Herbicidal compositions with substituted phenylsulfonylureas for controlling weeds in rice
View Patent ↗Herbicidal compositions comprising A) at least one herbicidally active compound from the group of the substituted phenylsulfonylureas of the formula I and their agriculturally accepted, i.e. acceptable and compatible, salts in which R 1 is (C 1 -C 8 )-alkyl, (C 3 -C 4 ) -alkenyl, (C 3 -C 4 )-alkynyl or (C 1 -C 4 )-alkyl, which is mono- to tetrasubstituted by radicals from the group consisting of halogen and (C 1 -C 2 )-alkoxy; R 2 is I or CH 2 NHSO 2 CH 3 ; R 3 is methyl or methoxy; and Z is N or CH; and B) at least one herbicidally active compound from the group of the compounds consisting of Ba) herbicides which are selective in rice, mainly against grasses, Bb) herbicides which are selective in rice, mainly against dicotyledonous harmful plants and cyperaceae, Bc) herbicides which are selective in rice, mainly against cyperaceae, and Bd) herbicides which are selective in rice, mainly against grasses an dicotyledenous harmful plants and also against harmful cyperaceae plants.
1. A herbicidal composition, comprising a synergistic combination of A) at least one synergistically herbicidally active compound from the group of the substituted phenylsulfonylureas of the formula I and their agriculturally accepted, i.e. acceptable and compatible, salts
in which
R 1 is (C 1 -C 8 )-alkyl, (C 3 -C 4 )-alkenyl, (C 3 -C 4 )-alkynyl or (C 1 -C 4 )-alkyl, which is mono- to tetrasubstituted by radicals from the group consisting of halogen and (C 1 -C 2 )-alkoxy;
R 2 is I or CH 2 NHSO 2 CH 3 when
Z is CH
or
R 2 is CH 2 NHSO 2 CH 3 when
Z is N
R 3 is methyl or methoxy
and
B) at least one synergistically herbicidally active compound from the group of the compounds consisting of
Ba) herbicides which are selective in rice, mainly against grasses, comprising
in which
R 1 is halogen, (C 1 -C 4 )-alkoxy, (C 1 -C 4 )-alkyl, (C 1 -C 4 )-haloalkyl, —NO 2 , —CN or S(O) n R 10 ;
R 2 and R 3 independently of one another are hydrogen, halogen, (C 1 -C 4 )-alkyl, (C 1 -C 4 )-alkoxy, (C 1 -C 4 )-haloalkoxy, (C 1 -C 4 )-haloalkyl, —NO 2 , —CN or S(O) m R 11 , —NR 12 R 13 , —NR 14 —CO—R 15 ;
R 4 is hydrogen, (C 1 -C 4 )-alkyl or —CO—O—(C 1 -C 4 )-alkyl;
R 5 , R 6 , R 7 , R 8 , R 9 independently of one another are hydrogen or (C 1 -C 4 )-alkyl or —CO—R 16 ;
R 10 is (C 1 -C 4 )-alkyl, (C 1 -C 4 )-haloalkyl or (C 1 -C 4 )-alkoxy;
R 11 is (C 1 -C 4 )-alkyl, (C 1 -C 4 )-haloalkyl, phenyl, benzyl or —NR 17 R 18 ;
R 12 and R 13 independently or one another are hydrogen or (C 1 -C 4 )-alkyl;
R 14 is hydrogen or (C 1 -C 4 )-alkyl;
R 15 is (C 1 -C 4 )-alkyl;
R 16 is hydrogen, (C 1 -C 4 )-alkyl, (C 1 -C 4 )-haloalkyl or (C 1 -C 4 )-alkoxy;
R 17 and R 18 independently of one another are hydrogen or (C 1 -C 4 )-alkyl; and
n and m independently or one another are 0, 1 or 2,
B15) cycloxydim
Bb) herbicides which are selective in rice, mainly against dicotyledonous harmful plants and cyperaceae, comprising
in which
R 1 is (C 1 -C 4 )-alkyl,
R 2 is (C 1 -C 4 )-alkyl, (C 1 -C 4 )-alkylthio or (C 1 -C 4 )-alkoxy, each radical of which may be substituted by one or more halogen atoms, or
R 1 and R 2 together from the group (CH 2 ) m where m=3 or 4
R 3 is hydrogen or halogen,
R 4 is hydrogen or (C 1 -C 4 )-alkyl,
R 5 is hydrogen, nitro, cyano or one of the groups —COOR 7 , —C(═X)NR 7 R 8 or —C(═X)R 10 ,
R 6 is hydrogen, halogen, cyano, (C 1 -C 4 )-alkyl, (C 1 -C 4 )-alkylthio or —NR 11 R 12 ,
R 7 and R 8 are identical or different and are hydrogen or (C 1 -C 4 )-alkyl, or
R 7 and R 8 are identical with the nitrogen to which they are attached form a saturated 5- or 6-membered carbocyclic ring,
R 10 is hydrogen or (C 1 -C 4 )-alkyl, where the latter may be unsubstituted or substituted by one or more halogen atoms, and
R 11 and R 12 are identical or different and are hydrogen, (C 1 -C 4 )-alkyl or (C 1 -C 4 )-alkoxycarbonyl, where
R 11 and R 12 together with the nitrogen to which they are attached may form a 3-, 5- or 6-membered carbocyclic or aromatic ring in which one carbon atom may optionally be replaced by an oxygen atom,
Bc) herbicides which are selective in rice, mainly against cyperaceae, comprising
and
Bd) herbicides which are selective in rice, mainly against grasses and dicotyledonous harmful plants and also against harmful cyperaceae plants, comprising
in which
a) R 1 is ethoxy, propoxy or isopropoxy and R 2 is halogen, NO 2 , CF 3 , CN, (C 1 -C 4 )-alkyl, (C 1 -C 4 )-alkoxy, (C 1 -C 4 )-alkylthio or ((C 1 -C 4 )-alkoxy)carbonyl and n is 0, 1, 2, or 3 or
b) R 1 is saturated or unsaturated (C 1 -C 8 )-alkoxy, which is substituted by halogen, saturated or unsaturated (C 1 -C 6 )-alkoxy, a radical of the formula ((C 1 -C 6 )-alkyl)-S—, ((C 1 -C 6 )-alkyl)-SO—, ((C 1 -C 6 )-alkyl)-SO 2 —, ((C 1 -C 6 )-alkyl)-O—CO—, NO 2 , CN or phenyl; furthermore (C 2 -C 8 )-alkenyloxy or -alkynyloxy and R 2 is saturated or unsaturated (C 1 -C 8 )-alkyl, phenyl, phenoxy, (C 1 -C 4 )-alkoxy)carbonyl, where all of the abovementioned radicals R 2 may be substituted by halogen, NO 2 , (C 1 -C 4 )-alkylsulfonyl or -sulfinyl and n is 0, 1, 2 or 3 or
c) R 1 is (C 1 -C 8 )-alkoxy and R 2 is (C 2 -C 8 )-alkenyl or —alkynyl, phenyl, phenoxy, where the radicals mentioned above for R 2 are unsubstituted or substituted by halogen, (C 1 -C 4 )-alkoxy or (C 1 -C 4 )-alkylthio, or (C 1 -C 4 )-alkylsulfonyl or -sulfinyl and n is 1, 2 or 3 or
d) R 1 is, in each case in the 2-position on the phenyl radical, halogen, methoxy, ethyl or propyl, R 2 is ((C 1 -C 4 )-alkoxy)carbonyl in the 6-position on the phenyl radical and n=1 and in all cases a) to d)
R 3 is hydrogen, saturated or unsaturated (C 1 -C 8 )-alkyl or (C 1 -C 4 )-alkoxy,
R 4 ,R 5 is independently of one another are hydrogen, halogen, (C 1 -C 4 )-alkyl, (C 1 -C 4 )-alkoxy, (C 1 -C 4 )-alkylthio, where the three last-mentioned radicals are unsubstituted or substituted by halogen, (C 1 -C 4 )-alkoxy or (C 1 -C 4 )-alkylthio,
Y is O or S and
E is CH or N,
with the proviso that
ii) compositions which comprise
A″) at least one compound from the group of the substituted phenylsulfonylureas of the formula I″ and their agriculturally accepted salts
in which
R 1 is (C 1 -C)-alkyl, (C 3 -C 4 )-alkenyl, (C 3 -C 4 )-alkyl or (C 1 -C 4 )-alkyl, which is mono- to tetrasubstituted by radicals from the group consisting of halogen and (C 1 -C 2 )-alkoxy
in combination with
B″) fenoxaprop, pendimethalin, mecoprop, MCPA, 2,4-D,dicamba, a compound of the abovementioned formula III, bentaxon, ioxynil, metosulam, or metsulfuron as the only herbicidally active compounds,
are excluded.
2. The herbicidal composition as claimed in claim 1 wherein the herbicide of the formula (I) or its salts, R 1 is methyl.
3. The herbicidal composition as claimed is claim 1 , wherein,
in the herbicide of the formula (I) or its salt
R 1 is methyl, ethyl, n- or isopropyl, n-, tert-, 2-butyl isobutyl, n-pentyl, isopentyl, n-hexyl, isohexyl, 1,3-dimethylbutyl, n-heptyl, 1-methylhexyl or 1,4-dimethylpentyl;
R 2 is CH 2 NHSO 2 CH 3 ;
R 3 is methoxy; and
Z is CH.
4. The herbicidal composition as claimed in claim 3 , wherein
in the herbicide of the formula (I) or its salts R 1 is methyl.
5. The herbicide composition as claimed in claim 4 , wherein
the composition comprises the compounds A2)
6. The herbicidal composition as claimed in claim 1 , wherein
the salt of the herbicide of the formula (I) is formed by replacing the hydrogen of the —SO 2 —NH— group by a cation from the group of the alkali metals, alkaline earth metals and ammonium.
7. The herbicidal composition as claimed in claim 6 , wherein the cation is sodium.
8. The herbicidal composition as claimed in claim 1 , wherein
the composition comprises, as herbicides of group 3, one or more herbicides which are selective in rice, mainly against grasses that are selected from the group consisting of chloracetanilides, thiocarbamates, quinolinecarboxylic acids, cyclohexanediones, cyclohexanedione oximes, NBA061, organophosphorus compounds, 2-(4-aryloxyphenoxy)propionic acids, or their esters, ureas, pyridincarbothioates, butyramides, menthyl benzyl ethers and triazoles.
9. The herbicidal composition as claimed in claim 8 wherein
the composition comprises, as herbicides of group B, at least on herbicide selected from the group consisting of
in which
R 1 is halogen (C 1 -C 4 )-alkoxy, (C 1 -C 4 )-alkyl, (C 1 -C 4 )-haloalkyl, —NO 2 , —CN or S(O) n R 10 ;
R 2 and R 3 independently of one another are hydrogen, halogen, (C 1 -C 4 )-alkyl, (C 1 -C 4 )-alkoxy, (C 1 -C 4 )-haloalkoxy, (C 1 -C 4 )-haloalkyl, —NO 2 , —CN or S(O) m R 11 , —NR 12 R 13 , —NR 14 —CO—R 15 ;
R 4 is hydrogen, (C 1 -C 4 )-alkyl or —CO—O—(C 1 -C 4 )-alkyl;
R 5 , R 6 , R 7 , R 8 , R 9 independently of one another are hydrogen or (C 1 -C 4 )-alkyl or —CO—R 16 ;
R 10 is (C 1 -C 4 )-alkyl, (C 1 -C 4 )-haloalkyl, phenyl, benzyl or —NR 17 R 18 ;
R 12 and R 13 independently of one another are hydrogen or (C 1 -C 4 )-alkyl;
R 14 is hydrogen or (C 1 -C 4 )-alkyl;
R 15 is (C 1 -C 4 )-alkyl;
R 16 is hydrogen, (C 1 -C 4 )-alkyl, (C 1 -C 4 )-haloalkyl or (C 1 -C 4 )-alkoxy;
R 17 and R 18 independently of one another are hydrogen or (C 1 -C 4 )-alkyl; and
n and m independently of one another are 0, 1 or 2,
10. The herbicidal composition as claimed in claim 5 , wherein
the composition comprises, as herbicides of group B, at least one herbicidal selected from the group consisting of anilofos, fenoxaprop, fenoxaprop-P, butachlor and propanil.
11. The herbicidal composition as claimed in claim 1 , wherein
the composition comprises, as herbicides of group B, one or more herbicides which are selective in rice, mainly against dicotyledonous harmful plants and cyperaceae, that are selected from the group consisting of aryloxyalkylcarboxylic acids, dicamba, nitrodiphenylethers, azoles, pyrazoles, sulfonylureas, hydroxybenzonitriles, pyridincarboxylic acids and triazoles.
12. The herbicidal composition as claimed in claim 10 wherein
the composition comprises, as herbicides of group B, at least one herbicide selected from the group consisting of
in which
R 1 is (C 1 -C 4 )-alkyl,
R 2 is (C 1 -C 4 )-alkyl, (C 1 -C 4 )-alkylthio or (C 1 -C 4 )-alkoxy, each radical of which may be substituted by one or more halogen atoms, or
R 1 and R 2 together form the group (CH 2 ) m where m=3 or 4,
R 3 is hydrogen or halogen,
R 4 is hydrogen or (C 1 -C 4 )-alkyl,
R 5 is hydrogen, nitro, cyano or one of the groups —COOR 7 , —C(═X)NR 7 R 8 or —C(═X)R 10 ,
R 6 is hydrogen, cyano, (C 1 -C 4 )-alkyl, (C 1 -C 4 )-alkylthio or —NR 11 R 12 ,
R 7 and R 6 are identical or different and are hydrogen or (C 1 -C 4 )-alkyl, or
R 7 and R 6 together with the nitrogen to which they are attached form a saturated 5- or 6-membered carbocyclic ring,
R 10 is hydrogen or (C 1 -C 4 )-alkyl, where the latter may be unsubstituted or substituted by one or more halogen atoms, and
R 11 and R 12 are identical or different and are hydrogen, (C 1 -C 4 )-alkyl or (C 1 -C 4 )-alkoxycarbonyl, where
R 11 and R 12 together with the nitrogen to which they are attached may form a 3-, 5-, or 6-membered carbocyclic or aromatic ring in which one carbon atom may optionally be replaced by and oxygen atom,
13. The herbicidal composition as claimed in claim one or more of the preceding claims 5 , wherein,
the composition comprises, at least one herbicide selected from the group consisting of 2,4-D, MCPA, mecoprop and dicamba.
14. The herbicidal composition as claimed in claim 1 , wherein
the composition comprises, as herbicides of group B, one or more herbicides which are selective in rice, mainly against cyperaceae, that are selected from the group consisting of bentazon, triclopyr, benzofuranyl compounds and ureas.
15. The herbicidal composition as claimed in claim 14 , wherein
the composition comprises, as herbicides of group B, at least one herbicide selected from the group consisting of
16. The herbicidal composition as claimed in claim 5 , wherein
the composition comprises, as herbicides of group B, at least one herbicide selected from the group consisting of bentazon and daimuron.
17. The herbicidal composition as claimed in claim 1 , wherein,
the composition comprises, as herbicides of group B, one or more herbicides which are selective in rice against grasses and dicotyledonous harmful plants on cyperacae that are selected from the group consisting of 2,6-dinitroanilines, pyrazoles, pyrimidinyloxobenzoic acids, oxadiazoles, anilides, diphenyl ethers, alkylcarboxylic acids, sulfonylureas given in formula I, 1,3,5-triazines, pyridines, organophosphorus compounds, pentoxazon, indanofan, LGC40863 and MY100.
18. The herbicidal composition as claimed in claim 17 , wherein
the composition comprises, as herbicides of group B, at least one herbicide selected from the group consisting of
in which
a) R 1 is ethoxy, propoxy or isopropoxy and R 2 is halogen, No 2 , CF 3 , CN, (C 1 -C 4 )-alkyl, (C 1 -C 4 )-alkoxy, (C 1 -C 4 )-alkylthio or ((C 1 -C 4 )-alkoxy)carbonyl and n is 0, 1, 2, or 3 or
b) R 1 is saturated or unsaturated (C 1 -C 6 )-alkoxy, which is substituted by halogen, saturated or unsaturated (C 1 14 C 6 )-alkoxy, a radical of the formula ((C 1 -C 6 )-alkyl)-S—, ((C 1 -C 6 )-alkyl)-O—CO—, NO 2 , CN or phenyl; furthermore (C 2 -C 8 )-alkenyloxy or -alkynyloxy and R 2 is saturated or unsaturated (C 1 -C 8 )-alkyl, phenyl, phenoxy, (C 1 -C 4 )-alkoxy, (C 1 -C 4 )-alkylthio, ((C 1 -C 4 )-alkoxy)carbonyl, where all of the abovementioned radicals R 2 may be substituted by halogen, (C 1 -C 4 )-alkoxy or (C 1 -C 4 )-alkylthio, or halogen, NO 2 , (C 1 -C 4 )-alkylsulfonyl or -sulfinyl and n is 0, 1, 2 or 3 or
c) R 1 is (C 1 -C 8 )-alkoxy and R 2 is (C 2 -C 8 )-alkenyl or -alkynyl, phenyl, phenoxy, where the radicals mentioned above for R 2 are unsubstituted or substituted by halogen, (C 1 -C 4 )-alkoxy or (C 1 -C 4 )-alkylthio, or (C 1 -C 4 )-alkylsulfonyl or -sulfinyl and n is 1, 2, or 3 or
d) R 1 is, in each case in the 2-position on the phenyl radical, halogen, methoxy, ethyl or propyl, R 2 is ((C 1 -C 4 )-alkoxy)carbonyl in the 6-position on the phenyl radical and n=1
and in all cases a) to d)
R 4 , R 5 independent of one another are hydrogen, halogen, (C 1 -C 4 )-alkylthio, where the three last-mentioned radicals are unsubstituted or substituted by halogen, (C 1 -C 4 )-alkoxy or(C 1 -C 4 )-alkylthio,
Y is O or S and
E is CH or N,
19. The herbicidal composition as claimed in claim 1 , wherein
the composition comprises the compounds of the formula I or their salts (group A compounds) and the compound from group B in a weight ratio of from 1:20,000 to 200:1.
20. The herbicidal composition as claimed in claim 19 , wherein
the weight ratio is from 1:8000 to 100:1.
21. The herbicidal composition as claimed in claim 19 , wherein
the weight ratio is from 1:4000 to 50:1.
22. The composition as claimed in claim 1 , wherein
the composition comprises from 0.1 to 99% by weight of the active compounds A and B, in addition to customary formulation auxiliaries.
23. A herbicidal composition, comprising a synergistic amount of B) at least on herbicidally active compound from the group of the substituted phenylsulfonylureas of the formula I and their agriculturally accepted, i.e., acceptable and compatible, salts
in which
R 1 is (C 1 -C 8 )-alkyl, (C 3 -C 4 )-alkenyl, (C 3 -C 4 )-alkynyl or(C 1 -C 4 )-alkyl, which is mono- to tetrasubstituted by radicals from the group consisting of halogen and (C 1 -C 2 )-alkoxy;
R 2 is I or (H 2 NHSO 2 CH 3 ) when
Z CH
or
R 2 is CH 2 NHSO 2 CH 3 when
Z is N
R 3 is methyl or methoxy,
in combination with
at least one herbicidally active compound from the group of the compounds B consisting of
B1) butachlor,
B2) butenachlor,
B3) thenylchlor
B4) pretilachlor
B5) mefenacet,
B5a) Bay FOE 5043
B6) naproanilid,
B7) propanil,
B8) etonenzanid,
B9) dimepiperate
B10) molinate,
B11) thiobencarb
B12) pyributicarb,
B13) quinclorac,
B14a) sulcotrione
B15) cycloxydim
B16) sethoxydim
B17) NBA 061
B18) piperophos,
B19) anilofos
B21) haloxyfop,
B22) cyhalofop,
B23) JC-940,
B24) dithiopyr,
B25) bromobutide,
B26) cinmethylin,
B27) CH-900,
B32) acifluorfen
B34) chlorimuron,
B37) picloram,
B38) carfentrazon,
B40) triclopyr,
B41) benfuresate,
B42) daimuron,
B44) clomazon,
B45) benzofenap,
B46) pyrazolnyate,
B47) pyrazoxyfen,
B49) KIH 6127
B50) oxadiazon,
B51) oxadiargyl,
B56) bensulfuron,
B58) bensulfuron,
B59) pyrazolsulfuron,
B60) cinosulfuron,
B61) imazosulfuron,
B62) AC 322, 140 (cyclosulfamuron)
B63a) ethoxysulfuron (HOE 095404)
B64) azimsulfuron (DPX-A8947)
B66) prometryn,
B67) simetryn,
B68) thiazopyr,
B69) pyrazophos,
B70) pentoxazone,
B71) indanofan,
B72) LGC 40863
and
B73) MY 100
or in connection with two or more herbicidally active compounds from the group of the compounds B″ consisting of
B1) butenachlor,
B2) butenachlor,
B3) thenylchlor,
B4) pretilachlor,
B5) mefenacet,
B5a) Bay FOE 5043,
B6) naproanilid,
B7) propanil,
B8) etobenzanid,
B9) dimepiperate,
B10) molinate,
B11) thiobencarb
B12) pyributicarb,
B13) quinclorac,
B14a) sulcotrione,
B15) cycloxydim,
B16) sethoxydim,
B17) NBA 061,
B18) piperophos,
B19) anilofos,
B20) fenoxaprop, fenoxaprop-P
B21) haloxyfop,
B22) cyhalofop,
B23) JC-940
B24) dithiopyr,
B25) bromobutide,
B26) cinmethylin,
B27) CH-900,
B30) MCPA,
B31) dicamba,
B32) acifluorfen,
B34) chlorimuron
B35) triasulfuron,
B36) ioxynil,
B37) picloram,
B38) carfentrazon,
B39) bentazon,
B40) triclopyr,
B41) benfuresate,
B42) daimuron
B43) pendimethalin,
B44) clomazon,
B45) benzofenap,
B46) pyrazolynate,
B47) pyazoxyfen,
B48) KIH 2023,
B49) KIH 6127,
B50) oxadiazon,
B51) oxadiargyl,
B52) acetochlor,
B53) metolachlor,
B54) metosulam,
B55) oxyfluorfen,
B56) dalapon
B57) metsulfuron,
B58) bensulfuron,
B60) cinosulfuron,
B61) imazosulfuron,
B62) AC 322, 140 (cyclosulfamuron),
B63a) ethoxysulfuron (HOE 095404),
B64) azimsulfuron (DPX-A8947)
B65) nicosulfuron,
B66) prometryn,
B67) simetryn,
B66) prometryn,
B67) simetryn,
B68) thiazopyr,
B69) pyrazophos,
B70) pentoxazone,
B71) indanofan,
B72) LGC 40863 and
B73) MY 100
wherein in the case B″ at least one of the compounds from the group B″ also has to belong to B′.
24. The herbicidal composition as claimed in claim 5 , which comprises at Least one group B herbicide selected from the group consisting of
25. A process for preparing a herbicidal composition as claimed in claim 1 which comprises, formulating the compounds of the formula I or their salts (group A compounds) with one or more compounds of group B analogously to a customary crop protection formulation selected from the group consisting of wettable powders, emulsifiable concentrates, aqueous solution, emulsions, sprayable solutions (tank mix), oil- or water-based dispersions, suspoemulsions, dusting agents, seed dressings, granules for soil application or application by broadcasting, water-dispersible granules, ULV formulations, microcapsules and waxes.
26. A method for controlling undesirable plants, which comprises, applying a herbicidally effective amount of herbicide compositions according to claim 1 , to the undesirable plants or to the area under cultivation.
27. The method as claimed in claim 26 , wherein the application rate for the compounds of the formula (I) or their salts (group A compounds) is from 0.1 to 100 g of ai/ha, and the application rates for the compounds of group B are from 1 to 5000 g of ai/ha.
28. The method as claimed in claim 27 , wherein the application rate for the compounds of group A are from 0.5 to 60 g of ai/ha.
29. The method as claimed in claim 27 , wherein the application rate for the compounds of group A is from 2 to 40 g of ai/ha.
30. The method as claimed in claim 26 , wherein the active compounds of types A and B are supplied simultaneously or at different times in a weight ratio of from 1:20,000 to 200:1.
31. The method as claimed in claim 26 , wherein the combinations are employed for the selective control of undesirable plants.
32. The method as claimed in claim 31 , wherein the combinations are employed in transgenic crops.
33. The method as claimed in claim 31 , wherein the combinations are employed in rice.
34. A method for controlling undesirable harmful plants in rice crops which comprises applying to said harmful plants or to an area where they reside an effective amount of a herbicidal composition comprising:
A) at least one herbicidally active compound from the group of the substituted phenylsulfonylureas of the formula I and their agriculturally accepted, salts
in which
R 1 is (C 1 -C 8 )-alkyl, (C 3 -C 4 )-alkenyl, (C 3 -C 4 )-alkynyl or (C 1 -C 4 )-alkyl, which is mono- to tetrasubstituted by radicals selected from the group consisting of halogen and/or (C 1 -C 2 )-alkoxy;
R 2 is I or CH 2 NHSO 2 CH 3 when
Z is CH
or
R 2 is CH 2 NHSO 2 CH 3 when
Z is N
R 3 is methyl or methoxy,
and
B) at least on herbidically active compound from the group of the compounds consisting of
Ba) herbicides which are selective in rice against grasses selected from the group consisting of
B1) butachlor,
B2) butenachlor,
B3) thenylchlor,
B4) pretilachlor,
B5) mefenacet,
B5a) Bay FOE 5043,
B6) naproanilid,
B7) propanil,
B8) etobenzanid,
B9) dimepiperate,
B10) molinate,
B11) thiobencarb,
B12) pyributicarb,
B13) quinclorac,
B14) cyclohexandiones of the formula II t, 2121
in which
R 1 is halogen, (C 1 -C 4 )-alkoxy, (C 1 -C 4 )-alkyl, (C 1 -C 4 )-haloalkyl, —NO 2 , —CN or S(O) n R 10 ;
R 2 and R 3 independently of one another are hydrogen, halogen, (C 1 -C 4 )-alkyl, (C 1 -C 4 )-alkoxy, (C 1 -C 4 )-haloalkoxy, (C 1 -C 4 )-alkyl, (C 1 -C 4 )-alkoxy, (C 1 -C 4 )-haloalkoxy, (C 1 -C 4 )-haloalkyl, —NO 2 , —CN or S(O) m R 11 , —NR 12 R 13 , —NR 14 —CO—R 15 ;
R 4 is hydrogen, (C 1 -C 4 )-alkyl or —CO—O—(C 1 -C 4 )-alkyl;
R 5 ,R 6 ,R 7 ,R 8 ,R 9 , independently of one another are hydrogen or (C 1 -C 4 )-alkyl or —CO—R 16 ;
R 10 is (C 1 -C 4 )-alkyl, (C 1 -C 4 )-haloalkyl or (C 1 -C 4 )-alkoxy;
R 11 is (C 1 -C 4 )-alkyl, (C 1 -C 4 )-haloalkyl, phenyl, benzyl or —NR 17 R 18 ;
R 12 and R 13 independently of one another are hydrogen or (C 1 -C 4 )-alkyl;
R 14 is hydrogen or (C 1 -C 4 )-alkyl
R 15 is (C 1 -C 4 )-alkyl;
R 16 is hydrogen, (C 1 -C 4 )-alkyl, (C 1 -C 4 )-haloalkyl or (C 1 -C 4 )-alkoxy;
R 17 and R 18 independently or one another are hydrogen or (C 1 -C 4 )-alkyl; and
n and m independently or one another are 0, 1 or 2,
B15) sethoxydim
B16) NBA 061,
B17) piperophos,
B18) anilofos,
B19) fenoxaprop, fenoxaprop-P,
B20) haloxyfop,
B21) cyhalofop,
B22) JC-940
B23) dithiopyr,
B24) bromobutide,
B25) cinmethylin and
B26) CH-900,
Bb) herbicides which are selective in rice against dicotyledonous harmful plants and cyperaceae selected from the group consisting of
B27) 2,4-D,
B28) mecoprop, mecoprop-P,
B29) MCPA,
B30) dicamba,
B31) acifluorfen,
B34) chlorimuron,
B35) triasulfuron,
B36) ioxynil
B37) picloram
and
B38) carfentrazon,
Bc) herbicides which are selective in rice against cyperaceae selected from the group consisting of
B39) bentazon,
B40) triclopyr,
B41) benfuresate,
and
B42) daimuron,
Bb) herbicides which are selective in rice against grasses and dicotyledonous harmful plants and harmful cyperaceae plants selected from the group consisting of
B43) pendimethalin,
B44) clomazon,
B45) benzofenap,
B46) pyrazolynate,
B47) pyrazoxyfen,
B48) KIH 2023,
B49) KIH 6127
B50) oxadiazon,
B51) oxadiargyl,
B52) acetochlor,
B53) metolachlor,
B54) metosulam,
B55) oxyfluorfen,
B56) dalapon,
B57) metsulfuron,
B58) bensulfuron,
B59) pyrazosulfuron
B60) cinosulfuron,
B61) imazosulfuron,
B62) AC 322, 140 (cyclosulfamuron),
B63a) ethoxysulfuron (HOE 095404)
B64) azimsulfuron (DPX-A8947),
B65) nicosulfuron,
B66) prometryn,
B67) simetryn,
B68) thiazopyr,
B69) pyrazophos,
B70) pentoxazone,
B71) indanofan,
B72) LGC 40863 and
B73) MY 100,
in a weight ratio A:B in the range from 1:20,000 to 200:1.
35. The method as claimed in claim 34 , wherein the amounts are synergistic.
36. The method as claimed in claim 34 , wherein the herbicidal compositions comprise at least one compound from A) and at least one compound from Ba).
37. The method as claimed in claim 34 , wherein the herbicidal compositions comprise at least one compound from A) and at least one compound from Bb).
38. The method as claimed in claim 34 , wherein the herbicidal composition comprises at least one compound from A) and at least on compound from Bc).
39. The method as claimed in claim 34 , wherein the herbicidal composition comprises at least one compound from A) and at least one compound from Bd).