AU664780B2

AU664780B2 - Substituted triazolinones

Info

Publication number: AU664780B2
Application number: AU51106/93A
Authority: AU
Inventors: Kurt Findeisen; Klaus Konig; Karl-Heinz Linker; Klaus-Helmut Muller; Hans-Joachim Santel; Otto Schallner; Robert R Schmidt
Original assignee: Bayer AG
Current assignee: Bayer AG
Priority date: 1992-10-12
Filing date: 1993-10-04
Publication date: 1995-11-30
Anticipated expiration: 2013-10-04
Also published as: WO1994009012A1; DE4234306A1; BR9307225A; AU5110693A; CA2146661A1; EP0663917A1; JPH08505837A; RU95113591A

Description

OPI DATE 09/05/94 APPLN. ID 51106/93 AOJP QATE,,21/07/94 PCT NUMBER PCT/EP93/02705 AU9351 106 (51) Internationale Patentkilassifkation 5 Internationale Vcr6ffentlichungsnummer: WNO 94/09012 C07F 7/08, 7/18, AO1N 55/00 Al (43) Internationales Ver6ffentlichungsdatumn: 28. April 1994 (28.04.94) (21) Interuationales Aktenzeichen: PCT/EP93/02705 (81) Bcstimmungsstaaten: AU, BR, BY, CA, CZ, RU, JP, KR, KZ, NZ, RU, SK, UA, US, europflisches Patent (AT, (22) IAnternationales Anmeldedatuin: 4. Oktober 1993 (04.10.93) BE, CR, DE, DK, ES, FR, GB, GR, IE, IT, LU, MC, NL, PT, SE).

Priori tftsdaten: P 42 34 306.2 12. Oktober 1992 (12.10.92) DE Veriiffentlicht Alit internationalem Recherchenbericlil.

(71) Anmelder (Iir alle Bestdmrn ngsstaazen ausser US): BAYE k n pi AKTI ENGESELLSCHAFT [DE/DE]; D-5 1368 Leverkusen (DE), (72) Erfinder; und Erlinder/Anmelder (nurfiir US) FINDEISEN, Kurt [DE/ DE]; Dfinfelder Strasse 28, D-5 1375 Leverkusen (DE).

LINKER, Karl-Heinz [DE/DE]; Albert-Schweizer- Strasse 3, D-51377 Leverkusen SCHALLNER, Otto Noldeweg 22, D-40789 Monheim (DE).

MULLER, Klaus-Relmut [AT/DE]; Solfstrasse 55, D- 40593 D~sseldorf KONIG, Klaus [DE/DE]; Zum, Hahnberg 40, D-51519 Odenthal SANTEL, Hans- Joachim [DE/DE]; GOfnstrasse 9a, D-51371 Leverkusen SCRMIDT, Robert, R. [DE/DE]; Im Waidwinkel 110, D-5 1467 Bergisch-Gladbach (DE).

(54) Title: SUBSTITUTED TRIAZOLINONES (54) Bezeichnung: S UBSTITUIERTE TRIAZOLINONE IRt

R

1~ 2 X '-NHA-Si-R 13

R

R R!

I

"'N

R!

(57) Abstract The invention relates to novel substituted triazolinones of general formula where Ret is a heterocycle of formula or and R 1

R

2

R

3 A, X 1

R

4

R

5

R

6

R

7 and X2 have the meanings given in the description, several processes for their production and their use as herbicides.

(57) Zusamnmenfassung Die Erfindung betrifft neue substituierte Triazolinone der allgemneinen Formel in der Het for einen Reterocyclus der Format, oder staht, und R1, R0 2

R

3 A, X I, R 4

R

5

R

6

R

7 und X2 die in der Beschreibung angegebenen Bedeutungen haben, mebrere Verfahren zu ibrer Herstellung und ihre Verwendung als Rerbizide.

4Ie BAYER AKIENGESELLSCHAFT Konzemverwaltung RP Patente Konzem 51368 Leverkusen Substituted triazolinones The invention relates to novel substituted triazolinones, to a number of processes for their preparation and to their use as herbicides.

It is known that certain substituted triazolinones, such as, for example, the compound 2-methyl-3- dimethylamino- 1- [N-(2,2-dimethyl- 1-propyl)aminocarbonyl]- 1,2,4-triazolin-5-one, possess herbicidal properties (cf. e.g. EP 431 390).

However, the herbicidal activity of these previously known compounds with respect to problem weeds, and their tolerance by important crop plants, is not completely satisfactory in all areas of application.

Novel substituted triazolinones have been found of the general formula (I) I 2 1 X ',8 in which Het represents a heterocycle of the formula Le A 29 399-PCT R R R I I

R

1

R

2 and R 3 independently of one another each represent halogen, alkyl, alkenyl, alkinyl or alkoxy or represent in each case optionally substituted arylalkyl, aryl or aryloxy, A represents a divalent alkanediyl radical, and X' represents oxygen or sulphur, where

R

4 represents hydrogen, halogen, cyano or nitro or represents optionally substituted alkyl, or represents alkenyl, alkinyl, halogenoalkenyl, halogenoalkinyl, alkoxy, alkylthio, alkylsulphinyl, alkylsulphonyl or alkoxycarbonyl, or represents in each case optionally substituted cycloalkyl, aryl or aryloxy, or represents a radical of the formula

R

5 represents hydrogen or cyano, or represents optionally substituted alkyl, or represents alkenyl, alkinyl, alkoxy, alkoxycarbonyl or aminocarbonyl, or represents amino, N-alkylamino, N,Ndialkylamino or alkylideneimino, or represents in each case optionally substituted cycloalkyl, aryl or aryloxy,

R

6 represents alkyl, alkoxy or alkylthio, or represents a radical of the Le A29 399-PCT -2-

R

formula _1

R

7 represents alkyl or cycloalkyl,

R

8 and R 9 either independently of one another each represent hydrogen, alkyl, alkenyl, alkinyl or cycloalkyl or represent in each case optionally substituted arylalkyl or aryl, or, together with the nitrogen atom to which they are attached, represent an optionally substituted heterocycle, R1 0 and R" either independently of one another each represent alkyl, alkenyl, alkinyl, halogenoalkyl, halogenoalkenyl, halogenoalkinyl, alkoxyalkyl, alkoxy, cycloalkyl or cycloalkylalkyl or represent in each case optionally substituted aryl, arylalkyl or heteroaryl, or, together with the nitrogen atom to which they are attached, represent an optionally substituted heterocycle, and

X

2 represents oxygen or sulphur.

The compounds of the formula-(I) may if appropriate, depending on the nature of the substituents, be present as geometrical and/or optical isomers or isomer mixtures of different composition. Both the pure isomers and the isomer mixtures are claimed according to the invention.

It has furthermore been found that the novel substituted triazolinones of the general formula (I)

R

I R X -A-Si-R

(I)

13

R

Le A 29 399 -3in which Het represents a heterocycle of the foimula R R! R! or Rp7 I

I

R

4 represents hydrogen, halogen, cyano or nitro or represents optionally substituted alkyl, or represents alkenyl, alkinyl, halogenoalkenyl, halogenoalkinyl, alkoxy, alkylthio, alkylsulphinyl, alkylsulphonyl or alkoxycarbonyl, or represents in each case optionally substituted cycloalkyl, aryl or aryloxy, or represents a radical of the formula 'R9

R

5 represents hydrogen or cyano, or represents optionally substituted alkyl, or represents alkenyl, alkinyl, alkoxy, alkoxycarbonyl or aminocarbonyl, or represents amino, N-alkylamino, N,Ndialkylamino or alkylideneimino, or represents in each case optionally substituted cycloalkyl, aryl or aryloxy, Le A 29 399 -4-

R

6 represents alkyl, alkoxy or alkylthio, or represents a radical of the

RE

formula

R

7 represents alkyl or cycloalkyl,

R

8 and R 9 either independently of one another each represent hydrogen, alkyl, alkenyl, alkinyl or cycloalkyl or represent in each case optionally substituted arylalkyl or aryl, or, together with the nitrogen atom to which they are attached, represent an optionally substituted heterocycle,

R

1 and R" either independently of one another each represent alkyl, alkenyl, alkinyl, halogenoalkyl, halogenoalkenyl, halogenoalkinyl, alkoxyalkyl, alkoxy, cycloalkyl or cycloalkylalkyl or represent in each case optionally substituted aryl, arylalkyl or heteroaryl, or, together with the nitrogen atom to which they are attached, represent an optionally substituted heterocycle, and

X

2 represents oxygen or sulphur, are obtained if a) 1-chloro(thio)carbonyltriazolinones of the formula (II) xL.C.C (II) in which Het and X' have the meanings given above Le A 29 399 are reacted with amines of the formula (III)

R

I 2 )N-A-Si--R m) in which R R 2

R

3 and A have the meanings given above, optionally in the presence of a diluent and optionally in the presence of a reaction auxiliary, or if b) 1-unsubstituted triazolinones of the formula (IV) Het-H (IV) in which Het has the meaning given above are reacted with iso(thio)cyanates of the formula (V)

R

X=C=N-A-Si-R

(V)

13

R

in which

R

2

R

3 A and X' have the meanings given above, optionally in the presence of a diluent and optionally in the presence of a reaction auxiliary.

-6- Finally it has been found that the novel substituted triazolinones of the general formula possess herbicidal properties.

SSurprisingly, the substituted triazolinones according to the aivention, of the general formula display a considerably improved herbicidal activity with respect to problem weeds, while at the same time being tolerated to a markedly increased extent by important crop plants, in comparison with the substituted triazolinones known from the prior art, such as, for example, the compound 2methyl-3- dimethylamino- 1- dimethyl- 1-propyl)- aminocarbonyl]- 1,2,4which compounds are closely related chemically and in terms of their mode of action.

A general definition of the substituted triazolinones according to the invention is given by the formula Preferred compounds of the formula are those in which Het represents a heterocycle of the formula 1N 6 R' R R N X or N I I

R

2 and R 3 independently of one another each represent fluorine, chlorine, bromine or iodine, or represent straight-chain or branched alkyl having 1 to 8 carbon atoms, or represent straight-chain or branched alkenyl having 2 to 8 carbon atoms, or represent straight-chain or branched alkinyl having 2 to 8 carbon atoms, or represent straight-chain or branched alkoxy having 1 to 8 carbon atoms, or represent arylalkyl, aryl or aryloxy having in each case 6 to 10 carbon atoms in the aryl moiety and appropriate 1 to 6 carbon atoms in the straight-chain or branched alkyl moiety, each of which is optionally monosubstituted or Le A 29 399 7polysubstituted by identical or different substituents, suitable substituents for aryl being in each case: halogen, cyano, nitro, in each case straight-chain or branched alkyl, alkoxy or alkylthio having in each case 1 co 6 carbon atoms, in each case straight-chain or branched halogenoalkyl, halogenoalkoxy or halogenoalkylthio having in each case 1 to 6 carbon atoms and 1 to 13 identical or different halogen atoms, in each case straight-chain or branched alkoxycarbonyl or alkoximinoalkyl having in each case 1 to 6 carbon atoms in the individual alkyl moieties, and phenyl which is optionally monosubstituted or polysubstituted by identical or different substituents consisting of halogen and/or straight- chain or branched alkyl having 1 to 6 carbon atoms, A represents a divalent alkanediyl radical having 1 to 8 carbon atoms, and X' represents oxygen or sulphur, where

R

4 represents hydrogen, fluorine, chlorine, bromine, iodine, cyano or nitro, or represents straight-chain or branched alkyl 4which is optionally monosubstituted or polysubstituted by identical or different substituents, suitable substituents being: fluorine, chlorine, bromine, iodine, hydroxyl, cyano, amino, in each case straight-chain or branched alkoxy, alkylthio, N-alkylamino or N,Ndialkylamino having in each case 1 to 8 carbon atoms in the individual alkyl moieties;

R

4 moreover represents in each case straight-chain or branched alkenyl or alkinyl having in each case 2 to 8 carbon atoms, or represents in each case straight-chain or branched halogenoalkenyl or halogenoalkinyl having in each case 2 to 6 carbon atoms and 1 to 11 identical or different halogen atoms, in particular fluorine, chlorine, bromine and/or iodine, Le A 29 399 8- I or represents in each case straight-chain or branched alkoxy, alkylthio, alkylsulphinyl, alkylsulphonyl or alkoxycarbonyl having in each case 1 to 8 carbon atoms in the individual alkyl moieties, or moreover represents cycloalkyl having 3 to 8 carbon atoms, each of which is optionally monosubstituted or polysubstituted by identical or different substituents consisting of halogen and/or straight-chain or branched alkyl having 1 to 4 carbon atoms, or furthermore represents aryl or aryloxy having in each case 6 to 10 carbon atoms, each of which is optionally monosubstituted or polysubstituted by identical or different substituents, suitable substituents for aryl being in each case: halogen, cyano, nitro, in each case straight-chain or branched alkyl, alkoxy or alkylthio having in each case 1 to 6 carbon atoms, in each case straight-chain or branched halogenoalkyl, halogenoalkoxy or halogenoalkylthio having in each case 1 to 6 carbon atoms and 1 to 13 identical or different halogen atoms, in each case straight-chain or branched alkoxycarbonyl or alkoximinoalkyl having in each case 1 to 6 carbon atoms in the individual alkyl moieties, and phenyl which is optionally monosubstituted or polysubstituted by identical or different substituents consisting ofhalogen and/or straight-chain or branched alkyl having 1 to 6 carbon atoms,

R'

or R represents a radical of the formula _W, \R9

R

5 represents hydrogen, cyano, amino or aminocarbonyl, or represents straight-chain or branched alkyl having 1 to 8 carbon atoms which is optionally monosubstituted or polysubstituted by identical or different substituents, suitable substituents being: fluorine, chlorine, bromine, iodine, hydroxyl, cyano, amino, in each case Le A 29 399 -9straight-chain or branched alkoxy, alkylthio, N-alkylamino or N,Ndialkylamino having in each case 1 to 8 carbon atoms in the individual alkyl moieties;

R

5 moreover represents in each case straight-chain or branched alkenyl or alkinyl having in each case 2 to 8 carbon atoms, or represents in each case straight-chain or branched alkoxy, alkoxycarbonyl, N-alkylamino, N,N-dialkylamino or alkylideneimino having in each case 1 to 8 carbon atoms in the individual alkyl moieties, oc furthermore represents cycloalkyl having 3 to 8 carbon atoms, each of which is optionally monosubstituted or polysubstituted by identical or different substituents consisting of halogen and/or straight-chain or branched alkyl having 1 to 4 carbon atoms, or furthermore represents aryl or aryloxy having in each case 6 to 10 carbon atoms, each of which is optionally monosubstituted or polysubstituted by identical or different substitucnts, suitable substituents for aryl being in each case: halogen, cyano, nitro, in each case straight-chain or branched alkyl, alkoxy or alkythio having in each case 1 to 6 carbon atoms, in each case straight-chain or branched halogenoalkyl, halogenoalkoxy or halogenoalkylthio having in each case 1 to 6 carbon atoms and 1 to 13 identical or different halogen atoms, in each case straight-chain or branched alkoxycarbonyl or alkoximinoalkyl having in each case 1 to 6 carbon atoms in the individual alkyl moieties, and phenyl which is optionally monosubstituted or polysubstituted by identical or different substituents consisting ofhalogen and/or straight-chain or branched alkyl having 1 to 6 carbon atoms,

R

6 represents in each case straight-chain or branched alkyl, alkoxy or alkylthio having in each case 1 to 8 carbon atoms, or represents a radical

R

of the formula _h y, Le A 29 399

R

7 represents straight-chain or branched alkyl having 1 to 8 carbon atoms or represents cycloalkyl having 3 to 8 carbon atoms,

R

8 and R 9 either independently of one another each represent hydrogen, or represent straight-chain or branched alkyl having 1 to 8 carbon atoms, or each represent straight-chain or branched alkenyl or alkinyl having in each case 2 to 8 carbon atoms, or represent cycloalkyl having 3 to 8 carbon atoms, or represent arylalkyl or aryl having in each case 6 to carbon atoms in the aryl moiety and if appropriate 1 to 6 carbon atoms in the straight-chain or branched alkyl moiety, each of which is optionally monosubstituted or polysubstituted by identical or different substituents, suitable substituents for aryl being in each case: halogen, cyano, nitro, in each case straight-chain or branched alkyl, alkoxy or alkylthio having in each case 1 to 6 carbon atoms, in each case straight-chain or branched halogenoalkyl, halogenoalkoxy, halogenoalkylthio having in each case 1 to 6 carbon atoms and 1 to 13 identical or different halogen atoms, in each case straight-chain or branched alkoxycarbonyl or alkoximinoalkyl having in each case 1 to 6 carbon atoms in the individual alkyl moieties, and phenyl which is optionally monosubstituted or polysubstituted by identical or different substituents consisting of halogen and/or straight-chain or branched alkyl having 1 to 6 carbon atoms; or R 8 and R 9 together with the nitrogen atom to which they are attached, represent a saturated five- to seven-membered heterocycle which may optionally contain 1 to 2 further heteroatoms in particular nitrogen, oxygen or sulphur and which is optionally monosubstituted or rolysubstituted by identical or different substituents consisting of straight-chain or branched alkyl having 1 to 4 carbon atoms,

R

1 and R" either independently of one another each represent straight-chain or branched alkyl having 1 to 8 carbon atoms, or represent in each case 11 I ~1 I straight-chain or branched alkenyl or alkinyl having in each case 2 to 8 carbon atoms, or represent straight-chain or branched halogenoalkyl having 1 to 6 carbon atoms and 1 to 13 identical or different halogen atoms, especially fluorine, chlorine, bromine and/or iodine, or represent in each case straight-chain or branched halogenoalkenyl or halogenoalkinyl having in each case 2 to 6 carbon atoms and 1 to 11 identical or different halogen atoms, especially fluorine, chlorine, bromine and/or iodine, or represent in each case straight-chain or branched alkoxyalkyl or alkoxy having in each case 1 to 8 carbon atoms in the individual alkyl moieties, or represent cycloalkyl having 3 to 8 carbon atoms, or represent cycloalkylalkyl having 3 to 8 carbon atoms in the cycloalkyl moiety and 1 to 6 carbon atoms in the straight-chain or branched alkyl moiety, or represent aryl or arylalkyl having in each case 6 to 10 carbon atoms in the aryl moiety and if appropriate 1 to 6 carbon atoms in the straight-chain or branched alkyl moiety, each of which is optionally monosubstituted or polysubstituted by identical or different substituents, or represent heteroaryl having 2 to 9 carbon atoms and 1 to 4 identical or different heteroatoms in particular nitrogen, oxygen and/or sulphur which is optionally monosubstituted or polysubstituted by identical or different substituents, suitable substituents for aryl and heteroaryl being in each case: halogen, cyano, nitro, in each case straight-chain or branched alkyl, alkoxy or alkylthio having in each case 1 to 6 carbon atoms, in each case straight-chain or branched halogenoalkyl, halogenoalkoxy, halogenoalkylthio having in each case 1 to 6 carbon atoms and 1 to 13 identical or different halogen atoms, in each case straight-chain or branched alkoxycarbonyl or alkoximinoalkyl having in each case 1 to 6 carbon atoms in the individual alkyl moieties, and phenyl which is optionally monosubstituted or polysubstituted by identical or different substituents consisting ofhalogen and/or straight-chain or branched alkyl having 1 to 6 carbon atoms; Le A 29 399 12or R' 0 and together with the nitrogen atom to which they are attached, represent a saturated five- to seven-membered heterocycle which may optionally contain 1 to 2 further heteroatoms in particular nitrogen, oxygen and/or sulphur which is optionally monosubstituted or polysubstituted by identical or different substituents consisting of straight-chain or branched alkyl having 1 to 4 carbon atoms, and

X

2 represents oxygen or sulphur.

Particularly preferred compounds of the formula are those in which Het represents a heterocycle of the formula

R

4

R

6 or R

R

2 and R 3 independently of one another each represent fluorine, chlorine or bromine, or represent straight-chain or branched alkyl having 1 to 6 carbon atoms, or represent straight-chain or branched alkenyl having 2 to 6 carbon atoms, or represent straight-chain or branched alkinyl having 2 to 6 carbon atoms, or represent straight-chain or branched alkoxy having 1 to 6 carbon atoms, or represent phenylalkyl, phenyl or phenoxy having if appropriate 1 to 4 carbon atoms in the straight-chain or branched alkyl moiety, each of which is optionally monosubstituted to trisubstituted by identical or different substituents, suitable substituents for phenyl being in each case: halogen, cyano, nitro, in each case straight-chain or branched alkyl, alkoxy or alkylthio having in each case 1 to 4 carbon atoms, in each case straight-chain or branched halogenoalkyl, halogenoalkoxy or Le A 29 399 13- I halogenoalkylthio having in each case 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms, in each case straight-chain or branched alkoxycarbonyl or alkoximinoalkyl having in each case 1 to 4 carbon atoms in the individual alkyl moieties, and phenyl which is optionally monosubstituted to trisubstituted by identical or different substituents consisting ofhalogen and/or straight-chain or branched alkyl having 1 to 4 carbon atoms, A represents a divalent alkanediyl radical having 1 to 6 carbon atoms, and X' represents oxygen or sulphur, where

R

4 represents hydrogen, fluorine, chlorine, bromine, cyano or nitro, or represents straight-chain or branched alkyl having 1 to 6 carbon atoms which is optionally monosubstituted, suitable substituents being: hydroxyl, cyano, amino, in each case straight-chain or branched alkoxy, alkylthio, N-alkylamino or N,N-dialkylamino having in each case 1 to 6 carbon atoms in the individual alkyl moieties;

R

4 moreover represents in each case straight-chain or branched alkenyl or alkinyl having in each case 2 to 6 carbon atoms, or represents straight-chain or branched halogenoalkyl having 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms, especially fluorine, chlorine, and/or bromine, or represents in each case straight-chain or branched halogenoalkenyl or halogenoalkinyl having in each case 2 to 4 carbon atoms and 1 to 7 identical or different halogen atoms, especially fluorine, chlroine and/or bromine, or represents in each case straightchain or branched alkoxy, alkylthio, alkylsulphinyl, alkylsulphonyl or alkoxycarbonyl having in each case 1 to 6 carbon atoms in the individual alkyl moieties, or furthermore represents cycloalkyl having 3 to 7 carbon atoms, each of which is optionally monosubstituted to pentasubstituted by identical or different substituents consisting of chlorine, bromine, Le A 29 399 methyl and/or ethyl, or furthermore represents phenyl or phenoxy each of which is optionally monosubstituted to trisubstituted by identical or different substituents, suitable substituents for phenyl being in each case: halogen, cyano, nitro, in each case straight-chain or branched alkyl, alkoxy or alkylthio having in each case 1 to 4 carbon atoms, in each case straight-chain or branched halogenoalkyl, halogenoalkoxy or halogenoalkylthio having in each case 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms, in each case straight-chain or branched alkoxycarbonyl or alkoximinoalkyl having in each case 1 to 4 carbon atoms in the individual alkyl moieties, and phenyl which is optionally monosubstituted to trisubstituted by identical or different substituents consisting ofhalogen and/or straight- chain or branched alkyl having 1 to 4 carbon atoms,

S

R

or R 4 represents a radical of the formula

\R!

R

5 represents hydrogen, cyano, amino or aminocarbonyl, or represents straight-chain or branched alkyl having 1 to 6 carbon atoms which is optionally monosubstituted or polysubstituted by identical or different substituents, suitable substituents being: fluorine, chlorine, bromine, hydroxyl, cyano, amino, in each case straight-chain or branched alkoxy, alkylthio, N-alkylamino or N,Ndialkylamino having in each case 1 to 4 carbon atoms in the individual alkyl moieties;

R

5 moreover represents in each case straight-chain or branched alkenyl or alkinyl having in each case 2 to 6 carbon atoms, or represents in each case straight-chain or branched alkoxy, alkoxycarbonyl, N-alkylamino, Le A 29 399 Y~I I N,N-dialkylamino or alkylideneimino having in each case 1 to 6 carbon atoms in the individual alkyl moieties, or furthermore represents cycloalkyl having 3 to 7 carbon atoms which is in each case optionally monosubstituted to pentasubstituted by identical or different substituents consisting of chlorine, bromine, methyl and/or ethyl, or furthermore represents phenyl or phenoxy each of which is optionally monosubstituted to trisubstituted by identical or different substituents, suitable substituents for phenyl being in each case: halogen, cyano, nitro, in each case straight-chain or branched alkyl, alkoxy or alkythio having in each case 1 to 4 carbon atoms, in each case straight-chain or branched halogenoalkyl, halogenoalkoxy or halogenoalkylthio having in each case 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms, in each case straight-chain or branched alkoxycarbonyl or alkoximinoalkyl having in each case 1 to 4 carbon atoms in the individual alkyl moieties, and phenyl which is optionally monosubstituted to trisubstituted by identical or different substituents consisting ofhalogen and/or straight-chain or branched alkyl having 1 to 4 carbon atoms,

R

6 represents in each case straight-chain or branched alkyl, alkoxy or alkylthio having in each case 1 to 6 carbon atoms, or represents a radical

R"

of the formula __i

'R

R

7 represents straight-chain or branched alkyl having 1 to 6 carbon atoms or represents cycloalkyl having 3 to 7 carbon atoms,

R

8 and R 9 either independently of one another each represent hydrogen, or represent straight-chain or branched alkyl having 1 to 6 carbon atoms, or represent in each case straight-chain or branched alkenyl or alkinyl having in each case 2 to 6 carbon atoms, or represent cycloalkyl having Le A 29 399 16h- 3 to 7 carbon atoms, or represent phenylalkyl or phenyl having if appropriate 1 to 4 carbon atoms in the straight-chain or branched alkyl Smoiety, each of which is optionally monosubstituted to trisubstituted by identical or different substituents, suitable substituents for phenyl being in each case: halogen, cyano, nitro, in each case straight-chain or branched alkyl, alkoxy or alkythio having in each case 1 to 4 carbon atoms, in each case straight-chain or branched halogenoalkyl, halogenoalkoxy or halogenoalkylthio having in each case 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms, in each case straight-chain or branched alkoxycarbonyl or alkoximinoalkyl having in each case 1 to 4 carbon atoms in the individual alkyl moieties, and phenyl which is optionally monosubstituted to trisubstituted by identical or different substituents consisting ofhalogen and/or straight- chain or branched alkyl having 1 to 4 carbon atoms; or R 8 and R 9 together with the nitrogen atom to which they are attached, represent a saturated five- to seven-membered heterocycle which may optionally contain 1 further heteroatom in particular nitrogen, oxygen or sulphur which is optionally monosubstituted to tetrasubstituted by identical or different substituents consisting of straight-chain or branched alkyl having 1 to 3 carbon afoms,

R'

0 and R" either independently of one another each represent straight-chain or branched alkyl having 1 to 6 carbon atoms, or represent in each case straight-chain or branched alkenyl or alkinyl having in each case 2 to 6 carbon atoms, or represent straight-chain or branched halogenoalkyl having 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms, especially fluorine, chlorine and/or bromine, or represent in each case straight-chain or branched halogenoalkenyl or halogenoalkinyl having in each case 2 to 4 carbon atoms and 1 to 7 identical or different halogen; toms, especially fluorine, chlorine and/or bromine, or represent 17- L--LII I I- I in each case straight-chain or branched alkoxyalkyl or alkoxy having in each case 1 to 6 carbon atoms in the individual alkyl moieties, or represent cycloalkyl having 3 to 7 carbon atoms, or represent cycloalkylalkyl having 3 to 7 carbon atoms in the cycloalkyl moiety and 1 to 4 carbon atoms in the straight-chain or branched alkyl moiety, or represent phenyl or phenylalkyl having if appropriate 1 to 4 carbon atoms in the straight-chain or branched alkyl moiety, each of which is optionally monosubstituted to trisubstituted by identical or different substituents, or represent heteroaryl having 2 to 9 carbon atoms and 1 to 3 identical or different heteroatoms in particular nitrogen, oxygen and/or sulphur which is optionally monosubstituted to trisubstituted by identical or different substituents, suitable substituents for aryl and heteroaryl being in each case: halogen, cyano, nitro, in each case straight-chain or branched alkyl, alkoxy or alkylthio having in each case 1 to 4 carbon atoms, in each case straight-chain or branched halogenoalkyl, halogenoalkoxy or halogenoalkylthio having in each case 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms, in each case straight-chain or branched alkoxycarbonyl or alkoximinoalkyl having in each case 1 to 4 carbon atoms in the individual alkyl moieties, and phenyl which is optionally monosubstituted to trisubstituted by identical or different substituents consisting ofhalogen and/ or straight- chain or branched alkyl having 1 to 4 carbon atoms; or R'O and together with the nitrogen atom to which they are attached, represent a saturated five- to seven-membered heterocycle which may optionally contain 1 further heteroatom in particular nitrogen, oxygen or sulphur which is optionally monosubstituted to tetrasubstituted by identical or different substituents consisting of straight-chain or branched alkyl having 1 to 3 carbon atoms, and

SX

2 represents oxygen or sulphur.

18- Very particularly preferred compounds of the formula are those in which Het represents a heterocycle of the formula R R R /N

_=N

or R 7

X

I I

R

2 and R3 independently of one another each represent fluorine, chlorine or bromine, or represent straight-chain or branched alkyl having 1 to 4 carbon atoms, or represent straight-chain or branched alkenyl having 2 to 4 carbon atoms, or represent straight-chain or branched alkinyl having 2 to 4 carbon atoms, or represent straight-chain or branched alkoxy having 1 to 4 carbon atoms, or represent phenylalkyl, phenyl or phenoxy having if appropriate 1 to 3 carbon atoms in the straight-chain or branched alkyl moiety, each of which is optionally monosubstituted or disubstituted by identical or different substituents, suitable substituents for phenyl being in each case: fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, n- or i-propyl, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, s- or tbutoxy, methylthio, ethylthio, trifluoromethyl, difluoromethyl, trifluoromethoxy, difluoromethoxy, trifluoromethylthio, methoxycarbonyl, ethoxycarbonyl, methoximinomethyl, methoximinoethyl, ethoximinomethyl, ethoximinoethyl or phenyl which is optionally monosubstituted to disubstituted by identical or different substituents consisting of fluorine, chlorine, bromine, methyl and/or ethyl; A represents a divalent alkanediyl radical having 1 to 4 carbon atoms, and Le A 29 399 19- I 0 X' represents oxygen or sulphur, where

R

4 represents hydrogen, fluorine, chlorine, bromine, cyano or nitro, or represents straight-chain or branched alkyl having 1 to 4 carbon atoms which is optionally monosubstituied, suitable substituents being: hydroxyl, cyano, amino, in each case straight-chain or branched alkoxy, alkylthio, N-alkylamino or N,N-dialkylamino having in each case 1 to 4 carbon atoms in the individual alkyl moieties;

R

4 moreover represents in each case straight-chain or branched alkenyl or alkinyl having in each case 2 to 4 carbon atoms, or represents halogenoa- Ikyl having 1 or 2 carbon atoms and 1 to 5 identical or different halogen atoms, especially fluorine, chlorine and/or bromine, or represents in each case straight-chain or branched halogenoalkenyl or halogenoalkinyl having in each case 2 to 3 carbon atoms and 1 to 5 identical or different halogen atoms, especially fluorine, chlorine and/or bromine, or represents in each case straight-chain or branched alkoxy, alkylthio, alkylsulphinyl, alkylsulphonyl or alkoxycarbonyl having in each case 1 to 4 carbon atoms in the individual alkyl moieties, or furthermore represents cycloalkyl having 3 to 6 carbon atoms, or furthermore represents phenyl or phenoxy, each of which is optionally monosubstituted or disubstituted by identical or different substituents, suitable substituents for phenyl being in each case: fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, n- or i-propyl, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, s- or tbutoxy, methylthio, ethylthio, trifluoromethyl, difluoromethyl, trifluoromethoxy, difluoromethoxy, trifluoromethylthio, methoxycarbonyl, ethoxycarbonyl, methoximinomethyl, methoximinoethyl, ethoximinomethyl, ethoximinoethyl or phenyl which is optionally monosubstituted to disubstituted by identical or different Ssubstituents consisting of fluorine, chlorine, bromine, methyl and/or SLe A 29 399 I i ethyl;

R!

or R 4 represents a radical of the formula 'R9

R

5 represents hydrogen, cyano, amino or aminocarbonyl, or represents straight-chain or branched alkyl having 1 to 4 carbon atoms which is optionally monosubstituted or polysubstituted by identical or different substituents, suitable substituents being: fluorine, chlorine, bromine, hydroxyl, cyano, amino, in each case straight-chain or branched alkoxy, alkylthio, N-alkylamino or N,Ndialkylamino having in each case 1 to 3 carbon atoms in the individual alkyl moieties;

R

5 moreover represents in each case straight-chain or branched alkenyl or alkinyl having in each case 2 to 4 carbon atoms, or represents in each case straight-chain or branched alkoxy, alkoxycarbonyl, N-alkylamino, N,N-diaikylamino or alkylideneimino having in each case 1 to 4 carbon atoms in the individual alkyl moieties, or furthermore represents cycloalkyl having 3 to 6 carbon atoms, or furthermore represents phenyl or phenoxy each of which is optionally monosubstituted or disubstituted by identical or different substituents, suitable substituents for phenyl being in each case: fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, n- or i-propyl, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, s- or tbutoxy, methylthio, ethylthio, trifluoromethyl, difluoromethyl, trifluoromethoxy, difluoromethoxy, trifluoromethylthio, methoxycarbonyl, ethoxycarbonyl, methoximinomethyl, methoximinoethyl, ethoximinomethyl, ethoximinoethyl or phenyl which Sis optionally monosubstituted to disubstituted by identical or different Le A 29 399 21-

I

suustituentA consisting of fluorine, chlorine, bromine, methyl and/or ethyl;

R

6 represents in each case straight-chain or branched alkyl, alkoxy or alkylthio having in each case 1 to 4 carbon atoms, or represents a radical

R"

of the formula _W

R

7 represents straight-chain or branched alkyl having 1 to 4 carbon atoms or represents cycloalkyl having 3 to 6 carbon atoms,

R

8 and R 9 either independently of one another each represent hydrogen, or represent straight-chai. or branched alkyl having 1 to 4 carbon atoms, or represent in each case straight-chain or branched alkenyl or alkinyl having in each case 2 to 4 carbon atoms, or represent cycloalkyl having 3 to 6 carbon atoms, or represent phenylalkyl or phenyl having if appropriate 1 to 3 carbon atoms in the straight-chain or branched alkyl moiety, each of which is optionally monosubstituted or disubstituted by identical or different substituents, suitable substituents for phenyl being in each case: fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, n- or i-propyl, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, s- or tbutoxy, methylthio, ethylthio, trifluoromethyl, difluoromethyl, trifluoromethoxy, difluoromethoxy, trifluoromethylthio, methoxycarbonyl, ethoxycarbonyl, methoximinomethyl, methoximinoethyl, ethoximinomethyl, ethoximinoethyl or phenyl which is optionally monosubstituted to disubstituted by identical or different substituents consisting of fluorine, chlorine, bromine, methyl and/or ethyl; Le A 29 399 -22-

A'

or R 8 and R 9 together with the nitrogen atom to which they are attached, represent a saturated five- to seven-membered heterocycle which may optionally contain 1 further heteroatom in particular nitrogen, oxygen or sulphur which is optionally monosubstituted or disubstituted by identical or different substituents consisting of methyl and/or ethyl,

R'

0 and R" either independently of one another each represent straight-chain or branched alkyl having 1 to 4 carbon atoms, or represent in each case straight-chain or branched alkenyl or alkinyl having in each case 2 to 4 carbon atoms, or represent straight-chain or branched halogenoalkyl having 1 to 3 carbon atoms and 1 to 7 identical or different halogen atoms, especially fluorine, chlorine and/ or bromine, or represent in each case straight-chain or branched halogenoalkenyl or halogenoalkinyl having in each case 2 to 3 carbon atoms and 1 to 5 identical or different halogen atoms, especiallyfluorine, chlorine and/or bromine, or represent in each case straight-chain or branched alkoxyalkyl or alkoxy having in each case 1 to 4 carbon atoms in the individual alkyl moieties, or represent cycloalkyl having 3 to 6 carbon atoms, or represent cycloalkylalkyl having 3 to 6 carbon atoms in the cycloalkyl moiety and 1 or 2 carbon atoms in the alkyl moiety, or represent phenyl or phenylalkyl having if appropriate 1 to 3 carbon atoms in the straight-chain or branched alkyl moeity, each of which is optionally monfosubstituted or disubstituted by "',entical or different substituents, or represent heteroaryl having 2 to 5 carbon atoms and 1 to 3 identical or different heteroatoms in particular nitrogen, oxygen and/or sulphur which is optionally monosubstituted or disubstituted by identical or different substituents, suitable substituents for aryl and/or heteroaryl being in each case: fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, n- or i-propyl, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, s- or tbutoxy, methylthio, ethylthio, trifluoromethyl, difluoromethyl, trifluoromethoxy, difluoromethoxy, trifluoromethylthio, 23r I I 2 methoxycarbonyl, ethoxycarbonyl, methoximinomethyl, methoximinoethyl, ethoximinomethyl, ethoximinoethyl or phenyl which is optionally monosubstituted to disubstituted by identical or different substituents consisting of fluorine, chlorine, bromine, methyl and/or ethyl; or R'O and together with the nitrogen atom to which they are attached, represent a saturated five- to seven-membered heterocycle which may optionally contain 1 further heteroatom in particular nitrogen, oxygen or sulphur vAich is optionally monosubstituted or disubstituted by identical or different substituents consisting of methyl and/or ethyl, and X represents oxygen or sulphur.

Apart from the compounds listed for the Preparation Examples, specific mention may be made of the following substituted triazolinones of the general formula LeA29 399 -24- 7- sil -I It R I 2 X "MN-A-Si-R 13

R

(I)

R

3

A

N'

0N~

C

2

H

5 -CH2-

(?QKOC

N,~

CH

3

OH

3

CH

3 n-C 3

H

7

-OH

2 0 OH3 n-C 3

H

7 CH2' 0 n-C 3

H

7

-(OH

2 3 0 Le A29 399 Bl e t 0l A c-

C

2 115

C

2 H5

*C

2 Hi5 ~l2 al C3C 2 HS -(CH23- 0 C6CS C61i5 C61i5 -(Cli2)3- 0 NR CH3 Cfl 3 C H2- 0 CH3 CH3 CE{3 -Cl~r __LeA29 3 -26- ERet Rl R 2

R

3 A XI q-c-o

CH

3

CH

3 CH 3

-CH

2 s

H

3 0

G'

N'2 0N~

C

2

H

5

C

2

H

5

-O-

cI -(CH 2 3 0

CH

3

CH

3

C

2

HS-O-

CH

3

CH

3

CI

CH

3

CH

3

CI

-CH

2 0

-CH

2 0

-CH

2 0 27 Het RIR 2

R

3 A XI q C 2

H

5

C

2

H

5

OH

3

-CH

2 0 )-m

I

C

2

HS

NNXo l CI

-CH

2 0

-OH

2 0 I; G N a C 3

C

2

H

5 F \F H 3

-OH

2 0

N

N)~0

-OH

2 0 Le A 29399 2 28- Ret

R

3

X

A\

CH

3

CH

3 C25

CH

2 0 il q CH 3

CH

3

CH

3

-CH

2 0 4c

CH

3

CH

3

C

6

H

5 CH. 0

CH

3

CH

3

CH

3

-CH

2 0

F

2 a _T a CH 3

CH

3

CH

3

(CH

2 3 0 0' Le A29-39 29 Het ol N F, W'-

N'

RI R 2

R

3

CH

3

CH

3

-CH

2

-CH=CH

2

CH

3

CH

3

-CH

2 0 Gl F~ ~~N0

C

2

H

5 -Cu 2 0

CH

3 CH3-0- CH 3

-(OH

2 3 0 Le A..29399 -30

I

Bet RI R 2

R

3 A Xl- H a CH3

CH

3 i-C 3

H

7

-CH

2 0 H CH 3

CH

3 0H3 -CH 2 0

CH

3

CH

3

CH

3

-CH

2 0 Ne

CH

3

GB

3

CH

3

-CH

2 0

N'

CH

3

CH

3

CH

3

-GB

2 0

'NN)'

Le A29 399 31- KAON/c R3A XI

OH

3

-OH

2 0 OC; H 3

H

2 N-Cf8 2 n.OqH CH3 (CE;V N'N

OH

3

CH

3

OH

3

OH-

3

-OH

2 0

-OH

2 0

-OH

2 0

-OH

2 0 qv c

N'

be A 29399 2 32- 0, Het RR2

R

3 A X cnNF H 3 OH 3 0113

-OH

2

CH

3 0113

OH

3 -OH 2 0 KNo ")2N>7C

CH

3 0113

CH

3 0 011C3 0113 013 -0112- 0 OF-- 'a

H

3 CH 3 0113 -0112- 0 Le A 29399 33- Bet RI

R

2 R3A

CH

3 CR 3 CH 3 -CH 2 0 Using for example, l-chlorocarbonyl-3-dimethylamino4methy- 1,2,4one and trimethylsilylmethylamine as starting materials, the course of reaction of process according to the invention can be represented by the following equation: 113--N C- N'c N" 0 -HCI base l~

IC

Using for example, 3- dimethylamino-2-methylb 1,2A4-triazolin- 5- one and trimethylsilylmethyl isocyanate as starting materials, the course of reaction of process according to the invention can be represented by the following equation: Le A29 399 3 34- I N -=C=--N-CE-Si-C H

N

H4C-N 0 'NH-C^-Si-0^ A general definition of the l-chloro(thio)carbonyltriazolinones required as starting materials for carrying out process according to the invention is given by the formula In this formula (II) Het and X' preferably represent those radicals which have already been mentioned, in connection with the description of the compounds of the formula (I) according to the invention, as being preferred for these substituents.

The l-chloro(thio)carbonyltriazolinones of the formula (II) are known.

(cf. e.g. EP 431 390; EP 283 876; EP 298 371).

A general definition of the amines also required as starting materials for carrying out process according to the invention is given by the formula (III). In this formula (III) R 2

R

3 and Apreferably represent those radicals which have already been mentioned, in connection with the description of the compounds of the formula according to the invention, as being preferred for these substituents.

The amines of the formula (III) are known. or are obtainable in analogy to known methods (cf e.g J. Amer. Chem. Soc., 213867 [1951]; Synth.

Le A 29 399 I Commun., 1, (16-17) 1975-1978).

A general definition of the 1-unsubstituted triazolinones required as starting materials for carrying out process according to the invention is given by the formula In this formula (IV) Het preferably represents those radicals which have already been mentioned, in connection with the description of the substances of the formula (I) according to the invention, as being preferred for these substituents.

The 1-unsubstituted triazolinones of the formula (IV) are known or are obtainable in analogy to known methods (cf e.g. EP 283 876; EP 431 390; EP 298 371).

A general definition of the iso(thio)cyanates also required as tarting materials for carrying out process according to the invention is given by the formula In this formula R 1

R

2

R

3 A and X' preferably represent those radicals which have already been mentioned, in connection with the description of the substances of the.formula

(I)

according to the invention, as being preferred for these substituents.

The iso(thio)cyanates of the formula are known or are obtainable in analogy to known methods (cf e.g. Zh. Obshch. Khim. 38, 1179-1185 [1968]; Zh. Obshch. Khim. 31, 1383-1385 [1967]; J. Org. Chem. 9, 2688-2691 [1984]).

Suitable diluents for carrying out process according to the invention are inert organic solvents. These include, in particular, aliphatic, alicyclic or aromatic, optionally halogenated hydrocarbons such as, for example, benzine, benzene, toluene, xylene, chlorobenzene, dichlorobenzene, petroleum ether, hexane, cyclohexane, dichloromethane, chloroform or carbon tetrachloride; ethers such as diethyl ether, diisopropyl ether, dioxane, tetrahydrofuran or ethylene Le A 29 399 36- LP1 dl M v glycol dimethyl or diethyl ether; ketones such as acetone, butanone or methyl isobutyl ketone; nitriles such as acetonitrile, propionitrile or benzonitrile; amides such as N,N-dimethylformamide, N,N-dimethylacetamide, N-methylformanilide, N-methylpyrrolidone or hexamethylphosphoric triamide; esters such as methyl acetate or ethyl acetate, or bases such as pyridine.

Process according to the invention is preferably carried out in the presence of a suitable reaction auxiliary. Suitable such auxiliaries are all conventional inorganic or organic bases. These include, for example, alkaline earth metal or alkali metal hydroxides, such as sodium hydroxide, calcium hydroxide, potassium hydroxide or else ammonium hydroxide, alkali metal carbonates, such as sodium carbonate, potassium carbonate, potassium hydrogen carbonate, sodium hydrogen carbonate, or ammonium carbonate, alkali metal or alkaline earth metal acetates, such as sodium acetate, potassium acetate, calcium acetate, or ammonium acetate, and tertiary amines, such as trimethylamine, triethylamine, tributylamine, N,N-dimethylaniline, pyridine, piperidine, N-methylpiperidine, N,N-dimethylaminopyridine, diazabicyclooctane (DABCO), diazabicyclononene (DBN) or diazabicycloundecene

(DBU).

It is also possible to employ the amine of the formula (III) used as reactant, in a corresponding excess, simultaneously as reaction auxiliary.

When carrying out process according to the invention the reaction temperatures can be varied over a relatively wide range. The process is in general carried out at temperatures of between 0 0 C and 150 0

C,

preferably at temperatures of between 10 0 C and To carry out process according to the invention, in general from to 5.0 mol, preferably from 1.0 to 2 mol, of amine of the formula (III) and, if appropriate, from 1.0 to 5.0 mol, preferably from 1.0 to 2 mol, of Le A 29 399 37base as reaction auxiliary are employed per mole of 1chloro(thio)carbonyltriazolinone of the formula The implementation of the reaction and the working-up and isolation of the reaction products are carried out by known methods (cf in this respect, for example, EP 283 876 or the Preparation Examples).

Suitable diluents for carrying out process according to the invention are inert organic solvents. It is preferred to use the soivents listed in the descriptiun of the implementation of process according to the invention.

Process according to the invention may if desired be carried out in the presence of a suitable, basic reaction auxiliary. Suitable such auxiliaries are all conventional inorganic or organic bases. Preference is given to using tertiary amines such as trimethylamine, triethylamine, tributylamine, N,N-dimethylaniline, pyridine, piperidine, Nmethylpiperidine, N,N-dimethylaminopyridine, diazabicyclooctane (DABCO), diazabicyclononene (DBN) or diazabicycloundecene (DBU).

The addition of basic reaction auxiliaries, however, is not absolutely necessary.

When carrying out process according to the invention the reaction temperatures can be varied over a relatively wide range. The process is in general carried out at temperatures of btween 0°C and +150C, preferably at temperatures of between +40°C and 120°C.

Process according to the invention is usu' y carried out under atmospheric pressure. However, it is also possible to work under elevated or reduced pressure.

To canry out process according to the invention, in general from 1,O LLeA-29-3 -38-

I--

t to 5.0 mol, preferably from 1.0 to 2.5 mol, of iso(thio)cyanate of the formula and, if appropriate, from 0.01 to 5.0 mol, preferably from 0.1 to 2.5 mol, of base as reaction auxiliary are employed per mole of 1unsubstituted triazolinone of the formula (IV).

The implementation of the reaction and the working-up and isolation of the reaction products are carried out by known methods (cf. in this respect, for example, EP 283 376 or the Preparation Examples).

The end products of the formula are purified with the aid of conventional methods, for example by column chromatography or by recrystallization.

Characterization is made by means of the melting point or, in the case of compounds which do not crystallize, with the aid of proton nuclear magnetic resonance spectroscopy ('H-NMR).

The active compounds according to the invention can be used as defoliants, desiccants, agents for destroying broad-leaved plants arid, especially, as weedkillers. By weeds, in the broadest sense, there are to be understood all plants which growin locations where they are not wanted.

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 ofthe genera: Sinapis, Lepidium, Galium, Stellaris 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, Le A 29 3-9-2 39- II i LL I I I~ Galeopsis, Papaver, Centaurea, Trifolium, Ranunculus and Taraxacum.

Dicotvledon cultures ofthe genera: Gossypium, Glycine, Beta, Daucus, Phaseolus, Pisum, Solanum, Linum, Ipomoea, Vicia, Nicotiana, Lycopersicon, Arachis, Brassica, Lactuca, Cucumis and Cucurbita.

Monocotyledon weeds of the gnera: 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 control ofweeds, for example on industrial terrain and rail tracks, and on paths and squares m~Wt and 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 plantations, cocoa plantations, soft fruit plantings and hopfields, and for the selective combating of weeds in annual cultures.

In this context the active compounds according to the invention can be employed with particular success to combat mono- and dicotyledon Le A 29 399 BI~ "I 117 weeds in monocotyledon crops such as, for example, maize.

The active compounds can be converted into the customary formulations, such as solutions, emulsions, suspensions, powders, foams, pastes, granules, aerosols, natural and synthetic materials impregnated with active compound, very fine capsules in polymeric substances.

These formulations are produced in a known manner, for example by mixing the active compounds with extenders, that is, liquid solvents, liquefied gases under pressure, and/or solid carriers, optionally with the use of surface-active agents, that is, emulsifying agents and/or dispersing agents, and/or foam-forming agents.

In the case of the use of water as an extender, organic solvents can, for example, also be used as auxiliary solvents. Suitable liquid solvents are in the main: aromatics, such as xylene, toluene or alkylnaphthalenes, chlorinated aromatics or chlorinated aliphatic hydrocarbons, such as chlorobenzenes, chloroethylenes or methylene chloride, aliphatic hydrocarbons, such as cyclohexane or paraffins, for example mineral oil fractions, 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 or dimethyl sulphoxide, as well as water.

Suitable solid carriers are: 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; suitable solid carriers for granules are: 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 Le A 29 399 -41- ~YICI I I I r stalks; suitable emulsifying and/or foam-forming agents are: for example nonionic 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; suitable dispersing agents are: for example lignin sulphite waste liquors and methylcellulose.

Adhesives such as carboxymethylcellulose and natural and synthetic polymers in the form of powders, granules or latices, such as gum arabic, polyvinyl alcohol and polyvinyl acetate, as well as natural phospholipids, such as cephalins and lecithins, and synthetic phospholipids can be used in the formulations. Further additives may be mineral and vegetable oils.

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

Suitable herbicides for the mixtures are known herbicides, such as, for example, anilides, for example diflufenican and propanil; arylcarboxylic acids such as dichloropicolinic acid, dicamba or picloram; aryloxyalkanoic acids such as 2,4-D, 2,4-DB, 2,4-DP, fluroxypyr, MCPA, MCPP and triclopyr; aryloxy-phenoxy-alkanoic esters, such as Le A 29 3- 2 -42- 4, -1 Idiclofopmethyl, fenoxaprop-ethyl, fluazifop-butyl, haloxyfop- methyl and quizalofop-ethyl; azinones such as chioridazone and norilurazone; carbamates such as chiorpropham, desmedipham, phenmedipham and propham; chioroacetanilides such as alachior, acetochior, butachior, metazachior, metolachior, pretilachior and propachor; dinitroanilines such as oryzalin, pendimethalin and trifluralin; diphenyl ethers such as acifluorfen, bifenoxy fluoroglycofen, fomesafen, halosafen, lactofen and oxyfluorfen; ureas such as chiorotoluron, diuron, fluometuron, isoproturon, linuron and methabenzthiazuron; hydroxylamines such as alloxydim, clethodim, cycloxydim, sethoxydim and tralkoxydim; imidazolinones, such as imazethapyr, imazamethabenz, imazapyr and imazaquin; nitriles, such as bromoxynil, dichiobenil and ioxynil; oxyacetamides, such as mefenacet; suiphonylureas, such as amidosulfuron, bensulfaron-methyl, chiorimuron-ethyl, chiorsulfon, cinosulfiron, metsulfiron- methyl, nicosulfuron, primisulfuiron, pyrazosulfuron-ethyl, thifensulfiron-rnethyl, triasulfuron and tribenuronmethyl; thiolcarbamates, such as butylate, cycloate, diallate, EPTC, esprocarb, molinate, prosulfocarb, thiobencarb and triallate; triazines, such as atrazine, cyanazin, simazin, simetryne, terbutryr and terbutylazine; triazinones, such as hexazinon, metamitron and metribuzine; and others such as aminotriazole, benfuresate, bentazone, cinmethylin, clomazone, clopyralid, -difenzoquat, dithiopyr, ethoflmesate, fluorochioridone, glufosinate, glyphosate, isoxaben, pyridate, quinchiorac, quinmerac, suiphosate and tridiphane.

A mixures with other known active compounds, such as fungicides, insecticides, acaricides, nematicides, bird repellants, plant nutrients and agents which improve soil structure, is 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 Le A 29 394 -43and 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 relatively wide range. It depends essentially on the nature of the desired effect. In general, the amounts used are between 0.01 and 10 kg of active compound per hectare of soil surface, preferably between 0.05 and 5 kg per hectare.

The preparation and the use of the active compounds according to the invention are evident from the following examples.

Le A 29 394 44- I- I -II I Preparation Examples: Example 1: cHf 3

YCN'

N

o O1- \MN-a;-J a (Process a) A solution of 2.68 g (0.025 mol of trimethylsilylmethylamine and 2.53 g (0.025 mol) of triethylamine in 50 ml of acetonitrile is added dropwise with stirring at room temperature to 5.1 g (0.025 mol) of 1-chlorocarbonyl-3-dimethylamino-4-methyl-1, 2 ,4-triazolin-5-one in 100 ml of acetonitrile and, after addition is complete, the mixture is stirred at room temperature for 60 minutes. For working up, precipitated triethylamine hydrochloride is filtered off the filtrate is concentrated in vacuo, and the residue is taken up in 150 ml of dichloromethane, washed with three times 50 ml ofwater, dried over sodium sulphate and again concentrated in vacuo. The residue is recrystallized from cyclohexane.

g (59% of theory) are obtained of 3 -dimethylamino-4-methyl- 1- (trimethylsilylmnethyl-arninocarbonyl)- 1, 2 ,4-triazolin-5-one with a melting point of 79-81 C.

Le A 29 394 'r le Example 2: 0 N

-N

Uc^\^0 C I Process (b) 3.87 g (0.03 mol) of trimethylsilyl isocyanate and 3 drops of 1,8diazabicyclo- [5.4.0]-undec-7-ene (DBU) are added at room temperature with stirring to 5.25 g (0.03 mol) of 2-methyl-3-(4-morpholinyl)-(1H)- 1,2,4-triazolin-5-one in 100 ml of acetonitrile, the mixture is subsequently stirred at room temperature for 4 hours and is then concentrated in vacuo, and the residue is recrystallized from cyclohexane/ethyl acetate g (69% of theory) are obtained of 2-methyl-3-(4-morpholinyl)-1- (trimethylsilylmethyl-aminocarbonyl)-1,2,4-triazolin-5-one with a melting point of 133-134C..

In a corresponding manner, and in accordance with the general preparation data, the following substituted triazolinones of the general formula are obtained: Le A 29 394 -46 FLAt

R

*X NNl ASi-R

(I)

13

R

Ex. No. Het 1AS- 2 physical properties N l 0 ntp.99-100 0

C

4 a-S l 0 fl2p. 130-132 0

C

(GEj OqA 0 mp. 46-47 0

C

N

-n9-Si.CAI 0.6-0.7;

N'

OCA 1. 18-1.23; I 2.65; 3.20 Le A 29399 4 -47- Ex. No.

R

1 2 -A-Si-R XI physical properties 613 613 613

CF;

o imp. 79-801C o imp. 139-140*C o mrp. 140-141*C o imp. 81-83*C o rmp103-104*C 0 imp. 63-64TC

N'

12 !q C 48 ii Ex. No.

1

R

I 2 -A-Si-R 1e

X

1 physical properties 13 H CI-;a n.p. 115-116 0

C

LoZ P lil~ NYX t 14 16 BrC 16 Br KA4~ N e

C

CI;

aJ 3 ~~if GhS -aCE &13b~a o imp.79-.81 0

C

o Imp. 87-891C o mp, 143-145 0

C

o 1H.N4*) 1.15-1.20; 3.22 o m~p. 92-93 0

C

NR

-N

.olt-xO Le A 29 399 -49- Ex. No.

C

4

H

qq N=C\

A

4Cy) i-C0

R

i-R2 aI3 &J3 physical XI properties 0 xdp,167-168 0

C

o nap. 50-5 1 C 0.9-0.93; 1.18-1.2; 1.9; 2.3-2.32 0 IMp. 68-69-C 0 iff.p. 117-118 0

C

Lg A 29399 Ex. No.

1

R

2

X

1 physical properties 2.0,2.35-2.38; 2.85 N4 -0 26

IA

27 NC,_n-Cl

L'

29 IC6\ dli dli

CI

clt o 1H-NMR 0.8; 2.8-2.82; o 1H-NW.

0.8; 1.25-1.28; 2.77-2.8 o H-NNR*): 0.85-0.92; 2.75-2.8; 3.63-3.7 o rap. 88-90 0

C

0 rap. 158-160C Le. A 29 39 51pm Ex. No, -1

R

XI physical xl roperties Br I- 0 M.P. 94-95 0

C

6;3 31 40Dc a 32 C1 f 33 w/I

N,

0 M.P. 1 12 0

C

013 6;3 0 imp. 1210C 0 m.p. 125 0

C

Le A 29 399 52

V

Ex, No.

I

R

A-Si--Rk k q 3 XI physical properties 0 oil 36 (a 2 N 0cH

NIX

S IH-NM*): 3.04; 3.08- 3. 10; 3.30; 11.0 *)The 'H-NMIR spectra wre recorded in deuterochioroform (CD Cl 3 or l eutero dim ethylsuiphoxide (DMSO- d 6 with tetramethylsilane (TMS) as internal standard, The value given is the chemical shift, 8, in ppm.

LeA 2939-9 53 Use Examples: Jn the following Use Examples the compound indicated below wvas employed as comparison substance:

_N

(A)

2- Methyl- 3- dimethylamino- 1 dimethyl- 1 propyl)aminocarbonyl]- 1 ,2,4-triazolin- 5- one (knoxwn from EP 431 390) Le A29 399 54- Example A: Pre-emergenc, test Solvent: 5 parts by weight of acetone Emulsifier: 1 part by weight ofalk aryl polyglycol ether To produce a suitable preparation of active compound, one 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 compound according to Preparation Example 3 exhibits a marked superiority in activity, and also a considerably improved selectivity by crop plants, in relation to the prior art.

Le A 29 399 TableA.- Pre-emergence test! greenhouse Active cempound (ala (knov~n) (Exampfe 3) Application rate 1ng/a125 125 Maize Echinochloa Abuthilon Cassia Chenopod1ium Galium Sinapis Solanum 0 100 100 100 Le A29 399 56 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, one 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 are 5 15 cm high are sprayed with the preparation of the active compound so as to apply the particular amounts of active compound desired per unit area. 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 (as in the untreated control) 100% total destruction In this test, for example, the .ompound according to Preparation Example 3 exhibits a marked superiority in activity, and also a considerably improved selectivity by crop plants, in relation to the prior art.

57- Table B: Post-emeigence test! Gnenhouse Active compound o, 1

N

(knov~n) (Example 3) Application rate in gf ha 125 125 Maize Galitum Stellafla 'Viola Le A 29399 58

Claims

1. Substituted triazolinones of the general formula (I) I R X 'N-A-Si-R (1) 13 R in which Het represents a heterocycle of the formula R 4 R 5 R6 1 IN or R7 R 2 and R 3 independently of one another each represent halogen, alkyl, alkenyl, alkinyl or alkoxy or represent in each case optionally substituted arylalkyl, aryl or aryloxy, A represents a divalent alkanediyl radical, and X' represents oxygen or sulphur, where R 4 represents hydrogen, halogen, cyano or nitro or represents optionally substituted alkyl, or represents alkenyl, alkinyl, halogenoalkenyl, halogenoalkinyl, alkoxy, alkylthio, alkylsulphinyl, alkylsulphonyl or alkoxycarbonyl, or represents in each case optionally substituted cycloalkyl, aryl or aryloxy, or represents a radical of the formula Le A 29 399-PCT 59- R -Y, R 9 R 5 represents hydrogen or cyano, or represents optionally substituted alkyl, or represents alkenyl, alkinyl, alkoxy, alkoxycarbonyl or aminocarbonyl, or represents amino, N-alkylamino, N,N- dialkylamino or alkylideneimino, or represents in each case option- ally substituted cycloalkyl, aryl or aryloxy, R 6 represents alkyl, alkoxy or alkylthio, or represents a radical of the RD formula 'R" R 7 represents alkyl or cycloalkyl, R 8 and R 9 either independently of one another each represent hydrogen, alkyl, alkenyl, alkinyl or cycloalkyl or represent in each case optionally substituted arylalkyl or aryl, or, together with the nitrogen atom to which they are attached, represent an optionally substituted heterocycle, R' 0 and R" either independently of one another each represent alkyl, alkenyl, alkinyl, halogenoalkyl, halogenoalkenyl, halogenoalkinyl, alkoxyalkyl, alkoxy, cycloalkyl or cycloalkylalkyl or represent in each case optionally substituted aryl, arylalkyl or heteroaryl, or, together with the nitrogen atom to which they are attached, represent an optionally substituted heterocycle, and X 2 represents oxygen or sulphur. Le A 29 399

2. Substituted triazolinones of the general formula according to Claim 1, characterized in that Het represents a heterocycle of the formula 4 5 6 R R! R! R or R R 2 and R 3 independently of one another each represent fluorine, chlorine, bromine or iodine, or represent straight-chain or branched alkyl having 1 to 8 carbon atoms, or represent straight-chain or branched alkenyl having 2 to 8 carbon atoms, or represent straight- chain or branched alklnyl having 2 to 8 carbon atoms, or represent straight-chain or branched alkoxy having 1 to 8 carbon atoms, or represent arylalkyl, aryl or aryloxy having in each case 6 to 10 carbon atoms in the aryl moiety and if appropriate 1 to 6 carbon atoms in the straight-chain or branched alkyl moiety, each of which is optionally monosubstituted or polysubstituted by identical or different substituents, suitable substituents for aryl being in each case: halogen, cyano, nitro, in each case straight-chain or branched alkyl, alkoxy or alkylthio having in each case 1 to 6 carbon atoms, in each case straight-chain or branched halogenoalkyl, halogenoalkoxy or halogenoalkylthio having in each case 1 to 6 carbon atoms and 1 to 13 identical or different halogen atoms, in each case straight-chain or branched alkoxycarbonyl or alkoximinoalkyl having in each case 1 to 6 carbon atoms in the individual alkyl moieties, and phenyl which is optionally monosubstituted or polysubstituted by identical or different substituents consisting of halogen and/or straight-chain or branched alkyl having 1 to 6 carbon atoms, Le A 29 399 61- A represents a divalent alkanediyl radical having 1 to 8 carbon atoms, and X' represents oxygen or sulphur, where R 4 represents hydrogen, fluorine, chlorine, bromine, iodine, cyano or nitro, or represents straight-chain or branched alkyl which is optionally monosubstituted or polysubstituted by identical or different substituents, suitable substituents being: fluorine, chlorine, bromine, iodine, hydroxyl, cyano, amino, in each case straight-chain or branched alkoxy, alkylthio, N-alkylamino or N,N-dialkylamino having in each case 1 to 8 carbon atoms in the individual alkyl moieties; R 4 moreover represents in each case straight-chain or branched alkenyl or alkinyl having in each case 2 to 8 carbon atoms, or represents in each case straight-chain or branched halogenoalkenyl or halogenoalkinyl having in each case 2 to 6 carbon atoms and 1 to 11 identical or different halogen atoms, in particular fluorine, chlorine, bromine and/or iodine, or represents in each case straight-chain or branched alkoxy, alkylthio, alkylsulphinyl, alkylsulphonyl or alkoxycarbonyl having in each case 1 to 8 carbon atoms in the individual alkyl moieties,.or moreover represents cycloalkyl having 3 to 8 carbon atoms, each of which is optionally monosubstituted or polysubstituted by identical or different substituents consisting of halogen and/ or straight-chain or branched alkyl having 1 to 4 carbon atoms, or furthermore represents aryl or aryloxy having in each case 6 to 10 carbon atoms, each of which is optionally monosubstituted or polysubstituted by identical or different substituents, suitable substituents for aryl being in each case: halogen, cyano, nitro, in each case straight-chain or branched alkyl, alkoxy or alkylthio having in each case 1 to 6 carbon atoms, in each Le A 29 399 -62- case straight-chain or branched halogenoalkyl, halogenoalkoxy or halogenoalkylthio having in each case 1 to 6 carbon atoms and 1 to 13 identical or different halogen atoms, in each case straight-chain or branched alkoxycarbonyl or alkoximinoalkyl having in each case 1 to 6 carbon atoms in the individual alkyl moieties, and phenyl which is optionally monosubstituted or polysubstituted by identical or different substituents consisting of halogen and/or straight-chain or branched alkyl having 1 to 6 carbon atoms, R! or R 4 represents a radical of the formula _W, '9 R 5 represents hydrogen, cyano, amino or aminocarbonyl, or represents straight-chain or branched alkyl having 1 to 8 carbon atoms which is optionally inonosubstituted or polysubstituted by identical or different substituents, suitable substituents being: fluorine, chlorine, bromine, iodine, hydroxyl, cyano, amino, in each case straight-chain or branched alkoxy, alkylthio, N-alkylamino or N,N-dialkylamino having in each case 1 to 8 carbon atoms in the individual alkyl moieties; R 5 moreover represents in each case straight-chain or branched alkenyl or alkinyl having in each case 2 to 8 carbon atoms, or represents in each case straight-chain or branched alkoxy, alkoxycarbonyl, N- alkylamino, N,N-dialkylamino or alkylideneimino having in each case 1 to 8 carbon atoms in the individual alkyl moieties, or furthermore represents cycloalkyl having 3 to 8 carbon atoms, each ofwhich is optionally monosubstituted or polysubsiituted by identical or different substituents consisting of halogen and/or straight-chain or branched alkyl having 1 to 4 carbon atoms, or furthermore Le A 29 399 63 I represents aryl or aryloxy having in each case 6 to 10 carbon atoms, each of which is optionally monosubstituted or polysubstituted by identical or different substituents, suitable substituents for aryl being in each case: halogen, cyano, nitro, in each case straight-chain o branched alkyl, alkoxy or alkythio having in each case 1 to 6 carbon atoms, in each case straight-chain or branched halogenoalkyl, halogenoalkoxy or halogenoalkylthio having in each case 1 to 6 carbon atoms and 1 to 13 identical of different halogen atoms, in each case straight-chain or branched alkoxycarbonyl or alkoximinoalkyl having in each case 1 to 6 carbon atoms in the individual alkyl moieties, and phenyl which is optionally monosubstituted or polysubstituted by identical or different substituents consisting of halogen and/or straight-chain or branched alkyl having 1 to 6 carbon atoms, R 6 represents in each case straight-chain or branched alkyl, alkoxy or alkylthio having in each case 1 to 8 carbon atoms, or represents a R radical of the formula 'Rn R 7 represents straight-chain or branched alkyl having 1 to 8 carbon atoms or represents cycloalkyl having 3 to 8 carbon atoms, R 8 and R 9 either independently of one another each represent hydrogen, or represent straight-chain or branched alkyl having 1 to 8 carbon atoms, or each represent straight-chain or branched alkenyl or alkinyl having in each case 2 to 8 carbon atoms, or represent cycloalkyl having 3 to 8 carbon atoms, or represent arylalkyl or aryl having in each case 6 to 10 carbon atoms in the aryl moiety and if appropriate 1 to 6 carbon atoms in the straight-chain or branched alkyl moiety, each of which is optionally monosubstituted or Le A 29 396 -64- polysubstituted by identical or different substituents, suitable substituents for aryl being in each case: halogen, cyano, nitro, in each case straight-chain or branched alkyl, alkoxy or alkylthio having in each case 1 to 6 carbon atoms, in each case straight-chain or branched halogenoalkyl, halogenoalkoxy, halogenoalkylthio having in each case 1 to 6 carbon atoms and 1 to 13 identical or different halogen atoms, in each case straight-chain or branched alkoxycarbonyl or alkoximinoalkyl having in each case 1 to 6 carbon atoms in the individual alkyl moieties, and phenyl which is optionally monosubstituted or polysubstituted by identical or different substituents consisting of halogen and/or straight-chain or branched alkyl having 1 to 6 carbon atoms; or R 8 and R 9 together with the nitrogen atom to which they are attached, represent a saturated five- to seven-membered heterocycle which may optionally contain 1 to 2 further heteroatoms in particular nitrogen, oxygen or sulphur and which is optionally monosubstituted or polysubstituted by identical or different substituents consisting ofstraight-chain or branched alkyl having 1 to 4 carbon atoms, R'I and R" either independently of one another each represent straight- chain or branched alkyl having 1 to 8 carbon atoms, or represent in each case straight-chain or branched alkenyl or alkiny having in each case 2 to 8 carbon atoms, or represent straight-chain or branched halogenoalkyl having 1 to 6 carbon atoms and 1 to 13 identical or different halogen atoms, especially fluorine, chlorine, bromine and/or iodine, or represent in each case straight-chain or branched halogenoalkenyl or halogenoalkinyl having in each case 2 to 6 carbon atoms and 1 to 11 identical or different halogen atoms, especially fluorine, chlorine, bromine and/or iodine, or represent in each case straight-chain or branched alkoxyalkyl or alkoxy having in each case i to 8 carbon atoms in the individual alkyl moieties, or Le A 29 399 I represent cycloalkyl having 3 to 8 carbon atoms, or represent cycloalkylalkyl having 3 to 8 carbon atoms in the cycloalkyl moiety and 1 to 6 carbon atoms in the straight-chain or branched alkyl moiety, or represent aryl or arylalkyl having in each case 6 to carbon atoms in the aryl moiety and if appropriate 1 to 6 carbon atoms in the straight-chain or branched alkyl moiety, each of which is optionally monosubstituted or polysubstituted by identical or different substituents, or represent heteroaryl having 2 to 9 carbon atoms and 1 to 4 identical or different heteroatoms in particu'ar nitrogen, oxygen and/or sulphur which is optic. ally monosubstituted or polysubstituted by identical or different substituents, suitable substituents for aryl and heteroaryl being in each case: halogen, cyano, nitro, in ecch case straight-chain or branched alkyl, alkoxy or alkylthio having in each case 1 to 6 carbon atoms, in each case straight-chain or branched halogenoalkyl, halogenoalkoxy. halogenoalkylthio having in each case 1 to 6 carbon atoms and 1 to 13 identical or different halogen atoms, in each case straight-chain or branched alkoxycarbonyl or alkoximinoalkyl having in each case 1 to 6 carbon atoms in the individual alkyl moieties, and phenyl which is optionally monosubstituted or polysubstituted by identical or different substituents consisting of halogen and/or straight-chain or branched alkyl having 1 to 6 carbon atoms; or R" and together with the nitrogen atom to which they are attached, represent a saturated five- to seven-membered heterocycle which may optionally contain 1 to 2 further heteroatoms in particular nitrogen, oxygen and/or sulphur which is optionally monosubstituted or polysubstituted by identical or different substituents consistingof straight-chain or branched alkyl having 1 to 4 carbon atoms, and X 2 represents oxygen or sulphur. Le A 29 399 66- La s

3. Substituted triazolinones of the general formula according to Claim 1, characterized in that Het represercs a heterocycle of the formula R 4 R! R 6 R 1 R 2 and R 3 independently of one another each represent fluorine, chlorine or bromine, or represent straight-chain or branched alkyl having 1 to 6 carbon atoms, or represent straight-chain or branched alkenyl having 2 to 6 carbon atoms, or represent straight-chain or branched alkinyl having 2 to 6 carbon atoms, or represent straight- chain or branched alkoxy having 1 to 6 carbon atoms, or represent phenylalkyl, phenyl or phenoxy having if appropriate 1 to 4 carbon atoms in the straight-chain or branched alkyl moiety, each of which is optionally monosubstituted to trisubstituted by identical or different substituents, suitable substituents for phenyl being in each case: halogen, cyano, nitro, in each case straight-chain or branched alkyl, alkoxy or alkylthio having in each case 1 to 4 carbon atoms, in each case straight-chain or branched halogenoalkyl, halogenoalkoxy or halogenoalkylthio having in each case 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms, in each case straight-chain or branched alkoxycarbonyl or alkoximinoalkyl having in each case 1 to 4 carbon atoms in the individual alkyl moieties, and phenyl which is optionally monosubstituted to trisubstituted by identical or different substituents consisting of halogen and/or straight-chain or branched alkyl having 1 to 4 carbon atoms, Le A 29 399 -67- A represents a divalent alkanediyl radical having 1 to 6 carbon atoms, and X' represents oxygen or sulphur, where R 4 represents hydrogen, fluorine, chlorine, bromine, cyano or nitro, or represents straight-chain or branched alkyl having 1 to 6 carbon atoms which is optionally monosubstituted, suitable substituents being: hydroxyl, cyano, amino, in each case straight-chain or branched alkoxy, alkylthio, N-alkylamino or N,N-dialkylamino having in each case 1 to 6 carbon atoms in the individual alkyl moieties; R 4 moreover represents in each case straight-chain or branched alkenyl or alkinyl having in each case 2 to 6 carbon atoms, or represents in each case straight-chain or branched halogenoalkyl having 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms, especially fluorine, chlorine, and/or bromine, or represents in each case straight-chain or branched halogenoal.enyl or halogenoalkinyl having in each case 2 to 4 carbon atoms and 1 to 7 identical or different halogen atoms, especially fluorine, chlorine and/or bromine, or represents .in each case straight-chain or branched aikoxy, alkylthio, alkylsulphinyl, alkylsulphonyl or alkoxycarbonyl having in each case 1 to 6 carbon atoms in the individual alkyl moieties, or furthermore represents cycloalkyl having 3 to 7 carbon atoms, each of which is optionally monosubstituted to pentasubstituted by identical or different substituents consisting of chlorine, bromine, methyl and/or ethyl, or furthermore represents phenyl or phenoxy each of which is optionally monosubstituted to trisubstituted by identical or different substituents, suitable substituents for phenyl being in each case: halogen, cyano, nitro, in each case straight-chain or branched alkyl, Le A 29 399 -68- alkoxy or alkylthio having in each case 1 to 4 carbon atoms, in each case straight-chain or branched halogenoalkyl, halogenoalkoxy or halogenoalkylthio having in each case 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms, in each case straight-chain or branched alkoxycarbonyl or alkoximinoalkyl having in each case 1 to 4 carbon atoms in the individual alkyl moieties, and phenyl which is optionally monosubstituted to trisubstituted by identical or different substituents consisting of halogen and/or straight-chain or branched alkyl having 1 to 4 carbon atoms, R or R 4 represents a radical of the formula \R9 R S represents hydrogen, cyano, amino or aminocarbonyl, or represents straight-chain or branched alkyl having 1 to 6 carbon atoms which is optionally monosubstituted or polysubstituted by identical or diffeient substituents, suitable substituents being fluorine, chlorine, bromine, hydroxyl, cyano, amino, in each case straight-chain or branched alkoxy, alkylthio, N-alkylamino or N,N- dialkylamino having in each case 1 to 4 carbon atoms in the individual alkyl moieties: R S moreover represents in each case straight-chain or branched alkenyl or alkinyl having in each case 2 to 6 carbon atoms, or represents in each case straight-chain or branched alkoxy, alkoxycarbonyl, N- alkylamino, N,N-dialkylamino or alkylideneimino having in each case 1 to 6 carbon atoms in the individual alkyl moieties, or furthermore represents cycloalkyl having 3 to 7 carbon atoms which is in each case optionally monosubstituted to pentasubstituted by identical or different substituents consisting of chlorine, bromine, methyl and/or ethyl, or furthermore represents phenyl or phenoxy Le A 29 399 69- each of which is optionally monosubstituted to trisubstituted by identical or different substitueiits, suitable substituents for phenyl being in each case: halogen, cyano, nitro, in each case straight-chain or branched alkyl, alkoxy or alkythio having in each case 1 to 4 carbon atoms, in each case straight-chain or branched halogenoalkyl, halogenoalkoxy or halogenoalkylthio having in each case 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms, in each case straight-chain or branched alkoxycarbonyl or alkoximinoalkyl having in each case 1 to 4 carbon atoms in the individual alkyl moieties, and phenyl which is optionally monosubstituted to trisubstituted by identical or different substituents consisting of halogen and/or straight-chain or branched alkyl having 1 to 4 carbon atoms, R 6 represents in each case straight-chain or branched alkyl, alkoxy or alkylthio having in each case 1 to 6 carbon atoms, or represents a R radical of the formula 'Rn R 7 represents straight-chain or branched alkyl having 1 to 6 carbon atoms or represents cycloalkyl having 3 to 7 carbon atoms, R 8 and R 9 either independently of one another each represent hydrogen, or represent straight-chain or branched alkyl having 1 to 6 carbon atoms, or represent in each case straight-chain or branched alkenyl or alkinyl having in each case 2 to 6 carbon atoms, or represent cycloalkyl having 3 to 7 carbon atoms, or represent phenylalkyl or phenyl having if appropriate 1 to 4 carbon atoms in the straight- chain or branched alkyl moiety, each of which is optionally monosubstituted to trisubstituted by identical or different substituents, suitable substituents for phenyl being in each case: Le A 29 399 halogen, cyano, nitro, in each case straight-chain or branched alkyl, alkoxy or alkythio having in each case 1 to 4 carbon atoms, in each case straight-chain or branched halogenoalkyl, halogenoalkoxy or halogenoalkylthio having in each case 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms, in each case straight-chain or branched alkoxycarbonyl or alkoximinoalkyl having in each case 1 to 4 carbon atoms in the individual alkyl moieties, and phenyl which is optionally monosubstituted to trisubstituted by identical or different substituents consisting of halogen and/or straight-chain or branched alkyl having 1 to 4 carbon atoms; or R 8 and R 9 together with the nitrogen atom to which they are attached, represent a saturated five- to seven-membered heterocycle which may optionally contain 1 further heteroatom in particular nitrogen, oxygen or sulphur which is optionally monosubstituted to tetrasubstituted by identical or different substituents consisting of straight-chain or branched alkyl having 1 to 3 carbon atoms, R' 0 and R" either independently of one another each represent straight- chain or branched alkyl having 1 to 6 carbon atoms, or represent in each case straight-chain or branched alkenyl or alkinyl having in each case 2 to 6 carbon atoms, or represent straight-chain or branched halogenoalkyl.having 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms, especially fluorine, chlorine and/or bromine, or represent in each case straight-chain or branched halogenoalkenyl or halogenoalkinyl having in each case 2 to 4 carbon atoms and 1 to 7 identical or different halogen atoms, especially fluorine, chlorine and/or bromine, or represent in each case straight- chain or branched alkoxyalkyl or alkoxy having in each case 1 to 6 carbon atoms in the individual alkyl moieties, or represent cycloalkyl having 3 to 7 carbon atoms, or represent cycloalkylalkyl having 3 to 7 carbon atoms in the cycloalkyl moiety and 1 to 4 carbon atom.st in the straight-chain or branched alkyl moiety, or represent phenyl or Le A 29 399 71- phenylalkyl having if appropriate 1 to 4 carbon atoms in the straight- chain or branched alkyl moeity, each of which is optionally monosubstituted to trisubstituted by identical or different sub- stituents, or represent heteroaryl having 2 to 9 carbon atoms and 1 to 3 identical or different heteroatoms in particular nitrogen, oxygen and/or sulphur which is optionally monosubstituted to trisubstituted by identical or different substituents, suitable substituents for aryl and heteroaryl being in each case: halogen, cyano, nitro, in each case straight-chain or branched alkyl, alkoxy or alkythio having in each case 1 to 4 carbon atoms, in each case straight-chain or branched halogenoalkyl, halogenoalkoxy or halogenoalkylthio having in each case 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms, in each case straight-chain or branched alkoxy A.yl or alkoximinoalkyl having in each case 1 to 4 carbon atoms in the individual alkyl moieties, and phenyl which is optionally monosubstituted to trisubstituted by identical or different substituents consisting of halogen and/or straight-chain or branched alkyl having 1 to 4 carbon atoms; or R'O and together with the nitrogen atom to which they are attached, represent a saturated five- to seven-membered heterocycle which may optionally contain 1 further heteroatom in particular nitrogen, oxygen or sulphur which is optionally monosubstituted to tetrasubstituted by identical or different substituents consisting of straight-chain or branched alkyl having 1 to 3 carbon atoms, and X? represents oxygen or sulphur.

4. Substituted triazolinones of the general formula according to Claim 1, characterized in that Het represents a heterocycle of the formula Le A 29 399 -72- 4 5 6 R R or R R 2 and R 3 independently of one another each represent fluorine, chlorine or bromine, or represent straight-chain or branched alkyl having 1 to 4 carbon atoms, or represent straight-chain or branched alkenyl having 2 to 4 carbon atoms, or represent straight-chain or branched alkinyl having 2 to 4 carbon atoms, or represent straight- chain or branched alkoxy having 1 to 4 carbon atoms, or represent phenylalkyl, phenyl or phenoxy having if appropriate 1 to 3 carbon atoms in the straight-chain or branched alkyl moiety, each of which is optionally monosubstituted or disubstituted by identical or different substituents, suitable substituents for phenyl being in each case: fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, n- or i- propyl, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, i-, s- or t-butoxy, methylthio, ethylthio, trifluoromethyl, difluoromethyl, trifluoromethoxy, difluoromethoxy, trifluoromethylthio, methoxycarbonyl, ethoxycarbonyl, methoximinomethyl, methoximinoethyl, ethoximinomethyl, ethoximinoethyl or phenyl which is optionally monosubstituted to disubstituted by identical or different substituents consisting of fluorine, chlorine, bromine, methyl and/or ethyl; A represents a divalent alkanediyl radical having 1 to 4 carbon atoms, and X' represents oxygen or sulphur, where io A 29 399 73- I R 4 represents hydrogen, fluorine, chlorine, bromine, cyano or nitro, or represents straight-chain or branched alkyl having 1 to 4 carbon atoms which is optionally monosubstituted, suitable substituents being: hydroxyl, cyano, amino, in each case straight-chain or branched alkoxy, alkylthio, N-alkylamino or N,N-dialkylamino having in each case 1 to 4 carbon atoms in the individual alkyl moieties; R 4 moreover represents in each case straight-chain or branched alkenyl or alkinyl having in each case 2 to 4 carbon atoms, or represents halogenoalkyl having 1 or 2 carbon atoms and 1 to 5 identical or different halogen atoms, especially fluorine, chlorine and/or bromine, or represents in each case straight-chain or branched halogenoalkenyl or halogenoalkinyl having in each case 2 to 3 carbon atoms and 1 to 5 identical or different halogen atoms, especially fluorine, chlorine and/or bromine, or represents in each case straight-chain or branched alkoxy, alkylthio, alkylsulphinyl, alkylsulphonyl or alkoxycarbonyl having in each case 1 to 4 carbon atoms in the individual alkyl moieties, or furthermore represents cycloalkyl having 3 to 6 carbon atoms, or furthermore represents phenyl or phenoxy, each of which is optionally monosubstituted or disubstituted by identical or different substituents, suitable substituents for phenyl being in each case: fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, n- or i- propyl, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, i-, s- or t-butoxy, methylthio, ethylthio, trifluoromethyl, difluoromethyl, trifluoromethoxy, difluoromethoxy, trifluoromethylthio, methoxycarbonyl, ethoxycarbonyl, methoximinomethyl, methoximinoethyl, ethoximinomethyl, ethoximinoethyl or phenyl which is optionally monosubstituted to disubstituted by identical or different substituents consisting of fluorine, chlorine, bromine, methyl and/or ethyl; Le A 29 399 -74- t R or R 4 represents a radical of the formula '9 R 5 represents hydrogen, cyano, amino or aminocarbonyl, or represents straight-chain or branched alkyl having 1 to 4 carbon atoms which is optionally monosubstituted or polysubstituted by identical or different substituents, suitable substituents being: fluorine, chlorine, bromine, hydroxyl, cyano, amino, in each case straight-chain or branched alkoxy, alkylthio, N-alkylamino or N,N- dialkylamino having in each case 1 to 3 carbon atoms in the individual alkyl moieties; R 5 moreover represents in each case straight-chain or branched alkenyl or alkinyl having in each case 2 to 4 carbon atoms, or represents in each case straight-chain or branched alkoxy, alkoxycarbonyl, N- alkylamino, N,N-dialkylamino or alkylideneimino having in each case 1 to 4 carbon atoms in the individual alkyl moieties, or furthermore represents cycloalkyl having 3 to 6 carbon atoms, or furthermore represents phenyl or phenoxy each of which is option- ally monosubstituted nr disubstituted by identical or different subtituents, suitable substituents for phenyl being in each case: fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, n- or i- propyl, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, i-, s- or t-butoxy, methylthio, ethylthio, trifluoromethyl, difluoromethyl, trifluoromethoxy, difluoromethoxy, trifluoromethylthio, methoxycarbonyl, ethoxycarbonyl, methoximinomethyl, methoximinoethyl, ethoximinomethyl, ethoximinoethyl or phenyl which is optionally monosubstituted to disubstituted by identical or different substituents consisting of fluorine, chlorine, bromine, methyl and/or ethyl; Le A 29 399 R 6 represents in each case straight-chain or branched alkyl, alkoxy or alkylthio having in each case 1 to 4 carbon atoms, or represents a RD radical of the formula 'R" R 7 represents straight-chain or branched alkyl having 1 to 4 carbon atoms or represents cycloalkyl having 3 to 6 carbon atoms, R 8 and R 9 either independently of one another each represent hydrogen, or represent straight-chain or branched alkyl having 1 to 4 carbon atoms, or represent in each case straight-chain or branched alkenyl or alkinyl having in each case 2 to 4 carbon atoms, or represent cycloalkyl having 3 to 6 carbon atoms, or represent phenylalkyl or phenyl having if appropriate 1 to 3 carbon atoms in the straight- chain or branched alkyl moiety, each of which is optionally monosubstituted or disubstituted by identical or different substituents, suitable substituents for phenyl being in each case: fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, n- or i- propyl, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, i-, s- or t-butoxy, methylthio, ethylthio, trifluoromethyl, difluoromethyl, trifluoromethoxy, difluoromethoxy, trifluoromethylthio, methoxycarbonyl, ethoxycarbonyl, methoximinomethyl, methoximinoethyl, ethoximinomethyl, ethoximinoethyl or phenyl which is optionally monosubstituted to disubstituted by identical or different substituents consisting of fluorine, chlorine, bromine, methyl and/or ethyl; or R 8 and R 9 together with the nitrogen atom to which they are attached, represent a saturated five- to seven-membered heterocycle which may optionally contain 1 further heteroatom in particular nitrogen, oxygen or sulphur which is optionally monosubstituted or Le A 29 399 -76- disubstituted by identical or different substituents consisting of methyl and/or ethyl, R' 0 and R" either independently of one another each represent straight- chain or branched alkyl having 1 to 4 carbon atoms, or represent in each case straight-chain or branched alkenyl or alkinyl having in each case 2 to 4 carbon atoms, or represent straight-chain or branched halogenoalkyl having 1 to 3 carbon atoms and 1 to 7 identical or different halogen atoms, especially fluorine, chlorine and/ or bromine, or represent in each case straight- chain or branched halogenoalkenyl or halogenoalkinyl having in each case 2 to 3 carbon atoms and 1 to 5 identical or different halogen atoms, especially fluorine, chlorine and/or bromine, or represent in each case straight- chain or branched alkoxyalkyl or alkoxy having in each case 1 to 4 carbon atoms in the individual alkyl moieties, or represent cycloalkyl having 3 to 6 carbon atoms, or represent cycloalkylalkyl having 3 to 6 carbon atoms in the cycloalkyl moiety and 1 or 2 carbon atoms in the alkyl moiety, or represent phenyl or phenylalkyl having if appro- priate 1 to 3 carbon atoms in the straight-chain or branched alkyl moiety, each of which is optionally monosubstituted or disubstituted by identical or different substituents, or represent heteroaryl having 2 to 5 carbon atoms and 1 to 3 identical or different heteroatoms in particular nitrogen, oxygen and/or sulphur which is optionally monosubstituted or disubstituted by identical or different sub- stituents, suitable substituents for aryl and/or heteroaryl being in each case: fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, n- or i- propyl, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, i-, s- or t-butoxy, methylthio, ethylthio, trifluoromethyl, difluoromethyl, trifluoromethoxy, difluoromethoxy, trifluoromethylthio, methoxycarbonyl, ethoxycarbonyl, methoximinomethyl, methoximinoethyl, ethoximinomethyl, Le A 29 399 77- c ethoximinoethyl or phenyl which is optionally monosubstituted to disubstituted by identical or different substituents consisting of fluorine, chlorine, bromine, methyl and/or ethyl; or RI 0 and together with the nitrogen atom to which they are attached, represent a saturated five- to seven-membered heterocycle which may optionally contain 1 further heteroatom in particular nitrogen, oxygen or sulphur which is optionally monosubstituted or disubstituted by identical or different substituents consisting methyl and/or ethyl, and X represents oxygen or sulphur. Process for the preparation of substituted triazolinones of the general formula (I) I-t 1 R R X "N-A-Si-R (I) 13 R Het represents a heterocycle of the formula R! R! R 6 4 5 6 or RX2 R 2 and R 3 independently of one another each represent halogen, alkyl, alkenyl, alkinyl or alkoxy or represents in each case optionally substituted arylalkyl, aryl or aryloxy, A represents a divalent alkanediyl radical, and Le A 29 399

78- X represents oxygen or sulphur, where R 4 represents hydrogen, halogen, cyano or nitro or represents optionally substituted alkyl, or represents alkenyl, alkinyl, halogenoalkenyl, halogenoalkinyl, alkoxy, alkylthio, alkylsulphinyl, alkylsulphonyl or alkoxycarbonyl, or represents in each case optionally substituted cycloalkyl, aryl or aryloxy, or represents a radical of the formula \R7 R 5 represents hydrogen or cyano, or represents optionally substituted alkyl, or represents alkenyl, alkinyl, alkoxy, alkoxycarbonyl or aminocarbonyl, or represents amino, N-alkylamino, N,N- dialkylamino or alkylideneimino, or represents in each case option- ally substituted cycloalkyl, aryl or aryloxy, R 6 represents alkyl, alkoxy or alkylthio, or represents a radical of the R formula i 'R" R 7 represents alkyl or cycloalkyl, R 8 and R 9 either independently of one another each represent hydrogen, alkyl, alkenyl, alkinyl or cycloalkyl or represent in each case optionally substituted arylalkyl or aryl, or, together with the nitrogen atom to which they are attached, represent an optionally substituted heterocycle, Le A 29 399

79- R 1 and R" either independently of one another each represent alkyl, alkenyl, alkinyl, halogenoalkyl, halogenoalkenyl, halogenoalkinyl, alkoxyalkyl, alkoxy, cycloalkyl or cycloalkylalkyl or represent in each case optionally substituted aryl, arylalkyl or heteroaryl, or, together with the nitrogen atom to which they are attached, represent an optionally substituted heterocycle, and X represents oxygen or sulphur, characterized in that a) 1-chloro(thio)carbonyltriazolinones of the formula (II) I X IC in which Het and X' have the meanings giv; above are reacted with amines of the formula (III) I 2 R HN-A-Si-R! 13 R (ff in which R 2 R 3 and A have the meanings given above, optionally in the presence of a diluent and optionally in the presence of a reaction auxiliary, or if Le A 29 399 81 b) 1-unsubstituted triazolinones of te formula (IV) Het-H (IV) in which Het has the meaning given above are reacted with iso(thio)cyanates of the formula (V) oc r o o r* r e c R SC I-A-S 2 XC=N-A-S i--R in which R 2 R 3 A and X' have the meanings given above, optionally in the presence of a diluent and optionally in the presence of a reaction auxiliary. 6. Herbicidal compositions, characterized in that they contain at least one substituted triazolinone of the general formula accordingto Claims 1 to 7. Method of combating unwanted plants, characterized in that substituted triazolinones of the general formula according to Claims 1 to 5 are allowed to act on plants and/or their habitat. 82 8. Process for the preparation of herbicidal compositions, chacterized in that substituted triazolinones of the general formula according to Claims 1 to 5 are mixed with extenders and/or surface-active substances. DATED this 19th day of September, 1995. BAYER AKTIENGESELLSCHAFT By Its Patent Attorneys 15 DAVIES COLLISON CAVE go** *o *go• p:\wpdocs\grs\543522\kd Ip I I INTERNATIONAL SEARCH REPORT n Intrr al Application No PCT/EP 93/02705 A. CLASSIFICATION OF SUBJECT MATTER IPC 5 C07F7/08 C07F7/18 A01N55/00 According to International Patent Classificaton (IPC or to both national classification and IPC B. FIELDS SEARCHED Mimn Am documentation searched (classificaon system followed by classficaton symbols) IPC 5 C07F AO1N Documentation searched other than minmmum documentation to the extent that such documents are included in the fields searched Electronic data base consulted during the ternational search (name of data base and, where practical, search terms used) C. DOCUMENTS CONSIDERED TO BE RELEVANT Category Citation of document, with indication, where appropriate, of the relevant passages Relevant to claim No. A WO,A,89 00573 (AGROLINZ AGRARCHEMIKALIEN 1 GMBH) 26 January 1989 see the whole document A DE,A,41 09 671 (BAYER AG) 24 September 1,6 1992 see the whole document SFurther documents are listed in the continuation of box C. M Patent famlymembers ar listed in annex. Special categories of ated documents later document published after the international filing date A' document defining the general state of the art which is not or pnonty date and not in conflict with the application but consdered to be of partcular relevance cted to understand the princple or theory underlying the invention E' earlier docuent but pulished on or after the nternatonal "X document of particular relevance; the claimed Invention filing date cannot be considered novel or cannot be considered to L document which may throw doubts on prnonty claim(s) or involve an inventive step when the document is taken alone which is ated to establish the publication date of another d o p r t c atation or other special reason (as specified) Y document of partcular relevance; the claimed inventon n, cannot be considw-d to involve an inventive step when the document refernng to an oral disclosure, use, exhibition or document is comn ined with one or more other such docu- othe' means ments, such co oination being obvious to a person slalled document published pnor to the International filing date but m the art. later than the prnonty date claimed document member of the same patent family Date of the actual completon of the internatonal search Date of mailing of the international search report 7 December 1993 2 112. 93 Name and mailing address of the ISA Authorized officer European Patent Office, P.B. 5818 Patentlaan 2 NL 2280 HV Rl)swilk Tel. (+31-70) 340-2040, Tx. 31 651 epo nl, R l Fa (+31-70) 340-3016 Rinkel, L I- .LIdvu Iics act Jl Y~ rorm rPCllSA/210 (fec9na Ineet) (July 199) 111 11 INTERNATIION AL SEARCH REPORT -fomaton n ptet fmil mc =Inften Wa Application No fomaton n ptet fmil icrnaiPCT/EP 9 3/02705 Patent document I Publication IPatent famifly I Publication cited in search report d ate member(s) j date WO-A-8900573 26-01-89 DE-A- 3723246 26-01-89 AU-A- 1980388 13-02-89 EP-A- 0303802 22-02-89 DE-A-4109671 24-09-92 EP-A- 0505819 30-09-92 JP-A- 5112539 07-05-93 Form PCT/ISAI2IO (patent family annex) (July 1992) INTERNATIONALER RECHERCHENBERICHT In" iWes Aktenzechcn PCT/EP 93/02705 A. KLASSI2FIZIERUNG DES ANMELDUNGSGEGENSTANDES IPK 5 C077/08 C077/18 AOIN55/00 Nacts der Intersutionalen Patentkjaanfikation (IPK) oider nach der naionalen Kassifikation und der IPK B. RECHERCHIERTE GEBIETE Recherchierter Mindesspndioff (Klassifikationscystemn und Klasofikationssymbole) IPK 5 C07F A0iN Recherchiertc aber nscht zumn Mindecstpriltstoff geh~rende Vertflendichungcn, soweit die tinter die recherchiertan Gebiece fallen Wlhrend der internatonalen Recherche konsuluerte elcktrorischc Datenbank (Name der Datenbank und evil. verwendete Suchbegniffe) C. ALS WESENTLICH ANGESEHENE UNTERLAGEN Kategone' Bezeickintrig der Verbifentliehung, sowait erforderlich tinter Angabe der in Betracht kommnendcn Teile Batr. Anspruch Nr. A WO,A,89 00573 (AGROLINZ AGRARCHEMIKALIEN 1 GMBH) 26. Januar 1989 siehe das ganze Dokument A DE,A,41 09 671 (BAYER AG) 24. September 1,6 1992 siehe das ganze Dokument WiceVerdifentlichungen sind der Fortsetzung von Feld C zu MY Siehe Ahn aetaii ennhien vIn Ineeee e~te~cugnAh BEsondere Kategone ongieene n c~fnhhmc T' Spe Veroffientliebuitng, die nach dem, internationalen. Anidedawum Veroffentlichung, die den aligemncmen Stand der Technik definiert, oer dem Priontatr.daturn ver6ffcntbcht worden ist und mit der aber nicht als besonders bedeutsam anzusehen ist Anmeldung nicht kollidiert, sondemn wsr z=iVerstandrus des der E ~Jere Dounsnt, as edoh mt amode nah dm Inemaicnlen Erfindung zugridehecgenden Prunps cder der ibs zugruneleliegenden ltces okumn% as edoc crt a odr nah dm iternticalThe1one angegcoen it Anmieldedlaturn verffentlicht worden it *X Verdifentlachung von besondecr Bed;!utung; die beanaruchte ErfindunE V Verdffentiichtmig, die geelgnet ist, einen Priontitsanspruch zweifelhalt er- kann allein aufgrund dieser Verdffentlichung nicht al eu oder auf sichcinen zu lassen, cider durch die dlas Vcr~ffentlichungsdatm, cuier crfindenicher Titigkezt beruhend betrachtet werden ande'ren im Recherchenbencht genannten Veroffentliehung belegt werdeli Verdffentlichung von bcsonderer Bedcutung; die beansprucbte ErfindunE soil oder die aus einemn andereni besondereri Grund angegeben ist (wie kann nieht als auf erfinderischer 'l'tigkeit beruhtend betrachtet ausgeftlbrt) werden, wenn die Vcr6ffentliehung vut esner odes mebhreren anderen Veroffentlichung, die ich auf elne enfindliche Offenbanaing, Ver6(Tentliehungen diescr Kategorie in Verbindung gebracht wird und esne Benuizung, emne Ausstellung oder andere Maflnahmen bezieht diese Verbzindung ftlr ctnen Facbm=n naheltegend ast Verwffentlichung, die vor dem inteinationalen Anmnieclatumn, aber nach dern beanpruchten PnontAsdaw~m verffentlicht warden ist& Verdifentlichung, dite Mitglied derselben Patentfnlie ist Datum des Abschlusses der internatialen Recherche Absendedatarm des trternationalen Recherchenbencbts 7. Dezember 1993 I Name und Postanxtthnft der Interrnatonale Recherclicnbehdrde Bevollmichugter Bediensteter Europaiselies Patentamt, P.B. 5818 Patentlaan 2 NL.- 2280 HV Pijswilk Tel. (r31-70) 340-2040, Tx. 31651 po nl, Rne Fax 31.70) 340-3016 ikl L -rynblatt P JISA/210 (Blatt 1) (Jul! 1992) INTERNATIONA LER RECHERCHENBERICHT Angaben zu Vcr6ffcndtcbui...,i, die zur scibcn Patentrantilic gchora P tles 93/02705 Im Recherchenbericht Datum der Mirglied(er) der Datum der angef~hrtes Patentdokument Veroffentlichung k'awntfamilie Veroffendichung WO-A-8900573 26-01-89 DE-A- 3723246 26-01-89 AU-A- 1980388 13-02-89 EP-A- 0303802 22-02-89 DE-A-4109671 24-C'9-92 EP-A- 0505819 30-09-92 JP-A- 511253S 07-05-93 Formblatt PC771SAJ210 (Anhang Patentfamitle)(Juli 1992)