenylsulphonyl isocyanate, dissolved in 2) ml of acetonitrile, are added to this solution -iith stirring. The reaction mixture is stirred for 6 hour; at 0 C and then concentrated. The residue which remaini is stirred with diethyl ether, and the product obtainer' in crystalline form is isolated by filtration with suct-on.

6.9 g (99 of theory) of 5-chloro-4-dimet'iyl- 1 5 amino-2-(2-methoxycarbonyl-phenylsulphonyl-am.-nocarbonyl) 4-dihydro- 3H-1, 2, 4-triazol- 3-one of mel :ing point 146 0 C are obtained.

Example 2 *C1 0 _S0 2 _NH-CO-N-jKN-N(CH 3 2

CH

3 Br Le A27 155 -42

I

(Process 1.9 g (12.5 mmol) of 1,8-diazabicyclo-[5.4.0]undec-7-ene (DBU) and 2.6 g (12.6 mmol) of 2-chloro-6methyl-benzenesulphonamide are added to a solution of 4.0 g (12.2 mmol) of 5-bromo-4-dimethylamino-2-phenoxycarbonyl-2,4-dihydro-3H-1,2,4-triazol-3-one in 60 ml of acetonitrile. The reaction mixture is stirred for 3 hours at 20'C, then poured into approximately twice the volume of ice-water and then brought to a pH of approximately 2 by adding 2N hydrochloric acid. The mixture is subsequently extracted using methylene chloride, and the organic phase is washed with water, dried with sodium sulphate and filtered. The filtrate is concentrated, the residue is stirred with diethyl ether, and the product which is obtained in crystalline form is isolated by filtration with suction.

g (19 of theory) of 5-bromo-4-dimethylamino-2-( 2 -chloro-6-methyl-phenylsulphonyl-aminocarbonyl)-2,4-dihydro-3H-1,2,4-triazol-3-one of melting point 163 0 C is obtained.

Other examples of the compounds which can be prepared analogously to Examples 1 and 2 and following the general description of the preparation processes according to the invention are those which are listed in Table 3 below.

0 SR3-SO 2 -NH-CO-N -N-R1

S(I)

2 5 So Le A 27 155 43

L

J

Table 3: Preparation examples of the compounds of the formula (I) Ex. R R R 3 Melting point No. 0

C)

COOCH

3 CH 3 4

CH

3 N (CH 3 2 6K 7K 8

C

3

H

7 9

C

3

H

7

COOCH

3 Br Br

COOCH

3

COOCH

3 Br

COOCH

3

COOCH

3 Br

C

COaCH 3 C1 170 173 139 155 148 120 119 Le A-27 155 44 Table 3: (continuation) Melting point Ex. 1 No. R R 0

C)

C1

CH

3 C1 4

CH

3 C1 11 CH 3

CH

3 C1 1 12 Br16

CH

3 C1 13 C1 4 162

OH

3

COOCH

3 *14 C 2

H

5 Br 14

COOCH

3

C

2

H

5 C1 4 161 o C1 0 30 16 C 2

H

5 Br "'161

OH

3 0 00 Le A 27 155 45 Table 3: (continuation) Ex.

NO.

R

1

R

2 Melting point (0 C)

C

2

H

5

-K

C 1 C1

CH

3 0CF 3

OCF

3 Br 5-

OCF

3

OCF

3 Br C5

OCF

3

OCF

3 Br

CH

3 156 142 134 144 169 122 133 174

CH-

3 22

C

2

H

5

C

2

H

5 24 Cl 1~

COOCH

3 00 Le A 27 155 -4 46 I Starting substances of the formula (II): Example (II-l) o H-N-N-NN(

CH

3 2 Stage 1:

O

H-NLXN,N(CH

3 2 3 2 856 g (4.0 mol) of diphenyl carbonate are dissolved in 588 g of ethylene chloride. With water-cooling, 245 g (4.0 mol) of dimethylhydrazine (98 are added dropwise, the mixture is then warmed slowly, and, after i0 4 hours, stirring is continued at After the mixture has cooled to 20 0 C, 200 g mol) of hydrazine hydrate are added dropwise and stirring is continued for 12 hours. The mixture is warmed to 70-80 0 C, and, after approximately 1 hour, stirred again. When cold, the solution is distilled in vacuo, during which process ethylene chloride and water are removed (bottom temperature in the end 100'C). The above phenolic dimethyl carbodihydrazide solution is added dropwise in the course of 90 minutes at reflux tempera- 20 ture (approximately 102 0 C) to 424 g (4.0 mol) of trimethyl orthoformate. After the methanol which has formed has been removed by distillation, phenol is distilled off in vacuo, and at a head temperature of 85-105"C, 282 g of Le A 27 155 47 L product mixture are subsequently obtained. This mixture is boiled with 600 ml of acetone and, after filtration at boiling temperature, the filtrate is cooled. The product which is obtained during this process in crystalline form is isolated by filtration with suction.

71 g (14 of theory) of 4-dimethylamino-2,4dihydro-3H-1,2,4-triazol-3-one of melting point 127"C are obtained.

Stage 2: 0 H-N-

N(CH

3 2

B

18. 7 mol) of bromine are added with icecooling in Louu B of 2 hours to a stirred mixture of 15.0 g (u.117 mo. of 4-dimethylamino-2,4-dihydro-3H- 1,2,4-triazol-3-one, 4.7 g (0.117 mol) of sodium hydroxide and 150 ml of water. The product which is obtained in crystalline form is subsequently isolated by filtration with suction.

19.6 g (81 of theory) of 5-bromo-4-dimethylamino-2,4-dihydro-3H-l,2,4-triazol-3-one of melting 163 C are obtained.

Le A 27 155 48 i-- Example (II-2) 0 H-NiJ' N/N(CH 3 )2 1 A mixture of 6.0 g (0.029 mol) of 5-bromo-4dimethylamino-2,4-dihydro-3H-1,2,4-triazol-3-one and 200 ml of concentrated hydrochloric acid is refluxed for 3 hours. The mixture is then concentrated, the residue is taken up in a little water, the mixture is rendered neutral using sodium hydrogen carbonate, and the product which is obtained in crystalline form is isolated by filtration with suction. The filtrate is extracted using ethyl acetate, the crystalline product which has previously been isolated is added to the organic phase, and the latter is dried with sodium sulphate and filtered.

The filtrate is concentrated, the residue is triturated with diethyl ether, and the product which is obtained in crystalline form during this process is isolated by filtration with suction.

3.1 g (66 of theory) of 5-chloro-4-dimethylamino-2,4-dihydro-3H-l,2,4-triazol-3-one of melting point 158"C are obtained.

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

Le A 27 155 49 0

R

2 (I I) Table 4: Example No.

Preparation examples of the compounds of the formula (II) R1R 2 Melting point 0

C)

11-3 1 1-4 1 1-5 J 1-6 11-7 11-8 11-9 11-10

-KH

C

3

H

7

C

2

H

5

C

2

H

5 C H 2 C H 2 137 9 8 121 91 142 1 12 I I Le--A 27 155 50 Starting substances of the formula (IV): Example (IV-1) 0 I I -O-CO-N-'N-N(CH3)2 N Br g (33.8 mmol) of 5-bromo-4-dimethylamino-2,4dihydro-3H-l,2,4-triazol-3-one are taken up in 100 ml of water and 100 ml of methylene chloride, and 0.2 g of tetrabutylammonium bromide and 1.5 g (37.5 mmol) of sodium hydroxide are added. 5.9 g (37.7 mmol) of phenyl chloroformate are then added dropwise at 20 0 C with vigorous stirring, and the reaction mixture is stirred for a further 12 hours at 20 0 C. The organic phase is separated off, washed with water, dried with sodium sulphate and filtered. The filtrate is concentrated, the residue is stirred with diethyl ether, and the product which is obtained in crystalline form in this process is isolated by filtration with suction.

8.7 g (79 of theory) of 5-bromo-4-dimethylamino-2-phenoxycarbonyl-2,4-dihydro-3H-l,2,4-triazol-3one of melting point 136 0 C are obtained.

Use Examples: In the following Use Examples, the known herbicide isocarbamid of formula below is used as comparison substance: Le A 27 155 51 Y" F7 HNr(NCO-NH-CH 2 CH (CH 3 )~2 0 (disclosed in BE 737,449; DE 1,795,117).

Le A,27 155 52 F I Example A 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 plants are sown in normal soil and, after 24 hours, watered with the preparation of the 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 denote: 0 no action (like untreated control) 100 total destruction In this test, for example the compounds of Preparation Example 3, 6 and 7 show a clearly suerior activity cormpared with the prior art.

Le A 27 155 53

L-

I_ I~ lilVCPLPIII~----- Example B 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 desired per unit area. The concentration of the spray liquor is so chosen that the particular amounts of active compound desired are applied in 2,000 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, for example the compounds of Preparation Example 3, 6 and 7 show a clearly superior activity compared with the prior ait.

Le A 27 155 54

Claims

1. Halogenated sulphonylaminocarbonyltriazolinores of the general formula (I) 0o R 3 -S0 2 -NH-CO-N N-R 1 (I) I in which R represents hydrogen, hydroxyl or amino, or repre- sents an optionally substituted radical from the series comprising alkyl, alkenyl, alkinyl, cyclo- alkyl, aralkyl, aryl, alkoxy, alkenyloxy, alkyl- amino, cycloalkylamino and dialkylamino, R 2 represents halogen and R 3 represents an optionally substituted radical from the series comprising alkyl, aralkyl, aryl and heteroaryl, as well as salts of compounds of the formula

2. Halogenated sulphonylaminocarbonyltriazolnones of the general formula (I) according to claim 1. in which R represents hydrogen, hydroxyl or amino, or repre- S° sents CI-C-alkyl which is optionally substituted by fluorine, chlorine, bromine, cyano, Ci-C 4 -alkoxy, o Ci-C4-alkylcarbonyl or Ci-C,-alkoxy-carbonyl, or represents C 3 -C 6 -alkenyl or C 3 -C 6 -alkinyl, each of which is optionally substituted by fluorine, chlor- ine and/or bromine, or represents C 3 -C 6 -cycloalkyl which is optionally substituted by fluorine, chlor- ine, bromine and/or CI-C 4 -alkyl, or represents phenyl-Ca-C 3 -alkyl which is optionally substituted by fluorine, chlorine, bromine, cyano, nitro, Le A 27 155 alkyl, trifluoromethyl, C,-C,-alkoxy and/or C 1 -C 4 alkoxy-carbonyl, or represents phenyl which is optionally substituted by fluorine, chlorine, bromine, cyano, nitro, Cl-C 4 -alkyl, trifluoromethyl, Cl-C 4 alkoxy, fluorine- and/or chlorine- substituted CI-C.-alkoxy, Cl-C,-alkylthio, fluorine- and/or chlorine- substituted Cl-C 3 -alkylthio, C,-C 4 -alkylsul- phinyl, Cl-C-alkylsulphonyl and/or C,-C-alkoxy- carbonyl, or represents Cl-C 6 -alkoxy which is option- ally substituted by fluorine, chlorine, cyano, C 1 -C 4 alkoxy or Cl-C 4 -alkoxy-carbonyl, or represents C 3 -C 4 alkenyloxy, or represents fluorine-, cyano-, phenyl-, C 1 -C 4 -alkoxy- or C,-C,-alkoxy-carbonyl- substituted C 1 -C 4 -alkylamino, C 3 -C.-cyc loal kyl amino, or represents di- (C,-C 4 -alkyl -amino, R 2 represents fluorine, chlorine, bromine or iodine and R 3 represents the group ,where R 4 R 4 and R'5 are identical or different and represent hydrogen, fluorine, chlorine, bromine, iodine, nitro, C,-C.-alkyl (which is optionally substi- tuted by fluorine, chlorine, bromine, cyano, carboxyl, Cl-C 4 -alkoxycarbonyl, C,-C 4 -alkyl- ainino-carbonyl, di- (Cl-C-alkyl amino-carbonyl, hydroxyl, Cl-C-alkoxy, formyloxy, C-C 4 -alkyl- carbonyloxy, Cl-C 4 -alkoxy-carbonyloxy, C 1 -C4- alkylamino-carbonyloxy, C-C 4 -alkylthio, C 1 -C 4 alkylsulphinyl, Cl-C 4 -alkylsulphonyl, di- (C 1 -C 4 alkyl) -aminosulphonyl, C 3 -C 6 cycloalkyl or phenyl), or represent C 2 -C,-alkenyl (which is optionally substituted by fluorine, chlorine, bromine, cyano, Cl-C 4 -alkoxy-carbonyl, carboxyl or phenyl) or represent C 2 -C 6 -aJlkinyl (which is Le. A27 155 .56- optionally substituted by fluorine, chlorine, bromine, cyano, C,-C 4 -alkoxy-carbonyl, carboxyl or phenyl), or represent Cl-C4-alkoxy (which is optionally substituted by fluorine, chlorine, bromine, cyano, carboxyl, C,-C,-alkoxy-carbonyl, Cl-C 4 -alkoxy, Cl-C-alkylthio, C-C 4 -alkyl- sulphinyl or r2-C-alkylsulphonyl) or represent C-C 4 -alkylthio (which is optionally substituted by fluorine, chlorine, bromine, cyano, car- boxyl, Cl-C-alkoxy-carbonyl, C,-C 4 -alkylthio, C,-C 4 -alkylsulphinyl or Cl-C-alkylsulphonyl) or represent C 3 -C-alkenyloxy (which is optionally substituted by fluorine, chlorine, bromine, cyano or C 1 -C 4 -alkoxy-carbonyl), or represent C 2 -C-alkenylthio (which is optionally sub- stituted by fluorine, chlorine, bromine, cyano, nitro, C,-C 3 -alkylthio or C,-C 4 -alkoxycarbonyl), C 3 -C-alkinyloxy, C 3 -C-alkinylthio or -the radical where p represents the numbers 1 or 2 and R 6 represents C 1 C-alkyl (which is optionally substituted by fluorine, chlorine, brom- ine, cyano or C,-C,-alkoxy-carbonyl) C 3 -C 5 alkenyl, C 3 -C,.-alkinyl, C 1 -C 4 -alkoxy, C 1 -C 4 alkoxy-CI-C 4 -alkylai'nino, C,-C-alkylamino, di- (C,-C-alkyl) -amino and phenyl, or represents the radical -NI-bR where R7 represents C,-C, 2 -alkyl (which is optionally substituted by fluorine, chlorine, cyano, Cl-C,-alkoxy, CI-C 4 Le A 27 155 57 alkylthio, Cl-C 4 -alkylsulphinyl, C 1 -C 4 alkylsuiphonyl, Cl-C-alkyl-carbonyl, C,-C-alkoxycarbonyl, C,-C 4 -alkylamino- carbonyl or di- (C,-C,-alkyl) -ainfo- carbonyl) or represents C 3 -Ce-alkenyl (which is optionally substituted by fluorine, chlorine or bromine), C 3 alkinyl, C 3 -C 6 -cycloalkyl, C 3 -C 8 cycloalkyl-C 1 -C 2 -alkyl, phenyl-Cl-C.- alkyl (which is optionally substitu- ted by fluorine, chlorine, nitro, cyano, C,-C,-alkyl, C,-C 4 -alkoxy or C,-C 4 -alkoxy-carbonyl) or represents benzhydryl, or represents phenyl (which is optionally substituted by fluorine, chlorine, nitro, cyano, Cl-C 4 -alkyl, trifluoromethyl, alkoxy, C,-C-f luoroalkoxy, CI-C 4 oalkylthio, trifluoromethylthio or Cl-C-alkoxycarbonyl), o R 4 and/or R 5 furthermore represent phenyl or phenoxy, or represent CI-C- alkyl carbonyl amino, C 1 alkoxy-c arbonyl amino, Cl-C 4 -alkylaxino-carbonyl- amino and di- (Cl-C 4 -alkyl) -amino-carbonyl amino or represent the radical -CO-R8, where Re represents Cl-C-alkyl, CI-C 6 -alkoxy, C3-C,- cycloalkoxy, C 3 -C-alkenyloxy, Cl-C-alkyl- thio, Cl-C 4 -alkylamino, C,-C-alkoxyamino, CIC-alkoxy-C 1 -C 4 alkyl -amino or di- (C 1 -C4- alkyl)-amino (which are optionally Le A 27 155 58 substituted by fluorine and/or chlorine), R 4 and/or R 5 furthermore represent trimethylsilyl, thiazolinyl, C 1 -C 4 -alkylsulphonyloxy or di- (C 1 -C 4 -alkyl)-aminosulphonylamino or represent the radical -CH=N-R 9 where Re is CI-C 6 -alkyl which is optionally substi- tuted by fluorine, chlorine, cyano, carboxyl, CI-C4-alkoxy, Ci-C 4 -alkylthio, C-C 4 -alkylsulphinyl or C,-C-alkylsul- phonyl, 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 phenyl which is optionally substituted by fluorine, chlorine, brom- ine, C 1 -C 4 -alkyl, Cl-C4-alkoxy, trifluoro- methyl, trifluoromethoxy or trifluoro- methylthio, or represent Ci-C 6 -alkoxy, C 3 -C6-alkenoxy, C 3 -C 6 -alkinoxy or benzyloxy, each of which is optionally substituted by fluorine and/or chlorine, or represents amino, Ci-C-alkylamino, di-(Ci-C 4 -alkyl)- amino, phenylamino, Ci-C,-alkyl-carbonyl- amino, Ci-C 4 -alkoxy-carbonyl-amino or Ci-C,- alkyl-sulphonylamino, or represents phenylsulphonylamino which is optionally substituted by fluorine, chlorine, bromine or methyl, furthermore Le A 27 155 59 L R 12 R 3 represents the radical C H where 1 0 R 1 1 R 10 represents hydrogen or Ci-C 4 -alkyl, R1 and R 12 are identical or different and represent hydrogen, fluorine, chlorine, bromine, nitro, cyano, Ci-C 4 -alkyl (which is optionally sub- stituted by fluorine and/or chlorine), C 1 alkoxy (which is optionally substituted by fluorine and/or chlorine), carboxyl, Ci-C,- alkoxy-carbonyl, dimethylaminocarbonyl, CI-C 4 alkylsulphonyl or di-(Ci-C 4 -alkyl)-amino- sulphonyl,; furthermore R 3 represents the radical R 1 3 R 1 4 where R 13 and R" 1 are identical or different and represent S 15 hydrogen, fluorine, chlorine, bromine, nitro, cyano, C 1 -C,-alkyl (which is optionally substi- tuted by fluorine and/or chlorine) or CI-C,- alkoxy (which is optionally substituted by fluorine and/or chlorine); furthermore R 3 represents the radical -where R 1 6 R 15 and R 16 are identical or different and represent hydrogen, fluorine, chlorine, bromine, nitro, cyano, Ci-C 4 -alkyl (which is optionally substi- S 25 tuted by fluorine and/or chlorine), C 1 -C 4 -alkoxy Le A 27 155 60 L (which is optionally substituted by fluorine and/or chlorine), or represent Ci-C 4 -alkylthio, C-C 4 -alkylsulphinyl or Ci-C4-alkylsulphonyl (which are optionally substituted by fluorine and/or chlorine), or represent aminosulphonyl, mono-(Ci-C4-alkyl)-aminosulphonyl, di-(CI-C 4 alkyl)-aminosulphonyl or C 1 -C 4 -alkoxy-carbonyl or dimethylaminocarbonyl; furthermore R represents the radical R 1 7 R 1 8 where R 17 and R 18 are identical or different and represent hydrogen, fluorine, chlorine, bromine, Ci-C,- alkyl (which is optionally substituted by fluorine and/or bromine), Ci-C 4 -alkoxy (which is optionally substituted by fluorine and/or chlorine), or represent Ci-C 4 -alkylthio, Ci-C,- alkylsulphinyl or C,-C,-alkylsulphonyl (which are optionally substituted by fluorine and/or chlorine), or represent di-(Ci-C,-alkyl)-amino- sulphonyl; furthermore R19 R 3 represents the radical R 20 where R 1 and R 20 are identical or different and represent hydrogen, fluorine, chlorine, bromine, cyano, nitro, Ci-C 4 -alkyl (which is optionally sub- stituted by fluorine and/or chlorine), Ci-C 4 Le A 27 155 61 L I alkoxy (which is optionally substituted by fluorine and/or chlorine), Ci-C,-alkylthio, C-C 4 -alkylsulphinyl or Cl-C4-alkylsulphonyl (which is optionally substituted by fluorine and/or chlorine), di-(C 1 -C 4 -alkyl)-amino- sulphonyl, C-C 4 -alkoxy-carbonyl or dimethyl- aminocarbonyl, and A represents oxygen, sulphur or the group N-Z 1 where Z 1 represents hydrogen, Ci-C4-alkyl (which is optionally substituted by fluorine, chlorine, bromine or cyano), C 3 -C 6 -cyclo- alkyl, benzyl, phenyl (which is optionally substituted by fluorine, chlorine, bromine or nitro), Cl-C4-alkylcarbonyl, Ci-C 4 alkoxy--carbonyl or di-(Ci-C 4 -alkyl)-amino- carbonyl; furthermore R 3 represents the radical R21 Y1 where R 21 and R 22 are identical or different and represent hydrogen, C,-C,-alkyl, halogen, Ci-C 4 -alkoxycar- bonyl, Ci-C,-alkoxy or C 1 -C 4 -halogenoalkoxy, Y1 represents sulphur or the group N-R 23 where R 23 represents hydrogen or Ci-C 4 -alkyl; furthermore R 3 represents the radical 26 R 2 4 where Le A 27 155 62 1 R 2 represents hydrogen, C 1 -C4-alkyl, benzyl, py,7idyl, quinolinyl or phenyl, 25 represents hydrogen, halogen, cyano, nitro, C,-C,-alkyl (which is optionally substituted by fluorine and/or chlorine), C 1 -C 4 -alkoxy (which is optionally substituted by fluorine and/or chlorine) dioxolanyl or Cl-C.-alkoxy-carbonyl and 2 6 represents hydrogen, halogen or Cl-C,*-alkyl; furthermore R 3 represents one of the groups listed below: H 3 c CC 02-CH H 3 C 5 ~NCH 2 C F 3 0 0 as well as salts or comipountds or thie formnula

3. Halogciiatcd sul phoinvla~inocarbonvltiazoclinionies of the genieral for-mula (I) accor-dinig to claimi 1, in whichi R represents hydrogen, or represents CI-C,-alkyl which is optionally substituted by fluorine, cyano, methoxy or ethoxy, or represents allyl, or repre- sents C 3 -CO-CYCloalkyl, or represents phenyl, or represents C,-C,-alkoxy, C 3 -C-alkenyloxy, or repre- sents Cl-C 3 -alkylamnino C 3 -C-cycloalkylamnino, or represents di-(Cj-C-alkyl) -amnino, R2 represents chlorine or bromine, and Le A 27 155 63 .63. R 3 represents the group where R' represents fluorine, chlorine, bromine, methyl, trifluoromethyl, methoxy, difluoromethoxy, trifluoromethoxy, 2-chloro-ethoxy, 2-methoxy- ethoxy, C-C 3 -alkylthio, C-C 3 -alkylsulphinyl, C,-C 3 -alkylsulphonyl, dimethylaxninosulphonyl, diethylaninosuiphonyl, N-methoxy-N-methylamino- suiphonyl, N-methoxyaininosulphonyl, phenyl, phenoxy or C 1 -C 3 -alkoxy-carbonyl, and R represents hydrogen, fluorine, chlorine or bromine; furthermore R 3 represents the radical -C12 RIO where R0 represents hydrogen, R 11 represents fluorine, chlorine, bromine, methyl, methoxy, difluoromethoxy, trifluoromethoxy, ethoxy, methoxycarbonyl, ethoxycarbonyl, niethylsuiphonyl or dimethylaminosulphonyl, and R12 Bpresents hydrogen; R 3 represents the radical RD-C S where R represents C 1 -C 4 -alkyl, or represents the radical where R represents CI-C 4 -alkyl. as well as ,,alts of compounds of the formnula 0 11 RD C- Le A.27 15564 -64-

4. Process for the preparation of halogenated sulphonylaminotriazolinones of the general formula (1) 0 (II in which R' represents hydrogen, hydroxyl or amino, or repre- sents an optionally substituted radical from the series comprising alkyl, alkenyl, alkinyl, cyclo- alkyl, aralkyl, aryl, alkoxy, alkenyloxy, alkyl- amino, cycloalkylamino and dialkylamino, R 2 represents halogen and JR 3 represents an optionally substituted radical from the series comprising alk-yl, aralkyl, aryl and heteroaryl, characterized in that a) halogenated triazol.Lnones of the general formula 0 in which R' and JR' have the meanings mentioned above are reacted with sulphonyl isocyanates of the general formula (III) R 3 _-S0 2 -N=C=O(I) in which JR 3 has the meaning mlentioned above, if appropriate in the Presence of a diluent, or in that Le A27 155 A b) halogenated triazolinone derivatives of the general formula (IV) Z-CO-N -N-R 1 (IV) N=-kR2 in which R 1 and R 2 have the meanings mentioned above and Z represents halogen, alkoxy, aralkoxy or aryloxy are reacted with sulphonamides of the general formula (V) R 3 -S0 2 -NH 2 (V) in which R 3 has the meaning mentioned above, if appropriate in the presence of an acid acceptor and if appropriate in the presence of a diluent, or in that c) halogenated triazolinones of the general formula (II) 0 HN N-R 1 (II) I- 2 in which R 1 and R 2 have the meanings mentioned above are reacted with sulphonamide derivatives of the general formula (VI) Le A 27 155 -66- 0301p:mmb 67 R -SO 2 -NH-CO-Z (VI) in which R has the meaning mentioned above and Z 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 desired, salts are formed by customary methods from the compounds of the formula prepared by process or Herbicidal agents, characterized in that they contain at least one halogenated sulphonylaminocarbonyltriazolinone of the formula according to claim 1 or 2, together with a herbidically acceptable carrier diluent or adjunct.

6. A method for combatting undesired plant growth by the administration of an effective dose of at least one compound as defined in claims 1 or 2 as active ingredient on its own or together with a suitable carrier or in the form of a herbicidal agent according to claim

7. Method of combating weeds, characterized in that halogenated sulphonylaminocarbonyltriazoninones of the general formula according to Claim 1 or 4 are allowed to act on the weeds or their environment.

8. Process for the preparation of herbicidal agents, characterized in that halogenated sulphonylaminocarbonyl- traizolinones of the general formula according to Claim 1 or 4 are mixed with extenders and/or surface-active agents.

9. Halogenated triazolinones of the general formula (IV) 0 Z-CO-N N-R1 (IV) N -1R 2 T~Z pj 0301p:mmb 68 in which 1 R represents hydrogen, hydroxyl or amino, or repre- sents an optionally substituted radical from the series comprising alkyl, alkenyl, alkinyl, cycloalkyl, aralkyl, aryl, alkoxy, alkenyloxy, alkylamino, cycloalkylamino and dialkylamino, 2 R represents halogen and Z represents halogen, alkoxy, aralkoxy or aryloxy. DATED this 10th day of February, 1992. BAYER AKTIENGESELLSCHAFT By Its Patent Attorneys DAVIES COLLISON CAVE s, L