Method for controlling herbicide resistant or tolerant weeds

Abstract

To provide a method for controlling herbicide resistant or tolerant weed species.SOLUTION: The herbicidal compound (±) -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 is applied.SELECTED DRAWING: None

Description

[Technical Field]

[0001] The present invention relates to a method and use for controlling herbicide-resistant or tolerant weed species by applying the herbicide (±)-2-exo-(2-methylbenzyloxy)-1-methyl-4-isopropyl-7-oxabicyclo[2.2.1]heptane, any of its individual enantiomers, or any non-racemic mixture of said enantiomers. The method and use are particularly suitable for crop protection. The present invention also relates to specific herbicidal compositions comprising said herbicide. [Background technology]

[0002] Herbicide-resistant weeds are becoming an increasingly common problem. These biotypes survive herbicide applications, usually at doses that effectively control the species. Resistant weed biotypes are the result of a fundamental evolutionary process: individuals best adapted to a particular practice are selected within a species and increase in number within a population. Once a weed population is exposed to a herbicide to which one or more plants are naturally resistant, the herbicide kills sensitive individuals, while resistant individuals are able to survive and reproduce. With repeated herbicide applications, resistant weeds, which initially appear as isolated plants or patches in the field, can rapidly spread and dominate the population and soil seed bank.

[0003] For example, herbicide resistance in weeds, especially grass weeds such as black foxglove (Alopecurus myosuroides) (ALOMY), common bramble (Apera spica-venti) (APESV) or Lolium species (LOLSS), is becoming a major problem for farmers and is causing dramatic weed control problems, for example in cereals. Herbicides from the ACCase inhibitor and ALS inhibitor groups, as well as various other types of herbicides, are also highly susceptible to resistance evolution.

[0004] WO 2007 / 023099 discloses herbicidal mixtures containing exo-(±)-1-methyl-4-(1-methylethyl)-2-[(2-methylphenyl)methoxy]-7-oxabicyclo[2.2.1]heptane and at least one dinitroaniline herbicide, such as trifluralin and pendimethalin. It is stated that these herbicidal mixtures are capable of very good control of undesirable vegetation, including grass weeds that are resistant or tolerant to certain herbicides.

[0005] WO 2007 / 030886 discloses herbicidal mixtures containing at least one dinitroaniline herbicide and a herbicidal compound having the IUPAC name 1,4-epoxy-p-2-yl-methylbenzyl ether (called cinmethylin), believed to have 1RS,2SR,4SR stereochemistry, and methods for controlling weeds by applying these mixtures. Example 5 discloses that trifluralin and cinmethylin were applied alone and in a mixture to a specific dinitroaniline-resistant annual ryegrass population.

[0006] Herbicide-tolerant or -resistant weed control by applying a mixture comprising (a) 4-amino-3-chloro-5-fluoro-6-(4-chloro-2-fluoro-3-methoxyphenyl)pyridine-2-carboxylic acid, or an agriculturally acceptable ester or salt thereof, and (b) an acetyl-CoA carboxylase (ACCase) inhibitor is described in US 2014 / 0031228 A1.

[0007] Nevertheless, there remains a need to further develop methods to prevent, delay, or manage herbicide resistance in weeds.

[0008] Furthermore, there is still room for improvement, for example with regard to activity, activity spectrum and compatibility with useful plants, especially with regard to the control of resistant weed biotypes. [Prior art documents] [Patent documents]

[0009] [Patent Document 1] WO 2007 / 023099 [Patent Document 2] WO 2007 / 030886 [Patent Document 3] US 2014 / 0031228 A1 Summary of the Invention [Problem to be solved by the invention]

[0010] Accordingly, an object of the present invention is the effective control of herbicide-resistant weed biotypes, particularly herbicide-resistant grass weeds.

[0011] It is also an object of the present invention to improve herbicidal activity against unwanted harmful plants and / or compatibility with useful plants, especially crop plants. [Means for solving the problem]

[0012] These and further objects are achieved by the following methods, uses and herbicidal compositions.

[0013] Thus, in one aspect of the present invention, there is provided a method for controlling undesirable vegetation comprising the step of applying a herbicidally effective amount of (±)-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) to the vegetation or locus thereof, or to the soil or water to prevent emergence or growth of the undesirable vegetation, wherein the undesirable vegetation comprises at least one herbicide-resistant or tolerant weed species.

[0014] As used herein, the term "herbicide A" refers to the racemic mixture (±)-2-exo-(2-methylbenzyloxy)-1-methyl-4-isopropyl-7-oxabicyclo[2.2.1]heptane (also referred to herein as the "exo-(±)-isomer", CAS RN 87818-31-3),

[0015] [ka] It is intended to include either of its individual enantiomers or any non-racemic mixtures thereof. The racemic mixture contains equal amounts of the two enantiomers (+)-2-exo-(2-methylbenzyloxy)-1-methyl-4-isopropyl-7-oxabicyclo[2.2.1]heptane (also referred to herein as the "exo-(+)-isomer", CAS RN 87818-61-9) and (-)-2-exo-(2-methylbenzyloxy)-1-methyl-4-isopropyl-7-oxabicyclo[2.2.1]heptane (also referred to herein as the "exo-(-)-isomer", CAS RN 87819-60-1). The exo-(±)-, exo-(+)- and exo-(-)-isomers, including their preparation and herbicidal properties, are disclosed in EP 0 081 893 A2 (see Examples 29, 34, 35 and 62). Further methods for preparing these compounds are described in US 4,487,945 (see Examples 46 and 48). The racemic mixture (±)-2-exo-(2-methylbenzyloxy)-1-methyl-4-isopropyl-7-oxabicyclo[2.2.1]heptane is also listed in The Pesticide Manual, Fourteenth Edition, Editor: CDS Tomlin, British Crop Production Council, 2006, entry 157, pages 195-196, under the common name cinmethylin, the IUPAC name (1RS,2SR,4SR)-1,4-epoxy-p-mentha-2-yl 2-methylbenzyl ether, and the Chemical Abstracts name exo-(±)-1-methyl-4-(1-methylethyl)-2-[(2-methylphenyl)methoxy]-7-oxabicyclo[2.2.1]heptane.

[0016] The term "herbicidally effective amount" means an amount of active ingredient sufficient to control undesirable plants, particularly in cultivated plants, without causing substantial injury to the plants being treated. Such amounts can vary widely and depend on various factors, such as the plants to be controlled, the cultivated plants or materials being treated, the climatic conditions, and the particular composition according to the invention being used.

[0017] As used herein, the terms "plant" and "vegetation" include germinated seeds, emerged seedlings, plants emerging from vegetative propagules, and established vegetation.

[0018] As used herein, the term "locus" means an area, usually a field, where vegetation or plants are growing or will grow.

[0019] As used herein, the terms "control" and "elimination" are synonymous.

[0020] As used herein, the terms "undesirable vegetation," "harmful plants," "undesirable plants," "weeds," and "weed species" are synonymous.

[0021] The present invention also relates to the use of (±)-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) for controlling herbicide-resistant or tolerant weed species.

[0022] The method of the invention may further comprise the step of applying at least one herbicide B (defined below) different from herbicide A. The method of the invention may further comprise the step of applying at least one safener C (defined below). The method of the invention may further comprise the step of applying one or more adjuvants (defined below) customary in crop protection.

[0023] In another aspect, the present invention relates to a method for controlling undesirable vegetation, comprising the step of applying to the vegetation or its locus, or to the soil or water, a composition comprising a herbicidally effective amount of a herbicide A to prevent the emergence or growth of the undesirable vegetation. The composition may further comprise at least one herbicide B (defined below) and / or at least one safener C (defined below) and / or one or more adjuvants (defined below) customary in crop protection.

[0024] In a further aspect, the present invention relates to a specific herbicidal composition comprising a herbicidally effective amount of a herbicide A and a herbicide B of a specific group defined below.

[0025] Further embodiments of the invention are evident from the description, the examples and the claims. It is to be understood that the features of the subject matter of the invention described above and subsequently exemplified below can be applied not only in the combination given in each particular case but also in other combinations without departing from the scope of the invention. DETAILED DESCRIPTION OF THE INVENTION

[0026] Surprisingly, it has been found that the herbicidal compound (±)-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) provides effective control of herbicide-resistant or tolerant weed species, particularly herbicide-resistant weed biotypes. For example, Herbicide A can effectively control herbicide-resistant grass weeds, such as black foxtail (ALOMY), common ragwort (APESV), Phalaris species (PHASS), or Lolium species (LOLSS). Herbicide A is also suitable for controlling herbicide-resistant broadleaf weeds, such as Papaver rhoeas (PAPRH, corn poppy), which have evolved resistance, particularly to ALS-inhibiting herbicides.

[0027] Another advantage of the present invention is that herbicide A can be used to control weed biotypes with target-site resistance as well as weed biotypes with non-target-site resistance. A particular advantage of the present invention is that herbicide A also provides effective control of weed biotypes with both target-site and non-target-site resistance, such as resistant populations of black-grass (ALOMY) or Lolium rigidum (LOLRI).

[0028] As used herein, "target site resistance" occurs due to mutations in the gene encoding the enzyme at the herbicide target site (restricting herbicide binding) or due to overproduction of the target enzyme (gene overexpression or amplification).

[0029] As used herein, "non-target site resistance" involves mechanisms that minimize the amount of active herbicide that reaches the target site (e.g., reduced herbicide uptake or translocation, increased herbicide sequestration, or enhanced herbicide metabolism).

[0030] In a preferred embodiment, herbicide A is (±)-2-exo-(2-methylbenzyloxy)-1-methyl-4-isopropyl-7-oxabicyclo[2.2.1]heptane.

[0031] In another embodiment, herbicide A is (+)-2-exo-(2-methylbenzyloxy)-1-methyl-4-isopropyl-7-oxabicyclo[2.2.1]heptane.

[0032] In another embodiment, herbicide A is (-)-2-exo-(2-methylbenzyloxy)-1-methyl-4-isopropyl-7-oxabicyclo[2.2.1]heptane.

[0033] In another embodiment, 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 amounts 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.

[0034] Exemplary herbicide-resistant or tolerant weed species include acetyl-CoA carboxylase (ACCase) inhibitors (HRAC Group A), acetolactate synthase (ALS) inhibitors (HRAC Group B), photosystem II (PSII) inhibitors (HRAC Groups C1, C2, and C3), photosystem I (PSI) 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-enolpyruvylshikimate-3-phosphate (EPSP) inhibitors (HRAC Group G), glutamine synthetase inhibitors (HRAC Group H), DHP synthase inhibitors (HRAC Group F5), and the like. These include, but are not limited to, biotypes that are resistant or tolerant to herbicides selected from the group consisting of HRAC inhibitors (HRAC group I), microtubule assembly inhibitors (HRAC group K1), mitosis / microtubule assembly inhibitors (HRAC group K2), very long chain fatty acid (VLCFA) inhibitors (HRAC group K3), cell wall synthesis inhibitors (HRAC group L), uncouplers (membrane disrupting) (HRAC group M), lipid synthesis inhibitors (HRAC group N), synthetic auxins (HRAC group O), auxin transport inhibitors (HRAC group P), and herbicides with unknown mode of action (HRAC group Z).

[0035] Preferably, the herbicide-resistant or tolerant weed species is selected from biotypes that are 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 (PSII) 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-enolpyruvylshikimate-3-phosphate (EPSP) inhibitors (HRAC group G), microtubule assembly inhibitors (HRAC group K1), very long-chain fatty acid (VLCFA) inhibitors (HRAC group K3), cell wall synthesis inhibitors (HRAC group L), and lipid synthesis inhibitors (HRAC group N).

[0036] More preferably, the herbicide-resistant or tolerant weed species is selected from biotypes that are 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 (PSII) inhibitors (HRAC groups C1, C2, and C3), microtubule assembly inhibitors (HRAC group K1), very long-chain fatty acid (VLCFA) inhibitors (HRAC group K3), and lipid synthesis inhibitors (HRAC group N).

[0037] In particular, the herbicide-resistant or tolerant weed species are selected from biotypes that are resistant or tolerant 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 (PSII) inhibitors (HRAC groups C1, C2, and C3).

[0038] In another embodiment, the resistant or tolerant biotype is a member of the genus Agropyron, Alopecurus, Apera, Avena, Brachiaria, Bromus, Cynodon, Digitalia, Echinochloa, Eleusine, Ischaemum, Leptochloa, Lolium, Panicum, Reed canary grass, Poa, Rottboellia, Setaria, or any of the genus The plant is selected from the genera Setaria, Anthemis, Amaranthus, Ambrosia, Capsella, Centaurea, Chenopodium, Conyza, Descurainia, Galium, Kochia, Matricaria, Papaver, Raphanus, Sinapis, Sisymbrium, Stellaria and Thlaspi.

[0039] Preferably, the resistant or tolerant biotype is selected from the genera Alopecia, Branca, Digitalia, Echinochloa, Leptogastrodus, Lolium, Reed canary grass, Poo, Setaria, Amaranthus, Anthemis, Shepherd's purse, Centaurea, Chenopodium, Descurania, Kochia, Deer daisy, Papaver somniferum, Stellaria and Shepherd's purse, more preferably Alopecia, Branca, Echinochloa, Leptogastrodus, Lolium , Reed canary grass, Papaver somniferum, Amaranthus, Chenopodium, Deer daisy, Papaver somniferum and Stellaria, even more preferably selected from Alopecurus, Echinochloa, Lolium, Reed canary grass, Papaver somniferum, Amaranthus, Chenopodium, Deer daisy, Papaver somniferum and Stellaria, even more preferably selected from Alopecurus, Echinochloa, Lolium, Reed canary grass, Papaver somniferum and Stellaria, especially selected from Alopecurus, Lolium, Reed canary grass and Papaver somniferum.

[0040] In another embodiment, the resistant or tolerant biotype is selected from the genera Alopecia, Branca, Digitalia, Echinochloa, Leptogastropoda, Reed canary grass, Poo, Setaria, Amaranthus, Anthemis, Shepherd's purse, Centaurea, Chenopodium, Descurania, Kochia, Deerflower, Papaver somniferum, Stellaria and Shepherd's purse, more preferably Alopecia, Branca and Echinochloa , Polygala, Reed canary grass, Pseudosia spp., Amaranthus, Chenopodium, Deer Daisy, Papaveraceae and Stellaria, even more preferably selected from Alopecurus, Echinochloa, Reed canary grass, Pseudosia spp., Amaranthus, Chenopodium, Deer Daisy, Papaveraceae and Stellaria, even more preferably selected from Alopecurus, Echinochloa, Reed canary grass, Pseudosia spp., Amaranthus, Chenopodium, Deer Daisy, Papaveraceae and Stellaria, and especially selected from Alopecurus, Reed canary grass and Papaveraceae.

[0041] In one embodiment, the resistant or tolerant biotype is a monocotyledonous weed species selected from the genera Alopecia, Common Weed, Digitalia, Echinochloa, Lorium, Reed Canary Worm, Pooja and Setaria, preferably selected from Alopecia, Common Weed, Echinochloa, Lorium, Reed Canary Worm and Pooja, more preferably selected from Alopecia, Echinochloa, Lolium, Reed Canary Worm and Pooja, especially Alopecia, Lolium and Pooja.

[0042] In another embodiment, the resistant or tolerant biotype is a monocotyledonous weed species selected from the genera Alopecia, Buttermilk, Digitalia, Echinochloa, Leptochloa, Reed canary grass, Pooja and Setaria, preferably selected from Alopecia, Buttermilk, Echinochloa, Leptochloa, Reed canary grass and Pooja, more preferably selected from Alopecia, Echinochloa, Reed canary grass and Pooja, especially Alopecia and Pooja.

[0043] In another embodiment, the resistant or tolerant biotype is a dicotyledonous weed species, preferably selected from the genera Amaranthus, Anthemis, Shepherd's Purse, Centaurea, Chenopodium, Descurania, Kochia, Deerflower, Papaver somniferum, Papaver somniferum, Stellaria and Shepherd's Purse, more preferably selected from the genera Amaranthus, Chenopodium, Deerflower, Papaver somniferum and Stellaria, especially Papaver somniferum.

[0044] In another embodiment, the herbicide resistant or tolerant weed species is selected from Alopecia, Cornus, Lolium, Poo, Reed canary grass, and Papaveraceae.

[0045] In another embodiment, the herbicide resistant or tolerant weed species is selected from Alopecia, Cornus, Lolium, Poo, and Papaveraceae.

[0046] In another embodiment, the herbicide resistant or tolerant weed species is selected from Alopecurus, Cornus, Poa, Reed canary grass, and Papaveraceae.

[0047] In another embodiment, the herbicide resistant or tolerant weed species is selected from Alopecia, Cornus, Pooja, and Papaver.

[0048] In another embodiment, the herbicide resistant or tolerant weed species is selected from the genera Alopecia, Cornus, and Papaver.

[0049] In another embodiment, the herbicide resistant or tolerant weed species is selected from the genera Alopecia, Lolium, and Papaveracea.

[0050] In another embodiment, the herbicide resistant or tolerant weed species is selected from the genera Alopecia and Papaveracea.

[0051] In another embodiment, the herbicide resistant or tolerant weed species is selected from the genera Cotton, Poa and Papaveraceae.

[0052] In another embodiment, the herbicide resistant or tolerant weed species is selected from the genera Cotton and Papaveracea.

[0053] In another embodiment, the herbicide resistant or tolerant weed species is selected from the genus Cotton.

[0054] In another embodiment, the herbicide resistant or tolerant weed species is selected from the genus Papaveracea.

[0055] In another embodiment, the herbicide resistant or tolerant weed species is selected from the genera Alopecia, Cornus, Lolium, and Poa.

[0056] In another embodiment, the herbicide resistant or tolerant weed species is selected from the genera Alopecia, Cornus, and Lolium.

[0057] In another embodiment, the herbicide resistant or tolerant weed species is selected from the genera Alopecia, Cornus, and Poa.

[0058] In another embodiment, the herbicide resistant or tolerant weed species is selected from the genera Alopecia and Lolium.

[0059] In another embodiment, the herbicide resistant or tolerant weed species is selected from the genera Alopecia and Brassica, particularly Alopecia.

[0060] In particular, resistant or tolerant biotypes include black foxtail, alopecurus aequalis, common bran, oat (Avena fatua), wild oat (Avena sterilis), Brachiaria plantaginea, Brachiaria decumbens, bromegrass (Bromus secalinus), rhubarb (Bromus sterilis), horsegrass (Bromus tectorum), large crabgrass (Digitaria ciliaris), large crabgrass (Digitaria insularis), large crabgrass (Digitaria ischaemum), large crabgrass (Digitaria sanguinalis), horse millet (Echinochloa colona), barnyard grass (Echinochloa crus-galli), Echinochloa crus-pavonis, Echinochloa erecta, barnyard grass (Echinochloa oryzoides), barnyard grass (Echinochloa phyllogogon), goosegrass (Eleusine indica), Taiwanese sedge (Ischaemum rugosum), Japanese pigweed (Leptochloa chinensis), Leptochloa panicoides, Leptochloa scabra, Leptochloa virgata, Lolium multiflorum, Lolium perenne, Japanese oak, Panicum capillare, Panicum dichotomiflorum, Phalaris brachystachyx, Phalaris minor, Phalaris paradoxa, Poa annua, Poa pratensis, Poa trifoliatatrivialis, Horned foxtail (Rottboellia exaltata), Autumn foxtail (Setaria faberi), Small foxtail (Setaria glauca), Golden foxtail (Setaria pumila), Rough foxtail (Setaria verticillata), Green foxtail (Setaria viridis), Little white birch (Amaranthus albus), American blackbird (Amaranthus blitoides), Narrow green amaranth (Amaranthus hybridus), Palmer's amaranth (Amaranthus palmeri), Long-legged amaranth (Amaranthus powellii), Redroot pigweed (Amaranthus retroflexus), Water chestnut (Amaranthus tuberculatus), Amaranthus rudis (Amaranthus rudis), Waterweed (Amaranthus viridis), Ragweed (Ambrosia artemisifolia), Chamomile (Anthemis arvensis), Shepherd's purse (Capsella bursa-pastoris), Cornflower (Centaurea cyanus), Chenopodium album, Common ragweed (Chenopodium ficifolium), Chenopodium polyspermum, Common pigweed (Chenopodium hybridum), Ragweed (Conyza bonariensis), Artemisia canadensis, Whale grass (Descurania sophia), Spotted grass (Galium aparine), Cleaver grass (Galium spurium), Common grass (Galium tricornutum), Kochia scoparia), chamomile (Matricaria chamomilla), daisy (Matricaria discoidea), chamomile (Matricaria inodora), corn poppy, wild radish (Raphanus raphanistrum), white mustard (Sinapisalba, Sinapis arvensis, Sisymbrium officinale, Sisymbrium orientale, Stellaria media and Thlaspi arvense, preferably black-edge grass, white-edge grass, common bran, northern crabgrass, large crabgrass, barnyard grass, barnyard grass, Chinese rice grass, loosegrass, ryegrass, ryegrass, ryegrass, Phalaris brachystachys, reed canary grass, Phalaris paradoxa, annual bluegrass, annual bluegrass, autumn foxtail, Japanese boxwood, Setaria pumilla), rough foxtail, green foxtail, common amaranthus retroflexus, redroot pigweed, water hyacinth, Amaranthus rudis, chamomile, shepherd's purse, cornflower, lamb's quarter, Descurania sophia, kochia, chamomile, dogwood, corn poppy, persimmon, chickweed and shepherd's purse, more preferably black-glove foxtail, common foxtail, branwort, barnyard grass, barnyard grass, pigweed, ryegrass, ryegrass, oak, ryegrass, oak, Phalaris brachystachys, reed canary grass, Phalaris paradoxa, annual bluegrass, common amaranthus retroflexus, redroot pigweed, water hyacinth, amaranth It is selected from the group consisting of false alder, Amaranthus rudis, Chenopodium album, chamomile, chamomile, corn poppy and chickweed, and particularly preferably selected from the group consisting of black foxtail, annual foxtail, common bran, barnyard grass, barnyard grass, Chinese ryegrass, woolly grass, reed canary grass and annual bluegrass, and in particular selected from the group consisting of black foxtail, black foxtail, woolly grass and reed canary grass.

[0061] In another embodiment, the resistant or tolerant biotype is selected from the group consisting of black foxtail, common foxtail, common bran, wild oat, wild oat, Brachiaria plantaginea, Brachiaria decumbens, common brome, common brome, common brome, large crabgrass, large crabgrass, common crabgrass, Japanese barnyard grass, barnyard grass, Echinochloa crus-pavonis, Echinochloa erecta, barnyard grass, barnyard grass, goosegrass, common eyefoot, Chinese pigweed, Leptochloa panicoides, Leptochloa scabra, Leptochloa virgata, common morning glory, common morning glory, Phalaris brachystachys brachystachyx), dwarf canary grass, Phalaris paradoxa, annual bluegrass, longgrass, annual bluegrass, hornwort, autumn foxtail, golden foxtail, rough foxtail, green foxtail, white birch, American blackfly, narrow-leaved amaranthus, large-leaved amaranthus, long-leaved amaranthus, redroot pigweed, false amaranthus, Amaranthus rudis, common water chestnut, ragweed, chamomile, shepherd's purse, common cornflower, common oak, common oak, Chenopodium polyspermum, parsley, ragweed, ragweed, common mugwort, common mugwort, and ragweed (Descurania sophia), white spotted grass, cleaver, Japanese tortoiseshell grass, broom tree, chamomile, daisy, chamomile, corn poppy, wild radish, white mustard, field mustard, persimmon mustard, wild mustard, chickweed and shepherd's purse, and preferably black-and-white foxtail, white-and-white foxtail, common bran, northern crabgrass, large crabgrass, barnyard grass, barnyard grass, Chinese chive, Phalaris brachystachis, reed canary grass, Phalaris paradoxa, annual bluegrass, annual bluegrass, autumn foxtail, Japanese boxwood, golden foxtail, Setaria pumilla), rough foxtail, green foxtail, redroot pigweed, redroot pigweed, water chestnut, Amaranthus rudis, chamomile, shepherd's purse, cornflower, lamb's quarter, and ragwort (Descuraniasophia), kochia, chamomile, chamomile, corn poppy, persimmon, chickweed and shepherd's purse, more preferably black-glove amaryllis, black-glove amaryllis, common branwort, barnyard grass, barnyard grass, Chinese pigweed, Phalaris brachystachys, reed canary grass, Phalaris paradoxa, annual bluegrass, red ivy, and bluegrass. It is selected from the group consisting of silverweed, water hyacinth, Amaranthus rudis, lamb's quarter, chamomile, chamomile, corn poppy and chickweed, and particularly preferably selected from the group consisting of black foxtail, annual foxtail, common bran, barnyard grass, barnyard grass, Chinese ryegrass, reed canary grass and annual bluegrass, and in particular black foxtail or reed canary grass.

[0062] In one embodiment, the resistant or tolerant biotype is selected from the group consisting of black foxtail, foxtail, common bran, northern crabgrass, large crabgrass, barnyard grass, barnyard grass, Chinese watergrass, pigweed, loosegrass, ryegrass, ryegrass, Phalaris brachystachys, reed canary grass, Phalaris paradoxa, annual bluegrass, annual bluegrass, foxtail grass, Japanese boxgrass, Setaria pumilla), rough foxtail, and green foxtail, preferably selected from the group consisting of black foxtail, annual foxtail, common bran, barnyard grass, barnyard grass, Echinochloa crus-galli, barnyard grass, loosegrass, ryegrass, ryegrass, Phalaris brachystachys, reed canary grass, Phalaris paradoxa, and annual bluegrass, more preferably selected from the group consisting of black foxtail, annual foxtail, common bran, barnyard grass, barnyard grass, barnyard grass, loosegrass, barnyard grass, ryegrass, ryegrass, reed canary grass, and annual bluegrass, in particular selected from the group consisting of black foxtail, barnyard grass, ryegrass, and reed canary grass.

[0063] In another embodiment, the resistant or tolerant biotype is selected from the group consisting of Amaranthus retroflexus, Amaranthus retroflexus, Amaranthus rudis, Chamomile, Shepherd's purse, Cornflower, Chenopodium album, Descurania sophia, Broomonia sieboldii, Chamomile, Anthemis nobilis, Corn poppy, Persimmon, Chickweed and Shepherd's purse, preferably Amaranthus retroflexus, Amaranthus retroflexus, Amaranthus rudis, Chenopodium album, Chamomile, Anthemis nobilis, Corn poppy and Chickweed, more preferably Corn poppy.

[0064] In particular, the methods, uses and compositions of the present invention are useful for the control of ACCase-resistant grass weeds, more particularly black-glove weeds, black-glove weeds, common bran, wild oat, common wild oat, Brachiaria plantaginea, Brachiaria decumbens, common brome, common brome, common brome, large crabgrass, large crabgrass, northern crabgrass, and common crabgrass. Barnyardgrass, Echinochloa crus-pavonis, Echinochloa erecta, Barnyardgrass, Barnyardgrass, Goosegrass, Taiwan grass, Leptochloa panicoides, Leptochloa scabra, Leptochloa virgata, Loose barnyardgrass, Ryegrass, Cornus gracilis, Oriental millet, Common millet, Phalaris brachystachys brachystachyx), reed canary grass, Phalaris paradoxa, annual bluegrass, longgrass, Poa annua, hornwort, foxtail, Japanese foxtail, golden foxtail, rough foxtail, and green foxtail, and preferably black foxtail, annual bluegrass, common bran, northern crabgrass, large crabgrass, barnyard grass, barnyard grass, Chinese watergrass, pigweed, ryegrass, ryegrass, oak, Phalaris brachystachys, reed canary grass, Phalaris paradoxa, annual bluegrass, Poa annua, hornwort, foxtail, golden foxtail, Setaria pumilla), rough foxtail, and green foxtail, more preferably selected from the group consisting of black foxtail, annual foxtail, European bran, barnyard grass, barnyard grass, Chinese watergrass, loosegrass, ryegrass, ryegrass, Phalaris brachystachys, reed canary grass, Phalaris paradoxa, and annual bluegrass, particularly preferably selected from the group consisting of black foxtail, annual foxtail, European bran, barnyard grass, barnyard grass, barnyard grass, loosegrass, ryegrass, ryegrass, ryegrass, Phalaris paradoxa, and annual bluegrass, and is particularly suitable for controlling ACCase-resistant grass weeds selected from the group consisting of black foxtail, barnyard grass, ryegrass, ryegrass, and ryegrass.

[0065] In another embodiment, the herbicide resistant or tolerant weed species is selected from black foxglove, common branwort, loosegrass, annual bluegrass, reed canary grass, and corn poppy.

[0066] In another embodiment, the herbicide resistant or tolerant weed species is selected from black foxglove, common branwort, loosestrife, annual bluegrass, and corn poppy.

[0067] In another embodiment, the herbicide resistant or tolerant weed species is selected from black foxglove, common branwort, annual bluegrass, reed canary grass, and corn poppy.

[0068] In another embodiment, the herbicide resistant or tolerant weed species is selected from black foxglove, common branwort, annual bluegrass, and corn poppy.

[0069] In another embodiment, the herbicide resistant or tolerant weed species is selected from black foxglove, common branwort, and corn poppy.

[0070] In another embodiment, the herbicide resistant or tolerant weed species is selected from black foxglove, Locust rye, and corn poppy.

[0071] In another embodiment, the herbicide resistant or tolerant weed species is black foxglove or corn poppy.

[0072] In another embodiment, the herbicide resistant or tolerant weed species is selected from: common branwort, annual bluegrass, and corn poppy.

[0073] In another embodiment, the herbicide resistant or tolerant weed species is branwort or corn poppy.

[0074] In another embodiment, the herbicide resistant or tolerant weed species is selected from black foxtail, branwort, wild oat, and annual bluegrass.

[0075] In another embodiment, the herbicide resistant or tolerant weed species is selected from black foxtail, branwort, and wild rye.

[0076] In another embodiment, the herbicide resistant or tolerant weed species is selected from black foxglove, common branwort, and annual bluegrass.

[0077] In another embodiment, the herbicide resistant or tolerant weed species is black foxtail or loosestrife.

[0078] In another embodiment, the herbicide resistant or tolerant weed species is black foxtail or bran, particularly black foxtail.

[0079] The methods, uses and compositions of the present invention are effective against ALS-resistant grass weeds, more particularly black-glove grass, common foxtail grass, common bran grass, wild oat, common wild oat, Brachiaria plantaginea, Brachiaria decumbens, common brome grass, common brome grass, common brome grass, large crabgrass, large crabgrass, northern crabgrass, large crabgrass, common wattle grass, and common oat. Barnyardgrass, Echinochloa crus-pavonis, Echinochloa erecta, Barnyardgrass, Barnyardgrass, Goosegrass, Taiwan grass, Leptochloa panicoides, Leptochloa scabra, Leptochloa virgata, Loose barnyardgrass, Ryegrass, Cornus gracilis, Oriental millet, Common millet, Phalaris brachystachys brachystachyx), reed canary grass, Phalaris paradoxa, annual bluegrass, longgrass, Poa annua, hornwort, foxtail, Japanese foxtail, golden foxtail, rough foxtail, and green foxtail, and preferably black foxtail, annual bluegrass, common bran, northern crabgrass, large crabgrass, barnyard grass, barnyard grass, Chinese watergrass, pigweed, ryegrass, ryegrass, oak, Phalaris brachystachys, reed canary grass, Phalaris paradoxa, annual bluegrass, Poa annua, hornwort, foxtail, golden foxtail, Setaria pumilla), rough foxtail, and green foxtail, more preferably selected from the group consisting of black foxtail, annual foxtail, bran nut, barnyard grass, barnyard grass, Chinese watergrass, loosegrass, ryegrass, ryegrass, Phalaris brachystachys, reed canary grass, Phalaris paradoxa, and annual bluegrass, particularly preferably selected from the group consisting of black foxtail, annual foxtail, barnyard grass, barnyard grass, barnyard grass, loosegrass, ryegrass, ryegrass, ryegrass, Phalaris paradoxa, and annual bluegrass, and particularly suitable for controlling ALS-resistant grass weeds selected from the group consisting of black foxtail, barnyard grass, ryegrass, ryegrass, and ryegrass.

[0080] The methods, uses and compositions of the present invention are effective against ALS-resistant dicotyledonous weeds, more specifically white birch, American redbud, narrow-leaved amaranthus, large brown amaranthus, long-legged amaranthus, redroot pigweed, water chestnut, Amaranthus rudis, common water chestnut, common ragweed, chamomile, shepherd's purse, common knapweed, common lamb's foot, common oak, Chenopodium polyspermum, parsley, ragweed, warbler, common mugwort, and ragweed (Descurania sophia), white spotted grass, cleaver, Japanese tortoiseshell, broom tree, chamomile, daisy, chamomile, corn poppy, wild radish, white mustard, field mustard, persimmon, mustard, chickweed, and shepherd's purse, and is preferably selected from the group consisting of redroot pigweed, beetroot, water chestnut, Amaranthus rudis, chamomile, shepherd's purse, cornflower, lamb's quarter, and ragwort (Descurania sophia), kochia, chamomile, Japanese anemone, corn poppy, persimmon, chickweed and shepherd's purse, more preferably selected from the group consisting of redroot pigweed, amaranthus retroflexus, water chestnut, Amaranthus rudis, lamb's quarter, chamomile, Japanese anemone, corn poppy and chickweed.

[0081] In particular, the methods, uses and compositions of the present invention are useful for the control of PSII-resistant grass weeds, more particularly black-glove weeds, common foxtail weeds, common bran, wild oat, wild oat, Brachiaria plantaginea, Brachiaria decumbens, common brome, common brome, common brome, large crabgrass, large crabgrass, common ... , Japanese barnyard grass, Echinochloa crus-pavonis, Echinochloa erecta, Barnyard grass, Barnyard grass, Goosegrass, Taiwan grass, Leptochloa panicoides, Leptochloa scabra, Leptochloa virgata, Loose barnyard grass, Ryegrass, Cornus gracilis, Common staghorn millet, Common staghorn millet, Phalaris brachystachys brachystachyx), reed canary grass, Phalaris paradoxa, annual bluegrass, longgrass, Poa annua, hornwort, foxtail, Japanese foxtail, golden foxtail, rough foxtail, and green foxtail, and preferably black foxtail, annual bluegrass, common bran, northern crabgrass, large crabgrass, barnyard grass, barnyard grass, Chinese watergrass, pigweed, ryegrass, ryegrass, oak, Phalaris brachystachys, reed canary grass, Phalaris paradoxa, annual bluegrass, Poa annua, hornwort, foxtail, golden foxtail, Setaria pumilla), rough foxtail, and green foxtail, more preferably selected from the group consisting of black foxtail, annual foxtail, European bran, barnyard grass, barnyard grass, Echinochloa crus-galli, barnyard grass, loosegrass, ryegrass, ryegrass, Phalaris brachystachys, reed canary grass, Phalaris paradoxa, and annual bluegrass, particularly preferably selected from the group consisting of black foxtail, annual foxtail, European bran, barnyard grass, barnyard grass, barnyard grass, loosegrass, barnyard grass, ryegrass, ryegrass, reed canary grass, and annual bluegrass, and is particularly suitable for controlling PSII-resistant grass weeds selected from the group consisting of black foxtail, barnyard grass, ryegrass, ryegrass, and reed canary grass.

[0082] The methods, uses and compositions of the present invention are effective against PSII-resistant dicotyledonous weeds, more specifically white birch, American blackbird, narrow-leaved amaranthus, large brown amaranthus, long-legged amaranthus, redroot pigweed, water chestnut, Amaranthus rudis, common water chestnut, common ragweed, chamomile, shepherd's purse, common knapweed, common lamb's foot, common oak, Chenopodium polyspermum, parsley, ragweed, warbler, common mugwort, and ragweed (Descurania sophia), white spotted grass, cleaver, Japanese tortoiseshell, broom tree, chamomile, daisy, chamomile, corn poppy, wild radish, white mustard, field mustard, persimmon, mustard, chickweed, and shepherd's purse, and preferably, redroot pigweed, beetroot, water chestnut, Amaranthus rudis, chamomile, shepherd's purse, cornflower, lamb's quarter, and ragwort (Descurania sophia), Kochia, Chamomile, British Columbia, Corn Poppy, Persimmon, Chickweed and Shepherd's Purse, more preferably Amaranthus retroflexus, Amaranthus retroflexus, Amaranthus rudis, Chenopodium album, Chamomile, British Columbia, Corn Poppy and Chickweed.

[0083] In one embodiment of the method / use of the present invention, herbicide A is applied alone, i.e. herbicide A is the only herbicidally active ingredient.

[0084] In another embodiment, the herbicide A is selected from the group b1) to b15): b1) lipid biosynthesis inhibitors, b2) acetolactate synthase inhibitors (ALS inhibitors), b3) photosynthesis inhibitors, b4) protoporphyrinogen-IX oxidase inhibitors; b5) bleaching herbicides; b6) enolpyruvylshikimate 3-phosphate synthase inhibitors (EPSP inhibitors), b7) glutamine synthetase inhibitors, b8) 7,8-dihydropteroate synthase inhibitors (DHP inhibitors), b9) mitotic inhibitors; b10) Very long-chain fatty acid synthesis inhibitors (VLCFA inhibitors), b11) cellulose biosynthesis inhibitors; b12) uncoupler herbicides; b13) synthetic auxins, b14) auxin transport inhibitors, and b15) Bromobutide, chlorflurenol, chlorflurenol-methyl, cumyluron, dalapon, dazomet, difenzoquat, difenzoquat-methyl sulfate, dimethipine, DSMA, dymron, endothal and its salts, etobenzanide, flamprop, flamprop-isopropyl, flamprop-methyl, flamprop-M-isopropyl, flamprop-M-methyl, flurenol, flurenol-butyl, flurprimidol, fosamine, fosamine-ammonium, indanofan, indaziflam, maleic hydrazide, mefluidide, metam, methiozoline (CAS 403640-27-7), other herbicides selected from the group consisting of methyl azide, methyl bromide, methyl-dymron, methyl iodide, MSMA, oleic acid, oxaziclomefone, pelargonic acid, pyributicarb, quinoclamine, triaziflam, tridiphane and 6-chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinol (CAS 499223-49-3), and salts and esters thereof; and agriculturally acceptable salts, esters or amides thereof It is applied in combination with at least one further herbicide B selected from

[0085] Preferably, the at least one herbicide B that can be used in combination with the herbicide A is b1) Lipid biosynthesis inhibitors: Alloxydim, Alloxydim-sodium, Butroxydim, Clethodim, Clodinafop, Clodinafop-propargyl, Cycloxydim, Cyhalofop, Cyhalofop-butyl, Diclofop, Diclofop-methyl, Fenoxaprop, Fenoxaprop-ethyl, Fenoxaprop-P, Fenoxaprop-P-ethyl, Fluazifop, Fluazifop-butyl, Fluazifop-P, Fluazifop-P-butyl, Haloxyfop, Haloxyfop-methyl, Haloxyfop-P, Haloxyfop ACC herbicides selected from quizalofop-P-methyl, metamifop, pinoxaden, profoxydim, propaquizafop, quizalofop, quizalofop-ethyl, quizalofop-tefuryl, quizalofop-P, quizalofop-P-ethyl, quizalofop-P-tefuryl, sethoxydim, tepraloxydim and tralkoxydim, 4-(4'-chloro-4-cyclopropyl-2'-fluoro[1,1'-biphenyl]-3-yl)-5-hydroxy-2,2,6,6-tetramethyl-2H-pyran-3(6H)-one (CAS 1312337-72-6; 4-(2',4'-dichloro-4-cyclopropyl[1,1'-biphenyl]-3-yl)-5-hydroxy-2,2,6,6-tetramethyl-2H-pyran-3(6H)-one (CAS 1312337-45-3); 4-(4'-chloro-4-ethyl-2'-fluoro[1,1'-biphenyl]-3-yl)-5-hydroxy-2,2,6,6-tetramethyl-2H-pyran-3(6H)-one (CAS 1033757-93-5); 4-(2',4'-dichloro-4-ethyl[1,1'-biphenyl]-3-yl)-2,2,6,6-tetramethyl-2H-pyran-3,5(4H,6H)-dione (CAS 1312340-84-3;5-(acetyloxy)-4-(4'-chloro-4-cyclopropyl-2'-fluoro[1,1'-biphenyl]-3-yl)-3,6-dihydro-2,2,6,6-tetramethyl-2H-pyran-3-one (CAS 1312337-48-6);5-(acetyloxy)-4-(2',4'-dichloro-4-cyclopropyl-[1,1'-biphenyl]-3-yl)-3,6-dihydro-2,2,6,6-tetramethyl-2H-pyran-3-one;5-(Acetyloxy)-4-(4'-chloro-4-ethyl-2'-fluoro[1,1'-biphenyl]-3-yl)-3,6-dihydro-2,2,6,6-tetramethyl-2H-pyran-3-one (CAS 1312340-82-1); 5-(Acetyloxy)-4-(2',4'-dichloro-4-ethyl[1,1'-biphenyl]-3-yl)-3,6-dihydro-2,2,6,6-tetramethyl-2H-pyran-3-one (CAS 1033760-55-2); 4-(4'-chloro-4-cyclopropyl-2'-fluoro[1,1'-biphenyl]-3-yl)-5,6-dihydro-2,2,6,6-tetramethyl-5-oxo-2H-pyran-3-ylcarboxylic acid methyl ester (CAS 1312337-51-1;4-(2',4'-dichloro-4-cyclopropyl-[1,1'-biphenyl]-3-yl)-5,6-dihydro-2,2,6,6-tetramethyl-5-oxo-2H-pyran-3-ylcarbonic acid methyl ester;4-(4'-chloro-4-ethyl-2'-fluoro[1,1'-biphenyl]-3-yl)-5,6-dihydro-2,2,6,6-tetramethyl-5-oxo-2H-pyran-3-ylcarbonic acid methyl ester (CAS 1312340-83-2);4-(2',4'-dichloro-4-ethyl[1,1'-biphenyl]-3-yl)-5,6-dihydro-2,2,6,6-tetramethyl-5-oxo-2H-pyran-3-ylcarbonic acid methyl ester (CAS 1033760-58-5); and non-ACC herbicides selected from benfuresate, butyrate, cycloate, dalapon, dimepiperate, EPTC, esprocarb, ethofumesate, flupropanate, molinate, orbencarb, pebulate, prosulfocarb, TCA, thiobencarb, thiocarbazyl, triallate, and vernolate; b2) ALS inhibitors: Amidosulfuron, azimsulfuron, bensulfuron, bensulfuron-methyl, chlorimuron, chlorimuron-ethyl, chlorsulfuron, cinosulfuron, cyclosulfamuron, ethametsulfuron, ethametsulfuron-methyl, ethoxysulfuron, flazasulfuron, flucetosulfuron, flupyrsulfuron, flupyrsulfuron-methyl-sodium, foramsulfuron, halosulfuron, halosulfuron-methyl, imazosulfuron, iodosulfuron, iodosulfuron-methyl-sodium, iofensulfuron, iofensulfuron-sodium, mesosulfuron, mesosulfuron sulfonylureas selected from pyrazosulfuron, primisulfuron-methyl, metazosulfuron, metsulfuron, metsulfuron-methyl, nicosulfuron, orthosulfamuron, oxasulfuron, primisulfuron, primisulfuron-methyl, propyrisulfuron, prosulfuron, pyrazosulfuron, pyrazosulfuron-ethyl, rimsulfuron, sulfometuron, sulfometuron-methyl, sulfosulfuron, thifensulfuron, thifensulfuron-methyl, triasulfuron, tribenuron, tribenuron-methyl, trifloxysulfuron, triflusulfuron, triflusulfuron-methyl and tritosulfuron; 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, penoxsulam, pyrimisulfan and pyroxsulam; pyrimidinyl benzoates selected from bispyribac, bispyribac-sodium, pyribenzoxim, pyriftalid, pyriminobac, pyriminobac-methyl, pyrithiobac, pyrithiobac-sodium, 4-[[[2-[(4,6-dimethoxy-2-pyrimidinyl)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), and N-(4-bromophenyl)-2-[(4,6-dimethoxy-2-pyrimidinyl)oxy]benzenemethanamine (CAS 420138-01-8); sulfonylaminocarbonyl-triazolinone herbicides selected from flucarbazone, flucarbazone-sodium, propoxycarbazone, propoxycarbazone-sodium, thiencarbazone and thiencarbazone-methyl, and triafamone, b3) Photosynthesis inhibitors: a triazine herbicide selected from ametryn, atrazine, cyanazine, desmetryn, dimethametryn, prometon, prometryn, propazine, simazine, simetryn, terbumeton, terbuthylazine, terbutryn, and trietazine; triazinones selected from hexazinone, metamitron and metribuzin; Triazolinones: amicarbazone, Pyridazinone: Chloridazon, ureas selected from chlorbromuron, chlorotoluron, chloroxuron, dimefuron, diuron, fluometuron, isoproturon, isouron, linuron, metamitron, methabenzthiazuron, metobenzuron, metoxuron, monolinuron, nebron, siduron, tebuthiuron and thidiazuron; phenylcarbamates selected from desmedipham, carbutilate, phenmedipham and phenmedipham-ethyl; a nitrile herbicide selected from bromofenoxime, bromoxynil, and ioxynil; uracils selected from bromacil, lenacil and terbacil; Bentazon, bentazon-sodium, pyridate, pyridahol, pentanochlor, propanil and a photosystem II inhibitor selected from diquat, diquat-dibromide, paraquat, paraquat-dichloride and paraquat-dimethylsulfate; b4) Protoporphyrinogen IX oxidase inhibitors: acifluorfen, acifluorfen-sodium, azafenidin, bencarbazone, benzfendizone, bifenox, butafenacil, carfentrazone, carfentrazone-ethyl, clomethoxyfen, cinidon-ethyl, fluazolate, flufenpyr, flufenpyr-ethyl, flumiclorac, flumiclorac-pentyl, flumioxazin, fluoroglycofen, fluoroglycofen-ethyl, fluthiacet, fluthiacet-me cil, fomesafen, halosafen, lactofen, oxadiargyl, oxadiazon, oxyfluorfen, pentoxazone, profluazole, pyraclonil, pyraflufen, pyraflufen-ethyl, saflufenacil, sulfentrazone, thidiazimine, thiafenacil, trifludimoxadine, ethyl [3-[2-chloro-4-fluoro-5-(1-methyl-6-trifluoromethyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-3-yl)phenoxy]-2-pyridyloxy]acetate (CAS 10141-10-1) 353292-31-6; S-3100), N-ethyl-3-(2,6-dichloro-4-trifluoromethylphenoxy)-5-methyl-1H-pyrazole-1-carboxamide (CAS 452098-92-9), N-tetrahydrofurfuryl-3-(2,6-dichloro-4-trifluoromethylphenoxy)-5-methyl-1H-pyrazole-1-carboxamide (CAS 915396-43-9), N-ethyl-3-(2-chloro-6-fluoro-4-trifluoromethylphenoxy)-5-methyl-1H-pyrazole-1-carboxamide (CAS 452099-05-7), N-tetrahydrofurfuryl-3-(2-chloro-6-fluoro-4-trifluoro-methylphenoxy)-5-methyl-1H-pyrazole-1-carboxamide (CAS 452100-03-7), 3-[7-fluoro-3-oxo-4-(prop-2-ynyl)-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl]-1,5-dimethyl-6-thioxo-[1,3,5]triazinane-2,4-dione (CAS 451484-50-7), 2-(2,2,7-trifluoro-3-oxo-4-prop-2-ynyl-3,4-dihydro- 1-methyl-6-trifluoromethyl-3-(2,2,7-trifluoro-3-oxo-4-prop-2-ynyl-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)-1H-pyrimidine-2,4-dione (CAS 1304113-05-0), methyl (E)-4-[2-chloro-5-[4-chloro-5-(difluoromethoxy)-1H-methyl-pyrazol-3-yl]-4-fluoro-phenoxy]-3-methoxy-but-2-enoate (CAS 948893-00-3), and 3-[7-chloro-5-fluoro-2-(trifluoromethyl)-1H-benzimidazol-4-yl]-1-methyl-6-(trifluoromethyl)-1H-pyrimidine-2,4-dione (CAS 212754-02-4); b5) bleaching herbicides: PDS inhibitors selected from beflubutamide, diflufenican, fluridone, flurochloridone, flurtamone, norflurazone, picolinafen, and 4-(3-trifluoromethylphenoxy)-2-(4-trifluoromethylphenyl)pyrimidine (CAS 180608-33-7); HPPD inhibitors selected from benzobicyclon, benzofenap, bicyclopyrone, fenquinotrione, isoxaflutole, isoxachlortole, mesotrione, pyrasulfotole, pyrazolinate, pyrazoxyfen, sulcotrione, tefuryltrione, tembotrione, tolpyralate and topramezone; DOXP synthase inhibitors selected from clomazone, a whitening agent of unknown target selected from aclonifen, amitrole and flumeturon; b6) EPSP synthase inhibitors: Glyphosate, glyphosate isopropylammonium, glyphosate potassium and glyphosate trimesium (sulfosate), b7) Glutamine synthase inhibitors: viranaphos (bialaphos), viranaphos-sodium, glufosinate, glufosinate-P and glufosinate-ammonium, b8) DHP synthase inhibitors: asulam, b9) Mitotic inhibitors: Compounds of the HRAC K1 group: dinitroanilines selected from benfluralin, butruarin, dinitramine, ethalfluralin, fluchloralin, oryzalin, pendimethalin, prodiamine and trifluralin, phosphoramidates selected from amiprophos, amiprophos-methyl and butamiphos, benzoic acid herbicides selected from chlorthal and chlorthal-dimethyl, pyridines selected from dithiopyr and thiazopyr, benzamides selected from propyzamide and tebutam, HRAC K2 group compounds: carbetamide, chlorpropham, flamprop, flamprop-isopropyl, flamprop-methyl, flamprop-M-isopropyl, flamprop-M-methyl and propham, b10) VLCFA inhibitors: chloroacetamides selected from acetochlor, alachlor, butachlor, dimethachlor, dimethenamid, dimethenamid-P, metazachlor, metolachlor, metolachlor-S, petoxamide, pretilachlor, propachlor, propisochlor and thenylchlor; oxyacetamides selected from flufenacet and mefenacet; Acetamides selected from diphenamide, naproanilide, napropamide and napropamide-M, tetrazolinones selected from fentrazamide and ipfencarbazone, other herbicides selected from anilophos, cafenstrole, fenoxasulfone, piperophos and pyroxasulfone, and herbicides of formula II.1, II.2, II.3, II.4, II.5, II.6, II.7, II.8 and II.9

[0086] [ka] an isoxazoline compound of the formula b11) Cellulose biosynthesis inhibitors: Chlorthiamid, dichlobenil, flupoxam, indaziflam, isoxaben, triaziflam and 1-cyclohexyl-5-pentafluorophenyloxy-1 4 -[1,2,4,6]thiatriazin-3-ylamine (CAS 175899-01-1), b12) Uncoupler herbicides: dinoseb, dinoterb and DNOC, b13) Synthetic auxins: 2,4-D, clacyfos, 2,4-DB, aminocyclopyrachlor, aminopyralid, aminopyralid-dimethylammonium, aminopyralid-tris(2-hydroxypropyl)ammonium, benazolin, benazolin-ethyl, chloramben, clomeprop, clopyralid, dicamba, dichlorprop, dichlorprop-P, fluroxypyr, fluroxypyr-butomethyl, fluroxypyr-meptyl, halaxifene (CAS 943832-60-8; MCPA, MCPA-thioethyl, MCPB, mecoprop, mecoprop-P, picloram, quinclorac, quinmerac, TBA(2,3,6), triclopyr, 4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)-5-fluoropyridine-2-carboxylic acid, and benzyl 4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)-5-fluoropyridine-2-carboxylate (CAS 1390661-72-9), b14) Auxin transport inhibitors: diflufenzopyr, diflufenzopyr-sodium, naptalam and naptalam-sodium; b15) Other herbicides: bromobutide, chlorflurenol, chlorflurenol-methyl, cumyluron, cyclopyrimorate (CAS 499223-49-3), dalapon, dazomet, difenzoquat, difenzoquat-methyl sulfate, dimethipine, DSMA, dymron, endothall, etobenzanide, flurenol, flurenol-butyl, flurprimidol, fosamine, fosamine-ammonium, indanofan, maleic hydrazide, mefluidide, metam, methiozoline (CAS 403640-27-7), methyl azide, methyl bromide, methyl-dymron, methyl iodide, MSMA, oleic acid, oxaziclomefone, pelargonic acid, pyributicarb, quinoclamine and tridiphane, and agriculturally acceptable salts, esters or amides thereof is selected from.

[0087] More preferably, the at least one herbicide B that can be used in combination with the herbicide A is selected from the group of b1) lipid biosynthesis inhibitors: Clethodim, clodinafop-propargyl, cycloxydim, cyhalofop-butyl, diclofop-methyl, fenoxaprop-p-ethyl, fluazifop-p-butyl, haloxyfop-p-methyl, metamifop, pinoxaden, profoxydim, propaquizafop, quizalofop-p-ethyl, quizalofop-p-tefuryl, sethoxydim, tepraloxydim, tralkoxydim, 4-(4'-chloro-4-cyclopropyl-2'-fluoro[1,1'-biphenyl]-3-yl)-5-hydroxy-2,2,6,6-tetramethyl-2H-pyran-3(6H)-one (CAS 1312337-72-6; 4-(2',4'-dichloro-4-cyclopropyl[1,1'-biphenyl]-3-yl)-5-hydroxy-2,2,6,6-tetramethyl-2H-pyran-3(6H)-one (CAS 1312337-45-3); 4-(4'-chloro-4-ethyl-2'-fluoro[1,1'-biphenyl]-3-yl)-5-hydroxy-2,2,6,6-tetramethyl-2H-pyran-3(6H)-one (CAS 1033757-93-5); 4-(2',4'-dichloro-4-ethyl[1,1'-biphenyl]-3-yl)-2,2,6,6-tetramethyl-2H-pyran-3,5(4H,6H)-dione (CAS 1312340-84-3;5-(acetyloxy)-4-(4'-chloro-4-cyclopropyl-2'-fluoro[1,1'-biphenyl]-3-yl)-3,6-dihydro-2,2,6,6-tetramethyl-2H-pyran-3-one (CAS 1312337-48-6);5-(acetyloxy)-4-(2',4'-dichloro-4-cyclopropyl-[1,1'-biphenyl]-3-yl)-3,6-dihydro-2,2,6,6-tetramethyl-2H-pyran-3-one;5-(acetyloxy)-4-(4'-chloro-4-ethyl-2'-fluoro[1,1'-biphenyl]-3-yl)-3,6-dihydro-2,2,6,6-tetramethyl-2H-pyran-3-one (CAS 1312340-82-1);5-(acetyloxy)-4-(2',4'-dichloro-4-ethyl[1,1'-biphenyl]-3-yl)-3,6-dihydro-2,2,6,6-tetramethyl-2H-pyran-3-one (CAS 1033760-55-2);4-(4'-chloro-4-cyclopropyl-2'-fluoro[1,1'-biphenyl]-3-yl)-5,6-dihydro-2,2,6,6-tetramethyl-5-oxo-2H-pyran-3-ylcarbonic acid methyl ester (CAS 1312337-51-1); 4-(2',4'-dichloro-4-cyclopropyl-[1,1'-biphenyl]-3-yl)-5,6-dihydro-2,2,6,6-tetramethyl-5-oxo-2H-pyran-3-ylcarbonic acid methyl ester; 4-(4'-chloro-4-ethyl-2'-fluoro[1,1'-biphenyl]-3-yl)-5,6-dihydro-2,2,6,6-tetramethyl-5-oxo-2H-pyran-3-ylcarbonic acid methyl ester (CAS 1312340-83-2;4-(2',4'-dichloro-4-ethyl[1,1'-biphenyl]-3-yl)-5,6-dihydro-2,2,6,6-tetramethyl-5-oxo-2H-pyran-3-ylcarbonic acid methyl ester (CAS 1033760-58-5);benfuresate, dimepiperate, EPTC, esprocarb, ethofumesate, molinate, orbencarb, prosulfocarb, thiobencarb and triallate; b2) ALS inhibitors: Amidosulfuron, azimsulfuron, bensulfuron-methyl, bispyribac-sodium, chlorimuron-ethyl, chlorsulfuron, cloransulam-methyl, cyclosulfamuron, diclosulam, ethametsulfuron-methyl, ethoxysulfuron, flazasulfuron, florasulam, flucarbazone-sodium, flucetosulfuron, flumetsulam, flupyrsulfuron-methyl-sodium, foramsulfuron, halosulfuron-methyl, imazamethabenz-methyl, imazamox, imazapic, imazapyr, imazaquin, imazethapyr, imazosulfuron, iodosulfuron, iodosulfuron-methyl-sodium, iofensulfuron, iofensulfuron-sodium, meso sulfuron, mesosulfuron-methyl, metazosulfuron, metosulam, metsulfuron-methyl, nicosulfuron, orthosulfamuron, oxasulfuron, penoxsulam, primisulfuron-methyl, propoxycarbazone-sodium, propyrisulfuron, prosulfuron, pyrazosulfuron-ethyl, pyribenzoxim, pyrimisulfan, pyriftalid, pyriminobac-methyl, pyrithiobac-sodium, pyroxsulam, rimsulfuron, sulfometuron-methyl, sulfosulfuron, thiencarbazone-methyl, thifensulfuron-methyl, triasulfuron, tribenuron-methyl, trifloxysulfuron, triflusulfuron-methyl, tritosulfuron and triafamone, b3) Group of photosynthesis inhibitors: ametryn, amicarbazone, atrazine, bentazone, bentazone-sodium, bromoxynil and its salts and esters, chloridazon, chlorotoluron, cyanazine, desmedipham, diquat-dibromide, diuron, fluometuron, hexazinone, ioxynil and its salts and esters, isoproturon, lenacil, linuron, metamitron, methabenzthiazuron, metribuzin, paraquat, paraquat-dichloride, phenmedipham, propanil, pyridate, simazine, terbutryn, terbuthylazine and thidiazuron, b4) Group of protoporphyrinogen-IX oxidase inhibitors: Acifluorfen-sodium, bencarbazone, benzfendizone, butafenacil, carfentrazone-ethyl, cinidon-ethyl, flufenpyr-ethyl, flumiclorac-pentyl, flumioxazin, fluoroglycofen-ethyl, fomesafen, lactofen, oxadiargyl, oxadiazon, oxyfluorfen, pentoxazone, pyraflufen, pyraflufen-ethyl, saflufenacil, sulfentrazone, thiafenacil, trifludimoxadine, ethyl [3-[2-chloro-4-fluoro-5-(1-methyl-6-trifluoromethyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-3-yl)phenoxy]-2-pyridyloxy]acetate (CAS 353292-31-6; S-3100), N-ethyl-3-(2,6-dichloro-4-trifluoromethylphenoxy)-5-methyl-1H-pyrazole-1-carboxamide (CAS 452098-92-9), N-tetrahydrofurfuryl-3-(2,6-dichloro-4-trifluoromethylphenoxy)-5-methyl-1H-pyrazole-1-carboxamide (CAS 915396-43-9), N-ethyl-3-(2-chloro-6-fluoro-4-trifluoromethylphenoxy)-5-methyl-1H-pyrazole-1-carboxamide (CAS 452099-05-7), N-tetrahydrofurfuryl-3-(2-chloro-6-fluoro-4-trifluoromethylphenoxy)-5-methyl-1H-pyrazole-1-carboxamide (CAS 452100-03-7), 3-[7-fluoro-3-oxo-4-(prop-2-ynyl)-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl]-1,5-dimethyl-6-thioxo-[1,3,5]triazinane-2,4-dione (CAS 451484-50-7), 2-(2,2,7-trifluoro-3-oxo-4-prop-2-ynyl-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)-4,5,6,7-tetrahydro-isoindole-1,3-dione (CAS 1300118-96-0);1-methyl-6-trifluoromethyl-3-(2,2,7-trifluoro-3-oxo-4-prop-2-ynyl-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)-1H-pyrimidine-2,4-dione (CAS 1304113-05-0), and 3-[7-chloro-5-fluoro-2-(trifluoromethyl)-1H-benzimidazol-4-yl]-1-methyl-6-(trifluoromethyl)-1H-pyrimidine-2,4-dione (CAS 212754-02-4); b5) Group of bleaching herbicides: Aclonifen, amitrole, beflubutamide, benzobicyclon, bicyclopyrone, clomazone, diflufenican, fenquinotrione, flumeturon, flurochloridone, flurtamone, isoxaflutole, isoxachlortole, mesotrione, norflurazon, picolinafen, pyrasulfotole, pyrazolinate, sulcotrione, tefuryltrione, tembotrione, tolpyralate, topramezone and 4-(3-trifluoromethylphenoxy)-2-(4-trifluoromethylphenyl)pyrimidine (CAS 180608-33-7), b6) group of EPSP synthase inhibitors: Glyphosate, glyphosate isopropylammonium, glyphosate potassium and glyphosate trimesium (sulfosate), b7) the group of glutamine synthase inhibitors; Glufosinate, glufosinate-P, glufosinate-ammonium, b8) The group of the DHP synthase inhibitors: asulam, b9) Mitotic inhibitors: Benfluralin, dithiopyr, ethalfluralin, flamprop, flamprop-isopropyl, flamprop-methyl, flamprop-M-isopropyl, flamprop-M-methyl, oryzalin, pendimethalin, thiazopyr and trifluralin, b10) VLCFA inhibitors: Acetochlor, alachlor, anilofos, butachlor, cafenstrole, dimethenamid, dimethenamid-P, fentrazamide, flufenacet, mefenacet, metazachlor, metolachlor, S-metolachlor, naproanilide, napropamide, napropamide-M, pretilachlor, fenoxasulfone, ipfencarbazone, pyroxasulfonthenylchlor, and the isoxazoline compounds of the above formulae II.1, II.2, II.3, II.4, II.5, II.6, II.7, II.8 and II.9, b11) the group of cellulose biosynthesis inhibitors: dichlobenil, flupoxam, indaziflam, isoxaben, triaziflam and 1-cyclohexyl-5-pentafluorophenyloxy-1 4 -[1,2,4,6]thiatriazin-3-ylamine (CAS 175899-01-1), b13) Group of synthetic auxins: 2,4-D and its salts and esters, aminocyclopyrachlor and its salts and esters, aminopyralid and its salts such as aminopyralid-dimethylammonium and aminopyralid-tris(2-hydroxypropyl)ammonium, and its esters, clopyralid and its salts and esters, dicamba and its salts and esters, dichlorprop-P and its salts and esters, fluroxypyr-meptyl, halaxifene and its salts and esters (CAS 943832-60-8), MCPA and its salts and esters, MCPB and its salts and esters, mecoprop-P and its salts and esters, picloram and its salts and esters, quinclorac, quinmerac, triclopyr and its salts and esters, 4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)-5-fluoropyridine-2-carboxylic acid and benzyl 4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)-5-fluoropyridine-2-carboxylate (CAS 1390661-72-9), b14) The group of auxin transport inhibitors: diflufenzopyr and diflufenzopyr-sodium, b15) Group of other herbicides: bromobutide, cumyluron, cyclopyrimorate (CAS 499223-49-3) and its salts and esters, dalapon, difenzoquat, difenzoquat methyl sulfate, DSMA, dymron (= daimuron), indanofan, metam, methyl bromide, MSMA, oxaziclomefone, pyributicarb and tridiphane is selected from.

[0088] Particularly preferably, the at least one herbicide B which can be used in combination with the herbicide A is selected from the group of the inhibitors of lipid biosynthesis: b1) clodinafop-propargyl, cycloxydim, cyhalofop-butyl, fenoxaprop-p-ethyl, pinoxaden, profoxydim, quizalofop-p-ethyl, tepraloxydim, tralkoxydim, 4-(4'-chloro-4-cyclopropyl-2'-fluoro[1,1'-biphenyl]-3-yl)-5-hydroxy-2,2,6,6-tetramethyl-2H-pyran-3(6H)-one (CAS 1312337-72-6); 4-(2',4'-dichloro-4-cyclopropyl[1,1'-biphenyl]-3-yl)-5-hydroxy-2,2,6,6-tetramethyl-2H-pyran-3(6H)-one (CAS 1312337-45-3;4-(4'-chloro-4-ethyl-2'-fluoro[1,1'-biphenyl]-3-yl)-5-hydroxy-2,2,6,6-tetramethyl-2H-pyran-3(6H)-one (CAS 1033757-93-5);4-(2',4'-dichloro-4-ethyl[1,1'-biphenyl]-3-yl)-2,2,6,6-tetramethyl-2H-pyran-3,5(4H,6H)-dione (CAS 1312340-84-3);5-(acetyloxy)-4-(4'-chloro-4-cyclopropyl-2'-fluoro[1,1'-biphenyl]-3-yl)-3,6-dihydro-2,2,6,6-tetramethyl-2H-pyran-3-one (CAS 1312337-48-6;5-(acetyloxy)-4-(2',4'-dichloro-4-cyclopropyl-[1,1'-biphenyl]-3-yl)-3,6-dihydro-2,2,6,6-tetramethyl-2H-pyran-3-one;5-(acetyloxy)-4-(4'-chloro-4-ethyl-2'-fluoro[1,1'-biphenyl]-3-yl)-3,6-dihydro-2,2,6,6-tetramethyl-2H-pyran-3-one (CAS 1312340-82-1);5-(acetyloxy)-4-(2',4'-dichloro-4-ethyl[1,1'-biphenyl]-3-yl)-3,6-dihydro-2,2,6,6-tetramethyl-2H-pyran-3-one (CAS 1033760-55-2);4-(4'-chloro-4-cyclopropyl-2'-fluoro[1,1'-biphenyl]-3-yl)-5,6-dihydro-2,2,6,6-tetramethyl-5-oxo-2H-pyran-3-ylcarbonic acid methyl ester (CAS 1312337-51-1); 4-(2',4'-dichloro-4-cyclopropyl-[1,1'-biphenyl]-3-yl)-5,6-dihydro-2,2,6,6-tetramethyl-5-oxo-2H-pyran-3-ylcarbonic acid methyl ester; 4-(4'-chloro-4-ethyl-2'-fluoro[1,1'-biphenyl]-3-yl)-5,6-dihydro-2,2,6,6-tetramethyl-5-oxo-2H-pyran-3-ylcarbonic acid methyl ester (CAS 1312340-83-2;4-(2',4'-dichloro-4-ethyl[1,1'-biphenyl]-3-yl)-5,6-dihydro-2,2,6,6-tetramethyl-5-oxo-2H-pyran-3-ylcarbonic acid methyl ester (CAS 1033760-58-5);Esprocarb, prosulfocarb, thiobencarb and triallate; b2) Group of ALS inhibitors: azimsulfuron, bensulfuron-methyl, bispyribac-sodium, cyclosulfamuron, diclosulam, ethametsulfuron-methyl, ethoxysulfuron, flumetsulam, flupyrsulfuron-methyl-sodium, foramsulfuron, imazamox, imazapic, imazapyr, imazaquin, imazethapyr, imazosulfuron, iodosulfuron, iodosulfuron-methyl-sodium, iofensulfuron, iofensulfuron-sodium, mesosulfuron, mesosulfuron-methyl, metazosulfuron, nicosulfuron, penoxsulam, propoxycarbazone-sodium, propyrisulfuron, pyrazosulfuron-ethyl, pyroxsulam, rimsulfuron, sulfosulfuron, thiencarbazone-methyl, tritosulfuron and triafamone, b3) Group of photosynthesis inhibitors: ametryn, atrazine, chlorotoluron, diuron, fluometuron, hexazinone, isoproturon, linuron, metribuzin, paraquat, paraquat-dichloride, propanil, terbutryn and terbuthylazine; b4) Group of protoporphyrinogen IX oxidase inhibitors: flumioxazin, oxyfluorfen, pyraflufen, pyraflufen-ethyl, saflufenacil, sulfentrazone, trifludimoxadine, ethyl [3-[2-chloro-4-fluoro-5-(1-methyl-6-trifluoromethyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-3-yl)phenoxy]-2-pyridyloxy]acetate (CAS 353292-31-6; S-3100), 3-[7-fluoro-3-oxo-4-(prop-2-ynyl)-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl]-1,5-dimethyl-6-thioxo-[1,3,5]triazinane-2,4-dione (CAS 451484-50-7), 2-(2,2,7-trifluoro-3-oxo-4-prop-2-ynyl-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)-4,5,6,7-tetrahydro-isoindole-1,3-dione (CAS 1300118-96-0), and 1-methyl-6-trifluoromethyl-3-(2,2,7-trifluoro-3-oxo-4-prop-2-ynyl-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)-1H-pyrimidine-2,4-dione (CAS 1304113-05-0); b5) group of bleaching herbicides: amitrole, bicyclopyrone, clomazone, diflufenican, fenquinotrione, flumeturon, flurtamone, flurochloridone, isoxaflutole, isoxachlorthole, mesotrione, picolinafen, sulcotrione, tefuryltrione, tembotrione, tolpyralate and topramezone; b6) The group of EPSP synthase inhibitors: glyphosate, glyphosate isopropylammonium, and glyphosate trimesium (sulfosate), b7) Group of the glutamine synthase inhibitors: glufosinate, glufosinate-P and glufosinate-ammonium, b9) The group of the antimitotic drugs: pendimethalin and trifluralin, b10) From the group of the VLCFA inhibitors: acetochlor, cafenstrole, dimethenamid-P, fentrazamide, flufenacet, mefenacet, metazachlor, metolachlor, S-metolachlor, fenoxasulfone, ipfencarbazone and pyroxasulfone, as well as the isoxazoline compounds of the above formulae II.1, II.2, II.3, II.4, II.5, II.6, II.7, II.8 and II.9, b11) the group of the cellulose biosynthesis inhibitors: indaziflam, isoxaben and triaziflam, b13) The group of synthetic auxins: 2,4-D and its salts and esters, such as clasifos, as well as aminocyclopyrachlor and its salts and esters, aminopyralid and its salts and esters, clopyralid and its salts and esters, dicamba and its salts and esters, fluroxypyr-meptyl, halaxifen, halaxifen-methyl, quinclorac, quinmerac, 4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)-5-fluoropyridine-2-carboxylic acid, and benzyl 4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)-5-fluoropyridine-2-carboxylate (CAS 1390661-72-9), b14) The group of auxin transport inhibitors: diflufenzopyr and diflufenzopyr-sodium, b15) Other group of herbicides: dymron (= daimuron), indanofan, oxaziclomefon is selected from.

[0089] In particular, the at least one herbicide B is selected from the herbicides B.1 to B.224, as listed below in Table B:

[0090] [Table 1] JPEG2026021457000004.jpg245143JPEG2026021457000005.jpg243144JPEG2026021457000006.jpg25143

[0091] In addition to herbicide A and optionally herbicide B, the method of the invention may further comprise the step of applying at least one safener C.

[0092] Thus, in one embodiment, the method of the invention comprises the step of applying a herbicide A, at least one safener C and optionally at least one herbicide B.

[0093] In another embodiment, the method of the invention comprises the step of applying a herbicide A, at least one herbicide B and at least one safener C.

[0094] Safeners are compounds that prevent or reduce damage to useful plants without significantly affecting the herbicidal action of herbicidal active ingredients on undesirable plants. Safeners can be applied before sowing (e.g., seed treatment), to sprouts or seedlings, and also in pre- or post-emergence treatment of useful plants and their habitat.

[0095] Suitable safeners include, for example, (quinoline-8-oxy)acetic acids, 1-phenyl-5-haloalkyl-1H-1,2,4-triazole-3-carboxylic acids, 1-phenyl-4,5-dihydro-5-alkyl-1H-pyrazole-3,5-dicarboxylic acids, 4,5-dihydro-5,5-diaryl-3-isoxazolecarboxylic acids, dichloroacetamides, alpha-oximinophenylacetonitriles, acetophenone oximes, 4,6-di Halo-2-phenylpyrimidines, N-[[4-(aminocarbonyl)phenyl]sulfonyl]-2-benzamides, 1,8-naphthalic anhydride, 2-halo-4-(haloalkyl)-5-thiazolecarboxylic acids, phosphorthiolates and N-alkyl-O-phenylcarbamates, and agriculturally acceptable salts thereof, as well as agriculturally acceptable derivatives thereof, such as amides, esters and thioesters, provided that they contain an acidic group.

[0096] Examples of preferred safeners C are benoxacor, cloquintocet, siometrinil, cyprosulfamide, dichlormid, dicyclonon, dietholate, fenchlorazole, fenclorim, flurazole, fluxofenim, furilazole, isoxadifen, mefenpyr, mephenate, naphthaleneacetic acid (NAA), naphthalic 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 52836-31-4), N-(2-methoxybenzoyl)-4-[(methylaminocarbonyl)amino]benzenesulfonamide (CAS 129531-12-0) and agriculturally acceptable salts, esters or amides thereof.

[0097] Particularly preferred safeners C are benoxacor, cloquintocet, cyprosulfamide, dichlormid, fenchlorazole, fenclorim, flurazole, fluxofenim, furilazole, isoxadifen, mefenpyr, naphthalic 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 52836-31-4), N-(2-methoxybenzoyl)-4-[(methylaminocarbonyl)amino]benzenesulfonamide (CAS 129531-12-0) and agriculturally acceptable salts, esters or amides thereof.

[0098] In particular, the at least one safener C is selected from the safeners C.1 to C.17, as listed below in Table C:

[0099] [Table 2]

[0100] Herbicide B and safener C are known herbicides and safeners, see, e.g., The Pesticide Manual, British Crop Protection Council, 16th Edition, 2012; The Compendium of Pesticide Common Names (http: / / www.alanwood.net / pesticides / ); Farm Chemicals Handbook 2000, Vol. 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 Edition, Weed Science Society of America, 1994; and K.K. Hatzios, Herbicide Handbook, Supplement for the 7th edition, Weed Science Society of America, 1998. 2,2,5-Trimethyl-3-(dichloroacetyl)-1,3-oxazolidine [CAS No. 52836-31-4] is also known as R-29148. 4-(Dichloroacetyl)-1-oxa-4-azaspiro[4.5]decane [CAS No. 71526-07-3] is also known as AD-67 and MON4660.

[0101] Where the herbicides B and / or safeners C described herein can form geometric isomers, such as E / Z isomers, both the pure isomers and mixtures thereof can be used in the methods, uses and compositions according to the invention.

[0102] Where the herbicides B and / or safeners C described herein have one or more chiral centers and consequently exist as enantiomers or diastereomers, both the pure enantiomers and diastereomers and mixtures thereof can be used in the methods, uses and compositions according to the invention.

[0103] When the herbicide B and / or safener C described herein have an ionic functional group, they can also be used in the form of an agriculturally acceptable salt. The term "agriculturally acceptable salt" is generally used herein to mean a salt of a cation and an acid addition salt of an acid whose cation and anion, respectively, do not adversely affect the herbicidal activity of the active compound.

[0104] Preferred cations are alkali metal ions, preferably lithium, sodium and potassium ions, alkaline earth metal ions, preferably calcium and magnesium ions, and transition metal ions, preferably manganese, copper, zinc and iron ions, as well as ammonium and substituted ammonium ions in which one to four hydrogen atoms are replaced by C1-C4-alkyl, hydroxy-C1-C4-alkyl, C1-C4-alkoxy-C1-C4-alkyl, hydroxy-C1-C4-alkoxy-C1-C4-alkyl, phenyl or benzyl, preferably ammonium, methylammonium, isopropylammonium, dimethylammonium, diisopropylammonium, trimethylammonium, heptylammonium, dodecylammonium, tetradecylammonium, tetramethylammonium, tetraethylammonium. , tetrabutylammonium, 2-hydroxyethylammonium (olamine salts), 2-(2-hydroxyeth-1-oxy)eth-1-ylammonium (diglycolamine salts), di(2-hydroxyeth-1-yl)ammonium (diolamine salts), tris(2-hydroxyethyl)ammonium (trolamine salts), tris(2-hydroxypropyl)ammonium, benzyltrimethylammonium, benzyltriethylammonium, N,N,N-trimethylethanolammonium (choline salts), also phosphonium ions, sulfonium ions, preferably tri(C1-C4-alkyl)sulfonium, such as trimethylsulfonium, and sulfoxonium ions, preferably tri(C1-C4-alkyl)sulfoxonium, and finally polybasic amine salts such as N,N-bis-(3-aminopropyl)methylamine and diethylenetriamine.

[0105] Useful anions of acid addition salts are primarily chloride, bromide, fluoride, iodide, hydrogensulfate, methylsulfate, sulfate, dihydrogenphosphate, hydrogenphosphate, nitrate, bicarbonate, carbonate, hexafluorosilicate, hexafluorophosphate, benzoate, and anions of C1-C4-alkanoic acids, preferably formate, acetate, propionate, and butyrate.

[0106] The herbicides B and / or safeners C described herein, which have carboxyl, hydroxy and / or amino groups, may be used in the form of acids, in the form of agriculturally suitable salts as described above, or in the form of agriculturally acceptable derivatives, for example as amides, such as mono- and di-C1-C6-alkylamides or arylamides, as esters, for example as allyl esters, propargyl esters, C1-C6 alkyl ... 10 as alkyl esters, alkoxyalkyl esters, tefuryl((tetrahydrofuran-2-yl)methyl) esters and as thioesters, for example C1-C 10 -alkylthioesters can be used. Preferred mono- and di-C1-C6-alkylamides are methyl and dimethylamides. Preferred arylamides are, for example, anilides and 2-chloroanilides. Preferred alkyl esters are, for example, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, pentyl, mexyl (1-methylhexyl), meptyl (1-methylheptyl), heptyl, octyl or isooctyl (2-ethylhexyl) esters. Preferred C1-C4-alkoxy-C1-C4-alkyl esters are linear or branched C1-C4-alkoxyethyl esters, for example 2-methoxyethyl, 2-ethoxyethyl, 2-butoxyethyl (butotyl), 2-butoxypropyl or 3-butoxypropyl esters. Linear or branched C1-C 10 An example of an alkyl thioester is the ethyl thioester.

[0107] In the case of dicamba, suitable salts include those in which the counterion is an agriculturally acceptable cation. For example, suitable salts of dicamba are dicamba-sodium, dicamba-potassium, dicamba-methylammonium, dicamba-dimethylammonium, dicamba-isopropylammonium, dicamba-diglycolamine, dicamba-olamine, dicamba-diolamine, dicamba-trolamine, dicamba-N,N-bis-(3-aminopropyl)methylamine, and dicamba-diethylenetriamine. Examples of suitable esters are dicamba-methyl and dicamba-butotyl.

[0108] Suitable salts of 2,4-D are 2,4-D-ammonium, 2,4-D-dimethylammonium, 2,4-D-diethylammonium, 2,4-D-diethanolammonium (2,4-D-diolamine), 2,4-D-triethanolammonium, 2,4-D-isopropylammonium, 2,4-D-triisopropanolammonium, 2,4-D-heptylammonium, 2,4-D-dodecylammonium, 2,4-D-tetradecylammonium, 2,4-D-triethylammonium, 2,4-D-tris(2-hydroxypropyl)ammonium, 2,4-D-tris(isopropyl)ammonium, 2,4-D-trolamine, 2,4-D-lithium, and 2,4-D-sodium. Examples of suitable 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 clasifos.

[0109] Suitable salts of 2,4-DB are, for example, 2,4-DB-sodium, 2,4-DB-potassium, and 2,4-DB-dimethylammonium. Suitable esters of 2,4-DB are, for example, 2,4-DB-butyl and 2,4-DB-isooctyl.

[0110] Suitable salts of dichlorprop are, for example, dichlorprop-sodium, dichlorprop-potassium and dichlorprop-dimethylammonium. Examples of suitable esters of dichlorprop are dichlorprop-butotyl and dichlorprop-isooctyl.

[0111] Suitable salts and esters of MCPA include MCPA-butotyl, MCPA-butyl, MCPA-dimethylammonium, MCPA-diolamine, MCPA-ethyl, MCPA-thioethyl, MCPA-2-ethylhexyl, MCPA-isobutyl, MCPA-isooctyl, MCPA-isopropyl, MCPA-isopropylammonium, MCPA-methyl, MCPA-olamine, MCPA-potassium, MCPA-sodium, and MCPA-trolamine.

[0112] A suitable salt of MCPB is sodium MCPB. A suitable ester of MCPB is MCPB-ethyl.

[0113] Suitable salts of clopyralid are clopyralid-potassium, clopyralid-olamine and clopyralid-tris-(2-hydroxypropyl)ammonium. An example of a suitable ester of clopyralid is clopyralid-methyl.

[0114] Examples of suitable esters of fluroxypyr are fluroxypyr-meptyl and fluroxypyr-2-butoxy-1-methylethyl, with fluroxypyr-meptyl being preferred.

[0115] Suitable salts of picloram are picloram-dimethylammonium, picloram-potassium, picloram-triisopropanolammonium, picloram-triisopropylammonium and picloram-trolamine. A suitable ester of picloram is picloram-isooctyl.

[0116] A suitable salt of triclopyr is triclopyr-triethylammonium. Suitable esters of triclopyr are, for example, triclopyr-ethyl and triclopyr-butotyl.

[0117] 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-potassium, and 2,3,6-TBA-sodium.

[0118] Suitable salts and esters of aminopyralid include aminopyralid-potassium and aminopyralid-tris(2-hydroxypropyl)ammonium.

[0119] Suitable salts of glyphosate are, for example, glyphosate ammonium, glyphosate diammonium, glyphosate dimethylammonium, glyphosate isopropylammonium, glyphosate potassium, glyphosate sodium, glyphosate trimesium, and the ethanolamine and diethanolamine salts, preferably glyphosate diammonium, glyphosate isopropylammonium and glyphosate trimesium (sulfosate).

[0120] A suitable salt of glufosinate is, for example, glufosinate-ammonium.

[0121] A suitable salt of glufosinate-P is, for example, glufosinate-P-ammonium.

[0122] Suitable salts and esters of bromoxynil are, for example, bromoxynil-butyrate, bromoxynil-heptanoate, bromoxynil-octanoate, bromoxynil-potassium and bromoxynil-sodium.

[0123] Suitable salts and esters of ioxynil are, for example, ioxynil-octanoate, ioxynil-potassium and ioxynil-sodium.

[0124] Suitable salts and esters of mecoprop include mecoprop-butotyl, mecoprop-dimethylammonium, mecoprop-diolamine, mecoprop-ethadyl, mecoprop-2-ethylhexyl, mecoprop-isooctyl, mecoprop-methyl, mecoprop-potassium, mecoprop-sodium, and mecoprop-trolamine.

[0125] Suitable salts of mecoprop-P are, for example, mecoprop-P-butotyl, mecoprop-P-dimethylammonium, mecoprop-P-2-ethylhexyl, mecoprop-P-isobutyl, mecoprop-P-potassium and mecoprop-P-sodium.

[0126] A suitable salt of diflufenzopyr is, for example, diflufenzopyr sodium.

[0127] A suitable salt of naptalam is, for example, naptalam-sodium.

[0128] Suitable salts and esters of aminocyclopyrachlor are, for example, aminocyclopyrachlor-dimethylammonium, aminocyclopyrachlor-methyl, aminocyclopyrachlor-triisopropanolammonium, aminocyclopyrachlor-sodium and aminocyclopyrachlor-potassium.

[0129] A suitable salt of quinclorac is, for example, quinclorac-dimethylammonium.

[0130] A suitable salt of quinmerac is, for example, quinclorac-dimethylammonium.

[0131] A suitable salt of imazamox is, for example, imazamox-ammonium.

[0132] Suitable salts of imazapic are, for example, imazapic-ammonium and imazapic-isopropylammonium.

[0133] Suitable salts of imazapyr are, for example, imazapyr-ammonium and imazapyr-isopropylammonium.

[0134] A suitable salt of imazaquin is, for example, imazaquin-ammonium.

[0135] Suitable salts of imazethapyr are, for example, imazethapyr-ammonium and imazethapyr-isopropylammonium.

[0136] A suitable salt of topramezone is, for example, topramezone-sodium.

[0137] In another embodiment of the method or use of the invention, a composition is applied comprising a herbicidally effective amount of herbicide A (in particular (±)-2-exo-(2-methylbenzyloxy)-1-methyl-4-isopropyl-7-oxabicyclo[2.2.1]heptane). In yet another embodiment, the composition further comprises at least one herbicide B (as defined herein).

[0138] Thus, in another embodiment of the method or use of the present invention, a composition comprising a herbicidally effective amount of herbicide A and optionally at least one herbicide B (as defined herein) is applied. In a preferred embodiment of the method or use of the present invention, a composition comprising a herbicidally effective amount of herbicide A and at least one herbicide B (as defined herein) is applied. In yet another embodiment of the method or use of the present invention, a composition comprising a herbicidally effective amount of herbicide A and at least one herbicide B (as defined herein) is applied, wherein herbicide A and herbicide B are the only active ingredients.

[0139] In another embodiment, the composition comprises a herbicidally effective amount of a herbicide A (in particular (±)-2-exo-(2-methylbenzyloxy)-1-methyl-4-isopropyl-7-oxabicyclo[2.2.1]heptane) and at least one herbicide B selected from lipid biosynthesis inhibitors (group b1 as defined herein). These are compounds that inhibit lipid biosynthesis. The inhibition of lipid biosynthesis can be effected either through the inhibition of acetyl-CoA carboxylase (hereinafter referred to as ACC herbicides) or through another mode of action (hereinafter referred to as non-ACC herbicides). ACC herbicides belong to group A of the HRAC classification system, and non-ACC herbicides belong to group N of the HRAC classification.

[0140] In another embodiment, the composition comprises a herbicidally effective amount of a herbicide A (in particular (±)-2-exo-(2-methylbenzyloxy)-1-methyl-4-isopropyl-7-oxabicyclo[2.2.1]heptane) and at least one herbicide B selected from ALS inhibitors (group b2 as defined herein). The herbicidal activity of these compounds is based on the inhibition of acetolactate synthase and therefore branched-chain amino acid biosynthesis. These inhibitors belong to group B of the HRAC classification system.

[0141] In another embodiment, the composition comprises a herbicidally effective amount of a herbicide A (in particular (±)-2-exo-(2-methylbenzyloxy)-1-methyl-4-isopropyl-7-oxabicyclo[2.2.1]heptane) and at least one herbicide B selected from photosynthesis inhibitors (group b3 as defined herein). The herbicidal activity of these compounds is based either on the inhibition of photosystem II in plants (so-called PSII inhibitors, groups C1, C2 and C3 of the HRAC classification) or on the diversion of electron transport in photosystem I in plants (so-called PSI inhibitors, group D of the HRAC classification), and thus on the inhibition of photosynthesis. Among these, PSII inhibitors are preferred.

[0142] In another embodiment, the composition comprises a herbicidally effective amount of a herbicide A (in particular (±)-2-exo-(2-methylbenzyloxy)-1-methyl-4-isopropyl-7-oxabicyclo[2.2.1]heptane) and at least one herbicide B selected from protoporphyrinogen-IX oxidase inhibitors (group b4 as defined herein). The herbicidal activity of these compounds is based on the inhibition of protoporphyrinogen-IX oxidase. These inhibitors belong to group E of the HRAC classification system.

[0143] In another embodiment, the composition comprises a herbicidally effective amount of a herbicide A (in particular (±)-2-exo-(2-methylbenzyloxy)-1-methyl-4-isopropyl-7-oxabicyclo[2.2.1]heptane) and at least one herbicide B selected from bleaching agents (group b5 as defined herein). The herbicidal activity of these compounds is based on the inhibition of carotenoid biosynthesis. These include compounds that inhibit carotenoid biosynthesis by inhibiting phytoene desaturase (so-called PDS inhibitors, group F1 of the HRAC classification), compounds that inhibit 4-hydroxyphenylpyruvate dioxygenase (HPPD inhibitors, group F2 of the HRAC classification), compounds that inhibit DOX synthase (group F4 of the HRAC class), and compounds that inhibit carotenoid biosynthesis through an unknown mode of action (bleaching agents - target unknown, group F3 of the HRAC classification).

[0144] In another embodiment, the composition comprises a herbicidally effective amount of a herbicide A (in particular (±)-2-exo-(2-methylbenzyloxy)-1-methyl-4-isopropyl-7-oxabicyclo[2.2.1]heptane) and at least one herbicide B selected from EPSP synthase inhibitors (group b6 as defined herein). The herbicidal activity of these compounds is based on the inhibition of enolpyruvylshikimate 3-phosphate synthase and therefore of amino acid biosynthesis in plants. These inhibitors belong to group G of the HRAC classification system.

[0145] In another embodiment, the composition comprises a herbicidally effective amount of a herbicide A (in particular (±)-2-exo-(2-methylbenzyloxy)-1-methyl-4-isopropyl-7-oxabicyclo[2.2.1]heptane) and at least one herbicide B selected from glutamine synthetase inhibitors (group b7 as defined herein). The herbicidal activity of these compounds is based on the inhibition of glutamine synthetase and therefore of amino acid biosynthesis in plants. These inhibitors belong to group H of the HRAC classification system.

[0146] In another embodiment, the composition comprises a herbicidally effective amount of a herbicide A (in particular (±)-2-exo-(2-methylbenzyloxy)-1-methyl-4-isopropyl-7-oxabicyclo[2.2.1]heptane) and at least one herbicide B selected from DHP synthase inhibitors (group b8 as defined herein). The herbicidal activity of these compounds is based on the inhibition of 7,8-dihydropteroate synthase. These inhibitors belong to group I of the HRAC classification system.

[0147] In another embodiment, the composition comprises a herbicidally effective amount of a herbicide A (in particular (±)-2-exo-(2-methylbenzyloxy)-1-methyl-4-isopropyl-7-oxabicyclo[2.2.1]heptane) and at least one herbicide B selected from mitotic inhibitors (group b9 as defined herein). The herbicidal activity of these compounds is based on the disruption or inhibition of microtubule formation or assembly, and thus on the inhibition of mitosis. These inhibitors belong to groups K1 and K2 of the HRAC classification system. Among these, compounds of group K1, in particular dinitroanilines, are preferred.

[0148] In another embodiment, the composition comprises a herbicidally effective amount of a herbicide A (in particular (±)-2-exo-(2-methylbenzyloxy)-1-methyl-4-isopropyl-7-oxabicyclo[2.2.1]heptane) and at least one herbicide B selected from VLCFA inhibitors (group b10 as defined herein). The herbicidal activity of these compounds is based on the inhibition of very long chain fatty acid synthesis and thus on the disruption or inhibition of cell division in plants. These inhibitors belong to group K3 of the HRAC classification system.

[0149] In another embodiment, the composition comprises a herbicidally effective amount of a herbicide A (in particular (±)-2-exo-(2-methylbenzyloxy)-1-methyl-4-isopropyl-7-oxabicyclo[2.2.1]heptane) and at least one herbicide B selected from cellulose biosynthesis inhibitors (group b11 as defined herein). The herbicidal activity of these compounds is based on the inhibition of cellulose biosynthesis and therefore cell wall synthesis in plants. These inhibitors belong to group L of the HRAC classification system.

[0150] In another embodiment, the composition comprises a herbicidally effective amount of a herbicide A (in particular (±)-2-exo-(2-methylbenzyloxy)-1-methyl-4-isopropyl-7-oxabicyclo[2.2.1]heptane) and at least one herbicide B selected from uncoupler herbicides (group b12 as defined herein). The herbicidal activity of these compounds is based on the disruption of cell membranes. These inhibitors belong to group M of the HRAC classification system.

[0151] In another embodiment, the composition comprises a herbicidally effective amount of a herbicide A (in particular (±)-2-exo-(2-methylbenzyloxy)-1-methyl-4-isopropyl-7-oxabicyclo[2.2.1]heptane) and at least one herbicide B selected from synthetic auxins (group b13 as defined herein). These include compounds that mimic auxins, i.e., plant hormones, and affect plant growth. These compounds belong to group O of the HRAC classification system.

[0152] In another embodiment, the composition comprises a herbicidally effective amount of a herbicide A (in particular (±)-2-exo-(2-methylbenzyloxy)-1-methyl-4-isopropyl-7-oxabicyclo[2.2.1]heptane) and at least one herbicide B selected from auxin transport inhibitors (group b14 as defined herein). The herbicidal activity of these compounds is based on the inhibition of auxin transport in plants. These compounds belong to group P of the HRAC classification system.

[0153] For a given mechanism of action and classification for an active substance, see, e.g., "HRAC (Herbicide Resistance Action Committee), Classification of Herbicides According to Site of Action," http: / / www.hracglobal.com / pages / classificationofherbicidesiteofaction.aspx.

[0154] In another aspect of the present invention, there is provided 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), and (b) at least one herbicide B selected from acetyl-CoA carboxylase inhibitors (ACCase inhibitors). Preferably, the ACCase inhibitor is selected from aryloxyphenoxypropionates, cyclohexanediones, and phenylpyrazolines. More preferably, the ACCase inhibitor is clodinafop, clodinafop-propargyl, cyhalofop, cyhalofop-butyl, diclofop, diclofop-methyl, 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, propaquizafop, quizalofop, quizalofop-ethyl, quizalofop-tefuryl, quizalofop-P, quizalofop-P-ethyl, quizalofop-P-tefuryl, alloxydim, allo The active ingredient is selected from the group consisting of quizalofop-sodium, butroxydim, clethodim, cycloxydim, profoxydim, sethoxydim, tepraloxydim, tralkoxydim, pinoxaden, and agriculturally acceptable salts, esters, or amides thereof, and more preferably selected from the group consisting of clethodim, clodinafop-propargyl, cycloxydim, cyhalofop-butyl, diclofop-methyl, fenoxaprop-p-ethyl, fluazifop-p-butyl, haloxyfop-p-methyl, metamifop, pinoxaden, profoxydim, propaquizafop, quizalofop-p-ethyl, quizaloxyfop-p-tefuryl, sethoxydim, tepraloxydim, and tralkoxydim.In one embodiment the ACCase inhibitor is selected from aryloxyphenoxypropionates, in particular clodinafop, clodinafop-propargyl, cyhalofop, cyhalofop-butyl, diclofop, diclofop-methyl, 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, propaquizafop, quizalofop, quizalofop-ethyl, quizalofop-tefuryl, quizalofop-P, quizalofop-P-ethyl and quizalofop-P-tefuryl, more preferably selected from the group consisting of clodinafop-propargyl, cyhalofop-butyl, diclofop-methyl, fenoxaprop-P-ethyl, fluazifop-P-butyl, haloxyfop-P-methyl, metamifop, propaquizafop, quizalofop-P-ethyl and quizalofop-P-tefuryl. In another embodiment, the ACCase inhibitor is selected from cyclohexanediones, in particular from the group consisting of alloxydim, alloxydim-sodium, butroxydim, clethodim, cycloxydim, profoxydim, sethoxydim, tepraloxydim, and tralkoxydim, more preferably from the group consisting of clethodim, cycloxydim, profoxydim, tepraloxydim, and tralkoxydim, hi yet another embodiment, the ACCase inhibitor is pinoxaden.

[0155] In yet another embodiment the ACCase inhibitor is selected from cyhalofop, cyhalofop-butyl, quizalofop and quizalofop-P-ethyl, more preferably cyhalofop-butyl and quizalofop-P-ethyl.

[0156] In yet another embodiment, the ACCase inhibitor is cyhalofop or cyhalofop-butyl, particularly cyhalofop-butyl.

[0157] In yet another embodiment the ACCase inhibitor is quizalofop or quizalofop-P-ethyl, in particular quizalofop-P-ethyl.

[0158] In yet another aspect of the present invention, there is provided 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), and (b) at least one herbicide B selected from sulfonylureas. Preferably, the sulfonylurea is selected from amidosulfuron, azimsulfuron, bensulfuron, bensulfuron-methyl, chlorimuron, chlorimuron-ethyl, chlorsulfuron, cinosulfuron, cyclosulfamuron, ethametsulfuron, ethametsulfuron-methyl, ethoxysulfuron, flazasulfuron, flucetosulfuron, flupyrsulfuron, flupyrsulfuron-methyl-sodium, foramsulfuron, halos ... Sulfuron-methyl, imazosulfuron, iodosulfuron, iodosulfuron-methyl-sodium, iofensulfuron, iofensulfuron-sodium, mesosulfuron, mesosulfuron-methyl, metazosulfuron, metsulfuron, metsulfuron-methyl, nicosulfuron, orthosulfamuron, oxasulfuron, primisulfuron, primisulfuron-methyl, propyrisulfuron, prosulfuron, pyrazosulfuron, It is selected from the group consisting of pyrazosulfuron-ethyl, rimsulfuron, sulfometuron, sulfometuron-methyl, sulfosulfuron, thifensulfuron, thifensulfuron-methyl, triasulfuron, tribenuron, tribenuron-methyl, trifloxysulfuron, triflusulfuron, triflusulfuron-methyl, tritosulfuron, and agriculturally acceptable salts, esters, and amides thereof, and more preferably selected from the group consisting of azimsulfuron, bensulfuron-methyl, cyclosulfamuron, ethametsulfuron-methyl, ethoxysulfuron, flupyrsulfuron-methyl-sodium, foramsulfuron, halosulfuron-methyl, iodosulfuron-methyl-sodium, mesosulfuron-methyl, nicosulfuron, pyrazosulfuron-ethyl, rimsulfuron, sulfosulfuron, tritosulfuron, and agriculturally acceptable salts, esters, and amides thereof.

[0159] In yet another embodiment, the sulfonylurea is metsulfuron or metsulfuron-methyl, particularly metsulfuron-methyl.

[0160] In yet another aspect of the present invention, there is provided 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), and (b) at least one herbicide B selected from triazolopyrimidines. Preferably, the triazolopyrimidine is selected from the group consisting of cloransulam, diclosulam, florasulam, flumetsulam, metosulam, penoxsulam, pyrimisulfan, pyroxsulam, and agriculturally acceptable salts, esters, or amides thereof. More preferably, the triazolopyrimidine is selected from the group consisting of cloransulam, diclosulam, florasulam, flumetsulam, metosulam, penoxsulam, piroxsulam, and agriculturally acceptable salts, esters, or amides thereof, and even more preferably from the group consisting of florasulam, penoxsulam, piroxsulam, and agriculturally acceptable salts, esters, or amides thereof. In particular, the triazolopyrimidine is piroxsulam. In another embodiment, the triazolopyrimidine is penoxsulam or pyrimisulfan.

[0161] In yet another aspect of the present invention, there is provided 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), and (b) at least one herbicide B selected from sulfonylaminocarbonyl-triazolinones. Preferably, the sulfonylaminocarbonyl-triazolinone is selected from the group consisting of flucarbazone, propoxycarbazone, thiencarbazone, and agriculturally acceptable salts, esters, or amides thereof.

[0162] In yet another aspect of the present invention, there is provided 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), and (b) at least one herbicide B selected from pyrimidinyl benzoates. Preferably, the pyrimidinyl benzoate is selected from the group consisting of bispyribac, pyribenzoxim, pyriftalid, pyriminobac, pyrithiobac, 4-[[[2-[(4,6-dimethoxy-2-pyrimidinyl)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), and agriculturally acceptable salts, esters or amides thereof. More preferably, the pyrimidinyl benzoate is selected from the group consisting of bispyribac, pyribenzoxim, pyriftalid, pyriminobac, and agriculturally acceptable salts, esters, or amides thereof. In particular, the pyrimidinyl benzoate is selected from the group consisting of bispyribac, bispyribac-sodium, pyribenzoxim, pyriftalid, pyriminobac, and pyriminobac-methyl.

[0163] In yet another aspect of the present invention, there is provided 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), and (b) at least one herbicide B selected from photosystem II inhibitors. Preferably, the photosystem II inhibitor is bentazone, propanil, or an agriculturally acceptable salt, ester, or amide thereof. In one embodiment, the photosystem II inhibitor is bentazone-sodium. In another embodiment, the photosystem II inhibitor is propanil.

[0164] In yet another aspect of the present invention, there is provided 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), and (b) at least one herbicide B selected from a protoporphyrinogen-IX oxidase inhibitor. Preferably, the protoporphyrinogen-IX oxidase inhibitor is selected from bifenox and oxadiazon.

[0165] In yet another aspect of the present invention, there is provided 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), and (b) at least one herbicide B selected from microtubule assembly inhibitors (HRAC K1 group). Preferably, the microtubule assembly inhibitor is selected from butruarin and dithiopyr.

[0166] In yet another aspect of the present invention, there is provided 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), and (b) at least one herbicide B selected from a VLCFA inhibitor. Preferably, the VLCFA inhibitor is selected from fentrazamide, ipfencarbazone, cafenstrole, fenoxasulfone, and agriculturally acceptable salts, esters, or amides thereof. In another embodiment, the VLCFA inhibitor is piperophos.

[0167] In yet another aspect of the present invention, there is provided 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), and (b) at least one herbicide B selected from the group of bleaching herbicides. Preferably, the bleaching herbicide is aclonifen.

[0168] In yet another aspect of the present invention, there is provided 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), and (b) at least one herbicide B selected from HPPD inhibitors. Preferably, the HPPD inhibitor is selected from benzobicyclon, benzofenap, bicyclopyrone, fenquinotrione, isoxaflutole, isoxaclortol, mesotrione, pyrasulfotole, pyrazolinate, pyrazoxyfen, sulcotrione, tefuryltrione, tembotrione, tolpyralate, topramezone, and agriculturally acceptable salts, esters, or amides thereof. More preferably, the HPPD inhibitor is selected from benzobicyclon, benzofenap, isoxaclortol, pyrazolinates, pyrazoxyfen, tefuryltrione, and agriculturally acceptable salts, esters, or amides thereof.

[0169] In yet another aspect of the present invention, there is provided 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), and (b) at least one herbicide B selected from the group of cellulose biosynthesis inhibitors, preferably indaziflam.

[0170] In yet another aspect of the present invention, there is provided 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), and (b) at least one herbicide B selected from synthetic auxins. Preferably, the synthetic auxin is selected from phenoxycarboxylic acids, benzoic acids, pyridinecarboxylic acids, and benazolin-ethyl. More preferably, the synthetic auxin is 2,4-D, 3,4-DA, MCPA, 2,4,5-T, 2,4-DP (dichlorprop), 2,4-DP-P, 4-CPP, 3,4-DP, fenoprop, CMPP (mecoprop), CMPP-P, 4-CPB, 2,4-DB, 3,4-DB, 2,4,5-TB, MCPB, dicamba, tricamba, chloramben, 2,3,6-TBA (2,3,6-trichlorobenzoic acid), aminopyralid, clopyralid, fluroxypyr, picloram, triclopyr, halaxifene, 4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)-5-fluoropyridine-2-carboxylic acid, benzyl 4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)-5-fluoropyridine-2-carboxylate (CAS 10147-10-1). 1390661-72-9), benazolin-ethyl, and agriculturally acceptable salts, esters, or amides thereof. In another embodiment, the synthetic auxin is selected from the group consisting of phenoxycarboxylic acids, particularly 2,4-D, 3,4-DA, MCPA, 2,4,5-T, 2,4-DP (dichlorprop), 2,4-DP-P, 4-CPP, 3,4-DP, fenoprop, CMPP (mecoprop), CMPP-P, 4-CPB, 2,4-DB, 3,4-DB, 2,4,5-TB, MCPB, and agriculturally acceptable salts, esters, or amides thereof. In another embodiment, the synthetic auxin is selected from the group consisting of benzoic acids, particularly dicamba, tricamba, chloramben, 2,3,6-TBA (2,3,6-trichlorobenzoic acid), and agriculturally acceptable salts, esters, or amides thereof.In another embodiment, the synthetic auxin is selected from the pyridine carboxylic acids, particularly aminopyralid, clopyralid, fluroxypyr, picloram, triclopyr, halauxifen, 4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)-5-fluoropyridine-2-carboxylic acid, benzyl 4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)-5-fluoropyridine-2-carboxylate (CAS 1390661-72-9), and agriculturally acceptable salts, esters, or amides thereof. In yet another embodiment, the synthetic auxin is benazolin-ethyl. In yet another embodiment, the synthetic auxin is benzyl 4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)-5-fluoropyridine-2-carboxylate (CAS 1390661-72-9).

[0171] In yet another aspect of the present invention, there is provided 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), and (b) at least one herbicide B selected from the group of herbicides with an unknown mode of action (HRAC group Z), preferably selected from indanofan, methiozoline (CAS 403640-27-7), oxaziclomefone, and agriculturally acceptable salts, esters, or amides thereof, more preferably indanofan.

[0172] In yet another embodiment of the present invention, 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), and (b) a compound of the group b1) Lipid biosynthesis inhibitors: cyhalofop, quizalofop, b2) ALS inhibitors: metsulfuron, penoxsulam, pyrimisulfan, bispyribac, pyribenzoxim, pyriftalid, pyriminobac, b3) Photosynthesis inhibitors: propanil, b5) bleaching herbicides: benzobicyclon, benzofenap, isoxachlorthol, pyrazolinate, pyrazoxyfen, tefuryltrione, b10) VLCFA inhibitors: fentrazamide, ipfencarbazone, cafenstrole, fenoxasulfone, b13) Synthetic auxin: benzyl 4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)-5-fluoropyridine-2-carboxylate (CAS 1390661-72-9), b15) Other herbicides: indanofan, methiozolin (CAS 403640-27-7), oxaziclomefone, and agriculturally acceptable salts, esters or amides thereof and a herbicidal composition comprising at least one herbicide B selected from

[0173] In yet another embodiment of the present invention, 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), and (b) a compound of the group b1) Lipid biosynthesis inhibitors: cyhalofop, cyhalofop-butyl, quizalofop, and quizalofop-P-ethyl; b2) ALS inhibitors: metsulfuron, metsulfuron-methyl, bispyribac, and bispyribac-sodium and a herbicidal composition comprising at least one herbicide B selected from

[0174] In yet another embodiment of the present invention, 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), and (b) a compound of the group b1) Lipid biosynthesis inhibitors: cyhalofop-butyl and quizalofop-p-ethyl, b2) ALS inhibitors: metsulfuron-methyl and bispyribac-sodium and a herbicidal composition comprising at least one herbicide B selected from

[0175] In yet another aspect of the present invention, there is provided a herbicidal composition comprising herbicidally effective amounts 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), and (b) cyhalofop or cyhalofop-butyl (herbicide B).

[0176] In yet another aspect of the present invention, there is provided a herbicidal composition comprising herbicidally effective amounts 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), and (b) quizalofop or quizalofop-p-ethyl (herbicide B).

[0177] In yet another aspect of the present invention, there is provided a herbicidal composition comprising herbicidally effective amounts 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), and (b) metsulfuron or metsulfuron-methyl (herbicide B).

[0178] In yet another aspect of the present invention, there is provided a herbicidal composition comprising herbicidally effective amounts 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), and (b) penoxsulam (herbicide B).

[0179] In yet another aspect of the present invention, there is provided a herbicidal composition comprising herbicidally effective amounts 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), and (b) pyrimisulfan (herbicide B).

[0180] In yet another aspect of the present invention, there is provided a herbicidal composition comprising herbicidally effective amounts 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), and (b) bispyribac or bispyribac-sodium (herbicide B).

[0181] In yet another aspect of the present invention, there is provided a herbicidal composition comprising herbicidally effective amounts 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), and (b) pyribenzoxim (herbicide B).

[0182] In yet another aspect of the present invention, there is provided a herbicidal composition comprising herbicidally effective amounts 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), and (b) pyriftalid (herbicide B).

[0183] In yet another aspect of the present invention, there is provided a herbicidal composition comprising herbicidally effective amounts 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), and (b) pyriminobac or pyriminobac-methyl (herbicide B).

[0184] In yet another aspect of the present invention, there is provided a herbicidal composition comprising herbicidally effective amounts 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), and (b) propanil (herbicide B).

[0185] In yet another aspect of the present invention, there is provided a herbicidal composition comprising herbicidally effective amounts 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), and (b) benzobicyclon (herbicide B).

[0186] In yet another aspect of the present invention, there is provided a herbicidal composition comprising herbicidally effective amounts 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), and (b) benzofenap (herbicide B).

[0187] In yet another aspect of the present invention, there is provided a herbicidal composition comprising herbicidally effective amounts 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), and (b) isoxaclorthol (herbicide B).

[0188] In yet another aspect of the present invention, there is provided 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), and (b) a pyrazolinate (herbicide B).

[0189] In yet another aspect of the present invention, there is provided a herbicidal composition comprising herbicidally effective amounts 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), and (b) pyrazoxyfen (herbicide B).

[0190] In yet another aspect of the present invention, there is provided a herbicidal composition comprising herbicidally effective amounts 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), and (b) tefuryltrione (herbicide B).

[0191] In yet another aspect of the present invention, there is provided a herbicidal composition comprising herbicidally effective amounts 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), and (b) fentrazamide (herbicide B).

[0192] In yet another aspect of the present invention, there is provided a herbicidal composition comprising herbicidally effective amounts 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), and (b) ipfencarbazone (herbicide B).

[0193] In yet another aspect of the present invention, there is provided 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), and (b) cafenstrole (herbicide B).

[0194] In yet another aspect of the present invention, there is provided a herbicidal composition comprising herbicidally effective amounts 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), and (b) fenoxasulfone (herbicide B).

[0195] In yet another aspect of the present invention, there is provided a herbicidal composition comprising herbicidally effective amounts 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), and (b) benzyl 4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)-5-fluoropyridine-2-carboxylate (CAS 1390661-72-9) (Herbicide B).

[0196] In yet another aspect of the present invention, there is provided a herbicidal composition comprising herbicidally effective amounts 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), and (b) indanofan (herbicide B).

[0197] In yet another aspect of the present invention, there is provided a herbicidal composition comprising herbicidally effective amounts 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), and (b) methiozoline (CAS 403640-27-7) (Herbicide B).

[0198] In yet another aspect of the present invention, there is provided a herbicidal composition comprising herbicidally effective amounts 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), and (b) oxaziclomefone (herbicide B).

[0199] In another aspect, the invention relates to the use of a composition as defined herein (in particular any one of the above herbicidal compositions comprising herbicide A and a particular herbicide B of groups b1, b2, b3, b5, b10, b13 and b15) for controlling undesirable vegetation.

[0200] In another aspect, the present invention relates to a method for controlling undesirable vegetation, comprising applying to the vegetation or the locus thereof, or to the soil or water, a composition as defined herein (in particular any one of the above herbicidal compositions comprising herbicide A and a specific herbicide B of groups b1, b2, b3, b5, b10, b13 and b15) to prevent the emergence or growth of the undesirable vegetation.

[0201] The herbicidal compositions comprising herbicide A and a specific herbicide B of groups b1, b2, b3, b5, b10, b13 and b15 are particularly suitable for selective weed control in rice crops (including but not limited to transplanted rice).

[0202] Thus, in another aspect, the present invention relates to the use of any one of the above compositions for selectively controlling undesirable vegetation in rice crops (including but not limited to transplanted rice).

[0203] In yet another aspect, the present invention relates to a method for selectively controlling undesirable vegetation in rice crops (including, but not limited to, transplanted rice) comprising the step of applying to a rice crop area any one of the above compositions.

[0204] In the above uses or methods, the undesirable vegetation is preferably selected from the genera Aesculus, Alopecia, Branwort, Avena sativa, Brachiaria, Bromeliad, Cynodon, Digitalia, Echinochloa, Goosegrass, Platypus, Leptolepis, Lolium, Panicum, Reed canary grass, Pueblo, Pseudopodiaceae, Setaria, Anthemis, Amaranthus, Ragweed, Shepherd's purse, Centaurea, Chenopodium, Conyza, Desclerinia, Cleaver, Kochia, Deerberry, Papaver, Radish, White mustard, Aleobacterium, Chickweed and Shepherd's purse.

[0205] More preferably, the undesired vegetation is selected from the genera Alopecia, Common Bran, Digitalia, Echinochloa, Leptochloa, Lolium, Reed Canary, Poo, Setaria, Amaranthus, Anthemis, Shepherd's Purse, Centaurea, Chenopodium, Descurania, Kochia, Deer, Papaver, Aster, Stellaria and Shepherd's Purse, more preferably from the genera Alopecia, Common Bran, Echinochloa, Leptochloa, Lolium, It is selected from the genera Reed canary, Poseua, Amaranthus, Chenopodium, Deer, Papavera and Stellaria, even more preferably from the genera Alopecia, Echinochloa, Lolium, Reed canary, Poseua, Amaranthus, Chenopodium, Deer, Papavera and Stellaria, even more preferably from the genera Alopecia, Echinochloa, Lolium, Reed canary, Poseua and Stellaria, especially from the genera Alopecia, Lolium, Reed canary, Poseua and Stellaria.

[0206] In another embodiment, the undesirable vegetation is selected from the genera Alopecia, Bromus, Brassica, Cleaver, Lolium, Deer, and Papaveracea.

[0207] In particular, undesirable vegetation includes black-glove weed, common weed, common bran, wild oat, common oat, Brachiaria plantaginea, Brachiaria decumbens, common brome, common brome, common brome, large crabgrass, large crabgrass, common crabgrass, Japanese barnyard grass, barnyard grass, Echinochloa cruz-pavonis, Echinochloa erecta, barnyard grass, barnyard grass, goosegrass, common oak, Chinese pigweed, Leptochloa panicoides, Leptochloa scabra, Leptochloa virgata, ryegrass, ryegrass, corngrass, common oat, common ryegrass, common corngrass, common corn millet, common corn millet, Phalaris brachystachys brachystachyx), dwarf canary grass, Phalaris paradoxa, annual bluegrass, longgrass, annual bluegrass, hornwort, autumn foxtail, golden foxtail, rough foxtail, green foxtail, white birch, American blackfly, narrow-leaved amaranthus, large-leaved amaranthus, long-leaved amaranthus, redroot pigweed, false amaranthus, Amaranthus rudis, common water chestnut, ragweed, chamomile, shepherd's purse, common cornflower, common oak, common oak, Chenopodium polyspermum, parsley, ragweed, ragweed, common mugwort, common mugwort, and ragweed (Descurania sophia), white spotted grass, cleaver, Japanese tortoiseshell grass, broom tree, chamomile, daisy, dogwood, corn poppy, wild radish, white mustard, field mustard, persimmon mustard, dogwood, chickweed and shepherd's purse, preferably black-and-white foxtail, white-and-white foxtail, common bran, northern crabgrass, large crabgrass, barnyard grass, barnyard grass, Chinese watergrass, Chinese pigweed, loosegrass, ryegrass, ryegrass, oak, Phalaris brachystachis, reed canary grass, Phalaris paradoxa, annual bluegrass, annual bluegrass, autumn foxtail, Japanese boxwood, golden foxtail, Setaria pumilla), rough foxtail, green foxtail, redroot pigweed, redroot pigweed, water chestnut, Amaranthus rudis, chamomile, shepherd's purse, cornflower, lamb's quarter, and ragwort (Descuraniasophia), kochia, chamomile, chamomile, corn poppy, persimmon, chickweed and shepherd's purse, more preferably black-glove foxtail, alpine foxtail, common bran, barnyard grass, barnyard grass, Chinese watergrass, pigweed, loosegrass, ryegrass, ryegrass, Phalaris brachystachys, reed canary grass, Phalaris paradoxa, annual bluegrass, American arugula, American amaranthus, American retroflexus, American redroot pigweed, and Amaranth It is selected from the group consisting of Japanese knotweed, Amaranthus rudis, Chenopodium album, chamomile, chamomile, corn poppy, and chickweed, and particularly preferably selected from the group consisting of black foxtail, annual foxtail, common bran, barnyard grass, barnyard grass, Chinese ryegrass, Japanese laurel wattle, reed canary grass, and annual bluegrass, and in particular selected from the group consisting of black foxtail, barnyard grass, Japanese laurel wattle, and reed canary grass.

[0208] In another embodiment, the undesirable vegetation is selected from black grass, brome grass, Brassica napus, white spotted grass, corn poppy, chamomile, and corn poppy.

[0209] In another embodiment, the compositions as defined herein may further comprise at least one safener C (as defined herein). In yet another embodiment, these compositions may further comprise one or more adjuvants (as defined herein) customary in crop protection.

[0210] Certain combinations of (a) herbicide A and (b) herbicide B may also result in a synergistic herbicidal effect.

[0211] Thus, in preferred embodiments of the compositions, uses and methods of the present invention, herbicide A and herbicide B are each present or applied in amounts sufficient to provide a synergistic herbicidal effect.

[0212] The term "synergistic herbicidal effect" refers to the herbicidal effect of a given combination of two herbicides when the herbicidal activity of the combination exceeds the sum of the individual herbicidal activities of the herbicides when applied separately. For this reason, a lower application rate of the composition based on the individual components can be used to achieve the same herbicidal effect as the individual components.

[0213] In some embodiments of the present invention, the Colby equation is applied to determine whether a combination of herbicide A and herbicide B exhibits a synergistic effect (see S.R. Colby, "Calculating synergistic and antagonistic responses of herbicide combinations," Weeds 1967, 15, pp. 20-22). E=X+Y-(X . Y / 100) During the ceremony, X = percent effectiveness of herbicide A at application rate a; Y = percent effectiveness of herbicide B at application rate b; E = predicted efficacy (%) of herbicide A + herbicide B at application rate a + b.

[0214] In Colby's formula, the value E corresponds to the effect (plant damage or injury) that would be expected if the activities of the individual compounds were additive. If the observed effect is higher than the value E calculated according to Colby's formula, a synergistic effect is present.

[0215] In one embodiment of the present invention, the methods, uses and compositions disclosed herein are synergistic as determined by the Colby formula, specifically, the synergistic herbicidal effect is determined according to the Colby formula.

[0216] In the methods, uses and compositions of the present invention, the weight ratio of herbicide A (especially (±)-2-exo-(2-methylbenzyloxy)-1-methyl-4-isopropyl-7-oxabicyclo[2.2.1]heptane) to herbicide B is generally in the range of 1:1000 to 1000:1, preferably in the range of 1:500 to 500:1, in particular in the range of 1:250 to 250:1, and particularly preferably in the range of 1:75 to 75:1, where each herbicide B that is an acid ester or salt is calculated as the acid.

[0217] In the methods, uses and compositions of the invention, the weight ratio of herbicide A (especially (±)-2-exo-(2-methylbenzyloxy)-1-methyl-4-isopropyl-7-oxabicyclo[2.2.1]heptane) to safener C is generally in the range of 1:1000 to 1000:1, preferably in the range of 1:500 to 500:1, in particular in the range of 1:250 to 250:1, and particularly preferably in the range of 1:75 to 75:1, whereby each safener C that is an acid ester or salt is calculated as the acid.

[0218] In the methods, uses and compositions of the present invention, the weight ratio of herbicide B to safener C is generally in the range of 1:1000 to 1000:1, preferably in the range of 1:500 to 500:1, in particular in the range of 1:250 to 250:1, and particularly preferably in the range of 1:75 to 75:1, where each herbicide B and safener C that is an acid ester or salt is calculated as the acid.

[0219] In the methods, uses and compositions of the present invention, the weight ratio of the combination of herbicides A (especially (±)-2-exo-(2-methylbenzyloxy)-1-methyl-4-isopropyl-7-oxabicyclo[2.2.1]heptane) and B to safener C is preferably in the range of 1:500 to 500:1, in particular in the range of 1:250 to 250:1, and particularly preferably in the range of 1:75 to 75:1, where each herbicide B and safener C, which is an acid ester or salt, is calculated as the acid.

[0220] The compositions defined herein are suitable as herbicides themselves or as appropriately formulated pesticide compositions. As used herein, the term "pesticide composition" refers to a composition that further comprises one or more adjuvants customary in crop protection.

[0221] Thus, the agrochemical composition comprises a herbicidally effective amount of a herbicide A, optionally at least one herbicide B (as defined herein), optionally at least one safener C (as defined herein), and one or more adjuvants customary in crop protection.

[0222] 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 conventional types of pesticide compositions, such as solutions, emulsions, suspensions, dusts, powders, pastes, granules, pressings, and mixtures thereof. These and further types of pesticide compositions are defined in "Catalogue of pesticide formulation types and international coding system," Technical Monograph No. 2, 6th Edition, May 2008, CropLife International.

[0223] The pesticide compositions can be formulated in known manner, such as those described in 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.

[0224] The term "adjuvants customary in crop protection" includes, but is not limited to, solvents, liquid carriers, solid carriers or fillers, surfactants, dispersants, emulsifiers, wetting agents, adjuvants, solubilizers, penetration enhancers, protective colloids, adhesives, thickeners, water-retaining agents, repellents, attractants, feeding stimulants, compatibilizers, bactericides, antifreeze agents, antifoaming agents, colorants, tackifiers and binders.

[0225] Suitable solvents and liquid carriers are water and organic solvents such as medium to high boiling mineral oil fractions, 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, benzyl alcohol, cyclohexanol; glycols; DMSO; ketones, e.g., cyclohexanone; esters, e.g., lactate esters, carbonate esters, fatty acid esters, gamma-butyrolactone; fatty acids; phosphonates; amines; amides, e.g., N-methylpyrrolidone, fatty acid dimethylamides; and mixtures thereof.

[0226] Suitable solid carriers or fillers are inorganic earths such as silicates, silica gel, talc, kaolin, limestone, lime, chalk, clay, dolomite, diatomaceous earth, bentonite, calcium sulfate, magnesium sulfate, magnesium oxide; polysaccharides such as cellulose, starch; fertilizers such as ammonium sulfate, ammonium phosphate, ammonium nitrate, ureas; plant-derived products such as grain flour, bark flour, wood flour, nut shell flour, and mixtures thereof.

[0227] 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 emulsifiers, dispersants, solubilizers, wetting agents, penetration enhancers, protective colloids, or adjuvants. Examples of surfactants are listed in McCutcheon's, Vol. 1: Emulsifiers & Detergents, McCutcheon's Directories, Glen Rock, USA, 2008 (International Edition or North American Edition).

[0228] Suitable anionic surfactants include alkali salts, alkaline earth salts, or ammonium salts of sulfonates, sulfates, phosphates, and carboxylates, and mixtures thereof. Examples of sulfonates include alkylarylsulfonates, diphenylsulfonates, alpha-olefin sulfonates, lignin sulfonates, sulfonates of fatty acids and oils, sulfonates of ethoxylated alkylphenols, sulfonates of alkoxylated arylphenols, sulfonates of condensed naphthalenes, sulfonates of dodecylbenzene and tridecylbenzene, sulfonates of naphthalene and alkylnaphthalenes, sulfosuccinates, or sulfosuccinamates. Examples of sulfates include sulfates of fatty acids and oils, sulfates of ethoxylated alkylphenols, sulfates of alcohols, sulfates of ethoxylated alcohols, or sulfates of fatty acid esters. Examples of phosphates include phosphoric acid esters. Examples of carboxylates include alkyl carboxylates, as well as carboxylated alcohol or alkylphenol ethoxylates.

[0229] Suitable nonionic surfactants include alkoxylates, N-substituted fatty acid amides, amine oxides, esters, sugar-based surfactants, polymeric surfactants, and mixtures thereof. Examples of alkoxylates include compounds such as alcohols, alkylphenols, amines, amides, arylphenols, fatty acids, or fatty acid esters that are alkoxylated with 1 to 50 equivalents. Ethylene oxide and / or propylene oxide can be used for the alkoxylation, with ethylene oxide being preferred. Examples of N-substituted fatty acid amides include fatty acid glucamides or fatty acid alkanolamides. Examples of esters include fatty acid esters, glycerol esters, or monoglycerides. Examples of sugar-based surfactants include sorbitan, ethoxylated sorbitan, sucrose and glucose esters, or alkyl polyglucosides. Examples of polymeric surfactants include homopolymers or copolymers of vinylpyrrolidone, vinyl alcohol, or vinyl acetate.

[0230] Suitable cationic surfactants are quaternary surfactants, such as quaternary ammonium compounds with one or two hydrophobic groups, or salts of long-chain primary amines. Suitable amphoteric surfactants are alkylbetaines and imidazolines. Suitable block polymers are AB or ABA block polymers containing polyethylene oxide and polypropylene oxide blocks, or ABC block polymers containing alkanol, polyethylene oxide, and polypropylene oxide. Suitable polyelectrolytes are polyacids or polybases. Examples of polyacids are polyacrylic acid or alkali salts of polyacid comb polymers. Examples of polybases are polyvinylamine or polyethyleneamine.

[0231] Suitable adjuvants are compounds that have little or no pesticidal activity themselves and improve the biological performance of Compound I against the target. Examples include surfactants, mineral or vegetable oils, and other adjuvants. Further examples are listed in Knowles, Adjuvants and additives, Agrow Reports DS256, T&F Informa UK, 2006, Chapter 5.

[0232] Suitable thickening agents are polysaccharides (eg xanthan gum, carboxymethylcellulose), inorganic clays (organically modified or unmodified), polycarboxylates, and silicates.

[0233] Suitable bactericides are bronopol and isothiazolinone derivatives such as alkylisothiazolinones and benzisothiazolinones.

[0234] Suitable antifreeze agents are ethylene glycol, propylene glycol, urea and glycerin.

[0235] Suitable antifoaming agents are silicones, long chain alcohols, and fatty acid salts.

[0236] Suitable colorants (e.g., red, blue, or green) are low-water-soluble pigments and water-soluble dyes. Examples are inorganic colorants (e.g., iron oxide, titanium oxide, iron hexacyanoferrate) and organic colorants (e.g., alizarin, azo, and phthalocyanine colorants).

[0237] Suitable tackifiers or binders are polyvinylpyrrolidone, polyvinyl acetate, polyvinyl alcohol, polyacrylates, biological or synthetic waxes, and cellulose ethers.

[0238] The pesticide composition generally contains between 0.01 and 95% by weight, preferably between 0.1 and 90% by weight, in particular between 0.5 and 75% by weight, of the active substance, which is used with a purity of 90% to 100%, preferably 95% to 100% (according to NMR spectroscopy).

[0239] Various types of oils, wetting agents, adjuvants, fertilizers or micronutrients, and further pesticides (e.g. herbicides, insecticides, fungicides, growth regulators, safeners) can be added to the active substances or to the compositions containing them as premixes, if desired just prior to use (tank mix). These agents can be mixed with the compositions defined herein in a weight ratio of 1:100 to 100:1, preferably 1:10 to 10:1.

[0240] Users typically apply pesticide compositions from predosage devices, backpack sprayers, spray tanks, spray aircraft, or irrigation systems. Typically, pesticide compositions are prepared to the desired application concentration with water, buffers, and / or additional adjuvants, resulting in a ready-to-use spray liquid or pesticide composition. Typically, 20 to 2000 liters, preferably 50 to 400 liters, of ready-to-use spray liquid are applied per hectare of useful agricultural area.

[0241] According to one embodiment, either the individual or partially pre-mixed components of the pesticide composition, for example the pesticide ingredients comprising herbicide A, optionally at least one herbicide B (as defined herein) and optionally at least one safener C (as defined herein), may be mixed by the user in a spray tank, and further adjuvants and additives may be added as appropriate.

[0242] In another embodiment, the individual components of the pesticide composition, such as parts of a kit or parts of a two- or three-component mixture, may be mixed by the user themselves in a spray tank, and further adjuvants may be added as appropriate.

[0243] In another embodiment, any of the individual or partially pre-mixed components of the pesticide composition, for example, the components comprising herbicide A, optionally at least one herbicide B (as defined herein), and optionally at least one safener C (as defined herein), can be applied together (e.g., after a tank mix) or sequentially.

[0244] Thus, the agrochemical composition can be provided in the form of a single-package formulation containing herbicide A, optionally at least one herbicide B (as defined herein), and optionally at least one safener C (as defined herein), together with a liquid and / or solid carrier, and optionally one or more surfactants, and optionally one or more further adjuvants customary in crop protection. The formulation can also be provided in the form of a two-package formulation, in which one package contains a formulation of herbicide A and the other package contains a formulation of at least one herbicide B and / or safener C, both formulations containing at least one carrier substance, optionally one or more surfactants, and optionally one or more further adjuvants customary in crop protection. The formulation can also be provided in the form of a two-package formulation, in which one package contains a formulation of herbicide A and optionally safener C, and the other package contains a formulation of at least one herbicide B, both formulations containing at least one carrier substance, optionally one or more surfactants, and optionally one or more further adjuvants customary in crop protection. In the case of a two-package formulation, the two formulations are preferably mixed before application. Preferably, the mixing is carried out as a tank mix, i.e. the formulations are mixed just before or during dilution with water.

[0245] The compositions defined herein are highly effective in controlling vegetation in non-crop areas, especially at high application rates.They act on broadleaf weeds and grass weeds in crops such as wheat, barley, rice, corn, sunflower, soybean and cotton without causing significant damage to crop plants.This effect is mainly observed at low application rates.

[0246] The compositions defined herein are applied to plants primarily by spraying. Here, application can be carried out, for example, using water as a carrier and conventional spraying techniques, using a spray liquid volume of about 50 to 1000 l / ha (e.g., 300 to 400 l / ha). The compositions defined herein can also be applied by the low-volume or ultra-low-volume method or in the form of microgranules.

[0247] The compositions defined herein can be applied before or after emergence, or together with the seeds of crop plants.The compounds and compositions can also be applied by applying the seeds of crop plants that have been pre-treated with the compositions defined herein.If a particular crop plant does not tolerate herbicide A and, if appropriate, herbicide B well, the application technique can be used in which the herbicidal composition is sprayed using a spraying device so that the herbicidal composition does not come into contact with the leaves of sensitive crop plants as much as possible, and the active compound reaches the leaves of undesirable plants growing below or the surface of exposed soil (post-directed, lay-by).

[0248] In a further embodiment, the compositions defined herein can be applied by treating seeds. Seed treatment includes substantially all procedures familiar to those skilled in the art based on the compositions defined herein (seed dressing, seed coating, seed dusting, seed soaking, seed film coating, seed multilayer coating, seed encrusting, seed dripping, and seed pelleting). Here, the compositions defined herein can be applied diluted or undiluted.

[0249] The term "seed" includes all types of seeds, such as grains, seeds, fruits, tubers, seedlings, and similar forms. Preferably, the term "seed" refers to grains and seeds. The seeds used may be seeds of the above-mentioned useful plants, as well as seeds of transgenic plants or plants obtained by conventional breeding methods.

[0250] Furthermore, it may be advantageous to apply the composition defined herein alone or in combination with other crop protection agents, such as agents for controlling pests or plant pathogenic fungi or bacteria, or active compounds for regulating growth.Also of interest is the compatibility with inorganic salt solutions used to treat nutrient deficiency and trace element deficiency.Non-phytotoxic oils and oil concentrates may be added.

[0251] When used in plant protection, the amount of active substance (i.e. herbicide A and, where appropriate, herbicide B) applied without formulation adjuvants is, depending on the type of effect desired, 0.0001 to 10 kg per hectare (kg / ha), preferably 0.001 to 3 kg / ha, more preferably 0.001 to 2.5 kg / ha, even more preferably 0.001 to 2 kg / ha, particularly preferably 0.005 to 2 kg / ha, in particular 0.05 to 0.9 kg / ha and most preferably 0.1 to 0.75 kg / ha.

[0252] In the methods and uses of the present invention, herbicide A (especially (±)-2-exo-(2-methylbenzyloxy)-1-methyl-4-isopropyl-7-oxabicyclo[2.2.1]heptane) is generally applied in an amount of 0.1 to 2000 grams per hectare (g / ha), preferably 10 to 1000 g / ha, more preferably 10 to 750 g / ha, and especially 10 to 500 g / ha. In another embodiment, herbicide A (especially (±)-2-exo-(2-methylbenzyloxy)-1-methyl-4-isopropyl-7-oxabicyclo[2.2.1]heptane) is applied in an amount of 50 to 1000 g / ha, preferably 75 to 750 g / ha, and more preferably 100 to 500 g / ha.

[0253] In the method and use of the present invention, the application rate of herbicide B (calculated as the acid in the case of a salt) is generally 0.0005 kg / ha to 10 kg / ha, preferably 0.005 kg / ha to 5 kg / ha, more preferably 0.001 kg / ha to 2 kg / ha.

[0254] In the method and use of the present invention, the application rate of the safener C (calculated as the acid in the case of a salt) is generally 0.0005 kg / ha to 2.5 kg / ha, preferably 0.005 kg / ha to 2 kg / ha, more preferably 0.01 kg / ha to 1.5 kg / ha.

[0255] In the treatment of plant propagation material such as seeds, for example by dusting, coating or drenching the seeds, amounts of active substance (i.e. herbicide A and, where appropriate, herbicide B) of 0.1 to 5000 g, preferably 5 to 2500 g, more preferably 50 to 2000 g, in particular 100 to 1500 g per 100 kilograms of plant propagation material (preferably seeds) are generally required.

[0256] In another embodiment of the invention, the amount of active substance applied for treating the seeds (ie herbicide A and, where appropriate, herbicide B) is generally used in an amount of 0.001 to 10 kg per 100 kg of seeds.

[0257] In the methods and uses of the present invention, herbicide A and, if any, herbicide B and / or safener C can be applied together or separately.

[0258] In the methods and uses of the present invention, herbicide A and, if present, herbicide B and / or safener C can be applied simultaneously or sequentially.

[0259] Preferably, herbicide A, and, if present, herbicide B and / or safener C, are applied simultaneously to the undesired vegetation. In another embodiment, herbicide A, and, if present, herbicide B and / or safener C, are provided as a herbicidal composition as defined herein (e.g., a tank mix comprising herbicide A, and, if present, herbicide B and / or safener C) that is applied to the undesired vegetation. Thus, in some embodiments of the methods of the present invention, a herbicidal composition as defined herein is applied to or to the locus of the undesired vegetation, or is applied to the soil or water to prevent the emergence or growth of the undesired vegetation.

[0260] When applied separately or successively, the order of application of herbicide A and, if any, herbicide B and / or safener C is of little importance. It is only necessary to apply herbicide A and, if any, herbicide B and / or safener C within a period allowing the active ingredients to act simultaneously on the plants to be controlled and / or rendered harmless, preferably within a period of at most 14 days, in particular within a period of at most 7 days.

[0261] In the methods and uses of the present invention, herbicide A, and, if any, herbicide B and / or safener C (or compositions as defined herein) can be applied pre-emergence (i.e. before emergence of undesirable vegetation) or post-emergence (i.e. during and / or after emergence of undesirable vegetation),

[0262] Preferably, herbicide A, and, if present, herbicide B and / or safener C (or a composition as defined herein) are applied before emergence (pre-emergence) of the undesired vegetation.

[0263] More preferably, herbicide A, and, if present, herbicide B and / or safener C (or a composition as defined herein) are applied before or during emergence (pre-emergence or early post-emergence) of the undesirable vegetation.

[0264] In another embodiment, herbicide A, and, if present, herbicide B and / or safener C (or a composition as defined herein) are applied after emergence of the undesirable vegetation.

[0265] For post-emergence treatments, herbicide A, and, if present, herbicide B and / or safener C (or a composition as defined herein) are preferably applied after the undesirable vegetation has emerged and developed to six leaves.

[0266] The methods, uses and compositions according to the invention are suitable for controlling unwanted vegetation in various crop plants. Examples of suitable crops are: Onion (Allium cepa) (onion), garlic (Allium sativum) (garlic), pineapple (Ananas comosus) (pineapple), groundnut (Arachis hypogaea) [peanut (groundnut)], asparagus (Asparagus) (Asparagus), oat (Avena sativa) (oats), Beta vulgaris spec. altissima (sugar beet), Beta vulgaris spec. rapa (turnip), Brassica napus var. napus (rapeseed, canola), Brassica napus var. napobrassica (sweed), Brassica rapa var. sylvestris rapa var. silvestris (winter turnip rape), Brassica oleracea (cabbage), black mustard (Brassica nigra) (black mustard), tea plant (Camellia sinensis) (tea plant), safflower (Carthamus tinctorius) (safflower), pecan (Carya illinoinensis) (pecan tree), lemon (Citrus limon) (lemon), coffea arabica (coffea canephora, coffea liberica) (coffee tree), cucumber (Cucumis sativus) (cucumber), and corngrass (Cynodon dactylon) (Cardiophora dactyla), Carrot (Daucus carota subspec.sativa (carrot), oil palm (Elaeis guineensis) (oil palm), strawberry (Fragaria vesca) (strawberry), soybean (Glycine max) (soybean), wild cotton (Gossypium hirsutum) (brown cotton (Gossypium arboreum), white cotton (Gossypium herbaceum), Gossypium vitifolium), sunflower (Helianthus annuus) (sunflower), rubber tree (Hevea brasiliensis) (rubber tree), barley (Hordeum vulgare) (barley), lupine (Humulus lupulus) (hops), sweet potato (Ipomoea batatas) (sweet potato), oak walnut (Juglans regia (walnut tree), Lentil (Lens culinaris) (lentil), Flax (Linum usitatissimum) (flax), Lycopersicon lycopersicum (tomato), Malus spec. (apple tree), Cassava (Manihot esculenta) (cassava), Medicago sativa (alfalfa (lucerne)], Musa spec. (banana tree), Nicotiana tabacum (N. rustica) (tobacco), Olive (Olea europaea) (olive tree), Rice (Oryza sativa) (rice), Lima bean (Phaseolus lunatus) (lima bean), Phaseolus vulgaris (kidney beans, green beans, dry beans), Norway spruce (Picea abies) (Norway spruce), Pinus spec.) (pine tree), pistachio (Pistacia vera) (pistachio), pea (Pisum sativum) (pea), sweet cherry (Prunus avium) (cherry tree), Prunus persica (peach tree), pear (Pyrus communis) (pear tree), apricot (Prunus armeniaca) (apricot), Prunus cerasus (Sweet cherry), Prunus dulcis (almond tree) and plum (prunus domestica) (plum tree), Ribes sylvestre (red currant), castor bean (Ricinus communis) (castor bean), sugarcane (Saccharum officinarum (sugar cane), rye (Secale cereale) (rye), white mustard, potato (Solanum tuberosum) (potato), sorghum (sorghum bicolor) (S. vulgare) (sorghum), cocoa (Theobroma cacao) (cocoa tree), red clover (Trifolium pratense) (red clover), wheat (Triticum aestivum) (wheat), triticale (triticale), durum (Triticum durum) (durum wheat, hard wheat), broad beans (Vicia faba) (fava beans), European grape (Vitis vinifera) (grape), and corn (Zea mays) (Indian corn, sweet corn, maize).

[0267] Preferred crops are onion, garlic, peanut, oat, Beta vulgaris spp. altissima, Brassica napus var. napus, Brassica oleracea, Cynodon dactylon, carrot, soybean, wild cotton (Gossypium vitifolium), sunflower, barley, lentil, flax, Lycopersicon lycopersicum, Malus spp., alfalfa, rice, lima bean, common bean, pea, sugarcane, rye, potato, sorghum (S. vulgare), triticale, wheat, durum wheat, broad bean, European grape, and maize.

[0268] In another embodiment, the crop plant is wheat, barley, rye, oats, triticale, corn (maize), sunflower, rice, legume crops (such as soybeans, peas, beans such as Vicia beans, Phaseolus beans, or Vigna beans, peanuts, chickpeas, lentils, alfalfa, lupin, etc.), oilseed rape, canola, cotton, potato, sugar beet, sugarcane, bulb vegetables (such as onion, garlic, shallot), carrot, tomato, brassica vegetables (such as cabbage, cauliflower, broccoli, Brussels sprouts, kale, kohlrabi), leafy vegetables (such as salad, lettuce, endive, radicchio, arugula, chicory, etc.), pepper The grasses are selected from among mango, cucumber, eggplant, pumpkin, melon, pepper, zucchini, parsley, parsnip, radish, horseradish, leek, asparagus, celery, artichoke, tobacco, hops, citrus fruits (orange, lemon, pomelo, grapefruit, mandarin, nectarine, etc.), stone fruits (apricot, cherry, peach, plum, etc.), pome fruits (apple, pear, quince, etc.), tree nuts (almond, walnut, etc.), grapes, oil palm, olive, and turfgrass (bahiagrass, bentgrass, cypress, bluegrass, buffalograss, carpetgrass, centipedegrass, fescue, kikuyugrass, ryegrass, St. Augustine grass, zoysiagrass, etc.).

[0269] In a preferred embodiment, the crop plant is selected from the group consisting of wheat, barley, rye, triticale, oats, corn (maize), sunflower, rice, soybean, pea, bean, peanut, oilseed rape, canola, cotton, potato, sugar beet, sugarcane, turfgrass, and vegetables.

[0270] In an even more preferred embodiment, the crop plant is selected from the group consisting of wheat, barley, rye, triticale, oats, corn (maize), sunflower, rice, soybean, pea, Vicia faba, Phaseolus vulgaris, peanut, oilseed rape, canola, cotton, potato, sugar beet, sugarcane, turfgrass, and vegetables.

[0271] In a particularly preferred embodiment, undesirable vegetation is controlled in cereals, in particular cereals selected from the group consisting of wheat, barley, rye, oats, and triticale.

[0272] In another particularly preferred embodiment, undesirable vegetation is controlled in rice (including but not limited to transplanted rice).

[0273] The methods, uses, and compositions of the present invention can also be used in genetically modified plants. The term "genetically modified plant" should be understood as a plant whose genetic material has been modified using recombinant DNA technology to contain an inserted DNA sequence that is not native to the genome of that plant species or to exhibit a deletion of DNA that was native to the genome of that species, and which modification is not readily obtainable through cross-breeding, mutagenesis, or natural recombination alone. Often, a particular genetically modified plant has inherited genetic modifications through natural breeding or propagation processes from an ancestor plant whose genome has been directly manipulated using recombinant DNA technology. Typically, one or more genes are incorporated into the genetic material of a genetically modified plant to improve specific plant characteristics. Such genetic modifications also include, but are not limited to, targeted post-translational modifications of proteins, oligopeptides, or polypeptides, for example, by including amino acid mutations that allow, reduce, or promote glycosylation or polymer addition, such as prenylation, acetylation, farnesylation, or PEG moiety attachment.

[0274] Plants that have been modified by breeding, mutagenesis, or genetic engineering may be treated, as a result of conventional breeding or genetic engineering, with, for example, auxin herbicides such as dicamba or 2,4-D; bleaching herbicides such as 4-hydroxyphenylpyruvate dioxygenase (HPPD) inhibitors or phytoene desaturase (PDS) inhibitors; acetolactate synthase (ALS) inhibitors such as sulfonylureas or imidazolinones; enolpyruvylshikimate 3-phosphate synthase (EPSP) inhibitors such as glyphosate; glutamine synthetase (GS) inhibitors such as glufosinate; protease inhibitors such as benzophenone; The plants have been made tolerant to the application of certain classes of herbicides, such as toporphyrinogen-IX oxidase inhibitors; lipid biosynthesis inhibitors, such as acetyl-CoA carboxylase (ACCase) inhibitors; or oxynil (i.e., bromoxynil or ioxynil) herbicides, and furthermore, the 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 another class of herbicide, such as an ALS inhibitor, an HPPD inhibitor, an auxin herbicide, or an ACCase inhibitor. These herbicide resistance technologies are described, for example, in Pest Management Science 61, 2005, 246; 61, 2005, 258; 61, 2005, 277; 61, 2005, 269; 61, 2005, 286; 64, 2008, 326; 64, 2008, 332; Weed Science 57, 2009, 108; Australian Journal of Agricultural Research 58, 2007, 708; Science 316, 2007, 1185; and references cited therein. Several cultivated plants, such as Clearfield® summer rapeseed (canola, BASF SE, Germany), which is tolerant to imidazolinones such as imazamox, or ExpressSun® sunflower (DuPont, USA), which is tolerant to sulfonylureas such as tribenuron, have been made tolerant to herbicides by mutagenesis and conventional breeding.Using genetic engineering methods, cultivated plants such as soybean, cotton, corn, beet, and rapeseed have been made tolerant to herbicides such as glyphosate, imidazolinones, and glufosinate, some of which have been developed or are commercially available under the trademarks or trade names RoundupReady® (glyphosate-tolerant, Monsanto, USA), Cultivance® (imidazolinone-tolerant, BASF SE, Germany), and LibertyLink® (glufosinate-tolerant, Bayer CropScience, Germany).

[0275] Furthermore, by using recombinant DNA techniques it is possible to produce one or more insecticidal proteins, in particular known insecticidal proteins from the bacteria Bacillus genus, in particular Bacillus thuringiensis, such as delta-endotoxins, e.g. CryIA(b), CryIA(c), CryIF, CryIF(a2), CryIIA(b), CryIIIA, CryIIIB(b1) or Cry9c; vegetative insecticidal proteins (VIPs), e.g. VIP1, VIP2, VIP3 or VIP3A; insecticidal proteins from bacteria colonizing nematodes, e.g. Photorhabdus spp. or Xenorhabdus spp. insecticidal proteins of Bombyx spp.); toxins produced by animals, such as scorpion venom, spider venom, bee venom, or other insect-specific neurotoxins; toxins produced by fungi, such as actinomycete toxins; plant lectins, such as pea or barley lectin; agglutinins; proteinase inhibitors, such as trypsin inhibitors, serine protease inhibitors, patatin, cystatin, or papain inhibitors; ribosome-inactivating proteins (RIPs), such as ricin, maize-RIP, abrin, luffin, saporin, or bryodin. Also included are plants capable of synthesizing IP; steroid metabolic enzymes such as 3-hydroxysteroid oxidase, ecdysteroid-IDP-glycosyltransferase, cholesterol oxidase, ecdysone inhibitor or HMG-CoA-reductase; ion channel blockers such as sodium or calcium channel blockers; juvenile hormone esterase; diuretic hormone receptor (helicokinin receptor); stilbene synthase, bibenzyl synthase, chitinase or glucanase. In the context of the present invention, these insecticidal proteins or toxins should also be clearly understood to include pretoxins, hybrid proteins, truncated proteins or proteins modified in other ways.Hybrid proteins are characterized by new combinations of protein domains (see, for example, WO 02 / 015701). Further examples of such toxins or genetically modified plants that can synthesize such toxins are disclosed, for example, in EP-A 374 753, WO 93 / 007278, WO 95 / 34656, EP-A 427 529, EP-A 451 878, WO 03 / 18810 and WO 03 / 52073. Methods for producing such genetically modified plants are generally known to those skilled in the art and are described, for example, in the above publications. These insecticidal proteins contained in genetically modified plants impart resistance to harmful pests from all taxa of arthropods, particularly beetles (Coleoptera), dipteran insects (Diptera), and moths (Lepidoptera) and nematodes (Nematoda) to the plants that produce these proteins.Genetically modified plants capable of synthesizing one or more insecticidal proteins are described, for example, in the above publications, some of which include YieldGard® (a corn cultivar that produces the Cry1Ab toxin), YieldGard® Plus (a corn cultivar that produces the Cry1Ab and Cry3Bb1 toxins), Starlink® (a corn cultivar that produces the Cry9c toxin), Herculex® RW (a corn cultivar that produces Cry34Ab1, Cry35Ab1 and the enzyme phosphinothricin-N-acetyltransferase [PAT]); NuCOTN® 33B (a corn cultivar that produces the Cry34Ab1, Cry35Ab1 and the enzyme phosphinothricin-N-acetyltransferase [PAT]); Cry1Ac toxin-producing cotton cultivars), Bollgard® I (Cry1Ac toxin-producing cotton cultivars), Bollgard® II (Cry1Ac and Cry2Ab2 toxins-producing cotton cultivars); VIPCOT® (VIP-toxin-producing cotton cultivars); NewLeaf® (Cry3A toxin-producing potato cultivars); Bt-Xtra®, NatureGard®, KnockOut®, BiteGard®, Protecta®, Bt11 (e.g., Agrisure® CB), and Syngenta Seeds SAS, France, Bt176 (a corn cultivar that produces a Cry1Ab toxin and a PAT enzyme), Syngenta Seeds SAS, France, MIR604 (a corn cultivar that produces a modified Cry3A toxin, see WO 03 / 018810), Monsanto Europe SA, Belgium, MON863 (a corn cultivar that produces a Cry3Bb1 toxin), Monsanto Europe SA, Belgium, IPC531 (a cotton cultivar that produces a modified Cry1Ac toxin), and Pioneer Overseas Corporation, Belgium, 1507 (a corn cultivar that produces a Cry1F toxin and a PAT enzyme).

[0276] Also included are plants that, through the use of recombinant DNA technology, are capable of synthesizing one or more proteins for increasing the plant's resistance or tolerance to bacterial, viral, or fungal pathogens. Examples of such proteins are so-called "infection-specific proteins" (PR proteins, see, for example, EP-A 392 225), plant disease resistance genes (e.g., potato cultivars from the Mexican wild potato, Solanum bulbocastanum, that express a resistance gene acting against Phytophthora infestans), or T4-lysozyme (e.g., potato cultivars capable of synthesizing these proteins and exhibiting increased resistance to bacteria such as Erwinia amylovora). Methods for producing such genetically modified plants are generally known to those skilled in the art and are described, for example, in the publications mentioned above.

[0277] Also included are plants that, through the use of recombinant DNA technology, are capable of synthesizing one or more proteins to increase the productivity of the plant (e.g., biomass production, grain yield, starch content, oil content, or protein content), resistance to drought, salinity, or other environmental factors that limit growth, or resistance to pests and fungal, bacterial, or viral pathogens.

[0278] Additionally, through the use of recombinant DNA technology, plants containing altered amounts of or new ingredients specifically to improve human or animal nutrition are also included, for example, oil crops that produce health-promoting long-chain omega-3 fatty acids or unsaturated omega-9 fatty acids (e.g., Nexera® rapeseed, Dow AgroSciences, Canada).

[0279] Additionally, plants that contain altered or new amounts of components, particularly to improve feedstock production through the use of recombinant DNA technology, are also included, such as potatoes that produce increased amounts of amylopectin (e.g., Amflora® potatoes, BASF SE, Germany).

[0280] The following examples serve to illustrate the invention. [Example]

[0281] I. Control of resistant weed biotypes The herbicidal activity of Herbicide A against resistant weed biotypes was tested in comparison with certain commercial herbicides in the following greenhouse experiment.

[0282] The culture vessels used were plastic pots containing loamy sand containing approximately 3.0% humus as a substrate. Seeds of the test plants were planted separately for each species. Six black-grass (ALOMY) biotypes (10-103, 10-170, 09-591, 10-123, 11-215, 11-146) and six ryegrass (LOLMU) biotypes (12-166, 12-143, 12-165, 12-307, 13-304, 13-313) with varying degrees of resistance to a wide range of modes of action according to the Herbicide Resistance Action Committee (HRAC) classification based on Mode of Action 2010 (see, e.g., http: / / www.hracglobal.com / pages / classificationofherbicidesiteofaction.aspx) were tested, along with two non-resistant biotypes (14-116 and 13-243). See Tables 1 and 2 below.

[0283] For post-emergence treatment, the test plants were first grown to a height of 3-15 cm, depending on the plant characteristics, and only then were they treated with the active ingredient suspended or emulsified in water. For this, the test plants were either planted directly and grown in the same container, or first grown separately as seedlings and transplanted into the test container a few days before treatment.

[0284] Depending on the species, plants were kept at 10-25°C or 20-35°C. The test period lasted 2-4 weeks, during which time the plants were cared for and their response to each treatment was assessed.

[0285] The racemic mixture (±)-2-exo-(2-methylbenzyloxy)-1-methyl-4-isopropyl-7-oxabicyclo[2.2.1]heptane was used as herbicide A and was formulated as an emulsifiable concentrate at active ingredient concentrations of 50 g / l, 100 g / l, or 750 g / l, respectively.

[0286] Flufenacet was used as a commercially available concentrated solution formulation (Cadou) with an active ingredient concentration of 500 g / l.

[0287] Imazamox was used as a water dispersible granule (70% WG).

[0288] Herbicidal activity was assessed using a scale of 0 to 100, with 100 indicating complete destruction of at least the aboveground parts and 0 indicating no damage or normal growth. Good herbicidal activity was given a value of at least 70, and very good herbicidal activity was given a value of at least 85.

[0289] [Table 3]

[0290] [Table 4]

[0291] As can be seen from the data in Tables 1 and 2, in post-emergence applications, Herbicide A exhibits very good herbicidal activity compared to commercial herbicides against various biotypes of black-glove (ALOMY) and ryegrass (LOLMU) with varying degrees of resistance to a wide range of modes of action according to the Herbicide Resistance Action Committee (HRAC) classification based on Mode of Action 2010.

[0292] II. Synergistic Interaction of Herbicides A and B The effect of herbicidal compositions of herbicides A and B of the invention, compared with the herbicidally active compounds alone, on undesirable plant growth is demonstrated in the following greenhouse experiment.

[0293] Test plants are sown separately for each species in plastic containers in sandy loam soil containing 5% organic matter.

[0294] In pre-emergence treatment, the active compound suspended or emulsified in water is applied directly after planting using a fine spray nozzle.To promote germination and growth, the container is gently irrigated, and then covered with a transparent plastic hood until the plants have rooted.This cover allows the test plants to germinate uniformly, unless the active compound has adverse effects.

[0295] For post-emergence treatment, plants are first grown to the two-leaf stage (GS12), at which point the herbicidal composition is suspended or emulsified with water as the spray medium and sprayed using a fine spray nozzle.

[0296] Plants are grown at 10-25° C. and 20-35° C. depending on individual requirements. Plants are irrigated as needed.

[0297] The racemic mixture (±)-2-exo-(2-methylbenzyloxy)-1-methyl-4-isopropyl-7-oxabicyclo[2.2.1]heptane is used as herbicide A and may be formulated, for example, as an emulsifiable concentrate in active ingredient concentrations of 50 g / l, 100 g / l or 750 g / l.

[0298] Herbicide B can be used, for example, as a commercially available formulation containing the appropriate concentrations of each active ingredient.

[0299] For example, the herbicidal activity of the individual herbicidal compositions (applied alone and in mixtures) can be evaluated at various time intervals after treatment, for example, 5, 10, 15 or 20 days after treatment (DAT).

[0300] The damage caused by the chemical composition to undesirable weeds is assessed in comparison to untreated control plants using a 0-100% scale, where 0 means no damage and 100 means the plants are completely destroyed.

[0301] Plants used in greenhouse experiments can be selected from the following species, among others:

[0302] [Table 5]

[0303] Colby's equation can be applied to determine whether a combination of herbicide A and herbicide B exhibits synergistic effects (see S.R. Colby, "Calculating synergistic and antagonistic responses of herbicide combinations," Weeds 1967, 15, pp. 20-22). E=X+Y-(X . Y / 100) During the ceremony, X = percent effectiveness of herbicide A at application rate a; Y = percent effectiveness of herbicide B at application rate b; E = predicted efficacy (%) of herbicide A + herbicide B at application rate a + b.

[0304] The value E corresponds to the effect (plant damage or injury) that would be expected if the activities of the individual compounds were additive. If the observed effect is higher than the value E calculated according to Colby's formula, a synergistic effect is present.

[0305] III. Synergistic Interaction of Herbicide A with Herbicides B.5 (Cyhalofop-Butyl), B.23 (Bispyribac-Sodium), B.53 (Metsulfuron-Methyl), and B.217 (Quizalofop-P-Ethyl) The effect of certain herbicidal compositions of herbicides A and B of the present invention on undesirable plant growth compared to the herbicidally active compounds alone was demonstrated in the following greenhouse experiment.

[0306] Test plants are sown separately for each species in plastic containers in sandy loam soil containing 5% organic matter.

[0307] For post-emergence treatment, plants were first grown to the two-leaf stage (GS12) and then treated at GS12 to GS19 depending on the species. The herbicidal compositions were suspended or emulsified in water as the spray medium and sprayed using a fine spray nozzle.

[0308] Plants were grown at 10-25°C and 20-35°C depending on individual requirements. Plants were irrigated as needed.

[0309] The racemic mixture (±)-2-exo-(2-methylbenzyloxy)-1-methyl-4-isopropyl-7-oxabicyclo[2.2.1]heptane was used as herbicide A and was formulated as an emulsifiable concentrate with an active ingredient concentration of 750 g / l.

[0310] Cyhalofop-butyl (herbicide B.5) was used as an emulsifiable concentrate (EC) formulation with an active ingredient concentration of 200 g / l.

[0311] Metsulfuron-methyl (herbicide B.53) was used as a granular water-soluble (SG) formulation with an active ingredient concentration of 20%.

[0312] Bispyribac-sodium (herbicide B.23) was used as a liquid solid (SL) formulation with an active ingredient concentration of 408 g / l.

[0313] Quizalofop-P-ethyl (herbicide B.217) was used as a suspension concentrate (SC) formulation with an active ingredient concentration of 106 g / l.

[0314] In the following experiments, the herbicidal activity of individual herbicide compounds (applied alone and in mixtures) was evaluated 20 days after treatment (DAT).

[0315] The assessment of damage to undesirable weeds caused by the chemical compositions was carried out in comparison with untreated control plants using a scale of 0 to 100%, where 0 means no damage and 100 means the plants were completely destroyed.

[0316] The plants used in the greenhouse experiments belonged to the following species:

[0317] [Table 6]

[0318] Colby's equation was applied to determine whether the combination of herbicide A and herbicide B exhibited a synergistic effect (see S.R. Colby, "Calculating synergistic and antagonistic responses of herbicide combinations," Weeds 1967, 15, pp. 20-22). E=X+Y-(X . Y / 100) During the ceremony, X = percent effectiveness of herbicide A at application rate a; Y = percent effectiveness of herbicide B at application rate b; E = predicted efficacy (%) of herbicide A + herbicide B at application rate a + b.

[0319] The value E corresponds to the effect (plant damage or injury) that would be expected if the activities of the individual compounds were additive. If the observed effect is higher than the value E calculated according to Colby's formula, a synergistic effect is present.

[0320] Tables 3 to 6 below relate to the herbicidal activity of the individual active substances and combinations applied at different amounts and rates in greenhouse tests, with post-emergence application 20 days after treatment (DAT).

[0321] [Table 7]

[0322] [Table 8]

[0323] [Table 9]

[0324] [Table 10]

[0325] As can be seen from the data in Tables 3-6, the combination of Herbicide A and Herbicide B exhibits unexpected synergy in that the herbicidal activity against various weed species in postemergence applications is significantly greater than would be predicted based on the values ​​for each compound individually.

Claims

1. 1. Use of (±)-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) for controlling herbicide-resistant or tolerant weed species.

2. 1. A method for controlling undesirable vegetation comprising the step of applying a herbicidally effective amount of (±)-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) to the vegetation or locus thereof, or to the soil or water to prevent emergence or growth of the undesirable vegetation, wherein the undesirable vegetation comprises at least one herbicide-resistant or tolerant weed species.

3. 3. The use according to claim 1 or the method according to claim 2, wherein the herbicide A is (±)-2-exo-(2-methylbenzyloxy)-1-methyl-4-isopropyl-7-oxabicyclo[2.2.1]heptane.

4. 4. The use according to claim 1 or 3, or the method according to claim 2 or 3, wherein the herbicide-resistant or tolerant weed species is a biotype that is resistant or tolerant 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 (PSII) inhibitors (HRAC groups C1, C2 and C3), microtubule assembly inhibitors (HRAC group K1), very long-chain fatty acid (VLCFA) inhibitors (HRAC group K3) and lipid synthesis inhibitors (HRAC group N).

5. 5. The use or method according to claim 4, wherein the herbicide-resistant or tolerant weed species is a biotype that is resistant or tolerant 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 (PSII) inhibitors (HRAC groups C1, C2, and C3).

6. Herbicide-resistant or tolerant weed species include: Triticum spp., Alopecurus spp., Common bean spp., Avena spp., Brachiaria spp., Bromegrass spp., Cardamom spp., Digitalia spp., Echinochloa spp., Goosegrass spp., Platypus spp., Leptolepis spp., Lolium spp., Panicum spp., Reed canary grass spp., Pseudoglossum spp., Atractylodes spp., Setaria spp., Anthemis spp., Amara spp.

6. The use according to any one of claims 1 and 3 to 5, or the method according to any one of claims 2 to 5, wherein the plant is selected from the genera Anthus, Ragweed, Shepherd's Purse, Centaurea, Chenopodium, Conyza, Desclerinia, Cleaver, Kochia, Deutzia, Papaver, Radish, White Mustard, Atractylodes, Stellaria and Shepherd's Purse.

7. 7. The use according to any one of claims 1 and 3 to 6, or the method according to any one of claims 2 to 6, wherein the herbicide-resistant or tolerant weed species is selected from the genera Alopecia, Brassica napus, Poa, Reed canary grass and Papaveraceae.

8. 8. The use according to any one of claims 1 and 3 to 7, or the method according to any one of claims 2 to 7, wherein the herbicide-resistant or tolerant weed species is selected from the genus Alopecurus.

9. 9. The use according to any one of claims 1 and 3 to 8, or the method according to any one of claims 2 to 8, wherein undesired vegetation is controlled in crop plants selected from wheat, barley, rye, triticale, oats, corn (maize), sunflower, rice, soybean, pea, Vicia faba, Phaseolus vulgaris, peanut, oilseed rape, canola, cotton, potato, sugar beet, sugarcane, turfgrass and vegetables.

10. 10. The use according to any one of claims 1 and 3 to 9, or the method according to any one of claims 2 to 9, wherein herbicide A is the only herbicidally active ingredient.

11. b1) to b15) group b1) Lipid biosynthesis inhibitors: Alloxydim, Alloxydim-sodium, Butroxydim, Clethodim, Clodinafop, Clodinafop-propargyl, Cycloxydim, Cyhalofop, Cyhalofop-butyl, Diclofop, Diclofop-methyl, 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, quizalofop-ethyl, quizalofop-tefuryl, quizalofop-P, quizalofop-P-ethyl, quizalofop-P-tefuryl, sethoxydim, tepraloxydim and tralkoxydim, 4-(4'-chloro-4-cyclopropyl-2'-fluoro[1,1'-biphenyl]-3-yl)-5-hydroxy-2,2,6,6-tetramethyl-2H-pyran-3(6H)-one (CAS 1312337-72-6; 4-(2',4'-dichloro-4-cyclopropyl[1,1'-biphenyl]-3-yl)-5-hydroxy-2,2,6,6-tetramethyl-2H-pyran-3(6H)-one (CAS 1312337-45-3); 4-(4'-chloro-4-ethyl-2'-fluoro[1,1'-biphenyl]-3-yl)-5-hydroxy-2,2,6,6-tetramethyl-2H-pyran-3(6H)-one (CAS 1033757-93-5); 4-(2',4'-dichloro-4-ethyl[1,1'-biphenyl]-3-yl)-2,2,6,6-tetramethyl-2H-pyran-3,5(4H,6H)-dione (CAS 1312340-84-3;5-(acetyloxy)-4-(4'-chloro-4-cyclopropyl-2'-fluoro[1,1'-biphenyl]-3-yl)-3,6-dihydro-2,2,6,6-tetramethyl-2H-pyran-3-one (CAS 1312337-48-6);5-(acetyloxy)-4-(2',4'-dichloro-4-cyclopropyl-[1,1'-biphenyl]-3-yl)-3,6-dihydro-2,2,6,6-tetramethyl-2H-pyran-3-one;5-(Acetyloxy)-4-(4'-chloro-4-ethyl-2'-fluoro[1,1'-biphenyl]-3-yl)-3,6-dihydro-2,2,6,6-tetramethyl-2H-pyran-3-one (CAS 1312340-82-1); 5-(Acetyloxy)-4-(2',4'-dichloro-4-ethyl[1,1'-biphenyl]-3-yl)-3,6-dihydro-2,2,6,6-tetramethyl-2H-pyran-3-one (CAS 1033760-55-2); 4-(4'-chloro-4-cyclopropyl-2'-fluoro[1,1'-biphenyl]-3-yl)-5,6-dihydro-2,2,6,6-tetramethyl-5-oxo-2H-pyran-3-yl carbonate methyl ester (CAS 1312337-51-1;4-(2',4'-dichloro-4-cyclopropyl-[1,1'-biphenyl]-3-yl)-5,6-dihydro-2,2,6,6-tetramethyl-5-oxo-2H-pyran-3-ylcarbonic acid methyl ester;4-(4'-chloro-4-ethyl-2'-fluoro[1,1'-biphenyl]-3-yl)-5,6-dihydro-2,2,6,6-tetramethyl-5-oxo-2H-pyran-3-ylcarbonic acid methyl ester (CAS 1312340-83-2);4-(2',4'-dichloro-4-ethyl[1,1'-biphenyl]-3-yl)-5,6-dihydro-2,2,6,6-tetramethyl-5-oxo-2H-pyran-3-ylcarbonic acid methyl ester (CAS 1033760-58-5); and non-ACC herbicides selected from benfuresate, butyrate, cycloate, dalapon, dimepiperate, EPTC, esprocarb, ethofumesate, flupropanate, molinate, orbencarb, pebulate, prosulfocarb, TCA, thiobencarb, thiocarbazyl, triallate and vernolate, b2) ALS inhibitors:; Amidosulfuron, azimsulfuron, bensulfuron, bensulfuron-methyl, chlorimuron, chlorimuron-ethyl, chlorsulfuron, cinosulfuron, cyclosulfamuron, ethametsulfuron, ethametsulfuron-methyl, ethoxysulfuron, flazasulfuron, flucetosulfuron, flupyrsulfuron, flupyrsulfuron-methyl-sodium, foramsulfuron, halosulfuron, halosulfuron-methyl, imazosulfuron, iodosulfuron, iodosulfuron-methyl-sodium, iofensulfuron, iofensulfuron-sodium, mesosulfuron, mesosulfuron sulfonylureas selected from pyrazosulfuron, primisulfuron-methyl, metazosulfuron, metsulfuron, metsulfuron-methyl, nicosulfuron, orthosulfamuron, oxasulfuron, primisulfuron, primisulfuron-methyl, propyrisulfuron, prosulfuron, pyrazosulfuron, pyrazosulfuron-ethyl, rimsulfuron, sulfometuron, sulfometuron-methyl, sulfosulfuron, thifensulfuron, thifensulfuron-methyl, triasulfuron, tribenuron, tribenuron-methyl, trifloxysulfuron, triflusulfuron, triflusulfuron-methyl and tritosulfuron; 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, penoxsulam, pyrimisulfan and pyroxsulam; pyrimidinyl benzoates selected from bispyribac, bispyribac-sodium, pyribenzoxim, pyriftalid, pyriminobac, pyriminobac-methyl, pyrithiobac, pyrithiobac-sodium, 4-[[[2-[(4,6-dimethoxy-2-pyrimidinyl)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), and N-(4-bromophenyl)-2-[(4,6-dimethoxy-2-pyrimidinyl)oxy]benzenemethanamine (CAS 420138-01-8); sulfonylaminocarbonyl-triazolinone herbicides selected from flucarbazone, flucarbazone-sodium, propoxycarbazone, propoxycarbazone-sodium, thiencarbazone and thiencarbazone-methyl; and triafamone, b3) Photosynthesis inhibitors: a triazine herbicide selected from ametryn, atrazine, cyanazine, desmetryn, dimethametryn, prometon, prometryn, propazine, simazine, simetryn, terbumeton, terbuthylazine, terbutryn, and trietazine; triazinones selected from hexazinone, metamitron and metribuzin; Triazolinones: amicarbazone, Pyridazinone: Chloridazon, ureas selected from chlorbromuron, chlorotoluron, chloroxuron, dimefuron, diuron, fluometuron, isoproturon, isouron, linuron, metamitron, methabenzthiazuron, metobenzuron, metoxuron, monolinuron, nebron, siduron, tebuthiuron and thidiazuron; phenylcarbamates selected from desmedipham, carbutilate, phenmedipham and phenmedipham-ethyl; a nitrile herbicide selected from bromofenoxime, bromoxynil, and ioxynil; uracils selected from bromacil, lenacil and terbacil; Bentazon, bentazon-sodium, pyridate, pyridahol, pentanochlor, propanil and a photosystem II inhibitor selected from diquat, diquat-dibromide, paraquat, paraquat-dichloride and paraquat-dimethylsulfate; b4) Protoporphyrinogen-IX oxidase inhibitors: acifluorfen, acifluorfen-sodium, azafenidin, bencarbazone, benzfendizone, bifenox, butafenacil, carfentrazone, carfentrazone-ethyl, clomethoxyfen, cinidon-ethyl, fluazolate, flufenpyr, flufenpyr-ethyl, flumiclorac, flumiclorac-pentyl, flumioxazin, fluoroglycofen, fluoroglycofen-ethyl, fluthiacet, fluthiacet-me cil, fomesafen, halosafen, lactofen, oxadiargyl, oxadiazon, oxyfluorfen, pentoxazone, profluazole, pyraclonil, pyraflufen, pyraflufen-ethyl, saflufenacil, sulfentrazone, thidiazimine, thiafenacil, trifludimoxadine, ethyl [3-[2-chloro-4-fluoro-5-(1-methyl-6-trifluoromethyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-3-yl)phenoxy]-2-pyridyloxy]acetate (CAS 10141-10-1) 353292-31-6; S-3100), N-ethyl-3-(2,6-dichloro-4-trifluoromethylphenoxy)-5-methyl-1H-pyrazole-1-carboxamide (CAS 452098-92-9), N-tetrahydrofurfuryl-3-(2,6-dichloro-4-trifluoromethylphenoxy)-5-methyl-1H-pyrazole-1-carboxamide (CAS 915396-43-9), N-ethyl-3-(2-chloro-6-fluoro-4-trifluoromethylphenoxy)-5-methyl-1H-pyrazole-1-carboxamide (CAS 452099-05-7), N-tetrahydrofurfuryl-3-(2-chloro-6-fluoro-4-trifluoromethylphenoxy)-5-methyl-1H-pyrazole-1-carboxamide (CAS 452100-03-7), 3-[7-fluoro-3-oxo-4-(prop-2-ynyl)-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl]-1,5-dimethyl-6-thioxo-[1,3,5]triazinane-2,4-dione (CAS 451484-50-7), 2-(2,2,7-trifluoro-3-oxo-4-prop-2-ynyl-3,4-dihydro 1-methyl-6-trifluoromethyl-3-(2,2,7-trifluoro-3-oxo-4-prop-2-ynyl-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)-1H-pyrimidine-2,4-dione (CAS 1304113-05-0), methyl (E)-4-[2-chloro-5-[4-chloro-5-(difluoromethoxy)-1H-methyl-pyrazol-3-yl]-4-fluoro-phenoxy]-3-methoxy-but-2-enoate (CAS 948893-00-3), and 3-[7-chloro-5-fluoro-2-(trifluoromethyl)-1H-benzimidazol-4-yl]-1-methyl-6-(trifluoromethyl)-1H-pyrimidine-2,4-dione (CAS 212754-02-4); b5) bleaching herbicides: PDS inhibitors selected from beflubutamide, diflufenican, fluridone, flurochloridone, flurtamone, norflurazone, picolinafen, and 4-(3-trifluoromethylphenoxy)-2-(4-trifluoromethylphenyl)pyrimidine (CAS 180608-33-7); HPPD inhibitors selected from benzobicyclon, benzofenap, bicyclopyrone, fenquinotrione, isoxaflutole, isoxachlortole, mesotrione, pyrasulfotole, pyrazolinate, pyrazoxyfen, sulcotrione, tefuryltrione, tembotrione, tolpyralate and topramezone; DOXP-synthase inhibitors selected from clomazone, b6) EPSP synthase inhibitors: Glyphosate, glyphosate isopropylammonium, glyphosate potassium, and glyphosate trimesium (sulfosate), b7) Glutamine synthase inhibitors: viranaphos (bialaphos), viranaphos-sodium, glufosinate, glufosinate-P and glufosinate-ammonium, b8) DHP synthase inhibitors: asulam, b9) Mitotic inhibitors: Compounds of the HRAC K1 group: dinitroanilines selected from benfluralin, butruarin, dinitramine, ethalfluralin, fluchloralin, oryzalin, pendimethalin, prodiamine and trifluralin, phosphoramidates selected from amiprophos, amiprophos-methyl and butamiphos, benzoic acid herbicides selected from chlorthal and chlorthal-dimethyl, pyridines selected from dithiopyr and thiazopyr, benzamides selected from propyzamide and tebutam, HRAC K2 group compounds: carbetamide, chlorpropham, flamprop, flamprop-isopropyl, flamprop-methyl, flamprop-M-isopropyl, flamprop-M-methyl and propham, b10) VLCFA inhibitors: chloroacetamides selected from acetochlor, alachlor, butachlor, dimethachlor, dimethenamid, dimethenamid-P, metazachlor, metolachlor, metolachlor-S, petoxamide, pretilachlor, propachlor, propisochlor and thenylchlor; oxyacetamides selected from flufenacet and mefenacet; Acetamides selected from diphenamide, naproanilide, napropamide and napropamide-M, tetrazolinones selected from fentrazamide and ipfencarbazone, other herbicides selected from anilophos, cafenstrole, fenoxasulfone, piperophos and pyroxasulfone, and herbicides of formula II.1, II.2, II.3, II.4, II.5, II.6, II.7, II.8 and II.9 【Chemistry 1】 【change】 an isoxazoline compound of the formula b11) Cellulose biosynthesis inhibitors: Chlorthiamid, dichlobenil, flupoxam, indaziflam, isoxaben, triaziflam and 1-cyclohexyl-5-pentafluorophenyloxy-1 4 -[1,2,4,6]thiatriazin-3-ylamine (CAS 175899-01-1), b12) Uncoupler herbicides: dinoseb, dinoterb and DNOC, b13) Synthetic auxins: 2,4-D, clasifos, 2,4-DB, aminocyclopyrachlor, aminopyralid, aminopyralid-dimethylammonium, aminopyralid-tris(2-hydroxypropyl)ammonium, benazolin, benazolin-ethyl, chloramben, clomeprop, clopyralid, dicamba, dichlorprop, dichlorprop-P, fluroxypyr, fluroxypyr-butomethyl, fluroxypyr-meptyl, halaxifene (CAS 943832-60-8; MCPA, MCPA-thioethyl, MCPB, mecoprop, mecoprop-P, picloram, quinclorac, quinmerac, TBA(2,3,6), triclopyr, 4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)-5-fluoropyridine-2-carboxylic acid, and benzyl 4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)-5-fluoropyridine-2-carboxylate (CAS 1390661-72-9), b14) Auxin transport inhibitors: diflufenzopyr, diflufenzopyr-sodium, naptalam and naptalam-sodium; b15) Other herbicides: bromobutide, chlorflurenol, chlorflurenol-methyl, cumyluron, cyclopyrimorate (CAS 499223-49-3), dalapon, dazomet, difenzoquat, difenzoquat-methyl sulfate, dimethipine, DSMA, dymron, endothall, etobenzanide, flurenol, flurenol-butyl, flurprimidol, fosamine, fosamine-ammonium, indanofan, maleic hydrazide, mefluidide, metam, methiozoline (CAS 403640-27-7), methyl azide, methyl bromide, methyl-dymron, methyl iodide, MSMA, oleic acid, oxaziclomefone, pelargonic acid, pyributicarb, quinoclamine and tridiphane, and agriculturally acceptable salts, esters or amides thereof 10. The use according to any one of claims 1 and 3 to 9, or the method according to any one of claims 2 to 9, further comprising the step of applying at least one herbicide B selected from:

12. Benoxacor, cloquintocet, siometrinil, cyprosulfamide, dichlormid, dicyclonone, dietholate, fenchlorazole, fenclorim, flurazole, fluxofenim, furilazole, isoxadifen, mefenpyr, mephenate, naphthaleneacetic acid (NAA), naphthalic anhydride (NA), oxabetrinil, 4-(dichloroacetyl)-1-oxa-4-azaspiro[4.5]decane (MON4660), 2,2,5 12. The use according to any one of claims 1 and 3 to 11, or the method according to any one of claims 2 to 11, further comprising the step of applying at least one safener C selected from the group consisting of -trimethyl-3-(dichloroacetyl)-1,3-oxazolidine (R-29148), N-(2-methoxybenzoyl)-4-[(methylaminocarbonyl)amino]benzenesulfonamide, and agriculturally acceptable salts, esters or amides thereof.

13. 13. The use according to any one of claims 1 and 3 to 12, or the method according to any one of claims 2 to 12, further comprising the step of applying one or more adjuvants customary in crop protection.

14. 14. The use according to any one of claims 1 and 3 to 13, or the method according to any one of claims 2 to 13, wherein a composition comprising a herbicidally effective amount of herbicide A and optionally at least one herbicide B is applied.

15. 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); and (b) a compound of the group b1) Lipid biosynthesis inhibitors: cyhalofop, quizalofop, b2) ALS inhibitors: metsulfuron, penoxsulam, pyrimisulfan, bispyribac, pyribenzoxim, pyriftalid, pyriminobac, b3) Photosynthesis inhibitors: propanil, b5) bleaching herbicides: benzobicyclon, benzofenap, isoxachlorthol, pyrazolinate, pyrazoxyfen, tefuryltrione, b10) VLCFA inhibitors: fentrazamide, ipfencarbazone, cafenstrole, fenoxasulfone, b13) Synthetic auxin: benzyl 4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)-5-fluoropyridine-2-carboxylate (CAS 1390661-72-9), b15) Other herbicides: indanofan, methiozolin (CAS 403640-27-7), oxaziclomefone, and agriculturally acceptable salts, esters or amides thereof A herbicidal composition comprising at least one herbicide B selected from:

16. At least one herbicide B is selected from the group b1) Lipid biosynthesis inhibitors: cyhalofop, cyhalofop-butyl, quizalofop, and quizalofop-P-ethyl; b2) ALS inhibitors: metsulfuron, metsulfuron-methyl, bispyribac, and bispyribac-sodium 16. The composition of claim 15, wherein the composition is selected from:

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