Note: Descriptions are shown in the official language in which they were submitted.
w
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Syner~istic herbicidal active compound combinations
The invention relates to novel synergistic herbicidally active compound
combinations
comprising tritosulfuron and known herbicidally active compounds and
optionally
compounds which improve crop plant compatibility, which combinations can be
used
with particularly good results for the selective control of weeds in various
crops of
useful plants.
As a herbicide with broad action, tritosulfuron (N-[[[4-methoxy-6-
(trifluoromethyl)-
1,3,5-triazin-2-yl]amino]carbonyl]-2-trifluoromethyl-benzenesulphonamide)
forms part
of the subject-matter of a number of patent applications (cf. DE-A 40 38 430,
WO-A 97/10714). However, this active compound has gaps in its activity.
Surprisingly, it has now been found that tritosulfuron, used jointly with
known
herbicidally active compounds from different substance classes, shows
pronounced
synergistic effects with respect to the activity against weeds, and that such
broadly
active combination preparations can be used particularly advantageously for
the
selective control of weeds in crops of useful plants, such as, for example
wheat and
maize.
Surprisngly, it has also been found that it may be possible to achieve
additional advan-
tageous effects using mixtures of tritosulfuron with further known
herbicidally active
compounds applied jointly with the crop-plant-compatibility-improving
compounds
(safeners/antidotes) described below.
The present invention provides compositions, characterized in that they
comprise a
synergistically effective amount of an active compound combination consisting
of
(a) tritosulfuron
and
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(b) one or more compounds from a group of herbicides consisting of the active
compounds mentioned below:
(5-trifluoromethyl-1,3,4-thiadiazol-2-yl-oxy)-N-isopropyl-N-(4-fluoro-
phenyl)-acetamide (flufenacet, DE-A-38 21 600), 2-(2-methoxycarbonyl-
phenylsulphonylaminocarbonyl)-4-methyl-5-n-propoxy-2,4-dihydro-3H-
1,2,4-triazol-3-one or the sodium salt of this compound (propoxycarba-
zone(-sodium)), EP-A-507171), 2-(2-trifluoromethoxy-phenylsulphonyl-
aminocarbonyl)-4-methyl-5-methoxy-2,4-dihydro-3H-1,2,4-triazol-3-one or
the sodium salt of this compound (flucarbazone(-sodium)), EP-A-507 171),
N-(3,4-dichlorophenyl)propanamide (propanil, DE-A-10 39 779), N-2-benzo-
thiazolyl-N,N'-dimethylurea (methabenzthiazuron, GB-A-1085430), 4-amino-
6-(l,l-dimethylethyl)-3-(methylthio)-1,2,4-triazin-5(4H)-one (metribuzin,
DE-A-17 95 784), 4-(2-chlorophenyl)-N-cyclohexyl-N-ethyl-4,5-dihydro-5-
oxo-1H-tetrazole-1-carboxamide (fentrazamide, EP-A-612 735), 4-amino-3-
methyl-6-phenyl-1,2,4-triazin-5(4H)-one (metamitron, DE-A-21 38 031), 2-
(2-benzothiazolyloxy)-N-methyl-N-phenylacetamide (mefenacet, DE-A-
28 22 155), 4-amino-6-(1,1-dimethylethyl)-3-(ethylthio)-1,2,4-triazin-5(4H)-
one (ethiozin, DE-A-15 42 873), 1-methylethyl 5-[4-bromo-1-methyl-5-(tri-
fluoromethyl)-1H-pyrazol-3-yl]-2-chloro-4-fluorobenzoate (fluazolate, WO-A
9206962)
("active compounds of group 1 ")
and optionally
(c) one or more compounds from a second group of herbicides which consists of
the active compounds mentioned below:
2-chloro-N-(ethoxymethyl)-N-(2-ethyl-6-methyl-phenyl)-acetamide (aceto-
chlor), 5-(2-chloro-4-trifluoromethyl-phenoxy)-2-nitro-benzoic acid sodium
salt
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(acifluorfen-sodium), 2-chloro-6-nitro-3-phenoxy-benzenamine (aclonifen), 2-
chloro-N-(methoxymethyl)-N-(2,6-diethyl-phenyl)-acetamide (alachlor), N-
ethyl-N'-i-propyl-6-methylthio-1,3,5-triazine-2,4-diamine (ametryn), 4-
arnino-N-( 1,1-dimethyl-ethyl)-4, 5-dihydro-3-( 1-methyl-ethyl)-5-oxo-1 H-
1,2,4-triazole-1-carboxamide (amicarbazone), N-(4,6-dimethoxypyrimidin-
2-yl)-N'-(N-methyl-N-methylsulphonyl-sulphamoyl)-urea (amidosulfuron),
1H-1,2,4-triazole-3-amine (amitrole), 6-chloro-4-ethylamino-2-isopropyl-
amino-1,3,5-triazine (atrazine), 2-[2,4-dichloro-5-(2-propinyloxy)-phenyl]-
5,6,7,8-tetrahydro-1,2,4-triazolo-[4,3-a]-pyridin-3(2H)-one (azafenidin), N-
(4,6-dimethoxy-pyrimidin-2-yl)-N '-[ 1-methyl-4-(2-methyl-2H-tetrazol-5-yl)-
1 H-pyrazol-5-ylsulphonylJ-urea (azimsulfuron), N-benzyl-2-(4-fluoro-3-tri-
fluoromethyl-phenoxy)-butanamide (beflubutamid), 4-chloro-2-oxo-3(2H)-
benzothiazoleacetic acid (benazolin), N-butyl-N-ethyl-2,6-dinitro-4-trifluoro-
methyl-benzenamine (benfluralin), N-(4,6-dimethoxy-pyrimidin-2-yl)-N'-(2-
methoxycarbonyl-phenylmethylsulphonyl)-urea (bensulfuron), methyl 2-[2-
[4-(3,6-dihydro-3-methyl-2,6-dioxo-4-trifluoromethyl-1 (2H)-pyrimidinyl-
phenoxymethylJ-5-ethyl-phenoxy-propanoate (benzfendizone), 3-(2-chloro-
4-methylsulphonyl-benzoyl)-4-phenylthio-bicyclo-[3.2.1 ]-oct-3-en-2-one
(benzobicyclon), ethyl N-benzoyl-N-(3,4-dichloro-phenyl)-DL-alaninate
(benzoylprop-ethyl), 3-i-propyl-1H-2,1,3-benzothiadiazin-4(3H)-one
(bentazone),
methyl 5-(2,4-dichloro-phenoxy)-2-nitro-benzoate (bifenox), 2,6-bis-(4,6-
dimethoxy-pyrimidin-2-yl-oxy)-benzoic acid sodium salt (bispyribac-
sodium), 2-bromo-3,3-dimethyl-N-(1-methyl-1-phenyl-ethyl)-butanamide
(bromobutide), 3,5-dibromo-4-hydroxy-benzaldehyde O-(2,4-dinitro-phenyl)
oxime (bromofenoxim), 3,5-dibromo-4-hydroxy-benzonitrile (bromoxynil),
N-butoxymethyl-2-chloro-N-(2,6-diethyl-phenyl)-acetamide (butachlor), [ 1,1-
dimethyl-2-oxo-2-(2-propenyloxy)]-ethyl 2-chloro-5-(3,6-dihydro-3-methyl-
2,6-dioxo-4-trifluoromethyl-1(2H)-pyrimidinyl)-benzoate (butafenacil-allyl),
2-( 1-ethoximino-propyl)-3 -hydroxy-5-[2,4,6-trimethyl-3-( 1-oxo-butyl)-
phenyl]-2-cyclohexen-1-one (butroxydim), S-ethyl bis-(2-methyl-propyl)-
thiocarbamate (butylate), N,N-diethyl-3-(2,4,6-trimethyl-phenylsulphonyl)-
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1H-1,2,4-triazole-1-carboxamide (cafenstrole), 2-[1-[(3-chloro-2-propenyl)-
oxy-imino]-propyl]-3-hydroxy-5-(tetrahydro-2H-pyran-4-yl)-2-cyclohexen-1-
one (caloxydim, tepraloxydim), 2-(4-chloro-2-fluoro-5-(2-chloro-2-ethoxy-
carbonyl-ethyl)-phenyl)-4-difluoromethyl-S-methyl-2,4-dihydro-3H-1,2,4-
triazol-3-one (carfentrazone-ethyl), 2,4-dichloro-1-(3-methoxy-4-nitro-
phenoxy)-benzene (chlomethoxyfen), 3-amino-2,5-dichloro-benzoic acid
(chloramben), N-(4-chloro-6-methoxy-pyrimidin-2-yl)-N'-(2-ethoxycarbonyl-
phenylsulphonyl)-urea (chlorimuron-ethyl), 1,3,5-trichloro-2-(4-nitro-
phenoxy)-benzene (chlornitrofen), N-(4-methoxy-6-methyl-1,3,5-triazin-2-
yl)-N'-(2-chloro-phenylsulphonyl)-urea (chlorsulfuron), N'-(3-chloro-4-
methyl-phenyl)-N,N-dimethyl-urea (chlorotoluron), ethyl 2-chloro-3-[2-chloro-
5-(1,3,4,5,6,7-hexahydro-1,3-dioxo-2H-isoindol-2-yl)-phenyl]-2-propanoate
(cini-
don-ethyl), N-(4,6-dimethoxy-1,3,5-triazin-2-yl)-N'-(2-(2-methoxy-ethoxy)-
phenylsulphonyl)-urea (cinosulfuron), 2-[1-[2-(4-chloro-phenoxy)-propoxy-
aminobutyl]-5-(tetrahydro-2H-thiopyran-3-yl)-1,3-cyclohexanedione (clef
oxydim), (E,E)-(+)-2-[1-[[(3-chloro-2-propenyl)-oxy]-imino]-propyl]-3-
hydroxy-2-cyclohexen-1-one (clethodim), 2-propinyl (R)-2-[4-(5-chloro-3-
fluoro-pyridin-2-yl-oxy)-phenoxy-propanoate (clodinafop-propargyl), 3,6-
dichloro-pyridine-2-carboxylic acid (clopyralid), methyl 3-chloro-2-[(S-eth-
oxy-7-fluoro [ 1,2,4] tri azolo [ 1, 5-c] pyrimidin-2-yl-sulphonyl)-amino]-
benzoate
(cloransulam-methyl), 2-chloro-4-ethylamino-6-(1-cyano-1-methyl-ethyl-
amino)-1,3,5-triazine (cyanazine), N-(4,6-dimethoxy-pyrimidin-2-yl)-N'-(2-
cyclopropylcarbonyl-phenylsulphonyl)-urea (cyclosulfamuron), 2-(1-ethox-
iminobutyl)-3-hydroxy-5-(tetrahydro-2H-thiopyran-3-yl)-2-cyclohexen-1-one
(cycloxydim), butyl (R)-2-[4-(4-cyano-2-fluoro-phenoxy)-phenoxy]-
propanoate (cyhalofop-butyl), 2,4-Dichloro-phenoxyacetic acid (2,4-D),
3,6-dichloro-2-methoxy-benzoic acid (dicamba), (R)-2-(2,4-dichloro-phen-
oxy)-propanoic acid (dichlorprop-P), methyl 2-[4-(2,4-dichloro-phenoxy)-
phenoxy]-propanoate (diclofop-methyl), N-(2,6-dichloro-phenyl)-5-ethoxy-7-
fluoro-[1,2,4]-triazolo-[1,5-c]-pyrimidine-2-sulphonamide (diclosulam), 1,2-
dimethyl-3,5-diphenyl-1H-pyrazolium methyl sulphate (difenzoquat), N-(2,4-
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difluoro-phenyl)-2-(3-trifluoromethyl-phenoxy)-pyridine-3-carboxamide (di-
flufenican), 2-[1-[(3,5-difluoro-phenyl)-amino-carbonyl-hydrazono]-ethyl]-
pyridine-3-carboxylic acid (diflufenzopyr), S-(1-methyl-1-phenyl-ethyl) 1-
piperidine carbothioate (dimepiperate), (S-) 2-chloro-N-(2,4-dimethyl-3-
thienyl)-N-(2-methoxy-1-methyl-ethyl)-acetamide ((S-) (dimethenamid), 2-
amino-4-(1-fluoro-1-methyl-ethyl)-6-(1-methyl-2-(3,5-dimethyl-phenoxy)-ethyl-
amino)-1,3,5-triazine (dimexyflam), N3,N3-diethyl-2,4-dinitro-6-trifluoro-
methyl-1,3-diamino-benzene (dinitramine), 6,7-dihydro-dipyrido[1,2-a:2',1'-
c]pyrazinediium (diquat), S,S-dimethyl-2-difluoromethyl-4-i-butyl-6-tri-
fluoromethyl-pyridine 3,5-dicarbothioate (dithiopyr), N'-(3,4-dichloro-
phenyl)-N,N-dimethyl-urea (diuron), 2-[2-(3-chloro-phenyl)-oxiranylmethyl]-
2-ethyl-1H-indene-1,3(2H)-dione (epropodan), S-ethyl dipropylthiocarbamate
(EPTC), S-(phenylmethyl) N-ethyl-N-(1,2-dimethyl-propyl)-thiocarbamate
(esprocarb), N-ethyl-N-(2-methyl-2-propenyl)-2,6-dinitro-4-trifluoromethyl-
benzenamine (ethalfluralin), (2-ethoxy-1-methyl-2-oxoethyl) (S)-2-chloro-5-
(2-chloro-4-trifluoromethyl-phenoxy)-benzoate (ethoxyfen), N-(4,6-di-
methoxy-pyrimidin-2-yl)-N'-(2-ethoxy-phenoxysulphonyl)-urea (ethoxy-
sulfuron), ethyl (R)-2-[4-(6-chloro-benzoxazol-2-yl-oxy)-phenoxy]-pro-
panoate (fenoxaprop-(P)-ethyl), 4-(2-chloro-phenyl)-N-cyclohexyl-N-ethyl-
4,5-dihydro-5-oxo-1H-tetrazole-1-carboxamide (fentrazamide), isopropyl N-
benzoyl-N-(3-chloro-4-fluoro-phenyl)-DL-alaninate (flamprop-isopropyl),
isopropyl N-benzoyl-N-(3-chloro-4-fluoro-phenyl)-L-alaninate (flamprop-iso-
propyl-L), methyl N-benzoyl-N-(3-chloro-4-fluoro-phenoxy)-DL-alaninate
(flamprop-methyl), N-(2,6-difluoro-phenyl)-8-fluoro-5-methoxy-[1,2,4]-
triazolo-[1,5-c]-pyrimidine-2-sulphonamide (florasulam), butyl (R)-2-[4-(5-
trifluoromethyl-pyridin-2-yl-oxy)-phenoxy]-propanoate (fluazifop, -butyl, -P-
butyl), i-propyl 5-(4-bromo-1-methyl-5-trifluoromethyl-1H-pyrazol-3-yl)-2-
chloro-4-fluoro-benzoate (fluazolate), 4,5-dihydro-3-methoxy-4-methyl-5-
oxo-N-[(2-trifluoromethoxy-phenyl)-sulphonyl]-1 H-1,2,4-triazole-1-carbox-
amide sodium salt (flucarbazone-sodium), N-(4-fluoro-phenyl)-N-i-propyl-2-
(5-trifluoromethyl-1,3,4-thiadiazol-2-yl-oxy)-acetamide (flufenacet), N-(2,6-
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difluoro-phenyl)-5-methyl-1,2,4-triazolo [ 1, 5-a]-pyrimidine-2-sulphonamide
(flumetsulam), pentyl [2-chloro-4-fluoro-5-(1,3,4,5,6,7-hexahydro-1,3-dioxo-
2H-isoindol-2-yl)-phenoxy]-acetate (flumiclorac-pentyl), 2-[7-fluoro-3,4-di-
hydro-3-oxo-4-(2-propinyl)-2H-1,4-benzoxazin-6-yl]-4,5,6,7-tetrahydro-1 H-
isoindole-1,3-dione (flumioxazin), 2-[4-chloro-2-fluoro-5-[(1-methyl-2-pro-
pinyl)-oxy]-phenyl]-4,5,6,7-tetrahydro-1H-isoindole-1,3(2H)-dione (flumi-
propyn), 3-chloro-4-chloromethyl-1-(3-trifluoromethyl-phenyl)-2-pyrroli-
dinone (fluorochloridone), ethoxycarbonylmethyl 5-(2-chloro-4-trifluoro-
methyl-phenoxy)-2-nitro-benzoate (fluoroglycofen-ethyl), 1-(4-chloro-3-
(2,2,3,3,3-pentafluoro-propoxymethyl)-phenyl)-5-phenyl-1 H-1,2,4-triazole-3-
carboxamide (flupoxam), 1-isopropyl-2-chloro-5-(3,6-dihydro-3-methyl-2,6-
dioxo-4-trifluoromethyl-1(2H)-pyrimidyl)-benzoate (flupropacil), N-(4,6-di-
methoxy-pyrimidin-2-yl)-N'-(3-methoxycarbonyl-6-trifluoromethyl-pyridin-
2-yl-sulphonyl)-urea sodium salt (flupyrsulfuron-methyl-sodium), 9-hydroxy-
9H-fluorene-9-carboxylic acid (flurenol), (2-butoxy-1-methyl-ethyl, 1-
methyl-heptyl) (4-amino-3,5-dichloro-6-fluoro-pyridin-2-yl-oxy)-acetate
(fluroxypyr, -butoxypropyl, -meptyl), 5-methylamino-2-phenyl-4-(3-tri-
fluoromethyl-phenyl)-3(2H)-furanone (flurtamone), methyl [(2-chloro-4-
fluoro-5-(tetrahydro-3-oxo-1 H,3H-[ 1,3,4]-thiadiazolo-[3,4-a]-pyridazin-1-
ylidene)-amino-phenyl]-thio-acetate (fluthiacet-methyl), 5-(2-chloro-4-tri-
fluoromethyl-phenoxy)-N-methylsulphonyl-2-nitro-benzamide (fomesafen),
2-[[[[(4,6-dimethoxy-2-pyrimidinyl)-amino]-carbonyl]-amino]-sulphonyl]-4-
formylamino-N,N-dimethyl-benzamide (foramsulfuron), 2-amino-4-(hydroxy-
methylphosphinyl)-butanoic acid (ammonium salt) (glufosinate (-am-
monium)), N-phosphonomethyl-glycine (isopropylammmonium salt),
(glyphosate, (-isopropylammonium)), (methyl, 2-ethoxy-ethyl, butyl) (R)-2-
[4-(3-chloro-5-trifluoromethyl-pyridin-2-yl-oxy)-phenoxy]-propanoate (hal-
oxyfop, -methyl, -P-methyl, -ethoxyethyl, -butyl), 3-cyclohexyl-6-dimethyl-
amino-1-methyl-1,3,5-triazine-2,4(1H,3H)-dione (hexazinone), methyl 2-(4,5-
dihydro-4-methyl-4-isopropyl-5-oxo-1 H-imidazol-2-yl)-4-methyl-benzoate
(imazamethabenz-methyl), 2-(4,5-dihydro-4-methyl-4-isopropyl-5-oxo-1H-
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imidazol-2-yl)-5-methyl-pyridine-3-carboxylic acid (imazamethapyr), 2-(4,5-
dihydro-4-methyl-4-isopropyl-5-oxo-1 H-imidazol-2-yl)-5-methoxymethyl-
pyridine-3-carboxylic acid (imazamox), 2-(4,5-dihydro-4-methyl-4-isopropyl-
5-oxo-1H-imidazol-2-yl)-quinoline-3-carboxylic acid (imazaquin), 2-(4,5-di-
hydro-4-methyl-4-i-propyl-5-oxo-1 H-imidazol-2-yl)-5-ethyl-pyridine-3-
carboxylic acid (imazethapyr), N-(4,6-dimethoxy-pyrimidin-2-yl)-N'-(2-
chloro-imidazo[1,2-a]-pyridin-3-yl-sulphonyl)-urea (imazosulphuron), N-(4-
methoxy-6-methyl-1,3,5-triazin-2-yl)-N'-(5-iodo-2-methoxycarbonyl-phenyl-
sulphonyl)-urea sodium salt (iodosulfuron-methyl-sodium), 4-hydroxy-3,5-
diiodo-benzonitrile (ioxynil), N,N-dimethyl-N'-(4-isopropyl-phenyl)-urea
(isoproturon), N-(3-(1-ethyl-1-methyl-propyl)-isoxazol-5-yl)-2,6-dimethoxy-
benzamide (isoxaben), (4-chloro-2-methylsulphonyl-phenyl)-(5-cyclopropyl-
isoxazol-4-yl)-methanone (isoxachlortole), (5-cyclopropyl-isoxazol-4-yl)-(2-
methylsulphonyl-4-trifluoromethyl-phenyl)-methanone (isoxaflutole), 2-[2-[4-
[(3,5-dichloro-2-pyridinyl)-oxy]-phenoxy]-1-oxo-propyl]-isoxazolidine (isoxa-
pyrifop), 2-ethoxy-1-methyl-2-oxo-ethyl 5-(2-chloro-4-trifluoromethyl-
phenoxy)-2-nitro-benzoate (lactofen), N'-(3,4-dichloro-phenyl)-N-methoxy-N-
methyl-urea (linuron), (4-chloro-2-methyl-phenoxy)-acetic acid (MCPA), 2-
(4-chloro-2-methyl-phenoxy)-propionic acid (mecoprop), 2-(2-benzothiazol-
yloxy)-N-methyl-N-phenyl-acetamide (mefenacet), 2-(4-methylsulphonyl-2-
nitro-benzoyl)-1,3-cyclohexanedione (mesotrione), 4-amino-3-methyl-6-
phenyl-1,2,4-triazin-5(4H)-one (metamitron), 2-chloro-N-(2,6-dimethyl-
phenyl)-N-(1H-pyrazol-1-yl-methyl)-acetamide (metazachlor), N'-(4-(3,4-di-
hydro-2-methoxy-2,4,4-trimethyl-2H-1-benzopyran-7-yl-oxy)-phenyl)-N-
methoxy-N-methyl-urea (metobenzuron), N'-(4-bromo-phenyl)-N-methoxy-
N-methylurea (metobromuron), (S)-2-chloro-N-(2-ethyl-6-methyl-phenyl)-N-
(2-methoxy-1-methyl-ethyl)-acetamide (metolachlor, S-metolachlor), N-(2,6-
dichloro-3-methyl-phenyl)-5,7-dimethoxy-1,2,4-triazolo[ 1, 5-a]-pyrimidine-2-
sulphonamide (metosulam), N'-(3-chloro-4-methoxy-phenyl)-N,N-dimethyl-
urea (metoxuron), 4-amino-6-tert-butyl-3-methylthio-1,2,4-triazin-5(4H)-one
(metribuzin), N-(4-methoxy-6-methyl-1,3,5-triazin-2-yl)-N'-(2-methoxy-
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carbonyl-phenylsulphonyl)-urea (metsulfuron-methyl), S-ethyl hexahydro-1 H-
azepine 1-carbothioate (molinate), 2-(2-naphthyloxy)-N-phenyl-propanamide
(naproanilide), N-butyl-N'-(3,4-dichloro-phenyl)-N-methyl-urea (neburon), N-
(4,6-dimethoxy-pyrimidin-2-yl)-N'-(3-dimethylcarbamoyl-pyridin-2-yl-
sulphonyl)-urea (nicosulfuron), S-(2-chloro-benzyl) N,N-diethyl-thio-
carbamate (orbencarb), 4-dipropylamino-3,5-dinitro-benzenesulphonamide
(oryzalin), 3-[2,4-dichloro-5-(2-propinyloxy)-phenyl]-5-(t-butyl)-1,3,4-oxadi-
azol-2(3H)-one (oxadiargyl), 3-[2,4-dichloro-5-(1-methyl-ethoxy)-phenyl]-5-
(t-butyl)-1,3,4-oxadiazol-2(3H)-one (oxadiazon), N-(4,6-dimethyl-pyrimidin-
2-yl)-N'-(2-oxetan-3-yl-oxycarbonyl-phenylsulphonyl)-urea (oxasulfuron),
3-[ 1-(3,S-dichloro-phenyl)-1-i-propyl]-2,3-dihydro-6-methyl-5-phenyl-4H-
1,3-oxazin-4-one (oxaziclomefone), 2-chloro-1-(3-ethoxy-4-nitro-phenoxy)-
4-trifluoromethyl-benzene (oxyfluorfen), 1,1'-dimethyl-4,4'-bipyridinium
(paraquat), 1-amino-N-(1-ethyl-propyl)-3,4-dimethyl-2,6-dinitro-benzene
(pendimethalin), 4-(t-butyl)-N-(1-ethyl-propyl)-2,6-dinitro-benzenamine
(pendralin), 4-amino-3,5,6-trichloro-pyridine-2-carboxylic acid (picloram), 2-
chloro-N-(2,6-diethyl-phenyl)-N-(2-propoxy-ethyl)-acetamide (pretilachlor),
N-(4,6-bis-difluoromethoxy-pyrimidin-2-yl)-N'-(2-methoxycarbonyl-phenyl-
sulphonyl)-urea (primisulfuron-methyl), 1-chloro-N-[2-chloro-4-fluoro-5-
[(6S,7aR)-6-fluoro-tetrahydro-1,3-dioxo-1 H-pyrrolo[ 1,2-c]imidazol-2(3H)-
yl]-phenyl]-methanesulphonamide (profluazol), 2-chloro-N-isopropyl-N-
phenyl-acetamide (propachlor), N-(3,4-dichloro-phenyl)-propanamide
(propanil), (R)-[2-[[(1-methyl-ethylidene)-amino]-oxy]-ethyl]-2-[4-(6-chloro-
2-quinoxalinyloxy)-phenoxy]-propanoate (propaquizafop), 2-chloro-N-(2-
ethyl-6-methyl-phenyl)-N-[(1-methyl-ethoxy)-methyl]-acetamide (propiso-
chlor), methyl 2-[[[(4,5-dihydro-4-methyl-5-oxo-3-propoxy-1H-1,2,4-triazol-
1-yl)-carbonyl]-amino]-sulphonyl]-benzoate sodium salt (propoxycarbazone-
sodium), S-phenylmethyl N,N-dipropyl-thiocarbamate (prosulfocarb), N-(4-
methoxy-6-methyl-1,3, 5-triazin-2-yl)-N'-(2-(3,3,3-trifluoro-propyl)-phenyl-
sulphonyl)-urea (prosulfuron), ethyl [2-chloro-5-(4-chloro-5-difluoro-
methoxy-1-methyl-1H-pyrazol-3-yl)-4-fluoro-phenoxy]-acetate (pyraflufen-
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ethyl), 1-(3-chloro-4,5,6,7-tetrahydro-pyrazolo[1,5-a]pyridin-2-yl)-5-(methyl-
2-propinylamino)-1H-pyrazole-4-carbonitrile (pyrazogyl), 4-(2,4-dichloro-
benzoyl)-1,3-dimethyl-5-(4-methyl-phenylsulphonyloxy)-pyrazole (pyrazo-
late), 4-(2,4-dichloro-benzoyl)-1,3-dimethyl-5-(phenylcarbonylmethoxy)-pyr-
azole (pyrazoxyfen), N-(4,6-dimethoxy-pyrimidin-2-yl)-N'-(4-ethoxy-
carbonyl-1-methyl-pyrazol-5-yl-sulphonyl)-urea (pyrazosulfiuon-ethyl), di-
phenylmethanone O-[2,6-bis-(4,6-dimethoxy-pyrimidin-2-yl-oxy)-benzoyl]
oxime (pyribenzoxim), 6-chloro-3-phenyl-4-pyridazinole (pyridafol), O-(6-
chloro-3-phenyl-pyridazin-4-yl) S-octyl thiocarbonate (pyridate), 6-chloro-3-
phenyl-pyridazin-4-of (pyridatol), 7-[(4,6-dimethoxy-2-pyrimidinyl)-thio]-3-
methyl-1(3H)-isobenzofuranone (pyriftalid), methyl 2-(4,6-dimethoxy-pyri-
midin-2-yl-oxy)-benzoate (pyriminobac-methyl), 2-chloro-6-(4,6-dimethoxy-
pyrimidin-2-ylthio)-benzoic acid sodium salt (pyrithiobac-sodium), 3,7-di-
chloro-quinoline-8-carboxylic acid (quinchlorac), 7-chloro-3-methyl-
quinoline-8-carboxylic acid (quinmerac), (ethyl, tetrahydro-2-furanyl-
methyl) 2-[4-(6-chloro-2-quinoxalinyloxy)-phenoxy]-propanoate (quizalofop,
-ethyl, -P-ethyl, -P-tefuryl), N-(4,6-dimethoxy-pyrimidin-2-yl)-N'-(3-ethyl-
sulphonyl-pyridin-2-yl-sulphonyl)-urea (rimsulfuxon), 2-(1-ethoximinobutyl)-
5-(2-ethylthiopropyl)-3-hydroxy-2-cyclohexen-1-one (sethoxydim), 6-chloro-
2,4-bis-ethylamino-1,3,5-triazine (simazine), 2-(2-chloro-4-methylsulphonyl-
benzoyl)-cyclohexane-1,3-dione (sulcotrione), 2-(2,4-dichloro-5-methyl-
sulphonylamino-phenyl)-4-difluoromethyl-5-methyl-2,4-dihydro-3H-1,2,4-
triazol-3-one (sulfentrazone), N-phosphonomethyl-glycine-trimethyl-
sulphonium (sulfosate), N-(4,6-dimethoxy-pyrimidin-2-yl)-N'-(2-ethyl-
sulphonyl-imidazo[1,2-a]pyridin-3-yl)sulphonamide (sulfosulfuron), 6-
chloro-4-ethylamino-2-tent-butylamino-1,3,5-triazine (terbuthylazine), 2-tert-
butylamino-4-ethylamino-6-methylthio-1,3,5-triazine (terbutryn), 2-chloro-N-
(2,6-dimethyl-phenyl)-N-(3-methoxy-2-thienyl-methyl)-acetamide (thenyl-
chlor), methyl 2-difluoromethyl-5-(4,5-dihydro-thiazol-2-yl)-4-(2-methyl-
propyl)-6-trifluoromethyl-pyridine-3-carboxylate (thiazopyr), 6-(6,7-dihydro-
6,6-dimethyl-3H,5H-pyrrolo[2,1-c]-1,2,4-thiadiazol-3-ylideneamino)-7-
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fluoro-4-(2-propinyl)-2H-1,4-benzoxazin-3(4H)-one (thidiazimin), N-(4-
methoxy-6-methyl-1,3,5-triazin-2-yl)-N'-(2-methoxycarbonyl-thien-3-yl-
sulphonyl)-urea (thifensulfuron-methyl), 2-(ethoximino-propyl)-3-hydroxy-
5-(2,4,6-trimethyl-phenyl)-2-cyclohexen-1-one (tralkoxydim), S-(2,3,3-tri-
chloro-2-propenyl) diisopropylcarbamothioate (triallate), N-(4-methoxy-6-
methyl-1,3,5-triazin-2-yl)-N'-[2-(2-chloro-ethoxy)-phenylsulphonyl]-urea
(triasulfuron), N-methyl-N-(4-methoxy-6-methyl-1,3,5-triazin-2-yl)-N'-(2-
methoxycarbonyl-phenylsulfonyl)-urea (tribenuron-methyl), (3,5,6-trichloro)-
pyridin-2-yl-oxy-acetic acid (triclopyr), 2-(3,5-dichloro-phenyl)-2-(2,2,2-tri-
chloro-ethyl)-oxirane (tridiphane), N-[[(4,6-dimethoxy-2-pyrimidinyl)-
amino]-carbonyl]-3-(2,2,2-trifluoro-ethoxy)-2-pyridinesulphonamide
sodium salt (trifloxysulfuron), 1-amino-2,6-dinitro-N,N-dipropyl-4-tri-
fluoromethyl-benzene (trifluralin), N-[4-dimethylamino-6-(2,2,2-trifluoro-
ethoxy)-1,3,5-triazin-2-yl]-N'-(2-methoxycarbonyl-phenylsulphonyl)-urea
(triflu-
sulfuron-methyl), N-[[(4,6-dimethoxy-2-pyrimidinyl)-amino]-carbonyl]-3-(N-
methyl-N-methylsulphonyl-amino)-2-pyridinesulphonamide (c~ WO-A-
92/10660), methyl 2-[[[[(4,6-dimethoxy-2-pyrimidinyl)-amino]-carbonyl]-
amino]-sulphonyl]-4-[[(methylsulphonyl)-amino]methyl]-benzoate (cf. DE-A-
4335297), 4-[4,5-dihydro-4-methyl-5-oxo-(3-trifluoromethyl)-1H-1,2,4-tri-
azol-1-yl]-2-[(ethylsulphonyl)amino]-5-fluoro-benzenecarbothioamide (c~
WO-A-95/30661)
("active compounds of group 2"),
and/or optionally
(d) a compound which improves crop plant compatibility, from the group of
compounds below
4-dichloroacetyl-1-oxa-4-aza-spiro[4.5]-decane (AD-67), 1-dichloroacetyl-
hexahydro-3,3,8a-trimethylpyrrolo[1,2-a]-pyrimidin-6(2H)-one (BAS-145138),
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4-dichloroacetyl-3,4-dihydro-3-methyl-2H-1,4-benzoxazine (benoxacor), 1-
methyl-hexyl 5-chloro-quinoxalin-8-oxy-acetate (cloquintocet-mexyl), a-
(cyanomethoximino)-phenylacetonitrile (cyometrinil), 2,4-dichlorophenoxy-
acetic acid (2,4-D), 2,2-dichloro-N-(2-oxo-2-(2-propenylamino)-ethyl)-N-(2-
propenyl)-acetamide (DKA-24), 2,2-dichloro-N,N-di-2-propenyl-acetamide
(dichlormid), N-(4-methyl-phenyl)-N'-(1-methyl-1-phenyl-ethyl)-urea (dym-
ron), 4,6-dichloro-2-phenyl-pyrimidine (fenclorim), ethyl 1-(2,4-dichloro-
phenyl)-5-trichloromethyl-1H-1,2,4-triazole-3-carboxylate (fenchlorazol-
ethyl), phenylmethyl 2-chloro-4-trifluoromethyl-thiazole-5-carboxylate (flur-
azole), 4-chloro-N-(1,3-dioxolan-2-yl-methoxy)-a-trifluoro-acetophenone
oxime (fluxofenim), 3-dichloroacetyl-5-(2-fiuanyl)-2,2-dimethyl-oxazolidine
(furilazole, MON-13900), ethyl 4,5-dihydro-5,5-diphenyl-3-isoxazole-
carboxylate (isoxadifen-ethyl), (4-chloro-2-methyl-phenoxy)-acetic acid
(MCPA), (+-)-2-(4-chloro-2-methylphenoxy)propanoic acid (mecoprop), di-
ethyl 1-(2,4-dichlorophenyl)-4,5-dihydro-5-methyl-1 H-pyrazole-3,5-
dicarboxylate
(mefenpyr-diethyl), 2-dichloromethyl-2-methyl-1,3-dioxolane (MG-191), 1,8-
naphthalic anhydride, a-(1,3-dioxolan-2-yl-methoximino)-phenylacetonitrile
(oxabetrinil), 2,2-dichloro-N-(1,3-dioxolan-2-yl-methyl)-N-(2-propenyl)-acet-
amide (PPG-1292) and 3-dichloroacetyl-2,2,5-trimethyl-oxazolidine (R-
29148)
("active compounds of group 3 ").
Mixing components from the active compounds of group 2 which are particularly
emphasized are:
2-chloro-N-(ethoxymethyl)-N-(2-ethyl-6-methyl-phenyl)-acetamide (acetochlor),
2-
chloro-N-(methoxymethyl)-N-(2,6-diethyl-phenyl)-acetamide (alachlor), 4-amino-
N-
( 1,1-dimethyl-ethyl)-4,5-dihydro-3-(1-methyl-ethyl)-5-oxo-1 H-1,2,4-triazole-
1-carbox-
amide (amicarbazone), N-(4,6-dimethoxy-pyrimidin-2-yl)-N'-(N-methyl-N-methyl-
sulphonyl-sulphamoyl)-urea (amidosulfuron), 6-chloro-4-ethylamino-2-isopropyl-
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amino-1,3,5-triazine (atrazine), N-benzyl-2-(4-fluoro-3-trifluoromethyl-
phenoxy)-
butanamide (beflubutamid), 3-i-propyl-1H-2,1,3-benzothiadiazin-4(3H)-one
(benta-
zone), methyl 5-(2,4-dichloro-phenoxy)-2-nitro-benzoate (bifenox), 2,6-bis-
(4,6-
dimethoxy-pyrimidin-2-yl-oxy)-benzoic acid sodium salt (bispyribac-sodium),
3,5-
dibromo-4-hydroxy-benzonitrile (bromoxynil), [1,1-dimethyl-2-oxo-2-(2-propenyl-
oxy)]ethyl 2-chloro-S-(3,6-dihydro-3-methyl-2,6-dioxo-4-trifluoromethyl-1 (2H)-
pyrimidinyl)-benzoate (butafenacil-allyl), 2-(4-chloro-2-fluoro-5-(2-chloro-2-
ethoxy-
carbonyl-ethyl)-phenyl)-4-difluoromethyl-5-methyl-2,4-dihydro-3H-1,2,4-triazol-
3-
one (carfentrazone-ethyl), N-(4-methoxy-6-methyl-1,3,5-triazin-2-yl)-N'-(2-
chloro-
phenylsulphonyl)-urea (chlorsulfuron), N'-(3-chloro-4-methyl-phenyl)-N,N-di-
methyl-urea (chlorotoluron), ethyl 2-chloro-3-[2-chloro-5-(1,3,4,5,6,7-
hexahydro-
1,3-dioxo-2H-isoindol-2-yl)-phenyl]-2-propanoate (cinidon-ethyl), 2-propinyl
(R)-2-
[4-(5-chloro-3-fluoro-pyridin-2-yl-oxy)-phenoxy-propanoate (clodinafop-
propargyl),
3,6-dichloro-pyridine-2-carboxylic acid (clopyralid), 2-chloro-4-ethylamino-6-
(1-
cyano-1-methyl-ethylamino)-1,3,5-triazine (cyanazine), N-(4,6-dimethoxy-
pyrimidin-
2-yl)-N'-(2-cyclopropylcarbonyl-phenylsulphonyl)-urea (cyclosulfamuron), 2,4-
dichloro-phenoxyacetic acid (2,4-D), 3,6-dichloro-2-methoxy-benzoic acid
(dicam-
ba), (R)-2-(2,4-dichloro-phenoxy)-propanoic acid (dichlorprop-P), methyl 2-[4-
(2,4-
dichloro-phenoxy)-phenoxy]-propanoate (diclofop-methyl), 1,2-dimethyl-3,5-
diphenyl-1H-pyrazolium methyl sulphate (difenzoquat), N-(2,4-difluoro-phenyl)-
2-
(3-trifluoromethyl-phenoxy)-pyridine-3-carboxamide (diflufenican), 2-[1-[(3,5-
difluoro-phenyl)-amino-carbonyl-hydrazono]-ethyl]-pyridine-3-carboxylic acid
(diflufenzopyr), (S-) 2-chloro-N-(2,4-dimethyl-3-thienyl)-N-(2-methoxy-1-
methyl-
ethyl)-acetamide (S-) (dimethenamid), S-ethyl dipropyl thiocarbamate (EPTC),
(S)-
(2-ethoxy-1-methyl-2-oxoethyl)-2-chloro-5-(2-chloro-4-trifluoromethyl-phenoxy)-
benzoate (ethoxyfen), N-(4,6-dimethoxy-pyrimidin-2-yl)-N'-(2-ethoxy-phenoxy-
sulphonyl)-urea (ethoxysulfuron), ethyl (R)-2-[4-(6-chloro-benzoxazol-2-yl-
oxy)-
phenoxy]-propanoate (fenoxaprop-(P)-ethyl), isopropyl N-benzoyl-N-(3-chloro-4-
fluoro-phenyl)-DL-alaninate (flamprop-isopropyl), isopropyl N-benzoyl-N-(3-
chloro-
4-fluoro-phenyl)-L-alaninate (flamprop-isopropyl-L), methyl N-benzoyl-N-(3-
chloro-
4-fluoro-phenoxy)-DL-alaninate (flamprop-methyl), N-(2,6-difluoro-phenyl)-8-
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fluoro-5-methoxy-[1,2,4]-triazolo-[1,5-c]-pyrimidine-2-sulphonamide
(florasulam),
i-propyl 5-(4-bromo-1-methyl-5-trifluoromethyl-1H-pyrazol-3-yl)-2-chloro-4-
fluorobenzoate (fluazolate), 4,5-dihydro-3-methoxy-4-methyl-5-oxo-N-[(2-tri-
fluoromethoxy-phenyl)-sulphonyl]-1H-1,2,4-triazole-1-carboxamide sodium salt
(flucarbazone-sodium), N-(4-fluoro-phenyl)-N-i-propyl-2-(5-trifluoromethyl-
1,3,4-
thiadiazol-2-yl-oxy)-acetamide (flufenacet), N-(2,6-difluoro-phenyl)-5-methyl-
1,2,4-
triazolo[1,5-a]-pyrimidine-2-sulphonamide (flumetsulam), ethoxycarbonylmethyl
5-
(2-chloro-4-trifluoromethyl-phenoxy)-2-nitro-benzoate (fluoroglycofen-ethyl),
1-(4-
chloro-3-(2,2,3,3,3-pentafluoro-propoxymethyl)-phenyl)-5-phenyl-1 H-1,2,4-
triazole-
3-carboxamide (flupoxam), N-(4,6-dimethoxy-pyrimidin-2-yl)-N'-(3-methoxy-
carbonyl-6-trifluoromethyl-pyridin-2-yl-sulphonyl)-urea sodium salt
(flupyrsulfuron-
methyl-sodium), 9-hydroxy-9H-fluorene-9-carboxylic acid (flurenol), (2-butoxy-
1-
methyl-ethyl, 1-methyl-heptyl) (4-amino-3,5-dichloro-6-fluoro-pyridin-2-yl-
oxy)
acetate, (fluroxypyr, -butoxypropyl, -meptyl), 5-methylamino-2-phenyl-4-(3-tri-
fluoromethyl-phenyl)-3(2H)-furanone (flurtamone), methyl [(2-chloro-4-fluoro-5-
(tetrahydro-3-oxo-1 H,3H-[ 1,3,4]-thiadiazolo-[3,4-a]-pyridazin-1-ylidene)-
amino-
phenyl]-thio-acetate (fluthiacet-methyl), 2-[[[[(4,6-dimethoxy-2-pyrimidinyl)-
amino]-carbonyl]-amino]-sulphonyl]-4-formylamino-N,N-dimethyl-benzamide
(foramsulfuron), 2-amino-4-(hydroxymethylphosphinyl)-butanoic acid (ammonium
salt) (glufosinate (ammonium)), N-phosphonomethyl-glycine (isopropylammmonium
salt), (glyphosate, isopropylammonium), methyl 2-(4,5-dihydro-4-methyl-4-iso-
propyl-5-oxo-1H-imidazol-2-yl)-4-methyl-benzoate (imazamethabenz-methyl), 2-
(4, 5-dihydro-4-methyl-4-isopropyl-5-oxo-1 H-imidazol-2-yl)-5-methyl-pyridine-
3-
carboxylic acid (imazamethapyr), 2-(4,5-dihydro-4-methyl-4-isopropyl-5-oxo-1H-
imidazol-2-yl)-5-methoxymethyl-pyridine-3-carboxylic acid (imazamox), 2-(4,5-
di-
hydro-4-methyl-4-isopropyl-5-oxo-1H-imidazol-2-yl)-quinoline-3-carboxylic acid
(imazaquin), 2-(4,5-dihydro-4-methyl-4-i-propyl-5-oxo-1H-imidazol-2-yl)-S-
ethyl-
pyridine-3-carboxylic acid (imazethapyr), N-(4-methoxy-6-methyl-1,3, 5-triazin-
2-
yl)-N'-(5-iodo-2-methoxycarbonyl-phenylsulphonyl)-urea sodium salt
(iodosulfuron-
methyl-sodium), 4-hydroxy-3,5-diiodo-benzonitrile (ioxynil), N,N-dimethyl-N'-
(4-
isopropyl-phenyl)-urea (isoproturon), N-(3-(1-ethyl-1-methyl-propyl)-isoxazol-
5-yl)-
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2,6-dimethoxy-benzamide (isoxaben), (4-chloro-2-methylsulphonyl-phenyl)-(5-
cyclopropyl-isoxazol-4-yl)-methanone (isoxachlortole), (5-cyclopropyl-isoxazol-
4-
yl)-(2-methylsulphonyl-4-trifluoromethyl-phenyl)-methanone (isoxaflutole), (4-
chloro-2-methyl-phenoxy)-acetic acid (MCPA), 2-(4-chloro-2-methyl-phenoxy)-
propionic acid (mecoprop), 2-(4-methylsulphonyl-2-nitro-benzoyl)-1,3-
cyclohexane-
dione (mesotrione), 2-chloro-N-(2,6-dimethyl-phenyl)-N-(1H-pyrazol-1-yl-
methyl)-
acetamide (metazachlor), (S)-2-chloro-N-(2-ethyl-6-methyl-phenyl)-N-(2-methoxy-
1-
methyl-ethyl)-acet-amide (metolachlor, S-metolachlor), N-(2,6-dichloro-3-
methyl-
phenyl)-5,7-dimethoxy-1,2,4-triazolo[1,5-a]-pyrimidine-2-sulphonamide (meto-
sulam), 4-amino-6-tert-butyl-3-methylthio-1,2,4-triazin-5(4H)-one
(metribuzin), N-
(4-methoxy-6-methyl-1,3,5-triazin-2-yl)-N'-(2-methoxycarbonyl-phenylsulphonyl)-
urea (metsulfuron-methyl), N-(4,6-dimethoxy-pyrimidin-2-yl)-N'-(3-dimethylcarb-
amoyl-pyridin-2-yl-sulphonyl)-urea (nicosulfiuon), 1-amino-N-(1-ethyl-propyl)-
3,4-
dimethyl-2,6-dinitro-benzene (pendimethalin), N-(4,6-bis-difluoromethoxy-pyri-
midin-2-yl)-N'-(2-methoxycarbonyl-phenylsulphonyl)-urea (primisulfuron-
methyl),
2-chloro-N-isopropyl-N-phenyl-acetamide (propachlor), N-(3,4-dichloro-phenyl)-
propanamide (propanil), methyl 2-[[[(4,5-dihydro-4-methyl-5-oxo-3-propoxy-1H-
1,2,4-tri-
azol-1-yl)-carbonyl]-amino]-sulphonyl]-benzoate sodium salt (propoxycarbazone-
sodium),
S-phenylmethyl N,N-dipropyl-thiocarbamate (prosulfocarb), N-(4-methoxy-6-
methyl-1,3,5-triazin-2-yl)-N'-(2-(3,3,3-trifluoro-propyl)-phenylsulphonyl)-
urea (pro-
sulfuron), ethyl [2-chloro-5-(4-chloro-5-difluoromethoxy-1-methyl-1H-pyrazol-3-
yl)-
4-fluoro-phenoxy]-acetate (pyraflufen-ethyl), O-(6-chloro-3-phenyl-pyridazin-4-
yl)
S-octyl thiocarbonate (pyridate), 7-chloro-3-methyl-quinoline-8-carboxylic
acid
(quinmerac), N-(4,6-dimethoxy-pyrimidin-2-yl)-N'-(3-ethylsulfonyl-pyridin-2-yl-
sulphonyl)-urea (rimsulfuron), 2-(1-ethoximinobutyl)-5-(2-ethylthiopropyl)-3-
hy-
droxy-2-cyclohexen-1-one (sethoxydim), 6-chloro-2,4-bis-ethylamino-1,3,5-
triazine
(simazine), 2-(2-chloro-4-methylsulphonyl-benzoyl)-cyclohexane-1,3-dione
(sulco-
trione), N-phosphonomethylglycine-trimethylsulfonium (sulfosate), N-(4,6-di-
methoxy-pyrimidin-2-yl)-N' -(2-ethyl sulphonyl-imidazo [ 1,2-a]pyridin-3-
yl)sulphon-
amide (sulfosulfuron), 6-chloro-4-ethylamino-2-tert-butylamino-1,3,5-triazine
(ter-
buthylazine), 2-tert-butylamino-4-ethylamino-6-methylthio-1,3,5-triazine
(terbutryn),
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N-(4-methoxy-6-methyl-1, 3, 5-triazin-2-yl)-N'-(2-methoxycarbonyl-thien-3-yl-
sulphonyl)-urea (thifensulfuron-methyl), 2-(ethoximino-propyl)-3-hydroxy-5-
(2,4,6-trimethyl-phenyl)-2-cyclohexen-1-one (tralkoxydim), S-(2,3,3-trichloro-
2-
propenyl) diisopropylcarbamothioate (triallate), N-(4-methoxy-6-methyl-1,3,5-
triazin-2-yl)-N'-[2-(2-chloro-ethoxy)-phenylsulphonyl]-urea (triasulfuron), N-
meth-
yl-N-(4-methoxy-6-methyl-1,3,5-triazin-2-yl)-N'-(2-methoxycarbonyl-phenyl-
sulphonyl)-urea (tribenuron-methyl), 2-(3,5-dichloro-phenyl)-2-(2,2,2-
trichloro-
ethyl)-oxirane (tridiphane), N-[[(4,6-dimethoxy-2-pyrimidinyl)-amino]-
carbonyl]-3-
(2,2,2-trifluoro-ethoxy)-2-pyridinesulphonamide sodium salt
(trifloxysulfuron), 1-
amino-2,6-dinitro-N,N-dipropyl-4-trifluoromethyl-benzene (trifluralin).
Mixing components from the active compounds of group 3 which are particularly
emphasized are:
1-methylhexyl 5-chloro-quinoxalin-8-oxy-acetate (cloquintocet), ethyl 1-(2,4-
di-
chloro-phenyl)-5-trichloromethyl-1H-1,2,4-triazole-3-carboxylate (fenchlorazol-
ethyl),
ethyl 4,5-dihydro-5,5-diphenyl-3-isoxazolecarboxylate (isoxadifen-ethyl),
diethyl 1-
(2,4-dichlorophenyl)-4,5-dihydro-5-methyl-1H-pyrazole-3,5-dicarboxylate (mefen-
pyr-diethyl) and 2,4-dichlorophenoxyacetic acid (2,4-D) and its derivatives.
The compounds diethyl 1-(2,4-dichlorophenyl)-4,5-dihydro-5-methyl-1H-pyrazole-
3,5-
dicarboxylate (mefenpyr-diethyl), 1-methylhexyl [(5-chloro-8-
quinolinyl)oxy]acetate
(cloquintocet-methyl) and ethyl 1-(2,4-dichlorophenyl)-5-(trichloromethyl)-1H-
1,2,4-
triazole-3-carboxylate (fenchlorazole-ethyl) are described in the following
patent
applications: DE-A-39 39 503, EP-A-191 736 and DE-A-35 25 205, respectively.
2,4-
D is a known herbicide.
Surprisingly, it has now been found that the active compound combinations
defined
above of tritosulfuron and the abovementioned active compounds of group 1,
optionally in combination with active compounds of group 2 andlor active
compounds
of group 3, have particularly high herbicidal activity combined with very good
crop
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plant compatibility and can be used in various crops, in particular in wheat,
but
additionally in maize and barley for the selective control of weeds.
Surprisingly, the herbicidal activity of the active compound combinations
according to
the invention of tritosulfuron and compounds of the abovementioned group 1 is
considerably higher than the sum of the activities of the individual active
compounds.
This means that there is not only a complementary action but also an
unforeseeable
synergistic effect. The novel active compound combinations are tolerated well
by a
large number of crops, and the novel active compound combinations also
effectively
control weeds which are otherwise difficult to control. The novel active
compound
combinations are therefore a valuable addition to the selective herbicides.
Furthermore, it has surprisingly been found that the active compound
combinations
defined above of tritosulfuron and a safenerlantidote ("active compounds of
group 3")
in combination with one or more of the abovementioned active compounds of
group 1
have particularly high herbicidal activity combined with very good crop plant
compatibility and can be used in various crops, in particular in cereals,
especially
wheat, but also soya, potato, maize and rice, for the selective control of
weeds.
Moreover, it has surprisingly been found that the safener role described above
can also
be played by the herbicidally active substance 2,4-dichlorophenoxy-acetic acid
(2,4-D)
and its derivatives.
Furthermore, it is surprising that, from a large number of known safeners or
antidotes
capable of antagonizing the damaging effect of a herbicide on the crop plants,
there are
specifically the active compounds of group 3 listed above which neutralize the
damaging effect of tritosulfuron in combination with one or more of the
abovementioned active compounds of group 1 on the crop plants virtually
completely
without adversely affecting the herbicidal activity against the weeds.
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The particularly advantageous effect of the particularly preferred combination
partners of group 3, in particular with respect to sparing cereal plants, such
as, for
example, rice, wheat, barley and rye, as crop plants, may be emphasized here.
Very particular emphasis is given to mixtures of tritosulfuron and propoxy-
carbazone(-sodium) in combination with one or more of the following active
compounds:
N-(4,6-dimethoxy-pyrimidin-2-yl)-N'-(N-methyl-N-methylsulphonyl-sulphamoyl)-
urea
(amidosulfuron), 2,6-bis-(4,6-dimethoxy-pyrimidin-2-yl-oxy)-benzoic acid
sodium
salt (bispyribac-sodium), 2-(4-chloro-2-fluoro-5-(2-chloro-2-ethoxycarbonyl-
ethyl)-
phenyl)-4-difluoromethyl-5-methyl-2,4-dihydro-3H-1,2,4-triazol-3-one
(carfentra-
zone-ethyl), ethyl 2-chloro-3-[2-chloro-5-(1,3,4,5,6,7-hexahydro-1,3-dioxo-2H-
iso-
indol-2-yl)-phenyl]-2-propanoate (cinidon-ethyl), 2,4-dichloro-phenyloxyacetic
acid
(2,4-D), (R)-2-(2,4-dichloro-phenoxy)-propanoic acid (dichlorprop-P), N-(2,4-
di-
fluoro-phenyl)-2-(3-trifluoromethyl-phenoxy)-pyridine-3-carboxamide
(diflufenican),
N-(4-fluoro-phenyl)-N-i-propyl-2-(5-trifluoromethyl-1,3,4-thiadiazol-2-yl-oxy)-
acet-
amide (flufenacet), N-(4,6-dimethoxy-pyrimidin-2-yl)-N'-(3-methoxycarbonyl-6-
tri-
fluoromethyl-pyridin-2-yl-sulphonyl)-urea sodium salt (flupyrsulfuron-methyl-
sodium), (2-butoxy-1-methyl-ethyl, 1-methyl-heptyl) (4-amino-3,5-dichloro-6-
fluoro-
pyridin-2-yl-oxy)-acetate (fluroxypyr, -butoxypropyl, -meptyl), N-(4-methoxy-6-
methyl-1,3,5-triazin-2-yl)-N'-(5-iodo-2-methoxycarbonyl-phenylsulphonyl)-urea
sodium salt (iodosulfuron-methyl-sodium), N,N-dimethyl-N'-(4-isopropyl-phenyl)-
urea (isoproturon), 2-(4-chloro-2-methyl-phenoxy)-propionic acid (mecoprop), 4-
amino-6-tent-butyl-3-methylthio-1,2,4-triazin-5(4H)-one {metribuzin), N-[[(4,6-
di-
methoxy-2-pyrimidinyl)-amino]-carbonyl]-3-(2,2,2-trifluoro-ethoxy)-2-pyridine-
sulphonamide sodium salt (trifloxysulfuron).
Furthermore, very particular emphasis is given to mixtures of tritosulfuron
and
flucarbazone(-sodium) in combination with one or more of the following active
compounds:
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2,6-bis-(4,6-dimethoxy-pyrimidin-2-yl-oxy)-benzoic acid sodium salt
(bispyribac-
sodium), 3,5-dibromo-4-hydroxy-benzonitrile (bromoxynil), 2-(4-chloro-2-fluoro-
5-
(2-chloro-2-ethoxycarbonyl-ethyl)-phenyl)-4-difluoromethyl-5-methyl-2,4-
dihydro-
3H-1,2,4-triazol-3-one (carfentrazone-ethyl), ethyl 2-chloro-3-[2-chloro-5-
(1,3,4,5,6,7-hexahydro-1,3-dioxo-2H-isoindol-2-yl)-phenyl]-2-propanoate (cini-
don-ethyl), 2-propinyl (R)-2-[4-(S-chloro-3-fluoro-pyridin-2-yl-oxy)-phenoxy-
propanoate (clodinafop-propargyl), 3,6-dichloro-pyridine-2-carboxylic acid
(clopyralid), 2,4-dichloro-phenoxyacetic acid (2,4-D), 3,6-dichloro-2-methoxy-
benzoic acid (dicamba), ethyl (R)-2-[4-(6-chloro-benzoxazol-2-yl-oxy)-phenoxy]-
propanoate (fenoxaprop-(P)-ethyl), N-(2,6-difluoro-phenyl)-8-fluoro-S-methoxy-
[ 1,2,4]-triazolo-[ 1,5-c]-pyrimidine-2-sulphonamide (florasulam), N-(4-fluoro-
phen-
yl)-N-i-propyl-2-(5-trifluoromethyl-1,3,4-thiadiazol-2-yl-oxy)-acetamide
(flufenacet),
N-(4,6-dimethoxy-pyrimidin-2-yl)-N'-(3-methoxycarbonyl-6-trifluoromethyl-
pyridin-2-yl-sulphonyl)-urea sodium salt (flupyrsulfuron-methyl-sodium), (2-
butoxy-1-methyl-ethyl, 1-methyl-heptyl) (4-amino-3,5-dichloro-6-fluoro-pyridin-
2-
yl-oxy)-acetate (fluroxypyr, -butoxypropyl, -meptyl), methyl 2-(4,5-dihydro-4-
methyl-4-isopropyl-5-oxo-1H-imidazol-2-yl)-4-methyl-benzoate (imazamethabenz-
methyl), 2-(4,5-dihydro-4-methyl-4-isopropyl-5-oxo-1H-imidazol-2-yl)-5-methoxy-
methyl-pyridine-3-carboxylic acid (imazamox), N-(4-methoxy-6-methyl-1,3,5-
triazin-2-yl)-N'-(5-iodo-2-methoxycarbonyl-phenylsulphonyl)-urea sodium salt
(iodosulfuron-methyl-sodium), N,N-dimethyl-N'-(4-isopropyl-phenyl)-urea
(isoprot-
uron), (4-chloro-2-methyl-phenoxy)-acetic acid (MCPA), 2-(4-chloro-2-methyl-
phen-
oxy)-propionic acid (mecoprop), 4-amino-6-tent-butyl-3-methylthio-1,2,4-
triazin-
5(4H)-one (metribuzin), methyl 2-[[[(4,5-dihydro-4-methyl-5-oxo-3-propoxy-1H-
1,2,4-triazol-1-yl)-carbonyl]-amino]-sulphonyl]-benzoate sodium salt
(propoxycarb-
azone-sodium), ethyl [2-chloro-5-(4-chloro-5-difluoromethoxy-1-methyl-1H-
pyrazol-
3-yl)-4-fluoro-phenoxy]-acetate (pyraflufen-ethyl), N-(4,6-dimethoxy-pyrimidin-
2-yl)-
N'-(2-ethylsulphonyl-imidazo[1,2-a]pyridin-3-yl)sulphonamide (sulfosulfuron),
N-
(4-methoxy-6-methyl-1,3,5-triazin-2-yl)-N'-(2-methoxycarbonyl-thien-3-yl-
sulphonyl)-urea (thifensulfuron-methyl), 2-(ethoximino-propyl)-3-hydroxy-5-
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(2,4,6-trimethyl-phenyl)-2-cyclohexen-1-one (tralkoxydim), S-(2,3,3-trichloro-
2-
propenyl) diisopropyl carbamothioate (triallate), N-[[(4,6-dimethoxy-2-
pyrimidinyl)-
amino]-carbonyl]-3-(2,2,2-trifluoro-ethoxy)-2-pyridinesulphonamide sodium salt
(tri-
floxysulfuron).
The active compound combinations according to the invention can be used, for
example, in connection with the following plants:
Dicotyledonous weeds of the e~ nera: Sinapis, Lepidium, Galium, Stellaria,
Matricaria,
Anthemis, Galinsoga, Chenopodium, Urtica, Senecio, Amaranthus, Portulaca,
Xanthium, Convolvulus, Ipomoea, Folygonum, Sesbania, Ambrosia, Cirsium,
Carduus,
Sonchus, Solanum, Rorippa, Rotala, Lindernia, Lamium, Veronica, Abutilon,
Emex,
Datura, Viola, Galeopsis, Papaver, Centaurea, Trifolium, Ranunculus,
Taraxacum.
Dicotyledonous crops of the eg nera_ Gossypium, Glycine, Beta, Daucus,
Phaseolus,
Pisum, Solanum, Linum, Ipomoea, Vicia, Nicotiana, Lycopersicon, Arachis,
Brassica,
Lactuca, Cucumis, Cucurbita.
Monocotyledonous weeds of the eg, nera: Echinochloa, Setaria, Panicum,
Digitaria,
Phleum, Poa, Festuca, Eleusine, Brachiaria, Lolium, Bromus, Avena, Cyperus,
Sorghum, Agropyron, Cynodon, Monochoria, Fimbristylis, Sagittaria, Eleocharis,
Scirpus, Paspalum, Ischaemum, Sphenoclea, Dactyloctenium, Agrostis,
Alopecurus,
Apera, Phalaris.
Monocotyledonous crops of the e~ nera: Oryza, Zea, Triticum, Hordeum, Avena,
Secale, Sorghum, Panicum, Saccharum, Ananas, Asparagus, Allium.
However, the use of the active compound combinations according to the
invention is in
no way restricted to these genera, but also extends in the same manner to
other plants.
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According to the invention, it is possible to treat all plants and parts of
plants. By
plants are understood here all plants and plant populations, such as desired
and
undesirable wild plants or crop plants (including naturally occurring crop
plants).
Crop plants can be plants which can be obtained by conventional breeding and
optimization methods or by biotechnological and genetic engineering methods or
combinations of these methods, including transgenic plants and including plant
varieties which can or cannot be protected by varietal property rights. Parts
of plants
are to be understood as meaning all above-ground and below-ground parts and
organs
of plants, such as shoot, leaf, flower and root, examples which may be
mentioned
being leaves, needles, stems, trunks, flowers, fruit-bodies, fruits and seeds
and also
roots, tubers and rhizomes. Parts of plants also include vegetative and
generative
propagation material, for example seedlings, tubers, rhizomes, cuttings and
seeds.
The treatment of the plants and parts of plants according to the invention
with the
active compounds is carned out directly or by action on their environment,
habitat or
storage area according to customary treatment methods, for example by dipping,
spraying, evaporating, atomizing, broadcasting, brushing on and, in the case
of
propagation material, in particular in the case of seeds, furthermore by one-
or multi-
layer coating.
The synergistic effect of the active compound combinations according to the
invention
is particularly strongly pronounced at certain concentration ratios. However,
the ratios
by weight of the active compounds in the active compound combinations can be
varied
within relatively wide ranges. In general, from 0.01 to 1000 parts by weight,
preferably
from 0.05 to 500 parts by weight and particularly preferably from 0.1 to 100
parts by
weight of one of the compounds of group 1 are present per part by weight of
trito-
sulfuron.
The advantageous effect of the crop plant compatibility of the active compound
combinations according to the invention is likewise particularly strongly
pronounced at
certain concentration ratios. However, the ratios by weight of the active
compounds in
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the active compound conbinations can be varied within relatively wide ranges.
In
general, from 0.001 to 1000 parts by weight, preferably from 0.01 to 100 parts
by
weight and particularly preferably from 0.1 to 10 parts by weight of active
compound
of group 3 are present per part by weight of tritosulfuron or its mixtures
with active
compounds of group 1 and optionally with active compounds of group 2.
The active compound combinations can be converted into the customary
formulations,
such as solutions, emulsions, wettable powders, suspensions, powders, dusts,
pastes,
soluble powders, granules, suspo-emulsion concentrates, natural and synthetic
substances impregnated with active compound, and very fine encapsulations in
poly-
meric substances.
These formulations are produced in a known manner, for example by mixing the
active
compounds with extenders, that is liquid solvents and/or solid Garners,
optionally with
the use of surface-active agents, that is emulsifying agents and/or dispersing
agents
and/or foam-forming agents.
If the extender used is water it is also possible to use, for example, organic
solvents as
auxiliary solvents. Suitable liquid solvents are in the main: aromatics, such
as xylene,
toluene or alkylnaphthalenes, chlorinated aromatics and chlorinated aliphatic
hydro-
carbons, such as chlorobenzenes, chloroethylenes or methylene chloride,
aliphatic
hydrocarbons, such as cyclohexane or paraffins, for example petroleum
fractions,
mineral and vegetable oils, alcohols, such as butanol or glycol as well as
their ethers
and esters, ketones, such as acetone, methyl ethyl ketone, methyl isobutyl
ketone or
cyclohexanone, strongly polar solvents, such as dimethylformamide and dimethyl
sulphoxide, as well as water.
Suitable solid carriers are:
for example ammonium salts and ground natural minerals, such as kaolins,
clays, talc,
chalk, quartz, attapulgite, montmorillonite or diatomaceous earth, and ground
synthetic
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minerals, such as finely divided silica, alumina and silicates; suitable solid
Garners for
granules are: for example crushed and fractionated natural rocks such as
calcite,
marble, pumice, sepiolite and dolomite, as well as synthetic granules of
inorganic and
organic meals, and granules of organic material such as sawdust, coconut
shells, maize
cobs and tobacco stalks; suitable emulsifying and/or foam-forming agents are:
for
example nonionic and anionic emulsifiers, such as polyoxyethylene fatty acid
esters,
polyoxyethylene fatty alcohol ethers, for example alkylaryl polyglycol ethers,
alkylsulphonates, alkyl sulphates, arylsulphonates as well as protein
hydrolysates;
suitable dispersing agents are: for example lignin-sulphite waste liquors and
methylcellulose.
Tackifiers such as carboxymethylcellulose and natural and synthetic polymers
in the
form of powders, granules or latexes, such as gum arabic, polyvinyl alcohol
and
polyvinyl acetate, as well as natural phospholipids, such as cephalins and
lecithins, and
synthetic phospholipids, can be used in the formulations. Other possible
additives are
mineral and vegetable oils.
It is possible to use colorants such as inorganic pigments, for example iron
oxide,
titanium oxide and Prussian Blue, and organic dyestuffs, such as alizarin
dyestuffs, azo
dyestuffs and metal phthalocyanine dyestuffs, and trace nutrients such as
salts of iron,
manganese, boron, copper, cobalt, molybdenum and zinc.
The formulations in general comprise between 0.1 and 95 per cent by weight,
preferably between 0.5 and 90%, of active compounds, including the safeners.
In general, the active compound combinations according to the invention are
applied in
the form of ready mixes. However, the active compounds which the active
compound
combinations comprise can also be formulated individually and mixed upon use,
i.e.
applied in the form of tank mixes.
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The novel active compound combinations can be used as such or in the form of
their
formulations, and furthermore also as mixtures with other known herbicides,
ready
mixes or tank mixes again being possible. They may also be mixed with other
known
active compounds, such as fungicides, insecticides, acaricides, nematicides,
bird
repellents, growth substances, plant nutrients and agents which improve soil
structure.
For particular application purposes, in particular when applied post-
emergence, it may
furthermore be advantageous to incorporate, in the formulations, mineral or
vegetable
oils which are tolerated by plants (for example the commercial product "Rako
Binol")
or ammonium salts such as, for example, ammonium sulphate or ammonium
thiocyanate, as further additives.
The novel active compound combinations can be used as such, in the form of
their
formulations or in the use forms prepared therefrom by further dilution, such
as ready-
to-use solutions, suspensions, emulsions, powders, pastes and granules. They
are used
in the customary manner, for example by watering, spraying, atomizing, dusting
or
scattering.
'The active compound combinations according to the invention can be applied
before
and after the plants have emerged, that is to say pre-emergence and post-
emergence.
They can also be incorporated into the soil before sowing.
A synergistic effect in herbicides is always present when the herbicidal
activity of the
active compound combination exceeds the activity of the active compounds when
applied individually.
The expected activity for a given combination of two herbicides can be
calculated as
follows (cf. COLBY, S.R.: "Calculating synergistic and antagonistic responses
of
herbicide combinations", Weeds 15, pages 20 - 22, 1967):
If X = % damage by herbicide A at an application rate of p kg/ha
and Y = % damage by herbicide B at an application rate of q kg/ha
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and E = the expected damage of the herbicides A and B at application rates of
p and q kg/ha,
then E = X + y - (X * Y/100).
If the actual damage exceeds the calculated value, then the activity of the
combination is superadditive, i.e. a synergistic effect exists.
For a combination of three herbicides, the fomula is:
E - X+Y+Z - ((X*Y + X*Z + Y*Z)/100) + (X*Y*Z/10,000),
where
Z - % damage by herbicide C at an application rate of r kglha.
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Use Examples
Customary formulations of the active compounds in question were used.
Propoxycarbazone-sodium was used as 70 WG and tritosulfuron as 71.4 WG
formulation. From the active compounds, an aqueous spray liquor containing 0.1
% of
the additive Renex-36 was prepared.
Egamule A
Post-emergence/greenhouse
Test plants are grown in a greenhouse under controlled conditions (temperature
and
light conditions). When the plants have reached a height of 5 to 15 cm, they
are
sprayed with the test solution. The concentration of the spray liquor is
chosen such
that the particular amounts of active compound desired are applied in 5001 of
water/ha.
After the spray treatment, the plant containers are stored in a greenhouse at
constant
light and temperature conditions.
After about 3 weeks, the degree of damage to the crop plants is rated in %
damage in
comparison to the development of the untreated control.
The figures denote:
0 % - no damage (like untreated control)
100 % = total destruction/damage
Active compounds, application rates, test plants and results are shown in the
tables
below, where the abbreviations used in the tables have the following meanings:
a.i. = active ingredient = active compound
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Table A-1
Application Bromus Bromus
rate secalinus secalinus
g of ai/ha observed calculated*
propoxycarbazone-sodium 3 0 95
tritosulfuron 15 0
8 0
propoxycarbazone-sodium 30+15 100 95
+ 30+8 100 95
tritosulfuron
Table A-2
Application Abutilon Abutilon
rate theophrastitheophrasti
g of ai/ha observed calculated*
propoxycarbazone-sodium 3 0 20
15 0
tritosulfuron 30 40
15 0
propoxycarbazone-sodium 30+30 80 52
+ 15+30 80 40
tritosulfuron 30+15 70 20
15+15 70 0
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Table A-3
ApplicationChenopodiurnChenopodium
rate album album
g of ai/haobserved calculated*
propoxycarbazone-sodium30 60
tritosulfuron 8 40
propoxycarbazone-sodium30+8 100 76
tritosulfuron
Table A-4
ApplicationPolco Polco
rate conudvulus conudvulus
g of ai/haobserved calculated*
propoxycarbazone-sodium30 0
tritosulfuron 30 50
8 0
propoxycarbazone-sodium30+30 80 50
+ 30+8 40 0
tritosulfuron
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Table A-5
ApplicationSolanum Solanum
rate nigrum nigrum
g of ai/haobserved calculated*
propoxycarbazone-sodium30 50
15 50
tritosulfuron 30 70
15 70
8 30
propoxycarbazone-sodium30+30 100 85
+ 15+30 98 85
tritosulfuron 30+15 98 85
15+15 95 85
30+8 98 65
Table A-6
ApplicationStellaria Stellaria
media media
rate observed calculated*
g of ai/ha
propoxycarbazone-sodium30 20
tritosulfuron 8 50
propoxycarbazone-sodium30+8 100 60
tritosulfuron
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Table A-7
ApplicationVeronica persicaVeronica persica
rate observed calculated*
g of ai/ha
propoxycarbazone-sodium30 20
tritosulfuron 3 0 40
propoxycarbazone-sodium30+30 90 52
tritosulfuron
Table A-8
ApplicationViola arvensisViola arvensis
rate observed calculated*
g of ai/ha
propoxycarbazone-sodium30 60
15 30
tritosulfuron 15 0
propoxycarbazone-sodium30+15 95 60
+ 15+15 70 30
tritosulfuron
* values calculated by the method of Colby
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