AU2019290961B2 - Herbicidal combination - Google Patents
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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
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Abstract
The present invention relates to herbicidal combination comprising (a) a herbicide A which is 2-(2,4-dichlorophenyl)methyl-4,4-dimethyl-3-isoxazolidone of the formula (I) and (b) a herbicide B which is (±)-2-exo-(2-Methylbenzyloxy)-1-methyl-4-isopropyl-7-oxabicy- clo[2.2.1]heptane, any of its individual enantiomers or any non-racemic mixture thereof. The herbicidal combination may further comprise a herbicide C which is different from herbicides A and B. This invention also provides agrochemical compositions comprising said specific herbicidal combination as well as methods and uses for controlling undesirable vegetation, in particular for the protection of crops..
Description
Herbicidal combination
The present invention relates to a herbidical combination comprising 2-(2,4-dichlorophenyl)me thyl-4,4-dimethyl-3-isoxazolidone as defined herein, (b) ()-2-exo-(2-Methylbenzyloxy)-1-methyl 4-isopropyl-7-oxabicyclo[2.2.1]heptane, any of its individual enantiomers or any non-racemic mixture thereof and optionally (c) at least one herbicide C different therefrom and to composi tions comprising said specific herbicidal combination. The invention also relates to methods and uses for controlling undesirable vegetation, in particular in crops.
Background of the invention
In crop protection, it is desirable, in principle, to increase the specific activity of an active com pound and the reliability of the effect. It is particularly desirable for the crop protection product to control the harmful plants effectively, but at the same time to be compatible with the useful I5 plants in question. Also desirable is a broad spectrum of activity allowing the simultaneous con trol of harmful plants. Frequently, this cannot be achieved using a single herbicidally active com pound.
Further, cases of herbicide-resistant weeds are becoming increasingly common. These biotypes survive herbicide application at doses that usually give effective control of the species. Re sistant weed biotypes are a consequence of basic evolutionary processes. Individuals within a species that are best adapted to a particular practice are selected for and will increase in the population. Once a weed population is exposed to a herbicide to which one or more plants are naturally resistant, the herbicide kills susceptible individuals, but allows resistant individuals to survive and reproduce. With repeated herbicide use, resistant weeds that initially appear as iso lated 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.
Thus, there is also a need to develop practices for preventing, delaying or managing herbicide resistance in weeds.
US 4,405,357 describes herbicidal 3- isoxazolidinones, inter alia the compound 2-(2,4-dichloro phenyl)methyl-4,4-dimethyl-3-isoxazolidone of the formula I (see Compound of Example 22).
WO 2012/148689 describes the use of at least one 3-isoxazolidone herbicide selected from the group consisting of 2-(2,4-dichlorophenyl)methyl-4,4-dimethyl-3 -isoxazolidone and 2-(2,5-di chlorophenyl)methyl-4,4-dimethyl-3-isoxazolidone as a selective herbicide in a grass or brassica crop selected from the group consisting of corn, rice, sorghum, barley, rye, and canola.
WO 2015/127259 describes compositions and uses of at least one 3-isoxazolidinone analog herbicide selected from 2-(2,4-dichlorophenyl)methyl-4,4-dimethyl-3- isoxazolidinone ("2,4-DC") and 2-(2,5-dichlorophenyl)methyl-4,4-dimethyl-3-isoxazolidinone ("2,5-DC"), including combina tions with a second herbicide.
WO 2017/025418 describes the use of herbicidal active compound 2-(2,4-dichlorophenyl)me thyl-4,4-dimethyl-3-isoxazolidone (referred to as "compound I") as foliar herbicide, combinations comprising compound I and a method for controlling undesired weeds by applying the com pound I or combinations comprising compound I to weeds or to the area in which the weeds I5 grow after emergence of the crop.
WO 2018/041762 discloses a method of reducing crop damage characterized by treating the seed of the crop with a safener before sowing and applying 2-(2,4-dichlorophenyl)methyl-4,4 dimethyl-3-isoxazolidinone or combinations/compositions comprising thereof and optionally a safener in a pre- or post-emergence treatment.
The racemic mixture (±)-2-exo-(2-Methylbenzyloxy)-1-methyl-4-isopropyl-7-oxabicy clo[2.2.1]heptane (common name: Cinmethylin, CAS RN 87818-31-3) and its individual enantio mers including their preparation and herbicidal properties are known from EP 0 081 893 A2 (see Examples 29, 34, 35 and 62).
WO 2017/009090 describes a herbicidal composition comprising cinmethylin and pyroxasul fone.
WO 2018/172442 describes herbicidal mixtures containing i) 2-[(2,4-dichlorophenyl)methyl]-4,4 dimethyl-3-isoxazolidinone and ii) cinmethylin, herbicidal compositions containing said mixtures and the use of said mixtures and compositions in the agricultural field for controlling weeds, in ter alia herbicide-resistant weeds.
The herbicidal properties of these known herbicidal compounds and combinations with regard to the harmful plants are not always entirely satisfactory.
Thus, there is still room for improvement, for example regarding the herbicidal activity against specific harmful plants (especially in the control of resistant weed biotypes), the spectrum of harmful plants which can be controlled with the herbicides, the application rates, and the selec tivity of herbicides in and the compatibility with useful plants.
Summary of the invention
It would be advantageous to provide herbicidal combinations, which show enhanced herbicide action against undesirable harmful plants and/or have improved compatibility with the useful plants (in particular crop plants). In particular, it would be advantageous to provide herbicidal combinations, which provide weed control comparable to the individual compounds with significantly reduced application rates. It would also be advantageous to provide herbicidal combinations, which provide significantly en hanced weed control with application rates comparable to those of the individual compounds. Furthermore, it would be advantageous to provide herbicidal combinations, which maintain or improve the level of weed control, while showing less damage in the cultured crop in compari son to the individual compounds. In addition, the combinations according to the invention should have a broad spectrum of activ ity. Another advantage lies in the effective control of herbicide-resistant weed biotypes, especially in herbicide-resistant grass weeds.
These and further advantages are achieved by the herbicidal combinations, compositions, uses and methods below.
Accordingly, in one aspect of the invention, there is provided a herbicidal combination compris ing
a) a herbicide A which is 2-(2,4-dichlorophenyl)methyl-4,4-dimethyl-3-isoxazolidone of the for mula I
H 3 C
and
b) a herbicide B which is ()-2-exo-(2-Methylbenzyloxy)-1-methyl-4-isopropyl-7-oxabicy clo[2.2.1]heptane, any of its individual enantiomers or any non-racemic mixture thereof.
The herbicide A, i.e. 2-(2,4-dichlorophenyl)methyl-4,4-dimethyl-3-isoxazolidone of the formula I, is a known herbicidal active compound (CAS RN 17777-95-9) and may be prepared by pro cesses such as those described in US 4,405,357 (see in particular Example 22).
The herbicide B includes the racemic mixture ()-2-exo-(2-Methylbenzyloxy)-1-methyl-4-isopro pyl-7-oxabicyclo[2.2.1]heptane (herein also referred to as the "exo-(±)- isomers", CAS RN 87818-31-3) any of its individual enantiomers or any non-racemic mixture thereof. The racemic mixture con tains equal parts of the two enantiomers (+)-2-exo-(2-Methylbenzyloxy)-1-methyl-4-isopropyl-7 oxabicyclo[2.2.1]heptane (herein also referred to as the "exo-(+)- isomer" , CAS RN 87818-61 9) and (-)-2-exo-(2-Methylbenzyloxy)-1-methyl-4-isopropyl-7-oxabicyclo[2.2.1]heptane (herein also referred to as the "exo-(-)- isomer", CAS RN 87819-60-1). The exo-(±)-isomers, the exo-(+)-isomer and the exo-(-)-isomer including their preparation and herbicidal properties are disclosed in EP 0 081 893 A2 (see Examples 29, 34, 35 and 62). Further preparation methods of these compounds are described in US 4,487,945 (see Embodiments 46 and 48). The race mic mixture (±)-2-exo-(2-Methylbenzyloxy)-1-methyl-4-isopropyl-7-oxabicyclo[2.2.1]heptane is also described in the The Pesticide Manual, Fourteenth Edition, Editor: C.D.S. Tomlin, British Crop Production Council, 2006, entry 157, pages 195-196 with its common name cinmethylin, its IUPAC name (1RS,2SR,4SR)-1,4-epoxy-p-menth-2-yl2-methylbenzyl ether and its Chemical Abstracts name exo-()-1-methyl-4-(1-methylethyl)-2-[(2-methylphenyl)methoxy]-7-oxabicy I5 clo[2.2.1]heptane.
In a preferred embodiment, the herbicide B is ()-2-exo-(2-Methylbenzyloxy)-1-methyl-4-isopro pyl-7-oxabicyclo[2.2.1]heptane. In another embodiment, the herbicide B is (+)-2-exo-(2-Methylbenzyloxy)-1-methyl-4-isopropyl 7-oxabicyclo[2.2.1]heptane. In another embodiment, the herbicide B is (-)-2-exo-(2-Methylbenzyloxy)-1-methyl-4-isopropyl-7 oxabicyclo[2.2.1]heptane. In another embodiment, herbicide B is a non-racemic mixture of (+)-2-exo-(2-Methylbenzyloxy) 1-methyl-4-isopropyl-7-oxabicyclo[2.2.1]heptane and (-)-2-exo-(2-Methylbenzyloxy)-1-methyl-4 isopropyl-7-oxabicyclo[2.2.1]heptane. The non-racemic mixture contains unequal parts of the exo-(+)-isomer and the exo-(-)-isomer. The weight ratio of the exo-(+)-isomer to the exo-(-)-iso mer in the non-racemic mixture can vary widely.
The herbicidal combination of the invention may further comprise at least one herbicide C (as defined hereinafter) which is different from the herbicides A and B.
The herbicidal combination of the invention may further comprise at least one safener D (as de fined hereinafter).
In another aspect, the present invention provides an agrochemical composition comprising a herbicidally effective amount of the herbicidal combination as defined herein and one or more auxiliaries customary in crop protection (as defined hereinafter).
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 composi tion according to the invention used.
In another aspect, the present invention relates to the use of the herbicidal combination or the agrochemical composition as defined herein for controlling undesirable vegetation.
The terms "plants" and "vegetation", as used herein, include germinant seeds, emerging seed lings, plants emerging from vegetative propagules, and established vegetation.
The terms "controlling" and "combating", as used herein, are synonyms. I5 The terms "undesirable vegetation", "harmful plants", "unwanted plants", "weeds" and "weed species", as used herein, are synonyms.
In another aspect, the present invention relates to a method for controlling undesirable vegeta tion which comprises applying to the vegetation or the locus thereof or applying to the soil or water to prevent the emergence or growth of the undesirable vegetation the herbicidal combina tion or the agrochemical composition as defined herein.
The term "locus", as used herein, means the area in which the vegetation or plants are growing or will grow, typically a field.
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 combination of (a) herbicide A and (b) herbicide B is ca pable of providing a synergistic herbicidal effect.
Thus, in the herbicidal combinations, compositions, uses and methods 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 combination can, based on the individual components, be used at lower application rates to achieve a herbicidal effect comparable to the individual components.
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 - (X-Y/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.
For three-way combinations (herbicide A + herbicide B + herbicide C) a modified Colby equation I5 can be used: E = X + Y + Z - [(X-Y+X-Z + Y-Z) /100] - X-Y-Z/10000 where E, X and Y are as defined above and Z is the herbicidal effect in percent using a herbi cide C (as defined herein) at an application rate c.
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 combinations, compositions, uses and methods disclosed herein are synergistic as determined by the Colby equation. Specifically, the synergistic herbicidal effect is determined according to the Colby equation.
Moreover, the herbicidal combinations, compositions, uses and methods of the present inven tion provide excellent pre- and post-emergence control of weeds. In particular, the herbicidal combinations, compositions and methods are useful for controlling undesirable vegetation be fore their emergence (pre-emergence).
The herbicidal combinations, compositions, uses and methods of the present invention also show good crop compatibility, i.e. the combined application of (a) herbicide A and (b) herbicide B in crops does not result in increased damage of the crop plants when compared to the individ ual application of herbicide A or herbicide B.
Furthermore, the herbicidal combinations, compositions, uses and methods of the present in vention provide effective control of herbicide resistant or tolerant weed species, in particular herbicide-resistant weed biotypes. For example, the herbicidal combinations, compositions, uses and methods of the present invention can effectively control herbicide-resistant grass 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). The herbicidal combinations, compositions, uses and methods of the present invention are also suitable for controlling herbicide-resistant broadleaf weeds such as, for exam ple, Papaver rhoeas (PAPRH, corn poppy) or Raphanus raphanistrum (RAPRA) or which have evolved resistance, especially against EPSP synthase-, ALS-, ACCase- or VLCFA-inhibiting herbicides.
In addition, the herbicidal combinations, compositions, uses and methods of the present inven tion can effectively control weed biotypes with target-site resistance but also weed biotypes with non-target site resistance. A particular advantage is that the herbicidal combinations, composi tions, uses and methods of the present invention also provide effective control of weed biotypes having both target-site resistance and non-target-site resistance, such as e.g. resistant popula tions of Alopecurus myosuroides (ALOMY) or Lolium rigidum (LOLRI) or Raphanus raphan istrum (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).
In one embodiment of herbicidal combinations of this invention, the herbicide A and herbicide B (in particular (±)-2-exo-(2-Methylbenzyloxy)-1-methyl-4-isopropyl-7-oxabicyclo[2.2.1]heptane) are the only herbicidally active ingredients.
In another embodiment, the herbicidal combination of this invention further comprises c) at least one herbicide C which is different from herbicides A and B.
Thus, in one embodiment, the herbicidal combination of the present invention comprises
(a) a herbicide A which is 2-(2,4-dichlorophenyl)methyl-4,4-dimethyl-3-isoxazolidone of the for mula I 0
H 3C N(I H3 C C CI
(b) a herbicide B which is ()-2-exo-(2-Methylbenzyloxy)-1-methyl-4-isopropyl-7-oxabicy clo[2.2.1]heptane, any of its individual enantiomers or any non-racemic mixture thereof and
(c) at least one herbicide C which is different from herbicides A and B.
The herbicide C may be selected from the groups c1) to c15): c1) lipid biosynthesis inhibitors; c2) acetolactate synthase inhibitors (ALS inhibitors); c3) photosynthesis inhibitors; c4) protoporphyrinogen-IX oxidase inhibitors, c5) bleacher herbicides; c6) enolpyruvyl shikimate 3-phosphate synthase inhibitors (EPSP inhibitors); c7) glutamine synthetase inhibitors; c8) 7,8-dihydropteroate synthase inhibitors (DHP inhibitors); c9) mitosis inhibitors; c10) inhibitors of the synthesis of very long chain fatty acids (VLCFA inhibitors); cl1) cellulose biosynthesis inhibitors; c12) decoupler herbicides; c13) synthetic auxins; c14) auxin transport inhibitors; and c15) 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, flam prop, flamprop-isopropyl, flamprop-methyl, flamprop-M-isopropyl, flamprop-M-me thyl, flurenol, flurenol-butyl, flurprimidol, fosamine, fosamine-ammonium, inda nofan, indaziflam, maleic hydrazide, mefluidide, metam, methiozolin (CAS 403640-27-7), methyl azide, methyl bromide, methyl-dymron, methyl iodide, MSMA, oleic acid, oxaziclomefone, pelargonic acid, pyributicarb, quinoclamine, triaziflam, tridiphane and 6-chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazino (CAS 499223-49-3) and its salts and esters; and agriculturally acceptable salts or derivatives thereof.
In another embodiment, the herbicidal combinations of this invention compise at least one herbi cide C selected from inhibitors of the lipid biosynthesis (group c1). These are compounds that inhibit lipid biosynthesis. Inhibition of the lipid biosynthesis can be affected either through inhibi tion of acetylCoA carboxylase (hereinafter termed ACC herbicides) or through a different mode of action (hereinafter termed non-ACC herbicides). The ACC herbicides belong to the group A of the HRAC classification system whereas the non-ACC herbicides belong to the group N of the HRAC classification.
In another embodiment, the herbicidal combinations of this invention compise at least one herbi cide C selected from ALS inhibitors (group c2). The herbicidal activity of these compounds is based on the inhibition of acetolactate synthase and thus on the inhibition of the branched chain amino acid biosynthesis. These inhibitors belong to the group B of the HRAC classification sys tem.
In another embodiment, the herbicidal combinations of this invention compise at least one herbi cide C selected from inhibitors of photosynthesis (group c3). The herbicidal activity of these compounds is based either on the inhibition of the photosystem II in plants (so-called PSll inhib itors, groups C1, C2 and C3 of HRAC classification) or on diverting the electron transfer in pho tosystem I in plants (so-called PSI inhibitors, group D of HRAC classification) and thus on an in hibition of photosynthesis. Amongst these, PSll inhibitors are preferred.
In another embodiment, the herbicidal combinations of this invention compise at least one herbi cide C selected from inhibitors of protoporphyrinogen-IX-oxidase (group c4). The herbicidal ac tivity of these compounds is based on the inhibition of the protoporphyrinogen-IX-oxidase. These inhibitors belong to the group E of the HRAC classification system.
In another embodiment, the herbicidal combinations of this invention compise at least one herbi cide C selected from bleacher herbicides (group c5). The herbicidal activity of these compounds is based on the inhibition of the carotenoid biosynthesis. These include compounds which inhibit carotenoid biosynthesis by inhibition of phytoene desaturase (so-called PDS inhibitors, group F1 of HRAC classification), compounds that inhibit the 4-hydroxyphenylpyruvate-dioxygenase (HPPD inhibitors, group F2 of HRAC classification), compounds that inhibit DOXsynthase (group F4 of HRAC class) and compounds which inhibit carotenoid biosynthesis by an unknown mode of action (bleacher - unknown target, group F3 of HRAC classification).
In another embodiment, the herbicidal combinations of this invention compise at least one herbi cide C selected from EPSP synthase inhibitors (group c6). The herbicidal activity of these com pounds is based on the inhibition of enolpyruvyl shikimate 3-phosphate synthase, and thus on the inhibition of the amino acid biosynthesis in plants. These inhibitors belong to the group G of the HRAC classification system.
In another embodiment, the herbicidal combinations of this invention compise at least one herbi cide C selected from glutamine synthetase inhibitors (group c7). The herbicidal activity of these compounds is based on the inhibition of glutamine synthetase, and thus on the inhibition of the aminoacid biosynthesis in plants. These inhibitors belong to the group H of the HRAC classifica tion system.
In another embodiment, the herbicidal combinations of this invention compise at least one herbi cide C selected from DHP synthase inhibitors (group c8). The herbicidal activity of these com pounds is based on the inhibition of 7,8-dihydropteroate synthase. These inhibitors belong to the group I of the HRAC classification system.
In another embodiment, the herbicidal combinations of this invention compise at least one herbi cide C selected from mitosis inhibitors (group c9). The herbicidal activity of these compounds is based on the disturbance or inhibition of microtubule formation or organization, and thus on the inhibition of mitosis. These inhibitors belong to the groups K1 and K2 of the HRAC classification system. Among these, compounds of the group K1, in particular dinitroanilines, are preferred.
In another embodiment, the herbicidal combinations of this invention compise at least one herbi cide C selected from VLCFA inhibitors (group c10). The herbicidal activity of these compounds is based on the inhibition of the synthesis of very long chain fatty acids and thus on the disturb ance or inhibition of cell division in plants. These inhibitors belong to the group K3 of the HRAC classification system.
In another embodiment, the herbicidal combinations of this invention compise at least one herbi cide C selected from cellulose biosynthesis inhibitors (group ci1). The herbicidal activity of these compounds is based on the inhibition of the biosynthesis of cellulose and thus on the inhi bition of the synthesis of cell walls in plants. These inhibitors belong to the group L of the HRAC classification system.
In another embodiment, the herbicidal combinations of this invention compise at least one herbi cide C selected from decoupler herbicides (group c12). The herbicidal activity of these com pounds is based on the disruption of the cell membrane. These inhibitors belong to the group M of the HRAC classification system. I5 In another embodiment, the herbicidal combinations of this invention compise at least one herbi cide C selected from synthetic auxins (group c13). These include compounds that mimic auxins, i.e. plant hormones, and affect the growth of the plants. These compounds belong to the group O of the HRAC classification system.
In another embodiment, the herbicidal combinations of this invention compise at least one herbi cide C selected from auxin transport inhibitors (group c14). The herbicidal activity of these com pounds is based on the inhibition of the auxin transport in plants. These compounds belong to the group P of the HRAC classification system.
As to the given mechanisms of action and classification of the active substances, see e.g. "HRAC, Classification of Herbicides According to Mode of Action", http://www.plantprotec tion.org/hrac/MOA.html).
Preference is given to those herbicidal combinations according to the present invention com prising at least one herbicide C selected from the herbicides of groups c, c2, c3, c4, c5, c6, c7, c9, c1O, c13 and c15.
Specific preference is given to those herbicidal combinations according to the present invention which comprise at least one herbicide C selected from the herbicides of groups ci, c2, c3, c4, c5, c9, c1O,c13 and c15.
In another preferred embodiment, the herbicide C is selected from
ci) 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, haoxyfop-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 I5 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-ylcarbonic acid methyl ester; 4-(4'-Chloro-4-ethyl-2'-fluoro[1,1'-biphenyl]-3-yl)-5,6-dihydro-2,2,6,6-tetramethyl-5-oxo 2H-pyran-3-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-ylcarbonic 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;
c2) 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; c3) photosynthesis inhibitors: amicarbazone, inhibitors of the photosystem || 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 I5 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.
c4) 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 1H pyrazole-1-carboxamide (CAS 452098-92-9), N-tetrahydrofurfuryl-3-(2,6-dichloro-4-trifluoro methylphenoxy)-5-methyl-1H pyrazole-1-carboxamide (CAS 915396-43-9), N-ethyl-3-(2-chloro 6-fluoro-4-trifluoromethylphenoxy)-5-methyl-1H pyrazole-1-carboxamide (CAS 452099-05-7), N-tetrahydrofurfuryl-3-(2-chloro-6-fluoro-4-trifluoromethylphenoxy)-5-methyl-1H pyrazole-1-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-2 H-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)-1H-pyrimidine-2,4-dione (CAS 1304113-05-0), methyl (E)-4-[2 chloro-5-[4-chloro-5-(difluoromethoxy)-1 /methyl-pyrazol-3-yl]-4-fluoro-phenoxy]-3-methoxy but-2-enoate (CAS 948893-00-3), and 3-[7-chloro-5-fluoro-2-(trifluoromethyl)-1H-benzimidazol 4-yl]-l-methyl-6-(trifluoromethyl)-1H-pyrimidine-2,4-dione (CAS 212754-02-4); c5) 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, amitroleflumeturon,2-chloro-3-methylsulfanyl-N-(1-methyltetrazol-5 yl)-4-(trifluoromethyl)benzamide (CAS 1361139-71-0) and 2-(2,5-dichlorophenyl)methyl-4,4-di methyl-3-isoxazolidinone (CAS 81778-66-7); c6) EPSP synthase inhibitors: glyphosate, glyphosate-isopropylammonium, glyposate-potassium and glyphosate-trimesium (sulfosate); c7) glutamine synthase inhibitors: bilanaphos (bialaphos), bilanaphos-sodium, glufosinate, glufosinate-P and glufosinate-ammo nium; c8) DHP synthase inhibitors: asulam; c9) 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; c1O) 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 formulae11.1,ll.2, 11.3, 11.4, 11.5, 11.6, 11.7, 11.8 and 11.9
F3C N F3C N F O O N-CH 3 O O N-OH 3
HC OCHF HOC OCHF H3C O-N 2 H3C 0 -N F 2
11.1 11.2
F30 N F 30 N F 30 N F NCH3 O/0 -CH O OCH3 H3 C N HO N H3 0 S N H3O 0 N H3 0 O-N F HO 0 -N
11.3 11.4 11.5 F3 C F3 0 N N-CH3 N-CH
F F OCHF2 3 F FN
11.6 II.7
F 3C N F3C N F 0\O0 N-OH F O0 N-CH H 3C H3 NN-OH H3C F F H3 HC o-NN F F OCHF 2 H3 0 -N
11.8 11.9
cl1) 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);
c12) decoupler herbicides: dinoseb, dinoterb and DNOC and its salts;
c13) 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-1H-indol-6-yl)picolinic acid (CAS 1629965-65-6); c14) auxin transport inhibitors: diflufenzopyr, diflufenzopyr-sodium, naptalam and naptalam-so dium; c15) 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, methiozolin (CAS 403640-27-7), 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
c1) lipid biosynthesis inhibitors: prosulfocarb and triallate;
c2) ALS inhibitors: imazamox;
c3) photosynthesis inhibitors: metribuzin, terbuthylazin, chlorotoluron and isoproturon;
c4) protoporphyrinogen-IX oxidase inhibitors: flumioxazin, saflufenacil, sulfentrazone and triflu dimoxazin;
c5) bleacher herbicides: diflufenican, picolinafen, flurtamone, aclonifen and clomazone;
c6) EPSP synthase inhibitors: glyphosate, glyphosate-isopropylammonium, glyphosate-potas sium and glyphosate-trimesium (sulfosate);
c7) glutamine synthase inhibitors: glufosinate, glufosinate-P and glufosinate-ammonium;
c9) mitosis inhibitors: pendimethalin and trifluralin;
c10) VLCFA inhibitors: acetochlor, dimethachlor, dimethenamid, dimethenamid-P, metazachlor, metolachlor, S-metolachlor, pethoxamid, pretilachlor, flufenacet, napropamide, napropamide-M and pyroxasulfone;
c13) synthetic auxins: aminopyralid and its salts selected from aminopyralid-dimethylammo nium, aminopyralid-tris(2-hydroxypropyl)ammonium and its esters, halauxifen and its salts and esters (CAS 943832-60-8), quinclorac, quinmerac, florpyrauxifen, florpyrauxifen-benzyl (CAS 1390661-72-9) and 4-amino-3-chloro-5-fluoro-6-(7-fluoro-1H-indol-6-yl)picolinic acid (CAS 1629965-65-6); c15) other herbicides: indanofan, methiozolin (CAS 403640-27-7) and oxaziclomefone.
Even more preferably, the herbicide B is selected from
c1) lipid biosynthesis inhibitors: prosulfocarb and triallate;
c2) ALS inhibitors: imazamox;
c3) photosynthesis inhibitors: metribuzin, terbuthylazin, chlorotoluron and isoproturon;
I5 c4) protoporphyrinogen-IX oxidase inhibitors: flumioxazin, saflufenacil, sulfentrazone and triflu dimoxazin;
c5) bleacher herbicides: diflufenican, picolinafen, flurtamone, aclonifen and clomazone;
c9) mitosis inhibitors: pendimethalin and trifluralin;
c10) VLCFA inhibitors: acetochlor, dimethachlor, dimethenamid, dimethenamid-P, metazachlor, metolachlor, S-metolachlor, pethoxamid, pretilachlor, flufenacet, napropamide, napropamide-M and pyroxasulfone;
c13) synthetic auxins: aminopyralid and its salts selected from aminopyralid-dimethylammo nium, aminopyralid-tris(2-hydroxypropyl)ammonium and its esters, halauxifen and its salts and esters (CAS 943832-60-8), quinclorac, quinmerac, florpyrauxifen, florpyrauxifen-benzyl (CAS 1390661-72-9) and 4-amino-3-chloro-5-fluoro-6-(7-fluoro-1H-indol-6-yl)picolinic acid (CAS 1629965-65-6);
c15) other herbicides: indanofan, methiozolin (CAS 403640-27-7) and oxaziclomefone.
In another embodiment, the herbicide C is selected from prosulfocarb and triallate.
In another embodiment, the herbicide C is prosulfocarb.
In another embodiment, the herbicide C is triallate.
In another embodiment, the herbicide C is imazamox.
In another embodiment, the herbicide C is selected from metribuzin, terbuthylazin, chlorotoluron and isoproturon.
In another embodiment, the herbicide C ismetribuzin.
In another embodiment, the herbicide C is terbuthylazin.
In another embodiment, the herbicide C ischiorotoluron.
In another embodiment, the herbicide Cis isoproturon.
In another embodiment, the herbicide C is selected from flumioxazin, saflufenacil, sulfentrazone and trifludimoxazin.
In another embodiment, the herbicide C is flumioxazin.
In another embodiment, the herbicide C is saflufenacil. I5 In another embodiment, the herbicide C is sulfentrazone.
In another embodiment, the herbicide C is trifludimoxazin.
In another embodiment, the herbicide C is selected from diflufenican, picolinafen, flurtamone, aclonifen and clomazone.
In another embodiment, the herbicide C is diflufenican.
In another embodiment, the herbicide C is picolinafen.
In another embodiment, the herbicide C is flurtamone.
In another embodiment, the herbicide C is aclonifen.
In another embodiment, the herbicide C is clomazone.
In another embodiment, the herbicide C is selected from glyphosate, glyphosate-isoprop ylammonium, glyphosate-potassium and glyphosate-trimesium (sulfosate).
In another embodiment, the herbicide C is selected from glufosinate, glufosinate-P and glufosinate-ammonium.
In another embodiment, the herbicide C is selected from pendimethalin and trifluralin.
In another embodiment, the herbicide C is pendimethalin.
In another embodiment, the herbicide C is trifluralin.
In another embodiment, the herbicide C is selected from acetochlor, dimethachlor, dimethena mid, dimethenamid-P, metazachlor, metolachlor, S-metolachlor, pethoxamid, pretilachlor, flufe nacet, napropamide, napropamide-M and pyroxasulfone (preferably from flufenacet and pyrox asulfone).
In another embodiment, the herbicide C is acetochlor.
In another embodiment, the herbicide C is dimethachlor.
In another embodiment, the herbicide C is dimethenamid or dimethenamid-P, preferably dime thenamid-P.
In another embodiment, the herbicide C is metazachlor.
I5 In another embodiment, the herbicide C is metolachlor or S-metolachlor, preferably S-metolachlor.
In another embodiment, the herbicide C is pethoxamid. In another embodiment, the herbicide C is pretilachlor. In another embodiment, the herbicide C is flufenacet. In another embodiment, the herbicide C is napropamide or napropamide-M, preferably napropa mide-M.
Most preferably, the herbicide C is pyroxasulfone.
In another embodiment, the herbicide C is selected from aminopyralid and its salts and esters, halauxifen (CAS 943832-60-8) and its salts and esters, quinclorac, quinmerac, florpyrauxifen, florpyrauxifen-benzyl (CAS 1390661-72-9) and 4-amino-3-chloro-5-fluoro-6-(7-fluoro-1 H-indol-6 yl)picolinic acide (CAS 1629965-65-6).
In another embodiment, the herbicide C is selected from aminopyralid and its salts and esters, preferably from aminopyralid, aminopyralid-dimethylammonium and aminopyralid-tris(2-hydroxy propyl)ammonium.
In another embodiment, the herbicide C is selected from halauxifen (CAS 943832-60-8) and its salts and esters.
In another embodiment, the herbicide C is quinclorac. In another embodiment, the herbicide C is quinmerac. In another embodiment, the herbicide C is florpyrauxifen. In another embodiment, the herbicide C is florpyrauxifen-benzyl. In another embodiment, the herbicide C is 4-amino-3-chloro-5-fluoro-6-(7-fluoro-1H-indol-6 yl)picolinic acide (CAS 1629965-65-6).
In another embodiment, the herbicide C is selected from indanofan, methiozolin (CAS 403640 27-7) and oxaziclomefone.
In another embodiment, the herbicide C is indanofan. In another embodiment, the herbicide C is methiozolin. In another embodiment, the herbicide C is oxaziclomefone.
In an especially preferred embodiment, the herbicidal combination of this invention comprises (more particulary consists of)
(a) a herbicide A which is 2-(2,4-dichlorophenyl)methyl-4,4-dimethyl-3-isoxazolidone of the for mula I,
(b) a herbicide B which is ()-2-exo-(2-Methylbenzyloxy)-1-methyl-4-isopropyl-7-oxabicy I5 clo[2.2.1]heptane, any of its individual enantiomers or any non-racemic mixture thereof (in particular (±)-2-exo-(2-Methylbenzyloxy)-1-methyl-4-isopropyl-7-oxabicyclo[2.2.1]heptane (cinmethylin)) and
(c) a herbicide C which is pyroxasulfone.
In another especially preferred embodiment, the herbicidal combination of this invention com prises
(a) a herbicide A which is 2-(2,4-dichlorophenyl)methyl-4,4-dimethyl-3-isoxazolidone of the for mula 1,
(b) a herbicide B which is ()-2-exo-(2-Methylbenzyloxy)-1-methyl-4-isopropyl-7-oxabicy clo[2.2.1]heptane, any of its individual enantiomers or any non-racemic mixture thereof (in particular (±)-2-exo-(2-Methylbenzyloxy)-1-methyl-4-isopropyl-7-oxabicyclo[2.2.1]heptane (cinmethylin)) and
(c) a herbicide C which is pyroxasulfone
wherein the herbicide A, the herbicide B (in particular ()-2-exo-(2-Methylbenzyloxy)-1-methyl-4 isopropyl-7-oxabicyclo[2.2.1]heptane) and the herbicide C are the only herbicidally active ingre dients.
Pyroxasulfone is the common name of the herbicidal compound with the IUPAC name 3-[5 (difluoromethoxy)-1-methyl-3-(trifluoromethyl)pyrazol-4-ylmethylsulfonyl]-4,5-dihydro-5,5-dime thyl-1,2-oxazole and the Chemical Abstracts name 3-[[[5-(difluoromethoxy)-1-methyl-3-(trifluoro methyl)-1H-pyrazol-4-yl]methyl]sulfonyl]-4,5-dihydro-5,5-dimethylisoxazole (CAS RN 447399 55-5) that is described in the The e-Pesticide Manual, Version 5.2, British Crop Production Council, 2008-2011, entry 752.
In addition to the herbicide A, herbicide B and the optional herbicide C, the herbicidal combina tions of the invention may further comprise at least one safener D.
Therefore, in one embodiment, the herbicidal combinations of the invention comprise
(a) a herbicide A which is 2-(2,4-dichlorophenyl)methyl-4,4-dimethyl-3-isoxazolidone of the for mula I,
(b) a herbicide B which is ()-2-exo-(2-Methylbenzyloxy)-1-methyl-4-isopropyl-7-oxabicy clo[2.2.1]heptane, any of its individual enantiomers or any non-racemic mixture thereof (in particular (±)-2-exo-(2-Methylbenzyloxy)-1-methyl-4-isopropyl-7-oxabicyclo[2.2.1]heptane (cinmethylin)),
(d) at least one safener D. I5 In another embodiment, the herbicidal combinations of the invention comprise
(a) a herbicide A which is 2-(2,4-dichlorophenyl)methyl-4,4-dimethyl-3-isoxazolidone of the for mula I,
(b) a herbicide B which is ()-2-exo-(2-Methylbenzyloxy)-1-methyl-4-isopropyl-7-oxabicy clo[2.2.1]heptane, any of its individual enantiomers or any non-racemic mixture thereof (in particular (±)-2-exo-(2-Methylbenzyloxy)-1-methyl-4-isopropyl-7-oxabicyclo[2.2.1]heptane (cinmethylin)),
(c) at least one herbicide C which is different from the hercides A and B (in particular pyrox asulfone) and
(d) at least one safener D.
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-1H-1,2,4-triazol-3 carboxylic acids, 1-phenyl-4,5-dihydro-5-alkyl-1H-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 D 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 31-4), metcamifen, 4-bromophenyl chloromethyl sulfone (BPCMS, CAS 54091-06-4) and agri culturally acceptable salts or derivatives thereof.
More preferably, the safener D 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 I5 phenyl chloromethyl sulfone (BPCMS, CAS 54091-06-4) and agriculturally acceptable salts or derivatives thereof.
Especially preferred safeners D 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 D 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 C and safeners D are known herbicides and safeners, see, for example, The Pesticide Manual, British Crop Protection Council, 16thedition, 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-Trimethyl-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 C and/or safeners D as described herein are capable of forming geometrical isomers, for example E/Z isomers, it is possible to use both, the pure isomers and mixtures thereof, in the methods and uses according to the invention.
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 and uses according to the invention.
If the herbicides C and/or safeners D 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. I5 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 byC 1 -C 4-alkyl, hydroxy-C 1 -C 4-alkyl, C1 -C 4 alkoxy-C 1-C 4-alkyl, hydroxy-C 1-C 4-alkoxy-C 1-C 4-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(C1 -C 4-alkyl)sulfonium, such as trimethylsulfonium, and sulfoxonium ions, preferably tri(C1 -C 4-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 anionsof C1 -C 4 -al kanoic acids, preferably formate, acetate, propionate and butyrate.
The herbicides C and/or safeners D as described herein having a carboxyl, hydroxy and/or an amino group can be employed in the form of the acid, in the form of an agriculturally suitable salt as mentioned above or else in the form of an agriculturally acceptable derivative, for exam ple as amides, such as mono- and di-C1 -C6-alkylamides or arylamides, as esters, for example as allyl esters, propargyl esters, C-Cio-alkyl esters, alkoxyalkyl esters, tefuryl ((tetrahydrofuran 2-yl)methyl) esters and also as thioesters, for example as C-Cio-alkylthio esters. Preferred mono- and di-C1 -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. PreferredC1 -C 4-alkoxy-C 1 -C 4-alky esters are the straight-chain or branched C1 -C 4-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 C-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 dicamba-butotyl. Suitable salts of 2,4-D are 2,4-D-ammonium, 2,4-D-dimethylammonium, 2,4-D-diethylammo nium, 2,4-D-diethanolammonium (2,4-D-diolamine), 2,4-D-triethanolammonium, 2,4-D-isoprop I5 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 ple 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-dimethylammonium, aminopyra lid-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 the herbicidal combinations of the present invention the weight ratio of herbicide A to herbi cide B (in particular ()-2-exo-(2-Methylbenzyloxy)-1-methyl-4-isopropyl-7-oxabicyclo[2.2.1]hep tane (cinmethylin)) is in general in the range from 1:0.05 to 1:20, preferably in the range from 1:0.1 to 1:15, more preferably in the range from 1:0.1 to 1:10, even more preferably in the range from 1:0.1 to 1:8 and in particular in the range from 1:0.2 to 1:5. In another embodiment, the weight ratio of herbicide A to herbicide B (in particular ()-2-exo-(2-Methylbenzyloxy)-1-methyl 4-isopropyl-7-oxabicyclo[2.2.1]heptane (cinmethylin)) is in the range from 1:0.1 to 1:2, prefera bly in the range from 1:0.1 to 1:1 and in particular in the range from 1:0.125 to 1:1.
The weight ratio of herbicide A to herbicide C is in general in the range from 1:0.002 to 1:160, preferably in the range from 1:0.003 to 1:107 and in particular in the range from 1:0.004 to 1:80.
The weight ratio of herbicide A to herbicide C which is pyroxasulfone is in general in the range from 1:0.01 to 1:15, preferably in the range from 1:0.02 to 1:6, more preferably in the range from 1:0.05 to 1:5, even more preferably in the range from 1:0.05 to 1:4 and in particular in the range from 1:0.05 to 1:3.
The weight ratio of herbicide B (in particular ()-2-exo-(2-Methylbenzyloxy)-1-methyl-4-isopro pyl-7-oxabicyclo[2.2.1]heptane (cinmethylin)) to herbicide C is in the range from 1:0.002 to 1:160, preferably in the range from 1:0.003 to 1:107 and in particular in the range from 1:0.004 to 1:80.
I5 The weight ratio of herbicide B (in particular ()-2-exo-(2-Methylbenzyloxy)-1-methyl-4-isopro pyl-7-oxabicyclo[2.2.1]heptane (cinmethylin)) to herbicide C which is pyroxasulfone is in general in the range from 1:0.01 to 1:15, preferably in the range from 1:0.02 to 1:6, more preferably in the range from 1:0.05 to 1:3 and in particular in the range from 1:0.1 to 1:1.
In an especially preferred embodiment, the herbicidal combination of this invention comprises (more particulary consists of)
(a) a herbicide A which is 2-(2,4-dichlorophenyl)methyl-4,4-dimethyl-3-isoxazolidone of the for mula I,
(b) a herbicide B which is ()-2-exo-(2-Methylbenzyloxy)-1-methyl-4-isopropyl-7-oxabicy clo[2.2.1]heptane, any of its individual enantiomers or any non-racemic mixture thereof (in particular (±)-2-exo-(2-Methylbenzyloxy)-1-methyl-4-isopropyl-7-oxabicyclo[2.2.1]heptane (cinmethylin)) and
(c) a herbicide C which is pyroxasulfone
wherein the weight ratio of herbicide A to herbicide B is in the range from 1:0.05 to 1:20, prefer ably in the range from 1:0.1 to 1:15, more preferably in the range from 1:0.1 to 1:10, even more preferably in the range from 1:0.1 to 1:8 and in particular in the range from 1:0.2 to 1:5, the weight ratio of herbicide A to herbicide C is in the range from 1:0.01 to 1:15, preferably in the range from 1:0.02 to 1:6, more preferably in the range from 1:0.05 to 1:5 and in particular in the range from 1:0.05 to 1:3 and the weight ratio of herbicide B to herbicide C is in the range from 1:0.01 to 1:15 preferably in the range from 1:0.02 to 1:6, more preferably in the range from 1:0.05 to 1:3 and in particular in the range from 1:0.1 to 1:1.
In another especially preferred embodiment, the herbicidal combination of this invention com prises
(a) a herbicide A which is 2-(2,4-dichlorophenyl)methyl-4,4-dimethyl-3-isoxazolidone of the for mula 1,
(b) a herbicide B which is ()-2-exo-(2-Methylbenzyloxy)-1-methyl-4-isopropyl-7-oxabicy clo[2.2.1]heptane, any of its individual enantiomers or any non-racemic mixture thereof (in particular (±)-2-exo-(2-Methylbenzyloxy)-1-methyl-4-isopropyl-7-oxabicyclo[2.2.1]heptane (cinmethylin)) and
(c) a herbicide C which is pyroxasulfone
wherein the herbicide A, the herbicide B (in particular ()-2-exo-(2-Methylbenzyloxy)-1-methyl-4 I5 isopropyl-7-oxabicyclo[2.2.1]heptane) and the herbicide C are the only herbicidally active ingre dients, the weight ratio of herbicide A to herbicide B is in the range from 1:0.05 to 1:20, preferably in the range from 1:0.1 to 1:15, more preferably in the range from 1:0.1 to 1:10, even more prefer ably in the range from 1:0.1 to 1:8 and in particular in the range from 1:0.2 to 1:5, the weight ratio of herbicide A to herbicide C is in the range from 1:0.01 to 1:15, preferably in the range from 1:0.02 to 1:6, more preferably in the range from 1:0.05 to 1:5 and in particular in the range from 1:0.05 to 1:3 and the weight ratio of herbicide B to herbicide C is in the range from 1:0.01 to 1:15 preferably in the range from 1:0.02 to 1:6, more preferably in the range from 1:0.05 to 1:3 and in particular in the range from 1:0.1 to 1:1.
The weight ratio of herbicide A to safener D is generally in the range of from 1:0.005 to 1:20, preferably in the range of from 1:0.01 to 1:7 and in particular in the range of from 1:0.04 tol:2, wherein each safener D being an ester or a salt of an acid is calculated as the acid.
The weight ratio of herbicide B (in particular ()-2-exo-(2-Methylbenzyloxy)-1-methyl-4-isopro pyl-7-oxabicyclo[2.2.1]heptane (cinmethylin)) to safener D is generally in the range of from 1:0.005 to 1:20, preferably in the range of from 1:0.01 to 1:7 and in particular in the range of from 1:0.04 to 1:2, wherein each safener D being an ester or a salt of an acid is calculated as the acid.
The weight ratio of herbicide C to safener D is generally in the range of from 1:0.0006 to 1:500, preferably in the range of from 1:0.001 to 1:250 and in particular in the range of from 1:0.003 to 1:100, wherein each herbicide C and safener D being an ester or a salt of an acid is calculated as the acid.
The weight ratio of herbicide C which is pyroxasulfone to safener D is generally in the range of from 1:0.007 to 1:100, preferably in the range of from 1:0.002 to 1:33 and in particular in the range of from 1:0.007 to 1:8, wherein each safener D being an ester or a salt of an acid is calcu lated as the acid.
The weight ratio of the combination of herbicides A and B to the safener D is generally in the range of from 1:0.003 to 1:20, preferably in the range of from 1:0.007 to 1:7 and in particular in the range of from 1:0.002 to 1:2, wherein each safener D being an ester or a salt of an acid is calculated as the acid.
The weight ratio of the combination of herbicides A, B and C to the safener D is generally in the range of from 1:0.0006 to 1:500, preferably in the range of from 1:0.003 to 1:50 and in particular in the range of from 1:0.007 to 1:10, wherein each herbicide C and safener D being an ester or a salt of an acid is calculated as the acid.
The herbicidal combinations as defined herein are suitable as herbicides as such or as appro I5 priately formulated agrochemical compositions. As used herein, the term "agrochemical compo sition" refers to a composition comprising the herbicidal combination of this invention and one or more auxiliaries customary in crop protection, in particular to a composition comprising a herbi cidally effective amount of the herbicidal combination of this invention and one or more auxilia ries customary in crop protection.
Thus, the agrochemical composition comprises the herbicidal combination of this invention and one or more auxiliaries customary in crop protection. In particular, the agrochemical composi tion comprises a herbicidally effective amount of the herbicidal combination of this invention and one or more auxiliaries customary in crop protection.
The herbicidal combination of this invention can be converted into customary types of agro chemical compositions, e. g. solutions, emulsions, suspensions, dusts, powders, pastes, gran ules, 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), capsules (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), in secticidal 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 de fined in the "Catalogue of pesticide formulation types and international coding system", Tech nical 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 I5 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 herbicidal combination or agrochemical composition of this invention onto plant propagation material, especially seeds include dressing, coating, pelleting, dusting, soaking and in-furrow application methods of the propagation material. Preferably, the herbi cides A and B, optionally at least one herbicide C and optionally at least one safener D (or the respective agrochemical composition) are applied onto the plant propagation material by a method such that germination is not induced, e. g. by seed dressing, pelleting, coating and dust ing.
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 herbicides A and B, option ally at least one herbicide C and optionally at least one safener D (or the respective agrochemi cal composition) 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 the herbicides A and B, optionally at least one herbicide C and optionally at least one safener D 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 herbicidal combination of this inven tion or partially premixed components, e. g. components comprising the herbicides A and B, op tionally at least one herbicide C and optionally at least one safener D 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 the herbicides A and B and optionally at least one herbicide C and option ally at least one safener D 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 for mulation may be provided in the form of a two, three or multi (e.g. four) package formulation, wherein one package comprises a formulation of herbicide A, the second package comprises a formulation of the herbicide B and optionally one or more further packages comprise one or more formulation(s) of the at least one herbicide C and/or the safener D, and wherein all formu lations comprise at least one carrier material, if desired, one or more surfactants and, if desired, one or more further auxiliaries customary in crop protection. In case of a two, three or multi (e.g. four) package formulation, the two or more formulations are preferably mixed prior to applica tion. Preferably, the mixing is performed as a tank mix, i.e. the formulations are mixed immedi ately prior or upon dilution with water.
The compositions of this invention can also control vegetation on non-crop areas very effi ciently, especially at high rates of application. They act against broad-leafed weeds and grass weeds in crops such as wheat, barley, rice, corn, sunflowers, soybeans and cotton without I5 causing any significant damage to the crop plants. This effect is mainly observed at low rates of application.
The compositions of this invention are applied to the plants mainly by spraying. Here, the appli cation can be carried out using, for example, water as carrier by customary spraying techniques using spray liquor amounts of from about 50 to 1000 I/ha (for example from 300 to 400 I/ha). The compositions as defined herein may also be applied by the low-volume or the ultra-low-vol ume method, or in the form of microgranules.
The herbicidal combinations or agrochemical compositions of this invention can be applied pre or post-emergence or together with the seed of a crop plant. It is also possible to apply the com binations and compositions by applying seed, pretreated with a combination or composition as defined herein, of a crop plant. If the herbicides A and B and, if appropriate, one or more herbi cides C are less well tolerated by certain crop plants, application techniques may be used in which the agrochemical 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 under neath, or the bare soil surface (post-directed, lay-by).
In a further embodiment, the herbicidal combinations or agrochemical compositions of this in vention can be applied by treating seed. The treatment of seed comprises essentially all proce dures 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 agrochemical compositions as defined 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 herbicidal combinations or agrochemical com positions of this invention on their own or jointly in combination with other crop protection agents, for example with agents for controlling pests or phytopathogenic fungi or bacteria or with groups of active compounds which regulate growth. Also of interest is the miscibility with mineral salt solutions which are employed for treating nutritional and trace element deficiencies. Non-phytotoxic oils and oil concentrates can also be added.
When employed in plant protection, the amounts of active substances applied (i.e. herbicides A and B and, if appropriate, one or more herbicides C) without formulation auxiliaries, are, de pending on the kind of effect 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, es pecially preferably from 0.005 to 2 kg/ha.
In the methods and uses of this invention, the herbicide A is generally applied in an amount of I5 from 0.1 to 2000 grams per hectare (g/ha), preferably 10 to 1000 g/ha, more preferably 10 to 750 g/ha and in particular 10 to 500 g/ha. In another embodiment, the herbicide A is applied in an amount of from 50 to 1000 g/ha, preferably 75 to 750 g/ha and more preferably 100 to 500 g/ha.
In the methods and uses of this invention, the application rate of the herbicide B is generally from 0.0005 kg/ha to 10 kg/ha, preferably from 0.005 kg/ha to 5 kg/ha and more preferably from 75 to 750 g/ha and most preferably from 100 to 500 g/ha.
In the methods and uses of this invention, the application rate of the herbicide C (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 kg/ha.
In the methods and uses of this invention, the application rate of the herbicide C which is pyroxasulfone is generally from 0.0005 kg/ha to 10 kg/ha, preferably from 0.005 kg/ha to 5 kg/ha, more preferably from 0.001 kg/ha to 2 kg/ha and even more preferably 10 g/ha to 750 g/ha.
In the methods and uses of this invention, the application rate of the safener D (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. herbicides A and B and, if appropriate, one or more herbicides C) 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. herbicides A and B and, if appropriate, one or more herbicides C) are generally em ployed 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, the herbicide B and, if present, the herbicide C and/or the safener D can be applied jointly or separately.
In the methods and uses of the invention, the herbicide A, the herbicide B and, if present, the herbicide C and/or the safener D can be applied simultaneously or in succession.
Preferably, the herbicide A, the herbicide B and, if present, the herbicide C and/or the safener D are applied simultaneously to the undesirable vegetation. In another embodiment, the herbicide A, the herbicide B and, if present, the herbicide C and/or the safener D are provided as an agro chemical composition as defined herein (e.g. a tank mixture containing the herbicide A, the I5 herbicide B and, if present, the herbicide C and/or the safener D) being applied to the undesira ble vegetation. Thus, in some embodiments of the method of this invention, the agrochemical composition as defined herein is applied to the undesirable vegetation or the locus thereof with or applied to the soil or water to prevent the emergence or growth of the undesirable vegetation.
In case of separate or successive application, the order of the application of the herbicide A, the herbicide B and, if present, the herbicide C and/or the safener D is of minor importance. It is only necessary that the herbicide A and, if present, the herbicide B and/or the safener C are ap plied 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 herbicidal combinations or agrochemical composi tions of this invention 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 vegeta tion).
In one embodiment, the herbicidal combinations or agrochemical compositions of this invention are applied before the emergence of the undesirable vegetation (pre-emergence).
In another embodiment, the herbicidal combinations or agrochemical compositions of this inven tion are applied before or during the emergence of the undesirable vegetation (pre-emergence or early-post emergence).
In another embodiment, the herbicidal combinations or agrochemical compositions of this inven tion are applied after emergence of the undesirable vegetation.
In case of post-emergence treatment, the herbicidal combinations or agrochemical composi tions of this invention are preferably applied after the undesirable vegetation has emerged and has developed up to 6 leaves.
The herbicidal combinations, agrochemical compositions, uses and methods of the present in vention are suitable for controlling a large number of undesirable vegetation (harmful plants), including monocotyledonous weeds and dicotyledonous weeds.
In one embodiment, the undesirable vegetation is selected from monocotyledonous weed spe cies. Preferably, the undesirable vegetation is selected from the family Poaceae. More prefera bly, the undesirable vegetation is selected from the tribes Aveneae, Bromeae, Paniceae and Poeae. In one embodiment, the undesirable vegetation is selected from the tribe Aveneae. In another embodiment, the undesirable vegetation is selected from the tribe Bromeae. In yet an other embodiment, the undesirable vegetation is selected from the tribe Paniceae. In still an other embodiment, the undesirable vegetation is selected from the tribe Poeae.
In particular, the herbicidal combinations, agrochemical compositions, uses and methods of the I5 present invention may be used for controlling annual weeds such as gramineous weeds (grass weeds) including, but not limited to, the genera AegilopssuchasAegilops cylindrical (AEGCY, jointed goatgrass); Agropyron such as Agropyron repens (AGRRE, common couchgrass); Alo pecurus such as Alopecurus myosuroides (ALOMY, blackgrass) or Alopecurus aequalis (ALOAE, foxtail); Apera such as Apera spica-venti (APESV, silky wind grass); Avena such as Avena fatua (AVEFA, wild oat) or Avena sterilis subsp. Sterilis (AVEST, sterile oat); Brachiaria such as Brachiaria plantaginea (BRAPL, Alexander grass) or Brachiaria decumbens (BRADC, Surinam grass); Bromus such as Bromus inermis (BROIN, awnless brome), Bromus sterilis (BROST, barren bromegrass), Bromus tectorum (BROTE, cheatgrass), Bromus arvensis (BROAV, field bromegrass), Bromus secalinus (BROSE, rye bromegrass) or Bromus hordeacus (BROMO, lopgrass); Cenchrus such as Cenchrus echinatus (CCHEC, Mossman River grass); Cynodon such as Cynodon dactylon (CYNDA, bermudagrass); Digitaria such as Digitaria ciliaris (DIGAD, southern crabgrass), Digitaria sanguinalis (DIGSA, hairy crabgrass), Digitaria insularis (TRCIN, sourgrass) or Digitaria ischaemum (DIGIS, smooth crabgrass); Echinochloa such as Echinochloa colonum (ECHCO, awnless barnyardgrass), Echinochloa crus-galli (ECHCG, com mon barnyard grass), Echinochloa crus-pavonis (ECHCV , Gulf cockspurgrass), Echinochloa oryzoides (ECHOR, early barnyardgrass) or Echinochloa phyllogogon (ECHPH, late barn yardgrass); Eleusine such as Eleusine indica (ELEIN, Indian goosegrass); Ischaemum such as Ischaemum rugusom (ISCRU, muraina grass); Leptochloa such as Leptochloa chinensis (LEFCH, Chinese sprangletop), Leptochloa fascicularis (LEFFA, salt-meadow grass), Lepto chloa filiformis (LEFPC, thread sprangletop), Leptochloa mucronata (LEFFI, red sprangletop), Leptochloa panicoides (LEFPA, tighthead sprangletop), Leptochloa scabra (LEFSC) or Lepto chloa virgata (LEFVI, tropical sprangletop); Lolium such as Lolium multiflorum (LOLMU, Italian ryegrass), Lolium perenne (LOLPE, English ryegrass) or Lolium rigidum (LOLRI, annual rye grass); Panicum such as Panicum capillare (PANCA, tumble panicgrass), Panicum dichotomi florum (PANDI, smooth witchgrass), Panicum laevifolium (PANLF, sweet panicgrass) or Pani cum miliaceum (PANMI, common millet); Phalaris such as Phalaris minor (PHAMI, lesser ca nary grass), Phalaris paradoxa (PHAPA, paradoxagrass), Phalaris canariensis (PHACA, ca narygrass) or Phalaris brachystachys (PHABR, short-spiked canarygrass); Poa such as Poa an nua (POAAN, annual bluegrass), Poa pratensis (POAPR, Kentucky bluegrass) or Poa trivialis
(POATR, rough meadowgrass); Rottboellia such as Rottboellia exaltata (ROOEX, guinea-fowl grass); Setaria auch as Setaria faberi (SETFA, giant foxtail), Setaria glauca (PESGL, pearl mil let), Setaria italic (SETIT, Italian millet), Setaria pumila (SETPU, yellow foxtail), Setaria verticil lata (SETVE, bristly foxtail) or Setaria viridis (SETVI, green foxtail); and Sorghum such as Sor ghum halepense (SORHA, Johnson grass).
Preferably, the undesirable vegetation is a monocotyledonous weed species selected from the genera Agropyron, Alopecurus, Apera, Avena, Brachiaria, Bromus, Cynodon, Digitaria, Echi nochloa, Eleusine, Ischaemum, Leptochloa, Lolium, Panicum, Phalaris, Poa, Rottboellia, Setaria and Sorghum.
More preferably, the undesirable vegetation is a monocotyledonous weed species selected from the genera Agropyron, Alopecurus, Apera, Avena, Brachiaria, Bromus, Cynodon, Digitaria, Echinochloa, Eleusine, Ischaemum, Leptochloa, Lolium, Panicum, Phalaris, Poa, Rottboellia, I5 and Setaria. Even more preferably, the undesirable vegetation is selected from the genera Alo pecurus, Apera, Avena, Digitaria, Echinochloa, Leptochloa, Lolium, Phalaris, Poa and Setaria. In particular, the undesirable vegetation is selected from the genera Alopecurus, Apera, Avena, Echinochloa, Leptochloa, Lolium, Phalaris and Poa. Most preferably, the undesirable vegetation is selected from the genera Alopecurus, Avena, Lolium and Phalaris.
In another preferred embodiment, the undesirable vegetation is a monocotyledonous weed spe cies selected from the genera Alopecurus, Avena, Brachiaria, Lolium and Setaria.
In another embodiment, the undesirable vegetation is a monocotyledonous weed species se lected from Agropyron repens, Alopecurus myosuroides, Alopecurus aequalis, Apera spica venti, Avena fatua, Avena sterilis subsp. sterilis, Brachiaria plantaginea, Brachiaria decumbens, Bromus inermis, Bromus sterilis, Bromus tectorum, Bromus arvensis, Bromus secalinus, Bro mus hordeacus, Cynodon dactylon, Digitaria ciliaris, Digitaria sanguinalis, Digitaria insularis, Digitaria ischemum, Echinochloa colona, Echinochloa crus-galli, Echinochloa crus-pavonis, Echinochloa erecta, Echinochloa oryzoides, Echinochloa phyllogogon, Eleusine indica, Ischae mum rugusom, Leptochloa chinensis, Leptochloa fascicularis, Leptochloa filliformis, Leptochloa panicoides, Leptochloa scabra, Leptochloa virgata, Lolium multiflorum, Lolium perenne, Lolium rigidum, Panicum capillare, Panicum dichotomiflorum, Panicum laevifolium, Panicum miliaceum, Phalaris minor, Phalaris paradoxa, Phalaris canariensis, Phalaris brachystachys, Poa annua, Poa pratensis, Poa trivialis, Rottboellia exaltata, Setaria faberi, Setaria glauca, Setaria italica, Setaria pumila, Setaria verticillata, Setaria viridis and Sorghum halepense.
Preferably, the undesirable vegetation is a monocotyledonous weed species selected from Ag ropyron repens, Alopecurus myosuroides, Alopecurus aequalis, Apera spica-venti, Avena fatua, Avena sterilis subsp. sterilis, Brachiaria plantaginea, Brachiaria decumbens, Bromus inermis, Bromus sterilis, Bromus tectorum, Bromus arvensis, Bromus secalinus, Bromus hordeacus, Cynodon dactylon, Digitaria ciliaris, Digitaria sanguinalis, Digitaria insularis, Digitaria ischemum, Echinochloa colona, Echinochloa crus-galli, Echinochloa crus-pavonis, Echinochloa erecta,
Echinochloa oryzoides, Echinochloa phyllogogon, Eleusine indica, Ischaemum rugusom, Lepto chloa chinensis, Leptochloa fascicularis, Leptochloa filliformis, Leptochloa panicoides, Lepto chloa scabra, Leptochloa virgata, Lolium multiflorum, Lolium perenne, Lolium rigidum, Panicum capillare, Panicum dichotomiflorum, Panicum laevifolium, Panicum miliaceum, Phalaris minor, Phalaris paradoxa, Phalaris canariensis, Phalaris brachystachys, Poa annua, Poa pratensis, Poa trivialis, Rottboellia exaltata, Setaria faberi, Setaria glauca, Setaria italica, Setaria pumila, Setaria verticillata, and Setaria viridis.
In particular, the monocotyledonous weed species is selected from Alopecurus myosuroides, Alopecurus aequalis, Apera spica-venti, Avena fatua, Avena sterilis subsp. sterilis, Echinochloa crus-galli, Echinochloa oryzoides, Leptochloa chinensis, Lolium multiflorum, Lolium perenne, Lolium rigidum, Phalaris minor, Phalaris paradoxa, Phalaris canariensis, Phalaris brachysta chys, Poa annua, Poa pratensis and Poa trivialis, more preferably from Alopecurus myosu roides, Alopecurus aequalis, Apera spica-venti, Avena fatua, Echinochloa grus-galli, Echi I5 nochloa oryzoides, Leptochloa chinensis, Lolium multiflorum, Lolium rigidum, Phalaris minor and Poa annua, and most preferably from Alopecurus myosuroides, Avena fatua, Lolium multi florum, Lolium rigidum and Phalaris minor.
In another preferred embodiment, the monocotyledonous weed species is selected from Alo pecurus myosuroides, Avena fatua, Brachiaria decumbens, Lolium multiflorum, Lolium perenne, Lolium rigidum and Setaria viridis.
The herbicidal combinations, agrochemical compositions, uses and methods of the present in vention are also suitable for controlling a large number of dicotyledonous weeds, in particular broadleaf weeds including, but not limited to, Polygonum species such as Polygonum convol volus (POLCO, wild buckwheat), Amaranthus species such as Amaranthus albus (AMAAL, tum ble pigweed), Amaranthus blitoides (AMABL, mat amaranth), Amaranthus hybridus (AMACH, green pigweed), Amaranthus palmeri (AMAPA, Palmer amaranth), Amaranthus powellii (AMAPO, Powell amaranth), Amaranthus retroflexus (AMARE, redroot pigweed), Amaranthus tuberculatus (AMATU, rough-fruit amaranth), Amaranthus rudis (AMATA, tall amaranth) or Ama ranthus viridis (AMAVI, slender amaranth), Chenopodium species such as Chenopodium album (CHEAL, common lambsquarters), Chenopodium ficifolium (CHEFI, fig-leaved goosefoot), Che nopodium polyspermum (CHEPO, many-seeded goosefoot) or Chenopodium hybridum (CHEHY, maple-leaf goosefoot), Sida species such as Sida spinosa L. (SIDSP, prickly sida), Ambrosia species such as Ambrosia artemisiifolia (AMBEL, common ragweed), Acanthosper mum species, Anthemis species such as Anthemis arvensis (ANTAR, field chamomile), Atriplex species, Cirsium species, Convolvulus species, Conyza species such as Conyza bonariensis (ERIBO, hairy horseweed) or Conyza canadensis (ERICA, Canada horseweed), Cassia spe cies, Commelina species, Datura species, Euphorbia species, Geranium species such as Ge ranium dissectum (GERDI, cut-leaf geranium), Geranium pusillium (GERPU, small-flower gera nium) or Geranium rotundifolium (GERRT, round-leaved cranesbill), Galinsoga species,Ipo moea species such as Ipomoea hederacea (IPOHE, morningglory), Lamium species, Malva species, Matricaria species such as Matricaria chamomilla (MATCH, wild chamomile), Matri caria discoidea (MATMT, pineapple weed) or Matricaria inodora (MATIN, false chamomille),
Sysimbrium species, Solanum species, Xanthium species, Veronica species, Viola species, Stellaria species such as Stellaria media (STEME, common chickweed), Abutilon theophrasti (ABUTH, velvet leaf), Hemp sesbania (Sesbania exaltata Cory, SEBEX, Colorado river hemp), Anoda cristata (ANVCR, cottonweed), Bidens pilosa (BIDPI, common blackjack), Centaurea species such as Centaurea cyanus (CENCY, cornflower), Galeopsis tetrahit (GAETE common hemp nettle), Galium aparine (GALAP, cleavers or goosegrass), Galium spurium (GALSP, false cleavers), Galium tricornutum (GALTC, corn cleavers), Helianthus annuus (HELAN, common sunflower), Desmodium tortuosum (DEDTO, giant beggar weed), Kochia scoparia (KCHSC, mock cypress), Mercurialis annua (MERAN, annual mercury), Myosotis arvensis (MY OAR, field forget-me-not), Papaver rhoeas (PAPRH, common poppy), Salsola kali (SASKA, prickly glasswort), Sonchus arvensis (SONAR, corn sowthistle), Tagetes minuta (TAGMI, Mexi can marigold), Richardia brasiliensis (RCHBR, Brazil pusley), cruciferous weeds such as Raphanus raphanistrum (RAPRA, wild radish), Sinapis alba (SINAL, white mustard), Sinapis arvensis (SINAR, wild mustard), Thlaspi arvense (THLAR, fanweed), Descurainia Sophia I5 (DESSO, flixweed), Capsella bursa-pastoris (CAPBP, shepherd's purse), Sisymbrium species such as Sisymbrium officinale (SSYOF, hedge mustard) or Sisymbrium orientale (SSYOR, ori ental mustard), Brassica kaber (SINAR wild mustard).
Preferably, the undesirable vegetation is a dicotyledonous weed species selected from the gen era Abutilon, Amaranthus, Ambrosia, Anthemis, Capsella, Centaurea, Chenopodium, Conyza, Descurainia, Galium, Geranium, Kochia, Matricaria, Papaver, Polygonum, Raphanus, Sinapis, Sisymbrium, Stellaria and Thlaspi.
More preferably, the undesirable vegetation is a dicotyledonous weed species selected from the genera Amaranthus, Ambrosia, Anthemis, Capsella, Centaurea, Chenopodium, Conyza, Des curainia, Galium, Geranium, Kochia, Matricaria, Papaver, Raphanus, Sinapis, Sisymbrium, Stel laria and Thlaspi, even more preferably from the genera Anthemis, Centaurea, Geranium, Matri caria, Papaver, Sisymbrium and Stellaria.
In another preferred embodiment, the undesirable vegetation is a dicotyledonous weed species selected from the genera Abutilon, Anthemis, Chenopodium, Galium, Geranium, Matricaria, Pa paver, Polygonum and Stellaria.
Still more preferably, the dicotyledonous weed species is selected from Abutilon theoprasti, Am aranthus albus, Amaranthus blitoides, Amaranthus hybridus, Amaranthus palmeri, Amaranthus powellii, Amaranthus retroflexus, Amaranthus tuberculatus, Amaranthus rudis, Amaranthus vi ridis, Ambrosia artemisiifolia, Anthemis arvensis, Capsella bursa-pastoris, Centaurea cyanus, Chenopodium album, Chenopodium ficifolium, Chenopodium polyspermum, Chenopodium hy bridum, Conyza bonariensis, Conyza canadensis, Descurania sophia, Galium aparine, Galium spurium, Galium tricornutum, Geranium dissectum, Geranium pusillum, Geranium rotundifolium, Kochia scoparia, Matricaria chamomilla, Matricaria discoidea, Matricaria inodora, Papaver rhoeas, Polygonum convolvulus, Raphanus raphanistrum, Sinapis alba, Sinapis arvensis, Si symbrium officinale, Sisymbrium orientale, Stellaria media and Thlaspi arvense.
In particular, the dicotyledonous weed species is selected from Amaranthus albus, Amaranthus blitoides, Amaranthus hybridus, Amaranthus palmeri, Amaranthus powellii, Amaranthus retro flexus, Amaranthus tuberculatus, Amaranthus rudis, Amaranthus viridis, Ambrosia artemisiifo lia, Anthemis arvensis, Capsella bursa-pastoris, Centaurea cyanus, Chenopodium album, Che nopodium ficifolium, Chenopodium polyspermum, Chenopodium hybridum, Conyza bonariensis, Conyza canadensis, Descurania sophia, Galium aparine, Galium spurium, Galium tricornutum, Geranium dissectum, Geranium pusillum, Geranium rotundifolium, Kochia scoparia, Matricaria chamomilla, Matricaria discoidea, Matricaria inodora, Papaver rhoeas, Raphanus raphanistrum, Sinapis alba, Sinapis arvensis, Sisymbrium officinale, Sisymbrium orientale, Stellaria media, and Thlaspi arvense. Most preferably, the dicotyledonous weed species is selected from Anthe mis arvensis, Centaurea cyanus, Geranium dissectum, Geranium pusillum, Geranium rotundifo lium Matricaria chamomilla, Matricaria inodora, Papaver rhoeas, Sisymbrium officinale and Stel laria media.
I5 In another preferred embodiment, the dicotyledonous weed species is selected from the group consisting of Abutilon theophrasti, Anthemis arvensis, Chenopodium album, Galium aparine, Geranium dissectum, Matricaria inodora, Papaver rhoeas, Polygonum convolvolus and Stellaria media.
In another embodiment, the undesirable vegetation is selected from the genera Agropyron, Alo pecurus, Apera, Avena, Brachiaria, Bromus, Cynodon, Digitaria, Echinochloa, Eleusine, Ischae mum, Leptochloa, Lolium, Panicum, Phalaris, Poa, Rottboellia, Setaria, Sorghum, Abutilon, An themis, Amaranthus, Ambrosia, Capsella, Centaurea, Chenopodium, Conyza, Descurainia, Ga lium, Geranium, Kochia, Matricaria, Papaver, Polygonum, Raphanus, Sinapis, Sisymbrium, Stel laria and Thlaspi.
Preferably, the undesirable vegetation is selected from the genera Agropyron, Alopecurus, Apera, Avena, Brachiaria, Bromus, Cynodon, Digitaria, Echinochloa, Eleusine, Ischaemum, Leptochloa, Lolium, Panicum, Phalaris, Poa, Rottboellia, Setaria, Anthemis, Amaranthus, Am brosia, Capsella, Centaurea, Chenopodium, Conyza, Descurainia, Galium, Kochia, Matricaria, Papaver, Raphanus, Sinapis, Sisymbrium, Stellaria and Thlaspi. More preferably, the undesirable vegetation is selected from the genera Alopecurus, Apera, Digitaria, Echinochloa, Leptochloa, Lolium, Phalaris, Poa, Setaria, Amaranthus, Anthemis, Capsella, Centaurea, Chenopodium, Descurania, Kochia, Matricaria, Papaver, Sisymbrium, Stellaria and Thlaspi, still more preferably selected from the genera Alopecurus, Apera, Echi nochloa, Leptochloa, Lolium, Phalaris, Poa, Amaranthus, Chenopodium, Matricaria, Papaver and Stellaria, even more preferably selected from the genera Alopecurus, Echinochloa, Lolium, Phalaris, Poa, Amaranthus, Chenopodium, Matricaria, Papaver and Stellaria, yet more prefera bly selected from the genera Alopecurus, Echinochloa, Lolium, Phalaris, Poa and Papaver and in particular selected from the genera Alopecurus, Lolium, Phalaris and Papaver.
In another preferred embodiment, the undesirable vegetation is selected from the genera Alo pecurus, Avena, Brachiaria, Lolium, Setaria, Abutilon, Anthemis, Chenopodium, Galium, Gera nium, Matricaria, Papaver, Polygonum and Stellaria.
In yet another embodiment, the undesirable vegetation is selected from the group consisting of Alopecurus myosuroides, Alopecurus aequalis, Apera spica-venti, Avena fatua, Avena sterilis, Brachiaria plantaginea, Brachiaria decumbens, Bromus secalinus, Bromus sterilis, Bromus tec torum, Digitaria ciliaris, Digitaria insularis, Digitaria ischaemum, Digitaria sanguinalis, Echi nochloa colona, Echinochloa crus-galli, Echinochloa crus-pavonis, Echinochloa erecta, Echi nochloa oryzoides, Echinochloa phyllogogon, Eleusine indica, Ischaemum rugosum, Leptochloa chinensis, Leptochloa panicoides, Leptochloa scabra, Leptochloa virgata, Lolium multiflorum, Lolium perenne, Lolium rigidum, 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, Setaria viridis, Sorghum halepense, Abutilon theoprasti, Amaranthus albus, Amaranthus blitoides, Amaranthus hybridus, Amaranthus palmeri, Amaranthus powellii, Amaranthus retroflexus, Amaranthus tu berculatus, Amaranthus rudis, Amaranthus viridis, Ambrosia artemisiifolia, Anthemis arvensis, I5 Capsella bursa-pastoris, Centaurea cyanus, Chenopodium album, Chenopodium ficifolium, Chenopodium polyspermum, Chenopodium hybridum, Conyza bonariensis, Conyza canaden sis, Descurania sophia, Galium aparine, Galium spurium, Galium tricornutum, Geranium dissec tum, Kochia scoparia, Matricaria chamomilla, Matricaria discoidea, Matricaria inodora, Papaver rhoeas, Polygonum convolvulus, Raphanus raphanistrum, Sinapis alba, Sinapis arvensis, Si symbrium officinale, Sisymbrium orientale, Stellaria media and Thlaspi arvense, preferably se lected from the group consisting of Alopecurus myosuroides, Alopecurus aequalis, Apera spica venti, Avena fatua, Avena sterilis, Brachiaria plantaginea, Brachiaria decumbens, Bromus secal inus, Bromus sterilis, Bromus tectorum, Digitaria ciliaris, Digitaria insularis, Digitaria ischaemum, Digitaria sanguinalis, Echinochloa colona, Echinochloa crus-galli, Echinochloa crus-pavonis, Echinochloa erecta, Echinochloa oryzoides, Echinochloa phyllogogon, Eleusine indica, Ischae mum rugosum, Leptochloa chinensis, Leptochloa panicoides, Leptochloa scabra, Leptochloa virgata, Lolium multiflorum, Lolium perenne, Lolium rigidum, Panicum capillare, Panicum di chotomiflorum, Phalaris brachystachyx, Phalaris minor, Phalaris 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 artemisiifolia, Anthemis arvensis, Capsella bursa-pastoris, Centaurea cyanus, Chenopodium album, Chenopodium ficifolium, Chenopodium polyspermum, Chenopodium hybridum, Conyza bonariensis, Conyza canaden sis, Descurania sophia, Galium aparine, Galium spurium, Galium tricornutum, Kochia scoparia, Matricaria chamomilla, Matricaria discoidea, Matricaria inodora, Papaver rhoeas, Raphanus raphanistrum, Sinapis alba, Sinapis arvensis, Sisymbrium officinale, Sisymbrium orientale, Stel laria media and Thlaspi arvense, more preferably selected from the group consisting of Alo pecurus myosuroides, Alopecurus aequalis, Apera spica-venti, Digitaria ischaemum, Digitaria sanguinalis, Echinochloa crus-galli, Echinochloa oryzoides, Leptochloa chinensis, Lolium multi florum, Lolium perenne, Lolium rigidum, Phalaris brachystachys, Phalaris minor, Phalaris para doxa, Poa annua, Poa trivialis, Setaria faberi, Setaria glauca, Setaria pumilla, Setaria verticil lata, Setaria viridis, Amaranthus powellii, Amaranthus retroflexus, Amaranthus tuberculatus,
Amaranthus rudis, Anthemis arvensis, Capsella bursa-pastoris, Centaurea cyanus, Chenopo dium album, Descurania sophia, Kochia scoparia, Matricaria chamomilla, Matricaria inodora, Papaver rhoeas, Sisymbrium officinale, Stellaria media and Thlaspi arvense, even more prefer ably selected from the group consisting of Alopecurus myosuroides, Alopecurus aequalis, Apera spica-venti, Echinochloa crus-galli, Echinochloa oryzoides, Leptochloa chinensis, Lolium multi florum, Lolium perenne, Lolium rigidum, Phalaris brachystachys, Phalaris minor, Phalaris para doxa, Poa annua, Amaranthus powellii, Amaranthus retroflexus, Amaranthus tuberculatus, Am aranthus rudis, Chenopodium album, Matricaria chamomilla, Matricaria inodora, Papaver rhoeas and Stellaria media, especially preferably selected from the group consisting of Alopecu rus myosuroides, Alopecurus aequalis, Apera spica-venti, Echinochloa crus-galli, Echinochloa oryzoides, Leptochloa chinensis, Lolium multiflorum, Lolium rigidum, Phalaris minor and Poa annua, and in particular selected from the group consisting of Alopecurus myosuroides, Lolium multiflorum, Lolium rigidum and Phalaris minor.
I5 In another preferred embodiment, the undesirable vegetation is selected from the species Alo pecurus aequalis, Apera spica-venti, Echinochloa crus-galli, Echinochloa oryzoides, Leptochloa chinensis, Lolium multiflorum, Lolium perenne, Phalaris brachystachys, Phalaris minor, Phalaris paradoxa, Poa annua, Amaranthus powellii, Amaranthus retroflexus, Amaranthus tuberculatus, Amaranthus rudis, Chenopodium album, Matricaria chamomilla, Matricaria inodora and Stellaria media.
In another preferred embodiment, the undesirable vegetation is selected from the group consist ing of Alopecurus myosuroides, Avena fatua, Brachiaria decumbens, Lolium multiflorum, Lolium perenne, Lolium rigidum, Setaria viridis, Abutilon theophrasti, Anthemis arvensis, Chenopodium album, Galium aparine, Geranium dissectum, Matricaria inodora, Papaver rhoeas, Polygonum convolvolus and Stellaria media.
In yet another preferred embodiment, the undesirable vegetation is selected from the genera Avena, Geranium, Lolium, Matricaria, Papaver and Stellaria (in particular from the genera Gera nium, Matricaria and Stellaria), preferably from the species Avena fatua, Geranium dissectum, Lolium multiflorum, Matricaria inodora, Papaver rhoeas and Stellaria media (more preferably from the species Geranium dissectum, Lolium multiflorum, Matricaria inodora and Stellaria me dia and in particular from the species Geranium dissectum, Matricaria inodora and Stellaria me dia).
In yet another preferred embodiment, the undesirable vegetation is selected from the genera Al opecurus, Avena, Brachiaria, Lolium, Setaria, Abutilon, Anthemis, Chenopodium, Galium, Gera nium, Matricaria, Papaver and Polygonum, preferably from the species Alopecurus myosu roides, Avena fatua, Brachiaria decumbens, Lolium multiflorum, Lolium perenne, Lolium rigidum, Setaria viridis, Abutilon theophrasti, Anthemis arvensis, Chenopodium album, Galium aparine, Geranium dissectum, Matricaria inodora and Polygonum convolvolus.
In yet another preferred embodiment, the undesirable vegetation is selected from the genera Al opecurus, Avena, and Lolium, preferably from the species Alopecurus myosuroides, Avena fatua, and Lolium multiflorum. In another embodiment, the undesirable vegetation is a herbicide resistant or tolerant weed spe cies.
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 1) inhibitors (HRAC Group D), protoporphyrinogen oxidase (PPO) inhibitors (HRAC Group E), 4-hydroxy phenyl-pyruvate-dioxygenase (HPPD) inhibitors (HRAC Group Fl), 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 I5 (HRAC Group G), glutamine synthetase inhibitors (HRAC Group H), DHP synthase inhibitors (HRAC Group 1), 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 0), 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-hydroxyphenyl-pyruvate-dioxygenase (HPPD) inhibitors (HRAC Group Fl), phytoene desaturase (PDS) inhibitors (HRAC Group F2), 5 enolpymvylshikimate-3-phosphate (EPSP) inhibitors (HRAC Group G), inhibitors of microtubuli assembly (HRAC Group K1), very long chain fatty acid (VLCFA) inhibitors (HRAC Group K3), Inhibitors of cell wall synthesis (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), 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).
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) and photosystem II (PS II) inhibitors (HRAC Groups C1, C2 and C3).
In another embodiment, the resistant or tolerant biotype is selected from the genera Agropyron, Alopecurus, Apera, Avena, Brachiaria, Bromus, Cynodon, Digitaria, Echinochloa, Eleusine, Is chaemum, Leptochloa, Lolium, Panicum, Phalaris, Poa, Rottboellia, Setaria, Sorghum, Abutilon, Anthemis, Amaranthus, Ambrosia, Capsella, Centaurea, Chenopodium, Conyza, Descurainia, Galium, Geranium, Kochia, Matricaria, Papaver, Polygonum, Raphanus, Sinapis, Sisymbrium, Stellaria and Thlaspi.
Preferably, the resistant or tolerant biotype is selected from the genera Agropyron, Alopecurus, Apera, Avena, Brachiaria, Bromus, Cynodon, Digitaria, Echinochloa, Eleusine, Ischaemum, Leptochloa, Lolium, Panicum, Phalaris, Poa, Rottboellia, Setaria, Anthemis, Amaranthus, Am brosia, Capsella, Centaurea, Chenopodium, Conyza, Descurainia, Galium, Kochia, Matricaria, Papaver, Raphanus, Sinapis, Sisymbrium, Stellaria and Thlaspi.
I5 More preferably, the resistant or tolerant biotype is selected from the genera Alopecurus, Apera, Digitaria, Echinochloa, Leptochloa, Lolium, Phalaris, Poa, Setaria, Amaranthus, Anthemis, Capsella, Centaurea, Chenopodium, Descurania, Kochia, Matricaria, Papaver, Sisymbrium, Stellaria and Thlaspi, still more preferably selected from the genera Alopecurus, Apera, Echi nochloa, Leptochloa, Lolium, Phalaris, Poa, Amaranthus, Chenopodium, Matricaria, Papaver and Stellaria, even more preferably selected from the genera Alopecurus, Echinochloa, Lolium, Phalaris, Poa, Amaranthus, Chenopodium, Matricaria, Papaver and Stellaria, yet more prefera bly selected from the genera Alopecurus, Echinochloa, Lolium, Phalaris, Poa and Papaver and in particular selected from the genera Alopecurus, Lolium, Phalaris and Papaver.
In another embodiment, the resistant or tolerant biotype is selected from the genera Alopecurus, Apera, Digitaria, Echinochloa, Leptochloa, Phalaris, Poa, Setaria, Amaranthus, Anthemis, Capsella, Centaurea, Chenopodium, Descurania, Kochia, Matricaria, Papaver, Sisymbrium, Stellaria and Thlaspi, more preferably selected from the genera Alopecurus, Apera, Echi nochloa, Leptochloa, Phalaris, Poa, Amaranthus, Chenopodium, Matricaria, Papaver and Stel laria, even more preferably selected from the genera Alopecurus, Echinochloa, Phalaris, Poa, Amaranthus, Chenopodium, Matricaria, Papaver and Stellaria, yet more preferably selected from the genera Alopecurus, Echinochloa, Phalaris, Poa and Papaver and in particular selected from the genera Alopecurus, Phalaris and Papaver.
In another embodiment, the resistant or tolerant biotype is selected from the genera Abutilon, Amaranthus, Anthemis, Avena, Chenopodium, Galium, Geranium, Lolium, Polygonum, Sor ghum and Stellaria.
In one embodiment, the resistant or tolerant biotype is a monocotyledonous weed species se lected from the genera Alopecurus, Apera, Digitaria, Echinochloa, Leptochloa, Lolium, Phalaris, Poa and Setaria, preferably selected from the genera Alopecurus, Apera, Echinochloa, Lepto chloa, Lolium, Phalaris and Poa, more preferably selected from the genera Alopecurus, Echi nochloa, Lolium, Phalaris and Poa, and in particular selected from the genera Alopecurus, Lo lium and Phalaris.
In another embodiment, the resistant or tolerant biotype is a monocotyledonous weed species, preferably a monocotyledonous weed species selected from the genera Alopecurus, Apera, Digitaria, Echinochloa, Leptochloa, Phalaris, Poa and Setaria, preferably selected from the gen era Alopecurus, Apera, Echinochloa, Leptochloa, Phalaris and Poa, more preferably selected from the genera Alopecurus, Echinochloa, Phalaris and Poa, and in particular selected from the genera Alopecurus and Phalaris.
In another embodiment, the resistant or tolerant biotype is a dicotyledonous weed species, pref erably a dicotyledonous weed species selected from the genera Amaranthus, Anthemis, Capsella, Centaurea, Chenopodium, Descurania, Kochia, Matricaria, Papaver, Sisymbrium, Stellaria and Thlaspi, more preferably selected from the genera Amaranthus, Chenopodium, Matricaria, Papaver and Stellaria and in particular selected from the genus Papaver.
I5 In another embodiment, the resistant or tolerant biotype is selected from the group consisting of Alopecurus myosuroides, Alopecurus aequalis, Apera spica-venti, Avena fatua, Avena sterilis, Brachiaria plantaginea, Brachiaria decumbens, Bromus secalinus, Bromus sterilis, Bromus tec torum, Digitaria ciliaris, Digitaria insularis, Digitaria ischaemum, Digitaria sanguinalis, Echi nochloa colona, Echinochloa crus-galli, Echinochloa crus-pavonis, Echinochloa erecta, Echi nochloa oryzoides, Echinochloa phyllogogon, Eleusine indica, Ischaemum rugosum, Leptochloa chinensis, Leptochloa panicoides, Leptochloa scabra, Leptochloa virgata, Lolium multiflorum, Lolium perenne, Lolium rigidum, 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, Setaria viridis, Sorghum halepense, Abutilon theoprasti, Amaranthus albus, Amaranthus blitoides, Amaranthus hybridus, Amaranthus palmeri, Amaranthus powellii, Amaranthus retroflexus, Amaranthus tu berculatus, Amaranthus rudis, Amaranthus viridis, Ambrosia artemisiifolia, Anthemis arvensis, Capsella bursa-pastoris, Centaurea cyanus, Chenopodium album, Chenopodium ficifolium, Chenopodium polyspermum, Chenopodium hybridum, Conyza bonariensis, Conyza canaden sis, Descurania sophia, Galium aparine, Galium spurium, Galium tricornutum, Geranium dissec tum, Kochia scoparia, Matricaria chamomilla, Matricaria discoidea, Matricaria inodora, Papaver rhoeas, Polygonum convolvulus, Raphanus raphanistrum, Sinapis alba, Sinapis arvensis, Si symbrium officinale, Sisymbrium orientale, Stellaria media and Thlaspi arvense.
In particular, the resistant or tolerant biotype is selected from the group consisting of Alopecurus myosuroides, Alopecurus aequalis, Apera spica-venti, Avena fatua, Avena sterilis, Brachiaria plantaginea, Brachiaria decumbens, Bromus secalinus, Bromus sterilis, Bromus tectorum, 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, 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, Setaria viridis, Amaranthus albus, Am aranthus blitoides, Amaranthus hybridus, Amaranthus palmeri, Amaranthus powellii, Amaran thus retroflexus, Amaranthus tuberculatus, Amaranthus rudis, Amaranthus viridis, Ambrosia ar temisiifolia, Anthemis arvensis, Capsella bursa-pastoris, Centaurea cyanus, Chenopodium al bum, Chenopodium ficifolium, Chenopodium polyspermum, Chenopodium hybridum, Conyza bonariensis, Conyza canadensis, Descurania sophia, Galium aparine, Galium spurium, Galium tricornutum, Kochia scoparia, Matricaria chamomilla, Matricaria discoidea, Matricaria inodora, Papaver 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, Digitaria ischae mum, Digitaria sanguinalis, Echinochloa crus-galli, Echinochloa oryzoides, Leptochloa chinen sis, Lolium multiflorum, Lolium perenne, Lolium rigidum, Phalaris brachystachys, Phalaris minor, Phalaris paradoxa, Poa annua, Poa trivialis, Setaria faberi, Setaria glauca, Setaria pumilla, Setaria verticillata, Setaria viridis, Amaranthus powellii, Amaranthus retroflexus, Amaranthus tu I5 berculatus, Amaranthus rudis, Anthemis arvensis, Capsella bursa-pastoris, Centaurea cyanus, Chenopodium album, Descurania sophia, Kochia scoparia, Matricaria chamomilla, Matricaria inodora, Papaver rhoeas, Sisymbrium officinale, Stellaria media and Thlaspi arvense, more preferably selected from the group consisting of Alopecurus myosuroides, Alopecurus aequalis, Apera spica-venti, Echinochloa crus-galli, Echinochloa oryzoides, Leptochloa chinensis, Lolium multiflorum, Lolium perenne, Lolium rigidum, Phalaris brachystachys, Phalaris minor, Phalaris paradoxa, Poa annua, Amaranthus powellii, Amaranthus retroflexus, Amaranthus tuberculatus, Amaranthus rudis, Chenopodium album, Matricaria chamomilla, Matricaria inodora, Papaver rhoeas and Stellaria media, especially preferably selected from the group consisting of Alopecu rus myosuroides, Alopecurus aequalis, Apera spica-venti, Echinochloa crus-galli, Echinochloa oryzoides, Leptochloa chinensis, Lolium multiflorum, Lolium rigidum, Phalaris minor and Poa annua, and in particular selected from the group consisting of Alopecurus myosuroides, Lolium multiflorum, Lolium rigidum and Phalaris minor.
In another embodiment, the resistant or tolerant biotype is selected from the group consisting of Alopecurus myosuroides, Alopecurus aequalis, Apera spica-venti, Avena fatua, Avena sterilis, Brachiaria plantaginea, Brachiaria decumbens, Bromus secalinus, Bromus sterilis, Bromus tec torum, Digitaria ciliaris, Digitaria insularis, Digitaria ischaemum, Digitaria sanguinalis, Echi nochloa colona, Echinochloa crus-galli, Echinochloa crus-pavonis, Echinochloa erecta, Echi nochloa oryzoides, Echinochloa phyllogogon, Eleusine indica, Ischaemum rugosum, Leptochloa chinensis, Leptochloa panicoides, Leptochloa scabra, Leptochloa virgata, Panicum capillare, Panicum dichotomiflorum, Phalaris brachystachyx, Phalaris minor, Phalaris paradoxa, Poa an nua, Poa pratensis, Poa trivialis, Rottboellia exaltata, Setaria faberi, Setaria glauca, Setaria pu mila, Setaria verticillata, Setaria viridis, Amaranthus albus, Amaranthus blitoides, Amaranthus hybridus, Amaranthus palmeri, Amaranthus powellii, Amaranthus retroflexus, Amaranthus tu berculatus, Amaranthus rudis, Amaranthus viridis, Ambrosia artemisiifolia, Anthemis arvensis, Capsella bursa-pastoris, Centaurea cyanus, Chenopodium album, Chenopodium ficifolium, Chenopodium polyspermum, Chenopodium hybridum, Conyza bonariensis, Conyza canaden sis, Descurania sophia, Galium aparine, Galium spurium, Galium tricornutum, Kochia scoparia, Matricaria chamomilla, Matricaria discoidea, Matricaria inodora, Papaver rhoeas, Raphanus raphanistrum, Sinapis alba, Sinapis arvensis, Sisymbrium officinale, Sisymbrium orientale, Stel laria media and Thlaspi arvense, preferably selected from the group consisting of Alopecurus myosuroides, Alopecurus aequalis, Apera spica-venti, Digitaria ischaemum, Digitaria sangui nalis, Echinochloa crus-galli, Echinochloa oryzoides, Leptochloa chinensis, Phalaris brachysta chys, Phalaris minor, Phalaris paradoxa, Poa annua, Poa trivialis, Setaria faberi, Setaria glauca, Setaria pumilla, Setaria verticillata, Setaria viridis, Amaranthus powellii, Amaranthus retroflexus, Amaranthus tuberculatus, Amaranthus rudis, Anthemis arvensis, Capsella bursa-pastoris, Cen taurea cyanus, Chenopodium album, Descurania sophia, Kochia scoparia, Matricaria chamo milla, Matricaria inodora, Papaver rhoeas, Sisymbrium officinale, Stellaria media and Thlaspi arvense, more preferably selected from the group consisting of Alopecurus myosuroides, Alo pecurus aequalis, Apera spica-venti, Echinochloa crus-galli, Echinochloa oryzoides, Leptochloa chinensis, Phalaris brachystachys, Phalaris minor, Phalaris paradoxa, Poa annua, Amaranthus powellii, Amaranthus retroflexus, Amaranthus tuberculatus, Amaranthus rudis, Chenopodium album, Matricaria chamomilla, Matricaria inodora, Papaver rhoeas and Stellaria media, espe I5 cially preferably selected from the group consisting of Alopecurus myosuroides, Alopecurus aequalis, Apera spica-venti, Echinochloa crus-galli, Echinochloa oryzoides, Leptochloa chinen sis, Phalaris minor and Poa annua, and in particular Alopecurus myosuroides or Phalaris mi nor.
In another embodiment, the resistant or tolerant biotype is selected from the group consisting of Avena fatua, Lolium multiflorum, Sorghum halepense, Abutilon theoprasti, Amaranthus retro flexus, Anthemis arvensis, Chenopodium album, Galium aparine, Geranium dissectum, Polygo num convolvulus and Stellaria media.
In one embodiment, the resistant or tolerant biotype is a monocotyledonous weed species se lected from the group consisting of Alopecurus myosuroides, Alopecurus aequalis, Apera spica venti, Digitaria ischaemum, Digitaria sanguinalis, Echinochloa crus-galli, Echinochloa oryzoides, Leptochloa chinensis, Lolium multiflorum, Lolium perenne, Lolium rigidum, Phalaris brachysta chys, Phalaris minor, Phalaris paradoxa, Poa annua, Poa trivialis, Setaria faberi, Setaria glauca, Setaria pumilla, Setaria verticillata and Setaria viridis, preferably selected from the group con sisting of Alopecurus myosuroides, Alopecurus aequalis, Apera spica-venti, Echinochloa crus galli, Echinochloa oryzoides, Leptochloa chinensis, Lolium multiflorum, Lolium perenne, Lolium rigidum, Phalaris brachystachys, Phalaris minor, Phalaris paradoxa and Poa annua, more pref erably selected from the group consisting of Alopecurus myosuroides, Alopecurus aequalis, Apera spica-venti, Echinochloa crus-galli, Echinochloa oryzoides, Leptochloa chinensis, Lolium multiflorum, Lolium rigidum, Phalaris minor and Poa annua and in particular selected from the group consisting of Alopecurus myosuroides, Lolium multiflorum, Lolium rigidum and Phalaris minor.
In another embodiment, the resistant or tolerant biotype is a dicotyledonous weed species se lected from the group consisting of Amaranthus powellii, Amaranthus retroflexus, Amaranthus tuberculatus, Amaranthus rudis, Anthemis arvensis, Capsella bursa-pastoris, Centaurea cy anus, Chenopodium album, Descurania sophia, Kochia scoparia, Matricaria chamomilla, Matri- caria inodora, Papaver rhoeas, Sisymbrium officinale, Stellaria media and Thlaspi arvense, pref erably selected from the group consisting of Amaranthus powellii, Amaranthus retroflexus, Ama ranthus tuberculatus, Amaranthus rudis, Chenopodium album, Matricaria chamomilla, Matricaria inodora, Papaver rhoeas and Stellaria media, and more preferably Papaver rhoeas.
In particular, the herbicidal combinations, agrochemical compositions, uses and methods of the present invention are suitable for controlling ACCase-resistant grass weeds, more specifically ACCase-resistant grass weeds selected from the group consisting of Alopecurus myosuroides, Alopecurus aequalis, Apera spica-venti, Avena fatua, Avena sterilis, Brachiaria plantaginea, Brachiaria decumbens, Bromus secalinus, Bromus sterilis, Bromus tectorum, Digitaria ciliaris, Digitaria insularis, Digitaria ischaemum, Digitaria sanguinalis, Echinochloa colona, Echinochloa crus-galli, Echinochloa crus-pavonis, Echinochloa erecta, Echinochloa oryzoides, Echinochloa phyllogogon, Eleusine indica, Ischaemum rugosum, Leptochloa chinensis, Leptochloa pani coides, Leptochloa scabra, Leptochloa virgata, Lolium multiflorum, Lolium perenne, Lolium I5 rigidum, 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, Digi taria ischaemum, Digitaria sanguinalis, Echinochloa crus-galli, Echinochloa oryzoides, Lepto chloa chinensis, Lolium multiflorum, Lolium perenne, Lolium rigidum, Phalaris brachystachys, Phalaris minor, Phalaris paradoxa, Poa annua, Poa trivialis, Setaria faberi, Setaria glauca, Setaria pumilla, Setaria verticillata and Setaria viridis, more preferably selected from the group consisting of Alopecurus myosuroides, Alopecurus aequalis, Apera spica-venti, Echinochloa crus-galli, Echinochloa oryzoides, Leptochloa chinensis, Lolium multiflorum, Lolium perenne, Lolium rigidum, Phalaris brachystachys, Phalaris minor, Phalaris paradoxa and Poa annua, es pecially preferably selected from the group consisting of Alopecurus myosuroides, Alopecurus aequalis, Apera spica-venti, Echinochloa crus-galli, Echinochloa oryzoides, Leptochloa chinen sis,Lolium multiflorum, Lolium rigidum, Phalaris minor and Poa annua, and in particular selected from the group consisting of Alopecurus myosuroides, Lolium multiflorum, Lolium rigidum and Phalaris minor.
The herbicidal combinations, agrochemical compositions, uses and methods of the present in vention are also suitable for controlling ALS-resistant grass weeds, more specifically ALS-re sistant grass weeds 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, Pani cum capillare, Panicum dichotomiflorum, Phalaris brachystachyx, Phalaris minor, Phalaris para doxa, 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, Digitaria ischae mum, Digitaria sanguinalis, Echinochloa crus-galli, Echinochloa oryzoides, Leptochloa chinen sis, Lolium multiflorum, Lolium perenne, Lolium rigidum, Phalaris brachystachys, Phalaris minor, Phalaris paradoxa, Poa annua, Poa trivialis, Setaria faberi, Setaria glauca, Setaria pumilla, Setaria verticillata and Setaria viridis, more preferably selected from the group consisting of Alo pecurus myosuroides, Alopecurus aequalis, Apera spica-venti, Echinochloa crus-galli, Echi nochloa oryzoides, Leptochloa chinensis, Lolium multiflorum, Lolium perenne, Lolium rigidum, Phalaris brachystachys, Phalaris minor, Phalaris paradoxa and Poa annua, especially prefera bly selected from the group consisting of Alopecurus myosuroides, Alopecurus aequalis, Apera spica-venti, Echinochloa crus-galli, Echinochloa oryzoides, Leptochloa chinensis, Lolium multi florum, Lolium rigidum Phalaris minor and Poa annua, and in particular selected from the group consisting of Alopecurus myosuroides, Lolium multiflorum, Lolium rigidum and Phalaris minor.
The herbicidal combinations, agrochemical compositions, uses and methods of the present in I5 vention are also suitable for controlling ALS-resistant dicotyledonous weeds, more specifically ALS-resistant dicotyledonous weeds selected from the group consisting of Amaranthus albus, Amaranthus blitoides, Amaranthus hybridus, Amaranthus palmeri, Amaranthus powellii, Ama ranthus retroflexus, Amaranthus tuberculatus, Amaranthus rudis, Amaranthus viridis, Ambrosia artemisiifolia, Anthemis arvensis, Capsella bursa-pastoris, Centaurea cyanus, Chenopodium al bum, Chenopodium ficifolium, Chenopodium polyspermum, Chenopodium hybridum, Conyza bonariensis, Conyza canadensis, Descurania sophia, Galium aparine, Galium spurium, Galium tricornutum, Kochia scoparia, Matricaria chamomilla, Matricaria discoidea, Matricaria inodora, Papaver rhoeas, Raphanus raphanistrum, Sinapis alba, Sinapis arvensis, Sisymbrium officinale, Sisymbrium orientale, Stellaria media, and Thlaspi arvense, preferably selected from the group consisting of Amaranthus powellii, Amaranthus retroflexus, Amaranthus tuberculatus, Amaran thus rudis, Anthemis arvensis, Capsella bursa-pastoris, Centaurea cyanus, Chenopodium al bum, Descurania sophia, Kochia scoparia, Matricaria chamomilla, Matricaria inodora, Papaver rhoeas, Sisymbrium officinale, Stellaria media and Thlaspi arvense, more preferably selected from the group consisting of Amaranthus powellii, Amaranthus retroflexus, Amaranthus tubercu latus, Amaranthus rudis, Chenopodium album, Matricaria chamomilla, Matricaria inodora, Papa ver rhoeas and Stellaria media, and in particular Papaver rhoeas.
In particular, the herbicidal combinations, agrochemical compositions, uses and methods of the present invention are suitable for controlling PS Il-resistant grass weeds, more specifically PS I-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, 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, Digitaria ischae mum, Digitaria sanguinalis, Echinochloa crus-galli, Echinochloa oryzoides, Leptochloa chinen sis, Lolium multiflorum, Lolium perenne, Lolium rigidum, Phalaris brachystachys, Phalaris minor, Phalaris paradoxa, Poa annua, Poa trivialis, Setaria faberi, Setaria glauca, Setaria pumilla, Setaria verticillata and Setaria viridis, more preferably selected from the group consisting of Alo pecurus myosuroides, Alopecurus aequalis, Apera spica-venti, Echinochloa crus-galli, Echi nochloa oryzoides, Leptochloa chinensis, Lolium multiflorum, Lolium perenne, Lolium rigidum, Phalaris brachystachys, Phalaris minor, Phalaris paradoxa and Poa annua, especially prefera bly selected from the group consisting of Alopecurus myosuroides, Alopecurus aequalis, Apera spica-venti, Echinochloa crus-galli, Echinochloa oryzoides, Leptochloa chinensis, Lolium multi florum, Lolium rigidum, Phalaris minor and Poa annua, and in particular selected from the group consisting of Alopecurus myosuroides, Lolium multiflorum, Lolium rigidum and Phalaris minor.
The herbicidal combinations, agrochemical compositions, uses and methods of the present in vention are also suitable for controlling PSII-resistant dicotyledonous weeds, more specifically PSll-resistant dicotyledonous weeds selected from the group consisting of Amaranthus albus, Amaranthus blitoides, Amaranthus hybridus, Amaranthus palmeri, Amaranthus powellii, Ama ranthus retroflexus, Amaranthus tuberculatus, Amaranthus rudis, Amaranthus viridis, Ambrosia artemisiifolia, Anthemis arvensis, Capsella bursa-pastoris, Centaurea cyanus, Chenopodium al bum, Chenopodium ficifolium, Chenopodium polyspermum, Chenopodium hybridum, Conyza bonariensis, Conyza canadensis, Descurania sophia, Galium aparine, Galium spurium, Galium tricornutum, Kochia scoparia, Matricaria chamomilla, Matricaria discoidea, Matricaria inodora, Papaver rhoeas, Raphanus raphanistrum, Sinapis alba, Sinapis arvensis, Sisymbrium officinale, Sisymbrium orientale, Stellaria media and Thlaspi arvense, preferably selected from the group consisting of Amaranthus powellii, Amaranthus retroflexus, Amaranthus tuberculatus, Amaran thus rudis, Anthemis arvensis, Capsella bursa-pastoris, Centaurea cyanus, Chenopodium al bum, Descurania sophia, Kochia scoparia, Matricaria chamomilla, Matricaria inodora, Papaver rhoeas, Sisymbrium officinale, Stellaria media and Thlaspi arvense, more preferably selected from the group consisting of Amaranthus powellii, Amaranthus retroflexus, Amaranthus tubercu latus, Amaranthus rudis, Chenopodium album, Matricaria chamomilla, Matricaria inodora, Papa ver rhoeas and Stellaria media, and in particular Papaver rhoeas.
The herbicidal combinations, agrochemical compositions, uses and methods of the present in vention 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 Ii 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), Triti I5 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 herbicidal combinations, agrochemical compositions, uses and methods of the present in vention are also suitable for controlling undesirable vegetation in crops which have been modi fied by mutagenesis 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 com 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, csrl-2, gm-hra, S4-HrA, for tolerance to ALS inhibitor herbicides: csrl-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, MZHGOJG, HCEM485, VCO 01981-5, 676, 678, 680, 33121, 4114, 59122, 98140, Bt0, 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, SYHTOH2, 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, BXN10222, BXN10224, 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, RF2and RF3.
Insect resistance has mainly been created by transferring bacterial genes for insecticidal pro I5 teins to plants. Transgenes which have most frequently been used are toxin genes of Bacillus spec. and synthetic variants thereof, like cry1A, crylAb, crylAb-Ac, crylAc, cry1A.105, cry1F, crylFa2, cry2Ab2, cry2Ae, mcry3A, ecry3.1Ab, cry3Bbl, cry34Abl, cry35Abl, 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, Btl0, Bt1, Bt176, MON801, MON802, MON809, MON810, MON863, MON87411, MON88017, MON89034, 33121, 4114, 5307, 59122, TC1507, TC6275, CBH-351, MIR162, DBT418 andMZIR098. Transgenic soybean events comprising genes for insecticidal proteins are for example, but not excluding others, MON87701, MON87751 and DAS-81419. Transgenic cotton events comprising genes for insecticidal proteins are for example, but not ex cluding others, SGK321, MON531, MON757, MON1076, MON15985, 31707, 31803, 31807, 31808, 42317, BNLA-601, Event1, 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 athbl7, 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 fatbl-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 us ing 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 W02017/011288.
The herbicidal combinations, agrochemical compositions, uses and methods of the present in vention 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 abi otic stress factors. Such effects may in particular comprise enhanced yield, enhanced re sistance or tolerance to insects, nematodes, fungal, bacterial, mycoplasma, viral or viroid patho gens 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 herbicidal combinations, agrochemical compositions, uses and methods of the present invention are also suitable for the defoliation and/or desicca tion of plant parts, for which crop plants such as cotton, potato, oilseed rape, sunflower, soy bean or field beans, in particular cotton, are suitable. In particular, the herbicidal combinations, agrochemical compositions, uses and methods of the present invention are suitable for desic cating the above-ground parts of crop plants such as potato, oilseed rape, sunflower and soy bean, 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
1. Binary combination of herbicides A and B
The effect of the herbicidal combination according to the invention of the herbicides A and B on the growth of undesirable plants compared to the herbicidally active compounds alone was demonstrated by the following greenhouse experiments:
The test plants have been 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 had rooted. This cover caused uniform germination of the test plants unless this was adversely affected by the active compounds.
The plants have been cultivated due to their individual requirements at 10 - 25°C and 20 - 35°C. The plants were irrigated due to their necessity.
Herbicide A (2-(2,4-dichlorophenyl)methyl-4, 4-dimethyl-3-isoxazolidone of the formula I, also ab breviated herein as "2,4-DC") was used as an EC (emulsifiable concentrate) formulation having an active ingredient concentration of 5 %.
Herbicide B, i.e. ()-2-exo-(2-Methylbenzyloxy)-1-methyl-4-isopropyl-7-oxabicyclo[2.2.1]heptane (common name: cinmethylin) was used as EC (emulsifiable concentrate) formulation having an active ingredient concentration of 750 g/l.
In the following experiments, the herbicidal activity for the individual herbicidal compositions (solo and mixture applications) was assessed 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 belonged to the following species:
EPPO Code Scientific name AVEFA Avena fatua GERDI Geranium dissectum LOLMU Lolium multiflorum MATIN Matricaria inodora PAPRH Papaver rhoeas STEME Stellaria media
Colby's equation was 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 - (X-Y/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.
Table 1 below relates to the herbicidal activity, in greenhouse trials, of the individual actives and the combinations applied at different rates and ratios, in preemergence application at 20 days after treatment (DAT).
Table 1: Preemergence application of herbicide A (2,4-DC) and herbicide B (Cinmethylin)
solo application combination herbicide A herbicide B herbicide A + herbicide B (2,4-DC) (Cinmethylin) (2,4-DC + Cinmethylin) Herbici-Cobex use herbicidal Colbyex Weed use rate herbicidal dal acti- use rate pected rate (g atvt species (g ai/ha) activity vity (g ai/ha) a herbicidal ai/ha) (%) (%) (%) activity E(%) 125+ LOLMU 125 65 31.25 75 31.25 95 91 125+ LOLMU 125 65 15.625 60 15.625 90 86 31.25+ LOLMU 31.25 30 31.25 75 31.25 85 83 solo application combination herbicide A herbicide B herbicide A + herbicide B (2,4-DC) (Cinmethylin) (2,4-DC + Cinmethylin) Herbici-Cobex use herbicidal Colbyex Weed use rate herbicidal dal acti- use rate pected rate (g atvt species (g ai/ha) activity ai/ha) vity (g ai/ha) a herbicidal (%) (%) activity E(%) 31.25+ AVEFA 31.25 0 31.25 30 31.25 35 30 31.25+ AVEFA 31.25 0 15.625 0 15.625 35 0 125+ MATIN 125 50 31.25 0 31.25 60 50 125+ MATIN 125 50 15.625 0 15.625 60 50 62.5+ MATIN 62.5 50 15.625 0 15.625 55 50 31.25+ PAPRH 31.25 30 31.25 60 31.25 60 58 15.625+ PAPRH 15.625 0 15.625 40 15.625 65 40 125+ GERDI 125 40 31.25 0 31.25 60 40 125+ GERDI 125 40 15.625 0 15.625 60 40 62.5+ GERDI 62.5 40 31.25 0 31.25 50 40 31.25+ STEME 31.25 98 31.25 0 31.25 100 98
As can be seen from the data in Table 1, the combination of herbicides A (2,4-DC) and B (cinmethylin) exhibits an unexpected synergistic effect in that the herbicidal activity against vari ous weed species in a pre-emergence treatment is significantly higher than would be predicted based on the values for each of the compounds individually.
II. Ternary combination of herbicides A, B and C
The herbicidal activity of a ternary combination of this invention of the herbicides A, B and C on the growth of undesirable plants was tested by greenhouse experiments under the same condi tions as outlined above under Section I for the binary combinations of the herbicides A and B.
In addition, pyroxasulfone as an example of the herbicide C was used as a WG (water dispersi ble granule) formulation having an active ingredient concentration of 85%.
Moreover, for the post emergence treatment, the plants were first grown to the 2-leaf stage (GS 12-13). Here, the herbicidal compositions were suspended or emulsified in water as distribution medium and sprayed using finely distributing nozzels.
The plants used in the greenhouse experiments belonged to the following species:
EPPO Code Scientific name ABUTH Abutilon theoprasti ALOMY Alopecurus myosuroides ANTAR Anthemis arvensis AVEFA Avena fatua BRADC Brachiaria decumbens CHEAL Chenopodium album GALAP Galium aparine GERDI Geranium dissectum LOLMU Lolium multiflorum LOLPE Lolium perenne LOLRI Lolium rigidum POLCO Polygonum convolvulus SETVI Setaria viridis
To evaluate whether there is a synergistic effect on the ternary combination of herbicides A (2,4-DC), B (Cinmethylin) and C (Pyroxasulfone) according to this invention in relation to the bi nary combination of Cinmethylin + Pyroxasulfone (herbicide B + herbicide C) as described in WO 2017/009090 and the sole active ingredient 2,4-DC (herbicide A) the Colby formula was used as follows:
E = X + Y - (X-Y/100) where:
X = effect in percent using the binary combination B+C at an application rate b+c; Y = effect in percent using herbicide A at an application rate a; E % = expected activity according to Colby of the ternary combination A+B+C at application rates a+b+c
If the value observed in this manner is higher than the value E calculated according to Colby, a synergistic effect is present.
Tables 2 and 3 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 plication at 20 days after treatment (DAT).
Table 2: Preemergence application of herbicides A (2,4-DC), B (Cinmethylin) and C (Pyroxasul fone) solo application Ternary combination combination B + C herbicide A (Cinmethylin
+ (2,4-DC) Pyroxasulfone) herbicide A + herbicide B + herbicide C according to WO 2017/009090
Herbici- Colby ex herbicidal pce Weed use rate herbicidal use rate aciit use rate dal pected species (g ai/ha) activity (g ai/ha) ati (g ai/ha) activity activityE (%) (%) ABUTH 125 40 200+80 95 125+200+80 100 97 ABUTH 125 40 100+40 90 125+100+40 95 94 ABUTH 62.5 40 75+40 95 62.5+75+40 100 97 ABUTH 31.25 0 50+15 50 31.25+50+15 65 50 ABUTH 31.25 0 25+7.5 40 31.25+25+7.5 55 40 ABUTH 15.6 0 37.5+15 55 15.6+37.5+15 65 55 ALOMY 31.25 60 25+7.5 98 31.25+25+7.5 100 99 ALOMY 15.6 10 37.5+15 98 15.6+37.5+15 100 98 ALOMY 15.6 10 18.75+7.5 98 15.6+18.75+7.5 100 98 ANTAR 125 45 100+40 95 125+100+40 98 97 ANTAR 62.5 30 75+40 90 62.5+75+40 100 93 ANTAR 15.6 20 150+60 95 15.6+150+60 98 96 AVEFA 125 70 200+80 85 125+200+80 98 96 AVEFA 125 70 25+10 80 125+25+10 95 94 AVEFA 31.25 10 200+60 95 31.25+200+60 98 96 AVEFA 31.25 10 100+30 85 31.25+100+30 98 87 AVEFA 15.6 10 75+30 85 15.6+75+30 90 87 BRADC 62.5 30 75+40 95 62.5+75+40 100 97 BRADC 31.25 0 25+7.5 30 31.25+25+7.5 80 30 BRADC 15.6 0 18.75+7.5 65 15.6+18.75+7.5 80 65 CHEAL 125 55 100+40 98 125+100+40 100 99 CHEAL 15.6 0 75+30 98 15.6+75+30 100 98 GALAP 125 80 200+80 95 125+200+80 100 99 GALAP 62.5 50 37.5+20 60 62.5+37.5+20 85 80 GALAP 31.25 50 100+30 90 31.25+100+30 100 95 GALAP 15.6 40 75+30 85 15.6+75+30 100 91 GALAP 15.6 40 37.5+15 60 15.6+37.5+15 80 76 GERDI 31.25 70 200+60 95 31.25+200+60 100 99 GERDI 31.25 70 25+7.5 80 31.25+25+7.5 95 94 LOLMU 31.25 45 50+15 98 31.25+50+15 100 99 LOLPE 15.6 5 150+60 98 15.6+150+60 100 98 solo application Ternary combination combination B + C herbicide A (Cinmethylin
+ (2,4-DC) Pyroxasulfone) herbicide A + herbicide B + herbicide C according to WO 2017/009090
Herbici- Colby ex herbicidal pce Weed use rate herbicidal use rate aciit use rate dal pected species (g ai/ha) activity (g ai/ha) ati (g ai/ha) activity activityE (%) (%) LOLRI 125 60 50+20 98 125+50+20 100 99 POLCO 62.5 0 75+40 65 62.5+75+40 75 65 POLCO 31.25 0 100+30 65 31.25+100+30 80 65 SETVI 15.6 0 37.5+15 98 15.6+37.5+15 100 98 SETVI 15.6 0 18.75+7.5 98 15.6+18.75+7.5 100 98 * Expected activity according to the Colby's equation wherein the activity of the combination of herbicides B and C (cinmethylin + pyroxasulfone) is calculated as activity of a single active in gredient
Table 3: Postemergence application of herbicides A (2,4-DC), B (Cinmethylin) and C (Pyrox asulfone)
solo application Ternary combination combination B + C
herbicide A (Cinmethylin +
(2,4-DC) Pyroxasulfone) herbicide A + herbicide B + herbicide C according to WO 2017/009090
herbici- Colby ex herbicidal pected Weed use rate herbicidal use rate aciit use rate (g dal hecid species (g ai/ha) activity (g ai/ha) ati ai/ha) activity activityE (%) (%) ALOMY 15.6 20 18.75+7.5 65 15.6+18.75+7.5 75 72 AVEFA 31.25 30 200+60 80 31.25+200+60 90 86 AVEFA 31.25 30 50+15 25 31.25+50+15 75 48 AVEFA 15.6 10 150+60 80 15.6+150+60 90 82 AVEFA 15.6 10 37.5+15 10 15.6+37.5+15 60 19 AVEFA 15.6 10 18.75+7.5 10 15.6+18.75+7.5 30 19 LOLMU 31.25 60 200+60 85 31.25+200+60 95 94 *Expected activity according to the Colby's equation wherein the activity of the combination of herbicides B and C (cinmethylin + pyroxasulfone) is calculated as activity of a single active in gredient
As can be seen from the data in Tables 2 and 3, the herbicidal activities of the ternary combina tion of herbicides A (2,4-DC), B (Cinmethylin) and C (Pyroxasulfone) were higher for several weed species in a pre- and post-emergence treatment than the expected Colby values that were calculated using the % activity results of the binary combination of herbicides B (Cinme thylin) and C (Pyroxasulfone) and the single herbicide A (2,4-DC). Thus, the addition of the herbicide A (2,4-DC) to the binary combination of herbicides B (Cinmethylin) and C (Pyroxasul fone) leads to a synergistic effect.
o It is to be understood that, if any prior art publication is referred to herein, such reference does not constitute an admission that the publication forms a part of the common general knowledge in the art, in Australia or any other country.
In the claims which follow and in the preceding description of the invention, except where the context requires otherwise due to express language or necessary implication, the word "com prise" or variations such as "comprises" or "comprising" is used in an inclusive sense, i.e. to specify the presence of the stated features but not to preclude the presence or addition of fur ther features in various embodiments of the invention.
Claims (1)
- Claims1. Use of an herbicidal combination, wherein the herbicidal combination comprises:a) an herbicide A which is 2-(2,4-dichlorophenyl)methyl-4,4-dimethyl-3-isoxazolidone of the formula I 0H3C I C () HC Caandb) an herbicide B which is ()-2-exo-(2-Methylbenzyloxy)-1-methyl-4-isopropyl-7-oxabi cyclo[2.2.1]heptane, any of its individual enantiomers or any non-racemic mixture thereoffor controlling undesirable vegetation, wherein the undesirable vegetation is Lolium multi florum; wherein the herbicide A and the herbicide B are applied simultaneously or in suc cession and, in case of successive application, the herbicide A and the herbicide B are applied in a time frame that allows simultaneous action of the active ingredients on the plants to be controlled;or the use of an agrochemical composition comprising a herbicidally effective amount of o the herbicidal combination and one or more auxiliaries customary in crop protection for controlling undesirable vegetation, wherein the undesirable vegetation is Lolium multiflo rum.2. A method for controlling undesirable vegetation which comprises applying to the vegetation or the locus thereof or applying to the soil or water to prevent the emergence or growth of the undesirable vegetation the herbicidal combination or the agrochemical composition of claim 1, wherein the undesirable vegetation is Lolium multiflorum.3. The use according to claim 1 or the method according to claim 2, wherein the herbicide B is (±)-2-exo-(2-Methylbenzyloxy)-1-methyl-4-isopropyl-7-oxabicyclo[2.2.1]heptane.4. The use or method according to any one of claims 1 to 3, wherein the herbicidal combination further comprises c) at least one herbicide C which is different from herbicides A and B.5. The use or method according to claim 4, wherein the herbicide C is selected fromc1) 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[1,1'-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[1,1'-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-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[1,1'-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-cyclo propyl- [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-tet o ramethyl-5-oxo-2H-pyran-3-yl carbonic acid methyl ester (CAS 1312340-83-2); 4-(2',4' Dichloro-4-ethyl[1,1'-biphenyl]-3-yl)-5,6-dihydro-2,2,6,6-tetramethyl-5-oxo-2H-pyran-3-y 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; c2) 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, pyrazosufuron-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 (CAS420138-41-6), 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;c3) photosynthesis inhibitors: amicarbazone, inhibitors of the photosystem || 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 o 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, pyridafol, pentanochlor and propanil and inhibitors of the photosystem I selected from diquat, diquat-dibromide, paraquat, paraquat-dichloride and paraquat dimetilsulfate.c4) 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-1H-pyrazole-1-carboxamide (CAS 452098-92-9), N-tetrahydrofurfuryl-3-(2,6-dichloro-4-trifluoromethylphenoxy)-5-methyl-1H pyrazole-1-carboxamide (CAS 915396-43-9), N-ethyl-3-(2-chloro-6-fluoro-4-trifluoro methylphenoxy)-5-methyl-1H-pyrazole-1-carboxamide (CAS 452099-05-7), N-tetrahydro furfuryl-3-(2-chloro-6-fluoro-4-trifluoromethylphenoxy)-5-methyl-1H-pyrazole-1-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 1300118-96-0), 1-methyl-6-trifluoromethyl-3-(2,2,7-trifluoro-3-oxo 4-prop-2-ynyl-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)-1H-pyrimidine-2,4-dione (CAS 1304113-05-0), methyl (E)-4-[2-chloro-5-[4-chloro-5-(difluoromethoxy)-1H-methyl-pyrazol 3-yl]-4-fluoro-phenoxy]-3-methoxy-but-2-enoate (CAS 948893-00-3), and 3-[7-chloro-5 fluoro-2-(trifluoromethyl)-1H-benzimidazol-4-yl]-1-methyl-6-(trifluoromethyl)-1H-pyrimidine 2,4-dione (CAS 212754-02-4);c5) 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 o 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 1361139-71-0) and 2-(2,5-dichlorophenyl)methyl-4,4-dimethyl-3-isoxazolidinone (CAS 81778-66-7);c6) EPSP synthase inhibitors: glyphosate, glyphosate-isopropylammonium, glyposate-potassium and glyphosate-tri mesium (sulfosate);c7) glutamine synthase inhibitors: bilanaphos (bialaphos), bilanaphos-sodium, glufosinate, glufosinate-P and glufosinate-am monium;c8) DHP synthase inhibitors: asulam;c9) 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; c10) 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, 11.2,11.3, 11.4, 11.5, 11.6, 11.7, 11.8 and 11.9F 3C N 0F 3C N N F O\ O N-H 3 0 ' HN-CH 3 H3 OCHF2 H OCHF H3C O-N 2 3C 0 -N 11.1 11.2F 30 N F3 N F 30 N F O\/9 N-H O\,9 NOH 04, 5 N-CH 3 T H3 0 N H 3 CO N H3O T N H3 0 -N H 3 0 O-N F H3 0 O-N11.3 11.4 11.5 F 3C F3 C N O N-CH N-OH" 3 0 0 N-CH 3 HCH 3C S NN-H 3 O F F OCHF 2 C FF N11.6 11.7F3C N F3C N FO O N-CH3 F O N-OH H3C H3C N SF F OCHF 2 HC NF FN11.8 11.9cl1) cellulose biosynthesis inhibitors: chlorthiamid, dichlobenil, flupoxam, indaziflam, isoxaben, triaziflam and 1-cyclohexyl-5 pentafluorphenyloxy-1 4 -[1,2,4,6]thiatriazin-3-ylamine (CAS 175899-01-1);c12) decoupler herbicides: dinoseb, dinoterb and DNOC and its salts; c13) 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-1H-indol-6-yl)picolinic acid (CAS 1629965-65-6); c14) auxin transport inhibitors: diflufenzopyr, diflufenzopyr-sodium, naptalam and nap talam-sodium; c15) other herbicides: bromobutide, chlorflurenol, chlorflurenol-methyl, cumyluron, cy o 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, methiozolin (CAS 403640-27-7), methyl azide, me thyl bromide, methyl-dymron, methyl iodide, MSMA, oleic acid, oxaziclomefone, pelar gonic acid, pyributicarb, quinoclamine and tridiphane.6. The use or method according to claims 4 or 5, wherein the herbicide C is selected fromc1) lipid biosynthesis inhibitors: prosulfocarb, triallate;c2) ALS inhibitors: imazamox;c3) photosynthesis inhibitors: metribuzin, terbuthylazin, chlorotoluron and isoproturon;c4) protoporphyrinogen-IX oxidase inhibitors: flumioxazin, saflufenacil, sulfentrazone and trifludimoxazin;c5) bleacher herbicides: diflufenican, picolinafen, flurtamone, aclonifen, and clomazone; c6) EPSP synthase inhibitors: glyphosate, glyphosate-isopropylammonium, glyphosate-potassium and glyphosate-tri mesium (sulfosate); c7) glutamine synthase inhibitors: glufosinate, glufosinate-P and glufosinate-ammonium; c9) mitosis inhibitors: pendimethalin and trifluralin; c10) VLCFA inhibitors: acetochlor, dimethachlor, dimethenamid, dimethenamid-P, metazachlor, metolachlor, S metolachlor, pethoxamid, pretilachlor, flufenacet, napropamide, napropamide-M and py roxasulfone; c13) synthetic auxins: aminopyralid and its salts selected from aminopyralid-dimethylammonium, aminopyralid tris(2-hydroxypropyl)ammonium and its esters, halauxifen and its salts and esters (CAS 943832-60-8), quinclorac, quinmerac, florpyrauxifen, florpyrauxifen-benzyl (CAS 1390661 72-9) and 4-amino-3-chloro-5-fluoro-6-(7-fluoro-1H-indol-6-yl)picolinic acid (CAS o 1629965-65-6); c15) other herbicides: indanofan, methiozolin (CAS 403640-27-7) and oxaziclomefone.7. The use or method according to any one of claims 3 to 5, wherein the herbicide C is pyroxasulfone.8. The use or method according to any one of claims 1 to 7, wherein the weight ratio of herbicide A to herbicide B is from 1:0.05 to 1:20.9. The use or method according to any one of claims 4 to 8, wherein the weight ratio of herbicide A to herbicide C is from 1:0.002 to 1:160.10. The use or method according to any one of claims 1 to 9, wherein the herbicidal combination further comprises d) at least one safener D 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.11. The use or method according to any one of claims 1 to 10, wherein the undesirable vegetation is controlled in crop plants selected from 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.12. An agrochemical composition comprising a herbicidally effective amount of an herbicidal combination comprising:(a) an herbicide A which is 2-(2,4-dichlorophenyl)methyl-4,4-dimethyl-3-isoxazolidone of the formula I0H 3C I Na (I) H3 3 C1(b) an herbicide B which is ()-2-exo-(2-Methylbenzyloxy)-1-methyl-4-isopropyl-7-oxabi cyclo[2.2.1]heptane, any of its individual enantiomers or any non-racemic mixture thereof, and(c) an herbicide C which is pyroxasulfone,wherein the herbicide A, the herbicide B and the herbicide C are the only herbicidally ac o tive ingredients; andone or more auxiliaries customary in crop protection.13. The agrochemical composition according to claim 12, wherein the weight ratio of herbicide A to herbicide B is in the range from 1:0.1 to 1:10, optionally in the range from 1:0.1 to 1:8, or optionally in the range from 1:0.2 to 1:5; the weight ratio of herbicide A to herbicide C is in the range from 1:0.02 to 1:6, optionally in the range from 1:0.05 to 1:5, or optionally in the range from 1:0.05 to 1:3; and the weight ratio of herbicide B to herbicide C is in the range from 1:0.02 to 1:6, optionally in the range from 1:0.05 to 1:3, or optionally in the range from 1:0.1 to 1:1.14. An agrochemical composition comprising a herbicidally effective amount of an herbicidal combination comprising(a) an herbicide A which is 2-(2,4-dichlorophenyl)methyl-4,4-dimethyl-3-isoxazolidone of the formula I0H3 C1 C1(b) an herbicide B which is ()-2-exo-(2-Methylbenzyloxy)-1-methyl-4-isopropyl-7-oxabi cyclo[2.2.1]heptane, any of its individual enantiomers or any non-racemic mixture thereof, and(c) an herbicide C which is pyroxasulfone;wherein the weight ratio of herbicide A to herbicide B is in the range from 1:0.1 to 1:10, optionally in the range from 1:0.1 to 1:8, or optionally in the range from 1:0.2 to 1:5; the weight ratio of herbicide A to herbicide C is in the range from 1:0.02 to 1:6, optionally in the range from 1:0.05 to 1:5, or optionally in the range from 1:0.05 to 1:3; and the weight ratio of herbicide B to herbicide C is in the range from 1:0.02 to 1:6, optionally in the range from 1:0.05 to 1:3, or optionally in the range from 1:0.1 to 1:1;and one or more auxiliaries customary in crop protection.
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| US4487945A (en) | 1981-12-16 | 1984-12-11 | Shell Oil Company | Preparation of 2-exo-Hydroxy-7-oxabicyclo[2.2.1]heptanes |
| RS53904B1 (en) | 2011-04-29 | 2015-08-31 | Fmc Corporation | USE OF 3-ISOXAZOLIDINONE AS SELECTIVE HERBICIDES FOR HERBS AND CROSS |
| EP3028573A1 (en) | 2014-12-05 | 2016-06-08 | Basf Se | Use of a triazole fungicide on transgenic plants |
| EA201890260A1 (en) | 2015-07-10 | 2018-07-31 | Басф Агро Б.В. | HERBICID COMPOSITION CONTAINING ZINMETHYLINE AND PYROXASULPHONE |
| BR112018000687B1 (en) | 2015-07-13 | 2021-05-04 | Fmc Corporation | compost, herbicide compositions, herbicide mixtures and methods for controlling the growth of unwanted vegetation |
| CN113749107A (en) | 2015-08-07 | 2021-12-07 | 拜耳作物科学股份公司 | 2-(2,4-Dichlorophenyl)methyl-4,4-dimethyl-3-isoxazolidinone as a foliar herbicide |
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2019
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- 2019-06-11 WO PCT/EP2019/065095 patent/WO2019243100A1/en not_active Ceased
- 2019-06-11 AU AU2019290961A patent/AU2019290961B2/en active Active
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2015127259A1 (en) * | 2014-02-23 | 2015-08-27 | Fmc Corporation | Use of 3-isoxazolidinones compounds as selective herbicides |
| WO2018041762A2 (en) * | 2016-08-30 | 2018-03-08 | Bayer Cropscience Aktiengesellschaft | Method of reducing crop damage |
| WO2018172442A1 (en) * | 2017-03-24 | 2018-09-27 | Bayer Aktiengesellschaft | Herbicidal mixtures |
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|---|---|
| WO2019243100A1 (en) | 2019-12-26 |
| EP3809848A1 (en) | 2021-04-28 |
| AU2019290961A1 (en) | 2020-12-24 |
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