Claims
- 1. A composition for the selective control of weeds in crops of useful plants, which comprises, as active ingredient, together with inert carriers and adjuvants, a mixture comprising
- a) a herbicidally effective amount of a pyridylsulfonylurea of formula I ##STR149## wherein R is hydrogen, halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy or C.sub.1 -C.sub.4 alkylthio, or is C.sub.1 -C.sub.4 alkyl mono- or poly-substituted by halogen; R.sub.1 is hydrogen or methyl; R.sub.2 is methyl or methoxy; A is --X--R.sub.3 or --N--(R.sub.4)R.sub.5 ; R.sub.3 is C.sub.1 -C.sub.6 alkyl, or C.sub.1 -C.sub.6 alkyl that is mono- or poly-substituted by halogen, C.sub.1 -C.sub.6 alkoxy, C.sub.3 -C.sub.6 alkenyloxy, C.sub.3 -C.sub.6 alkynyloxy or by C.sub.3 -C.sub.6 cycloalkyl, which may for its part be interrupted by oxygen; or is C.sub.3 -C.sub.6 alkenyl, or C.sub.3 -C.sub.6 alkenyl that is mono- or poly-substituted by halogen, C.sub.1 -C.sub.6 alkoxy, C.sub.3 -C.sub.6 alkenyloxy or by C.sub.3 -C.sub.6 alkynyloxy; or is C.sub.4 -C.sub.6 cycloalkyl, or C.sub.4 -C.sub.6 cycloalkyl that is mono- or poly-substituted by halogen or by C.sub.1 -C.sub.6 alkoxy; or is C.sub.3 -C.sub.6 cycloalkyl that is interrupted by oxygen; or is C.sub.3 -C.sub.6 alkynyl; X is oxygen or S(O).sub.n ; n is 0, 1 or 2; R.sub.4 is hydrogen, C.sub.1 -C.sub.6 alkyl, or C.sub.1 -C.sub.6 alkyl that is mono- or poly-substituted by halogen, C.sub.1 -C.sub.6 alkoxy, C.sub.3 -C.sub.6 alkenyloxy, C.sub.3 -C.sub.6 alkynyloxy or by C.sub.1 -C.sub.6 alkylthio; R.sub.5 is hydrogen, C.sub.1 -C.sub.6 alkyl, or C.sub.1 -C.sub.6 alkyl that is mono- or poly-substituted by halogen, C.sub.1 -C.sub.6 alkoxy, C.sub.3 -C.sub.6 alkenyloxy, C.sub.3 -C.sub.6 alkynyloxy or by C.sub.1 -C.sub.6 alkylthio, or is C(O)R.sub.6 ; and R.sub.6 is hydrogen, C.sub.1 -C.sub.6 alkyl, C.sub.3 -C.sub.6 cycloalkyl or C.sub.2 -C.sub.6 alkynyl; or is C.sub.1 -C.sub.6 alkyl or C.sub.3 -C.sub.6 cycloalkyl each substituted by halogen or by C.sub.1 -C.sub.4 alkoxy; or is C.sub.2 -C.sub.6 alkenyl, or C.sub.2 -C.sub.6 alkenyl substituted by halogen; or is phenyl, benzyl, naphthyl or OR.sub.12, or phenyl, benzyl or naphthyl each substituted by halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 haloalkoxy, C.sub.3 -C.sub.6 alkenyloxy, C.sub.3 -C.sub.6 alkynyloxy, nitro, cyano, COOR.sub.13, NR.sub.15 R.sub.16, C(O)NR.sub.17 R.sub.18, X.sub.1 R.sub.20, SO.sub.2 NR.sub.21 R.sub.22 or by X.sub.2 R.sub.23 ; R.sub.12 is C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 haloalkyl, oxetan-3-yl, or C.sub.4 -C.sub.6 cycloalkyl, which may for its part be substituted by halogen, C.sub.1 -C.sub.4 alkyl or by C.sub.1 -C.sub.4 alkoxy; or is phenyl, benzyl or naphthyl, or phenyl, benzyl or naphthyl each substituted by C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 haloalkoxy, C.sub.1 -C.sub.4 alkylthio, C.sub.1 -C.sub.4 haloalkylthio, C.sub.1 -C.sub.4 alkylsulfonyl, C.sub.1 -C.sub.4 alkylsulfinyl, nitro, cyano, COOR.sub.27, NR.sub.25 R.sub.26, CONR.sub.28 R.sub.29 or by SO.sub.2 NR.sub.30 R.sub.14 ; or is C.sub.1 -C.sub.6 alkyl substituted by C.sub.1 -C.sub.4 alkoxy, C.sub.3 -C.sub.6 cycloalkyl, cyano, COOR.sub.24 or by CONR.sub.32 R.sub.33 ; or is C.sub.3 -C.sub.6 alkenyl, C.sub.3 -C.sub.6 haloalkenyl, C.sub.3 -C.sub.6 alkynyl, C.sub.3 -C.sub.6 haloalkynyl, X.sub.3 R.sub.35 or X.sub.4 R.sub.36 ; R.sub.13 is hydrogen, C.sub.1 -C.sub.6 alkyl, C.sub.3 -C.sub.6 alkenyl, C.sub.3 -C.sub.6 alkynyl or oxetan-3-yl; R.sub.14, R.sub.15, R.sub.16, R.sub.17, R.sub.18, R.sub.21, R.sub.22, R.sub.25, R.sub.26, R.sub.28, R.sub.29, R.sub.30, R.sub.32 and R.sub.33 are each independently of the others hydrogen, C.sub.1 -C.sub.4 alkyl, C.sub.3 -C.sub.6 alkenyl or C.sub.3 -C.sub.6 alkynyl; or R.sub.15 and R25 are each independently of the other the groups --C(O)--X.sub.5 --C.sub.1 -C.sub.4 alkyl or --C(O)--C.sub.1 -C.sub.4 alkyl, which may for their part be substituted by halogen; or R.sub.15 and R.sub.16 or R.sub.17 and R.sub.18 or R.sub.21 and R.sub.22 or R.sub.25 and R.sub.26 or R.sub.28 and R.sub.29 or R.sub.30 and R.sub.14 or R.sub.32 and R.sub.33 together form a C.sub.4 -C.sub.5 alkylene chain, which may for its part be interrupted by oxygen or by NR.sub.19, R.sub.19 is hydrogen, C.sub.1 -C.sub.4 alkyl, C.sub.3 -C.sub.6 alkenyl or C.sub.3 -C.sub.6 alkynyl; R.sub.20 and R.sub.35 are each independently of the other C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.4 haloalkyl; R.sub.23 and R.sub.36 are each independently of the other C.sub.1 -C.sub.4 alkyl substituted by COOR.sub.34 ; R.sub.24, R.sub.27 and R.sub.34 are each independently of the other hydrogen or C.sub.1 -C.sub.4 alkyl; X.sub.1 and X.sub.3 are each independently of the other sulfur, SO or SO.sub.2 ; X.sub.2 and X.sub.4 are each independently of the other oxygen or sulfur; X.sub.5 is oxygen or NR.sub.37 ; and R.sub.37 is hydrogen, C.sub.1 -C.sub.4 alkyl, C.sub.3 -C.sub.6 alkenyl or C.sub.3 -C.sub.6 alkynyl; or an N-oxide or a salt of a compound of formula I, and
- b) a herbicide-antagonistically effective amount of a sulfamoylphenylurea of formula II ##STR150## wherein A.sub.2 is a radical from the group ##STR151## R.sub.7 and R.sub.8 are each independently of the other hydrogen, C.sub.1 -C.sub.8 alkyl, C.sub.3 -C.sub.8 cycloalkyl, C.sub.3 -C.sub.6 alkenyl, C.sub.3 -C.sub.6 alkynyl or ##STR152## or are C.sub.1 -C.sub.4 alkyl substituted by C.sub.1 -C.sub.4 alkoxy or by ##STR153## R.sub.7 and R.sub.8 together form a C.sub.4 -C.sub.6 alkylene bridge, or a C.sub.4 -C.sub.6 alkylene bridge interrupted by oxygen, sulfur, SO, SO.sub.2, NH or by --N(C.sub.1 -C.sub.4 alkyl)--; R.sub.9 is hydrogen or C.sub.1 -C.sub.4 alkyl; R.sub.10 and R.sub.11 are each independently of the other hydrogen, halogen, cyano, nitro, trifluoromethyl, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 alkylthio, C.sub.1 -C.sub.4 alkylsulfinyl, C.sub.1 -C.sub.4 alkylsulfonyl, --COOR.sub.j, CONR.sub.k R.sub.m, --COR.sub.n, --SO.sub.2 NR.sub.k R.sub.m or --OSO.sub.2 --C.sub.1 -C.sub.4 alkyl; or R.sub.10 and R.sub.11 together form a C.sub.3 -C.sub.4 alkylene bridge, which may be substituted by halogen or by C.sub.1 -C.sub.4 alkyl, or a C.sub.3 -C.sub.4 alkenylene bridge, which may be substituted by halogen or by C.sub.3 - or C.sub.4 -alkyl, or a butadienylene bridge, which may be substituted by halogen or by C.sub.1 -C.sub.4 alkyl, and R.sub.g and R.sub.h are each independently of the other hydrogen, halogen, C.sub.1 -C.sub.4 alkyl, trifluoromethyl, methoxy, methylthio or --COOR.sub.j ; R.sub.c is hydrogen, halogen, C.sub.1 -C.sub.4 alkyl or methoxy; R.sub.d is hydrogen, halogen, nitro, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 alkylthio, C.sub.1 -C.sub.4 alkylsulfinyl, C.sub.1 -C.sub.4 alkylsulfonyl, --COOR.sub.j or --CONR.sub.k R.sub.m ; and R.sub.e is hydrogen, halogen, halo-C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkyl, --COOR.sub.j, trifluoromethyl or methoxy; or R.sub.d and R.sub.e together form a C.sub.3 -C.sub.4 alkylene bridge; R.sub.f is hydrogen, halogen or C.sub.1 -C.sub.4 alkyl; R.sub.x and R.sub.y are each independently of the other hydrogen, halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 alkylthio, --COOR.sub.17, trifluoromethyl, nitro or cyano; R.sub.17 is hydrogen, C.sub.1 -C.sub.10 alkyl, C.sub.1 -C.sub.4 alkoxy-C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkylthio-C.sub.1 -C.sub.4 alkyl, di-C.sub.1 -C.sub.4 alkylamino-C.sub.1 -C.sub.4 alkyl, halo-C.sub.1 -C.sub.8 alkyl, C.sub.2 -C.sub.8 alkenyl, halo-C.sub.2 -C.sub.8 alkenyl, C.sub.3 -C.sub.8 alkynyl, C.sub.3 -C.sub.7 cycloalkyl, halo-C.sub.3 -C.sub.7 cycloalkyl, C.sub.1 -C.sub.8 alkylcarbonyl, allylcarbonyl, C.sub.3 -C.sub.7 cycloalkylcarbonyl, benzoyl that is unsubstituted or mono- to tri-substituted in the phenyl ring by the same or different substituents selected from halogen, C.sub.1 -C.sub.4 alkyl, halo-C.sub.1 -C.sub.4 alkyl, halo-C.sub.1 -C.sub.4 alkoxy and C.sub.1 -C.sub.4 alkoxy; or is furoyl or thienyl; or is C.sub.1 -C.sub.4 alkyl substituted by phenyl, halophenyl, C.sub.1 -C.sub.4 alkylphenyl, C.sub.1 -C.sub.4 alkoxyphenyl, halo-C.sub.1 -C.sub.4 alkylphenyl, halo-C.sub.1 -C.sub.4 alkoxyphenyl, C.sub.1 -C.sub.6 alkoxycarbonyl, C.sub.1 -C.sub.4 alkoxy-C.sub.1 -C.sub.8 alkoxycarbonyl, C.sub.3 -C.sub.8 alkenyloxycarbonyl, C.sub.3 -C.sub.8 alkynyloxycarbonyl, C.sub.1 -C.sub.8 alkylthiocarbonyl, C.sub.3 -C.sub.8 alkenylthiocarbonyl, C.sub.3 -C.sub.8 alkynylthiocarbonyl, carbamoyl, mono-C.sub.1 -C.sub.4 alkylaminocarbonyl or by di-C.sub.1 -C.sub.4 alkylaminocarbonyl; or is phenylaminocarbonyl that is unsubstituted or mono- to tri-substituted in the phenyl ring by the same or different substituents selected from halogen, C.sub.1 -C.sub.4 alkyl, halo-C.sub.1 -C.sub.4 alkyl, halo-C.sub.1 -C.sub.4 alkoxy and C.sub.1 -C.sub.4 alkoxy or that is mono-substituted in the phenyl ring by cyano or by nitro; or is dioxolan-2-yl that is unsubstituted or substituted by one or two C.sub.1 -C.sub.4 alkyl radicals; or is dioxan-2-yl that is unsubstituted or substituted by one or two C.sub.1 -C.sub.4 alkyl radicals; or is C.sub.1 -C.sub.4 alkyl that is substituted by cyano, nitro, carboxy or by C.sub.1 -C.sub.8 alkylthio-C.sub.1 -C.sub.8 alkoxycarbonyl; R.sub.j, R.sub.k and R.sub.m are each independently of the others hydrogen or C.sub.1 -C.sub.4 alkyl; or R.sub.k and R.sub.m together form a C.sub.4 -C.sub.6 alkylene bridge, or a C.sub.4 -C.sub.6 alkylene bridge interrupted by oxygen, NH or by --N(C.sub.1 -C.sub.4 alkyl)--; and R.sub.n is C.sub.1 -C.sub.4 alkyl, phenyl, or phenyl substituted by halogen, C.sub.1 -C.sub.4 alkyl, methoxy, nitro or by trifluoromethyl; or a salt of a compound of formula II.
- 2. A composition according to claim 1, wherein R.sub.6 is hydrogen, C.sub.1 -C.sub.6 alkyl or C.sub.3 -C.sub.6 cycloalkyl.
- 3. A composition according to claim 1, wherein R.sub.3 is C.sub.1 -C.sub.6 alkyl, or C.sub.1 -C.sub.6 alkyl that is mono- or poly-substituted by halogen, C.sub.1 -C.sub.6 alkoxy, C.sub.3 -C.sub.6 alkenyloxy, C.sub.3 -C.sub.6 alkynyloxy or by C.sub.3 -C.sub.6 cycloalkyl, which may for its part be interrupted by oxygen; or is C.sub.3 -C.sub.6 alkenyl, or C.sub.3 -C.sub.6 alkenyl that is mono- or poly-substituted by halogen, C.sub.1 -C.sub.6 alkoxy, C.sub.3 -C.sub.6 alkenyloxy or by C.sub.3 -C.sub.6 alkynyloxy; or is C.sub.4 -C.sub.6 cycloalkyl, or C.sub.4 -C.sub.6 cycloalkyl that is mono- or poly-substituted by halogen or by C.sub.1 -C.sub.6 alkoxy or may be interrupted by oxygen; or is C.sub.3 -C.sub.6 alkynyl; and R.sub.6 is hydrogen or C.sub.1 -C.sub.6 alkyl.
- 4. A composition according to claim 1, wherein R.sub.6 is hydrogen, C.sub.1 -C.sub.6 alkyl, C.sub.3 -C.sub.6 cycloalkyl or C.sub.2 -C.sub.6 alkynyl; or is C.sub.1 -C.sub.6 alkyl or C.sub.3 -C.sub.6 cycloalkyl each substituted by halogen or by C.sub.1 -C.sub.4 alkoxy; or is C.sub.2 -C.sub.6 alkenyl, or C.sub.2 -C.sub.6 alkenyl substituted by halogen.
- 5. A composition according to claim 1, wherein, in the compound of formula II, A.sub.2 is a radical of the formula ##STR154## wherein R.sub.g and R.sub.h are each independently of the other hydrogen, halogen, C.sub.1 -C.sub.4 alkyl, trifluoromethyl, methoxy, methylthio or COOR.sub.j ; R.sub.c is hydrogen, halogen, C.sub.1 -C.sub.4 alkyl or methoxy; R.sub.d is hydrogen, halogen, nitro, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 alkylthio, C.sub.1 -C.sub.4 alkylsulfinyl, C.sub.1 -C.sub.4 alkylsulfonyl, --COOR.sub.j or --CONR.sub.k R.sub.m ; and R.sub.e is hydrogen, halogen, C.sub.1 -C.sub.4 alkyl, --COOR.sub.j, trifluoromethyl or methoxy; or R.sub.d and R.sub.e together form a C.sub.3 - or C.sub.4 -alkylene bridge; R.sub.f is hydrogen, halogen or C.sub.1 -C.sub.4 alkyl; R.sub.j, R.sub.k and R.sub.m are each independently of the others hydrogen or C.sub.1 -C.sub.4 alkyl; or R.sub.k and R.sub.m together form a C.sub.4 -C.sub.6 alkylene bridge, or a C.sub.4 -C.sub.6 alkylene bridge interrupted by oxygen, NH or by --N(C.sub.1 -C.sub.4 alkyl)--.
- 6. A composition according to claim 5, wherein, in the compound of formula II, R.sub.c, R.sub.d, R.sub.e, R.sub.g and R.sub.h are each independently of the others hydrogen, C.sub.1 -C.sub.4 alkyl or methoxy.
- 7. A composition according to claim 1, wherein, in the compound of formula II, each of R.sub.10 and R.sub.11 is hydrogen.
- 8. A composition according to claim 1, wherein, in the compound of formula II, each of R.sub.9, R.sub.10 and R.sub.11 is hydrogen.
- 9. A composition according to claim 1, wherein the pyridylsulfonylurea of formula I is a compound of formula Ia ##STR155##
- 10. A composition according to claim 9, wherein R is hydrogen.
- 11. A composition according to claim 10, wherein each of R and R.sub.1 is hydrogen and A is the group ##STR156## or --SO.sub.2 --C.sub.1 -C.sub.4 alkyl.
- 12. A composition according to claim 9, wherein A is --X--R.sub.3.
- 13. A composition according to claim 9, wherein A is --N--(R.sub.4)R.sub.5.
- 14. A composition according to claim 9, wherein R.sub.5 is C(O)R.sub.6.
- 15. A composition according to claim 9, wherein each of R and R.sub.1 is hydrogen and A is difluoromethoxy or the group ##STR157##
- 16. A composition according to claim 9, wherein the sulfamoylphenylurea of formula II is a compound of formula IIf ##STR158## and A.sub.3 is the group ##STR159##
- 17. A composition according to claim 16, wherein, in the compound of formula IIf, each of R.sub.8 and R.sub.9 is hydrogen or methyl.
- 18. A composition according to claim 9, which comprises as compound of formula II a compound of formula IIa ##STR160## or of formula IIb ##STR161## or of formula IIc ##STR162## or of formula IId ##STR163## or of formula IIe ##STR164##
- 19. A compound of the formula Ib ##STR165## wherein R is hydrogen, halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy or C.sub.1 -C.sub.4 alkylthio, or is C.sub.1 -C.sub.4 alkyl mono- or poly-substituted by halogen; R.sub.1 is hydrogen or methyl; R.sub.2 is methyl or methoxy; R.sub.4 is hydrogen, C.sub.1 -C.sub.6 alkyl, or C.sub.1 -C.sub.6 alkyl that is mono- or poly-substituted by halogen, C.sub.1 -C.sub.6 alkoxy, C.sub.3 -C.sub.6 alkenyloxy, C.sub.3 -C.sub.6 alkynyloxy or by C.sub.1 -C.sub.6 alkylthio; R.sub.6 is hydrogen, C.sub.1 -C.sub.6 alkyl, C.sub.3 -C.sub.6 cycloalkyl or C.sub.2 -C.sub.6 alkynyl; or is C.sub.1 -C.sub.6 alkyl or C.sub.3 -C.sub.6 cycloalkyl each substituted by halogen or by C.sub.1 -C.sub.4 alkoxy; or is C.sub.2 -C.sub.6 alkenyl, or C.sub.2 -C.sub.6 alkenyl substituted by halogen; or is phenyl, benzyl, naphthyl or OR.sub.12, or phenyl, benzyl or naphthyl each substituted by halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 - C.sub.4 haloalkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 haloalkoxy, C.sub.3 -C.sub.6 alkenyloxy, C.sub.3 -C.sub.6 alkynyloxy, nitro, cyano, COOR.sub.13, NR.sub.15 R.sub.16, C(O)NR.sub.17 R.sub.18, X.sub.1 R.sub.20, SO.sub.2 NR.sub.21 R.sub.22 or by X.sub.2 R.sub.23 ; R.sub.12 is C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 haloalkyl, oxetan-3-yl, or C.sub.4 -C.sub.6 cycloalkyl, which may for its part be substituted by halogen, C.sub.1 -C.sub.4 alkyl or by C.sub.1 -C.sub.4 alkoxy; or is phenyl, benzyl or naphthyl, or phenyl, benzyl or naphthyl each substituted by C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 haloalkoxy, C.sub.1 -C.sub.4 alkylthio, C.sub.1 -C.sub.4 haloalkylthio, C.sub.1 -C.sub.4 alkylsulfonyl, C.sub.1 -C.sub.4 alkylsulfinyl, nitro, cyano, COOR.sub.27, NR.sub.25 R.sub.26, CONR.sub.28 R.sub.29 or by SO.sub.2 NR.sub.30 R.sub.14 ; or is C.sub.1 -C.sub.6 alkyl substituted by C.sub.1 -C.sub.4 alkoxy, C.sub.3 -C.sub.6 cycloalkyl, cyano, COOR.sub.24 or by CONR.sub.32 R.sub.33 ; or is C.sub.3 -C.sub.6 alkenyl, C.sub.3 -C.sub.6 haloalkenyl, C.sub.3 -C.sub.6 alkynyl, C.sub.3 -C.sub.6 haloalkynyl, X.sub.3 R.sub.35 or X.sub.4 R.sub.36 ; R.sub.13 is hydrogen, C.sub.1 -C.sub.6 alkyl, C.sub.3 -C.sub.6 alkenyl, C.sub.3 -C.sub.6 alkynyl or oxetan-3-yl; R.sub.14, R.sub.15, R.sub.16, R.sub.17, R.sub.18, R.sub.21, R.sub.22, R.sub.25, R.sub.26, R.sub.28, R.sub.29, R.sub.30, R.sub.32 and R.sub.33 are each independently of the others hydrogen, C.sub.1 -C.sub.4 alkyl, C.sub.3 -C.sub.6 alkenyl or C.sub.3 -C.sub.6 alkynyl; or R.sub.15 and R.sub.25 are each independently of the other the groups --C(O)--X.sub.5 --C.sub.1 -C.sub.4 alkyl or --C(O)--C.sub.1 -C.sub.4 alkyl, which may for their part be substituted by halogen; or R.sub.15 and R.sub.16 or R.sub.17 and R.sub.18 or R.sub.21 and R.sub.22 or R.sub.25 and R.sub.26 or R.sub.28 and R.sub.29 or R.sub.30 and R.sub.14 or R.sub.32 and R.sub.33 together form a C.sub.4 -C.sub.5 alkylene chain, which may for its part be interrupted by oxygen or by NR.sub.19, R.sub.19 is hydrogen, C.sub.1 -C.sub.4 alkyl, C.sub.3 -C.sub.6 alkenyl or C.sub.3 -C.sub.6 alkynyl; R.sub.20 and R.sub.35 are each independently of the other C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.4 haloalkyl; R.sub.23 and R.sub.36 are each independently of the other C.sub.1 -C.sub.4 alkyl substituted by COOR34; R.sub.24, R.sub.27 and R.sub.34 are each independently of the other hydrogen or C.sub.1 -C.sub.4 alkyl; X.sub.1 and X.sub.3 are each independently of the other sulfur, SO or SO.sub.2 ; X.sub.2 and X.sub.4 are each independently of the other oxygen or sulfur; X.sub.5 is oxygen or NR.sub.37 ; and R.sub.37 is hydrogen, C.sub.1 -C.sub.4 alkyl, C.sub.3 -C.sub.6 alkenyl or C.sub.3 -C.sub.6 alkynyl.
- 20. A compound according to claim 19, wherein R.sub.6 is hydrogen or C.sub.1 -C.sub.6 alkyl.
- 21. A method of selectively controlling weeds and grasses in crops of useful plants, which comprises treating the crops, their seed or the crop area thereof with an effective amount of a pyridylsulfonylurea herbicide of formula I ##STR166## or an N-oxide or a salt thereof, and a herbicide-antagonistically effective amount of a sulfamoylphenylurea compound of formula II ##STR167## or a salt thereof, simultaneously or independently of one another, wherein R is hydrogen, halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy or C.sub.1 -C.sub.4 alkylthio, or is C.sub.1 -C.sub.4 alkyl mono- or poly-substituted by halogen; R.sub.1 is hydrogen or methyl; R.sub.2 is methyl or methoxy; A is --X--R.sub.3 or --N--(R.sub.4)R.sub.5 ; R.sub.3 is C.sub.1 -C.sub.6 alkyl, or C.sub.1 -C.sub.6 alkyl that is mono- or poly-substituted by halogen, C.sub.1 -C.sub.6 alkoxy, C.sub.3 -C.sub.6 -alkenyloxy C.sub.3 -C.sub.6 alkynyloxy or by C.sub.3 -C.sub.6 cycloalkyl, which may for its part be interrupted by oxygen; or is C.sub.3 -C.sub.6 alkenyl, or C.sub.3 -C.sub.6 alkenyl that is mono- or poly-substituted by halogen, C.sub.1 -C.sub.6 alkoxy, C.sub.3 -C.sub.6 alkenyloxy or by C.sub.3 -C.sub.6 alkynyloxy; or is C.sub.4 -C.sub.6 cycloalkyl, or C.sub.4 -C.sub.6 cycloalkyl that is mono- or poly-substituted by halogen or by C.sub.1 -C.sub.6 alkoxy; or is C.sub.3 -C.sub.6 cycloalkyl that is interrupted by oxygen; or is C.sub.3 -C.sub.6 alkynyl; X is oxygen or S(O).sub.n ; n is0, 1 or2; R.sub.4 is hydrogen, C.sub.1 -C.sub.6 alkyl, or C.sub.1 -C.sub.6 alkyl that is mono- or poly-substituted by halogen, C.sub.1 -C.sub.6 alkoxy, C.sub.3 -C.sub.6 alkenyloxy, C.sub.3 -C.sub.6 alkynyloxy or by C.sub.1 -C.sub.6 alkylthio; R.sub.5 is hydrogen, C.sub.1 -C.sub.6 alkyl, or C.sub.1 -C.sub.6 alkyl that is mono- or poly-substituted by halogen, C.sub.1 -C.sub.6 alkoxy, C.sub.3 -C.sub.6 alkenyloxy, C.sub.3 -C.sub.6 alkynyloxy or by C.sub.1 -C.sub.6 alkylthio, or is C(O)R.sub.6 ; and R.sub.6 is hydrogen, C.sub.1 -C.sub.6 alkyl, C.sub.3 -C.sub.6 cycloalkyl or C.sub.2 -C.sub.6 alkynyl; or is C.sub.1 -C.sub.6 alkyl or C.sub.3 -C.sub.6 cycloalkyl each substituted by halogen or by C.sub.1 -C.sub.4 alkoxy; or is C.sub.2 -C.sub.6 alkenyl, or C.sub.2 -C.sub.6 alkenyl substituted by halogen; or is phenyl, benzyl, naphthyl or OR.sub.12, or phenyl, benzyl or naphthyl each substituted by halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 haloalkoxy, C.sub.3 -C.sub.6 alkenyloxy, C.sub.3 -C.sub.6 alkynyloxy, nitro, cyano, COOR.sub.13, NR.sub.15 R.sub.16, C(O)NR.sub.17 R.sub.18, X.sub.1 R.sub.20, SO.sub.2 NR.sub.21 R.sub.22 or by X.sub.2 R.sub.23 ; R.sub.12 is C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 haloalkyl, oxetan-3-yl, or C.sub.4 -C.sub.6 cycloalkyl, which may for its part be substituted by halogen, C.sub.1 -C.sub.4 alkyl or by C.sub.1 -C.sub.4 alkoxy; or is phenyl, benzyl or naphthyl, or phenyl, benzyl or naphthyl each substituted by C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.6 haloalkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 haloalkoxy, C.sub.1 -C.sub.4 C.sub.1 -C.sub.4 haloalkylthio, C.sub.1 -C.sub.4 alkylsulfonyl, C.sub.1 -C.sub.4 alkylsulfinyl, nitro, cyano, COOR.sub.27, NR.sub.25 R.sub.26, CONR.sub.28 R.sub.29 or by SO.sub.2 NR.sub.30 R.sub.14 ; or is C.sub.1 -C.sub.6 alkyl substituted by C.sub.1 -C.sub.4 alkoxy, C.sub.3 -C.sub.6 -cycloalkyl cyano, COOR.sub.24 or by CONR.sub.32 R.sub.33 ; or is C.sub.3 -C.sub.6 alkenyl, C.sub.3 -C.sub.6 haloalkenyl, C.sub.3 -C.sub.6 alkynyl, C.sub.3 -C.sub.6 haloalkynyl, X.sub.3 R.sub.35 or X.sub.4 R.sub.36 ; R.sub.13 is hydrogen, C.sub.1 -C.sub.6 alkyl, C.sub.3 -C.sub.6 alkenyl, C.sub.3 -C.sub.6 alkynyl or oxetan-3-yl; R.sub.14, R.sub.15, R.sub.16, R.sub.17, R.sub.18, R.sub.21, R.sub.22, R.sub.25, R.sub.26, R.sub.28, R.sub.29, R.sub.30, R.sub.32 and R.sub.33 are each independently of the others hydrogen, C.sub.1 -C.sub.4 alkyl, C.sub.3 -C.sub.6 alkenyl or C.sub.3 -C.sub.6 alkynyl; or R.sub.15 and R.sub.25 are each independently of the other the groups --C(O)--X.sub.5 --C.sub.1 -C.sub.4 alkyl or --C(O)--C.sub.1 -C.sub.4 alkyl, which may for their part be substituted by halogen; or R.sub.15 and R.sub.16 or R.sub.17 and R.sub.18 or R.sub.21 and R.sub.22 or R.sub.25 and R.sub.26 or R.sub.28 and R.sub.29 or R.sub.30 and R.sub.14 or R.sub.32 and R.sub.33 together form a C.sub.4 -C.sub.8 alkylene chain, which may for its part be interrupted by oxygen or by NR.sub.19, R.sub.19 is hydrogen, C.sub.1 -C.sub.4 alkyl, C.sub.3 -C.sub.6 alkenyl or C.sub.3 -C.sub.6 alkynyl; R.sub.20 and R.sub.35 are each independently of the other C.sub.1 -C.sub.6 alkyl or C.sub.1 -C.sub.4 haloalkyl; R.sub.23 and R.sub.36 are each independently of the other C.sub.1 -C.sub.4 alkyl substituted by COOR.sub.34 ; R.sub.24, R.sub.27 and R.sub.34 are each independently of the other hydrogen or C.sub.1 -C.sub.4 alkyl; X.sub.1 and X.sub.3 are each independently of the other sulfur, SO or SO.sub.2 ; X.sub.2 and X.sub.4 are each independently of the other oxygen or sulfur; X.sub.5 is oxygen or NR.sub.37 ; R.sub.37 is hydrogen, C.sub.1 -C.sub.4 alkyl, C.sub.3 -C.sub.6 alkenyl or C.sub.3 -C.sub.6 alkynyl; A.sub.2 is a radical from the group ##STR168## R.sub.7 and R.sub.8 are each independently of the other hydrogen, C.sub.1 -C.sub.8 alkyl, C.sub.3 -C.sub.8 cycloalkyl, C.sub.3 -C.sub.6 alkenyl, C.sub.3 -C.sub.6 alkynyl or ##STR169## or are C.sub.1 -C.sub.4 alkyl substituted by C.sub.1 -C.sub.4 alkoxy or by ##STR170## R.sub.7 and R.sub.8 together form a C.sub.4 -C.sub.6 alkylene bridge, or a C.sub.4 -C.sub.6 alkylene bridge interrupted by oxygen, sulfur, SO, SO.sub.2, NH or by --N(C.sub.1 -C.sub.4 alkyl)--; R.sub.9 is hydrogen or C.sub.1 -C.sub.4 alkyl; R.sub.10 and R.sub.11 are each independently of the other hydrogen, halogen, cyano, nitro, trifluoromethyl, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 alkylthio, C.sub.1 -C.sub.4 alkylsulfinyl, C.sub.1 -C.sub.4 alkylsulfonyl, --COOR.sub.j, CONR.sub.k R.sub.m, --COR.sub.n, --SO.sub.2 NR.sub.k R.sub.m or --OSO.sub.2 -C.sub.1 -C.sub.4 alkyl; or R.sub.10 and R.sub.11 together form a C.sub.3 -C.sub.4 alkylene bridge, which may be substituted by halogen or by C.sub.1 -C.sub.4 alkyl, or a C.sub.3 -C.sub.4 alkenylene bridge, which may be substituted by halogen or by C.sub.3 - or C.sub.4 -alkyl, or a butadienylene bridge, which may be substituted by halogen or by C.sub.1 -C.sub.4 alkyl, and R.sub.g and R.sub.h are each independently of the other hydrogen, halogen, C.sub.1 -C.sub.4 alkyl, trifluoromethyl, methoxy, methylthio or --COOR.sub.j ; R.sub.c is hydrogen, halogen, C.sub.1 -C.sub.4 alkyl or methoxy; R.sub.d is hydrogen, halogen, nitro, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 alkylthio, C.sub.1 -C.sub.4 alkylsulfinyl, C.sub.1 -C.sub.4 alkylsulfonyl, --COOR.sub.j or --CONR.sub.k R.sub.m ; and R.sub.e is hydrogen, halogen, halo-C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkyl, --COOR.sub.j, trifluoromethyl or methoxy; or R.sub.d and R.sub.e together form a C.sub.3 -C.sub.4 alkylene bridge; R.sub.f is hydrogen, halogen or C.sub.1 -C.sub.4 alkyl; R.sub.x and R.sub.y are each independently of the other hydrogen, halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 alkylthio, --COOR.sub.17, trifluoromethyl, nitro or cyano; R.sub.17 is hydrogen, C.sub.1 -C.sub.10 alkyl, C.sub.1 -C.sub.4 alkoxy-C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkylthio-C.sub.1 -C.sub.4 alkyl, di-C.sub.1 -C.sub.4 alkylamino-C.sub.1 -C.sub.4 alkyl, halo-C.sub.1 -C.sub.8 alkyl, C.sub.2 -C.sub.8 alkenyl, halo-C.sub.2 -C.sub.8 alkenyl, C.sub.3 -C.sub.8 alkynyl, C.sub.3 -C.sub.7 cycloalkyl, halo-C.sub.3 -C.sub.7 cycloalkyl, C.sub.1 -C.sub.8 alkylcarbonyl, allylcarbonyl, C.sub.3 -C.sub.7 cycloalkylcarbonyl, benzoyl that is unsubstituted or mono- to tri-substituted in the phenyl ring by the same or different substituents selected from halogen, C.sub.1 -C.sub.4 alkyl, halo-C.sub.1 -C.sub.4 alkyl, halo-C.sub.1 -C.sub.4 alkoxy and C.sub.1 -C.sub.4 alkoxy; or is furoyl or thienyl; or is C.sub.1 -C.sub.4 alkyl substituted by phenyl, halophenyl, C.sub.1 -C.sub.4 alkylphenyl, C.sub.1 -C.sub.4 -alkoxyphenyl, halo-C.sub.1 -C.sub.4 alkylphenyl, halo-C.sub.1 -C.sub.4 alkoxyphenyl, C.sub.1 -C.sub.6 alkoxycarbonyl, C.sub.1 -C.sub.4 alkoxy-C.sub.1 -C.sub.8 alkoxycarbonyl, C.sub.3 -C.sub.8 alkenyloxycarbonyl, C.sub.3 -C.sub.8 alkynyloxycarbonyl, C.sub.1 -C.sub.8 alkylthiocarbonyl, C.sub.3 -C.sub.8 alkenylthiocarbonyl, C.sub.3 -C.sub.8 alkynylthiocarbonyl, carbamoyl, mono-C.sub.1 -C.sub.4 alkylaminocarbonyl or by di-C.sub.1 -C.sub.4 alkylaminocarbonyl; or is phenylaminocarbonyl that is unsubstituted or mono- to tri-substituted in the phenyl ring by the same or different substituents selected from halogen, C.sub.1 -C.sub.4 alkyl, halo-C.sub.1 -C.sub.4 alkyl, halo-C.sub.1 -C.sub.4 alkoxy and C.sub.1 -C.sub.4 alkoxy or that is mono-substitute in the phenyl ring by cyano or by nitro; or is dioxolan-2-yl that is unsubstituted or substituted by one or two C.sub.1 -C.sub.4 alkyl radicals; or is dioxan-2-yl that is unsubstituted or substituted by one or two C.sub.1 -C.sub.4 alkyl radicals; or is C.sub.1 -C.sub.4 alkyl that is substituted by cyano, nitro, carboxy or by C.sub.1 -C.sub.8 alkylthio-C.sub.1 -C.sub.8 alkoxycarbonyl; R.sub.j, R.sub.k and R.sub.m are each independently of the others hydrogen or C.sub.1 -C.sub.4 alkyl; or R.sub.k and R.sub.m together form a C.sub.4 -C.sub.6 alkylene bridge, or a C.sub.4 -C.sub.6 alkylene bridge interrupted by oxygen, NH or by --N(C.sub.1 -C.sub.4 alkyl)--; and R.sub.n is C.sub.1 -C.sub.4 alkyl, phenyl, or phenyl substituted by halogen, C.sub.1 -C.sub.4 alkyl, methoxy, nitro or by trifluoromethyl.
- 22. A method according to claim 21, wherein the crops or the crop area is treated with from 0.001 to 2 kg/ha of the pyridylsulfonylurea herbicide of formula I or the N-oxide or salt thereof and from 0.005 to 0.5 kg/ha of the sulfamoylphenylurea compound of formula II or the salt thereof.
- 23. A method according to claim 21 wherein the crops of useful plants are maize or sugar cane.
Priority Claims (4)
Number |
Date |
Country |
Kind |
3697/92 |
Dec 1992 |
CHX |
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213/93 |
Jan 1993 |
CHX |
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397/93 |
Feb 1993 |
CHX |
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906/93 |
Mar 1993 |
CHX |
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Parent Case Info
This is a continuation of Ser. No. 291,319, filed Aug. 16, 1994, abandoned, which is a continuation of Ser. No. 157,870, filed Nov. 24, 1993, abandoned.
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Continuations (2)
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Date |
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Parent |
291319 |
Aug 1994 |
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Parent |
157870 |
Nov 1993 |
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