Title of Invention

HERBICIDAL COMPOSITIONS FOR SELECTIVE CONTROL OF WEEDS

Abstract "HERBICIDAL COMPOSITIONS FOR SELECTIVE CONTROL OF WEEDS" Herbicidal compositions, characterized in that they comprise an effective amount of an active compound combination comprising (a) at least one phenoxypyrimidine derivative of the general formula (I). (b) one or more compounds from a second group of herbicides comprising the active compounds. (c) at least one compound which improves crop plant compatibility. 5 NOV 2007
Full Text FORM 2
THE PATENTS ACT 1970
[39 OF 1970]
&
THE PATENTS RULES, 2003
COMPLETE SPECIFICATION
[See Section 10; rule 13]
"HERBICIDAL COMPOSITIONS FOR SELECTIVE CONTROL OF WEEDS"
BAYER AKTIENGESELLSCHAFT, a body corporate organized under the laws of Germany, D-51368 Leverkusen, Germany,
GRANTED
The following specification particularly describes the invention and the manner in which it is to be performed:

ORGN
825/MUM/2000

5 NOV 2007 5-11-2007

The present invention relates to herbicidal composition for selective control of weeds.
The invention relates to novel herbicidal synergistic active compound combinations comprising, on the one hand, known pyrimidine derivatives and, on the other hand, known herbicidally active compounds and/or safeners, which combinations can be used particularly successfully for the selective control of weeds in various crops of useful plants.
Pyrimidine derivatives, as broad-spectrum herbicides, form part of the subject-matter of a'number of patent applications (cf. US 4 906 285, EP-A-321 846, EP-A658 549, US 4 248 619, US 4 427 437). However, the known pyrimidine derivatives have a number of gaps in their activity. Likewise, the compatibility of these compounds with crop plants is not always entirely satisfactory.
Surprisingly, it has now been found that a number of known active compounds from the group of the phenoxypyrimidine derivatives, when used together with known herbicidally active compounds from various substance classes, have pronounced synergistic effects with respect to the activity against weeds and can be used par-. ticularly advantageously as broad-spectrum combination preparations for the selective . control of weeds in crops of useful plants, such as cereals, for example wheat, barley, rye and rice.
Surprisingly, it has also been found that the phenoxypyrimidine derivatives, on their own or together with known herbicidally active compounds, when used together with the compounds described below, which improve crop plant compatibility (safeners/-antidotes) prevent damage to the crop plants particularly effectively, and they can be used particularly advantageously as broad-spectrum combination preparations for the selective control of weeds in crops of useful plants, such as cereals, for example wheat, barley, rye and rice.





The invention provides selective herbicidal compositions, characterized in that they comprise an effective amount of an active compound combination comprising
(a) at least one phenoxypyrimidine derivative of the general formula (I)



in which
R represents hydrogen, -CH2CH2S(0)nRi (where R\ represents C4-C4-alkyl and n represents 0, 1 or 2) or

where
R2 represents hydrogen, halogen, cyano, phenyl, C^-Cg-allcyl, Ci-C4-alkoxy, Ci-C4-alkylthio, Ci-C4-alkoxycarbonyl, mono-or oU-Ci-C4-alkylaminocarbonyl, phenyl-Ci-C4-alkylarnino-carbonyl, where the phenyl group may optionally be substituted by halogen, Ci-C2-alkyl or Ci-C2-alkoxy, furylmemylamino--carbonly or phenyl, and
R3 represents in each case optionally halogen-, cyano-, nitro-, Ci-C4-alkyl-, C][-C4-alkoxy- or allyloxy-substituted phenyl, represents optionally Ci-C4-aIkyl-, phenoxy-, benzyloxy- or acetoxy-substituted amino, represents Ci-C4-alkylthio or repre-

sents the grouping -COR4, where R4 represents C1-C4-alkoxy, C1-C4-alkyl, benzyloxy or benzylamino,
A represents chlorine or methoxy and
D and E, which can be identical or different, represent hydrogen, halogen, C1-C8-alkyl, C1-C8-alkoxy or halogen-substituted C1-C8-alkoxy,
and/or a salt of a compound of the formula (I) ("active compounds of group"),
one or more compounds from a second group of herbicides comprising the active compounds mentioned below:
N-isopropyl-N-(4-fluorophenyI)-(5-trifluoromethyl-1,3,4-thiadiazol-2-yl-oxy)-acetamide (DE-A-38 21 600, FOE 5043), 2-(2-methoxycarbonyl-phenylsulphonylaminocarbonyl)-4-methyl-5-n-propoxy-2,4-dihydro-3H-l,2,4-triazol-3-one or a.sodium salt of this compound (EP-A-507 171, MKH 6561), 2-(2-trifluoromethoxy-phenylsulphonylaminocarbonyl)-4-methyl-5-methoxy-2,4-dihydro-3H-l,2,4-triazol-3-one or a sodium salt of this com¬pound (EP-A-507 171, MKH 6562), 4-amino-5-(l-methyl-ethyl)-2-(l,l-dimethyl-ethyl-aminocarbonyl)-2,4-dihydro-3H-l,2,4-triazol-3-one (ami-carbazone, MKH 3586), 2-chloro-N-(ethoxymethyl)-N-(2-ethyl-6-methyl-phenyl)-acetamide (acetochlor), 2-chloro-6-nitro-3-phenoxy-aniline (aclo-nifen), N-(4,6-dimethoxy-pyrimidin-2-yl)-N'-(N-methyl-N-methylsulphonyl-sulphamoyl)-urea (amidosulfuron), 2-(4-fluoro-3-trifluoromethyl-phenoxy)-N-phenylmethyl-butanamide (beflubutamid), ethyl N-benzoyl-N-(3,4-di-chloro-phenyl)-DL-alaninate (benzoylprop-ethyl), 3-i-propyl-1H-2,1,3-benzo-thiadiazin-4(3H)-one (bentazone), methyl 5-(2,4-dichloro-phenoxy)-2-nitro-

benzoate (bifenox), 2-bromo-3,3 -dimethyl-N-(l -methyl-1-phenyl-ethyl)-
butanamide (bromobutide), 3,5-dibromo-4-hydroxy-benzaldehyde 0-(2,4-
dinitro-phenyl) oxime (bromofenoxim), 3,5-dibromo-4-hydroxy-benzonitrile
(bromoxynil), N-butoxymethyl-2-chloro-N-(2,6-diethyl-phenyl)-acetamide
(butachlor), S-ethyl bis(2-methyl-propyl)-thiocarbamate (butylate), 2-(4-
chJoro-2-fluoro-5-(2-chloro-2-ethoxycarbonyl-ethy])-pheny])-4-difluoro-
methyl-5-methyl-2,4-dihydro-3H-1,2,4-triazol-3-one (carfentrazone-ethyl,
F-8426), 2,4-dichloro-l -(3-methoxy-4-nitro-phenoxy)-benzene (chlometh-
oxyfen), 3-amino-2,5-dichloro-benzoic acid (chloramben), l,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 (chlortoluron), N-(4,6-dimeth-
oxy-l,3,5-triazin-2-yl)-N'-(2-(2-methoxy-ethoxy)-phenylsulphonyl)-urea
(cinosulfuron), 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), N-(4,6-dimethoxy-pyrimidin-2-yl)-N'-(3-chloro-
4-methoxycarbonyl-1 -methyl-pyrazol-5-yI-sulphonyl)-urea (clopyrasulfuron,
halosulfuron, NC-319), methyl 3-chloro-2-[(5-ethoxy-7-fluoro[l,2,4]tri-
azolo[ 1,5-c]pyrimidin-2-yl-sulphonyl)-amino]-benzoate (cloransulam-me-
thyl), 2-chloro-4-ethylamino-6-(l-cyano-1 -methyl-ethylamino)-1,3,5-triazine
(cyanazine), N-(4,6-dimethoxy-pyrimidin-2-yl)-N'-(2-cyclopropylcarbonyl-
phenylsulphonyl)-urea (cyclosulfamuron, AC-322140), 2,4-dichloro-phen-
oxyacetic 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 methyl sulphate (difenzoquat), N-(2,4-difluoro-
phenyl)-2-(3-trifluoromethyl-phenoxy)-pyridine-3-carboxamide (diflu-
fenican), 2-chloro-N-(2,4-dimethyl-3-thienyl)-N-(2-methoxy-1 -methyl-ethyl)-acetamide (dimethenamid, SAN-582), 2-amino-4-(l-fluoro-l-methyl-ethyl)-6-(l-methyl-2-(3,5-dimethyl-phenoxy)-ethylamino)-l,3,5-triazme (dimexy-flam, IDH-1105), N3,N3-diethyl-2,4-dinitro-6-trifluoromethyl-l,3-diamino-

benzene (dinitramine), N-(4,6-dimethoxy-pyrimidin-2-yl)-N'-(3-methoxy-
carbonyl-6-txifluoromethyl-pyridin-2-yl-sulphonyl)-urea sodium salt (DPX-
KE459), 6,7-dihydro-dipyrido[l,2-a:2',l'-c]pyrazinediium (diquat), S,S-di-
methyl 2-difluoromethyl-4-i-butyl-6-txifluoromethyl-pyridine-3,5-dicarbo-
thioate (dithiopyr), S-ethyl dipropylthiocarbamate (EPTC), S-(phenylmethyl)
N-ethyl-N-(l,2-dimethyl-propyl)-thiocarbamate (esprocarb), ethyl [2-chloro-
5-(4-chloro-5-difluoromethoxy-l-methyl-lH-pyrazol-3-yl)-4-fluoro-phen-
oxy]-acetate (ET-751), (S)-(2-ethoxy-l -methyl-2-oxoethyl)-2-chloro-5-(2-
chloro-4-trifluoromethyl-phen6xy)-benzoate (ethoxyfen), N-(4,6-dimethoxy-
pyrimidin-2-yl)-N'-(2-ethoxy-phenoxysulphonyl)-urea (ethoxysulfuron,
HOE-095404), ethyl 2-[4-(6-chloro-benzoxazol-2-yl-oxy)-phenoxy]-propanoate (fenoxaprop-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), 2-[4-chloro-2-fluoro-5-[(l-methyl-2-propinyl)-oxy]-phenyl]-4,5,6,7-tetra-hydro-lH-isoindole-l,3(2H)-dione (flumipropyn), ethoxycarbonylmethyl 5-(2-chloro-4-trifluoromethyl-phenoxy)-2-nitro-benzoate (fluoroglycofen-ethyl), l-isopropyl-2-chloro-5-(3,6-dihydro-3-methyl-2,6-dioxo-4-trifluoro-methyl-1 (2H)-pyrimidyl)-benzoate (flupropacil), 9-hydroxy-9H-fluorene-9-carboxylic acid (flurenol), (4-amino-3,5-dichloro-6-fluoro-pyridin-2-yl-oxy)-acetic acid (fluroxypyr), 5-methylamino-2-phenyl-4-(3-trifluoromethyl-phenyl)-3(2H)-furanone (flurtamone), methyl-[(2-chloro-4-fluoro-5-(tetra-hydro-3-oxo-lH^H-[l,3,4]4Madiazolo-[3,4-a]-pyridazin^-ylidene)-amino-phenyl]-thio-acetate (fluthiacet-methyl, KIH-9201), 2-amino-4-(hydroxy-methylphosphinyl)-butanoic acid (ammonium salt) (glufosinate-(ammo-nium)), N-phosphonomethyl-glycine (isopropylammonium), (glyphosate, -isopropylammonium), methyl 2-(4,5-dihydro-4-methyl-4-isopropyl-5-oxo-lH-imidazol-2-yl)-4-methyl-benzoate (imazamethabenz-methyl), 2-(4,5-di-hydro-4-methyl-4-isopropyl-5-oxo-lH-imidazol-2-yl)-5-methyl-pyridine-3-carboxylic acid (imazamethapyr), 2-(4,5-dihydro-4-methyl-4-isopropyl-5-

oxo-lH-imidazol-2-yl)-5-methoxymethyl-pyridine-3-carboxylic acid (imaza-
mox), 2-(4,5-dihydro-4-methyl-4-isopropyl-5-oxo-lH-imidazol-2-yl)-quino-
line-3-carboxylic acid (imazaquin), 2-(4,5-dihydro-4-methyl-4-i-propyl-5-
oxo-lH-imidazol-2-yl)-5-ethyl-pyridine-3-carboxylic acid (imazethapyr),
methyl 4-iodo-2-[[[[(4-methoxy-6-methyl-l,3,5-triazin-2-yl)-amino]-carb-
onyl]-amino]-sulphonyl]-benzoate (monosodium salt) (iodosulfuron-methyl-
sodium), 4-hydroxy-3,5-diiod6-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), (5-cyclopropyl-isoxa-
zol-4-yl)-(2-methylsulphonyl-4-trifluoromethyl-phenyl)-methanone (isoxa-
flutole, RPA-201772), 2-[2-[4-[3,5-dichloro-2-pyridinyl)-oxy]-phenoxy]-l-
oxo-propyl]-isoxazolidine (isoxapyrifop), 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), methyl-
2-[[[[(4,6-dimethoxy-2-pyrimidinyl)amino]carbonyl]amino]sulfonyl]-4-
[[(methylsulfonyl)amino]methyl]-benzoate (mesosulfuron), 2-(4-methyl-
sulphony]-2-mtro-benzoyl)-l,3-cycIohexanedione (mesotrione), N'-(4-(3,4-
dihydro-2-methoxy-2,4,4-trimethyl-2H-1 -benzopyran-7-yl-oxy)-phenyl)-N-
methoxy-N-methyl-urea (metobenzuron, UMP-488), N'-(4-bromo-phenyl)-N-
methoxy-N-methylurea (metobromuron), 2-chloro-N-(2-ethyl-6-methyl-
phenyl)-N-(2-methoxy-l -methyl-ethyl)-acet-amide (metolachlor), N-(2,6-
dichloro-3-methyl-phenyl)-5,7-dimethoxy-l,2,4-triazolo[l,5-a]-pyrimidine-2-
sulphonamide (metosulam, DE-511), 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), 2-[[[[(4-methoxy-6-methyl-l ,3,5-triazin-2-yl)-
amino]-carbonyl]-amino]-sulphonyl]-benzoic acid (metsulfuron), methyl
2-[[[[(4-methoxy-6-methyl-l,3,5-triazin-2-yl)-amino]-carbonyl]-amino]-
sulphonyl]-benzoate (metsulfuron-methyl), 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-sulphonyI)-urea (nicosulfuron), S-(2-chloro-benzyl) N,N-diethyl-

thiocarbamate (orbencarb), N-(4,6-dimethyl-pyrimidin-2-yl)-N'-(2-oxetan-3-
yl-oxycarbonyl-phenylsulphonyl)-urea (oxasulfuron), 1,1 '-dimethyl-4,4'-bi-
pyridinium (paraquat), 1 -amino-N-(l-ethyl-propyl)-3,4-dimethyl-2,6-dirritro-
benzene (pendimethalin), N-(4-fluorophenyl)-6-[3-(trifluoromethyl)phenoxy]
2-pyridinecarboxamide (picolinafen), N-(4,6-bis-difluoromethoxy-pyrimidin-
2-yl)-N'-(2-methoxycarbonyl-phenylsu]phonyl)-urea (primisulfuron-methyl),
S-pheny]methyl-N,N-dipropyl-thiocarbamate (prosulfocarb), N-(4-methoxy-
6-methyl-l,3,5-triazin-2-yl)-N'-(2-(3,3,3-trifluoro-propyl)-phenylsulphonyl)-
urea (prosulfuron), 2-chloro-N-(2,6-diethyl-phenyl)-N-(2-propoxy-ethyl)-
acetamide (pretilachlor), 2-chloro-N-isopropyl-N-phenyl-acetamide (propa-
chlor), 0-(6-chloro-3-phenyl-pyridazin-4-yl) S-octy] thiocarbonate (pyridate),
4-(2,4-dichloro-benzoyl)-l,3-dimethy]-5-(4-methyl-phenylsulphonyIoxy)-
pyrazole (pyrazolate), 4-(2,4-dichloro-benzoyl)-l ,3-dim ethyl-5-(phenyl-
carbonylmethoxy)-pyrazole (pyrazoxyfen), N-(4,6-dimethoxy-pyrimidin-2-
y])-N,-(4-ethoxycarbonyl-l-methyl-pyrazol-5-yl-sulphonyl)-urea (pyrazosulf-
uron-ethyl), 7-chloro-3-methyl-quinoline-8-carboxylic acid (quinmerac), N-
(4,6-dimethoxy-pyrimidin-2-yl)-N'-(3-ethylsulphonyI-pyridin-2-yl-sulfonyl)-
urea (rimsulfuron), 6-chloro-2,4-bis-ethylamino-l,3,5-triazine (simazine), 2-
(2-chloro-4-methylsulphonyl-benzoyl)-cyclohexane-1,3-dione (sulcotrione),
2-(2,4-dichloro-5-methylsulphonylamino-phenyl)-4-difluoromethyl-5-methyl-
2,4-dihydro-3H-l,2,4-triazol-3-one (sulfentrazone, F-6285), N-phosphono-
methyl-glycine-trirnethylsulphoniurn (sulfosate), N-(4,6-dimethoxy-
pyrirnidin-2-yl)-N'-(2-ethylsulphonyl)-imidazo[l,2-a]pyridine-3-sulphon-amide (sulfosulfuron, MON-37500), 6-chloro-4-ethylamino-2-tert-butyl-amino-l,3,5-triazine (terbuthylazine), 2-tert-butylarnino-4-ethylarnino-6-me-thylthio-l,3,5-triazine (terbutryn), 2-chloro-N-(2,6-dimethyl-phenyl)-N-(3-methoxy-2-thienyl-methyl)-acetamide (thenylchlor), 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-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-l-one (tralkoxydim), S-(2,3,3-trichloro-2-propenyl) diisopropylcarbamothioate (triallate), N-(4-methoxy-6-methyl-l,3,5-triazin-2-yl)-N'-[2-(2-chloro-ethoxy)-phenylsulphonyl]-urea (triasulfuron), N-methyl-N-(4-methoxy-6-methyl-l,3,5-triazin-2-yl)-N'-(2-methoxycarbonyl-phenyl-sulphonyl)-urea (tribenuron-methyl), 2-(3,5-dichloro-phenyl)-2-(2,2,2-tri-chloro-ethyl)-oxirane (tridiphane), 1 -amino-2,6-dinitro-N,N-dipropyl-4-tri-fluoromethyl-benzene (trifluralin), N-[[(4,6-dimethoxy-2-pyrimidinyl)ami-no]carbonyl]-3-[methyl(methylsulphonyl)amino] 2-pyridinesulphonamide, (WO 91/10 660), N-[[[4-methoxy-6-(trifluoromethyl)-l,3,5-triazin-2-yl]ami-no]carbony]]-2-(trifluoromethyl)-benzenesulphonamide (tritosulfuron)
("active compounds of group 2"),
and optionally
(c) at least one compound which improves crop plant compatibility, from the following group of compounds:
a-(l,3-dioxolan-2-yl-methoximino)-phenylacetonitrile (oxabetrinil), a-(cya-nomethoximino)-phenylacetonitrile (cyometrinil), 4-chloro-N-(l ,3-dioxolan-2-yl-methoxy)-a-trifluoro-acetophenone oxime (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-di-chloro-phenyl)-5-trichloromethyl-lH-l,2,4-triazole-3-carboxylate (fenchlor-azol-ethyl), phenylmethyl 2-chloro-4-trifluoromethyl-thiazole-5-carboxylate (flurazole), 3-dichloroacetyl-5-(2-furanyl)-2,2-dimethyl-oxazolidine (furil-azole, 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-di-



chloro-N,N-di-2-propenyl-acetamide (dichlormid), N-(4-methyl-phenyl)-N'-
(l-methyl-l-phenyl-ethyl)-urea(dymron), l-dichloroacetyl-hexahydro-3,3,8a-
trimethylpyrrolo[l,2-a]-pyrimidin-6(2H)-one (BAS-145138), N-(2-methoxy-
benzoyl)-4-(methylaminocarbonylamino)-benzenesulphonamide, ethyl 4,5-di-
hydro-5,5-diphenyl-3-isoxazolecarboxylate (isoxadifen-ethyl), (4-chloro-2-
methylphenoxy)-acetic acid (MCPA), 2-(4-chloro-2-methylphenoxy)-
propionic acid (mecoprop), diethyl l-(2,4-dichlorophenyl)-4,5-dihydro-5-
methyl-lH-pyrazole-3,5-dicarboxylate (mefenpyr-diethyl) and 2,4-dichloro-
phenoxyacetic acid (2,4-D) and its derivatives ("active compounds of group
3").
Preferred substituents of the radicals listed in the formula (I) shown above are illustrated below.
R preferably represents hydrogen or

where
R2 preferably represents hydrogen, chlorine, cyano, phenyl, C\-Cg-alkyl, methoxy,
methylthio, Ci-C2-alkoxycarbonyl, propylaminocarbonyl, dimethylamino-carbonyl, benzylaminocarbonyl (where the benzyl group is optionally substituted by chloro, methyl or methoxy), 2'-phenylemylaminocarbonyl or furylmemylarninocarbonyl, and
R3 preferably represents optionally chlorine-, fluorine-, cyano-, nitro-, methyl-, methoxy-, ethoxy-, butoxy-, allyloxy-, methylthio-, dimethylamino-, phenoxy-, benzyloxy- or acetoxy-substituted phenyl or represents -COR4, where R4 represents methoxy, ethoxy, methyl, benzyloxy or benzylamino,



A preferably represents chlorine or methoxy and
D and E, which can be identical or different, preferably.represent hydrogen, methoxy or ethoxy.
E-2 particularly preferably represents hydrogen, methyl, methylthio, cyano, methoxycarbonyl or phenyl.
R3 particularly preferably represents optionally methyl- or methoxy-substituted phenyl.
A particularly preferably represents methoxy.
D and E particularly preferably represent methoxy.
R2 very particularly preferably represents phenyl.
R3 very particularly preferably represents phenyl.
Particular emphasis is given to the following mixture components from among the active compounds of group 2:
N-isopropyl-N-(4-fluorophenyl)-(5-trifluoromethyl-l,3,4-thiadiazol-2-yl-oxy)-acetamide, 2-(2-methoxycarbonyl-phenylsulphonylaminocarbonyl)-4-methyl-5-n-propoxy-2,4-dihydro-3H-l,2,4-triazol-3-one or a sodium salt of this compound, 2-(2-trifluoromethoxy-phenylsulphonylaminocarbonyl)-4-methyl-5-methoxy-2,4-dihydro-3H-l,2,4-triazol-3-one or a sodium salt of this compound, 2-(4-fluoro-3-trifluoromethyl-phenoxy)-N-phenylmethyl-butanamide (beflubutamid), methyl 2-[[[[(4,6-dimethoxy-2-pyrirm^myl)amino]carbonyl]amino]sulphonyl]-6-(trifluoro-methy])-3-pyridinecarboxylate (monosodium salt) (flupyrsulfuron-methyl-sodium), methyl 4-iodo-2[[[[(4-methoxy-6-methyl-l,3,5-triazin-2-yl)amino]carbonyl]amino]-



sulphonyljbenzoate (monosodium salt) (iodosulfuron-methyl-sodium), N,N-dimethyl-N'-(4-isopropyl-phenyl)-urea (isoproturon), methyl-2-[[[[(4,6-dimethoxy-2-pyrimidinyl)ammo]carbonyl]amino]sulfonyl]-4-[[(methylsulfonyl)amino]methyl]-benzoate (mesosulfuron), 2-[[[[(4-methoxy-6-methyM,3,5-rriazin-2-yl)-amino]-carbonyl]-amino]-sulphonyl]-benzoic acid (metsulfuron), N-(4,6-dimethoxy-pyrimidin-2-yl)-N'-(2-ethylsulphonyl)-imidazo[l)2-a]pyridine-3-sulphonamide (sulfosulfuron, MON-37500), 2-propinyl (R)-2-[4-(5-chloro-3-fluoro-pyridin-2-yI-oxy)-phenoxy]-propanoate (clodinafop-propargyl), N-(2,4-difluorophenyl)-2-(3-trifluoromethyl-phenoxy)-pyridine-3-carboxarnide (diflufenican), ethyl 2-[4-(6-chloro-benzoxazol-2-yl-oxy)-phenoxy]-propanoate (fenoxaprop-ethyl), 2-(ethox-imino-propyl)-3-hydroxy-5-(2,4,6-trimethyl-phenyl)-2-cyclohexen-l-one (tralkoxy-dim), N-(4-fluorophenyI)-6-[3-(trifluoromethyl)phenoxy]-2-pyridinecarboxamide (picolinafen), N-[[(4,6-dimethoxy-2-pyrimidinyl)amino]carbonyl]-3-[methyl(methyl-sulphonyl)amino]-2-pyridinesulphonamide (WO 91/10 660), N-[[[4-methoxy-6-(tri-fluoromethyl)-l,3,5-triazin-2-yl]amino]carbonyl]-2-(trifluoromethyl)-beiizenesul-phonamide (tritosulfuron).
Particular emphasis is given to the following mixture components from among the active compounds of group 3:
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), (4-chloro-2-methylphenoxy)-acetic acid (MCPA), 2-(4-chloro-2-methylphenoxy)-pro-pionic acid (mecoprop), diethyl l-(2,4-dichlorophenyl)-4,5-dihydro-5-methyl-lH-pyrazole-3,5-dicarboxylate (mefenpyr-diethyl) and 2,4-dichlorophenoxyacetic acid (2,4-D) and its derivatives.
Very particular preference according to the invention is given to selective herbicidal compositions which are characterized in that they comprise an active compound combination comprising





at least one phenoxypyrimidine derivative from the following group of compounds:
2,6-bis[(4,6-dimethoxy-2-pyrimidinyl)oxy]-benzoate (sodium), (bispyribac-sodium, KIH 2023) of the formula



diphenyl-methanone 0-[2,6-bis[(4,6-dimethoxy-2-pyrirnidinyl)oxy]benzoyl] oxime (pyribenzoxrm) of the formula

and
one or more compounds from a second group of herbicides which comprises the active compounds mentioned above under b), where particular preference is given to the active compounds






N-isopropyl-N-(4-fluorophenyl)-(5-trifluoromethyl-l,3,4-thiadiazol-2-yl-oxy)-acetamide of the formula

2-(2-methoxycarbonyl-phenylsulphonylaminocarbonyl)-4-methyl-5-n-propoxy-2,4-dihydro-3H-l,2,4-triazol-3-one or a sodium salt of this compound of the formula

COOCH3 0 O
2-^N ^N N 3
© and
2-(2-txifluoromemoxy-phenylsulphonylaminocarbonyl)-4-methyl-5-methoxy-2,4-dihydro-3H-l,2,4-triazol-3-one or a sodium salt of this compound of the formula


and optionally





c) at least one of the compounds of group 3, which improve crop plant compatibility, where preference is given to those compounds which are mentioned above in preferred ranges.
Most preference according to the invention is given to selective herbicidal compositions which are characterized in that they comprise an amount of an active compound combination comprising
2,6-bis[(4,6-dimemoxy-2-pyrimidinyl)oxy]-benzoate (sodium), (bispyribac-sodium) of the formula

and

one or more compounds from a second group of herbicides which comprises the active compounds mentioned above under b), where particular preference is given to the active compounds

N-isopropyl-N-(4-fluorophenyl)-(5-trifluoromethyl-l,3,4-thiadiazol-2-yl-oxy)-acetamide of the formula



2-(2-methoxycarbonyl-phenylsulphonylaminocarbonyl)-4-methyl-5-n-propoxy-2,4-dihydro-3H-l,2,4-triazol-3-one or a sodium salt of this compound of the formula

and
2-(2-tTifluoromemoxy-phenylsulphonylaminocarbonyl)-4-methyl-5-methoxy-2,4-dihydro-3H-l,2,4-triazol-3-one or a sodium salt of this compound of the formula

and optionally
at least one of the compounds of group 3, which improve crop plant compatibility, where preference is given to those compounds which are mentioned above in preferred ranges.
Surprisingly, it has now been found that the active compound combinations denned above of the phenoxypyrimidine derivatives of the formula (I) and the active compounds of group 2 listed above in combination with active compounds of group 3, have particularly high herbicidal activity combined with very good useful plant


compatibility and can be used in various crops, in particular in rice and 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 compounds of groups 1 and 2 listed above is considerably higher than the sum of the activities of the individual active compounds.
This means that there is not only a supplementary action but 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 phenoxypyrimidine derivatives of the formula (I) and/or their salts and a safener/antidote ("active compound 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 useful 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 MCPA and the substance 2,4-dichlorophenoxy-acetic acid (2,4-D) and its derivatives.
A preferred embodiment is therefore also a mixture comprising, on the one hand, a compound of the formula (I) and/or its salts and, on the other hand, 2,4-D and/or its derivatives, optionally in combination with one or more of the abovementioned active compounds of group 2. Typical derivatives of 2,4-D are, for example, its esters.




A preferred embodiment is furthermore a mixture comprising, on the one hand, a compound of the formula (I) and/or its salts and, on the other hand, MCP A, optionally in combination with one or more of the abovementioned active compounds of group 2.
The compounds diethyl l-(2,4-dichlorophenyl)-4,5-dihydro-5-methyl-lH-pyrazole-3,5-dicarboxylate (mefenpyr-diethyl), (l-methylhexyl)-[(5-chloro-8-quinolinyl)oxy]acetate (cloquintocet-mexyl) and ethyl l-(2,4-dichlorophenyl)-5-(trichloromethyI)-lH-l,2,4-triazole-3-carboxylate (fenchlorazole-ethyl) are described in the patent applications below: DE-A-39 39 503, EP-A-191 736 and DE-A-35 25 205, respectively. 2,4-D is a known herbicide. (4-Chloro-2-methylphenoxy)-acetic acid (MCPA) is likewise a known herbicide.
Furthermore, it is surprising that, &om a large number of known safeners or antidotes capable of antagonizing the damaging effect of a herbicide on the crop plants, specifically the compounds of group (c) listed above which neutralize the damaging effect of compounds of the formula (I) and their salts, optionally also 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 partners of group (c), 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 employed, for 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,








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, Lactuca, Cucumis, Cuburbita.
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, Apera, Phalaris.
Monocotyledonous crops of the genera: Oryza, Zea, Triticum, Hordeum, Avena, Secale, Sorghum, Panicum, Saccharum, Ananas, Asparagus, Alhum.
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.
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 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 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 bis 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 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 mentioned above under (c), which improve crop plant compatibility (antidotes/safeners), are present per part by weight of active compound of the formula (I), 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


substances impregnated with active compound, and very fine capsules 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 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 and also 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, and also 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 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 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, alkylsulphates, arylsulphonates as well as protein hydrolysates; suitable dispersing agents are: for example lignin-sulphite waste liquors and methylcellulose.





Tackifiefs 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 safening active compounds.
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.
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.


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 broadcasting.
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 (active compound of the formula I)
at an application rate of p kg/ha
and Y = % 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
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.




Examples Example 1
MKH 6561 and bispyribac-sodium (wheat / post-emergence spring)
To examine a possible synergism, the compounds MKH 6561 and bispyribac-sodium (KIH 2023) were tested under outdoor conditions in one of the main cultivation areas of winter wheat in Great Britain against the economically important weed grass Alopecurus myosuroides Huds. The small-plot experiment was carried out on cultivated land under agricultural use. An area with particularly extensive weed growth was chosen.
The active compounds were applied across the area by the spray method, with a medium droplet size, post-emergence in spring. To produce a suitable preparation of active compound, the active compounds were formulated as 70 WG (70% w/w water-dispersible powder) or 400 SC (400 g/1 suspension concentrate) and suspended in water. The spray liquor was then applied at a water application rate of 200 1/ha, which is customary in practice.
To assess the crop compatibility, after the treatment, plant growth inhibitions or paling of the leaf area was assessed in % damage in comparison to the development of the untreated control. At the time of blossom, the herbicidal activity was assessed as % reduction in comparison to the untreated control, based on the number of ears. The figures denote:
0 % = no damage of the crops or no herbicidal effect, 100 % = total destruction of the crops or the weeds.
In this test, MKH 6561 and KIH 2023 showed a highly pronounced synergism in the action against Alopecurus myosuroides (Table 1). The activity was considerably



higher than the value which had been expected for the mixture according to Colby's formula. Damage to the crop did not occur.
Tablel

Species
Activity (%)
MKH 6561 KTH 2023 MKH6561 Value
(42 g (50 g +KIH 2023 according to
a.i./ha) a.i./ha) (42+50 g Colby
95.2 0
79.9 0
59.3 0
a.i./ha) (1967)
Alopecurus myosuroides 50.5
Crop damage 0
Example 2
MCPA and bispyribac-sodium (rice, post-emergence)
To examine a possible safener action, the compound MCPA was tested together with bispyribac-sodium in rice against Echinochloa spp. (E. crus-galli, E. erecta).



The active compounds were applied post-emergence in spring. The undesirable plants were in a development stage of from 13 to 15 or from 21 to 23 according to the BBCH scale for standard classification of the phenological development stages of mono- and dicotyledonous plants. The rice plants were in a development stage of from 13 to 14 or from 21 to 22, according to the BBCH scale (Feller et al. 1995, Nachrichtenbl. Deut. Pflanzenschutzd. 47, 193-206).
To assess the safener effect of MCPA, the phytotoxicity of bispyribac-sodium (KTH 2023) was tested with and without MCPA, and the yield in kg/ha, the number of ears per m2 and the weight of the rice grains (weight per 1000 grains in g) were determined (Table 2).







Without MCPA, there was a slight phytotoxicity. This is not observed when MCPA is present. With respect to the yield, there was a statistically significant difference (8210 kg/ha without and 11,010 kg/ha with MCPA). There were also differences in the number of ears per m^ and the weight of 1000 grains.
Table 2

Treatment Rate
(gof a.i./ha) Phytotoxicit
y
(%) 15 days
after
treatment Phytotoxici
ty
(%) 30 days after treatment Yield (kg/ha) Ears/ m^ Weight
of
1000
grains
ing
KIH 2023 + S 75+0.1% 7 2 8210 531 30
KTH 2023 + S + MCPA 75+0.1% +1000 0 0 11,010 573 30,8
S = Surfactant TREND
Example 3
FOE 5043 and KTH 2023 (pre-emergence/post-emergence)
To examine a possible synergism, the compounds FOE 5043 and KIH 2023 were tested under greenhouse conditions against various weeds.
To this end, the amount of active substance required in each case is dissolved in a few millilitres, in general 2-3 ml, of the solvent (acetone or DMF), emulsifiers added (1 ml) and the resulting concentrate is diluted with water to the desired concentration.









Mixtures of two or more active compounds are prepared by mixing the concentrates, prepared as above, of the active compounds in question, adding, if appropriate, further active compounds, formulations or other substances, followed by dilution with water to the desired concentration.
In general, a surfactant, for example Renex 36, is added in a concentration of 0.1% (w/v) to the spray liquors intended for the post-emergence test.
The amount of active compound or its formulation in the solutions to be tested corresponds to the desired application rates per ha.
Pre-emergence
Seeds of the test plants are sown in normal soil. After 24 h, the desired amount of active substance, as active ingredient or formulation, is sprayed onto the surface of the soil. The concentration of the active substance in the spray liquor is chosen so that the desired application rate can be applied in 500 1 of water/ha.
Post-emergence
Test plants are grown under controlled temperature and light conditions. When the plants have reached a height of from 5 to 15 cm, the test solution is sprayed.

The concentration of the active substance in the spray liquor is chosen so that the desired application rate can be applied in 500 1 water/ha.
Evaluation is carried out about three weeks after application. The herbicidal activity is assessed visually in comparison to the untreated control. The figures denote
0% = no herbicidal effect, corresponds to the untreated control
100% = total destruction of the test plants.



In these tests, FOE .5043 and KIH 2023 showed a highly pronounced synergism in the action against various weeds (Tables 3-15; the values marked (*) were calculated according to Colby, 1967).
Table 3: FOE 5043 + KIH 2023 (Pre-emergence)

Application rate g of a.i./ha Bromus
secalinus
observed Bromus secalinus calculated*
FOE 5043 125 20
KIH2023 8 0
FOE 5043
+
KIH2023 125 + 8 95 20

Table 4: FOE 5043 + KIH 2023 (Pre-emergence)

Application rate g of a.i./ha Lolium
perenne
observed Lolium
perenne
calculated*
FOE 5043 125 95
KIH2023 15 4 0 0
FOE 5043
+
KIH 2023 30+15 125 + 4 90 100 10 95


Table 5: FOE 5043 + KIH 2023 (Pre-emergence)

Application rate g of a.i./ha Chenopodium
album
observed Chenopodium
album
calculated*
FOE 5043 125 30
KIH2023 15 20
FOE 5043
+
KIH2023 125 + 15 100 44
Table 6: FOE 5043 + KIH 2023 (Pre-emergence)

Application rate g of a.i./ha Avena
fatua
observed Avena
fatua
Calculated*
FOE 5043 125 60 90 70
KIH2023 4 0
FOE 5043
+
KIH 2023 • 125 + 4 60 + 4 100 100 90
70
Table 7: FOE 5043 + KIH 2023 (Pre-emergence)

Application rate g of a.i./ha Polygonum
convolvulus
observed Avena
convolvulus
calculated*
FOE 5043 125 0
KIH2023 15 10
FOE 5043
+
KIH 2023 125+15 90 10


Le A 33 983-ForeisflTountries

Table 8: FOE 5043 + KIH 2023 (Pre-emergence)

Application rate Veronica Veronica
g of a.i./ha persica persica
observed calculated*
FOE 5043 125 30
60 20
KIH2023 8 60
4 20
FOE 5043 125 + 8 100 72
+ 60 + 4 98 36
KIH2023
Table 9: FOE 5043 + KIH 2023 (Post-emergence)

Application rate Galium Galium
g of a.i./ha aparine aparine
observed calculated*
FOE 5043 60 80
30 70
KIH2023 4 0
FOE 5043 60 + 4 98 80
+ 30 + 4 98 70
KIH2023


Table 10: FOE 5043 + KIH 2023 (Post-emergence)

Application rate gof a.i./ha Polygonum
convolvulus
observed Polygonum
convolvulus
calculated*
FOE 5043 125
60
30 0 0 0
KIH2023 4 0
FOE 5043
+
KIH2023 125 + 4 60 + 4 30 + 4 95 98 90 0
0 ' 0

Table 11: FOE 5043 + KIH 2023 (Post-emergence)

Application rate g of a.i./ha Veronica persicum observed Veronica persicum calculated*
FOE 5043 12S 60 30 30
KIH2023 4 50
FOE 5043
+
KIH 2023 125 + 4 60 + 4 95 90 65 65




Table 12: FOE 5043 + KIH 2023 (Post-emergence)

Application rate Viola Viola
g of a.i./ha arvensis arvensis
observed calculated*
FOE 5043 60 0
30 0
KIH2023 4 70
FOE 5043 60 + 4 95 70
+ 30 + 4 95 70
KIH2023

Table 13: FOE 5043 + KIH 2023 (Post-emergence)

Application rate g of a.i./ha Solanum
nigrum
observed Solanum
nigrum
calculated*
FOE 5043 60 0
KIH2023 4 90
FOE 5043
+
KIH2023 60 + 4 100 90





Example 4
Flupyrsulfliron and KIH 2023 (Pre-emergence/post-emergence)
To examine a possible synergism, the compounds flupyrsulfuron and KIH 2023 were tested under greenhouse conditions against various weeds.
For the pre- and post-emergence experiments, application was carried out as described in Example 3.
Evaluation was likewise carried out as described in Example 3.
Once more, the figures denote
0% = no herbicidal effect, corresponds to the untreated control 100% = total destruction of the test plants
In these tests, flupyrsulfuron and KIH 2023 showed a highly pronounced synergism in the activity, against various weeds (Tables 16-27; the values marked (*) were calculated according to Colby, 1967).



Table 14: Flupyrsulfuron + KIH 2023 (Pre-emergence)

Application rate g of a.i./ha Brassica observed Brassica calculated*
Flupyrsulfuron 8 4 20 20
KJH2023 15 4 0 0
Flupyrsulfuron
+
KIH2023 8 + 15 4+15 8 + 4 4 + 4 95 60 90 60 20 20 20 20

Table 15: Flupyrsulfuron + KIH 2023 (Pre-emergence)

Application rate g of a.i./ha Ipomoea
hederacea
observed Ipomoea
hederacea
calculated*
Flupyrsulfuron 2 30
KIH 2023 4 0
Flupyrsulfuron
+
KIH2023 2 + 4 70 30





Table 16: Flupyrsulfuron + KIH 2023 (Pre-emergence)

Application rate Setaria Setaria
g of a.i./ha viridis viridis
observed calculated*
Flupyrsulfuron 8 20
4 20
2 0
KIH2023 15 0
4 0
Flupyrsulfuron 8+15 90 20
+ 4+15 50 20
KIH2023 2 + 4 70 0
Table 17: Flupyrsulfuron + KIH 2023 (Post-emergence)

Application rate Alopecurus Alopecurus
g of a.i./ha myosuroides myosuroides
observed calculated*
Flupyrsulfuron 8 80
4 80
2 50
KIH2023 15 0
8 0
Flupyrsulfuron 8+15 98 80
+ 4+15 95 80
KIH2023 2+15 90 50
8 + 8 98 80
4 + 8 90 80


Table 18: Flupyrsulfuron + KIH 2023 (Post-emergence)

Application rate g of a.i./ha Bromus
secalinus
observed Bromus
secalinus
calculated*
Flupyrsulfuron 8 0
KIH 2023 15 80
Flupyrsulfuron
+
KIH2023 8 + 15 100 80
Table 19: Flupyrsulfuron + KIH 2023 (Post-emergence)


Application rate g of a.i./ha Abutilon
theophrasti
observed Abutilon
theoprasti
calculated*
Flupyrsulfuron 8 60
KIH2023 4 0
Flupyrsulfuron
+
KIH2023 8 + 4 95 60
Table 20: Flupyrsulfuron + KIH 2023 (Post-emergence)

Application rate g of a.i./ha Chenopodium
album
observed Chenopodium
album
calculated*
Flupyrsulfuron 2 40
KIH2023 4 0
Flupyrsulfuron
+
KIH 2023 2 + 4 80 40



Table 21: Flupyrsulfuron + KIH 2023 (Post-emergence)

Application rate Matricaria Matricaria
g of a.i./ha inodora inodora
observed calculated*
Flupyrsulfuron 4 90
2 50
KIH2023 4 0
Flupyrsulfuron 4 + 4 100 90
+ 2 + 4 98 50
KIH2023

Table 22: Flupyrsulfuron + KIH 2023 (Post-emergence)

Application rate Polygonum Polygonum
g of a.i./ha convolvulus convolvulus
observed calculated*
Flupyrsulfuron 8 80
- 4 80
2 70
KIH2023 4 0
Flupyrsulfuron 8 + 4 100 80
+ 4 + 4 100 80
KIH2023 2 + 4 90 70


Table 23: Flupyrsulfuron + KIH 2023 (Post-emergence)

Application rate g of a.i./ha Solanum
nigrum
observed Solanum
nigrum
calculated*
Flupyrsulfuron 8 0
KIH2023 4 90
Flupyrsulfuron
+
KIH2023 8 + 4 100 90
Table 24: Flupyrsulfuron + KIH 2023 (Post-emergence)

Application rate g of a.i./ha Veronica persicum observed Veronica persicum calculated*
Flupyrsulfuron 8 0
KIH2023 4 50
Flupyrsulfuron
+
KIH2023 8 + 4 90 50
Table 25: Flupyrsulfuron + KIH 2023 (Post-emergence)

L Application rate g of a.i./ha Viola
arvensis
observed Viola
arvensis
calculated*
Flupyrsulfuron 8 4 2 30
0
0 -
KIH2023 8 4 90
70
Flupyrsulfuron
+
KIH 2023 4 + 8 2 + 8 8 + 4 4 + 4 100 100 100 100 90 90 79 70






Example 5
Cloquintocet and KIH 2023 (barley/wheat, post-emergence)
To examine the safener effect of cloquintocet, this compound was tested together with KIH 2023 in barley and wheat.
To assess the safener effect of cloquintocet, the phytotoxicity of KIH 2023 was tested with and without MCPA (see Tab. 28 and 29).
The assessment itself was carried out according to Example 1, i.e. the crop compatibility was rated in % damage, based on the development of the untreated control. Again, the figures denote:
0% = no damage of the crop or no herbicidal effect
100% = total destruction of the crop.
In the tests, cloquintocet showed a considerable safener effect.


Cloquintocet and KIH 2023 (Post-emergence)

Active compound Application rate in g/ha Damage barley [%]
KIH2023 60 50
KIH2023 30 35
KIH2023 15 20
KIH 2023 + cloquintocet 60 + 60 20
KIH 2023 + cloquintocet 30 + 30 10
KIH 2023 + cloquintocet 15 + 15 5
Table 27: Cloquintocet und KIH 2023 (Post-emergence)

Active compound. Application rate in g/ha Damage wheat [%]
KIH2023 250 45
KIH 2023 125 20
KIH 2023 60 10
KIH 2023 + cloquintocet 250 + 250 20
KIH 2023 + cloquintocet 125 + 125 10
KIH 2023 + cloquintocet 60 + 60 5
KIH 2023 + cloquintocet 250 + 30 20
KIH 2023 + cloquintocet 125 + 30 15
KIH 2023 + cloquintocet 60 + 30 5




Example 6
Mefenpyr and KIH 2023 (barley/wheat, post-emergence)
To examine the safener effect of mefenpyr, this compound was tested together with KIH 2023 in barley and wheat.
The safener effect of mefenpyr was assessed analogously to Example 5 (see Tables 30 and 31).
Additionally, the compatibility of mefenpyr alone was tested in cereal (post-emergence) (see Tables 31-35).

In these tests, mefenpyr showed a highly pronounced safener effect.




Table 28: Mefenpyr and KIH 2023 (Post-emergence)

Active compound Application rate in g/ha Damage barley [%]
KIH2023 60 50
KIH 2023 30 35
KIH2023 15 20
KIH 2023 + mefenpyr 60 + 60 20
KIH 2023 + mefenpyr 30+30 . 5
KIH 2023 + mefenpyr 15 + 15 5
KIH 2023 + mefenpyr 60 + 30 20
KIH 2023 + mefenpyr 30 + 30 15
KIH 2023 + mefenpyr 15 + 30 5
Table 29: Mefenpyr and KIH 2023 (Post-emergence)

Active compound Application rate in g/ha Damage wheat [%]
KIH 2023 250 45
KIH2023 125 20
KIH2023 60 10
KIH 2023 + mefenpyr 250 + 250 10
KIH 2023 + mefenpyr 125 + 125 5
KIH 2023 + mefenpyr 60 + 60 5
Kffl 2023 + mefenpyr 250 + 30 25
KIH 2023 + mefenpyr 125 + 30 10
KIH 2023 + mefenpyr 60 + 30 5



Table 30: Compatibility of mefenpyr in cereal (Post-emergence)

Application rate in g/ha Wheat (14 days) [%]
1000 0
500' 0
100 0
Table 31: Compatibility of mefenpyr in cereal (Post-emergence)

Application rate in g/ha Damage wheat (15 days) [%] Damage
barley (15 days) [%1
500 0 0
100 0 0
50 0 0
10 0 0
Table 32: Compatibility of mefenpyr in cereal (Post-emergence)

Application rate in g/ha Damage wheat (3 days) [%] Damage wheat (7 days) [%] Damage wheat (21 days)
[%]
200 0 0 0
100 0 0 0
50 0 0 0




Table 33: Compatibility of mefenpyr in cereal (Post-emergence)

Application rate in g/ha Damage barley (3 days) [%) Damage barley (7 days) [%] Damage barley (21 days)
200 0 0 0
100 0 0 0
50 . 0 0 0





Example 7
Fenchlorazole and KIH 2023 (wheat/post-emergence)
To examine the safener effect of fenchlorazole, this compound was tested together with KIH 2023 in wheat.
The safener effect of fenchlorazole was assessed analogously to Example 5 (see Tables 36 and 37).

In the tests, fenchlorazole showed a considerable safener effect.


Le A 33 983-Foreign Countries
-45-
Table 34: Fenchlorazole and KIH 2023 (Post-emergence)

Active compound Application rate . in g/ha Damage wheat [%]
KIH2023 250 45
KIH 2023 125 20
KIH 2023 60 10
KIH 2023 + fenchlorazole 250 + 250 20
KIH 2023 + fenchlorazole 125 + 125 10
KIH 2023 + fenchlorazole 60 + 60 5
KIH 2023 + fenchlorazole 250 + 30 15
KIH 2023 + fenchlorazole 125 + 30 10
KIH 2023 + fenchlorazole 60 + 30 5
Table 35: Compatibility of fenchlorazole in cereal, post-emergence
5

Active compound Damage wheat (14 days)
[%) Damage barley (14 days) [%]
100 0 0
10 0 0


We Claim:
1. Herbicidal compositions, characterized in that they comprise an effective amount of an active compound combination comprising
(a) at least one phenoxypyrimidine derivative of the general formula (I)


where
R2 represents phenyl (and R3 represent phenyl, A represents methoxy and
and/or a salt of a compound of the formula (I)
("active compounds of group 1").
and
(b) one or more compounds from a second group of herbicides selected from the group consisting of:
N-isopropyl-N-(4-fluorophenyl)-5-trifluoromethyl-1,3,4-
thiadiazol-2-yloxy)-acetamide (fTufenacet), 2-(2-


methoxycarbonyl-phenylsulphonylaminocarbonyl)-4-methyl-
5-n-propoxy-2,4-dihydro-3H-l,2,4-triazol-3-one or a sodium
salt of this compound (propoxycarbazone(-sodium)), ethyl 2-
[4-(6-chlorobenzoxazol-2-yloxy)phenoxy]propanoate
(fenoxaprop-ethyl), methyl2-[[[[(4,6-dimethoxy-2-
pyrimidinyl) amino] carbonyl] amino] sulphonyl] -6 -
(trifluoromethyl)3-pyridinecarboxylate(monosodium salt)
(flupyrsulfuron-methyl(-sodium)) ("active compounds of group 2");
and optionally
(c) at least one compound which improves crop plant compatibility, selected from the group consisting of:
a-(1,3-dioxolan-2-yl-methoximino)-phenylacetonitrile (oxabetrinil),
a-(cyanomethoximino)-phenylacetonitrile (cyometrinil), 4-chloro-N-
(l,3-dioxolan-2-yl-methoxy)-a-trifluoro-acetophenone oxime
(fluxofenim), 4,6-dichloro-2-phenyl-pyrimidine (fenclorim), 4-
dichloroacetyl-3,4-dihydro-3-methyl-2H-1,4-benzox-azine
(benoxacor), 1-methyl-hexyl 5-chloro-quinoxalin-8-oxy-acetate
(cloquinlocet), 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-lH-l,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-
methylphenyl)-N'-(l-methyl-l-phenyl-ethyl)-urea (dymron), 1-
dichloroacetyl-hexahydro-3,3,8a-trimethylpyrrolo[ 1,2-a]-pyrimidin-
6(2H)-one (BAS-145138), N-(2-methoxy-benzoyl)-4-
(methylaminocarbonylamino)-benzenesulphonamide, ethyl
4,5dihydro-5,5-diphenyl-3-isoxazolecarboxylate (isoxadifen-ethyl),

diethyl l-(2,4-dichlorophenyl)-4,5-dihydro-5-methyl-lH-pyrazole-
3,5-dicarboxylate (mefenpyr-diethyl) and 2,4-
dichlorophenoxyacetlc acid (2,4-D) and its derivatives ("active compounds of group 3").
2. Herbicidal compositions as claimed in claim 1, wherein vthey comprise, as active compound of group 2, the following compound: ethyl 2- [4-(6-chlorobenzoxazol-2-yloxy)phenoxy]propanoate.
3. Herbicidal compositions as claimed in claim 1 or 2, wherein they comprise, as active compound of group 3, at least one compound which improves crop plant compatibility, from the following group of compounds:
1-methylhexyl 5-chloro-quinoxalin-8-oxy-acetate (cloquintocel), 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-
isoxazolecarboxy-late (isoxadifen-ethyl), diethyl l-(2,4-
dichlorophenyl)-4,5-dihydro-5-methyl-lH-pyrazole-3,5-dicarboxylate (mefenpyr-diethyl) and 2,4-dichlorophenoxyacetic acid (2,4-D) and its derivatives.
4. Herbicidal compositions as claimed in any of claims 1 to 3, wherein they comprise, as active compound of group 1, 2,6-bis[(4,6-dimethoxy 2-pyrimidinyl)oxy]-benzoate (sodium) (bispyribac-sodium) or diphenyl-methanone 0-[2,6-bis[(4,6-dimethoxy-2-pyrimidinyl)oxy]benzoyl) oxime (pyribenzoxim).
5. Herbicidal compositions as claimed in any of claims 1 to 4, wherein they comprise, as active compound of group 1, 2,6-bis[(4,6-dimethoxy-2-pyrimidinyl)oxy]-benzoate (sodium), (bispyribac-sodium).
6. Herbicidal composition as claimed in any of claims 1 and 3 to 5 wherein it comprises, as active compound of group 2, flufenacet.

7. Herbicidal composition as claimed in any of claims 1 and 3 to 5 wherein it comprises, as active compound of group 2, propoxycarbazone or the sodium salt thereof.
8. Herbicidal composition as claimed in any of claims 1 and 3 to 5 wherein it comprises, as active compound of group 2, flupyrsulfuron-methyl or the sodium salt thereof.
9. Herbicidal compositions substantially as herein described with reference to the foregoing examples.
Dated this 11th day of September, 2000.
(RANJNA MEHTA-DUTT)
OF REMFRY AND SAGAR
ATTORNEY FOR THE APPLICANTS


Documents:

825-mum-2000-abstract(05-11-2007).doc

825-mum-2000-abstract(05-11-2007).pdf

825-mum-2000-cancelled pages(05-11-2007).pdf

825-mum-2000-claims(granted)-(05-11-2007).doc

825-mum-2000-claims(granted)-(05-11-2007).pdf

825-mum-2000-correspondence 1(08-11-2007).pdf

825-mum-2000-correspondence 2(06-09-2006).pdf

825-mum-2000-correspondence(ipo)-(15-10-2007).pdf

825-mum-2000-form 1(05-11-2007).pdf

825-mum-2000-form 1(24-08-2007).pdf

825-mum-2000-form 13(24-08-2007).pdf

825-mum-2000-form 18(15-12-2005).pdf

825-mum-2000-form 2(granted)-(05-11-2007).doc

825-mum-2000-form 2(granted)-(05-11-2007).pdf

825-mum-2000-form 3(01-03-2001).pdf

825-mum-2000-form 3(24-07-2007).pdf

825-mum-2000-form 5(05-11-2007).pdf

825-mum-2000-form 5(24-08-2007).pdf

825-mum-2000-pct-isa-210(11-09-2000).pdf

825-mum-2000-petition under rule 137(24-08-2007).pdf

825-mum-2000-petition under rule 138(24-08-2007).pdf

825-mum-2000-power of authority(11-09-2000).pdf

825-mum-2000-power of authority(24-08-2007).pdf


Patent Number 213277
Indian Patent Application Number 825/MUM/2000
PG Journal Number 43/2008
Publication Date 24-Oct-2008
Grant Date 26-Dec-2007
Date of Filing 11-Sep-2000
Name of Patentee BAYER AKTIENGESELLSCHAFT
Applicant Address D-51368 LEVERKUSEN,
Inventors:
# Inventor's Name Inventor's Address
1 DIETER FEUCHT Ackereg 9, 40789 Monheim
2 MATHIAS KREMER HEDDINGHOFENER STR. 31, 51399 BURSCHEID,
3 DIETER FEUCHT Ackereg 9, 40789 Burscheid
4 DIETER FEUCHT Ackereg 9, 40789 BMonheim
5 DIETER FEUCHT Ackereg 9, 40789 Monheim
6 HELMUT FURSCH Birkenstr. 3c, 42799 Leichlingen
7 ARNDT WELLMANN Neustrasse 3, 40789 Monheim
PCT International Classification Number A01N 43/54
PCT International Application Number N/A
PCT International Filing date
PCT Conventions:
# PCT Application Number Date of Convention Priority Country
1 19947918.6 1999-10-06 Germany