CA2029105C - Halogenated sulphonylaminocarbonyltriazolinones - Google Patents

Halogenated sulphonylaminocarbonyltriazolinones Download PDF

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CA2029105C
CA2029105C CA002029105A CA2029105A CA2029105C CA 2029105 C CA2029105 C CA 2029105C CA 002029105 A CA002029105 A CA 002029105A CA 2029105 A CA2029105 A CA 2029105A CA 2029105 C CA2029105 C CA 2029105C
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chlorine
alkyl
fluorine
alkoxy
optionally substituted
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CA2029105A1 (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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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
    • 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
    • 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
    • C07D403/14—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 three or more hetero rings
    • 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

Abstract

Herbicidal halogenated sulphanylaminocarbonyl-triazolinones of the formula (see formula I) in which R1 represents hydrogen, hydroxyl or amino, or repre-sents an optionally substituted radical from the group consisting of alkyl, alkenyl, alkynyl, cyclo-alkyl, aralkyl, aryl, alkoxy, alkenyloxy, alkyl-amino, cycloalkylamino and dialkylamino, R2 represents halogen and R3 represents an optionally substituted radical from the group consisting of alkyl, aralkyl, aryl and heteroaryl, and salts thereof.

Description

The invention relates to new halogenated sul-phonylaminocarbonyltriazolinones, to several processes for their preparation, and to their use as herbicides.
It is known that certain substituted aminocarbon ylimidazolinones, such as, for example, 1-isobutylamino carbonyl-2-imidazolidinone (isocarbamid), have herbicidal properties (cf. R. Wegler, Chemie der Pflanzenschutz- and 5chadlingsbekampfungsmittel [Chemistry of Plant Protec tion Agents and Pesticides], Vol. 5, p. 219, Springer Verlag, Berlin-Heidelberg-New York, 1977). However, the action of this compound is not satisfactory in all respects.
The new halogenated sulphonylaminocarbonyl-triazolinones of the general formula (I) R3-SOZ-NH-CO-Nr\N-R1 (I) ~R2 in which R1 represents hydrogen, hydroxyl or amino, or repre-sents an optionally substituted radical from the series comprising alkyl, alkenyl, alkinyl, cyclo-alkyl, aralkyl, aryl, alkoxy, alkenyloxy, al 1 amino, cycloalkylamino and dialkylamino, R2 represents halogen and R3 represents an optionally substituted radical from the series comprising alkyl, aralkyl, aryl and Le A 27 155 _ 1 heteroaryl, as well as salts of compounds of the formula (I) have now been found.
The new halogenated sulphonylaminocarbonyltri-azolinones of the general formula (I) are obtained when a) halogenated triazolinones of the general formula (II) HN~N-R1 (II) in which R' and RZ have the abovementioned meanings are reacted with sulphonyl isocyanates of the general formula (III) R3-SOZ-N=C=0 ( I I I ) in which I5 R3 has the abovementioned meaning, if appropriate in the presence of a diluent, or when b) halogenated triazolinone derivatives of the general formula (IV) Z-CO-N~N-R1 (IV) ~R2 Le A 27 155 in which Rr and Rz h ve the abovementioned meanings and Z represents halogen, alkoxy, aralkoxy or aryloxy are reacted with sulphonamides of the general formula (V) R3-S~z-~z f V) in which R3 has the abovementioned meaning, if ,appropriate in the presence of an acid acceptor ld and if appropriate in the presence of a diluent, or when c) halogenated triazolinones of the general formula (II) O
HN~N-R1 (II) ~R2 in which R' and Rz have the abovementioned meanings are reacted with sulphonamide derivatives of the general formula (VI) R3-sot-rrx-c~-z ~ vI ~
2a in which R3 has the abovementioned meaning and Z represents halogen, alkoxy, aralkoxy or Le A 27 155 - 3 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 halogenated sulphonylaminocarbonyltri-azolinones 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 known herbicide 1-isobutylaminocarbonyl-2-imidazolidinone (isocarbamid), which has a similar structure.
The invention preferably relates to compounds of the formula (I) in which R1 represents hydrogen, hydroxyl or amino, or repre-sents C1-C6-alkyl which is optionally substituted by fluorine, chlorine, bromine, cyano, C1-Ca-alkoxy, C1-Ca-alkylcarbonyl or C1-Ca-alkoxy-carbonyl, or represents C3-Cs-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-Ca-alkyl, or represents phenyl-Cl-C3-alkyl which is optionally substituted by fluorine, chlorine, bromine, cyano, nitro, C1-Ca-alkyl, trifluoromethyl, C1-Ca-alkoxy and/or C1-Ca-alkoxy-carbonyl, or represents phenyl which is optionally substituted by fluorine, chlorine, bromine, cyano, nitro, C~-Ca-alkyl, trifluoromethyl, he A 27 155 C1-C4-alkoxy, fluorine- and/or chlorine-substituted C1-C3-alkoxy, C~-C4-alkylthio, fluorine- and/or chlorine-substituted C1-C3-alkylthio, Cl-C4-alkylsul-phinyl, C1-C4-alkylsulghonyl and/or Cl-C,,-alkoxy-carbonyl, or represents C1-Cs-alkoxy which is option-ally substituted by fluorine, chlorine, cyano, C1-C4-alkoxy or Cl-C,,-alkoxy-c _rbonyl, or represents C~-C4-alkenyloxy, or represents fluorine-, cyano-, phenyl-, C1-Ca-alkoxy- or C1-C4-alkoxy-carbonyl-ZO substituted Cl-C4-alkylamino, C3-C6-cycloalkylamino, or represents di- ( C1-C,,-alkyl ) -amino, RZ represents fluorine, chlorine, bromine or iodine and R3 represents the group ~ , where R° and RS are identical or different and represent hydrogen, fluorine, chlorine, bromine, iodine, nitro, C1-C6-alkyl (which is optionally substi-tuted by fluorine, chlorine, bromine, cyano, carboxyl, C1-C4-alkoxycarbonyl, C1-C4-alkyl-amino-carbonyl, di-(Cl-C4-alkyl)amino-carbonyl, hydroxyl, C1-C,,-alkoxy, formyloxy, C,-Cw-alkyl-carbonyloxy, C1-C4-alkoxy-carbonyloxy, C~-C4-alkylamino-carbonyloxy, C1-C4-alkylthio, C1-C4_ alkylsulphinyl, Cl-C4-alkylsulphonyl, di- ( C1-C,,-alkyl)-aminosulphonyl, C3-C6-cycloalkyl or phenyl), or represent CZ-Cs-alkenyl (which is optionally substituted by fluorine, chlorine, bromine, cyano, C1-C4-alkoxy-carbonyl, carboxyl or phenyl ) , or represent C2-C6-alkinyl (which is Le A 27 155 - 5 -~~2~~~~
optionally substituted by fluorine, chlorine, bromine, cyano, C1-C,,-alkoxy-carbonyl, carboxyl or phenyl), or represent C1-C4-alkoxy (which is optionally substituted by fluorine, chloxine, bromine, cyano, carboxyl, C1-C4-alkoxy-carbonyl, G1-C4-alkoxy, Cl-C~-alkylthio, C1-G4-alkyl-sulphinyl or C1-C4-alkylsulphonyl ) , or represent C1-C4-alkylthio (which is optionally substituted by fluorine, chlorine, bromine, cyano, car-boxyl, C1-C4-alkoxy-carbonyl, C1-C4-alkylthio, C1-C4-alkylsulphinyl or C1-C4-alkylsulphanyl ) , ar represent C~-Cs-alkenyloxy (which is optionally substituted by fluorine, chlorine, bromine, cyano or C1-C4-alkoxy-carbonyl), or represent CZ-Cs-alkenylthio (which is optionally sub-stituted by fluorine, chlorine, bromine, cyano, nitro, Ci-C3-alkylthio or C1-C,,-alkoxycarbonyl ) , C~-Cs-alkinyloxy, C3-Cs-alkinylthio ar the radical -~ ( O ) p-Rs, where p represents the numbers 1 or 2 and Rs represents C1-C4-alkyl (which is optionally substituted by fluorine, chlorine, brom-ine, cyano or C1-C4-alkoxy-carbonyl ) , C3-Cs-alkenyl, C3-Cs~alkinyl, C1-C4-alkoxy, C1-C4-alkoxy-C1-Cw-alkylamino, Cl-C4-alkylamino, di-(C1-CH-alkyl)-amino and phenyl, ar represents the radical -IdHOR', where R' represents C1-C12-alkyl (which is optionally substituted by fluorine, chlorine, cyano, C1-C4-alkaxy, C1-C4-Le A 27 155 - 6 -alkylthio, C1-C4-alkylsulphinyl, Cl-C4_ alkylsulphonyl, C1-Ca-alkyl-carbonyl, Cl-Ca-alkoxycarbonyl, Cl-Ca-alkylamino-carbonyl or di-(C1-Ca-alkyl)-amino-carbonyl ) , or represents C3-Cs-alkenyl (which is optionally substituted by fluorine, chlorine or bromine ) , C3-Cs-alkinyl, C3-Cs-cycloalkyl, C3-Cs-cycloalkyl-C1-CZ-alkyl, phenyl-Cl-CZ_ alkyl (which is optionally substitu ,, ted by fluorine, chlorine, vitro, cyano, C1-Ca-alkyl, C1-Ca-alkoxy or C1-Ca-alkoxy-carbonyl ) , or represents benzhydryl, or represents phenyl (which is optionally substituted by fluorine, chlorine, vitro, cyano, C1-Ca-alkyl, trifluoromethyl, C1-Ca-alkoxy, C1-C2-fluoroalkoxy, C1-Ca-alkylthio, trifluoromethylthio or C1-Ca-alkoxycarbonyl ) , Ra and/or RS furthermore represent phenyl or phenoxy, or represent C1-Ca-alkylcarbonylamino, Cl-Ca-alkoxy-carbonylamino, Cl-Ca-alkylamino-carbonyl-amino and di-(C1-Ca-alkyl)-amino-carbonylamino or represent the radical -CO-Red where Rs represents C1-Cs-alkyl, C1-Cs-alkoxy, C3-Cs-cycloalkoxy, C3-Cs-alkenyloxy, Cl-ca-alkyl-thio, Cx-Ca-alkylamino, Cl-Ca-alkoxyamino, C1-Ca-alkoxy-C1-Ca-allyl-amino or di- ( C1-Ca_ alkyl)-amino (which are optionally Le A 27 155 - 7 ~~2~:~
substituted by fluorine and/or chlorine), R'' and/or RS furthermore represent trimethylsilyl, thiazolinyl, C1-C,,-alkylsulphonyloxy or di (C1-C4-alkyl)-aminosulphonylamino or represent the radical -CH=N-R9, where R9 is C1-C6-alkyl which is optionally substi-tuted by fluorine, chlorine, cyano, carboxyl, Cl-C4-alkoxy, C1-C~-alkylthio, Cl-C,,-alkylsulphinyl or C1-C4-alkylsul-phonyl, or represents benzyl which is optionally substituted by fluorine or chlorine, or represents C3-C6-alkenyl or G3-C6-alkinyl, each of which is optionally substituted by fluorine or chlorine, or represents phenyl which is optionally substituted by fluorine, chlorine, brow-ine, C~-C4-alkyl, C1-C4-alkoxy, trifluoro-methyl, trifluoromethoxy or trifluoro-methylthio, or represent C1-Cs-alkoxy, C3-C6-alkenoxy, 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, phenylamino, C1-C4-alkyl-carbonyl-amino, C1-C4-alkoxy-carbonyl-amino or C1-C4-alkyl-sulphonylamino, or represents phenylsulphonylamino which is optionally substituted by fluorine, chlorine, bromine or methyl, furthermore Le A 27 155 R3 represents the radical '~H ~ _ where R10 ~I1 Rz° represents hydrogen or C1-Ca-alkyl, R11 and R12 are identical or different and represent hydrogen, fluorine, chlorine, bromine, vitro, cyano, C1-Ca-alkyl (which is optionally sub stituted by fluorine and/or chlorine), C1-Ca-alkoxy (which is optionally substituted by fluorine and/or chlorine), carboxyl, C1-Ca-alkoxy-carbonyl, dimethylaminocarbonyl, C~-Ca-" alkylsulphonyl or di-(C1-Ca-alkyl)-amino-sulphonyl furthermore R3 represents the radical R13 ~ ~~ s R14 where Y
R13 and R'a are identical or different and represent hydrogen, fluorine, chlorine, bromine, vitro, cyano, C1-Ca-alkyl (which is optionally substi-tuted by fluorine and/or chlorine) or C1-Ca-alkoxy (which is optionally substituted by fluorine and/or chlorine);
furthermore R3 represents the radical ~ ~ where ~N
fib R15 and R16 are identical or different and represent hydrogen, fluorine, chlorine, bromine, vitro, cyano, C~-Ca-alkyl (which is optionally substi tuted by fluorine and/or chlorine) , C1-Ga-alkoxy Le A 27 155 - 9 -(which is optionally substituted by fluorine and/or chlorine), or represent C1-C4-alkylthio, Cz-C4-alkylsulphinyl or C1-C4-alkylsulphonyl (which are optionally substituted by fluorine and/or chlorine), ar represent aminosulphonyl, mono- ( C1-C4-alkyl ) -aminosulphonyl, di- ( C1-Ck-alkyl)-aminosulphonyl or C1-C~-alkoxy-carbonyl or dimethylaminocarbonyl;
furthermore R3 rep,,resents the radical R1 ~ ~) ~~R1 a Rl' and Rl8 are identical or different and represent hydrogen, fluorine, chlorine, bromine, C1-C4-alkyl (which is optionally substituted by fluarine 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-C,,-alkylsulphonyl (which are optionally substituted by fluorine and/or chlorine), or represent di-(C1-C4-alkyl)-amino sulphonyl;
furthermore Rz~
R3 represents the radical -~R20 where A
R19 and Rz° are identical or different and represent hydrogen, fluorine, chlorine, bromine, cyano, nitro, C1-C4-alkyl (which is optionally sub-stituted by fluorine and/or chlorine), Cl-CA-Le .~. 27 ? 55 - 10 -~~~J ~.~~
alkoxy (which is optionally substituted by fluorine and/or chlorine), C1-Ca-alkylthio, C1-Cu-alkylsulphinyl or C,-C4-alkylsulphonyl (which is optionally substituted by fluorine and/or chlorine), di-(C1-C,,-alkyl}-amino-sulphonyl, C1-C4-alkoxy-carbonyl or dimethyl-aminocarbonyl, and A represents oxygen, sulphur or the group N-Z'', where IO Z1 represents hydrogen, C1-Ca-alkyl (which is optionally substituted by fluorine, chlorine, bromine or cyano), C3-Cs-cyclo-alkyl, benzyl, phenyl (which is optionally substituted by fluorine, chlorine, bromine or vitro), C1-C6-alkylcarbonyl, Cl-C4-alkoxy-carbonyl or di- ( C1-C4-alkyl ) -amino-carbonyl;
furthermore ~-~- N
R3 represents the radical ~-~-f-R2z where Y~
R21 and R22 are identical or different and represent hydrogen, C1-C4-alkyl, halogen, C1-C4-alkoxycar-bonyl, C1-C,,-alkoxy or C1-C4-halogenoalkoxy, Y1 represents sulphur or the group N-Rz3, where R23 represents hydrogen or C1-C~-alkyl;
furthermore R3 represents the radical ( where Id~N~

R2~1 Le A 2? 155 - 11 -Rz4 represents hydrogen, C1-C4-alkyl , benzyl , pyridyl, quinolinyl or phenyl, Rz5 represents hydrogen, halogen, cyano, vitro, C1-Ca-alkyl (which is optionally substituted by fluorine and/or chlorine), C1-C4-alkoxy (which is optionally substituted by fluorine and/or chlorine) , dioxolanyl or C1-C4-alkoxy-carbonyl and Rzs represents hydrogen, halogen or C1-C,~-alkyl;
furthermore R3 represents one of the groups listed below:
H3C0 ~ H3C I I
S-'N-C4H9 ; N~~ CHZCF3 Il o The invention also 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- ( C1-Cz-alkyl ) benzyl-ammonium salts of compounds of the formula (I) in which R1, Rz and R3 have the meanings indicated above as being preferred.
The invention particularly relates to compaunds of the formula (I) in which Le A 27 155 - 12 -R1 represents hydrogen, or represents C,-C4-alkyl which is optionally substituted by fluorine, cyano, methoxy or ethoxy, or represents allyl, or repre-sents C3-C6-cycloalkyl, or represents phenyl, or represents C1-C,,-alkoxy, C3-C4-alkenyloxy, or repre-sents C1-C3-alkyl amino, C3-C6-cycloalkylamino, or represents di-(C~-C3-alkyl)-amino, RZ represents chlorine or bromine, and R3 represents the group -~j where ~ , RR
R° represents fluorine, chlorine, bromine, methyl, trifluoromethyl, methoxy, difluoromethoxy, trifluoromethoxy, 2-chloro-ethoxy, 2-methoxy-ethoxy, Cl-C~-alkylthio, Cz-C3-alkylsulphinyl, C1-C3-alkylsulphonyl, dimethylaminosulphonyl, diethylaminosulphonyl, N-methoxy-N-methylamino-sulphonyl, N-methoxyaminosulphonyl, phenyl, phenoxy or C1-G3-alkoxy-carbonyl, and RS represents hydrogen, fluorine, chlorine or bromine;
furthermore _ R12 R3 represents the radical -cH ~ ~ where y o Ri° represents hydrogen, R'1 represents fluorine, chlorine, bromine, methyl, methoxy, difluoromethoxy, trifluoromethoxy, ethoxy, methoxycarbonyl, ethoxycarbonyl, methylsulphonyl or dimethylaminosulphonyl, and Le A 27 155 - 13 -R12 represents hydrogen;
furthermore R3 represents the radical Ro-c'~S

where R represents C~-Ca-alkyl, or p Ro-c ~
represents the radical ~N~'N
where R represents Cl-C4-alkyl. ~E

Examples of the compounds according to the invention are listed in fable 1 below - cf. also the Preparation Examples.
Le A 27 X55 - 14 O
R3-SOZ-NH-CO-N~N-R1 N~R2 Table 1: Examples the compounds o the ormula (I) o F
Br \ _ /

_ \

-OCF~
Br CH

SCH~
F
C
H
OCH2CH~C1 CHICH=CH2 C1 Le A 27 155 ° 15 r Table 1: (continuation) ~a R3 C1 ~
~

~

~COOCH

~ COOGH3 C 2 ( ?--C H
-Z

~
' CH3 Br -~ CH2- .

/
' CH3 Br -~ CH2-C2H5 C1 ~CH~-SO~CH3 O-CHI-CH=GH2 C1 Le A z7 ls5 - is -~~2~:~~~
Table 1: (continuation) Ri R2 Rs F

S02-N(CH3)2 CH3 Br SO'NHOCH~

C3Hy C1 N~N~

--rCOOCH3 C ~~ ~~1 N~N~

N\~~

~COOC~HS

NON

Le ~ 27 1.55 _ 17 _ _ ~a'~,'~~.~
Table 1: (continuation) N(CH3)Z C1 ~ ~

o CF3 N(CH3>Z F
\N~

CON(CH3)2 CH3 ~ C2 ~ ~~
/~

N~

C2H5 C1 ~CON(CH3)2 ' ~~~

Br \

--Br F J
\

~

Le A 27 155 - 18 -Table 1: (continuation) Ri Rz Rs CH2-~ Br /

S02 /-\
CH3 Br / \
/ \
CH3 C1 /!\ _ 0 /-\
F
NlCH3)2 C1 /

CH3 C1 / \

CHI Br / \
Br Le A 27 155 - 19 -Table 1: (continuation) ~2 ~3 CH3 F' CH3"~

CH2 ~-~ C1 ~~'~ CHL_ .. OC2H5 CH N-B

r S

Si(CH3)~

'I CON(CH3)z Br ~COOCH3 C I! ,I

wtd~

i w r CH2-CH=CH2 Br N>N~

Le .~ 27 i55 _ 2p ~,~2~~.~~
Table is (continuation) Ri Ra Rs CH2-CHBr-CH2-8r Br f-\ CH -Z

S02NCH3(OCH3) CH3 Br /-\
Sp2CH3 CH3 C1 ~ ' CN3 F ~ ' CZ
C2H5 C1 ~ ' CH2_ C2H5 Br \

C3H~-n Br Le A 27 155 - 21 -Table 1: (continuation) SCH(CH3)2 CH3 Br /-~
If, for example, 2,6-difluoro-phenylsulphonyl isocyanate and 5-bromo-4-ethyl-2,4-dihydro-3H-1,2,4-triazol-3-one are used as starting substances, the course of the reaction in process (a) according to the invention can be outlined by the following equation:

F ~, H-N~N-C2H5 S02-N=C=0 +
N'~B r F
F O
'~ S02-NH-CO~N~N-C2H5 F ~Br Le A 27 155 - 22 -If, for example, 2-methoxy-benzenesulphonamide and 5-chloro-2-chlorocarbonyl-4-methoxy-2,4-dihydro-3H-1,2,4-triazol-3-one are used as starting substances, the course of the reaction in process (b) according to the invention can be outlined by the following equation:

OCH3 ll C1-CO-N~N-OCH3 502-NH2 + f ~C1 .. OCH3 O
/-_\ ~
---~ S02-NH-CO~N~N-OCH3 ~C 1 If, for example, 5-bromo-4-dimethylamino-2,4-dihydro-3H-1,2,4-triazol-3-one and N-methoxycarbonyl-2-trifluoromethyl-benzenesulphonamide are used as starting substances, the course of the reaction in process (c) according to the invention can be outlined by the follow-ing equation:

CF3 ~
\ H-N~N-N(CH3)2 ~S02-NH-COOCH3 + ~
~Br -°'° ~-~ S02-NH-CO~N~N-N(CN3)2 -HOCH3 ~
~Br Le A 27 155 - 2~ -Formula (II) provides a general definition of the halogenated triazolinones to be used as starting substan-ces in processes (a) and (e) according to the invention for the preparation of compounds of the formula (I).
In formula (II), R1 and RZ preferably, or in particular, have those meanings which have already been given above in connection with the description of the compounds of the formula (I) according to the invention as being preferred, or particularly preferred, for R1 and RZ .
~:Yamples of the starting substances of the formula (II) are listed in Table 2 below.

HN~N~R1 N--~R2 ( I I ) Table 2: Examples of the starting substances of the formula (II):
~z H Br CH3 Br C2H5 Br C3H7 Br CH(CH3)2 C1 Bs CH2-CH=CHI gs Le A 27 155 _ 2~ -Table 2: (continuation) Ra Rz CH(CH3)2 F

C3H~ CI

/~\
Br N(CH3)2 Br N(CH3)2 CI

NH-CH3 Br OCH3 Br C3H~ F

F

OOHS Br CH2-C I Br CH2~ C1 C(CH3)3 Br CH2-CH(CH3)2 Br CH2-CH(CH3)2 C1 CH2~ Br 0-CBH~-n Br Le .A 27 155 _ 25 Table 2: (continuation) CH2 Br ~' C 1 CZHS I
CqHg Br iH-C2H5 Br ~H-CZHS~ C1 CH(CH3)2 C1 CHZ-CHBr-CH2Br Br CHZ-CHBr-CHZBr C1 Br F

Br Le A a~ i5s _ 2s Table 2: (continuation) Ri RZ
Br Br OC3N~ C1 The starting substances of the formula (II) are known andlor can be prepared by processes known per se (cf. Chem. Ber. 102 (1969), 755-766 and the Preparation Examples).
Formula (III) provides a general definition of the sulphonyl isocyanates also to be used as starting substances in process (a) according to the invention for the preparation of compounds of the formula (I).
In formula ( I II ) , 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 preferred, or particularly preferred, for R3.
The following may be mentioned as examples of the starting substances of the formula (III): 2-fluoro-, 2-Le A 27 155 .. 27 ~~~~s~3 chloro-, 2-bromo-, 2-methyl-, 2-methoxy-, 2-trifluoro-methyl-, 2-difluoro-methoxy-, 2-trifluoromethoxy-, 2-methylthio-, 2-ethylthio-, 2-propylthio-, 2-methyl-sulphinyl-, 2-methylsulphonyl-, 2-dimethylaminosulpho-nyl-, 2-diethylaminosulphanyl-, 2-(N-methoxy-N-methyl)-aminosulphonyl-, 2-phenyl-, 2-phenoxy-, 2-methoxy-carbonyl-, 2-ethoxycarbonyl-, 2-propoxycarbonyl- and 2-isopropoxycarbonyl-phenylsulphonyl isocyanate,2-fluoro-, 2-chloro-, 2-difluoromethoxy-, 2-trifluoromethoxy-, 2-methoxycarbonyl- and 2-ethoxycarbonyl-benzylsulphonyl isocyanate, 2-methoxycarbonyl-3-thienyl-sulphonyl iso-cyanate, 4-methoxycarbonyl- and 4-ethoxycarbonyl-1-methyl-pyrazol-5-yl-sulphonyl isocyanate.
The sulphonyl isocyanates of the formula (TII) are known and/or can be prepared by processes known per se (cf. US Patent 4,127,405, 4,169,719, 4,371,391 EP-A
7,687, 13,480, 21,641, 23,141, 23,422, 30,139, 35,893, 44,808, 44,809, 48,143, 51,466, 64,322, 70,041, 1?3,312).
Process (a) according to the invention for the preparation of 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 aromatic, 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, tetrahydrafuran and dioxane, Le A 27 155 - 28 _ ketones, such as acetone, methyl ethyl ketone, methyl isopropyl ketone and methyl isobutyl ketone, esters, such as methyl acetate and ethyl acetate, nitriles, such as, for example, acetonitrile and propionitxile, amides, such as, for example, dimethylformamide, dimethylacetamide and N-methyl-pyrrolidone, and also dimethyl sulphoxide, tetramethylene sulphone and hexamethylphosphoric triamide.
When carrying out process (a) according to the invention, the reaction temperatures can be varied within a substantial range. In general, the process is carried out at temperatures between 0°C and 150°C, preferably at temperatures between 10°C and 80°C.
Process (a) according to the invention is gener-ally carried out under atmospheric pressure.
Far 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, concentrated, and the crude product which remains in the xesidue is crystallized using a suitable solvent, such as, for example, diethyl ether.
The product of the formula (I) which is obtained as crystals is isolated by filtration with suction.
Formula (IV) provides a general definition of the triazolinone derivatives to be used as starting substan ces in process (b) according to the invention for the Le A 27 155 - 2g _ ~~~~=~~.~3.~
preparation of compounds of the formula (I).
In formula (IV), R1 and Rz 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 R1 and R2, and Z preferably represents chlorine, C1-C4-alkoxy, benzyloxy or phenoxy, in particular methoxy or phenoxy.
:..xamples which may be given for the starting substances of the formula (IV) are the compounds of 'the formula (IV) to be prepared from the compounds of the formula (II) listed in Table 2 and phosgene, methyl 25 chloroformate, benzyl chloro~~rmate, phenyl chloroformate or diphenyl carbonate.
The starting substances of the formula (IV) were hitherto unknown.
The new halogenated triazolinone derivatives of ZO the formula (IV) are obtained when triazolinones of the general formula (II) HN~N~R1 (II) N~R 2 in which R1 and Rz have the abovementioned meanings, 25 are reacted with carbonic acid derivatives of the general Le A 27 Z55 -. 30 formula (XI) z-CO-Z1 (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, fox example, tetrahydrofuran, and if appropriate in the presence of an acid acceptor, such as, for example, sodium hydride or potassium tert-butylate, at tempera-tures between -20°C and +100°C (cf. also the Preparation Examples).
Formula (V) grovides a general definition of the sulphonamides also to be used as starting substances in 35 process (b) according to the invention for the prepara tion of compounds of the formula (I). _ 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 prefer-red, or particularly preferred, for R3.
The following may be mentioned as examples of the starting substances of the formula (V): 2-fluaro-, 2-chloro-, 2-bromo-, 2-methyl-, 2-methoxy-, 2-trifluoro-methyl-, 2-difluoro-methoxy-, 2-trifluoromethoxy-, 2-methylthio-, 2-ethylthio-, 2-propylthio-, 2-methyl-sulphinyl-,2-methylsulphonyl-,2-dimethylaminosulphonyl-2-diethylaminosulphonyl-, 2-(R1-methoxy-N-methyi) aminosulphonyl-, 2-phenyl-, 2-phenoxy-, 2-methoxy_ carbonyl-, 2-ethoxycarbonyl-, 2-propoxycarbonyl- and 2 I~e .A 2 7 15 5 _ 31 _ ~~~3 ~. ~~
isopropoxycarbonyl-benzenesulphonamide, 2-fluoro-, 2-chloro-, 2-difluoromethoxy-, 2-trifluoromethoxy-, 2-methoxycarbonyl- and 2-ethoxycarbonyl-phenylmethane-sulphonamide, 2-methoxycarbonyl-3-thiophenesulphonamide, 4-methoxycarbonyl- and 4-ethoxycarbonyl-1-methyl-pyrazole-5-sulphonamide.
The sulphonamides of the formula (V) are known andlor can be prepared by processes known per se (ef. US
Patent 4,12?,405, 4,169,719, 4,371,391; EP-A 7,687, 13,480, 21,641, 23,141, 23,422, 30,139, 35,893, 44,808, 44,809, 48,143, 51,466, 64,322, 70,041, 173,312).
Process (b) according to the invention prepara-tion of the new compounds of the formula (I) is prefera bly carried out using diluents. Suitable diluents for this purpose are virtually all inert organic solvents, for example those which are indicated above for process (a) according to the invention.
Acid acceptors which can be employed in process (b) according to the invention are all acid-binding agents which can customarily be employed for reactions of this type. The following are preferably suitable: alkali metal hydroxides, such as, for 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 tart-butylate and potassium tart-butylate, furthermore aliphatic, aromatic or heterocyclic amines, for example triethylamine, trimethylamine, dimethylaniline, dimethylbenzylamine, pyridine, 1,5-diazabicyclo-[4.3.0]-non-5-ene (DEN), 1,8-he A 27 155 - 32 ~~2~~.0~
diazabicyclo-[5.4.0]-undec-7-ene (DBU) and 1,4-diaza-bicyclo-[2.2.2]-octane (DABCO).
When carrying out process (b) according to the invention, the reaction temperatures can be varied within a substantial range. In general, the process is carried out at temperatures between 0°C and 100°C, preferably at temperatures between 10°C and 60°C.
Process (b) according to the invention is gener ally 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 specifically employed components in a substantial excess. The reactions are generally carried out in a suitable diluent in the presence of an acid acceptor, and the reaction mixture is stirred for several hours at the ZO specifically required temperature. Working-up in process (b) according to the invention is carried out in each case by customary methods.
The halogenated triazolinones of the formula (II) to be used as starting substances in process (c) accord ing 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 for Le A 27 155 - 33 -~~U~~~.~~
the preparation of compounds of the formula (I}.
In formula (VI), R3 and Z preferably, or in particular, have those meanings which have already peen indicated 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, f or R3 and Z .
Process (c) according to the invention is prefer-ably carried out using diluents. Suitable diluents for this purpose are the same organic solvents which have been mentioned above in connection with the description of process (a) according to the invention.
If appropriate, process (c) is carried out in the presence of an acid acceptor. Suitable acid-binding agents for this purpose are the same which have been mentioned above in connection with the description of process (b) according to the invention.
When carrying out process (c) according to the invention, the reaction temperatures can be varied within a substantial range. In general, the process is carried out at temperatures between 0°C and 100°C, preferably at temperatures between 10°C and 60°C.
Process (c) according to the invention is gener ally carried aut under atmospheric pressure. However, it is also possible 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 equimolar amounts. However, it is also possible to use one of the Le A 27 155 - 3~ -two specifically employed components in a substantial excess. The reactions are generally carried out in a suitable diluent in the presence of an acid acceptor, and the reaction mixture is stirred for several hours at the specifically recyuired temperature. Working-up in process (c) according to the invention is carried out in each case by customary methods.
To convert the compounds of the formula ( I ) to salts, they are stirred with suitable salt formers, such as, for example, sodium hydroxide, sodium methylate, sodium ethylate, potassium hydroxide, potassium methylate or potassium ethylate, ammonia, isopropylamine, dibutyl-amine or triethylamine, in suitable diluents, such as, for example, water, methanol or ethanol. The salts can then be isolated as crystalline products, if necessary after concentration.
The active compounds according to the invention can be used as defoliants, desiccants, agents for des-troying 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 aenera° Sinapis, Lepidium, Galium, Stellaria, Matricaria, Anthemis, Galinsoga, Chenopodium, Urtica, Senecio, Amaranthus, Le ~ 27 155 _ 35 _ Portulaca, Xanthium, Canvolvulus, Ipomoea, Polygonum, Sesbania, Ambrosia, Cirsium, Carduus, Sonchus, Solarium, Rorippa, Rotala, Lindernia, Lamium, Veronica, Abutilon, Emex, Datura, Viola, Galeopsis, Papaver, Centaurea, Trifolium, Ranunculus and Taraxacum.
Dicotvledon cultures of the genera~ Gossypium, Glycine, Beta, Daueus, Phaseolus, Pisum, Solarium, Linum, Ipomoea, Vicia, Nicotiana, Lycopersicon, Arachis, Bras-sica, Lactuca, Cucumis and Cucurbita.
Monocotyledon weeds of the genera~ Echinochloa, Setaria, Panicum, Digitaria, Phleum, Poa, Festuca, Eleusine, Brachiaria, Lolium, Bromus, Avena, Cyperus, Sorghum, Agropyron, Cynodon, Monochoria, Fimbristylis, Sagittaria, Eleocharis, Scirpus, Paspalum, Ischaemum, Sphenoclea, Dactyloctenium, Agrastis, 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 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, far 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 planta-tions, tea plantations, rubber plantations, oil palm Le A 27 155 - 3s -plantations, cocoa plantations, soft fruit plantings arid hopfields, in ornamental lawns, sports fields and grazing land, and for the selective combating of weeds in annual cultures.
The compounds of the formula (I) according to the invention are particularly suitable for selectively combating monocotyledon and dicotyledon weeds in mono cotyledon crops, using the pre-emergence or the post emergence method. They are markedly more effective than, for example, isocarbamid.
To a certain extent, the compounds according to the invention also have a fungicidal action, for example against powdery mildew on vines arid against Pyricularia oryzae on rice.
The active compounds can be converted into the customary formulations, such as solutions, emulsions, wettable powders, suspensions, powders, dusting agents, pastes, soluble powders, granules, suspension-emulsion concentrates, natural and synthetic materials impregnated with active compound, and very fine capsules in polymeric substances.
These formulations ,are produced in a known manner, for example by mixing the active compounds with extenders, that is liquid solvents and/or solid carriers, optionally with the use of surface-active agents, that is emulsifying agents and/or dispersing agents and/or foam-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 Le A 27 155 - 37 suitable in the main: aromatics, such as xylene, toluene, ox alkylnaphthalenes, chlorinated aromatics and chlorina-ted aliphatic hydrocarbons, such as chlorobenzenes, chloroethylenes or methylene chloride, aliphatic hydro-carbons, such as cyclohexane or paraffins, for example petroleum fractions, mineral and vegetable oils, alcohols, such as butanol or glycol as well as their ethers and esters, ketones, such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents, such as dimethylformamide and dimethyl sulphoxide, as well as water.
As solid carriers there are suitable: for example ammonium salts and ground natural minerals, such as kaolins, clays, talc, chalk, quartz, attapulgite, mon~tmo-rillonite or diatomaceous earth, and ground synthetic minerals, such as highly disperse silica, alumina and silicates, as solid carriers for granules there are suitable: for example crushed and fractionated natural rocks such as calcite, marble, pumice, sepiolite and dolomite, as well as synthetic granules of inorganic and organic meals, and granules of organic material such as sawdust, coconut shells, maize cobs and tobacco stalks;
as emulsifying and/or foamforming agents there are suitable: for example non-ionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethy-lene fatty alcohol ethers, for example alkylaryl polygly-col ethers, alkylsulphonates, alkyl sulphates, arylsul-phonates as well as albumen hydrolysis products; as dispersing agents there are suitable: for example lignin-sulphite waste liquors and methylcellulose.
he A 27 155 - 3g _ ~~~~~a~
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.
It is possible to use colorants such as inorganic pigments, far example iron oxide, titanium oxide and Prussian Hlue, 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 (AMETFIYDIONE) or N-(2-benzothiazolyl)-N, N'-dimethylurea (3KETABENZTAIAZURON) for combating weeds in cereals; 4-amino-3-methyl-6-phenyl-1,2,4-triazin-5(4~I)-one {I~IETAMITRON) for combating weeds in sugar beet, and 4-amino-6-(1,1-di.methylethyl)-3-methylthio-1,2,4-triazi.n-5(4H)-.one (PiETRIBUZIN) for combating weeds i.n soya beans;
Le A 27 155 - 3g -furthermore also 2,4-dichlorophenoxyacetic acid (2,4-D);
4-(2,4-dichlorophenoxyj-butyric acid (2,4-DBj; 2,4-dichlorophenoxypropionic 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 (BROI~IOXYNIL); 2-chloro-N~[(4ametlnoxy-6-methyl-1,3,5-triazin-2-yl)-amino]-carbonyl}-benzenesulphonamide (CHLORSULFURON); N,N-di-methyl-N'-(3-chloro-4-methylphenyl)-urea (CHLORTOLURON);
4-amino-6-t-butyl-3-ethylthio-1,2,4-triazin-5(4H)-one (ETHIOZIN); [(4-amino-3,5-dichloro-6-fluoro-2-pyridinyl)-oxy]-acetic acid or its 1-methylheptyl ester (FLUROXYPYR);methyl2-[4,5-dihydro-4-methyl -4-(1-methyl-ethyl)-5-oxo-1H-imidazol-2-yl]-4(5)-methylbenzoate (IMAZAMETHABENZ); 3,5-diiodo-4-hydroxybenzonitrile (IOXYNIL); N,N-dimethyl-N'-(4-isopropylphenyl)-urea (ISOPROTURONj; (2-methyl-4-chlorophenoxy)-acetic acid (MCPA); (4-chloro-2-methylphenoxy)-propionic acid (MCPP);
N-methyl-2-(1,3-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); O-(6-chloro 3-phenyl-pyridazin-4-yl) S-octyl thiocarbonate (PYRIDATE);
4-ethylamino-2-t-butylamino-6-methylthio-s-triazine (TERBUTRYNE); methyl 3-[[[[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)-amino]-carbonyl]-amino]-sulphonyl]-thiophene-2-carboxylate (THTAMETURON) and 5-(2,3,3-trichloroallyl) N,N-diisopropylthiocarbamate (TRI-Le A 27 155 - 40 -ALLATE). Surprisingly, some mixtures also show synergistic action.
Mixtures with other known active compounds, such as fungicides, insecticides, acaricides, nematicides, bird repellents, plant nutrients and agents which improve soil structure, are also possible.
The active compounds can be used as such, in the foran of their formulations or in the use forans prepared therefrom by further dilution, such as ready-to-use solutions, suspensions, emulsions, powders, pastes and granules. They are used in the customary manner, for example by watering, spraying, atomizing or scattering.
The active compounds according to the invention can be applied either before or after emergence of the plants.
They can also be incorporated into the soil bafore 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.
Le A 27 155 _ 41 Preparation Examples Example 1 ~ S02-NH-CO-N~N-N(CH3?2 ~1 (Process (a)) P2.8 g (I7.2 mmol) of 5-chloro-4-dimethylam._no-2,4-dihydro-3H-I,2,4-triazol-3-one are dissolved in 6~ ml of acetonitrile and 6.6 g (27.4 mmol) of 2-meth~xy-carbonyl-phenylsulphonyl isocyanate, dissolved in 2? ml of acetonitrile, are added to this solution ~~ith stirring. The reaction mixture is stirred for 6 hour: at 20°C and then concentrated. The residue which remains is stirred with diethyl ether, and the product obtaine<in crystalline form is isolated by filtration with suct._on.
6 . 9 g ( 99 ~ of theory) of 5-chloro-4-dimet:iyl amino-2-(2-methoxycarbonyl-phenylsulphonyl-am_no carbonyl)-2,4-dihydro-3H-1,2,4-triazol-3-one of mel~:ing point 145°C are obtained.
Example 2 S02-NH-CO-N~N-N(CH3?2 CH 3 N~'~B r Le A 27 155 - 42 -~(~~~~ ~~
(Process (b)) 1.9 g (12.5 mmol) of 1,8-diazabicyclo-[5.4.0]-undec-7-ene (DBU) and 2.6 g (12.6 mmol) of 2-chloro-6-methyl-benzenesulphonamide are added to a solution of 4.0 g (12.2 mmol) of 5-bromo-4-dimethylamino-2-phenoxy-carbonyl-2,4-dihydro-3H-1,2,4-triazol-3-one in 60 ml of acetonitrile. The reaction mixture is stirred for 3 hours at 20°C, then poured into approximately twice the volume of ice-water and then brought to a pH of approximately 2 by adding 2~1 hydrochloric acid. The mixture is subse-quentlyP extracted using methylene chloride, and the organic phase is washed with water, dried with sodium sulphate and filtered. The filtrate is concentrated, the residue is stirred with diethyl ether, and the product which is obtained in crystalline form is isolated by filtration with suction.
1.0 g (19 $ of theory) of 5-bromo-4-dimethyl amino-2-(2-chloro-6-methyl-phenylsulphonyl-amino carbonyl)-2,4-dihydro-3H-1,2,4-triazol-3-one of melting point 163°C is obtained.
Other examples of the compounds which can be prepared analogously to Examples 1 and 2 and following the general description of the preparation processes according to the invention are those which are listed in 2S Table 3 below.

R3-S02-NH-CO-N~N-RI
N~ ----.~R 2 Le A 27 155 - 43 Table 3:
Preparation examples of the compounds of the formula (I) Ex. R1 R2 R3 Melting point No. ('~) ~

3 CH3 C1 -~ 170 ~

4 CH3 Br -~ 173 N(CH3)2 Br ~ _~ 139 6 -a Br ~-~ I55 7 ~ C1 ~-~ 148 ~
8 C3H7 Br -~ 120 ~
9 C3H7 C1 -~ lI9 Le A ~7 155 - 44 -fable 3: (continuation) Ex. Melting point Duo R~ R2 R3 ( C ) .

CH3 C1 ~ ~ 191 to C1 11 CH3 Br ~ 159 12 --a Br ~ 168 CI

13 "'q C1 ~ ~ 162 19 C2H5 Hr !-~ 197 15 C2H5 C1 ~-' 161 16 C2H5 Hr ~ 161 Le A 27 155 ~; ,(~ a Wi~Ed~.l.~v Table 3: (continuation) Ex. Melting point No. R1 R2 R3 (C>

17 C2H5 C1 ~ 156 18 ""~ C 1 ~

19 -~ Br ~ 134 CH3 C1 ~-~ 144 21 CH3 Br 22 C2H5 C1 ~ 122 23 C2H5 Br ~ 133 24 --~ C1 ~ ' 174 La A 27 155 - 46 r~~~~~~
Startin4 substances of the formula (II~~
Example r( II-1~, H-N~N~N(CH3)2 ~Br Stage 1:

H-N~N~N(CH3>2 H
856 g (4.0 mol) of diphenyl carbonate are dis-solved in 5B8 g of ethylene chloride. With water-cooling, 245 g (4.0 mol) of dimethylhydrazine (98 ~) are added dropwise, the mixture is then warmed slowly, and, after 4 hours, stirring is continued at 60°C.
After the mixture has cooled to 20°C, 200 g (4.0 mol) of hydrazine hydrate are added dropwise and stirring is continued for 12 hours. The mixture is warmed to 70-80°C, and, after approximately 1 hour, stirred again. When cold, the solution is distilled in vacuo, during which process ethylene chloride and water are removed (bottom temperature in the end 100°C). The above phenolic dimethyl carbodihydrazide solution is added dropwise in the course of 90 minutes at reflux tempera-ture (approximately 102°C) to 424 g (4.0 mol) of tri-methyl orthoformate. After the methanol which has formed has been removed by distillation, phenol is distilled off in vacuo, and at a head temperature of 85-105°C, 282 g of Le A 27 155 _ 97 ~U2U~.~3~
product mixture are subsequently obtained. This mixture is boiled with 600 ml of acetone and, after filtration at boiling temperature, the filtrate is cooled. The product which is obtained during this process in crystalline form is isolated by filtration with suction.
71 g (14 ~ of theory) of 4-dimethylamino-2,4-dihydro-3H-1,2,4-triazol-3-one of melting point 127°C are obtained.
Sta_c~e 2:

H-N~N~'N(CH3)2 Br 18.8 g (0.117 mol) of bromine are added with ice-caoling in the course of 2 hours to a stirred mixture of 15.0 g (0.117 mol) of 4-dimethylamino-2,4-dihydro-3H-1,2,4-triazol-3-one, 4.7 g (O.lI7 mol) of sodium hydr-oxide and 150 ml of water. The product which is obtained in crystalline form is subsequently isolated by filtra-tion with suction.
19.6 g (81 ~ of theory) of 5-bromo-4-dimethyl amino-2,4-dihydro-3H-I,2,4-triazol-3-one of melting 163°C
are obtained.
Le .A 27 155 Example ~( I I-2 J, O , H-N~N~N(CH3>2 ~C1 A mixture of 6.0 g (0.029 molj of 5-bromo-4-dimethylamino-2,4-dihydro-3H-1,2,4-triazol-3-one and 200 ml of concentrated hydrochloric acid is refluxed for 3 hours. The mixture is then concentrated, the residue is taken up in a little water, the mixture is rendered neutral using sodium hydrogen carbonate, and the product which is obtained in crystalline form is isolated by filtration with suction. The filtrate is extracted using ethyl acetate, the crystalline product which has previ-ously been isolated is added to the organic phase, and the latter is dried with sodium sulphate and filtered.
The filtrate is concentrated, the residue is triturated with diethyl ether, and the product which is obtained in crystalline form during this process is isolated by filtration with suction.
3.1 g (66 ~ of theory) of 5-chloro-4-dimethyl amino-2,4-dihydro-3H-1,2,4-triazol-3-one of melting point 158°C are obtained.
Other exaanples of compounds of the formula (IIj which can be prepared analogously to Examples (II-lj and (II-2j are those listed in Table 4 below.
Le A 27 155 HN~N~R1 (II) ~R2 Table 4: Preparation examples of the compounds of the formula (II) Example R1 R2 Melting point No. (°C) II-3 -~ Br 137 lI-4 C3H7 Br X18 II-5 --~ C1 121 II-6 C3H7 C1 yl II-7 C2H5 Br 142 II-9 CH2~ Br II-10 CH2-~ CI
Le ~ 27 155 ~L~~~fl~
Starting substances of the formula ~IV)~
Example ~j IV-11 O
~ 0-CO-N~N-N(CH3>2 NAB r 7.0 g (33.8 mmol) of 5-bromo-4-dimethylamino-2,4-da_hydro-3H-1,2,4-triazol-3-one are taken up in 100 ml of water and 100 ml of methylene chloride, and 0.2 g of tetrabutylammonium bromide and 1.5 g (37.5 mmol) of sodium hydroxide are added. 5.9 g (37.7 mmol) of phenyl chloroformate are then added dropwise at 20°C with vigorous stirring, and the reaction mixture is stirred for a further 12 hours at 20°C. The organic phase is separated off, washed with water, dried with sodium sulphate and filtered. The filtrate is concentrated, the residue is stirred with diethyl ether, and the product which is abtai.ned in crystalline form in this process is isolated by filtration with suction.
8.7 g (79 ~ of theory) of 5-bromo-4-dimethyl-amino-2-phenoxycarbonyl-2,4-dihydro-3H-1,2,4-tri.azol-3-one of melting point 136°C are obtained.
Use Examples:
In the following Use Examples, the known her-bicide isocarbamid of formula (A) below is used as comparison substances Le A 27 155 ~~2~:~.~~
n (A, HN~-CO-NH-CH2CH(CH3)2 (disclosed in EE 737,449; DE 1,795,117).
T~e A 27 155 Example A
Pre-emergence test Solvent: 5 parts :oy weight of acetone Emulsifier: 1 part by weight of alkylaryl polyglycol ether To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amount of solvent, the stated amount of emulsifier is added and the concentrate is diluted with water to the desired concentration.
Seeds of the test plants are sown in normal soil and, after 24 hours, watered with the preparation of the active compound. It is expedient to keep constant the amount of water per unit area. The con;:entration 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 da~r~age 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 Tn this test, for example the compounds of Pre~_ar-ation Example 3 , 6 and 7 show a clearly superior activity com-pared with the prior art.
Le A 27 155 ' ~~~~'~.fl Example B
Post-emergence test Solvent: 5 parts by weight of acetone Emulsifier: 1 part by weight of alkylaryl polyglycol ether To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amount of solvent, the stated amount of emulsifier is added and the concentrate is diluted with water to the desired concentration.
Test plants which have a height of 5 - 15 cm are sprayed with the preparation of the active compound in such a way as to apply the particular amounts of active compound desired per unit area. The concentration of the spray liquor is so chosen that the particular amounts of active compound desired are applied in 2,000 1 of water/ha. After three weeks, the degree of damage to the plants is rated in ~ damage in comparison to the development of the untreated control. The figures denote:
0~ = no action (like untreated control) 100 = total destruction In this test, for example the compounds of Pre~ar-ation Example 3 , 6 and 7 show a clearly sur~erior acti~ritv_ 'com-pared with the prior art.
he A 27 155

Claims (26)

1. A halogenated sulphonylaminocarbonyltriazolinone of the formula:
in which R1 represents hydrogen, hydroxyl or amino, or represents C1-C6-alkyl which is optionally substituted by fluorine, chlorine, bromine, cyano, C1-C4-alkoxy, C1-C4-alkylcarbonyl or C1-C4-alkoxy-carbonyl, or represents C3-C6-alkenyl or C3-C6-alkinyl, each of which is optionally substituted by at least one of fluorine, chlorine and bromine, or represents C3-C6-cycloalkyl which is optionally substituted by at least one of fluorine, chlorine, bromine and C1-C4-alkyl, or represents phenyl-C1-C3-alkyl which is optionally substituted by at least one of fluorine, chlorine, bromine, cyano, nitro, C1-C4-alkyl, trifluoromethyl, C1-C4-alkoxy and C1-C4-alkoxy-carbonyl, or represents phenyl which is optionally substituted by at least one of 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 C1-C4-alkoxycarbonyl, or represents C1-C6-alkoxy which is optionally substituted by fluorine, chlorine, cyano, C1-C4-alkoxy or C1-C4-alkoxy-carbonyl, or represents C3-C4-alkenyloxy, or represents fluorine-, cyano-, phenyl-, C1-C4-alkoxy- or C1-C4-alkoxy-carbonyl- substituted C1-C4-alkylamino, C3-C6-cycloalkylamino, or represents di- (C1-C4-alkyl) -amino, R2 represents fluorine, chlorine, bromine or iodine and R3 represents the group 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-alkyl-amino-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-alkyl-sulphinyl or C1-C4-alkylsulphonyl), or represent C1-C4-alkylthio (which is optionally substituted by fluorine, chlorine, bromine, cyano, carboxyl, C1-C4-alkoxy-carbonyl, C1-C4-alkylthio, C1-C4-alkylsulphinyl or C1-C4-alkylsulphonyl) or represent C3-C6-alkenyloxy (which is optionally substituted by fluorine, chlorine, bromine, cyano or C1-C4-alkoxy-carbonyl), or represent C2-C6-alkenylthio (which is optionally substituted by fluorine, chlorine, bromine, cyano, nitro, C1-C3-alkylthio or C1-C4-alkoxycarbonyl), C3-C6-alkinyloxy, C3-C6-alkinylthio or the radical -S(O)p-R6, where P represents the numbers 1 or 2 and R6 represents C1-C4-alkyl(which is optionally substituted by fluorine, chlorine, bromine, cyano or C1-C4-alkoxy-carbonyl), C3-C6-alkenyl, C3-C6-alkynyl, C1-C4-alkoxy, C1-C4-alkoxy-C1-C4-alkylamino, C1-C4-alkylamino, di-(C1-C4-alkyl) -amino, N-methoxy-N-methylamino, N-methylamino, 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-alkyl-carbonyl, C1-C4-alkoxycarbonyl, C1-C4-alkylamino-carbonyl or di-(C1-C4-alkyl)-amino-carbonyl), or represents C3-C6-alkenyl (which is optionally substituted by fluorine, chlorine or bromine), C3-C6-alkynyl, C3-C6-cycloalkyl, C3-C6-cycloalkyl-C1-C2-alkyl, phenyl-C1-C2-alkyl (which is optionally substituted by fluorine, chlorine, nitro, cyano, C1-C4-alkyl, C1-C4-alkoxy or C1-C4-alkoxy-carbonyl), or represents benzhydryl, or represents phenyl (which is optionally substituted by fluorine, chlorine, nitro, cyano, C1-C4-alkyl, trifluoromethyl, C1-C4-alkoxy, C1-C2-fluoroalkoxy, C1-C4-alkylthio, trifluoromethylthio or C1-C4-alkoxycarbonyl), or R4 and R5 each independently represents phenyl or phenoxy, or represents C1-C4-alkylcarbonylamino, C1-C4-alkoxy-carbonylamino, C1-C4-alkylamino-carbonyl-amino or di-(C1-C4-alkyl)-amino-carbonylamino or the radical -CO-R8, where R8 represents C1-C6-alkyl, C1-C6-alkoxy, C3-C6-cycloalkoxy, C3-C6-alkenyloxy, C1-C4-alkylthio, C1-C4-alkylamino, C1-C4-alkoxyamino, C1-C4-alkoxy-C1-C4-alkyl-amino or di- (C1-C4-alkyl) -amino (which are optionally substituted by at least one of fluorine and chlorine), or R4 and R5 each independently represents trimethylsilyl, thiazolinyl, C1-C4-alkylsulphonyloxy or di-(C1-C4-alkyl) -aminosulphonylamino or represents the radical -CH=N-R9, where R9 is 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-alkynyl, 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 at least one of fluorine and chlorine, or represents amino, C1-C4-alkylamino, di-(C1-C4-alkyl)-amino, phenylamino, C1-C4-alkyl-carbonyl-amino, C1-C4-alkoxy-carbonyl-amino or C1-C4-alkyl-sulphonylamino, or represents phenylsulphonylamino which is optionally substituted by fluorine, chlorine, bromine or methyl, or R3 represents the radical where R10 represents hydrogen or C1-C4-alkyl, R11 and R12 are identical or different and represent hydrogen, fluorine, chlorine, bromine, nitro, cyano, C1-C4-alkyl (which is optionally substituted by at least one of fluorine and chlorine), C1-C4-alkoxy (which is optionally substituted by at least one of fluorine and chlorine), carboxyl, C1-C4-alkoxy-carbonyl, dimethylaminocarbonyl, C1-C4-alkylsulphonyl or di-(C1-C4-alkyl)-amino-sulphonyl; or 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 at least one of fluorine and chlorine) or C1-C4-alkoxy (which is optionally substituted by at least one of fluorine and chlorine); or 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 at least one of fluorine and chlorine), C1-C4-alkoxy (which is optionally substituted by at least one of fluorine and chlorine), or represent C1-C4-alkylthio, C1-C4-alkylsulphinyl or C1-C4-alkylsulphonyl (which are optionally substituted by at least one of fluorine and chlorine), or represent aminosulphonyl, mono-(C1-C4-alkyl)-aminosulphonyl, di- (C1-C4-alkyl) -aminosulphonyl or C1-C4-alkoxy-carbonyl or dimethylaminocarbonyl; or 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 at least one of fluorine and bromine), C1-C4-alkoxy (which is optionally substituted by at least one of fluorine and chlorine), or represent C1-C4-alkylthio, C1-C4-alkylsulphinyl or C1-C4-alkylsulphonyl (which are optionally substituted by at least one of fluorine and chlorine) , or represent: di- (C1-C4-alkyl) -amino-sulphonyl; or 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 at least one of fluorine and chlorine), C1-C4-alkoxy (which is optionally substituted by at least one of fluorine and chlorine), C1-C4-alkylthio, C1-C4-alkylsulphinyl or C1-C4-alkylsulphonyl (which is optionally substituted by at least one of fluorine and chlorine), di- (C1-C4-alkyl) -amino-sulphonyl, C1-C4-alkoxy-carbonyl or dimethyl-aminocarbonyl, 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-cyclo-alkyl, benzyl, phenyl, (which is optionally substituted by fluorine, chlorine, bromine or nitro), C1-C4-alkylcarbonyl, C1-C4-alkoxy-carbonyl or di-(C1-C4-alkyl)-amino-carbonyl; or R3 represents the radical where R21 and R22 are identical or different and represent hydrogen, C1-C4-alkyl, halogen, C1-C4-alkoxycarbonyl, C1-C4-alkoxy or C1-C4-halogenoalkoxy, Y1 represents sulphur or the group N-R23, where R23 represents hydrogen or C1-C4-alkyl; or 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 at least one of fluorine and chlorine), C1-C4-alkoxy (which is optionally substituted by at least one of fluorine and chlorine), dioxolanyl or C1-C4-alkoxy-carbonyl and R26 represents hydrogen, halogen or C1-C4-alkyl; or R3 represent:
2. A halogenated sulphonylaminocarbonyltriazolinone or salt thereof according to claim 1, in which R1 represents hydrogen, or represent: C1-C4-alkyl which is optionally substituted by fluorine, cyano, methoxy or ethoxy, or represents allyl, or represents C3-C6-cycloalkyl, or represents phenyl, or represents C1-C4-alkoxy, C3-C4-alkenyloxy, or represents C1-C3-alkylamino, C3-C6-cycloalkylamino, or represents di-(C1-C3-alkyl)-amino, R2 represents chlorine, or bromine, 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, N-, phenyl, phenoxy or C1-C3-alkoxy-carbonyl, and R5 represents hydrogen, fluorine, chlorine or bromine; or R3 represent: 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; or furthermore, R3 represents the radical where R represents C1-C4-alkyl.
3. 5-Chloro-4-methyl-2-(2-methoxy carbonylphenylsulphonyl-amino-carbonyl)-2,4-dihydro-3H-1,2,4-triazol-3-one of the formula or a salt thereof.
4. 5-Bromo-4-cyclopropyl-2-(2-methoxy carbonylphenyl-sulphonyl-amino-carbonyl)-2,4-dihydro-3H-1,2,4-triazol-3-one of the formula or a salt thereof.
5. 5-Chloro-4-cyclopropyl-2-(2-methoxy-carbonylphenyl-sulphonyl-amino-carbonyl)-2,4-dihydro-3H-1,2,4-triazol-3-one of the formula or a salt thereof.
6. A herbicidal composition comprising a herbicidally effective amount of a compound according to any one of claims 1 to 5 in admixture with a suitable carrier or diluent.
7. A herbicidal composition comprising a herbicidally effective amount of a compound according to any one of claims 1 to 5 in admixture with an extender or a surface-active agent.
8. 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 5.
9. 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 5 in admixture with a suitable carrier or diluent.
10. 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 5 in admixture with a suitable carrier or diluent.
11. 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 0.5and 90% by weight of a compound according to any one of claims 1 to 5 in admixture with a suitable carrier or diluent.
12, A method of combating weeds which comprises applying to the weeds, or to a habitat thereof, a herbicidally effective amount of a compound according to any one of claims 1 to 5 wherein the compound is applied as a pre-emergence herbicide.
13. 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 5 wherein the compound is applied as a post-emergence herbicide.
14. 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 5 wherein the compound is applied to an area of cultivation at a rate of between 0.01 and 15 kg/ha.
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 5 wherein the compound is applied to an area of cultivation at a rate of between 0.05 and 10 kg/ha.
16. A process for preparing a compound according to claim 1, wherein R1, R2 and R3 are as defined in claim 1, which process comprises a) reacting a halogenated triazolinone of the general formula (II) in which R1 and R2 have the meanings as defined in claim 1 with a sulphonyl isocyanate of the general formula (III) R3-SO2-N=C=O (III) in which R3 has the meaning as defined in claim 1, or b) reacting halogenated triazolinone derivative of the general formula (IV) in which R1 and R2 have the meanings as defined on and 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 as defined in claim 1, or c) reacting a halogenated triazolinone of the general formula (II) in which R1 and R2 have the meanings as defined in claim 1 with a sulphonamide derivative of the general formula (VI) R3-SO2-NH-CO-Z (VI) in which R3 has the meaning as defined in claim 1 and Z represents chlorine, C1-C4 alkoxy, benzyloxy or phenoxy, and salts thereof.
17. A process according to claim 16 wherein Z is methoxy or phenoxy.
18. A process for preparing a herbicidal composition which comprises admixing a halogenated sulphonylaminocarbonyltriazolinone according to any one of claims 1 to 5 with a carrier and/or surface-active agent.
19. A halogenated triazolinone of the general formula (IV) in which R1 and R2 are as defined in claim 1, and Z represents chlorine, C1-C4 alkoxy, benzoloxy or phenoxy.
20. A compound according to claim 19 wherein Z is methoxy or phenoxy.
21. A compound of the formula in which R1 is C3-C6-cycloalkyl, C1-C6-alkoxy or di- (C1-C4-alkyl)-amino, and R2 is fluorine, chlorine or bromine.
22. A compound according to claim 21 wherein R1 is C3-C6-cycloalkyl, C1-C4-alkoxy or di- (C1-C3-alkyl)-amino, and R2 is chlorine or bromine.
23. 5-Bromo-4-cyclopropyl-2,4-dihydro-3H-1,2,4-triazol-3-one of the formula
24. 5-Chloro-4-cyclopropyl-2,4-dihydro-3H-1,2,4-triazol-3-one of the formula
25. 5-Bromo-4-dimethylamino-2,4-dihydro-3H-1,2,4-triazol-3-one of the formula
26. 5-Chloro-4-dimethylamino-2,4-dihydro-3H-1,2,4-triazol-3-one of the formula
CA002029105A 1989-11-03 1990-11-01 Halogenated sulphonylaminocarbonyltriazolinones Expired - Fee Related CA2029105C (en)

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ZA908799B (en) 1991-08-28
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JP2965661B2 (en) 1999-10-18
CA2029105A1 (en) 1991-05-04
ES2081334T3 (en) 1996-03-01
JPH03153674A (en) 1991-07-01
DK0425948T3 (en) 1996-04-22
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AU623284B2 (en) 1992-05-07
DE3936622A1 (en) 1991-05-08
KR910009675A (en) 1991-06-28
EP0661262A1 (en) 1995-07-05
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DE59009966D1 (en) 1996-01-25
AU6360290A (en) 1991-05-09

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