Claims
- 1. A sulphonylaminocarbonyltriazolinone of the formula ##STR519## in which R.sup.1 represents hydrogen; methyl optionally substituted by fluorine, chlorine, cyano or C.sub.1 -C.sub.4 -alkoxy; or cyclopropyl;
- R.sup.2 represents C.sub.1 -C.sub.6 -alkyl optionally substituted by fluorine, chlorine, C.sub.3 -C.sub.6 -cycloalkyl or C.sub.1 -C.sub.4 -alkoxy; C.sub.3 -C.sub.6 -alkenyl optionally substituted by at least one of fluorine, chlorine and bromine; C.sub.3 -C.sub.6 -alkinyl; C.sub.3 -C.sub.6 -cycloalkyl; phenyl; or fluorophenyl,
- R.sup.3 represents the group ##STR520## in which R.sup.4 and R.sup.5 are identical or different and represent hydrogen, fluorine, chlorine, bromine, iodine, nitro, C.sub.1 -C.sub.6 -alkyl (which is optionally substituted by fluorine, chlorine, bromine, cyano, carboxyl, C.sub.1 -C.sub.4 -alkoxycarbonyl, C.sub.1 -C.sub.4 -alkylaminocarbonyl, di-(C.sub.1 -C.sub.4 -alkyl ) amino-carbonyl, hydroxyl, C.sub.1 -C.sub.4 -alkoxy, formyloxy, C.sub.1 -C.sub.4 -alkyl-carbonyloxy, C.sub.1 -C.sub.4 -alkoxy-carbonyloxy, C.sub.1 -C.sub.4 -alkylamino-carbonyloxy, C.sub.1 -C.sub.4 -alkylthio, C.sub.1 -C.sub.4 -alkylsulphinyl, C.sub.1 -C.sub.4 -alkylsulphonyl, di-(C.sub.1 -C.sub.4 -alkyl)-aminosulphonyl, C.sub.3 -C.sub.6 -cycloalkyl or phenyl), or represent C.sub.2 -C.sub.6 -alkenyl (which is optionally substituted by fluorine, chlorine, bromine, cyano, C.sub.1 -C.sub.4 -alkoxy-carbonyl, carboxyl or phenyl), or represent C.sub.2 -C.sub.6 -alkinyl (which is optionally substituted by fluorine, chlorine, bromine, cyano, C.sub.1 -C.sub.4 -alkoxy-carbonyl, carboxyl or phenyl), or represent C.sub.1 -C.sub.4 -alkoxy (which is optionally substituted by fluorine, chlorine, bromine, cyano, carboxyl, C.sub.1 -C.sub.4 -alkoxy-carbonyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -alkylthio, C.sub.1 -C.sub.4 -alkylsulphinyl or C.sub.1 -C.sub.4 -alkylsulphonyl), or represent C.sub.1 -C.sub.4 -alkylthio (which is optionally substituted by fluorine, chlorine, bromine, cyano, carboxyl, C.sub.1 -C.sub.4 -alkoxy-carbonyl, C.sub.1 -C.sub.4 -alkylthio, C.sub.1 -C.sub.4 -alkylsulphinyl or C.sub.1 -C.sub.4 -alkylsulphonyl), or represent C.sub.3 -C.sub.6 -alkenyloxy (which is optionally substituted by fluorine, chlorine, bromine, cyano or C.sub.1 -C.sub.4 -alkoxy-carbonyl), or represent C.sub.2 -C.sub.6 -alkenylthio (which is optionally substituted by fluorine, chlorine, bromine, cyano, nitro, C.sub.1 -C.sub.3 -alkylthio or C.sub.1 -C.sub.4 -alkoxycarbonyl), C.sub.3 -C.sub.6 -alkinyloxy, C.sub.3 -C.sub.6 -alkinylthlo or the radical --S(O).sub.p --R.sup.6 where
- P represents the numbers 1 or 2 and
- R.sup.6 represents C.sub.1 -C.sub.4 -alkyl (which is optionally substituted by fluorine, chlorine, bromine, cyano or C.sub.1 -C.sub.4 -alkoxy-carbonyl), C.sub.3 -C.sub.6 -alkenyl, C.sub.3 -C.sub.6 -alkinyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -alkoxy-C.sub.1 -C.sub.4 -alkylamino, C.sub.1 -C.sub.4 -alkylamino, di-(C.sub.1 -C.sub.4 -alkyl)-amine, phenyl or the radical --NHOR.sup.7 where
- R.sup.7 represents C.sub.1l -C.sub.12 -alkyl (which is optionally substituted by fluorine, chlorine, cyano, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -alkylthio. C.sub.1 -C.sub.4 -alkylsulphinyl, C.sub.1 -C.sub.4 -alkylsulphonyl, C.sub.1 -C.sub.4 -alkyl-carbonyl, C.sub.1 -C.sub.4 -alkoxy-carbonyl, C.sub.1 -C.sub.4 -alkylamino-carbonyl or di-(C.sub.1 -C.sub.4 -alkyl)-amino-carbonyl), or represents C.sub.3 -C.sub.6 -alkenyl (which is optionally substituted by fluorine, chlorine or bromine), C.sub.3 -C.sub.6 -alkinyl, C.sub.3 -C.sub.6 -cycloalkyl, C.sub.3 -C.sub.6 -cycloalkyl-C.sub.1 -C.sub.2 -alkyl, phenyl-C.sub.1 -C.sub.2 -alkyl (which is optionally substituted by fluorine, chlorine, nitro, cyano, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy or C.sub.1 -C.sub.4 -alkoxy-carbonyl), or represents benzhydryl, or represents phenyl (which is optionally substituted by fluorine, chlorine, nitro, cyano, c.sub.1 -c.sub.4 -alkyl, trifluoromethyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -fluoroalkoxy, C.sub.1 -C.sub.4 -alkylthio, trifluoromethylthio or C.sub.1 -c.sub.4 -alkoxy-carbonyl),
- R.sup.4 and/or R.sup.5 furthermore represent phenyl or phenoxy, or represent C.sub.1 -C.sub.4 -alkylcarbonylamino, C.sub.1 -C.sub.4 -alkoxycarbonylamino, C.sub.1 -C.sub.4 -alkylamino-carbonyl-amino, di-(C.sub.1 -C.sub.4 -alkyl)-amino-carbonylamino, or the radical --CO--R.sup.8 where
- R.sup.8 represents C.sub.1 -C.sub.6 -alkyl, C.sub.1 -C.sub.6 -alkoxy, C.sub.3 -C.sub.6 -cycloalkoxy, C.sub.3 -C.sub.6 -alkenyloxy, C.sub.1 -C.sub.4 -alkylthio, C.sub.1 -C.sub.4 -alkylamino, C.sub.1 -C.sub.4 -alkoxyamino, C.sub.1 -C.sub.4 -alkoxy-C.sub.1 -C.sub.4 -alkyl-amino or di-(C.sub.1 -C.sub.4 -alkyl)-amino (which are optionally substituted by fluorine and/or chlorine),
- R.sup.4 and/or R.sup.5 furthermore represent trimethylsilyl, C.sub.1 -C.sub.4 -alkylsulphonyl, di-(C.sub.1 -C.sub.4 -alkyl)-aminosulphonylamino or the radical --CH.dbd.N--R.sup.9 where
- R.sup.9 represents C.sub.1 -C.sub.6 -alkyl which is optionally substituted by fluorine, chlorine, cyano, carboxyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -alkylthio, C.sub.1 -C.sub.4 -alkylsulphinyl or C.sub.1 -C.sub.4 -alkylsulphonyl, or represents benzyl which is optionally substituted by fluorine or chlorine, or represents C.sub.3 -C.sub.6 -alkenyl or C.sub.3 -C.sub.6 -alkinyl, each of which is optionally substituted by fluorine or chlorine, or represents phenyl which is optionally substituted by fluorine, chlorine, bromine, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, trifluoromethyl, trifluoromethoxy or trifluoromethylthio, or represents optionally fluorine- and/or chlorine-substituted C.sub.1 -c.sub.6 -alkoxy, C.sub.3 -C.sub.6 -alkenoxy, C.sub.3 -C.sub.6 -alkinoxy or benzyloxy, or represents amino, C.sub.1 -C.sub.4 -alkylamino, di-(C.sub.1 -C.sub.4 -alkyl)-amino, phenylamino. C.sub.1 -C.sub.4 -alkyl-carbonyl-amino, C.sub.1 -C.sub.4 -alkoxycarbonylamino or C.sub.1 -C.sub.4 -alkyl-sulphonylamino, or represents phenylsulphonylamino which is optionally substituted by fluorine, chlorine, bromine or methyl,
- furthermore
- R.sup.3 represents the radical ##STR521## where R.sup.10 represents hydrogen or C.sub.1 -C.sub.4 -alkyl,
- R.sup.11 and R.sup.12 are identical or different and represent hydrogen, fluorine, chlorine, bromine, nitro, cyano, C.sub.1 -C.sub.4 -alkyl (which is optionally substituted by fluorine and/or chlorine), C.sub.1 -C.sub.4 -alkoxy (which is optionally substituted by fluorine and/or chlorine), carboxyl, C.sub.1 -C.sub.4 -alkoxy-carbonyl, dimethylaminocarbonyl, C.sub.1 -C.sub.4 -alkylsulphonyl or di-(C.sub.1 -c.sub.4 -alkyl)aminosulphonyl;
- furthermore
- R.sup.3 represents the radical ##STR522## where R.sup.13 and R.sup.14 are identical or different and represent hydrogen, fluorine, chlorine, bromine, nitro, cyano, C.sub.1 -C.sub.4 -alkyl (which is optionally substituted by fluorine and/or chlorine) or C.sub.1 -C.sub.4 -alkoxy (which is optionally substituted by fluorine and/or chlorine)
- or a salt thereof,
- with the exception of the compounds:
- 2-(2-methoxycarbonyl-phenylsulphonylaminocarbonyl)-4-methyl-5-methoxy-2,4-dihydro-3H-1,2,4-triazol-3-one, and
- 2-(2-trifluoromethoxy-phenylsulphonylaminocarbonyl)-4-cyclopropyl-5-methoxy-2,4-dihydro-3H-1,2,4-triazol-3-one.
- 2. A sulphonylaminocarbonyl-triazolinone or salt thereof according to claim 1, in which
- R.sup.1 represents hydrogen, methyl which is optionally substituted by fluorine, cyano, methoxy or ethoxy, or represents cyclopropyl,
- R.sup.2 represents C.sub.1 -C.sub.4 -alkyl which is optionally substituted by fluorine and/or chlorine, methoxy or ethoxy, or represents C.sub.3 -C.sub.4 -alkenyl which is optionally substituted by fluorine and/or chlorine, or represents C.sub.3 -C.sub.6 -cycloalkyl, and
- R.sup.3 represents the group ##STR523## where R.sup.4 represents fluorine, chlorine, bromine, methyl trifluoromethyl, methoxy, difluoromethoxy, trifluoromethoxy, 2-chloro-ethoxy, 2-methoxy-ethoxy, C.sub.1 -C.sub.3 -alkylthio, C.sub.1 -C.sub.3 -alkylsulphinyl, C.sub.1 -C.sub.3 -alkylsulphonyl, dimethylaminosulphonyl, diethylaminosulphonyl, N-methoxy-N-methylaminosulphonyl, methoxyaminosulphonyl, phenyl, phenoxy or C.sub.1 -C.sub.3 -alkoxy-carbonyl and
- R.sup.5 represents hydrogen, fluorine, chlorine or bromine;
- furthermore
- R.sup.3 represent the radical ##STR524## where R.sup.10 represents hydrogen,
- R.sup.11 represents fluorine, chlorine, bromine, methyl, methoxy, difluoromethoxy, trifluoromethoxy, ethoxy, methoxycarbonyl, ethoxycarbonyl, methylsulphonyl or dimethylaminosulphonyl and
- R.sup.12 represents hydrogen;
- with the exception of the compounds:
- 2-(2-methoxycarbonyl-phenylsulphonylaminocarbonyl)-4-methyl-5-methoxy-2,4-dihydro-3H-1,2,4-triazol-3-one, and
- 2-(2-trifluoromethoxy-phenylsulphonylaminocarbonyl)-4-cyclopropyl-5-methoxy-2,4-dihydro-3H-1,2,4-triazol-3-one.
- 3. A sulphonylaminocarbonyltriazolinone or salt thereof according to claim 1, in which
- R.sup.1 represents methyl or cyclopropyl,
- R.sup.2 represents C.sub.1 -C.sub.6 -alkyl or phenyl, and
- R.sup.3 represents ##STR525## , in which R.sup.4 represents chlorine, bromine, methyl optionally substituted by fluorine, methoxy which is substituted by fluorine or the radical --COOCH.sub.3, and
- R.sup.5 represents hydrogen or methyl, with the exception of the compounds:
- 2-(2-methoxycarbonyl-phenylsulphonylaminocarbonyl)-4-methyl-5-methoxy-2,4-dihydro-3H-1,2,4-triazol-3-one, and
- 2-(2-trifluoromethoxy-phenylsulphonylaminocarbonyl)-4-cyclopropyl-5-methoxy-2,4-dihydro-3H-1,2,4-triazol-3-one.
- 4. A compound or salt thereof according to claim 3, wherein the compound is selected from the group consisting of those of the following table:
- ______________________________________--R.sup.1 --R.sup.2 --R.sup.4 --R.sup.5______________________________________CH.sub.3 --C.sub.2 H.sub.5 COOCH.sub.3 HCH.sub.3 --C.sub.3 H.sub.7 -n COOCH.sub.3 HCH.sub.3 --C.sub.3 H.sub.7 -i COOCH.sub.3 HCyclopropyl --C.sub.2 H.sub.5 OCHF.sub.2 HCyclopropyl --C.sub.3 H.sub.7 -n OCF.sub.3 HCH.sub.3 CH.sub.3 OCF.sub.3 HCyclopropyl C.sub.2 H.sub.5 COOCH.sub.3 HCH.sub.3 C.sub.6 H.sub.5 CH.sub.3 HCH.sub.3 C.sub.6 H.sub.5 COOCH.sub.3 HCH.sub.3 C.sub.6 H.sub.5 Cl 6-CH.sub.3CH.sub.3 C.sub.6 H.sub.5 OCF.sub.3 HCH.sub.3 C.sub.6 H.sub.5 Br HCH.sub.3 CH.sub.3 CH.sub.3 HCH.sub.3 CH.sub.3 Br HCH.sub.3 CH.sub.3 Cl 6-CH.sub.3CH.sub.3 CH.sub.3 CF.sub.3 HCH.sub.3 C.sub.6 H.sub.5 CF.sub.3 HCH.sub.3 C.sub.2 H.sub.5 OCF.sub.3 HCH.sub.3 C.sub.2 H.sub.5 CF.sub.3 HCH.sub.3 CH.sub.3 OCHF.sub.2 HCyclopropyl C.sub.2 H.sub.5 Br HCyclopropyl C.sub.2 H.sub.5 Cl HCyclopropyl C.sub.2 H.sub.5 Cl 6-CH.sub.3CH.sub.3 C.sub.2 H.sub.5 Cl HCH.sub.3 C.sub.2 H.sub.5 Cl 6-CH.sub.3______________________________________
- 5. A compound or salt thereof according to claim 3, wherein R.sup.5 represents hydrogen and the compound is selected from the group consisting of those of the following table:
- ______________________________________--R.sup.1 --R.sup.2 --R.sup.4______________________________________CH.sub.3 --C.sub.2 H.sub.5 COOCH.sub.3CH.sub.3 C.sub.3 H.sub.7 -n COOCH.sub.3CH.sub.3 C.sub.3 H.sub.7 -i COOCH.sub.3CH.sub.3 --CH.sub.3 --OCF.sub.3CH.sub.3 --C.sub.2 H.sub.5 --OCF.sub.3CH.sub.3 --C.sub.3 H.sub.7 -n --OCF.sub.3CH.sub.3 --C.sub.3 H.sub.7 -i --OCF.sub.3CH.sub.3 --CH.sub.3 --CF.sub.3CH.sub.3 --C.sub.2 H.sub.5 --CF.sub.3CH.sub.3 --C.sub.3 H.sub.7 -n --CF.sub.3CH.sub.3 --C.sub.3 H.sub.7 -i --CF.sub.3Cyclopropyl --C.sub.2 H.sub.5 COOCH.sub.3Cyclopropyl --C.sub.3 H.sub.7 -n COOCH.sub.3Cyclopropyl --C.sub.2 H.sub.5 --OCF.sub.3Cyclopropyl --C.sub.3 H.sub.7 -n --OCF.sub.3Cyclopropyl --CH.sub.3 --CF.sub.3Cyclopropyl --C.sub.2 H.sub.5 --CF.sub.3Cyclopropyl --C.sub.3 H.sub.7 -n --CF.sub.3______________________________________
- 6. A compound or salt thereof according to claim 1, wherein such compound is ##STR526##
- 7. A compound or salt thereof according to claim 1, wherein such compound is ##STR527##
- 8. A compound or salt thereof according to claim 1, wherein such compound is ##STR528##
- 9. A compound or salt thereof according to claim 2, wherein such compound is ##STR529##
- 10. A compound or salt thereof according to claim 1, wherein such compound is ##STR530##
- 11. A compound or salt thereof according to claim 1, wherein such compound is ##STR531##
- 12. A compound or salt thereof according to claim 1, wherein such compound is ##STR532##
- 13. A compound or salt thereof according to claim 1, wherein such compound is ##STR533##
- 14. A compound or salt thereof according to claim 1, wherein such compound is ##STR534##
- 15. A compound or salt thereof according to claim 1, wherein such compound is ##STR535##
- 16. A compound or salt thereof according to claim 1, wherein such compound is ##STR536##
- 17. A compound or salt thereof according to claim 1, wherein such compound is ##STR537##
- 18. A herbicidal composition comprising a herbicidally effective amount of a compound or salt thereof according to claim 1 and a diluent.
- 19. A method of combatting unwanted vegetation which comprises applying to such vegetation or to a locus from which it is desired to exclude such vegetation a herbicidally effective amount of a compound or salt thereof according to claim 1.
- 20. A method of combatting unwanted vegetation which comprises applying to such vegetation or to a locus from which it is desired to exclude such vegetation a herbicidally effective amount of a compound or salt thereof according to claim 4.
Priority Claims (1)
Number |
Date |
Country |
Kind |
41 10 795.0 |
Apr 1991 |
DEX |
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Parent Case Info
This application is a continuation of application Ser. No. 08/048,026, filed Apr. 15, 1993, now abandoned, which is a continuation-in-part of Ser. No. 07/857,025, filed on Mar. 24, 1992, now abandoned.
US Referenced Citations (1)
Number |
Name |
Date |
Kind |
5057144 |
Daum et al. |
Oct 1991 |
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Continuations (1)
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Number |
Date |
Country |
Parent |
48026 |
Apr 1993 |
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Continuation in Parts (1)
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Number |
Date |
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Parent |
857025 |
Mar 1992 |
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