Classifications

• • 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

Definitions

• the present invention relates to a herbicidal composition comprising metazachlor and imazamox, any of its individual isomers or agriculturally acceptable salts, esters or amides thereof.
• the invention also relates to methods and uses for controlling undesirable vegetation, in particular in crops.
• Resistant weed biotypes are a consequence of basic evolutionary processes. Individuals within a species that are best adapted to a particular practice are selected for and will increase in the population. Once a weed population is exposed to a herbicide to which one or more plants are naturally resistant, the herbicide kills susceptible individuals, but allows resistant individuals to survive and reproduce. With repeated herbicide use, resistant weeds that initially appear as isolated plants or patches in a field can quickly spread to dominate the population and the soil seed bank.
• herbicide resistance within weeds in particular grass weeds such as, for example, Alopecurus myosuroides (ALOMY), Apera spica-venti (APESV) or Lolium species (LOLSS) has become a major concern for farmers, resulting in dramatic weed control problems, for example in cereal crops.
• Herbicides from the group of ACCase- and ALS-inhibitors are most affected by resistance evolution but also various other types of herbicides.
• Metazachlor is the common name of the herbicidal compound with the lUPAC name 2-chloro-N- (pyrazol-1-ylmethyl)acet-2',6'-xylidide and the Chemical Abstracts name 2-chloro-N-(2,6- dimethylphenyl)-N-(1 H-pyrazol-1 -ylmethyl)acetamide (CAS RN 67129-08-2) that is described in the The Pesticide Manual, Fourteenth Edition, Editor: C.D.S. Tomlin, British Crop Production Council, 2006, entry 543, pages 687-689.
• Metazachlor can be used for pre-emergence and early post-emergence control of winter and annual grasses and broad-leaved weeds in various crops including oilseed rape. Metazachlor exists in different polymorphic forms. The monoclinic form is disclosed in EP 41 1408. The polymorphs of Metazachlor are further described in U. J. Griesser, D. Weigand, J. M. Rollinger, M. Haddow, E. Gstrein, J. Therm. Anal. Calorim., 77 (2004) 51 1 and D. Weigand, Ph.D. thesis, Innsbruck, 2001.
• Imazamox is the common name of the herbicidal compound with the lUPAC name 2-[(RS)-4- isopropyl-4-methyl-5-oxo-2-imidazolin-2-yl]-5-methoxymethylnicotinic acid and the Chemical Abstracts name ( ⁇ )-2-[4,5-dihydro-4-methyl-4-(1-methylethyl)-5-oxo-1 H-imidazol-2-yl]-5- (methoxymethyl)-3-pyridinecarboxylic acid (CAS RN 1 1431 1-32-9) that is described e.g. in US 5,334,576 and the The Pesticide Manual, Fourteenth Edition, Editor: C.D.S.
• the R-isomer of imazamox is known from e.g. US 5,972,154 or US 6,339,158 B1 .
• the ammonium salt of imazamox (common name: imazamox-ammonium; lUPAC name: ammonium 2-[(RS)-4-isopropyl-4-methyl-5-oxo-2- imidazolin-2-yl]-5-methoxymethylnicotinate; Chemical Abstracts name: ammonium 2-[4,5- dihydro-4-methyl-4-(1 -methylethyl)-5-oxo-1 H-imidazol-2-yl]-5-(methoxymethyl)-3- pyridinecarboxylate, CAS RN 247057-22-3) is also described in the The Pesticide Manual, Fourteenth Edition, Editor: C.D.S.
• Imazamox is an effective herbicide for the control of both terrestrial and aquatic vegetation and is a member of the imidazolinone class of herbicides. All imidazolinone herbicides share a common mechanism of herbicidal action that involves the inhibition of acetolactate synthase (ALS).
• Lolas, P. C "Cinmethylin, imazaquin and metazachlor performance for weed control in tobacco"
• Proceedings - British Crop Protection Conference-Weeds (1985), (3), pages 841-848 discloses field trials wherein the herbicides cinmethylin, imazaquin and metazachlor were tested for tobacco weed control.
• cinmethylin was applied alone or as tank mix with pebulate or ethofumesate pre-plant incorporated or pre-emergence. Metazachlor was applied alone early post-emergence over the top of tobacco.
• WO 2009/010475 discloses a method for controlling aquatic weeds by applying a herbicidally effective amount of a VLCFA inhibitor to the water body of aquatic weeds and/or their aqueous habitat containing seeds or other propagating organs of said aquatic weeds.
• the VLCFA inhibitor may be an acetamide, a chloroacetamide, an oxyacetamide, a tetrazolinone or is selected from anilophos, cafenstrole, indanofan and piperophos. Metazachlor is mentioned as an example of chloroacetamides.
• the VLCFA inhibitor can also be applied in combination with one or more other herbicides selected from various active compounds, inter alia cinmethylin.
• WO 2007/071655 discloses a method of controlling the aquatic weed Hydrilla verticillata tree by applying the herbicide imazamox or an agriculturally acceptable salt thereof to the aquatic weed and/or its aqueous habitat containing seeds or other propagating organs of said aquatic weed.
• Imazamox can be applied in combination with various additional herbicides, inter alia
• WO 2010/046268 discloses a method of controlling Chinese tallow tree by applying the herbicide imazamox or an agriculturally acceptable salt or derivative thereof to Chinese tallow tree, its seeds or other propagating organs or its habitat.
• Imazamox can be applied in combination with various additional herbicides, inter alia cinmethylin.
• WO2005/096814 discloses a herbicidal mixture comprising imazamox and metazachlor.
• the herbicidal combination of metazachlor, quinmerac and imazamox is marketed by BASF under the trade name Clearfield ® -Vantiga ® for weed control in oilseed rape.
• WO 2009/153246 describes ternary herbicidal combinations of aminopyralid, imazamox and at least one herbicide B which may be selected from various active ingredients, inter alia metazachlor (see Table A) or cinmethylin (see Claim 1 , component b).
• herbicidal compositions which provide weed control comparable to the individual compounds with significantly reduced application rates. It is also an object of the present invention to provide herbicidal compositions, which provide significantly enhanced weed control with application rates comparable to those of the individual compounds.
• herbicidal compositions which maintain or improve the level of weed control, while showing less damage in the cultured crop in comparison to the individual compounds.
• compositions according to the invention should have a broad spectrum of activity.
• Another object of the present invention lies in the effective control of herbicide-resistant weed biotypes, in particular in herbicide-resistant grass weeds.
• a herbicidal composition comprising a herbicidally effective amount of (a) ( ⁇ )-2-exo-(2-Methylbenzyloxy)-1-methyl-4- isopropyl-7-oxabicyclo[2.2.1 ]heptane, any of its individual enantiomers or any non-racemic mixture thereof (herbicide A), (b) metazachlor (herbicide B) and (c) imazamox, any of its individual isomers or an agriculturally acceptable salt, ester or amide thereof (herbicide C).
• herbicide A as used herein is meant to include the racemic mixture ( ⁇ )-2-exo-(2- Methylbenzyloxy)-1-methyl-4-isopropyl-7-oxabicyclo[2.2.1]heptane (herein also referred to as the "exo-( ⁇ )- isomers", CAS RN 87818-31 -3)
• racemic mixture contains equal parts of the two enantiomers (+)-2-exo-(2-Methylbenzyloxy)-1-methyl-4- isopropyl-7-oxabicyclo[2.2.1 ]heptane (herein also referred to as the "exo-(+)- isomer” , CAS RN 87818-61 -9) and (-)-2-exo-(2-Methylbenzyloxy)-1 -methyl-4-isopropyl-7-oxabicyclo[2.2.1 ]heptane (herein also referred to as the "exo-(-)- isomer", CAS RN 87819-60-1 ).
• the herbicide A is ( ⁇ )-2-exo-(2-Methylbenzyloxy)-1-methyl-4- isopropyl-7-oxabicyclo[2.2.1 ]heptane.
• the herbicide A is (+)-2-exo-(2-Methylbenzyloxy)-1 -methyl-4-isopropyl- 7-oxabicyclo[2.2.1 ]heptane.
• the herbicide A is (-)-2-exo-(2-Methylbenzyloxy)-1 -methyl-4-isopropyl-7- oxabicyclo[2.2.1 ]heptane.
• herbicide A is a non-racemic mixture of (+)-2-exo-(2-Methylbenzyloxy)- 1 -methyl-4-isopropyl-7-oxabicyclo[2.2.1]heptane and (-)-2-exo-(2-Methylbenzyloxy)-1-methyl-4- isopropyl-7-oxabicyclo[2.2.1 ]heptane.
• the non-racemic mixture contains unequal parts of the exo-(+)-isomer and the exo-(-)-isomer.
• the weight ratio of the exo-(+)- isomer to the exo-(-)- isomer in the non-racemic mixture can vary widely.
• the composition of this invention comprises metazachlor (herbicide B) in its monoclinic form or triclinic form or as a mixture thereof.
• the herbicide B is metazachlor in its monoclinic or triclinic form, in particular in its monoclinic form.
• herbicide C as used herein is meant to include imazamox (i.e. the racemic mixture 2- [(RS)-4-isopropyl-4-methyl-5-oxo-2-imidazolin-2-yl]-5-methoxymethylnicotinic acid), any of its individual isomers (i.e.
• herbicide C examples include those where the cations are the ions of the alkali metals, preferably of lithium, sodium and potassium, of the alkaline earth metals, preferably of calcium and magnesium, and of the transition metals, preferably of manganese, copper, zinc and iron, furthermore ammonium and substituted ammonium in which one to four hydrogen atoms are replaced by Ci-C4-alkyl, hydroxy-Ci-C4-alklyl, Ci-C4-alkoxy-Ci-C4-alklyl, hydroxyl- Ci-C4-alkoxy-Ci-C4-alkyl, phenyl or benzyl, preferably methyl-ammonium, isopropylammonium, dimethylammonium,
• diisopropylammonium trimethylammonium, tetramethylammonium, tetraethylammonium, tetrabutylammo-nium, 2-hydroxyethylammonium, 2-(2-hydroxyethoxy)eth-1-ylammonium, di(2- hydroxyeth-1-yl)ammonium, benzyltrimethylammonium, benzyltriethylammonium, furthermore phosphonium ions, sulfonium ions, preferably tri(Ci-C4-alkyl)sulfonium such as
• ammonium salt of imazamox i.e. imazamox-ammonium
• imazamox-ammonium is particularly preferred.
• Exemplary agriculturally acceptable esters encompassed by the definition of herbicide C include, for example allyl esters, propargyl esters, Ci-Cio-alkyl esters or alkoxyalkyl esters, and also thioesters, for example Ci-Cio-alkyl thioester.
• Preferred alkyl esters are, for example, the methyl, ethyl, propyl, isopropyl, butyl, isobu-tyl, pentyl, mexyl(l-methylhexyl) or isooctyl(2- ethylhexyl)ester.
• Ci-C4-alkoxy-Ci-C4-alkyl esters are the straight-chain or branched Ci-C4-alkoxyethyl esters, for example the methoxyethyl, ethoyethyl or butoxyethyl ester.
• An example of the straight-chain or branched Ci-Cio-alkyl thioesters is the ethyl thioester.
• Exemplary agriculturally acceptable amides encompassed by the definition of herbicide C include, for example mono- or di-Ci-C6-alkylamides or arylamides.
• Preferred mono- and di- Ci-C6-alkylamides are methyl- and the dimethylamide.
• Preferred arylamides are, for example, the anilidine and the 2-chloroanilide.
• the herbicide C is imazamox, the R-isomer of imazamox or an agriculturally acceptable salt thereof.
• the herbicide C is imazamox, the R-isomer of imazamox or imazamox-ammonium. In another embodiment, the herbicide C is imazamox (herein also referred to as “herbicide C.1 " or “C.1 "). In another embodiment, the herbicide C is the R-isomer of imazamox (herein also referred to as "herbicide C.2" or “C.2").
• the herbicide C is imazamox-ammonium (herein also referred to as “herbicide C.3” or “C.3”).
• herbicidal effective amount denotes an amount of the active ingredients, which is sufficient for controlling unwanted plants, especially for controlling unwanted plants in cultivated plants and which does not result in a substantial damage to the treated plants. Such an amount can vary in a broad range and is dependent on various factors, such as the plants to be controlled, the treated cultivated plant or material, the climatic conditions and the specific composition according to the invention used.
• composition of the invention may further comprise at least one herbicide D (as defined hereinafter) which is different from the herbicides A, B and C.
• composition of the invention may further comprise at least one safener E (as defined hereinafter).
• composition of the invention may further comprise one or more auxiliaries customary in crop protection (as defined hereinafter).
• the present invention relates to the use of the composition as defined herein for controlling undesirable vegetation.
• plants and “vegetation”, as used herein, include germinant seeds, emerging seedlings, plants emerging from vegetative propagules, and established vegetation.
• controlling and “combating”, as used herein, are synonyms.
• undesirable vegetation are synonyms.
• undesirable vegetation are synonyms.
• the present invention relates to a method for controlling undesirable vegetation which comprises applying to the vegetation or the locus thereof or applying to the soil or water to prevent the emergence or growth of the undesirable vegetation a herbicidally effective amount of (a) ( ⁇ )-2-exo-(2-Methylbenzyloxy)-1-methyl-4-isopropyl-7- oxabicyclo[2.2.1 ]heptane, any of its individual enantiomers or any non-racemic mixture thereof (herbicide A), (b) metazachlor (herbicide B) and (c) imazamox, any of its individual isomers or an agriculturally acceptable salt, ester or amide thereof (herbicide C).
• the method of the invention may further comprise applying at least one herbicide D (as defined hereinafter) which is different from the herbicides A, B and C.
• the method of the invention may further comprise applying at least one safener E.
• the method of the invention may further comprise applying one or more auxiliaries customary in crop protection.
• locus means the area in which the vegetation or plants are growing or will grow, typically a field.
• the present invention relates to a method for controlling undesirable vegetation which comprises applying to the vegetation or the locus thereof or applying to the soil or water to prevent the emergence or growth of the undesirable vegetation the composition according to the invention.
• the herbicide A, herbicide B and herbicide C are each present or applied in an amount sufficient to provide a synergistic herbicidal effect.
• compositions can, based on the individual components, be used at lower application rates to achieve a herbicidal effect comparable to the individual components.
• Colby's equation can be applied to determine whether the combination of two active ingredients (e.g. herbicide A and herbicide B) shows a synergistic effect (see S. R. Colby, "Calculating synergistic and antagonistic responses of herbicide combinations", Weeds 1967, 15, pp. 20-22).
• E, X and Y are as defined above and Z is the herbicidal effect in percent using a herbicide C (as defined herein) at an application rate c.
• the value E corresponds to the effect (plant damage or injury) which is to be expected if the activity of the individual compounds is additive. If the observed effect is higher than the value E calculated according to the Colby equation, a synergistic effect is present.
• compositions, uses and methods disclosed herein are synergistic as determined by the Colby equation.
• the synergistic herbicidal effect is determined according to the Colby equation.
• compositions, uses and methods of the present invention provide excellent pre- and post-emergence control of weeds.
• compositions and methods are useful for controlling undesirable vegetation before their emergence (pre-emergence).
• compositions, uses and methods of the present invention also show good crop
• compositions, uses and methods of the present invention provide effective control of herbicide resistant or tolerant weed species, in particular herbicide-resistant weed biotypes.
• the compositions, uses and methods of the present invention can effectively control herbicide-resistant grass weeds such as, for example, Alopecurus
• compositions, uses and methods of the present invention are also suitable for controlling herbicide-resistant broadleaf weeds such as, for example, Papaver rhoeas (PAPRH, corn poppy) which has evolved resistance, especially against ALS-inhibiting herbicides.
• herbicide-resistant broadleaf weeds such as, for example, Papaver rhoeas (PAPRH, corn poppy) which has evolved resistance, especially against ALS-inhibiting herbicides.
• compositions, uses and methods of the present invention can effectively control weed biotypes with target-site resistance but also weed biotypes with non-target site resistance.
• a particular advantage is that the compositions, uses and methods of the present invention also provide effective control of weed biotypes having both target-site resistance and non-target-site resistance, such as e.g. resistant populations of Alopecurus myosuroides (ALOMY) or Lolium rigidum (LOLRI).
• target-site resistance occurs by mutation within a gene coding for an herbicide target-site enzyme (limiting the herbicide binding) or by overproduction of the target enzyme (gene overexpression or amplification).
• Non-target-site resistance involves mechanisms that minimize the amount of active herbicide reaching the target site (e.g. reduced herbicide uptake or translocation, increased herbicide sequestration, or enhanced herbicide metabolism).
• compositions of the present invention the weight ratio of herbicide A (in particular ( ⁇ )-2- exo-(2-Methylbenzyloxy)-1-methyl-4-isopropyl-7-oxabicyclo[2.2.1 ]heptane) to metazachlor
• (herbicide B) is in general in the range from 1 :0.1 to 1 :40, preferably in the range from 1 :0.2 to 1 :20 and more preferably in the range from 1 :0.5 to 1 :10.
• the weight ratio of herbicide A in particular ( ⁇ )-2- exo-(2-Methylbenzyloxy)-1-methyl-4-isopropyl-7-oxabicyclo[2.2.1]heptane) to herbicide C herbicide C (preferably imazamox (C.1 ), the R-isomer of imazamox (C.2) or imazamox- ammonium (C.3)) is in general in the range from 1 :0.002 to 1 :4, preferably in the range from 1 :0.005 to 1 :2 and more preferably in the range from 1 :0.02 to 1 :0.5.
• herbicide A in particular ( ⁇ )-2- exo-(2-Methylbenzyloxy)-1-methyl-4-isopropyl-7-oxabicyclo[2.2.1]heptane
• herbicide C herbicide C preferably imazamox (C.1 ), the R-isomer of imazamox (C.2) or imazamox- ammoni
• the weight ratio of herbicide B (metazachlor) to herbicide C is in general in the range from 1 :0.01 to 1 :2, preferably in the range from 1 :0.003 to 1 :1 and more preferably in the range from 1 :0.01 to 1 :0.2.
• the composition of the invention may further comprise at least one herbicide D which is different from the herbicides A, B and C.
• compositions of the present invention comprise herbicide A (in particular ( ⁇ )-2-exo-(2-Methylbenzyloxy)-1-methyl-4-isopropyl-7-oxabicyclo[2.2.1 ]heptane), metazachlor (herbicide B), imazamox, any of its individual isomers or an agriculturally acceptable salt, ester or amide thereof (herbicide C) (preferably imazamox (C.1 ), the R-isomer of imazamox (C.2) or imazamox-ammonium (C.3)) and at least one herbicide D.
• herbicide A in particular ( ⁇ )-2-exo-(2-Methylbenzyloxy)-1-methyl-4-isopropyl-7-oxabicyclo[2.2.1 ]heptane
• herbicide B metazachlor
• imazamox any of its individual isomers or an agriculturally acceptable salt, ester or amide thereof
• herbicide C preferably imazamo
• the herbicide D is selected from the group consisting of acetochlor (D.1 ), aclonifen (D.2), amicarbazone (D.3), amidosulfuron (D.4), aminopyralid (D.5), amitrole (D.6), asulam (D.7), atrazine (D.8), azimsulfuron (D.9), beflubutamid (D.10), benfluralin (D.1 1 ), bensulfuron (D.12), bensulide (D.13), bentazone (D.14), benzobicyclon (D.15), bicyclopyrone (D.16), bifenox (D.17), bispyribac (D.18), bromoxynil (D.19), carbetamide (D.20), carfentrazone (D.21 ), chloridazon (D.22), chlorpropham (D.23), chlorsulfuron (D.24), chlorthal (D.
• the herbicide D is selected from the group consisting of acetochlor (D.1 ), aclonifen (D.2), aminopyralid (D.5), atrazine (D.8), azimsulfuron (D.9), beflubutamid (D.10), bensulfuron (D.12), bentazone (D.14), benzobicyclon (D.15), bicyclopyrone (D.16), bispyribac (D.18), bromoxynil (D.19), carbetamide (D.20), chloridazon (D.22), chlortoluron (D.26), clethodim (D.27), clodinafop (D.28), clomazone (D.29), clopyralid (D.30), cyclosulfamuron (D.31 ), cycloxydim (D.32), cyclopyrimorate (D.33), cyhalofop (D.34), 2,
• the herbicide D is selected from the group consisting of aclonifen (D.2), aminopyralid (D.5), azimsulfuron (D.9), bensulfuron (D.12), bentazone (D.14), bispyribac (D.18), clethodim (D.27), clopyralid (D.30), cyclosulfamuron (D.31 ), cycloxydim (D.32), cyhalofop (D.34), 2,4-D (D.35), dicamba (D.39), dimethachlor (D.45), dimethenamid (D.46),
• aclonifen D.2
• aminopyralid D.5
• azimsulfuron D.9
• bensulfuron D.12
• bentazone D.14
• bispyribac D.18
• clethodim D.27
• clopyralid D.30
• dimethenamid-P D.47
• ethametsulfuron D.51
• flufenacet D.61
• glyphosate D.71
• halauxifen D.72
• imazethapyr D.79
• isoxaflutole D.86
• mesosulfuron D.93
• metsulfuron D.103
• pendimethalin D.1 15
• penoxsulam D.1 16
• napropamide D.106
• napropamide-M D.107
• pethoxamid D.1 17
• picloram D.1 19
• pretilachlor D.122
• profoxydim D.124
• propanil D.126
• propaquizafop D.127
• propoxycarbazone D.128)
• propyzamide D.129
• prosulfocarb D.130
• pyroxasulfone D.134
• pyroxsulfone
• the herbicide D is selected from the group consisting of aminopyralid (D.5), azimsulfuron (D.9), bensulfuron (D.12), bentazone (D.14), bispyribac (D.18), clethodim (D.27), clopyralid (D.30), cyclosulfamuron (D.31 ), cycloxydim (D.32), cyhalofop (D.34), 2,4-D (D.35), dicamba (D.39), dimethachlor (D.45), dimethenamid (D.46), dimethenamid-P (D.47), ethametsulfuron (D.51 ), glyphosate (D.71 ), halauxifen (D.72), imazethapyr (D.79), isoxaflutole (D.86), mesosulfuron (D.93), metsulfuron (D.103)
• the herbicide D is selected from the group consisting of aclonifen (D.2), cycloxydim (D.32), 2,4-D (D.35), dicamba (D.39), dimethenamid (D.46), dimethenamid-P (D.47), pendimethalin (D.1 15), pyroxasulfone (D.134), saflufenacil (D.142), sulfentrazone (D.147), tribenuron (D.159), trifludimoxazin (D.162), and agriculturally acceptable salts, esters or amides thereof.
• the aforementioned herbicides D are particularly suitable for use in sunflower.
• the herbicide D is selected from the group consisting of bentazone (D.14), cycloxydim (D.32), dicamba (D.39), dimethenamid (D.46), dimethenamid-P (D.47), glyphosate (D.71 ), imazethapyr (D.79), isoxaflutole (D.86), mesosulfuron (D.93), pendimethalin (C1 15), pyroxasulfone (D.134), saflufenacil (D.142), sulfentrazone (D.147), trifludimoxazin (D.162), and agriculturally acceptable salts, esters or amides thereof.
• the aforementioned herbicides D are particularly suitable for use in legumes.
• the herbicide D is selected from the group consisting of flufenacet (D.61 ), halauxifen (D.72), mesosulfuron (D.93), metsulfuron (D.103), pendimethalin (D.1 15), propoxycarbazone (D.128), prosulfocarb (D.130), pyroxasulfone (D.134), pyroxsulam (D.135), quinclorac (D.136), quinmerac (D.137), saflufenacil (D.142), sulfentrazone (D.147), tribenuron (D.159), trifludimoxazin (D.162), pyrasulfotole (D.168), and agriculturally acceptable salts, esters or amides thereof.
• the aforementioned herbicides D are particularly suitable for use in cereals, in particular wheat.
• the compositions D are particularly suitable for use in cereals, in particular wheat.
• Safeners are chemical compounds which prevent or reduce damage on useful plants without having a major impact on the herbicidal action of the herbicidal active components towards unwanted plants. Safeners can be applied before sowings (e.g. seed treatments), on shoots or seedlings as well as in the pre-emergence or post-emergence treatment of useful plants and their habitat.
• compositions of the present invention comprise herbicide A, herbicide B (metazachlor), herbicide C (preferably imazamox (C.1 ), the R-isomer of imazamox (C.2) or imazamox-ammonium (C.3)), at least one safener E and optionally at least one herbicide D.
• herbicide A herbicide B (metazachlor)
• herbicide C preferably imazamox (C.1 ), the R-isomer of imazamox (C.2) or imazamox-ammonium (C.3)
• at least one safener E optionally at least one herbicide D.
• compositions of the present invention comprise herbicide A, herbicide B (metazachlor), herbicide C (preferably imazamox (C.1 ), the R-isomer of imazamox (C.2) or imazamox-ammonium (C.3)), at least one herbicide D and at least one safener E.
• herbicide A herbicide B (metazachlor)
• herbicide C preferably imazamox (C.1 ), the R-isomer of imazamox (C.2) or imazamox-ammonium (C.3)
• herbicide D preferably imazamox (C.1 ), the R-isomer of imazamox (C.2) or imazamox-ammonium (C.3)
• herbicide D preferably imazamox (C.1 ), the R-isomer of imazamox (C.2) or imazamox-ammonium (C.3)
• herbicide D preferably imazamox (C.
• cyprosulfamide (E.4), dichlormid (E.5), dicyclonon (E.6), dietholate (E.7), fenchlorazole (E.8), fenclorim (E.9), flurazole (E.10), fluxofenim (E.1 1 ), furilazole (E.12), isoxadifen (E.13), mefenpyr (E.14), mephenate (E.15), naphthaleneacetic acid (E.16), naphthalic anhydride (E.17), oxabetrinil (E.18), 4-(dichloroacetyl)-1-oxa-4-azaspiro[4.5]decane (MON4660, CAS 71526-07-3) (E.19), 2,2,5-trimethyl-3-(dichloroacetyl)-1 ,3-oxazolidine (R-29148, CAS 52836-31-4) (E.20), N- (2-
• the safener E is selected from the group consisting of benoxacor (E.1 ), cloquintocet (E.2), cyprosulfamide (E.4), dichlormid (E.5), dicyclonon (E.6), fenchlorazole (E.8), fenclorim
• the safener E is selected from the group consisting of benoxacor (E.1 ), cloquintocet-mexyl (E.2a), cyprosulfamide (E.4), dichlormid (E.5), dicyclonon (E.6),
• the safener E is selected from the group consisting of benoxacor (E.1 ), cloquintocet (E.2), cyprosulfamide (E.4), dichlormid (E.5), fenclorazole (E.8), fenclorim (E.9), isoxadifen (E.13), mefenpyr (E.14), and agriculturally acceptable salts, esters or amides thereof.
• the safener E is selected from the group consisting of benoxacor (E.1 ), cloquintocet-mexyl (E.2a), cyprosulfamide (E.4), dichlormid (E.5), fenclorazole-ethyl (E.8a), fenclorim (E.9), isoxadifen-ethyl (E.13a), and mefenpyr-diethyl (E.14a).
• the safener E is selected from the group consisting of benoxacor (E.1 ),
• the safener D is selected from the group consisting of benoxacor (E.1 ), cloquintocet-mexyl (E.2a), cyprosulfamide (E.4), isoxadifen-ethyl (E.13a), and mefenpyr-diethyl (E.14a).
• herbicides D and safeners E are known herbicides and safeners, see, for example, The Pesticide Manual, British Crop Protection Council, 16 th edition, 2012; The Compendium of
• Pesticide Common Names http://www.alanwood.net/pesticides/); Farm Chemicals Handbook 2000 volume 86, Meister Publishing Company, 2000; B. Hock, C. Fedtke, R. R. Schmidt, Herbizide [Herbicides], Georg Thieme Verlag, Stuttgart 1995; W. H. Ahrens, Herbicide
• herbicides D and/or safeners E as described herein are capable of forming geometrical isomers, for example E/Z isomers, it is possible to use both, the pure isomers and mixtures thereof, in the compositions, uses and methods according to the invention.
• herbicides D and/or safeners E as described herein have one or more centers of chirality and, as a consequence, are present as enantiomers or diastereomers, it is possible to use both, the pure enantiomers and diastereomers and their mixtures, in the compositions, uses and methods according to the invention.
• herbicides D and/or safeners E as described herein have ionizable functional groups, they can also be employed in the form of their agriculturally acceptable salts.
• agriculturally acceptable salts is used herein to mean in general, the salts of those cations and the acid addition salts of those acids whose cations and anions, respectively, have no adverse effect on the herbicidal activity of the active compounds.
• Preferred cations are the ions of the alkali metals, preferably of lithium, sodium and potassium, of the alkaline earth metals, preferably of calcium and magnesium, and of the transition metals, preferably of manganese, copper, zinc and iron, further ammonium and substituted ammonium in which one to four hydrogen atoms are replaced by Ci -C4-alkyl, hydroxy-Ci-C4-alkyl, C1 -C4- alkoxy-Ci-C4-alkyl, hydroxy-Ci-C4-alkoxy-Ci -C4-alkyl, phenyl or benzyl, preferably ammonium, methylammonium, isopropylammonium, dimethylammonium, diisopropylammonium, trimethylammonium, heptylammonium, dodecylammonium, tetradecylammonium,
• Anions of useful acid addition salts are primarily chloride, bromide, fluoride, iodide,
• the herbicides D and/or safeners E as described herein having a carboxyl, hydroxy and/or an amino group can be employed in the form of the acid, in the form of an agriculturally suitable salt as mentioned above or else in the form of an agriculturally acceptable derivative, for example as amides, such as mono- and di-Ci-C6-alkylamides or arylamides, as esters, for example as allyl esters, propargyl esters, Ci-Cio-alkyl esters, alkoxyalkyl esters, tefuryl ((tetrahydrofuran-2-yl)methyl) esters and also as thioesters, for example as Ci-Cio-alkylthio esters.
• amides such as mono- and di-Ci-C6-alkylamides or arylamides
• esters for example as allyl esters, propargyl esters, Ci-Cio-alkyl esters, alkoxyalky
• Preferred mono- and di-Ci-C6-alkylamides are the methyl and the dimethylamides.
• Preferred arylamides are, for example, the anilides and the 2-chloroanilides.
• Preferred alkyl esters are, for example, the methyl, ethyl, propyl, isopropyl, butyl, isobutyl, pentyl, mexyl (1 -methylhexyl), meptyl (1 -methylheptyl), heptyl, octyl or isooctyl (2-ethylhexyl) esters.
• Ci-C4-alkoxy-Ci-C4-alkyl esters are the straight-chain or branched Ci-C4-alkoxy ethyl esters, for example the 2-methoxyethyl, 2-ethoxyethyl, 2-butoxyethyl (butotyl), 2-butoxypropyl or 3- butoxypropyl ester.
• An example of a straight-chain or branched Ci-Cio-alkylthio ester is the ethylthio ester.
• Exemplary agriculturally acceptable salts or esters of aminopyralid include aminopyralid- dimethylammonium (D.5a), aminopyralid-potassium (D.5b), aminopyralid-tris(2- hydroxypropyl)ammonium (D.5c), and mixtures thereof.
• Exemplary agriculturally acceptable salts or esters of asulam include asulam-potassium (D.7a), asulam-sodium (D.7b), and mixtures thereof.
• Exemplary agriculturally acceptable salts or esters of bensulfuron (D.12) include bensulfuron- methyl (D.12a).
• Exemplary agriculturally acceptable salts or esters of bentazone include bentazone- sodium (D.14a).
• Exemplary agriculturally acceptable salts or esters of bispyribac (D.18) include bispyribac- sodium (D.18a).
• Exemplary agriculturally acceptable salts or esters of bromoxynil (D.19) include bromoxynil butyrate (D.19a), bromoxynil heptanoate (D.19b), bromoxynil octanoate (D.19c), bromoxynil- potassium (D.19d), and mixtures thereof.
• Exemplary agriculturally acceptable salts or esters of carfentrazone (D.21 ) include
• Exemplary agriculturally acceptable salts or esters of chlorthal include chlorthal-dimethyl (DCPA) (D.25a), chlorthal-monomethyl (D.25b), and mixtures thereof.
• Exemplary agriculturally acceptable salts or esters of clodinafop include clodinafop- propargyl (D.28a).
• Exemplary agriculturally acceptable salts or esters of clopyralid include clopyralid- potassium (D. 30a), clopyralid-olamine (D. 30b), clopyralid-tris(2-hydroxypropyl)ammonium (D. 30c), ciopyralid-methyl (D. 30d), and mixtures thereof.
• clopyralid is provided as an amine salt, such as clopyralid-olamine salt (D. 30b, see above), dimethylamine (DMA) salt (D. 30e), monoethanolamine (MEA) salt (D. 30f), triisopropanolamine (TIPA) salt (D. 30g), and mixtures thereof.
• Exemplary agriculturally acceptable salts or esters of cyhalofop include cyhalofop-butyl (D.34a).
• Exemplary agriculturally acceptable salts or esters of 2,4-D include 2,4-D-ammonium (D.35a), 2,4-D-butotyl (D.35b), 2,4-D-2-butoxypropyl (D.35c), 2,4-D-3-butoxypropyl (D.35d), 2,4- D-butyl (D.35e), 2,4-D-diethylammonium (D.35f), 2,4-D-dimethylammonium (D.35g), 2,4-D- diolamine (D.35h), 2,4-D-dodecylammonium (D.35i), 2,4-D-ethyl (D.35j), 2,4-D-2-ethylhexyl (D.35k), 2,4-D-heptylammonium (D.35I), 2,4-D-isobutyl (D.35m), 2,4-D-isoctyl (D.35n),
• Exemplary agriculturally acceptable salts or esters of 2,4-DB (D.37) include 2,4-DB-butyl (D.37a), 2,4-DB-dimethylammonium (D.37b), 2,4-DB-isoctyl (D.37c), 2,4-DB-potassium (D.37d), 2,4-DB-sodium (D.37e), and mixtures thereof.
• Exemplary agriculturally acceptable salts or esters of dicamba include dicamba-sodium (D.39a), dicamba-potassium (D.39b), dicamba-methylammonium (D.39c), dicamba- dimethylammonium (D.39d), dicamba-isopropylammonium (D.39e), dicamba-diglycolamine (D.39f), dicamba-olamine (D.39g), dicamba-diolamine (D.39h), dicamba-trolamine (D.39i), dicamba-N,N-bis-(3-aminopropyl)methylamine (D.39j), dicamba-diethylenetriamine (D.39k), dicamba-methyl (D.39I), dicamba-butotyl (D.39m), and mixtures thereof.
• Exemplary agriculturally acceptable salts or esters of dichlorprop include dichlorprop-butotyl (D.40a), dichlorprop-dimethylammonium (D.40b), dichlorprop-ethylammonium (D.40c), dichlorprop-2-ethylhexyl (D.40d), dichlorprop-isoctyl (D.40e), dichlorprop-methyl (D.40f), dichlorprop-potassium (D.40g), dichlorprop-sodium (D.40h), and mixtures thereof.
• Exemplary agriculturally acceptable salts or esters of dichlorprop-P include dichlorprop-P- dimethylammonium (D.41 a), dichlorprop-P-2-ethylhexyl (D.41 b), dichlorprop-P-potassium (D.41 c), dichlorprop-P-sodium (D.41 d), and mixtures thereof.
• Exemplary agriculturally acceptable salts or esters of diclofop (D.42) include diclofop-methyl (D.42a).
• Exemplary agriculturally acceptable salts or esters of diflufenzopyr include diflufenzopyr- sodium (D.44a).
• Exemplary agriculturally acceptable salts or esters of diquat include diquat dibromide (D.48a).
• Exemplary agriculturally acceptable salts or esters of ethametsulfuron include
• Exemplary agriculturally acceptable salts or esters of fenoxaprop include fenoxaprop- ethyl (D.53a).
• Exemplary agriculturally acceptable salts or esters of fenoxaprop-P include fenoxaprop- P-ethyl (D.54a).
• Exemplary agriculturally acceptable salts or esters of fluazifop include fluazifop-methyl (D.58a), fluazifop-butyl (D.58b), and mixtures thereof.
• Exemplary agriculturally acceptable salts or esters of fluazifop-P include fluazifop-P-butyl
• Exemplary agriculturally acceptable salts or esters of flucarbazone include flucarbazone- sodium (D.60a).
• Exemplary agriculturally acceptable salts or esters of flupyrsulfuron include
• f!upyrsulfuron-methy! (D.64a), flupyrsulfuron-methyl-sodium (D.64b), and mixtures thereof.
• Exemplary agriculturally acceptable salts or esters of fluroxypyr include fluroxypyr- butomethyl (D.66a), fluroxypyr-meptyl (D.66b), and mixtures thereof.
• Exemplary agriculturally acceptable salts or esters of glufosinate (D.69) include glufosinate- ammonium (D.69a).
• Exemplary agriculturally acceptable salts or esters of glufosinate-P include glufosinate-P- ammonium (D.70a), glufosinate-P-sodium (D.70b), and mixtures thereof.
• Exemplary agriculturally acceptable salts or esters of glyphosate include glyphosate- ammonium (D.71 a), glyphosate-diammonium (D.71 b), giyphoste-dimethylammonium (D.71 c), glyphosate-isopropylammonium (D.71 d), glyphosate-potassium (D.71 e), glyphosate-sodium (D.71f), glyphosate-sesquisodium (D.71 g), glyphosate-trimesium (D.71 h), glyphosate- ethanolamine (D.71 i), glyphosate-diethanolamine (D.71 j), and mixtures thereof.
• Exemplary agriculturally acceptable salts or esters of halauxifen include halauxifen- methyl (D.72a).
• Exemplary agriculturally acceptable salts or esters of halosulfuron include halosulfuron- methyl (D.73a).
• Exemplary agriculturally acceptable salts or esters of haloxyfop-P include haloxyfop-P- etotyl (D. 74a), haloxyfop-P-methyl (D. 74b), and mixtures thereof.
• Exemplary agriculturally acceptable salts or esters of imazapic include imazapic- ammonium (D.76a).
• Exemplary agriculturally acceptable salts or esters of imazapyr include imazapyr- isopropylammonium (D.77a).
• Exemplary agriculturally acceptable salts or esters of imazaquin include imazaquin - ammonium (D.78a), imazaquin-methyl (D.78b), imazaquin-sodium (D.78c), and mixtures thereof.
• Exemplary agriculturally acceptable salts or esters of imazethapyr include imazethapyr- ammonium (D.79a).
• Exemplary agriculturally acceptable salts or esters of lodosulfuron include iodosulfuron- methyl (D.81 a), iodosulfuron-methyl-sodium (D.81 b), and mixtures thereof.
• Exemplary agriculturally acceptable salts or esters of lofensulfuron include iofensulfuron- sodium (D.82a).
• Exemplary agriculturally acceptable salts or esters of ioxynil include ioxynil-lithium (D.83a), ioxynil octanoate (D.83b), ioxynil-sodium (D.83c), and mixtures thereof.
• Exemplary agriculturally acceptable salts or esters of MCPA include MCPA-butotyl (D.89a), MCPA-butyl (D. 89b), MCPA-dimethylammonium (D. 89c), MCPA-diolamine (D. 89d), MCPA-ethyl (D. 89e), MCPA-2-ethylhexyl (D. 89f), MCPA-isobutyl (D. 89g), MCPA-isoctyl (D. 89h), MCPA-isopropyl (D. 89i), MCPA-methyl (D. 89j), MCPA-olamine (D. 89k), MCPA- potassium (D. 89I), MCPA-sodium (D. 89m), MCPA-trolamine (D. 89n), and mixtures thereof.
• Exemplary agriculturally acceptable salts or esters of MCPB include MCPB-ethyl (D. 90a), MCPB-methyl (D. 90b), MCPB-sodium (D. 90c), and mixtures thereof.
• Exemplary agriculturally acceptable salts or esters of mecoprop include mecoprop- dimethylammonium (D. 91 a), mecoprop-diolamine (D. 91 b), mecoprop-ethadyl (D. 91 c), mecoprop-2-ethylhexyl (D. 91 d), mecoprop-isoctyl (D. 91 e), mecoprop-methyl (D. 91f), mecoprop-potassium (D. 91 g), mecoprop-sodium (D. 91 h), mecoprop-trolamine (D. 91 i), and mixtures thereof.
• Exemplary agriculturally acceptable salts or esters of mecoprop-P include mecoprop-P- dimethylammonium (D.92a), mecoprop-P-2-ethylhexyl (D. 92b), mecoprop-P-isobutyl (D. 92c), mecoprop-P-potassium (D. 92d), and mixtures thereof.
• Exemplary agriculturally acceptable salts or esters of mesosulfuron include
• Exemplary agriculturally acceptable salts or esters of metam include metam-ammonium (D. 95a), metam-potassium (D. 95b), metam-sodium (D. 95c), and mixtures thereof.
• Exemplary agriculturally acceptable salts or esters of metsulfuron include metsulfuron- methyl (D.103a).
• Exemplary agriculturally acceptable salts or esters of phenmedipham include phenmedipham-ethyl (D.1 18a).
• Exemplary agriculturally acceptable salts or esters of picloram include picloram- dimethylammonium (D. 1 19a), picloram-2-ethylhexyl (D. 1 19b), picloram-isoctyl (D. 1 19c), picloram-methyl (D. 1 19d), picloram-olamine (D. 1 19e), picloram-potassium (D. 1 19f), picloram- triethylammonium (D. 1 19g), picloram-tris(2-hydroxypropyl)ammonium (D. 1 19h), picloram- trolamine (D. 1 19i), and mixtures thereof.
• Exemplary agriculturally acceptable salts or esters of propoxycarbazone include propoxycarbazone-sodium (D.128a).
• Exemplary agriculturally acceptable salts or esters of pyraflufen include pyrafluf en-ethyl (D.132a).
• Exemplary agriculturally acceptable salts or esters of quinclorac include quinclorac- dimethylammonium (D.136a).
• Exemplary agriculturally acceptable salts or esters of quizalofop include quizalofop- ethyl (D.139a).
• Exemplary agriculturally acceptable salts or esters of quizalofop-P include quizalofop-P- ethyl (D.140a), quizalofop-P-tefuryl (D.140b), and mixtures thereof.
• Exemplary agriculturally acceptable salts or esters of thiencarbazone include thiencarbazone-methyl (D.152a).
• Exemplary agriculturally acceptable salts or esters of thifensulfuron include
• Exemplary agriculturally acceptable salts or esters of topramezone include
• Exemplary agriculturally acceptable salts or esters of tribenuron include tribenuron- methyl (D.159a).
• Exemplary agriculturally acceptable salts or esters of triclopyr include triclopyr-butotyl (D.160a), triclopyr-ethyl (D.160b), triclopyr-triethylammonium (D.160c) and mixtures thereof.
• Exemplary agriculturally acceptable salts or esters of trifloxysulfuron include
• trifloxysulfuron-sodium (D.161 a).
• exemplary agriculturally acceptable salts or esters of triflusulfuron (D.164) include triflusulfuron- methyl (D.164a).
• Exemplary agriculturally acceptable salts or esters of cloquintocet include cloquintocet- mexyl (E.2a).
• Exemplary agriculturally acceptable salts or esters of fenchlorazole include fenchlorazole- ethyl (E.8a).
• Exemplary agriculturally acceptable salts or esters of isoxadifen include isoxadifen-ethyl (E.13a).
• Exemplary agriculturally acceptable salts or esters of mefenpyr include mefenpyr-diethyl (E.14a).
• the composition comprises herbicide A (in particular ( ⁇ )-2-exo-(2-Methylbenzyloxy)-1-methyl-4-isopropyl-7-oxabicyclo[2.2.1]heptane), herbicide B (metazachlor), herbicide C (preferably imazamox (C.1 ), the R-isomer of imazamox (C.2) or imazamox-ammonium (C.3)), as the only active ingredients.
• herbicide A in particular ( ⁇ )-2-exo-(2-Methylbenzyloxy)-1-methyl-4-isopropyl-7-oxabicyclo[2.2.1]heptane
• herbicide B metalazachlor
• herbicide C preferably imazamox (C.1 ), the R-isomer of imazamox (C.2) or imazamox-ammonium (C.3)
• the composition comprises, as the only active ingredients, herbicide A (in particular ( ⁇ )-2-exo-(2-Methylbenzyloxy)-1-methyl-4-isopropyl-7- oxabicyclo[2.2.1 ]heptane), herbicide B (metazachlor), herbicide C (preferably imazamox (C.1 ), the R-isomer of imazamox (C.2) or imazamox-ammonium (C.3)) and at least one (preferably one to three, more preferably one or two and most preferably one) safener E selected from the safeners E.1 to E.21 and agriculturally acceptable salts, esters or amides thereof (preferably selected from the group consisting of benoxacor (E.1 ), cloquintocet (E.2), cyprosulfamide (E.4), dichlormid (E.5), dicyclonon (E.6), fenchlorazole (E.8), fenclo
• herbicide A in particular
• fenclorazole-ethyl E.8a
• fenclorim E.9
• flurazole E.10
• furilazole E.12
• isoxadifen-ethyl E.13a
• mefenpyr-diethyl E.14a
• 4-(dichloroacetyl)-1 -oxa-4-azaspiro[4.5]decane MON4660, CAS 71526-07-3) (E.19
• 2,2,5-trimethyl-3-(dichloroacetyl)-1 ,3-oxazolidine R-29148, CAS 52836-31 -4)
• the composition comprises, as the only active ingredients, herbicide A (in particular ( ⁇ )-2-exo-(2-Methylbenzyloxy)-1-methyl-4-isopropyl-7- oxabicyclo[2.2.1 ]heptane), herbicide B (metazachlor), herbicide C (preferably imazamox (C.1 ), the R-isomer of imazamox (C.2) or imazamox-ammonium (C.3)), and at least one (preferably one to three, more preferably one or two and most preferably one) herbicide D selected from the group consisting of herbicides D.1 to D.168 and agriculturally acceptable salts, esters or amides thereof (preferably selected from the group consisting of acetochlor (D.1 ), aclonifen (D.2), aminopyralid (D.5), atrazine (D.8), azimsulfuron (D.9), beflubutamid (D.10), bens
• herbicide A in particular
• aclonifen D.2
• aminopyralid D.5
• azimsulfuron D.9
• bensulfuron D.12
• bentazone D.14
• bispyribac D.18
• clethodim D.27
• clopyralid D.30
• propoxycarbazone (D.128), propyzamide (D.129), prosulfocarb (D.130), pyroxasulfone (D.134), pyroxsulam (D.135), quinclorac (D.136), quinmerac (D.137), quizalofop (D.139), quizalofop-P (D.140), saflufenacil (D.142), sulfentrazone (D.147), tribenuron (D.159), trifludimoxazin (D.162), 4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)-5-fluoropyridine-2-carboxylic acid (D.166), benzyl 4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)-5-fluoropyridine-2-carboxylic acid (D.166), benzyl
• the composition comprises, as the only active ingredients, herbicide A (in particular ( ⁇ )-2-exo-(2-Methylbenzyloxy)-1-methyl-4-isopropyl-7- oxabicyclo[2.2.1]heptane), herbicide B (metazachlor), herbicide C (preferably imazamox (C.1 ), the R-isomer of imazamox (C.2) or imazamox-ammonium (C.3)), at least one (preferably one to three, more preferably one or two and most preferably one) herbicide D selected from the group consisting of herbicides D.1 to D.168 and agriculturally acceptable salts, esters or amides thereof (preferably selected from the group consisting of acetochlor (D.1 ), aclonifen (D.2), aminopyralid (D.5), atrazine (D.8), azimsulfuron (D.9), beflubutamid (D.10), bensulfur
• herbicide A in particular
• dimethenamid-P (D.47), dithiopyr (D.49), ethametsulfuron (D.51 ), ethofumesate (D.52), fenoxaprop (D.53), fenoxaprop-P (D.54), fenquinotrione (D.55), flazasulfuron (D.56), florasulam (D.57), fluazifop (D.58), fluazifop-P (D.59), flucarbazone (D.60), flufenacet (D.61 ), flumioxazin (D.62), flupyrsulfuron (D.64), flurochloridone (D.65), fluroxypyr (D.66), flurtamone (D.67), foramsulfuron (D.68), glufosinate (D.69), glufosinate-P (D.70), glyphosate (D.71 ), halaux
• propoxycarbazone (D.128), propyzamide (D.129), prosulfocarb (D.130), pyroxasulfone (D.134), pyroxsulam (D.135), quinclorac (D.136), quinmerac (D.137), quizalofop (D.139), quizalofop-P (D.140), saflufenacil (D.142), sulfentrazone (D.147), tribenuron (D.159), trifludimoxazin (D.162), 4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)-5-fluoropyridine-2-carboxylic acid (D.166), benzyl 4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)-5-fluoropyridine-2-carboxylic acid (D.166), benzyl
• agriculturally acceptable salts, esters or amides thereof preferably selected from the group consisting of benoxacor (E.1 ), cloquintocet (E.2), cyprosulfamide (E.4), dichlormid (E.5), dicyclonon (E.6), fenchlorazole (E.8), fenclorim (E.9), flurazole (E.10), furilazole (E.12), isoxadifen (E.13), mefenpyr (E.14), 4-(dichloroacetyl)-1-oxa-4-azaspiro[4.5]decane (MON4660, CAS 71526-07-3) (E.19), 2,2,5-trimethyl-3-(dichloroacetyl)-1 ,3-oxazolidine (R-29148, CAS 52836-31 -4) (E.20), and agriculturally acceptable salts, esters or amides thereof, more preferably selected from the group consisting of be
• herbicidal compositions comprising the following combinations of four active ingredients (herbicide A+herbicide B+herbicide
• A+B+C.1 (or C.2 or C.3)+D.1 1 A+B+C.1 (or C.2 or C.3)+D.12, A+B+C.1 (or C.2 or C.3)+D.12a, A+B+C.1 (or C.2 or C.3)+D.13, A+B+C.1 (or C.2 or C.3)+D.14, A+B+C.1 (or C.2 or C.3)+D.14a, A+B+C.1 (or C.2 or C.3)+D.15, A+B+C.1 (or C.2 or C.3)+D.16, A+B+C.1 (or C.2 or C.3)+D.17, A+B+C.1 (or C.2 or C.3)+D.18, A+B+C.1 (or C.2 or C.3)+D.18a, A+B+C.1 (or C.2 or C.3)+D.1
• herbicidal compositions comprising the following combinations of four active ingredients (herbicide A+herbicide B+herbicide C+ safener E):
• herbicidal compositions comprising the following combinations of five active ingredients (herbicide A+herbicide B+herbicide C+ herbicide D+safener E):
• A+B+C.1 (or C.2 or C.3)+D.7a+E.2a, A+B+C.1 (or C.2 or C.3)+D.7b+E.2a, A+B+C.1 (or C.2 or C.3)+D.8+E.2a, A+B+C.1 (or C.2 or C.3)+D.9+E.2a, A+B+C.1 (or C.2 or C.3)+D.10+E.2a, A+B+C.1 (or C.2 or C.3)+D.1 1 +E.2a, A+B+C.1 (or C.2 or C.3)+D.12+E.2a, A+B+C.1 (or C.2 or C.3)+D.12a+E.2a, A+B+C.1 (or C.2 or C.3)+D.13+E.2a, A+B+C.1 (or C.2 or C.3)
• A+B+C.1 (or C.2 or C.3)+D.1 +E.6, A+B+C.1 (or C.2 or C.3)+D.2+E.6, A+B+C.1 (or C.2 or C.3)+D.3+E.6, A+B+C.1 (or C.2 or C.3)+D.4+E.6, A+B+C.1 (or C.2 or C.3)+D.5+E.6, A+B+C.1 (or C.2 or C.3)+D.5a+E.6, A+B+C.1 (or C.2 or C.3)+D.5b+E.6, A+B+C.1 (or C.2 or C.3)+D.5c+E.6, A+B+C.1 (or C.2 or C.3)+D.6+E.6, A+B+C.1 (or C.2 or C.3)+D.7+E.6, A+B+C.1 (or C.
• A+B+C.1 (or C.2 or C.3)+D.9+E.6, A+B+C.1 (or C.2 or C.3)+D.10+E.6, A+B+C.1 (or C.2 or C.3)+D.1 1 +E.6, A+B+C.1 (or C.2 or C.3)+D.12+E.6, A+B+C.1 (or C.2 or C.3)+D.12a+E.6, A+B+C.1 (or C.2 or C.3)+D.13+E.6, A+B+C.1 (or C.2 or C.3)+D.14+E.6, A+B+C.1 (or C.2 or C.3)+D.14a+E.6, A+B+C.1 (or C.2 or C.3)+D.15+E.6, A+B+C.1 (or C.2 or C.3)+D.16+E.6, A+B+C.1 (or C.
• A+B+C.1 (or C.2 or C.3)+D.7a+E.8a, A+B+C.1 (or C.2 or C.3)+D.7b+E.8a, A+B+C.1 (or C.2 or C.3)+D.8+E.8a, A+B+C.1 (or C.2 or C.3)+D.9+E.8a, A+B+C.1 (or C.2 or C.3)+D.10+E.8a, A+B+C.1 (or C2 or C.3)+D.1 1 +E.8a, A+B+C.1 (or C.2 or C.3)+D.12+E.8a, A+B+C.1 (or C.2 or C.3)+D.12a+E.8a, A+B+C.1 (or C.2 or C.3)+D.13+E.8a, A+B+C.1 (or C.2 or C.3)+
• A+B+C.1 (or C.2 or C.3)+D.25a+E.9, A+B+C.1 (or C.2 or C.3)+D.25b+E.9, A+B+C.1 (or C.2 or C.3)+D.26+E.9, A+B+C.1 (or C.2 or C.3)+D.27+E.9, A+B+C.1 (or C.2 or C.3)+D.28+E.9, A+B+C.1 (or C.2 or C.3)+D.28a+E.9, A+B+C.1 (or C.2 or C.3)+D.29+E.9, A+B+C.1 (or C.2 or C.3)+D.30+E.9, A+B+C.1 (or C.2 or C.3)+D.30a+E.9, A+B+C.1 (or C.2 or C.3)+D.30b+E.9
• A+B+C.1 (or C.2 or C.3)+D.48a+E.9, A+B+C.1 (or C.2 or C.3)+D.49+E.9, A+B+C.1 (or C.2 or C.3)+D.50+E.9, A+B+C.1 (or C.2 or C.3)+D.51 +E.9, A+B+C.1 (or C.2 or C.3)+D.51 a+E.9, A+B+C.1 (or C.2 or C.3)+D.52+E.9, A+B+C.1 (or C.2 or C.3)+D.53+E.9, A+B+C.1 (or C.2 or C.3)+D.53a+E.9, A+B+C.1 (or C.2 or C.3)+D.54+E.9, A+B+C.1 (or C.2 or C.3)+D.54+E.9,
• the weight ratio of herbicide A (in particular ( ⁇ )-2- exo-(2-Methylbenzyloxy)-1 -methyl-4-isopropyl-7-oxabicyclo[2.2.1]heptane) to herbicide D is in general in the range from 1 :0.002 to 1 :128, preferably from 1 :0.0026 to 1 :86 and more preferably from 1 :0.004 to 1 :64, wherein each herbicide D being an ester or a salt of an acid is calculated as the acid.
• the weight ratio of herbicide A (in particular ( ⁇ )- 2-exo-(2-Methylbenzyloxy)-1-methyl-4-isopropyl-7-oxabicyclo[2.2.1]heptane) to herbicide D is in the range from 1 :0.002 to 1 :60, preferably from 1 :0.0026 to 1 :40 and more preferably from 1 :0.004 to 1 :30, wherein each herbicide D being an ester or a salt of an acid is calculated as the acid.
• the weight ratio of herbicide B (metazachlor) to herbicide D is in general in the range from 1 :0.001 to 1 :64, preferably from 1 :0.0013 to 1 :44 and more preferably from 1 :0.002 to 1 :26, wherein each herbicide D being an ester or a salt of an acid is calculated as the acid.
• the weight ratio of herbicide B metalazachlor
• herbicide D is in the range from 1 :0.001 to 1 :30, preferably from 1 :0.001 to 1 :20 and more preferably from 1 :0.002 to 1 :12, wherein each herbicide D being an ester or a salt of an acid is calculated as the acid.
• the weight ratio of herbicide C preferably imazamox (C.1 ), the R-isomer of imazamox (C.2) or imazamox-ammonium (C.3)
• herbicide D is in general in the range from 1 :0.01 to 1 :3000, preferably from 1 :0.013 to 1 :1200 and more preferably from 1 :0.04 to 1 :600, wherein each herbicide D being an ester or a salt of an acid is calculated as the acid.
• the weight ratio of herbicide C preferably imazamox (C.1 ), the R- isomer of imazamox (C.2) or imazamox-ammonium (C.3)) to herbicide D is in the range from 1 :0.1 to 1 :1500, preferably from 1 :0.1 to 1 :600 and more preferably from 1 :0.4 to 1 :300, wherein each herbicide D being an ester or a salt of an acid is calculated as the acid.
• weight ratios are particularly suitable for use in oilseed rape.
• the weight ratio of herbicide C (preferably imazamox (C.1 ), the R- isomer of imazamox (C.2) or imazamox-ammonium (C.3)) to herbicide D is in the range from 1 :0.01 to 1 :1500, preferably from 1 :0.01 to 1 :600 and more preferably from 1 :0.04 to 1 :300, wherein each herbicide D being an ester or a salt of an acid is calculated as the acid.
• the aforementioned weight ratios are particularly suitable for use in sunflower.
• the weight ratio of herbicide C (preferably imazamox (C.1 ), the R- isomer of imazamox (C.2) or imazamox-ammonium (C.3)) to herbicide D is in the range from 1 :0.05 to 1 :900, preferably from 1 :0.06 to 1 :360 and more preferably from 1 :0.2 to 1 :180, wherein each herbicide D being an ester or a salt of an acid is calculated as the acid.
• the aforementioned weight ratios are particularly suitable for use in cereals (in particular wheat).
• the composition contains the safener E in an effective amount, which is generally at least 0.1 % by weight, in particular at least 0.2 or at least 0.5% by weight, based on the total amount of herbicide A, herbicide B, herbicide C and, if present, herbicide D.
• the weight ratio of the herbicide A (in particular ( ⁇ )-2-exo-(2-Methylbenzyloxy)-1-methyl-4- isopropyl-7-oxabicyclo[2.2.1 ]heptane) to the safener E is generally in the range from 1 :0.002 to 1 :24, preferably from 1 :0.004 to 1 :12 and more preferably from 1 :0.012 to 1 :5, wherein each safener E being an ester or a salt of an acid is calculated as the acid.
• the weight ratio of herbicide B (metazachlor) to the safener E is generally in the range from 1 :0.0005 to 1 :5, preferably from 1 :0.001 to 1 :3 and more preferably from 1 :0.0025 to 1 :1 , wherein each safener E being an ester or a salt of an acid is calculated as the acid.
• the weight ratio of herbicide C (preferably imazamox (C.1 ), the R-isomer of imazamox (C.2) or imazamox-ammonium (C.3)) to the safener E is generally in the range from 1 :0.0005 to 1 :5, preferably from 1 :0.001 to 1 :3 and more preferably from 1 :0.0025 to 1 :1 , wherein each safener E being an ester or a salt of an acid is calculated as the acid.
• the herbicides A, B and C are preferably applied within the same weight ratios as defined herein for the composition of this invention.
• the herbicide A and the herbicide D are preferably applied within the same weight ratios as defined herein for the composition of this invention.
• the herbicide B and the herbicide D are preferably applied within the same weight ratios as defined herein for the composition of this invention.
• the herbicide C and the herbicide D are preferably applied within the same weight ratios as defined herein for the composition of this invention.
• the herbicide A and the safener E are preferably applied within the same weight ratios as defined herein for the composition of this invention.
• the herbicide B and the safener E are preferably applied within the same weight ratios as defined herein for the composition of this invention.
• the herbicide C and the safener E are preferably applied within the same weight ratios as defined herein for the composition of this invention.
• the herbicide A, the herbicide B, the herbicide C and, if present, the herbicide D and/or the safener E can be applied jointly or separately.
• the herbicide A, the herbicide B, the herbicide C and, if present, the herbicide D and/or the safener E can be applied simultaneously or in succession.
• the herbicide A, the herbicide B, the herbicide C and, if present, the herbicide D and/or the safener E are applied simultaneously to the undesirable vegetation.
• the herbicide A, the herbicide B, the herbicide C and, if present, the herbicide D and/or the safener E are provided as herbicidal composition according to the invention (e.g. a tank mixture containing the herbicide A, the herbicide B, the herbicide C and, if present, the herbicide D and/or the safener E) being applied to the undesirable vegetation.
• the herbicidal composition of this invention is applied to the undesirable vegetation or the locus thereof with or applied to the soil or water to prevent the emergence or growth of the undesirable vegetation.
• the order of the application of the herbicide A, the herbicide B, the herbicide C and, if present, the herbicide D and/or the safener E is of minor importance. It is only necessary that the herbicide A, the herbicide B, the herbicide C and, if present, the herbicide D and/or the safener E are applied in a time frame that allows
• the herbicide A, the herbicide B, the herbicide C and, if present, the herbicide D and/or the safener E can be applied pre-emergence (before the emergence of undesirable vegetation) or post- emergence (i.e., during and/or after emergence of the undesirable vegetation).
• the herbicide A, the herbicide B, the herbicide C and, if present, the herbicide D and/or the safener E (or the composition according to the invention) are/is applied before the emergence of the undesirable vegetation (pre-emergence).
• the herbicide A, the herbicide B, the herbicide C and, if present, the herbicide D and/or the safener E are/is applied before or during the emergence of the undesirable vegetation (pre-emergence or early-post emergence).
• the herbicide A, the herbicide B, the herbicide C and, if present, the herbicide D and/or the safener E are/is applied after emergence of the undesirable vegetation.
• the herbicide A, the herbicide B, the herbicide C and, if present, the herbicide D and/or the safener E are/is preferably applied after the undesirable vegetation has emerged and has developed up to 6 leaves.
• compositions and methods of the present invention are suitable for controlling a large number of undesirable vegetation (harmful plants), including monocotyledonous weeds and dicotyledonous weeds.
• the undesirable vegetation is selected from monocotyledonous weed species.
• the undesirable vegetation is selected from the family Poaceae. More preferably, the undesirable vegetation is selected from the tribes Aveneae, Bromeae, Paniceae and Poeae. In one embodiment, the undesirable vegetation is selected from the tribe Aveneae. In another embodiment, the undesirable vegetation is selected from the tribe Bromeae. In yet another embodiment, the undesirable vegetation is selected from the tribe Paniceae. In still another embodiment, the undesirable vegetation is selected from the tribe Poeae.
• compositions and methods of the present invention may be used for controlling annual weeds such as gramineous weeds (grass weeds) including, but not limited to, the genera Aegilops such as Aegilops cylindrical (AEGCY, jointed goatgrass); Agropyron such as Agropyron repens (AGRRE, common couchgrass); Alopecurus such as Alopecurus myosuroides (ALOMY, blackgrass) or Alopecurus aequalis (ALOAE, foxtail); Apera such as Apera spica-venti (APESV, silky wind grass); Avena such as Avena fatua (AVEFA, wild oat) or Avena sterilis subsp.
• grass weeds including, but not limited to, the genera Aegilops such as Aegilops cylindrical (AEGCY, jointed goatgrass); Agropyron such as Agropyron repens (AGRRE, common couchgrass); Alopecurus such as Alopecurus myosuroides
• AVEST sterile oat
• Brachiaria such as Brachiaria plantaginea (BRAPL, Alexander grass) or Brachiaria decumbens (BRADC, Surinam grass
• Bromus such as Bromus inermis (BROIN, awnless brome), Bromus sterilis (BROST, barren bromegrass), Bromus tectorum (BROTE, cheatgrass), Bromus arvensis (BROAV, field bromegrass), Bromus secalinus (BROSE, rye bromegrass) or Bromus hordeacus (BROMO, lopgrass); Cenchrus such as Cenchrus echinatus (CCHEC, Mossman River grass); Cynodon such as Cynodon dactylon (CYNDA, bermudagrass); Digitaria such as Digitaria ciliaris (DIGAD, southern crabgrass), Digitaria sanguinalis (DIGSA, hairy crabgrass), Digitaria insularis (TRCIN
• LEFPC thread sprangletop
• Leptochloa mucronata Leptochloa panicoides
• LEFPA tighthead sprangletop
• Leptochloa scabra Leptochloa virgata
• Lolium such as Lolium multiflorum (LOLMU, Italian ryegrass), Lolium perenne (LOLPE, English ryegrass) or Lolium rigidum (LOLRI, annual ryegrass
• Panicum such as Panicum capillare (PANCA, tumble panicgrass), Panicum
• Phalaris such as Phalaris minor (PHAMI, lesser canary grass), Phalaris paradoxa (PHAPA, paradoxagrass), Phalaris canariensis (PHACA, canarygrass) or Phalaris brachystachys (PHABR, short-spiked canarygrass); Poa such as Poa annua (POAAN, annual bluegrass), Poa pratensis (POAPR, Kentucky bluegrass) or Poa trivialis (POATR, rough meadowgrass); Rottboellia such as Rottboellia exaltata (ROOEX, guinea-fowl grass); Setaria such as Setaria faberi (SETFA, giant foxtail), Setaria glauca (PESGL, pearl millet), Setaria italic (SETIT, Italian
• the undesirable vegetation is a monocotyledonous weed species selected from the genera Agropyron, Alopecurus, Apera, Avena, Brachiaria, Bromus, Cynodon, Digitaria,
• Echinochloa Eleusine, Ischaemum, Leptochloa, Lolium, Panicum, Phalaris, Poa, Rottboellia, and Setaria. More preferably, the undesirable vegetation is selected from the genera
• the undesirable vegetation is selected from the genera Alopecurus, Apera, Avena, Digitaria, Echinochloa, Leptochloa, Lolium, Phalaris, Poa and Setaria.
• the undesirable vegetation is selected from the genera Alopecurus, Apera, Avena, Echinochloa, Leptochloa, Lolium, Phalaris and Poa.
• the undesirable vegetation is selected from the genera Alopecurus, Avena, Lolium and Phalaris.
• the undesirable vegetation is a monocotyledonous weed species selected from the genera Alopecurus, Apera, Lolium and Poa. In another embodiment, the undesirable vegetation is a monocotyledonous weed species selected from Agropyron repens, Alopecurus myosuroides, Alopecurus aequalis, Apera spica- venti, Avena fatua, Avena sterilis subsp.
• the monocotyledonous weed species is selected from Alopecurus myosuroides, Alopecurus aequalis, Apera spica-venti, Avena fatua, Avena sterilis subsp. sterilis, Echinochloa crus-galli, Echinochloa oryzoides, Leptochloa chinensis, Lolium multiflorum, Lolium perenne, Lolium rigidum, Phalaris minor, Phalaris paradoxa, Phalaris canariensis, Phalaris
• brachystachys Poa annua, Poa pratensis and Poa trivialis, more preferably from Alopecurus myosuroides, Alopecurus aequalis, Apera spica-venti, Avena fatua, Echinochloa grus-galli, Echinochloa oryzoides, Leptochloa chinensis, Lolium multiflorum, Lolium rigidum, Phalaris minor and Poa annua, and most preferably from Alopecurus myosuroides, Avena fatua, Lolium multiflorum, Lolium rigidum and Phalaris minor.
• the monocotyledonous weed species is selected from Alopecurus myosuroides, Apera spica-venti, Lolium multiflorum and Poa annua.
• compositions and methods of the present invention are also suitable for controlling a large number of dicotyledonous weeds, in particular broadleaf weeds including, but not limited to, Polygonum species such as Polygonum convolvolus (POLCO, wild buckwheat), Amaranthus species such as Amaranthus albus (AMAAL, tumble pigweed), Amaranthus blitoides (AMABL, mat amaranth), Amaranthus hybridus (AMACH, green pigweed), Amaranthus palmeri (AMAPA, Palmer amaranth), Amaranthus powellii (AMAPO, Powell amaranth), Amaranthus retroflexus (AMARE, redroot pigweed), Amaranthus tuberculatus (AMATU, rough-fruit amaranth),
• Polygonum species such as Polygonum convolvolus (POLCO, wild buckwheat)
• Amaranthus species such as Amaranthus albus (AMAAL, tumble pigweed), Amaranthus bli
• Amaranthus rudis (AMATA, tall amaranth) or Amaranthus viridis (AMAVI, slender amaranth), Aethusa species such as Aethusa cynapium (AETCY, fool's parsley), Ammi species such as Ammi majus (AMIMI), Conium species such as Conium maculatum (COIMA, poison hemlock), Chenopodium species such as Chenopodium album (CHEAL, common lambsquarters), Chenopodium ficifolium (CHEFI, fig-leaved goosefoot), Chenopodium polyspermum (CHEPO, many-seeded goosefoot) or Chenopodium hybridum (CHEHY, maple-leaf goosefoot), Sida species such as Sida spinosa L.
• Aethusa species such as Aethusa cynapium (AETCY, fool's parsley
• Ammi species such as Ammi majus (AMIMI)
• SI DSP prickly sida
• Ambrosia species such as Ambrosia artemisiifolia (AMBEL, common ragweed), Acanthospermum species, Anthemis species such as Anthemis arvensis (ANTAR, field chamomile), Atriplex species, Cirsium species, Convolvulus species, Conyza species such as Conyza bonariensis (ERIBO, hairy horseweed) or Conyza canadensis (ERICA, Canada horseweed), Cassia species, Commelina species, Datura species, Euphorbia species, Geranium species such as Geranium dissectum (GERDI, cut-leaf geranium), Geranium pusillium (GERPU, small-flower geranium) or Geranium rotundifolium (GERRT, round-leaved cranesbill), Galinsoga species, Ipomoea species such as Ipomoea hederacea (I POHE, morningglory), Lamium species,
• GALTC corn cleavers
• HELAN Helianthus annuus
• Desmodium tortuosum (DEDTO, giant beggar weed), Kochia scoparia (KCHSC, mock cypress), Mercurialis annua (MERAN, annual mercury), Myosotis arvensis (MYOAR, field forget-me-not), Papaver rhoeas (PAPRH, common poppy), Salsola kali (SASKA, prickly glasswort), Sonchus arvensis (SONAR, corn sowthistle), Tagetes minuta (TAGMI, Mexican marigold), Richardia brasiliensis (RCHBR, Brazil pusley), cruciferous weeds such as Raphanus raphanistrum
• RPA RaPRA
• Sinapis alba SINAL, white mustard
• Sinapis arvensis SINAR, wild mustard
• Thlaspi arvense THLAR
• DESSO Thlaspi arvense
• CAPBP Capsella bursa-pastoris
• Sisymbrium species such as Sisymbrium officinale (SSYOF, hedge mustard) or Sisymbrium orientale (SSYOR, oriental mustard), Brassica kaber (SINAR, wild mustard).
• the undesirable vegetation is a dicotyledonous weed species selected from the genera Amaranthus, Ambrosia, Aethusa, Ammi, Conium, Anthemis, Capsella, Centaurea, Chenopodium, Conyza, Descurainia, Galium, Geranium, Kochia, Matricaria, Papaver,
• Raphanus Sinapis, Sisymbrium, Stellaria and Thlaspi, more preferably from the genera
• the dicotyledonous weed species is selected from Amaranthus albus, Amaranthus blitoides, Amaranthus hybridus, Amaranthus palmeri, Amaranthus powellii, Amaranthus retroflexus, Amaranthus tuberculatus, Amaranthus rudis, Amaranthus viridis, Ambrosia artemisiifolia, Aethusa cynapium, Ammi majus, Conium maculatum, Anthemis arvensis, Capsella bursa-pastoris, Centaurea cyanus, Chenopodium album, Chenopodium ficifolium, Chenopodium polyspermum, Chenopodium hybridum, Conyza bonariensis, Conyza
• the dicotyledonous weed species is selected from
• the undesirable vegetation is selected from the genera Agropyron, Alopecurus, Apera, Avena, Brachiaria, Bromus, Cynodon, Digitaria, Echinochloa, Eleusine, Ischaemum, Leptochloa, Lolium, Panicum, Phalaris, Poa, Rottboellia, Setaria, Aethusa, Amaranthus, Ambrosia, Ammi, Anthemis, Capsella, Centaurea, Chenopodium, Conium, Conyza, Descurainia, Galium, Kochia, Matricaria, Papaver, Raphanus, Sinapis, Sisymbrium, Stellaria and Thlaspi.
• the undesirable vegetation is selected from the genera Agropyron, Alopecurus, Apera, Avena, Brachiaria, Bromus, Cynodon, Digitaria, Echinochloa, Eleusine, Ischaemum, Leptochloa, Lolium, Panicum,
• the undesirable vegetation is selected from the group consisting of Alopecurus myosuroides, Alopecurus aequalis, Apera spica-venti, Avena fatua, Avena sterilis, Brachiaria plantaginea, Brachiaria decumbens, Bromus secalinus, Bromus sterilis, Bromus tectorum, Digitaria ciliaris, Digitaria insularis, Digitaria ischaemum, Digitaria sanguinalis, Echinochloa colona, Echinochloa crus-galli, Echinochloa crus-pavonis, Echinochloa erecta, Echinochloa oryzoides, Echinochloa phyllogogon, Eleusine indica, Ischaemum rugosum, Leptochloa chinensis, Leptochloa panicoides, Leptochloa scabra, Lept
• Alopecurus aequalis Apera spica-venti, Echinochloa crus-galli, Echinochloa oryzoides,
• Leptochloa chinensis Lolium multiflorum, Lolium rigidum, Phalaris minor and Poa annua, Galium aparine and in particular selected from the group consisting of Alopecurus myosuroides, Lolium multiflorum, Lolium rigidum, Phalaris minor and Galium aparine.
• the undesirable vegetation is a herbicide resistant or tolerant weed species.
• Exemplary herbicide resistant or tolerant weed species include, but are not limited to, biotypes resistant or tolerant to herbicides selected from the group consisting of acetyl CoA carboxylase (ACCase) inhibitors (HRAC Group A), acetolactate synthase (ALS) inhibitors (HRAC Group B), photosystem II (PS II) inhibitors (HRAC Groups C1 , C2 and C3), photosystem I (PS I) inhibitors (HRAC Group D), protoporphyrinogen oxidase (PPO) inhibitors (HRAC Group E), 4- hydroxyphenyl-pyruvate-dioxygenase (HPPD) inhibitors (HRAC Group F1 ), phytoene desaturase (PDS) inhibitors (HRAC Group F2), carotenoid biosynthesis inhibitors (HRAC Group F3), DOXP synthase inhibitors (HRAC Group F4), 5- enolpymvylshikimate-3-phosphate (EPSP) inhibitors (H
• the herbicide resistant or tolerant weed species is selected from biotypes resistant or tolerant to herbicides selected from the group consisting of acetyl CoA carboxylase (ACCase) inhibitors (HRAC Group A), acetolactate synthase (ALS) inhibitors (HRAC Group B), photosystem II (PS II) inhibitors (HRAC Groups C1 , C2 and C3), protoporphyrinogen oxidase (PPO) inhibitors (HRAC Group E), 4-hydroxyphenyl-pyruvate-dioxygenase (HPPD) inhibitors (HRAC Group F1 ), phytoene desaturase (PDS) inhibitors (HRAC Group F2), 5- enolpymvylshikimate-3-phosphate (EPSP) inhibitors (HRAC Group G), inhibitors of microtubuli assembly (HRAC Group K1 ), very long chain fatty acid (VLCFA) inhibitors (HRAC Group K3), Inhibitors of cell wall synthesis (H
• the herbicide resistant or tolerant weed species is selected from biotypes resistant or tolerant to herbicides selected from the group consisting of acetyl CoA carboxylase (ACCase) inhibitors (HRAC Group A), acetolactate synthase (ALS) inhibitors (HRAC Group B), photosystem II (PS II) inhibitors (HRAC Groups C1 , C2 and C3), inhibitors of microtubuli assembly (HRAC Group K1 ), very long chain fatty acid (VLCFA) inhibitors (HRAC Group K3) and inhibitors of lipid synthesis (HRAC Group N).
• ACCase acetyl CoA carboxylase
• ALS acetolactate synthase
• PS II photosystem II
• HRAC Groups C1 , C2 and C3 inhibitors of microtubuli assembly
• VLCFA very long chain fatty acid
• the herbicide resistant or tolerant weed species is selected from biotypes with resistance or tolerance to at least one herbicide selected from the group consisting of acetyl CoA carboxylase (ACCase) inhibitors (HRAC Group A), acetolactate synthase (ALS) inhibitors (HRAC Group B) and photosystem II (PS II) inhibitors (HRAC Groups C1 , C2 and C3).
• ACCase acetyl CoA carboxylase
• ALS acetolactate synthase
• PS II photosystem II
• the resistant or tolerant biotype is selected from the genera Agropyron, Alopecurus, Apera, Avena, Brachiaria, Bromus, Cynodon, Digitaria, Echinochloa, Eleusine, Ischaemum, Leptochloa, Lolium, Panicum, Phalaris, Poa, Rottboellia, Setaria, Anthemis, Amaranthus, Ambrosia, Capsella, Centaurea, Chenopodium, Conyza, Descurainia, Galium, Kochia, Matricaria, Papaver, Raphanus, Sinapis, Sisymbrium, Stellaria and Thlaspi.
• the resistant or tolerant biotype is selected from the genera Alopecurus, Apera, Digitaria, Echinochloa, Leptochloa, Lolium, Phalaris, Poa, Setaria, Amaranthus, Anthemis, Capsella, Centaurea, Chenopodium, Descurania, Kochia, Matricaria, Papaver, Sisymbrium, Stellaria and Thlaspi, more preferably selected from the genera Alopecurus, Apera, Digitaria, Echinochloa, Leptochloa, Lolium, Phalaris, Poa, Setaria, Amaranthus, Anthemis, Capsella, Centaurea, Chenopodium, Descurania, Kochia, Matricaria, Papaver, Sisymbrium, Stellaria and Thlaspi, more preferably selected from the genera Alopecurus, Apera,
• the resistant or tolerant biotype is selected from the genera Alopecurus, Apera, Digitaria, Echinochloa, Leptochloa, Phalaris, Poa, Setaria, Amaranthus, Anthemis, Capsella, Centaurea, Chenopodium, Descurania, Kochia, Matricaria, Papaver, Sisymbrium, Stellaria and Thlaspi, more preferably selected from the genera Alopecurus, Apera, Digitaria, Echinochloa, Leptochloa, Phalaris, Poa, Setaria, Amaranthus, Anthemis, Capsella, Centaurea, Chenopodium, Descurania, Kochia, Matricaria, Papaver, Sisymbrium, Stellaria and Thlaspi, more preferably selected from the genera Alopecurus, Apera,
• Echinochloa, Leptochloa, Phalaris, Poa Amaranthus, Chenopodium, Matricaria, Papaver and Stellaria, even more preferably selected from the genera Alopecurus, Echinochloa, Phalaris, Poa, Amaranthus, Chenopodium, Matricaria, Papaver and Stellaria, yet more preferably selected from the genera Alopecurus, Echinochloa, Phalaris, Poa and Papaver and in particular selected from the genera Alopecurus, Phalaris and Papaver.
• the resistant or tolerant biotype is a monocotyledonous weed species selected from the genera Alopecurus, Apera, Digitaria, Echinochloa, Leptochloa, Lolium, Phalaris, Poa and Setaria, preferably selected from the genera Alopecurus, Apera, Echinochloa, Leptochloa, Lolium, Phalaris and Poa, more preferably selected from the genera Alopecurus, Echinochloa, Lolium, Phalaris and Poa, and in particular selected from the genera Alopecurus, Lolium and Phalaris.
• the resistant or tolerant biotype is a monocotyledonous weed species, preferably a monocotyledonous weed species selected from the genera Alopecurus, Apera, Digitaria, Echinochloa, Leptochloa, Phalaris, Poa and Setaria, preferably selected from the genera Alopecurus, Apera, Echinochloa, Leptochloa, Phalaris and Poa, more preferably selected from the genera Alopecurus, Echinochloa, Phalaris and Poa, and in particular selected from the genera Alopecurus and Phalaris.
• the resistant or tolerant biotype is a monocotyledonous weed species selected from the genera Alopecurus, Apera, Lolium and Poa.
• the resistant or tolerant biotype is a dicotyledonous weed species, preferably a dicotyledonous weed species selected from the genera Amaranthus, Anthemis, Capsella, Centaurea, Chenopodium, Descurania, Kochia, Matricaria, Papaver, Sisymbrium, Stellaria and Thiaspi, more preferably selected from the genera Amaranthus, Chenopodium, Matricaria, Papaver and Stellaria and in particular selected from the genus Papaver.
• a dicotyledonous weed species selected from the genera Amaranthus, Anthemis, Capsella, Centaurea, Chenopodium, Descurania, Kochia, Matricaria, Papaver, Sisymbrium, Stellaria and Thiaspi, more preferably selected from the genera Amaranthus, Chenopodium, Matricaria, Papaver and Stellaria and in particular selected from the genus Papaver.
• the resistant or tolerant biotype is selected from the group consisting of Alopecurus myosuroides, Alopecurus aequalis, Apera spica-venti, Avena fatua, Avena sterilis, Brachiaria plantaginea, Brachiaria decumbens, Bromus secalinus, Bromus sterilis, Bromus tectorum, Digitaria ciliaris, Digitaria insularis, Digitaria ischaemum, Digitaria sanguinalis, Echinochloa colona, Echinochloa crus-galli, Echinochloa crus-pavonis, Echinochloa erecta, Echinochloa oryzoides, Echinochloa phyllogogon, Eleusine indica, Ischaemum rugosum, Leptochloa chinensis, Leptochloa panicoides, Leptochloa scabra,
• Matricaria discoidea Matricaria inodora, Papaver rhoeas, Raphanus raphanistrum, Sinapis alba, Sinapis arvensis, Sisymbrium officinale, Sisymbrium orientale, Stellaria media and Thiaspi arvense, preferably selected from the group consisting of Alopecurus myosuroides, Alopecurus aequalis, Apera spica-venti, Digitaria ischaemum, Digitaria sanguinalis, Echinochloa crus-galli, Echinochloa oryzoides, Leptochloa chinensis, Lolium multiflorum, Lolium perenne, Lolium rigidum, Phalaris brachystachys, Phalaris minor, Phalaris paradoxa, Poa annua, Poa trivialis, Setaria faberi, Setaria glauca, Setaria pumilla, Setaria verticillata,
• Leptochloa chinensis Lolium multiflorum, Lolium rigidum, Phalaris minor and Poa annua, and in particular selected from the group consisting of Alopecurus myosuroides, Lolium multiflorum, Lolium rigidum and Phalaris minor.
• the resistant or tolerant biotype is selected from the group consisting of Alopecurus myosuroides, Alopecurus aequalis, Apera spica-venti, Avena fatua, Avena sterilis, Brachiaria plantaginea, Brachiaria decumbens, Bromus secalinus, Bromus sterilis, Bromus tectorum, Digitaria ciliaris, Digitaria insularis, Digitaria ischaemum, Digitaria sanguinalis, Echinochloa colona, Echinochloa crus-galli, Echinochloa crus-pavonis, Echinochloa erecta, Echinochloa oryzoides, Echinochloa phyllogogon, Eleusine indica, Ischaemum rugosum, Leptochloa chinensis, Leptochloa panicoides, Leptochloa scabra
• Amaranthus tuberculatus, Amaranthus rudis, Chenopodium album, Matricaria chamomilla, Matricaria inodora, Papaver rhoeas and Stellaria media especially preferably selected from the group consisting of Alopecurus myosuroides, Alopecurus aequalis, Apera spica-venti, Echinochloa crus-galli, Echinochloa oryzoides, Leptochloa chinensis, Phalaris minor and Poa annua, and in particular Alopecurus myosuroides or Phalaris minor.
• the resistant or tolerant biotype is a monocotyledonous weed species selected from the group consisting of Alopecurus myosuroides, Alopecurus aequalis, Apera spica-venti, Digitaria ischaemum, Digitaria sanguinalis, Echinochloa crus-galli, Echinochloa oryzoides, Leptochloa chinensis, Lolium multiflorum, Lolium perenne, Lolium rigidum, Phalaris brachystachys, Phalaris minor, Phalaris paradoxa, Poa annua, Poa trivialis, Setaria faberi, Setaria glauca, Setaria pumilla, Setaria verticillata and Setaria viridis, preferably selected from the group consisting of Alopecurus myosuroides, Alopecurus aequalis, Apera spica-venti,
• the resistant or tolerant biotype is selected from Alopecurus
• the resistant or tolerant biotype is a dicotyledonous weed species selected from the group consisting of Amaranthus powellii, Amaranthus retroflexus, Amaranthus tuberculatus, Amaranthus rudis, Anthemis arvensis, Capsella bursa-pastoris, Centaurea cyanus, Chenopodium album, Descurania sophia, Kochia scoparia, Matricaria chamomilla,
• Matricaria inodora Papaver rhoeas, Sisymbrium officinale, Stellaria media and Thiaspi arvense, preferably selected from the group consisting of Amaranthus powellii, Amaranthus retroflexus, Amaranthus tuberculatus, Amaranthus rudis, Chenopodium album, Matricaria chamomilla, Matricaria inodora, Papaver rhoeas and Stellaria media, and more preferably Papaver rhoeas.
• compositions, uses and methods of this invention are suitable for controlling ACCase-resistant grass weeds, more specifically ACCase-resistant grass weeds selected from the group consisting of Alopecurus myosuroides, Alopecurus aequalis, Apera spica-venti, Avena fatua, Avena sterilis, Brachiaria plantaginea, Brachiaria decumbens, Bromus secalinus, Bromus sterilis, Bromus tectorum, Digitaria ciliaris, Digitaria insularis, Digitaria ischaemum, Digitaria sanguinalis, Echinochloa colona, Echinochloa crus-galli, Echinochloa crus-pavonis, Echinochloa erecta, Echinochloa oryzoides, Echinochloa phyllogogon, Eleusine indica,
• compositions, uses and methods of this invention are also suitable for controlling ALS- resistant grass weeds, more specifically ALS-resistant grass weeds selected from the group consisting of Alopecurus myosuroides, Alopecurus aequalis, Apera spica-venti, Avena fatua, Avena sterilis, Brachiaria plantaginea, Brachiaria decumbens, Bromus secalinus, Bromus sterilis, Bromus tectorum, Digitaria ciliaris, Digitaria insularis, Digitaria ischaemum, Digitaria sanguinalis, Echinochloa colona, Echinochloa crus-galli, Echinochloa crus-pavonis, Echinochloa erecta, Echinochloa oryzoides, Echinochloa phyllogogon, Eleusine indica, Ischaemum rugosum, Leptochloa chinens
• Alopecurus myosuroides Lolium multiflorum, Lolium rigidum and Phalaris minor.
• compositions, uses and methods of this invention are also suitable for controlling ALS- resistant dicotyledonous weeds, more specifically ALS-resistant dicotyledonous weeds selected from the group consisting of Amaranthus albus, Amaranthus blitoides, Amaranthus hybridus, Amaranthus palmeri, Amaranthus powellii, Amaranthus retroflexus, Amaranthus tuberculatus, Amaranthus rudis, Amaranthus viridis, Ambrosia artemisiifolia, Anthemis arvensis, Capsella bursa-pastoris, Centaurea cyanus, Chenopodium album, Chenopodium ficifolium, Chenopodium polyspermum, Chenopodium hybridum, Conyza bonariensis, Conyza
• compositions, uses and methods of this invention are suitable for controlling PS ll-resistant grass weeds, more specifically PS ll-resistant grass weeds selected from the group consisting of Alopecurus myosuroides, Alopecurus aequalis, Apera spica-venti, Avena fatua, Avena sterilis, Brachiaria plantaginea, Brachiaria decumbens, Bromus secalinus, Bromus sterilis, Bromus tectorum, Digitaria ciliaris, Digitaria insularis, Digitaria ischaemum, Digitaria sanguinalis, Echinochloa colona, Echinochloa crus-galli, Echinochloa crus-pavonis, Echinochloa erecta, Echinochloa oryzoides, Echinochloa phyllogogon, Eleusine indica, Ischaemum rugosum, Leptochloa
• compositions, uses and methods of this invention are also suitable for controlling PSII- resistant dicotyledonous weeds, more specifically PSII-resistant dicotyledonous weeds selected from the group consisting of Amaranthus albus, Amaranthus blitoides, Amaranthus hybridus, Amaranthus palmeri, Amaranthus powellii, Amaranthus retroflexus, Amaranthus tuberculatus, Amaranthus rudis, Amaranthus viridis, Ambrosia artemisiifolia, Anthemis arvensis, Capsella bursa-pastoris, Centaurea cyanus, Chenopodium album, Chenopodium ficifolium,
• compositions according to the invention are suitable as herbicides as such or as appropriately formulated agrochemical compositions.
• agrochemical composition refers to a composition according to the invention further comprising one or more auxiliaries customary in crop protection.
• the invention also relates to agrochemical compositions comprising a herbicidally effective amount of herbicide A, herbicide B (metazachlor), herbicide C (preferably imazamox (C.1 ), the R-isomer of imazamox (C.2) or imazamox-ammonium (C.3)), optionally at least one herbicide D (as defined herein, in particular quinmerac (D.137)), optionally at least one safener E (as defined herein) and one or more auxiliaries customary in crop protection.
• herbicide A herbicide B (metazachlor)
• herbicide C preferably imazamox (C.1 ), the R-isomer of imazamox (C.2) or imazamox-ammonium (C.3)
• at least one herbicide D as defined herein, in particular quinmerac (D.137)
• optionally at least one safener E as defined herein
• auxiliaries customary in crop protection customary in crop protection.
• the herbicide A, herbicide B, herbicide C, optionally at least one herbicide D (as defined herein) and optionally at least one safener E (as defined herein) can be converted into customary types of agrochemical compositions, e. g. solutions, emulsions, suspensions, dusts, powders, pastes, granules, pressings, and mixtures thereof.
• agrochemical compositions e. g. solutions, emulsions, suspensions, dusts, powders, pastes, granules, pressings, and mixtures thereof.
• compositions are defined in the "Catalogue of pesticide formulation types and international coding system", Technical Monograph No. 2, 6 th Ed. May 2008, CropLife International.
• the agrochemical compositions can be prepared in a known manner, such as described by Mollet and Grubemann, Formulation technology, Wiley VCH, Weinheim, 2001 ; or Knowles, New developments in crop protection product formulation, Agrow Reports DS243, T&F Informa, London, 2005.
• the invention also relates to a process for preparing the composition (more specifically the agrochemical composition) as defined herein which comprises mixing herbicide A, herbicide B, herbicide C, optionally herbicide D and/or safener E and one or more auxiliaries customary in crop protection.
• auxiliaries customary in crop protection includes but is not limited to solvents, liquid carriers, solid carriers or fillers, surfactants, dispersants, emulsifiers, wetters, adjuvants, solubilizers, penetration enhancers, protective colloids, adhesion agents, thickeners, humectants, repellents, attractants, feeding stimulants, compatibilizers, bactericides, anti- freezing agents, anti-foaming agents, colorants, tackifiers and binders.
• Suitable solvents and liquid carriers are water and organic solvents, such as mineral oil fractions of medium to high boiling point, e.g. kerosene, diesel oil; oils of vegetable or animal origin; aliphatic, cyclic and aromatic hydrocarbons, e. g. toluene, paraffin,
• tetrahydronaphthalene alkylated naphthalenes
• alcohols e.g. ethanol, propanol, butanol, benzylalcohol, cyclohexanol
• glycols DMSO
• ketones e.g. cyclohexanone
• esters e.g. lactates, carbonates, fatty acid esters, gamma-butyrolactone
• fatty acids phosphonates
• amines amides, e.g. N-methylpyrrolidone, fatty acid dimethylamides; and mixtures thereof.
• Suitable solid carriers or fillers are mineral earths, e.g. silicates, silica gels, talc, kaolins, limestone, lime, chalk, clays, dolomite, diatomaceous earth, bentonite, calcium sulfate, magnesium sulfate, magnesium oxide; polysaccharides, e.g. cellulose, starch; fertilizers, e.g. ammonium sulfate, ammonium phosphate, ammonium nitrate, ureas; products of vegetable origin, e.g. cereal meal, tree bark meal, wood meal, nutshell meal, and mixtures thereof.
• mineral earths e.g. silicates, silica gels, talc, kaolins, limestone, lime, chalk, clays, dolomite, diatomaceous earth, bentonite, calcium sulfate, magnesium sulfate, magnesium oxide
• polysaccharides e.g. cellulose, starch
• fertilizers
• Suitable surfactants are surface-active compounds, such as anionic, cationic, nonionic and amphoteric surfactants, block polymers, polyelectrolytes, and mixtures thereof. Such surfactants can be used as emusifier, dispersant, solubilizer, wetter, penetration enhancer, protective colloid, or adjuvant. Examples of surfactants are listed in McCutcheon's, Vol.1 : Emulsifiers & Detergents, McCutcheon's Directories, Glen Rock, USA, 2008 (International Ed. or North American Ed.).
• Suitable anionic surfactants are alkali, alkaline earth or ammonium salts of sulfonates, sulfates, phosphates, carboxylates, and mixtures thereof.
• sulfonates are alkylarylsulfonates, diphenylsulfonates, alpha-olefin sulfonates, lignine sulfonates, sulfonates of fatty acids and oils, sulfonates of ethoxylated alkylphenols, sulfonates of alkoxylated arylphenols, sulfonates of condensed naphthalenes, sulfonates of dodecyl- and tridecylbenzenes, sulfonates of naphthalenes and alkylnaphthalenes, sulfosuccinates or sulfosuccinamates.
• Examples of sulfates are sulfates of fatty acids and oils, of ethoxylated alkylphenols, of alcohols, of ethoxylated alcohols, or of fatty acid esters.
• Examples of phosphates are phosphate esters.
• Examples of carboxylates are alkyl carboxylates, and carboxylated alcohol or alkylphenol ethoxylates.
• Suitable nonionic surfactants are alkoxylates, N-subsituted fatty acid amides, amine oxides, esters, sugar-based surfactants, polymeric surfactants, and mixtures thereof.
• alkoxylates are compounds such as alcohols, alkylphenols, amines, amides, arylphenols, fatty acids or fatty acid esters which have been alkoxylated with 1 to 50 equivalents.
• Ethylene oxide and/or propylene oxide may be employed for the alkoxylation, preferably ethylene oxide.
• N-subsititued fatty acid amides are fatty acid glucamides or fatty acid alkanolamides.
• esters are fatty acid esters, glycerol esters or monoglycerides.
• sugar-based surfactants are sorbitans, ethoxylated sorbitans, sucrose and glucose esters or alkylpolyglucosides.
• polymeric surfactants are home- or copolymers of vinylpyrrolidone, vinylalcohols, or vinylacetate.
• Suitable cationic surfactants are quaternary surfactants, for example quaternary ammonium compounds with one or two hydrophobic groups, or salts of long-chain primary amines.
• Suitable amphoteric surfactants are alkylbetains and imidazolines.
• Suitable block polymers are block polymers of the A-B or A-B-A type comprising blocks of polyethylene oxide and polypropylene oxide, or of the A-B-C type comprising alkanol, polyethylene oxide and polypropylene oxide.
• Suitable polyelectrolytes are polyacids or polybases. Examples of polyacids are alkali salts of polyacrylic acid or polyacid comb polymers. Examples of polybases are polyvinylamines or polyethyleneamines.
• Suitable adjuvants are compounds, which have a neglectable or even no pesticidal activity themselves, and which improve the biological performance of the compound I on the target.
• examples are surfactants, mineral or vegetable oils, and other auxilaries. Further examples are listed by Knowles, Adjuvants and additives, Agrow Reports DS256, T&F Informa UK, 2006, chapter 5.
• Suitable thickeners are polysaccharides (e.g. xanthan gum, carboxymethylcellulose), anorganic clays (organically modified or unmodified), polycarboxylates, and silicates.
• Suitable bactericides are bronopol and isothiazolinone derivatives such as alkylisothiazolinones and benzisothiazolinones.
• Suitable anti-freezing agents are ethylene glycol, propylene glycol, urea and glycerin.
• Suitable anti-foaming agents are silicones, long chain alcohols, and salts of fatty acids.
• Suitable colorants are pigments of low water solubility and water- soluble dyes.
• examples are inorganic colorants (e.g. iron oxide, titan oxide, iron
• organic colorants e.g. alizarin-, azo- and phthalocyanine colorants.
• Suitable tackifiers or binders are polyvinylpyrrolidone, polyvinylacetates, polyvinyl alcohols, polyacrylates, biological or synthetic waxes, and cellulose ethers.
• the agrochemical compositions generally comprise between 0.01 and 95%, preferably between 0.1 and 90%, and in particular between 0.5 and 75%, by weight of active substance.
• the active substances are employed in a purity of from 90% to 100%, preferably from 95% to 100% (according to NMR spectrum).
• Various types of oils, wetters, adjuvants, fertilizer, or micronutrients, and further pesticides e.g. herbicides, insecticides, fungicides, growth regulators, safeners
• pesticides e.g. herbicides, insecticides, fungicides, growth regulators, safeners
• These agents can be admixed with the compositions according to the invention in a weight ratio of 1 :100 to 100:1 , preferably 1 :10 to 10:1.
• the user applies the agrochemical composition according to the invention usually from a predosage device, a knapsack sprayer, a spray tank, a spray plane, or an irrigation system.
• the agrochemical composition is made up with water, buffer, and/or further auxiliaries to the desired application concentration and the ready-to-use spray liquor or the agrochemical composition according to the invention is thus obtained.
• 20 to 2000 liters, preferably 50 to 400 liters, of the ready-to-use spray liquor are applied per hectare of useful agricultural area.
• either individual components of the agrochemical composition according to the invention or partially premixed components e. g. agrochemical components comprising herbicide A, herbicide B, herbicide C, optionally at least one herbicide D (as defined herein) and optionally at least one safener E (as defined herein) may be mixed by the user in a spray tank and further auxiliaries and additives may be added, if appropriate.
• agrochemical components comprising herbicide A, herbicide B, herbicide C, optionally at least one herbicide D (as defined herein) and optionally at least one safener E (as defined herein) may be mixed by the user in a spray tank and further auxiliaries and additives may be added, if appropriate.
• individual components of the agrochemical composition according to the invention such as parts of a kit or parts of a binary or ternary mixture may be mixed by the user himself in a spray tank and further auxiliaries may be added, if appropriate.
• either individual components of the agrochemical composition according to the invention or partially premixed components e. g. components comprising herbicide A, herbicide B, herbicide C, optionally at least one herbicide D (as defined herein) and optionally at least one safener E (as defined herein) can be applied jointly (e.g. after tank mixing) or consecutively.
• the agrochemical composition may be provided in the form of a single package formulation comprising herbicide A, herbicide B, herbicide C, optionally at least one herbicide D (as defined herein) and optionally at least one safener E (as defined herein) together with liquid and/or solid carriers, and, if desired, one or more surfactants and, if desired, one or more further auxiliaries customary in crop protection.
• the formulation may be provided in the form of a two package formulation, wherein one package comprises a formulation of herbicide A, herbicide B and herbicide C while the other package comprises a formulation comprising at least one herbicide D and/or safener E, and wherein both formulations comprise at least one carrier material, if desired, one or more surfactants and, if desired, one or more further auxiliaries customary in crop protection.
• the formulation may also be provided in the form of a two package formulation, wherein one package comprises a formulation of herbicide A, herbicide B and herbicide C and optionally the safener E, while the other package comprises a formulation of the at least one herbicide D, and wherein both formulations comprises at least one carrier material, if desired, one or more surfactants and, if desired, one or more further auxiliaries customary in crop protection.
• the two formulations are preferably mixed prior to application.
• the mixing is performed as a tank mix, i.e. the formulations are mixed immediately prior or upon dilution with water.
• compositions according to the invention control vegetation on non-crop areas very efficiently, especially at high rates of application. They act against broad-leafed weeds and grass weeds in crops such as wheat, barley, rice, corn, sunflowers, soybeans and cotton without causing any significant damage to the crop plants. This effect is mainly observed at low rates of application.
• the compositions according to the invention are applied to the plants mainly by spraying.
• the application can be carried out using, for example, water as carrier by customary spraying techniques using spray liquor amounts of from about 50 to 1000 l/ha (for example from 300 to 400 l/ha).
• the herbicidal compositions may also be applied by the low-volume or the ultra-low- volume method, or in the form of microgranules.
• the herbicidal compositions according to the present invention can be applied pre- or post- emergence or together with the seed of a crop plant. It is also possible to apply the compounds and compositions by applying seed, pretreated with a composition of the invention, of a crop plant. If the herbicides A, B and C and, if appropriate, herbicide D, are less well tolerated by certain crop plants, application techniques may be used in which the herbicidal compositions are sprayed, with the aid of the spraying equipment, in such a way that as far as possible they do not come into contact with the leaves of the sensitive crop plants, while the active compounds reach the leaves of undesirable plants growing underneath, or the bare soil surface (post-directed, lay-by).
• the composition according to the invention can be applied by treating seed.
• the treatment of seed comprises essentially all procedures familiar to the person skilled in the art (seed dressing, seed coating, seed dusting, seed soaking, seed film coating, seed multilayer coating, seed encrusting, seed dripping and seed pelleting) based on compositions according to the invention.
• the herbicidal compositions can be applied diluted or undiluted.
• seed comprises seed of all types, such as, for example, corns, seeds, fruits, tubers, seedlings and similar forms.
• seed describes corns and seeds.
• the seed used can be the seed of the useful plants mentioned above, but also the seed of transgenic plants or plants obtained by customary breeding methods.
• compositions of the present invention may be advantageous to apply on their own or jointly in combination with other crop protection agents, for example with agents for controlling pests or phytopathogenic fungi or bacteria or with groups of active compounds which regulate growth. Also of interest is the miscibility with mineral salt solutions which are employed for treating nutritional and trace element deficiencies. Non-phytotoxic oils and oil concentrates can also be added. When employed in plant protection, the amounts of active substances applied, i.e.
• herbicides A, B and C and, if appropriate, herbicide D, without formulation auxiliaries are, depending on the kind of effect desired, from 0.1 to 10000 grams per hectare (g/ha), preferably 10 to 7500 g/ha, more preferably 25 to 5000 g/ha and in particular 50 to 3000 g/ ha.
• the application rate of the herbicide A is generally from 0.1 to 2000 g/ha, preferably 10 to 1000 g/ha, more preferably 10 to 750 g/ha and in particular 10 to 500 g/ha. In another embodiment, the application rate of the herbicide A is from 50 to 1000 g/ha, preferably 75 to 750 g/ha and more preferably 100 to 500 g/ha.
• the application rate of the herbicide B is generally from 0.1 to 5000 g/ha, preferably 10 to 2000 g/ha, more preferably 10 to 1500 g/ha and in particular 10 to 1000 g/ha. In another embodiment, the application rate of the herbicide B is from 100 to 2000 g/ha, preferably 150 to 1500 g/ha and more preferably 250 to 1000 g/ha.
• the application rate of the herbicide C is generally from 0.1 to 1000 g/ha, preferably 2 to 200 g/ha, more preferably 2 to 150 g/ha and in particular 2 to 50 g/ha.
• the application rate of the herbicide C is from 5 to 150 g/ha, preferably 10 to 50 g/ha.
• the application rate of the herbicide D is generally from 0.1 to 10000 g/ha, preferably 2 to 6400 g/ha, more preferably 2 to 6000 g/ha and in particular 2 to 3000 g/ha.
• the application rate of the herbicide D (in case of salts calculated as the acid) is from 20 to 3000 g/ha.
• the aforementioned application rate is particularly suitable for use in oilseed rape.
• the application rate of the herbicide D (in case of salts calculated as the acid) is from 2 to 3000 g/ha.
• the aforementioned application rate is particularly suitable for use in sunflower.
• the application rate of the herbicide D (in case of salts calculated as the acid) is from 10 to 1800g/ha.
• the aforementioned application rate is particularly suitable for use in cereals (in particular wheat).
• the application rate of the herbicide D is from 2 to 1800 g/ha.
• the aforementioned application rate is particularly suitable for use in legumes.
• the application rate of the herbicide D.137 (quinmerac) is generally from 0.1 to 5000 g/ha, preferably 10 to 1400 g/ha, more preferably 10 to 700 g/ha and in particular 10 to 400 g/ha.
• the application rate of the herbicide D.137 (quinmerac) is from 20 to 1400 g/ha, preferably 45 to 700 g/ha and more preferably 100 to 400 g/ha.
• the application rate of the safener E (in case of salts calculated as the acid) is generally from 1 to 2500 g/ha, preferably 2 to 2000 g/ha and more preferably 10 to 1500 g/ha.
• amounts of active substance of from 0.1 to 5000 g, preferably from 5 to 2500 g, more preferably from 50 to 2000 g and in particular from 100 to 1500 g, per 100 kilogram of plant propagation material (preferably seeds) are generally required.
• the amounts of active substances applied i.e. herbicides A, B and C and, if appropriate, herbicide D are generally employed in amounts of from 0.001 to 10 kg per 100 kg of seed.
• the compositions and methods according to the invention are useful for controlling undesirable vegetation in various crop plants. Examples of suitable crops are the following:
• silvestris (winter turnip rape), Brassica oleracea (cabbage), Brassica nigra (black mustard), Camellia sinensis (tea plants), Carthamus tinctorius (safflower), Carya illinoinensis (pecan trees), Citrus limon (lemons), Citrus sinensis (orange trees), Coffea arabica (Coffea canephora, Coffea liberica) (coffee plants), Cucumis sativus (cucumber), Cynodon dactylon (Bermudagrass), Daucus carota subspec. sativa (carrot), Elaeis guineensis (oil palms), Fragaria vesca
• Gossypium herbaceum Gossypium vitifolium
• Helianthus annuus unsunflowers
• Hevea brasiliensis rubber plants
• Hordeum vulgare barley
• Humulus lupulus hops
• Ipomoea batatas sweet potatoes
• Juglans regia walnut trees
• Lens culinaris lentil
• Preferred crops are Allium cepa, Allium sativum, Arachis hypogaea, Beta vulgaris spec, altissima, Brassica napus var. napus, Brassica oleracea, Cynodon dactylon, Daucus carota subspec.
• Phaseolus lunatus Phaseolus vulgaris, Pisum sativum, Saccharum officinarum, Secale cereale, Solanum tuberosum, Sorghum bicolor (s. vulgare), Triticale, Triticum aestivum, Triticum durum, Vicia faba, Vitis vinifera and Zea mays.
• the crop plant is selected from wheat, barley, rye, oat, triticale, maize, sunflower, rice, legume crops (like soybeans, peas, Vicia-beans, Phaseolus-beans, Vigna- beans, peanuts, chickpeas, lentils, alfalfa, lupins etc.), oilseed rape, canola, cotton, potato, sugarbeet, sugarcane, bulb vegetables (like onion, garlic, shallot, etc), carrot, tomato, brassica vegetable (like cabbage, cauliflower, broccoli, brussel sprouts, curly kale, kohlrabi, etc), leaf vegetable (like salad, lettuce, endive, radicchio, rucola, chicory, etc.), bell pepper, cucumber, eggplant, pumpkin, melon, pepper, zucchini, parsley, parsnip, radish, horseradish, leek, asparagus, celery, artichoke, tobacco, hop, citrus fruits (like orange, lemon, limon, pomelo, grape
• carpetgrass centipedegrass, fescues, kikuyugrass, ryegrass, St. Augustinegrass, zoysiagrass.
• the crop plant is selected from the group consisting of wheat, barley, rye, triticale, oat, corn (maize), sunflower, rice, soybeans, peas, beans, peanuts, oilseed rape, canola, cotton, potato, sugarbeet, sugarcane, turfgrasses and vegetables.
• the crop plant is selected from the group consisting of wheat, barley, rye, triticale, oat, corn (maize), sunflower, rice, soybeans, peas, Vicia-beans, Phaseolus-beans, peanuts, oilseed rape, canola, cotton, potato, sugarbeet, sugarcane, turfgrasses and vegetables.
• the undesirable vegetation is controlled in oilseed rape, sunflower, cereals and legumes.
• the undesirable vegetation is controlled selected from the genus Brassica, in particular oilseed rape.
• the undesirable vegetation is controlled in sunflower.
• the undesirable vegetation is controlled in cereals.
• the cereals are selected from the group consisting of wheat, barley, rye, oat, and triticale (more preferably wheat).
• the undesirable vegetation is controlled in legumes.
• the compositions, uses and methods according to the invention can also be used in genetically modified plants.
• genetically modified plants is to be understood as plants whose genetic material has been modified by the use of recombinant DNA techniques to include an inserted sequence of DNA that is not native to that plant species'genome or to exhibit a deletion of DNA that was native to that species'genome, wherein the modification(s) cannot readily be obtained by cross breeding, mutagenesis or natural recombination alone.
• a particular genetically modified plant will be one that has obtained its genetic modification(s) by inheritance through a natural breeding or propagation process from an ancestral plant whose genome was the one directly treated by use of a recombinant DNA technique.
• one or more genes have been integrated into the genetic material of a genetically modified plant in order to improve certain properties of the plant.
• Such genetic modifications also include but are not limited to targeted post-translational modification of protein(s), oligo- or polypeptides, e. g., by inclusion therein of amino acid mutation(s) that permit, decrease, or promote glycosylation or polymer additions such as prenylation, acetylation farnesylation, or PEG moiety attachment.
• auxinic herbicides such as dicamba or 2,4-D
• bleacher herbicides such as 4-hydroxyphenylpyruvate dioxygenase (HPPD) inhibitors or phytoene desaturase (PDS) inhibitors
• acetolactate synthase (ALS) inhibitors such as sulfonylureas or imidazolinones
• enolpyruvyl shikimate 3-phosphate synthase (EPSP) inhibitors such as glyphosate
• glutamine synthetase (GS) inhibitors such as glufosinate
• protoporphyrinogen-IX oxidase inhibitors lipid biosynthesis inhibitors such as acetylCoA carboxylase (ACCase) inhibitors; or oxynil (i.
• herbicides as a result of conventional methods of breeding or genetic engineering; furthermore, plants have been made resistant to multiple classes of herbicides through multiple genetic modifications, such as resistance to both glyphosate and glufosinate or to both glyphosate and a herbicide from another class such as ALS inhibitors, HPPD inhibitors, auxinic herbicides, or ACCase inhibitors.
• RoundupReady® (glyphosate tolerant, Monsanto, USA), Cultivance® (imidazolinone tolerant, BASF SE, Germany) and LibertyLink® (glufosinate tolerant, Bayer CropScience, Germany).
• plants are also covered that are by the use of recombinant DNA techniques capable to synthesize one or more insecticidal proteins, especially those known from the bacterial genus Bacillus, particularly from Bacillus thuringiensis, such as delta-endotoxins, e. g., CrylA(b), CrylA(c), CrylF, CrylF(a2), CryllA(b), CrylllA, CrylllB(bl ) or Cry9c; vegetative insecticidal proteins (VIP), e. g., VIP1 , VIP2, VIP3 or VIP3A; insecticidal proteins of bacteria colonizing nematodes, e. g., Photorhabdus spp.
• delta-endotoxins e. g., CrylA(b), CrylA(c), CrylF, CrylF(a2), CryllA(b), CrylllA, CrylllB(bl ) or Cry9c
• VIP vegetative insecticid
• toxins produced by animals such as scorpion toxins, arachnid toxins, wasp toxins, or other insect-specific neurotoxins
• toxins produced by fungi such as Streptomycetes toxins, plant lectins, such as pea or barley lectins; agglutinins
• proteinase inhibitors such as trypsin inhibitors, serine protease inhibitors, patatin, cystatin or papain inhibitors
• ribosome-inactivating proteins (RIP) such as ricin, maize-RIP, abrin, luffin, saporin or bryodin
• steroid metabolism enzymes such as 3- hydroxy-steroid oxidase, ecdysteroid-IDP-glycosyl-transferase, cholesterol oxidases, ecdysone inhibitors or HMG-CoA-reductase
• ion channel blockers such as blockers of sodium
• these insecticidal proteins or toxins are to be understood expressly also as including pre-toxins, hybrid proteins, truncated or otherwise modified proteins.
• Hybrid proteins are characterized by a new combination of protein domains, (see, e. g., WO 02/015701 ).
• Further examples of such toxins or genetically modified plants capable of synthesizing such toxins are disclosed, e. g., in EP-A 374 753, WO 93/007278, WO 95/34656, EP-A 427 529, EP-A 451 878, WO 03/18810 und WO 03/52073.
• Plants capable to synthesize one or more insecticidal proteins are, e. g., described in the publications mentioned above, and some of which are commercially available such as YieldGard® (corn cultivars producing the CrylAb toxin), YieldGard® Plus (corn cultivars producing CrylAb and Cry3Bb1 toxins),
• Starlink® corn cultivars producing the Cry9c toxin
• Herculex® RW corn cultivars producing Cry34Ab1 , Cry35Ab1 and the enzyme Phosphinothricin-N-Acetyltransferase [PAT]
• NuCOTN® 33B cotton cultivars producing the CrylAc toxin
• Bollgard® I cotton cultivars producing the CrylAc toxin
• Bollgard® II cotton cultivars producing CrylAc and Cry2Ab2 toxins
• VIPCOT® cotton cultivars producing a VIP-toxin
• NewLeaf® potato cultivars producing the Cry3A toxin
• Bt-Xtra® NatureGard®, KnockOut®, BiteGard®, Protecta®, Bt1 1 (e.
• plants are also covered that are by the use of recombinant DNA techniques capable to synthesize one or more proteins to increase the resistance or tolerance of those plants to bacterial, viral or fungal pathogens.
• proteins are the so-called "pathogenesis-related proteins" (PR proteins, see, e.g., EP-A 392 225), plant disease resistance genes (e. g., potato culti-vars, which express resistance genes acting against Phytophthora infestans derived from the Mexican wild potato, Solanum bulbocastanum) or T4-lyso-zym (e.g., potato cultivars capable of synthesizing these proteins with increased resistance against bacteria such as Erwinia amylovora).
• PR proteins pathogenesis-related proteins
• plant disease resistance genes e. g., potato culti-vars, which express resistance genes acting against Phytophthora infestans derived from the Mexican wild potato, Solanum bulbocastanum
• T4-lyso-zym
• plants are also covered that are by the use of recombinant DNA techniques capable to synthesize one or more proteins to increase the productivity (e.g., bio-mass production, grain yield, starch content, oil content or protein content), tolerance to drought, salinity or other growth-limiting environmental factors or tolerance to pests and fungal, bacterial or viral pathogens of those plants.
• productivity e.g., bio-mass production, grain yield, starch content, oil content or protein content
• tolerance to drought e.g., salinity or other growth-limiting environmental factors or tolerance to pests and fungal, bacterial or viral pathogens of those plants.
• plants are also covered that contain by the use of recombinant DNA techniques a modified amount of ingredients or new ingredients, specifically to improve human or animal nutrition, e. g., oil crops that produce health-promoting long-chain omega-3 fatty acids or unsaturated omega-9 fatty acids (e. g., Nexera® rape, Dow AgroSciences, Canada).
• a modified amount of ingredients or new ingredients specifically to improve human or animal nutrition, e. g., oil crops that produce health-promoting long-chain omega-3 fatty acids or unsaturated omega-9 fatty acids (e. g., Nexera® rape, Dow AgroSciences, Canada).
• plants are also covered that contain by the use of recombinant DNA techniques a modified amount of ingredients or new ingredients, specifically to improve raw material production, e.g., potatoes that produce increased amounts of amylopectin (e.g. Amflora® potato, BASF SE, Germany).
• a modified amount of ingredients or new ingredients specifically to improve raw material production, e.g., potatoes that produce increased amounts of amylopectin (e.g. Amflora® potato, BASF SE, Germany).
• test plants are seeded, separately for each species, in plastic containers in sandy loamy soil containing 5% of organic matter.
• the active compounds suspended or emulsified in water, are applied directly after sowing by means of finely distributing nozzles.
• the containers are irrigated gently to promote germination and growth and subsequently covered with transparent plastic hoods until the plants have rooted. This cover causes uniform germination of the test plants unless this is adversely affected by the active compounds.
• the plants are first grown to the 2 leaf station (GS 12).
• the herbicidal compositions are suspended or emulsified in water as distribution medium and sprayed using finely distributing nozzels.
• the plants are cultivated due to their individual requirements at 10 - 25°C and 20 - 35°C.
• the plants are irrigated due to their necessity.
• the racemic mixture ( ⁇ )-2-exo-(2-Methylbenzyloxy)-1-methyl-4-isopropyl-7- oxabicyclo[2.2.1]heptane may be used as herbicide A and formulated as emulsifiable concentrates with an active ingredient concentration of 50g/l, 100 g/l or 750 g/l respectively.
• Metazachlor (herbicide B) may be used as commercial suspension concentrate (Butisan ® 500) having an active ingredient concentration of 500 g/l.
• Imazamox (herbicide C.1 ) may be used as a water-dispersible granule formulation (70% WG).
• the herbicidal activity for the individual herbicidal compositions can be assessed e.g. 20 days after treatment (DAT).
• the evaluation for the damage on undesired weeds caused by the chemical compositions is carried out using a scale from 0 to 100%, compared to the untreated control plants.
• 0 means no damage
• 100 means complete destruction of the plants.
• the plants used in the greenhouse experiments can be selected, inter alia, from the following species:
• Colby's equation can be applied to determine whether a combination of two active ingredients (e.g. herbicide A and herbicide B) shows a synergistic effect (see S. R. Colby, "Calculating synergistic and antagonistic responses of herbicide combinations", Weeds 1967, 15, pp. 20-22).
• E, X and Y are as defined above and Z is the herbicidal effect in percent using a herbicide C (as defined herein) at an application rate c.
• the value E corresponds to the effect (plant damage or injury) which is to be expected if the activity of the individual compounds is additive. If the observed effect is higher than the value E calculated according to the Colby equation, a synergistic effect is present.

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• 2016
  • 2016-07-06 EA EA201890264A patent/EA201890264A1/ru unknown
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