Claims
- 1. A sulphonylaminoguanidinoazine of the formula ##STR567## in which R.sup.1 stands for the radical ##STR568## wherein R.sup.9 and R.sup.10 are identical or different and stand for hydrogen, fluorine, chlorine, bromine, iodine, cyano, 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 -alkylcarbonyloxy, 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), for 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), for 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), for 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), for 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), for C.sub.3 -C.sub.6 -alkenyloxy (which is optionally substituted by fluorine, chlorine, bromine, cyano or C.sub.1 -C.sub.4 -alkoxycarbonyl), for 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 -alkinylthio or for the radical --S(O).sub.p --R.sup.11,
- wherein
- p stands for the numbers 1 or 2 and
- R.sup.11 stands for 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)-amino or for the radical --NHOR.sup.12,
- wherein
- R.sup.12 stands for C.sub.1 -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 -alkylcarbonyl, 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), for 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 -alkoxycarbonyl), for benzylhydryl or for 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.2 -fluoroalkoxy, C.sub.1 -C.sub.4 -alkylthio, trifluoromethylthio or C.sub.1 -C.sub.4 -alkoxy-carbonyl),
- R.sup.9 and R.sup.10 furthermore stand for phenyl or phenoxy, for amino, C.sub.1 -C.sub.4 -alkylcarbonylamino, C.sub.1 -C.sub.4 -alkoxy-carbonylamino, C.sub.1 -C.sub.4 -alkylamino-carbonylamino, di-(C.sub.1 -C.sub.4 -alkyl)-amino-carbonylamino, or for the radical --CO--R.sup.13,
- wherein
- R.sup.13 stands for 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 -alkylamino or di-(C.sub.1 -C.sub.4 -alkyl)-amino (which are optionally substituted by fluorine and/or chlorine),
- R.sup.9 and R.sup.10 furthermore stand for C.sub.1 -C.sub.4 -alkylsulphonyloxy, di-(C.sub.1 -C.sub.4 -alkyl)-aminosulphonylamino, thiazolyloxy or for the radical --CH.dbd.N--R.sup.14,
- wherein
- R.sup.14 stands for 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, for benzyl which is optionally substituted by fluorine or chlorine, for C.sub.3 -C.sub.6 -alkenyl or C.sub.3 -C.sub.6 -alkinyl which are optionally substituted by fluorine or chlorine, for 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, for C.sub.1 -C.sub.6 -alkoxy, C.sub.3 -C.sub.6 -alkenoxy, C.sub.3 -C.sub.6 -alkinoxy or benzyloxy which are optionally substituted by fluorine and/or chlorine, for 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 -alkoxy-carbonylamino, C.sub.1 -C.sub.4 -alkyl-sulphonylamino or for phenylsulphonylamino which is optionally substituted by fluorine, chlorine, bromine or methyl,
- in addition,
- R.sup.1 stands for the radical ##STR569## wherein R.sup.15 stands for hydrogen or C.sub.1 -C.sub.4 -alkyl,
- R.sup.16 and R.sup.17 are identical or different and stand for 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, C.sub.1 -C.sub.4 -alkylsulphonyl or di-(C.sub.1 -C.sub.4 -alkyl)-aminosulphonyl;
- in addition
- R.sup.1 stands for the radical ##STR570## wherein R.sup.18 and R.sup.19 are identical or different and stand for 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);
- in addition
- R.sup.1 stands for the radical ##STR571## wherein R.sup.20 and R.sup.21 are identical or different and stand for 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), for C.sub.1 -C.sub.4 -alkylthio, C.sub.1 -C.sub.4 -alkylsulphinyl or C.sub.1 -C.sub.4 -alkylsulphonyl (which are optionally substituted by fluorine and/or chlorine) and also for di-(C.sub.1 -C.sub.4 -alkyl)-aminosulphonyl or C.sub.1 -C.sub.4 -alkoxy-carbonyl;
- in addition
- R.sup.1 stands for the radical ##STR572## wherein R.sup.22 and R.sup.23 are identical or different and stand for hydrogen, fluorine, chlorine, bromine, C.sub.1 -C.sub.4 -alkyl (which is optionally substituted by fluorine and/or bromine), C.sub.1 -C.sub.4 -alkoxy (which is optionally substituted by fluorine and/or chlorine), for C.sub.1 -C.sub.4 -alkylthio, C.sub.1 -C.sub.4 -alkylsulphinyl or C.sub.1 -C.sub.4 -alkylsulphonyl (which are optionally substituted by fluorine and/or chlorine), or for di-(C.sub.1 -C.sub.4 -alkyl)-aminosulphonyl;
- in addition
- R.sup.1 stands for the radical ##STR573## wherein R.sup.24 and R.sup.25 are identical or different and stand for hydrogen, fluorine, chlorine, bromine, cyano, nitro, 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), C.sub.1 -C.sub.4 -alkylthio, C.sub.1 -C.sub.4 -alkylsulphinyl or C.sub.1 -C.sub.4 -alkylsulphonyl (which is optionally substituted by fluorine and/or chlorine), di-(C.sub.1 -C.sub.4 -alkyl)-amino-sulphonyl or C.sub.1 -C.sub.4 -alkoxy-carbonyl, and
- A satnds for oxygen, sulphur or the grouping N--Z.sup.1,
- wherein
- Z.sup.1 stands for hydrogen, C.sub.1 -C.sub.4 -alkyl (which is optionally substituted by fluorine, chlorine, bromine or cyano), C.sub.3 -C.sub.6 -cycloalkyl, benzyl, phenyl (which is optionally substituted by fluorine, chlorine, bromine or nitro), C.sub.1 -C.sub.4 -alkylcarbonyl, C.sub.1 -C.sub.4 -alkoxy-carbonyl or di-(C.sub.1 -C.sub.4 -alkyl)-aminocarbonyl;
- in addition
- R.sup.1 stands for the radical ##STR574## wherein R.sup.26 stands for hydrogen, C.sub.1 -C.sub.5 -alkyl or halogen,
- R.sup.27 satnds for hydrogen or C.sub.1 -C.sub.5 -alkyl and
- Y.sup.1 stands for sulphur or the grouping N--R.sup.28,
- wherein
- R.sup.28 stands for hydrogen or C.sub.1 -C.sub.5 -alkyl,
- in addition
- R.sup.1 stands for the radical ##STR575## wherein R.sup.29 stands for hydrogen, C.sub.1 -C.sub.4 -alkyl or phenyl,
- R.sup.30 stands for hydrogen, halogen, cyano, nitro, 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) or C.sub.1 -C.sub.4 -alkoxy-carbonyl and
- R.sup.31 stands for hydrogen, halogen or C.sub.1 -C.sub.4 -alkyl,
- in addition,
- R.sup.1 stands for the radical ##STR576## wherein R.sup.32 stands for C.sub.1 -C.sub.3 -alkyl and
- R.sup.33 stands for C.sub.1 -C.sub.4 -alkyl,
- in addition
- R.sup.1 stands for the radical ##STR577## in addition R.sup.2 has the meaning given above for R.sup.1, but does not have to be identical with R.sup.1 in each individual case, and in addition can stand for di-(C.sub.1 -C.sub.3 -alkyl)-amino or for C.sub.1 -C.sub.8 -alkyl which is optionally substituted by halogen, provided, however, that R.sup.2 cannot be unsubstituted phenyl or fluorine-, chlorine-, bromine-or methyl-substituted phenyl,
- in addition
- R.sup.3 stands for hydrogen, fluorine, chlorine, bromine, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -halogenoalkyl, C.sub.1 -C.sub.2 -alkoxy-C.sub.1 -C.sub.2 -alkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -halogenoalkoxy, C.sub.1 -C.sub.4 -alkylthio, C.sub.1 -C.sub.4 -halogenoalkylthio, amino, C.sub.1 -C.sub.4 -alkylamino, dimethylamino or diethylamino,
- R.sup.5 stands for hydrogen, fluorine, chlorine, bromine, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -halogenoalkoxy, C.sub.1 -C.sub.4 -alkylthio, C.sub.1 -C.sub.4 -alkylamino, dimethylamino or diethylamino, and
- M stands for hydrogen or a sodium equivalent, a potassium equivalent or a calcium equivalent, an ammonium equivalent, a C.sub.1 -C.sub.6 -alkylammonium equivalent, a di-(C.sub.1 -C.sub.4 -alkyl)-ammonium or a tri-(C.sub.1 -C.sub.4 -alkyl)-ammonium equivalent.
- 2. A sulphonylaminoguanidinoazine according to claim 1,
- in which
- R.sup.1 stands for the radical ##STR578## wherein R.sup.9 stands for fluorine, chlorine, bromine, methyl, trifluoromethyl, methoxy, difluoromethoxy, trifluoromethoxy, 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, phenyl, phenoxy or C.sub.1 -C.sub.3 -alkoxy-carbonyl and
- R.sup.10 stands for hydrogen;
- in addition
- R.sup.1 stands for the radical ##STR579## wherein R.sup.15 satnds for hydrogen,
- R.sup.16 stands for fluorine, chlorine, bromine, methyl, methoxy, ethoxy, difluoromethoxy, trifluoromethoxy, methoxycarbonyl, ethoxycarbonyl, methylsulphonyl or dimethylaminosulphonyl and
- R.sup.17 stands for hydrogen;
- in addition
- R.sup.1 stands for the radical ##STR580## wherein R stands for C.sub.1 -C.sub.2 -alkyl, or
- R.sup.1 stands for the radical ##STR581## wherein R stands for C.sub.1 -C.sub.2 -alkyl;
- in addition
- R.sup.2 stands for C.sub.1 -C.sub.4 -alkyl which is optionally substituted by fluorine or chlorine or for substituted phenyl which is substituted by ethyl-, propyl-, trifluoromethyl chlorodifluoromethyl, methoxy, ethoxy, difluoromethoxy, trifluoromethoxy, amino, acetamido, methoxycarbonyl and/or ethoxycarbonyl,
- R.sup.3 stands for hydrogen, fluorine, chlorine, bromine, methyl, trifluoromethyl, methoxy, ethoxy, difluoromethoxy, methylthio, ethylthio, amino, methylamino, ethylamino, dimethylamino or diethylamino,
- R.sup.5 stands for hydrogen, fluorine, chlorine, bromine, methyl, ethyl, methoxy, ethoxy, propoxy, isopropoxy, difluoromethoxy, methylthio, ethylthio, methylamino, ethylamino, dimethylamino or diethylamino, and
- M stands for hydrogen or a sodium equivalent, potassium equivalent or calcium equivalent, an ammonium equivalent or a C.sub.1 -C.sub.4 -alkyl-ammonium equivalent.
- 3. A compound according to claim 1, wherein such compound is N'-(4-methoxy-6-methyl-s-triazin-2-yl)-N"-(2-methoxycarbonyl-phenylsulphonylamino)-N'"-(2-ethoxycarbonyl-phenylsulphonyl)-guanidine.
- 4. A compound according to claim 1, wherein such compound is N'-(4,6-dimethoxy-s-triazin-2-yl)-N"-(2-methoxycarbonyl-phenylsulphonylamino)-N'"-(2-methoxycarbonyl-phenylsulphonyl)-guanidine.
- 5. A compound according to claim 1, wherein such compound is N'-(4-methoxy-6-methyl-s-triazin-2-yl)-N"-[2-(2-methoxyethoxy)-carbonyl-phenylsulphonylamino]-N'"-(2-ethoxycarbonyl-phenylsulphonyl)-guanidine.
- 6. A compound according to claim 1, wherein such compound is N'-(4-methoxy-6-methyl-s-triazin-2-yl)-N"-(2-methoxycarbonyl-phenylsulphonylamino)-N'"-(2-n-propoxycarbonyl-phenylsulphonyl)-guanidine.
- 7. A compound according to claim 1, wherein such compound is N'-(4-methoxy-6-methyl-s-triazin-2-yl)-N"-(2-n-propoxycarbonyl-phenylsulphonylamino)-N'"-(2-n-propoxycarbonyl-phenylsulphonyl)-guanidine.
- 8. A compound according to claim 1, wherein such compound is N'-(4-methoxy-6-methyl-s-triazin-2-yl)-N"-(2-methoxycarbonyl-phenylsulphonylamino)-N'"-(2-isopropoxycarbonyl-phenylsulphonyl)-guanidine.
- 9. A compound according to claim 1, wherein such compound is N'-(4-methoxy-6-methyl-s-triazin-2-yl)-N"-(2-ethoxycarbonyl-phenylsulphonylamino)-N'"-(2-ethoxycarbonyl-phenylsulphonyl)-guanidine.
- 10. A herbicidal composition comprising a herbicidally effective amount of a compound according to claim 1 and a diluent.
- 11. A method of combating unwanted vegetation which comprises applying to such vegetation or to a habitat from which it is desired to exclude such vegetation a herbicidally effective amount of a compound according to claim 1.
- 12. A method of combating unwanted vegetation which comprises applying to such vegetation or to a habitat from which it is desired to exclude such vegetation a herbicidally effective amount of a compound selected from the group consisting of
- N'-(4-methoxy-6-methyl-s-triazin-2-yl)-N"-(2-methoxycarbonyl-phenylsulphonylamino)-N'"-(2-ethoxy-carbonyl-phenylsulphonyl)-guanidine,
- N'-(4,6-dimethoxy-s-triazin-2-yl)-N"-(2-methoxycarbonyl-phenylsulphonylamino)-N'"-(2-methoxy-carbonyl-phenylsulphonyl)-guanidine,
- N'-(4-methoxy-6-methyl-s-triazin-2-yl)-N"-[2-(2-methoxyethoxy)-carbonyl-phenylsulphonylamino]-N'"-(2-ethoxycarbonyl-phenylsulphonyl)-guanidine,
- N'-(4-methoxy-6-methyl-s-triazin-2-yl)-N"-(2-methoxycarbonyl-phenylsulphonylamino)-N'"-(2-n-propoxy-carbonyl-phenylsulphonyl)-guanidine,
- N'-(4-methoxy-6-methyl-s-triazin-2-yl)-N"-(2-n-propoxycarbonyl-phenylsulphonylamino)-N'"-(2-n-propoxycarbonyl-phenylsulphonyl)-guanidine,
- N'-(4-methoxy-6-methyl-s-triazin-2-yl)-N"-(2-methoxycarbonyl-phenylsulphonylamino)-N'"-(2-isopropoxy-carbonyl-phenylsulphonyl)-guanidine and
- N'-(4-methoxy-6-methyl-s-triazin-2-yl)-N"-(2-ethoxycarbonyl-phenylsulphonylamino)-N'"-(2-ethoxy-carbonyl-phenylsulphonyl)-guanidine.
Priority Claims (3)
Number |
Date |
Country |
Kind |
3726269 |
Aug 1987 |
DEX |
|
3927770 |
Aug 1989 |
DEX |
|
4104154 |
Feb 1991 |
DEX |
|
Parent Case Info
This is a continuation-in-part of application Ser. No. 521,055, filed May 2, 1990, now abandoned (which is a division of Ser. No. 227,587, filed Aug. 2, 1988, now U.S. Pat. No. 4,952,233) and of Ser. No. 561,857, filed Aug. 1, 1990, now U.S. Pat. No. 5,125,960.
US Referenced Citations (3)
Number |
Name |
Date |
Kind |
4602938 |
Moriya et al. |
Jul 1986 |
|
4725303 |
Moriya et al. |
Feb 1988 |
|
4743294 |
Diehr et al. |
May 1988 |
|
Divisions (1)
|
Number |
Date |
Country |
Parent |
227587 |
Aug 1988 |
|
Continuation in Parts (1)
|
Number |
Date |
Country |
Parent |
521055 |
May 1990 |
|