Sulfonated heterocyclic carboxamides and their use as herbicides, and growth regulators

Claim 1

A compound of the formula I or its salts ##STR42## in which R 1 is hydrogen, (C 1 -C 4 )alkyl, (C 2 -C 6 )alkenyl or (C 2 -C 6 )-alkynyl; R 2 , R 3 independently of one another are hydrogen, (C 1 -C 3 )-alkyl or phenyl; W is O, S, NR 7 or NOR 7 ; X is CHR 2 , O, NR 7 or NOR 7 ; R 4 , R 5 independently of one another are hydrogen, hydroxyl, halogen, (C 1 -C 6 )alkyl, (C 1 -C 6 )alkoxy or (C 1 -C 6 )alkylthio, where the three abovementioned radicals can be monosubstituted or polysubstituted by halogen or monosubstituted or disubstituted by (C 1 -C 4 )alkoxy or (C 1 -C 4 )alkylthio; --NR 8 R 9 , (C 3 -C 6 )-cycloalkyl, --OCHR 8 CO 2 R 10 , (C 2 -C 5 )alkenyl, (C 2 -C 4 )-alkynyl, (C 3 -C 5 )alkenyloxy or (C 3 -C 5 )alkynyloxy; R 6 is hydrogen, halogen, (C 1 -C 3 )alkyl, (C 1 -C 3 )alkoxy, --CN, --NO 2 , --CO--R 11 , --CO 2 R 12 , (C 1 -C 3 )alkylthio, --SO--R 12 , --SO 2 --R 12 or --CO--NR 8 R 9 ; R 7 is hydrogen, (C 1 -C 3 )alkyl, (C 1 -C 3 )haloalkyl or phenyl; R 8 is hydrogen or (C 1 -C 4 )alkyl or R 8 and R 9 together are --(CH 2 ) 2 (CH 2 ) c (CH 2 ) 2 -- or --(CH 2 ) 2 O(CH 2 ) 2 --; R 9 is hydrogen, (C 1 -C 4 )alkyl, (C 1 -C 4 )alkoxy, (C 2 -C 4 )alkenyl or R 8 and R 9 together are --(CH 2 ) 2 --(CH 2 ) c --(CH 2 2 -- or --(CH 2 ) 2 O(CH 2 ) 2 --; R 10 is hydrogen, (C 1 -C 4 )alkyl which is unsubstituted, or monosubstituted or polysubstituted by halogen or monosubstituted or disubstituted by CN, CO 2 --R 12 , --NR 8 R 9 , OR 12 or Si(CH 3 ) 3 ; (C 3 -C 4 )alkynyl or (C 3 -C 4 )--alkenyl, where the two abovementioned radicals are unsubstituted or substituted by CH 3 or --Si(CH 3 ) 3 ; (C 3 -C 6 )cycloalkyl which is unsubstituted or substituted by (C 1 -C 4 )alkyl or (C 1 -C 4 )alkoxy; or Si(CH 3 ) 3 ; R 11 is hydrogen, (C 1 -C 4 )alkyl, (C 1 -C 4 )alkyl which is monosubstituted or polysubstituted by halogen or (C 1 -C 3 )alkoxy; (C 3 -C 6 )cycloalkyl which is unsubstituted, or monosubstituted or polysubstituted by halogen or CH 3 ; (C 2 -C 4 )alkenyl or (C 2 -C 4 )alkynyl; R 12 is (C 1 -C 3 )alkyl; L is a hetero- or isocyclic radical of the formulae (L1) to (L5) ##STR43## R 13 is hydrogen, halogen, NO 2 , CN, (C 1 -C 4 )alkyl which is unsubstituted, or monosubstituted or polysubstituted by halogen, or monosubstituted by CN, OCH 3 or SCH 3 ; (C 2 -C 4 )alkenyl which is unsubstituted, or monosubstituted or polysubstituted by halogen, or monosubstituted by OCH 3 ; (C 2 -C 4 )alkynyl which is unsubstituted, or monosubstituted or polysubstituted by halogen, or monosubstituted by OCH 3 or Si(CH 3 ) 3 ; (C 3 -C 6 )cycloalkyl which is unsubstituted, or monosubstituted or polysubstituted by halogen or CH 3 ; --CO--R 11 , --OCH 2 CH 2 OR 11 , --OH, --C(R 11 )(OR 17 )(OR 18 ); --CO 2 R 10 , --CO--NR 8 R 9 , --N 3 , SO 2 NR 8 R 9 , --SO 3 R 19 , --OSO 2 R 20 ; phenyl which is unsubstituted, or monosubstituted or polysubstituted by halogen, CH 3 or OCH 3 ; E--R 21 or --(CH 2 ) e --G; R 14 is hydrogen, halogen; CN, NO 2 , (C 1 -C 4 )alkyl which is unsubstituted, or monosubstituted or polysubstituted by halogen or monosubstituted or disubstituted by --CO 2 R 10 , --SO 2 NR 8 R 9 , --NR 8 R 9 , (C 1 -C 2 )alkoxy, --E--R 22 , (C 1 -C 2 )haloalkoxy, (C 1 -C 2 )alkylthio, (C 1 -C 2 )haloalkylthio, --CN, --OH or SH; --CO 2 R 10 , --SO 2 NR 8 R 9 , --NR 8 R 9 or --E--R 22 ; R 15 is hydrogen, (C 1 -C 4 )alkyl, (C 1 -C 4 )haloalkyl, (C 2 -C 4 )-alkenyl, phenyl or phenyl which is monosubstituted or polysubstituted by halogen or --E--R 22 ; --E--R 22 or halogen; R 16 is hydrogen, (C 1 -C 4 )alkyl, (C 1 -C 4 )haloalkyl, halogen, --CO 2 R 10 , --SO 2 NR 8 R 9 , --OSO 2 R 20 , --E--R 22 , --CN or --NO 2 ; E, Z independently of one another are O or S(O) f ; a, b, c, d, e independently of one another are 0 or 1; f is 0, 1 or 2; R 17 , R 18 independently of one another are (C 1 -C 4 )alkyl, or R 17 and R 18 together are --CH 2 CH 2 --, --CH 2 OCH 2 -- or --CH 2 --C(CH 3 ) 2 CH 2 --; R 19 is (C 1 -C 4 )alkyl or (C 1 -C 4 )haloalkyl, R 20 is (C 1 -C 4 )alkyl, --NR 8 R 9 or (C 1 -C 4 )haloalkyl, R 21 is (C 1 -C 4 )alkyl, (C 1 -C 4 )haloalkyl, (C 2 -C 4 )alkoxyalkyl, (C 2 -C 4 )alkenyl, (C 3 -C 4 )alkynyl, phenyl or phenyl which is monosubstituted or polysubstituted by halogen, (C 1 -C 3 )alkyl, (C 1 -C 3 )alkoxy or (C 1 -C 3 )haloalkyl; or (C 2 -C 4 )haloalkenyl; R 22 is (C 1 -C 4 )alkyl or (C 1 -C 4 )alkyl which is monosubstituted or polysubstituted by halogen or monosubstituted by OR 19 ; R 23 is hydrogen, (C 1 -C 4 )alkyl which is unsubstituted, or monosubstituted or polysubstituted by halogen or monosubstituted by phenyl, or (C 2 -C 4 )alkenyl, phenyl or phenyl which is monosubstituted or polysubstituted by halogen, (C 1 -C 4 )alkyl, (C 1 -C 4 )haloalkyl, --NO 2 , --CN or (C 1 -C 4 )alkoxy, G is a heterocyclic radical from the group comprising (G1)-(G25); ##STR44## and R 24 is hydrogen or (C 1 -C 4 )alkyl; R 25 is hydrogen, (C 1 -C 3 )alkyl or (C 2 -C 4 )alkenyl.