EP3809849A1 - Verfahren zur bekämpfung von herbizidresistentem oder -tolerantem unkraut - Google Patents

Verfahren zur bekämpfung von herbizidresistentem oder -tolerantem unkraut

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Publication number
EP3809849A1
EP3809849A1 EP19729756.7A EP19729756A EP3809849A1 EP 3809849 A1 EP3809849 A1 EP 3809849A1 EP 19729756 A EP19729756 A EP 19729756A EP 3809849 A1 EP3809849 A1 EP 3809849A1
Authority
EP
European Patent Office
Prior art keywords
methyl
cas
inhibitors
herbicide
salts
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Pending
Application number
EP19729756.7A
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English (en)
French (fr)
Inventor
Helmut Kraus
Matthias Witschel
Bernd Sievernich
Andreas Landes
Gerd Kraemer
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
BASF Agro BV
Original Assignee
BASF Agro BV
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Filing date
Publication date
Application filed by BASF Agro BV filed Critical BASF Agro BV
Publication of EP3809849A1 publication Critical patent/EP3809849A1/de
Pending legal-status Critical Current

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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
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/80—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,2

Definitions

  • the present invention relates to methods and uses for controlling herbicide resistant or tolerant weed species by applying the compound 2-(2,4-dichlorophenyl)methyl-4,4-dimethyl-3-isoxazoli- done of the formula I (herbicide A)
  • the methods and uses are particularly suitable for the protection of crops.
  • herbicide resistance within weeds in particular grass weeds such as, for example, Alopecurus myosuroides (ALOMY), Apera spica-venti (APESV) or Lolium species (LOLSS), but also broadleaf weeds like Amaranthus species (AMASS) and Raphanus species (RAPSS), has become a major concern for farmers, resulting in dramatic weed control problems, for example in cereal crops.
  • Herbicides from the group of EPSP synthase-, ACCase- and ALS-inhibitors are most affected by resistance evolution but also various other types of herbicides.
  • WO 2012/148689 describes the use of at least one 3 -isoxazolidone herbicide selected from the group consisting of 2-(2,4-dichlorophenyl)methyl-4,4-dimethyl-3-isoxazolidone and 2-(2,5-di- chlorophenyl)methyl-4,4-dimethyl-3-isoxazolidone as a selective herbicide in a grass or brassica crop selected from the group consisting of corn, rice, sorghum, barley, rye, and canola.
  • WO 2015/127259 (equivalent to US 2017/042155) describes compositions and uses of at least one 3-isoxazolidinone analog herbicide selected from 2-(2,4-dichlorophenyl)methyl-4,4-dime- thyl-3-isoxazolidinone (“2,4-DC”) and 2-(2,5-dichlorophenyl)methyl-4,4-dimethyl-3-isoxazoli- dinone (“2,5-DC”), including combinations with a second herbicide.
  • 2-(2,4-dichlorophenyl)methyl-4,4-dime- thyl-3-isoxazolidinone 2,4-DC
  • 2-(2,5-dichlorophenyl)methyl-4,4-dimethyl-3-isoxazoli- dinone 2,5-DC
  • WO 2015/127259 or US 2017/042155 also describe a method of controlling undesired vegetation in a crop comprising applying to the locus of such vegetation a herbicidally-effective amount of a compo- sition comprising a first herbicide selected from the group consisting of 2,4- DC and 2,5-DC, wherein the crop may be selected from various crop plants, and the undesired vegetation may be selected from various weed species including herbicide-resistant blackgrass, and a method of controlling undesirable plants and weeds using either 2, 4 DC or 2,5 DC alone against vari- ous weed species including herbicide-resistant black grass.
  • WO 2017/025418 describes the use of herbicidal active compound 2-(2,4-dichlorophenyl)me- thyl-4,4-dimethyl-3-isoxazolidone (referred to as“compound I”) as foliar herbicide, combinations comprising compound I and a method for controlling undesired weeds by applying the corn- pound I or combinations comprising compound I to weeds or to the area in which the weeds grow after emergence of the crop.
  • compound I herbicidal active compound 2-(2,4-dichlorophenyl)me- thyl-4,4-dimethyl-3-isoxazolidone
  • WO 2017/025396 describes herbicidal compositions comprising a component A (i.e. certain te- trazole- or oxadiazol benzamide herbicides referred to as“A1” to“A6”) and a component B (i.e.
  • WO 2018/029031 describes the use of a triazolone-type compound of formula (I), in particular bencarbazone of the formula (1 ).1 or of a herbicidal composition comprising them for controlling PPO resistant weeds.
  • Such herbicidal composition may comprise at least one compound of for- mula (I), at least one further active compound selected from herbicides B and/or safeners C.
  • the further herbicidal compound B is preferably selected from the herbicides of classes b1 ) to b15), inter alia from class b5) (bleacher herbicides). 2-(2,4- dichlorophenyl)methyl-4,4-dimethyl-
  • 3-isoxazolidone is mentioned as an example of bleacher herbicides among various other corn- pounds.
  • WO 2018/041762 discloses a method of reducing crop damage characterized by treating the seed of the crop with a safener before sowing and applying 2-(2,4-dichlorophenyl)methyl-4,4- dimethyl-3-isoxazolidinone or combinations/compositions comprising thereof and optionally a safener in a pre- or post-emergence treatment.
  • WO 2018/119338 describes herbicidal compositions containing a first herbicide beflubutamid, or an optically enriched form thereof, and a second herbicide selected from various groups and a method of controlling undesired vegetation in a crop by applying to the locus of such vegetation a herbicidally effective amount of the herbicidal composition. Further, it is described that the combination of beflubutamid with 2- (2,4-dichlorophenyl)methyl-4,4-dimethyl-3-isoxazolidinone is particularly useful for the control of certain weed species, inter alia the herbicide resistant blackgrass strain (HR3).
  • HR3 herbicide resistant blackgrass strain
  • WO 2018/172442 describes herbicidal mixtures containing i) 2-[(2,4-dichlorophenyl)methyl]-4,4- dimethyl-3-isoxazolidinone and ii) cinmethylin, herbicidal compositions containing said mixtures and the use of said mixtures and compositions in the agricultural field for controlling weeds, in- ter alia herbicide-resistant weeds.
  • an object of the present invention lies in the effective control of herbicide-resistant weed biotypes, especially in herbicide-resistant grass and/or broadleaf weeds.
  • 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 2-(2,4-dichlorophenyl)methyl-4,4-dimethyl-3-isoxazolidone of the formula I (herbicide A)
  • the undesirable vegetation comprises at least one herbicide resistant or tolerant weed species.
  • 2-(2,4-dichlorophenyl)methyl-4,4-dimethyl-3-isoxazolidone of the formula I (herbicide A) is a known herbicidal active compound and may be prepared by processes such as those described in US 4,405,357 (see in particular Example 22).
  • herbase 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 con- trolled, the treated cultivated plant or material, the climatic conditions and the specific composi- tion according to the invention used.
  • plants and “vegetation”, as used herein, include germinant seeds, emerging seed- lings, plants emerging from vegetative propagules, and established vegetation.
  • locus means the area in which the vegetation or plants are growing or will grow, typically a field.
  • the present invention also relates to the use of 2-(2,4-dichlorophenyl)methyl-4,4-dimethyl-3- isoxazolidone of the formula I (herbicide A)
  • the use or method of the invention may further comprise applying at least one herbicide B (as defined hereinafter) which is different from the herbicide A.
  • a herbicidal composition comprising a) the herbicide A and b) at least one herbicide B different from herbicide A and may be used or applied in the use or method of this invention.
  • the method of the invention may further comprise applying at least one safener C (as defined herein).
  • the present invention relates to the use of a herbicidal composition
  • a herbicidal composition comprising a) the herbicide A, b) a herbicide B which is pyroxasulfone and optionally c) at least one safener C (as defined herein) as a post-emergence herbicide.
  • the present invention relates to a method for controlling undesirable vegetation which comprises applying to the vegetation or the locus thereof a herbicidal composition comprising a) the herbicide A, b) a herbicide B which is pyroxasulfone and optionally c) at least one safener C (as defined herein), wherein the herbicidal composition is applied after emergence of the undesirable vegetation.
  • herbicidal compound 2-(2,4-dichlorophenyl)methyl-4,4- dimethyl-3-isoxazolidone of the formula I provides effective control of herbicide re- sistant or tolerant weed species, in particular herbicide-resistant weed biotypes.
  • herbicide A can effectively control herbicide-resistant grass weeds such as, for example, Alo- pecurus myosuroides (ALOMY), Apera spica-venti (APESV), Avena fatua (AVEFA), Bromus species (BROSS), Phalaris species (PHASS), Poa annua (POAAN) or Lolium species (LOLSS).
  • Herbicide A is also suitable for controlling herbicide-resistant broadleaf weeds such as, for ex- ample, Papaver rhoeas (PAPRH, corn poppy) or Raphanus raphanistrum (RAPRA) or which have evolved resistance, especially against EPSP synthase-, ALS-, ACCase- or VLCFA-inhibit- ing herbicides.
  • herbicide-resistant broadleaf weeds such as, for ex- ample, Papaver rhoeas (PAPRH, corn poppy) or Raphanus raphanistrum (RAPRA) or which have evolved resistance, especially against EPSP synthase-, ALS-, ACCase- or VLCFA-inhibit- ing herbicides.
  • herbicide A can be used for controlling weed bio- types with target-site resistance but also weed biotypes with non-target site resistance.
  • a partic- ular advantage of the invention is that herbicide A also provides effective control of weed bio- types having both target-site resistance and non-target-site resistance, such as e.g. resistant populations of Alopecurus myosuroides (ALOMY), Lolium rigidum (LOLRI) or Raphanus raphanistrum (RAPRA).
  • Target-site resistance occurs by mutation within a gene coding for an herbi- cide target-site enzyme (limiting the herbicide binding) or by overproduction of the target en- zyme (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, in- creased herbicide sequestration, or enhanced herbicide metabolism).
  • 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-hydroxy- phenyl-pyruvate-dioxygenase (HPPD) inhibitors (HRAC Group F1), phytoene desaturase (PDS) inhibitors (HRAC Group F2), carotenoid biosynthesis inhibitors (HRAC Group F3), DOXP syn- thase inhibitors (HRAC Group F4), 5-enolpymvylshikimate-3-phosphate (EPSP) inhibitors
  • 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-hyd roxyphenyl-pyruvate-d ioxygenase (HPPD) inhibitors (HRAC Group F1), phytoene desaturase (PDS) inhibitors (HRAC Group F2), 5- enolpymvylshikimate-3-phosphate (EPSP) inhibitors (HRAC Group G), glutamine synthetase inhibitors (HRAC Group H), inhibitors of microtubuli assembly (HRAC Group K1), very long chain fatty acid (VLCFA
  • 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), 5-enolpymvylshikimate-3- phosphate (EPSP) inhibitors (HRAC Group G), glutamine synthetase inhibitors (HRAC Group H), 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 acetolactate synthase
  • 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), photosystem II (PS II) inhibitors (HRAC Groups C1 , C2 and C3), 5- enolpymvylshikimate-3-phosphate (EPSP) inhibitors (HRAC Group G), glutamine synthetase inhibitors (HRAC Group H), inhibitors of microtubuli assembly (HRAC Group K1 ) and very long chain fatty acid (VLCFA) inhibitors (HRAC Group K3).
  • ACCase acetyl CoA carboxylase
  • ALS acetolactate synthase
  • PS II photosystem II
  • HRAC Groups C1 , C2 and C3 5- enolpymvylshikimate-3-phosphate
  • 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), photosystem II (PS II) inhibitors (HRAC Groups C1 , C2 and C3), inhibitors of microtubuli assembly (HRAC Group K1 ) and very long chain fatty acid (VLCFA) inhibitors (HRAC Group K3).
  • ACCase acetyl CoA carboxylase
  • ALS acetolactate synthase
  • PS II photosystem II
  • HRAC Group K1 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 acetyl CoA carboxylase (ACCase) inhibitors (HRAC Group A).
  • ACCase acetyl CoA carboxylase
  • the herbicide resistant or tolerant weed species is selected from biotypes with resistance or tolerance to at least one herbicide selected from acetolactate synthase (ALS) inhibitors (HRAC Group B).
  • ALS acetolactate synthase
  • the herbicide resistant or tolerant weed species is selected from biotypes with resistance or tolerance to at least one herbicide selected from photosystem II (PS II) inhibitors (HRAC Groups C1 , C2 and C3).
  • PS II photosystem II
  • the herbicide resistant or tolerant weed species is selected from biotypes with resistance or tolerance to at least one herbicide selected from 5- enolpymvylshikimate-3-phosphate (EPSP) inhibitors (HRAC Group G).
  • EPP 5- enolpymvylshikimate-3-phosphate
  • the herbicide resistant or tolerant weed species is selected from biotypes with resistance or tolerance to at least one herbicide selected from glutamine synthetase inhibitors (HRAC Group H).
  • the herbicide resistant or tolerant weed species is selected from biotypes with resistance or tolerance to at least one herbicide selected from inhibitors of microtubuli assembly (HRAC Group K1 ) and very long chain fatty acid (VLCFA) inhibitors (HRAC Group K3).
  • HRAC Group K1 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 very long chain fatty acid (VLCFA) inhibitors (HRAC Group K3).
  • VLCFA very long chain fatty acid
  • the herbicide resistant or tolerant weed species is selected from the genera Agropyron, Alopecurus, Apera, Avena, Brachiaria, Bromus, Cynodon, Digitaria, Echi- sangloa, Eleusine, Ischaemum, Leptochloa, Lolium, Panicum, Phalaris, Poa, Rottboellia, Setaria, Anthemis, Amaranthus, Ambrosia, Capsella, Centaurea, Chenopodium, Commelina, Conyza, Descurainia, Galium, Kochia, Matricaria, Papaver, Raphanus, Sinapis, Sisymbrium, Stellaria and Thlaspi, preferably selected from the genera Alopecurus, Apera, Avena, Lolium, Phalaris, Poa, Commelina, Papaver and Raphanus, more preferably selected from the genera Alopecurus, Apera, Avena, Lolium, Phalaris, Poa, Papaver
  • the herbicide resistant or tolerant weed species is selected from the genera Agropyron, Apera, Avena, Brachiaria, Bromus, Cynodon, Digitaria, Echinochloa, Eleu- sine, Ischaemum, Leptochloa, Lolium, Panicum, Phalaris, Poa, Rottboellia, Setaria, Anthemis, Amaranthus, Ambrosia, Capsella, Centaurea, Chenopodium, Commelina, Conyza, Descurainia, Galium, Kochia, Matricaria, Papaver, Raphanus, Sinapis, Sisymbrium, Stellaria and Thlaspi, preferably selected from the genera Apera, Avena, Lolium, Phalaris, Poa, Commelina, Papaver and Raphanus, more preferably selected from the genera Apera, Avena, Lolium, Phalaris, Poa, Papaver and Raphanus and even more preferably selected from the genera Agropyron
  • the herbicide resistant or tolerant weed species is a monocotyledonous weed species selected from the genera Agropyron, Alopecurus, Apera, Avena, Brachiaria, Bro- mus, Cynodon, Digitaria, Echinochloa, Eleusine, Ischaemum, Leptochloa, Lolium, Panicum, Phalaris, Poa, Rottboellia and Setaria, preferably selected from the genera Alopecurus, Apera, Avena, Bromus, Lolium, Phalaris and Poa, more preferably selected from the genera Alopecu- rus, Apera, Avena, Lolium, Phalaris and Poa and even more preferably selected from the gen- era Alopecurus, Avena, and Lolium.
  • the herbicide resistant or tolerant weed species is selected from the genera Alopecurus and Lolium.
  • the herbicide resistant or tolerant weed species is a monocotyledonous weed species selected from the genera Agropyron, Apera, Avena, Brachiaria, Bromus, Cyno- don, Digitaria, Echinochloa, Eleusine, Ischaemum, Leptochloa, Lolium, Panicum, Phalaris, Poa, Rottboellia and Setaria, preferably selected from the genera Apera, Avena, Bromus, Lolium, Phalaris and Poa, more preferably selected from the genera Apera, Avena, Lolium, Phalaris and Poa and even more preferably selected from the genera Avena and Lolium.
  • the herbicide resistant or tolerant weed species is selected from the ge- nus Alopecurus.
  • the herbicide resistant or tolerant weed species is selected from the ge- nus Apera.
  • the herbicide resistant or tolerant weed species is selected from the ge- nus Avena.
  • the herbicide resistant or tolerant weed species is selected from the ge- nus Bromus.
  • the herbicide resistant or tolerant weed species is selected from the ge- nus Lolium.
  • the herbicide resistant or tolerant weed species is selected from the ge- nus Phalaris.
  • the herbicide resistant or tolerant weed species is selected from the ge- nus Poa.
  • the herbicide resistant or tolerant weed species is a dicotyledonous weed species, preferably a dicotyledonous weed species selected from the genera Anthemis, Amaranthus, Ambrosia, Capsella, Centaurea, Chenopodium, Commelina, Conyza, Descurainia, Galium, Kochia, Matricaria, Papaver, Raphanus, Sinapis, Sisymbrium, Stellaria and Thlaspi, preferably selected from the genera Commelina, Papaver and Raphanus, more preferably from the genera Papaver and Raphanus and in particular selected from the genus Raphanus.
  • the herbicide resistant or tolerant weed species is selected from the genus Papaver.
  • the herbicide resistant or tolerant weed species is selected from the genus Commelina.
  • the herbicide resistant or tolerant weed species is selected from the group consist- ing of Alopecurus myosuroides, Alopecurus aequalis, Apera spica-venti, Avena fatua, Avena sterilis, Brachiaria plantaginea, Brachiaria decumbens, Bromus secalinus, Bromus sterilis, Bro- mus 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, Lepto- chloa chinensis, Leptochloa panicoides, L
  • the herbicide resistant or tolerant weed species is selected from the group consisting of Alopecurus myosuroides and Alopecurus aequalis. In another embodiment, the herbicide resistant or tolerant weed species is Alopecurus myosuroides. In another embodi- ment, the herbicide resistant or tolerant weed species is Alopecurus aequalis. In another embodiment, the herbicide resistant or tolerant weed species is Apera spica-venti.
  • the herbicide resistant or tolerant weed species is selected from the group consisting of Avena fatua and Avena sterilis. In another embodiment, the herbicide resistant or tolerant weed species is Avena fatua. In another embodiment, the herbicide resistant or tolerant weed species is Avena sterilis.
  • the herbicide resistant or tolerant weed species is selected from the group consisting of Lolium multiflorum, Lolium perenne, Lolium rigidum and Lolium x hybridum, preferably from the group consisting of Lolium multiflorum, Lolium rigidum and Lolium x hybridum. In another embodiment, the herbicide resistant or tolerant weed species is Lolium multiflorum.
  • the herbicide resistant or tolerant weed species is Lolium perenne.
  • the herbicide resistant or tolerant weed species is Lolium rigidum.
  • the herbicide resistant or tolerant weed species is Lolium x hybridum.
  • the herbicide resistant or tolerant weed species is selected from the group consisting of Phalaris brachystachyx, Phalaris minor and Phalaris paradoxa.
  • the herbicide resistant or tolerant weed species is Phalaris bra- chystachyx.
  • the herbicide resistant or tolerant weed species is Phalaris minor.
  • the herbicide resistant or tolerant weed species is Phalaris paradoxa.
  • the herbicide resistant or tolerant weed species is selected from the group consisting of Poa annua, Poa pratensis and Poa trivialis.
  • the herbicide resistant or tolerant weed species is Poa annua.
  • the herbicide resistant or tolerant weed species is Poa pratensis.
  • the herbicide resistant or tolerant weed species is Poa trivialis.
  • the herbicide resistant or tolerant weed species is Commelina bengha- lensis.
  • the herbicide resistant or tolerant weed species is Papaver rhoeas.
  • the herbicide resistant or tolerant weed species is Raphanus raphan- istrum.
  • the herbicide resistant or tolerant weed species is selected from the group consisting of Apera spica-venti, Avena fatua, Avena sterilis, Brachiaria plantaginea, Bra- Canalia decumbens, Bromus secalinus, Bromus sterilis, Bromus tectorum, Digitaria ciliaris, Digi- taria 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 pani- coides, Leptochloa scabra, Leptochloa virgata
  • Raphanus raphanistrum even more preferably selected from the group consisting of Avena fatua, Avena sterilis, Lolium multiflorum, Lolium perenne, Lolium rigidum, Lolium x hybridum and Raphanus raphanistrum, in particular selected from the group consisting of Lolium multiflo- rum, Lolium perenne, Lolium rigidum and Lolium x hybridum.
  • the herbicide resistant or tolerant weed species is a monocotyledonous weed species selected from the group consisting of Alopecurus myosuroides, Alopecurus aequalis, Apera spica-venti, Avena fatua, Avena sterilis, Brachiaria plantaginea, Brachiaria de- cumbens, Bromus secalinus, Bromus sterilis, Bromus tectorum, Digitaria ciliaris, Digitaria insu- laris, Digitaria ischaemum, Digitaria sanguinalis, Echinochloa colona, Echinochloa crus-galli, Echinochloa crus-pavonis, Echinochloa erecta, Echinochloa oryzoides, Echinochloa phyllogo- gon, Eleusine indica, Ischaemum rugosum, Leptochloa chinensis,
  • the herbicide resistant or tolerant weed species is a monocotyledonous weed species selected from the group consisting of Apera spica-venti, Avena fatua, Avena steri- lis, Brachiaria plantaginea, Brachiaria decumbens, Bromus secalinus, Bromus sterilis, Bromus tectorum, Digitaria ciliaris, Digitaria insularis, Digitaria ischaemum, Digitaria sanguinalis, Echi- sangloa colona, Echinochloa crus-galli, Echinochloa crus-pavonis, Echinochloa erecta, Echi- sangloa oryzoides, Echinochloa phyllogogon, Eleusine indica, Ischaemum rugosum, Leptochloa chinensis, Leptochloa panicoides, Leptochloa scabra,
  • Poa trivialis Rottboellia exaltata, Setaria faberi, Setaria glauca, Setaria pumila, Setaria verticil- late and Setaria viridis, preferably selected from the group consisting of Apera spica-venti, Av- ena fatua, Avena sterilis, Lolium multiflorum, Lolium perenne, Lolium rigidum, Lolium x hy- bridum, Phalaris brachystachyx, Phalaris minor, Phalaris paradoxa, Poa annua, Poa pratensis and Poa trivialis, more preferably selected from the group consisting of Avena fatua, Avena sterilis, Lolium multiflorum, Lolium perenne, Lolium rigidum and Lolium x hybridum, even more preferably selected from the group consisting of Lolium multiflorum, Lolium rigidum and Lolium x hybridum .
  • the herbicide resistant or tolerant weed species is a dicotyledonous weed species selected from the genera Amaranthus albus, Amaranthus blitoides, Amaranthus hybridus, Amaranthus palmeri, Amaranthus powellii, Amaranthus retroflexus, Amaranthus tu- berculatus, Amaranthus rudis, Amaranthus viridis, Ambrosia artemisifolia, Anthemis arvensis, Capsella bursa-pastoris, Centaurea cyanus, Chenopodium album, Chenopodium ficifolium, Chenopodium polyspermum, Chenopodium hybridum, Commelina benghalensis, Conyza bon- ariensis, Conyza canadensis, Descurania sophia, Galium aparine, Galium spurium, Galium tri- cornutum, Kochia scoparia, Matricaria chamomilla, Matricaria discoidea, Ma
  • the methods and uses of this invention are suitable for controlling ACCase-re- sistant 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 steri lis, Bromus tectorum, Digitaria ciliaris, Digitaria insularis, Digitaria ischaemum, Digitaria sangui- nalis, Echinochloa colona, Echinochloa crus-galli, Echinochloa crus-pavonis, Echinochloa erecta, Echinochloa oryzoides, Echinochloa phyllogogon, Eleusine indica, Ischae, A
  • the methods and uses of this invention are 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 tec- torum, Digitaria ciliaris, Digitaria insularis, Digitaria ischaemum, Digitaria sanguinalis, Echi- sangloa colona, Echinochloa crus-galli, Echinochloa crus-pavonis, Echinochloa erecta, Echi- sangloa oryzoides, Echinochloa phyllogogon, Eleusine indica, Ischaemum rugosum, Leptochloa chinen
  • Poa trivialis Rottboellia exaltata, Setaria faberi, Setaria glauca, Setaria pumila, Setaria verticil lata and Setaria viridis, preferably selected from the group consisting of Alopecurus myosu- roides, Alopecurus aequalis, Apera spica-venti, Avena fatua, Avena sterilis, Lolium multiflorum, Lolium perenne, Lolium rigidum, Lolium x hybridum, Phalaris brachystachys, Phalaris minor, Phalaris paradoxa, Poa annua and Poa trivialis, more preferably selected from the group con- sisting of Alopecurus myosuroides, Alopecurus aequalis, Avena fatua, Avena sterilis, Lolium multiflorum, Lolium perenne, Lolium rigidum and Lolium x hybridum, especially preferably se- l
  • 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 steri- lis, Brachiaria plantaginea, Brachiaria decumbens, Bromus secalinus, Bromus sterilis, Bromus tectorum, Digitaria ciliaris, Digitaria insularis, Digitaria ischaemum, Digitaria sanguinalis, Echi- sangloa colona, Echinochloa crus-galli, Echinochloa crus-pavonis, Echinochloa erecta, Echi- sangloa oryzoides, Echinochloa phyllogogon, Eleusine indica, Ischaemum rugosum, Leptochl
  • Poa trivialis Rottboellia exaltata, Setaria faberi, Setaria glauca, Setaria pumila, Setaria verticil- lata and Setaria viridis, preferably selected from the group consisting of Alopecurus myosu- roides, Alopecurus aequalis, Apera spica-venti, Avena fatua, Avena sterilis, Lolium multiflorum, Lolium perenne, Lolium rigidum, Lolium x hybridum, Phalaris brachystachys, Phalaris minor, Phalaris paradoxa, Poa annua and Poa trivialis, more preferably selected from the group con- sisting of Alopecurus myosuroides, Alopecurus aequalis, Avena fatua, Avena sterilis, Lolium multiflorum, Lolium perenne, Lolium rigidum and Lolium x hybridum, especially preferably se-
  • HRAC Group G- resistant grass weeds more specifically HRAC Group G-resistant grass weeds selected from the group consisting of Alopecurus myosuroides, Alopecurus aequalis, Apera spica-venti, Av- ena fatua, Avena sterilis, Brachiaria plantaginea, Brachiaria decumbens, Bromus secalinus, Bromus sterilis, Bromus tectorum, Digitaria ciliaris, Digitaria insularis, Digitaria ischaemum, Digi- taria sanguinalis, Echinochloa colona, Echinochloa crus-galli, Echinochloa crus-pavonis, Echi- sangloa erecta, Echinochloa oryzoides, Echinochloa phyllogogon, Eleusine indica, Ischaemum rugosum, L
  • HRAC Group H- resistant grass weeds more specifically HRAC Group H-resistant grass weeds selected from the group consisting of Alopecurus myosuroides, Alopecurus aequalis, Apera spica-venti, Av- ena fatua, Avena sterilis, Brachiaria plantaginea, Brachiaria decumbens, Bromus secalinus, Bromus sterilis, Bromus tectorum, Digitaria ciliaris, Digitaria insularis, Digitaria ischaemum, Digi taria sanguinalis, Echinochloa colona, Echinochloa crus-galli, Echinochloa crus-pavonis, Echi- sangloa erecta, Echinochloa oryzoides, Echinochloa phyllogogon, Eleusine indica, Ischaemum rugosum, Lept
  • HRAC Group K1 -resistant grass weeds more specifically HRAC Group K1 -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, Digi- taria sanguinalis, Echinochloa colona, Echinochloa crus-galli, Echinochloa crus-pavonis, Echi- sangloa erecta, Echinochloa oryzoides, Echinochloa phyllogogon, Eleusine indica, Ischaemum rugosum,
  • HRAC Group K3-resistant grass weeds more specifically HRAC Group K3-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, Digi- taria sanguinalis, Echinochloa colona, Echinochloa crus-galli, Echinochloa crus-pavonis, Echi- sangloa erecta, Echinochloa oryzoides, Echinochloa phyllogogon, Eleusine indica, Ischaemum rugosum, Lept
  • the methods and uses of this invention are suitable for controlling broadleaf weeds having resistance to herbicides selected from the group consisting of 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), 5-enolpymvylshikimate-3- phosphate (EPSP) inhibitors (HRAC Group G), glutamine synthetase inhibitors (HRAC Group H), inhibitors of microtubuli assembly (HRAC Group K1 ) and inhibitors of lipid synthesis (HRAC Group N).
  • ALS acetolactate synthase
  • PS II photosystem II
  • PPO protoporphyrinogen oxidase
  • E 5-enolpymvylshikimate-3- phosphate
  • E 5-enolpymvylshikimate-3- phosphate
  • the herbicide A is applied alone, i.e. the herbicide A is the only herbicidally active ingredient.
  • the herbicide A is applied in combination with at least one herbicide B different from herbicide A.
  • a herbicidal composition comprising a) the herbicide A and b) at least one herbicide B different from herbicide A and is used or applied.
  • the herbicide B may be selected from the groups b1 ) to b15):
  • ALS inhibitors acetolactate synthase inhibitors
  • EBP inhibitors enolpyruvyl shikimate 3-phosphate synthase inhibitors
  • DHP inhibitors 7,8-dihydropteroate synthase inhibitors
  • mitosis inhibitors b8-dihydropteroate synthase inhibitors
  • VLCFA inhibitors inhibitors of the synthesis of very long chain fatty acids
  • herbicides selected from the group consisting of bromobutide, chlorflurenol, chlorflurenol-methyl, cinmethylin, cumyluron, dalapon, dazomet, difenzoquat, dif- enzoquat-metilsulfate, dimethipin, DSMA, dymron, endothal and its salts, etoben- zanid, flamprop, flamprop-isopropyl, flamprop-methyl, flamprop-M-isopropyl, flam- prop-M-methyl, flurenol, flurenol-butyl, flurprimidol, fosamine, fosamine-ammo- nium, indanofan, indaziflam, maleic hydrazide, mefluidide, metam, methiozolin (CAS 403640-27-7), methyl azide, methyl bromide, methyl-dymron,
  • the herbicide B is selected from b1) lipid biosynthesis inhibitors:
  • ACCase inhibitors selected from alloxydim, alloxydim-sodium, butroxydim, clethodim, clodinafop, clodinafop-propargyl, cycloxydim, cyhalofop, cyhalofop-butyl, diclofop, diclofop-me- thyl, fenoxaprop, fenoxaprop-ethyl, fenoxaprop-P, fenoxaprop-P-ethyl, fluazifop, fluazifop-butyl, fluazifop-P, fluazifop-P-butyl, haloxyfop, haloxyfop-methyl, haloxyfop-P, haloxyfop-P-methyl, metamifop, pinoxaden, profoxydim, propaquizafop, quizalofop, quizalofo
  • sulfonylureas selected from amidosulfuron, azimsulfuron, bensulfuron, bensulfuron-methyl, chlorimuron, chlorimuron-ethyl, chlorsulfuron, cinosulfuron, cyclosulfamuron, ethametsulfuron, ethametsulfuron-methyl, ethoxysulfuron, flazasulfuron, flucetosulfuron, flupyrsulfuron, flupyrsul- furon-methyl-sodium, foramsulfuron, halosulfuron, halosulfuron-methyl, imazosulfuron, iodosul- furon, iodosulfuron-methyl-sodium, iofensulfuron, iofensulfuron-sodium, mesosulfuron, met- azosulfuron, metsulfuron, metsulfuron-methyl,
  • imidazolinones selected from imazamethabenz, imazamethabenz-methyl, imazamox, imazapic, imazapyr, imazaquin and imazethapyr, triazolopyrimidine herbicides and sulfonanilides selected from cloransulam, cloransulam-methyl, diclosulam, flumetsulam, florasulam, metosulam, penox- sulam, pyrimisulfan and pyroxsulam,
  • pyrimidinylbenzoates selected from bispyribac, bispyribac-sodium, pyribenzoxim, pyriftalid, py- riminobac, pyriminobac-methyl, pyrithiobac, pyrithiobac-sodium, 4-[[[2-[(4,6-dimethoxy-2-pyrim- idinyl)oxy]phenyl]methyl]amino]-benzoic acid-1 -methylethyl ester (CAS 420138-41-6), 4-[[[2- [(4,6-dimethoxy-2-pyrimidinyl)oxy]phenyl]methyl]amino]-benzoic acid propyl ester (CAS 420138- 40-5), N-(4-bromophenyl)-2-[(4,6-dimethoxy-2-pyrimidinyl)oxy]benzenemethanamine (CAS 420138-01-8),
  • sulfonylaminocarbonyl-triazolinone herbicides selected from flucarbazone, flucarbazone-so- dium, propoxycarbazone, propoxycarbazone-sodium, thiencarbazone and thiencarbazone-me- thyl; and triafamone; b3) photosynthesis inhibitors:
  • inhibitors of the photosystem II selected from 1-(6-tert-butylpyrimidin-4-yl)-2-hy- droxy-4-methoxy-3-methyl-2H-pyrrol-5-one (CAS 1654744-66-7), 1-(5-tert-butylisoxazol-3-yl)-2- hydroxy-4-methoxy-3-methyl-2H-pyrrol-5-one (CAS 1637455-12-9), 1-(5-tert-butylisoxazol-3-yl)- 4-chloro-2-hydroxy-3-methyl-2H-pyrrol-5-one (CAS 1637453-94-1), 1-(5-tert-butyl-1-methyl-py- razol-3-yl)-4-chloro-2-hydroxy-3-methyl-2H-pyrrol-5-one (CAS 1654057-29-0), 1-(5-tert-butyl-1- methyl-pyrazol-3-yl)-3-chloro-2-hydroxy-4-methyl-2H-pyrrol-5-
  • acifluorfen acifluorfen-sodium, azafenidin, bencarbazone, benzfendizone, bifenox, butafenacil, carfentrazone, carfentrazone-ethyl, chlomethoxyfen, chlorphthalim, cinidon-ethyl, cyclopyranil, fluazolate, flufenpyr, flufenpyr-ethyl, flumiclorac, flumiclorac-pentyl, flumioxazin, fluoroglycofen, fluoroglycofen-ethyl, fluthiacet, fluthiacet-methyl, fomesafen, halosafen, lactofen, oxadiargyl, oxadiazon, oxyfluorfen, pentoxazone, profluazol, pyraclonil, pyraflufen, pyraflufen-ethyl, saflufen
  • PDS inhibitors beflubutamid, diflufenican, fluridone, flurochloridone, flurtamone, norflurazon, picolinafen, and 4-(3-trifluoromethylphenoxy)-2-(4-trifluoromethylphenyl)pyrimidine (CAS 180608-33-7), HPPD inhibitors: benzobicyclon, benzofenap, bicyclopyrone, clomazone, fenquinotrione, isoxaflutole, mesotrione, oxotrione (CAS 1486617-21-3), pyrasulfotole, pyrazol- ynate, pyrazoxyfen, sulcotrione, tefuryltrione, tembotrione, tolpyralate, topramezone , bleacher, unknown target: aclonifen, amitrole flumeturon,2-chloro-3-methylsulfanyl-N-(1-methyltetrazol-5
  • bilanaphos (bialaphos), bilanaphos-sodium, glufosinate, glufosinate-P and glufosinate-ammo- nium; b8) DHP synthase inhibitors:
  • compounds of group K1 dinitroanilines selected from benfluralin, butralin, dinitramine, ethalflu- ralin, fluchloralin, oryzalin, pendimethalin, prodiamine and trifluralin, phosphoramidates selected from amiprophos, amiprophos-methyl, and butamiphos, benzoic acid herbicides selected from chlorthal, chlorthal-dimethyl, pyridines selected from dithiopyr and thiazopyr, benzamides se- lected from propyzamide and tebutam; compounds of group K2: carbetamide, chlorpropham, flamprop, flamprop-isopropyl, flamprop-methyl, flamprop-M-isopropyl, flamprop-M-methyl and propham; b10) VLCFA inhibitors:
  • chloroacetamides selected from acetochlor, alachlor, amidochlor, butachlor, dimethachlor, di- methenamid, dimethenamid-P, metazachlor, metolachlor, S-metolachlor, pethoxamid, preti- lachlor, propachlor, propisochlor and thenylchlor, oxyacetanilides selected from flufenacet and mefenacet, acetanilides selected from diphenamid, naproanilide, napropamide and napropa- mide-M, tetrazolinones such fentrazamide, and other herbicides selected from anilofos, cafen- strole, fenoxasulfone, ipfencarbazone, piperophos, pyroxasulfone and isoxazoline compounds of the formulae 11.1 , II.2, II.3, II.4, II.5, II.6, II.7, II.8
  • 2,4-D and its salts and esters selected from clacyfos, 2,4-DB and its salts and esters, aminocy- clopyrachlor and its salts and esters, aminopyralid and its salts selected from aminopyralid-di- methylammonium, aminopyralid-tris(2-hydroxypropyl)ammonium and its esters, benazolin, benazolin-ethyl, chloramben and its salts and esters, clomeprop, clopyralid and its salts and es- ters, dicamba and its salts and esters, dichlorprop and its salts and esters, dichlorprop-P and its salts and esters, flopyrauxifen, fluroxypyr, fluroxypyr-butometyl, fluroxypyr-meptyl, halauxifen and its salts and esters (CAS 943832-60-8); MCPA and its salts and esters, MCPA-thioeth
  • the herbicide B is selected from b1 ) lipid biosynthesis inhibitors: prosulfocarb and triallate; b2) ALS inhibitors: imazamox; b3) photosynthesis inhibitors: metribuzin, terbuthylazin, chlorotoluron and isoproturon; b4) protoporphyrinogen-IX oxidase inhibitors: flumioxazin, saflufenacil, sulfentrazone and triflu- dimoxazin; b5) bleacher herbicides: diflufenican, picolinafen, flurtamone, aclonifen and clomazone; b9) mitosis inhibitors: pendimethalin and trifluralin; b10) VLCFA inhibitors: acetochlor, dimethachlor, dimethenamid, dimethenamid-P, metazachlor, metolachlor, S-metolachlor, petho
  • the use or method of this invention may further comprise applying at least one safener C.
  • the use or method of the present invention comprises applying herbicide A, at least one safener C and optionally at least one herbicide B.
  • the use or method of the present invention comprises applying herbi- cide A, at least one herbicide B and at least one safener C.
  • a composition comprising the herbicide A is applied.
  • a composition comprising the herbicide A and at least one herbicide B is applied.
  • a composition comprising the herbicide A and at least one safener C is applied.
  • a composition comprising the herbicide A, at least one herbicide B (as defined herein) and at least one safener C is applied.
  • 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 un- wanted 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.
  • Suitable safeners are e.g. (quinolin-8-oxy)acetic acids, 1 -phenyl-5-haloalkyl-1 H-1 ,2,4-triazol-3- carboxylic acids, 1 -phenyl-4, 5-d i hyd ro-5-a I kyl- 1 H-pyrazol-3,5-dicarboxylic acids, 4,5-dihydro- 5,5-diaryl-3-isoxazol carboxylic acids, dichloroacetamides, alpha-oximinophenylacetonitriles, acetophenonoximes, 4,6-dihalo-2-phenylpyrimidines, N-[[4-(aminocarbonyl)phenyl]sulfonyl]-2- benzoic amides, 1 ,8-naphthalic anhydride, 2-halo-4-(haloalkyl)-5-thiazol carboxylic acids, phosphorthiolates and N-alkyl
  • the safener C is selected from the group consisting of benoxacor, cloquintocet, cy- ometrinil, cyprosulfamide, dichlormid, dicyclonon, dietholate, fenchlorazole, fenclorim, flurazole, fluxofenim, furilazole, isoxadifen, mefenpyr, mephenate, naphthaleneacetic acid (NAA), naph- thalic anhydride (NA), oxabetrinil, 4-(dichloroacetyl)-1 -oxa-4-azaspiro[4.5]decane (MON4660, CAS 71526-07-3), 2,2,5-trimethyl-3-(dichloroacetyl)-1 ,3-oxazolidine (R-29148, CAS 52836- SI -4), metcamifen, 4-bromophenyl chloromethyl sulfone (BPCMS, CAS 540
  • the safener C is selected from the group consisting of benoxacor, cloquintocet, cyometrinil, cyprosulfamide, dichlormid, dicyclonon, dietholate, fenchlorazole, fenclorim, flu razole, fluxofenim, furilazole, isoxadifen, mefenpyr, mephenate, naphthalic anhydride (NA), oxa- betrinil, 4-(dichloroacetyl)-1 -oxa-4-azaspiro[4.5]decane (MON4660, CAS 71526-07-3), 2,2,5-tri- methyl-3-(dichloroacetyl)-1 ,3-oxazolidine (R-29148, CAS 52836-31 -4), metcamifen, 4-bromo- phenyl chloromethyl sulfone (BPCMS, CAS 54091-06-4) and agriculturally acceptable salts or derivative
  • Especially preferred safeners C are benoxacor, cloquintocet, cyprosulfamide, dichlormid, fenchlorazole, fenclorim, flurazole, fluxofenim, furilazole, isoxadifen, mefenpyr, naphthalic anhy- dride (NA), oxabetrinil, 4-(dichloroacetyl)-1 -oxa-4-azaspiro[4.5]decane (MON4660, CAS 71526- 07-3), 2, 2, 5-trimethyl-3-(dichloroacetyl)-1 ,3-oxazolidine (R-29148, CAS 52836-31 -4), metcam- ifen and agriculturally acceptable salts or derivatives thereof.
  • Particularly preferred safeners C are benoxacor, cloquintocet, cyprosulfamide, dichlormid, fenchlorazole, fenclorim, furilazole, isoxadifen, mefenpyr, naphthalic anhydride (NA), 4-(dichlo- roacetyl)-1 -oxa-4-azaspiro[4.5]decane (MON4660, CAS 71526-07-3), 2,2,5-trimethyl-3-(dichlo- roacetyl)-1 ,3-oxazolidine (R-29148, CAS 52836-31 -4), metcamifen and agriculturally acceptable salts or derivatives thereof.
  • the herbicides B and safeners C are known herbicides and safeners, see, for example, The Pesticide Manual, British Crop Protection Council, 16 th edition, 2012; The Compendium of Pesti- cide 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 Handbook, 7th edi tion, Weed Science Society of America, 1994; and K. K.
  • the allocation of the active compounds to the respective modes of action is based on current knowledge. If several modes of action apply to one active compound, this compound was only allocated to one mode of action.
  • herbicides B and/or safeners C 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 methods and uses according to the invention.
  • herbicides B and/or safeners C 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 methods and uses according to the invention.
  • herbicides B and/or safeners C as described herein have ionizable functional groups, they can also be employed in the form of their agriculturally acceptable salts.
  • the term“agriculturally acceptable salts” is used herein to mean in general, the salts of those cations and the acid addi- tion 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-C 4 -alkyl, hydroxy-Ci-C 4 -alkyl, Ci-C 4 - alkoxy-Ci-C 4 -alkyl, hydroxy-Ci-C 4 -alkoxy-Ci-C 4 -alkyl, phenyl or benzyl, preferably ammonium, methylammonium, isopropylammonium, dimethylammonium, diisopropylammonium, trime- thylammonium, heptylammonium, dodecylammonium, tetradecylammonium, tetramethylammo- nium,
  • Anions of useful acid addition salts are primarily chloride, bromide, fluoride, iodide, hydrogensul- fate, methylsulfate, sulfate, dihydrogenphosphate, hydrogenphosphate, nitrate, bicarbonate, carbonate, hexafluorosilicate, hexafluorophosphate, benzoate and also the anions of Ci-C 4 -al- kanoic acids, preferably formate, acetate, propionate and butyrate.
  • the herbicides B and/or safeners C as described herein having a carboxyl, hydroxy and/or an lamino 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 exam- pie as amides, such as mono- and di-Ci-C 6 -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-C 6 -alkylamides or arylamides
  • esters for example as allyl esters, propargyl esters, Ci-Cio-alkyl esters
  • Preferred mono- and di-Ci-C 6 -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-methoxy- ethyl, 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.
  • suitable salts include those, where the counterion is an agriculturally ac- ceptable cation.
  • suitable salts of dicamba are dicamba-sodium, dicamba-potas- sium, dicamba-methylammonium, dicamba-dimethylammonium, dicamba-isopropylammonium, dicamba-diglycolamine, dicamba-olamine, dicamba-diolamine, dicamba-trolamine, dicamba- N,N-bis-(3-aminopropyl)methylamine and dicamba-diethylenetriamine.
  • a suitable ester are dicamba-methyl and dicamba-butotyl.
  • Suitable salts of 2,4-D are 2,4-D-ammonium, 2,4-D-dimethylammonium, 2,4-D-diethylammo- nium, 2,4-D-diethanolammonium (2,4-D-diolamine), 2,4-D-triethanolammonium, 2,4-D-isoprop- ylammonium, 2,4-D-triisopropanolammonium, 2,4-D-heptylammonium, 2,4-D-dodecylammo- nium, 2,4-D-tetradecylammonium, 2,4-D-triethylammonium, 2,4-D-tris(2-hydroxypropyl)ammo- nium, 2,4-D-tris(isopropyl)ammonium, 2,4-D-trolamine, 2,4-D-lithium, 2,4-D-sodium and 2,4-D- N,N,N-trimethylethanolammonium
  • esters of 2,4-D are 2,4- D-butotyl, 2,4-D-2-butoxypropyl, 2,4-D-3-butoxypropyl, 2,4-D-butyl, 2,4-D-ethyl, 2,4-D- ethylhexyl, 2,4-D-isobutyl, 2,4-D-isooctyl, 2,4-D-isopropyl, 2,4-D-meptyl, 2,4-D-methyl, 2,4-D- octyl, 2,4-D-pentyl, 2,4-D-propyl, 2,4-D-tefuryl and clacyfos.
  • Suitable salts of 2,4-DB are for example 2,4-DB-sodium, 2,4-DB-potassium and 2,4-DB-dime- thylammonium.
  • Suitable esters of 2,4-DB are for example 2,4-DB-butyl and 2,4-DB-isoctyl.
  • Suitable salts of dichlorprop are for example dichlorprop-sodium, dichlorprop-potassium and di- chlorprop-dimethylammonium. Examples of suitable esters of dichlorprop are dichlorprop-buto- tyl and dichlorprop-isoctyl.
  • Suitable salts and esters of MCPA include MCPA-butotyl, MCPA-butyl, MCPA-dimethylammo- nium, MCPA-diolamine, MCPA-ethyl, MCPA-thioethyl, MCPA-2-ethylhexyl, MCPA-isobutyl, MCPA-isoctyl, MCPA-isopropyl, MCPA-isopropylammonium, MCPA-methyl, MCPA-olamine, MCPA-potassium, MCPA-sodium and MCPA-trolamine.
  • a suitable salt of MCPB is MCPB sodium.
  • a suitable ester of MCPB is MCPB-ethyl.
  • Suitable salts of clopyralid are clopyralid-potassium, clopyralid-olamine and clopyralid-tris-(2- hydroxypropyl)ammonium.
  • Example of suitable esters of clopyralid is clopyralid-methyl.
  • Examples of a suitable ester of fluroxypyr are fluroxypyr-meptyl and fluroxypyr-2-butoxy-1-meth- ylethyl, wherein fluroxypyr-meptyl is preferred.
  • Suitable salts of picloram are picloram-dimethylammonium, picloram-potassium, picloram-triiso- propanolammonium, picloram-triisopropylammonium and picloram-trolamine.
  • a suitable ester of picloram is picloram-isoctyl.
  • a suitable salt of triclopyr is triclopyr-triethylammonium.
  • Suitable esters of triclopyr are for exam- pie triclopyr-ethyl and triclopyr-butotyl.
  • Suitable salts and esters of chloramben include chloramben-ammonium, chloramben-diolamine, chloramben-methyl, chloramben-methylammonium and chloramben-sodium.
  • Suitable salts and esters of 2,3,6-TBA include 2,3,6-TBA-dimethylammonium, 2,3,6-TBA-lithium, 2,3,6-TBA-potas- sium and 2,3,6-TBA-sodium.
  • Suitable salts and esters of aminopyralid include aminopyralid-potassium and aminopyralid- tris(2-hydroxypropyl)ammonium.
  • Suitable salts of glyphosate are for example glyphosate-ammonium, glyphosate-diammonium, glyphoste-dimethylammonium, glyphosate-isopropylammonium, glyphosate-potassium, glypho- sate-sodium, glyphosate-trimesium as well as the ethanolamine and diethanolamine salts, pref- erably glyphosate-diammonium, glyphosate-isopropylammonium and glyphosate-trimesium (sulfosate).
  • a suitable salt of glufosinate is for example glufosinate-ammonium.
  • a suitable salt of glufosinate-P is for example glufosinate-P-ammonium.
  • Suitable salts and esters of bromoxynil are for example bromoxynil-butyrate, bromoxynil-hep- tanoate, bromoxynil-octanoate, bromoxynil-potassium and bromoxynil-sodium.
  • Suitable salts and esters of ioxonil are for example ioxonil-octanoate, ioxonil-potassium and iox- onil-sodium.
  • Suitable salts and esters of mecoprop include mecoprop-butotyl, mecoprop-dimethylammonium, mecoprop-diolamine, mecoprop-ethadyl, mecoprop-2-ethylhexyl, mecoprop-isoctyl, mecoprop- methyl, mecoprop-potassium, mecoprop-sodium and mecoprop-trolamine.
  • Suitable salts of mecoprop-P are for example mecoprop-P-butotyl, mecoprop-P-dimethylammo- nium, mecoprop-P-2-ethylhexyl, mecoprop-P-isobutyl, mecoprop-P-potassium and mecoprop-P- sodium.
  • a suitable salt of diflufenzopyr is for example diflufenzopyr-sodium.
  • a suitable salt of naptalam is for example naptalam-sodium.
  • Suitable salts and esters of aminocyclopyrachlor are for example aminocyclopyrachlor-dime- thylammonium, aminocyclopyrachlor-methyl, aminocyclopyrachlor-triisopropanolammonium, aminocyclopyrachlor-sodium and aminocyclopyrachlor-potassium.
  • a suitable salt of quinclorac is for example quinclorac-dimethylammonium.
  • a suitable salt of quinmerac is for example quinclorac-dimethylammonium.
  • a suitable salt of imazamox is for example imazamox-ammonium.
  • Suitable salts of imazapic are for example imazapic-ammonium and imazapic-isopropylammo- mum.
  • Suitable salts of imazapyr are for example imazapyr-ammonium and imazapyr-isopropylammo- nium.
  • a suitable salt of imazaquin is for example imazaquin-ammonium.
  • Suitable salts of imazethapyr are for example imazethapyr-ammonium and imazethapyr-iso- propylammonium.
  • a suitable salt of topramezone is for example topramezone-sodium.
  • compositions may further comprise one or more auxiliaries customary in crop protection (as defined herein).
  • herbicide A and herbicide B may also be capable of providing a synergistic herbicidal effect.
  • the herbicide A and herbicide B are each present or applied in an amount sufficient to provide a synergistic herbi- cidal effect.
  • compositions can, based on the individual components, be used at lower application rates to achieve a herbi- cidal effect comparable to the individual components.
  • Colby's equation is applied to determine whether the combination of herbicide A and herbicide B shows a synergistic effect (see S. R. Colby, "Calcu- lating synergistic and antagonistic responses of herbicide combinations", Weeds 1967, 15, pp. 20-22).
  • 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 pre- sent.
  • the composition comprising herbicide A and the at least one herbicide B is synergistic as determined by the Colby equation. Specifically, the syner- gistic herbicidal effect is determined according to the Colby equation.
  • the weight ratio of herbicide A to herbicide B is gener- ally in the range of from 1 :1000 to 1000:1 , preferably in the range of from 1 :500 to 500:1 , in par- ticular in the range of from 1 :250 to 250:1 and particularly preferably in the range of from 1 :75 to 75:1 , wherein each herbicide B being an ester or a salt of an acid is calculated as the acid.
  • the weight ratio of herbicide A to safener C is gener- ally in the range of from 1 :1000 to 1000:1 , preferably in the range of from 1 :500 to 500:1 , in par- ticular in the range of from 1 :250 to 250:1 and particularly preferably in the range of from 1 :75 to 75:1 , wherein each safener C being an ester or a salt of an acid is calculated as the acid.
  • the weight ratio of herbicide B to safener C is gener- ally in the range of from 1 :1000 to 1000:1 , preferably in the range of from 1 :500 to 500:1 , in par- ticular in the range of from 1 :250 to 250:1 and particularly preferably in the range of from 1 :75 to 75:1 , wherein each herbicide B and safener C being an ester or a salt of an acid is calculated as the acid.
  • the weight ratio of the combination of herbicides A and B to the safener C is preferably in the range of from 1 :500 to 500:1 , in particu- lar in the range of from 1 :250 to 250:1 and particularly preferably in the range of from 1 :75 to 75:1 , wherein each herbicide B and safener C being an ester or a salt of an acid is calculated as the acid.
  • herbicidal compositions as defined herein are suitable as herbicides as such or as appropri- ately formulated agrochemical compositions.
  • agrochemical composi- tion refers to a composition further comprising one or more auxiliaries customary in crop pro- tection.
  • the agrochemical composition comprises the herbicide A, optionally at least one herbicide B (as defined herein), optionally at least one safener C (as defined herein) and one or more auxiliaries customary in crop protection.
  • the herbicide A optionally at least one herbicide B (as defined herein) and optionally at least one safener C (as defined herein) can be converted into customary types of agrochemical corn- positions, e. g. solutions, emulsions, suspensions, dusts, powders, pastes, granules, pressings, capsules, and mixtures thereof.
  • agrochemical composition types are suspensions (e.g. SC, OD, FS), emulsifiable concentrates (e.g. EC), emulsions (e.g. EW, EO, ES, ME), cap- sules (e.g. CS, ZC), pastes, pastilles, wettable powders or dusts (e.g.
  • WP WP
  • SP WS
  • DP DS
  • pressings e.g. BR, TB, DT
  • granules e.g. WG, SG, GR, FG, GG, MG
  • insecticidal articles e.g. LN
  • gel formulations for the treatment of plant propagation materials such as seeds (e.g. GF).
  • 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, Lon- don, 2005.
  • auxiliaries customary in crop protection includes but is not limited to solvents, liquid carriers, solid carriers or fillers, surfactants, dispersants, emulsifiers, wetters, adjuvants, solubil- izers, penetration enhancers, protective colloids, adhesion agents, thickeners, humectants, re- pellents, 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 frac- tions 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, alkyl- ated naphthalenes; alcohols, e.g. ethanol, propanol, butanol, benzylalcohol, cyclohexanol; gly cols; DMSO; ketones, e.g. cyclohexanone; esters, e.g.
  • mineral oil frac- tions of medium to high boiling point e.g. kerosene, diesel oil
  • oils of vegetable or animal origin oils of vegetable or animal origin
  • aliphatic, cyclic and aromatic hydrocarbons e. g. toluene, paraffin, tetrahydr
  • 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, lime- stone, 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. ce- real meal, tree bark meal, wood meal, nutshell meal, and mixtures thereof.
  • mineral earths e.g. silicates, silica gels, talc, kaolins, lime- stone, lime, chalk, clays, dolomite, diatomaceous earth, bentonite, calcium sulfate, magnesium sulfate, magnesium oxide
  • polysaccharides e.g. cellulose, star
  • Suitable surfactants are surface-active compounds, such as anionic, cationic, nonionic and am- photeric surfactants, block polymers, polyelectrolytes, and mixtures thereof. Such surfactants can be used as emusifier, dispersant, solubilizer, wetter, penetration enhancer, protective col- loid, or adjuvant. Examples of surfactants are listed in McCutcheon’s, Vol.1 : Emulsifiers & De- tergents, 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 con- densed 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, es- ters, sugar-based surfactants, polymeric surfactants, and mixtures thereof.
  • alkox- ylates 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 sur- factants are sorbitans, ethoxylated sorbitans, sucrose and glucose esters or alkylpolygluco- sides.
  • polymeric surfactants are home- or copolymers of vinylpyrrolidone, vinylal- cohols, 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 pol- ymers of the A-B or A-B-A type comprising blocks of polyethylene oxide and polypropylene ox ide, or of the A-B-C type comprising alkanol, polyethylene oxide and polypropylene oxide.
  • Suita- ble polyelectrolytes are polyacids or polybases. Examples of polyacids are alkali salts of poly- acrylic acid or polyacid comb polymers. Examples of polybases are polyvinylamines or polyeth- yleneamines.
  • 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. Ex- amples 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-sol- uble dyes.
  • examples are inorganic colorants (e.g. iron oxide, titan oxide, iron hexacyanoferrate) and organic colorants (e.g. alizarin-, azo- and phthalocyanine colorants).
  • Suitable tackifiers or binders are polyvinylpyrrolidons, polyvinylacetates, polyvinyl alcohols, pol- yacrylates, 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% (ac- cording to NMR spectrum).
  • Solutions for seed treatment (LS), suspoemulsions (SE), flowable concentrates (FS), powders for dry treatment (DS), water-dispersible powders for slurry treatment (WS), water-soluble pow- ders (SS), emulsions (ES), emulsifiable concentrates (EC) and gels (GF) are usually employed for the purposes of treatment of plant propagation materials, particularly seeds.
  • the composi- tions in question give, after two-to-tenfold dilution, active substance concentrations of from 0.01 to 60% by weight, preferably from 0.1 to 40% by weight, in the ready-to-use preparations. Appli- cation can be carried out before or during sowing.
  • Methods for applying the herbicide A, optionally at least one herbicide B and optionally at least one safener C (or a composition comprising the herbicide A, optionally at least one herbicide B and optionally at least one safener C) onto plant propagation material, especially seeds include dressing, coating, pelleting, dusting, soaking and in-furrow application methods of the propaga- tion material.
  • the herbicide A, optionally at least one herbicide B and optionally at least one safener C (or a composition comprising the herbicide A, optionally at least one herbi- cide B and optionally at least one safener C) are applied onto the plant propagation material by a method such that germination is not induced, e. g. by seed dressing, pelleting, coating and dusting.
  • oils, wetters, adjuvants, fertilizer, or micronutrients, and further pesticides may be added to the active substances or the compositions comprising them as premix or, if appropriate not until immedi- ately prior to use (tank mix).
  • pesticides e.g. herbicides, insecticides, fungicides, growth regulators, safeners
  • These agents can be admixed with the herbicide A, optionally at least one herbicide B and optionally at least one safener C (or the composition comprising the herbicide A, optionally at least one herbicide B and optionally at least one safener C) used or applied in this invention in a weight ratio of 1 : 100 to 100:1 , preferably 1 : 10 to 10:1.
  • the user applies the agrochemical composition used or applied in this 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 agricultural useful area.
  • either individual components of the agrochemical composition or partially premixed components e. g. agrochemical components comprising herbicide A, option- ally at least one herbicide B and optionally at least one safener C 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 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 or par- tially premixed components e. g. components comprising herbicide A, optionally at least one herbicide B and optionally at least one safener C can be applied jointly (e.g. after tank mixing) or consecutively.
  • the agrochemical composition may be provided in the form of a single package for- mulation comprising herbicide A, optionally at least one herbicide B and optionally at least one safener C 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 formula- tion of herbicide A while the other package comprises a formulation comprising at least one herbicide B and/or safener C, and wherein both formulations comprise at least one carrier mate- rial, 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 formula- tion, wherein one package comprises a formulation of herbicide A and optionally the safener C, while the other package comprises a formulation of the at least one herbicide B, 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 as defined herein control vegetation on non-crop areas very efficiently, espe- cially 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.
  • compositions as defined herein are applied to the plants mainly by spraying.
  • the ap- plication can be carried out using, for example, water as carrier by customary spraying tech- niques using spray liquor amounts of from about 50 to 1000 l/ha (for example from 300 to 400 l/ha).
  • the compositions as defined herein may also be applied by the low-volume or the ultra- low-volume method, or in the form of microgranules.
  • compositions as defined herein 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 as defined herein, of a crop plant. If the herbicide A and, if appropriate, the herbicide B 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). In a further embodiment, the compositions as defined herein 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 the compositions as de- fined herein.
  • seed dressing seed coating, seed dusting, seed soaking, seed film coating, seed multilayer coating, seed encrusting, seed dripping and seed pelleting
  • the compositions as defined herein 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 trans- genic plants or plants obtained by customary breeding methods.
  • compositions as defined herein 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.
  • 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.
  • miscibility with mineral salt solutions which are employed for treat- ing nutritional and trace element deficiencies.
  • Non-phytotoxic oils and oil concentrates can also be added.
  • the amounts of active substances applied are, depending on the kind of ef- fect desired, 0.0001 to 10 kg per hectare (kg/ha), preferably 0.001 to 3 kg/ha, more preferably from 0.001 to 2.5 kg/ha, even more preferably from 0.001 to 2 kg/ha, especially preferably from 0.005 to 2 kg/ha, in particular from 0.05 to 0.9 kg/ha and most preferably from 0.1 to 0.8 kg/ha.
  • the herbicide A is generally applied in an amount of from 0.1 to 2000 grams per hectare (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 herbicide A is applied in an amount of 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 0.0005 kg/ha to 10 kg/ha, preferably from 0.005 kg/ha to 5 kg/ha and more preferably from 0.001 kg/ha to 2.5 kg/ha.
  • the application rate of the safener C is generally from 0.0005 kg/ha to 2.5 kg/ha, preferably from 0.005 kg/ha to 2 kg/ha and more preferably from 0.01 kg/ha to 1.5 kg/ha.
  • amounts of active substance i.e. herbicide A and, if appropriate, herbicide B
  • amounts of active substance are generally required.
  • the amounts of active substances ap- plied are generally employed in amounts of from 0.001 to 10 kg per 100 kg of seed.
  • the herbicide A and, if present, the herbicide B and/or the safener C can be applied jointly or separately.
  • the herbicide A and, if present, the herbicide B and/or the safener C can be applied simultaneously or in succession.
  • the herbicide A and, if present, the herbicide B and/or the safener C are applied sim- ultaneously to the undesirable vegetation.
  • the herbicide A and, if pre- sent, the herbicide B and/or the safener C are provided as herbicidal composition as defined herein (e.g. a tank mixture containing the herbicide A and, if present, the herbicide B and/or the safener C) being applied to the undesirable vegetation.
  • the herbicidal composition as defined herein is applied to the undesira- ble 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 and, if present, the herbicide B and/or the safener C is of minor importance. It is only necessary that the herbicide A and, if present, the herbicide B and/or the safener C are applied in a time frame that allows simultaneous action of the active ingredients on the plants to be controlled and/or safened, preferably within a time frame of at most 14 days, in particular at most 7 days.
  • the herbicide A and, if present, the herbicide B and/or the safener C can be applied pre-emergence (i.e. before the emergence of undesirable vegetation) or post-emergence (i.e., during and/or after emer gence of the undesirable vegetation).
  • the herbicide A and, if present, the herbicide B and/or the safener C are/is applied before the emergence of the undesirable vegeta- tion (pre-emergence).
  • the herbicide A and, if present, the herbicide B and/or the safener C are/is applied before or during the emergence of the undesir- able vegetation (pre-emergence or early-post emergence).
  • the herbicide A and, if present, the herbicide B and/or the safener C are/is applied after emergence of the undesirable vegetation.
  • a herbicidal composition comprising a) the herbicide A, b) a herbicide B which is pyroxasulfone and optionally c) at least one safener C as defined herein is used as a post-emergence herbicide.
  • a herbicidal composition comprising a) the herbicide A, b) a herbicide B which is pyroxasulfone and optionally c) at least one safener C as defined herein is applied after emergence of the undesirable vegetation.
  • the herbicide A and, if present, the herbicide B and/or the safener C are/is preferably applied after the undesirable vegetation has emerged and has developed up to 6 leaves.
  • the methods and uses according to the invention are suitable for controlling undesirable vege- tation in various crop plants.
  • suitable crops are the following:
  • Allium cepa (onions) Allium sativum (garlic), Ananas comosus (pineapples), Arachis hypogaea [peanuts (groundnuts)], Asparagus officinalis (asparagus), Avena sativa (oat), Beta vulgaris spec altissima (sugar beet), Beta vulgaris spec rapa (turnips), Brassica napus var. napus (rapeseed, canola), Brassica napus var. napobrassica (swedes), Brassica rapa var.
  • 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 li- berica) (coffee plants), Cucumis sativus (cucumber), Cynodon dactylon (Bermudagrass), Dau- cus carotasubspec.
  • Preferred crops are Allium cepa, Allium sativum, Arachis hypogaea, Avena sativa, Beta vulgaris spec altissima, Brassica napus var. napus, Brassica oleracea, Cynodon dactylon, Daucus carota subspec.
  • the crop plant is selected from the group consisting of cereals, corn (maize), sunflower, rice, soybeans, peas, Vicia-beans, Phaseolus-beans, peanuts, oilseed rape, canola, cotton, potato, sugarbeet, sugarcane, turfgrasses and vegetables, in particular 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 crop plant is selected from the group consisting of cereals, corn (maize), sunflower, rice, soybeans, peas, beans, peanuts, oilseed rape, canola, cotton, potato, sugarbeet, sugarcane, turfgrasses and vegetables, in particular 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 undesirable vegetation is controlled in cereals.
  • the cereals are selected from the group consisting of wheat, barley, rye, oat, and triticale.
  • the methods and uses according to the invention are also suitable for controlling undesirable vegetation in crops which have been modified by mutagenesis or genetic engineering in order to provide a new trait to a plant or to modify an already present trait.
  • crops as used herein includes also (crop) plants which have been modified by muta- genesis or genetic engineering in order to provide a new trait to a plant or to modify an already present trait.
  • Mutagenesis includes techniques of random mutagenesis using X-rays or mutagenic chemicals, but also techniques of targeted mutagenesis, in order to create mutations at a specific locus of a plant genome.
  • Targeted mutagenesis techniques frequently use oligonucleotides or proteins like CRISPR/Cas, zinc-finger nucleases, TALENs or meganucleases to achieve the targeting effect.
  • Genetic engineering usually uses recombinant DNA techniques to create modifications in a plant genome which under natural circumstances cannot readily be obtained by cross breeding, mutagenesis or natural recombination.
  • one or more genes are integrated into the ge- nome of a plant in order to add a trait or improve a trait. These integrated genes are also re- ferred to as transgenes in the art, while plant comprising such transgenes are referred to as transgenic plants.
  • the process of plant transformation usually produces several transformation events, wich differ in the genomic locus in which a transgene has been integrated. Plants corn- prising a specific transgene on a specific genomic locus are usually described as comprising a specific“event”, which is referred to by a specific event name. Traits which have been intro- prised in plants or hae been modified include in particular herbicide tolerance, insect resistance, increased yield and tolerance to abiotic conditions, like drought.
  • Herbicide tolerance has been created by using mutagenesis as well as using genetic engineer- ing. Plants which have been rendered tolerant to acetolactate synthase (ALS) inhibitor herbi- cides by conventional methods of mutagenesis and breeding comprise plant varieties commer- cially available under the name Clearfield ® . However, most of the herbicide tolerance traits have been created via the use of transgenes.
  • ALS acetolactate synthase
  • Herbicide tolerance has been created to glyphosate, glufosinate, 2,4-D, dicamba, oxynil herbi- cides, like bromoxynil and ioxynil, sulfonylurea herbicides, ALS inhibitor herbicides and 4-hy- droxyphenylpyruvate dioxygenase (HPPD) inhibitors, like isoxaflutole and mesotrione.
  • HPPD 4-hy- droxyphenylpyruvate dioxygenase
  • Transgenes wich have been used to provide herbicide tolerance traits comprise: for tolerance to glyphosate: cp4 epsps, epsps grg23ace5, mepsps, 2mepsps, gat4601 , gat4621 and goxv247, for tolerance to glufosinate: pat and bar, for tolerance to 2,4-D: aad-1 and aad-12, for tolerance to dicamba: dmo, for tolerance to oxynil herbicies: bxn, for tolerance to sulfonylurea herbicides: zm-hra, csr1-2, gm-hra, S4-HrA, for tolerance to ALS inhibitor herbicides: csr1-2, for tolerance to HPPD inhibitor herbicides: hppdPF, W336 and avhppd-03.
  • Transgenic corn events comprising herbicide tolerance genes are for example, but not exclud- ing others, DAS40278, MON801 , MON802, MON809, MON810, MON832, MON87411 , MON87419, MON87427, MON88017, MON89034, NK603, GA21 , MZHG0JG, HCEM485, VCO- 01981-5, 676, 678, 680, 33121 , 4114, 59122, 98140, Bt10, Bt176, CBH-351 , DBT418, DLL25, MS3, MS6, MZIR098, T25, TC1507 and TC6275.
  • Transgenic soybean events comprising herbicide tolerance genes are for example, but not ex- cluding others, GTS 40-3-2, MON87705, MON87708, MON87712, MON87769, MON89788, A2704-12, A2704-21 , A5547-127, A5547-35, DP356043, DAS44406-6, DAS68416-4, DAS- 81419-2, GU262, SYHT0H2, W62, W98, FG72 and CV127.
  • Transgenic cotton events comprising herbicide tolerance genes are for example, but not exclud- ing others, 19-51a, 31707, 42317, 81910, 281-24-236, 3006-210-23, BXN10211 , BXN10215, BXN 10222, BXN 10224, MON1445, MON1698, MON88701 , MON88913, GHB119, GHB614, LLCotton25, T303-3 and T304-40.
  • Transgenic canola events comprising herbicide tolerance genes are for example, but not ex- cluding others, MON88302, HCR-1 , HCN10, HCN28, HCN92, MS1 , MS8, PHY14, PHY23, PHY35, PHY36, RF1 , RF2 and RF3.
  • Insect resistance has mainly been created by transferring bacterial genes for insecticidal pro- teins to plants.
  • Transgenes which have most frequently been used are toxin genes of Bacillus spec and synthetic variants thereof, like cry1A, crylAb, cry1Ab-Ac, crylAc, cry1A.105, cry1 F, cry1 Fa2, cry2Ab2, cry2Ae, mcry3A, ecry3.1Ab, cry3Bb1 , cry34Ab1 , cry35Ab1 , cry9C, vip3A(a), vip3Aa20.
  • genes of plant origin have been transferred to other plants.
  • In particu- lar genes coding for protease inhibitors like CpTI and pinll.
  • a further approach uses transgenes in order to produce double stranded RNA in plants to target and downregulate insect genes.
  • An example for such a transgene is dvsnf7.
  • Transgenic com events comprising genes for insecticidal proteins or double stranded RNA are for example, but not excluding others, Bt10, Bt11 , Bt176, MON801 , MON802, MON809, MON810, MON863, MON8741 1 , MON88017, MON89034, 33121 , 4114, 5307, 59122, TC1507, TC6275, CBH-351 , MIR162, DBT418 and MZIR098.
  • Transgenic soybean events comprising genes for insecticidal proteins are for example, but not excluding others, MON87701 , MON87751 and DAS-81419.
  • Transgenic cotton events comprising genes for insecticidal proteins are for example, but not ex- cluding others, SGK321 , MON531 , MON757, MON1076, MON15985, 31707, 31803, 31807, 31808, 42317, BNLA-601 , Eventl , COT67B, COT102, T303-3, T304-40, GFM Cry1A, GK12, MLS 9124, 281-24-236, 3006-210-23, GHB119 and SGK321.
  • Increased yield has been created by increasing ear biomass using the transgene athb17, being present in corn event MON87403, or by enhancing photosynthesis using the transgene bbx32, being present in the soybean event MON87712.
  • Crops comprising a modified oil content have been created by using the transgenes: gm-fad2-1 , Pj.D6D, Nc.Fad3, fad2-1A and fatb1-A. Soybean events comprising at least one of these genes are: 260-05, MON87705 and MON87769.
  • Tolerance to abiotic conditions, in particular to tolerance to drought, has been created by using the transgene cspB, comprised by the corn event MON87460 and by using the transgene Hahb- 4, comprised by soybean event IND-00410-5.
  • Traits are frequently combined by combining genes in a transformation event or by combining different events during the breeding process.
  • Preferred combination of traits are herbicide toler- ance to different groups of herbicides, insect tolerance to different kind of insects, in particular tolerance to lepidopteran and coleopteran insects, herbicide tolerance with one or several types of insect resistance, herbicide tolerance with increased yield as well as a combination of herbi- cide tolerance and tolerance to abiotic conditions.
  • Plants comprising singular or stacked traits as well as the genes and events providing these traits are well known in the art.
  • detailed information as to the mutagenized or inte- grated genes and the respective events are available from websites of the organizations“Inter- national Service for the Acquisition of Agri-biotech Applications (ISAAA)”
  • the methods and uses according to the invention may result in effects which are specific to a crop comprising a certain gene or event. These effects might involve changes in growth behav- ior or changed resistance to biotic or abiotic stress factors. Such effects may in particular corn- prise enhanced yield, enhanced resistance or tolerance to insects, nematodes, fungal, bacterial, mycoplasma, viral or viroid pathogens as well as early vigour, early or delayed ripening, cold or heat tolerance as well as changed amino acid or fatty acid spectrum or content. Furthermore, 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 produc- tion, e.g., potatoes that produce increased amounts of amylopectin (e.g. Amflora® potato, BASF SE, Germany).
  • amylopectin e.g. Amflora® potato, BASF SE, Germany
  • the methods and uses according to the invention are also suitable for the defoliation and/or desiccation of plant parts, for which crop plants such as cot- ton, potato, oilseed rape, sunflower, soybean or field beans, in particular cotton, are suitable.
  • the methods and uses according to the invention are suitable for desiccating the above-ground parts of crop plants such as potato, oilseed rape, sunflower and soybean, but also cereals. This makes possible the fully mechanical harvesting of these important crop plants.
  • herbicide A (2-(2,4-dichlorophenyl)methyl-4,4-dimethyl-3-isoxazolidone of the formula I, also abbreviated herein as“2,4-DC”) on resistant weed biotypes was tested in comparison with a commercial herbicide with the common name clomazone (chemical name: 2- [(2-chlorophenyl)methyl]-4,4-dimethyl-3-isoxazolidinone) by the following greenhouse experi- ments:
  • the culture containers used were plastic flowerpots containing loamy sand with approximately 3.0% of humus as the substrate.
  • the seeds of the test plants were sown separately for each species.
  • Fourteen blackgrass (ALOMY) biotypes (BT-01352, BT-01369, BT-01367, BT-01365, BT-01666, BT-01672, BT-011 18, BT-06274, BT-06275, BT-01138, BT-01375, BT-01355, BT- 01 137 and BT-02342) and twelve ryegrass (LOLSS) biotypes (BT-02173, BT-02183, BT-02213, BT-02214, BT-02215, BT-06008, BT-06591 , BT-02264, BT-02265, BT-07240, BT-07248 and BT-06008) with varying degrees of resistance towards a range of modes of action according to the HRAC (Herbicide Resistance Action Committee)
  • test plants were first grown to a height of 3 to 15 cm, depending on the plant habit, and only then treated with the active ingredients which had been suspended or emulsified in water.
  • the test plants were either sown directly and grown in the same containers, or they were first grown separately as seedlings and transplanted into the test containers a few days prior to treatment.
  • the plants were kept at 10-25°C or 20-35°C.
  • the test period extended over 2 to 4 weeks. During this time, the plants were tended, and their response to the individual treatments was evaluated.
  • Herbicide A was formulated as an emulsion concentrate (EC) with an active ingredient concen- tration of 5%.
  • Clomazone was used as a commercial capsule suspension (CS) formulation (Command ® ) having an active ingredient concentration of 360 g/l.
  • Evaluation of the herbicidal activity was carried out using a scale from 0 to 100. 100 means complete destruction of at least the aerial moieties, and 0 means no damage, or normal course of growth. A good herbicidal activity is given at values of at least 70 and a very good herbicidal activity is given at values of at least 85.
  • Table 1 Herbicidal activity of clomazone and herbicide A (2,4-DC) applied post-emergence on blackgrass (ALOMY) biotypes
  • herbicide A in a post-emergence treatment when corn- pared against the commercial herbicide Clomazone, herbicide A exhibits a superior herbicidal activity against various biotypes of blackgrass (ALOMY) and ryegrass (LOLSS) with varying de- grees of resistance towards a range of modes of action according to the HRAC (Herbicide Re- sistance Action Committee) classification on mode of action 2010.
  • AOMY blackgrass
  • LLSS ryegrass

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