Title of Invention

SELECTIVE HERBICIDES BASED ON 2,6-DISUBSTITUTED PYRIDINE DERIVATIVES

Abstract The inventon relates to novel herbicidal synergistic active compound combinations comprising,on the one hand,known 2,6-distributed pyridine derivatives and,on the other hand,known and herbicidally active compounds and/or safeners and which can be used particularly sucessfully for the control of weeds in various crops of useful plants,in particular cereal.
Full Text FORM 2
THE PATENTS ACT 1970
[39 OF 1970]
COMPLETE SPECIFICATION
[See Section 10]
"SELECTIVE HERBICIDES BASED ON 2,6-DISUBSTITUTED PYRIDINE DERIVATIVES"


BAYER AKTIENGESELLSCHAFT, A company of Germany., D-51368 Leverkusen, Germany

GRANTED
30-8-2007
The following specification particularly describes and ascertain the nature of the invention and the manner in which it is to be performed :-


Selective herbicides based on 2,6-disubstituted pyridine derivatives
The invention relates to novel herbicidal synergistic active compound combinations
comprising, on the one hand, known 2,6-disubstituted pyridine derivatives and, on the
other hand, known herbicidally active compounds and/or safeners and which can be
used particularly successfully for the selective control of weeds in various crops of useful plants.
As herbicides with broad action, 2,6-disubstituted pyridine derivatives form part of the subject-matter of a number of patent applications (cf. EP-A 447 004, WO-A 94/22833). However, the known pyridine derivatives have a number of gaps in their activity. The compatibility of these compounds with crop plants is likewise not entirely satisfactory under all conditions.
Surprisingly, it has now been found that a number of known active compounds from
the group of the 2,6-disubstituted pyridine derivatives, used jointly with known herbicidally active compounds from different substance classes, show pronounced synergistic effects with respect to the activity against weeds, and that such broadly active compound preparations can be used particularly advantageously for the selective
control of weeds in crops of useful plants, such as, for example, wheat.
Surprisingly, it has also been found that the 2,6-disubstituted pyridine derivatives, on
their own or together with known herbicidally active compounds, when used jointly
with the crop-plant-compatibility-improving compounds (safeners/antidotes) described
below, prevent damage to the crop plants particularly well and can be used particularly
advantageously as a broadly active combination preparation for the selective control of weeds in crops of useful plants, for example cereal.
The invention provides selective herbicidal compositions, characterized in that they
comprise an effective amount of an active compound combination comprising


(a) at least one 2,6-disubstituted pyridine derivative of the general formula (I)

in which
R1 represents a 5- or 6-membered heterocycle comprising 1 to 3 nitrogen atoms which is optionally mono- or polysubstituted by halogen and/or C1-C3-halogenoalkyl or represents a phenyl radical which is optionally mono- or polysubstituted by halogen and/or C1-C3-halogenoalkyl,
R represents a phenoxy radical which is optionally substituted by halogen and/or C1-C3-halogenoalkyl,
R represents a hydrogen atom or methyl, and
W represents oxygen or the group -CO-NH-,
("active compounds of group 1")
and
b) one or more compounds of a second group of herbicides comprising the active compounds mentioned below:
N-isopropyl-N-(4-fluorophenyl)-(5-trifluoromethyl-l,3,4-thiadiazol-2-yl-oxy)-acetamide (flufenacet, DE-38 21 600), 2-(2-methoxycarbonyl-phenylsulphonylaminocarbonyl)-4-methyl-5-n-propoxy-2,4-dihydro-3H-l,2,4-triazol-3-one or the sodium salt of this compound (propoxycarbazone-

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sodium, EP-A-507 171), 2-(2-trifluoromethoxy-phenylsulphonylamino-carbonyl)-4-methyl-5-methoxy-2,4-dihydro-3H-l,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 1039779), N-2-benzothiazolyl-N,N"-dimethylurea (methabenzthiazuron, GB-A 1085430), 4-amino-6-(l,l-dimethy lethy l)-3 -(methyl thio)-1,2,4-triazin-5 (4H)-one (metribuzin, DE-A 1795784), 4-(2-chlorophenyl)~N-cyclohexyl-N-ethyl-4,5-dihydro-5-oxo-lH-tetrazol-1-carboxamide (fentrazamide, EP-A 612 735), 4-amino-3-methyl-6-phenyl-l,2,4-triazin-5(4H)-one (metamitron, DE-A 2138031), 2-(2-benzo-thiazolyloxy)-N-methyl-N-phenylacetamide (mefenacet, DE-A 2822155), 4-amino-6-( 1,1 -dimethylethyl)-3 -(ethylthio)-1,2,4-triazin-5(4H)-one (ethio-zin, DE-A 1542873) or 1-methylethyl 5-[4-bromo-l-methyl-5-(trifluoro-methyl)-lH-pyrazol-3-yl]-2-chloro-4-fluorobenzoate (fluazolate, WO-A 9206962)
("active compounds of group 2"),
and optionally
(c) additionally at least one crop-plant-compatibility-improving compound from the following group of compounds:
a-(l,3-dioxolan-2-yl-methoximino)-phenylacetonitrile (oxabetrinil), a-(cyanomethoximino)-phenylacetonitrile (cyometrinil), 4-chloro-N-(l,3-di-oxolan-2-yl-methoxy)-a-trifluoro-acetophenoneoxime (fluxofenim), 4,6-dichloro-2-phenyl-pyrimidine (fenclorim), 4-dichloroacetyl-3,4-dihydro-3-methyl-2H-l,4-benzoxazine (benoxacor), 1-methyl-hexyl 5-chloro-quin-oxaIin-8-oxy-acetate (cloquintocet), 2,2-dichloro-N-(2-oxo-2-(2-propenyl-amino)-ethyl)-N-(2-propenyl)-acetamide (DKA-24), 1,8-naphthalic anhy¬dride, ethyl 1 -(2,4-dichloro-phenyl)-5-trichloromethyl-1H-1,2,4-triazole-3-carboxylate (fenchlorazol-ethyl), phenylmethyl 2-chloro-4-trifluoromethyl-


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thiazole-5-carboxylate (flurazole), 3-dichloroacetyl-5-(2-furanyl)-2,2-dimeth-yl-oxazolidine (furilazole, MON-13900), 4-dichloroacetyl-l-oxa-4-aza-spiro[4.5]-decane (AD-67), 2-dichloromethyl-2-methyl-l,3-dioxolane (MG-191), 2,2-dichloro-N-( 1,3 -dioxolan-2-y l-methyl)-N-(2-propeny l)-acetamide (PPG-1292), 2,2-dichloro-N,N-di-2-propenyl-acetamide (dichlormid), N-(4-methyl-phenyl)-N"-(l -methyl- l-phenyl-ethyl)-urea (dymron), 1 -dichlor-oacetyl-hexahydro-3,3,8a-trimethylpyrrolo[l,2-a]-pyrimidin-6(2H)-one (B AS-145138), N-(2-methoxy-benzoyl)-4-(methylaminocarbonylamino)-benzenesulphonamide, ethyl 4,5-dihydro-5,5-diphenyl-3-isoxazolecarboxylate (isoxadifen-ethyl), diethyl 1 -(2,4-dichlorophenyl)-4,5-dihydro-5-methyl-lH-pyrazole-3,5 -dicarboxylate (mefenpyr-diethyl) (4-chloro-2-methyl-phenoxy)-acetic acid (MCPA), (+-)-2-(4-chloro-2-methylphenoxy)propanoic acid (mecoprop), 3-dichloroacetyl-2,2,5-trimethyl-oxazolidine (R-29148) and 2,4-dichlorophenoxyacetic acid (2,4-D) and its derivatives
("active compounds of group 3"),
and optionally
20 (d) additionally one or more compounds from a third group of herbicides
comprising 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
25 salt (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-l ,3,5-triazine-2,4-diamine (ametryn), 4-amino-N-( 1,1 -dimethyl-ethyl)-4,5-dihydro-3-( 1 -methyl-ethyl)-5-oxo-1H-1,2,4-triazole-1 -carboxamide (amicarbazone), N-(4,6-dimetb.oxy-pyrimidin-
3 0 2-yl)-N"-(N-methyl-N-methylsulphonyl-sulphamoyl)-urea (amidosulfuron),
lH-l,2,4-triazol-3-amine (amitrole), 6-chloro-4-ethylamino-2-isopropyl-


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amino-1,3,5-triazine (atrazine), 2-[2,4-dichloro-5-(2-propinyloxy)-phenyl]-5,6,7,8-tetrahydro-l,2,4-triazolo-[4,3-a]-pyridin-3(2H)-one (azafenidin), N-(4,6-dimethoxy-pyrimidin-2-yl)-N"-[l-methyl-4-(2-methyl-2H-tetrazol-5-yl)-lH-pyrazol-5-ylsulphonyl]-urea (azimsulfuron), N-benzyl-2-(4-fluoro-3-tri-fluoromethyl-phenoxy)-butanamide (beflubutamide), 4-chloro-2-oxo-3(2H)-benzothiazoleacetic acid (benazolin), N-butyl-N-ethyl-2,6-dinitro-4-tri-fluoromethyl-benzenamine (benfluralin), N-(4,6-dirnethoxy-pyrimidin-2-yl)-N"-(2-methoxycarbonyl-phenylmethylsulphonyl)-urea (bensulfiiron), methyl 2-[2-[4-(3,6-dihydro-3-methyl-2,6-dioxo-4-trifluoromethyl-l(2H)-pyrimidin-
10 yl)phenoxy]methyl]-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-lH-2,1,3-benzothiadiazin-4(3H)-one (benta-zone), methyl 5-(2,4-dichloro-phenoxy)-2-nitro-benzoate (bifenox), 2,6-bis-
1 5 (4,6-dimethoxy-pyrimidin-2-yl-oxy)-benzoic acid sodium salt (bispyribac-
sodium), 2-bromo-3,3-dimethyl-N-(l-methyl-l-phenyl-ethyl)-butanamide (bromobutide), 0-(2,4-dinitro-phenyl) 3,5-dibromo-4-hydroxy-benzaldehyde-oxime (bromofenoxim), 3,5-dibromo-4-hydroxy-benzonitrile (bromoxynil), N-butoxymethyl-2-chloro-N-(2,6-diethyl-phenyl)-acetamide (butachlor), [1,1-
20 dimethyl-2-oxo-2-(2-propenyloxy)]-ethyl 2-chloro-5-(3,6-dihydro-3-methyl-
2,6-dioxo-4-trifluoromethyl-l(2H)-pyrimidinyl)-benzoate (butafenacil-allyl), 2-(l-ethoximino-propyl)-3-hydroxy-5-[2,4,6-trimethyl-3-(l-oxo-butyl)-phenyl]-2-cyclohexen-l-one (butroxydim), S-ethyl bis-(2-methyl-propyl)-thiocarbamate (butylate), N,N-diethyl-3-(2,4,6-trimethyl-phenylsulphonyl)-
25 lH-l,2,4-triazole-l-carboxamide (cafenstrole), 2-[l-[(3-chloro-2-propenyl)-
oxy-imino]-propyl]-3-hydroxy-5-(tetrahydro-2H-pyran-4-yl)-2-cyclohexen-l-one (caloxydim, tepraloxydim), 2-(4-chloro-2-fluoro-5-(2-chloro-2-ethoxy-caibonyl-emyl)-phenyl)-4-difluoromemyl-5-memyl-2,4-dihydro-3H-l,2,4-triazol-3-one (carfentrazone-ethyl), 2,4-dichloro-l-(3-methoxy-4-nitro-phenoxy)-
30 benzene (chlomethoxyfen), 3-amino-2,5-dichloro-benzoic acid (chlor-
amben), N-(4-chloro-6-methoxy-pyrimidin-2-yl)-N"-(2-ethoxycarbonyl-


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phenylsulphonyI)-urea (chlorimuron-ethyl), 1,3,5-trichIoro-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 (chlortoluron), ethyl 2-chloro-3-[2-chloro-5-(l,3,4,5,6,7-hexahydro-l,3-dioxo-2H-isoindol-2-yl)-phenyl]-2-propanoate (cinidon-ethyl), N-(4,6-dimethoxy-l,3,5-triazin-2-yl)-N"-(2-(2-methoxy-ethoxy)-phenylsulphonyl)-urea (cinosulfuron), 2-[1-[2-(4-chloro-phenoxy)-propoxyamino]butyl]-5-(tetrahydro-2H-thiopyran-3-yl)-l,3-cyclo-hexanedione (clefoxydim), (E,E)-(+)-2-[ 1 -[[(3-chloro-2-propenyl)-oxyJ-
l0 imino]-propyl]-3-hydroxy-2-cyclohexen-l-one (clethodim), prop-2-inyl (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-[(5-ethoxy-7-fluoro[ 1,2,4]triazolo[ 1,5-c]pyrimidin-2-yl-sulphon-yl)-amino]-benzoate (cloransulam-methyl), 2-chloro-4-ethylamino-6-(l-
15 cyano-l-methyl-ethylamino)-l,3,5-triazine (cyanazine), N-(4,6-dimethoxy-
pyrimidin-2-yl)-N"-(2-cyclopropylcarbonyl-phenylsulphonyl)-urea (cyclo-sulfamuron), 2-(l-ethoximinobutyl)-3-hydroxy-5-(tetrahydro-2H-thiopyran-3-yl)-2-cyclohexen-l-one (cycloxydim), butyl (R)-2-[4-(4-cyano-2-fluoro-phenoxy)-phenoxy]-propanoate (cyhalofop-butyl), 2,4-dichloro-phenoxy-
20 acetic acid (2,4-D), 3,6-dichloro-2-methoxy-benzoic acid (dicamba), (R)-2-
(2,4-dichloro-phenoxy)-propanoic acid (dichlorprop-P), methyl-2-[4-(2,4-di-chloro-phenoxy)-phenoxy]-propanoate (diclofop-methyl), N-(2,6-dichIoro-phenyl)-5-ethoxy-7-fluoro-[l,2,4]-triazolo-[l,5-c]-pyrimidine-2-sulphon-amide (diclosulam), l,2-dimethyl-3,5-diphenyl-lH-pyrazolium methyl -
25 sulphate (difenzoquat), N-(2,4-difluoro-phenyl)-2-(3-trifluoromethyl-phen-
oxy)-pyridine-3-carboxamide (diflufenican), 2-[l-[(3,5-dihuoro-phenyl)-amino-carbonyl-hydrazono]-ethyl]-pyridine-3-carboxyIic acid (diflufenzo-pyr), S-(l-methyl-1-phenyl-ethyl) 1-piperidine-carbothioate (dimepiperate), (S-) 2-chloro-N-(2,4-dimethyl-3-thienyl)-N-(2-methoxy-1 -methyl-ethyl)-acet-
30 amide (S-) (dimethenamid), 2-amino-4-(l-fluoro-l-methyl-ethyl)-6-(l-
methyl-2-(3,5-dimethyl-phenoxy)-ethylamino)-l,3,5-triazine (dimexyflam),


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N3,N3-diethyl-2,4-dinitro-6-trifluoromethyl-l,3-diamino-benzene
(dinitramine), 6,7-dihydro-dipyrido[l,2-a:2",l "-c]pyrazinediium (diquat),
S,S-dimethyl 2-difluoromethyl-4-i-butyl-6-trifluoromethyl-pyridine-3,5-di-
carbothioate (dithiopyr), N"-(3,4-dichloro-phenyl)-N,N-dimethyl-urea (di-
5 uron), 2-[2-(3-chloro-phenyl)-oxiranylmethyl]-2-ethyl-1 H-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-
10 phenoxy)-benzoate (ethoxyfen), N-(4,6-dimethoxy-pyrimidin-2-yl)-N"-(2-
ethoxy-phenoxysulphonyl)-urea (ethoxysulfuron), ethyl (R)-2-[4-(6-chloro-benzoxazol-2-yl-oxy)-phenoxy]-propanoate (fenoxaprop-(P)-ethyl), 4-(2-chloro-phenyl)-N-cyclohexyl-N-ethyl-4,5-dihydro-5-oxo-lH-tetrazole-l-carboxamide (fentrazamide), isopropyl N-benzoyl-N-(3-chloro-4-fluoro-
15 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-fluoro-5-methoxy-[l,2,4]-triazolo-[l,5-c]-pyrimidine-2-sulphonamide (florasulam), butyl (R)-2-[4-(5-trifluoromethyl-pyridin-2-yl-
20 oxy)-phenoxy]-propanoate (fluazifop, -butyl, -P-butyl), i-propyl 5-(4-bromo-
l-methyl-5-trifluoromethyl-lH-pyrazol-3-yl)-2-chloro-4-fluoro-benzoate (flu-azolate), 4,5-dihydro-3-methoxy-4-methyl-5-oxo-N-[(2-trifluoromethoxy-phenyl)-sulphonyl]-l-H-l,2,4-triazoIe-l-carboxarnide sodium salt (flucarb-azone-sodium), N-(4-fluoro-phenyl)-N-i-propyl-2-(5-trifluoromethyl-1,3,4-
25 thiadiazol-2-yl-oxy)-acetamide (flufenacet), N-(2,6-difluoro-phenyl)-5-
methyl-l,2,4-triazolo[l,5-a]-pyrimidine-2-sulphonamide (flumetsulam), pentyl [2-chloro-4-fluoro-5-(l,3,4,5,6,7-hexahydro-l,3-dioxo-2H-isoindol-2-yl)-phenoxy]-acetate (flumiclorac-pentyl), 2-[7-fluoro-3,4-dihydro-3-oxo-4-(2-propinyl)-2H-1,4-benzoxazin-6-yl]-4,5,6,7-tetrahydro-1H-isoindole-1,3-dione (flumioxazin), 2-[4-chloro-2-fluoro-5-[(l-methyl-2-propinyl)-oxy]-phenyl]-4,5,6,7-tetrahydro-lH-isoindole-l,3(2H)-dione (flumipropyn), 3-


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chloro-4-chloromethyl-1 -(3-trifluoromethyl-phenyl)-2-pyrrolidinone (fluoro-
chloridone), ethoxycarbonylmethyl 5-(2-chloro-4-trifluoromethyl-phenoxy)-
2-nitro-benzoate (fluoroglycofen-ethyl), 1 -(4-chloro-3-(2,2,3,3,3-penta-
fluoro-propoxymethyl)-phenyl)-5-phenyl-lH-l,2,4-triazole-3-carboxamide
5 (flupoxam), 1 -isopropyI-2-chloro-5-(3,6-dihydro-3-methyl-2,6-dioxo-4-tri-
fluoromethyl-l(2H)-pyrimidyl)-benzoate (flupropacil), N-(4,6-dimethoxy-pyrimidm-2-yl)-K-(3-memoxycaroonyl-6-trifluoromethyl-pyridin-2-yl-sulphonyl)-urea sodium salt (flupyrsulfuron-methyl-sodium), 9-hydroxy-9H-fluorene-9-carboxylic acid (flurenol), (4-amino-3,5-dichloro-6-fluoro-pyridin-2-yl-oxy)-
10 acetic acid (2-butoxy-l-methyl-ethyl ester, 1-methyl-heptyl ester) (fluroxy-
pyr, -butoxypropyl, -meptyl), 5-methylamino-2-phenyl-4-(3-trifluoromethyl-phenyl)-3(2H)-furanone (flurtamone), methyl [(2-chloro-4-fluoro-5-(tetra-hydro-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-trifluoromethyl-
phenoxy)-N-methylsulphonyl-2-nitro-benzamide (fomesafen), 2-[[[[(4,6-di-
methoxy-2-pyrimidinyl)-amino]-carbonyl]-amino]-sulphonyl]-4-formyl-amino-N,N-dimethyI-benzamide (foramsulfuron), 2-amino-4-(hydroxymethyl-phosphinyl)-butanoic acid (ammonium salt) (glufosinate-(ammonium)), N-phosphonomethyl-glycine (isopropylammonium salt), (glyphosate, iso-
20 propylammonium), (R)-2-[4-(3-chloro-5-trifluoromethyl-pyridin-2-yl-oxy)-
phenoxy-propanoic acid (methyl ester, 2-ethoxy-ethyl ester, butyl ester) (haloxyfop, -methyl, -P-methyl, -ethoxyethyl, -butyl), 3-cyclohexyl-6-di-methylamino-1 -methyl-1,3,5-triazine-2,4( 1 H,3H)-dione (hexazinone), methyl 2-(4,5-dihydro-4-methyl-4-isopropyl-5-oxo-lH-imidazol-2-yl)-4-methyl-
20 benzoate (imazamethabenz-methyl), 2-(4,5-dihydro-4-methyl-4-isopropyl-5-
oxo-1H-imidazol-2-yl)-5-methyl-pyridine-3-carboxylic acid (imazametha-pyr), 2-(4,5-dihydro-4-methyl-4-isopropyl-5-oxo-lH-imidazol-2-yl)-5-methoxymethyl-pyridine-3-carboxylic acid (imazamox), 2-(4,5-dihydro-4-methyl-4-isopropyl-5-oxo-lH-imidazol-2-yl)-qumoline-3-earboxylic acid
30 (imazaquin), 2-(4,5-dihydro-4-methyl-4-i-propyl-5-oxo-lH-imidazol-2-yl)-5-
ethyl-pyridine-3-carboxylic acid (imazethapyr), N-(4,6-dimethoxy-pyrimidin-


2-yl)-N"-(2-chloro-imidazo[l,2-a]-pyridin-3-yl-sulphonyl)-urea (imazosulf-uron), N-(4-methoxy-6-methyl-l,3,5-triazin-2-yl)-N"-(5-iodo-2-methoxy-carbonyl-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-(l -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 (is-oxaflutole), 2-[2-[4-[(3,5-dichloro-2-pyridmyl)-oxy]-phenoxy]-l-oxo-propyl]-
l0 isoxazolidine (isoxapyrifop), (2-ethoxy-l-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 (meco-prop), 2-(2-benzothiazolyloxy)-N-methyl-N-phenyl-acetamide (mefenacet), 2-(4-methylsulphonyl-2-nitro-benzoyl)-1,3-cyclohexanedione (mesotrione), 4-amino-3-methyl-6-phenyM ,2,4-triazin-5(4H)-one (metamitron), 2-chloro-N-(2,6-dimethyl-phenyl)-N-( 1 H-pyrazol-1 -yl-methyl)-acetamide (metaza-chlor), N"-(4-(3,4-dihydro-2-methoxy-2,4,4-trimethyl-2H-1 -benzopyran-7-yl-oxy)-phenyl)-N-methoxy-N-methyl-urea (metobenzuron), N"-(4-bromo-
20 phenyl)-N-methoxy-N-methyl urea (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[l,5-a]-pyrimidine-2-sulphonamide (metosulam), N"-(3-chloro-4-methoxy-phenyl)-N,N-dimethyl-urea (metoxuron), 4-amino-6-tert-butyl-3-
25 methylthio-l,2,4-triazin-5(4H)-one (metribuzin), N-(4-methoxy-6-methyl-
1,3,5-triazin-2-yl)-N"-(2-methoxycarbonyl-phenylsulphonyl)-urea (metsulf-uron-methyl), S-ethyl-hexahydro-lH-azepine-1-carbothioate (molinate), 2-(2-naphthyloxy)-N-phenyl-propanamide (naproanilide), N-butyl-N"-(3,4-di-chloro-phenyl)-N-methyl-urea (neburon), N-(4,6-dimethoxy-pyrimidin-2-yl)-
30 N"-(3-dimethylcarbamoyl-pyridin-2-yl-sulphonyl)-urea (nicosulfuron), S-
(2-chloro-benzyl)-N,N-diethyl-thiocarbamate (orbencarb), 4-dipropylamino-

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3,5-dinitro-benzenesulphonamide (oryzalin), 3-[2,4-dichloro-5-(2-propinyl-
oxy)-phenyl]-5-(t-butyl)-l,3,4-oxadiazol-2(3H)-one (oxadiargyl), 3-[2,4-
dichloro-5-(l-methyl-ethoxy)-phenyl]-5-(t-butyl)-l,3,4-oxadiazol-2(3H)-one
(oxadiazon), N-(4,6-dimethyl-pyrimidin-2-yl)-N"-(2-oxetan-3-yl-oxycarbonyl-
5 phenylsulphonyl)-urea (oxasulfiiron), 3-[l-(3,5-dichloro-phenyl)-l-i-
propyl]-2,3-dihydro-6-methyl-5-phenyl-4H-l,3-oxazin-4-one (oxaziclo-mefone), 2-chloro-1 -(3-ethoxy-4-nitro-phenoxy)-4-trifluoromethylbenzene (oxyfluorfen), l,r-dimethyl-4,4"-bipyridinium (paraquat), l-amino-N-(l-ethyl-propyl)-3,4-dimethyl-2,6-dinitro-benzene (pendimethalin), 4-(t-butyl)-
10 N-(l-ethyl-propyl)-2,6-dinitro-benzenamine (pendralin), 4-amino-3,5,6-tri-
chloro-pyridine-2-carboxylic acid (picloram), 2-chloro-N-(2,6-diethyl-phenyl)-N-(2-propoxy-ethyl)-acetamide (pretilachlor), N-(4,6-bisdifluo-romethoxy-pyrimidin-2-yl)-N"-(2-methoxycarbonyl-phenylsulphonyl)-urea (primisulfuron-methyl), l-chloro-N-[2-chloro-4-fluoro-5-[(6S,7aR)-6-fluoro-
15 tetrahydro-1,3-dioxo-1 H-pyrrolo[l ,2-c]imidazol-2(3H)-yl]-phenyl]-methan-
esulphonamide (profluazol), 2-chloro-N-isopropyl-N-phenyl-acetamide (propachlor), N-(3,4-dichloro-phenyl)-propanamide (propanil), (R)-[2-[[(l-methyl-ethylidene)-amino]-oxy]-ethyl]-2-[4-(6-chloro-2-quinoxalinyloxy)-phenoxy]-propanoate(propaquizafop), 2-chloro-N-(2-ethyl-6-methyl-phenyl)-
2) N-[(l-methyl-ethoxy)-methyl]-acetamide (propisochlor), methyl 2-[[[(4,5-di-
hydro-4-methyl-5-oxo-3-propoxy-lH-l,2,4-triazol-l-yl)-carbonyl]-amino]-sulphonyl-benzoate sodium salt (propoxycarbazone-sodium), S-phenyl-methyl N,N-dipropyl-thiocarbamate (prosulfocarb), N-(4-methoxy-6-methyl-l,3,5-triazin-2-yl)-N-(2-(3;3,3-trifluoro-propyl)-phenylsulphoryl)-urea (pro-
25 sulfuron), ethyl [2-chloro-5-(4-chloro-5-difluoromethoxy-l-methyl-lH-pyr-
azol-3-yl)-4-fluoro-phenoxy]-acetate (pyraflufen-ethyl), l-(3-chloro-4,5,6,7-tetrahydro-pyrazoIo[l,5-a]pyridin-2-yl)-5-(methyl-2-propinylamino)-lH-pyr-azole-4-carbonitrile (pyrazogyl), 4-(2,4-dichloro-benzoyl)-1,3-dimethyl-5-(4-methyl-phenylsulphonyloxy)-pyrazole (pyrazolate), 4-(2,4-dichloro-benzoyl)-
3 0 l,3-dimethyl-5-(phenylcarbonylmethoxy)-pyrazole (pyrazoxyfen), N-(4,6-di-
methoxy-pyrimidin-2-yl)-N"-(4-ethoxycarbonyl-l-methyl-pyrazol-5-yl-

Le A 34 090 foretgn Countries


"sulphonyl)-urea (pyrazosulfuron-ethyl), 0-[2,6-bis-(4,6-dimethoxy-pyri-
m.idin-2-yl-oxy)-benzoyl] diphenylmethanone-oxime (pyribenzoxim), 6-
chloro-3-phenyl-4-pyridazinol (pyridafol), 0-(6-chloro-3-phenyl-pyridazin-4-
yl) S-octyl thiocarbonate (pyridate), 6-chloro-3-phenylpyridazin-4-ol
5 (pyridatol), 7-[(436-dimethoxy-2-pyrimidinyl)-thio] -3 -methyl- l(3H)-iso-
benzofuranone (pyriftalid), methyl 2-(4,6-dimethoxy-pyrimidin-2-yl-oxy)-benzoate (pyriminobac-methyl), 2-chloro-6-(4,6-dimethoxy-pyrimidin-2-yl-thio)-benzoic acid sodium salt (pyrithiobac-sodium), 3,7-dichloro-quinoline-8-carboxylic acid (quinchlorac), 7-chloro-3-methyl-quinoline-8-carboxylic
10 acid (quinmerac), 2-[4-(6-chloro-2-quinoxalinyloxy)-phenoxy]-propanoic
acid (ethyl ester, tetrahydro-2-furanyl-methyl ester) (quizalofop, -ethyl, -P-ethyl, -P-tefury1), N-(4,6-dimethoxy-pyrimidin-2-yl)-N"-(3-ethylsulphonyl-pyridin-2-yl-sulphonyl)-urea (rimsulfuron), 2-(1-ethoximinobutyl)-5-(2-ethyl-thiopropyl)-3-hydroxy-2-cyclohexen-l -one (sethoxydim), 6-chloro-2,4-bis-
1|5 ethylamino-l,3,5-triazine (simazin), 2-(2-chloro-4-methylsulphonyl-benzoyl)-
cyclohexane-1,3-dione (sulcotrione), 2-(2,4-dichloro-5-methylsulphonyl-amino-phenyl)-4-difluoromethyl-5-methyl-2,4-dihydro-3H-l,2,4-triazol-3-one (sulfentrazone), N-phosphonomethyl-glycine-trimethylsulphonium (sulfosate), N-(4,6-dimethoxy-pyrimidin-2-yl)-N"-(2-ethylsulphonyl)-imidazo[l,2-a]-
20 pyridine-3-sulphonamide (sulfosulfuron), 6-chloro-4-ethylamino-2-tert-
butylamino-l,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 (thenylchlor), methyl 2-difluoro-methyl-5-(4,5-dihydro-thiazol-2-yl)-4-(2-methyl-propyl)-6-trifluoromethyl-
25 pyridine-3-carboxylate (thiazopyr), 6-(6,7-dihydro-6,6-dimethyl-3H,5H-
pyrrolo[2,l-c]-l,2,4-thiadiazol-3-ylideneamino)-7-fluoro-4-(2-propinyl)-2H-l,4-benzoxazin-3(4H)-one (thidiazimin), N-(4-methoxy-6-methyl-l,3,5-tri-azin-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) diisopropyl-carbamothioate (triallate), N-(4-methoxy-6-methyl-1,3,5-triazin-2-yl)-N"-[2-


Le A 34 090-Foreign Countries
(2-chloro-ethoxy)-phenylsulphonyl]-urea (triasulfuron), N-methyl-N-(4-
methoxy-6-methyl-l,3,5-triazin-2-yl)-N"-(2-methoxycarbonyl-phenylsulphonyl)-
urea (tribenuron-methyl), (3,5,6-trichloro)-pyridin-2-yl-oxy-acetic acid (triclo-
pyr), 2-(3,5-dichloro-phenyl)-2-(2,2,2-trichloro-ethyl)-oxirane (tridiphane),
5 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), N-[4-di-methylamino-6-(2,2,2-trifluoro-ethoxy)-l,3,5-triazin-2-yl]-N"-(2-methoxy-carbonyl-phenylsulphonyl)-urea (triflusulfuron-methyl), N-(4-methoxy-6-
1 () trifluoromethoxy-1,3,5-triazin-2-yl)-N"-(2-trifluoromethyl-phenylsulphonyl)-
urea (tritosulfuron), 2-pyridinesulphonamide N-[[(4,6-dimethoxy-2-pyrimi-dinyl)amino]carbonyl]-3-(N-methyl-N-methylsulphonyl-amino) (cf. WO-A-92/10660), 2-[[[[(4,6-dimethoxy-2-pyrimidiny l)amino]carbony1] amino] -sulphonyl]-4-[[(methylsulphonyl)amino]methyl]-methyl benzoate (cf.
15 DE-A43 35 297), 4-[4,5-dihydro-4-methyl-5-oxo-(3-trifluoromethyl)-lH-
1,2,4-triazol-1 -yl]-2-[(ethylsulphonyl)amino]-5-fluoro-benzenecarbothio-amide (cf. WO-A-95/30661)
("active compounds of group 4"), 20
where the compound under (b) does not represent flufenacet if the compound under (a) is 2-(3,4-difluorophenoxy)-4-methyl-6-(l-methyl-3-trifluoromethyl-pyrazol-5-yl)-pyridine.
25 Preferred substituents of the radicals listed in formula (I) shown above are illustrated
below.
R1 preferably represents a pyrazolyl radical which is optionally mono- or
polysubstituted by trifluoromethyl and methyl or represents a phenyl radical
30 which is optionally mono- or polysubstituted by fluorine.


R2 preferably represents an optionally halogen- and/or C1-C3-halogenoalkyl-substituted phenoxy radical.
R3 preferably represents a hydrogen atom or methyl.
W preferably represents oxygen or the group -CO-NH-.
Among the active compounds of group 3, particular emphasis is given to the following mixing components:

15
1-methylhexyl 5-chloro-quinoxalin-8-oxy-acetate (cloquintocet), ethyl l-(2,4-dichloro-phenyl)-5-trichloromethyl-1H-1,2,4-triazole-3-carboxylate (fenchlorazol-ethyl), ethyl 4,5-dihydro-5,5-diphenyl-3-isoxazolecarboxylate (isoxadifen-ethyl), diethyl l-(2,4-dichlorophenyI)-4,5-dihydro-5-methyl-lH-pyrazole-3,5-dicarboxylate (mefenpyr-diethyl) and 2,4-dichlorophenoxyacetic acid (2,4-D) and its derivatives.
As described, the activity properties of the combinations described above can be
improved even more, if appropriate, by adding a compound from the third group of
herbicides ("active compounds of group 4"). Among the "active compounds of group
20 4", particular emphasis is given to the following mixing components:
4-amino-N-( 1,1 -dimethyl-ethyl)-4,5-dihydro-3-( 1 -methyl-ethyl)-5 -oxo-1H-1,2,4-triazole-1 -carboxamide (amicarbazone), N-(4,6-dimethoxy-pyrimidin-2-yl)-N"-(N-methyl-N-methylsulphonyl-sulphamoyl)-urea (amidosulfuron), N-benzyl-2-(4-
25 fluoro-3-trifluoromethyl-phenoxy)-butanamide (beflubutamide), 3-i-propyl-lH-2,l,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), 3,5-dibromo-4-hydroxy-benzonitrile (bromoxynil), N-butoxymethyl-2-chloro-N-(2,6-diethyl-phenyl)-acetamide (butachlor), [1,1-dimethyl-
30 2-oxo-2-(2-propenyloxy)]-ethyl 2-chloro-5-(3,6-dihydro-3-methyl-2,6-dioxo-4-tri-
fluoromethyl-l(2H)-pyrimidinyl)-benzoate (butafenacil-allyl), 2-(4-chloro-2-fluoro-


5-(2-chloro-2-ethoxycarbonyl-ethyl)-phenyl)-4-difluoromethyl-5-methyl-2,4-dihy-
dro-3H-l,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-dimethyl-urea (chlortoluron), ethyl 2-chloro-3-[2-chloro-5-
5 (1,3,4,5,6,7-hexahydro-1,3-dioxo-2H-isoindol-2-yl)-phenyl]-2-propanoate (cini-
don-ethyl), prop-2-inyl (R)-2-[4-(5-chloro-3-fluoro-pyridin-2-yl-oxy)-phenoxy]-pro-panoate (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
10 (cyclosulfamuron), 2,4-dichIoro-phenoxyacetic acid (2,4-D), 3,6-dichloro-2-
methoxy-benzoic acid (dicamba), (R)-2-(2,4-dichloro-phenoxy)-propanoic acid (dichlorprop-P), methyl-2-[4-(2,4-dichloro-phenoxy)-phenoxy]-propanoate (diclofop-methyl), l,2-dimethyl-3,5-diphenyl-lH-pyrazolium methylsulphate (difenzoquat), 2-ethoxy-1 -methyl-2-oxoethyl (S)-2-chloro-5-(2-chloro-4-trifluoromethyl-phenoxy)-
15 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)-phenoxyj-propanoate (fenoxaprop-(P)-ethyl), 4-(2-chloro-phenyl)-N-cyclohexyl-N-ethyl-4,5-dihydro-5-oxo-lH-tetrazole-l-carboxamide (fentrazamid), isopropyl N-benzoyl-N-(3-chloro-4-fluoro-phenyl)-DL-alaninate (flamprop-isopropyl), isopropyl
20 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-fluoro-5-methoxy-[l,2,4]-triazolo-[l,5-c]-pyrimidine-2-sulphon-amide (florasulam), i-propyl 5-(4-bromo-l-methyl-5-trifluoromethyl-lH-pyrazoI-3-yl)-2-chloro-4-fluoro-benzoate (fluazolate), 4,5-dihydro-3-methoxy-4-methyl-5-oxo-
25 N-[(2-trifluoromethoxy-phenyl)-sulphonyl]-1 -H-l ,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[l ,5-a]-pyrimidine-2-suIphonamide (flumetsulam), ethoxycarbonyl-methyl 5-(2-chloro-4-trifluoromethyl-phenoxy)-2-nitro-benzoate (fluoroglycofen-
30 ethyl), 1 -(4-chloro-3-(2,2,3,3,3-pentafluoro-propoxymethyl)-phenyl)~5-phenyl-1H-
1,2,4-triazole-3-carboxamide (flupoxam), N-(4,6-dimethoxy-pyrirnidin-2-yl)-N"-(3-

Le A 34 090-ForginCountries
-15-
methoxycarbonyl-6-trifluoromethyl-pyridin-2-yl-sulphonyl)-urea sodium salt (flu-pyrsulfuron-methyl-sodium), 9-hydroxy-9H-fluorene-9-carboxylic acid (flurenol), (4-amino-3,5-dichloro-6-fluoro-pyridin-2-yl-oxy)-acetic acid (2-butoxy-1 -methyl-ethyl ester, 1-methyl-heptyl ester) (fluroxypyr, -butoxypropyl, -meptyl), 5-methylamino-2-
5 phenyl-4-(3-trifluoromethyl-phenyl)-3(2H)-furanone (flurtamone), 2-amino-4-

(hydroxymethylphosphinyl)-butanoic acid (ammonium salt) (glufosinate-
(ammonium)), N-phosphonomethyl-glycine (isopropylammonium salt), (glyphosate,
isopropylammonium), methyl 2-(4,5-dihydro-4-methyl-4-isopropyl-5-oxo-lH-imid-
azol-2-yl)-4-methyl-benzoate (imazamethabenz-methyl), 2-(4,5-dihydro-4-methyl-4-
10 isopropyl-5-oxo-lH-imidazol-2-yl)-5-methoxymethyl-pyridine-3-carboxylic acid
(imazamox), 2-(4,5-dihydro-4-methyl-4-i-propyl-5-oxo-lH-imidazol-2-yl)-5-ethyl-pyridine-3-carboxylic acid (imazethapyr), N-(4-methoxy-6-methyl-l,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)-2,6-dimethoxy-benzamide (isoxaben), (4-chloro-2-methyl-phenoxy)-acetic acid (MCPA), 2-(4-chloro-2-methyl-phenoxy)-propionic acid (mecoprop), 2-(2-benzo-thiazolyloxy)-N-methyl-N-phenyl-acetamide (mefenacet), 4-amino-3-methyl-6-phenyl-1,2,4-triazin-5(4H)-one (metamitron), N-(2,6-dichloro-3-methyl-phenyl)-5,7-
20 dimethoxy-l,2,4-triazolo[l,5-a]-pyrimidine-2-sulphonamide (metosulam), 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 (metsulf-uron-methyl), 1-amino-N-(1-ethyl-propyl)-3,4-dimethyl-2,6-dinitro-benzene (pendi-methalin), N-(3,4-dichloro-phenyl)-propanamide (propanil), methyl 2-[[[(4,5-di-
25 hydro-4-methyl-5-oxo-3-propoxy-lH-l,2,4-triazol-l-yl)carbonyl]amino]sulphonyl]-
benzoate sodium salt (propoxycarbazone-sodium), S-phenylmethyl N,N-dipropyl-thiocarbamate (prosulfocarb), ethyl [2-chloro-5-(4-chloro-5-difluoromethoxy-l-methyl-lH-pyrazol-3-yl)-4-fluoro-phenoxy]-acetate (pyraflufen-ethyl), 7-chloro-3-methyl-quinoline-8-carboxyIic acid (quinmerac), N-phosphonomethyl-giycine-tri-
30 methylsulphonium (sulfosate), N-(4,6-dimethoxy-pyrimidin-2-yl)-N"-(2-ethyl-
sulphonyl)-imidazo[l,2-a]pyridine-3-sulphonamide (sulfosulfuron), 2-tert-butyl-


Le A 34 090-Foreign countries

amino-4-ethylamino-6-methylthio-1,3,5-triazine (terbutryn), N-(4-methoxy-6-meth-
yl-1,3,5-triazin-2-yl)-N"-(2-methoxycarbonyl-thien-3-yl-sulphony])-urea (thifensulf-
uron-methyl), 2-(ethoximino-propyl)-3-hydroxy-5-(2,4,6-trimethyl-phenyl)-2-cyclo-
hexen-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)-phenyl-
sulphonyl]-urea (triasulfuron), N-methyl-N-(4-methoxy-6-methyl-1,3,5-triazin-2-yl)-
N"-(2-methoxycarbonyl-phenylsulphonyl)-urea (tribenuron-methyl), N-[[(4,6-di-
methoxy-2-pyrimidinyl)amino]carbonyl]-3-(2,2,2-trifluoro-ethoxy)-2-pyridin-
sulphonamide sodium salt (trifloxysulfuron), l-amino-2,6-dinitro-N,N-dipropyl-
10 4-trifluoromethyl-benzene (trifluralin), N-(4-methoxy-6-trifluoromethoxy-1,3,5-
triazin-2-yl)-N"-(2-trifluoromethyl-phenylsulphonyl)-urea(tritosulfuron)
Very particular preference according to the invention is given to selective herbicidal
compositions which are characterized in that they comprise an active compound
15 combination comprising
a) N-(4-fluorophenyl)-6-[3-(trifluoromethyl)phenoxy]-2-pyridinecarboxamide (picolinafen) or 2-(3,4-difluorophenoxy)-4-methyl-6-(l-methyl-3-trifluoro-methylpyrazol-5 -yl)-pyridine
25
and

25

b) one or more compounds from a second group of herbicides which contains the active compounds mentioned above under (b) ("active compounds of group 2"),
where the compound from group (b) does not represent flufenacet if the compound (a) is 2-(3,4-difluorophenoxy)-4-methyl-6-(l-methyl-3*trifluoro-methylpyrazo 1-5 -y l)-pyridine,



30 and optionally




Le A 34 090-Foreign Countries
c) at least one of the abovementioned crop-plant-compatibility-improving compounds of the active compounds of group 3, where preference is given to those compounds which were emphasized above.
Most preference according to the invention is given to the selective herbicidal compositions which comprise, as compound of the active compounds of group 1, picolinafen.
Emphasis is furthermore given to selective herbicidal compositions which are characterized in that they comprise an active compound combination comprising
(a) picolinafen and
(b) N-isopropyl-N-(4-fluorophenyl)-(5-trifluoromethyl-1,3,4-thiadiazol-2-yl~ 15 oxy)-acetamide (flufenacet) and
(c) optionally one or more compounds from the group consisting of 2,6-bis-(4,6-
dimethoxy-pyrimidin-2-yl-oxy)-benzoic acid sodium salt (bispyribac-
sodium), N-(2,6-difluoro-phenyl)-8-fluoro-5-methoxy-[l,2,4]-triazolo-[l,5-
20 c]-pyrimidine-2-sulphonamide (florasulam), N-(4,6-dimethoxy-pyrimidin-2-
yl)-N-(3-methoxycarbonyl-6-trifluoromethyl-pyridin-2-yl-sulphonyl)-urea sodium salt (flupyrsulfuron-methyl-sodium), N,N-dimethyl-N"-(4-isopropyl-phenyl)-urea (isoproturon), N-(2,6-dichloro-3-methyl-phenyl)-5,7-dimethoxy-l,2,4-triazolo[l,5-a]-pyrimidine-2-sulphonamide (metosulam), l-amino-N-(l-
25 ethyl-propyl)-3,4-dimethyl-2,6-dinitro-benzene (pendimethalin) and ethyl-[2-
chloro-5-(4-chloro-5-difluoromethoxy-1-methyl-1 H-pyrazol-3-yl)-4-fluoro-phenoxy]-acetate (pyraflufen-ethyl).
Emphasis is also given to selective herbicidal compositions which are characterized in
30 that they comprise an active compound combination comprising


picolinafen and
2-(2-methoxycarbonyl-phenylsulphonylaminocarbonyl)-4-methyl-5-n-propoxy-2,4-dihydro-3H-l,2,4-triazol-3-one or the sodium salt of this compound (propoxycarbazone-sodium) and
optionally one or more compounds from the group consisting of N-(4,6-di-methoxy-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-chIoro-2-fluoro-5-(2-chloro-2-ethoxycarbonyl-ethyl)-phenyl)-4-difluoromethyl-5-methyl-2,4-dihydro-3H-l,2,4-triazol-3-one (carfentrazone-ethyl), ethyl 2-chloro-3-[2-chloro-5-(l,3,4,5,6,7-hexahydro-l,3-dioxo-2H-isoindol-2-yl)-phenyl]-2-propanoate (cinidon-ethyl), 2-chloro-4-ethylamino-6-( 1 -cyano-1 -methyl-ethylamino)-1,3,5-triazine (cyanazine), 2,4-dichloro-phenoxyacetic acid (2,4-D), (R)-2-(2,4-dichloro-phenoxy)-propanoic acid (dichlorprop-P), N-(2,6-difluoro-phenyl)-8-fluoro-5-methoxy-[ 1,2,4]-triazolo-[ 1,5-c]-pyrimidine-2-sulphon-amide (florasulam), N-(4-fluoro-phenyl)-N-i-propyl-2-(5-trifluoromethyl-1,3,4-thiadiazol-2-yl-oxy)-acetamide (flufenacet), N-(4,6-dimethoxy-pyri-midin-2-yl)-N"-(3-methoxycarbonyl-6-trifluoromethyl-pyridin-2-yl-sulphon-yl)-urea sodium salt (flupyrsulfuron-methyl-sodium), (4-amino-3,5-dichloro-6-fluoro-pyridin-2-yl-oxy)-acetic acid (-2-butoxy-l -methyl-ethyl ester, -1-methyl-heptyl ester) (fluroxypyr, -butoxypropyl, -meptyl), N-(4-methoxy-6-methyl-l,3,5-triazin-2-yl)-N"-(5-iodo-2-methoxycarbonyl-phenylsulphonyl)-urea sodium salt (iodosulfuron-methyl-sodium), N,N-dimethyl-N"-(4-iso-propyl-phenyl)-urea (isoproturon), 2-(4-chloro-2-methyl-phenoxy)-propionic acid (mecoprop), N-(2,6-dichloro-3-methyl-phenyl)-5,7-dimethoxy-l,2,4-tri-azolo[ 1,5-a]-pyrimidine-2-sulphonamide (metosulam), 4-amino-6-tert-butyl-3-methylthio-l ,2,4-triazin-5(4H)-one (metribuzin), N-(4-methoxy-6-methyl-l,3,5-triazin-2-yl)-N"-(2-methoxycarbonyl-phenylsulphonyl)-urea (metsulf-uron-methyl), l-amino-N-(l-ethyl-propyl)-3,4-dimethyl-2,6-dinitro-benzene
Le A 34 090-ForeignCountries

(pendimethalin), N-(4-methoxy-6-methyl-1,3,5-triazin-2-yl)-N"-(2-methoxy-carbonyl-thien-3-yl-sulphonyl)-urea (thifensulfuron-methyl), N-methyl-N-(4-methoxy-6-methyl-l,3)5-triazin-2-yl)-N"-(2-methoxycarbonyl-phenylsulphon-yl)-urea (tribenuron-methyl), N-[[(4,6-dimethoxy-2-pyrimidinyl)-amino]-carbonyl]-3-(2,2,2-trifluoro-ethoxy)-2-pyridinesulfonamide sodium salt (tri-floxysulfuron), N-(4-methoxy-6-trifluoromethoxy-l,3,5-triazin-2-yl)-N"-(2-trifluoromethy l-phenylsulphonyl)-urea (tritosulfuron).
Emphasis is also given to selective herbicidal compositions which are characterized in
10 that they comprise an active compound combination comprising
(a) picolinafen and
(b) 2-(2-trifluoromethoxy-pheny Isulphony laminocarbony l)-4-methy 1- 5 -methoxy-15 2,4-dihydro-3H-l,2,4-triazol-3-one or the sodium salt of this compound
(flucarbazone-sodium) and
(c) optionally one or more compounds from the group consisting of 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-meth-
yl-2,4-dihydro-3H-l,2,4-triazol-3-one (carfentrazone-ethyl), ethyl 2-chloro-3-
[2-chloro-5-(l,3,4,5,6,7-hexahydro-l,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), 2,4-dichloro-phenoxyacetic acid (2,4-D), 3,6-
dichloro-2-methoxy-benzoic acid (dicamba), ethyl (R)-2-[4-(6-chloro-benzox-
azol-2-yl-oxy)-phenoxy]-propanoate (fenoxaprop-(P)-ethyl), N-(2,6-difluoro-
phenyI)-8-fiuoro-5-methoxy-[l,2,4]-triazolo-[l,5-c]-pyrimidine-2-sulphon-
amide (florasulam), N-(4-fluoro-phenyl)-N-i-propyl-2-(5-trifluoromethyl-
l,3,4-thiadiazol-2-yl-oxy)-acetamide (flufenacet), N-(4,6-dimethoxy-pyrimi-


Le A 34 090-Foreign Countries
din-2-yl)-N"-(3-methoxycarbonyl-6-trifluoromethyl-pyridin-2-yl-sulphonyl)-
urea sodium salt (flupyrsulfuron-methyl-sodium), (4-amino-3,5-dichloro-6-
fluoro-pyridin-2-yl-oxy)-acetic acid (-2-butoxy-l-methyl-ethyl ester, -1-
methyl-heptyl ester) (fluroxypyr, -butoxypropyl, -meptyl), methyl 2-(4,5-di-
5 hydro-4-methyl-4-isopropyl-5-oxo-lH-imidazol-2-yl)-4-methyl-benzoate
(imazamethabenz-methyl), 2-(4,5-dihydro-4-methyl-4-isopropyl-5-oxo-1H-imidazol-2-yl)-5-methoxymethyl-pyridine-3-carboxylic acid (imazamox), N-(4-methoxy-6-methyl-l,3,5-triazin-2-yl)-N"-(5-iodo-2-methoxycarbonyl-phenylsulphonyl)-urea sodium salt (iodosulfuron-methyl-sodium), N,N-di-
10 methyl-N"-(4-isopropyl-phenyl)-urea (isoproturon), (4-chloro-2-methyl-phen-
oxy)-acetic acid (MCPA), 2-(4-chloro-2-methyl-phenoxy)-propionic acid
(mecoprop), N-(2,6-dichloro-3-methyl-phenyl)-5,7-dimethoxy-1,2,4-triazolo-
[1,5-a]-pyrimidine-2-sulphonamide (metosulam), 4-amino-6-tert-butyl-3-
methylthio-1,2,4-triazin-5(4H)-one (metribuzin), N-(4-methoxy-6-methyl-
15 l,3,5-triazin-2-yl)-N"-(2-methoxycarbonyl-phenylsulphonyl)-urea (metsulf-
uron-methyl), l-amino-N-(l-ethyl-propyl)-3,4-dimethyl-2,6-dinitro-benzene (pendimethalin), methyl 2-[[[(4,5-dihydro-4-methyl-5-oxo-3-propoxy-lH-l,2,4-triazol-l-yl)-carbonyl]-amino]-sulphonyl]-benzoate sodium salt (prop-oxycarbazone-sodium), ethyl [2-chloro-5-(4-chloro-5-difluoromethoxy-1 -
20 methyl- lH-pyrazol-3-yl)-4-fluoro-phenoxy]-acetate (pyraflufen-ethyl), N-
(4,6-dimethoxy-pyrimidin-2-yl)-N"-(2-ethylsulphonyl-imidazo[l,2-a]pyri-dine-3-sulphonamide (sulfosulfuron), N-(4-methoxy-6-methyl-l,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-cy-
25 clohexen-1-one (tralkoxydim), S-(2,3,3-trichloro-2-propenyl) diisopropyl-
carbamothioate (triallate), N-methyl-N-(4-methoxy-6-methyl-l,3,5-triazin-2-yl)-N"-(2-methoxycarbonyl-phenylsulphonyl)-urea (tribenuron-methyl), N-[[(4,6-dimethoxy-2-pyrimidinyl)-amino]-carbonyl]-3-(2,2,2-trifluoro-ethoxy)-2-pyridinesulphonamide sodium salt (trifloxysulfuron), N-(4-methoxy-6-tri-
30 fluoromethoxy-l,3,5-triazin-2-yl)-N"-(2-trifluoromethyl-phenylsulphonyl)-
urea (tritosulfuron).



Le A 34 090-Foreiegn countries

Surprisingly, it has now been found that the active compound combinations defined above of the 2,6-disubstituted pyridine derivatives of the formula (I) and the active compounds of group 2 listed above, optionally in combination with active compounds of groups 3 and 4, have particularly high herbicidal activity combined with very good compatibility with useful plants and can be used in various crops, in particular in wheat, but additionally also in rice, maize and barley for the selective control of weeds.
Surprisingly, the herbicidal activity of the inventive active compound combinations of compounds of the abovementioned groups 1 and 2 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
15 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
2|0 defined above of 2,6-disubstituted pyridine derivatives of the formula (I) and a
safener/antidote ("active compounds of group 3") in combination with one or more of the abovementioned active compounds of group 2 have particularly high herbicidal activity combined with very good compatibility with useful plants and can be used in various crops, in particular in cereals and maize, especially wheat, but also in soya, potatoes 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.
The compounds diethyl l-(2,4-dichlorophenyl)-4,5-dihydro-5-methyl-lH-pyrazole-3,5-


Le A 34 090-Foreign Countries
dicarboxylate (mefenpyr-diethyl), 1-methylhexyl [(5-chloro-8-quinolinyl)oxy]acetate
(cloquintocet-mexyl) and ethyl l-(2,4-dichlorophenyl)-5-(trichioromethyl)-lH-l,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. 2,4-D is a known
5 herbicide.
Furthermore, it is surprisng that, from a large number of known safeners or antidotes
capable of antagonizing the damaging effect of a herbicide on the crop plants, it is
specifically the active compounds of group 3 listed above which neutralize the
10 damaging effect of compounds of the formula (I), in combination with one or more of
the abovementioned active compounds of group 2, on the crop plants virtually completely without adversely affecting the herbicidal activity against the weeds.
The particularly advantageous effect of the particularly preferred combination
15" partners among the active compounds 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.
The active compound combinations according to the invention can be used, for
25 example, in connection with the following plants:
Dicotyledonous weeds of the genera: Sinapis, Lepidium, Galium, Stellaria, Matricaria,
Anthemis, Galinsoga, Chenopodium, Urtica, Senecio, Amaranthus, Portulaca,
Xanthium, Convolvulus, Ipomoea, Polygonum, Sesbania, Ambrosia, Cirsium, Carduus,
2i Sonchus, Solanum, Rorippa, Rotala, Lindernia, Lamium, Veronica, Abutilon, Emex,
Datura, Viola, Galeopsis, Papaver, Centaurea, Trifolium, Ranunculus, Taraxacum.
Dicotyledonous crops of the genera: Gossypium, Glycine, Beta, Daucus, Phaseolus,
Pisum, Solanum, Linum, Ipomoea, Vicia, Nicotiana, Lycopersicon, Arachis, Brassica,
30 Lactuca, Cucumis, Cucurbita.


Le A 34 090-Foreign Countries
Monocotyledonous weeds of the genera: 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,
5 Apera, Phalaris.
Monocotyledonous crops of the genera: Oryza, Zea, Triticum, Hordeum, Avena, Secale, Sorghum, Panicum, Saccharum, Ananas, Asparagus, Allium.
10 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.
15
2f
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 harvested crops and vegetative and generative propagation material, for example seedlings, tubers, rhizomes, cuttings and seeds.
30
The treatment of the plants and parts of plants according to the invention with the active compounds is carried 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


Le A 34 090-Foreign Countries
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 active compound of group 2 are present per part by weight of active
10 compound of the formula (I).
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
the active compound combinations 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 one of the
compounds (antidotes/safeners) mentioned above under (c) which improve the crop
plant tolerability are present per part by weight of active compound of the formula (I),
20 its salts or its mixtures 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
25 substances impregnated with active compound, and very fine encapsulations in
polymeric 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 carriers, optionally with
30 the use of surface-active agents, that is emulsifying agents and/or dispersing agents
and/or foam-forming agents.



Le A 34 090-Foreign Countries
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-
5 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

10 sulphoxide, as well as water.
Suitable solid carriers are:
for example ammonium salts and ground natural minerals, such as kaolins, clays, talc,
1 5 chalk, quartz, attapulgite, montmorillonite or diatomaceous earth, and ground synthetic
minerals, such as finely divided silica, alumina and silicates; suitable solid carriers 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
20 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
25 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
30 synthetic phospholipids, can be used in the formulations. Other possible additives are
mineral and vegetable oils.


Le A 34 090-ForeignCountries
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.
15 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 "Oleo DuPont HE") or ammonium salts such as, for example, ammonium sulphate or ammonium thiocyanate, as further additives.
25!
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
30 scattering.



Le A 34 090-Foreign Countries
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):
IfX = % damage by herbicide A (active compound of the formula I) at an
application rate of p kg/ha
andY = % damage by herbicide B (active compound of the formula II) at an
application rate of q kg/ha
and E = the expected damage of the herbicides A and B at application rates of p and q kg/ha,
thenE = 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.


Accordingly the present invention relates to a herbicidal composition
comprising an effective amount of an active compound combination
comprising (a) N-(4-fluorophenyl)-6-[3-(trifluoromethyl)phenoxy]-2-
pyridincarboxamide (picolinafen), and (b) 2-(2-

methoxycarbonylphenylsulphonylamino-carbonyl)-4-methyl-5-n-propoxy-2, 4-dihydro-3H-l,2,4-triazol-3-one or the sodium salt thereof (propoxycarbazone-sodium).


Le A 34 090-Foreign countries

Use Examples
Customary formulations of the active compounds in question were used. Propoxycarbazone-sodium was used as 70 WG, flufenacet as 60 WG and picolinafen as 75 WG formulation. From the active compounds, an aqueous spray liquor containing 0.1% of the additive Renex-36 was prepared.
Example 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 500 1 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 shownin the tables below, where the abbreviations used in the tables have the following meaning: a.i. = active ingredient = active compound









e A 34 090-foreign Countries Table A-l

Application rate g of ai/ha Avenua
observed Avenua
calculated*
flufenacet 60 30 10 10
picolinafen 30 8 20 0
flufenacet
+
picolinafen 60 + 30 30 + 30 60 + 8 70 70 70 28 28 10
* values calculated by the method of Colby
Table A-2

Application rate g of ai/ha Digitaria
observed Digitaria
calculated*
flufenacet 125 60 10 0
picolinafen 30 50
flufenacet
+
picolinafen 125 + 30 60 + 30 90 90 55 50
* values calculated by the method of Colby

Le A 34 090-Foreign Countries
-,30-
Table A-3

Application rate g of ai/ha Echinochloa
observed Echinochloa
calculated*
flufenacet 60 60
picolinafen 8 10
flufenacet
+
picolinafen 60 + 8 90 64
* values calculated by the method of Colby
Table A-4

Application rate g of ai/ha Cassia
observed Cassia
calculated*
flufenacet 125 0
picolinafen 30 40
flufenacet
+
picolinafen 125 + 30 100 40
* values calculated by the method of Colby


Le A 34 090-Foreign countries
Table A-5

Application rate g of ai/ha Ipomoea
observed Ipomoea
calculated*
flufenacet 125 60 30 30
picolinafen 30 15 8 70 70 70
flufenacet
+
picolinafen 125 + 30
125 + 15
125 + 8
60 + 8 100 100 98 98 79 79 79 79
* values calculated by the method of Colby Table A-6

Application rate g of ai/ha Viola
observed Viola
calculated*
flufenacet 60 0
picolinafen 8 90
flufenacet
+
picolinafen 60 + 8 100 90
* values calculated by the method of Colby 10


Le A 34 090-Foreign Countries
Table A-7

Application rate g of ai/ha Avenua
observed Avenua
calculated*
propoxycarbazone-sodium 60 30 15 60 50 50
picolinafen 30 15 20 10
propoxycarbazone-
sodium
+
picolinafen 60 + 30 30 + 30 15 + 30 60+15 30+15 15+15 80 80 80 80 80 80 68 60 60 64
55 55
* values calculated by the method of Colby
5 Table A-8

Application rate g of ai/ha Loliutn
observed Lolium
calculated*
propoxycarbazone-sodium 30 15 20 0
picolinafen 30 15 20 0
propoxycarbazone-
sodium
+
picolinafen 30 + 30 30+15 15+15 50 50 30 36
20
0
* values calculated by the method of Colby


Le A 34 090-Foreign countries

Table A-9
Application rate Polygonum Polygonum
g of ai/ha observed calculated*
propoxycarbazone- 60 0
sodium 30 0
15 0
picolinafen 30 70
15 70
propoxycarbazone- 60+30 80 70
sodium 30+30 80 70
+ 15+30 80 70
picolinafen 60+15 90 70
30+15 80 70
15+15 80 70


Le A 34 090-foreign Countries
Example B
Outdoor trials
5 Cereal
Post-emergence spring
To examine a possible synergism, the compounds picolinafen and propoxy-
carbazone-sodium were tested under outdoor conditions in cereal against
10 economically important weed grasses. The small-plot experiments were conducted
on areas used for agricultural cultivation. The selected areas had a high weed content.
The active compounds were applied in spring by the post-emergence method and
over the entire area, using spray application with a medium droplet size. To prepare
15 an advantageous preparation of active compound, the active compounds were
formulated as 70 WG (70% w/w water-dispersible powder) or 75 WG (75% w/w water-dispersible powder) and suspended in water. The spray liquor was then applied in a water application rate customarily used in practice.
20 About 8-10 weeks after the application of the spray liquor, the herbicidal activity
was scored visually. The figures denote:
0 % = no herbicidal effect, 100 % = total destruction of the crop or the weeds. 25
In this experiment, the active compound mixtures showed a highly pronounced synergism in the activity against various weeds. The activity exceeded the value, which was expected for the mixture according to Colby"s formula (COLBY 1967), considerably (see the tables below).


Le A 34 090-Fofeign Countries Table B-l

Application
rate
g of ai/ha Matricaria ch.
observed Matricaria ch.
calculated*


1st location 2nd location 1st location 2nd location
propoxycarbazone-sodium 42 60 10
picolinafen 75 0 0
propoxycarbazone-
sodium
+
picolinafen 42 + 75 92 70 60 10
Table B-2

Application rate g of ai/ha Lactuca observed Lactuca
calculated*
propoxycarbazone-sodium 42 10
picolinafen 75 0
propoxycarbazone-
sodium
+
picolinafen 42 + 75 70 10


Le A 34 090-Foreign"Countries

Table B-3

Application rate g of ai/ha Stellaria observed Stella ria
calculated*
propoxycarbazone-sodium 42 30
picolinafen 75 20
propoxycarbazone-
sodium
+
picolinafen 42 + 75 62 44
Table B-4

Application rate g of ai/ha Matricaria in. observed
75 Matricaria in.
calculated*
propoxycarbazone-sodium 42

picolinafen 75 45
propoxycarbazone-
sodium
+
picolinafen 42 + 75 98 86


egnr Countrk
Le A 34 090-ForeigniCountries


Table B-5

Application rate g of ai/ha Legousia observed Legousia
calculated*
propoxycarbazone-sodium 42 0
picolinafen 75 0
propoxycarbazone-
sodium
+
picolinafen 42 + 75 50 0
Table B-6

Application rate g of ai/ha Galium observed Galium
calculated*
propoxycarbazone-sodium 42 0
picolinafen 75 30
propoxycarbazone-
sodium
+
picolinafen 42 + 75 65 30


Le A 34 090-Foreign Countries

Table B-7

Application rate g of ai/ha Lactuca observed Lactuca
calculated*
propoxycarbazone-sodium 42 10
picolinafen 75 0
propoxycarbazone-
sodium
+
picolinafen 42 + 75 70 10


WE CLAIM: fresh & duplicate
947/mum/2000
1. A herbicidal composition comprising an effective amount of an active compound combination comprising (a) N-(4-fluorophenyl)-6-[3-(trifluoromethyl)phenoxy]-2-pyridincarboxamide (picolinafen), and (b) 2-(2-methoxycarbonylphenylsulphonylamino-carbonyl)-4-methyl-5-n-propoxy-2, 4-dihydro-3H-l,2,4-triazol-3-one or the sodium salt thereof (propoxycarbazone-sodium).
2. The herbicidal composition as claimed in claim 1, wherein it optionally comprises at least one crop-plant-compatibility-improving compound selected from the group consisting of 1-methylhexyl 5-chloro-quinoxalin-8-oxy-acetate (cloquintocet), ethyl l-(2,4-dichloro-phenyl)-5-trichloromethyl-lH-l,2,4-triazole-3-carboxylate (fenchlorazol-ethyl), ethyl 4,5-dihydro-5,5-diphenyl-3-isoxazolecarboxylate (isoxadifen-ethyl), diethyl l-(2,4-dichlorophenyl)-4,5-dihydro-5-methyl-lH-pyrazole-3,5-dicarboxylate (mefenpyr-diethyl), 2,4-dichlorophenoxyacetic acid (2,4-D) and derivatives thereof.
3. The herbicidal composition as claimed in claim 1, wherein it comprises (a) picolinafen, and (b) propoxycarbazone-sodium.
4. The herbicidal composition as claimed in claim 1, wherein it optionally comprises (c) at least one crop-plant-compatibility-improving compound selected from the group consisting of a-(l,3-dioxolan-2-yl-methoximino)-phenylacetonitrile (oxabetrinil), a-(cyanomethoximino)-phenylacetonitrile (cyometrinil), 4-chloro-N-( 1,3-dioxolan-2-yl-methoxy)-a-trifluoro-acetophenoneoxime (fluxofenim), 4,6-dichloro-2-phenyl-pyrimidine (fenclorim), 4-dichloroacetyl-3,4-dihydro-3-methyl-2H-1,4-benzoxazine (benoxacor), 1-methyl-hexyl 5-chloro-quinoxalin-8-oxy-acetate (cloquintocet), 2,2-dichloro-N-(2-oxo-2-(2-propenylamino)-ethyl)-N-(2-propenyl)-acetamide (DKA-24), 1,8-naphthalic anhydride, ethyl l-(2,4-dichloro-phenyl)-5-trichloromethyl- 1H-1,2,4-triazole-3-carboxylate (fenchlorazol-ethyl), phenylmethyl 2-chloro-4-trifluoromethyl-thiazole-5-carboxylate (flurazole), 3-dichloroacetyl-5-(2-furanyl)-2,2-dimethyl-

oxazolidine (furilazole, MON-13900), 4-dichloroacetyl-l-oxa-4-aza-spiro[4.5]-
decane (AD-67), 2-dichloromethyl-2-methyl-l,3-dioxolane (MG-191), 2,2-
dichloro-N-(l,3-dioxolan-2-yl-methyl)-N-(2-propenyl)-acetamide (PPG-1292),
2,2-dichloro-N,N-di-2-propenyl-acetamide (dichlormid), N-(4-methyl-phenyl)-
N"-(1 -methyl-1-phenyl-ethyl)-urea (dymron), 1-dichloroaceryl-hexahydro-
3,3,8a-trimethylpyrrolo[l,2-a]-pyrimidin-6(2H)- one (BAS-145138), N-(2-
methoxy-benzoyl)-4-(methylaminocarbonylamino)-benzenesulphonamide,
ethyl 4,5-dihydro-5,5-diphenyl-3-isoxazolecarboxylate (isoxadifen-ethyl),
diethyl l-(2,4-dichlorophenyl)-4,5-dihydro-5-methyl-lH-pyrazole-3,5-
dicarboxylate (mefenpyr-diethyl) (4-chloro-2-methyl-phenoxy)-acetic acid
(MCPA), (+-)-2-(4-chloro-2-methylphenoxy)propanoic acid (mecoprop), 3-
dichloroaceryl-2,2,5-trimethyl-oxazolidine (R-29148), 2,4-
dichlorophenoxyacetic acid (2,4-D) and derivatives thereof, and optionally (d)
one or more compounds selected from the group consisting of 2-chloro-N-
(ethoxymethyl)-N-(2-ethyl-6-methyl-phenyl)-acetamide (acetochlor), 5-(2-
chloro-4-trifluoromethyl-phenoxy)-2-nitro-benzoic acid sodium salt
(acifluorfen-sodiurn), 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-l,3,5-triazine-2,4-diamine (ametryn), 4-
amino-N-(1, l-dimethyl-ethyl)-4,5-dihydro-3-(l-methyl-ethyl)-5-oxo-1H-1,2
,4-triazole-l-carboxamide (amicarbazone), N-(4,6-dimethoxy-pyrimidin-2-yl)-
N"-(N-methyl-N-methylsulphonyl-sulphamoyl )-urea (amidosulfuron), 1H-
1,2,4-triazol-3-amine (amitrole), 6-chloro-4-ethylamino-2-isopropylamino-
1,3,5-triazine (atrazine), 2-[2,4-dichloro-5(2-propynyloxy)-phenyl]-5,6,7,8-
tetrahydro-l,2,4-triazolo -[4,3-a]-pyridin-3(2H)-one (azafenidin), N-(4,6-
dimethoxy-pyrimidin-2-yl)-N"-[l-methyl-4-(2-methyl-2H-tetrazol-5-yl )-lH-
pyrazol-5-ylsulphonyl]-urea (azimsulfuron), N-benzyl-2-(4-fluoro-3-
trifluoromethyl-phenoxy)-butanamide (beflubutamide), 4-chloro-2-oxo-3(2H)-benzothiazoleacetic acid (benazolin), N-butyl-N-ethyl-2,6-dinitro-4-trifluoromethyl-benzenamine (benfluralin), N-(4,6-dimethoxy-pyrimidin-2-yl)-N"-(2-methoxycarbonyl-phenylmethylsulphon yl)-urea (bensulfuron), methyl 2-[2-[4-(3,6-dihydro-3-methyl-2,6-dioxo-4-trifluoro-methyl-1(2H)-pyrimidin yl)phenoxy]methyl]-5-ethyl-phenoxy-propanoate (benzfendizone), 3-(2-chloro-4-methylsulphonyl-benzoyl)-4-phenylthio-bicyclo-[3.2. l]-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-yloxy)-benzoic acid sodium salt
(bispyribac-sodium), 2-bromo-3,3-dimethyl-N-( 1 -methyl-1-phenyl-ethyl)-
butanamide (bromobutide), 0-(2,4-dinitro-phenyl) 3,5-dibromo-4-hydroxy-
benzaldehyde-oxime (bromofenoxim), 3,5-dibromo-4-hydroxy-benzo-nitrile
(bromoxynil), N-butoxymethyl-2-chloro-N-(2,6-diethyl-phenyl)-acetamide
(butachlor), [l,l-dimethyl-2-oxo-2-(2-propenyloxy)]-ethyl 2-chloro~5-(3,6-
dihydro-3-methyl-2,6-dioxo-4-trifluoromethyl-1(2H)-pyrimid inyl)-benzoate
(butafenacil-allyl), 2-(1-ethoximino-propyl)-3-hydroxy-5-[2,4,6-trimethyl-3-
(l-oxo-butyl)-pheny l]-2-cyclohexen-l-one (butroxydim), S-ethyl bis-(2-
methyl-propylj-thiocarbamate (butylate), N,N-diethyl-3-(2,4,6-trimethyl-
phenyl-sulphonyl)-lH-l,2,4-triazole-l-carbo xamide (cafenstrole), 2-[l-[(3-
chloro-2-propenyl)-oxy-imino]-propyl]-3-hydroxy-5-(tetrahydro-2H- pyran-4-
yl)-2-cyclohexen-l-one (caloxydim, tepraloxydim), 2-(4-chloro-2-fluoro-5-(2-
chloro-2 -ethoxycarbonyl-ethyl) -phenyl) -4-difluor omethyl-5-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)-ur ea (chlorsulfuron), N"-(3-
chloro-4-methyl-phenyl)-N,N-dimethyl-urea (chlortoluron), 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), N-(4,6-dimethoxy-l,3,5-triazm-2-yl)-N"-(2-(2-
methoxy-ethoxy)-phenylsulpho nyl)-urea (cinosulfuron), 2-[l-[2-(4-chloro-
phenoxy)-propoxyamino]-butyl]-5-(tetrahydro-2H-thiopyran -3-yl)-1,3-
cyclohexanedione (clefoxydim), (E,E)-(+)-2-[l-[[(3-chloro-2-propenyl)-oxy]-
imino]-propyl]-3-hydroxy-2-cyc lohexen-1-one (clethodim), prop-2-ynyl (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-[(5-ethoxy-7-fluoro[1,2,4]-triazolo[ 1,5-c]pyrimidin-2-yl-sulpho nyl)-amino]-benzoate (cloransulam-methyl), 2-chloro-4~ethylamino-6-(l-cyano-l-methyl-ethylamino)-l,3,5-triazine (cyanazine), N-(4,6-dimethoxy-pyrimidin-2-yl)-N"-(2-cyclopropylcarbonyl-phenylsulphonyl )-urea (cyclosulfamuron), 2-

(l-ethoximinobutyl)-3-hydroxy-5-(tetrahydro-2H-thiopyran-3-yl)-2-cyclohe
xen-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-phenoxy)-
propanoic acid (dichlorprop-P), methyl-2-[4-(2,4-dichloro-phenoxy)-
phenoxy]-propanoate (diclofop-methyl), N-(2,6-dichloro-phenyl)-5-ethoxy-7-
fluoro-[l,2,4]-triazolo-[l,5-c]-pyrimid ine-2-sulphonamide (diclosulam), 1,2-
dimethyl-3,5-diphenyl-lH-pyrazolium methyl sulphate (difenzoquat), N-{2,4-
difluoro-phenyl)-2-(3-trifluoromethyl-phenoxy)-pyridine-3-carboxami de
(diflufenican), 2-[1-[(3,5-difluoro-phenyl)-amino-carbonyl-hydrazono] -ethyl]-
pyridine-3-ca rboxylic acid (diflufenzopyr), S-(1-methyl-1-phenyl-ethyl) 1-
piperidine-carbothioate (dimepiperate), (S-) 2-chloro-N-(2,4-dimethyl-3-
thienyl)-N-(2-methoxy-l-methyl-ethyl)-acetamide (S-) (dimethenamid), 2-
amino-4-(l-fluoro-l-methyl-ethyl)-6-(l-methyl-2-(3,5-dimethyl-phenoxy)-e
thylamino)-l,3,5-triazine (dimexyflam), N3,N3-diethyl-2,4-dinitro-6-
trifluoromethyl-l,3-diamino-benzene (dinitramine), 6,7-dihydro-
dipyrido[1,2-a:2", 1"-c]pyra2mediium (diquat), S,S-dimethyl 2-difluoromethyl-
4-i-butyl-6-trifluoromethyl-pyridine-3,5-dicarbothioate (dithiopyr), N"-(3,4-
dichloro-phenyl)-N,N-dimethyl-urea (diuron), 2-[2-(3-chloro-phenyl)-
oxiranyl-methyl]-2-ethyl-1H-indene-1,3(2H)-dione (epropodan), S-ethyl
dipropylthiocarbamate (EPTC), S-(phenylmethyl) N-ethyl-N-(l,2-dimethyl-
propyl)-thiocarbamate (esprocarb), N-ethyl-N-(2-methyl-2-propenyl)-2,6-
dinitro-4-trifluoro-methyl-benzenamine (ethalfluralin), 2-ethoxy- l-methyl-2-
oxoethyl (S)-(2-ethoxy-1-methyl-2-oxoethyl)-2-chloro-5-(2-chloro-4-
trifluoromethyl- phenoxyj-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),
4-(2-chloro-phenyl)-N-cyclohexyl-N-ethyl-4,5-dihydro-5-oxo-lH-tetrazole-l-
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-isopropyl-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]-pyrimi dine-2-
sulphonamide (florasulam), butyl (R)-2-[4-(5-trifluoromethyl-pyridin-2-yl-oxy)-phenoxy]-propanoate (fluazifop, -butyl, -P-butyl), i-propyl 5-(4-bromo-l-

methyl-5-trifluoromethyl-1 H-pyrazol-3-yl)-2-chloro-4-fluoro-b enzoate
(fluazolate), 4,5-dihydro-3-methoxy-4-methyl-5-oxo-N-[(2-trifluoromethoxy-
phenyl)-sulpho nyl]-l-H-l,2,4-triazole-l-carboxamide sodium salt
(flucarbazone-sodium), N-(2,6-difluoro-phenyl)-5-methyl-1,2,4-triazolo[1,5-
a]-pyrimidine-2-sulpho namide (flumetsulam), pentyl [2-chloro-4-fluoro-5-
(1,3,4,5,6,7-hexahydro-1,3-dioxo-2H-isoindol-2-yl)-ph enoxy]-acetate
(flumiclorac-pentyl), 2-[7-fluoro-3,4-dihydro-3-oxo-4-(2-propynyl)-2H-1,4-
benzoxazin-6-yl]-4,5,6 ,7-te1xahydro-lH-isoindole-l,3-dione (flumioxazin), 2-
[4-chloro-2-fluoro-5-[(1-methyl-2-propynyl)-oxy]-phenyl]4,5,6,7-tetrahyd ro-
1H-isoindole-1,3(2H)-dione (flumipropyn), 3-chloro-4-chloromethyl-1-(3-
trifluoromethyl-phenyl)-2-pyrrolidinone (fluorochloridone),
ethoxycarbonylmethyl 5-(2-chloro-4-trifluoromethyl-phenoxy)-2-nitro-
benzoate (fluoroglycofen-ethyl), l-(4-chloro-3-(2,2,3,3,3-pentafiuoro-
propoxymethyl)-phenyl)-5-phenyl-lH-l, 2,4-triazole-3-carboxamide
(flupoxam), l-isopropyl-2-chloro-5-(3,6-dihydro-3-methyl-2,6-dioxo-4-
trifluoromethyl-1 (2H)-pyrimidyl)-benzoate (flupropacil), N-(4,6-dimethoxy-
pyrimidin-2-yl)-N"-(3-methoxycarbonyl-6-trifluoromethyl-p yridin-2-yl-
sulphonyl)-urea sodium salt (flupyrsulfuron-methyl-sodium), 9-hydroxy-9H-
fluorene-9-carboxylic acid (flurenol), (4-amino-3,5-dichloro-6-fluoro-pyridin-
2-yl-oxy)-acetic acid (2-butoxy-l-methyl-ethyl ester, 1-methyl-heptyl ester)
(fluroxypyr, -butoxy-propyl, -meptyl), 5-methylamino-2-phenyl-4-(3-
trifluoromethyl-phenyl)-3(2H)-furanone (flurtamone), methyl[(2-chloro-4-
fluoro-5-(tetrahydro-3-oxo-1H,3H-[1,3,4]-thiadiazolo-[3 ,4-a]-pyridazin-1-
ylidene)-amino)-phenyl]-thio-acetate (fluthiacet-methyl), 5-(2-chloro-4-
trifluoromethyl-phenoxy)-N-methylsulphonyl-2-nitro-benzamide (fomesafen),
2-[[[[(4,6-dimethoxy-2-pyrimidinyl)-amino]-carbonyl]-amino]-sulphonyl]-4-f
ormylamino-N,N-dimethyl-benzamide (foramsulfuron), 2-amino-4-
(hydroxymethylphosphinyl)-butanoic acid (ammonium salt) (glufosinate-(ammonium)), N-phosphonomethyl-glycine (isopropylammonium salt), (glyphosate, isopropylammonium), (R)-2-[4-(3-chloro-5-trifluoromethyl-pyridin-2-yl-oxy)-phenoxy]-propanoic acid (methyl ester, 2-ethoxy-ethyl ester, butyl ester) (haloxyfop, -methyl, -P-methyl, -ethoxyethyl, -butyl), 3-cyclohexyl-6-dimethylamino-l-methyl-l,3,5-triazine-2,4(lH,3H)-dione (hexazinone), methyl 2-(4,5-dihydro-4-methyl-4-isopropyl-5-oxo-lH-imidazol-2-yl)-4-methyl-benzo ate (imazamethabenz-methyl), 2-(4,5-dihydro-

4-methyl-4-isopropyl-5-oxo-1H-imidazol-2-yl)-5-methyl-pyrid ine-3-
carboxylic acid (imazamethapyr), 2-(4,5-dihydro-4-methyl-4-isopropyl-5-oxo-
lH-imidazol-2-yl)-5-methoxymethy l-pyridine-3-carboxylic acid (imazamox),
2-(4,5-dihydro-4-methyl-4-isopropyl-5-oxo-lH-imidazol-2-yl)quinoline-3-car
boxylic acid (imazaquin), 2-(4,5-dihydro-4-methyl-4-i-propyl-5-oxo-lH-
imidazol-2-yl)-5-ethyl-pyridin e-3-carboxylic acid (imazethapyr), N-(4,6-
dimethoxy-pyrimidin-2-yl)-N"-(2-chloro-imidazo[ 1,2-a]-pyridin-3-yl-
sulphonyl)-urea (imazosulfuron), N-(4-methoxy-6-methyl-1,3,5-triazin-2-yl)-
N-(5-iodo-2-methoxycarbonyl-phe nyl-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)-methanon e
(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 (isoxapyrifop), (2-
ethoxy-1-methyl-2-oxo-ethyl)-5-(2-chloro-4-trifluoromethyl-phenoxy)-2-n
itro-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)-l,3-cyclohexanedione (mesotrione), 4-amino-3-methyl-6-phenyl-
l,2,4-triazin-5(4H)-one (metamitron), 2-chloro-N-(2,6-dimethyl-phenyl)-N-
(lH-pyrazol-l-yl-methyl)-acetamide (metazachlor), N"-(4-(3,4-dihydro-2-
methoxy-2,4,4-trimethyl-2H-1-benzopyran-7-yl-oxy)-phe nyl)-N-methoxy-N-
methyl-urea (metobenzuron), N"-(4-bromo-phenyl)-N-methoxy-N-methyl urea
(metobromuron), (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]-pyrim idine-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-
methoxycarbonyl-phenylsulp honyl)-urea (metsulfuron-methyl), S-ethyl-hexahydro-lH-azepine-1-carbothioate (molinate), 2-(2-naphthyloxy)-N-phenyl-propanamide (naproanilide), N-buryl-N"-(3,4-dichloro-phenyl)-N-

methyl-urea (neburon), N-(4,6-dimethoxy-pyrimidin-2-yl)-N"-(3-
dimethylcarbamoyl-pyridin-2-yl-sulp honyl)-urea (nicosulfuron), S-(2-chloro-
ben2yl)-N,N-diethyl-thiocarbamate (orbencarb), 4-dipropylamino-3,5-dinitro-
benzenesulphonamide (oryzalin), 3-[2,4-dichloro-5-(2-propynyl-oxy)-phenyl]-
5-(t-butyl)-l,3,4-oxadiazol-2(3 H)-one (oxadiargyl), 3-[2,4-dichloro-5-(l-
methyl-ethoxy)-phenyl]-5-(t-butyl)-l,3,4-oxadiazol-2( 3H)-one (oxadiazon), N-
(4,6-dimethyl-pyrimidin-2-yl)-N"-(2-oxetan-3-yl-oxycarbonyl-phenylsulpho
nyl)-urea (oxasulfuron), 3-[ 1-(3,5-dichloro-phenyl)-1-i-propyl]-2,3-dihydro-6-
methyl-5-phenyl-4H-1, 3-oxazin-4-one (oxaziclomefone), 2-chloro-1-(3-
et±ioxy-4-nitxo-phenoxy)-4-trifluoromet±iylbenzene (oxyfluorfen), 1,1"-
dimethyl-4,4"-bipyridinium (paraquat), l-amino-N-(l-ethyl-propyl)-3,4-
dimethyl-2,6-dinitro-benzene (pendimethalin), 4-(t-butyl)-N-(l-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-bisdifluoromethoxy-pyrimidin-2-yl)-N"-
(2-methoxy-carbonyl-phenylsul phonyl)-urea (primisulfuron-methyl), 1-
chloro-N-[2-chloro-4-fluoro-5-[(6S,7aR)-6-fluoro-tetrahydro-1,3-dioxo-1H
pyrrolo[1,2-c]imidazol-2-(3H)-yl]-phenyl]-methanesulphonamide (profluazol),
2-chloro-N-isopropyl-N-phenyl-acetamide (propachlor), N-(3,4-dichloro-
phenyl) -propaneamide (propanil), (R)-[2-[[(1 -methyl-ethylidene) -amino] -oxy]-
ethyl] -2 - [4-(6-chloro-2 -quinoxa linyloxy)-phenoxy]-propanoate
(propaquizafop), 2-chloro-N-(2-ethyl-6-methyl-phenyl)-N-[(l-methyl-ethoxy)-
methyl]-acetamid e (propisochlor), S-phenylmethyl N,N-dipropyl-
thiocarbamate (prosulfocarb), N-(4-methoxy-6-methyl-l,3,5-triazin-2-yl)-N"-
(2-(3,3,3-trifluoro-propyl)-p henylsulphonyl)-urea (prosulfuron), ethyl[2-
chloro-5-(4-chloro-5-difluoromethoxy-1 -methyl-1H-pyrazol-3-yl)-4-f luoro-
phenoxy]-acetate (pyraflufen-ethyl), l-(3-chloro-4,5,6,7-tetrahydro-
pyrazolo[ 1,5-a]pyridin-2-yl)-5-(methyl-2-pr opynylamino)-1 H-pyrazole-4-
carbonitrile (pyrazogyl), 4-(2,4-dichloro-benzoyl)-1,3-dimethyl-5-(4-methyl-
phenylsulphonyloxy)-pyra zole (pyrazolate), 4-(2,4-dichloro-benzoyl)-l,3-
dimethyl-5-(phenylcarbonylmethoxy)-pyrazole (pyrazoxyfen), N-(4,6-
dimethoxy-pyrimidin-2-yl)-N"-(4-ethoxycarbonyl-1 -methyl-pyrazol-5-y 1-
sulphonyl)-urea (pyrazosulfuron-ethyl), 0-[2,6-bis-(4,6-dimethoxy-
pyrimidin-2-yl-oxy)-benzoyl]diphenylmethanone-ox ime (pyribenzoxim), 6-chloro-3-phenyl-4-pyridazinol (pyridafol), 0-(6-chloro-3-phenyl-pyridazin-4-


pyrimidinyl)-amino]-carbonyl]-3-(2,2,2-trifluoro-etho xy)-2-
pyridinesulphonamide sodium salt (trifloxysulfuron), l-amino-2,6-dinitro-
N,N-dipropyl-4-trifluoromethyl-benzene (trifluralin), N-[4-dimethylamino-6-
(2,2,2-txifluoro-ethoxy)-1,3,5-triazin-2-yl]-N"-(2-me thoxycarbonyl-phenyl-
sulphonyl)-urea (triflusulfuron-methyl), N-(4-methoxy-6-txifluoromethoxy-
1,3,5-triazin-2-yl)-N,-(2-trifluoro-methyl -phenylsulphonyl)-urea
(tritosulfuron), 2-pyridinesulphonamide N-[[(4,6-dimethoxy-2-
pyrimidinyl)amino]carbonyl]-3-(N-methyl-N-methylsulph onyl-amino),
methyl 2-[[[[(4,6-dimethoxy-2-pyrimidinyl)amino]carbonyl]amino]sulphonyl]-4-[[(me thylsulphonyl)amino]methyl]benzoate and 4-[4,5-dihydro-4-methyl-5-oxo-(3-trifluoromethyl)-1H-1,2,4-triazol-1-yl]-2 -[(ethylsulphonyl)-amino]-5-fluoro-benzenecarbothioamide.
5. The herbicidal composition as claimed in claim 1, wherein it
optionally comprises (d) one or more compounds selected from the group
consisting of 2,6-bis-(4,6-dimethoxy-pyrimidin-2-yl-oxy)-benzoic acid
sodium salt (bispyribac-sodium), N-(2,6-difluoro-phenyl)-8-fluoro-5-
methoxy-[l,2,4]-triazolo-[l,5-c]-pyrimi dine-2-sulphonamide (florasulam), N-
(4,6-dimethoxy--pyrimidin-2-yl)-N"-(3-methoxy-carbonyl-trifluoromethyl-py
rid-2-yl-sulphonyl)-urea sodium salt (flupyrsulfron-methyl-sodium), N,N-
dimethyl-N"-(4-isopropyl-phenyl)-urea (isoproturon), N-(2,6-dichloro-3-
methyl-phenyl)-5,7-dimethoxy-1,2,4-triazolo[ 1,5-alpyrimi dine-2-
sulphonamide (metosulam), 1-amino-N-(1-ethyl-propyl)-3,4-dimethyl-2,6-
dinitro-benzene (pendimethalin), and ethyl-[2-chloro-5-(4-chloro-5-
difluoromethoxy-l-methyl-lH-pyrazol-3~yl)-4- fluoro-phenoxy]acetate
(pyraflufen-ethyl).
6. A herbicidal composition substantially as hereinbefore described with
reference to the foregoing examples.
Dated this October 23, 2000.
(DR. ANUSHRI GUPTA)
OF REMFRY AND SAGAR ATTORNEY
FOR THE APPLICANTS

11. Herbicidal compositions substantially as herein described with reference to the foregoing examples.
Dated this 23rd day of October, 2000.
(B. KOMBI)
OF REMFRY & SAGAR
AGENT FOR THE APPLICANTS

Documents:

947-mum-2000-abstract(23-10-2000).doc

947-mum-2000-abstract(23-10-2000).pdf

947-mum-2000-cancelled pages(30-8-2007).pdf

947-mum-2000-claims(granted)-(30-8-2007).doc

947-mum-2000-claims(granted)-(30-8-2007).pdf

947-mum-2000-correspondence(18-9-2007).pdf

947-mum-2000-correspondence(ipo)-(13-8-2007).pdf

947-mum-2000-form 1(23-10-2000).pdf

947-mum-2000-form 13(13-8-2007).pdf

947-mum-2000-form 18(28-12-2005).pdf

947-mum-2000-form 2(granted)-(30-8-2007).doc

947-mum-2000-form 2(granted)-(30-8-2007).pdf

947-mum-2000-form 3(14-12-2000).pdf

947-mum-2000-form 3(23-10-2000).pdf

947-mum-2000-form 3(26-12-2000).pdf

947-mum-2000-form 3(29-6-2007).pdf

947-mum-2000-form 5(23-10-2000).pdf

947-mum-2000-petition under rule 138(29-6-2007).pdf

947-mum-2000-power of authority(23-10-2000).pdf

947-mum-2000-power of authority(29-6-2007).pdf


Patent Number 210424
Indian Patent Application Number 947/MUM/2000
PG Journal Number 43/2007
Publication Date 26-Oct-2007
Grant Date 03-Oct-2007
Date of Filing 23-Oct-2000
Name of Patentee BAYER AKTIENGESELLSCHAFT
Applicant Address D-51368 Leverkusen,
Inventors:
# Inventor's Name Inventor's Address
1 MATHIAS KREMER Heddinghonfener Str. 31, 51399 Burscheid
2 DIETER FEUCHT Ackerweg 9, 40789 Monheim
3 ARNDT WELLMANN Neustr.3, 40789 Monheim
4 BIRGIT KRAUSKOPF Osenauer Str.12a, 51519 Odenthal,
5 PETER DAHMEN Altebrucker Str.61, 41470 Neuss
PCT International Classification Number A01N 43/40
PCT International Application Number N/A
PCT International Filing date
PCT Conventions:
# PCT Application Number Date of Convention Priority Country
1 19960778.8 1999-12-16 Germany
2 19955128.6 1999-11-17 Germany