ZA200208479B - Selective heteroaryloxy-acetamide-based herbicides. - Google Patents

Selective heteroaryloxy-acetamide-based herbicides. Download PDF

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ZA200208479B
ZA200208479B ZA200208479A ZA200208479A ZA200208479B ZA 200208479 B ZA200208479 B ZA 200208479B ZA 200208479 A ZA200208479 A ZA 200208479A ZA 200208479 A ZA200208479 A ZA 200208479A ZA 200208479 B ZA200208479 B ZA 200208479B
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methyl
ethyl
chloro
phenyl
dichloro
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ZA200208479A
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Dieter Feucht
Peter Dahmen
Mark Wilhelm Drewes
Rolf Pontzen
Mathias Kremer
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Bayer Cropscience Ag
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    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/82—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with three ring hetero atoms

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  • Life Sciences & Earth Sciences (AREA)
  • Agronomy & Crop Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)

Description

Co. Le A 34 480-Foreign Countries LWKr/NT 0
Selective herbicides based on heteroaryloxy-acetamides : The invention relates to novel selective-herbicidal synergistic active compound combinations comprising known heteroaryloxy-acetamides and known herbicidally active compounds and/or compounds which improve crop plant tolerance, which active
E compound combinations can be used with particularly good results for the selective control of weeds in crops of various useful plants.
As strong herbicides, which are active in particular against monocotyledonous weeds, heteroaryloxy-acetamides have been the subject of a number of patent applications (cf. EP-A 5501, EP-A 18497, EP-A 29171, EP-A 94514, EP-A 100044, EP-A 100045, EP-A 161602, EP-A 195237, EP-A 348734, EP-A 348737, DE-A 4317323).
However, the activity of these compounds and/or their compatibility with crop plants is/are not always entirely satisfactory.
Furthermore, active compound combinations of heteroaryloxy-acetamides and other
Co herbicidally active compounds for obtaining a synergistic effect (cf. WO-A 94/02014, - WO-A-96/07323, WO-A-96/11575, WO-A-96/17519, WO-A-98/08383, cf. also
US-A-5858920, US-A-5945379, US-A-5985797) or of heteroaryloxy-acetamides and compounds which can improve the crop plant tolerance of herbicides (cf. ~~ DE-A 3418167, cf. also S-A-5858920) have been disclosed. However, the use properties of these combination products are likewise not always entirely satisfactory. :
Surprisingly, it has now been found that a number of known active compounds from the group of the heteroaryloxy-acetamides, when used together with known herbicidally active compounds from various substance classes and/or compounds which improve crop plant tolerance, show pronounced synergistic effects with respect to the action against weeds and/or have significantly improved crop plant tolerance and can be used particularly advantageously as broad-spectrum combination preparations for the selective control of weeds in crops of useful plants, : d
) " Le A 34 480-Foreign Countries such as, for example, in cotton, barley, maize, potatoes, oilseed rape, rice, soya beans, sunflowers, wheat and sugar cane.
The invention provides selective herbicidal compositions, characterized in that they comprise an effective amount of an active compound combination consisting of (a) a heteroaryloxy-acetamide of the general formula (I)
Het N 0) in which
Ar represents optionally halogen-, C;-C4-alkyl- or C1-C4-halogenoalkyl- substituted phenyl,
Het represents thiadiazolyl, which is substituted by halogen or by in each case optionally halogen-substituted C1-Cy4-alkyl or phenyl, and
R represents alkyl, alkenyl or alkinyl having in each case up to 4 carbon atoms, + ("active compounds of group 1") and (b) one or more compounds from a second group of herbicides containing the active compounds mentioned hereinbelow: 1H-1,2,4-triazol-3-amine ~~ (amitrole), 2-[2,4-dichloro-5-(2-propinyloxy)- phenyl]-5,6,7,8-tetrahydro-1,2,4-triazolo-[4,3-a]-pyridin-3(2H)-one (azafen- idin), N-(4,6-dimethoxy-pyrimidin-2-yl)-N’-[ 1-methyl-4-(2-methyl-2H-
N Le A 34 480-Foreign Countries tetrazol-5-yl)-1H-pyrazol-5-ylsulphonyljurea (azimsulfuron), N-benzyl-2-(4- fluoro-3-trifluoromethyl-phenoxy)-butanamide (beflubutamid), N-butyl-N- ethyl-2,6-dinitro-4-trifluoromethyl-benzeneamine (benfluralin), methyl 2-[2- : [4-(3,6-dihydro-3-methyl-2,6-diox o-4-trifluoromethyl-1(2H)-pyrimidinyl- phenoxymethyl]-5-ethyl-phenoxy-propanoate (benzfendizone), 3-(2-chloro- : 4-methylsulphonyl-benzoyl)-4-phenylthio-bicyclo-[3.2.1]-oct-3-en-2-one (benzobicyclon), [1,1-dimethyl-2-ox0-2-(2-propenyloxy)]-ethyl 2-chloro- 5-(3,6-dihydro-3-methyl-2,6-dioxo-4-trifluoromethyl-1(2H)-pyrimidinyl)-
Co benzoate (butafenacil-allyl), 2-(1-ethoximino-propyl)-3-hydroxy-5-[2,4,6-tri- methyl-3-(1-oxo-butyl)-phenyl]-2-cyclohexen-1-one (butroxydim), 2-[1-[(3- chloro-2-propenyl)-oxy-imino]-propyl]}-3-hydroxy-5-(tetrahydro-2H-pyran- : oT * 4-yl)-2-cyclohexen-1-one (caloxydim, tepraloxydim), ethyl 2-chloro-3-[2-
Co chloro-5-(1,3,4,5,6,7-hexahydro-1,3-dioxo-2H-isoindol-2-yl)-phenyl}- 2-propanoate (cinidon-ethyl), 2-[1-[2-(4-chloro-phenoxy)]-propoxyamino- butyl]-5-(tetrahydro-2H-thiopyran-3-yl)-1,3-cyclohexanedione (clefoxydim), : (E,E)-(+)-2-[1-[[(3-chloro-2-propenyl)-oxy]-imino]-propyl]-3-hydroxy- -2-cyclohexen-1-one (clethodim), methyl 3-chloro-2-[[(5-ethoxy-
Co 7-fluoro[ 1,2,4]triazolo{1,5-c]pyrimidin-2-yl)sulphonyl Jamino]-benzoate : (cloransulam-methyl), 2-(1-ethoximinobutyl)-3-hydroxy-5-(tetrahydro-2H- thiopyran-3-yl)-2-cyclohexen-1-one (cycloxydim), N-(2,6-dichloro-phenyl)- : 5-ethoxy-7-fluoro-{1,2,4]-triazolo-[1,5-c]-pyrimidine-2-sulphonamide (diclosulam), 2-[1-[(3,5-difluoro-phenyl)-amino-carbonyl-hydrazono]-ethyl}- : pyridine-3-carboxylic acid (diflufenzopyr), (S)-2-chloro-N-(2,4-dimethyl- + 3-thienyl)-N-(2-methoxy-1-methyl-ethyl)-acetamide (dimethenamid-P), 2-[2- + 25 (3-chloro-phenyl)-oxiranylmethyl]-2-ethyl-1H-indene-1,3(2H)-dione (epropodan), (R)-ethyl = 2-[4-(6-chloro-benzoxazol-2-yl-oxy)-phenoxy]- : : propanoate (fenoxaprop-P-ethyl), N-(2,6-difluoro-phenyl)-8-fluoro- 5-methoxy-[1,2,4]-triazolo-[1,5-c]-pyrimidine-2-sulphonamide (florasulam), butyl - (R)-2-[4-(5-trifluoromethyl-pyridin-2-yl-oxy)-phenoxy]-propanoate ‘(fluazifop-P-butyl), the sodium salt of 4,5-dihydro-3-methoxy-4-methyi- 5-0x0-N-[(2-trifluoromethoxy-phenyl)-sulphonyl}-1H-1,2,4-triazole-1- - carboxamide (flucarbazone-sodium), ethyl [2-chloro-4-fluoro-5-(5-methyl- : 6-o0x0-4-trifluoromethyl-1(6H)-pyridazinyl)-phenoxy}-acetate (flufenpyr), - 2-[7-fluoro-3,4-dihydro-3-ox0-4-(2-propinyl)-2H-1,4-benzoxazin-6-yl}- 4,5,6,7-tetrahydro-1H-isoindole-1,3-dione (flumioxazin), the sodium salt of
N-(4,6-dimethoxy-pyrimidin-2-yl)-N’-(3-methoxycarbonyl-6-trifluoromethyl-
. Le A 34 480-Foreign Countries pyridin-2-yl-sulphonyl)-urea (flupyrsulfuron-methyl-sodium), 2-[[[[(4.6- dimethoxy-2-pyrimidinyl)-amino}-carbonyl}-amino}-sulphonyl]-4- formylamino-N,N-dimethyl-benzamide (foramsulfuron), (R)-2-[4-(3-chloro- 5-trifluoromethyl-pyridin-2-yl-oxy)-phenoxy]-propanoic acid (and its methyl, -2-ethoxy-ethyl and butyl esters) (haloxyfop, -methyl, -P-methyl, -ethoxyethyl, -butyl), 2-[4,5-dihydro-4-methyl-4-(1-methylethyl)-5-oxo0-1H- imidazol-2-yl)-5-(methoxymethyl)-3-pyridinecarboxylic acid (imazamox), the sodium salt of N-(4-methoxy-6-methyl-1,3,5-triazin-2-yl)-N’-(5-iodo-2- methoxycarbonyl-phenylsulphonyl)-urea (iodosulfufon-methyl-sodium), (4- chloro-2-methylsulphonyl-phenyl)-(5-cyclopropyl-isoxazol-4-yl)-methanone (isoxachlortole), methyl 2-[[[[(4,6-dimethoxy-2-pyrimidinyl)}-amino]- . : carbonyl}-amino]-sulphonyl]-4-[[(methylsulphonyl)-amino]-methyl]-benzoate (mesosulfuron), 2-(4-methylsulphonyl-2-nitro-benzoyl)-1,3-cyclohexanedione (mesotrione), 3-[1-(3,5-dichloro-phenyl)-1-i-propyl]-2,3-dihydro-6-methyl- 5-phenyl-4H-1,3-0xazin-4-one ~~ (oxaziclomefone), 2-chloro-1-(3-ethoxy- 4-nitro-phenoxy)-4-trifluoromethyl-benzene (oxyfluorfen), 2-(2,2-difluoro- ethoxy)-N-(5,8-dimethoxy{1,2,4]triazolo[1,5-c]pyrimidin-2-y1)-6- trifluoromethylbenzenesulphonamide (penoxsulam), 2-chloro-N-(2-ethoxy- ethyl)-N-(2-methyl-1-phenyl-1-propenyl)-acetamide (pethoxamid), the : sodium salt of methyl 2-[[[(4,5-dihydro-4-methyl-5-0x0-3-propoxy-1H-1,2 4- triazol-1-yl)-carbonyl}-amino]-sulphonyl]-benzoate (procarbazone-sodium), 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), ~ (R)-[2-[[(1-methyl-ethylidene)-amino]-oxy]-ethyl] 2-[4-(6-chloro- 2-quinoxalinyloxy)-phenoxy]-propanoate (propaquizafop), 2-chloro-N-(2- ethyl-6-methyl-phenyl)-N-[(1-methyl-ethoxy)-methyl]-acetamide oo ~ (propisochlor), 1-(3-chloro-4,5,6,7-tetrahydropyrazolo[ 1,5-alpyridin-2-y1)- 5-(methyl-2-propinylamino)-1H-pyrazol-4-carbonitrile ~~ (pyraclonil), ethyl [2-chloro-5-(4-chloro-5-difluoromethoxy-1-methyl-1H-pyrazol-3-yl)-4- fluoro-phenoxy]-acetate (pyraflufen-ethyl), 6-chloro-3-phenyl-pyridazin-4-ol (pyridatol), 7-[(4,6-dimethoxy-2-pyrimidinyl)-thio]-3-methyl-1(3H)- ~ 1sobenzofuranone (pyriftalide), methyl 2-(4,6-dimethoxy-pyrimidin-2-yl-oxy)- : benzoate (pyriminobac-methyl), the sodium salt of 2-chloro-6-(4,6- ‘dimethoxy-pyrimidin-2-ylthio)-benzoate (pyrithiobac-sodium), 3,7-dichloro- quinoline-8-carboxylic acid (quinchlorac), (R)-2-[4-(6-chloro-2- quinoxalinyloxy)-phenoxy]-propanoic acid (and its ethyl and tetrahydro-2-
, N Le A 34 480-Foreign Countries furanyl-methyl esters) (quizalofop-P-ethyl, -P-tefuryl), methyl 2- difluoromethyl-5-(4,5-dihydro-thiazol-2-yl)-4-(2-methyl-propyl)-6-trifluoro- methyl-pyridine-3-carboxylate (thiazopyr), (3,5,6-trichloro)-pyridin-2-yl-oxy- acetic acid (triclopyr), the sodium salt of N-[[(4,6-dimethoxy-2-pyrimidinyl)- | amino]-carbonyl]-3-(2,2,2-trifluoro-ethoxy)-2-pyridinesulphonamide (trifloxysulfuron), N-[4-dimethylamino-6-(2,2,2-trifluoro-ethoxy)-1,3,5- triazin-2-y1]-N’-(2-methoxycarbonyl-phenylsulphonyl)-urea (triflusulfuron- methyl), N-[[(4,6-dimethoxy-2-pyrimidinyl)-amino]-carbonyl]-3-(N-methyl-
N-methylsulphonyl-amino])-2-pyridinesulphonamide (cf. WO-A-92/10660), oo (“active compounds of group 27), and, if appropriate, additionally (c) a compound which improves crop plant tolerance, from amongst the following group of compounds: 4-dichloroacetyl-1-oxa-4-aza-spiro[4.5}-decane (AD-67), 1-dichloroacetyl- hexahydro-3,3,8a-trimethylpyrrolo[1,2-a)-pyrimidin-6(2H)-one (dicyclonon,
BAS-145138), 4-dichloroacetyl-3,4-dihydro-3-methyl-2H-1,4-benzoxazine (benoxacor), 1-methyl-hexyl 5-chloro-quinoline-8-oxy-acetate (cloquintocet- mexyl), a-(cyanomethoximino)-phenylacetonitrile (cyometrinil), 2,2-dichloro- - N-(2-0x0-2-(2-propenylamino)-ethyl)-N-(2-propenyl)-acetamide (DKA-24), : 2,2-dichloro-N,N-di-2-propenyl-acetamide (dichlormid), N-(4-methyl- phenyl)-N’-(1-methyl-1-phenyl-ethyl)-urea (dymron), 4,6-dichloro-2-phenyl- pyrimidine (fenclorim), ethyl 1-(2,4-dichloro-phenyl)-5-trichloromethyl-1H- 1,2,4-triazole-3-carboxylate (fenchlorazol-ethyl), phenylmethyl 2-chloro- : 4-trifluoromethyl-thiazole-5-carboxylate (flurazole), 4-chloro-N-(1,3- dioxolan-2-yl-methoxy)-a-trifluoro-acetophenone ~~ oxime (fluxofenim),
' ' Le A 34 480-Foreign Countries 3-dichloroacetyl-5-(2-furanyl)-2,2-dimethyl-oxazolidine (furilazole,
MON-13900), ethyl 4,5-dihydro-5,5-diphenyl-3-isoxazolecarboxylate (isoxadifen-ethyl), diethyl-1-(2,4-dichlorophenyl)-4,5-dihydro-5-methyl-1H- pyrazole-3,5-dicarboxylate (mefenpyr-diethyl), 2-dichloromethyl-2-methyl- : 5 1,3-dioxolane (MG-191), 1,8-naphthalenedicarboxylic anhydride, a-(1,3- dioxolan-2-yl-methoximino)-phenylacetonitrile (oxabetrinil), 2,2-dichloro-N- (1,3-dioxolan-2-yl-methyl)-N-(2-propenyl)-acetamide (PPG-1292), 3- dichloroacetyl-2,2-dimethyl-oxazolidine (R-28725), 3-dichloroacetyl-2,2,5- trimethyl-oxazolidine (R-29148), methyl 1-(2-chloro-phenyl)-5-phenyl-1H- : +100 pyrazole-3-carboxylate and N-(2-methoxy-benzoyl)-4-[(methylamino- carbonyl)-amino}-benzenesulphonamide ("active compounds of group 3”).
Preferred meanings of the radicals listed in the formula (I) shown above are : illustrated below.
Co : Ar preferably represents optionally fluorine-, chlorine-; bromine-, methyl-, ethyl- or trifluoromethyl-substituted phenyl.
Het = preferably - represents 1,2,4-thiadiazolyl or 1,3,4-thiadiazolyl which is : : . substituted by fluorine, chlorine, bromine or by in each case optionally
CE ~~ fluorine- and/or chlorine-substituted methyl, ethyl, n- or i-propyl or phenyl. - R preferably represents methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, : - 2-propenyl, 1-methyl-2-propenyl, 2-butenyl, 2-propinyl, 1-methyl-2-propinyl, 2-butinyl. Co
Ar particularly preferably represents optionally fluorine-, chlorine-, bromine-, methyl- or trifluoromethyl-substituted phenyl.
Le A 34 480-Foreign Countries
Het particularly preferably represents 1,2,4-thiadiazolyl or 1,3,4-thiadiazolyl which is substituted by fluorine, chlorine, bromine or by in each case optionally fluorine- and/or chlorine-substituted methyl, ethyl or phenyl.
R particularly preferably represents methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, 2-propenyl, 1-methyl-2-propenyl, 2-butenyl, 2-propinyl, 1-methyl- 2-propinyl, 2-butinyl. + Ar very particularly preferably represents optionally fluorine- or chlorine- substituted phenyl.
Het very particularly preferably represents 1,3,4-thiadiazolyl which is substituted by chlorine, bromine or by fluorine- and/or chlorine-substituted methyl.
R very particularly preferably represents methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl.
Examples of compounds of the formula (I) to be used as mixing partners according to . the invention are: : N-i-propyl-N-phenyl-a-(5-trifluoromethyl-1,3,4-thiadiazol-2-yl-oxy)-acetamide, N-i- . propyl-N-(2-chloro-phenyl)-a-(5-trifluoromethyl-1,3,4-thiadiazol-2-yl-oxy)-acet- : amide, N-i-propyl-N-(3-chloro-phenyl)-a-(5-trifluoromethyl-1,3,4-thiadiazol-2-yl- oxy)-acetamide, N-i-propyl-N-(4-chloro-phenyl)-a-(5-trifluoromethyl-1,3,4-thiadi- azol-2-yl-oxy)-acetamide, N-i-propyl-N-(2-fluoro-phenyl)-a-(5-trifluoromethyl-1,3,4- thiadiazol-2-yl-oxy)-acetamide, N-i-propyl-N-(3-fluoro-phenyl)-a-(5-trifluoromethyl- 1,3,4-thiadiazol-2-yl-oxy)-acetamide, N-i-propyl-N-(4-fluoro-phenyl)-a-(5-trifluoro- methyl-1,3,4-thiadiazol-2-yl-oxy)-acetamide.

Claims (1)

  1. Le A 34 480-Foreign Countries Patent Claims
    1. Composition, comprising an effective amount of an active compound combination consisting of
    5 . (a) a heteroaryloxy-acetamide of the general formula (I) : : Het N. Co Soya g
    C10. ~~ in which oo Ar represents optionally ~~ halogen-, C1-C4-alkyl- or C1-C4-halo genoalkyl-substituted phenyl, Het represents thiadiazolyl, which is substituted by halogen or by in each case optionally halogen-substituted Cy-Cg-alkyl or g phenyl, and R represents alkyl, alkenyl or alkinyl having in each case up to 4 carbon atoms, : © ("active compounds of group 1") and (b) one or more compounds from a second group of herbicides containing - 25 the active compounds mentioned hereinbelow: 1H-1,2,4-triazol-3-amine (amitrole), 2-[2,4-dichloro-5-(2-propinyloxy)-phe- nyl}-5,6,7,8-tetrahydro-1,2 ,4-triazolo-[4,3-a}-pyridin-3(2H)-one (azafenidin), N-(4,6-dimethoxy-pyrimidin-2-y1)-N’ -[1-methyl-4-(2-methyl-2H-tetrazol-
    Le A 34 480-Foreign Countries
    5-yl)-1H-pyrazol-5-ylsulphonylJurea (azimsulfuron), N-benzyl-2-(4-fluoro- 3-trifluoromethyl-phenoxy)-butanamide (beflubutamid), N-butyl-N-ethyl-2,6- dinitro-4-trifluoromethyl-benzeneamine (benfluralin), methyl 2-[2-[4-(3,6-di- hydro-3-methyl-2,6-dioxo-4-trifluoromethyl-1(2H)-pyrimidinylphenoxy-
    methyl]-5-ethyl-phenoxy-propanoate (benzfendizone), 3-(2-chloro-4-methyl- sulphonyl-benzoyl)-4-phenylthio-bicyclo-[3.2.1]-oct-3-en-2-one (benzobi- cyclon), [1,1-dimethyl-2-oxo0-2-(2-propenyloxy)]-ethyl 2-chloro-5-(3,6-di-
    hydro-3-methyl-2,6-dioxo-4-trifluoromethyl-1(2H)-pyrimidinyl)-benzoate (butafenacil-allyl), ~~ 2-(1-ethoximino-propyl)-3-hydroxy-5-[2,4,6-trimethyl- : 10 3-(1-oxo-butyl)-phenyl]-2-cyclohexen-1-one (butroxydim), 2-[1-[(3-chloro- 2-propenyl)-oxy-imino}-propyl}-3-hydroxy-5-(tetrahydro-2H-pyran-4-yl)- ' 2-cyclohexen-1-one (caloxydim, tepraloxydim), ethyl 2-chloro-3-[2-chloro- 5-(1,3,4,5,6,7-hexahydro-1,3-dioxo-2H-isoindol-2-yl)-phenyl]-2-propanoate ~ (cinidon-ethyl), 2-[1-[2-(4-chloro-phenoxy)]-propoxyaminobutyl]-5-(tetra- hydro-2H-thiopyran-3-yl)-1,3-cyclohexanedione (clefoxydim), (E,E)-(+)-2-[1- : [[(3-chloro-2-propenyl)-oxy]-imino]-propyl}-3-hydroxy-2-cyclohexen-1-one (clethodim), methyl 3-chloro-2-[[(5-ethoxy-7-fluoro[1,2,4]triazolo- ~ [1,5-c]pyrimidin-2-yl)sulphonyl]amino]-benzoate (cloransulam-methyl), 2-(1- ethoximinobutyl)-3-hydroxy-5-(tetrahydro-2H-thiopyran-3-yl)-2-cyclohexen- l-one (cycloxydim), N-(2,6-dichloro-phenyl)-5-ethoxy-7-fluoro-[1,2,4]- triazolo-{1,5-c]-pyrimidine-2-sulphonamide (diclosulam), 2-[1-[(3,5-difluoro- phenyl)-amino-carbonyl-hydrazono]-ethyl]-pyridine-3-carboxylic acid (diflufenzopyr), (S)-2-chloro-N-(2,4-dimethyl-3-thienyl)-N-(2-methoxy- 1-methyl-ethyl)-acetamide (dimethenamid-P), 2-[2-(3-chloro-phenyl)- oxiranylmethyl]-2-ethyl-1H-indene-1,3(2H)-dione (epropodan), (R)-ethyl : 2-[4-(6-chloro-benzoxazol-2-yl-oxy)-phenoxy]-propanoate (fenoxaprop- P-ethyl), N-(2,6-difluoro-phenyl)-8-fluoro-5-methoxy-[ 1,2,4]-triazolo-[ 1 ,9-c]- pyrimidine-2-sulphonamide (florasulam), butyl (R)-2-[4-(5-trifluoromethyl- : pyridin-2-yl-oxy)-phenoxy]-propanoate (fluazifop-P-butyl), the sodium salt of 4,5-dihydro-3-methoxy-4-methyl-5-0xo-N-[(2-trifluoromethoxy-phenyl)- sulphonyl]-1H-1,2,4-triazole-1-carboxamide (flucarbazone-sodium), ethyl : [2-chloro-4-fluoro-5-(5-methyl-6-oxo0-4-triflucromethyl- 1(6H)-pyridazinyl)- phenoxy]-acetate (flufenpyr), 2-[7-fluoro-3,4-dihydro-3-0x0-4-(2-propinyl)- 2H-1,4-benzoxazin-6-yl]-4,5,6,7-tetrahydro-1H-isoindole-1,3-dione (flumioxazin), the sodium salt of N-(4,6-dimethoxy-pyrimidin-2-yl)-N’-(3- methoxycarbonyl-6-trifluoromethyl-pyridin-2-yl-sulphonyl)-urea
    . . Le A 34 480-Foreign Countries (flupyrsulfuron-methyl-sodium), 2-[[[[(4,6-dimethoxy-2-pyrimidinyl)-amino}- : carbonyl]-amino]-sulphonyl]-4-formylamino-N,N-dimethyl-benzamide (foramsulfuron), (R)-2-[4-(3-chloro-5-trifluoromethyl-pyridin-2-yl-oxy)- phenoxy]-propanoic acid (and its methyl, -2-ethoxy-ethyl and butyl esters) (haloxyfop, -methyl, -P-methyl, -ethoxyethyl, -butyl), 2-[4,5-dihydro- 4-methyl-4-(1-methylethyl)-5-oxo- 1H-imidazol-2-yl)-5-(methoxymethyl)- 3-pyridinecarboxylic acid (imazamox), the sodium salt of N-(4-methoxy-6- : methyl-1,3,5-triazin-2-yl)-N’-(5-iodo-2-methoxycarbonyl-phenylsulphonyl)- urea (iodosulfuron-methyl-sodium), (4-chloro-2-methylsulphonyl-phenyl)-(5- cyclopropyl-isoxazol-4-yl)-methanone (isoxachlortole), methyl 2-[[[[(4,6- dimethoxy-2-pyrimidinyl)-amino]-carbonyl}-amino}-sulphonyl}-
    . 4-[[(methylsulphonyl)-amino]-methyl]-benzoate (mesosulfuron), 2-(4- methylsulphonyl-2-nitro-benzoyl)-1,3-cyclohexanedione (mesotrione), 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-ethoxy-4-nitro-phenoxy)- 4-trifluoromethyl-benzene (oxyfluorfen), 2-(2,2-difluoro-ethoxy)-N-(5,8- dimethoxy[1,2,4]triazolo[ 1,5-c]pyrimidin-2-yl)-6-trifluoromethylbenzene- sulphonamide (penoxsulam), 2-chloro-N-(2-ethoxy-ethyl)-N-(2-methyl- 1-phenyl-1-propenyl)-acetamide (pethoxamid), the sodium salt of methyl 2-[{[(4,5-dihydro-4-methyl-5-0x0-3-propoxy-1H-1,2,4-triazol-1-yl)- carbonyl]-amino]-sulphonyl}-benzoate (procarbazone-sodium), 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), : (R)-[2-[[(1-methyl-ethylidene)-amino]-oxy]-ethyl] 2-[4-(6-chloro-2- quinoxalinyloxy)-phenoxy}-propanoate (propaquizafop), 2-chloro-N-(2-ethyl- 6-methyl-phenyl)-N-[(1-methyl-ethoxy)-methyl]-acetamide (propisochlor), 1- oo | (3-chloro-4,5,6,7-tetrahydropyrazolo[ 1,5-a]pyridin-2-yl)-5-(methyl-2- . “propinylamino)- 1H-pyrazol-4-carbonitrile (pyraclonil), ethyl [2-chloro-5-(4- chloro-5-difluocromethoxy-1-methyl-1H-pyrazol-3-yl)-4-fluoro-phenoxy}- acetate (pyraflufen-ethyl), 6-chloro-3-phenyl-pyridazin-4-ol (pyrdatol), 7- [(4,6-dimethoxy-2-pyrimidinyl)-thio]-3-methyl-1(3H)-isobenzofuranone (pyniftalide), | methyl 2-(4,6-dimethoxy-pyrimidin-2-yl-oxy)-benzoate (pyriminobac-methyl), the sodium salt of 2-chloro-6-(4,6-dimethoxy- ~~ pyrimidin-2-ylthio)-benzoate (pyrithiobac-sodium), 3,7-dichloro-quinoline-8- carboxylic acid (quinchlorac), (R)-2-[4-(6-chloro-2-quinoxalinyloxy)- phenoxy]-propanoic acid (and its ethyl and tetrahydro-2-furanyl-methyl
    So WO 01/89301 PCT/EP01/05242 esters) (quizalofop-P-ethyl, -P-tefuryl), methyl 2-difluoromethyl-5-(4,5- dihydro-thiazol-2-yl)-4-(2-methyl-propyl)-6-trifluoromethyl-pyridine-3- carboxylate (thiazopyr), (3,5,6-trichloro)-pyridin-2-yl-oxy-acetic acid (triclopyr), the sodium salt of N-[[(4,6-dimethoxy-2-pyrimidinyl)-amino]- carbonyl-3-(2,2,2-trifluoro-ethoxy)-2-pyridinesulphonamide (trifloxysulfuron), N-[4-dimethylamino-6-(2,2,2-trifluoro-ethoxy)-1,3,5- triazin-2-yl}-N’-(2-methoxycarbonyl-phenylsulphonyl)-urea (triflusulfuron-methyl), N-[[(4,6-dimethoxy-2-pyrimidinyl)-amino]- carbonyl]-3-(N-methyl-N-methylsulphonyl-amino])-2- pyridinesulphonamide (cf. WO-A-92/10660), (“active compounds of group 2”),
    2. A composition according to Claim 1, characterized in that the active compound combination includes: ©) a compound which improves crop plant tolerance, from amongst the following group of compounds: 4-dichloroacetyl-1-oxa-4-aza-spiro[4.5]-decane = (AD-67), 1-dichloroacetyl- hexahydro-3,3,8a-trimethylpyrrolo[ 1,2-a}-pyrimidin-6(2H)-one (dicyclonon, BAS-145138), 4-dichloroacetyl-3,4-dihydro-3-methyl-2H-1,4-benzoxazine (benoxacor), 1-methyl-hexyl 5-chloro-quinoline-8-oxy-acetate (cloquintocet- mexyl), a-(cyanomethoximino)-phenylacetonitrile (cyometrinil),2,2-dichloro-N- (2-0x0-2-(2-propenylamino)-ethyl)-N-(2-propenyl)-acetamide (DKA-24), 2,2- dichloro-N,N-di-2-propenyl-acetamide (dichlormid), N-(4-methyl-phenyl)-N’- (1-methyl-1-phenyl-ethyl)-urea (dymron), 4,6-dichloro-2-phenyl-pyrimidine (fenclorim), ethyl 1-(2,4-dichloro-phenyl)-5-trichloromethyl-1H-1,2,4-triazole- 3-carboxylate (fenchlorazol-ethyl), phenylmethyl 2-chloro- 4-trifluoromethyl- thiazole-5-carboxylate (flurazole), 4-chloro-N-(1,3-dioxolan-2-yl-methoxy)- a- trifluoro-acetophenone oxime (fluxofenim), 3-dichloroacetyl-5-(2-furanyl)-2,2- dimethyl-oxazolidine (furilazole, MON-13900), ethyl 4,5-dihydro-5,5-diphenyl- AMENDED SHEET
    © woouseson PCT/EP01/05242 3-isoxazolecarboxylate (isoxadifen-ethyl), diethyl-1-(2,4-dichlorophenyl)-4,5- dihydro-5-methyl-1H-pyrazole-3,5-dicarboxylate (mefenpyr-diethyl), 2- dichloromethyl-2-methyl-1,3-dioxolane (MG-191), 1,8-naphthalenedicarboxylic anhydride, o-(1,3-dioxolan-2-yl-methoximino)-phenylacetonitrile (oxabetrinil), 2,2-dichloro-N-(1,3-dioxolan-2-yl-methyl)-N-(2-propenyl)-acetamide (PPG- 1292), 3-dichloroacetyl-2,2-dimethyl-oxazolidine (R-28725), 3-dichloroacetyl- 2,2,5-trimethyl-oxazolidine (R-29148), methyl 1-(2-chloro-phenyl)-5-phenyl- 1H-pyrazole-3-carboxylate and N-(2-methoxy-benzoyl)-4-[(methylamino- carbonyl)-amino]-benzenesulphonamide (“active compounds of group 3”).
    3. Composition according to Claim 1 or Claim 2, characterized in that in the formula (I) Ar represents optionally fluorine-, chlorine-, bromine-, methyl-, ethyl- or trifluoromethyl-substituted phenyl, Het represents 1,2,4-thiadiazolyl or 1,3,4-thiadiazolyl which is substituted by fluorine, chlorine, bromine or by in each case optionally fluorine- and/or chlorine-substituted methyl, ethyl, n- or i-propyl or phenyl, and R represents methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, 2-propenyl, 1- methyl-2-propynel, 2-butenyl, 2-propinyl, 1-methyl-2-propinyl, 2- butinyl.
    4. Composition according to Claim 1 or Claim 2, characterized in that the heteroaryloxy-acetamide of the general formula (I) is the compound N-i-propyl- N-(4-fluoro-phenyl)- a-(5-trifluoromethyl-1,3,4-thiadiazol-2-yl-oxy)-acetamide (flufenacet). AMENDED SHEET oo
    "woos PCT/EPO1/05242
    S. Composition according to any of Claims 1 to 4, characterized in that the compounds from the second group of herbicides (component (b)) are selected from the active compounds mentioned hereinbelow: azimsulfuron, beflubutamid, butafenacil-allyl, cinidon-ethyl, clefoxydim, cloransulam-methyl, diclosulam, fenoxaprop-p-ethyl, florasulam, flupyrsulf- uron-methyl-sodium, foramsulfuron, imazamox, iodosulfuron-methyl-sodium, isoxachlortole, mesosulfuron, oxaziclomefone, procarbazone-sodium, pyriftalid, pyrithiobac-sodium, quinclorac, trifloxysulfuron.
    6. Composition according to any of Claims 2 to 5, characterized in that the compounds which improve crop plant tolerance (compound (c)) are selected from the active compounds mentioned hereinbelow: 1-methyl-hexyl 5-chloro-quinoline-8-oxy-acetate (cloquintocet-mexyl), ethyl 4,5-dihydro-5,5-diphenyl-3-isoxazolecarboxylate (isoxadifen-ethyl) and di- ethyl-1-(2,4-dichloro-phenyl)-4,5-dihydro-5-methyl-1H-pyrazole-3,5-dicarb- oxylate (mefenpyr-diethyl) to improve tolerance in cereals, and 4-dichloro- acetyl-1-oxa-4-aza-spiro[4.5]-decane (AD-67), 1-dichloroacetyl-hexahydro- 3,3,8a-trimethylpyrrolo[ 1,2-a]-pyrimidin-6(2H)-one (BAS-145138), 4- dichloroacetyl-3,4-dihydro-3-methyl-2H-1,4-benzoxazine (benoxacor), 2,2- dichloro-N, N-di-2-propenyl-acetamide(dichlormid), 2,2-dichloro-N-(2-0x0-2- (2-propenylamino)-ethyl)-N-(2-propenyl)-acetamide (DKA-24), 3-dichloro- acetyl-5-(2-furanyl)-2,2-dimethyl-oxazolidine (furilazole, MON-13900), 3- dichloroacetyl-2,2,5-trimethyl-oxazolidine (R-21948).
    7. Composition according to any of Claims 1 to 6, characterized in that from 0.01 to 1000 parts by weight of the active compound(s) from the second group of herbicides (component (b)) are used per part by weight of active compound of the formula (I). AMENDED SHEET oo
    8. Composition according to any of Claims 2 to 6, characterized in that from 0.001 to 1000 parts by weight of the compound(s) which improve(s) crop plant tolerance (component (c)) are used per part by weight of active compound of the formula (I) or its mixtures with active compounds from the second group of herbicides (component (b)).
    9. Use of a composition according to any of Claims 1 to 8 for controlling undesirable plants.
    10. Method for controlling undesirable plants, characterized in that compositions according to any of Claims 1 to 8 are allowed to act on the undesirable plant and/or their habitat.
    11. Process for preparing a herbicidal composition characterized in that a composition according to Claims 1 to 8 is mixed with surfactants and/or extenders. AMENDED SHEET -
ZA200208479A 2000-05-22 2002-10-21 Selective heteroaryloxy-acetamide-based herbicides. ZA200208479B (en)

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