Herbicidal sulphonylated carboxamides

Herbicidal sulphonylated carboxamides of the formula R.sup.1 --CO--NH--SO.sub.2 --(A).sub.n --R.sup.2 (I) in which n represents the numbers 0 or 1, A represents oxygen, iminio (NH) or methylene (CH.sub.2), R.sup.1 represents a five-membered heteroaryl radical which contains 1 or 2 nitrogen atoms and additionally one oxygen or sulphur atom in the ring and which is optionally substituted by halogen or by alkyl, alkoxy, alkylthio, alkylsulphinyl, alkylsulphonyl, alkylamino, dialkylamino or phenyl which are in each case optionally substituted, and R.sup.2 represents aryl or heteroaryl which are in each case optionally substituted, or salts thereof, with the exclusion of the compound 2-dimethylamino-N-(4-methyl-phenylsulphonyl)-5-thiazole carboxamide.

We claim:

1. A sulphonylated carboxamide of the formula

R.sup.1 --CO--NH--SO.sub.2 --(A).sub.n --R.sup.2 (I)

in which

n represents the number 0 or 1,

A represents oxygen, imino (NH) or methylene (CH.sub.2),

R.sup.1 represents a five-membered heretoaryl radical from the group consisting of oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, oxadiazolyl and thiadiazolyl, which is optionally monosubstituted or polysubstitututed by identical or different halogen or by optionally halogen-substituted C.sub.1 -C.sub.6 -alkyl, phenyl, C.sub.1 -C.sub.6 -alkoxy, C.sub.1 -C.sub.6 -alkylthio, C.sub.1 -C.sub.6 -alkylsulphinyl, C.sub.1 -C.sub.6 -alkylsulphonyl, C.sub.1 -C.sub.6 -alkylamino or di-(C.sub.1 -C.sub.6 -alkyl)amino, and

R.sup.2 represents the radical ##STR136## in which R.sup.3 and R.sup.4 are identical or different and represent hydrogen, fluorine, chlorine, bromine, iodine, cyano, nitro, carboxyl or 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 -alkylamino-carbonyl, di-(C.sub.1 -C.sub.4 -alkyl)aminocarbonyl, hydroxyl, C.sub.1 -C.sub.4 -alkoxy, formyloxy, C.sub.1 -C.sub.4 -alkyl-carbonyloxy, C.sub.1 -C.sub.4 -alkoxycarbonyloxy, 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 R.sup.3 and R.sup.4 furthermore independently of one another represent C.sub.2 -C.sub.6 -alkenyl which is optionally substituted by fluorine, chlorine, bromine, cyano, C.sub.1 -C.sub.4 -alkoxycarbonyl, carboxyl or phenyl, or R.sup.3 and R.sup.4 additionally independently of one another 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; C.sub.1 -C.sub.4 -alkoxy which is optionally substituted by fluorine, chlorine, bromine, cyano, carboxyl, C.sub.1 -C.sub.4 -alkoxyacarbonyl, 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; C.sub.1 -C.sub.4 -alkylthio which is optionally substituted by fluorine, chlorine, bromine, cyano, carboxyl, C.sub.1 -C.sub.4 -alkoxycarbonyl, C.sub.1 -C.sub.4 -alkylthio, C.sub.1 -C.sub.4 -alkylsulphinyl or C.sub.1 -C.sub.4 -alkylsulphonyl; 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, 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 -alkoxy-carbonyl; C.sub.3 -C.sub.6 -alkynyloxy, C.sub.3 -C.sub.6 -alkylthio or the radical --S(O).sub.p --R.sup.5, or

R.sup.3 and R.sup.4 furthermore represent phenyl or phenoxy, C.sub.1 -C.sub.4 -alkylcarbonylamino, C.sub.1 -C.sub.4 -alkoxycarbonylamino, C.sub.1 -C.sub.4 -alkylamino-carbonylamino, di-(C.sub.1 -C.sub.4 -alkyl)-amino-carbonylamino, or the radical --CO--R.sup.6, or R.sup.3 and R.sup.4 furthermore represent C.sub.1 -C.sub.4 -alkylsulphonyloxy, di-(C.sub.1 -C.sub.4 -alkyl)-aminosulphonylamino or the radical --CH.dbd.N--R.sup.7, in which

p represents the numbers 1 or 2 and

R.sup.5 represents C.sub.1 -C.sub.4 -alkyl which is optionally substituted by fluorine, chlorine, bromine, cyano or C.sub.1 -C.sub.4 -alkoxycarbonyl, or R.sup.5 represents C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -alkoxy-C.sub.1 -C.sub.4 -alkylamino or di-(C.sub.1 -C.sub.4 -alkyl)-amino,

R.sup.6 represents C.sub.1 -C.sub.6 -alkyl, C.sub.1 -C.sub.6 -alkoxy which is optionally substituted by fluorine, chlorine, methoxy or ethoxy; C.sub.3 -C.sub.6 -cycloalkoxy, C.sub.3 -C.sub.6 -alkenyloxy, C.sub.1 -C.sub.4 -alkylthio, amino, 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 or chlorine and

R.sup.7 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, benzyl which is optionally substituted by fluorine or chlorine, C.sub.3 -C.sub.6 -alkenyl or C.sub.3 -C.sub.6 -alkynyl which are optionally substituted by fluorine or chlorine, 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, C.sub.1 -C.sub.6 -alkoxy, C.sub.3 -C.sub.6 -alkenyloxy, C.sub.3 -C.sub.6 -alkynyloxy or benzyloxy which are optionally substituted by fluorine or chlorine, or R.sup.7 furthermore 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-carbonylamino, C.sub.1 -C.sub.4 -alkoxycarbonylamino, C.sub.1 -C.sub.4 -alkyl-sulphonylamino or phenyl sulphonylamino which is optionally substituted by fluorine, chlorine, bromine or methyl,

R.sup.10 and R.sup.11 are identical or different and represent hydrogen, fluorine, chlorine, bromine, nitro, cyano, or C.sub.1 -C.sub.4 -alkyl which is optionally substituted by fluorine or chlorine; C.sub.2 -C.sub.4 -alkenyl which is optionally substituted by fluorine or chlorine, C.sub.1 -C.sub.4 -alkoxy which is optionally substituted by fluorine 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 are optionally substituted by fluorine or chlorine; and di-(C.sub.1 -C.sub.4 -alkyl)-aminosulphonyl, C.sub.1 -C.sub.4 -alkoxy-carbonyl, dimethylaminocarbonyl or dioxolanyl;

or a salt thereof, with the exclusion of the compound 2-(dimethylamino)-N-[(4-methylphenyl)sulphonyl]-5-thiazole carboxamide.

2. A sulphonylated carboxamide according to claim 1, in which

n represents the numbers 0 or 1,

A represents oxygen, imino (NH) or methylene (CH.sub.2),

R.sup.1 represents a five-membered heteroaryl radical from the group consisting of oxazolyl, isoxazolyl, thiazolyl, 1,2,4-oxadiazolyl, 1,3,4-oxadiazolyl, 1,2,4-thiadiazolyl and 1,3,4-thiadiazolyl, which is optionally substituted by fluorine, chlorine, bromine, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, fluoromethyl, chloromethyl, difluoromethyl, dichloromethyl, trifluoromethyl, trichloromethyl, chlorofluoromethyl, chlorodifluoromethyl fluorodichloromethyl, phenyl, methoxy, ethoxy, propoxy, isopropyloxy, difluoromethoxy, trifluoromethoxy, chlorodifluoromethoxy, methylthio, ethylthio, propylthio, isopropylthio, difluoromethylthio, trifluoromethylthio, chlorodifluoromethylthio, methylsulphinyl, ethylsulphinyl, propylsulphinyl, methylsulphonyl, ethylsulphonyl, propylsulphonyl, methylamino, ethylamino, propylamino, isopropylamino or dimethylamino, and

R.sup.2 represents the radical ##STR137## in which R.sup.3 represents hydrogen, fluorine, chlorine, bromine, cyano, nitro, carboxyl, methyl, trifluoromethyl, methoxy, ethoxy, 2-chloroethoxy, difluoromethoxy, trifluoromethoxy, C.sub.1 -C.sub.3 -alkylthio, C.sub.1 -C.sub.3 -alkyl-sulphinyl, C.sub.1 -C.sub.3 -alkylsulphonyl, dimethylaminosulphonyl, diethylaminosulphonyl, N-methoxy-N-methylaminosulphonyl, phenyl, phenoxy or C.sub.1 -C.sub.3 -alkoxycarbonyl and

R.sup.4 represents hydrogen, fluorine, chlorine, bromine, methyl, trifluoromethyl or methoxy,

R.sup.10 represents dimethylaminocarbonyl or C.sub.1 -C.sub.4 -alkylsulphonyl, and

R.sup.11 represents hydrogen, fluorine or chlorine

or a salt thereof, with the exclusion of the compound 2-(dimethylamino)-N-[(4-methylphenyl)-sulphonyl]-5-thiazole carboxamide.

3. A method of combating unwanted vegetation which comprises applying to such vegetation or to a locus from which is it desired to exclude such vegetation a herbicidally effective amount of a sulphonylated carboxamide of the formula

R.sup.1 --CO--NH--SO.sub.2 --(A).sub.n --R.sup.2 (I)

in which

n represents the numbers of 0 or 1,

A represents oxygen, imino (NH) or methylene (CH.sub.2),

R.sup.1 represents a five-membered heteroaryl radical from the group consisting of oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, oxadiazolyl and thiadiazolyl, which is optionally monosubstituted or polysubstituted by identical to different halogen or by optionally halogen-substituted C.sub.1 -C.sub.6 -alkyl, phenyl, C.sub.1 -C.sub.6 -alkoxy, C.sub.1 -C.sub.6 -alkylthio, C.sub.1 -C.sub.6 -alkylsulphinyl, C.sub.1 -C.sub.6 -alkylsulphonyl, C.sub.1 -C.sub.6 -alkylamino or di-(C.sub.1 -C.sub.4 -alkyl)amino, and

R.sup.2 represents the radical ##STR138## in which R.sup.3 and R.sup.4 are identical or different and represent hydrogen, fluorine, chlorine, bromine, iodine, cyano, nitro, carboxyl or 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 -alkylamino-carbonyl, di-(C.sub.1 -C.sub.4 -alkyl)aminocarbonyl, hydroxyl, C.sub.1 -C.sub.4 -alkoxy, formyloxy, C.sub.1 -C.sub.4 -alkyl-carbonyloxy, C.sub.1 -C.sub.4 -alkoxycarbonyloxy, 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 R.sup.3 and R.sup.4 furthermore independently of one another represent C.sub.2 -C.sub.6 -alkenyl which is optionally substituted by fluorine, chlorine, bromine, cyano, C.sub.1 -C.sub.4 -alkoxycarbonyl, carboxyl or phenyl, or R.sup.3 and R.sup.4 additionally independently of one another 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; C.sub.1 -C.sub.4 -alkoxy which is optionally substituted by fluorine, chlorine, bromine, cyano, carboxyl, C.sub.1 -C.sub.4 -alkoxycarbonyl, 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; C.sub.1 -C.sub.4 -alkylthio which is optionally substituted by fluorine, chlorine, bromine, cyano, carboxyl, C.sub.1 -C.sub.4 -alkoxycarbonyl, C.sub.1 -C.sub.4 -alkylthio, C.sub.1 -C.sub.4 -alkylsulphinyl or C.sub.1 -C.sub.4 -alkylsulphonyl; 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, 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 -alkoxy-carbonyl; C.sub.3 -C.sub.6 -alkynyloxy, C.sub.3 -C.sub.6 -alkynylthio or the radical --S(O).sub.p --R.sup.5, or

R.sup.3 and R.sup.4 furthermore represent phenyl or phenoxy, C.sub.1 -C.sub.4 -alkylcarbonylamino, C.sub.1 -C.sub.4 -alkoxycarbonylamino, C.sub.1 -C.sub.4 -alkylamino-carbonylamino, di-(C.sub.1 -C.sub.4 -alkyl)-amino-carbonylamino, or the radical --CO--R.sup.6, or R.sup.3 and R.sup.4 furthermore represent C.sub.1 -C.sub.4 -alkylsulphonyloxy, di-(C.sub.1 -C.sub.4 -alkyl)-aminosulphonylamino or the radical --CH.dbd.N--R.sup.7, in which

p represents the numbers 1 or 2and

R.sup.5 represents C.sub.1 -C.sub.4 -alkyl which is optionally substituted by fluorine, chlorine, bromine, cyano or C.sub.1 -C.sub.4 -alkoxycarbonyl, or R.sup.5 represents C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -alkoxy-C.sub.1 -C.sub.4 -alkylamino or di(C.sub.1 -C.sub.4 -alkyl)-amino,

R.sup.6 represents C.sub.1 -C.sub.6 -alkyl, C.sub.1 -C.sub.6 -alkoxy which is optionally substituted by fluorine, chlorine, methoxy or ethoxy; C.sub.3 -C.sub.6 -cycloalkoxy, C.sub.3 -C.sub.6 -alkenyloxy, C.sub.1 -C.sub.4 -alkylthio, amino, 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 or chlorine and

R.sup.7 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, benzyl which is optionally substituted by fluorine or chlorine, C.sub.3 -C.sub.6 -alkenyl or C.sub.3 -C.sub.6 -alkynyl which are optionally substituted by fluorine or chlorine, phenyl which is optionally substituted by fluorine, chlorine, bromine, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, trifluoromethylthio, C.sub.1 -C.sub.6 -alkoxy, C.sub.3 -C.sub.6 -alkenyloxy, C.sub.3 -C.sub.6 -alkynyloxy or benzyloxy which are optionally substituted by fluorine or chlorine, or R.sup.7 furthermore 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-carbonylamino, C.sub.1 -C.sub.4 -alkoxycarbonylamino, C.sub.1 -C.sub.4 -alkyl-sulphonylamino or phenyl sulphonylamino which is optionally substituted by fluorine, chlorine, bromine or methyl,

R.sup.10 and R.sup.11 are identical or different and represent hydrogen, fluorine, chlorine, bromine, nitro, cyano, or C.sub.1 -C.sub.4 -alkyl which is optionally substituted by fluorine or chlorine; C.sub.2 -C.sub.4 -alkenyl which is optionally substituted by fluorine or chlorine, C.sub.1 -C.sub.4 -alkoxy which is optionally substituted by fluorine 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 are optionally substituted by fluorine or chlorine; and di-(C.sub.1 -C.sub.4 -alkyl)-aminosulphonyl, C.sub.1 -C.sub.4 -alkoxy-carbonyl, dimethylaminocarbonyl or dioxolanyl; or a salt thereof.

4. A salt of a compound according to claim 1, with the hydroxide, hydride, amide or carbonate or sodium potassium or calcium, the C.sub.1 -C.sub.4 -alkoxide of sodium or potassium, ammonia, an C.sub.1 -C.sub.4 -alkylamine, di-(C.sub.1 -C.sub.4 -alkyl)-amine or tri-(C.sub.1 -C.sub.4 -alkyl)-amine.

5. A sulphonylated carboxamide according to claim 1, in which

R.sup.2 represents the radical ##STR139##

6. A sulphonylated carboxamide according to claim 5, in which R.sup.4 is hydrogen.

7. A compound according to claim 1, wherein such compound is N-(2-methoxycarbonyl-phenylsulphonyl)-5-methyl-isoxazole-3-carboxamide of the formula ##STR140## or a salt thereof.

8. A herbicidal composition comprising a herbicidally effective amount of a compound of salt according to claim 1 and a diluent.

9. A method of combating 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 according to claim 7.

10. A sulphonylated carboxamide of the formula ##STR141## in which n represents the numbers 0 or 1,

A represents oxygen, imino (NH) or methylene (CH.sub.2),

R.sup.1 represents a five-membered heteroaryl radical from the group consisting of oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, oxadiazolyl and thiadiazolyl, which is optionally monosubstituted or polysubstituted by identical or different halogen or by optionally halogen-substituted C.sub.1 -C.sub.6 -alkyl, phenyl, C.sub.1 -C.sub.6 -alkoxy, C.sub.1 -C.sub.6 -alkylthio, C.sub.1 -C.sub.6 -alkylsulphinyl, C.sub.1 -C.sub.6 -alkylsulphonyl, C.sub.1 -C.sub.6 -alkylamino or di-(C.sub.1 -C.sub.4 -alkyl)-amino, and

R.sup.2 represents fluorine, chlorine, bromine, iodine, cyano, nitro, carboxyl, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -alkylthio, phenyl, C.sub.1 -C.sub.4 -alkylsulphinyl, C.sub.1 -C.sub.4 -alkylsulphonyl, di-(C.sub.1 -C.sub.4 -alkyl)-aminosulphonyl, or the radical --S(O).sub.p --R.sup.5,

p represents the numbers 1 or 2 and

R.sup.5 represents C.sub.1 -C.sub.4 -alkoxy-C.sub.1 -C.sub.4 -alkylamino which are optionally substituted by fluorine or chlorine, furthermore represents C.sub.1 -C.sub.4 -alkoxycarbonyl, which is optionally substituted by fluorine, chlorine, or C.sub.1 -C.sub.4 -alkoxy,

R.sup.3 represents hydrogen, fluorine, chlorine, bromine, methyl, or a salt thereof, with the exclusion of the compound 2-(dimethylamino)-N-[(4-methylphenyl) sulphonyl]-5-thiazole carboxamide.

11. A compound according to claim 1, wherein such compound is N-(2-methoxycarbonyl-phenylsulphonyl)-3-methyl-1,2,4-oxadiazole-5-carboxam ide of the formula ##STR142##