WO2010059676A2 - Protection contre les dommages herbicides causés par un 4-amino-2-pyridinecarboxylate de 6-(phényle trisubstitué) sur des cultures de céréales - Google Patents

Protection contre les dommages herbicides causés par un 4-amino-2-pyridinecarboxylate de 6-(phényle trisubstitué) sur des cultures de céréales Download PDF

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WO2010059676A2
WO2010059676A2 PCT/US2009/064920 US2009064920W WO2010059676A2 WO 2010059676 A2 WO2010059676 A2 WO 2010059676A2 US 2009064920 W US2009064920 W US 2009064920W WO 2010059676 A2 WO2010059676 A2 WO 2010059676A2
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Prior art keywords
herbicide
safener
amino
wheat
ethyl
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PCT/US2009/064920
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English (en)
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WO2010059676A3 (fr
Inventor
Norbert Satchivi
Paul Schmitzer
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Dow Agrosciences Llc
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Priority to JP2011537565A priority Critical patent/JP5734863B2/ja
Priority to UAA201107884A priority patent/UA106735C2/uk
Priority to AU2009316667A priority patent/AU2009316667B2/en
Priority to CN200980147356.5A priority patent/CN102325454B/zh
Priority to EP09764125.2A priority patent/EP2361014B1/fr
Priority to MX2011005485A priority patent/MX2011005485A/es
Priority to PL09764125T priority patent/PL2361014T3/pl
Application filed by Dow Agrosciences Llc filed Critical Dow Agrosciences Llc
Priority to ES09764125.2T priority patent/ES2658616T3/es
Priority to CA2741665A priority patent/CA2741665C/fr
Priority to MX2014012911A priority patent/MX338423B/es
Priority to DK09764125.2T priority patent/DK2361014T3/en
Priority to BRPI0921193-4A priority patent/BRPI0921193B1/pt
Priority to EA201100838A priority patent/EA019494B1/ru
Publication of WO2010059676A2 publication Critical patent/WO2010059676A2/fr
Priority to ZA2011/02904A priority patent/ZA201102904B/en
Priority to IL213122A priority patent/IL213122A/en
Publication of WO2010059676A3 publication Critical patent/WO2010059676A3/fr
Priority to IL246492A priority patent/IL246492A/en
Priority to IL250245A priority patent/IL250245B/en

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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
    • A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
    • A01N25/32—Ingredients for reducing the noxious effect of the active substances to organisms other than pests, e.g. toxicity reducing compositions, self-destructing compositions
    • 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
    • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/18—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
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    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
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    • A01N43/14—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom six-membered rings
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    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
    • A01N43/24—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with two or more hetero atoms
    • A01N43/26—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with two or more hetero atoms five-membered rings
    • A01N43/28—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with two or more hetero atoms five-membered rings with two hetero atoms in positions 1,3
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    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
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    • A—HUMAN NECESSITIES
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    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
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    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/56—1,2-Diazoles; Hydrogenated 1,2-diazoles
    • A—HUMAN NECESSITIES
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    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
    • A01N43/647—Triazoles; Hydrogenated triazoles
    • A01N43/653—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
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    • 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
    • A01N43/74—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 one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
    • A01N43/76—1,3-Oxazoles; Hydrogenated 1,3-oxazoles
    • 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
    • A01N43/80—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 one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,2
    • 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
    • A01N43/84—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 six-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,4
    • 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
    • A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
    • 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
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
    • A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
    • 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
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
    • A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
    • A01N47/30—Derivatives containing the group >N—CO—N aryl or >N—CS—N—aryl
    • 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
    • A01N57/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds
    • A01N57/18—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-carbon bonds
    • A01N57/20—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-carbon bonds containing acyclic or cycloaliphatic radicals
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
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    • A01N2300/00—Combinations or mixtures of active ingredients covered by classes A01N27/00 - A01N65/48 with other active or formulation relevant ingredients, e.g. specific carrier materials or surfactants, covered by classes A01N25/00 - A01N65/48

Definitions

  • This application claims the benefit of United States Provisional Application Serial Number 61/117,332 filed on November 24, 2008.
  • This invention concerns the safening of the herbicidal injury caused by 6-(trisubstituted phenyl)-4-amino-2-pyridinecarboxylates in cereal crops.
  • the cultivated plants When agrochemicals, such as plant protection agents and especially herbicides, are used, the cultivated plants may be damaged to a certain degree, depending on factors such as the dose of agrochemicals and their method of application, the species of cultivated plant, the nature of the soil and climatic conditions, for example, length of time of exposure to light, temperature and amounts of precipitation. Thus, it is known that cultivated plants which are to be protected from the adverse effect of undesirable plant growth may be damaged to a certain degree when an effective dose of herbicide is used.
  • Various substances which are capable of specifically preventing the adverse effect of an herbicide on the cultivated plants i.e.
  • U.S. Patent 7,314,849 B2 describes certain 6-(polysubstituted aryl)-4-amino-2- pyridinecarboxylate compounds and their use as herbicides. While certain of these compounds have been shown to be particularly effective herbicides for controlling undesirable vegetation in cereal crops, they have also been shown to produce slight amounts of damage to both wheat and barley at concentrations required to adequately control the undesirable vegetation.
  • the present invention concerns a method of protecting cereal crops from the harmful effects of a 6- (trisubstituted phenyl)-4-amino-2-pyridinecarboxylate herbicide of the formula (I)
  • hal represents F, Cl or Br
  • R represents methyl or ethyl
  • a safener or a compatible herbicide capable of safening, selected from the group consisting of AD67 (MON 4660), benoxacor, 2-CBSU, daimuron, dichlormid, dicyclonon (BAS 145 138H), fenchlorazole- ethyl, fenclorim, fluxofenim, furilazole (MON 13900), glyphosate, isoxadifen-ethyl, mefenpyr-diethyl, naphthalic anhydride, oxabetrinil and mixtures thereof.
  • a safener or a compatible herbicide capable of safening, selected from the group consisting of AD67 (MON 4660), benoxacor, 2-CBSU, daimuron, dichlormid, dicyclonon (BAS 145 138H), fenchlorazole- ethyl, fenclorim, fluxofenim, furilazole (MON 13900), glyphosate, isox
  • the present invention also concerns a composition for protecting wheat and barley from the harmful effects of a 6-(trisubstituted phenyl)-4-amino-2-pyridinecarboxylate herbicide of the formula (I)
  • hal represents F, Cl or Br
  • R represents methyl or ethyl
  • a safener or compatible herbicide capable of safening selected from the group consisting of AD67 (MON4660), benoxacor, 2-CBSU, daimuron, dichlormid, dicyclonon (BAS 145 138H), fenchlorazole-ethyl, fenclorim, fluxofenim, furilazole (MON 13900), glyphosate, isoxadifen- ethyl, mefenpyr-diethyl, naphthalic anhydride, oxabetrinil, and mixtures thereof.
  • the 6-(trisubstituted phenyl)-4-amino-2-pyridinecarboxylate herbicide is a 4- amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)-2-pyridinecarboxylic acid derivative or a 4-amino-3-chloro-6-(2,4-dichloro-3-methoxyphenyl)-2-pyridinecarboxylic acid derivative.
  • 67 (MON 4660) in composition with a pyridinecarboxylate herbicide of the formula (I) exhibits a protecting effect against the phytotoxicity of the pyridinecarboxylate herbicide of formula (I) on wheat (Triticum aestivum L; TRZAS) and barley (Hordeum vulgare L; HORVS) without losing the herbicidal effects on weeds such as cleavers (Galium aparine L; GALAP), purple deadnettle (Lamium purpureum L; LAMPU), corn poppy (Papaver rhoeas L; PAPRH).
  • dichloroacetamide safeners such as benoxacor, dichlormid, dicyclonon (BAS 145 138H), furilazole (MON 13900) and a pyridinecarboxylate herbicide of formula (I) resulted in an unexpected safening effect against the phytotoxicity of the pyridinecarboxylate herbicide of formula (I) on wheat (Triticum aestivum L; TRZAS) and barley (Hordeum vulgare L; HORVS) without reduction of the herbicidal effects on weeds such as cleavers (Galium aparine L; GALAP), purple deadnettle (Lamium purpureum L; LAMPU), corn poppy (Papaver rhoeas L; PAPRH), chickweed (Stellaria media L; STEME), bird's-eye speedwell (Veronica per sica L; VERPE).
  • dichloroacetamide safeners such as benoxacor, dichlormid, dicyclonon (BAS 145
  • a mixture of a benzenesulfonamide safener such as 2-CBSU and a pyridinecarboxylate herbicide of formula (I) exhibits a safening effect against the phytotoxicity of the pyridinecarboxylate herbicide of formula (I) on wheat (Triticum aestivum L; TRZAS) and barley (Hordeum vulgare L; HORVS) without losing the herbicidal effects on weeds such as cleavers (Galium aparine L; GALAP), purple deadnettle (Lamium purpureum L; LAMPU), corn poppy (Papaver rhoeas L; PAPRH).
  • the mixture of phenyl pyrazole safeners such as fenchlorazole-ethyl, mefenpyr-diethyl and a pyridinecarboxylate herbicide of formula (I) shows a safening effect against the phytotoxicity of the pyridinecarboxylate herbicide of formula (I) on wheat (Triticum aestivum L; TRZAS) and barley (Hordeum vulgare L; HORVS) without reducing the herbicidal effects on weeds such as cleavers (Galium aparine L; GALAP), purple deadnettle (Lamium purpureum L; LAMPU), corn poppy (Papaver rhoeas L; PAPRH), bird's-eye speedwell (Veronica persica L; VERPE), Russian thistle (Salsola iberica L; SASKR), wild pansy ⁇ Viola tricolor L; VIOTR).
  • cleavers Gialium aparine L; GALAP
  • a phenylpyrimidine safener such as fenclorim and a pyridinecarboxylate herbicide of formula (I) exhibits a safening effect against the phytotoxicity of the pyridinecarboxylate herbicide of formula (I) on wheat (Triticum aestivum L; TRZAS) and barley (Hordeum vulgare L; HORVS) without losing the herbicidal effects on weeds such as cleavers (Galium aparine L; GALAP), purple deadnettle (Lamium purpureum L; LAMPU), corn poppy (Papaver rhoeas L; PAPRH), wild buckwheat (Polygonum convolvulus L; POLCO).
  • the mixture of oxime ether safeners such as isoxadifen-ethyl, and a pyridinecarboxylate herbicide of formula (I) shows a safening effect against the phytotoxicity of the pyridinecarboxylate herbicide of formula (I) on wheat (Triticum aestivum L; TRZAS), durum wheat (Triticum durum L; TRZDU), and barley (Hordeum vulgare L; HORVS) without reducing the herbicidal effects on weeds such as purple deadnettle (Lamium purpureum L; LAMPU), corn poppy (Papaver rhoeas L; PAPRH).
  • the mixture of a naphthopyranone safener such as naphthalic anhydride and a pyridinecarboxylate herbicide of formula (I) shows an unexpected safening effect against the phytotoxicity of the pyridinecarboxylate herbicide of formula (I) on wheat (Triticum aestivum L; TRZAS) and barley (Hordeum vulgare L; HORVS) without reduction of the herbicidal effects on weeds such as cleavers (Galium aparine L; GALAP), purple deadnettle (Lamium purpureum L; LAMPU), corn poppy (Papaver rhoeas L; PAPRH), kochia (Kochia scoparia L; KCHSC), wild pansy (Viola tricolor L; VIOTR).
  • cleavers Gialium aparine L; GALAP
  • purple deadnettle Liamium purpureum L; LAMPU
  • corn poppy Paperaver rhoeas L; PA
  • a pyridinecarboxylate herbicide of formula (I) and a phenylurea herbicide such as daimuron exhibits a surprising safening effect against the phytotoxicity of the pyridinecarboxylate herbicide of formula (I) on wheat (Triticum aestivum L; TRZAW), durum wheat (Triticum durum L; TRZDU), and barley (Hordeum vulgare L; HORVS) without reducing the herbicidal effects on weeds such as purple deadnettle (Lamium purpureum L; LAMPU), corn poppy (Papaver rhoeas L; PAPRH).
  • the pyridinecarboxylates of formula I are a new class of compounds having herbicidal activity.
  • a number of pyridinecarboxylate compounds are described in U.S. Patent 7,314,849, including 4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)pyridine-2- carboxylic acid (compound 1) and 4-amino-3-chloro-6-(2,4-dichloro-3-methoxyphenyl)- pyridine-2-carboxylic acid (compound 2).
  • the pyridinecarboxylates of formula (I) control annual grass weeds and broadleaf weeds in wheat and barley but are also phytotoxic to wheat and barley at commercially herbicidal doses.
  • AD67 (MON 4660) is the common name for 4-(dichloroacetyl)- 1 -oxa-4- azaspiro[4,5]decane. Its safening activity is described in The Pesticide Manual, Thirteenth Edition, 2003. AD67 (MON 4660) is used as a safener in maize.
  • Benoxacor is the common name for (+)-4-(dichloroacetyl)-3,4-dihydro-3-methyl-2H- 1,4-benzoxazine. Its safening activity is described in The Pesticide Manual, Fourteenth Edition, 2006. Benoxacor is used as a safener in maize.
  • 2-CBSU is the common name for N-(aminocarbonyl)-2-chlorobenzenesulfonamide.
  • Daimuron is the common name for N-(4-methylphenyl)-N'-(l -methyl- 1- phenylethyl)urea. Its herbicidal activity is described in The Pesticide Manual, Fourteenth Edistion, 2006. Daimuron is used as a selective herbicide of cyperaceous weeds and annual grass weeds in paddy rice.
  • Dichlormid is the common name for N,N-diallyl-2,2-dichloroacetamide. Its safening activity is described in The Pesticide Manual, Fourteenth Edition, 2006. Dichlormid is used as a safener for maize and sorghum.
  • Dicyclonon (BAS 145 138H) is the common name for ( ⁇ 5)-l-dichloroacetyl-3,3,8a- trimethylperhydropyrrolo[l,2]pyrimidin-6-one. Its safening activity is described in Pesticide Biochemistry and Physiology 1992, 42, 128-139. Dicyclonon (BAS 145 138H) is used as a safener for maize.
  • Fenchlorazole is the common name for l-(2,4-dichlorophenyl)-5-(trichloromethyl)- lH-l,2,4-triazole-3-carboxylic acid. Its safening activity is described in The Pesticide Manual, Fourteenth Edition, 2006. Fenchlorazole is used as a safener in wheat, rye and triticale.
  • Fenclorim is the common name for 4,6-dichloro-2-phenylpyrimidine. Its safening activity is described in The Pesticide Manual, Fourteenth Edition, 2006. Fenclorim is used as a safener in direct-seeded rice.
  • Fluxofenim is the common name for l-(4-chlorophenyl)-2,2,2-trifluoroethanone O- (l,3-dioxolan-2-ylmethyl)oxime. Its safening activity is described in The Pesticide Manual, Fourteenth Edition, 2006. Fluxofenim is used as a safener in sorghum.
  • Furilazole (MO ⁇ 13900) is the common name for 3-(dichloroacetyl)-5-(2-furanyl)-
  • Isoxadifen-ethyl is the common name for ethyl 4,5-dihydro-5,5-diphenyl-3- isoxazolecarboxylate. Its safening activity is described in The Pesticide Manual, Fourteenth Edition, 2006. Isoxadifen is used as a safener in maize.
  • Glyphosate is the common name for N-(phosphonomethyl)glycine. Its herbicidal activity is described in The Pesticide Manual, Fourteenth Edition, 2006. Glyphosate controls a wide range of annual and perennial, broadleaf and grass weeds. Mefenpyr is the common name for l-(2,4-dichlorophenyl)-4,5-dihydro-5-methyl-lH- pyrazole-3,5-dicarboxylic acid. Its safening activity is described in The Pesticide Manual, Fourteenth Edition, 2006. Mefenpyr is used as a safener in wheat, rye, triticale and barley.
  • Naphthalic anhydride is the common name for iH,3H-naphtho[l,8-of
  • Oxabetrinil is the common name for ⁇ -[(l,3-dioxolan-2-yl)methoxyimino]benzene- acetonitrile. Its safening activity is described in The Pesticide Manual, Fourteenth Edition, 2006. Oxabetrinil is used as a safener in sorghum.
  • herbicide is used herein to mean an active ingredient that kills, controls or otherwise adversely modifies the growth of plants.
  • An herbicidally effective or vegetation controlling amount is an amount of active ingredient which causes an adversely modifying effect and includes deviations from natural development, killing, regulation, desiccation, retardation, and the like.
  • plants and vegetation include germinant seeds, emerging seedlings and established vegetation.
  • safener refers to a compound that selectively protects crop plants from herbicide damage without significantly reducing activity in target weed species.
  • ⁇ erbicidal activity is exhibited by the compounds when they are applied directly to the plant or to the locus of the plant via foliar, soil, or water application at any stage of growth or before planting or emergence.
  • the effect observed depends upon the plant species to be controlled, the stage of growth of the plant, the application parameters of dilution and spray drop size, the particle size of solid components, the environmental conditions at the time of use, the specific compound employed, the specific adjuvants and carriers employed, the soil type, and the like, as well as the amount of chemical applied. These and other factors can be adjusted as is known in the art to promote non-selective or selective herbicidal action.
  • Safening means preventing the adverse effect of an herbicide on the cultivated plants, i.e., protecting the cultivated plants without, at the same time, noticeably influencing the herbicidal action on weeds to be combated.
  • the weight ratio of the safener to the pyridinecarboxylate of formula (I) at which the herbicidal effect on the cultivated plant is safened lies within the range of between 16:1 and 1 :32.
  • the weight ratio of the safener to the pyridinecarboxylate of formula (I) at which the herbicidal effect on the cultivated plant is safened lies within the range of between 4:1 and 1 :8.
  • the rate at which the safened composition is applied will depend upon the particular type of weed to be controlled, the degree of control required, and the timing and method of application.
  • the composition of the invention can be applied at an application rate of between 4 grams per hectare (g/ha) and 1200 g/ha based on the total amount of pyridinecarboxylate of formula (I) and safener in the composition.
  • the pyridinecarboxylate of formula (I) and the safener of the present invention can be applied either separately or together as part of a multipart herbicidal system.
  • the herbicide-safener mixture of the present invention can be applied in conjunction with one or more other herbicides to control a wider variety of undesirable vegetation.
  • the composition can be formulated with the other herbicide or herbicides, tank mixed with the other herbicide or herbicides or applied sequentially with the other herbicide or herbicides.
  • the safened composition of the present invention can, further, be used in conjunction with glyphosate, glufosinate, dicamba, imidazolinones or 2,4-D on glyphosate-tolerant, glufosinate-tolerant, dicamba-tolerant, imidazolinone-tolerant or 2,4-D-tolerant crops. It is generally preferred to use the herbicide-safener mixture of the present invention in combination with herbicides that are selective for the crop being treated and which complement the spectrum of weeds controlled by these compounds at the application rate employed. It is further generally preferred to apply the safened composition of the present invention and other complementary herbicides at the same time, either as a combination formulation or as a tank mix.
  • the safened composition of the present invention in mixtures containing an herbicidally effective amount of the herbicidal components along with at least one agriculturally acceptable adjuvant or carrier.
  • Suitable adjuvants or carriers should not be phytotoxic to valuable crops, particularly at the concentrations employed in applying the compositions for selective weed control in the presence of crops, and should not react chemically with herbicidal components or other composition ingredients.
  • Such mixtures can be designed for application directly to weeds or their locus or can be concentrates or formulations that are normally diluted with additional carriers and adjuvants before application.
  • They can be solids, such as, for example, dusts, granules, water dispersible granules, or wettable powders, or liquids, such as, for example, emulsifiable concentrates, solutions, emulsions or suspensions.
  • Suitable agricultural adjuvants and carriers that are useful in preparing the herbicidal mixtures of the invention are well known to those skilled in the art.
  • Some of these adjuvants include, but are not limited to, crop oil concentrate (mineral oil (85%) + emulsifiers (15%)); nonylphenol ethoxylate; benzylcocoalkyldimethyl quaternary ammonium salt; blend of petroleum hydrocarbon, alkyl esters, organic acid, and anionic surfactant; Cg-Cn alky lpoly glycoside; phosphated alcohol ethoxylate; natural primary alcohol (Ci 2 -Ci6) ethoxylate; di-seobutylphenol EO-PO block copolymer; polysiloxane-methyl cap; nonylphenol ethoxylate + urea ammonium nitrate; emulsified methylated seed oil; tridecyl alcohol (synthetic) ethoxylate (8EO); tallow amine
  • Liquid carriers that can be employed include water, toluene, xylene, petroleum naphtha, crop oil, acetone, methyl ethyl ketone, cyclohexanone, trichloroethylene, perchloroethylene, ethyl acetate, amyl acetate, butyl acetate, propylene glycol monomethyl ether and diethylene glycol monomethyl ether, methyl alcohol, ethyl alcohol, isopropyl alcohol, amyl alcohol, ethylene glycol, propylene glycol, glycerine, N-methyl-2- pyrrolidinone, N,N-dimethyl alkylamides, dimethyl sulfoxide, liquid fertilizers and the like. Water is generally the carrier of choice for the dilution of concentrates.
  • Suitable solid carriers include talc, pyrophyllite clay, silica, attapulgus clay, kaolin clay, kieselguhr, chalk, diatomaceous earth, lime, calcium carbonate, bentonite clay, Fuller's earth, cotton seed hulls, wheat flour, soybean flour, pumice, wood flour, walnut shell flour, lignin, and the like.
  • compositions of the present invention are advantageously employed in both solid and liquid compositions, especially those designed to be diluted with carrier before application.
  • the surface-active agents can be anionic, cationic or nonionic in character and can be employed as emulsifying agents, wetting agents, suspending agents, or for other purposes.
  • Surfactants conventionally used in the art of formulation and which may also be used in the present formulations are described, inter alia, in "McCutcheon' s Detergents and Emulsifiers Annual," MC Publishing Corp., Ridgewood, New Jersey, 1998 and in “Encyclopedia of Surfactants,” Vol. I-III, Chemical Publishing Co., New York, 1980- 81.
  • Typical surface-active agents include salts of alkyl sulfates, such as diethanolammonium lauryl sulfate; alkylarylsulfonate salts, such as calcium dodecylbenzenesulfonate; alkylphenol-alkylene oxide addition products, such as nonylphenol-Ci8 ethoxylate; alcohol- alky lene oxide addition products, such as tridecyl alcohol-Ci6 ethoxylate; soaps, such as sodium stearate; alkylnaphthalene- sulfonate salts, such as sodium dibutyl- naphthalenesulfonate; dialkyl esters of sulfosuccinate salts, such as sodium di(2-ethylhexyl) sulfosuccinate; sorbitol esters, such as sorbitol oleate; quaternary amines, such as lauryl trimethylammonium chloride; polyethylene glyco
  • compositions may also contain other compatible components, for example, other herbicides, plant growth regulants, fungicides, insecticides, and the like and can be formulated with liquid fertilizers or solid, particulate fertilizer carriers such as ammonium nitrate, urea and the like.
  • the concentration of the active ingredients in the herbicide-safener mixture of the present invention is generally from 0.001 to 98 percent by weight. Concentrations from 0.01 to 90 percent by weight are often employed. In compositions designed to be employed as concentrates, the active ingredients are generally present in a concentration from 5 to 98 weight percent, preferably 10 to 90 weight percent. Such compositions are typically diluted with an inert carrier, such as water, before application. The diluted compositions usually applied to weeds or the locus of weeds generally contain 0.0001 to 1 weight percent active ingredient and preferably contain 0.001 to 0.05 weight percent. The present compositions can be applied to weeds or their locus by the use of conventional ground or aerial dusters, sprayers, and granule applicators, or irrigation water, and by other conventional means known to those skilled in the art.
  • Seeds of the desired test plant species were planted in Sun Gro MetroMix® 306 planting mixture, which typically has a pH of 6.0 to 6.8 and an organic matter content of 30 percent, in plastic pots with a surface area of 103.2 square centimeters (cm 2 ).
  • a fungicide treatment and/or other chemical or physical treatment was applied.
  • the plants were grown for 7-36 days (d) in a greenhouse with an approximate 14-hour (h) photoperiod which was maintained at 18 0 C during the day and 17 0 C during the night.
  • Nutrients and water were added on a regular basis and supplemental lighting was provided with overhead metal halide 1000- Watt lamps as necessary. The plants were employed for testing when they reached the second or third true leaf stage.
  • Compound requirements are based upon a 12 mL application volume at a rate of 187 liters per hectare (L/ha).
  • Stocks solutions of the safeners were prepared following the same procedure.
  • Spray solutions of the safeners and experimental compound mixtures were prepared by adding the stock solutions to the appropriate amount of dilution solution to form a 12 mL spray solution with active ingredients in two-way combinations.
  • Formulated compounds were applied to the plant material with an overhead Mandel track sprayer equipped with 8002E nozzles calibrated to deliver 187 L/ha over an application area of 0.503 square meters (m 2 ) at a spray height of 18 inches (43 centimeters (cm)) above average plant canopy. Control plants were sprayed in the same manner with the solvent blank.
  • the treated plants and control plants were placed in a greenhouse as described above and watered by sub-irrigation to prevent wash-off of the test compounds. After 20-22 d, the condition of the test plants as compared with that of the control plants was determined visually and scored on a scale of 0 to 100 percent where 0 corresponds to no injury and 100 corresponds to complete kill.
  • 140 140 140 1: 1 7 26 5 16 100 100 91 94 100 99 78 80
  • 140 140 1: 1 100 100 98 100 85 88 99 94 85 85 78 69
  • 140 140 140 1: 1 5 26 4 16 100 100 85 94 100 99 78 80
  • 140 140 1: 1 100 100 97 100 89 88 98 94 85 85 50 69
  • 140 140 140 1: 1 15 26 20 16 100 100 100 94 100 99 73 80
  • 140 70 2 1 100 100 99 100 80 84 90 94 93 85 65 69
  • 140 140 140 1: 1 6 26 4 16 100 100 95 94 100 99 78 80
  • 140 140 1: 1 100 100 99 100 85 88 94 94 93 85 65 69
  • 140 140 140 1: 1 6 26 4 16 100 100 86 94 100 99 70 80
  • 140 140 140 1 : 1 1 26 3 16 100 100 75 94 100 99 70 80
  • 140 140 1: 1 13 26 8 16 100 100 91 94 100 99 93 80
  • 140 70 2 1 100 100 100 100 100 100 89 88 95 94 85 85 75 69
  • 140 140 140 1 : 1 20 26 16 16 100 100 92 94 100 99 93 80
  • TRZAS Triticum aestivum (spring wheat)
  • PAPRH Papaver rhoeas (corn poppy)
  • HORVS Hordeum vulgare (spring barley)
  • POLCO Polygonum convolvulus(wil ⁇ buckwheat)
  • GALAP Galium aparine (cleavers)
  • SASKR Salsola iberica (Russian thistle)
  • KCHSC Kochia scoparia (kochia)
  • STEME Stellaria media (common chickweed)
  • LAMPU Lamium purpureum (purple deadnettle)
  • VERPE Veronica persica (bird' s-eye speedwell)
  • MATCH Matricaria chamomila (scented mayweed)
  • VIOTR Viola tricolor (wild pansy)
  • Ob Observed values

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Abstract

Selon la présente invention, les dommages herbicides causés par des 4-amino-2-pyridinecarboxylates de 6-(phényle trisubstitué) chez le blé et l’orge sont réduits par l’utilisation de AD67 (MON 4660), benoxacor, 2-CBSU, daimuron, dichlormid, dicyclonon (BAS 145 138H), fenchlorazole-éthyle, fenclorim, fluxofénim, furilazole (MON 13900), glyphosate, isoxadifen-éthyle, méfenpyr-diéthyle, anhydride naphtalique, oxabétrinil et des mélanges de ceux-ci.
PCT/US2009/064920 2008-11-24 2009-11-18 Protection contre les dommages herbicides causés par un 4-amino-2-pyridinecarboxylate de 6-(phényle trisubstitué) sur des cultures de céréales WO2010059676A2 (fr)

Priority Applications (17)

Application Number Priority Date Filing Date Title
EA201100838A EA019494B1 (ru) 2008-11-24 2009-11-18 Защита от действия 6-(тризамещенный фенил)-4-амино-2-пиридинкарбоксилатного гербицида, повреждающего зерновые культуры
AU2009316667A AU2009316667B2 (en) 2008-11-24 2009-11-18 Safening 6-(trisubstituted phenyl)-4-amino-2-pyridinecarboxylate herbicide injury on cereal crops
CN200980147356.5A CN102325454B (zh) 2008-11-24 2009-11-18 谷类作物的6-(三取代的苯基)-4-氨基-吡啶-2-羧酸类除草剂损害的安全剂
EP09764125.2A EP2361014B1 (fr) 2008-11-24 2009-11-18 Protection contre les dommages herbicides causés par un 4-amino-2-pyridinecarboxylate de 6-(phényle trisubstitué) sur des cultures de céréales
MX2011005485A MX2011005485A (es) 2008-11-24 2009-11-18 Herbicida 6-(trisustituido fenil)-4-amino-2-piridinacarboxilato protector de daños en el cultivo de cereales.
PL09764125T PL2361014T3 (pl) 2008-11-24 2009-11-18 Zabezpieczanie upraw zbożowych przed uszkodzeniami powodowanymi przez 6-(tripodstawiony fenylo)-4-amino-2-pirydynokarboksylanowy herbicyd
MX2014012911A MX338423B (es) 2008-11-24 2009-11-18 Herbicida 6- (trisustituido fenil) -4-amino-2-piridinacarboxilato protector de daños en el cultivo de cereales.
ES09764125.2T ES2658616T3 (es) 2008-11-24 2009-11-18 Protección de cultivos de cereales contra los efectos nocivos de un herbicida de 6-(fenil trisustituido)-4-amino-2-piridinocarboxilato
CA2741665A CA2741665C (fr) 2008-11-24 2009-11-18 Protection contre les dommages herbicides causes par un 4-amino-2-pyridinecarboxylate de 6-(phenyle trisubstitue) sur des cultures de cereales
JP2011537565A JP5734863B2 (ja) 2008-11-24 2009-11-18 禾穀類に対する６−（三置換フェニル）−４−アミノ−２−ピリジンカルボキシレート除草剤損傷の薬害軽減
DK09764125.2T DK2361014T3 (en) 2008-11-24 2009-11-18 PROTECTION OF CORN CROPS FROM DAMAGE CAUSED BY 6- (TRISUBSTITUTED PHENYL) -4-AMINO-2-PYRIDINE CARBOXYLATE HERBICIDE
BRPI0921193-4A BRPI0921193B1 (pt) 2008-11-24 2009-11-18 Composição e método para proteção de trigo e cevada contra os efeitos nocivos de um herbicida de 6-(fenila trissubstituída)-4-amino-2-piridinacarboxilato
UAA201107884A UA106735C2 (uk) 2008-11-24 2009-11-18 Захист від дії 6-(тризаміщений феніл)-4-аміно-2-піридинкарбоксилатного гербіциду, що пошкоджує зернові культури
ZA2011/02904A ZA201102904B (en) 2008-11-24 2011-04-18 Safening 6-(trisubstituted phenyl)-4-amino-2-pyridinecarboxylate herbicide injury on cereal crops
IL213122A IL213122A (en) 2008-11-24 2011-05-24 Protects cereal crops from herbicide damage 6 - (tri-converted phenyl) - 4 - amino - 2 - pyridinecarboxylate
IL246492A IL246492A (en) 2008-11-24 2016-06-27 Protects grain crops from herbicide damage 6– (tri-converted phenyl) –4 – amino – 2 – pyridine – carboxylate
IL250245A IL250245B (en) 2008-11-24 2017-01-23 Protects cereal crops from herbicide damage 6-(tri-mutated phenyl)-4-amino-2-pyridine-carboxylate

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US61/117,332 2008-11-24

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WO2011012862A1 (fr) 2009-07-31 2011-02-03 Syngenta Limited Diones cycliques substituées par hétéroaryle à activité herbicide ou dérivés de celles-ci
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WO2014195327A1 (fr) 2013-06-05 2014-12-11 Syngenta Limited Composés de 2-(phényl substitué)-cyclopentane-1,3-dione à activité herbicide et leurs dérivés
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WO2017027442A1 (fr) * 2015-08-10 2017-02-16 Dow Agrosciences Llc Compositions herbicides phytoprotectrices comprenant des acides carboxyliques pyridiniques
CN107318847B (zh) * 2017-08-01 2019-11-12 江苏绿利来股份有限公司 一种含有氟氯吡啶酯和乙草胺的除草剂组合物
CN107372518A (zh) * 2017-08-01 2017-11-24 江苏绿利来股份有限公司 提高氟氯吡啶酯安全性的除草组合物
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WO2010059671A2 (fr) * 2008-11-24 2010-05-27 Dow Agrosciences Llc Protection contre les dommages herbicides causés par un 4-amino-2-pyridinecarboxylate de 6-(phényle trisubstitué) sur du riz paddy directement semé et transplanté
WO2010059680A2 (fr) * 2008-11-24 2010-05-27 Dow Agrosciences Llc Composition de protection à base d'herbicides de 4-amino-2-pyridinecarboxylate de 6-(phényle trisubstitué) et de cloquintocet-mexyle pour des cultures de céréales
WO2010060581A2 (fr) * 2008-11-29 2010-06-03 Bayer Cropscience Ag Association d'herbicide(s) et de phytoprotecteur(s)

Cited By (15)

* Cited by examiner, † Cited by third party
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US8916498B2 (en) 2008-11-24 2014-12-23 Dow Agrosciences, Llc. Safening 6-(trisubstituted phenyl)-4-amino-2-pyridinecarboxylate herbicide injury on direct seeded and transplanted paddy rice
US8921267B2 (en) 2008-11-24 2014-12-30 Dow Agrosciences, Llc. Safening 6-(trisubstituted phenyl)-4-amino-2-pyridinecarboxylate herbicide injury on cereal crops
WO2010059680A3 (fr) * 2008-11-24 2011-08-11 Dow Agrosciences Llc Composition de protection à base d'herbicides de 4-amino-2-pyridinecarboxylate de 6-(phényle trisubstitué) et de cloquintocet-mexyle pour des cultures de céréales
WO2010059671A3 (fr) * 2008-11-24 2011-08-18 Dow Agrosciences Llc Protection contre les dommages herbicides causés par un 4-amino-2-pyridinecarboxylate de 6-(phényle trisubstitué) sur du riz paddy directement semé et transplanté
US8530383B2 (en) 2008-11-24 2013-09-10 Dow Agrosciences Llc Safening 6-(trisubstituted phenyl)-4-amino-2-pyridinecarboxylate herbicide injury on cereal crops
US8609586B2 (en) 2008-11-24 2013-12-17 Dow Agrosciences, Llc. Safening composition of 6-(trisubstituted phenyl)-4-amino-2-pyridinecarboxylate herbicides and cloquintocet-mexyl for cereal crops
CN107258792A (zh) * 2008-11-24 2017-10-20 陶氏益农公司 用于保护直播水稻和移植水稻的组合物
US9040458B2 (en) 2008-11-24 2015-05-26 Dow Agrosciences Llc Safening composition of 6-(trisubstituded phenyl)-4-amino-2-pyridinecarboxylate herbicides and cloquintocet-mexyl for cereal crops
EA019904B1 (ru) * 2008-11-24 2014-07-30 ДАУ АГРОСАЙЕНСИЗ ЭлЭлСи Защитная композиция из 6-(тризамещенных фенил)-4-амино-2-пиридинкарбоксилатных гербицидов и клоквинтоцета для злаковых культур
US8962523B2 (en) 2008-11-29 2015-02-24 Bayer Cropscience Ag Herbicide/safener combination
WO2011007146A1 (fr) 2009-07-16 2011-01-20 Syngenta Limited Dérivés 2-(substitution phényle)-cyclopentane-1,3-dione à activité herbicide
WO2011012862A1 (fr) 2009-07-31 2011-02-03 Syngenta Limited Diones cycliques substituées par hétéroaryle à activité herbicide ou dérivés de celles-ci
JP2013544813A (ja) * 2010-11-05 2013-12-19 ダウ アグロサイエンシィズ エルエルシー ４−アミノ−３−クロロ−６−（４−クロロ−２−フルオロ−３−メトキシフェニル）ピリジン−２−カルボン酸及びその塩又はエステルによるフェノキシアルカン酸除草剤耐性雑草の防除
KR101918308B1 (ko) 2010-11-05 2018-11-13 다우 아그로사이언시즈 엘엘씨 4-아미노-3-클로로-6-(4-클로로-2-플루오로-3-메톡시페닐)피리딘-2-카르복실산 및 그의 염 또는 에스테르를 사용한 펜옥시알칸산 제초제-내성 잡초의 방제
WO2014195327A1 (fr) 2013-06-05 2014-12-11 Syngenta Limited Composés de 2-(phényl substitué)-cyclopentane-1,3-dione à activité herbicide et leurs dérivés

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MX2011005485A (es) 2011-06-16
HUE038503T2 (hu) 2018-10-29
IL213122A0 (en) 2011-07-31
US20130281293A1 (en) 2013-10-24
US20100130362A1 (en) 2010-05-27
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AU2009316667B2 (en) 2015-03-12
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EA201100838A3 (ru) 2013-01-30
US8921267B2 (en) 2014-12-30
CA2922383A1 (fr) 2010-05-27
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BRPI0921193B1 (pt) 2019-07-02
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CA2741665A1 (fr) 2010-05-27
ES2658616T3 (es) 2018-03-12
JP5734863B2 (ja) 2015-06-17
EP2361014A2 (fr) 2011-08-31
PL2361014T3 (pl) 2018-05-30
DK2361014T3 (en) 2018-03-05
ZA201102904B (en) 2012-06-27
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