WO2019243101A1 - Method for controlling herbicide resistant or tolerant weeds - Google Patents

Method for controlling herbicide resistant or tolerant weeds Download PDF

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WO2019243101A1
WO2019243101A1 PCT/EP2019/065096 EP2019065096W WO2019243101A1 WO 2019243101 A1 WO2019243101 A1 WO 2019243101A1 EP 2019065096 W EP2019065096 W EP 2019065096W WO 2019243101 A1 WO2019243101 A1 WO 2019243101A1
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methyl
herbicide
cas
inhibitors
lolium
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PCT/EP2019/065096
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French (fr)
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Helmut Kraus
Andreas Landes
Gerd Kraemer
Matthias Witschel
Eva HOLLENBACH
Ruth CAMPE
Tobias MENTZEL
Jens Lerchl
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Basf Se
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    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/80—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,2

Abstract

The present invention relates to methods and uses for controlling herbicide resistant or tolerant weed species by applying the compound (5/RS)-5-[(2,6-difluorobenzyloxy)methyl]-4,5-dihydro-5- methyl-3-(3-methyl-2-thienyl)-1,2-oxazole of the formula I any of its individual enantiomers or any non-racemic mixture thereof (herbicide A). The methods and uses are particularly suitable for the protection of crops. The invention also relates to herbicidal combinations comprising said herbicide A and a herbicide B which is different from herbicide A.

Description

Method for controlling herbicide resistant or tolerant weeds
The present invention relates to methods and uses for controlling herbicide resistant or tolerant weed species by applying the compound (5/?S)-5-[(2,6-difluorobenzyloxy)methyl]-4,5-dihydro-5- methyl-3-(3-methyl-2-thienyl)-1 ,2-oxazole of the formula I
Figure imgf000002_0001
any of its individual enantiomers or any non-racemic mixture thereof (herbicide A). The methods and uses are particularly suitable for the protection of crops. The invention also relates to herbi- cidal combinations comprising said herbicide A and a herbicide B which is different from herbi- cide A.
Background of the invention
Cases of herbicide-resistant weeds are becoming increasingly common. These biotypes survive herbicide application at doses that usually give effective control of the species. Resistant weed biotypes are a consequence of basic evolutionary processes. Individuals within a species that are best adapted to a specific practice are selected for and will increase in the population. Once a weed population is exposed to a herbicide to which one or more plants are naturally resistant, the herbicide kills susceptible individuals, but allows resistant individuals to survive and repro- duce. With repeated herbicide use, resistant weeds that initially appear as isolated plants or patches in a field can quickly spread to dominate the population and the soil seed bank.
For example, herbicide resistance within weeds, in particular grass weeds such as, for example, Alopecurus myosuroides (ALOMY), Apera spica-venti (APESV) or Lolium species (LOLSS), but also broadleaf weeds like Amaranthus species (AMASS) and Raphanus species (RAPSS), has become a major concern for farmers, resulting in dramatic weed control problems, for example in cereal crops. Herbicides from the group of EPSP synthase-, ACCase- and ALS-inhibitors are most affected by resistance evolution but also various other types of herbicides.
US 2004/0023808 describes herbicidal 5-benzyloxymethyl-1 ,2-isoxazoline derivatives, inter alia 5-(2,6-difluorobenzyl)oxymethyl-5-methyl-3-(4-methyl thiophene-5-yl)-1 ,2-isoxazoline (see ex- ample 8), which corresponds to the compound of formula I.
US 2008/0318784 A1 and US 2011/0306496 describe the use of 5-benzyloxymethyl-1 ,2-isoxa- zoline derivatives, inter alia 5-(2,6-difluorobenzyl)oxymethyl-5-methyl-3-(4-methyl thiophene-5- yl)-1 ,2-isoxazoline (see compound of formual II) against certain gramineous weeds for upland crops, turfgrasses and direct-seeded rice. WO 2018/019845 discloses a method for controlling PPO resistant weeds by appliying saflufenacil to the PPO resistant weeds. A composition comprising saflufenacil and at least one further herbicide B can also be applied wherein the herbicide B may be selected from various compounds, inter alia methiozolin.
It is known that compositions comprising cinmethylin and further herbicides B) such as pyrox- asulfone (WO 2017/009090), flufenacet (WO 2017/009124), metolachlor or S-metolachlor (WO 2017/009092), pendimethalin (WO 2017/009095), diflufenican or picolinafen (WO
2017/009143), saflufenacil (WO 2017/009061 ), flumioxazin and sulfentrazone (WO
2017/009145 or pendimethalin and flufenacet (WO 2017/009088) can be used for controlling re- sistant or tolerant weeds. Such compositions may further comprise a herbicide C which may be selected from various compounds, inter alia methiozolin.
James T. Brosnan et al.,“Controlling Herbicide-Resistant Annual Bluegrass (Poa annua) Phe- notypes with Methiozolin”, Weed Technology, Vol. 31 , No. 03 (2017) describes that methiozolin controlled annual bluegrass phenotypes with target-site resistance to photosystem II (PSII) or enolpyruvylshikimate-3-phosphate synthase (EPSPS)-inhibiting herbicides (i.e. glyphosate), as well as phenotypes with multiple resistance to microtubule and EPSPS or PSII and acetolactate synthase (ALS)-inhibiting.
Nevertheless, there is still a need to further develop practices for preventing, delaying or man- aging herbicide resistance in weeds.
Further, there is still room for improvement, for example regarding the activity, spectrum of ac- tivity and compatibility with useful plants, especially in respect of the control of resistant weed biotypes.
Summary of the invention
Thus, an object of the present invention lies in the effective control of herbicide-resistant weed biotypes, especially in herbicide-resistant grass and/or broadleaf weeds.
It is also an object of the present invention to improve the herbicidal activity against undesirable harmful plants and/or the compatibility with the useful plants (in particular crop plants).
These and further objects are achieved by the methods and uses below.
Accordingly, in one aspect of the invention, there is provided a method for controlling undesira- ble vegetation which comprises applying to the vegetation or the locus thereof or applying to the soil or water to prevent the emergence or growth of the undesirable vegetation a herbicidally ef- fective amount of (5/?S)-5-[(2,6-difluorobenzyloxy)methyl]-4,5-dihydro-5-methyl-3-(3-methyl-2- thienyl)-1 ,2-oxazole of the formula I
Figure imgf000004_0002
any of its individual enantiomers or any non-racemic mixture thereof (herbicide A) wherein the undesirable vegetation comprises at least one herbicide resistant or tolerant weed species.
(5/?S)-5-[(2,6-difluorobenzyloxy)methyl]-4,5-dihydro-5-methyl-3-(3-methyl-2-thienyl)-1 ,2-oxazole of the formula I is a known herbicidal active compound (CAS Registry No. 403640-27-7, see e.g. Pesticide Manual Online, British Crop Protection Council, 2016 and Compendium of Pesti- cide Common Names accessible through the website http://www.alanwood.net/pesticides/me- thiozolin.html) and may be prepared by processes such as those described in
US 2004/0023808 (see Example 8) and US 2015/0158852. Other names for the compound of formula I include, for example, /ac-(5/\ -5-{[(2,6-difluorophenyl)methoxy]methyl}-5-methyl-3-(3- methylthiophen-2-yl)-4,5-dihydro-1 ,2-oxazole, 5-[[(2,6-difluorophenyl)methoxy]methyl]-4,5-dihy- dro-5-methyl-3-(3-methyl-2-thienyl)isoxazole or methiozolin.
(5/?S)-5-[(2,6-difluorobenzyloxy)methyl]-4,5-dihydro-5-methyl-3-(3-methyl-2-thienyl)-1 ,2-oxazole of the formula I is a chiral molecule and contains equal parts of the two enantiomers (SJ-5-(2,6- Difluorobenzyloxymethyl)-5-methyl-3-(3-methylthiophen-2-yl)-4,5-dihydroisoxazole of the for- mula l-S (herein also referred to as YS methiozolin") and (7?)-5-(2,6-Difluorobenzyloxymethyl)- 5-methyl-3-(3-methylthiophen-2-yl)-4,5-dihydroisoxazole of the formula l-R (herein also referred to as " 7?)-methiozolin").
Figure imgf000004_0001
(I-S) (l-R)
The synthesis and herbidical activities of (SYmethiozolin and 7?)-methiozolin are described in Bull. Korean Chem. Soc. 2012, Vol. 33, No. 1 , 297-300.
The term "herbicidally effective amount" denotes an amount of the active ingredients, which is sufficient for controlling unwanted plants, especially for controlling unwanted plants in cultivated plants and which does not result in a substantial damage to the treated plants. Such an amount can vary in a broad range and is dependent on various factors, such as the plants to be con- trolled, the treated cultivated plant or material, the climatic conditions and the specific combina- tions/compositions according to the invention used.
The terms "plants" and "vegetation", as used herein, include germinant seeds, emerging seed- lings, plants emerging from vegetative propagules, and established vegetation.
The term "locus", as used herein, means the area in which the vegetation or plants are growing or will grow, typically a field.
The terms "controlling" and "combating", as used herein, are synonyms.
The terms "undesirable vegetation", "harmful plants",“unwanted plants”,“weeds” and“weed species”, as used herein, are synonyms.
The present invention also relates to the use of (5/?S)-5-[(2,6-difluorobenzyloxy)methyl]-4,5-di- hydro-5-methyl-3-(3-methyl-2-thienyl)-1 ,2-oxazole of the formula I
Figure imgf000005_0001
any of its individual enantiomers or any non-racemic mixture thereof (herbicide A) for controlling herbicide resistant or tolerant weed species.
The use or method of the invention may further comprise applying at least one herbicide B (as defined hereinafter) which is different from the herbicide A.
Thus, in another aspect, a herbicidal combination comprising a) the herbicide A and b) at least one herbicide B different from herbicide A may be used or applied in the use or method of this invention.
The method of the invention may further comprise applying at least one safener C (as defined herein).
In another aspect, the present invention relates to the use of a herbicidal combination comprising a) the herbicide A, b) a herbicide B which is different from herbicide A and optionally c) at least one safener C (as defined herein). In another aspect, the present invention relates to a method for controlling undesirable vegetation which comprises applying to the vegetation or the locus thereof a herbicidal combination comprising a) the herbicide A, b) a herbicide B which is different from herbicide A and optionally c) at least one safener C (as defined herein).
In another aspect, the present invention relates to a herbicidal combination comprising a) the herbicide A, b) at least one herbicide B which is different from herbicide A and optionally c) at least one safener C (as defined herein).
In another aspect, the present invention provides an agrochemical composition comprising a herbicidally effective amount of the herbicide A or the herbicidal combination as defined herein and one or more auxiliaries customary in crop protection (as defined hereinafter).
Further embodiments of the invention are evident from the description, the examples and the claims. It is to be understood that the features mentioned above and still to be illustrated below of the subject matter of the invention can be applied not only in the combination given in each particular case but also in other combinations, without leaving the scope of the invention.
Detailed description of the invention
Surprisingly, it has been found that the herbicidal compound (5/?S)-5-[(2,6-difluoroben- zyloxy)methyl]-4,5-dihydro-5-methyl-3-(3-methyl-2-thienyl)-1 ,2-oxazole of the formula I, any of its individual enantiomers or any non-racemic mixture thereof (herbicide A) provides effective control of herbicide resistant or tolerant weed species, in particular herbicide-resistant weed bio- types. For example, herbicide A can effectively control herbicide-resistant grass weeds such as, for example, Alopecurus myosuroides (ALOMY), Apera spica-venti (APESV), Avena fatua (AVEFA), Bromus species (BROSS), Phalaris species (PHASS), Poa annua (POAAN) or Lolium species (LOLSS). Herbicide A is also suitable for controlling herbicide-resistant broadleaf weeds such as, for example, Papaver rhoeas (PAPRH, corn poppy) or Raphanus raphanistrum (RAPRA) or which have evolved resistance, especially against EPSP synthase-, ALS-, AC- Case- or VLCFA-inhibiting herbicides.
Another advantage of this invention is that herbicide A can be used for controlling weed bio- types with target-site resistance but also weed biotypes with non-target site resistance. A partic- ular advantage of the invention is that herbicide A also provides effective control of weed bio- types having both target-site resistance and non-target-site resistance, such as e.g. resistant populations of Alopecurus myosuroides (ALOMY), Lolium rigidum (LOLRI) or Raphanus raphanistrum (RAPRA).
"Target-site resistance", as used herein, occurs by mutation within a gene coding for an herbi- cide target-site enzyme (limiting the herbicide binding) or by overproduction of the target en- zyme (gene overexpression or amplification). "Non-target-site resistance", as used herein, involves mechanisms that minimize the amount of active herbicide reaching the target site (e.g. reduced herbicide uptake or translocation, in- creased herbicide sequestration, or enhanced herbicide metabolism).
The term "herbicide A" as used herein is meant to include racemic methiozolin, i.e. (5/?S)-5- [(2,6-difluorobenzyloxy)methyl]-4,5-dihydro-5-methyl-3-(3-methyl-2-thienyl)-1 ,2-oxazole of the formula I, any of its individual enantiomers S methiozolin and 7?)-methiozolin, i.e. (S)- 5-(2,6- Difluorobenzyloxymethyl)-5-methyl-3-(3-methylthiophen-2-yl)-4,5-dihydroisoxazole of the for- mula l-S and (7?)-5-(2,6-Difluorobenzyloxymethyl)-5-methyl-3-(3-methylthiophen-2-yl)-4,5-dihy- droisoxazole of the formula l-R, or any non-racemic mixture thereof.
In a preferred embodiment, the herbicide A is (5/?S)-5-[(2,6-difluorobenzyloxy)methyl]-4,5-dihy- dro-5-methyl-3-(3-methyl-2-thienyl)-1 ,2-oxazole of the formula I, i.e. methiozolin.
In another embodiment, the herbicide A is (2>)-5-(2,6-Difluorobenzyloxymethyl)-5-methyl-3-(3- methylthiophen-2-yl)-4,5-dihydroisoxazole of the formula l-S or 7?)-5-(2,6-Difluorobenzyloxyme- thyl)-5-methyl-3-(3-methylthiophen-2-yl)-4,5-dihydroisoxazole of the formula l-R.
In another embodiment, herbicide A is a non-racemic mixture of (2>)-5-(2,6-Difluoroben- zyloxymethyl)-5-methyl-3-(3-methylthiophen-2-yl)-4,5-dihydroisoxazole of the formula l-S and (7?)-5-(2,6-Difluorobenzyloxymethyl)-5-methyl-3-(3-methylthiophen-2-yl)-4,5-dihydroisoxazole of the formula l-R. The non-racemic mixture contains unequal parts of S/methiozolin and (R)- me- thiozolin. The weight ratio of S methiozolin to 7?)-methiozolin in the non-racemic mixture can vary widely.
Exemplary herbicide resistant or tolerant weed species include, but are not limited to, biotypes resistant or tolerant to herbicides selected from the group consisting of acetyl CoA carboxylase (ACCase) inhibitors (HRAC Group A), acetolactate synthase (ALS) inhibitors (HRAC Group B), photosystem II (PS II) inhibitors (HRAC Groups C1 , C2 and C3), photosystem I (PS I) inhibitors (HRAC Group D), protoporphyrinogen oxidase (PPO) inhibitors (HRAC Group E), 4-hydroxy- phenyl-pyruvate-dioxygenase (HPPD) inhibitors (HRAC Group F1 ), phytoene desaturase (PDS) inhibitors (HRAC Group F2), carotenoid biosynthesis inhibitors (HRAC Group F3), DOXP syn- thase inhibitors (HRAC Group F4), 5-enolpymvylshikimate-3-phosphate (EPSP) inhibitors (HRAC Group G), glutamine synthetase inhibitors (HRAC Group H), DHP synthase inhibitors (HRAC Group I), inhibitors of microtubuli assembly (HRAC Group K1 ), inhibitors of mitosis/mi- crotubuli organization (HRAC Group K2), very long chain fatty acid (VLCFA) inhibitors (HRAC Group K3), Inhibitors of cell wall synthesis (HRAC Group L), uncoupler (membran disruption) (HRAC Group M), Inhibitors of lipid synthesis (HRAC Group N), synthetic auxins (HRAC Group O), auxin transport inhibitors (HRAC Group P) and herbicides with unknown mode of action (HRAC Group Z).
Preferably, the herbicide resistant or tolerant weed species is selected from biotypes resistant or tolerant to herbicides selected from the group consisting of acetyl CoA carboxylase (ACCase) inhibitors (HRAC Group A), acetolactate synthase (ALS) inhibitors (HRAC Group B), photosystem II (PS II) inhibitors (HRAC Groups C1 , C2 and C3), protoporphyrinogen oxidase (PPO) inhibitors (HRAC Group E), 4-hyd roxyphenyl-pyruvate-d ioxygenase (HPPD) inhibitors (HRAC Group F1), phytoene desaturase (PDS) inhibitors (HRAC Group F2),
5-enolpymvylshikimate-3-phosphate (EPSP) inhibitors (HRAC Group G), glutamine synthetase inhibitors (HRAC Group H), inhibitors of microtubuli assembly (HRAC Group K1), very long chain fatty acid (VLCFA) inhibitors (HRAC Group K3), Inhibitors of cell wall synthesis (HRAC Group L) and inhibitors of lipid synthesis (HRAC Group N).
More preferably, the herbicide resistant or tolerant weed species is selected from biotypes resistant or tolerant to herbicides selected from the group consisting of acetyl CoA carboxylase (ACCase) inhibitors (HRAC Group A), acetolactate synthase (ALS) inhibitors (HRAC Group B), photosystem II (PS II) inhibitors (HRAC Groups C1 , C2 and C3), 5-enolpymvylshikimate-3- phosphate (EPSP) inhibitors (HRAC Group G), glutamine synthetase inhibitors (HRAC Group H), inhibitors of microtubuli assembly (HRAC Group K1 ), very long chain fatty acid (VLCFA) inhibitors (HRAC Group K3) and inhibitors of lipid synthesis (HRAC Group N).
Even more preferably, the herbicide resistant or tolerant weed species is selected from biotypes with resistance or tolerance to at least one herbicide selected from the group consisting of acetyl CoA carboxylase (ACCase) inhibitors (HRAC Group A), acetolactate synthase (ALS) inhibitors (HRAC Group B), photosystem II (PS II) inhibitors (HRAC Groups C1 , C2 and C3), 5- enolpymvylshikimate-3-phosphate (EPSP) inhibitors (HRAC Group G), glutamine synthetase inhibitors (HRAC Group H), inhibitors of microtubuli assembly (HRAC Group K1 ) and very long chain fatty acid (VLCFA) inhibitors (HRAC Group K3).
In particular, the herbicide resistant or tolerant weed species is selected from biotypes with resistance or tolerance to at least one herbicide selected from the group consisting of acetyl CoA carboxylase (ACCase) inhibitors (HRAC Group A), acetolactate synthase (ALS) inhibitors (HRAC Group B), photosystem II (PS II) inhibitors (HRAC Groups C1 , C2 and C3), inhibitors of microtubuli assembly (HRAC Group K1 ) and very long chain fatty acid (VLCFA) inhibitors (HRAC Group K3).
In one embodiment, the herbicide resistant or tolerant weed species is selected from biotypes with resistance or tolerance to at least one herbicide selected from acetyl CoA carboxylase (ACCase) inhibitors (HRAC Group A).
In another embodiment, the herbicide resistant or tolerant weed species is selected from biotypes with resistance or tolerance to at least one herbicide selected from acetolactate synthase (ALS) inhibitors (HRAC Group B).
In another embodiment, the herbicide resistant or tolerant weed species is selected from biotypes with resistance or tolerance to at least one herbicide selected from photosystem II (PS II) inhibitors (HRAC Groups C1 , C2 and C3).
In another embodiment, the herbicide resistant or tolerant weed species is selected from biotypes with resistance or tolerance to at least one herbicide selected from 5- enolpymvylshikimate-3-phosphate (EPSP) inhibitors (HRAC Group G).
In another embodiment, the herbicide resistant or tolerant weed species is selected from biotypes with resistance or tolerance to at least one herbicide selected from glutamine synthetase inhibitors (HRAC Group H).
In another embodiment, the herbicide resistant or tolerant weed species is selected from biotypes with resistance or tolerance to at least one herbicide selected from inhibitors of microtubuli assembly (HRAC Group K1 ) and very long chain fatty acid (VLCFA) inhibitors (HRAC Group K3).
In another embodiment, the herbicide resistant or tolerant weed species is selected from biotypes with resistance or tolerance to at least one herbicide selected from very long chain fatty acid (VLCFA) inhibitors (HRAC Group K3).
In another embodiment, the herbicide resistant or tolerant weed species is selected from the genera Agropyron, Alopecurus, Apera, Avena, Brachiaria, Bromus, Cynodon, Digitaria, Echi- nochloa, Eleusine, Ischaemum, Leptochloa, Lolium, Panicum, Phalaris, Poa, Rottboellia,
Setaria, Anthemis, Amaranthus, Ambrosia, Capsella, Centaurea, Chenopodium, Commelina, Conyza, Descurainia, Galium, Kochia, Matricaria, Papaver, Raphanus, Sinapis, Sisymbrium, Stellaria and Thlaspi, preferably selected from the genera Alopecurus, Apera, Avena, Lolium, Phalaris, Poa, Commelina, Papaver and Raphanus, more preferably selected from the genera Alopecurus, Apera, Avena, Lolium, Phalaris, Poa, Papaver and Raphanus and even more pref- erably selected from the genera Alopecurus, Avena, Lolium and Raphanus.
In another embodiment, the herbicide resistant or tolerant weed species is selected from the genera Agropyron, Alopecurus, Apera, Avena, Brachiaria, Bromus, Cynodon, Digitaria, Eleu- sine, Leptochloa, Lolium, Phalaris, Rottboellia, Anthemis, Amaranthus, Ambrosia, Capsella, Centaurea, Chenopodium, Commelina, Conyza, Descurainia, Galium, Kochia, Matricaria, Papa- ver, Raphanus, Sinapis, Sisymbrium, Stellaria and Thlaspi, preferably selected from the genera Alopecurus, Apera, Avena, Lolium, Phalaris, Commelina, Papaver and Raphanus, more prefer- ably selected from the genera Alopecurus, Apera, Avena, Lolium, Phalaris, Papaver and Raphanus and even more preferably selected from the genera Alopecurus, Avena, Lolium and Raphanus.
In one embodiment, the herbicide resistant or tolerant weed species is a monocotyledonous weed species selected from the genera Agropyron, Alopecurus, Apera, Avena, Brachiaria, Bro- mus, Cynodon, Digitaria, Echinochloa, Eleusine, Ischaemum, Leptochloa, Lolium, Panicum, Phalaris, Poa, Rottboellia and Setaria, preferably selected from the genera Alopecurus, Apera, Avena, Bromus, Lolium, Phalaris and Poa, more preferably selected from the genera Alopecu- rus, Apera, Avena, Lolium, Phalaris and Poa, even more preferably selected from the genera Alopecurus, Avena, and Lolium and still more preferably selected from the genera Alopecurus and Lolium. In another embodiment, the herbicide resistant or tolerant weed species is a monocotyledonous weed species selected from the genera Agropyron, Alopecurus, Apera, Avena, Brachiaria, Bro- mus, Cynodon, Digitaria, Eleusine, Leptochloa, Lolium, Phalaris and Rottboellia, preferably se- lected from the genera Alopecurus, Apera, Avena, Lolium, Phalaris and Commelina, more pref- erably selected from the genera Alopecurus, Apera, Avena, Lolium and Phalaris, even more preferably selected from the genera Alopecurus, Avena and Lolium and still more preferably se- lected from the genera Alopecurus and Lolium.
In another embodiment, the herbicide resistant or tolerant weed species is selected from the ge- nus Alopecurus.
In another embodiment, the herbicide resistant or tolerant weed species is selected from the ge- nus Apera.
In another embodiment, the herbicide resistant or tolerant weed species is selected from the ge- nus Avena.
In another embodiment, the herbicide resistant or tolerant weed species is selected from the ge- nus Bromus.
In another embodiment, the herbicide resistant or tolerant weed species is selected from the ge- nus Lolium.
In another embodiment, the herbicide resistant or tolerant weed species is selected from the ge- nus Phalaris.
In another embodiment, the herbicide resistant or tolerant weed species is selected from the ge- nus Poa.
In another embodiment, the herbicide resistant or tolerant weed species is a dicotyledonous weed species, preferably a dicotyledonous weed species selected from the genera Anthemis, Amaranthus, Ambrosia, Capsella, Centaurea, Chenopodium, Commelina, Conyza, Descurainia, Galium, Kochia, Matricaria, Papaver, Raphanus, Sinapis, Sisymbrium, Stellaria and Thlaspi, preferably selected from the genera Commelina, Papaver and Raphanus, more preferably from the genera Papaver and Raphanus and in particular selected from the genus Raphanus. In an- other embodiment, the herbicide resistant or tolerant weed species is selected from the genus Papaver. In another embodiment, the herbicide resistant or tolerant weed species is selected from the genus Commelina.
In particular, the herbicide resistant or tolerant weed species is selected from the group consist- ing of Alopecurus myosuroides, Alopecurus aequalis, Apera spica-venti, Avena fatua, Avena sterilis, Brachiaria plantaginea, Brachiaria decumbens, Bromus secalinus, Bromus sterilis, Bro- mus tectorum, Digitaria ciliaris, Digitaria insularis, Digitaria ischaemum, Digitaria sanguinalis, Echinochloa colona, Echinochloa crus-galli, Echinochloa crus-pavonis, Echinochloa erecta, Echinochloa oryzoides, Echinochloa phyllogogon, Eleusine indica, Ischaemum rugosum, Lepto- chloa chinensis, Leptochloa panicoides, Leptochloa scabra, Leptochloa virgata, Lolium multiflo- rum, Lolium perenne, Lolium rigidum, Lolium x hybridum, Panicum capillare, Panicum di- chotomiflorum, Phalaris brachystachyx, Phalaris minor, Phalahs paradoxa, Poa annua, Poa pratensis, Poa trivialis, Rottboellia exaltata, Setaria faberi, Setaria glauca, Setaria pumila,
Setaria verticillata, Setaria viridis, Amaranthus albus, Amaranthus blitoides, Amaranthus hy- bridus, Amaranthus palmeri, Amaranthus powellii, Amaranthus retroflexus, Amaranthus tuber- culatus, Amaranthus rudis, Amaranthus viridis, Ambrosia artemisifolia, Anthemis arvensis, Capsella bursa-pastoris, Centaurea cyanus, Chenopodium album, Chenopodium ficifolium, Chenopodium polyspermum, Chenopodium hybridum, Commelina benghalensis, Conyza bon- ariensis, Conyza canadensis, Descurania sophia, Galium aparine, Galium spurium, Galium tri- cornutum, Kochia scoparia, Matricaria chamomilla, Matricaria discoidea, Matricaria inodora, Pa- paver rhoeas, Raphanus raphanistrum, Sinapis alba, Sinapis arvensis, Sisymbrium officinale, Sisymbrium orientale, Stellaria media and Thlaspi arvense, preferably selected from the group consisting of Alopecurus myosuroides, Alopecurus aequalis, Apera spica-venti, Avena fatua, Avena sterilis, Lolium multiflorum, Lolium perenne, Lolium rigidum, Lolium x hybridum, Phalaris brachystachyx, Phalaris minor, Phalaris paradoxa, Poa annua, Poa pratensis, Poa trivialis, Commelina benghalensis, Papaver rhoeas and Raphanus raphanistrum, more preferably se- lected from the group consisting of Alopecurus myosuroides, Alopecurus aequalis, Apera spica- venti, Avena fatua, Avena sterilis, Lolium multiflorum, Lolium perenne, Lolium rigidum, Lolium x hybridum, Phalaris brachystachyx, Phalaris minor, Phalaris paradoxa, Poa annua, Poa praten- sis, Poa trivialis, Papaver rhoeas and Raphanus raphanistrum, even more preferably selected from the group consisting of Alopecurus myosuroides, Alopecurus aequalis, Avena fatua, Avena sterilis, Lolium multiflorum, Lolium perenne, Lolium rigidum, Lolium x hybridum and Raphanus raphanistrum and in particular selected from the group consisting of Alopecurus myosuroides, Lolium multiflorum, Lolium rigidum and Lolium x hybridum.
In another embodiment, the herbicide resistant or tolerant weed species is selected from the group consisting of Alopecurus myosuroides and Alopecurus aequalis. In another embodiment, the herbicide resistant or tolerant weed species is Alopecurus myosuroides. In another embodi- ment, the herbicide resistant or tolerant weed species is Alopecurus aequalis.
In another embodiment, the herbicide resistant or tolerant weed species is Apera spica-venti.
In another embodiment, the herbicide resistant or tolerant weed species is selected from the group consisting of Avena fatua and Avena sterilis. In another embodiment, the herbicide resistant or tolerant weed species is Avena fatua. In another embodiment, the herbicide resistant or tolerant weed species is Avena sterilis.
In another embodiment, the herbicide resistant or tolerant weed species is selected from the group consisting of Lolium multiflorum, Lolium perenne, Lolium rigidum and Lolium x hybridum, preferably from the group consisting of Lolium multiflorum, Lolium rigidum and Lolium x hybridum. In another embodiment, the herbicide resistant or tolerant weed species is Lolium multiflorum. In another embodiment, the herbicide resistant or tolerant weed species is Lolium perenne.
In another embodiment, the herbicide resistant or tolerant weed species is Lolium rigidum.
In another embodiment, the herbicide resistant or tolerant weed species is Lolium x hybridum.
In another embodiment, the herbicide resistant or tolerant weed species is selected from the group consisting of Phalaris brachystachyx, Phalaris minor and Phalaris paradoxa.
In another embodiment, the herbicide resistant or tolerant weed species is Phalaris bra- chystachyx.
In another embodiment, the herbicide resistant or tolerant weed species is Phalaris minor.
In another embodiment, the herbicide resistant or tolerant weed species is Phalaris paradoxa.
In another embodiment, the herbicide resistant or tolerant weed species is selected from the group consisting of Poa annua, Poa pratensis and Poa trivialis.
In another embodiment, the herbicide resistant or tolerant weed species is Poa annua.
In another embodiment, the herbicide resistant or tolerant weed species is Poa pratensis.
In another embodiment, the herbicide resistant or tolerant weed species is Poa trivialis.
In another embodiment, the herbicide resistant or tolerant weed species is Commelina bengha- lensis.
In another embodiment, the herbicide resistant or tolerant weed species is Papaver rhoeas.
In another embodiment, the herbicide resistant or tolerant weed species is Raphanus raphan- istrum.
In another embodiment, the herbicide resistant or tolerant weed species is selected from the group consisting of Alopecurus myosuroides, Alopecurus aequalis, Apera spica-venti, Avena fatua, Avena sterilis, Brachiaria plantaginea, Brachiaria decumbens, Bromus secalinus, Bromus sterilis, Bromus tectorum, Eleusine indica, Lolium multiflorum, Lolium perenne, Lolium rigidum, Lolium x hybridum, Phalaris brachystachyx, Phalaris minor, Phalaris paradoxa, Rottboellia exal- tata, Setaria faberi, Amaranthus albus, Amaranthus blitoides, Amaranthus hybridus, Amaran- thus palmeri, Amaranthus powellii, Amaranthus retroflexus, Amaranthus tuberculatus, Amaran- thus rudis, Amaranthus viridis, Ambrosia artemisifolia, Anthemis arvensis, Capsella bursa-pas- toris, Centaurea cyanus, Chenopodium album, Chenopodium ficifolium, Chenopodium polysper- mum, Chenopodium hybridum, Commelina benghalensis, Conyza bonariensis, Conyza cana- densis, Descurania sophia, Galium aparine, Galium spurium, Galium tricornutum, Kochia sco- paria, Matricaria chamomilla, Matricaria discoidea, Matricaria inodora, Papaver rhoeas,
Raphanus raphanistrum, Sinapis alba, Sinapis arvensis, Sisymbrium officinale, Sisymbrium ori- entale, Stellaria media and Thlaspi arvense, preferably selected from the group consisting of Al- opecurus myosuroides, Alopecurus aequalis, Apera spica-venti, Avena fatua, Avena sterilis, Lo- lium multiflorum, Lolium perenne, Lolium rigidum, Lolium x hybridum, Phalaris brachystachyx, Phalaris minor, Phalaris paradoxa, Commelina benghalensis, Papaver rhoeas and Raphanus raphanistrum, more preferably selected from the group consisting of Alopecurus myosuroides, Alopecurus aequalis, Apera spica-venti, Avena fatua, Avena sterilis, Lolium multiflorum, Lolium perenne, Lolium rigidum, Lolium x hybridum, Phalaris brachystachyx, Phalaris minor, Phalaris paradoxa, Poa annua, Poa pratensis, Poa trivialis, Papaver rhoeas and Raphanus raphan- istrum, even more preferably selected from the group consisting of Alopecurus myosuroides, Al- opecurus aequalis, Avena fatua, Avena sterilis, Lolium multiflorum, Lolium perenne, Lolium rigidum, Lolium x hybridum and Raphanus raphanistrum and in particular selected from the group consisting of Alopecurus myosuroides, Lolium multiflorum, Lolium rigidum and Lolium x hybridum.
In another embodiment, the herbicide resistant or tolerant weed species is a monocotyledonous weed species selected from the group consisting of Alopecurus myosuroides, Alopecurus aequalis, Apera spica-venti, Avena fatua, Avena sterilis, Brachiaria plantaginea, Brachiaria de- cumbens, Bromus secalinus, Bromus sterilis, Bromus tectorum, Digitaria ciliaris, Digitaria insu- laris, Digitaria ischaemum, Digitaria sanguinalis, Echinochloa colona, Echinochloa crus-galli, Echinochloa crus-pavonis, Echinochloa erecta, Echinochloa oryzoides, Echinochloa phyllogo- gon, Eleusine indica, Ischaemum rugosum, Leptochloa chinensis, Leptochloa panicoides, Lep- tochloa scabra, Leptochloa virgata, Lolium multiflorum, Lolium perenne, Lolium rigidum, Lolium x hybridum, Panicum capillare, Panicum dichotomiflorum, Phalaris brachystachyx, Phalaris mi- nor, Phalaris paradoxa, Poa annua, Poa pratensis, Poa trivialis, Rottboellia exaltata, Setaria fa- beri, Setaria glauca, Setaria pumila, Setaria verticillate and Setaria viridis, preferably selected from the group consisting of Alopecurus myosuroides, Alopecurus aequalis, Apera spica-venti, Avena fatua, Avena sterilis, Lolium multiflorum, Lolium perenne, Lolium rigidum, Lolium x hy- bridum, Phalaris brachystachyx, Phalaris minor, Phalaris paradoxa, Poa annua, Poa pratensis and Poa trivialis, more preferably selected from the group consisting of Alopecurus myosu- roides, Alopecurus aequalis, Avena fatua, Avena sterilis, Lolium multiflorum, Lolium perenne, Lolium rigidum and Lolium x hybridum, even more preferably selected from the group consisting of Alopecurus myosuroides, Lolium multiflorum, Lolium rigidum and Lolium x hybridum.
In another embodiment, the herbicide resistant or tolerant weed species is a monocotyledonous weed species selected from the group consisting of Alopecurus myosuroides, Alopecurus aequalis, Apera spica-venti, Avena fatua, Avena sterilis, Brachiaria plantaginea, Brachiaria de- cumbens, Bromus secalinus, Bromus sterilis, Bromus tectorum, Eleusine indica, Lolium multiflo rum, Lolium perenne, Lolium rigidum, Lolium x hybridum, Phalaris brachystachyx, Phalaris mi- nor, Phalaris paradoxa and Rottboellia exaltata, preferably selected from the group consisting of Alopecurus myosuroides, Alopecurus aequalis, Apera spica-venti, Avena fatua, Avena sterilis, Lolium multiflorum, Lolium perenne, Lolium rigidum, Lolium x hybridum, Phalaris brachystachyx, Phalaris minor and Phalaris paradoxa, more preferably selected from the group consisting of Al- opecurus myosuroides, Alopecurus aequalis, Avena fatua, Avena sterilis, Lolium multiflorum, Lolium perenne, Lolium rigidum and Lolium x hybridum, even more preferably selected from the group consisting of Alopecurus myosuroides, Lolium multiflorum, Lolium rigidum and Lolium x hybridum.
In another embodiment, the herbicide resistant or tolerant weed species is a dicotyledonous weed species selected from the genera Amaranthus albus, Amaranthus blitoides, Amaranthus hybridus, Amaranthus palmeri, Amaranthus powellii, Amaranthus retroflexus, Amaranthus tu- berculatus, Amaranthus rudis, Amaranthus viridis, Ambrosia artemisifolia, Anthemis arvensis, Capsella bursa-pastoris, Centaurea cyanus, Chenopodium album, Chenopodium ficifolium, Chenopodium polyspermum, Chenopodium hybridum, Commelina benghalensis, Conyza bon- ariensis, Conyza canadensis, Descurania sophia, Galium aparine, Galium spurium, Galium tri- cornutum, Kochia scoparia, Matricaria chamomilla, Matricaria discoidea, Matricaria inodora, Pa- paver rhoeas, Raphanus raphanistrum, Sinapis alba, Sinapis arvensis, Sisymbrium officinale, Sisymbrium orientale, Stellaria media and Thlaspi arvense, preferably selected from the group consisting of Commelina benghalensis, Papaver rhoeas and Raphanus raphanistrum, more preferably selected from the group consisting of Papaver rhoeas and Raphanus raphanistrum and is in particular Raphanus raphanistrum.
In particular, the methods, uses, herbicidal combinations and compositions of this invention are suitable for controlling ACCase-resistant grass weeds, more specifically ACCase-resistant grass weeds selected from the group consisting of Alopecurus myosuroides, Alopecurus aequalis, Apera spica-venti, Avena fatua, Avena sterilis, Brachiaria plantaginea, Brachiaria decumbens, Bromus secalinus, Bromus sterilis, Bromus tectorum, Digitaria ciliaris, Digitaria insularis, Digi- taria ischaemum, Digitaria sanguinalis, Echinochloa colona, Echinochloa crus-galli, Echinochloa crus-pavonis, Echinochloa erecta, Echinochloa oryzoides, Echinochloa phyllogogon, Eleusine indica, Ischaemum rugosum, Leptochloa chinensis, Leptochloa panicoides, Leptochloa scabra, Leptochloa virgata, Lolium multiflorum, Lolium perenne, Lolium rigidum, Lolium x hybridum, Panicum capillare, Panicum dichotomiflorum, Phalaris brachystachyx, Phalaris minor, Phalaris paradoxa, Poa annua, Poa pratensis, Poa trivialis, Rottboellia exaltata, Setaria faberi, Setaria glauca, Setaria pumila, Setaria verticillata and Setaria viridis, preferably selected from the group consisting of Alopecurus myosuroides, Alopecurus aequalis, Apera spica-venti, Avena fatua, Avena sterilis, Lolium multiflorum, Lolium perenne, Lolium rigidum, Lolium x hybridum, Phalaris brachystachys, Phalaris minor, Phalaris paradoxa, Poa annua and Poa trivialis, more preferably selected from the group consisting of Alopecurus myosuroides, Alopecurus aequalis, Avena fatua, Avena sterilis, Lolium multiflorum, Lolium perenne, Lolium rigidum and Lolium x hy- bridum, especially preferably selected from the group consisting of Alopecurus myosuroides, Al- opecurus aequalis, Lolium multiflorum, Lolium perenne, Lolium rigidum and Lolium x hybridum, and in particular selected from the group consisting of Alopecurus myosuroides, Lolium multiflo- rum, Lolium rigidum and Lolium x hybridum.
In particular, the methods, uses, herbicidal combinations and compositions of this invention are suitable for controlling ALS-resistant grass weeds, more specifically ALS-resistant grass weeds selected from the group consisting of Alopecurus myosuroides, Alopecurus aequalis, Apera spica-venti, Avena fatua, Avena sterilis, Brachiaria plantaginea, Brachiaria decumbens, Bromus secalinus, Bromus sterilis, Bromus tectorum, Digitaria ciliaris, Digitaria insularis, Digitaria is- chaemum, Digitaria sanguinalis, Echinochloa colona, Echinochloa crus-galli, Echinochloa crus- pavonis, Echinochloa erecta, Echinochloa oryzoides, Echinochloa phyllogogon, Eleusine indica, Ischaemum rugosum, Leptochloa chinensis, Leptochloa panicoides, Leptochloa scabra, Lepto- chloa virgata, Lolium multiflorum, Lolium perenne, Lolium rigidum, Lolium x hybridum, Panicum capillare, Panicum dichotomiflorum, Phalaris brachystachyx, Phalaris minor, Phalaris paradoxa, Poa annua, Poa pratensis, Poa trivialis, Rottboellia exaltata, Setaria faberi, Setaria glauca, Setaria pumila, Setaria verticillata and Setaria viridis, preferably selected from the group con- sisting of Alopecurus myosuroides, Alopecurus aequalis, Apera spica-venti, Avena fatua, Avena sterilis, Lolium multiflorum, Lolium perenne, Lolium rigidum, Lolium x hybridum, Phalaris bra- chystachys, Phalaris minor, Phalaris paradoxa, Poa annua and Poa trivialis, more preferably se- lected from the group consisting of Alopecurus myosuroides, Alopecurus aequalis, Avena fatua, Avena sterilis, Lolium multiflorum, Lolium perenne, Lolium rigidum and Lolium x hybridum, es- pecially preferably selected from the group consisting of Alopecurus myosuroides, Alopecurus aequalis, Lolium multiflorum, Lolium perenne, Lolium rigidum and Lolium x hybridum, and in particular selected from the group consisting of Alopecurus myosuroides, Lolium multiflorum, Lolium rigidum and Lolium x hybridum.
In particular, the methods, uses, herbicidal combinations and compositions of this invention are suitable for controlling PS ll-resistant grass weeds, more specifically PS ll-resistant grass weeds selected from the group consisting of Alopecurus myosuroides, Alopecurus aequalis, Apera spica-venti, Avena fatua, Avena sterilis, Brachiaria plantaginea, Brachiaria decumbens, Bromus secalinus, Bromus sterilis, Bromus tectorum, Digitaria ciliaris, Digitaria insularis, Digi- taria ischaemum, Digitaria sanguinalis, Echinochloa colona, Echinochloa crus-galli, Echinochloa crus-pavonis, Echinochloa erecta, Echinochloa oryzoides, Echinochloa phyllogogon, Eleusine indica, Ischaemum rugosum, Leptochloa chinensis, Leptochloa panicoides, Leptochloa scabra, Leptochloa virgata, Lolium multiflorum, Lolium perenne, Lolium rigidum, Lolium x hybridum, Panicum capillare, Panicum dichotomiflorum, Phalaris brachystachyx, Phalaris minor, Phalaris paradoxa, Poa annua, Poa pratensis, Poa trivialis, Rottboellia exaltata, Setaria faberi, Setaria glauca, Setaria pumila, Setaria verticillata and Setaria viridis, preferably selected from the group consisting of Alopecurus myosuroides, Alopecurus aequalis, Apera spica-venti, Avena fatua, Avena sterilis, Lolium multiflorum, Lolium perenne, Lolium rigidum, Lolium x hybridum, Phalaris brachystachys, Phalaris minor, Phalaris paradoxa, Poa annua and Poa trivialis, more preferably selected from the group consisting of Alopecurus myosuroides, Alopecurus aequalis, Avena fatua, Avena sterilis, Lolium multiflorum, Lolium perenne, Lolium rigidum and Lolium x hy- bridum, especially preferably selected from the group consisting of Alopecurus myosuroides, Al- opecurus aequalis, Lolium multiflorum, Lolium perenne, Lolium rigidum and Lolium x hybridum, and in particular selected from the group consisting of Alopecurus myosuroides, Lolium multiflo- rum, Lolium rigidum and Lolium x hybridum.
In particular, the methods, uses, herbicidal combinations and compositions of this invention of this invention are suitable for controlling HRAC Group G-resistant grass weeds, more specifi- cally HRAC Group G-resistant grass weeds selected from the group consisting of Alopecurus myosuroides, Alopecurus aequalis, Apera spica-venti, Avena fatua, Avena sterilis, Brachiaria plantaginea, Brachiaria decumbens, Bromus secalinus, Bromus sterilis, Bromus tectorum, Digi taria ciliaris, Digitaria insularis, Digitaria ischaemum, Digitaria sanguinalis, Echinochloa colona, Echinochloa crus-galli, Echinochloa crus-pavonis, Echinochloa erecta, Echinochloa oryzoides, Echinochloa phyllogogon, Eleusine indica, Ischaemum rugosum, Leptochloa chinensis, Lepto- chloa panicoides, Leptochloa scabra, Leptochloa virgata, Lolium multiflorum, Lolium perenne, Lolium rigidum, Lolium x hybridum, Panicum capillare, Panicum dichotomiflorum, Phalaris bra- chystachyx, Phalaris minor, Phalaris paradoxa, Poa annua, Poa pratensis, Poa trivialis, Rott- boellia exaltata, Setaria faberi, Setaria glauca, Setaria pumila, Setaria verticillata and Setaria viridis, preferably selected from the group consisting of Alopecurus myosuroides, Alopecurus aequalis, Apera spica-venti, Avena fatua, Avena sterilis, Lolium multiflorum, Lolium perenne, Lolium rigidum, Lolium x hybridum, Phalaris brachystachys, Phalaris minor, Phalaris paradoxa, Poa annua and Poa trivialis, more preferably selected from the group consisting of Alopecurus myosuroides, Alopecurus aequalis, Avena fatua, Avena sterilis, Lolium multiflorum, Lolium perenne, Lolium rigidum and Lolium x hybridum, especially preferably selected from the group consisting of Alopecurus myosuroides, Alopecurus aequalis, Lolium multiflorum, Lolium perenne, Lolium rigidum and Lolium x hybridum, and in particular selected from the group con- sisting of Alopecurus myosuroides, Lolium multiflorum, Lolium rigidum and Lolium x hybridum.
In particular, the methods, uses, herbicidal combinations and compositions of this invention are suitable for controlling HRAC Group H-resistant grass weeds, more specifically HRAC Group H- resistant grass weeds selected from the group consisting of Alopecurus myosuroides, Alopecu- rus aequalis, Apera spica-venti, Avena fatua, Avena sterilis, Brachiaria plantaginea, Brachiaria decumbens, Bromus secalinus, Bromus sterilis, Bromus tectorum, Digitaria ciliaris, Digitaria in- sularis, Digitaria ischaemum, Digitaria sanguinalis, Echinochloa colona, Echinochloa crus-galli, Echinochloa crus-pavonis, Echinochloa erecta, Echinochloa oryzoides, Echinochloa phyllogo- gon, Eleusine indica, Ischaemum rugosum, Leptochloa chinensis, Leptochloa panicoides, Lep- tochloa scabra, Leptochloa virgata, Lolium multiflorum, Lolium perenne, Lolium rigidum, Lolium x hybridum, Panicum capillare, Panicum dichotomiflorum, Phalaris brachystachyx, Phalaris mi- nor, Phalaris paradoxa, Poa annua, Poa pratensis, Poa trivialis, Rottboellia exaltata, Setaria fa- beri, Setaria glauca, Setaria pumila, Setaria verticillata and Setaria viridis, preferably selected from the group consisting of Alopecurus myosuroides, Alopecurus aequalis, Apera spica-venti, Avena fatua, Avena sterilis, Lolium multiflorum, Lolium perenne, Lolium rigidum, Lolium x hy- bridum, Phalaris brachystachys, Phalaris minor, Phalaris paradoxa, Poa annua and Poa trivialis, more preferably selected from the group consisting of Alopecurus myosuroides, Alopecurus aequalis, Avena fatua, Avena sterilis, Lolium multiflorum, Lolium perenne, Lolium rigidum and Lolium x hybridum, especially preferably selected from the group consisting of Alopecurus myo- suroides, Alopecurus aequalis, Lolium multiflorum, Lolium perenne, Lolium rigidum and Lolium x hybridum, and in particular selected from the group consisting of Alopecurus myosuroides, Lo- lium multiflorum, Lolium rigidum and Lolium x hybridum.
In particular, the methods, uses, herbicidal combinations and compositions of this invention are suitable for controlling HRAC Group K1 -resistant grass weeds, more specifically HRAC Group K1 -resistant grass weeds selected from the group consisting of Alopecurus myosuroides, Alo- pecurus aequalis, Apera spica-venti, Avena fatua, Avena sterilis, Brachiaria plantaginea, Brachi- aria decumbens, Bromus secalinus, Bromus sterilis, Bromus tectorum, Digitaria ciliaris, Digitaria insularis, Digitaria ischaemum, Digitaria sanguinalis, Echinochloa colona, Echinochloa crus- galli, Echinochloa crus-pavonis, Echinochloa erecta, Echinochloa oryzoides, Echinochloa phyl- logogon, Eleusine indica, Ischaemum rugosum, Leptochloa chinensis, Leptochloa panicoides, Leptochloa scabra, Leptochloa virgata, Lolium multiflorum, Lolium perenne, Lolium rigidum, Lo- lium x hybridum, Panicum capillare, Panicum dichotomiflorum, Phalaris brachystachyx, Phalaris minor, Phalaris paradoxa, Poa annua, Poa pratensis, Poa trivialis, Rottboellia exaltata, Setaria faberi, Setaria glauca, Setaria pumila, Setaria verticillata and Setaria viridis, preferably selected from the group consisting of Alopecurus myosuroides, Alopecurus aequalis, Apera spica-venti, Avena fatua, Avena sterilis, Lolium multiflorum, Lolium perenne, Lolium rigidum, Lolium x hy- bridum, Phalaris brachystachys, Phalaris minor, Phalaris paradoxa, Poa annua and Poa trivialis, more preferably selected from the group consisting of Alopecurus myosuroides, Alopecurus aequalis, Avena fatua, Avena sterilis, Lolium multiflorum, Lolium perenne, Lolium rigidum and Lolium x hybridum, especially preferably selected from the group consisting of Alopecurus myo- suroides, Alopecurus aequalis, Lolium multiflorum, Lolium perenne, Lolium rigidum and Lolium x hybridum, and in particular selected from the group consisting of Alopecurus myosuroides, Lo- lium multiflorum, Lolium rigidum and Lolium x hybridum.
In particular, the methods, uses, herbicidal combinations and compositions of this invention are suitable for controlling HRAC Group K3-resistant grass weeds, more specifically HRAC Group K3-resistant grass weeds selected from the group consisting of Alopecurus myosuroides, Alo- pecurus aequalis, Apera spica-venti, Avena fatua, Avena sterilis, Brachiaria plantaginea, Brachi- aria decumbens, Bromus secalinus, Bromus sterilis, Bromus tectorum, Digitaria ciliaris, Digitaria insularis, Digitaria ischaemum, Digitaria sanguinalis, Echinochloa colona, Echinochloa crus- galli, Echinochloa crus-pavonis, Echinochloa erecta, Echinochloa oryzoides, Echinochloa phyl- logogon, Eleusine indica, Ischaemum rugosum, Leptochloa chinensis, Leptochloa panicoides, Leptochloa scabra, Leptochloa virgata, Lolium multiflorum, Lolium perenne, Lolium rigidum, Lo- lium x hybridum, Panicum capillare, Panicum dichotomiflorum, Phalaris brachystachyx, Phalaris minor, Phalaris paradoxa, Poa annua, Poa pratensis, Poa trivialis, Rottboellia exaltata, Setaria faberi, Setaria glauca, Setaria pumila, Setaria verticillata and Setaria viridis, preferably selected from the group consisting of Alopecurus myosuroides, Alopecurus aequalis, Apera spica-venti, Avena fatua, Avena sterilis, Lolium multiflorum, Lolium perenne, Lolium rigidum, Lolium x hy- bridum, Phalaris brachystachys, Phalaris minor, Phalaris paradoxa, Poa annua and Poa trivialis, more preferably selected from the group consisting of Alopecurus myosuroides, Alopecurus aequalis, Avena fatua, Avena sterilis, Lolium multiflorum, Lolium perenne, Lolium rigidum and Lolium x hybridum, especially preferably selected from the group consisting of Alopecurus myo- suroides, Alopecurus aequalis, Lolium multiflorum, Lolium perenne, Lolium rigidum and Lolium x hybridum, and in particular selected from the group consisting of Alopecurus myosuroides, Lo- lium multiflorum, Lolium rigidum and Lolium x hybridum.
In particular, the methods, uses, herbicidal combinations and compositions of this invention are suitable for controlling broadleaf weeds having resistance to herbicides selected from the group consisting of acetolactate synthase (ALS) inhibitors (HRAC Group B), photosystem II (PS II) in- hibitors (HRAC Groups C1 , C2 and C3), protoporphyrinogen oxidase (PPO) inhibitors (HRAC Group E), 5-enolpymvylshikimate-3-phosphate (EPSP) inhibitors (HRAC Group G), glutamine synthetase inhibitors (HRAC Group H), inhibitors of microtubuli assembly (HRAC Group K1 ) and inhibitors of lipid synthesis (HRAC Group N). In one embodiment of the method/use of this invention, the herbicide A is applied alone, i.e. the herbicide A is the only herbicidally active ingredient.
In another embodiment, the herbicide A is applied in combination with at least one herbicide B different from herbicide A.
In another embodiment, a herbicidal combination comprising a) the herbicide A and b) at least one herbicide B different from herbicide A and is used or applied.
The herbicide B may be selected from the groups b1 ) to b15):
b1 ) lipid biosynthesis inhibitors;
b2) acetolactate synthase inhibitors (ALS inhibitors);
b3) photosynthesis inhibitors;
b4) protoporphyrinogen-IX oxidase inhibitors,
b5) bleacher herbicides;
b6) enolpyruvyl shikimate 3-phosphate synthase inhibitors (EPSP inhibitors);
b7) glutamine synthetase inhibitors;
b8) 7,8-dihydropteroate synthase inhibitors (DHP inhibitors);
b9) mitosis inhibitors;
b10) inhibitors of the synthesis of very long chain fatty acids (VLCFA inhibitors);
b11 ) cellulose biosynthesis inhibitors;
b12) decoupler herbicides;
b13) synthetic auxins;
b14) auxin transport inhibitors; and
b15) other herbicides selected from the group consisting of bromobutide, chlorflurenol,
chlorflurenol-methyl, cumyluron, dalapon, dazomet, difenzoquat, difenzoquat-metilsulfate, dimethipin, DSMA, dymron, endothal and its salts, etobenzanid, flamprop, flamprop-iso- propyl, flamprop-methyl, flamprop-M-isopropyl, flamprop-M-methyl, flurenol, flurenol-butyl, flurprimidol, fosamine, fosamine-ammonium, indanofan, indaziflam, maleic hydrazide, mefluidide, metam, methyl azide, methyl bromide, methyl-dymron, methyl iodide, MSMA, oleic acid, oxaziclomefone, pelargonic acid, pyributicarb, quinoclamine, triaziflam, tridip- hane and 6-chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinol (CAS 499223-49-3) and its salts and esters; and agriculturally acceptable salts or derivatives thereof.
Preferably, the herbicide B is selected from b1) lipid biosynthesis inhibitors:
ACCase inhibitors selected from alloxydim, alloxydim-sodium, butroxydim, clethodim, clodinafop, clodinafop-propargyl, cycloxydim, cyhalofop, cyhalofop-butyl, diclofop, diclofop-me- thyl, fenoxaprop, fenoxaprop-ethyl, fenoxaprop-P, fenoxaprop-P-ethyl, fluazifop, fluazifop-butyl, fluazifop-P, fluazifop-P-butyl, haloxyfop, haloxyfop-methyl, haloxyfop-P, haloxyfop-P-methyl, metamifop, pinoxaden, profoxydim, propaquizafop, quizalofop, quizalofop-ethyl, quizalofop-te- furyl, quizalofop-P, 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-tetrame- thyl-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 carbonic 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-yl carbonic 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-yl carbonic acid methyl ester (CAS 1312340-83-2); 4-(2',4'-Dichloro-4-ethyl[1 ,1 '-bi- phenyl]-3-yl)-5,6-dihydro-2,2,6,6-tetramethyl-5-oxo-2H-pyran-3-yl carbonic acid methyl ester (CAS 1033760-58-5); and non ACC herbicides selected from benfuresate, butylate, cycloate, dalapon, dimepiperate, EPTC, esprocarb, ethofumesate, flupropanate, molinate, orbencarb, pebulate, prosulfocarb, TCA, thiobencarb, tiocarbazil, triallate and vernolate; b2) ALS inhibitors:
sulfonylureas selected from amidosulfuron, azimsulfuron, bensulfuron, bensulfuron-methyl, chlorimuron, chlorimuron-ethyl, chlorsulfuron, cinosulfuron, cyclosulfamuron, ethametsulfuron, ethametsulfuron-methyl, ethoxysulfuron, flazasulfuron, flucetosulfuron, flupyrsulfuron, flupyrsul- furon-methyl-sodium, foramsulfuron, halosulfuron, halosulfuron-methyl, imazosulfuron, iodosul- furon, iodosulfuron-methyl-sodium, iofensulfuron, iofensulfuron-sodium, mesosulfuron, met- azosulfuron, metsulfuron, metsulfuron-methyl, nicosulfuron, orthosulfamuron, oxasulfuron, primisulfuron, primisulfuron-methyl, propyrisulfuron, prosulfuron, pyrazosulfuron, pyrazosulfu- ron-ethyl, rimsulfuron, sulfometuron, sulfometuron-methyl, sulfosulfuron, thifensulfuron, thifen- sulfuron-methyl, triasulfuron, tribenuron, tribenuron-methyl, trifloxysulfuron, triflusulfuron, tri- flusulfuron-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, penox- sulam, pyrimisulfan and pyroxsulam,
pyrimidinylbenzoates selected from bispyribac, bispyribac-sodium, pyribenzoxim, pyriftalid, py- riminobac, pyriminobac-methyl, pyrithiobac, pyrithiobac-sodium, 4-[[[2-[(4,6-dimethoxy-2-pyrim- idinyl)oxy]phenyl]methyl]amino]-benzoic acid-1 -methylethyl ester (CAS 420138-41-6), 4-[[[2- [(4,6-dimethoxy-2-pyrimidinyl)oxy]phenyl]methyl]amino]-benzoic acid propyl ester (CAS 420138- 40-5), N-(4-bromophenyl)-2-[(4,6-dimethoxy-2-pyrimidinyl)oxy]benzenemethanamine (CAS 420138-01-8), sulfonylaminocarbonyl-triazolinone herbicides selected from flucarbazone, flucarbazone-so- dium, propoxycarbazone, propoxycarbazone-sodium, thiencarbazone and thiencarbazone-me- thyl; and triafamone; b3) photosynthesis inhibitors:
amicarbazone, inhibitors of the photosystem II selected from 1-(6-tert-butylpyrimidin-4-yl)-2-hy- droxy-4-methoxy-3-methyl-2H-pyrrol-5-one (CAS 1654744-66-7), 1-(5-tert-butylisoxazol-3-yl)-2- hydroxy-4-methoxy-3-methyl-2H-pyrrol-5-one (CAS 1637455-12-9), 1-(5-tert-butylisoxazol-3-yl)- 4-chloro-2-hydroxy-3-methyl-2H-pyrrol-5-one (CAS 1637453-94-1), 1-(5-tert-butyl-1-methyl-py- razol-3-yl)-4-chloro-2-hydroxy-3-methyl-2H-pyrrol-5-one (CAS 1654057-29-0), 1-(5-tert-butyl-1- methyl-pyrazol-3-yl)-3-chloro-2-hydroxy-4-methyl-2H-pyrrol-5-one (CAS 1654747-80-4), 4-hy- droxy-1-methoxy-5-methyl-3-[4-(trifluoromethyl)-2-pyridyl]imidazolidin-2-one; (CAS 2023785-78-
4), 4-hydroxy-1 ,5-dimethyl-3-[4-(trifluoromethyl)-2-pyridyl]imidazolidin-2-one (CAS 2023785-79-
5), 5-ethoxy-4-hydroxy-1 -methyl-3-[4-(trifluoromethyl)-2-pyridyl]imidazolidin-2-one (CAS
1701416-69-4), 4-hydroxy-1 -methyl-3-[4-(trifluoromethyl)-2-pyridyl]imidazolidin-2-one (CAS 1708087-22-2), 4-hydroxy-1 ,5-dimethyl-3-[1 -methyl-5-(trifluoromethyl)pyrazol-3-yl]imidazolidin- 2-one (CAS 2023785-80-8), 1-(5-tert-butylisoxazol-3-yl)-4-ethoxy-5-hydroxy-3-methyl-imidazoli- din-2-one (CAS 1844836-64-1 ), triazine herbicides, including of chlorotriazine, triazinones, tria- zindiones, methylthiotriazines and pyridazinones selected from ametryn, atrazine, chloridazone, cyanazine, desmetryn, dimethametryn, hexazinone, metribuzin, prometon, prometryn, pro- pazine, simazine, simetryn, terbumeton, terbuthylazin, terbutryn and trietazin, aryl urea selected from chlorobromuron, chlorotoluron, chloroxuron, dimefuron, diuron, fluometuron, isoproturon, isouron, linuron, metamitron, methabenzthiazuron, metobenzuron, metoxuron, monolinuron, neburon, siduron, tebuthiuron and thiadiazuron, phenyl carbamates selected from
desmedipham, karbutilat, phenmedipham, phenmedipham-ethyl, nitrile herbicides selected from bromofenoxim, bromoxynil and its salts and esters, ioxynil and its salts and esters, uraciles se- lected from bromacil, lenacil and terbacil, and bentazon and bentazon-sodium, pyridate, pyri- dafol, pentanochlor and propanil and inhibitors of the photosystem I selected from diquat, di- quat-dibromide, paraquat, paraquat-dichloride and paraquat-dimetilsulfate. b4) protoporphyrinogen-IX oxidase inhibitors:
acifluorfen, acifluorfen-sodium, azafenidin, bencarbazone, benzfendizone, bifenox, butafenacil, carfentrazone, carfentrazone-ethyl, chlomethoxyfen, chlorphthalim, cinidon-ethyl, cyclopyranil, fluazolate, flufenpyr, flufenpyr-ethyl, flumiclorac, flumiclorac-pentyl, flumioxazin, fluoroglycofen, fluoroglycofen-ethyl, fluthiacet, fluthiacet-methyl, fomesafen, halosafen, lactofen, oxadiargyl, oxadiazon, oxyfluorfen, pentoxazone, profluazol, pyraclonil, pyraflufen, pyraflufen-ethyl, saflufenacil, sulfentrazone, thidiazimin, tiafenacil, trifludimoxazin, ethyl [3-[2-chloro-4-fluoro-5-(1- methyl-6-trifluoromethyl-2,4-dioxo-1 ,2,3,4-tetrahydropyrimidin-3-yl)phenoxy]-2-pyridyloxy]ace- tate (CAS 353292-31-6; S-3100), N-ethyl-3-(2,6-dichloro-4-trifluoromethylphenoxy)-5-methyl- 1 TT-pyrazole-l -carboxamide (CAS 452098-92-9), N-tetrahydrofurfuryl-3-(2,6-dichloro-4-trifluoro- methylphenoxy)-5-methyl-1 TT-pyrazole-l -carboxamide (CAS 915396-43-9), N-ethyl-3-(2-chloro- 6-fluoro-4-trifluoromethylphenoxy)-5-methyl-1 TT-pyrazole-l -carboxamide (CAS 452099-05-7), N-tetrahydrofurfuryl-3-(2-chloro-6-fluoro-4-trifluoromethylphenoxy)-5-methyl-1 TT-pyrazole-l-car- boxamide (CAS 452100-03-7), 3-[7-fluoro-3-oxo-4-(prop-2-ynyl)-3,4-dihydro-2H-benzo[1 ,4]oxa- zin-6-yl]-1 ,5-dimethyl-6-thioxo-[1 ,3,5]triazinan-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-dihy- dro-2H-benzo[1 ,4]oxazin-6-yl)-1 H-pyrimidine-2,4-dione (CAS 1304113-05-0), methyl (£)- 4-[2- chloro-5-[4-chloro-5-(difluoromethoxy)-1 /T-methyl-pyrazol-S-ylH-fluoro-phenoxyl-S-methoxy- but-2-enoate (CAS 948893-00-3), and 3-[7-chloro-5-fluoro-2-(trifluoromethyl)-1 H-benzimidazol-
4-yl]-1-methyl-6-(trifluoromethyl)-1 H-pyrimidine-2,4-dione (CAS 212754-02-4); b5) bleacher herbicides:
PDS inhibitors: beflubutamid, diflufenican, fluridone, flurochloridone, flurtamone, norflurazon, picolinafen, and 4-(3-trifluoromethylphenoxy)-2-(4-trifluoromethylphenyl)pyrimidine (CAS 180608-33-7), HPPD inhibitors: benzobicyclon, benzofenap, bicyclopyrone, clomazone, fenquinotrione, isoxaflutole, mesotrione, oxotrione (CAS 1486617-21-3), pyrasulfotole, pyrazol- ynate, pyrazoxyfen, sulcotrione, tefuryltrione, tembotrione, tolpyralate, topramezone , bleacher, unknown target: aclonifen, amitrole, flumeturon, 2-chloro-3-methylsulfanyl-N-(1-methyltetrazol-
5-yl)-4-(trifluoromethyl)benzamide (CAS 1361139-71-0), 2-(2,4-dichlorophenyl)methyl-4,4-dime- thyl-3-isoxazolidone (CAS 81777-95-9) and 2-(2,5-dichlorophenyl)methyl-4,4-dimethyl-3-isoxa- zolidinone (CAS 81778-66-7); b6) EPSP synthase inhibitors:
glyphosate, glyphosate-isopropylammonium, glyphosate-potassium and glyphosate-trimesium (sulfosate); b7) glutamine synthase inhibitors:
bilanaphos (bialaphos), bilanaphos-sodium, glufosinate, glufosinate-P and glufosinate-ammo- nium; b8) DHP synthase inhibitors:
asulam; b9) mitosis inhibitors:
compounds of group K1 : dinitroanilines selected from benfluralin, butralin, dinitramine, ethalflu- ralin, fluchloralin, oryzalin, pendimethalin, prodiamine and trifluralin, phosphoramidates selected from amiprophos, amiprophos-methyl, and butamiphos, benzoic acid herbicides selected from chlorthal, chlorthal-dimethyl, pyridines selected from dithiopyr and thiazopyr, benzamides se- lected from propyzamide and tebutam; compounds of group K2: carbetamide, chlorpropham, flamprop, flamprop-isopropyl, flamprop-methyl, flamprop-M-isopropyl, flamprop-M-methyl and propham; b10) VLCFA inhibitors:
chloroacetamides selected from acetochlor, alachlor, amidochlor, butachlor, dimethachlor, di- methenamid, dimethenamid-P, metazachlor, metolachlor, S-metolachlor, pethoxamid, preti- lachlor, propachlor, propisochlor and thenylchlor, oxyacetanilides selected from flufenacet and mefenacet, acetanilides selected from diphenamid, naproanilide, napropamide and napropa- mide-M, tetrazolinones such fentrazamide, and other herbicides selected from anilofos, cafen- strole, fenoxasulfone, ipfencarbazone, piperophos, pyroxasulfone and isoxazoline compounds of the formulae 11.1 , II.2, II.3, II.4, II.5, II.6, II.7, II.8 and II.9
Figure imgf000022_0001
b1 1 ) cellulose biosynthesis inhibitors:
chlorthiamid, dichlobenil, flupoxam, indaziflam, isoxaben, triaziflam and 1 -cyclohexyl-5-pen- tafluorphenyloxy-14-[1 ,2,4,6]thiatriazin-3-ylamine (CAS 175899-01 -1 ); b12) decoupler herbicides:
dinoseb, dinoterb and DNOC and its salts; b13) synthetic auxins:
2,4-D and its salts and esters selected from clacyfos, 2,4-DB and its salts and esters, aminocy- clopyrachlor and its salts and esters, aminopyralid and its salts selected from aminopyralid-di- methylammonium, aminopyralid-tris(2-hydroxypropyl)ammonium and its esters, benazolin, benazolin-ethyl, chloramben and its salts and esters, clomeprop, clopyralid and its salts and es- ters, dicamba and its salts and esters, dichlorprop and its salts and esters, dichlorprop-P and its salts and esters, flopyrauxifen, fluroxypyr, fluroxypyr-butometyl, fluroxypyr-meptyl, halauxifen and its salts and esters (CAS 943832-60-8); MCPA and its salts and esters, MCPA-thioethyl, MCPB and its salts and esters, mecoprop and its salts and esters, mecoprop-P and its salts and esters, picloram and its salts and esters, quinclorac, quinmerac, TBA (2,3,6) and its salts and esters, triclopyr and its salts and esters, florpyrauxifen, florpyrauxifen-benzyl (CAS 1390661 -72- 9) and 4-amino-3-chloro-5-fluoro-6-(7-fluoro-1 H-indol-6-yl)picolinic acid (CAS 1629965-65-6); b14) auxin transport inhibitors: diflufenzopyr, diflufenzopyr-sodium, naptalam and naptalam-so- dium; and b15) other herbicides: bromobutide, chlorflurenol, chlorflurenol-methyl, cumyluron, cyclopy- rimorate (CAS 499223-49-3) and its salts and esters, dalapon, dazomet, difenzoquat, difen- zoquat-metilsulfate, dimethipin, DSMA, dymron, endothal and its salts, etobenzanid, flurenol, flurenol-butyl, flurprimidol, fosamine, fosamine-ammonium, indanofan, maleic hydrazide, meflu- idide, metam, methyl azide, methyl bromide, methyl-dymron, methyl iodide, MSMA, oleic acid, oxaziclomefone, pelargonic acid, pyributicarb, quinoclamine and tridiphane.
More preferably, the herbicide B is selected from b1 ) lipid biosynthesis inhibitors: prosulfocarb and triallate; b3) photosynthesis inhibitors: metribuzin, chlorotoluron and isoproturon; b4) protoporphyrinogen-IX oxidase inhibitors: flumioxazin, saflufenacil, sulfentrazone and triflu- dimoxazin; b5) bleacher herbicides: diflufenican, picolinafen, flurtamone, aclonifen and 2-(2,4-dichloro- phenyl)methyl-4,4-dimethyl-3-isoxazolidone (CAS 81777-95-9); b9) mitosis inhibitors: pendimethalin and trifluralin; b10) VLCFA inhibitors: metolachlor, S-metolachlor, flufenacet and pyroxasulfone; b13) synthetic auxins: halauxifen and its salts and esters (CAS 943832-60-8), florpyrauxifen, florpyrauxifen-benzyl (CAS 1390661 -72-9) and 4-amino-3-chloro-5-fluoro-6-(7-fluoro-1 H-indol-6- yl)picolinic acid (CAS 1629965-65-6); and b15) other herbicides: indanofan and oxaziclomefone.
In another embodiment, the herbicide B is selected from b1 ) lipid biosynthesis inhibitors: prosulfocarb and triallate; b3) photosynthesis inhibitors: metribuzin, chlorotoluron and isoproturon; b4) protoporphyrinogen-IX oxidase inhibitors: flumioxazin, saflufenacil, sulfentrazone and triflu- dimoxazin; b5) bleacher herbicides: diflufenican, picolinafen, flurtamone, aclonifen and 2-(2,4-dichloro- phenyl)methyl-4,4-dimethyl-3-isoxazolidone (CAS 81777-95-9); b9) mitosis inhibitors: pendimethalin and trifluralin; b10) VLCFA inhibitors: metolachlor, S-metolachlor and flufenacet; b13) synthetic auxins: halauxifen and its salts and esters (CAS 943832-60-8), florpyrauxifen, florpyrauxifen-benzyl (CAS 1390661 -72-9) and 4-amino-3-chloro-5-fluoro-6-(7-fluoro-1 H-indol-6- yl)picolinic acid (CAS 1629965-65-6); and b15) other herbicides: indanofan and oxaziclomefone.
In yet another embodiment, the herbicide B is selected from b1 ) lipid biosynthesis inhibitors: prosulfocarb and triallate; b3) photosynthesis inhibitors: metribuzin, chlorotoluron and isoproturon; b4) protoporphyrinogen-IX oxidase inhibitors: flumioxazin, saflufenacil, sulfentrazone and triflu- dimoxazin; b5) bleacher herbicides: diflufenican, picolinafen, flurtamone, aclonifen and 2-(2,4-dichloro- phenyl)methyl-4,4-dimethyl-3-isoxazolidone (CAS 81777-95-9); b9) mitosis inhibitors: trifluralin; b10) VLCFA inhibitors: metolachlor, S-metolachlor and flufenacet; b13) synthetic auxins: halauxifen and its salts and esters (CAS 943832-60-8), florpyrauxifen, florpyrauxifen-benzyl (CAS 1390661 -72-9) and 4-amino-3-chloro-5-fluoro-6-(7-fluoro-1 H-indol-6- yl)picolinic acid (CAS 1629965-65-6); and b15) other herbicides: indanofan and oxaziclomefone.
In still another embodiment, the herbicide B is selected from b1 ) lipid biosynthesis inhibitors: triallate; b4) protoporphyrinogen-IX oxidase inhibitors: saflufenacil; b5) bleacher herbicides: diflufenican and picolinafen; b9) mitosis inhibitors: pendimethalin and trifluralin; and b10) VLCFA inhibitors: flufenacet and pyroxasulfone.
In another embodiment, the herbicide B is selected from prosulfocarb and triallate.
In another embodiment, the herbicide B is prosulfocarb.
In another embodiment, the herbicide B is triallate.
In another embodiment, the herbicidal combination comprises a) the herbicide A (preferably (5/?S)-5-[(2,6-difluorobenzyloxy)methyl]-4,5-dihydro-5-methyl-3-(3-methyl-2-thienyl)-1 ,2-oxazole of the formula I, i.e. methiozolin) and b) a herbicide B which is triallate wherein the herbicide A and the herbicide B are the only herbicidally active ingredients.
Another embodiment of this invention relates to the use of a herbicidal combination comprising a) the herbicide A (preferably (5/?S)-5-[(2,6-difluorobenzyloxy)methyl]-4,5-dihydro-5-methyl-3- (3-methyl-2-thienyl)-1 ,2-oxazole of the formula I, i.e. methiozolin) and b) a herbicide B which is triallate wherein the herbicide A and the herbicide B are the only herbicidally active ingredients for controlling undesirable vegetation selected from the genera Alopecurus, Avena, Bromus, and Lolium (preferably selected from Alopecurus myosuroides, Avena fatua, Bromus sterilis, Lolium multiflorum and Lolium rigidum).
Another embodiment of this invention relates to a method for controlling undesirable vegetation which comprises applying to the vegetation or the locus thereof or applying to the soil or water to prevent the emergence or growth of the undesirable vegetation a herbicidal combination comprising a) the herbicide A (preferably (5/?S)-5-[(2,6-difluorobenzyloxy)methyl]-4,5-dihydro-5- methyl-3-(3-methyl-2-thienyl)-1 ,2-oxazole of the formula I, i.e. methiozolin) and b) a herbicide B which is triallate wherein the herbicide A and the herbicide B are the only herbicidally active ingredients and the undesirable vegetation is selected from the genera Alopecurus, Avena, Bromus, and Lolium (preferably selected from Alopecurus myosuroides, Avena fatua, Bromus sterilis, Lolium multiflorum and Lolium rigidum).
In another embodiment, the herbicide B is selected from metribuzin, chlorotoluron and isopro- turon.
In another embodiment, the herbicide B is metribuzin.
In another embodiment, the herbicide B is chlorotoluron.
In another embodiment, the herbicide B is isoproturon. In another embodiment, the herbicide B is selected from flumioxazin, saflufenacil, sulfentrazone and trifludimoxazin.
In another embodiment, the herbicide B is flumioxazin.
In another embodiment, the herbicide B is saflufenacil.
In another embodiment, the herbicidal combination comprises a) the herbicide A (preferably (5/?S)-5-[(2,6-difluorobenzyloxy)methyl]-4,5-dihydro-5-methyl-3-(3-methyl-2-thienyl)-1 ,2-oxazole of the formula I, i.e. methiozolin) and b) a herbicide B which is saflufenacil wherein the herbicide A and the herbicide B are the only herbicidally active ingredients.
Another embodiment of this invention relates to the use of a herbicidal combination comprising a) the herbicide A (preferably (5/?S)-5-[(2,6-difluorobenzyloxy)methyl]-4,5-dihydro-5-methyl-3- (3-methyl-2-thienyl)-1 ,2-oxazole of the formula I, i.e. methiozolin) and b) a herbicide B which is saflufenacil wherein the herbicide A and the herbicide B are the only herbicidally active ingredients for controlling undesirable vegetation selected from the genus Bromus (which is preferably Bromus sterilis).
Another embodiment of this invention relates to a method for controlling undesirable vegetation which comprises applying to the vegetation or the locus thereof or applying to the soil or water to prevent the emergence or growth of the undesirable vegetation a herbicidal combination comprising a) the herbicide A (preferably (5/?S)-5-[(2,6-difluorobenzyloxy)methyl]-4,5-dihydro-5- methyl-3-(3-methyl-2-thienyl)-1 ,2-oxazole of the formula I, i.e. methiozolin) and b) a herbicide B which is saflufenacil wherein the herbicide A and the herbicide B are the only herbicidally active ingredients and the undesirable vegetation is selected from the genus Bromus (which is preferably Bromus sterilis).
In another embodiment, the herbicide B is sulfentrazone.
In another embodiment, the herbicide B is trifludimoxazin.
In another embodiment, the herbicide B is selected from diflufenican, picolinafen, flurtamone, aclonifen and 2-(2,4-dichlorophenyl)methyl-4,4-dimethyl-3-isoxazolidone (CAS 81777-95-9).
In another embodiment, the herbicide B is diflufenican.
In another embodiment, the herbicidal combination comprises a) the herbicide A (preferably (5/?S)-5-[(2,6-difluorobenzyloxy)methyl]-4,5-dihydro-5-methyl-3-(3-methyl-2-thienyl)-1 ,2-oxazole of the formula I, i.e. methiozolin) and b) a herbicide B which is diflufenican wherein the herbicide A and the herbicide B are the only herbicidally active ingredients.
Another embodiment of this invention relates to the use of a herbicidal combination comprising a) the herbicide A (preferably (5/?S)-5-[(2,6-difluorobenzyloxy)methyl]-4,5-dihydro-5-methyl-3- (3-methyl-2-thienyl)-1 ,2-oxazole of the formula I, i.e. methiozolin) and b) a herbicide B which is diflufenican wherein the herbicide A and the herbicide B are the only herbicidally active ingredients for controlling undesirable vegetation selected from the genera Alopecurus, Avena, Bromus and Lolium (preferably selected from Alopecurus myosuroides, Avena fatua, Bromus sterilis, Lolium multiflorum and Lolium rigidum).
Another embodiment of this invention relates to a method for controlling undesirable vegetation which comprises applying to the vegetation or the locus thereof or applying to the soil or water to prevent the emergence or growth of the undesirable vegetation a herbicidal combination comprising a) the herbicide A (preferably (5/?S)-5-[(2,6-difluorobenzyloxy)methyl]-4,5-dihydro-5- methyl-3-(3-methyl-2-thienyl)-1 ,2-oxazole of the formula I, i.e. methiozolin) and b) a herbicide B which is diflufenican wherein the herbicide A and the herbicide B are the only herbicidally active ingredients and the undesirable vegetation is selected from the genera Alopecurus, Avena, Bromus and Lolium (preferably selected from Alopecurus myosuroides, Avena fatua, Bromus sterilis, Lolium multiflorum and Lolium rigidum).
In another embodiment, the herbicide B is picolinafen.
In another embodiment, the herbicidal combination comprises a) the herbicide A (preferably (5/?S)-5-[(2,6-difluorobenzyloxy)methyl]-4,5-dihydro-5-methyl-3-(3-methyl-2-thienyl)-1 ,2-oxazole of the formula I, i.e. methiozolin) and b) a herbicide B which is picolinafen wherein the herbicide A and the herbicide B are the only herbicidally active ingredients.
Another embodiment of this invention relates to the use of a herbicidal combination comprising a) the herbicide A (preferably (5/?S)-5-[(2,6-difluorobenzyloxy)methyl]-4,5-dihydro-5-methyl-3- (3-methyl-2-thienyl)-1 ,2-oxazole of the formula I, i.e. methiozolin) and b) a herbicide B which is picolinafen wherein the herbicide A and the herbicide B are the only herbicidally active ingredients for controlling undesirable vegetation selected from the genera Bromus and Lolium (preferably selected from Bromus sterilis and Lolium multiflorum).
Another embodiment of this invention relates to a method for controlling undesirable vegetation which comprises applying to the vegetation or the locus thereof or applying to the soil or water to prevent the emergence or growth of the undesirable vegetation a herbicidal combination comprising a) the herbicide A (preferably (5/?S)-5-[(2,6-difluorobenzyloxy)methyl]-4,5-dihydro-5- methyl-3-(3-methyl-2-thienyl)-1 ,2-oxazole of the formula I, i.e. methiozolin) and b) a herbicide B which is picolinafen wherein the herbicide A and the herbicide B are the only herbicidally active ingredients and the undesirable vegetation is selected from the genera Bromus and Lolium (preferably selected from Bromus sterilis and Lolium multiflorum).
In another embodiment, the herbicide B is flurtamone.
In another embodiment, the herbicide B is aclonifen. In another embodiment, the herbicide B is 2-(2,4-dichlorophenyl)methyl-4,4-dimethyl-3-isoxazol- idone (CAS 81777-95-9).
In another embodiment, the herbicide B is selected from pendimethalin and trifluralin.
In another embodiment, the herbicide B is pendimethalin.
In another embodiment, the herbicidal combination comprises a) the herbicide A (preferably (5/?S)-5-[(2,6-difluorobenzyloxy)methyl]-4,5-dihydro-5-methyl-3-(3-methyl-2-thienyl)-1 ,2-oxazole of the formula I, i.e. methiozolin) and b) a herbicide B which is pendimethalin wherein the herbi- cide A and the herbicide B are the only herbicidally active ingredients.
Another embodiment of this invention relates to the use of a herbicidal combination comprising a) the herbicide A (preferably (5/?S)-5-[(2,6-difluorobenzyloxy)methyl]-4,5-dihydro-5-methyl-3- (3-methyl-2-thienyl)-1 ,2-oxazole of the formula I, i.e. methiozolin) and b) a herbicide B which is pendimethalin wherein the herbicide A and the herbicide B are the only herbicidally active ingredients for controlling undesirable vegetation selected from the genera Alopecurus, Avena and Lolium (preferably selected from Alopecurus myosuroides, Avena fatua, Lolium multiflorum and Lolium rigidum).
Another embodiment of this invention relates to a method for controlling undesirable vegetation which comprises applying to the vegetation or the locus thereof or applying to the soil or water to prevent the emergence or growth of the undesirable vegetation a herbicidal combination comprising a) the herbicide A (preferably (5/?S)-5-[(2,6-difluorobenzyloxy)methyl]-4,5-dihydro-5- methyl-3-(3-methyl-2-thienyl)-1 ,2-oxazole of the formula I, i.e. methiozolin) and b) a herbicide B which is pendimethalin wherein the herbicide A and the herbicide B are the only herbicidally active ingredients and the undesirable vegetation is selected from the genera Alopecurus,
Avena and Lolium (preferably selected from Alopecurus myosuroides, Avena fatua, Lolium multiflorum and Lolium rigidum).
In another embodiment, the herbicide B is trifluralin.
In another embodiment, the herbicidal combination comprises a) the herbicide A (preferably (5/?S)-5-[(2,6-difluorobenzyloxy)methyl]-4,5-dihydro-5-methyl-3-(3-methyl-2-thienyl)-1 ,2-oxazole of the formula I, i.e. methiozolin) and b) a herbicide B which is trifluralin wherein the herbicide A and the herbicide B are the only herbicidally active ingredients.
Another embodiment of this invention relates to the use of a herbicidal combination comprising a) the herbicide A (preferably (5/?S)-5-[(2,6-difluorobenzyloxy)methyl]-4,5-dihydro-5-methyl-3- (3-methyl-2-thienyl)-1 ,2-oxazole of the formula I, i.e. methiozolin) and b) a herbicide B which is trifluralin wherein the herbicide A and the herbicide B are the only herbicidally active ingredients for controlling undesirable vegetation selected from the genera Alopecurus, Bromus and Lolium (preferably selected from Alopecurus myosuroides, Bromus sterilis, Lolium multiflorum and Lolium rigidum). Another embodiment of this invention relates to a method for controlling undesirable vegetation which comprises applying to the vegetation or the locus thereof or applying to the soil or water to prevent the emergence or growth of the undesirable vegetation a herbicidal combination comprising a) the herbicide A (preferably (5/?S)-5-[(2,6-difluorobenzyloxy)methyl]-4,5-dihydro-5- methyl-3-(3-methyl-2-thienyl)-1 ,2-oxazole of the formula I, i.e. methiozolin) and b) a herbicide B which is trifluralin wherein the herbicide A and the herbicide B are the only herbicidally active ingredients and the undesirable vegetation is selected from the genera Alopecurus, Bromus and Lolium (preferably selected from Alopecurus myosuroides, Bromus sterilis, Lolium multiflorum and Lolium rigidum).
In another embodiment, the herbicide B is selected from metolachlor, S-metolachlor, flufenacet and pyroxasulfone.
In yet another embodiment, the herbicide B is selected from metolachlor, S-metolachlor and flufenacet.
In another embodiment, the herbicide B is metolachlor or S-metolachlor, preferably
S-metolachlor.
In another embodiment, the herbicide B is flufenacet.
In another embodiment, the herbicidal combination comprises a) the herbicide A (preferably (5/?S)-5-[(2,6-difluorobenzyloxy)methyl]-4,5-dihydro-5-methyl-3-(3-methyl-2-thienyl)-1 ,2-oxazole of the formula I, i.e. methiozolin) and b) a herbicide B which is flufenacet wherein the herbicide A and the herbicide B are the only herbicidally active ingredients.
Another embodiment of this invention relates to the use of a herbicidal combination comprising a) the herbicide A (preferably (5/?S)-5-[(2,6-difluorobenzyloxy)methyl]-4,5-dihydro-5-methyl-3- (3-methyl-2-thienyl)-1 ,2-oxazole of the formula I, i.e. methiozolin) and b) a herbicide B which is flufenacet wherein the herbicide A and the herbicide B are the only herbicidally active ingredients for controlling undesirable vegetation selected from the genera Alopecurus, Avena, Bromus and Lolium (preferably selected from Alopecurus myosuroides, Avena fatua, Bromus sterilis, Lolium multiflorum and Lolium rigidum).
Another embodiment of this invention relates to a method for controlling undesirable vegetation which comprises applying to the vegetation or the locus thereof or applying to the soil or water to prevent the emergence or growth of the undesirable vegetation a herbicidal combination comprising a) the herbicide A (preferably (5/?S)-5-[(2,6-difluorobenzyloxy)methyl]-4,5-dihydro-5- methyl-3-(3-methyl-2-thienyl)-1 ,2-oxazole of the formula I, i.e. methiozolin) and b) a herbicide B which is flufenacet wherein the herbicide A and the herbicide B are the only herbicidally active ingredients and the undesirable vegetation is selected from the genera Alopecurus, Avena, Bromus and Lolium (preferably selected from Alopecurus myosuroides, Avena fatua, Bromus sterilis, Lolium multiflorum and Lolium rigidum). In another embodiment, the herbicide B is pyroxasulfone.
In another embodiment, the herbicidal combination comprises a) the herbicide A (preferably (5/?S)-5-[(2,6-difluorobenzyloxy)methyl]-4,5-dihydro-5-methyl-3-(3-methyl-2-thienyl)-1 ,2-oxazole of the formula I, i.e. methiozolin) and b) a herbicide B which is pyroxasulfone wherein the herbi- cide A and the herbicide B are the only herbicidally active ingredients.
Another embodiment of this invention relates to the use of a herbicidal combination comprising a) the herbicide A (preferably (5/?S)-5-[(2,6-difluorobenzyloxy)methyl]-4,5-dihydro-5-methyl-3- (3-methyl-2-thienyl)-1 ,2-oxazole of the formula I, i.e. methiozolin) and b) a herbicide B which is pyroxasulfone wherein the herbicide A and the herbicide B are the only herbicidally active ingredients for controlling undesirable vegetation selected from the genera Alopecurus, Bromus and Lolium (preferably selected from Alopecurus myosuroides, Bromus sterilis, Lolium multiflorum and Lolium rigidum).
Another embodiment of this invention relates to a method for controlling undesirable vegetation which comprises applying to the vegetation or the locus thereof or applying to the soil or water to prevent the emergence or growth of the undesirable vegetation a herbicidal combination comprising a) the herbicide A (preferably (5/?S)-5-[(2,6-difluorobenzyloxy)methyl]-4,5-dihydro-5- methyl-3-(3-methyl-2-thienyl)-1 ,2-oxazole of the formula I, i.e. methiozolin) and b) a herbicide B which is pyroxasulfone wherein the herbicide A and the herbicide B are the only herbicidally ac- tive ingredients and the undesirable vegetation is selected from the genera Alopecurus, Bromus and Lolium (preferably selected from Alopecurus myosuroides, Bromus sterilis, Lolium multiflo- rum and Lolium rigidum).
In another embodiment, the herbicide B is selected from halauxifen and its salts and esters (CAS 943832-60-8), florpyrauxifen, florpyrauxifen-benzyl (CAS 1390661-72-9) and 4-amino-3- chloro-5-fluoro-6-(7-fluoro-1 H-indol-6-yl)picolinic acid (CAS 1629965-65-6).
In another embodiment, the herbicide B is selected from halauxifen (CAS 943832-60-8) and its salts and esters.
In another embodiment, the herbicide B is florpyrauxifen.
In another embodiment, the herbicide B is florpyrauxifen-benzyl.
In another embodiment, the herbicide B is 4-amino-3-chloro-5-fluoro-6-(7-fluoro-1 H-indol-6- yl)picolinic acid (CAS 1629965-65-6).
In another embodiment, the herbicide B is selected from indanofan and oxaziclomefone.
In another embodiment, the herbicide B is indanofan. In another embodiment, the herbicide B is oxaziclomefone.
In addition to the herbicide A and the optional herbicide B, the use or method of this invention may further comprise applying at least one safener C.
Therefore, in one embodiment, the use or method of the present invention comprises applying herbicide A, at least one safener C and optionally at least one herbicide B.
In another embodiment, the use or method of the present invention comprises applying herbi- cide A, at least one herbicide B and at least one safener C.
In another embodiment of the methods or uses of this invention, a composition comprising the herbicide A is applied. In a preferred embodiment of the methods or uses of this invention, a herbicidal combination or composition comprising the herbicide A and at least one herbicide B (as defined herein) is applied. In yet another embodiment of the methods or uses of this invention, a herbicidal combination or composition comprising the herbicide A and at least one safener C (as defined herein) is applied. In still another embodiment of the methods or uses of this invention, a herbicidal combination or composition comprising the herbicide A, at least one herbicide B (as defined herein) and at least one safener C (as defined herein) is applied.
Safeners are chemical compounds which prevent or reduce damage on useful plants without having a major impact on the herbicidal action of the herbicidal active components towards un- wanted plants. Safeners can be applied before sowings (e.g. seed treatments), on shoots or seedlings as well as in the pre-emergence or post-emergence treatment of useful plants and their habitat.
Suitable safeners are e.g. (quinolin-8-oxy)acetic acids, 1-phenyl-5-haloalkyl-1 H-1 ,2,4-triazol-3- carboxylic acids, 1 -phenyl-4, 5-d i hyd ro-5-a I kyl- 1 H-pyrazol-3,5-dicarboxylic acids, 4,5-dihydro- 5,5-diaryl-3-isoxazol carboxylic acids, dichloroacetamides, alpha-oximinophenylacetonitriles, acetophenonoximes, 4,6-dihalo-2-phenylpyrimidines, N-[[4-(aminocarbonyl)phenyl]sulfonyl]-2- benzoic amides, 1 ,8-naphthalic anhydride, 2-halo-4-(haloalkyl)-5-thiazol carboxylic acids, phosphorthiolates and N-alkyl-O-phenylcarbamates and their agriculturally acceptable salts and their agriculturally acceptable derivatives such amides, esters, and thioesters, provided they have an acid group.
Preferably, the safener C is selected from the group consisting of benoxacor, cloquintocet, cy- ometrinil, cyprosulfamide, dichlormid, dicyclonon, dietholate, fenchlorazole, fenclorim, flurazole, fluxofenim, furilazole, isoxadifen, mefenpyr, mephenate, naphthaleneacetic acid (NAA), naph- thalic anhydride (NA), oxabetrinil, 4-(dichloroacetyl)-1-oxa-4-azaspiro[4.5]decane (MON4660, CAS 71526-07-3), 2,2,5-trimethyl-3-(dichloroacetyl)-1 ,3-oxazolidine (R-29148, CAS 52836- SI -4), metcamifen, 4-bromophenyl chloromethyl sulfone (BPCMS, CAS 54091-06-4) and agri culturally acceptable salts or derivatives thereof. More preferably, the safener C is selected from the group consisting of benoxacor, cloquintocet, cyometrinil, cyprosulfamide, dichlormid, dicyclonon, dietholate, fenchlorazole, fenclorim, flu- razole, fluxofenim, furilazole, isoxadifen, mefenpyr, mephenate, naphthalic anhydride (NA), oxa- betrinil, 4-(dichloroacetyl)-1 -oxa-4-azaspiro[4.5]decane (MON4660, CAS 71526-07-3), 2,2,5-tri- methyl-3-(dichloroacetyl)-1 ,3-oxazolidine (R-29148, CAS 52836-31 -4), metcamifen, 4-bromo- phenyl chloromethyl sulfone (BPCMS, CAS 54091-06-4) and agriculturally acceptable salts or derivatives thereof.
Especially preferred safeners C are benoxacor, cloquintocet, cyprosulfamide, dichlormid, fenchlorazole, fenclorim, flurazole, fluxofenim, furilazole, isoxadifen, mefenpyr, naphthalic anhy- dride (NA), oxabetrinil, 4-(dichloroacetyl)-1 -oxa-4-azaspiro[4.5]decane (MON4660, CAS 71526- 07-3), 2, 2, 5-trimethyl-3-(dichloroacetyl)-1 ,3-oxazolidine (R-29148, CAS 52836-31 -4), metcam- ifen and agriculturally acceptable salts or derivatives thereof.
Particularly preferred safeners C are benoxacor, cloquintocet, cyprosulfamide, dichlormid, fenchlorazole, fenclorim, furilazole, isoxadifen, mefenpyr, naphthalic anhydride (NA), 4-(dichlo- roacetyl)-1 -oxa-4-azaspiro[4.5]decane (MON4660, CAS 71526-07-3), 2,2,5-trimethyl-3-(dichlo- roacetyl)-1 ,3-oxazolidine (R-29148, CAS 52836-31 -4), metcamifen and agriculturally acceptable salts or derivatives thereof.
The herbicides B and safeners C are known herbicides and safeners, see, for example, The Pesticide Manual, British Crop Protection Council, 16th edition, 2012; The Compendium of Pesti- cide Common Names (http://www.alanwood.net/pesticides/); Farm Chemicals Handbook 2000 volume 86, Meister Publishing Company, 2000; B. Hock, C. Fedtke, R. R. Schmidt, Herbizide [Herbicides], Georg Thieme Verlag, Stuttgart 1995; W. H. Ahrens, Herbicide Handbook, 7th edi tion, Weed Science Society of America, 1994; and K. K. Hatzios, Herbicide Handbook, Supple- ment for the 7th edition, Weed Science Society of America, 1998. 2,2,5-T rimethyl-3-(dichloroa- cetyl)-1 ,3-oxazolidine [CAS No. 52836-31 -4] is also referred to as R-29148. 4-(Dichloroacetyl)- 1 -oxa-4-azaspiro[4.5]decane [CAS No. 71526-07-3] is also referred to as AD-67 and MON 4660.
The allocation of the active compounds to the respective modes of action is based on current knowledge. If several modes of action apply to one active compound, this compound was only allocated to one mode of action.
If the herbicides B and/or safeners C as described herein are capable of forming geometrical isomers, for example E/Z isomers, it is possible to use both, the pure isomers and mixtures thereof, in the the methods, uses, herbicidal combinations and compositions according to the invention.
If the herbicides B and/or safeners C as described herein have one or more centers of chirality and, as a consequence, are present as enantiomers or diastereomers, it is possible to use both, the pure enantiomers and diastereomers and their mixtures, in the methods, uses, herbicidal combinations and compositions according to the invention. If the herbicides B and/or safeners C as described herein have ionizable functional groups, they can also be employed in the form of their agriculturally acceptable salts. The term“agriculturally acceptable salts” is used herein to mean in general, the salts of those cations and the acid addi- tion salts of those acids whose cations and anions, respectively, have no adverse effect on the herbicidal activity of the active compounds.
Preferred cations are the ions of the alkali metals, preferably of lithium, sodium and potassium, of the alkaline earth metals, preferably of calcium and magnesium, and of the transition metals, preferably of manganese, copper, zinc and iron, further ammonium and substituted ammonium in which one to four hydrogen atoms are replaced by Ci-C4-alkyl, hydroxy-Ci-C4-alkyl, Ci-C4- alkoxy-Ci-C4-alkyl, hydroxy-Ci-C4-alkoxy-Ci-C4-alkyl, phenyl or benzyl, preferably ammonium, methylammonium, isopropylammonium, dimethylammonium, diisopropylammonium, trime- thylammonium, heptylammonium, dodecylammonium, tetradecylammonium, tetramethylammo- nium, tetraethylammonium, tetrabutylammonium, 2-hydroxyethylammonium (olamine salt), 2-(2- hydroxyeth-1-oxy)eth-1-ylammonium (diglycolamine salt), di(2-hydroxyeth-1-yl)ammonium (di- olamine salt), tris(2-hydroxyethyl)ammonium (trolamine salt), tris(2-hydroxypropyl)ammonium, benzyltrimethylammonium, benzyltriethylammonium, N,N,N-trimethylethanolammonium (choline salt), furthermore phosphonium ions, sulfonium ions, preferably tri(Ci-C4-alkyl)sulfonium, such as trimethylsulfonium, and sulfoxonium ions, preferably tri(Ci-C4-alkyl)sulfoxonium, and finally the salts of polybasic amines such as N,N-bis-(3-aminopropyl)methylamine and diethylenetri- amine.
Anions of useful acid addition salts are primarily chloride, bromide, fluoride, iodide, hydrogensul- fate, methylsulfate, sulfate, dihydrogenphosphate, hydrogenphosphate, nitrate, bicarbonate, carbonate, hexafluorosilicate, hexafluorophosphate, benzoate and also the anions of Ci-C4-al- kanoic acids, preferably formate, acetate, propionate and butyrate.
The herbicides B and/or safeners C as described herein having a carboxyl, hydroxy and/or an lamino group can be employed in the form of the acid, in the form of an agriculturally suitable salt as mentioned above or else in the form of an agriculturally acceptable derivative, for exam- pie as amides, such as mono- and di-Ci-C6-alkylamides or arylamides, as esters, for example as allyl esters, propargyl esters, Ci-Cio-alkyl esters, alkoxyalkyl esters, tefuryl ((tetrahydrofuran- 2-yl)methyl) esters and also as thioesters, for example as Ci-Cio-alkylthio esters. Preferred mono- and di-Ci-C6-alkylamides are the methyl and the dimethylamides. Preferred arylamides are, for example, the anilides and the 2-chloroanilides. Preferred alkyl esters are, for example, the methyl, ethyl, propyl, isopropyl, butyl, isobutyl, pentyl, mexyl (1-methylhexyl), meptyl (1- methylheptyl), heptyl, octyl or isooctyl (2-ethylhexyl) esters. Preferred Ci-C4-alkoxy-Ci-C4-alkyl esters are the straight-chain or branched Ci-C4-alkoxy ethyl esters, for example the 2-methoxy- ethyl, 2-ethoxyethyl, 2-butoxyethyl (butotyl), 2-butoxypropyl or 3-butoxypropyl ester. An example of a straight-chain or branched Ci-Cio-alkylthio ester is the ethylthio ester. In the case of dicamba, suitable salts include those, where the counterion is an agriculturally ac- ceptable cation. For example, suitable salts of dicamba are dicamba-sodium, dicamba-potas- sium, dicamba-methylammonium, dicamba-dimethylammonium, dicamba-isopropylammonium, dicamba-diglycolamine, dicamba-olamine, dicamba-diolamine, dicamba-trolamine, dicamba- N,N-bis-(3-aminopropyl)methylamine and dicamba-diethylenetriamine. Examples of a suitable ester are dicamba-methyl and dicam ba-butotyl.
Suitable salts of 2,4-D are 2,4-D-ammonium, 2,4-D-dimethylammonium, 2,4-D-diethylammo- nium, 2,4-D-diethanolammonium (2,4-D-diolamine), 2,4-D-triethanolammonium, 2,4-D-isoprop- ylammonium, 2,4-D-triisopropanolammonium, 2,4-D-heptylammonium, 2,4-D-dodecylammo- nium, 2,4-D-tetradecylammonium, 2,4-D-triethylammonium, 2,4-D-tris(2-hydroxypropyl)ammo- nium, 2,4-D-tris(isopropyl)ammonium, 2,4-D-trolamine, 2,4-D-lithium, 2,4-D-sodium and 2,4-D- N,N,N-trimethylethanolammonium (2,4-D choline). 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 clacyfos.
Suitable salts of 2,4-DB are for example 2,4-DB-sodium, 2,4-DB-potassium and 2,4-DB-dime- thylammonium. Suitable esters of 2,4-DB are for example 2,4-DB-butyl and 2,4-DB-isoctyl. Suitable salts of dichlorprop are for example dichlorprop-sodium, dichlorprop-potassium and di- chlorprop-dimethylammonium. Examples of suitable esters of dichlorprop are dichlorprop-buto- tyl and dichlorprop-isoctyl.
Suitable salts and esters of MCPA include MCPA-butotyl, MCPA-butyl, MCPA-dimethylammo- nium, MCPA-diolamine, MCPA-ethyl, MCPA-thioethyl, MCPA-2-ethylhexyl, MCPA-isobutyl, MCPA-isoctyl, MCPA-isopropyl, MCPA-isopropylammonium, MCPA-methyl, MCPA-olamine, MCPA-potassium, MCPA-sodium and MCPA-trolamine.
A suitable salt of MCPB is MCPB sodium. A suitable ester of MCPB is MCPB-ethyl.
Suitable salts of clopyralid are clopyralid-potassium, clopyralid-olamine and clopyralid-tris-(2- hydroxypropyl)ammonium. Example of suitable esters of clopyralid is clopyralid-methyl.
Examples of a suitable ester of fluroxypyr are fluroxypyr-meptyl and fluroxypyr-2-butoxy-1-meth- ylethyl, wherein fluroxypyr-meptyl is preferred.
Suitable salts of picloram are picloram-dimethylammonium, picloram-potassium, picloram-triiso- propanolammonium, picloram-triisopropylammonium and picloram-trolamine. A suitable ester of picloram is picloram-isoctyl.
A suitable salt of triclopyr is triclopyr-triethylammonium. Suitable esters of triclopyr are for exam- pie triclopyr-ethyl and triclopyr-butotyl.
Suitable salts and esters of chloramben include chloramben-ammonium, chloramben-diolamine, chloramben-methyl, chloramben-methylammonium and chloramben-sodium. Suitable salts and esters of 2,3,6-TBA include 2,3,6-TBA-dimethylammonium, 2,3,6-TBA-lithium, 2,3,6-TBA-potas- sium and 2,3,6-TBA-sodium.
Suitable salts and esters of aminopyralid include aminopyralid-potassium and aminopyralid- tris(2-hydroxypropyl)ammonium.
Suitable salts of glyphosate are for example glyphosate-ammonium, glyphosate-diammonium, glyphoste-dimethylammonium, glyphosate-isopropylammonium, glyphosate-potassium, glypho- sate-sodium, glyphosate-trimesium as well as the ethanolamine and diethanolamine salts, pref- erably glyphosate-diammonium, glyphosate-isopropylammonium and glyphosate-trimesium (sulfosate).
A suitable salt of glufosinate is for example glufosinate-ammonium.
A suitable salt of glufosinate-P is for example glufosinate-P-ammonium.
Suitable salts and esters of bromoxynil are for example bromoxynil-butyrate, bromoxynil-hep- tanoate, bromoxynil-octanoate, bromoxynil-potassium and bromoxynil-sodium.
Suitable salts and esters of ioxonil are for example ioxonil-octanoate, ioxonil-potassium and iox- onil-sodium.
Suitable salts and esters of mecoprop include mecoprop-butotyl, mecoprop-dimethylammonium, mecoprop-diolamine, mecoprop-ethadyl, mecoprop-2-ethylhexyl, mecoprop-isoctyl, mecoprop- methyl, mecoprop-potassium, mecoprop-sodium and mecoprop-trolamine.
Suitable salts of mecoprop-P are for example mecoprop-P-butotyl, mecoprop-P-dimethylammo- nium, mecoprop-P-2-ethylhexyl, mecoprop-P-isobutyl, mecoprop-P-potassium and mecoprop-P- sodium.
A suitable salt of diflufenzopyr is for example diflufenzopyr-sodium.
A suitable salt of naptalam is for example naptalam-sodium.
Suitable salts and esters of aminocyclopyrachlor are for example aminocyclopyrachlor-dime- thylammonium, aminocyclopyrachlor-methyl, aminocyclopyrachlor-triisopropanolammonium, aminocyclopyrachlor-sodium and aminocyclopyrachlor-potassium.
A suitable salt of quinclorac is for example quinclorac-dimethylammonium.
A suitable salt of quinmerac is for example quinclorac-dimethylammonium.
A suitable salt of imazamox is for example imazamox-ammonium.
Suitable salts of imazapic are for example imazapic-ammonium and imazapic-isopropylammo- nium.
Suitable salts of imazapyr are for example imazapyr-ammonium and imazapyr-isopropylammo- nium.
A suitable salt of imazaquin is for example imazaquin-ammonium.
Suitable salts of imazethapyr are for example imazethapyr-ammonium and imazethapyr-iso- propylammonium.
A suitable salt of topramezone is for example topramezone-sodium.
In yet another embodiment, these compositions may further comprise one or more auxiliaries customary in crop protection (as defined herein).
Certain combinations of (a) herbicide A and (b) herbicide B may also be capable of providing a synergistic herbicidal effect.
Thus, in a preferred embodiment of the methods, uses, herbicidal combinations and composi- tions of this invention, the herbicide A and herbicide B are each present or applied in an amount sufficient to provide a synergistic herbicidal effect.
The term "synergistic herbicidal effect" refers to the herbicidal effect for a given combination of two herbicides where the herbicidal activity of the combination exceeds the total of the individual herbicidal activities of the herbicides when applied separately. For this reason, the herbicidal combinations or compositions of this invention can, based on the individual components, be used at lower application rates to achieve a herbicidal effect comparable to the individual com- ponents.
In some embodiments of this invention, Colby's equation is applied to determine whether the combination of herbicide A and herbicide B shows a synergistic effect (see S. R. Colby, "Calcu- lating synergistic and antagonistic responses of herbicide combinations", Weeds 1967, 15, pp. 20-22).
E = X + Y - (CΎ/100) where X = effect in percent using herbicide A at an application rate a;
Y = effect in percent using herbicide B at application rate b;
E = expected effect (in %) of herbicide A + herbicide B at application rates a + b.
In Colby's equation, the value E corresponds to the effect (plant damage or injury) which is to be expected if the activity of the individual compounds is additive. If the observed effect is higher than the value E calculated according to the Colby equation, a synergistic effect is pre- sent.
In one embodiment of the present invention, the herbicidal combination or composition compris- ing herbicide A and the at least one herbicide B is synergistic as determined by the Colby equa- tion. Specifically, the synergistic herbicidal effect is determined according to the Colby equation.
In the methods, uses, herbicidal combinations and compositions of the invention, the weight ra- tio of herbicide A to herbicide B is generally in the range of from 1 : 1000 to 1000:1 , preferably in the range of from 1 :500 to 500:1 , in particular in the range of from 1 :250 to 250:1 and particu- larly preferably in the range of from 1 :75 to 75:1 , wherein each herbicide B being an ester or a salt of an acid is calculated as the acid.
In another embodiment, the herbicidal combination comprises a) the herbicide A (preferably (5/?S)-5-[(2,6-difluorobenzyloxy)methyl]-4,5-dihydro-5-methyl-3-(3-methyl-2-thienyl)-1 ,2-oxazole of the formula I, i.e. methiozolin) and b) a herbicide B which is triallate wherein the herbicide A and the herbicide B are the only herbicidally active ingredients and the weight ratio of herbicide A to herbicide B is from 10:1 to 1 :10 (preferably from 5:1 to 1 :5).
Another embodiment of this invention relates to the use of a herbicidal combination comprising a) the herbicide A (preferably (5/?S)-5-[(2,6-difluorobenzyloxy)methyl]-4,5-dihydro-5-methyl-3- (3-methyl-2-thienyl)-1 ,2-oxazole of the formula I, i.e. methiozolin) and b) a herbicide B which is triallate wherein the herbicide A and the herbicide B are the only herbicidally active ingredients and the weight ratio of herbicide A to herbicide B is from 10:1 to 1 :10 (preferably from 5:1 to 1 :5) for controlling undesirable vegetation selected from the genera Alopecurus, Avena, Bromus and Lolium (preferably selected from Alopecurus myosuroides, Avena fatua, Bromus sterilis, Lolium multiflorum and Lolium rigidum). Another embodiment of this invention relates to a method for controlling undesirable vegetation which comprises applying to the vegetation or the locus thereof or applying to the soil or water to prevent the emergence or growth of the undesirable vegetation a herbicidal combination comprising a) the herbicide A (preferably (5/?S)-5-[(2,6-difluorobenzyloxy)methyl]-4,5-dihydro-5- methyl-3-(3-methyl-2-thienyl)-1 ,2-oxazole of the formula I, i.e. methiozolin) and b) a herbicide B which is triallate wherein the herbicide A and the herbicide B are the only herbicidally active ingredients and the weight ratio of herbicide A to herbicide B is from 10:1 to 1 :10 (preferably from 5:1 to 1 :5) wherein the undesirable vegetation is selected from the genera Alopecurus, Avena, Bromus and Lolium (preferably selected from Alopecurus myosuroides, Avena fatua, Bromus sterilis, Lolium multiflorum and Lolium rigidum).
In another embodiment, the herbicidal combination comprises a) the herbicide A (preferably (5/?S)-5-[(2,6-difluorobenzyloxy)methyl]-4,5-dihydro-5-methyl-3-(3-methyl-2-thienyl)-1 ,2-oxazole of the formula I, i.e. methiozolin) and b) a herbicide B which is saflufenacil wherein the herbicide A and the herbicide B are the only herbicidally active ingredients and the weight ratio of herbi- cide A to herbicide B is from 100:1 to 1 :1 (preferably from 50:1 to 1 :1 ).
Another embodiment of this invention relates to the use of a herbicidal combination comprising a) the herbicide A (preferably (5/?S)-5-[(2,6-difluorobenzyloxy)methyl]-4,5-dihydro-5-methyl-3- (3-methyl-2-thienyl)-1 ,2-oxazole of the formula I, i.e. methiozolin) and b) a herbicide B which is saflufenacil wherein the herbicide A and the herbicide B are the only herbicidally active ingredients and the weight ratio of herbicide A to herbicide B is from 100:1 to 1 :1 (preferably from 50:1 to 1 :1 ) for controlling undesirable vegetation selected from the genus Bromus (which is preferably Bromus sterilis).
Another embodiment of this invention relates to a method for controlling undesirable vegetation which comprises applying to the vegetation or the locus thereof or applying to the soil or water to prevent the emergence or growth of the undesirable vegetation a herbicidal combination comprising a) the herbicide A (preferably (5/?S)-5-[(2,6-difluorobenzyloxy)methyl]-4,5-dihydro-5- methyl-3-(3-methyl-2-thienyl)-1 ,2-oxazole of the formula I, i.e. methiozolin) and b) a herbicide B which is saflufenacil wherein the herbicide A and the herbicide B are the only herbicidally active ingredients and the weight ratio of herbicide A to herbicide B is from 100:1 to 1 :1 (preferably from 50:1 to 1 :1 ) wherein the undesirable vegetation is selected from the genus Bromus (which is preferably Bromus sterilis).
In another embodiment, the herbicidal combination comprises a) the herbicide A (preferably (5/?S)-5-[(2,6-difluorobenzyloxy)methyl]-4,5-dihydro-5-methyl-3-(3-methyl-2-thienyl)-1 ,2-oxazole of the formula I, i.e. methiozolin) and b) a herbicide B which is diflufenican wherein the herbicide A and the herbicide B are the only herbicidally active ingredients and the weight ratio of herbi- cide A to herbicide B is from 10:1 to 1 :1.
Another embodiment of this invention relates to the use of a herbicidal combination comprising a) the herbicide A (preferably (5/?S)-5-[(2,6-difluorobenzyloxy)methyl]-4,5-dihydro-5-methyl-3- (3-methyl-2-thienyl)-1 ,2-oxazole of the formula I, i.e. methiozolin) and b) a herbicide B which is diflufenican wherein the herbicide A and the herbicide B are the only herbicidally active ingredients and the weight ratio of herbicide A to herbicide B is from 10:1 to 1 :1 for controlling undesirable vegetation selected from the genera Alopecurus, Avena, Bromus and Lolium (preferably selected from Alopecurus myosuroides, Avena fatua, Bromus sterilis, Lolium multiflorum and Lolium rigidum).
Another embodiment of this invention relates to a method for controlling undesirable vegetation which comprises applying to the vegetation or the locus thereof or applying to the soil or water to prevent the emergence or growth of the undesirable vegetation a herbicidal combination comprising a) the herbicide A (preferably (5/?S)-5-[(2,6-difluorobenzyloxy)methyl]-4,5-dihydro-5- methyl-3-(3-methyl-2-thienyl)-1 ,2-oxazole of the formula I, i.e. methiozolin) and b) a herbicide B which is diflufenican wherein the herbicide A and the herbicide B are the only herbicidally active ingredients and the weight ratio of herbicide A to herbicide B is from 10:1 to 1 :1 wherein the undesirable vegetation is selected from the genera Alopecurus, Avena, Bromus and Lolium (preferably selected from Alopecurus myosuroides, Avena fatua, Bromus sterilis, Lolium multiflorum and Lolium rigidum).
In another embodiment, the herbicidal combination comprises a) the herbicide A (preferably (5/?S)-5-[(2,6-difluorobenzyloxy)methyl]-4,5-dihydro-5-methyl-3-(3-methyl-2-thienyl)-1 ,2-oxazole of the formula I, i.e. methiozolin) and b) a herbicide B which is picolinafen wherein the herbicide A and the herbicide B are the only herbicidally active ingredients and the weight ratio of herbi- cide A to herbicide B is from 25:1 to 1 :1.
Another embodiment of this invention relates to the use of a herbicidal combination comprising a) the herbicide A (preferably (5/?S)-5-[(2,6-difluorobenzyloxy)methyl]-4,5-dihydro-5-methyl-3- (3-methyl-2-thienyl)-1 ,2-oxazole of the formula I, i.e. methiozolin) and b) a herbicide B which is picolinafen wherein the herbicide A and the herbicide B are the only herbicidally active ingredients and the weight ratio of herbicide A to herbicide B is from 25:1 to 1 :1 for controlling undesirable vegetation selected from the genera Bromus and Lolium (preferably selected from Bromus sterilis and Lolium multiflorum).
Another embodiment of this invention relates to a method for controlling undesirable vegetation which comprises applying to the vegetation or the locus thereof or applying to the soil or water to prevent the emergence or growth of the undesirable vegetation a herbicidal combination comprising a) the herbicide A (preferably (5/?S)-5-[(2,6-difluorobenzyloxy)methyl]-4,5-dihydro-5- methyl-3-(3-methyl-2-thienyl)-1 ,2-oxazole of the formula I, i.e. methiozolin) and b) a herbicide B which is picolinafen wherein the herbicide A and the herbicide B are the only herbicidally active ingredients and the weight ratio of herbicide A to herbicide B is from 25:1 to 1 :1 wherein the undesirable vegetation is selected from the genera Bromus and Lolium (preferably selected from Bromus sterilis and Lolium multiflorum).
In another embodiment, the herbicidal combination comprises a) the herbicide A (preferably (5/?S)-5-[(2,6-difluorobenzyloxy)methyl]-4,5-dihydro-5-methyl-3-(3-methyl-2-thienyl)-1 ,2-oxazole of the formula I, i.e. methiozolin) and b) a herbicide B which is pendimethalin wherein the herbi- cide A and the herbicide B are the only herbicidally active ingredients and the weight ratio of herbicide A to herbicide B is from 1 :1 to 1 :10 (preferably from 1 :1 to 1 :5).
Another embodiment of this invention relates to the use of a herbicidal combination comprising a) the herbicide A (preferably (5/?S)-5-[(2,6-difluorobenzyloxy)methyl]-4,5-dihydro-5-methyl-3- (3-methyl-2-thienyl)-1 ,2-oxazole of the formula I, i.e. methiozolin) and b) a herbicide B which is pendimethalin wherein the herbicide A and the herbicide B are the only herbicidally active ingredients and the weight ratio of herbicide A to herbicide B is from 1 :1 to 1 :10 (preferably from 1 :1 to 1 :5) for controlling undesirable vegetation selected from the genera Alopecurus, Avena and Lolium (preferably selected from Alopecurus myosuroides, Avena fatua, Lolium multiflorum and Lolium rigidum).
Another embodiment of this invention relates to a method for controlling undesirable vegetation which comprises applying to the vegetation or the locus thereof or applying to the soil or water to prevent the emergence or growth of the undesirable vegetation a herbicidal combination comprising a) the herbicide A (preferably (5/?S)-5-[(2,6-difluorobenzyloxy)methyl]-4,5-dihydro-5- methyl-3-(3-methyl-2-thienyl)-1 ,2-oxazole of the formula I, i.e. methiozolin) and b) a herbicide B which is pendimethalin wherein the herbicide A and the herbicide B are the only herbicidally active ingredients and the weight ratio of herbicide A to herbicide B is from 1 :1 to 1 :10
(preferably from 1 :1 to 1 :5) wherein the undesirable vegetation is selected from the genera Alopecurus, Avena and Lolium (preferably selected from Alopecurus myosuroides, Avena fatua, Lolium multiflorum and Lolium rigidum).
In another embodiment, the herbicidal combination comprises a) the herbicide A (preferably (5/?S)-5-[(2,6-difluorobenzyloxy)methyl]-4,5-dihydro-5-methyl-3-(3-methyl-2-thienyl)-1 ,2-oxazole of the formula I, i.e. methiozolin) and b) a herbicide B which is trifluralin wherein the herbicide A and the herbicide B are the only herbicidally active ingredients and the weight ratio of herbicide A to herbicide B is from 10:1 to 1 :10 (preferably from 5:1 to 1 :5).
Another embodiment of this invention relates to the use of a herbicidal combination comprising a) the herbicide A (preferably (5/?S)-5-[(2,6-difluorobenzyloxy)methyl]-4,5-dihydro-5-methyl-3- (3-methyl-2-thienyl)-1 ,2-oxazole of the formula I, i.e. methiozolin) and b) a herbicide B which is trifluralin wherein the herbicide A and the herbicide B are the only herbicidally active ingredients and the weight ratio of herbicide A to herbicide B is from 10:1 to 1 :10 (preferably from 5:1 to 1 :5) for controlling undesirable vegetation selected from the genera Alopecurus, Bromus and Lolium (preferably selected from Alopecurus myosuroides, Bromus sterilis, Lolium multiflorum and Lolium rigidum).
Another embodiment of this invention relates to a method for controlling undesirable vegetation which comprises applying to the vegetation or the locus thereof or applying to the soil or water to prevent the emergence or growth of the undesirable vegetation a herbicidal combination comprising a) the herbicide A (preferably (5/?S)-5-[(2,6-difluorobenzyloxy)methyl]-4,5-dihydro-5- methyl-3-(3-methyl-2-thienyl)-1 ,2-oxazole of the formula I, i.e. methiozolin) and b) a herbicide B which is trifluralin wherein the herbicide A and the herbicide B are the only herbicidally active ingredients and the weight ratio of herbicide A to herbicide B is from 10:1 to 1 :10 (preferably from 5:1 to 1 :5) wherein the undesirable vegetation is selected from the genera Alopecurus, Bromus and Lolium (preferably selected from Alopecurus myosuroides, Bromus sterilis, Lolium multiflorum and Lolium rigidum).
In another embodiment, the herbicidal combination comprises a) the herbicide A (preferably (5/?S)-5-[(2,6-difluorobenzyloxy)methyl]-4,5-dihydro-5-methyl-3-(3-methyl-2-thienyl)-1 ,2-oxazole of the formula I, i.e. methiozolin) and b) a herbicide B which is flufenacet wherein the herbicide A and the herbicide B are the only herbicidally active ingredients and the weight ratio of herbi- cide A to herbicide B is from 10:1 to 1 :1.
Another embodiment of this invention relates to the use of a herbicidal combination comprising a) the herbicide A (preferably (5/?S)-5-[(2,6-difluorobenzyloxy)methyl]-4,5-dihydro-5-methyl-3- (3-methyl-2-thienyl)-1 ,2-oxazole of the formula I, i.e. methiozolin) and b) a herbicide B which is flufenacet wherein the herbicide A and the herbicide B are the only herbicidally active ingredients and the weight ratio of herbicide A to herbicide B is from 10:1 to 1 :1 for controlling undesirable vegetation selected from the genera Alopecurus, Avena, Bromus, and Lolium (preferably selected from Alopecurus myosuroides, Avena fatua, Bromus sterilis, Lolium multiflorum and Lolium rigidum).
Another embodiment of this invention relates to a method for controlling undesirable vegetation which comprises applying to the vegetation or the locus thereof or applying to the soil or water to prevent the emergence or growth of the undesirable vegetation a herbicidal combination comprising a) the herbicide A (preferably (5/?S)-5-[(2,6-difluorobenzyloxy)methyl]-4,5-dihydro-5- methyl-3-(3-methyl-2-thienyl)-1 ,2-oxazole of the formula I, i.e. methiozolin) and b) a herbicide B which is flufenacet wherein the herbicide A and the herbicide B are the only herbicidally active ingredients and the weight ratio of herbicide A to herbicide B is from 10:1 to 1 :1 wherein the undesirable vegetation is selected from the genera Alopecurus, Avena, Bromus and Lolium (preferably selected from Alopecurus myosuroides, Avena fatua, Bromus sterilis, Lolium multiflorum and Lolium rigidum).
In another embodiment, the herbicidal combination comprises a) the herbicide A (preferably (5/?S)-5-[(2,6-difluorobenzyloxy)methyl]-4,5-dihydro-5-methyl-3-(3-methyl-2-thienyl)-1 ,2-oxazole of the formula I, i.e. methiozolin) and b) a herbicide B which is pyroxasulfone wherein the herbi- cide A and the herbicide B are the only herbicidally active ingredients and the weight ratio of herbicide A to herbicide B is from 40:1 to 1 :1 (preferably from 40:1 to 10:1 ).
Another embodiment of this invention relates to the use of a herbicidal combination comprising a) the herbicide A (preferably (5/?S)-5-[(2,6-difluorobenzyloxy)methyl]-4,5-dihydro-5-methyl-3- (3-methyl-2-thienyl)-1 ,2-oxazole of the formula I, i.e. methiozolin) and b) a herbicide B which is pyroxasulfone wherein the herbicide A and the herbicide B are the only herbicidally active ingredients and the weight ratio of herbicide A to herbicide B is from 40:1 to 1 :1 (preferably from 40:1 to 10:1 ) for controlling undesirable vegetation selected from the genera Alopecurus, Bromus and Lolium (preferably selected from Alopecurus myosuroides, Bromus sterilis, Lolium multiflorum and Lolium rigidum).
Another embodiment of this invention relates to a method for controlling undesirable vegetation which comprises applying to the vegetation or the locus thereof or applying to the soil or water to prevent the emergence or growth of the undesirable vegetation a herbicidal combination comprising a) the herbicide A (preferably (5/?S)-5-[(2,6-difluorobenzyloxy)methyl]-4,5-dihydro-5- methyl-3-(3-methyl-2-thienyl)-1 ,2-oxazole of the formula I, i.e. methiozolin) and b) a herbicide B which is pyroxasulfone wherein the herbicide A and the herbicide B are the only herbicidally active ingredients and the weight ratio of herbicide A to herbicide B is from 40:1 to 1 : 1
(preferably from 40:1 to 10:1 ) wherein the undesirable vegetation is selected from the genera Alopecurus, Bromus and Lolium (preferably selected from Alopecurus myosuroides, Bromus sterilis, Lolium multiflorum and Lolium rigidum).
In the methods, uses, herbicidal combinations and compositions of the invention, the weight ra- tio of herbicide A to safener C is generally in the range of from 1 :1000 to 1000:1 , preferably in the range of from 1 :500 to 500:1 , in particular in the range of from 1 :250 to 250:1 and particu- larly preferably in the range of from 1 :75 to 75:1 , wherein each safener C being an ester or a salt of an acid is calculated as the acid.
In the methods, uses, herbicidal combinations and compositions of the invention, the weight ra- tio of herbicide B to safener C is generally in the range of from 1 :1000 to 1000:1 , preferably in the range of from 1 :500 to 500:1 , in particular in the range of from 1 :250 to 250:1 and particu- larly preferably in the range of from 1 :75 to 75:1 , wherein each herbicide B and safener C being an ester or a salt of an acid is calculated as the acid.
In the methods, uses, herbicidal combinations and compositions of the invention, the weight ra- tio of the combination of herbicides A and B to the safener C is preferably in the range of from 1 :500 to 500:1 , in particular in the range of from 1 :250 to 250:1 and particularly preferably in the range of from 1 :75 to 75:1 , wherein each herbicide B and safener C being an ester or a salt of an acid is calculated as the acid.
The herbicide A or the herbicidal combinations as defined herein are suitable as herbicides as such or as appropriately formulated agrochemical compositions. As used herein, the term“agro- chemical composition” refers to a composition further comprising one or more auxiliaries cus- tomary in crop protection.
Thus, the agrochemical composition comprises the herbicide A, optionally at least one herbicide B (as defined herein), optionally at least one safener C (as defined herein) and one or more auxiliaries customary in crop protection.
The herbicide A, optionally at least one herbicide B (as defined herein) and optionally at least one safener C (as defined herein) can be converted into customary types of agrochemical corn- positions, e. g. solutions, emulsions, suspensions, dusts, powders, pastes, granules, pressings, capsules, and mixtures thereof. Examples for agrochemical composition types are suspensions (e.g. SC, OD, FS), emulsifiable concentrates (e.g. EC), emulsions (e.g. EW, EO, ES, ME), cap- sules (e.g. CS, ZC), pastes, pastilles, wettable powders or dusts (e.g. WP, SP, WS, DP, DS), pressings (e.g. BR, TB, DT), granules (e.g. WG, SG, GR, FG, GG, MG), insecticidal articles (e.g. LN), as well as gel formulations for the treatment of plant propagation materials such as seeds (e.g. GF). These and further agrochemical compositions types are defined in the“Ca- talogue of pesticide formulation types and international coding system”, Technical Monograph No. 2, 6th Ed. May 2008, CropLife International.
The agrochemical compositions can be prepared in a known manner, such as described by Mollet and Grubemann, Formulation technology, Wiley VCH, Weinheim, 2001 ; or Knowles, New developments in crop protection product formulation, Agrow Reports DS243, T&F Informa, Lon- don, 2005.
The term "auxiliaries customary in crop protection" includes but is not limited to solvents, liquid carriers, solid carriers or fillers, surfactants, dispersants, emulsifiers, wetters, adjuvants, solubil- izers, penetration enhancers, protective colloids, adhesion agents, thickeners, humectants, re- pellents, attractants, feeding stimulants, compatibilizers, bactericides, anti-freezing agents, anti- foaming agents, colorants, tackifiers and binders.
Suitable solvents and liquid carriers are water and organic solvents, such as mineral oil frac- tions of medium to high boiling point, e.g. kerosene, diesel oil; oils of vegetable or animal origin; aliphatic, cyclic and aromatic hydrocarbons, e. g. toluene, paraffin, tetrahydronaphthalene, alkyl- ated naphthalenes; alcohols, e.g. ethanol, propanol, butanol, benzylalcohol, cyclohexanol; gly cols; DMSO; ketones, e.g. cyclohexanone; esters, e.g. lactates, carbonates, fatty acid esters, gamma-butyrolactone; fatty acids; phosphonates; amines; amides, e.g. N-methylpyrrolidone, fatty acid dimethylamides; and mixtures thereof.
Suitable solid carriers or fillers are mineral earths, e.g. silicates, silica gels, talc, kaolins, lime- stone, lime, chalk, clays, dolomite, diatomaceous earth, bentonite, calcium sulfate, magnesium sulfate, magnesium oxide; polysaccharides, e.g. cellulose, starch; fertilizers, e.g. ammonium sulfate, ammonium phosphate, ammonium nitrate, ureas; products of vegetable origin, e.g. ce- real meal, tree bark meal, wood meal, nutshell meal, and mixtures thereof.
Suitable surfactants are surface-active compounds, such as anionic, cationic, nonionic and am- photeric surfactants, block polymers, polyelectrolytes, and mixtures thereof. Such surfactants can be used as emusifier, dispersant, solubilizer, wetter, penetration enhancer, protective col- loid, or adjuvant. Examples of surfactants are listed in McCutcheon’s, Vol.1 : Emulsifiers & De- tergents, McCutcheon’s Directories, Glen Rock, USA, 2008 (International Ed. or North American Ed.).
Suitable anionic surfactants are alkali, alkaline earth or ammonium salts of sulfonates, sulfates, phosphates, carboxylates, and mixtures thereof. Examples of sulfonates are alkylarylsulfonates, diphenylsulfonates, alpha-olefin sulfonates, lignine sulfonates, sulfonates of fatty acids and oils, sulfonates of ethoxylated alkylphenols, sulfonates of alkoxylated arylphenols, sulfonates of con- densed naphthalenes, sulfonates of dodecyl- and tridecylbenzenes, sulfonates of naphthalenes and alkylnaphthalenes, sulfosuccinates or sulfosuccinamates. Examples of sulfates are sulfates of fatty acids and oils, of ethoxylated alkylphenols, of alcohols, of ethoxylated alcohols, or of fatty acid esters. Examples of phosphates are phosphate esters. Examples of carboxylates are alkyl carboxylates, and carboxylated alcohol or alkylphenol ethoxylates.
Suitable nonionic surfactants are alkoxylates, N-subsituted fatty acid amides, amine oxides, es- ters, sugar-based surfactants, polymeric surfactants, and mixtures thereof. Examples of alkox- ylates are compounds such as alcohols, alkylphenols, amines, amides, arylphenols, fatty acids or fatty acid esters which have been alkoxylated with 1 to 50 equivalents. Ethylene oxide and/or propylene oxide may be employed for the alkoxylation, preferably ethylene oxide. Examples of N-subsititued fatty acid amides are fatty acid glucamides or fatty acid alkanolamides. Examples of esters are fatty acid esters, glycerol esters or monoglycerides. Examples of sugar-based sur- factants are sorbitans, ethoxylated sorbitans, sucrose and glucose esters or alkylpolygluco- sides. Examples of polymeric surfactants are home- or copolymers of vinylpyrrolidone, vinylal- cohols, or vinylacetate.
Suitable cationic surfactants are quaternary surfactants, for example quaternary ammonium compounds with one or two hydrophobic groups, or salts of long-chain primary amines. Suitable amphoteric surfactants are alkylbetains and imidazolines. Suitable block polymers are block pol- ymers of the A-B or A-B-A type comprising blocks of polyethylene oxide and polypropylene ox ide, or of the A-B-C type comprising alkanol, polyethylene oxide and polypropylene oxide. Suita- ble polyelectrolytes are polyacids or polybases. Examples of polyacids are alkali salts of poly- acrylic acid or polyacid comb polymers. Examples of polybases are polyvinylamines or polyeth- yleneamines.
Suitable adjuvants are compounds, which have a neglectable or even no pesticidal activity themselves, and which improve the biological performance of the compound I on the target. Ex- amples are surfactants, mineral or vegetable oils, and other auxilaries. Further examples are listed by Knowles, Adjuvants and additives, Agrow Reports DS256, T&F Informa UK, 2006, chapter 5.
Suitable thickeners are polysaccharides (e.g. xanthan gum, carboxymethylcellulose), anorganic clays (organically modified or unmodified), polycarboxylates, and silicates.
Suitable bactericides are bronopol and isothiazolinone derivatives such as alkylisothiazolinones and benzisothiazolinones.
Suitable anti-freezing agents are ethylene glycol, propylene glycol, urea and glycerin.
Suitable anti-foaming agents are silicones, long chain alcohols, and salts of fatty acids. Suitable colorants (e.g. in red, blue, or green) are pigments of low water solubility and water-sol- uble dyes. Examples are inorganic colorants (e.g. iron oxide, titan oxide, iron hexacyanoferrate) and organic colorants (e.g. alizarin-, azo- and phthalocyanine colorants).
Suitable tackifiers or binders are polyvinylpyrrolidons, polyvinylacetates, polyvinyl alcohols, pol- yacrylates, biological or synthetic waxes, and cellulose ethers.
The agrochemical compositions generally comprise between 0.01 and 95%, preferably between 0.1 and 90%, and in particular between 0.5 and 75%, by weight of active substance. The active substances are employed in a purity of from 90% to 100%, preferably from 95% to 100% (ac- cording to NMR spectrum).
Solutions for seed treatment (LS), suspoemulsions (SE), flowable concentrates (FS), powders for dry treatment (DS), water-dispersible powders for slurry treatment (WS), water-soluble pow- ders (SS), emulsions (ES), emulsifiable concentrates (EC) and gels (GF) are usually employed for the purposes of treatment of plant propagation materials, particularly seeds. The composi- tions in question give, after two-to-tenfold dilution, active substance concentrations of from 0.01 to 60% by weight, preferably from 0.1 to 40% by weight, in the ready-to-use preparations. Appli- cation can be carried out before or during sowing.
Methods for applying the herbicide A, optionally at least one herbicide B and optionally at least one safener C (or a composition comprising the herbicide A, optionally at least one herbicide B and optionally at least one safener C) onto plant propagation material, especially seeds include dressing, coating, pelleting, dusting, soaking and in-furrow application methods of the propaga- tion material. Preferably the herbicide A, optionally at least one herbicide B and optionally at least one safener C (or a composition comprising the herbicide A, optionally at least one herbi- cide B and optionally at least one safener C) are applied onto the plant propagation material by a method such that germination is not induced, e. g. by seed dressing, pelleting, coating and dusting.
Various types of oils, wetters, adjuvants, fertilizer, or micronutrients, and further pesticides (e.g. herbicides, insecticides, fungicides, growth regulators, safeners) may be added to the active substances or the compositions comprising them as premix or, if appropriate not until immedi- ately prior to use (tank mix). These agents can be admixed with the herbicide A, optionally at least one herbicide B and optionally at least one safener C (or the composition comprising the herbicide A, optionally at least one herbicide B and optionally at least one safener C) used or applied in this invention in a weight ratio of 1 : 100 to 100:1 , preferably 1 : 10 to 10:1.
The user applies the agrochemical composition used or applied in this invention usually from a predosage device, a knapsack sprayer, a spray tank, a spray plane, or an irrigation system. Usually, the agrochemical composition is made up with water, buffer, and/or further auxiliaries to the desired application concentration and the ready-to-use spray liquor or the agrochemical composition according to the invention is thus obtained. Usually, 20 to 2000 liters, preferably 50 to 400 liters, of the ready-to-use spray liquor are applied per hectare of agricultural useful area. According to one embodiment, either individual components of the agrochemical composition or partially premixed components, e. g. agrochemical components comprising herbicide A, option- ally at least one herbicide B and optionally at least one safener C may be mixed by the user in a spray tank and further auxiliaries and additives may be added, if appropriate.
In another embodiment, individual components of the agrochemical composition such as parts of a kit or parts of a binary or ternary mixture may be mixed by the user himself in a spray tank and further auxiliaries may be added, if appropriate.
In another embodiment, either individual components of the agrochemical composition or par- tially premixed components, e. g. components comprising herbicide A, optionally at least one herbicide B and optionally at least one safener C can be applied jointly (e.g. after tank mixing) or consecutively.
Accordingly, the agrochemical composition may be provided in the form of a single package for- mulation comprising herbicide A, optionally at least one herbicide B and optionally at least one safener C together with liquid and/or solid carriers, and, if desired, one or more surfactants and, if desired, one or more further auxiliaries customary in crop protection. The formulation may be provided in the form of a two-package formulation, wherein one package comprises a formula- tion of herbicide A while the other package comprises a formulation comprising at least one herbicide B and/or safener C, and wherein both formulations comprise at least one carrier mate- rial, if desired, one or more surfactants and, if desired, one or more further auxiliaries customary in crop protection. The formulation may also be provided in the form of a two-package formula- tion, wherein one package comprises a formulation of herbicide A and optionally the safener C, while the other package comprises a formulation of the at least one herbicide B, and wherein both formulations comprises at least one carrier material, if desired, one or more surfactants and, if desired, one or more further auxiliaries customary in crop protection. In the case of two package formulations, the two formulations are preferably mixed prior to application. Preferably, the mixing is performed as a tank mix, i.e. the formulations are mixed immediately prior or upon dilution with water.
The compositions as defined herein control vegetation on non-crop areas very efficiently, espe- cially at high rates of application. They act against broad-leafed weeds and grass weeds in crops such as wheat, barley, rice, corn, sunflowers, soybeans and cotton without causing any significant damage to the crop plants. This effect is mainly observed at low rates of application.
The compositions as defined herein are applied to the plants mainly by spraying. Here, the ap- plication can be carried out using, for example, water as carrier by customary spraying tech- niques using spray liquor amounts of from about 50 to 1000 l/ha (for example from 300 to 400 l/ha). The compositions as defined herein may also be applied by the low-volume or the ultra- low-volume method, or in the form of microgranules.
The compositions as defined herein can be applied pre- or post-emergence or together with the seed of a crop plant. It is also possible to apply the compounds and compositions by applying seed, pretreated with a composition as defined herein, of a crop plant. If the herbicide A and, if appropriate, the herbicide B are less well tolerated by certain crop plants, application techniques may be used in which the herbicidal compositions are sprayed, with the aid of the spraying equipment, in such a way that as far as possible they do not come into contact with the leaves of the sensitive crop plants, while the active compounds reach the leaves of undesirable plants growing underneath, or the bare soil surface (post-directed, lay-by).
In a further embodiment, the compositions as defined herein can be applied by treating seed. The treatment of seed comprises essentially all procedures familiar to the person skilled in the art (seed dressing, seed coating, seed dusting, seed soaking, seed film coating, seed multilayer coating, seed encrusting, seed dripping and seed pelleting) based on the compositions as de- fined herein. Here, the compositions as defined herein can be applied diluted or undiluted.
The term "seed" comprises seed of all types, such as, for example, corns, seeds, fruits, tubers, seedlings and similar forms. Here, preferably, the term seed describes corns and seeds. The seed used can be the seed of the useful plants mentioned above, but also the seed of trans- genic plants or plants obtained by customary breeding methods.
Moreover, it may be advantageous to apply the compositions as defined herein on their own or jointly in combination with other crop protection agents, for example with agents for controlling pests or phytopathogenic fungi or bacteria or with groups of active compounds which regulate growth. Also of interest is the miscibility with mineral salt solutions which are employed for treat- ing nutritional and trace element deficiencies. Non-phytotoxic oils and oil concentrates can also be added.
When employed in plant protection, the amounts of active substances applied (i.e. herbicide A and, if appropriate, herbicide B) without formulation auxiliaries, are, depending on the kind of ef- fect desired, 0.0001 to 10 kg per hectare (kg/ha), preferably 0.001 to 3 kg/ha, more preferably from 0.001 to 2.5 kg/ha, even more preferably from 0.001 to 2 kg/ha, especially preferably from 0.005 to 2 kg/ha, in particular from 0.05 to 1 kg/ha.
In the methods and uses of this invention, the herbicide A is generally applied in an amount of from 0.1 to 2000 grams per hectare (g/ha), preferably 10 to 1000 g/ha, more preferably 100 to 1000 g/ha. In another embodiment, the herbicide A is applied in an amount of from 50 to 1000 g/ha, preferably 75 to 1000 g/ha and more preferably 100 to 1000 g/ha.
In the methods and uses of this invention, the application rate of the herbicide B (in case of salts calculated as the acid) is generally from 0.0005 kg/ha to 10 kg/ha, preferably from 0.005 kg/ha to 5 kg/ha and more preferably from 0.001 kg/ha to 2.5 kg/ha.
In the methods and uses of this invention, the application rate of the safener C (in case of salts calculated as the acid) is generally from 0.0005 kg/ha to 2.5 kg/ha, preferably from 0.005 kg/ha to 2 kg/ha and more preferably from 0.01 kg/ha to 1.5 kg/ha.
In treatment of plant propagation materials such as seeds, e. g. by dusting, coating or drenching seed, amounts of active substance (i.e. herbicide A and, if appropriate, herbicide B) of from 0.1 to 5000 g, preferably from 5 to 2500 g, more preferably from 50 to 2000 g and in particular from 100 to 1500 g, per 100 kilogram of plant propagation material (preferably seeds) are generally required.
In another embodiment of the invention, to treat the seed, the amounts of active substances ap- plied (i.e. herbicide A and, if appropriate, herbicide B) are generally employed in amounts of from 0.001 to 10 kg per 100 kg of seed.
In the methods and uses of the invention, the herbicide A and, if present, the herbicide B and/or the safener C can be applied jointly or separately.
In the methods and uses of the invention, the herbicide A and, if present, the herbicide B and/or the safener C can be applied simultaneously or in succession.
Preferably, the herbicide A and, if present, the herbicide B and/or the safener C are applied sim- ultaneously to the undesirable vegetation. In another embodiment, the herbicide A and, if pre- sent, the herbicide B and/or the safener C are provided as herbicidal composition as defined herein (e.g. a tank mixture containing the herbicide A and, if present, the herbicide B and/or the safener C) being applied to the undesirable vegetation. Thus, in some embodiments of the method of this invention, the herbicidal composition as defined herein is applied to the undesira- ble vegetation or the locus thereof with or applied to the soil or water to prevent the emergence or growth of the undesirable vegetation.
In case of separate or successive application, the order of the application of the herbicide A and, if present, the herbicide B and/or the safener C is of minor importance. It is only necessary that the herbicide A and, if present, the herbicide B and/or the safener C are applied in a time frame that allows simultaneous action of the active ingredients on the plants to be controlled and/or safened, preferably within a time frame of at most 14 days, in particular at most 7 days.
In the methods and uses of the invention, the herbicide A and, if present, the herbicide B and/or the safener C (or the herbicidal combination or composition as defined herein) can be applied pre-emergence (i.e. before the emergence of undesirable vegetation) or post-emergence (i.e., during and/or after emergence of the undesirable vegetation).
In one embodiment, the herbicide A and, if present, the herbicide B and/or the safener C (or the herbicidal combination or composition as defined herein) are/is applied before the emergence of the undesirable vegetation (pre-emergence).
In another embodiment, the herbicide A and, if present, the herbicide B and/or the safener C (or the herbicidal combination or composition as defined herein) are/is applied before or during the emergence of the undesirable vegetation (pre-emergence or early-post emergence).
In another embodiment, the herbicide A and, if present, the herbicide B and/or the safener C (or the herbicidal combination or composition as defined herein) are/is applied after emergence of the undesirable vegetation. In case of post-emergence treatment, the herbicide A and, if present, the herbicide B and/or the safener C (or the herbicidal combination or composition as defined herein) are/is preferably ap- plied after the undesirable vegetation has emerged and has developed up to 6 leaves.
The methods, uses, herbicidal combinations and compositions according to the invention are suitable for controlling undesirable vegetation in various crop plants. Examples of suitable crops are the following:
Allium cepa (onions) , Allium sativum (garlic), Ananas comosus (pineapples), Arachis hypogaea [peanuts (groundnuts)], Asparagus officinalis (asparagus), Avena sativa (oat), Beta vulgaris spec altissima (sugar beet), Beta vulgaris spec rapa (turnips), Brassica napus var. napus (rapeseed, canola), Brassica napus var. napobrassica (swedes), Brassica rapa var. silvestris (winter turnip rape), Brassica oleracea (cabbage), Brassica nigra (black mustard), Camellia sinensis (tea plants), Carthamus tinctorius (safflower), Carya illinoinensis (pecan trees), Citrus limon (lemons), Citrus sinensis (orange trees), Coffea arabica (Coffea canephora, Coffea li- berica) (coffee plants), Cucumis sativus (cucumber), Cynodon dactylon (Bermudagrass), Dau- cus carotasubspec. sativa (carrot), Elaeis guineensis (oil palms), Fragaria vesca (strawberries), Glycine max (soybeans), Gossypium hirsutum (Gossypium arboreum, Gossypium herbaceum, Gossypium vitifolium), Helianthus annuus (sunflowers), Hevea brasiliensis (rubber plants), Hordeum vulgare (barley), Humulus lupulus (hops), Ipomoea batatas (sweet potatoes), Juglans regia (walnut trees), Lens culinaris (lentil), Linum usitatissimum (flax), Lycopersicon lycopersi- cum (tomatoes), Malus spec (apple trees), Manihot esculenta (cassava), Medicago sativa [al- falfa (lucerne)], Musa spec (banana plants), Nicotiana tabacum (N.rustica) (tobacco), Olea eu- ropaea (olive trees), Oryza sativa (rice), Phaseolus lunatus (limabeans), Phaseolus vulgaris (snapbeans, green beans, dry beans), Picea abies (Norway spruce), Pinus spec (pine trees), Pistacia vera (pistachio), Pisum sativum (English peas), Prunus avium (cherry trees), Prunus persica (peach trees), Pyrus communis (pear trees), Prunus armeniaca (apricot), Prunus cerasus (sour cherry), Prunus dulcis (almond trees) and prunus domestica (plum trees), Ribes sylvestre (redcurrants), Ricinus communis (castor-oil plants), Saccharum officinarum (sugar cane), Secale cereale (rye), Sinapis alba, Solanum tuberosum (Irish potatoes), Sorghum bicolor (s. vulgare) (sorghum), Theobroma cacao (cacao plants), Trifolium pratense (red clover), T riti- cum aestivum (wheat), Triticale (triticale), Triticum durum (durum wheat, hard wheat), Vicia faba (tick beans), Vitis vinifera (grapes), Zea mays (Indian corn, sweet corn, maize).
Preferred crops are Allium cepa, Allium sativum, Arachis hypogaea, Avena sativa, Beta vulgaris spec altissima, Brassica napus var. napus, Brassica oleracea, Cynodon dactylon, Daucus carota subspec. Sativa, Glycine max, Gossypium hirsutum, (Gossypium arboreum, Gossypium herbaceum, Gossypium vitifolium), Helianthus annuus, Hordeum vulgare, Lens culinaris, Linum usitatissimum, Lycopersicon lycopersicum, Malus spec., Medicago sativa, Oryza sativa, Phaseolus lunatus, Phaseolus vulgaris, Pisum sativum, Saccharum officinarum, Secale cereale, Solanum tuberosum, Sorghum bicolor (s. vulgare), Triticale, Triticum aestivum, Triticum durum, Vicia faba, Vitis vinifera and Zea mays.
In a preferred embodiment, the crop plant is selected from the group consisting of cereals, corn (maize), sunflower, rice, soybeans, peas, Vicia-beans, Phaseolus-beans, peanuts, oilseed rape, canola, cotton, potato, sugarbeet, sugarcane, turfgrasses and vegetables, in particular selected from the group consisting of wheat, barley, rye, triticale, oat, corn (maize), sunflower, rice, soybeans, peas, Vicia-beans, Phaseolus-beans, peanuts, oilseed rape, canola, cotton, potato, sugarbeet, sugarcane, turfgrasses and vegetables.
In an even more preferred embodiment, the crop plant is selected from the group consisting of cereals, corn (maize), sunflower, rice, soybeans, peas, beans, peanuts, oilseed rape, canola, cotton, potato, sugarbeet, sugarcane, turfgrasses and vegetables, in particular selected from the group consisting of wheat, barley, rye, triticale, oat, corn (maize), sunflower, rice, soybeans, peas, beans, peanuts, oilseed rape, canola, cotton, potato, sugarbeet, sugarcane, turfgrasses and vegetables.
In an especially preferred embodiment, the undesirable vegetation is controlled in cereals. In particular, the cereals are selected from the group consisting of wheat, barley, rye, oat, and triticale.
The methods, uses, herbicidal combinations and compositions according to the invention are also suitable for controlling undesirable vegetation in crops which have been modified by muta- genesis or genetic engineering in order to provide a new trait to a plant or to modify an already present trait.
The term "crops" as used herein includes also (crop) plants which have been modified by muta- genesis or genetic engineering in order to provide a new trait to a plant or to modify an already present trait.
Mutagenesis includes techniques of random mutagenesis using X-rays or mutagenic chemicals, but also techniques of targeted mutagenesis, in order to create mutations at a specific locus of a plant genome. Targeted mutagenesis techniques frequently use oligonucleotides or proteins like CRISPR/Cas, zinc-finger nucleases, TALENs or meganucleases to achieve the targeting effect.
Genetic engineering usually uses recombinant DNA techniques to create modifications in a plant genome which under natural circumstances cannot readily be obtained by cross breeding, mutagenesis or natural recombination. Typically, one or more genes are integrated into the ge- nome of a plant in order to add a trait or improve a trait. These integrated genes are also re- ferred to as transgenes in the art, while plant comprising such transgenes are referred to as transgenic plants. The process of plant transformation usually produces several transformation events, wich differ in the genomic locus in which a transgene has been integrated. Plants corn- prising a specific transgene on a specific genomic locus are usually described as comprising a specific“event”, which is referred to by a specific event name. Traits which have been intro- duced in plants or hae been modified include in particular herbicide tolerance, insect resistance, increased yield and tolerance to abiotic conditions, like drought. Herbicide tolerance has been created by using mutagenesis as well as using genetic engineer- ing. Plants which have been rendered tolerant to acetolactate synthase (ALS) inhibitor herbi- cides by conventional methods of mutagenesis and breeding comprise plant varieties commer- cially available under the name Clearfield®. However, most of the herbicide tolerance traits have been created via the use of transgenes.
Herbicide tolerance has been created to glyphosate, glufosinate, 2,4-D, dicamba, oxynil herbi- cides, like bromoxynil and ioxynil, sulfonylurea herbicides, ALS inhibitor herbicides and 4-hy- droxyphenylpyruvate dioxygenase (HPPD) inhibitors, like isoxaflutole and mesotrione.
Transgenes wich have been used to provide herbicide tolerance traits comprise: for tolerance to glyphosate: cp4 epsps, epsps grg23ace5, mepsps, 2mepsps, gat4601 , gat4621 and goxv247, for tolerance to glufosinate: pat and bar, for tolerance to 2,4-D: aad-1 and aad-12, for tolerance to dicamba: dmo, for tolerance to oxynil herbicies: bxn, for tolerance to sulfonylurea herbicides: zm-hra, csr1-2, gm-hra, S4-HrA, for tolerance to ALS inhibitor herbicides: csr1-2, for tolerance to HPPD inhibitor herbicides: hppdPF, W336 and avhppd-03.
Transgenic corn events comprising herbicide tolerance genes are for example, but not exclud- ing others, DAS40278, MON801 , MON802, MON809, MON810, MON832, MON87411 , MON87419, MON87427, MON88017, MON89034, NK603, GA21 , MZHG0JG, HCEM485, VCO- 01981-5, 676, 678, 680, 33121 , 41 14, 59122, 98140, Bt10, Bt176, CBH-351 , DBT418, DLL25, MS3, MS6, MZIR098, T25, TC1507 and TC6275.
Transgenic soybean events comprising herbicide tolerance genes are for example, but not ex- cluding others, GTS 40-3-2, MON87705, MON87708, MON87712, MON87769, MON89788, A2704-12, A2704-21 , A5547-127, A5547-35, DP356043, DAS44406-6, DAS68416-4, DAS- 81419-2, GU262, SYHT0H2, W62, W98, FG72 and CV127.
Transgenic cotton events comprising herbicide tolerance genes are for example, but not exclud- ing others, 19-51a, 31707, 42317, 81910, 281-24-236, 3006-210-23, BXN10211 , BXN10215, BXN 10222, BXN 10224, MON1445, MON1698, MON88701 , MON88913, GHB119, GHB614, LLCotton25, T303-3 and T304-40.
Transgenic canola events comprising herbicide tolerance genes are for example, but not ex- cluding others, MON88302, HCR-1 , HCN10, HCN28, HCN92, MS1 , MS8, PHY14, PHY23, PHY35, PHY36, RF1 , RF2 and RF3.
Insect resistance has mainly been created by transferring bacterial genes for insecticidal pro- teins to plants. Transgenes which have most frequently been used are toxin genes of Bacillus spec and synthetic variants thereof, like cry1A, crylAb, cry1Ab-Ac, crylAc, cry1A.105, cry1 F, cry1 Fa2, cry2Ab2, cry2Ae, mcry3A, ecry3.1Ab, cry3Bb1 , cry34Ab1 , cry35Ab1 , cry9C, vip3A(a), vip3Aa20. However, also genes of plant origin have been transferred to other plants. In particu- lar genes coding for protease inhibitors, like CpTI and pinll. A further approach uses transgenes in order to produce double stranded RNA in plants to target and downregulate insect genes. An example for such a transgene is dvsnf7.
Transgenic corn events comprising genes for insecticidal proteins or double stranded RNA are for example, but not excluding others, Bt10, Bt1 1 , Bt176, MON801 , MON802, MON809, MON810, MON863, MON8741 1 , MON88017, MON89034, 33121 , 41 14, 5307, 59122, TC1507, TC6275, CBH-351 , MIR162, DBT418 and MZIR098.
Transgenic soybean events comprising genes for insecticidal proteins are for example, but not excluding others, MON87701 , MON87751 and DAS-81419.
Transgenic cotton events comprising genes for insecticidal proteins are for example, but not ex- cluding others, SGK321 , MON531 , MON757, MON1076, MON15985, 31707, 31803, 31807, 31808, 42317, BN LA-601 , Eventl , COT67B, COT102, T303-3, T304-40, GFM Cry1A, GK12, MLS 9124, 281-24-236, 3006-210-23, GHB119 and SGK321.
Increased yield has been created by increasing ear biomass using the transgene athb17, being present in corn event MON87403, or by enhancing photosynthesis using the transgene bbx32, being present in the soybean event MON87712.
Crops comprising a modified oil content have been created by using the transgenes: gm-fad2-1 , Pj.D6D, Nc.Fad3, fad2-1A and fatb1-A. Soybean events comprising at least one of these genes are: 260-05, MON87705 and MON87769.
Tolerance to abiotic conditions, in particular to tolerance to drought, has been created by using the transgene cspB, comprised by the corn event MON87460 and by using the transgene Hahb- 4, comprised by soybean event IND-00410-5.
Traits are frequently combined by combining genes in a transformation event or by combining different events during the breeding process. Preferred combination of traits are herbicide toler- ance to different groups of herbicides, insect tolerance to different kind of insects, in particular tolerance to lepidopteran and coleopteran insects, herbicide tolerance with one or several types of insect resistance, herbicide tolerance with increased yield as well as a combination of herbi- cide tolerance and tolerance to abiotic conditions.
Plants comprising singular or stacked traits as well as the genes and events providing these traits are well known in the art. For example, detailed information as to the mutagenized or inte- grated genes and the respective events are available from websites of the organizations“Inter- national Service for the Acquisition of Agri-biotech Applications (ISAAA)”
(http://www.isaaa.org/gmapprovaldatabase) and the“Center for Environmental Risk Assess- ment (CERA)” (http://cera-gmc.org/GMCropDatabase), as well as in patent applications, like EP3028573 and WO2017/01 1288.
The methods, uses, herbicidal combinations and compositions according to the invention may result in effects which are specific to a crop comprising a certain gene or event. These effects might involve changes in growth behavior or changed resistance to biotic or abiotic stress fac- tors. Such effects may in particular comprise enhanced yield, enhanced resistance or tolerance to insects, nematodes, fungal, bacterial, mycoplasma, viral or viroid pathogens as well as early vigour, early or delayed ripening, cold or heat tolerance as well as changed amino acid or fatty acid spectrum or content.
Furthermore, plants are also covered that contain by the use of recombinant DNA techniques a modified amount of ingredients or new ingredients, specifically to improve raw material produc- tion, e.g., potatoes that produce increased amounts of amylopectin (e.g. Amflora® potato, BASF SE, Germany). Furthermore, it has been found that the methods, uses, herbicidal combinations and composi- tions according to the invention are also suitable for the defoliation and/or desiccation of plant parts, for which crop plants such as cotton, potato, oilseed rape, sunflower, soybean or field beans, in particular cotton, are suitable. In particular, the methods, uses, herbicidal combina- tions and compositions according to the invention are suitable for desiccating the above-ground parts of crop plants such as potato, oilseed rape, sunflower and soybean, but also cereals. This makes possible the fully mechanical harvesting of these important crop plants.
Also of economic interest is the facilitation of harvesting, which is made possible by concentrat- ing within a certain period of time the dehiscence, or reduction of adhesion to the tree, in citrus fruit, olives and other species and varieties of pomaceous fruit, stone fruit and nuts. The same mechanism, i.e. the promotion of the development of abscission tissue between fruit part or leaf part and shoot part of the plants is also essential for the controlled defoliation of useful plants, in particular cotton.
Moreover, a shortening of the time interval in which the individual cotton plants mature leads to an increased fiber quality after harvesting.
The following examples serve to illustrate the invention.
Examples
I. Control of resistant weed biotypes
The herbicidal activity of herbicide A ((5/?S)-5-[(2,6-difluorobenzyloxy)methyl]-4,5-dihydro-5-me- thyl-3-(3-methyl-2-thienyl)-1 ,2-oxazole of the formula I, also designated herein as“methiozolin”) on resistant weed biotypes was demonstrated by the following greenhouse experiments:
The culture containers used were plastic flowerpots containing loamy sand with approximately 3.0% of humus as the substrate. The seeds of the test plants were sown separately for each species. Various blackgrass (ALOMY), annual bluegrass (POAAN) and ryegrass (LOLSS) bio- types (with varying degrees of resistance towards a range of modes of action according to the HRAC (Herbicide Resistance Action Committee) classification on mode of action 2010 (see e.g http://www.hracglobal.com/pages/classificationofherbicidesiteofaction.aspx) were tested along- side non-resistant blackgrass, bluegrass and ryegrass biotypes (see Tables 1 to 4 below).
For the pre-emergence treatment, the active ingredients, which had been suspended or emulsified in water, were applied directly after sowing by means of finely distributing nozzles. The containers were irrigated gently to promote germination and growth and subsequently covered with transparent plastic hoods until the plants had rooted. This cover caused uniform germination of the test plants, unless this had been impaired by the active ingredients.
For the post-emergence treatment, the test plants were first grown to a height of 3 to 15 cm, depending on the plant habit, and only then treated with the active ingredients which have been suspended or emulsified in water. For this purpose, the test plants were either sown directly and grown in the same containers, or they were first grown separately as seedlings and transplanted into the test containers a few days prior to treatment.
Depending on the species, the plants were kept at 10-25°C or 20-35°C. The test period extended over 2 to 4 weeks. During this time, the plants were tended, and their response to the individual treatments was evaluated. Herbicide A (methiozolin) was used as a SC formulation, having an active ingredient concentra- tion of 250 g/l.
Evaluation of the herbicidal activity was carried out using a scale from 0 to 100. 100 means complete destruction of at least the aerial moieties, and 0 means no damage, or normal course of growth. A good herbicidal activity is given at values of at least 70 and a very good herbicidal activity is given at values of at least 85.
Pre-emergence treatments were assessed at 41 days after treatment (DAT). Post-emergence treatments were assessed at 20 days after treatment (DAT).
Table 1 : Herbicidal activity of methiozolin applied pre-emergence on blackgrass (ALOMY) and ryegrass (LOLMU) biotypes
Figure imgf000053_0001
Table 2: Herbicidal activity of methiozolin applied pre-emergence on annual bluegrass (POAAN) biotypes
Figure imgf000054_0001
Table 3: Herbicidal activity of methiozolin applied pre-emergence on blackgrass (ALOMY) bio- types
Figure imgf000054_0002
Table 4: Herbicidal activity of methiozolin applied post-emergence on ryegrass (LOLMU) bio- types
Figure imgf000054_0003
As can be seen from the data in Tables 1 to 4, herbicide A (methiozolin) exhibits good to very good herbicidal activities against various biotypes of blackgrass (ALOMY), annual bluegrass (POAAN) and ryegrass (LOLMU) with varying degrees of resistance towards a range of modes of action according to the HRAC (Herbicide Resistance Action Committee) classification on mode of action 2010.
II. Synergistic interaction of herbicides A and B
The effect of herbicidal combinations according to the invention of herbicide A ((5/?S)-5-[(2,6- difluorobenzyloxy)methyl]-4,5-dihydro-5-methyl-3-(3-methyl-2-thienyl)-1 ,2-oxazole of the formula I, also designated herein as“methiozolin”) and various herbicides B (i.e tri-allate, saflufenacil, diflufenican, picolinafen, pendimethalin, trifluralin, flufenacet and pyroxasulfone) on the growth of undesirable plants compared to the herbicidally active compounds alone was demonstrated by the following greenhouse experiments:
The test plants were seeded, separately for each species, in plastic containers in sandy loamy soil containing 5% of organic matter.
For the pre-emergence treatment, the active compounds, suspended or emulsified in water, were applied directly after sowing by means of finely distributing nozzles. The containers were irrigated gently to promote germination and growth and subsequently covered with transparent plastic hoods until the plants have rooted. This cover causes uniform germination of the test plants unless this is adversely affected by the active compounds.
For the post emergence treatment, the plants were first grown to the 2-leaf stage (GS 12). Here, the herbicidal compositions were suspended or emulsified in water as distribution medium and sprayed using finely distributing nozzels.
The plants were cultivated due to their individual requirements at 10 - 25°C and 20 - 35°C. The plants were irrigated due to their necessity.
Herbicide A (methiozolin) was used as a SC formulation, having an active ingredient concentra- tion of 250 g/l.
Tri-Allate was used as CS formulation having an active ingredient concentration of 450 g/l. Saflufenacil was used as SC formulation having an active ingredient concentration of 342 g/l. Diflufenican was used as SC formulation having an active ingredient concentration of 500 g/l. Picolinafen was used as WG formulation having an active ingredient concentration of 75 %.
Pendimethalin was used as CS formulation having an active ingredient concentration of 400 g/l. Trifluralin was used as EC formulation having an active ingredient concentration of 480 g/l.
Flufenacet was used as SC formulation having an active ingredient concentration of 500 g/l.
Pyroxasulfone was used as WG formulation having an active ingredient concentration of 85 %
The herbicidal activity for the individual herbicidal compositions (solo and mixture applications) was assessed at 20 days after treatment (DAT).
The evaluation for the damage on undesired weeds caused by the chemical compositions was carried out using a scale from 0 to 100%, compared to the untreated control plants. Here, 0 means no damage and 100 means complete destruction of the plants.
The plants used in the greenhouse experiments were selected from the following species:
Figure imgf000056_0001
Colby's equation can be applied to determine whether the combination of herbicide A and herbi- cide B shows a synergistic effect (see S. R. Colby, "Calculating synergistic and antagonistic re- sponses of herbicide combinations", Weeds 1967, 15, pp. 20-22).
E = X + Y - (CΎ/100) where X = effect in percent using herbicide A at an application rate a;
Y = effect in percent using herbicide B at application rate b;
E = expected effect (in %) of herbicide A + herbicide B at application rates a + b.
The value E corresponds to the effect (plant damage or injury) which is to be expected if the ac- tivity of the individual compounds is additive. If the observed effect is higher than the value E calculated according to the Colby equation, a synergistic effect is present.
Tables 5 to 18 below relate to the herbicidal activity, in greenhouse trials, of the individual ac- tives and the combinations applied at different rates and ratios, in pre- and post-emergence ap- plications at 20 days after treatment (DAT).
Table 5: Preemergence application of herbicide A (methiozolin) and herbicide B (tri-allate)
Figure imgf000057_0001
Table 6: Postemergence application of herbicide A (methiozolin) and herbicide B (tri-allate)
Figure imgf000057_0002
Table 7: Postemergence application of herbicide A (methiozolin) and herbicide B (saflufenacil)
Figure imgf000058_0001
Table 8: Preemergence application of herbicide A (methiozolin) and herbicide B (diflufenican)
Figure imgf000058_0002
Table 9: Postemergence application of herbicide A (methiozolin) and herbicide B (diflufenican)
Figure imgf000058_0003
Figure imgf000059_0001
Table 10: Postemergence application of herbicide A (methiozolin) and herbicide B (picolinafen)
Figure imgf000059_0002
Table 11 : Preemergence application of herbicide A (methiozolin) and herbicide B (pendime- thalin)
Figure imgf000060_0001
Table 12: Postemergence application of herbicide A (methiozolin) and herbicide B (pendime- thalin)
Figure imgf000060_0002
Table 13: Preemergence application of herbicide A (methiozolin) and herbicide B (trifluralin)
Figure imgf000060_0003
Figure imgf000061_0001
Table 14: Postemergence application of herbicide A (methiozolin) and herbicide B (trifluralin)
Figure imgf000061_0002
Table 15: Preemergence application of herbicide A (methiozolin) and herbicide B (flufenacet)
Figure imgf000061_0003
Figure imgf000062_0001
Table 16: Postemergence application of herbicide A (methiozolin) and herbicide B (flufenacet)
Figure imgf000062_0002
Table 17: Preemergence application of herbicide A (methiozolin) and herbicide B (pyroxasul- fone)
Figure imgf000063_0001
Table 18: Postemergence application of herbicide A (methiozolin) and herbicide B (pyroxasul- fone)
Figure imgf000063_0002
As can be seen from the data in Tables 5 to 18, the combination of herbicide A (methiozolin) and various herbicdes B (i.e tri-allate, saflufenacil, diflufenican, picolinafen, pendimethalin, triflu- ralin, flufenacet and pyroxasulfone) exhibits an unexpected synergistic effect in that the herbi- cidal activity against various weed species in a pre- and/or post-emergence treatment is signifi cantly higher than would be predicted based on the values for each of the compounds individu- ally.

Claims

Claims
1. Use of (5/?S)-5-[(2,6-difluorobenzyloxy)methyl]-4,5-dihydro-5-methyl-3-(3-methyl-2- thienyl)-1 ,2-oxazole of the formula I
Figure imgf000064_0001
any of its individual enantiomers or any non-racemic mixture thereof (herbicide A) for controlling herbicide resistant or tolerant weed species.
2. A method for controlling undesirable vegetation which comprises applying to the vegeta- tion or the locus thereof or applying to the soil or water to prevent the emergence or growth of the undesirable vegetation a herbicidally effective amount of (5/?S)-5-[(2,6- difluorobenzyloxy)methyl]-4,5-dihydro-5-methyl-3-(3-methyl-2-thienyl)-1 ,2-oxazole of the formula I
Figure imgf000064_0002
any of its individual enantiomers or any non-racemic mixture thereof (herbicide A) wherein the undesirable vegetation comprises at least one herbicide resistant or tolerant weed species.
3. The use according to claim 1 or the method according to claim 2 wherein the herbicide A is (5/?S)-5-[(2,6-difluorobenzyloxy)methyl]-4,5-dihydro-5-methyl-3-(3-methyl-2-thienyl)-1 ,2- oxazole of the formula I.
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 with resistance or tolerance to at least one herbicide selected from the group consisting of acetyl CoA carboxylase
(ACCase) inhibitors (HRAC Group A), acetolactate synthase (ALS) inhibitors (HRAC Group B), photosystem II (PS II) inhibitors (HRAC Groups C1 , C2 and C3),
protoporphyrinogen oxidase (PPO) inhibitors (HRAC Group E), 4-hydroxyphenyl-pyruvate- dioxygenase (HPPD) inhibitors (HRAC Group F1), phytoene desaturase (PDS) inhibitors (HRAC Group F2), 5- enolpymvylshikimate-3-phosphate (EPSP) inhibitors (HRAC Group G), glutamine synthetase inhibitors (HRAC Group H), inhibitors of microtubuli assembly (HRAC Group K1 ), very long chain fatty acid (VLCFA) inhibitors (HRAC Group K3), Inhibitors of cell wall synthesis (HRAC Group L) and inhibitors of lipid synthesis (HRAC Group N).
5. The use according to any one of claims 1 , 3 and 4 or the method according to any one of claims 2 to 4 wherein the herbicide resistant or tolerant weed species is a biotype with resistance or tolerance to at least one herbicide selected from the group consisting of acetyl CoA carboxylase (ACCase) inhibitors (HRAC Group A), acetolactate synthase (ALS) inhibitors (HRAC Group B), photosystem II (PS II) inhibitors (HRAC Groups C1 , C2 and C3), inhibitors of microtubuli assembly (HRAC Group K1 ) and very long chain fatty acid (VLCFA) inhibitors (HRAC Group K3).
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 herbicide resistant or tolerant weed species is selected from the genera Agropyron, Alopecurus, Apera, Avena, Brachiaria, Bromus, Cynodon, Digitaria, Echinochloa, Eleusine, Ischaemum, Leptochloa, Lolium, Panicum, Phalaris, Poa, Rottboellia, Setaria, Anthemis, Amaranthus, Ambrosia, Capsella, Centaurea, Chenopodium, Commelina, Conyza, Descurainia, Galium, Kochia, Matricaria, Papaver, Raphanus, Sinapis, Sisymbrium, Stellaria and Thlaspi.
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 Alopecurus, Apera, Avena, Lolium, Phalaris, Poa, Commelina, Papaver and Raphanus.
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 genera Alopecurus and Lolium.
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 the undesirable vegetation is controlled in crop plants selected from cereals, corn (maize), sunflower, rice, soybeans, peas, Vicia-beans, Phaseolus- beans, peanuts, oilseed rape, canola, cotton, potato, sugarbeet, sugarcane, turfgrasses and vegetables.
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 the undesirable vegetation is controlled in crop plants selected from cereals.
1 1. The use or method according to claim 10 wherein the cereals are selected from wheat, barley, rye, triticale and oat.
12. The use according to any one of claims 1 and 3 to 1 1 or the method according to any one of claims 2 to 1 1 wherein the herbicide A is the only herbicidally active ingredient.
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, wherein a herbicidal combination comprising a) the herbicide A and b) at least one herbicide B different from herbicide A is used or applied.
14. The use or method according to claim 13 , wherein the herbicide B is selected from b1) lipid biosynthesis inhibitors:
ACCase inhibitors selected from alloxydim, alloxydim-sodium, butroxydim, clethodim, clodinafop, clodinafop-propargyl, cycloxydim, cyhalofop, cyhalofop-butyl, diclofop, diclo- fop-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, tralkoxydim, 4-(4'-Chloro-4-cyclopropyl-2'-fluoro[1 ,T-biphenyl]-
3-yl)-5-hydroxy-2,2,6,6-tetramethyl-2H-pyran-3(6H)-one (CAS 1312337-72-6); 4-(2',4'-Di- chloro-4-cyclopropyl[1 ,T-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 ,T-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 ,T-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 ,T-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 ,T-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 ,T-biphenyl]-3-yl)-3,6-dihydro-2,2,6,6-tetrame- thyl-2H-pyran-3-one (CAS 1312340-82-1); 5-(Acetyloxy)-4-(2\4'-dichloro-4-ethyl[1 ,1 '-bi- phenyl]-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 ,T-biphenyl]-3-yl)-5,6-dihydro-2,2,6,6-tetramethyl-5-oxo- 2H-pyran-3-yl carbonic acid methyl ester (CAS 1312337-51-1 ); 4-(2',4'-Dichloro -4-cyclo- propyl- [1 ,T-biphenyl]-3-yl)-5,6-dihydro-2,2,6,6-tetramethyl-5-oxo-2H-pyran-3-yl carbonic acid methyl ester; 4-(4'-Chloro-4-ethyl-2'-fluoro[1 ,T-biphenyl]-3-yl)-5,6-dihydro-2,2,6,6-tet- ramethyl-5-oxo-2H-pyran-3-yl carbonic acid methyl ester (CAS 1312340-83-2); 4-(2',4'- Dichloro-4-ethyl[1 ,T-biphenyl]-3-yl)-5,6-dihydro-2,2,6,6-tetramethyl-5-oxo-2H-pyran-3-yl carbonic acid methyl ester (CAS 1033760-58-5); and non ACC herbicides selected from benfuresate, butylate, cycloate, dalapon, dimepiperate, EPTC, esprocarb, ethofumesate, flupropanate, molinate, orbencarb, pebulate, prosulfocarb, TCA, thiobencarb, tiocarbazil, triallate and vernolate; b2) ALS inhibitors:
sulfonylureas selected from amidosulfuron, azimsulfuron, bensulfuron, bensulfuron-me- thyl, chlorimuron, chlorimuron-ethyl, chlorsulfuron, cinosulfuron, cyclosulfamuron, etham- etsulfuron, ethametsulfuron-methyl, ethoxysulfuron, flazasulfuron, flucetosulfuron, flupyr- sulfuron, flupyrsulfuron-methyl-sodium, foramsulfuron, halosulfuron, halosulfuron-methyl, imazosulfuron, iodosulfuron, iodosulfuron-methyl-sodium, iofensulfuron, iofensulfuron-so- dium, mesosulfuron, metazosulfuron, metsulfuron, metsulfuron-methyl, nicosulfuron, or- thosulfamuron, oxasulfuron, primisulfuron, primisulfuron-methyl, propyrisulfuron, prosulfu- ron, pyrazosulfuron, pyrazosulfuron-ethyl, rimsulfuron, sulfometuron, sulfometuron-methyl, sulfosulfuron, thifensulfuron, thifensulfuron-methyl, triasulfuron, tribenuron, tribenuron-me- thyl, trifloxysulfuron, triflusulfuron, triflusulfuron-methyl and tritosulfuron,
imidazolinones selected from imazamethabenz, imazamethabenz-methyl, imazamox, ima- zapic, imazapyr, imazaquin and imazethapyr, triazolopyrimidine herbicides and sulfonan- ilides selected from cloransulam, cloransulam-methyl, diclosulam, flumetsulam, florasu- lam, metosulam, penoxsulam, pyrimisulfan and pyroxsulam,
pyrimidinylbenzoates 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), N-(4-bromophenyl)-2-[(4,6-dimethoxy-2-pyrimidi- nyl)oxy]benzenemethanamine (CAS 420138-01-8),
sulfonylaminocarbonyl-triazolinone herbicides selected from flucarbazone, flucarbazone- sodium, propoxycarbazone, propoxycarbazone-sodium, thiencarbazone and thiencarba- zone-methyl; and triafamone; b3) photosynthesis inhibitors:
amicarbazone, inhibitors of the photosystem II selected from 1-(6-tert-butylpyrimidin-4-yl)- 2-hydroxy-4-methoxy-3-methyl-2H-pyrrol-5-one (CAS 1654744-66-7), 1-(5-tert-butylisoxa- zol-3-yl)-2-hydroxy-4-methoxy-3-methyl-2H-pyrrol-5-one (CAS 1637455-12-9), 1 -(5-tert- butylisoxazol-3-yl)-4-chloro-2-hydroxy-3-methyl-2H-pyrrol-5-one (CAS 1637453-94-1), 1- (5-tert-butyl-1-methyl-pyrazol-3-yl)-4-chloro-2-hydroxy-3-methyl-2H-pyrrol-5-one (CAS 1654057-29-0), 1 -(5-tert-butyl-1 -methyl-pyrazol-3-yl)-3-chloro-2-hydroxy-4-methyl-2H-pyr- rol-5-one (CAS 1654747-80-4), 4-hydroxy-1-methoxy-5-methyl-3-[4-(trifluoromethyl)-2- pyridyl]imidazolidin-2-one; (CAS 2023785-78-4), 4-hydroxy-1 ,5-dimethyl-3-[4-(trifluorome- thyl)-2-pyridyl]imidazolidin-2-one (CAS 2023785-79-5), 5-ethoxy-4-hydroxy-1-methyl-3-[4- (trifluoromethyl)-2-pyridyl]imidazolidin-2-one (CAS 1701416-69-4), 4-hydroxy-1-methyl-3- [4-(trifluoromethyl)-2-pyridyl]imidazolidin-2-one (CAS 1708087-22-2), 4-hydroxy-1 ,5-dime- thyl-3-[1-methyl-5-(trifluoromethyl)pyrazol-3-yl]imidazolidin-2-one (CAS 2023785-80-8), 1- (5-tert-butylisoxazol-3-yl)-4-ethoxy-5-hydroxy-3-methyl-imidazolidin-2-one (CAS 1844836- 64-1 ), triazine herbicides, including of chlorotriazine, triazinones, triazindiones, methylthio- triazines and pyridazinones selected from ametryn, atrazine, chloridazone, cyanazine, desmetryn, dimethametryn, hexazinone, metribuzin, prometon, prometryn, propazine, si- mazine, simetryn, terbumeton, terbuthylazin, terbutryn and trietazin, aryl urea selected from chlorobromuron, chlorotoluron, chloroxuron, dimefuron, diuron, fluometuron, isopro- turon, isouron, linuron, metamitron, methabenzthiazuron, metobenzuron, metoxuron, mon- olinuron, neburon, siduron, tebuthiuron and thiadiazuron, phenyl carbamates selected from desmedipham, karbutilat, phenmedipham, phenmedipham-ethyl, nitrile herbicides selected from bromofenoxim, bromoxynil and its salts and esters, ioxynil and its salts and esters, uraciles selected from bromacil, lenacil and terbacil, and bentazon and bentazon- sodium, pyridate, pyhdafol, pentanochlor and propanil and inhibitors of the photosystem I selected from diquat, diquat-dibromide, paraquat, paraquat-dichloride and paraquat- dimetilsulfate. b4) protoporphyrinogen-IX oxidase inhibitors:
acifluorfen, acifluorfen-sodium, azafenidin, bencarbazone, benzfendizone, bifenox, bu- tafenacil, carfentrazone, carfentrazone-ethyl, chlomethoxyfen, chlorphthalim, cinidon- ethyl, cyclopyranil, fluazolate, flufenpyr, flufenpyr-ethyl, flumiclorac, flumiclorac-pentyl, flumioxazin, fluoroglycofen, fluoroglycofen-ethyl, fluthiacet, fluthiacet-methyl, fomesafen, halosafen, lactofen, oxadiargyl, oxadiazon, oxyfluorfen, pentoxazone, profluazol, pyra- clonil, pyraflufen, pyraflufen-ethyl, saflufenacil, sulfentrazone, thidiazimin, tiafenacil, triflu- dimoxazin, ethyl [3-[2-chloro-4-fluoro-5-(1 -methyl-6-trifluoromethyl-2,4-dioxo-1 ,2,3,4-tetra- hydropyrimidin-3-yl)phenoxy]-2-pyridyloxy]acetate (CAS 353292-31 -6; S-3100), N-ethyl-3- (2,6-dichloro-4-trifluoromethylphenoxy)-5-methyl-1 A pyrazole-l -carboxamide (CAS 452098-92-9), N-tetrahydrofurfuryl-3-(2,6-dichloro-4-trifluoromethylphenoxy)-5-methyl-1 H- pyrazole-1 -carboxamide (CAS 915396-43-9), N-ethyl-3-(2-chloro-6-fluoro-4-trifluoro- methylphenoxy)-5-methyl-1 A pyrazole-l -carboxamide (CAS 452099-05-7), N-tetrahydro- furfuryl-3-(2-chloro-6-fluoro-4-trifluoromethylphenoxy)-5-methyl-1 A pyrazole-l -carbox- amide (CAS 452100-03-7), 3-[7-fluoro-3-oxo-4-(prop-2-ynyl)-3,4-dihydro-2H-benzo[1 ,4]ox- azin-6-yl]-1 ,5-dimethyl-6-thioxo-[1 ,3,5]triazinan-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-iso- indole-1 ,3-dione (CAS 13001 18-96-0), 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)-1 H-pyrimidine-2,4-dione (CAS 13041 13-05-0), methyl (£)-4-[2-chloro-5-[4-chloro-5-(difluoromethoxy)-1 A methyl-pyrazol- 3-yl]-4-fluoro-phenoxy]-3-methoxy-but-2-enoate (CAS 948893-00-3), and 3-[7-chloro-5- fluoro-2-(trifluoromethyl)-1 H-benzimidazol-4-yl]-1 -methyl-6-(trifluoromethyl)-1 H-pyrimidine- 2,4-dione (CAS 212754-02-4); b5) bleacher herbicides:
PDS inhibitors: beflubutamid, diflufenican, fluridone, flurochloridone, flurtamone, norflu- razon, picolinafen, and 4-(3-trifluoromethylphenoxy)-2-(4-trifluoromethylphenyl)pyrimidine (CAS 180608-33-7), HPPD inhibitors: benzobicyclon, benzofenap, bicyclopyrone, cloma- zone, fenquinotrione, isoxaflutole, mesotrione, oxotrione (CAS 1486617-21 -3), pyrasul- fotole, pyrazolynate, pyrazoxyfen, sulcotrione, tefuryltrione, tembotrione, tolpyralate, to- pramezone , bleacher, unknown target: aclonifen, amitrole, flumeturon, 2-chloro-3-methyl- sulfanyl-N-(1 -methyltetrazol-5-yl)-4-(trifluoromethyl)benzamide (CAS 1361 139-71 -0), 2- (2,4-dichlorophenyl)methyl-4,4-dimethyl-3-isoxazolidone (CAS 81777-95-9) and 2-(2,5- dichlorophenyl)methyl-4,4-dimethyl-3-isoxazolidinone (CAS 81778-66-7); b6) EPSP synthase inhibitors:
glyphosate, glyphosate-isopropylammonium, glyphosate-potassium and glyphosate-tri- mesium (sulfosate); b7) glutamine synthase inhibitors: bilanaphos (bialaphos), bilanaphos-sodium, glufosinate, glufosinate-P and glufosinate-am- monium; b8) DHP synthase inhibitors:
asulam; b9) mitosis inhibitors:
compounds of group K1 : dinitroanilines selected from benfluralin, butralin, dinitramine, ethalfluralin, fluchloralin, oryzalin, pendimethalin, prodiamine and trifluralin, phosphorami- dates selected from amiprophos, amiprophos-methyl, and butamiphos, benzoic acid herbi- cides selected from chlorthal, chlorthal-dimethyl, pyridines selected from dithiopyr and thi- azopyr, benzamides selected from propyzamide and tebutam; compounds of group K2: carbetamide, chlorpropham, flamprop, flamprop-isopropyl, flamprop-methyl, flamprop-M- isopropyl, flamprop-M-methyl and propham; b10) VLCFA inhibitors:
chloroacetamides selected from acetochlor, alachlor, amidochlor, butachlor, dimethachlor, dimethenamid, dimethenamid-P, metazachlor, metolachlor, S-metolachlor, pethoxamid, pretilachlor, propachlor, propisochlor and thenylchlor, oxyacetanilides selected from flufe- nacet and mefenacet, acetanilides selected from diphenamid, naproanilide, napropamide and napropamide-M, tetrazolinones such fentrazamide, and other herbicides selected from anilofos, cafenstrole, fenoxasulfone, ipfencarbazone, piperophos, pyroxasulfone and isoxazoline compounds of the formulae 11.1 , II.2, II.3, II.4, II.5, II.6, II.7, II.8 and II.9
Figure imgf000069_0001
11.6 11.7
Figure imgf000070_0001
b1 1 ) cellulose biosynthesis inhibitors:
chlorthiamid, dichlobenil, flupoxam, indaziflam, isoxaben, triaziflam and 1 -cyclohexyl-5- pentafluorphenyloxy-14-[1 ,2,4,6]thiatriazin-3-ylamine (CAS 175899-01 -1 ); b12) decoupler herbicides:
dinoseb, dinoterb and DNOC and its salts; b13) synthetic auxins:
2,4-D and its salts and esters selected from clacyfos, 2,4-DB and its salts and esters, ami- nocyclopyrachlor and its salts and esters, aminopyralid and its salts selected from amino- pyralid-dimethylammonium, aminopyralid-tris(2-hydroxypropyl)ammonium and its esters, benazolin, benazolin-ethyl, chloramben and its salts and esters, clomeprop, clopyralid and its salts and esters, dicamba and its salts and esters, dichlorprop and its salts and esters, dichlorprop-P and its salts and esters, flopyrauxifen, fluroxypyr, fluroxypyr-butometyl, flu- roxypyr-meptyl, halauxifen and its salts and esters (CAS 943832-60-8); MCPA and its salts and esters, MCPA-thioethyl, MCPB and its salts and esters, mecoprop and its salts and esters, mecoprop-P and its salts and esters, picloram and its salts and esters, quin- clorac, quinmerac, TBA (2,3,6) and its salts and esters, triclopyr and its salts and esters, florpyrauxifen, florpyrauxifen-benzyl (CAS 1390661 -72-9) and 4-amino-3-chloro-5-fluoro- 6-(7-fluoro-1 H-indol-6-yl)picolinic acid (CAS 1629965-65-6); b14) auxin transport inhibitors: diflufenzopyr, diflufenzopyr-sodium, naptalam and nap- talam-sodium; and b15) other herbicides: bromobutide, chlorflurenol, chlorflurenol-methyl, cumyluron, cy- clopyrimorate (CAS 499223-49-3) and its salts and esters, dalapon, dazomet, difen- zoquat, difenzoquat-metilsulfate, dimethipin, DSMA, dymron, endothal and its salts, eto- benzanid, flurenol, flurenol-butyl, flurprimidol, fosamine, fosamine-ammonium, indanofan, maleic hydrazide, mefluidide, metam, methyl azide, methyl bromide, methyl-dymron, me- thyl iodide, MSMA, oleic acid, oxaziclomefone, pelargonic acid, pyributicarb, quinoclamine and tridiphane.
15. The use or method according to claim 13 or 14, wherein the herbicide B is selected from b1 ) lipid biosynthesis inhibitors: prosulfocarb and triallate; b3) photosynthesis inhibitors: metribuzin, chlorotoluron and isoproturon; b4) protoporphyrinogen-IX oxidase inhibitors: flumioxazin, saflufenacil, sulfentrazone and trifludimoxazin; b5) bleacher herbicides: diflufenican, picolinafen, flurtamone, aclonifen and 2-(2,4-dichlo- rophenyl)methyl-4,4-dimethyl-3-isoxazolidone (CAS 81777-95-9); b9) mitosis inhibitors: pendimethalin and trifluralin; b10) VLCFA inhibitors: metolachlor, S-metolachlor, flufenacet and pyroxasulfone; b13) synthetic auxins: halauxifen and its salts and esters (CAS 943832-60-8), florpyrauxi- fen, florpyrauxifen-benzyl (CAS 1390661-72-9) and 4-amino-3-chloro-5-fluoro-6-(7-fluoro- 1 H-indol-6-yl)picolinic acid (CAS 1629965-65-6); and b15) other herbicides: indanofan and oxaziclomefone.
16. The use according to any one of claims 1 and 3 to 15 or the method according to any one of claims 2 to 15, further comprising applying at least one safener C selected from the group consisting of benoxacor, cloquintocet, cyometrinil, 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), metcamifen, 4-bromophenyl chloromethyl sulfone (BPCMS, CAS 54091-06-4) and agriculturally acceptable salts or derivatives thereof.
17. A herbicidal combination comprising a) a herbicide A which is selected from (5/?S)-5-[(2,6-difluorobenzyloxy)methyl]-4,5-dihy- dro-5-methyl-3-(3-methyl-2-thienyl)-1 ,2-oxazole of the formula I
Figure imgf000071_0001
any of its individual enantiomers or any non-racemic mixture thereof; and b) at least one herbicide B which is different from herbicide A wherein the herbicide B is selected from b1) lipid biosynthesis inhibitors: prosulfocarb and triallate; b3) photosynthesis inhibitors: metribuzin, chlorotoluron and isoproturon; b4) protoporphyrinogen-IX oxidase inhibitors: flumioxazin, saflufenacil, sulfentrazone and trifludimoxazin; b5) bleacher herbicides: diflufenican, picolinafen, flurtamone, aclonifen and 2-(2,4- dichlorophenyl)methyl-4,4-dimethyl-3-isoxazolidone (CAS 81777-95-9); b9) mitosis inhibitors: pendimethalin and trifluralin; b10) VLCFA inhibitors: metolachlor, S-metolachlor, flufenacet and pyroxasulfone; b13) synthetic auxins: halauxifen and its salts and esters (CAS 943832-60-8), florpyrauxifen, florpyrauxifen-benzyl (CAS 1390661-72-9) and 4-amino-3-chloro-5- fluoro-6-(7-fluoro-1 H-indol-6-yl)picolinic acid (CAS 1629965-65-6); and b15) other herbicides: indanofan and oxaziclomefone.
18. The herbicidal combination according to claim 17 wherein the herbicide B is selected from b1) lipid biosynthesis inhibitors: triallate; b4) protoporphyrinogen-IX oxidase inhibitors: saflufenacil; b5) bleacher herbicides: diflufenican and picolinafen; b9) mitosis inhibitors: pendimethalin and trifluralin; and b10) VLCFA inhibitors: flufenacet and pyroxasulfone.
19. The herbicidal combination according to claim 17 or 18 wherein the herbicide A is (5 RS}- 5-[(2,6-difluorobenzyloxy)methyl]-4,5-dihydro-5-methyl-3-(3-methyl-2-thienyl)-1 ,2-oxazole of the formula I.
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