CA2029132C - Sulphonylaminocarbonyltriazolinones having substituents which are bonded via sulphur - Google Patents

Sulphonylaminocarbonyltriazolinones having substituents which are bonded via sulphur Download PDF

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CA2029132C
CA2029132C CA002029132A CA2029132A CA2029132C CA 2029132 C CA2029132 C CA 2029132C CA 002029132 A CA002029132 A CA 002029132A CA 2029132 A CA2029132 A CA 2029132A CA 2029132 C CA2029132 C CA 2029132C
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alkyl
fluorine
chlorine
optionally substituted
alkoxy
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CA2029132A1 (en
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Klaus-Helmut Muller
Peter Babczinski
Hans-Joachim Santel
Robert R. Schmidt
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Bayer AG
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
    • A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
    • A01N47/38—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the group >N—CO—N< where at least one nitrogen atom is part of a heterocyclic ring; Thio analogues thereof
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
    • C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
    • C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
    • C07D249/10—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D249/12—Oxygen or sulfur atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Agronomy & Crop Science (AREA)
  • Engineering & Computer Science (AREA)
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Abstract

Herbicidal sulphonylaminocarbonyl-triazolinones having substituents which are bonded via sulphur, of the formula in which n represents the numbers 0, 1 or 2, R1 represents hydrogen, hydroxyl or amino, or represents an optionally substituted radical from the series comprising alkyl, alkenyl, alkinyl, cycloalkyl, aralkyl, aryl, alkoxy, alkenyloxy, alk.ylamino, cycloalkylamino and dialkylamino, R2 represents an optionally substituted radical from the series comprising alkyl, alkenyl, alkinyl, cycloalkyl, cycloalkenyl, aralkyl and aryl, and R3 represents an optionally substituted radical from the series comprising alkyl, aralkyl, aryl and heteroaryl, as well as salts of compounds for the formula (I).
Also new are the compounds for the following formula:
in which N, R1 and R2 have the abovementioned meanings and Z
represents halogen, alkoxy, aralkoxy or aryloxy.

Description

~~~r~~.3 The invention relates to new sulphonylamino-carbonyltriazolinones having substituents which are bonded via sulphur, to a variety of processes for their preparation, and to their use as herbicides.
It is known that certain substituted amino-carbonyliruidazolinones, such as, for example, 1-isobutyl-aminocarbonyl-2-imidazolidinone (isocarbamid), have herbicidal properties (cf. R. Wegler, Chemie der Pflanzenschutz-and and Schadlingsbekampfungsmittel [Chemistry of Plant Protection Agents and Pesticides], Volume 5, p. 219, Springer-Verlag, Berlin-Heidelberg-New York, 197?). However, the action of this compound is not satisfactory in all resgects.
The new sulphonylaminocarbonyl-triazolinones having substituents which are bonded via sulphur, of the formula (I) ' R3-S02-NI-i-CO-N~N-R1 ( I ) ~S(0)n-R2 in which n represents the numbers 0, 1 or 2, Rx represents hydrogen, hydroxyl or amino, or repre seats an optionally substituted radical from the series comprising alkyl, alkenyl, alkinyl, cyclo alkyl, aralkyl, aryl, alkoxy, alkenyloxy, al 1 ky -Le A 27 156 - I -~~?~13?
amino, cycloalkylamino and dialkylamino, RZ represents an optionally substituted radical from the series comprising alkyl, alkenyl, alkinyl, cycloalkyl, cycloalkenyl, aralkyl and aryl, and R3 represents an optionally substituted radical from the series comprising alkyl, aralkyl, aryl and heteroaryl, as well as salts of compounds of the formula ( I ) , have now been found.
The new sulphonylaminocarbonyltriazolinones having substituents which are bonded via sulphur, of the general formula (I), are obtained when a) triazolinones of the general formula (II) ~ (II) HN~N-R1 ~S(O)n-R2 in which n, R~ and RZ have the abovementioned meanings, are reacted with sulphonyl isocyanates of the general formula (III) R3-S02-N~~=p (III) in which R3 has the abovementioned meaning, if appropriate in the presence of a diluent, or when b) triazolinone derivatives of the general formula (IV) Le A 27 156 _ z Z-CO-N~N-R1 (zv) ~S(OJn-R2 in which n, Rl and RZ have the abovementioned meanings and Z represents halogen, alkoxy, aralkoxy or aryloxy, are reacted with sulphonamides of the general formula (V) R3-S02-NHZ (V) in which R3 has trxe abovementioned meaning, if appropriate in the presence of an acid acceptor and if appropriate in the presence of a diluent, or when c) triazolinones of the general formula (II) O
u II
HN~N-R1 ( ) ~S(0)n-R2 in which nr R~ and RZ have the abovementioned meanings, are reacted with sulphonamide derivatives of the Le A 27 156 general formula (VI) R3-S02-NH-C0-Z (vI) in which R~ has the abovementioned meaning and z represents halogen, alkoxy, aralkoxy or aryloxy, if appropriate in the presence of an acid acceptor and if appropriate in the presence of a diluent, and, if desired, salts are formed by customary methods from the compounds of the formula (I) prepared by process (a), (b) or (c).
The new sulphonylaminocarbonyltriazolinones having substituents which are bonded via sulphur, of the general formula (I), and their salts are distinguished by a powerful herbicidal activity.
Surprisingly, the new compounds of the formula (I) have a considerably better herbicidal action than the herbicide 1-isobutylaminocarbonyl-2-imidazol-idinone (isocarbamid), which is known and has a similar structure.
The invention preferably relates to compounds of the formula (I) in which n represents the numbers 0, 1 or 2, R1 represents hydrogen, hydroxyl or amino, or repre sents C1-C6-alkyl which is optionally substituted by fluorine, chlorine, bromine, cyano, C~-C4-alkoxy, Ca-Ca-alkylcarbonyl or C1-C4-alkoxy-carbonyl, or represents C3-C6-alkenyl or C3-Cs-alkinyl, each of which is optionally substituted by fluorine, chlor-Le ~, 27 156 _ q, ine and/or bromine, or represents C3-Cs-cycloalkyl which is optionally substituted by fluorine, chlor-ine, bromine and/or C1-C4-alkyl, or represents phenyl-C1-C3-alkyl which is optionally substituted by fluorine, chlorine, bromine, cyano, vitro, Cl-C4-alkyl, trifluoromethyl, C1-Cb-alkoxy and/or C1-C4-alkoxy-carbonyl, or represents phenyl which is optionally substituted by fluorine, chlorine, bromine, cyano, vitro, C,-C4-alkyl, trifluoromethyl, C1-C4-alkoxy, fluorine- and/or chlorine-substituted C1-C3-alkoxy, C1-C4-alkylthio, fluorine- and/or chlorine-substituted C1-C3-alkylthio, Cl-C4-alkylsul-phinyl, Cl-C4-alkylsulghonyl and/or Cl-C4-alkoxy-carbonyl, or represents C1-Cfi-alkoxy which is option-ally substituted by fluorine, chlorine, cyano, phenyl, C1-C4-alkoxy or C~-C4-alkoxy-carbonyl, or represents C3-C,;-alkenyloxy, ar represents Cl-C4-alkylamino which is optionally substituted by f luorine, cyano, C1-C4-alkoxy or C~-Ca-alkoxy-carbonyl, ar represents C3-C6-cycloalkylamino or di-( Cl-C4-alkyl ) -amino, R2 represents Cl-Cfi-alkyl which is optionally substi-tuted by fluorine, chlorine, bromine, cyano, C3-C6-cycloalkyl, C1-C4-alkoxy or C1-C4-alkoxycarbonyl, or represents C3-C6-alkenyl or C3-C6-alkinyl, each of which is optionally substituted by fluorine, chlor-ine and/or bromine, or represents C3-C6-cycloalkyl which is optionally substituted by fluorine, chlor-ine, bromine and/or C1-C4-alkyl, or represents cyclohexenyl, or represents phenyl-C~-C3-alkyl which Le A 27 156 - 5 -is optionally substituted by fluorine, chlorine, bromine, cyano, vitro, C1-C4-alkyl, trifluoromethyl, C1-C4-alkoxy and/or C1-C,,-alkoxycarbonyl, or repre-sents phenyl which is optionally substituted by fluorine, chlorine, bromine, cyano, vitro, C
alkyl, trifluoromethyl, C1-C4-alkoxy, fluorine-and/or chlorine-substituted C1-C3-alkoxy, C1-C4-alkylthio, fluorine- and/or chlorine-substituted C1-C3-alkylthio, C1-G4-alkyl-sulphinyl, Cl-C4-alkyl-sulphonyl and/or C1-C4-alkoxy-carbonyl, and R3 represents the group ~ ~ where R4 and RS are identical or different and represent hydrogen, fluorine, chlorine, bromine, iodine, vitro, C1-C6-alkyl (which is optionally substituted by fluorine, chlorine, bromine, cyano, carboxyl, C1-C4-alkoxycarbonyl, C1-C4-alkylamino-carbonyl, di-( C1-C,,-alkyl ) amino-carbonyl, hydroxyl, C1-C4-alkoxy, formyloxy, C1-C4-alkyl-carbonyloxy, C1-C4-alkoxy-carbonyloxy, C1-C4-alkylamino-carbonyloxy, C1-C4-alkylthio, C1-C4-alkylsulphinyl, C1-C,,-alkylsulphonyl, di- ( C1-C4-alkyl ) -aminosulphonyl , C3-Cs-cycloalkyl or phenyl ) , or represent CZ-Cs-alkenyl (which is option-ally substituted by fluorine, chlorine, bromine, cyano, Cl-C4-alkoxy-carbonyl, carboxyl or phenyl ) , or represent Cy-C6-alkinyl (which is optionally substi-tuted by fluorine, chlorine, broanine, cyano, C1-C4-alkoxy-carbonyl, carboxyl or phenyl), or represent Le A 27 156 - S -~p~~~~?
C1-C4-alkoxy (which is optionally substituted by fluorine, chlorine, bromine, cyano, carboxyl, C~-C~-alkoxy-carbonyl, C~-C4-alkoxy, C~-C4-alkylthio, C1-C4-alkylsulphinyl or C1-C4-alkylsulphonyl ) , or represent Cl-C4-alkylthio (which is optionally substituted by fluorine, chlorine, bromine, cyano, carboxyl, C1-C4-alkoxy-carbonyl, C1-C4-alkylthio, C1-C4-alkylsulphinyl or Cl-C4-alkylsulphonyl ) , or represent C3-C6-alkenyl-oxy (which is optionally substituted by fluorine, chlorine, bromine, cyano or C1-C,~-alkoxy-carbonyl}, or represent C2-Cs-alkenylthio (which is optionally substituted by fluorine, chlorine, bromine, cyano, nitro, C1-C3-alkylthio or Gl-C,,-alkoxycarbonyl ) , C3-G6-alkinyloxy or C3-C6-alkinylthio, or represent the radical -S(O)p-R6 where p represents the numbers 1 or 2 and R6 represents C1-C,,-alkyl (which is optionally substituted by fluorine, chlorine, bromine, cyano ar C1-C4-alkoxy-carbonyl ) , C3-C6-alkenyl, C3-Cs-a7.kinyl, C1-C4-alkoxy, C1-C4-alkoxy-C1-C4-alkylamino, Cl-C,,-alkylamino, di- ( Cl-C4-alkyl ) -amino or phenyl, or represents the radical -NHOR' where R' represents C1-C1z-alkyl (which is optionally substituted by fluorine, chlorine, cyano, C1-C,,-alkoxy, C1-C4-alkylthio, C1-C~,-alkylsul phinyl, Cl-C4-alkylsulphonyl, Cl-C4-alkyl carbonyl, Cl-C~-alkoxycarbonyl, C1-C4-alkyl amino-carbonyl or di-(Cl-C4-alkyl}-amino carbonyl), or represents C3-C6-alkenyl (which Le A 27 156 - 7 -~~~~~~~
is optionally substituted by fluorine, chlorine or bromine ) , C3-Cs-alkinyl, C3-Cs-cycloalkyl, C3-Cs-cycloalkyl-C1-CZ-alkyl, phenyl-C1-CZ-alkyl (which is optionally substituted by fluorine, chlorine, vitro, cyano, C1-Ca-alkyl, Cl-C4-alkoxy or C1-C4-alkoxy-carbonyl), or represents benzhydryl, or represents phenyl (which is optionally substituted by fluorine, chlorine, vitro, cyano, Ci-C4-alkyl, trifluoromethyl, C1-C,,-alkoxy, C1-C2-fluoroalkoxy, Cl-C4-alkylthio, trifluoromethylthio or C~-C4-alkoxycarbonyl), R4 and/or RS furthermore represent phenyl or phenoxy, ar represent Cl-C4-alkylcarbonylamino, C1-C4 alkoxycarbonyiamino, C1-C~-alkylamino-carbonyl amino or di-(C1-C4-alkyl)-amino-carbonylamina, or represent the radical -CO-RB where Rs represents C1-Cs-alkyl, Cl-Cs-alkoxy, C3-Cs cycloalkoxy, C3-Cs-alkenyloxy, Cl-C4 alkylthio, C1-C4-alkylamino, Cl-C4-alkoxyamino, Cl-C,,_ alkoxy-Cl-C4-alkyl-amino or di- ( Cl-Ck-alkyl ) -amino (each of which is optionally substi-tuted by fluorine and/or chlorine), R" and/or RS furthermore represent trimethylsilyl, thiazolinyl, C1-C4-alkylsulphonyloxy or di-(Ci-C4 alkyl)-aminosulphonylamino, or represent the radical -CH=N-R9 where R9 represents C~-Cs-alkyl which is optionally substituted by fluorine, chlorine, cyano, carboacyl, C1-C~-alkoxy, C1-C4-alkylthio, Ci-C4 Le A 27 156 -- 8 alkylsulphinyl or C1-Ca-alkylsulphonyl, or represents benzyl which is optionally sub-stituted by fluorine or chlorine, or repre-sents C3-Cs-alkenyl or C3-Cs-alkinyl, each of which is optionally substituted by fluorine or chlorine, or represents phenyl which is optionally substituted by fluorine, chlorine, bromine, C1-C4-alkyl, C1-C4-alkoxy, trifluoro-methyl, trifluoromethoxy or trifluoromethyl-thic, or represents C,-Cs-alkoxy, G3-Cs-alken-oxy, C3-Cs-alkinoxy or benzyloxy, each of which is optionally substituted by fluorine and/or chlorine, or represents amino, C1-C4-alkylamino, di-(C1-C4-alkyl)-amino, phenyl-amino, C1-C4-alkyl-carbonyl-amino, C1-C4--alkoxy-carbonylamino or C1-C4-alkyl-sulphonyl-amino, or represents phenylsulphonylamino which is optionally substituted by fluorine, chlorine, bromine or methyl, furthermore -CH ' R3 represents the radical R10 Rii ~ where R1° represents hydrogen or C1-C~-alkyl, Rli and Rlz are identical or different and represent hydrogen, fluorine, chlorine, bromine, vitro, cyano, C1-C4-alkyl (which is optionally substi tuted by fluorine and/or chlorine), Ca-Ca-alkaxy (which is optionally substituted by fluorine and/or chlorine), carboxyl, Cl-C4-alkoxy-carbonyl, Le A 27 156 ~ g -dimethylaminocarbonyl, C1-C4-alkylsulphonyl or di-(Ca-C4-alkyl)-aminosulphonyl; furthermore R3 represents the radical R13 ~ f ~ R14 where Rl3and R1" are identical or different and represent hydxogen, fluorine, chlorine, bromine, vitro, cyano, C1-C~-alkyl (which is optionally substituted by fluorine and/or chlorine) or Ci-C4-alkoxy (which is optionally substituted by fluorine and/or chlorine);
furthermore R15 R3 represents the radical / ~ where R15 and R16 are identical or different and represent hydrogen, fluorine, chlorine, bromine, vitro, cyano, C1-C4-alkyl {which is optionally substituted by fluorine and/or chlorine), C~-C~-alkoxy (which is optionally substituted by fluorine and/or chlorine), or represents C1-C4-alkylthio, C1-C4-alkylsulphinyl or C1-C4-alkyl-sulphonyl (each of which is optionally substi-tuted by fluorine and/or chlorine) , or represents ami.nosulphonyl, mono-(Cl-C4-alkyl)-aminosulphonyl, or represents di-{C1-Cs-alkyl)-aminosulphonyl or C1-C4-alkoxycarbonyl or dimethylaminocarbonyl;
furthermore R3 represents the radical R17 ~ ( ~Rlg where w N' Le A 27 156 _ 10 Rl' and RI8 are identical or different and represent hydrogen, fluorine, chlorine, bromine, C1-C4-alkyl (which is optionally substituted by fluorine and/or bromine), Cl-C4-alkoxy (which is optionally substi-toted by fluorine and/or chlorine), or represent C1-C4-alkylthio, C1-C,,-alkylsulphinyl or Cl-Ca-alkyl-sulphonyl (which is optionally substituted by fluorine and/or chlorine), or represent di-(C1-C4-alkyl)-aminosulphonyl;
furthermore R3 represents the radical _~2o where R1~ and RZ° are identical or different and represent hydrogen, fluorine, chlorine, bromine, cyano, vitro, C,-C4-alkyl (which is optionally substi-I5 toted by fluorine and/or chlorine}, Cl-C4-alkoxy (which is optionally substituted by fluorine and/or chlorine), C1-C,,-alkylthio, C~-C4-alkylsul-phinyl or C1-C4-alkylsulphonyl (which is option-ally substituted by fluorine and/or chlorine), di- ( Ci-C,,-alkyl ) -amino-sulphonyl, C1-C,,-alkoxy-car-bonyl or dimethylaminocarbonyl, and A represents oxygen, sulphur or the group N-Z1 where Z1 represents hydrogen, Cl-C4-alkyl (which is optionally substituted by fluorine, chlorine, bromine or cyano), C3-C6-cycloalkyl, ben~yl, phenyl (which is optionally substituted by L~e A 2 7 15 6 - 11 ~~~~1~°~
fluorine, chlorine, bromine or nitro), C1-Ca-alkylcarbonyl, C1-Ca-alkoxy-carbonyl or di-( CmCa-alkyl ) -aminocarbonyl;
furthermore R3 represents the radical ~22 where Z
R21 and R22 are identical or different and represent hydrogen, C,-Ca-alkyl, halogen, C1-Ca-alkoxycar-bonyl, Cl-Ca-alkoxy or Cl-Ca-halogenoalkoaty, Y1 represents sulphur or the group N-R2a where Ras represents hydrogen or C~-Ca-alkyl;
furthermore R3 represents the radical '~, where N~N~ 2 5 R

RZa represents hydrogen, Ci-Ca-alkyl, benzyl, pyri-dyl, quinolinyl or phenyl, R25 represents hydrogen, halogen, cyano, nitro, C1-Ca-alkyl (which is optionally substituted by fluorine and/or chlorine), C1-Ca-alkoxy (which is optionally substituted by fluorine and/or chlorine), dioxolanyl or C1-Ca-alkoxy-carbonyl and RZS represents hydrogen, halogen or C1-Ca-alkyl;
furthermore Le A 27 156 - 12 -R3 represents one of the groups listed below, H3C0 ~~ ' H3C
S~'N-C~H9 ; NHS CH2GF3 The invention furthermore preferably relates to sodium salts, potassium salts, magnesium salts, calcium salts, ammonium salts, C1-C4-alkyl-ammonium salts, di-(C1-C4-alkyl)-ammonium salts, tri-(C1-C4-alkyl)-ammonium salts, CS- or Cs-cycloalkyl-ammonium salts and di-(Cl-CZ-alkyl)-benzyl-ammonium salts of compounds of the formula ( I ) in which n, R1, RZ and R3 have the meanings indicated above as being preferred.
In particular, the invention relates to compounds of the formula (I) in which n represents the numbers 0, 1 or 2, R1 represents hydrogen ar amino, or represents CI-C4 alkyl which is optionally substituted by fluorine, cyano, methoxy or ethoxy, or represents allyl, or represents C3-C6-cycloalkyl, or represents benzyl, or represents phenyl, or represents Cl-C4-alkoxy, or represents C3-C~-alkenyloxy, or represents C1-C3 alkylamino, C3-C6-cycloalkylamina, or represents di 2 0 ( C1-C3-alkyl ) -amino, Le A 27 156 - 13 -~~~~~c~"t~
Rz represents hydrogen, or represents C1-G4-alkyl which is optionally substituted by fluorine and/or chlor-ine, methoxy or ethoxy, or represents C3-C4-alkenyl which is optionally substituted by fluorine and/or chlorine, or represents C3-C6-cycloalkyl, or repre-sents benzyl which is optionally substituted by fluorine, chlorine and/or methyl, and RS
R3 represents the group ~ where R'1 R° represents fluorine, chlorine, bromine, methyl, trifluoromethyl, methoxy, difluoromethoxy, trifluoromethoxy, 2-chloro-ethoxy, 2-methoxy-ethoxy, C1-C3-alkylthio, C1-C3-alkylsulphinyl, C1-C3-alkylsulphonyl, dimethylaminosulphonyl, diethylaminosulphonyl, N-methoxy-N-methylamino-sulphonyl, methoxyaminosulphonyl, phenyl, phenoxy or C1-C3-alkoxy-carbonyl, and RS represents hydrogen, fluorine, chlorine or bromine furthermore ~--~ R12 2d R3 represents the radical -CH~ where ~1 ~0 R1° represents hydrogen, R11 represents fluorine, chlorine, bromine, methyl, Le A 27 156 _ 14 -~~~~~.3~ .
methoxy, difluoromethoxy, trifluoromethoxy, ethoxy, methoxycarbonyl, ethoxycarbonyl, methyl-sulphonyl or dimethylaminosulphonyl, and R12 represents hydrogen;
furthermore R3 represents the radical ~ I
RO-C S

where R represents C1-C4-alkyl, or represents the radical RO-CI
N~N
I
where R represents Cl-C4-alkyl. CH3 Examples of the compounds according to the invention are listed in Table 1 below - cf. also the Preparation Examples.

R3-S02-NH-CO-N~N-R1 (I) S(0)n-R2 Le .A 2? 15s - 15 -Table to Examples of the compounds of the formula (T) R~ R~ R3 n F
CH3 /-\ 0 CH3 /~\ 0 CH3 C2N5 /'\ 0 OCHF'2 CH3 CH2-CH=CHI -\ 0 S02N(CH372 CHO CH3 -\

CH3 CH3 /~\ H2- 0 CHO C2H5 ~ ~ 0 NON

Le A 27 156 - 16 -.
Table 1: (Continuation) R~ R2 R~ n CH3 C2H5 ' ~ 0 CH3 C2H5 / \ 0 J \
C2H5 C2H5 /-\ 0 / i \

OCFO
CH3 /~\ H2- 0 C2H5 /-\. 0 CH(CH312 ~ ~ CON(CH3)2 0 Le A 27 156 - 17 -Table (Continuation) 1:

R1 R2 R3 n s CH3 CH(CH312 ~ 0 SCH(CH312 ~

CH3 CHZ-CH=CH2 ~~ 1 C2H5 CH3 ~ 2 ~

F

C2H5 C~HS ~-~ 0 Si(CH313 CH3 C2H5 ~ 0 ~

-/

C2H5 C3H7 ~\ 0 CON(CH312 ~1 ~e .~ 27 156 _ lg ~fl~~~:l.~
Tabie 1: (Continuation) R1 R2 R3 n Br CH2 /-\ CH3 / \ 0 C2H5 \ 0 /

-r CHI L I o NON

S02N(CH3)2 C2H5 \ 0 /

_ OCHF~
C3H7-n \ H2- 0 /

-COOCH(CH3)2 \

Le A 27 156 - 19 -~~~~~J~
Table 1: (Continuation) R1 R2 R3 n CHO CH3 \ 0 CH3 C2H5 p / ~ \
CH3 -CH2-C=CH / \ p S
N

/ \

C2H5 I ( 0 NON
i I

v CH3 N'N ~ 0 N~ w i Le A 27 156 - 20 -Table 1: (Continuation) n CH3 CHO ~ ~

NHS

CON(CHO)Z

CHO COH7 _ \ 0 ~

HOC

C2H5 C2Hg ~ 0 ~

S OOCHO

COOCHO
~
~

CH2-CH=CH2 C2HS ~

CH2-CH=CH2 CHO ~ f NON

CHO

COOCHO
~
\

OCHO CHO ~

S02NCH0(0CH0) Le A 27 156 _ 21 _ ~~?'~~.~~
Table 1: (Continuation) R2 R2 R3 n OC3Hp CH?-CH=CH2 /~\ 0 CH3 CHO /-\ 0 C2H5 / \

Br C2H5 / \ 0 CHO

C2H5 C2H5 ~ ~ 0 N'~N

CH3 CZHS /-\ 0 S02 /-\
Le A 27 156 - 22 ->~~~
Table 1: (Continuation) R1 R2 R3 n CH3 C~H7 f~~ H2- 0 OCH3 CH3 ~ ' 0 OCZHS CH3 f~~ 0 OCH2CH~-C1 OC2H5 C2H5 f'~ 0 F
0-CH2-CH=CH2 C2H5 f-~ 0 CH3 CzHS ~ 0 r CF3 ~'N
Le A27 156 w 23 -Table 1: (Continuation) gl g2 g3 n N(CH31Z CH3 w I
r ~N

CH ~
S

N(CH312 CH3 0 Ze A 27 156 - 24 -If, for example, 2,6-difluoro-phenyl isocyanate and 5-ethyl.thio-4-methoxy-2,4-dihydro-3H-1,2,4-triazol-3-one are used as starting substances, the course of the reaction in grocess (a) according to the invention can be outlined by the following equation:

S02-N=C=0 + H~N~NiOCHS >
F ~SC2HS

S02-NH-CO~N~Ni0CH3 F ~SC2H5 If, for example, 2-methylthio-benzenesulphonamide and 2-chlorocarbonyl-4-dimethylamino-5-propylthio-2,4-dihydro-3H-1,2,4-triazol-3-one are used as starting substances, the course of the reaction in process (b) according to the invention can be outlined by the follow-ing equation:

(. ,r°S02-NH2 + C 1-CO~N~N~N ( CH3 ) 2 -°->
'~% (~~ - HC 1 ~SC3H7 ~S02-NH-CO~N~N~'N ( CH3 ) 2 ~SG3H7 Le A 27 156 - 25 -If, for example, N-methoxycarbonyl-2-methoxy-benzenesulphonamide and 5-methylsulphonyl-4-difluoro-methyl-2,4-dihydro-~H-1,2,4-triazol-3-one are used as starting substances, the course of the reaction in process (c) according to the invention can be outlined by the following equation:

~ f~t~N~N~'CHF 2 ~S02-NH-COOCH3 + ~--~~[
~S02CH3 -'> ~-S02-NH-CO~N~N~'CHFz ~S02CH3 Formula (IIj provides a general definition of the triazolinones to be used as starting substances in processes (a) and (cj according to the invention for the preparation of compounds of the formula (Ij.
In Formula ( II ) , n, R1 and RZ preferably, or in particular, have those meanings which have already been mentioned above in connection with the description of the Le A 27 156 - 2~

~~~~~~.3 compounds of the formula (I) according to the invention as being preferred, or particularly preferred, for n, R1 and R2.
Examples of the starting substances of the formula (II) are listed in Table 2 below.

HN~N~R1 ~- ' (II) ~S(0)n-g2 Table 2s Examples of the starting substances of the formula (II) n H CHg 0 CH(CHS12 CH

Le A 27 156 _ 27 - ~~8~~~~~
TaL~le 2: (Continuation R1 R2 n CH3 C3H~ 0 CH3 CH(CH312 0 CH3 CH2-CH=CH2 0 CH3 CH2 ~y~ 0 CH3 CH2-G=CH p C2H5 , 0 CH2-GH=CH2 C2H5 0 CH2-CHBr-CH2Br G2H~ p CH2-CH=CH2 0 Le A 27 156 - 28 -~fl~~~.3~
Table 2: (Continuation R1 R2 n CH(CH3)2 0 C2H5 CH(CH3)2 0 C3H~ CH(CH3)Z 0 CH2-CH=CH2 C3H~ 0 C2H5 -CH2-C=CH 0 CgH7 C3H~ 0 Le A 27 156 - 29 -The starting substances of the formula ~II~ are known and/or can be prepared by processes known per se (cf. J. Heterocycl. Chem. 15 (1978), pp. 377-384; DE-OS
(German Published Specification) 2,250,572; DE-OS (German Published Specification) 2,527,676; DE-OS (German Published Specification) 3,709,574; US Patent 4,098,896;
US Patent 4,110 X32; JP-A-52-125 168).
Formula (III) provides a general definition of the sulphonyl isocyanates also to be used as starting substances in process (a) according to the invention for the preparation of compounds of the formula (I).
In formula ( III ) , R3 preferably, or in particular, has the meaning which has already been mentioned above in connection with the description of the compounds of the formula (I) according to the invention as being pre-ferred, or particularly preferred, for R3.
Examples of the starting substances of the formula (III) which may be mentioned are:
2-fluoro-, 2-chloro-, 2-bromo-, 2-methyl-, 2-methoxy-, 2 trifluoromethyl-, 2-difluoromethoxy-, 2-trifluorometh oxy-, 2-methylthio-, 2-ethylthio-, 2-propylthio-, 2 methylsulphinyl-,2-methylsulphonyl-,2-dimethylaminosul phonyl-, 2-diethylaminosulphonyl-, 2-(N-methoxy-N
methyl)-aminosulphonyl-, 2-phenyl-, 2-phenoxy-, 2-meth oxycarbonyl-, 2-ethoxycarbonyl-, 2-propoxycarbonyl- and 2-isopropoxycarbonyl-phenylsulphonyl isocyanate, 2-fluoro-, 2-chloro-, 2-difluoromethoxy-, 2-trifluorometh-oxy-, 2-methoxycarbonyl- and 2-ethoxycarbonyl-benzylsul-phonyl isocyanate, 2-methoxycarbonyl-3-thienyl-sulphonyl isocyanate, 4-methoxycarbonyl- and 4-ethoxycarbonyl-1-Le A 27 156 - 30 -methyl-pyrazol-5-yl-sulphonylisocyanate.
The sulphonyl isocyanates of the formula (ITI) are known and/'or can be prepared by processes known per se (cf. US Patent 4,127,405, 4,169,719, 4,3?1,391;
EP-A 7,687, 13,480, 21,641, 23,141, 23,422, 30,139, 35,893, 44,808, 44,809, 48,143, 51,466, 64,322, 70,041, 173,312).
Process (a) according to the invention for the preparation of the new compounds of the formula ( I ) is preferably carried out using diluents. Suitable diluents for this purpose are virtually all inert organic sol-vents. These preferably include aliphatic and aramatic, optionally halogenated hydrocarbons, such as pentane, hexane, heptane, cyclohexane, petroleum ether, benzine, ligroin, benzene, toluene, xylene, methylene chloride, ethylene chloride, chloroform, carbon tetrachloride, chlorobenzene and o-dichlorobenzene, ethers, such as diethyl ether and dibutyl ether, glycol dimethyl ether and diglycol dimethyl ether, tetrahydrofuran and dioxane, ketones, such as acetone, methyl ethyl ketone, methyl isopropyl ketone and methyl isobutyl ketone, esters, such as methyl acetate and ethyl acetate, nitriles, such as, for example, acetonitrile and propionitrile, amides, such as, for example, dimethylformamide, dimethylacetamide and N-methyl-pyrrolidone, and also dimethyl sulphoxide, tetramethylene sulphone and hexamethylphosphoric tri-amide.
In process (a) according to 'the invention, the reaction temperatures can be varied within a substantial range. In general, the process is carried out at he A 27 156 - 31 -~~~~~.~a temperatures between 0°C and 150°C, preferably at temper-atures between 10°C and 00°C.
Process (a) according to the invention is gener-ally carried out under atmospheric pressure.
For carrying out process (a) according to the invention, between 1 and 3 moles, preferably between 1 and 2 moles, of sulphonyl isocyanate of the formula (III) are generally employed per mole of triazolinone of the formula (II).
The reactants can be combined in any desired sequence. The reaction mixture is stirred until the reaction is complete, and the product is isolated by filtration with suction. In another work-up variant, the mixture is concentrated, and the crude product which remains in the residue is crystallized with a suitable solvent, such as, for example, diethyl ether. The product of the formula (I), which in this process is obtained in crystalline form, is isolated by filtration with suction.
Formula (IV) provides a general definition of the triazolinone derivatives to be used as starting sub stances in process (b) according to the invention for the preparation of compounds of the formula (I).
In formula (IV), n, R1 and R2 preferably, or in particular, have those meanings which have already been mentioned above in connection with the description of the compounds of the formula (I) according to the invention as being preferred, or particularly preferred, for n, R1 and RZ, and Z preferably represents chlorine, C1-C4-alkoxy, benzyl-oxy or phenoxy, in particular methoxy or phenoxy.
he A 27 156 - 32 -r~a Possible examples of the starting substances of formula (IV) are the compounds of the formula (IV) to be prepared from the compounds of the formula (II) listed in Table 2 and phosgene, methyl chloroformate, benzyl chloroformate, phenyl chloroformate or dipheny.l carbonate.
The starting substances of the formula (IV) were hitherto unknown.
The new triazolinone derivatives of the formula (IV) are obtained when triazolinones of the general formula (I2) HN~NiRj (II) ~StO)n-Ft2 in which n, R1 and RZ have the abovementioned meanings, are reacted with carbonic acid derivatives of the general formula (XI) z-co-zI (xz) in which Z has the abovementioned meaning and Z1 represents a leaving group, such as chlorine, methoxy, benzyloxy or phenoxy, if appropriate in the presence of a diluent, such as, far Le A 2Z 156 _ 33 _ ~ ') ~a~~~ ~p~
example, tetrahydrofuran, and if appropriate in the presence of an acid acceptor, such as, for example, sodium hydride or potassium tent-butylate, at temper atures between -20°C and +100°C (cf. also the Preparation Examples).
Formula (V) provides a general definition of the sulphonamides also to be used as starting substances in process (b) according to the invention far the prepar-ation of compounds of the formula (I).
ZO In formula (V), R3 preferably, or in particular, has the meaning which has already been mentioned above in connection with the description of the compounds of the formula (I) according to the invention as being pre-ferred, or particularly preferred, for R3.
Examples of the starting substances of the formula (V) which may be mentioned are:
2-fluoro-, 2-chloro-, 2-bromo-, 2-methyl-, 2-methoxy-, 2-trifluoromethyl-, 2-difluoromethoxy-, 2-trifluorometh-oxy-, 2-methylthio-, 2-ethylthio-, 2-propylthio-, 2-methylsulphinyl-,2-methylsulphonyl-,2-dimethylaminosul-phonyl-, 2-diethylaminosulphonyl-, 2-(N-methoxy-N-methyl)-aminosulphonyl-, 2-phenyl-, 2-phenoxy-, 2-meth-oxycarbonyl-, 2-ethoxycarbonyl-, 2-propoxycarbonyl- and 2-isopropoxycarbonyl-benzenesulphonamide, 2-fluoro-, 2-chloro-, 2-.difluoromethoxy-, 2-trifluoromethoxy-, 2-methoxycarbonyl- and 2-ethoxycarbonyl-phenylmethanesul-phonamide, 2-methoxycarbonyl-3-thioghenesulphonamide, 4-methoxycarbonyl- and 4-ethoxycarbonyl-1-methyl-pyrazol-5-sulphonamide.
The sulphonamides of the formula (V) are known Le A 27 156 - 34 -and/or can be prepared by processes known per se (cf.US
Patents 4,127,405, 4,169,719, 4,371,391; EP-A 7,687, 13,480, 21,641, 23,141, 23,422, 30,139, 35,893, 44,808, 44,809, 48,143, 51,466, 64,322, 70,041, 173,312).
In process (b) according to the invention, prepar-ation of the new compounds of the formula (I) is prefer-ably carried out using diluents. Diluents which are suitable for this purpose are virtually all inert organic solvents, for example those which have been indicated above for process (a) according to the invention.
Acid acceptors which can be employed in pro-cess (b) according to the invention are all acid-binding agents which can customarily be used for reactions of this type. The following are preferably suitable: alkali metal hydroxides, such as, for example, sodium hydroxide and potassium hydroxide, alkaline earth metal hydroxides, such as, for example, calcium hydroxide, alkali metal carbonates and alkali metal alcoholates, such as sodium carbonate, potassium carbonate, sodium tert-butylate and potassium tert-butylate, furthermore aliphatic, aromatic or heterocyclic amines, for example triethylamine, trimethylamine, dimethylaniline, dimethylbenzylamine, pyridine, 1,5-diazabicyclo-[4,3,0]-non-5-ene (DBN), 1,8-diazabicyclo-[5,4,0]-undec-7-ene (DBU) and 1,4-diazabi-cyclo[2,2,2]-octane (DABCO).
In process (b) according to the invention, the reaction temperatures can be varied within a substantial range. In general, the process is carried out at temper atures between 0°C and 100°C, preferably at temperatures between 10°C and 60°C.
Z,e A 27 156 - 35 Cb fx ~ ~
.J
In general, process (b) according to the invention is carried out under atmospheric pressure.
However, it is also possible to carry out the process under increased or reduced pressure.
For carrying out process (b) according to the invention, the specifically required starting substances are generally employed in approximately equimolar amounts. However, it is also possible to use one of the two components employed in each case in a substantial excess . In general, the reactions are carried out in a suitable diluent in the presence of an acid acceptor, and the reaction mixture is stirred for several hours at the specifically required temperature. In process (b) accord-ing to the invention, working-up is carried out in each case by customary methods.
The triazolinones of the formula (TI) to be used as starting substances in process (c) according to the invention for the preparation of compounds of the formula (I) have already been described as starting substances for process (a) according to the invention.
Formula (VI) provides a general definition of the sulphonamide derivatives also to be used as starting substances in process (c) according to the invention far the preparation of compounds of the formula (I).
In formula (VI), R3 and Z preferably, or in particular, have those meanings which have already been mentioned above in connection with the description of the compounds of the formula (I), or (IV), according to the invention as being preferred, or particularly preferred, for R3 and Z .
Le A 27 156 - 36 -~,~,.~~
Process (c) according to the invention is preferably carried out using diluents. The same organic solvents which have been mentioned above in connection with the description of process (a) according to the invention are suitable for this purpose.
If appropriate, process (c) is carried out in the presence of an acid acceptor. The same acid-binding agents which have been mentioned above in connection with the description of process (b) according to the invention are suitable for this purpose.
In process (c) according to the invention, the reaction temperatures can be varied within a substantial range. In general, the process is carried out at temper atures between 0°C and 100°C, preferably at temperatures between 10°C and 60°C.
In general, process (c) according to the inven-tion is carried out under atmospheric pressure. However, it is also gossible to carry out the process under increased or reduced pressure.
For carrying out process (c) according to the invention, the specifically required starting substances are generally employed in approximately equi.molar amounts. However, it is also possible to use one of the two specifically employed components in a substantial excess . In general, the reactions are carried out in a suitable diluent in the presence of an acid acceptor, and the reaction mixture is stirred for several hours at the specifically required temperature. In process (c) accord-ing to the invention, working-up is carried out in each case by customary methods.
Le A 27 156 - 37 -S
y 1 ~ ~ ~ ~,~ :/J
Y ) k .:
For converting the compounds of the formula (I) into salts, they are stirred with suitable salt formers, such as, fox example, sodium hydroxide, sodium methylate, sodium ethylate, potassium hydroxide, potassium methylate or potassium ethylate, ammonia, isopropylamine, dibutyl-amine or triethylamine, in suitable diluents, such as, for example, water, methanol or ethanol. The salts can be isolated as crystalline products - then if appropriate after concentration.
The active compounds according to the invention can be used as defoliants, desiccants, agents for de-stroying broad-leaved plants and, especially, as weed-killers. By weeds, in the broadest sense, there are to be understood all plants which grow in locations where they are undesired. Whether the substances according to the invention act as total or selective herbicides depends essentially on the amount used.
The active compounds according to the invention can be used, for example, in connection with the follow ing plants:
Dicotyledon weeds of the genera: Sinapis, Lepidium, Galium, Stellaria, Matricaria, Anthernis, Galinsoga, Chenopodium, Urtica, Senecio, Amaranthus, Portulaca, Xanthium, Convolvulus, Ipomoea, Polygonum, Sesbania, Ambrosia, Cirsium, Carduus, Sonchus, Solanum, Rorippa, Rotala, Lindernia, Lamium, Veronica, Abutilon, Emex, Datura, Viola, Galeopsis, Papaver, Centaurea, Trifolium, Ranunculus and Taraxacum.
Dicotyledon cultures of the Genera: Gossypium, Glycine, Beta, Daucus, Phaseolus, Pisum, Solanum, Linum, Ipomoea, Vicia, Nicotiana, Lycopersicon, Arachis, Le A 27 256 - 38 -I r~ ~~ ~ oh. ~ ;i~
r l1 a a ~. cy r~
Brassica, Lactuca, Cucumis and Cucurbita.
Monocotyledon weeds of the genera: Echinochloa, Setaria, Panicum, Digitaria, Phleum, Poa, Festuca, Eleusine, Brachiaria, holium, Bromus, Avena, Cyperus, Sorghum, Agropyron, Cynodon, Monochoria, Fimbristylis, Sagittaria, Eleocharis, Scirpus, Paspalum, Ischaemum, Sphenoclea, Dactyloctenium, Agrostis, Alopecurus and Apera.
Monocotyledon cultures of the genera: 0ryza, ZO Zea, Triticum, Hordeum, Avena, Secale, Sorghum, Panicum, Saccharum, Ananas, Asparagus and Allium.
However, the use of the active compounds accord ing to the invention is in no way restricted to these genera, but also extends in the same manner to other plants.
The compounds are suitable, depending on the concentration, for the total combating of weeds, for example on industrial terrain and rail tracks, and on paths and squares with or without tree plantings.
Equally, the compounds can be employed for combating weeds in perennial cultures, for example afforestations, decorative tree plantings, orchards, vineyards, citrus groves, nut orchards, banana plantations, coffee plant a-tions, tea plantations, rubber plantations, oil palm plantations, cocoa plantations, soft fruit plantings and hop-fields, on lawn, turf and pasture-land, and for the selective combating of weeds in annual cultures.
In particular, the compounds of the formula (I) according to the invention are suitable for selectively combating monocotyledon and dicotyledon weeds in mono Le A 27 156 - 39 -t'~ rig ;x -~. ~ '!~
~~ ~e7 .c c~ .;4. e9 .-,r cotyledon crops, either using the pre-emergence or the post-emergence method. They are markedly more effective than, fox example, isocarbamid.
To a certain extent, the compounds according to the invention also show fungicidal action, for example against Pyricularia on rice.
The active compounds can be converted into the customary formulations, such as solutions, emulsions, wettable powders, suspensions, powders, dusting agents, pastes, soluble powders, granules, suspension-emulsion concentrates, natural and synthetic materials impregnated with active compound, and very fine capsules in polymeric substances.
These formulations are produced in a known manner, fox examgle by mixing the active compounds with extenders, that is liquid solvents and/or solid carriers, optionally with the use of surface-active agents, that is emulsifying agents and/or dispersing agents andlor foam forming agents.
In the case of the use of water as an extender, organic solvents can, for example, also be used as auxiliary solvents. As liquid solvents, there are suit-able in the main: aromatics, such as xylene, toluene or alkylnaphthalenes, chlorinated aromatics and chlorinated aliphatic hydrocarbons, such as chlorobenzenes, chloro-ethylenes or methylene chloride, aliphatic hydrocarbons, such as cyclohexane or paraffins, for example petroleum fractions, mineral and vegetable oils, alcohols, such as butanol or glycol as well as their ethers and esters, ketones, such as acetone, methyl ethyl ketone, methyl Le A 27 156 - 40 -isobutyl ketone or cyclohexanone, strongly polar sol-vents, such as dimethylformamide and dimethyl sulphoxide, as well as water.
As solid carriers there are suitable: for example ammonium salts and ground natural minerals, such as kaolins, clays, talc, chalk, quartz, attapulgite, mont morillonite or diatomaceous earth, and ground synthetic minerals, such as highly-disperse silica, alumina and silicates, as solid carriers for granules there are suitable: fox example crushed and fractionated natural rocks such as calcite, marble, pumice, sepiolite and dolomite, as well as synthetic granules of inorganic and organic meals, and granules of organic material such as sawdust, coconut shells, maize cobs and tobacco stalks as emulsifying and/or foam-forming agents there are suitable: for example non-ionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethyl-ene fatty alcohol ethers, for example alkylaryl poly-glycol ethers, alkylsulphonates, alkyl sulphates, aryl-sulphonates as well as albumen hydrolysis products; as dispersing agents there are suitable: for example lignin-sulphite waste liquors and methylcellulose.
Adhesives such as carboxymethylcellulose and natural and synthetic polymers in the form of powders, granules or latexes, such as gum arabic, polyvinyl alcohol and polyvinyl acetate, as well as natural phos-pholipids, such as cephalins and lecithins, and synthetic phospholipids, can be used in the formulations. Further additives can be mineral and vegetable oils.
39 It is possible to use colorants such as inorganic Le A 27 156 - 41 -~~ ~3 ; ~ t~
pigments, for example iron oxide, titanium oxide and Prussian Blue, and organic dyestuffs, such as alizarin dyestuffs, azo dyestuffs and metal phthalocyanine dye-stuffs, and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc.
The formulations in general contain between 0.1 and 95 per cent by weight of active compound, preferably between 0.5 and 90$.
For combating weeds, the active compounds accord ing to the invention, as such or in the form of their formulations, can also be used as mixtures with known herbicides, finished formulations or tank mixes being possible.
Suitable herbicides for the mixtures are known herbicides, such as, for example, 1-amino-6-ethylthio-3 (2,2-dimethylpropyl)-1,3,5-triazine-2,4-(1H,3H)-dione (AMETHYDIONE) or N-(2-benzothiazolyl)-N, N'-dimethylurea (METABENZTHIAZURON) for combating weeds in cereals; 4 amino-3-methyl-6-phenyl-1,2,4-triazin-5(4H)-one (METAMITRON) for combating weeds in sugar beet, and 4-amino-6-(1,1-dimethylethyl)-3-methylthio-1,2,4-triazin-5(4H)-one (METRIBUZIN) for combating weeds in soya beans;
furthermore also 2,4-dichlrophenoxyacetic acid (2,4-D);
4-(2,4-dichlorophenoxy)-butyric acid (2,4-DB); 2,4-di-chlorophenoxypropionic acid (2,4-DP}; 3-isopropyl-2,1,3-benzothiadiazin-4-one 2,2-dioxide (BENTAZONE); methyl 5-(2,4-dichlorophenoxy)-2-nitrobenzoate (BIFENOX); 3,5-dibromo-4-hydroxy-benzonitrile (BROMOXYNIL); 2-chloro-N~[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)-amino]-car-bonyl~benzenesulphonamide (CHLORSULFURON}; N,N-di.methyl-Le A 2? 156 - 42 -J 1 J i.,l ;. E.Y :.1 N'-(3-chloro-4-methylphenyl)-urea (CHLORTOLURON); 2-[4-(2,4-dichlorophenoxy)-phenoxy]-propionic acid, its methyl ester or its ethyl ester (DICLOFOP); 4-amino-6-t-butyl-3-ethylthio-1,2,4-triazin-5(4H)-one(ETHIOZIN);2-~4-[(6-chloro-2-benzoxazolyl)-oxy)-phenoxy}-propanoic acid, its methyl ester or its ethyl ester (FENOXAPROP); [(4-amino-3,5-dichloro-6-fluoro-2-pyridin-yl)-oxy]-acetic acid or its 1-methylheptyl ester (FLUROXYPYR); N-phosphonomethyl-glycin (GLYPHOSATE); methyl 2-[4,5-dihydro-4-methyl-4-(1-methylethyl)-5-oxo-1H-imidazol-2-yl]-4(5)-methylbenzoate (IMAZAMETHABENZ); 3,5-diiodo-4-hydroxybenzonitrile (IOXYNIL); N,N-dimethyl-N'-(4-isopropylphenyl)-urea (ISOPROTURON); (2-methyl-4-chlorophenoxy)-acetic acid (MCPA); (4-chloro-2-methylphenoxy)-propionic acid (MCPP);
N-methyl-2-(i,3-benzothiazol-2-yloxy)-acetanilide (MEFENACET);2-~[[((4-methoxy-6-methyl-1,3,5-triazin-2-yl)amino)-carbonyl]-amino]-sulphonyl}-benzoic acid or its methyl ester (METSULFURON); N-(1-ethylpropyl)-3,4-di-methyl-2,6-dinitroaniline (PENDIMETHALIN); 0-(6-chloro-3-phenyl-pyridazin-4-yl)-S-octyl thiocarbamate (PYRIDATE); 4-ethylamino-2-t-butylamino-6-methylthio-s-triazine (TERBUTRYNE) and methyl 3-[[[[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)-amino]-carbonyl]-amino]-sulphonyl]-thiophene-2-carboxylate (THIAMETURON). Sur-prisingly, some mixtures also show synergistic action.
Mixtures with other known active compounds, such as fungicides, insecticides, acaricides, nematicides, bird repellents, plant nutrients and agents which improve soil structure, are also possible.
The active compounds can be used as such, in the Le A 27 156 - 43 -form of their formulations or in the use forms prepared therefrom by further dilution, such as ready-to-use solutions, suspensions, emulsions, powders, pastes and granules. They are used in the customary manner, for example by watering, spraying, atomizing or scattering.
The active compounds according to the invention can be applied either before ox after emergence of the plants. They can also be incorporated into the soil before sowing.
The amount of active compound used can vary within a substantial range. It depends essentially on the nature of the desired effect. In general, the amounts used are between 0.01 and 15 kg of active compound per hectare of soil surface, preferably between 0.05 and 10 kg per ha.
The preparation and use of the active compounds according to the invention can be seen from the following examples.
Preparation Examples Example 1 S02-NH-CO-N~N-CH3 ~S-CH3 (Process (a)) 3.0 g (20.? mmol) of 4-methyl-5-methylthio-2,4-dihydro-3H-1,2,4-triazol-3-one are dissolved in 60 ml of 7Ge A 2? 156 _ 44 _ acetonitrile, and 7.0 g (29 mmol) of 2-methoxycarbonyl-phenylsulphonyl-isocyanate, dissolved in 20 ml of acetonitrile, are added to this solution with stirring.
The reaction mixture is stirred at 20°C for 6 hours. The product which is obtained in crystalline form is then isolated by filtration with suction.
This gives 6.0 g (75 ~ of theory) of 4-methyl-5 methylthio-2-(2-methoxycarbonyl-phenylsulphonyl-amino carbonyl)-2,4-dihydro-3H-1,2,4 -triazol-3-one of melting point 184°C.
Example 2 502-NH-CO-N~N-NH2 ~S-CH3 (Process (b)) 1.7 g (11.2 mmol) of 1,8-diazabicyclo-(5,4,0]
undec-7-ene (DBU) and 2.7 g (11.2 mmol) of 2-trifluoro methoxybenzenesulphonamide are added to a solution of 3.0 g (11.3 mmol) of 4-amino-5-methylthio-2-phenoxy-carbonyl-2,4-dihydro-3H-1,2,4-triazol-3-one in 60 ml of methylene chloride. The reaction mixture is stirred for 4 hours at 20°C, then washed twice with 1 ~ strength hydrochloric acid and three times with water, dried with sodimn sulphate, and filtered. The filtrate is concen-trated, the residue is stirred with diethyl ether, and the product which is obtained in crystalline form is Le A 27 156 - 45 -isolated by filtration with suction.
This gives 2.1 g (45 ~ of theory) of 4-amino-5-methylthio-2-(2-trifluoromethoxy-phenylsul phonyl-aminocarbonyl)-2,4-dihydro-3H-1,2,4-triazol-3-one of melting point 136°C.
For example, the compounds of the formula (I) listed in Table 3 below can also be prepared analogously to Examples 1 and 2 and following the general description of the preparation processes according to the invention.
o R3-S02-NH-CO~N~N~RZ (I) ~S(O1n-R2 Le A 27 156 - 46 -Table 3: compounds Preparation of ExampJ.es the of the foxznula ( I
) Ex. Rl R2 R3 n Melting NO. point (C) ~

3 CH3 C2H5 ~ 0 I49 ~

4 CH3 CH(CH3)2 ~ ~ 0 161 ~
5 CH3 CH2CH=CH2 ~ 0 I40 ~
6 C2H5 C2H5 ~ ~ 0 128 8 C2H5 CH2C6H5 ~ 0 285 Le ~ z~ ass - 4~ -Table 3: (Continuation) Ex. R' RZ R3 n Melting No. point (°C) CH3 CH2C6H5 \ ~ 0 143 20 CH2C6H5 CH3 \ ~ 0 134 ' 11 CH(CH3>2 CH3 \ ~ 0 142 I2 ~ \
-\ CH3 ~ 0 205 Ci 13 CH3 C3H7 / \
o I4z I4 C2H5 -CH2CH=CH2 ~- \ 0 Le A 27 156 _ 4g _ ~, Table 3: (Continuation) Esc. R1 RZ R3 n Melting No. point (°C) 15 C2H5 C3H7 ~~ 0 125 16 C2H5 CH(CH3)2 ~- ~ 0 131 17 CH3 CH3 ~~ 0 150 18 C3H7 -CH2CH=CH2 ~- ~ 0 128 19 C3H7 C3H~ ~ 0 137 20 C3H7 CH(CH3)2 7a~ 0 221 21 CH3 C2H5 ~-~ 0 133 Le ~. 27 156 _ 4g _ C
Table 3: (Continuation) Ex. R1 R2 R3 n Melting No. point ('C) 22 ~ -CH2CH=CH2 ~ 0 151 ~

-23 ~ C3H7 ~ 0 199 ~

_ 24 ~ CH(CH ~ 0 163 ) ~

3 _~

~

25 C3H7 CH3 _~ 0 144 ~

26 C3H7 C2H5 -~ 0 130 27 ~ C2H5 ~ 0 173 ' 28 ~ CH ~ 0 173 ~

Le A 27 z56 - 50 -~?:~ ~
Table 3:
(Continuation) Ex. R1 Rz R3 n Melting No. point (C) /

29 -CH2-CH=CH2 CH3 '~ 0 137 ~

30 -CH2-CH=CH2 C2H5 _~ 0 128 31 ~ CH3 ~ 0 182 ~

-32 ~ C ~ 0 152 H ~

~

33 CH3 CH3 -~ 2 176 34 CH3 C2H5 / ~ 0 138 Le A 27 156 - 51 -Table 3:
(Continuation) Ex. R1 RZ R3 n Melting No. point (C) C1 ' 35 CH3 CH3 ~ ~ 0 175 ~
~

36 ~ 0 101 -CHZ-CH=CH2 -CH2-CH=CH2 37 ~ CH3 ~ ~ 0 190 Ci 3g ~ C2H5 ~ ~ 0 163 ~

39 -CH2-CH=CH2 CH3 -~ 0 163 ~

-CHZ-CH=CH2 C2H5 ~~ 0 133 Le A 27 156 - 52 -Table 3: (Continuation) E~ . R1 RZ R3 n Melting No. point (°C) 41 CH3 C3H7 7-~ 0 133 92 C2H5 -CH2-CH=CH2 ~-~ 0 107 43 ~ C3H7 /~~ 0 121 44 -CH2-CH=CH2 C3H7 /-~ 0 124 45 -CH2-CH=CH2 CH(CH3)2 /-~ 0 94 4o CH3 CH(CH3)2 / ~ 0 142 Le A 27 156 - 53 -, Table 3:
(Continuation) Ex. R1 RZ R3 n Melting , No. point (C) 47 -CH2-CH=CH2 CH3 ~ ~ 0 165 48 -CH2-CH=CH2 C2H5 ~ ~ 0 140 ~ C1 49 ~ CH(CH3)2 ~ ~ 0 131 H \

52 C2H5 C2H5 ~ ~ 0 129 Le 27 156 - 54 -A

t~~~ ~~.~~
Table (Continuation) 3:

Ex. R' RZ R3 n Melting No. point (C) CZ

53 CH3 C3H~ ~ ~ 0 146 54 CH3 -CH2-CH=CH2 ~ ~ 0 125 55 ~ -CH2-CH=CH2 ~ ~ 0 141 ~

56 C2H5 C3H7 ~ 0 122 57 C2H5 -CH2-CH=CH2 ~-.\ 0 96 58 -CH2-CH=CH2 -CH2-CH=CH2 113 / ~ 0 Le A 27 156 - 55 -~~~~~~~
Table 3:
(Continuation) Ex R1 R3 n Melting . RZ

No. point ('C) 59 -CH2-CH=CH2 ~ ~ 0 102 60 -CH2-CH=CH2 ~ ~ 0 122 CH(CH3)2 /

61 CH3 -_\ 0 106 CH(CH3)2 ~

62 CH3 _~ 0 125 -CH2-CH=CH2 63 ~ /-~ 0 12S
-CH2-CH=CH2 64 ~ CH(CH ~ 0 127 ) ~

3 ~

Le A 27 156 - 56 °

Table 3: (Continuation]
Ex. R1 RZ R3 n Melting NO. point ('Cj ~

65 C2H5 CH3 -~ 0 171 ~

66 C2H5 C2H5 -~ 0 238 ~
~

67 -CH2-CH=CH2C3H7 - 89 ~

68 C2H5 C3H7 ~ 0 ? 27 -~

69 -CH2-CH=CH2CH(CH3)2-~ 0 117 ~
~

70 -CH2-CH=CH2-CH2-CH=CH2 79 -Le A 27 156 - 57 -~~~~.~,~
r r ~ lF J
Table 3: (Continuation) Ex. R1 RZ R3 n Melting No. point (°C) i0 71 C2H5 CH(CH3)2 ~ ~ 0 137 72 CH3 CH3 ~ ~ 0 193-194 S~COOCH3 73 CH3 C2H5 ~ ~ 0 176-177 S~COOCH3 74 ~ CH3 ~ ~ 0' 175-177 75 ~ C2H5 ~ ~ 0 153-155 Le A 27 156 - 58 -~~~.'~' Table 3: (Continuation) Ex. R1 RZ R3 n Melting No. point (°C) 76 N(CH3)2 GH3 -~ 0 178-179 77 N(CH3)2 C2H5 7~~ 0 139-136 78 ~ CH3 ~ ( 0 188-191 I~I~N

Br 79 CH3 CH3 ~-~ 0- 176- 179 Br 80 CH3 C2H5 ~~~ 0 , 154-156 I,e A 27 X56 - 59 -Table 3: (Continuation) Ex. R1 RZ R3 n Melting No. point (°C) Br 81 ~ CH3 /~\ 0 192-195 $r 82 ~ C2H5 7-\ 0 151-154 83 CH3 CH3 -\ 0 157 C Y. 3 89 ~ 7 \

Le A 27 156 - 60 -Table 3: (Continuation) Ex. R' RZ R3 n Melting No. point (°C) ZO

86 ~ C2H5 ~-~ 0 137 87-CH2-CH=CH2 -CH2-C=CH ~_~ 0 95 r 88 ~ -CH2-C=CH ~ 0 128-131 89 CH3 -CH2-C=CH ~~~ 0 143-144 90 CH3 -CH(CH3)2 /-~ 0 107-109 Br 91 CH3 - CH ( CH3 ) 2 ~-~~ 0 103- 104 Le A 27 156 - 61 --Table 3: (Continuation) Ex. R' RZ R3 n Melting No. point ('C) 92 CH3 -CH(CH3)2 /~~ 0 lI9-117 93 ~ CH3 ~ 0 199-195 /

, ~

94 C2H5 '~ 0 150-152 '.

95 CH3 C2H5 /-~ - 0 146-148 Le A 27 156 - 62 -Starting substances of the formula ~ II ) Examgle (-,II-11 H-N~N-CH3 ~S-CH3 Step 1 S

A solution of 175 g (2.4 mol) of methyl isothio-cyanate in 300 ml of diethyl ether is added to a solution of 250 g (2.4 mol) of ethyl hydrazinoformate, with stir-ring. The reaction mixture is stirred for 12 hours at 20°C and then cooled to about 10°C, and the product which is obtained in crystalline form is isolated by filtration with suction. This gives 404 g (95 ~ of theory) of 4-methyl-1-ethoxycarbonylthiosemicarbazide of melting point I30°C.
The following are obtained analogously:
4-ethyl-1-methoxycarbonyl-thiosemicarbazide I5 (melting points 142°C);
4-propyl-1-methoxycarbonyl-thiosemicarbazide (melting point: 117°C
4-cyclopropyl-1-methoxycarbonyl-thiosemicarbazide (melting point: 148°C);
4-allyl-1-methoxycarbonyl-thiosemicarbazide (melting point: 151°C);
4-dimethylamino-1-methoxycarbonyl-thiosemicarbazide (melting point: 144oC).
Le A 27 156 - 63 -Step 2 C
H-N~N-CH3 ~SeKe A mixture of lO.Og (56.5 mmol) of 4-methyl-1-ethoxycarbonyl-thiosemicarbazide (cf. Step 1), 4.0 g (29 mmol) of potassium carbonate and 80 ml of ethanol is refluxed until the evolution of gas has ceased (about 3 hours). When the mixture is cold, it is concentrated, the residua is stirred with 50 ml of methylene chloride, and the product, which has remained undissolved, is isolated by filtration with suction.
This gives 9.2 g (96 ~ of 'theory) of the potas-sium salt of 5-mercapto-4-methyl-2,4-dihydro-3H-1,2,4-triazol-3-one (melting point >230°C).
The potassium salts of 5-mercapto-4-ethyl-2,4-dihydro-3H-1,2,4-triazol-3-one, 5-mercapto-4-propyl-2,4-dihydro-3H-1,2,4-triazol-3-one, 5-mercapto-4-cyclopropyl-2,4-dihydro-3H-1,2,4-triazol-3-one,and 5-mercapto-4-allyl~2,4-dihydro-3H-1,2,4-triazol-3-one, and 5-mercapto-4-dimethylamino-2,4-dihydro-3H-1,2,4-triazol-3-one, all of which melt above 230 oC, are obtained analogously.
Le A 27 156 - 64 -G ~ ~~ ~A ~.9~ '~
lJ ~ ~nl N7 ~ .~.1 Step 3 H-N~N-CH3 ~S-CH3 A mixture of 4.0 g (23.'7 mmol) of the potassium salt of 5-mercapto-4-methyl-2,4-dihydro-3H-1,2,4-triazol-3-one (cf. Step 2), 4.1 g (28.9 mmol) of methyl iodide and 80 ml of methanol is stirred for 12 hours at 20°C.
The mixture is then concentrated, the residue is stirred with methylene chloride, and the potassium iodide, which has remained undissolved, is separated off by filtration.
The filtrate is concentrated, the residue is stirred with 500 ml of diethyl ether/petroleum ether (lel by vol.), and the product which has been obtained in crystalline from is isolated by filtration with suction.
This gives 3.4 g (99 ~ of theory) of 4-methyl-5 methylthio-2,4-dihydro-3H-1,2,4-triazol-3-one o~ melting point 97°C.
For example the compounds of the formula (II) listed in Table 4 below can also be prepared analogously to Example (II-1).

(II}
H-N~N-R~
~S(0)n-R2 Le A 2? 156 - 65 -Table 4 Preparation Examples of the compounds of the formula (II) Ex. R1 RZ n m>p. C) ( No. (Refra ctive index) --II-9 CH3 CH(CH3)2 0 91 II-5 CH3 -CH2CH=CH2 0 58 ' II-i0 C2H5 CH(CH3)2 0 42 II-i1 C2H5 -CH2CH=CH2 0 (nD: 1,5400) ~5 II-12 C2H5 -CH2C6H5 0 II-14 C3H7 C2H5 0 (nD; 1,5215) II-16 C3H7 CH(CH3)2 0 55 II-17 C3H7 -CH2CH=CH2 0 (nD: 1,5350) II-18 CH(CH3)2 CH3 0 II-19 --a CH3 0 160 II-20 -~ C2H5 0 119 Le A 27 156 - 66 -~~~~~ 3~ ._ Table 4 (Continuation) Ex. R1 RZ n m.p. ( °C) No. (Refractive index) II-21 --a C3H7 0 94 II-22 --~ CH(CH3)2 0 94 II-23 --a -CH2CH=CH2 0 105 II-25 -CH2CH=CH2 CH3 0 70 II-26 -CH2CH=CH2 C2H5 0 55 II-28 -CH2-CH=CH2 -CH2-CH=CH2 0 (amorphous)*

II-29 _CH2_CH=CH2 CH(CH3)2 0 57 II-30 -CH2-CH=CH2 C3H7 0 45 II-31 -Id(CH3)2 CH3 0 168-169 I I-32-J~I(CH3)2 C2H5 0 146 II-33 CH3 -CH2-C=CH 0 153 II-34 --~a -CH2-C=CH 0 153-154 II-35 -CH2-CH=CH2 -CH2--C=CH 0 102-103 * 1H -1~17~fR (D6-DI~5S0,360 I~Hz ) 3, 66 S-CH2-) ;
: 8 = (d, 4, 17 (m, 1y-CH2-);4,95-5,28 2CH2=);
(m, 5, 75-5,99 (m, ppm.
2CH=); 12,0 (13H) Le A 27 156 - 67 -., Startincr substances of the formula (IVJv:
Example Iy-1)_ 0-CO-N~N-NH2 ~S-CH3 22.1 g (0.141 mol) of phenyl chloroformate are added to a mixture of 20.Og (0.137 mol) of 4-amino-5-methylthio-2,4-dihydro-3H-1,2,4-triazol-3-one, 5.6 g (0.141 mol) of sodium hydroxide, 0.2 g of tetrabutylam-monium bromide and 200 ml of methylene chloride/water (1:1, by vol.), with vigorous stirring. The reaction mixture is stirred for 12 hours at 20°C, and the product which is obtained in crystalline form is isolated by filtration with suction. This gives 34.8 g (95 ~ of theory) of 4-amino-5-methylthio-2-phenoxycarbonyl-2,4-dihydro-3H-1,2,4-triazol-3-one of melting point 211°C.
For example the compounds of the formula (IV) listed in Table 5 below can also be prepared analogously to Example (IV-1).

Z-CO-N~N-R1. (IV) ~S(0)n-R2 Le A 2? 156 - 68 -/~: ~ s'~ -t f~ui lj ~~
Table 5 Preparation of the compounds of the Examples formula (IV) Ex . R1 Rz n Z Melting No. point (C) ~
~

-~
\

-IV-5 CH3 C3H~ 0 C1 IV-6 CH3 CH2-CH=CH2 0 /- \

IV-7 ~ CH3 0 /-\ 193 IV-8 ~ C2H5 0 ~~~ 89 IV-9 ~ C3H7 0 Le A 27 156 - 69 Table 5 (Continuation) Ex. R1 RZ n Z Melting No. point (C) IV-10 ~ CH2-CH=CH2 0 IV-13 OCH2-CH=CH2 0 IV-14 ~ CH(CH3)2 0 C1 IV-16 C2H5 C3H~ 0 ~~~

IV-18 NH-CH3 C2H5 0 ~~~
Le A 27 15~ ~ 70 -Table 5 (Continuation) Ex. R1 R2 n Z Melting No. point (C) IV-19 N(CH3)2 C2H5 0 IV-20 NH-CH3 C3H7 0 /-~

IV-21 NH-CH3 CH(CH3)2 0 ~ ' ~

IV-22 NH-CH3 CH2-CH=CH2 IV-23 CH2-CH=CH2 C2H5 0 Le A 27 156 - 71 -~~~~~.3~~' Use Examples:
In the Use Examples which follow, the known herbicide isocarbamid, of the formula (A) below, is used as comparison substance:
n I-i~-CO-NH-CH2CH(CH3)2 ~0 (disclosed in, for example, DE-1,795,117).
In the text below, the formulae of the compounds according to the invention used for the Use Examples are listed individually, the numbers being those of the Preparation Examples:

502-NH-CO~N~N~CH3 (1) ~S-CH3 S02-NH-CO~N~N~CH3 (3) ~S-C2H5 S02-NH-CO~N~N~CH3 (9) ~S-CH(CH3)2 Le A 27 156 - 72 -~ S02-NH-CO~N~N~CH3 (5) ~S-CH2CH=CH2 \ ~ S02-1QH-CO~N~NiC2H5 ( 6 ) N°~SC2H5 ~ ~ S02-l~H-C0~1J~N~C2H5 ( 7 ) ~S-CH3 ~ ~ S02-NH-CO~Id~~?~l~Ci':g ( 9 ) ?~S-CH2C6H5 502-?'?H-C0~?I~?J~CH3 ( 13 ) ;~~5-C3H~-n ~ S02-NH-CO~ld~N~'C2H5 ( 14 ) ~S-CH2CH=CH2 ~ S02-NH-CO~I~~?~I~C2H5 ( 15 ) ~S-C3H7-n Le A 27 156 a 73 ~~a ,~y ~
Y~,7 ~Y YHI y~ .~- 0:d rJ

_ ~
~ S02-1~H-CO~l~~N~C2H5 ( 16 ) ~S-CH(CH3)2 ~ S02-l~tH-COT N~CH3 ( 17 ) I~S-CH3 ~ ~ S02-NN-CO~N~1~~C3H~-n (20) N-~S-CH(CH3)2 ~'~ S02-NH-CO~I~~N~CH3 ( 2? ) I~S-C2H5 ~ S02-NH-C0~1~~N ( 22 ) [
I~S-CH2CH=CH2 ~ S02-NH-CO~N~N (23) 1~S-C3H7-n ~ S02-NH-CO~N~N (29) ~S-CH(CH3)2 Le A 27 156 - 74 -_ ~ S02-NH-CO~N~NiC3H7-n (25) ~S-CH3 ~ S02-NH-CO~l~~la~C3H7-n ( 26 ) ~S_C2H5 ~ 7 S02-IJH-CO~I~~N ( 27 ) ~S-C2H5 ~~ ~ S02-NH-CO~N~Iv' ( 28 ) N~S-CH3 S02-IJH-CO~I~I~I,;~CH2-CH=CH2 ( 29 ) ~~~
~S-CH3 ~502-NH-CO~N~N~CH2-CH=CH2 (30) I
~S-C2H5 S02-1v'H-CO~N~N~ ( 31 ) I~S-~CN3 Le A 27 156 - 75 -i /~
~ S02-NH-C0~I4~N~ ( 32 ) 1~S -~CJ2H 5 ~ S02-NH-CO~IJ~N~CH3 ( 34 ) CH3 ~S-C2H5 ~~~ S02-I~H-CO~Id~I~i~'CH3 ( 35 ) CH3 l~S-CH3 ~ ~ S02-1~H-CO~N~L1~ ( 37 ) CH3 1~S °~C133 502-1QH-CO~N~LT ( 3g ) j CH3 I'T~~S'CZHS

~ S02-IQH-C0~13~N~CH2-CH=CH2 ( 4 0 ) N-~S-C2H5 Le A 27 156 ~ 70 -~~~,~,~ ~;~
Example A
Pre-emergence test Solvent: 5 parts by weight of acetone Emulsifier: 1 part by weight of alkylaryl polyglycol ether To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amount of solvent, the stated amount of emulsifier is added and the concentrate is diluted with water to the desired concentration.
Seeds of the test plants are sown in normal soil and, after 24 hours, watered with the preparation of the active compound. It is expedient to keep the amount of water per unit area constant. 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, a clearly superior activity com-pared with the prior art is shown, for example, by the compounds of Preparation Examples:
l, 3, 4, 5, 6, 7, 13, 17, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 31, 32, 34, 35, 37.
Le A 27 156 - 77 -Example B
Post-emergence test Solvent: 5 parts by weight of acetone Emulsifier: 1 part by weight of alkylaryl polyglycol ether To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amount of solvent, the stated amount of emulsifier is added and the concentrate is diluted with water to the desired concentration.
Test plants which have a height of 5 - 15 cm are sprayed with the preparation of the active compound in such a way as to apply the particular amounts of active compound desired per unit area. The concentration of the spray liquor is so chosen that the particular amounts of active compound desired are applied in 1,000 1 of water/ha. After three weeks, the degree of damage to the plants is rated in ~ damage in comparison to the develop-ment of the untreated control. The figures denote:
0~ = no action (like untreated control) 100 _ total destruction In this test, a clearly superior activity com-pared with the prior art is shown, for example, by the compounds of Preparation Examples:
1, 3, 4, 5, 6, 7, 13, 14, 16, 17, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 31, 32, 34, 35, 37, 38, 40.
Le A 27 156 - 78 -~~'~~~~?~
Example C
Pyricularia test (rice) / protective Solvent: 12,5 parts by weight of acetone Emulsifier: 0,3 parts by weight of alkylarylpolyglycol ether To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amount of solvent, and the concentrate is diluted with water and the stated amount of emulsifier, to the desired concentration.
To test for protective activity, young rice plants are sprayed with the preparation of active compound until dripping wet. After the spray coating has dried off, the plants are inoculated with an aqueous spore suspension of Pyricularia orycae. The plants are then placed in a greenhouse at 100 o relative atmospheric humidity and 25°C.
Evaluation of the disease infestation is carried out 4 days after the inoculation.
Tn this test, a clearly superior activity compared with the prior art is shown, for example, by the compounds according to the following preparation examples:
1, 3, 4, 5, 7, 9.
Le A 27 156 - ?9 -Example D
Pyricularia test (rice) / systemic Solvent . 12,5 parts by weight of acetone Emulsifier: 0,3 parts by weight of alkylarylpolyglycol ether To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amount of solvent, and the concentrate is diluted with water and the stated amount of emulsifier, to the desired concentration.
To test for systemic properties, standard soil in which young rice plants have been grown is watered with 90 ml of the preparation of active compound. 7 days after the treatment, the plants are inoculated with an aaueous spore suspension of Pyricularia oryzae.
Thereafter, the plants remain in a greenhouse at a tempera-ture of 25° and a relative atmospheric humidity of 100 until they are evaluated.
Evaluation of the disease infestation is carried out 4 days after the inocualtion.
In this test, a clearly superior activity compared with the prior art is shown, for example, by the compounds according to the following preparation examples:
l, 3, 4, 5, 7, 15, 17, 21, 22, 25.
I~e A 27 156 - 80

Claims (30)

1. A compound of the general formula (I), in which n represents the numbers 0, 1 or 2, R1 represents hydrogen, hydroxyl or amino, or represent C1-C6-alkyl which is optionally substituted by fluorine, chlorine, bromine, cyano, C1-C4-alkoxy, C1-C4-alkylcarbonyl or C1-C4-alkoxycarbonyl, or represents C3-C6-alkenyl or C3-C6-alkinyl, each of which is optionally substituted by fluorine, chlorine and/or bromine, or represents C3-C6-cycloalkyl which is optionally substituted by fluorine, chlorine, bromine and/ar C1-C4-alkyl, or represents phenyl-C1-C3-alkyl which is optionally substituted by fluorine, chlorine, bromine, cyano, nitro, C1-C4-alkyl, trifluoromethyl, C1-C4-alkoxy and/or C1-C4-alkoxycarbonyl, or represents phenyl which is optionally substituted by fluorine, chlorine, bromine, cyano, nitro, C1-C4-alkyl, trifluoromethyl, C1-C4-alkoxy, fluorine- and/or chlorine-substituted C1-C3-alkoxy, C1-C4-alkylthio, fluorine- and/or chlorine-substituted C1-C3-alkylthio, C1-C4-alkylsulphinyl, C1-C4-alkylsulphonyl and/or C1-C4-alkoxycarbonyl, or represents C1-C6-alkoxy which is optionally substituted by fluorine, chlorine, cyano, phenyl, C1-C4-alkoxy or C1-C4-alkoxycarbonyl, or represents C3-C4-alkenyloxy, or represents C1-C4-alkylamino which is optionally substituted by fluorine, cyano, C1-C4-alkoxy or C1-C4-alkoxy-carbonyl, or represents C3-C6-cycloalkylamino or di-(C1-C4-alkyl)-amino, R2 represents C1-C6-alkyl which is optionally substituted by fluorine, chlorine, bromine, cyano, C3-C6-cycloalkyl, C1-C4-alkoxy or C1-C4-alkoxycarbonyl, or represents C3-C6-alkenyl or C3-C6-alkinyl, each of which is optionally substituted by fluorine, chlorine and/or bromine, or represents C3-C6-cycloalkyl which is optionally substituted by fluorine, chlorine, bromine and/or C1-C4-alkyl, or represents cyclohexenyl, or represents phenyl-C1-C3-alkyl which is optionally substituted by fluorine, chlorine, bromine, cyano, nitro, C1-C4-alkyl, trifluoromethyl, C1-C4-alkoxy and/or C1-C4-alkoxycarbonyl, or represents phenyl which is optionally substituted by fluorine, chlorine, bromine, cyano, nitro, C1-C4-alkyl, trifluoromethyl, C1-C4-alkoxy, fluorine- and/or chlorine-substituted C1-C3-alkoxy, C1-C4-alkylthio, fluorine-and/or chlorine-substituted C1-C3-alkylthio, C1-C4-alkyl-sulphinyl, C1-C4-alkylsulphonyl and/or C1-C4-alkoxycarbonyl, and R3 represents the group <IMG > where R4 and R5 are identical or different and represent hydrogen, fluorine, chlorine, bromine, iodine, nitro, C1-C6-alkyl (which is optionally substituted by fluorine, chlorine, bromine, cyano, carboxyl, C1-C4-alkoxycarbonyl, C1-C4-alkylamino-carbonyl, di-(C1-C4-alkyl)amino-carbonyl, hydroxyl, C1-C4-alkoxy, formyloxy, C1-C4-alkyl-carbonyloxy, C1-C4-alkoxy-carbonyloxy, C1-C4-alkylamino-carbonyloxy, C1-C4-alkylthio, C1-C4-alkylsulphinyl, C1-C4-alkylsulphonyl, di-(C1-C4-alkyl)-aminosulphonyl, C3-C6-cycloalkyl or phenyl), or represent C2-C6-alkenyl (which is optionally substituted by fluorine, chlorine, bromine, cyano, C1-C4-alkoxy-carbonyl, carboxyl or phenyl), or represent C2-C6-alkinyl (which is optionally substituted by fluorine, chlorine, bromine, cyano, C1-C4-alkoxy-carbonyl, carboxyl or phenyl), or represent phenoxy or C1-C4-alkoxy (which is optionally substituted by fluorine, chlorine, bromine, cyano, carboxyl, C1-C4-alkoxy-carbonyl, C1-C4-alkoxy, C1-C4-alkylthio, C1-C4-alkylsulphinyl or C1-C4-alkylsulphonyl), or represent C1-C4-alkylthio (which is optionally substituted by fluorine, chlorine, bromine, cyano, carboxyl, C1-C4-alkoxy-carbonyl, C1-C4-alkylthio, C1-C4-alkylsulphinyl or C1-C4-alkylsulphonyl), or represent C3-C6-alkenyl-oxy (which is optionally substituted by fluorine, chlorine, bromine, cyano or C1-C4-alkoxy-carbonyl), or represent C2-C6-alkenyl.thio (which is optionally substituted by fluorine, chlorine, bromine, cyano, nitro, C1-C3-alkylthio or C1-C4-alkoxycarbonyl), C3-C6-alkinyloxy or C3-C6-alkinylthio, or represent the radical -C(O)p-R6 where p represents the number 1 or 2 and R6 represents C1-C4-alkyl (which is optionally substituted by fluorine, chlorine, bromine, cyano or C1-C4-alkoxycarbonyl), C3-C6-alkenyl, C3-C6-alkinyl, C1-C4-alkoxy, C1-C4-alkoxy-C1-C4-alkylamino, C1-C4-alkylamino, di-(C1-C4-alkyl)-amino N-methoxy-N-methylamino, methoxyamino, or phenyl, or represents the radical -NHOR7 where R7 represents C1-C12-alkyl (which is optionally substituted by fluorine, chlorine, cyano, C1-C4-alkoxy, C1-C4-alkylthio, C1-C4-alkylsulphinyl, C1-C4-alkylsulphonyl, C1-C4-alkylcarbonyl, C1-C4-alkoxycarbonyl, C1-C4-alkyl-amino-carbonyl or di-(C1-C4-alkyl)-amino-carbonyl), or represent C3-C6-alkenyl (which is optionally substituted by fluorine, chlorine or bromine), C3-C6-alkinyl, C3-C6-cycloalkyl, C3-C6-cycloalkyl-C1-C2-alkyl, phenyl-C1-C2-alkyl (which is optionally substituted by fluorine, chlorine, nitro, cyano, C1-C4-alkyl, C1-C4-alkoxy or C1-C4-alkoxycarbonyl), or represents benzhydryl, or represents phenyl (which is optionally substituted by fluorine, chlorine, nitro, cyano, C1-C4-alkyl, trifluoromethyl, C1-C4-alkoxy, C1-C2-fluoroalkoxy, C1-C4-alkylthio, trifluoromethylthio or C1-C4-alkoxycarbonyl), R4 and/or R5 furthermore represent phenyl or phenoxy, or represent C1-C4-alkylcarbonylamino, C1-C4-alkoxycarbonylamino, C1-C4-alkylamino-carbonylamino or di-(C1-C4-alkyl)-amino-carbonylamino, or represent the radical -CO-R8 where R8 represents C1-C6-alkyl, C1-C6-alkoxy, C3-C6-cycloalkoxy, C3-C6-alkenyloxy, C1-C4-alkylthio, C1-C4-alkylamino, C1-C4-alkoxyamino, C1-C4-alkoxy-C1-C4-alkyl-amino or di-(C1-C4-alkyl)-amino (each of which is optionally substituted by fluorine and/or chlorine).
R4 and/or R5 furthermore represent trimethylsilyl, thiazolinyl, C1-C4-alkylsulphonyloxy or di-(C1-C4-alkyl)-aminosulphonylamino, or represent the radical -CH=N-R9 where R9 represents C1-C6-alkyl which is optionally substituted by fluorine, chlorine, cyano, carboxyl, C1-C4-alkoxy, C1-C4-alkylthio, C1-C4-alkylsulphinyl or C1-C4-alkylsulphonyl, or represents benzyl which is optionally substituted by fluorine or chlorine, or represents C3-C6-alkenyl or C3-C6-alkinyl, each of which is optionally substituted by fluorine or chlorine, or represents phenyl which is optionally substituted by fluorine, chlorine, bromine, C1-C4-alkyl, C1-C4-alkoxy, trifluoromethyl, trifluoromethoxy or trifluoromethylthio, or represents C1-C6-alkoxy, C3-C6-alkenoxy, C3-C6-alkinoxy, or benzyloxy, each of which is optionally substituted by fluorine and/or chlorine, or represents amino, C1-C4-alkylamino, di-(C1-C4-alkyl)-amino, phenyl-amino, C1-C4-alkyl-carbonylamino, C1-C4-alkoxy-carbonylamino or C1-C4-alkyl-sulphonylamino, or represents phenylsulphonylamino which is optionally substituted by fluorine, chlorine, bromine or methy, furthermore R3 represents the radical where R11 represents hydrogen or C1-C4-alkyl, R11 and R12 are identical or difference and represent hydrogen, fluorine, chlorine, bromine, nitro, cyano, C1-C4-alkyl (which is optionally substituted by fluorine and/or chlorine), C1-C4-alkoxy (which is optionally substituted by fluorine and/or chlorine), carboxyl, C1-C4-alkoxycarbonyl, dimethylaminocarbonyl, C1-C4-alkylsulphonyl or di-(C1-C4-alkyl)-aminosulphonyl;

furthermore R3 represents the radical where R13 and R14 are identical or different and represent hydrogen, fluorine, chlorine, bromine, nitro, cyano, C1-C4-alkyl (which is optionally substituted by fluorine and/or chlorine) or C1-C4-alkoxy (which is optionally substituted by fluorine and/or chlorine);

furthermore R3 represents the radical where R15 and R16 are identical or different and represent hydrogen, fluorine, chlorine, bromine, nitro, cyano, C1-C4-alkyl (which is optionally substituted by fluorine and/or chlorine), C1-C4-alkoxy (which is optionally substituted by fluorine and/or chlorine), or represents C1-C4-alkylthio, C1-C4-alkylsulphinyl or C1-C4-alkylsulphonyl (each of which is optionally substituted by fluorine and/or chlorine), or represents aminosulphonyl, mono-(C1-C4-alkyl)-aminosulphonyl, or represents di-(C1-C4-alkyl)-aminosulphonyl or C1-C4-alkoxycarbonyl or dimethylaminocarbonyl;

furthermore R3 represents the radical where R17 and R18 are identical or different and represent hydrogen, fluorine, chlorine, bromine, C1-C4-alkyl (which is optionally substituted by fluorine and/or bromine), C1-C4-alkoxy (which is optionally substituted by fluorine and/or chlorine), or represent C1-C4-alkylthio, C1-C4-alkylsulphinyl or C1-C4-alkylsulphonyl (which is optionally substituted by fluorine and/or chlorine), or represent di-(C1-C4-alkyl)-aminosulphonyl;

furthermore R3 represents the radical where R19 and R20 are identical or different and represent hydrogen, fluorine, chlorine, bromine, cyano, nitro, C1-C4-alkyl (which is optionally substituted by fluorine and/or chlorine), C1-C4-alkoxy (which is optionally substituted by fluorine and/or chlorine), C1-C4-alkylthio, C1-C3-alkylsulphinyl or C1-C4-alkylsulphonyl (which is optionally substituted by fluorine and/or chlorine), di-(C1-C4-alkyl)-aminosulphonyl, C1-C4-alkoxycarbonyl or dimethylaminocarbonyl and A represents oxygen, sulphur or the group N-Z1 where Z1 represents hydrogen, C1-C4-alkyl (which is optionally substituted by fluorine, chlorine, bromine or cyano), C3-C6-cycloalkyl, benzyl, phenyl-(which is optionally substituted by fluorine, chlorine, bromine or nitro), C1-C4-alkylcarbonyl, C1-C4-alkoxycarbonyl or di-(C1-C4-alkyl)-aminocarbonyl;

furthermore R3 represent the radical where R21 and R22 are identical or different and represent hydrogen, C1-C4-alkyl, halogen, C1-C4-alkoxycarbonyl, C1-C4-alkoxy or Cl-C4-halogenoalkoxy, Y1 represents sulphur or the group N-R23 where R23 represents hydrogen or C1-C4-alkyl;

furthermore R3 represents the radical where R24 represents hydrogen, C1-C4-alkyl, benzyl, pyridyl, quinolinyl or phenyl;

R25 represents hydrogen, halogen, cyano, nitro, C1-C4-alkyl (which is optionally substituted by fluorine and/or chlorine), C1-C4-alkoxy (which is optionally substituted by fluorine and/or chlorine), dioxolanyl or C1-C4-alkoxycarbonyl and R26 represents hydrogen, halogen or C1-C4-alkyl;
furthermore R3 represents one of the groups listed below,
2. A compound according to claim 1 wherein n represents the number 0, 1 or 2 R1 represents hydrogen or amino, or represents C1-C4-alkyl which is optionally substituted by fluorine, cyano, methoxy or ethoxy, or represents allyl, or represents C3-C6-cycloalkyl, or represents benzyl, or represents phenyl, or represents C1-C4-alkoxy, or represents C3-C4-alkenyloxy, or represents C1-C3-alkylamino, C3-C6-cycloalkylamino, or represents di-(C1-C3-alkyl)-amino, R2 represents hydrogen, or represents C1-C4-alkyl which is optionally substituted by fluorine and/or chlorine, methoxy or ethoxy, or represents C3-C4-alkenyl which is optionally substituted by fluorine and/or chlorine, or represents C3-C6-cycloalkyl, or represents benzyl which is optionally substituted by fluorine, chlorine and/or methyl, and R3 represents the group where R4 represents fluorine, chlorine, bromine, methyl, trifluoromethyl, methoxy, difluoromethoxy, trifluoromethoxy, 2-chloro-ethoxy, 2-methoxy-ethoxy, C1-C3-alkylthio, C1-C3-alkylsulphinyl, C1-C3-alkylsulphonyl, dimethylaminosulphonyl, diethylaminosulphonyl, N-methoxy-N-methylamino-sulphonyl, methoxyaminosulphonyl, phenyl, phenoxy or C1-C3-alkoxy-carbonyl, and R5 represents hydrogen, fluorine, chlorine or bromine, furthermore R3 represents the radical where R10 represents hydrogen, R11 represents fluorine, chlorine, bromine, methyl, methoxy, difluoromethoxy, trifluoromethoxy, ethoxy, methoxycarbonyl, ethoxycarbonyl, methylsulphonyl or dimethylaminosulphonyl, and R12 represents hydrogen;

furthermore R3 represents the radical where R represents C1-C4-alkyl, or represents the radical where R represents C1-C4-alkyl.
3. A compound of the formula
4. A compound of the formula
5. A compound of the formula
6. A compound of the formula
7. A compound of the formula
8. A compound of the formula
9. A compound of the formula
10. A compound of the formula
11. A compound of the formula
12. A salt of a compound according to any one of claims 1 to 11 wherein the salt is selected from sodium salts, potassium salts, magnesium salts, calcium salts, ammonium salts, C1-C4-alkyl-ammonium salts, di-(C1-C4-alkyl)-ammonium salts, tri-(C1-C4-alkyl)-ammonium salts, C5- or C6- cycloalkylammonium salts and di-(C1-C2-alkyl)-benzyl-ammonium salts
13. A herbicidal composition comprising a herbicidally effective amount of a compound according to any one of claims 1 to 11 in admixture with a suitable carrier or diluent.
14. A herbicidal composition comprising a herbicidally effective amount of a compound according to any one of claims 1 to 11 in admixture with an extender or a surface active agent.
15. A method of combating weeds which comprises applying to the weeds, or to a habitat thereof, a herbicidally effective amount of a compound according to any one of claims 1 to 11.
16. A method of combating weeds which comprises applying to the weeds, or to a habitat thereof, a herbicidally effective amount of a composition containing a compound according to any one of claims 1 to 11 in admixture with a suitable carrier or diluent.
17. A method of combating weeds which comprises applying to the weeds, or to a habitat thereof, a herbicidally effective amount of a composition containing between 0.1 and 95% by weight of a compound according to any one of claims 1 to 11 in admixture with a suitable carrier or diluent.
18. A method of combating weeds which comprises applying to the weeds, or to a habitat thereof, a herbicidally effective amount of a composition containing between 0.5 and 90% by weight of a compound according to any one of claims 1 to 11 in admixture with a suitable carrier or diluent.
19. A method of combating weeds which comprises applying to the weeds, or to a habitat thereof, a herbicidally effective amount of a compound according to any one of claims 1 to 11 wherein the compound is applied as a pre-emergence herbicide.
20. A method of combating weeds which comprises applying to the weeds, or to a habitat thereof, a herbicidally effective amount of a compound according to any one of claims 1 to 11 wherein the compound is applied as a post-emergence herbicide.
21. A method of combating weeds which comprises applying to the weeds, or to a habitat thereof, a herbicidally effective amount of a compound according to any one of claims 1 to 11 wherein the compound is applied to an area of cultivation at a rate of between 0.01 and 15 kg/ha.
22. A method of combating weeds which comprises applying to the weeds, or to a habitat thereof, a herbicidally effective amount of a compound according to any one of claims 1 to 11 wherein the compound is applied to an area of cultivation at a rate of between 0.05 and 10 kg/ha.
23. A process for preparing a compound of the general formula (I) according to claim 1, which process comprises a) reacting a triazolinone of the general formula in which n, R1 and R2 have the meanings indicated in claim 1, with a sulphonyl isocyanate of the general formula (III) R3-SO2-N=C=O (III) in which R3 has the meaning indicated in claim 1, or b) reaching a triazolinone derivative of the general formula (IV) in which n, R1 and R2 have the meanings indicated in claim 1 and Z represents chlorine, C1-C4-alkoxy, benzyloxy or phenoxy, with a sulphonamide of the general formula (V) R3-SO2-NH2 (V) in which R3 has the meaning indicated in claim 1, or c) reacting a triazolinone of the general formula (II) in which n, R1 and R2 have the meanings indicated in claim 1, with a sulphonamide derivative of the general formula (VI) R3-SO2-NH-CO-Z (VI) in which R3 has the meaning indicated in claim 1 and Z represents chlorine, C1-C4-alkoxy, benzyloxy or phenoxy, and where required, forming a salt thereof.
24. A process according to claim 23 wherein Z represent methoxy or phenoxy.
25. A process for preparng a herbicidal composition which process comprises admixing a sulphonylaminocarbonyltriazolinone of the general formula (I) according to claim 1 with a carrier and/or surface-active agent.
26. A compound of the general formula (IV) in which n, R1 and R2 are as defined in claim 1, 2 or 3 and Z represents chlorine, C1-C4-alkoxy, benzyloxy or phenoxy.
27. A compound according to claim 26 wherein Z represents methoxy or phenoxy.
28. A compound of the formula in which n is 0 (zero), R1 is NH-CH3, and R2 is CH3, C2H5, C3H7, CH(CH3)2 or CH2-CH=CH2.
29. A compound of the formula in which R1 is and R2 is (c) C3H7 (d) CH (CH2) 2 (e) CH2-CH=CH2 (f) CH2-CH=CH2 C2H5 (g) CH2-CH=CH2 CH2-CH=CH2 (h) CH2-CH=CH2 CH(CH3)2 (i) CH2-CH=CH2 C3H7 (j) CH2-C=CH

(k) CH2-CH=CH2 CH2-C=CH

(l) OCH3 CH3 (m) OCH3 C2H5 (n) OC2H5 CH3 (o) OC2H5 C2H5 (p) OC3H7-n CH2-CH=CH2 (q) OCH2-CH=CH2 C2H5
30. A compound of the formula in which n represents the number 0, 1, or 2, R1 represents di-(C1-C4-alkyl)-amino, and R2 represents C1-C6-alkyl.
CA002029132A 1989-11-03 1990-11-01 Sulphonylaminocarbonyltriazolinones having substituents which are bonded via sulphur Expired - Fee Related CA2029132C (en)

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DE3936622A1 (en) * 1989-11-03 1991-05-08 Bayer Ag HALOGENED SULFONYLAMINOCARBONYLTRIAZOLINONE
DE4131842A1 (en) * 1991-09-25 1993-04-01 Bayer Ag SULFONYLAMINOCARBONYLTRIAZOLINONE WITH TWO OXYGEN SUBSTITUTES
DE4110795A1 (en) * 1991-04-04 1992-10-08 Bayer Ag SULFONYLAMINOCARBONYLTRIAZOLINONE WITH OXYGEN SUBSTITUTES
DE3928662A1 (en) * 1989-08-30 1991-03-07 Bayer Ag SUBSTITUTED 4,5-DIAMINO-1,2,4-TRIAZOL-3- (THI) ONE
DE4435547A1 (en) * 1994-10-05 1996-04-11 Bayer Ag Sulfonylaminocarbonyltriazolinone with substituents bonded via oxygen and sulfur
DE19502579A1 (en) * 1995-01-27 1996-08-01 Bayer Ag Sulfonylamino (thio) carbonyl-triazolin (thi) one
DE19508119A1 (en) * 1995-03-08 1996-09-12 Bayer Ag Sulfonylaminocarbonyltriazolinone with haloalkylthio substituents
DE19517505A1 (en) * 1995-05-12 1996-11-14 Bayer Ag Sulfonylamino (thio) carbonyltriazolin (thi) ones with aryloxy or arylthio substituents
DE19525974A1 (en) * 1995-07-17 1997-01-23 Bayer Ag Substituted arylsulfonylamino (thio) carbonyltriazolin (thi) one
DE19540737A1 (en) 1995-11-02 1997-05-07 Bayer Ag Substituted sulfonylamino (thio) carbonyl compounds
ZA974703B (en) * 1996-05-30 1997-12-30 Bayer Ag Substituted sulfonylamino(thio)carbonyl compounds.
DE19632945A1 (en) * 1996-08-16 1998-02-19 Bayer Ag Substituted sulfonylamino (thio) carbonyl compounds
DE19802697A1 (en) 1998-01-24 1999-07-29 Bayer Ag Selective, synergistic herbicidal composition, especially for weed control in wheat
DE19843766A1 (en) * 1998-09-24 2000-03-30 Bayer Ag Substituted thiazole (in) ylidene aminosulfonylamino (thio) carbonyl triazolinones
KR20050083214A (en) * 2004-02-03 2005-08-26 이석희 Manufacturing method of canned crab
EP1717228A1 (en) 2005-04-28 2006-11-02 Bayer CropScience GmbH Sulfonylamino(thio)carbonylderivatives as herbicides or plant growth regulators
WO2014202510A1 (en) 2013-06-20 2014-12-24 Bayer Cropscience Ag Aryl sulfide derivatives and aryl sulfoxide derivatives as acaricides and insecticides
JOP20190094A1 (en) 2016-10-27 2019-04-25 Broad Inst Inc 2,4,5-trisubstituted 1,2,4-triazolones useful as inhibitors of dhodh
CN117402121A (en) * 2022-07-14 2024-01-16 武汉智汇农耀科技有限公司 Triazolinone structure-containing compound, and preparation method and application thereof

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